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WO2013026866A2 - Novel microbiocides - Google Patents

Novel microbiocides Download PDF

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Publication number
WO2013026866A2
WO2013026866A2 PCT/EP2012/066312 EP2012066312W WO2013026866A2 WO 2013026866 A2 WO2013026866 A2 WO 2013026866A2 EP 2012066312 W EP2012066312 W EP 2012066312W WO 2013026866 A2 WO2013026866 A2 WO 2013026866A2
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WIPO (PCT)
Prior art keywords
alkyl
ch2ch2ch2
halogen
alkoxy
independently selected
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PCT/EP2012/066312
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French (fr)
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WO2013026866A3 (en
Inventor
Werner Zambach
Laura Quaranta
Clara Massol-Frieh
Stephan Trah
Daniel Stierli
Martin Pouliot
Kurt Nebel
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Syngenta Participations Ag
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Publication of WO2013026866A2 publication Critical patent/WO2013026866A2/en
Publication of WO2013026866A3 publication Critical patent/WO2013026866A3/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C—CHEMISTRY; METALLURGY
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the present invention relates to novel microbiocidally active, in particular fungicidally active heterocyclic compounds. It further relates to intermediates used in the preparation of these compounds, to compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by
  • phytopathogenic microorganisms preferably fungi.
  • Fungicidally active 2-(pyridin-2-yl)-pyrimidines are described in WO 2007/116079.
  • the disclosed compounds are characterised by a condensed aliphatic carbocycle or heterocycle. Surprisingly, it has been found that several heterocyclic systems, including novel compounds have microbiocidal activity.
  • the present invention relates to a method comprising applying to useful plants, the locus thereof or propagation material thereof a compound of formula (I)
  • L 1 is N or C-D 1 ;
  • L 2 is N or C-D 2 ;
  • L 3 is N or C-D 3 ;
  • L 4 is N or C-D 4 ;
  • L 5 is N or C-D 5 ;
  • L 6 is N or C-D 6 ;
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR 1 , OR 2 , SH, d-C 8 alkylthio, d-C 8 alkylsulphinyl, Ci-C 8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R ⁇ CON(R
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , or D 4 and D 6 independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , or D 4 and D 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH,
  • X represents X-2, X-3, X-4 or X-5:
  • groupings X-2, X-3, X-4 and X-5 contain at most one ring which contains either only one of the radicals Z 1 to Z 14 or two radicals Z 1 to Z 14 or three radicals Z 1 to Z 14 or four radicals Z 1 to Z 14 as ring members; and wherein none of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 and Z 14 represent a carbon atom substituted by two OH;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
  • each Y 1 , Y 2 , Y 3 and Y 4 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-Cs alkyl, C 3 -C 8 cydoalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR 1 , OR 2 , SH, d-C 8 alkylthio, d-C 8 alkylsulphinyl, Ci-C 8 a I kyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R
  • Y 1 and D 1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • R 12 and D 1 together may be
  • Q' is selected from the group consisting of Q- ⁇ , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'
  • each Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR 1 , OR 2 , SH, d-C 8 alkylthio, d-C 8 alkylsulphinyl, Ci-C 8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C
  • Y 4' independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1' and Y 2' , Y 2' and Y 3' , or Y 3' and Y 4' is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-Q alkyl, d-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio; when Q' is Q
  • each G 1 and G 2 independently of one another represent -C(R 14 R 15 )-;
  • each G 3 independently of one another represents -C(R 14 R 15 )-, 0, N(R 16 ) or S;
  • each p independently of one another represents 0, 1 or 2;
  • each R 1 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 2 independently of one another represents hydrogen, CrC 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Q-G, alkyl, Ci-C 4 -haloalkyl, Q-G, alkoxy, Q-G, haloalkoxy and G-C 4 -alkoxy-Ci-C 4 -alkyl;
  • each R 3 independently of one another represents hydrogen, OH, G-C 8 alkyl, G-C 8 alkoxy, G-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl or COR 1 , wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen;
  • radicals R 3 wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups
  • halogen independently selected from halogen, CN, NH 2 , N0 2 , OH, G-C 4 alkyl, G-C 4 haloalkyl, G-C 4 alkoxy and G-C 4 haloalkoxy;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH,
  • each R 6 and R 7 independently of one another represent hydrogen, halogen, d-C 4 alkyl or Ci-C 4 haloalkyi;
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, d-C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -
  • R 8 and R 9 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • each R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, C 2 -C 4 alkenyloxy or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, CrC 4 alkyl, d-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • R 12 and R 12' independently of one another represent hydrogen, halogen, CN, SH, d-
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-Q alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 14 and R 15 independently of one another represents hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or d-C 4 haloalkoxy;
  • each R 16 indepenently of one another represents hydrogen, OH, d-C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 cycloalkyl, d-C 8 alkylcarbonyl or d-C 8 haloalkylcarbonyl;
  • the invention covers all agronomically acceptable salts, isomers, structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers, atropisomers and N-oxides of those compounds.
  • the compounds of formula I may exist in different geometric or optical isomeric forms or in different tautomeric forms. One or more centres of chirality may be present, in which case compounds of the formula I may be present as pure enantiomers, mixtures of enantiomers, pure diastereomers or mixtures of diastereomers.
  • This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. Also
  • Atropisomerism may occur as a result of a restricted rotation about a single bond.
  • the method is a method of controlling or preventing phytopathogenic diseases on useful plants or on propagation material thereof, more preferably a method of controlling or preventing phytopathogenic fungal diseases on useful plants or on propagation material thereof.
  • Halogen either as a lone substituent or in combination with another substituent (e.g. haloalkyl) is generally fluorine, chlorine, bromine or iodine, and usually fluorine, chlorine or bromine.
  • Each alkyl moiety (including the alkyl moiety of alkoxy, alkylthio, etc.) is a straight or branched chain and, depending on the number of carbon atoms it contains, is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, / ' so-propyl, sec-butyl, / ' so-butyl, tert-butyl, neo-pentyl, n-heptyl or 1,3-dimethylbutyl, and usually methyl or ethyl.
  • the alkenyl group is an unsaturated straight or branched chain having at least one carbon-carbon double bond and, depending on the number of carbon atoms it contains, is, for example ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3- butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2- pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l- butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2- methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l
  • the alkynyl group is an unsaturated straight or branched chain having at least one carbon-carbon triple bond and, depending on the number of carbon atoms it contains, is, for example ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2- propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-l-butynyl, l-methyl-2- butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, l,l-dimethyl-2-propynyl, l-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-l-p
  • Haloalkyl moieties are alkyl moieties which are substituted by one or more of the same or different halogen atoms and are, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, 2,2, 2-tr if I uoroethyl , 2,2- difluoroethyl, 2-fluoroethyl, 1,1-d if I uoroethyl, 1-f I uoroethyl, 2-chloroethyl, pentafl uoroethyl, l,l-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, and typically trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, /so-propoxy, n-butoxy, /so-butoxy, sec-butoxy and tert-butoxy, and usually methoxy or ethoxy.
  • Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy, and usually difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.
  • Alkylthio is, for example, methylthio, ethylthio, propylthio, /so-propylthio, n-butylthio, /so-butylthio, sec-butylthio or tert-butylthio, and usually methylthio or ethylthio.
  • Alkylsulphonyl is, for example, methylsulphonyl, ethylsulphonyl, propylsulphonyl, iso- propylsulphonyl, n-butylsulphonyl, / ' so-butylsulphonyl, sec-butylsulphonyl or tert- butylsulphonyl, and usually methylsulphonyl or ethylsulphonyl.
  • Alkylsulphinyl is, for example, methylsulphinyl, ethylsulphinyl, propylsulphinyl, iso- propylsulphinyl, n-butylsulphinyl, / ' so-butylsulphinyl, sec-butylsulphinyl or tert-butylsulphinyl, and usually methylsulphinyl or ethylsulphinyl.
  • Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl,
  • Cycloalkyl may be saturated or partially unsaturated, preferably fully saturated, and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Aryl includes phenyl, naphthyl, anthracyl, fluorenyl and indanyl, but is usually phenyl.
  • Carbocycle includes cycloalkyl groups and aryl groups.
  • Heterocycloalkyl is a non-aromatic ring that may be saturated or partially
  • examples include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,4-dioxanyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, oxazinanyl, dioxolane, dithiolane, morpholinyl,
  • thiomorpholinyl imidazolidinyl, pyrazolidinyl and piperazinyl, preferably morpholinyl, pyrrolidinyl, piperdinyl and piperazinyl, more preferably dioxolane, dithiolane, morpholinyl and pyrollidinyl.
  • Heteroaryl is, for example, a monovalent monocyclic or bicyclic aromatic hydrocarbon radical.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiadiazolyl.
  • bicyclic groups include quinolinyl, cinnolinyl, quinoxalinyl, benzimidazolyl, benzothiophenyl, and benzothiadiazolyl.
  • Monocyclic heteroaryl groups are preferred, preferably pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, pyridyl and imidazolyl being most preferred.
  • heterocycle and “heterocyclic ring” are used interchangeably and are defined to include heterocycloalkyl and heteroaryl groups. Any reference herein to a heterocycle or heterocyclic ring preferably refers to the specific examples given under the definition of heteroaryl and heterocycloalkyl above, and are preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl and imidazolyl.
  • No heterocycle contains adjacent oxygen atoms, adjacent sulphur atoms, or adjacent oxygen and sulphur atoms.
  • a moiety is indicated as being (optionally) substituted, e.g. alkyl, this includes those moieties where they are part of a larger group, e.g. the alkyl in the alkylthio group and the alkyl in the alkoxy group etc.. The same applies, e.g. to the phenyl moiety in phenylthio etc.
  • a moiety is indicated as being optionally substituted by one or more other groups, preferably there are one to five optional substituents, more preferably one to three optional substituents.
  • a moiety is substituted by a cyclic group, e.g. aryl, heteroaryl, cycloalkyl, preferably there are no more than two such substituents, more preferably no more than one such substituent.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to four heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen, COR 1 , OR 2 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R ⁇ CON(R 3 ) 2 ,
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocycle as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g.
  • 1,2,4 triazolyl more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl), COR 1 , OR 2 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R 1 , CON(R 3 ) 2 , NR 3 COR ⁇ CR ⁇ -OR 2 , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OR 2 , Q-C, alkyl, d-C 4 haloalkyl
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, OR 2 , Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl, phenyl, pyridyl, C0 2 R 2 , N(R 3 ) 2 , NR 3 COR ⁇ C ⁇ N-OR ⁇ SH, Ci-C 8 -alkylthio, d-C 8 -alkylsulphinyl, Ci-C 8 - alkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OR 2 , Ci-C 8 alky
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, OR 2 , CN, d-C 4 alkyl, C 3 -C 6 cycloalkyl, N(R 3 ) 2 , phenyl, C0 2 R 2 or NR 3 COR ⁇ wherein the alkyl, cycloalkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, d-C 4 - haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, OH, CN, Ci-C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl, N(R 3 ) 2 , phenyl or C0 2 R 2 , wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups,
  • halogen independently selected from halogen, CN, d-C 4 alkyl, d-C 4 -haloalkyl, d-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, d-C 4 alkyl, CN or d-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , d-C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, CN, Ci-C 4 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , Ci-G, alkyl, C1-C4 alkoxy and Ci-G, haloalkyl.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl, a 5- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, Ci-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl.
  • a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl, a 5- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, Ci-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl.
  • a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , d-C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another preferably represent hydrogen, CN, d-C 4 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , d-C 4 alkyl, d-C 4 alkoxy and C1-C4 haloalkyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another more preferably represent hydrogen, d-C 4 alkyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C 4 alkoxy, d-C 4 alkyl and Ci-C 4 haloalkyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another even more preferably represent hydrogen, d-C 4 alkyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkoxy and Ci-C 4 haloalkoxy, wherein D 5 and D 6 are as defined above.
  • D 1 , D 2 , D 3 and D 4 independently of one another more preferably represent hydrogen, Ci-C 4 alkyl, CN or d-C 4 alkoxy, wherein D 5 and D 6 are as defined above.
  • D 1 , D 2 , D 3 and D 4 most preferably each represent hydrogen, wherein D 5 and D 6 are as defined above.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, d-C 8 alkyl, C 2 -C 8 alkynyl, d-C 8 alkoxy or Ci-Cs alkylthio.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, d-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy or Ci-C 4 alkylthio. Even more preferably in this group of compounds, D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, methoxy or methylthio.
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , or D 4 and D 6 may form a carbocyclic or heterocyclic ring.
  • This possibility and preferences thereof are described below, which may be combined with any of the definitions above.
  • the above definitions may exclude the possibility of rings formed by D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , or D 4 and D 6 .
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 is optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-Q alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R 3 ), and wherein the ring formed by D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 is optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d- C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, CrC 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 together with the fragment of the ring to which they are attached do not form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R 3 ).
  • X represents X-2, X-3, X-4 or X-5.
  • X represents X-3, X-4 or X-5.
  • X represents X-3 or X-5.
  • X represents X-3.
  • X is X-2, preferably one of Z 1 and Z 2 is methylene or halomethylene, preferably methylene.
  • Z 3 , Z 4 and Z 5 are substituted only by hydrogen or halogen, preferably hydrogen, more preferably two of Z 3 , Z 4 and Z 5 are independently methylene or halomethylene, preferably methylene.
  • Z 3 and Z 5 are methylene or halomethylene, preferably methylene.
  • X is X-4, preferably at least three of Z 6 , Z 7 , Z 8 and Z 9 are substituted only by hydrogen or halogen, preferably hydrogen, more preferably at least three of Z 6 , Z 7 , Z 8 and Z 9 are independently methylene or halomethylene, preferably methylene.
  • Z 10 , Z 11 , Z 12 , Z 13 and Z 14 are substituted only by hydrogen or halogen, preferably hydrogen more preferably four of Z 10 , Z 11 , Z 12 , Z 13 and Z 14 are independently methylene or halomethylene, preferably methylene.
  • Z 10 , Z 11 , Z 13 and Z 14 are independently methylene or halomethylene, preferably methylene.
  • the groupings X-2, X-3, X-4 and X-5 contain at most one ring which contains either only one of the radicals Z 1 to Z 14 or two radicals Z 1 to Z 14 or three radicals Z 1 to Z 14 or four radicals Z 1 to Z 14 as ring members. None of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 and Z 14 represent a carbon atom substituted by two OH groups. Optionally radicals Z 1 , Z 3 , Z 6 and Z 10 are not substituted by OH.
  • the groupings X-2, X-3, X-4 and X-5 do not contain any rings which contain any of the radicals Z 1 to Z 14 .
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9.
  • Q-l, Q2, Q-3 and Q-9 are preferred.
  • Q' is selected from the group consisting of Q- , Q- 2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'.
  • Q- ⁇ , Q2', Q-3' and Q-9' are preferred.
  • Q is selected from the group consisting of Q-l, Q-2, Q- 4, Q-5, Q-6, Q-7, Q-8 and Q-9.
  • Q-l, Q2 and Q-9 are preferred.
  • Q' is selected from the group consisting of Q-l', Q-2', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'.
  • Q- ⁇ , Q2' and Q-9' are preferred.
  • Each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2 , Y 3' and Y 4 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, C 3 -C 8 cydoalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, benzyl, a 5- or 6- membered heterocyde containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocyde as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g.
  • 1,2,4 triazolyl more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl), COR 1 , OR 2 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R 1 , CON(R 3 ) 2 , NR 3 COR ⁇ CR ⁇ -OR 2 , wherein the alkyl, cydoalkyi, alkenyl, alkynyl, phenyl, benzyl and heterocyde are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OR 2 , d-Q alkyl and d
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, CN, OR 2 , d-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cydoalkyi, phenyl, pyridyl, N(R 3 ) 2 , C0 2 R 2 , NR 3 COR ⁇ SH, d-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl, wherein the alkyl, alkenyl, alkynyl, cydoalkyi, phenyland pyridyl are optionally substituted by one or
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OR 2 , CN, d-C 4 alkyl, C 3 -C 6 cydoalkyi, N(R 3 ) 2 , CrC 4 alkylthio, Ci-C 4 alkylsulphinyl, d-C 4 alkylsulphonyl, phenyl, C0 2 R 2 or NR ⁇ OR 1 wherein the alkyl, cydoalkyi and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, CN, Ci-C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 alkenyloxy, C 3 - C 6 cydoalkyi, N(R 3 ) 2 , CrC 4 alkylthio, d-C 4 alkylsulphinyl, d-C 4 alkylsulphonyl, phenyl, phenyloxyl or C0 2 R 2 , wherein the alkyl, alkoxy, alkenyloxy, cydoalkyi and phenyl are optionally substituted by one or more groups, e.g.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2 , Y 3' and Y 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, CN, Ci-C 4 alkyl, Ci-C 4 alkoxy, phenyl, wherein the alkyl, alkoxy and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, CrC 4 -haloalkyl, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another preferably represent hydrogen, halogen, OH, Ci-C 4 alkyl, d-C 4 alkoxy, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another more preferably represent hydrogen, halogen, OH, Ci-C 4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkyl.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another even more preferably represent hydrogen, halogen, OH, Ci-C 4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another yet more preferably represent hydrogen, OH, Ci-C 4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl.
  • each Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or Ci-C 4 alkyl;
  • each Y 4 and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl.
  • each Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another preferably represent hydrogen or Ci-C 4 alkyl;
  • each Y 4 and Y 4' independently of one another preferably represent hydrogen, OH, d- C 4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, Ci-C 8 alkyl, C 2 -C 8 alkynyl, d-C 8 alkoxy or Ci-Cs alkylthio.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy or Ci-C 4 alkylthio.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
  • Y 4' independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
  • each Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, methoxy or methylthio.
  • Q When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7 then Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 independently of the other, together with the fragment to which they are attached may form a carbocyclic or heterocyclic ring.
  • Q' is Q- , Q-2', Q-3', Q-4', Q-6' or Q-7' then Y 1' and Y 2' , Y 2' and Y 3' , or Y 3' and Y 4' may form a carbocyclic or heterocyclic ring. This possibility and preferences thereof are described below, which may be combined with any of the definitions above.
  • Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 together with the fragment of the ring to which they are attached may form a ring system selected from isoquinoline; 5,6,7,8- tetrahydro-isoquinoline; 6,7-dihydro-5H-[2]pyrindine; 3,4-dihydro-lH-pyrano[3,4-c]pyridine; 6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine; [l,7]naphthyridine; quinoline; 5,6,7,8- tetrahydro-quinoline; 6,7-dihydro-5H-[l]pyrindine; [l,8]naphthyridine; 6,7,8,9-tetrahydro- 5H-cyclohepta[b]pyridine; and 7,8-dihydro-5H-pyrano[4,3-b]pyridine), and where
  • each combination of Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R 3 ), and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 is optionally substituted by one or more groups, e.g.
  • halogen CN, NH 2 , N0 2 , OH, Ci-G, alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio.
  • Y 1' and Y 2' , Y 2' and Y 3' , or Y 3' and Y 4' are independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-G, alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio.
  • each combination of Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio.
  • groups e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio
  • each Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy,
  • Ci-C 4 haloalkoxy and Ci-C 4 alkylthio The same applies to Y 2' and Y 3' .
  • Y 2 and Y 3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and d-
  • Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl.
  • groups e.g. one to five groups, independently selected from Ci-C 4 alkyl.
  • Y 2 and Y 3 together with the fragment of the ring to which they are attached may only form a ring when Q is Q-2. The same applies to Y 2' and Y 3' .
  • Y 2 and Y 3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups, e.g.
  • Y 1 and D 1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g.
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7- membered heterocyclic ring containing one or two heteroatoms independently selected from N and N(R 3 ), wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g.
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio.
  • Y 1' and D 4 when Q' is Q- ⁇ , Q-3', Q-4', Q-7' or Q-8'. More preferably, when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L 1 is C-D 1 , then Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g.
  • Y 1' and D 4 when Q' is Q- ⁇ , Q-3', Q-4', Q-7' or Q-8'.
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one or two independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, d-C 4 haloalkoxy and Ci-C 4 alkylthio.
  • groups e.g. one or two independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, d-C 4 haloalkoxy and Ci-C 4 alkylthio.
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6- membered carbocydic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy.
  • groups e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy.
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to four groups, independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio.
  • groups e.g. one to four groups, independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio.
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy.
  • groups e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy.
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring.
  • Q is Q-l and/or Q' is Q-l'.
  • Q is Q-9 and L 1 is C-D 1 then R 12 and D 1 together ma Likewise when Q' is Q-9' and L 4 is C-D 4 , then R 12 and D 4 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 , wherein each R 21 independently of one another represents hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or d-C 4 haloalkoxy, preferably hydrogen or d-C 4 alkyl. More preferably, G 1 , G 2 and G 3 represent methylene.
  • Each p independently of one another represents 0, 1 or 2, preferably 1 or 2, more preferably 1.
  • Each R 1 independently of one another represents hydrogen, CrC 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g.
  • each R 1 independently of one another represents hydrogen, Ci-C 8 alkyl or d-C 8 haloalkyl.
  • each R 1 independently of one another represents hydrogen, d-d alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • groups e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • each R 1 independently of one another represents hydrogen, d-C 4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • each R 1 independently of one another represents hydrogen, d-C 4 alkyl or phenyl, wherein the phenyl maybe substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • each R 1 independently of one another represents hydrogen or phenyl, wherein the phenyl may be substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • each R 1 independently of one another represents hydrogen or phenyl.
  • Each R 2 independently of one another represents hydrogen, CrC 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups, e.g.
  • the heterocycle is preferably one as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl.
  • each R 2 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 - haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 -alkoxy-CrC 4 -alkyl.
  • each R 2 independently of one another represents hydrogen, Ci-C 8 alkyl,
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • each R 2 independently of one another represents hydrogen, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d- C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • each R 2 independently of one another represents hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 haloalkenyl.
  • each R 2 independently of one another represents hydrogen, d- C 4 alkyl or Ci-C 4 haloalkyl.
  • each R 2 independently of one another represents hydrogen, d-C 4 alkyl or C 3 -C 6 alkenyl.
  • Each R 3 independently of one another represents hydrogen, OH, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl or COR 1 , wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more, e.g.
  • radicals R 3 one to five, halogen; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; wherein when two radicals R 3 are attached to the same nitrogen atom, both of these radicals cannot be OH, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • each R 3 independently of one another represents hydrogen, d-C 8 alkyl or COR 1 ; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl.
  • each R 3 independently of one another represents hydrogen or Ci-C 4 alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl.
  • each R 3 independently of one another represents hydrogen or Ci-C 4 alkyl.
  • each R 3 represents hydrogen.
  • Each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-C 6 alkoxy, C 3 -C 6 alkenyloxy, Cr
  • R 4 and R 5 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-Cealkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, Ci-Ce alkylthio, Ci-Cs alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR 3 COR ⁇ CR ⁇ -OR 2 , phenyl or 5- or 6-membered heterocycle containing one to four heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-C, alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C, alkoxy, C 3 -C 4 alkenyloxy, d-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, d-C 4 alkoxy, d-C 4 haloalkoxy and NH 2 .
  • each R 4 and R 5 independently of one another represent hydrogen, Ci-C 4 alkyl, C r C 4 alkoxy, d-C 4 alkoxycarbonyl, CON(R 3 ) 2 , NH 2 , NR ⁇ O ⁇ or C ⁇ N-OR 2 , wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN and NH 2 .
  • each R 4 and R 5 independently of one another represent hydrogen
  • Ci-C 4 alkyl or Ci-C 4 alkoxycarbonyl wherein the alkyl are optionally substituted by one or more groups independently selected from halogen.
  • each R 4 and R 5 independently of one another represent hydrogen, Ci-C 4 alkyl or Ci-C 4 alkoxycarbonyl.
  • each R 4 and R 5 independently of one another represent hydrogen
  • Ci-C 4 alkyl or d-C 2 alkoxycarbonyl are examples of compounds that are used in the d-C 2 alkoxycarbonyl.
  • each R 4 and R 5 independently of one another represent hydrogen or d-d alkoxycarbonyl.
  • each R 4 and R 5 represents hydrogen.
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce alkenyl, d-C 6 alkynyl, Ci-Cealkoxy, Ci-Cs alkenyloxy, Ci-Cealkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C 3 -C 6 cycloalkyl, phenyl or 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-Q alkyl, d-Q haloalkyl,
  • heterocylces include dioxolane, dithiolane, morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably dioxolane, dithiolane, pyridyl or imidazolyl.
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkenyl, Ci-Ce haloalkenyl, d- C 6 alkynyl, Ci-dhaloalkynyl, d-C 6 alkoxy, d-C 6 haloalkoxy, Ci-Ce alkenyloxy, Ci-Ce
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 alkenyloxy or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R 4 and R 5 together with the carbon atom to which they are attached may form a
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkenyloxy or Ci-C 4 haloalkyl; or R 4 and R 5 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyl group.
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, d-C 4 alkyl or d-C 4 haloalkyl.
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, d-C 4 alkyl, Ci-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy; or R 4 and R 5 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • Each R 6 and R 7 independently of one another represent hydrogen, halogen, CrC 4 alkyl or Ci-C 4 haloalkyl. Preferably, each R 6 and R 7 independently of one another represent hydrogen, halogen, methyl or halomethyl.
  • each R 6 and R 7 represent hydrogen.
  • Each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 - C 6 alkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR 3 COR ⁇ CR ⁇ -OR 2 , phenyl or 5- or 6-membered heterocyde containing one to four heteroatoms independently selected from 0, S and N providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyde are optionally substituted by
  • R 8 and R 9 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, d-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR 3 COR ⁇ CR ⁇ -OR 2 , phenyl or 5- or 6-membered heterocyde containing one to four heteroatoms independently selected from O, S and N providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyde are
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-G, alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C r C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, d-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(Ci-C 4 alkyl), CON(C r C 4 alkyl) 2 , NH 2 , NR 3 CO(C r C 4 alkyl), NR 3 CO(C 2 -C 4 alkenyl), NR 3 CO(C 2 -C 4 alkynyl), NR 3 COphenyl, CHN-OR 2 , phenyl or 5-membered heterocyde containing one to four heteroatoms independently selected from 0 and N providing that the heterocyde does not
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, d-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(Ci-C 4 alkyl), CON(C r C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, Ci-G, alkyl, C 2 -C 4 alkenyl, Ci-G, alkoxy, C 3 -C 4 alkenyloxy, Ci-G, alkoxycarbonyl, CONH 2 , CONH(Ci-C 4 alkyl), CON(C r C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy, benzyloxy, NH
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, Ci-G, alkyl, C 2 -C 4 alkenyl, Ci-G, alkoxy, C 3 -C 4 alkenyloxy, Ci-G, alkoxycarbonyl, CONH 2 , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, Ci-C 4 alkoxy, benzyloxy, NH 2 , NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl.
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, C1-C4 alkyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-G, alkoxycarbonyl, CHN-OH, or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, benzyloxy and phenyl.
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, d-C 6 alkyl, d-C 6 alkenyl, d-C 6 alkynyl, d-C 6 alkoxy, Ci-Ce alkenyloxy, d-C 6 alkynyloxy, d-C 6 alkylthio, d-C 6 alkoxycarbonyl, C 3 -C 6 cycloalkyl, phenyl or 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-Q alkyl, d-Q
  • heterocylces include dioxolane, dithiolane, morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably dioxolane, dithiolane, pyridyl or imidazolyl.
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, d-C 6 alkyl, d-C 6 haloalkyi, d-C 6 alkenyl, d-C 6 haloalkenyl, d- C 6 alkynyl, Ci-dhaloalkynyl, d-C 6 alkoxy, d-C 6 haloalkoxy, Ci-Ce alkenyloxy, d-C 6
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, Ci-C 4 alkenyloxy or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R 8 and R 9 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-Q alkoxy, Ci-C 4 alkenyloxy or Ci-C 4 haloalkyi; or R 8 and R 9 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • R 8 , R 9 , R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, d-C 4 alkoxy and Ci-C 4 haloalkoxy; or R 8 and R 9 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • Each R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 haloalkyi or phenyl, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, C1-C4 alkyl, Ci-Q haloalkyi, d-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • each R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.
  • R 12 and R 12' independently of one another represent hydrogen, halogen, CN, SH, d- C 8 alkylthio, Ci-C 8 alkylsulphinyl, d-C 8 alkylsulphonyl, NH 2 , C1-C10 alkyl, C 3 -C 8 cycloalkyi, C 2 - C 8 alkenyl, C 2 -C 8 alkynyl, (R 2 0)carbonyl(Ci-C 4 alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g.
  • heterocycle preferably one as defined herein, e.g.
  • morpholinyl pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl.
  • R 12 and R 12' independently of one another represent hydrogen, d-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyi, phenyl, pyridyl, or (R 2 0)carbonyl(d-C 4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g.
  • one to five groups independently selected from halogen, CN, OR 2 , NH 2 , NH-Ci-C 8 alkyl, N(d-C 8 alkyl) 2 , d-C 4 alkyl, Ci-C 4 haloalkyi, C 3 -C 6 cycloalkyi and pyridyl.
  • R 12 and R 12' independently of one another represent hydrogen, d-C 4 alkyl, C 2 -C 4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, NH 2 , NH-Ci-C 4 alkyl, N(Ci-C 4 alkyl) 2 , Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, d-C 4 haloalkoxy and C 3 -C 6 cycloalkyi.
  • groups e.g. one to five groups, independently selected from halogen, CN, OH, NH 2 , NH-Ci-C 4 alkyl, N(Ci-C 4 alkyl) 2 , Ci-C 4 alkyl, Ci-C 4
  • R 12 and R 12' independently of one another represent hydrogen, d-C 4 alkyl.
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl.
  • R 12 and R 12' independently of one another represent hydrogen, d-C 4 alkyl, C 2 -C 4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups,
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 4 alkyl, d-C 4 haloalkyi, phenyl or pyridin-2-yl, wherein the phenyl and pyridin-2-yl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • R 13 and R 13' independently of one another represent hydrogen, d-C 8 alkyl,
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl, C 3 -
  • C 6 alkenyl, C 3 -C 6 alkynyl or benzyl wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • R 13 and R 13' independently of one another represent hydrogen, d-C 8 alkyl, or d-C 8 haloalkyi.
  • R 13 and R 13' independently of one another represent hydrogen, C1-C4 alkyl or Ci-G, haloalkyi.
  • R 13 and R 13' independently of one another represent hydrogen or Ci-Q alkyl.
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl.
  • R 13 and R 13' independently of one another represent hydrogen, d-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl, d-C 4 haloalkyi, halogen, CN, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • R 13 and R 13' independently of one another represent hydrogen, methyl orpropargyl.
  • Each R 14 and R 15 independently of one another represent hydrogen, halogen, CrC 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or d-C 4 haloalkoxy, preferably hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
  • R 16 represents hydrogen, OH, d-C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 cycloalkyi, Ci-Cs alkylcarbonyl or Ci-C 8 haloalkylcarbonyl, preferably hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
  • no more than one of L 1 , L 5 and L 2 is N, and no more than one of L 3 , L 6 and L 4 is N.
  • L 1 is C-D 1
  • L 2 is C-D 2
  • L 5 is C-D 5 .
  • L 1 is C-D 1
  • L 2 is C-D 2
  • L 3 is C-D 3
  • L 4 is C-D 4
  • L 5 is C-D 5 and
  • L 6 is C-D 6 .
  • L 1 is C-D 1
  • L 2 is N
  • L 5 is C-D 5 .
  • L 1 is C-D 1
  • L 2 and L 3 are N
  • L 4 is C-D 4
  • L 5 is C-D 5
  • L 6 is
  • L 1 is N
  • L 2 is C-D 2
  • L 5 is C-D 5 .
  • L 1 and L 4 are N, L 2 is C-D 2 , L 3 is C-D 3 , L 5 is C-D 5 and L 6 is
  • L 1 is N or C-D 1 ;
  • L 2 is C-D 2 ;
  • L 3 is C-D 3 ;
  • L 4 is N or C-D 4 ;
  • L 5 is C-D 5 ;
  • L 6 is C-D 6 .
  • L 1 is the same as L 4
  • L 5 is the same as L 6
  • L 2 is the same as L 3
  • Q is the same as Q'.
  • In one group of compounds Q is Q-9 and G 1 , G 2 and G 3 represent methylene. In one group of compounds Q' is Q-9' and G 1 , G 2 and G 3 represent methylene. In one group of compounds Q is Q-9 and Q' is Q-9' and G 1 , G 2 and G 3 represent methylene.
  • L 1 is N or C-D 1 ;
  • L 2 is C-D 2 ;
  • L 3 is C-D 3 ;
  • L 4 is N or C-D 4 ;
  • L 5 is C-D 5 ;
  • L 6 is C-D 6 ;
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, OH, CN, Ci-C, alkyl, d-C 4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 cycloalkyi, N(R 3 ) 2 , phenyl or C0 2 R 2 , wherein the alkyl, alkoxy, alkenyloxy, cycloalkyi and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and d-C 4 haloalkoxy; or
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy; X represents X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9;
  • each Y 1 , Y 2 , Y 3 , Y 4 independently of one another represent hydrogen, halogen, OH, CN, Ci-C 4 alkyl, C1-C4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl, N(R 3 ) 2 , Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl, Ci-C 4 alkyl sulphonyl, phenyl, phenyloxyl or C0 2 R 2 , wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, CrC 4 -haloalkyl, d-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, Ci-C 4 haloalkoxy and d-C 4 alkylthio;
  • R 12 and D 1 together may be
  • Q' is selected from the group consisting of Q- ⁇ , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
  • each Y 1' , Y 2' , Y 3' , Y 4' independently of one another represent hydrogen, halogen, OH, CN, Ci-C 4 alkyl, d-C 4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl, N(R 3 ) 2 , Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl, Ci-C 4 alkyl sulphonyl, phenyl, phenyloxyl or C0 2 R 2 , wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, d-C 4 -haloalkyl, d-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Y 1' and Y 2' , Y 2' and Y 3' , or Y 3' and Y 4' independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y 1' and Y 2' , Y 2' and Y 3' , or Y 3' and Y 4' is optionally substituted by one or more groups independently selected from halogen, CN, d-Q alkyl, d-C 4 haloalkyi, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups independently selected from halogen, CN, OH, d-C 4 alkyl, Ci-C 4 haloalkyi, d-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • R 12 and D 4 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 ;
  • each p independently of one another represents 1 or 2;
  • each R 2 independently of one another represents hydrogen, d-C 8 alkyl, Ci-Cs haloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • each R 3 independently of one another represents hydrogen or d-C 4 alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkenyloxy or Ci-C 4 haloalkyi; or R 4 and R 5 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • each R 6 and R 7 independently of one another represent hydrogen, halogen, d-C 4 alkyl or Ci-C 4 haloalkyi;
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, d-C 6 haloalkyi, d-C 6 alkenyl, d-C 6 haloalkenyl, d-C 6 alkynyl, d- Cehaloalkynyl, d-C 6 alkoxy, d-C 6 haloalkoxy, Ci-Ce alkenyloxy, Ci-Ce haloalkenyloxy, d- C 6 alkynyloxy, Ci-dhaloalkynyloxy, d-C 6 alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl or phenyl, wherein the phenyl is optionally
  • R 8 and R 9 together with the carbon atom to which they are attached may form a
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 4 alkyi, C 2 -C 4 alkenyl, phenyl or pyridyl, wherein the alkyi, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OH, NH 2 , NH- C1-C4 alkyi, N(Ci-C 4 alkyl) 2 , C1-C4 alkyi, Ci-Q haloalkyl, Ci-Q alkoxy, Ci-Q haloalkoxy and C 3 - C 6 cycloalkyl;
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyi, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyi, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 21 independently of one another represents hydrogen, halogen, Ci-C 4 alkyi, d-
  • L 1 is N or C-D 1 ;
  • L 2 is C-D 2 ;
  • L 3 is C-D 3 ;
  • L 4 is N or C-D 4 ;
  • L 5 is C-D 5 ;
  • L 6 is C-D 6 .
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, d-C 4 alkyi, CN or d-C 4 alkoxy, wherein the alkyi and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • X represents X-3 or X-5:
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • each Y 1 , Y 2 , Y 3 and Y 4 independently of one another represent hydrogen, Ci-C 4 alkyi, CN or d-C 4 alkoxy, wherein the alkyi and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • Y 2 and Y 3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic and wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyi, d-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyi, d-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • R 12 and D 1 together may be
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9'; each Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, CrC 4 alkyl, CN or CrC 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • Y 2' and Y 3' together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic and wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, d-C 4 haloalkyi, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and d- C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic or and wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, d-C 4 haloalkyi, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • R 12' and D 4 together may be
  • each G 1 , G 2 and G 3 independently of one another represent -C(R 14 R 15 )-;
  • each p is 1;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl or Ci-C 4 haloalkyi;
  • each R 6 and R 7 independently of one another represent hydrogen, halogen, d-C 4 alkyl or d-C 4 haloalkyi;
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce haloalkyi, Ci-Ce alkenyl, Ci-Ce haloalkenyl, d-C 6 alkynyl, d- Cehaloalkynyl, d-C 6 alkoxy, d-C 6 haloalkoxy, Ci-Ce alkenyloxy, Ci-Ce haloalkenyloxy, d- C 6 alkynyloxy, Ci-dhaloalkynyloxy, d-C 6 alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl or phenyl, wherein the phenyl is optionally substituted by
  • R 8 and R 9 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, d-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • R 13 and R 13' independently of one another represent hydrogen, Ci-Cs alkyl, or Ci-Q. haloalkyi; each R 14 and R 15 independently of one another represents hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or d-C 4 haloalkoxy.
  • L 1 is N or C-D 1 ;
  • L 2 is C-D 2 ;
  • L 3 is C-D 3 ;
  • L 4 is N or C-D 4 ;
  • L 5 is C-D 5 ;
  • L 6 is C-D 6 ;
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen,
  • D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D 1 and D 5 , D 2 and D 5 , D 3 and D 6 , D 4 and D 6 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • X represents X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9; each Y 1 , Y 2 , Y 3 , Y 4 independently of one another represent hydrogen, halogen, OH, CN, Ci-C 4 alkyl, d-C 4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 cycloalkyi, N(R 3 ) 2 , Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl, Ci-C 4 alkyl sulphonyl, phenyl, phenyloxyl or C0 2 R 2 , wherein the alkyl, alkoxy, alkenyloxy, cycloalkyi and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, d-C 4 -haloalkyl, d-C 4 alk
  • Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, Ci-C 4 haloalkoxy and d-C 4 alkylthio;
  • R 12 and D 1 together may be -(G G ⁇ G 3 -;
  • Q' is selected from the group consisting of Q- , Q-2', Q-4', Q-5', Q-6', Q-7', Q-8' and
  • each Y 1' , Y 2' , Y 3' , Y 4' independently of one another represent hydrogen, halogen, OH, CN, C1-C4 alkyl, C1-C4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl, N(R 3 ) 2 , C1-C4 alkylthio, C1-C4 alkylsulphinyl, Ci-C 4 a I kyl sulphonyl, phenyl, phenyloxyl or C0 2 R 2 , wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, CrC 4 -haloalkyl, d-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Y 1' and Y 2 , Y 2' and Y 3' , or Y 3' and Y 4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y 1' and Y 2' , Y 2' and Y 3' , or Y 3' and Y 4' is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, d-C 4 haloalkyi, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, d-C 4 alkoxy, Ci-C 4 haloalkoxy and d-C 4 alkylthio;
  • R 12' and D 4 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 ;
  • each p independently of one another represents 1 or 2;
  • each R 2 independently of one another represents hydrogen, d-C 8 alkyl, Ci-Cs haloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • each R 3 independently of one another represents hydrogen or d-C 4 alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, C1-C4 alkoxy, Ci-C 4 alkenyloxy or Ci-C 4 haloalkyi; or R 4 and R 5 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • each R 6 and R 7 independently of one another represent hydrogen, halogen, d-C 4 alkyl or Ci-C 4 haloalkyl;
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH,
  • R 8 and R 9 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OH, NH 2 , NH- Ci-C 4 alkyl, N(Ci-C 4 alkyl) 2 , Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and C 3 - C 6 cycloalkyl;
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 21 independently of one another represents hydrogen, halogen, Ci-C 4 alkyl, d- C 4 haloalkyl, Ci-C 4 alkoxy or d-C 4 haloalkoxy.
  • L 1 is N or C-D 1 ;
  • L 2 is C-D 2 ;
  • L 3 is C-D 3 ;
  • L 4 is N or C-D 4 ;
  • L 5 is C-D 5 ;
  • L 6 is C-D 6 ;
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, d-C 4 alkyl, CN or d-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • X represents X-3 or X-5:
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2 and Q-9;
  • each Y 1 , Y 2 , Y 3 and Y 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or d-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy; when Q is Q-l or Q-2 then Y 2 and Y 3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic and wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-Q alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio; when Q is Q-l then Y 1 and D 1 together with the fragment to which they are attached may form a fully unsaturated 6-membered
  • Q' is selected from the group consisting of Q- , Q-2' and Q-9';
  • each Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, d-C 4 alkyl, CN or CrC 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • R 12' and D 4 together may be
  • each G 1 , G 2 and G 3 independently of one another represent -C(R 14 R 15 )-;
  • each p is 1;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl or d-C 4 haloalkyl;
  • each R 6 and R 7 independently of one another represent hydrogen, halogen, d-C 4 alkyl or Ci-C 4 haloalkyl;
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH,
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 8 alkyl, or Ci-C 8 haloalkyl
  • each R 14 and R 15 independently of one another represents hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or d-C 4 haloalkoxy.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , d-C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • alkylsulphonyl phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R 1 , CON(R 3 ) 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OR 2 , Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X represents X-3, X-4 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7, Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R 3 ), and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-Q alkyl, Q-
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C4 alkyl, G-C 4 haloalkyl, G-C 4 alkoxy, G-C 4 haloalkoxy and G-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C 4 alkyl, G-C 4 haloalkyl, G-C 4 alkoxy, G-C 4 haloalkoxy and G-C 4 alkylthio;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may be -(G -G 2 -G 3 '
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 , wherein each R 21 independently of one another represents hydrogen, halogen, G-C 4 alkyl, G-C 4 haloalkyl, G-C 4 alkoxy or G-C 4 haloalkoxy;
  • Each p independently of one another represents 1 or 2;
  • each R 1 independently of one another represents hydrogen, G-C 4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and G-C 4 alkyl, G-C 4 haloalkyl, G-C 4 alkoxy and G-C 4 haloalkoxy; each R 2 independently of one another represents hydrogen, G-C 8 alkyl, G-C 8 haloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, CrC 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and
  • each R 3 independently of one another represents hydrogen or d-C 4 alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH,
  • Each R 6 and R 7 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyi, CONH 2 , CONH(Ci-C 4 alkyl), CON(Ci-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optional
  • each R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • R 12 and R 12' independently of one another represent hydrogen, Ci-Cs alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyi, phenyl, pyridyl, or (R 2 0)carbonyl(d-C 4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g.
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X represents X-3 or X-5;
  • Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d-C 4 alkyl;
  • each Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groupsindependently selected from halogen, CN, d-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • each Y 2' and Y 3' together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g.
  • Y 1' and D 4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • R 12 and D 1 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 ;
  • each R 21 independently of one another represents hydrogen or d-C 4 alkyl
  • Each p independently of one another represents 1 or 2;
  • each R 4 and R 5 independently of one another represent hydrogen, d-C 4 alkyl or Ci-C 4 alkoxycarbonyl;
  • each R 6 and R 7 represent hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(Ci-C 4 alkyl), CON(Ci-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optional
  • R 12 and R 12' independently of one another represent hydrogen or d-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen or d-C 4 alkyl.
  • D 1 , D 2 , D 3 and D 4 each represent hydrogen
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9
  • Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or C1-C4 alkyl;
  • each Y 4 and Y 4' independently of one another represent hydrogen, halogen, OH, d-Q alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may b
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 and R 5 independently of one another represent hydrogen or Ci-C 2
  • each R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, CONH 2 , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C 4 alkoxy, benzyloxy, NH 2 , NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl.
  • D 1 , D 2 , D 3 and D 4 each represent hydrogen
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl or a
  • 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
  • Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or CrC 4 alkyl
  • each Y 4 and Y 4' independently of one another represent hydrogen, OH, Ci-C 4 alkyl or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d-C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may be -(G ⁇ p -G ⁇ G 3 ;
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 , R 5 , R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, d- alkoxycarbonyl, CHN-OH or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, d-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy, benzyloxy and phenyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , CrC 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, d-C 4 alkoxy, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • X represents X-3, X-4 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
  • Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y ⁇ Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkyl, d-C 4 -haloalkyl, d-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocydic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, C1-C4 alkyl, d-Q haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocydic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • R 12 and D 1 together may be
  • R 12 and D 4 together may be -(G -G 2 -G 3 '
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 , wherein each R 21 independently of one another represents hydrogen, halogen, d-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • Each p independently of one another represents 1 or 2;
  • each R 1 independently of one another represents hydrogen, d-C 4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy; each R 2 independently of one another represents hydrogen, d-C 8 alkyl, Ci-Cs haloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4
  • each R 3 independently of one another represents hydrogen or d-C 4 alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, d-C 4 haloalkoxy and NH 2 ;
  • Each R 6 and R 7 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH,
  • each R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH,
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cydoalkyi, phenyl, pyridyl, or (R 2 0)carbonyl(d-C 4 alkyl), wherein the alkyl, alkenyl, alkynyl, cydoalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g.
  • one to five groups independently selected from halogen, CN, OR 2 , NH 2 , NH-Ci-C 8 alkyl, N(d-C 8 alkyl) 2 , Ci-C 4 alkyl, d-C 4 haloalkyl, C 3 -C 6 cydoalkyi and pyridyl;
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, CN, d-C 4 alkyl, Ci-C 4 alkoxy, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C 4 alkoxy, d-C 4 alkyl and Ci-C 4 haloalkyl;
  • X represents X-3 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d- C 4 alkyl;
  • each Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • each Y 2' and Y 3' together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • Y 1' and D 4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • R 12 and D 1 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 ;
  • each R 21 independently of one another represents hydrogen or d-C 4 alkyl
  • Each p independently of one another represents 1 or 2;
  • each R 4 and R 5 independently of one another represent hydrogen, d-C 4 alkyl or Ci-C 4 alkoxycarbonyl;
  • each R 6 and R 7 represent hydrogen; each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C1-C4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(Ci-C 4 alkyl), CON(Ci-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms
  • R 12 and R 12' independently of one another represent hydrogen or d-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or Ci-C 4 alkyl;
  • each Y 4 and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d- C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may b
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 and R 5 independently of one another represent hydrogen or Ci-C 2
  • each R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, CONH 2 , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C 4 alkoxy, benzyloxy, NH 2 , NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9'; Y 1 , Y 2 , ⁇ 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or CrC 4 alkyl;
  • each Y 4 and Y 4' independently of one another represent hydrogen, OH, Ci-C 4 alkyl, d- C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may be -(G ⁇ p -G ⁇ G 3 ;
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 , R 5 , R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, d-d alkoxy, C 3 -C 4 alkenyloxy, d-d alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, CN, NH 2 , NHCOphenyl, d-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by d-C 4 alkyl;
  • R 12 and R 12' independently of one another represent d-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, d-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, d-C 4 alkyl, CN or d-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, CrC 4 alkoxy and Ci-C 4 haloalkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , CrC 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • alkylsulphonyl phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R 1 , CON(R 3 ) 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OR 2 , Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X represents X-3, X-4 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
  • Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkyl, d-C 4 -haloalkyl, d-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, C1-C4 alkyl, d-Q haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may be -(G -G 2 -G 3 '
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 , wherein each R 21 independently of one another represents hydrogen, halogen, d-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • Each p independently of one another represents 1 or 2;
  • each R 1 independently of one another represents hydrogen, d-C 4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy; each R 2 independently of one another represents hydrogen, d-C 8 alkyl, Ci-Cs haloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4
  • each R 3 independently of one another represents hydrogen or d-C 4 alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, CHO, C1-C4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, d-C 4 haloalkoxy and NH 2 ;
  • Each R 6 and R 7 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH,
  • each R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH,
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyi, phenyl, pyridyl, or (R 2 0)carbonyl(d-C 4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g.
  • one to five groups independently selected from halogen, CN, OR 2 , NH 2 , NH-Ci-C 8 alkyl, N(d-C 8 alkyl) 2 , Ci-C 4 alkyl, d-C 4 haloalkyl, C 3 -C 6 cycloalkyi and pyridyl;
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, CN or Ci-C 4 alkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X represents X-3 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d- C 4 alkyl;
  • each Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • each Y 2' and Y 3' together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • Y 1' and D 4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • R 12 and D 1 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 ;
  • each R 21 independently of one another represents hydrogen or d-C 4 alkyl
  • Each p independently of one another represents 1 or 2; each R 4 and R 5 independently of one another represent hydrogen, CrC 4 alkyi or Ci-C 4 alkoxycarbonyl;
  • each R 6 and R 7 represent hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC 4 alkyi, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C1-C4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(Ci-C 4 alkyi), CON(Ci-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyi), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyi are optional
  • R 12 and R 12' independently of one another represent hydrogen or d-C 4 alkyi
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyi or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 and D 4 each represent hydrogen
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyi, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C 4 alkoxy, Ci-C 4 alkyi and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 1 ', Y 2 ' and Y 3 ' independently of one another represent hydrogen or C1-C4 alkyi;
  • each Y 4 and Y 4 ' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyi, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d- C 4 alkyi;
  • Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from d-C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may b
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 and R 5 independently of one another represent hydrogen or Ci-C 2
  • each R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, CONH 2 , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C 4 alkoxy, benzyloxy, NH 2 , NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 and D 4 each represent hydrogen
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
  • Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or CrC 4 alkyl
  • each Y 4 and Y 4' independently of one another represent hydrogen, OH, Ci-C 4 alkyl or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d-C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may be -(G ⁇ p -G ⁇ G 3 ;
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 , R 5 , R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, NH 2 , NHCOphenyl, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , d-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, d-C 4 alkoxy, Ci-C 4 alkylthio, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • alkylsulphonyl phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R 1 , CON(R 3 ) 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OR 2 , d-C 4 alkyl and Ci-C 4 haloalkyl;
  • X represents X-3, X-4 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, C 2 -C 6 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • one to five groups independently selected from halogen, CN, OH, Ci-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy, d-C 4 haloalkoxy and d-C 4 alkylthio;
  • R 12 and D 1 together may be
  • R 12 and D 4 together may b
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 , wherein each R 21 independently of one another represents hydrogen, halogen, d-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • Each p independently of one another represents 1 or 2;
  • each R 1 independently of one another represents hydrogen, d-C 4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy; each R 2 independently of one another represents hydrogen, d-C 8 alkyl, Ci-Cs haloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4
  • each R 3 independently of one another represents hydrogen or d-C 4 alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, d-C 4 haloalkoxy and NH 2 ;
  • Each R 6 and R 7 independently of one another represent hydrogen, halogen, methyl or halomethyl;
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C1-C4 alkoxycarbonyl, C 3 -C 6 cycloalkyi, CONH 2 , CONH(Ci-C 4 alkyl), CON(Ci-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optional
  • each R 10 and R 11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • R 12 and R 12' independently of one another represent hydrogen, Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyi, phenyl, pyridyl, or (R 2 0)carbonyl(d-C 4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g.
  • one to five groups independently selected from halogen, CN, OR 2 , NH 2 , NH-Ci-C 8 alkyl, N(d-C 8 alkyl) 2 , Ci-C 4 alkyl, d-C 4 haloalkyl, C 3 -C 6 cycloalkyi and pyridyl;
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, CN, Ci-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, d-C 4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, Ci-C 4 alkoxy, Ci-C 4 alkyl and d-C 4 haloalkyl;
  • X represents X-3 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, C 2 -C 8 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d-C 4 alkyl;
  • each Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • each Y 2' and Y 3' together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • Y 1' and D 4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • R 12 and D 1 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 ;
  • each R 21 independently of one another represents hydrogen or d-C 4 alkyl
  • Each p independently of one another represents 1 or 2;
  • each R 4 and R 5 independently of one another represent hydrogen, d-C 4 alkyl or Ci-C 4 alkoxycarbonyl;
  • each R 6 and R 7 represent hydrogen; each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C1-C4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(Ci-C 4 alkyl), CON(Ci-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms
  • R 12 and R 12' independently of one another represent hydrogen or d-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, d-d alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, d-C 4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d-C 4 alkoxy, d-C 4 alkyl and d-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen, halogen, d-C 4 alkyl, C 2 -C 8 alkynyl, d-C 4 alkoxy or Ci-C 4 alkylthio;
  • each Y 4 and Y 4' independently of one another represent hydrogen, halogen, OH, d-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d- alkyl;
  • Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from d-C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may be -(G ⁇ p -G ⁇ G 3 ;
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 and R 5 independently of one another represent hydrogen or Ci-C 2
  • each R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, CONH 2 , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C 4 alkoxy, benzyloxy, NH 2 , NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 , D 4 , D 5 and D 6 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, Ci-C 4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
  • Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen, halogen, C1-C4 alkyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio;
  • each Y 4 and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, C 2 -C 8 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from C1-C4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may b
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 , R 5 , R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, NH 2/ NHCOphenyl, d-C, alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl. Yet more preferably in this group of compounds, each D 1 , D 2 , D 3 , D 4 , D 5 , D 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, Ci-Q alkyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy or Ci-C 4 alkylthio.
  • each D 1 , D 2 , D 3 , D 4 , D 5 , D 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
  • each D 1 , D 2 , D 3 , D 4 , D 5 , D 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
  • Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, methoxy or methylthio.
  • R 13 and R 13' independently of one another represent hydrogen, methyl or ethynyl.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, CN, Ci-C 4 alkylthio or d-C 4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, halogen, CN, N0 2 , d-C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, d-C 4 alkylthio, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g.
  • a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl
  • X represents X-3, X-4 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
  • Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 4 ', Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, G-C 4 alkyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, G-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Y 1 and D 1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C 4 alkyl, G-C 4 haloalkyl, G-C 4 alkoxy, G-C 4 haloalkoxy and G-C 4 alkylthio;
  • Y 1' and D 4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C 4 alkyl, G-C 4 haloalkyl, G-C 4 alkoxy, G-C 4 haloalkoxy and G-C 4 alkylthio;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may be -(G ⁇ p-G ⁇ G 3 ' G 1 , G 2 and G 3 represent C(R 21 ) 2 , wherein each R 21 independently of one another represents hydrogen, halogen, d-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • Each p independently of one another represents 1 or 2;
  • each R 1 independently of one another represents hydrogen, d-C 4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy; each R 2 independently of one another represents hydrogen, CrC 8 alkyl, d-C 8 haloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, d-C 8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d- alkyl, d-d-haloalkyl, d-d alkoxy and
  • each R 3 independently of one another represents hydrogen or d-d alkyl; wherein when two radicals R 3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
  • each R 4 and R 5 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-d alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, C 3 -C 4 alkenyloxy, d-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CON(R 3 ) 2 , NH 2 , NR ⁇ OR 1 or CR ⁇ -OR 2 , wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-d alkyl, Ci-d haloalkyl, Ci-d alkoxy, d-C 4 haloalkoxy and NH 2 ;
  • Each R 6 and R 7 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-d alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, Ci-d alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(d-C 4 alkyl), CON(d-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from O and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by
  • R 12 and R 12' independently of one another represent hydrogen, C1-C3 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C3-C3 cycloalkyi, phenyl, pyridyl, or (R 2 0)carbonyl(d-C 4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g.
  • one to five groups independently selected from halogen, CN, OR 2 , NH 2 , NH-Ci-Cs alkyl, N(d-C 8 alkyl) 2 , Ci-C 4 alkyl, d-G, haloalkyl, C 3 -C 6 cycloalkyi and pyridyl;
  • R 13 and R 13' independently of one another represent Ci-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkoxy and d-C 4 haloalkoxy.
  • D 1 , D 2 , D 3 and D 4 independently of one another represent hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, CN, d-C 4 alkylthio or Ci-C 4 alkoxy;
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, Ci-C 4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C 4 alkoxy, d-C 4 alkyl and d-C 4 haloalkyl;
  • X represents X-3 or X-5;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y ⁇ Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d-C 4 alkyl;
  • each Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • each Y 2' and Y 3' together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio;
  • Y 1 and D 1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • Y 1' and D 4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D 4 and Y 1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
  • R 12 and D 1 together may be
  • G 1 , G 2 and G 3 represent C(R 21 ) 2 ;
  • each R 21 independently of one another represents hydrogen or d-C 4 alkyl
  • Each p independently of one another represents 1 or 2;
  • each R 4 and R 5 independently of one another represent hydrogen, d-C 4 alkyl or Ci-C 4 alkoxycarbonyl;
  • each R 6 and R 7 represent hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, Ci-C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl, CONH 2 , CONH(Ci-C 4 alkyl), CON(Ci-C 4 alkyl) 2 , NH 2 , NHCO(Ci-C 4 alkyl), NHCO(C 2 -C 4 alkenyl), NHCO(C 2 -C 4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from O and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optional
  • R 12 and R 12' independently of one another represent hydrogen or d-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 and D 4 each represent hydrogen, halogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy or Ci-C 4 alkylthio;
  • D 5 and D 6 independently of one another represent hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy, Ci-C 4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C 4 alkoxy, Ci-C 4 alkyl and Ci-C 4 haloalkyl;
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
  • each Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or Ci-C 4 alkyl;
  • each Y 4 and Y 4' independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C 4 alkyl;
  • Y 2 and Y 3 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2' and Y 3' is optionally substituted by one or more groups independently selected from d-C 4 alkyl;
  • R 12 and D 4 together may b
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 and R 5 independently of one another represent hydrogen or Ci-C 2
  • each R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, G- G alkyl, C 2 -C 4 alkenyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, G-G, alkoxycarbonyl, CONH 2 , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, G-C 4 alkoxy, benzyloxy, NH 2 , NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by G-C 4 alkyl;
  • R 12 and R 12' independently of one another represent G-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, G-C 4 alkyl or C 3 -C 6 alkynyl.
  • D 1 , D 2 , D 3 and D 4 each represent hydrogen, halogen, G-C 4 alkyl, C 2 -C 4 alkynyl, G-C 4 alkoxy or G-C 4 alkylthio;
  • D 5 and D 6 independently of one another represent hydrogen, halogen, G-C 4 alkyl, C 2 -
  • X is X-3 or X-5;
  • Z 3 , Z 5 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent CR 4 R 5 ;
  • Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
  • Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
  • Y 1 , Y 2 , Y 3 , Y 1' , Y 2' and Y 3' independently of one another represent hydrogen or G-C 4 alkyl
  • each Y 4 and Y 4' independently of one another represent hydrogen, halogen, OH, G-C 4 alkyl, C 2 -C 4 alkynyl, G-C 4 alkoxy, G-C 4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from G-C 4 alkyl; when Q is Q-2, Y 2 and Y 3 , together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 2 and Y 3 is optionally substituted by one or more groups independently selected from d-C 4 alkyl;
  • R 12 and D 1 together may be
  • R 12' and D 4 together may b
  • G 1 , G 2 and G 3 represent methylene
  • p 1;
  • each R 4 , R 5 , R 6 and R 7 represents hydrogen
  • each R 8 and R 9 independently of one another represent hydrogen, CN, OH, CHO, d- C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 4 alkenyloxy, Ci-C 4 alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, NH 2 , NHCOphenyl, d-G, alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by Ci-C 4 alkyl;
  • R 12 and R 12' independently of one another represent Ci-C 4 alkyl
  • R 13 and R 13' independently of one another represent hydrogen, Ci-C 4 alkyl or C 3 -C 6 alkynyl.
  • each D 1 , D 2 , D 3 , D 4 , D 5 , D 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, C 2 -C 4 alkynyl, d-C 4 alkoxy or Ci-C 4 alkylthio.
  • each D 1 , D 2 , D 3 , D 4 , D 5 , D 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
  • each D 1 , D 2 , D 3 , D 4 , D 5 , D 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
  • Y 1' , Y 2' , Y 3' and Y 4' independently of one another represent hydrogen, methoxy or methylthio. Most preferably in this group of compounds, R 13 and R 13' independently of one another represent hydrogen, methyl or ethynyl.
  • Novel compounds of formula (I) also form part of the present invention. Accordingly, in a further aspect the invention provides a compound of formula I as defined as defined above, wherein X is X-3, X-4 or X-5 and the compound of formula I is not a compound of formul
  • R a is hydrogen or phenyl, R b is primary alkyl and n is 4 or 5;
  • each R c is independently hydrogen or methyl
  • n 3
  • R d and R e are both methyl
  • R f and R 9 are both hydrogen
  • n 3
  • R d and R e are both paramethoxyphenyl, R f and R 9 are both hydrogen; or n is 4, R d and R e are both hydrogen, R f and R 9 are both hydrogen; or
  • n 4 , R d and R e are both paraformylphenyl, R f and R 9 are both hydrogen; or
  • R f and R 9 are both hydrogen; or
  • n 4
  • R d and R e are both n-butyl
  • R f and R 9 are both hydrogen
  • n 4
  • R d and R e are both hydrogen
  • R f and R 9 are both hydrogen
  • n 4, R d and R e are both parahydroxyphenyl, R f and R 9 are both hydrogen; or n is 4, R d and R e are both paramethoxyphenyl, R f and R 9 are both hydrogen; or n is 5, R d and R e are both n-butyl, R f and R 9 are both hydrogen; or
  • n 4
  • R d and R e are both hydrogen
  • R f and R 9 are both paramethoxyphenyl
  • Y 1 and D 1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D 1 and Y 1 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, CrC 4 alkyl, Ci-C 4 haloalkyl, C1-C4 alkoxy and d-C 4 haloalkoxy (i.e. Y 1 and D 1 do not together form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered hetero
  • R 8 represents hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce alkenyl, d- C 6 alkynyl, Ci-C 6 alkoxy, Ci-Ce alkenyloxy, Ci-C 6 alkynyloxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, C 3 -C 6 cycloalkyl, phenyl or 5- or 6-membered heterocycle containing one to three
  • heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, OH, CN, C1-C4 alkyl, Ci-G, haloalkyl, Ci-G, alkoxy, Ci-G, haloalkoxy, Ci-G, alkylthio and Ci-G, haloalkylthio;
  • Y 4 represents hydrogen, halogen, CN, N0 2 , Ci-Q alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, COR 1 , OR 2 , SH, Ci-Ce alkylthio, Ci-Ce alkylsulphinyl, Ci-Cs alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R 3 ) 2 , C0 2 R 2 , 0(CO)R ⁇ CON(R 3 ) 2 , NR 3 COR ⁇ C ⁇ N-OR 2 , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, and phenyl are optionally substituted by one or more groups e.g. one to five groups, independently selected from halogen, CN, NH 2
  • Y 4 together with Y 3 and together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R 3 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 3 and Y 4 is optionally substituted by one or more groups e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d- C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 alkylthio.
  • one of Q and Q' together with the fragment to which it is attached is not phenanthroline.
  • R 8 and R 9 cannot both be alkoxycarbonyl.
  • Y 4 is not a heterocyclic ring.
  • R 8 and R 9 cannot both be alkoxycarbonyl, and when Q is Q-1 then Y 4 is not a heterocyclic ring.
  • the invention may not claim compounds of formula I"" in which R d and R e are hydrogen or hydrocarbon and R f and R 9 are hydrogen.
  • the invention provides a compound of formula Int-2
  • L 1 , L 2 , L 3 L 4 , L 5 , L 6 and X are as defined herein for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferred definitions of L 1 , L 2 , L 3 L 4 , L 5 , L 6 and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-2).
  • Particularly preferred are compounds of formula (int-2) where L 1 , L 2 , L 3 L 4 , L 5 and L 6 are each C-H.
  • the invention provides a compound of formula Int-3
  • L 1 , L 2 , L 3 L 4 , L 5 , L 6 , Q and X are as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferred definitions of L 1 , L 2 , L 3 L 4 , L 5 , L 6 , Q and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-3).
  • the invention provides a compound of formula Int-4
  • L 1 , L 2 , L 3 L 4 , L 5 , L 6 , Q and X are as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferred definitions of L 1 , L 2 , L 3 L 4 , L 5 , L 6 , Q and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-4).
  • the invention provides a compound of formula Int-5
  • L 1 , L 2 , L 3 L 4 , L 5 , L 6 , Q and X are as defined for compounds of formula (I) and R 29 is is a halogen in particular chlorine, bromine or iodine; or a salt or N-oxide thereof.
  • R 29 is is a halogen in particular chlorine, bromine or iodine; or a salt or N-oxide thereof.
  • the preferred definitions of L 1 , L 2 , L 3 L 4 , L 5 , L 6 , Q and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-4).
  • the compounds of formula (I) may exist as different geometric or optical isomers or in different tautomeric forms. These may be separated and isolated by well-known (usually chromatographic) techniques, and all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms, such as deuterated compounds, are part of the present invention.
  • the invention also includes salts and N-oxides of compounds of the invention.
  • Table 1 illustrates embodiments of

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Abstract

The present invention relates to methods of controlling or preventing phytopathogenic diseases on useful plants or on propagation material thereof comprising applying to useful plants, the locus thereof or propagation material thereof a compound of formula (I) wherein Q, Q', L1, L2, L3, L4, L5, L6 and X are as defined in claim 1. The invention also relates to novel compounds that may be used in said methods, as well as intermediates useful for the preparation of the novel compounds.

Description

Novel Microbiocides
The present invention relates to novel microbiocidally active, in particular fungicidally active heterocyclic compounds. It further relates to intermediates used in the preparation of these compounds, to compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by
phytopathogenic microorganisms, preferably fungi.
Fungicidally active 2-(pyridin-2-yl)-pyrimidines are described in WO 2007/116079. The disclosed compounds are characterised by a condensed aliphatic carbocycle or heterocycle. Surprisingly, it has been found that several heterocyclic systems, including novel compounds have microbiocidal activity.
The present invention relates to a method comprising applying to useful plants, the locus thereof or propagation material thereof a compound of formula (I)
Figure imgf000002_0001
(I)
wherein
L1 is N or C-D1;
L2 is N or C-D2;
L3 is N or C-D3;
L4 is N or C-D4;
L5 is N or C-D5;
L6 is N or C-D6;
D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, Ci-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR1, OR2, SH, d-C8 alkylthio, d-C8 alkylsulphinyl, Ci-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups
independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl and Ci-C4 haloalkyl; or D1 and D5, D2 and D5, D3 and D6, or D4 and D6 independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and D5, D2 and D5, D3 and D6, or D4 and D6 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy;
X represents X-2, X-3, X-4 or X-5:
#—∑—∑—# #— z— z— z— # #—∑—∑—∑—∑—#
X-2 X-3 X-4
„ -.10 -.11 -.12 -.13 -.14 „
#— z— z— z— z— z— #
X-5
Z1, Z2, Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5, C=0 or C=CR6R7;
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7;
wherein the groupings X-2, X-3, X-4 and X-5 contain at most one ring which contains either only one of the radicals Z1 to Z14 or two radicals Z1 to Z14 or three radicals Z1 to Z14 or four radicals Z1 to Z14 as ring members; and wherein none of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13 and Z14 represent a carbon atom substituted by two OH;
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
Q-9
Figure imgf000003_0001
Q-6 Q-7 Q-8 Q-9 each Y1, Y2, Y3 and Y4 independently of one another represent hydrogen, halogen, CN, N02, Ci-Cs alkyl, C3-C8 cydoalkyi, C2-C8 alkenyl, C2-C8 alkynyl, benzyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR1, OR2, SH, d-C8 alkylthio, d-C8 alkylsulphinyl, Ci-C8 a I kyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, benzyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl and d-d haloalkyl; when Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7 then Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
when Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000004_0001
Q' is selected from the group consisting of Q-Γ, Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'
Figure imgf000004_0002
Q-6' Q-7' Q-8' Q-9' each Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, CN, N02, Ci-C8 alkyl, C3-C8 cycloalkyi, C2-C8 alkenyl, C2-C8 alkynyl, benzyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR1, OR2, SH, d-C8 alkylthio, d-C8 alkylsulphinyl, Ci-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, benzyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl and Ci-C4 haloalkyl; when Q' is Q-Γ, Q-3', Q-2', Q-4', Q-6' or Q-7' then Y1' and Y2', Y2' and Y3', or Y3' and
Y4' independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-Q alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio; when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be
Figure imgf000005_0001
each G1 and G2 independently of one another represent -C(R14R15)-;
each G3 independently of one another represents -C(R14R15)-, 0, N(R16) or S;
or each combination of G1 and G2, or G2 and G3, or G1 and G1 may independently of one another together represent -CR14=CR15-;
each p independently of one another represents 0, 1 or 2;
each R1 independently of one another represents hydrogen, d-C8 alkyl, C3-C8 cycloalkyi, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
each R2 independently of one another represents hydrogen, CrC8 alkyl, C3-C8 cycloalkyl, C3-C8 alkenyl, C3-C8 alkynyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Q-G, alkyl, Ci-C4-haloalkyl, Q-G, alkoxy, Q-G, haloalkoxy and G-C4-alkoxy-Ci-C4-alkyl;
each R3 independently of one another represents hydrogen, OH, G-C8 alkyl, G-C8 alkoxy, G-C8-alkoxy-Ci-C4-alkyl, C3-C8 alkenyl, C3-C8 alkynyl or COR1, wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen;
wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different;
wherein when two radicals R3 are attached to the same nitrogen atom, both of these radicals cannot be OH, G-C4 alkoxy or G-C4 haloalkoxy;
and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B- 2, B-3, B-4, B-5, B-6, B-7 or B-8:
Figure imgf000006_0001
wherein the cycle formed is optionally substituted by one or more groups
independently selected from halogen, CN, NH2, N02, OH, G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy and G-C4 haloalkoxy;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH,
SH, CHO, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6alkynyl, G-C6alkoxy, C3-C6 alkenyloxy, C3- C6alkynyloxy, G-C6 alkylthio, G-C6 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocycle containing one to four heteroatoms independently selected from O, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, OR2, CN, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, CON(R3)2, NH2, NR^OR1 and phenyl; or R4 and R5 together with the carbon atom to which they are attached may form a
C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
each R6 and R7 independently of one another represent hydrogen, halogen, d-C4 alkyl or Ci-C4 haloalkyi;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6alkynyl, d-C6alkoxy, C3-C6 alkenyloxy, C3-
C6alkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocyde containing one to four heteroatoms independently selected from 0, S and N providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyde are optionally substituted by one or more groups independently selected from halogen, OH, OR2, CN, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, CON(R3)2, NH2, NR^OR1 and phenyl;
or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, C2-C4 alkenyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, C2-C4 alkenyloxy or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, CrC4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
R12 and R12' independently of one another represent hydrogen, halogen, CN, SH, d-
C8 alkylthio, Ci-C8 alkylsulphinyl, d-C8 alkylsulphonyl, NH2, CrCio alkyl, C3-C8 cycloalkyl, C2- C8 alkenyl, C2-C8 alkynyl, (R20)carbonyl(Ci-C4 alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, NH-Ci-C8 alkyl, N(Ci-C8 alkyl)2, N02, OR2, Ci-C4 alkyl, d-C4 haloalkyi, C3-C6 cycloalkyl and a 5- or 6- membered heterocyde containing one to three heteroatoms independently selected from O, S and N providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms;
R13 and R13' independently of one another represent hydrogen, Ci-C8 alkyl, C3-C8 cycloalkyl, C3-C8 alkenyl, C3-C8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d-Q alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
each R14 and R15 independently of one another represents hydrogen, halogen, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy;
each R16 indepenently of one another represents hydrogen, OH, d-C4 alkyl, Ci-C4 alkoxy, C3-C6 cycloalkyl, d-C8 alkylcarbonyl or d-C8 haloalkylcarbonyl;
or a salt or N-oxide thereof.
The invention covers all agronomically acceptable salts, isomers, structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers, atropisomers and N-oxides of those compounds. The compounds of formula I may exist in different geometric or optical isomeric forms or in different tautomeric forms. One or more centres of chirality may be present, in which case compounds of the formula I may be present as pure enantiomers, mixtures of enantiomers, pure diastereomers or mixtures of diastereomers. There may be double bonds present in the molecule, such as C=C or C=N bonds, in which case compounds of formula I may exist as single isomers or mixtures of isomers. Centres of tautomerisation may be present. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. Also
atropisomerism may occur as a result of a restricted rotation about a single bond.
Preferably the method is a method of controlling or preventing phytopathogenic diseases on useful plants or on propagation material thereof, more preferably a method of controlling or preventing phytopathogenic fungal diseases on useful plants or on propagation material thereof.
Halogen, either as a lone substituent or in combination with another substituent (e.g. haloalkyl) is generally fluorine, chlorine, bromine or iodine, and usually fluorine, chlorine or bromine.
Each alkyl moiety (including the alkyl moiety of alkoxy, alkylthio, etc.) is a straight or branched chain and, depending on the number of carbon atoms it contains, is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, /'so-propyl, sec-butyl, /'so-butyl, tert-butyl, neo-pentyl, n-heptyl or 1,3-dimethylbutyl, and usually methyl or ethyl.
The alkenyl group is an unsaturated straight or branched chain having at least one carbon-carbon double bond and, depending on the number of carbon atoms it contains, is, for example ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3- butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2- pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l- butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2- methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l-propenyl, 1.2- dimethyl-2-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5- hexenyl, 1-methyl-l-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l- pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2- pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3- pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4- pentenyl, l,l-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2- dimethyl-2-butenyl, l,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl,
1.3- dimethyl-3-butenyl, and usually 2-propenyl, l-methyl-2-propenyl, 2-butenyl, 2-methyl-2- propenyl.
The alkynyl group is an unsaturated straight or branched chain having at least one carbon-carbon triple bond and, depending on the number of carbon atoms it contains, is, for example ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2- propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-l-butynyl, l-methyl-2- butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, l,l-dimethyl-2-propynyl, l-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-l-pentynyl, 4- methyl-l-pentynyl, l-methyl-2-pentynyl, 4-methyl-2-pentynyl, l-methyl-3-pentynyl, 2- methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 3,3,- dimethyl-l-butynyl, l-ethyl-2-butynyl, l,l-dimethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3- butynyl, l,l-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl.
Haloalkyl moieties are alkyl moieties which are substituted by one or more of the same or different halogen atoms and are, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, 2,2, 2-tr if I uoroethyl , 2,2- difluoroethyl, 2-fluoroethyl, 1,1-d if I uoroethyl, 1-f I uoroethyl, 2-chloroethyl, pentafl uoroethyl, l,l-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, and typically trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and
dichlorofluoromethyl.
Alkoxy is, for example, methoxy, ethoxy, propoxy, /so-propoxy, n-butoxy, /so-butoxy, sec-butoxy and tert-butoxy, and usually methoxy or ethoxy.
Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy, and usually difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.
Alkylthio is, for example, methylthio, ethylthio, propylthio, /so-propylthio, n-butylthio, /so-butylthio, sec-butylthio or tert-butylthio, and usually methylthio or ethylthio.
Alkylsulphonyl is, for example, methylsulphonyl, ethylsulphonyl, propylsulphonyl, iso- propylsulphonyl, n-butylsulphonyl, /'so-butylsulphonyl, sec-butylsulphonyl or tert- butylsulphonyl, and usually methylsulphonyl or ethylsulphonyl. Alkylsulphinyl is, for example, methylsulphinyl, ethylsulphinyl, propylsulphinyl, iso- propylsulphinyl, n-butylsulphinyl, /'so-butylsulphinyl, sec-butylsulphinyl or tert-butylsulphinyl, and usually methylsulphinyl or ethylsulphinyl.
Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl,
ethoxyethyl, n-propoxymethyl, n-propoxyethyl, /'so-propoxymethyl or /'so-propoxyethyl.
Cycloalkyl may be saturated or partially unsaturated, preferably fully saturated, and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Aryl includes phenyl, naphthyl, anthracyl, fluorenyl and indanyl, but is usually phenyl.
Carbocycle includes cycloalkyl groups and aryl groups.
Heterocycloalkyl is a non-aromatic ring that may be saturated or partially
unsaturated, preferably fully saturated, containing carbon atoms as ring members and at least one heteroatom selected from 0, S and N as ring members. Examples include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,4-dioxanyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, oxazinanyl, dioxolane, dithiolane, morpholinyl,
thiomorpholinyl, imidazolidinyl, pyrazolidinyl and piperazinyl, preferably morpholinyl, pyrrolidinyl, piperdinyl and piperazinyl, more preferably dioxolane, dithiolane, morpholinyl and pyrollidinyl.
Heteroaryl is, for example, a monovalent monocyclic or bicyclic aromatic hydrocarbon radical. Examples of monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiadiazolyl. Examples of bicyclic groups include quinolinyl, cinnolinyl, quinoxalinyl, benzimidazolyl, benzothiophenyl, and benzothiadiazolyl. Monocyclic heteroaryl groups are preferred, preferably pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, pyridyl and imidazolyl being most preferred.
The terms "heterocycle" and "heterocyclic ring" are used interchangeably and are defined to include heterocycloalkyl and heteroaryl groups. Any reference herein to a heterocycle or heterocyclic ring preferably refers to the specific examples given under the definition of heteroaryl and heterocycloalkyl above, and are preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl and imidazolyl. No heterocycle contains adjacent oxygen atoms, adjacent sulphur atoms, or adjacent oxygen and sulphur atoms.
Where a moiety is indicated as being (optionally) substituted, e.g. alkyl, this includes those moieties where they are part of a larger group, e.g. the alkyl in the alkylthio group and the alkyl in the alkoxy group etc.. The same applies, e.g. to the phenyl moiety in phenylthio etc. Where a moiety is indicated as being optionally substituted by one or more other groups, preferably there are one to five optional substituents, more preferably one to three optional substituents. Where a moiety is substituted by a cyclic group, e.g. aryl, heteroaryl, cycloalkyl, preferably there are no more than two such substituents, more preferably no more than one such substituent.
The following substituents definitions, including preferred definitions, may be combined in any combination:
D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, Ci-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to four heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen, COR1, OR2, SH, Ci-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl, d-C4 haloalkyl.
Preferably, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, Ci-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl), COR1, OR2, SH, Ci-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R1, CON(R3)2, NR3COR\ CR^-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, Q-C, alkyl, d-C4 haloalkyl.
More preferably, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, OR2, Ci-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, phenyl, pyridyl, C02R2, N(R3)2, NR3COR\ C^N-OR^ SH, Ci-C8-alkylthio, d-C8-alkylsulphinyl, Ci-C8- alkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OR2, Ci-C4 alkyl and Ci-C4 haloalkyl.
Even more preferably, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, OR2, CN, d-C4 alkyl, C3-C6 cycloalkyl, N(R3)2, phenyl, C02R2 or NR3COR\ wherein the alkyl, cycloalkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, d-C4- haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
More preferably again, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, OH, CN, Ci-C4 alkyl, Ci-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyl, N(R3)2, phenyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups,
independently selected from halogen, CN, d-C4 alkyl, d-C4-haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy.
Yet more preferably D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, d-C4 alkyl, CN or d-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
In one group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkoxy and Ci-C4 haloalkoxy;
D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, d-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), COR1, OR2, SH, d-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R1, CON(R3)2, NR3COR\ CR^-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, Ci-C4 alkyl and Ci-C4 haloalkyl.
Preferably in this group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy;
D5 and D6 independently of one another represent hydrogen, CN, Ci-C4 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, Ci-G, alkyl, C1-C4 alkoxy and Ci-G, haloalkyl.
More preferably in this group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl, a 5- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, Ci-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl.
Even more preferably in this group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl, a 5- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, Ci-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl.
In another group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, d-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), COR1, OR2, SH, Ci-C8 alkylthio, Ci-C8 alkylsulphinyl, d-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, C1-C4 alkyl and d-C4 haloalkyl.
In this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another preferably represent hydrogen, CN, d-C4 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, d-C4 alkyl, d-C4 alkoxy and C1-C4 haloalkyl.
In this group of compounds D1, D2, D3, D4, D5 and D6 independently of one another more preferably represent hydrogen, d-C4 alkyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C4 alkoxy, d-C4 alkyl and Ci-C4 haloalkyl.
In this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another even more preferably represent hydrogen, d-C4 alkyl, phenyl, a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl.
In a sub-group of this group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkoxy and Ci-C4 haloalkoxy, wherein D5 and D6 are as defined above.
In a sub-group of this group of compounds, D1, D2, D3 and D4 independently of one another more preferably represent hydrogen, Ci-C4 alkyl, CN or d-C4 alkoxy, wherein D5 and D6 are as defined above.
In a sub-group of this group of compounds D1, D2, D3 and D4 most preferably each represent hydrogen, wherein D5 and D6 are as defined above.
In a further group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, d-C8 alkyl, C2-C8 alkynyl, d-C8 alkoxy or Ci-Cs alkylthio.
More preferably in this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, d-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy or Ci-C4 alkylthio. Even more preferably in this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
More preferably again in this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
Most preferably in this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, methoxy or methylthio. D1 and D5, D2 and D5, D3 and D6, or D4 and D6 may form a carbocyclic or heterocyclic ring. This possibility and preferences thereof are described below, which may be combined with any of the definitions above. Optionally the above definitions may exclude the possibility of rings formed by D1 and D5, D2 and D5, D3 and D6, or D4 and D6.
D1 and D5, D2 and D5, D3 and D6, D4 and D6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and D5, D2 and D5, D3 and D6, D4 and D6 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, d-Q alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy. Examples of possible ring fragments formed by D1 and D5, D2 and D5, D3 and D6, D4 and D6 include -CH=CH-CH=CH-, -CH2-CH2-CH2-CH2-, - CH2-CH2-CH2-, -N=CH-N=CH-, -CH=N-CH=N-, -N=N-CH=N-, -N=CH-N=N-, -CH=CH-S-, -S- CH=CH-, -CH=CH-NH-, -NH-CH=CH-, in each case any hydrogen atom may be substituted as indicated.
Preferably D1 and D5, D2 and D5, D3 and D6, D4 and D6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by D1 and D5, D2 and D5, D3 and D6, D4 and D6 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, d- C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
More preferably D1 and D5, D2 and D5, D3 and D6, D4 and D6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D1 and D5, D2 and D5, D3 and D6, D4 and D6 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, CrC4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
In one preferred group of compounds, D1 and D5, D2 and D5, D3 and D6, D4 and D6 together with the fragment of the ring to which they are attached do not form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3).
X represents X-2, X-3, X-4 or X-5. Preferably X represents X-3, X-4 or X-5. More Preferably X represents X-3 or X-5. Yet more preferably X represents X-3.
Z1, Z2, Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5, C=0 or C=CR6R7, preferably CR4R5 or C=CR6R7, more preferably CR4R5.
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7, preferably CR8R9 or C=CR6R7.
When X is X-2, preferably one of Z1 and Z2 is methylene or halomethylene, preferably methylene.
When X is X-3, preferably at least two of Z3, Z4 and Z5 are substituted only by hydrogen or halogen, preferably hydrogen, more preferably two of Z3, Z4 and Z5 are independently methylene or halomethylene, preferably methylene. Preferably, Z3 and Z5 are methylene or halomethylene, preferably methylene.
When X is X-4, preferably at least three of Z6, Z7, Z8 and Z9 are substituted only by hydrogen or halogen, preferably hydrogen, more preferably at least three of Z6, Z7, Z8 and Z9 are independently methylene or halomethylene, preferably methylene.
When X is X-5, preferably at least four of Z10, Z11, Z12, Z13 and Z14 are substituted only by hydrogen or halogen, preferably hydrogen more preferably four of Z10, Z11, Z12, Z13 and Z14 are independently methylene or halomethylene, preferably methylene. Preferably, Z10, Z11, Z13 and Z14 are independently methylene or halomethylene, preferably methylene.
The groupings X-2, X-3, X-4 and X-5 contain at most one ring which contains either only one of the radicals Z1 to Z14 or two radicals Z1 to Z14 or three radicals Z1 to Z14 or four radicals Z1 to Z14 as ring members. None of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13 and Z14 represent a carbon atom substituted by two OH groups. Optionally radicals Z1, Z3, Z6 and Z10 are not substituted by OH.
In one preferred group of compounds, the groupings X-2, X-3, X-4 and X-5 do not contain any rings which contain any of the radicals Z1 to Z14.
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9. Q-l, Q2, Q-3 and Q-9 are preferred. Q' is selected from the group consisting of Q- , Q- 2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'. Q-Γ, Q2', Q-3' and Q-9' are preferred. In one group of compounds, Q is selected from the group consisting of Q-l, Q-2, Q- 4, Q-5, Q-6, Q-7, Q-8 and Q-9. Q-l, Q2 and Q-9 are preferred. Q' is selected from the group consisting of Q-l', Q-2', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'. Q-Γ, Q2' and Q-9' are preferred.
Each Y1, Y2, Y3, Y4, Y1', Y2, Y3' and Y4 independently of one another represent hydrogen, halogen, CN, N02, Ci-C8 alkyl, C3-C8 cydoalkyi, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, benzyl, a 5- or 6- membered heterocyde containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocyde as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl), COR1, OR2, SH, Ci-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R1, CON(R3)2, NR3COR\ CR^-OR2, wherein the alkyl, cydoalkyi, alkenyl, alkynyl, phenyl, benzyl and heterocyde are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, d-Q alkyl and d-Q haloalkyl.
Preferably, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, CN, OR2, d-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cydoalkyi, phenyl, pyridyl, N(R3)2, C02R2, NR3COR\ SH, d-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8 alkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl, wherein the alkyl, alkenyl, alkynyl, cydoalkyi, phenyland pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OR2, d-C4 alkyl and Ci-C4 haloalkyl.
More preferably, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OR2, CN, d-C4 alkyl, C3-C6 cydoalkyi, N(R3)2, CrC4 alkylthio, Ci-C4 alkylsulphinyl, d-C4 alkylsulphonyl, phenyl, C02R2 or NR^OR1 wherein the alkyl, cydoalkyi and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
Yet more preferably, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, CN, Ci-C4 alkyl, Ci-C4 alkoxy, C3-C6 alkenyloxy, C3- C6 cydoalkyi, N(R3)2, CrC4 alkylthio, d-C4 alkylsulphinyl, d-C4 alkylsulphonyl, phenyl, phenyloxyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cydoalkyi and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy. Yet more preferably each Y1, Y2, Y3, Y4, Y1', Y2, Y3' and Y4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkoxy and Ci-C4 haloalkoxy.
In one group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, CN, Ci-C4 alkyl, Ci-C4 alkoxy, phenyl, wherein the alkyl, alkoxy and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, CrC4-haloalkyl, d-C4 alkoxy and d-C4 haloalkoxy.
In this group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another preferably represent hydrogen, halogen, OH, Ci-C4 alkyl, d-C4 alkoxy, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
In this group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another more preferably represent hydrogen, halogen, OH, Ci-C4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkyl.
In this group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another even more preferably represent hydrogen, halogen, OH, Ci-C4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl.
In this group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another yet more preferably represent hydrogen, OH, Ci-C4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl.
In another group of compounds, each Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or Ci-C4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl.
In this group of compounds, each Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another preferably represent hydrogen or Ci-C4 alkyl;
each Y4 and Y4' independently of one another preferably represent hydrogen, OH, d- C4 alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl. In a further group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, Ci-C8 alkyl, C2-C8 alkynyl, d-C8 alkoxy or Ci-Cs alkylthio.
More preferably in this group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, Ci-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy or Ci-C4 alkylthio.
Even more preferably in this group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
More preferably again in this group of compounds each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and
Y4' independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
Most preferably in this group of compounds, each Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, methoxy or methylthio.
When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7 then Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment to which they are attached may form a carbocyclic or heterocyclic ring. Likewise, Q' is Q- , Q-2', Q-3', Q-4', Q-6' or Q-7' then Y1' and Y2', Y2' and Y3', or Y3' and Y4' may form a carbocyclic or heterocyclic ring. This possibility and preferences thereof are described below, which may be combined with any of the definitions above.
When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7 then Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. Y1 and Y2, Y2 and Y3, or Y3 and Y4 together with the fragment of the ring to which they are attached may form a ring system selected from isoquinoline; 5,6,7,8- tetrahydro-isoquinoline; 6,7-dihydro-5H-[2]pyrindine; 3,4-dihydro-lH-pyrano[3,4-c]pyridine; 6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine; [l,7]naphthyridine; quinoline; 5,6,7,8- tetrahydro-quinoline; 6,7-dihydro-5H-[l]pyrindine; [l,8]naphthyridine; 6,7,8,9-tetrahydro- 5H-cyclohepta[b]pyridine; and 7,8-dihydro-5H-pyrano[4,3-b]pyridine), and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, C1-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio. The same applies to Y1' and Y2, Y2 and Y3', or Y3' and Y4 when Q' is Q-Γ, Q-2', Q-3', Q-4', Q-6' or Q-7'.
Preferably each combination of Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, Ci-G, alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio. The same applies to Y1' and Y2', Y2' and Y3', or Y3' and Y4'.
More preferably each combination of Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio. The same applies to Y1' and Y2', Y2' and Y3', or Y3' and Y4'.
More preferably each Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy,
Ci-C4 haloalkoxy and Ci-C4 alkylthio. The same applies to Y2' and Y3'.
More preferably Y2 and Y3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and d-
C4 alkylthio. The same applies to Y2' and Y3'.
In one group of compounds, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl. The same applies to Y2' and
Y3'.
In another group of compounds, Y2 and Y3, together with the fragment of the ring to which they are attached may only form a ring when Q is Q-2. The same applies to Y2' and Y3'. In a further group of compounds, Y2 and Y3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio.When Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached may form a carbocyclic or heterocyclic ring. Likewise, when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8' then Y1' and D4 together with the fragment to which they are attached may form a carbocyclic or heterocyclic ring. This possibility and preferences thereof are described below, which may be combined with any of the definitions above.
When Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, d-C, alkyl, Ci-C, haloalkyi, Ci-G, alkoxy, Ci-G, haloalkoxy and Ci-C4 alkylthio. The same applies to Y1' and D4 when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8'. Examples of ring fragments that may be formed by Y1 and D1, Y1' and D4 include -CH=CH-, - CH2-CH2-, -CH2-CH2-CH2-, CH2-NH-CH2-, -CH2-0-CH2-, in each case any hydrogen atom may be substituted as indicated.
Preferably, when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7- membered heterocyclic ring containing one or two heteroatoms independently selected from N and N(R3), wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, d-C4 alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio. The same applies to Y1' and D4 when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8'.
Preferably, when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio. The same applies to Y1' and D4 when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8'. More preferably, when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to four groups, independently selected from halogen, CN, OH, d-Q alkyl, d-Q haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio. The same applies to Y1' and D4 when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8'.
Even more preferably, when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, d-C4 haloalkoxy and Ci-C4 alkylthio. The same applies to Y1' and D4 when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8'.
Most preferably, when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6- membered carbocydic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy. The same applies to Y1' and D4 when Q' is Q- Γ, Q-3', Q-4', Q-7' or Q-8'.
In one group of compounds, wherein Q is Q-l or Q-3 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to four groups, independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio. The same applies to Y1' and D4 in the group of compounds wherein Q' is Q- or Q- 3'.
More preferably in this group of compounds, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy. The same applies to Y1' and D4 in the group of compounds wherein Q' is Q-Γ or Q-3'.
Most preferably in this group of compounds, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocydic ring. The same applies to Y1' and D4 in the group of compounds wherein Q- or Q' is Q-3'. Preferably in this group of compounds, Q is Q-l and/or Q' is Q-l'.When Q is Q-9 and L1 is C-D1 then R12 and D1 together ma Likewise when Q' is Q-9' and L4 is C-D4, then R12 and D4 together may be
Figure imgf000023_0001
G1 and G2 independently of one another represent -C(R14R15)-; G3 represents - C(R14R15)-, 0, N(R16) or S; or G1 and G2, or G2 and G3, or G1 and G1 together represent - CR14=CR15-. Preferably, G1, G2 and G3 represent C(R21)2, wherein each R21 independently of one another represents hydrogen, halogen, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy, preferably hydrogen or d-C4 alkyl. More preferably, G1, G2 and G3 represent methylene.
Each p independently of one another represents 0, 1 or 2, preferably 1 or 2, more preferably 1.
Each R1 independently of one another represents hydrogen, CrC8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, C1-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy. Preferably, each R1 independently of one another represents hydrogen, Ci-C8 alkyl or d-C8 haloalkyl.
In one group of compounds, each R1 independently of one another represents hydrogen, d-d alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy and d-C4 haloalkoxy.
Preferably in this group of compounds, each R1 independently of one another represents hydrogen, d-C4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy and d-C4 haloalkoxy.
More preferably in this group of compounds, each R1 independently of one another represents hydrogen, d-C4 alkyl or phenyl, wherein the phenyl maybe substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy and d-C4 haloalkoxy.
Even more preferably in this group of compounds, each R1 independently of one another represents hydrogen or phenyl, wherein the phenyl may be substituted by one or more groups, e.g. one to five groups, independently selected from halogen, d-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy and d-C4 haloalkoxy.
Most preferably in this group of compounds, each R1 independently of one another represents hydrogen or phenyl. Each R2 independently of one another represents hydrogen, CrC8 alkyl, C3-C8 cycloalkyi, C3-C8 alkenyl, C3-C8 alkynyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4-haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4-alkyl-CrC4-alkoxy and d-C4-alkoxy-d-C4-alkyl. The heterocycle is preferably one as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl.
Preferably, each R2 independently of one another represents hydrogen, Ci-C8 alkyl, C3-C8 cycloalkyi, C3-C8 alkenyl, C3-C8 alkynyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, Ci-C4- haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4-alkoxy-CrC4-alkyl.
Preferably, each R2 independently of one another represents hydrogen, Ci-C8 alkyl,
Ci-C8 haloalkyl, C3-C8 cycloalkyi, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, Ci-C4-haloalkyl, d-C4 alkoxy and d-C4 haloalkoxy.
More preferably, each R2 independently of one another represents hydrogen, Ci-C8 alkyl, Ci-C8 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, d- C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
More preferably, each R2 independently of one another represents hydrogen, Ci-C4 alkyl, Ci-C4 haloalkyl, C3-C6 alkenyl or C3-C6 haloalkenyl.
Yet more preferably, each R2 independently of one another represents hydrogen, d- C4 alkyl or Ci-C4 haloalkyl.
In one group of compounds, each R2 independently of one another represents hydrogen, d-C4 alkyl or C3-C6 alkenyl. Each R3 independently of one another represents hydrogen, OH, Ci-C8 alkyl, Ci-C8 alkoxy, Ci-C8-alkoxy-Ci-C4-alkyl, C3-C8 alkenyl, C3-C8 alkynyl or COR1, wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more, e.g. one to five, halogen; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; wherein when two radicals R3 are attached to the same nitrogen atom, both of these radicals cannot be OH, Ci-C4 alkoxy or Ci-C4 haloalkoxy;
and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B- 2, B-3, B-4, B-5, B-6, B-7 or B-8, wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
Preferably, each R3 independently of one another represents hydrogen, d-C8 alkyl or COR1; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl.
More preferably, each R3 independently of one another represents hydrogen or Ci-C4 alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl.
More preferably, each R3 independently of one another represents hydrogen or Ci-C4 alkyl.
Most preferably, each R3 represents hydrogen.
Each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-C6 alkyl, C2-C6 alkenyl, C2-C6alkynyl, Ci-C6alkoxy, C3-C6 alkenyloxy, Cr
C6alkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocyde containing one to four heteroatoms independently selected from O, S and N providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyde are optionally substituted by one or more groups independently selected from halogen, OH, OR2, CN, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, CON(R3)2, NH2, NF^COR1 and phenyl;
or R4 and R5 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group.
Preferably, each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6alkynyl, Ci-Cealkoxy, C3-C6 alkenyloxy, C3-C6alkynyloxy, Ci-Ce alkylthio, Ci-Cs alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocycle containing one to four heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, OR2, CN, Ci-C4 alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, CON(R3)2, NH2, NR^OR1 and phenyl.
More preferably, each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-C, alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C, alkoxy, C3-C4 alkenyloxy, d-C4 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR^OR1 or CR^-OR2, wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C4 alkyl, Ci-C4 haloalkyi, d-C4 alkoxy, d-C4 haloalkoxy and NH2.
More preferably, each R4 and R5 independently of one another represent hydrogen, Ci-C4 alkyl, CrC4 alkoxy, d-C4 alkoxycarbonyl, CON(R3)2, NH2, NR^O^ or C^N-OR2, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN and NH2.
More preferably, each R4 and R5 independently of one another represent hydrogen,
Ci-C4 alkyl or Ci-C4 alkoxycarbonyl, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen.
More preferably, each R4 and R5 independently of one another represent hydrogen, Ci-C4 alkyl or Ci-C4 alkoxycarbonyl.
More preferably, each R4 and R5 independently of one another represent hydrogen,
Ci-C4 alkyl or d-C2 alkoxycarbonyl.
More preferably, each R4 and R5 independently of one another represent hydrogen or d-d alkoxycarbonyl.
Most preferably, each R4 and R5 represents hydrogen.
In one group of compounds, each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce alkenyl, d-C6alkynyl, Ci-Cealkoxy, Ci-Cs alkenyloxy, Ci-Cealkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C3-C6cycloalkyl, phenyl or 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-Q alkyl, d-Q haloalkyl, d-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio and d-C4 haloalkylthio; or R4 and R5 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyi group or a C3-C6 halocycloalkyl group. Examples of heterocylces include dioxolane, dithiolane, morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably dioxolane, dithiolane, pyridyl or imidazolyl.
Preferably, each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkenyl, Ci-Ce haloalkenyl, d- C6alkynyl, Ci-dhaloalkynyl, d-C6alkoxy, d-C6haloalkoxy, Ci-Ce alkenyloxy, Ci-Ce
haloalkenyloxy, Ci-Cealkynyloxy, Ci-Cehaloalkynyloxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, d- C6 alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C3-C6cycloalkyl, C3-C6halocycloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy;or R4 and R5together with the carbon atom to which they are attached may form a C3-C6 cycloalkyi group or a C3-C6 halocycloalkyl group.
Preferably, each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 alkenyloxy or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R4 and R5 together with the carbon atom to which they are attached may form a
C3-C6 cycloalkyi group or a C3-C6 halocycloalkyl group.
More preferably, each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 alkoxy, Ci-C4 alkenyloxy or Ci-C4 haloalkyl; or R4 and R5 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyi group or a C3-C6 halocycloalkyl group.
More preferably, each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, d-C4 alkyl or d-C4 haloalkyl.
In one group of compounds each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, d-C4 alkyl, Ci-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy; or R4 and R5 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group.
Each R6 and R7 independently of one another represent hydrogen, halogen, CrC4 alkyl or Ci-C4 haloalkyl. Preferably, each R6 and R7 independently of one another represent hydrogen, halogen, methyl or halomethyl.
Most preferably, each R6 and R7 represent hydrogen.
Each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6alkynyl, Ci-C6alkoxy, C3-C6 alkenyloxy, C3- C6alkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocyde containing one to four heteroatoms independently selected from 0, S and N providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyde are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-G, alkoxy, CrC4 haloalkoxy, benzyloxy, CrC4 alkylthio, CrC4 haloalkylthio, CON(R3)2, NH2, NR^OR1 and phenyl;
or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group.
Preferably, each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, d-C6 alkyl, C2-C6 alkenyl, C2-C6alkynyl, Ci-C6alkoxy, C3-C6 alkenyloxy, C3-C6alkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocyde containing one to four heteroatoms independently selected from O, S and N providing that the heterocyde does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyde are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy, benzyloxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, CON(R3)2, NH2, NR^OR1 and phenyl.
More preferably, each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-G, alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, d-C4 alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(Ci-C4 alkyl), CON(CrC4 alkyl)2, NH2, NR3CO(CrC4 alkyl), NR3CO(C2-C4 alkenyl), NR3CO(C2-C4 alkynyl), NR3COphenyl, CHN-OR2, phenyl or 5-membered heterocyde containing one to four heteroatoms independently selected from 0 and N providing that the heterocyde does not contain adjacent oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyde are optionally substituted by one or more groups independently selected from halogen, OH, CN, C1-C4 alkyl, C1-C4 haloalkyl, Ci-G, alkoxy, Ci-G, haloalkoxy, benzyloxy, NH2, NHCO(d-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl.
Even more preferably, each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, d-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, d-C4 alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(Ci-C4 alkyl), CON(CrC4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(d-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the heterocycle is substituted by one or more d-C4 alkyl.
Yet more preferably, each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, Ci-G, alkyl, C2-C4 alkenyl, Ci-G, alkoxy, C3-C4 alkenyloxy, Ci-G, alkoxycarbonyl, CONH2, CONH(Ci-C4 alkyl), CON(CrC4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl.
More preferably still, each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, Ci-G, alkyl, C2-C4 alkenyl, Ci-G, alkoxy, C3-C4 alkenyloxy, Ci-G, alkoxycarbonyl, CONH2, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, Ci-C4 alkoxy, benzyloxy, NH2, NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl.
Most preferably, each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, C1-C4 alkyl, d-C4 alkoxy, C3-C4 alkenyloxy, Ci-G, alkoxycarbonyl, CHN-OH, or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy and phenyl.
In one group of compounds, each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, d-C6 alkyl, d-C6 alkenyl, d-C6alkynyl, d-C6alkoxy, Ci-Ce alkenyloxy, d-C6alkynyloxy, d-C6 alkylthio, d-C6 alkoxycarbonyl, C3-C6cycloalkyl, phenyl or 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-Q alkyl, d-Q haloalkyi, d-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio and d-C4 haloalkylthio; or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group. Examples of heterocylces include dioxolane, dithiolane, morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably dioxolane, dithiolane, pyridyl or imidazolyl.
Preferably, each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, d-C6 alkyl, d-C6 haloalkyi, d-C6 alkenyl, d-C6 haloalkenyl, d- C6alkynyl, Ci-dhaloalkynyl, d-C6alkoxy, d-C6haloalkoxy, Ci-Ce alkenyloxy, d-C6
haloalkenyloxy, d-C6alkynyloxy, d-C6haloalkynyloxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, d- C6 alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C3-C6cycloalkyl, C3-C6halocycloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy;or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group.
Preferably, each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 alkenyloxy or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group.
More preferably, each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-Q alkoxy, Ci-C4 alkenyloxy or Ci-C4 haloalkyi; or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group.
In one group of compounds R8, R9, R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyi or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyi, d-C4 alkoxy and Ci-C4 haloalkoxy; or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group.
Each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, C2-C4 alkenyl, Ci-C4 haloalkyi or phenyl, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, C1-C4 alkyl, Ci-Q haloalkyi, d-C4 alkoxy and Ci-C4 haloalkoxy.
Preferably, each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyi or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.
R12 and R12' independently of one another represent hydrogen, halogen, CN, SH, d- C8 alkylthio, Ci-C8 alkylsulphinyl, d-C8 alkylsulphonyl, NH2, C1-C10 alkyl, C3-C8 cycloalkyi, C2- C8 alkenyl, C2-C8 alkynyl, (R20)carbonyl(Ci-C4 alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, NH-Ci-C8 alkyl, N(Ci-C8 alkyl)2, N02, OR2, Ci-G, alkyl, d-C4 haloalkyi, C3-C6 cycloalkyi and a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms. The heterocycle is preferably one as defined herein, e.g. morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl.
Preferably, R12 and R12' independently of one another represent hydrogen, d-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyi, phenyl, pyridyl, or (R20)carbonyl(d-C4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g. one to five groups, independently selected from halogen, CN, OR2, NH2, NH-Ci-C8 alkyl, N(d-C8 alkyl)2, d-C4 alkyl, Ci-C4 haloalkyi, C3-C6 cycloalkyi and pyridyl.
More preferably, R12 and R12' independently of one another represent hydrogen, d-C4 alkyl, C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, NH2, NH-Ci-C4 alkyl, N(Ci-C4 alkyl)2, Ci-C4 alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, d-C4 haloalkoxy and C3-C6 cycloalkyi.
More preferably, R12 and R12' independently of one another represent hydrogen, d-C4 alkyl.
Most preferably, R12 and R12' independently of one another represent Ci-C4 alkyl.
In one group of compounds, R12 and R12' independently of one another represent hydrogen, d-C4 alkyl, C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups,
independently selected from halogen, CN, d-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy and Ci-C4 haloalkoxy. Preferably in this group of compounds, R12 and R12' independently of one another represent hydrogen, Ci-C4 alkyl, d-C4 haloalkyi, phenyl or pyridin-2-yl, wherein the phenyl and pyridin-2-yl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.
R13 and R13' independently of one another represent hydrogen, Ci-C8 alkyl, C3-C8 cycloalkyl, C3-C8 alkenyl, C3-C8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
Preferably, R13 and R13' independently of one another represent hydrogen, d-C8 alkyl,
Ci-C8 haloalkyi, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, benzyl or pyridyl, wherein the, benzyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
More preferably, R13 and R13' independently of one another represent Ci-C4 alkyl, C3-
C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkoxy and Ci-C4 haloalkoxy.
More preferably, R13 and R13' independently of one another represent hydrogen, d-C8 alkyl, or d-C8 haloalkyi.
Even more preferably, R13 and R13' independently of one another represent hydrogen, C1-C4 alkyl or Ci-G, haloalkyi.
More preferably again, R13 and R13' independently of one another represent hydrogen or Ci-Q alkyl.
Most preferably, R13 and R13' independently of one another represent Ci-C4 alkyl.
In one group of compounds R13 and R13' independently of one another represent hydrogen, d-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl, d-C4 haloalkyi, halogen, CN, d-C4 alkoxy and d-C4 haloalkoxy.
More preferably in this group of compounds, R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
Most preferably in this group of compounds, R13 and R13' independently of one another represent hydrogen, methyl orpropargyl. Each R14 and R15 independently of one another represent hydrogen, halogen, CrC4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy, preferably hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
R16 represents hydrogen, OH, d-C4 alkyl, Ci-C4 alkoxy, C3-C6 cycloalkyi, Ci-Cs alkylcarbonyl or Ci-C8 haloalkylcarbonyl, preferably hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
In one group of compounds no more than one of L1, L5 and L2 is N, and no more than one of L3, L6 and L4 is N.
In one group of compounds L1 is C-D1, L2 is C-D2 and L5 is C-D5.
In one group of compounds L1 is C-D1, L2 is C-D2, L3 is C-D3, L4 is C-D4, L5 is C-D5 and
L6 is C-D6.
In one group of compounds L1 is C-D1, L2 is N, and L5 is C-D5.
In one group of compounds L1 is C-D1, L2 and L3 are N, L4 is C-D4, L5 is C-D5 and L6 is
C-D6.
In one group of compounds L1 is N, L2 is C-D2 and L5 is C-D5.
In one group of compounds L1 and L4 are N, L2 is C-D2, L3 is C-D3, L5 is C-D5 and L6 is
C-D6.
In one group of compounds L1 is N or C-D1; L2 is C-D2; L3 is C-D3; L4 is N or C-D4; L5 is C-D5; L6 is C-D6.
In one group of compounds L1 is the same as L4, L5 is the same as L6, L2 is the same as L3, Q is the same as Q'.
In one group of compounds Q is Q-9 and G1, G2 and G3 represent methylene. In one group of compounds Q' is Q-9' and G1, G2 and G3 represent methylene. In one group of compounds Q is Q-9 and Q' is Q-9' and G1, G2 and G3 represent methylene.
In one group of compounds
L1 is N or C-D1; L2 is C-D2; L3 is C-D3; L4 is N or C-D4; L5 is C-D5; L6 is C-D6;
D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, OH, CN, Ci-C, alkyl, d-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyi, N(R3)2, phenyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyi and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy; or
D1 and D5, D2 and D5, D3 and D6, D4 and D6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D1 and D5, D2 and D5, D3 and D6, D4 and D6 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy; X represents X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9;
each Y1, Y2, Y3, Y4 independently of one another represent hydrogen, halogen, OH, CN, Ci-C4 alkyl, C1-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyl, N(R3)2, Ci-C4 alkylthio, Ci-C4 alkylsulphinyl, Ci-C4 alkyl sulphonyl, phenyl, phenyloxyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, CrC4-haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy;
when Q is Q-l, Q-2, Q-3, Q-4, Q-6, or Q-7 then Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, Ci-C4 haloalkoxy and d-C4 alkylthio;
when Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000034_0001
Q' is selected from the group consisting of Q-Γ, Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
each Y1', Y2', Y3', Y4' independently of one another represent hydrogen, halogen, OH, CN, Ci-C4 alkyl, d-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyl, N(R3)2, Ci-C4 alkylthio, Ci-C4 alkylsulphinyl, Ci-C4 alkyl sulphonyl, phenyl, phenyloxyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, d-C4-haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy;
when Q' is Q-Γ, Q-2', Q-3', Q-4', Q-6', or Q-7' then Y1' and Y2', Y2' and Y3', or Y3' and Y4' independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, d-Q alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups independently selected from halogen, CN, OH, d-C4 alkyl, Ci-C4 haloalkyi, d-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q' is Q-9' and L4 is C-D4, then R12 and D4 together may be
Figure imgf000035_0001
G1, G2 and G3 represent C(R21)2;
each p independently of one another represents 1 or 2;
each R2 independently of one another represents hydrogen, d-C8 alkyl, Ci-Cs haloalkyi, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy;
each R3 independently of one another represents hydrogen or d-C4 alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 alkoxy, Ci-C4 alkenyloxy or Ci-C4 haloalkyi; or R4 and R5 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
each R6 and R7 independently of one another represent hydrogen, halogen, d-C4 alkyl or Ci-C4 haloalkyi;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, d-C6 haloalkyi, d-C6 alkenyl, d-C6 haloalkenyl, d-C6alkynyl, d- Cehaloalkynyl, d-C6alkoxy, d-C6haloalkoxy, Ci-Ce alkenyloxy, Ci-Ce haloalkenyloxy, d- C6alkynyloxy, Ci-dhaloalkynyloxy, d-C6 alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C3-C6cycloalkyl, C3-C6halocycloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyi, d-C4 alkoxy, d-C4 haloalkoxy;
or R8 and R9 together with the carbon atom to which they are attached may form a
C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group; R12 and R12' independently of one another represent hydrogen, Ci-C4 alkyi, C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyi, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OH, NH2, NH- C1-C4 alkyi, N(Ci-C4 alkyl)2, C1-C4 alkyi, Ci-Q haloalkyl, Ci-Q alkoxy, Ci-Q haloalkoxy and C3- C6 cycloalkyl;
R13 and R13' independently of one another represent Ci-C4 alkyi, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyi, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
each R21 independently of one another represents hydrogen, halogen, Ci-C4 alkyi, d-
C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy.
In one group of compounds
L1 is N or C-D1; L2 is C-D2; L3 is C-D3; L4 is N or C-D4; L5 is C-D5; L6 is C-D6.
D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, d-C4 alkyi, CN or d-C4 alkoxy, wherein the alkyi and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
X represents X-3 or X-5:
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
each Y1, Y2, Y3 and Y4 independently of one another represent hydrogen, Ci-C4 alkyi, CN or d-C4 alkoxy, wherein the alkyi and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy;
when Q is Q-l, Q-2 or Q-3 then Y2 and Y3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic and wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyi, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l or Q-3 then Y1 and D1 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyi, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000036_0001
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9'; each Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, CrC4 alkyl, CN or CrC4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy;
when Q' is Q- , Q-2' or Q-3' then Y2' and Y3' together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic and wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy and d- C4 alkylthio;
when Q' is Q- or Q-3' then Y1' and D4 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic or and wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be
Figure imgf000037_0001
each G1, G2 and G3 independently of one another represent -C(R14R15)-;
each p is 1;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl or Ci-C4 haloalkyi;
each R6 and R7 independently of one another represent hydrogen, halogen, d-C4 alkyl or d-C4 haloalkyi;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce haloalkyi, Ci-Ce alkenyl, Ci-Ce haloalkenyl, d-C6alkynyl, d- Cehaloalkynyl, d-C6alkoxy, d-C6haloalkoxy, Ci-Ce alkenyloxy, Ci-Ce haloalkenyloxy, d- C6alkynyloxy, Ci-dhaloalkynyloxy, d-C6 alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C3-C6cycloalkyl, C3-C6halocycloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyi, d-C4 alkoxy, d-C4 haloalkoxy;
or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
R12 and R12' independently of one another represent hydrogen, Ci-C4 alkyl, C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
R13 and R13' independently of one another represent hydrogen, Ci-Cs alkyl, or Ci-Q. haloalkyi; each R14 and R15 independently of one another represents hydrogen, halogen, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy.
In one group of compounds
L1 is N or C-D1; L2 is C-D2; L3 is C-D3; L4 is N or C-D4; L5 is C-D5; L6 is C-D6;
D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen,
OH, CN, Ci-Q alkyl, Ci-C, alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyi, N(R3)2, phenyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyi and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy; or
D1 and D5, D2 and D5, D3 and D6, D4 and D6 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D1 and D5, D2 and D5, D3 and D6, D4 and D6 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
X represents X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9; each Y1, Y2, Y3, Y4 independently of one another represent hydrogen, halogen, OH, CN, Ci-C4 alkyl, d-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyi, N(R3)2, Ci-C4 alkylthio, Ci-C4 alkylsulphinyl, Ci-C4 alkyl sulphonyl, phenyl, phenyloxyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyi and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, d-C4-haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy;
when Q is Q-l, Q-2, Q-4, Q-6, or Q-7 then Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, Ci-C4 haloalkoxy and d-C4 alkylthio;
when Q is Q-9 and L1 is C-D1 then R12 and D1 together may be -(G G^G3-; Q' is selected from the group consisting of Q- , Q-2', Q-4', Q-5', Q-6', Q-7', Q-8' and
Q-9';
each Y1', Y2', Y3', Y4' independently of one another represent hydrogen, halogen, OH, CN, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyl, N(R3)2, C1-C4 alkylthio, C1-C4 alkylsulphinyl, Ci-C4 a I kyl sulphonyl, phenyl, phenyloxyl or C02R2, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, CrC4-haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy;
when Q' is Q-Γ, Q-2', Q-4', Q-6', or Q-7' then Y1' and Y2, Y2' and Y3', or Y3' and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyi, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q' is Q-Γ, Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyi, d-C4 alkoxy, Ci-C4 haloalkoxy and d-C4 alkylthio;
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be
Figure imgf000039_0001
G1, G2 and G3 represent C(R21)2;
each p independently of one another represents 1 or 2;
each R2 independently of one another represents hydrogen, d-C8 alkyl, Ci-Cs haloalkyi, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy;
each R3 independently of one another represents hydrogen or d-C4 alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, C1-C4 alkoxy, Ci-C4 alkenyloxy or Ci-C4 haloalkyi; or R4 and R5 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
each R6 and R7 independently of one another represent hydrogen, halogen, d-C4 alkyl or Ci-C4 haloalkyl;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH,
SH, CHO, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-C6 alkenyl, Ci-Ce haloalkenyl, Ci-C6alkynyl, d- Cehaloalkynyl, d-C6alkoxy, CrC6haloalkoxy, Ci-Ce alkenyloxy, Ci-Ce haloalkenyloxy, d- C6alkynyloxy, Ci-dhaloalkynyloxy, d-C6 alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C3-C6cycloalkyl, C3-C6halocycloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy;
or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
R12 and R12' independently of one another represent hydrogen, Ci-C4 alkyl, C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OH, NH2, NH- Ci-C4 alkyl, N(Ci-C4 alkyl)2, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and C3- C6 cycloalkyl;
R13 and R13' independently of one another represent Ci-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
each R21 independently of one another represents hydrogen, halogen, Ci-C4 alkyl, d- C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy.
In one group of compounds, L1 is N or C-D1; L2 is C-D2; L3 is C-D3; L4 is N or C-D4; L5 is C-D5; L6 is C-D6;
D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, d-C4 alkyl, CN or d-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
X represents X-3 or X-5:
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2 and Q-9;
each Y1, Y2, Y3 and Y4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or d-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy; when Q is Q-l or Q-2 then Y2 and Y3 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic and wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-Q alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio; when Q is Q-l then Y1 and D1 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio; when Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000041_0001
Q' is selected from the group consisting of Q- , Q-2' and Q-9';
each Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, d-C4 alkyl, CN or CrC4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy;
when Q' is Q- or Q-2' then Y2' and Y3' together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic and wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio; when Q' is Q- then Y1' and D4 together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic or and wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be
Figure imgf000041_0002
each G1, G2 and G3 independently of one another represent -C(R14R15)-;
each p is 1;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl or d-C4 haloalkyl;
each R6 and R7 independently of one another represent hydrogen, halogen, d-C4 alkyl or Ci-C4 haloalkyl;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH,
SH, CHO, Ci-Ce alkyl, d-C6 haloalkyl, Ci-Q alkenyl, Ci-Q haloalkenyl, d-C6alkynyl, d- Cehaloalkynyl, d-C6alkoxy, d-C6haloalkoxy, Ci-Q alkenyloxy, Ci-Q haloalkenyloxy, d- C6alkynyloxy, Ci-dhaloalkynyloxy, d-C6 alkylthio, Ci-Ce haloalkylthio, Ci-Q alkoxycarbonyl, Ci-Ce haloalkoxycarbonyl, C3-C6cycloalkyl, C3-C6halocycloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy; or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
R12 and R12' independently of one another represent hydrogen, Ci-C4 alkyl, C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
R13 and R13' independently of one another represent hydrogen, Ci-C8 alkyl, or Ci-C8 haloalkyl;
each R14 and R15 independently of one another represents hydrogen, halogen, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy.
In another group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkoxy and Ci-C4 haloalkoxy;
D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, d-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), COR1, OR2, SH, d-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8
alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R1, CON(R3)2, NR^OR1 or CR^-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, Ci-C4 alkyl and Ci-C4 haloalkyl;
X represents X-3, X-4 or X-5;
Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7;
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, Ci-C4 alkoxy or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy; When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7, Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-Q alkyl, Q-G, haloalkyl, Ci-G, alkoxy, C1-C4 haloalkoxy and G-C4 alkylthio;
When Q' is Q-l', Q-2', Q-3', Q-4', Q-6' or Q-7', Y1' and Y2', Y2' and Y3', or Y3' and Y4' independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-Q alkyl, G-C4 haloalkyl, Q-G, alkoxy, Q-G, haloalkoxy and Q-G, alkylthio;
When Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy, G-C4 haloalkoxy and G-C4 alkylthio;
When Q is Q-l', Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy, G-C4 haloalkoxy and G-C4 alkylthio;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000043_0001
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be -(G -G2-G3'
G1, G2 and G3 represent C(R21)2, wherein each R21 independently of one another represents hydrogen, halogen, G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy or G-C4 haloalkoxy;
Each p independently of one another represents 1 or 2;
each R1 independently of one another represents hydrogen, G-C4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy and G-C4 haloalkoxy; each R2 independently of one another represents hydrogen, G-C8 alkyl, G-C8 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, CrC4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy;
each R3 independently of one another represents hydrogen or d-C4 alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH,
CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR^OR1 or CR^-OR2, wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, d-C4 haloalkoxy and NH2;
Each R6 and R7 independently of one another represent hydrogen, halogen, methyl or halomethyl;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, d-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci-C4 alkoxycarbonyl, C3-C6 cycloalkyi, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the heterocycle is substituted by one or more d-C4 alkyl;
each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
R12 and R12' independently of one another represent hydrogen, Ci-Cs alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyi, phenyl, pyridyl, or (R20)carbonyl(d-C4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g. one to five groups, independently selected from halogen, CN, OR2, NH2, NH-Ci-Cs alkyl, N(d-C8 alkyl)2, Ci-C4 alkyl, d-C4 haloalkyl, C3-C6 cycloalkyi and pyridyl; R13 and R13' independently of one another represent Ci-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy;
In another group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X represents X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7; Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d-C4 alkyl;
each Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groupsindependently selected from halogen, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
each Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy; When Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12 and D4 together may
Figure imgf000046_0001
G1, G2 and G3 represent C(R21)2;
each R21 independently of one another represents hydrogen or d-C4 alkyl;
Each p independently of one another represents 1 or 2;
each R4 and R5 independently of one another represent hydrogen, d-C4 alkyl or Ci-C4 alkoxycarbonyl;
each R6 and R7 represent hydrogen;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, d-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci-C4 alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the heterocycle is substituted by one or more d-C4 alkyl;
R12 and R12' independently of one another represent hydrogen or d-C4 alkyl;
R13 and R13' independently of one another represent hydrogen or d-C4 alkyl.
In another group of compounds, D1, D2, D3 and D4 each represent hydrogen;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9; Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
each Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or C1-C4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, d-Q alkyl, phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may b
Figure imgf000047_0001
G1, G2 and G3 represent methylene;
p represents 1;
each R4 and R5 independently of one another represent hydrogen or Ci-C2
alkoxycarbonyl;
each R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, C2-C4 alkenyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, CONH2, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C4 alkoxy, benzyloxy, NH2, NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent Ci-C4 alkyl.
In another group of compounds, D1, D2, D3 and D4 each represent hydrogen;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl or a
5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X is X-3 or X-5; Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or CrC4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, OH, Ci-C4 alkyl or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d-C4 alkyl;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000048_0001
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be -(G^p-G^G3;
G1, G2 and G3 represent methylene;
p represents 1;
each R4, R5, R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, d-C4 alkoxy, C3-C4 alkenyloxy, d- alkoxycarbonyl, CHN-OH or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy and phenyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent Ci-C4 alkyl.
In one group of compounds In another group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, CrC8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, d-C4 alkoxy, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), COR1, OR2, SH, Ci-Ce alkylthio, Ci-C8 alkylsulphinyl, Ci-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR^OR1 or C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl and d-C4 haloalkyl;
X represents X-3, X-4 or X-5;
Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7;
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
each Y1, Y2, Y3, Y\ Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkyl, d-C4-haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy;
When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7, Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q' is Q-l', Q-2', Q-3', Q-4', Q-6' or Q-7', Y1' and Y2', Y2' and Y3', or Y3' and Y4' independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-Q alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, Ci-G, haloalkoxy and Ci-Q alkylthio;
When Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocydic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, C1-C4 alkyl, d-Q haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q is Q-l', Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocydic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000050_0001
when Q' is Q-9' and L4 is C-D4, then R12 and D4 together may be -(G -G2-G3'
G1, G2 and G3 represent C(R21)2, wherein each R21 independently of one another represents hydrogen, halogen, d-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy or Ci-C4 haloalkoxy;
Each p independently of one another represents 1 or 2;
each R1 independently of one another represents hydrogen, d-C4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy; each R2 independently of one another represents hydrogen, d-C8 alkyl, Ci-Cs haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy;
each R3 independently of one another represents hydrogen or d-C4 alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR^OR1 or CR^-OR2, wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, d-C4 haloalkoxy and NH2;
Each R6 and R7 independently of one another represent hydrogen, halogen, methyl or halomethyl;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH,
CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 alkoxycarbonyl, C3-C6 cydoalkyi, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the heterocycle is substituted by one or more d-C4 alkyl;
each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH,
Ci-C4 alkyl, Ci-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
R12 and R12' independently of one another represent hydrogen, Ci-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cydoalkyi, phenyl, pyridyl, or (R20)carbonyl(d-C4 alkyl), wherein the alkyl, alkenyl, alkynyl, cydoalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g. one to five groups, independently selected from halogen, CN, OR2, NH2, NH-Ci-C8 alkyl, N(d-C8 alkyl)2, Ci-C4 alkyl, d-C4 haloalkyl, C3-C6 cydoalkyi and pyridyl;
R13 and R13' independently of one another represent Ci-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy;
In another group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, CN, d-C4 alkyl, Ci-C4 alkoxy, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C4 alkoxy, d-C4 alkyl and Ci-C4 haloalkyl;
X represents X-3 or X-5; Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7; Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d- C4 alkyl;
each Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
each Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l or Q-3 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q' is Q-Γ or Q-3' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may
Figure imgf000052_0001
G1, G2 and G3 represent C(R21)2;
each R21 independently of one another represents hydrogen or d-C4 alkyl;
Each p independently of one another represents 1 or 2;
each R4 and R5 independently of one another represent hydrogen, d-C4 alkyl or Ci-C4 alkoxycarbonyl;
each R6 and R7 represent hydrogen; each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl, and wherein the heterocycle is substituted by one or more d-C4 alkyl;
R12 and R12' independently of one another represent hydrogen or d-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
In another group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or Ci-C4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d- C4 alkyl;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl; when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may b
Figure imgf000054_0001
G1, G2 and G3 represent methylene;
p represents 1;
each R4 and R5 independently of one another represent hydrogen or Ci-C2
alkoxycarbonyl;
each R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, C2-C4 alkenyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, CONH2, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C4 alkoxy, benzyloxy, NH2, NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
In another group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9'; Y1, Y2, Υ3, Y1', Y2' and Y3' independently of one another represent hydrogen or CrC4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, OH, Ci-C4 alkyl, d- C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000055_0001
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be -(G^p-G^G3;
G1, G2 and G3 represent methylene;
p represents 1;
each R4, R5, R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, d-d alkoxy, C3-C4 alkenyloxy, d-d alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, CN, NH2, NHCOphenyl, d-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by d-C4 alkyl;
R12 and R12' independently of one another represent d-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, d-C4 alkyl or C3-C6 alkynyl.
In another group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, d-C4 alkyl, CN or d-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, CrC4 alkoxy and Ci-C4 haloalkoxy;
D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, CrC8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), COR1, OR2, SH, d-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8
alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R1, CON(R3)2, NR^OR1 or CR^-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, Ci-C4 alkyl and Ci-C4 haloalkyl;
X represents X-3, X-4 or X-5;
Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7;
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C4 alkyl, d-C4-haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy;
When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7, Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q' is Q-l', Q-2', Q-3', Q-4', Q-6' or Q-7', Y1' and Y2', Y2' and Y3', or Y3' and Y4' independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-Q alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and Ci-Q alkylthio;
When Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, C1-C4 alkyl, d-Q haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q is Q-l', Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000057_0001
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be -(G -G2-G3'
G1, G2 and G3 represent C(R21)2, wherein each R21 independently of one another represents hydrogen, halogen, d-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy or Ci-C4 haloalkoxy;
Each p independently of one another represents 1 or 2;
each R1 independently of one another represents hydrogen, d-C4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy; each R2 independently of one another represents hydrogen, d-C8 alkyl, Ci-Cs haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy;
each R3 independently of one another represents hydrogen or d-C4 alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, d-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR^OR1 or CR^-OR2, wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, d-C4 haloalkoxy and NH2;
Each R6 and R7 independently of one another represent hydrogen, halogen, methyl or halomethyl;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH,
CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyi, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the heterocycle is substituted by one or more d-C4 alkyl;
each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH,
Ci-C4 alkyl, Ci-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
R12 and R12' independently of one another represent hydrogen, Ci-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyi, phenyl, pyridyl, or (R20)carbonyl(d-C4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g. one to five groups, independently selected from halogen, CN, OR2, NH2, NH-Ci-C8 alkyl, N(d-C8 alkyl)2, Ci-C4 alkyl, d-C4 haloalkyl, C3-C6 cycloalkyi and pyridyl;
R13 and R13' independently of one another represent Ci-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy.
In another group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, CN or Ci-C4 alkoxy;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X represents X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7; Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d- C4 alkyl;
each Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
each Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l or Q-3 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q' is Q-Γ or Q-3' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may
Figure imgf000059_0001
G1, G2 and G3 represent C(R21)2;
each R21 independently of one another represents hydrogen or d-C4 alkyl;
Each p independently of one another represents 1 or 2; each R4 and R5 independently of one another represent hydrogen, CrC4 alkyi or Ci-C4 alkoxycarbonyl;
each R6 and R7 represent hydrogen;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC4 alkyi, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(Ci-C4 alkyi), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyi), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyi are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyi, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyi), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl, and wherein the heterocycle is substituted by one or more d-C4 alkyi;
R12 and R12' independently of one another represent hydrogen or d-C4 alkyi;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyi or C3-C6 alkynyl.
In another group of compounds, D1, D2, D3 and D4 each represent hydrogen;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyi, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C4 alkoxy, Ci-C4 alkyi and Ci-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or C1-C4 alkyi;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyi, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d- C4 alkyi;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may b
Figure imgf000061_0001
G1, G2 and G3 represent methylene;
p represents 1;
each R4 and R5 independently of one another represent hydrogen or Ci-C2
alkoxycarbonyl;
each R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, C2-C4 alkenyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, CONH2, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C4 alkoxy, benzyloxy, NH2, NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
In another group of compounds, D1, D2, D3 and D4 each represent hydrogen;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d- C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5; Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or CrC4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, OH, Ci-C4 alkyl or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d-C4 alkyl;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000062_0001
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be -(G^p-G^G3;
G1, G2 and G3 represent methylene;
p represents 1;
each R4, R5, R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, d-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, NH2, NHCOphenyl, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
In another group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, d-C8 alkyl, C3-C8 cycloalkyi, C2-C8 alkenyl, C2-C8 alkynyl, d-C4 alkoxy, Ci-C4 alkylthio, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), COR1, OR2, SH, d-C8 alkylthio, C1-C3 alkylsulphinyl, C1-C3
alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R1, CON(R3)2, NR^OR1 or CR^-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl and Ci-C4 haloalkyl;
X represents X-3, X-4 or X-5;
Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7;
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, C2-C6 alkynyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7, Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C, alkyl, d-C4 haloalkyl, Q-C, alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q' is Q-l', Q-2', Q-3', Q-4', Q-6' or Q-7', Y1' and Y2', Y2' and Y3', or Y3' and Y4' independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C, alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio; When Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q is Q-l', Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, Ci-C4 alkyl, d-C4 haloalkyl, d-C4 alkoxy, d-C4 haloalkoxy and d-C4 alkylthio;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12 and D4 together may b
Figure imgf000064_0001
G1, G2 and G3 represent C(R21)2, wherein each R21 independently of one another represents hydrogen, halogen, d-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy or Ci-C4 haloalkoxy;
Each p independently of one another represents 1 or 2;
each R1 independently of one another represents hydrogen, d-C4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy; each R2 independently of one another represents hydrogen, d-C8 alkyl, Ci-Cs haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and d-C4 haloalkoxy;
each R3 independently of one another represents hydrogen or d-C4 alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR^OR1 or CR^-OR2, wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, d-C4 haloalkoxy and NH2; Each R6 and R7 independently of one another represent hydrogen, halogen, methyl or halomethyl;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyi, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the heterocycle is substituted by one or more d-C4 alkyl;
each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, Ci-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
R12 and R12' independently of one another represent hydrogen, Ci-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyi, phenyl, pyridyl, or (R20)carbonyl(d-C4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g. one to five groups, independently selected from halogen, CN, OR2, NH2, NH-Ci-C8 alkyl, N(d-C8 alkyl)2, Ci-C4 alkyl, d-C4 haloalkyl, C3-C6 cycloalkyi and pyridyl;
R13 and R13' independently of one another represent Ci-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy.
Preferably in this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, Ci-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy, d-C4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, Ci-C4 alkoxy, Ci-C4 alkyl and d-C4 haloalkyl;
X represents X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7; Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, C2-C8 alkynyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d-C4 alkyl;
each Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
each Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l or Q-3 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q' is Q-Γ or Q-3' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may
Figure imgf000066_0001
G1, G2 and G3 represent C(R21)2;
each R21 independently of one another represents hydrogen or d-C4 alkyl;
Each p independently of one another represents 1 or 2;
each R4 and R5 independently of one another represent hydrogen, d-C4 alkyl or Ci-C4 alkoxycarbonyl;
each R6 and R7 represent hydrogen; each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from 0 and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl, and wherein the heterocycle is substituted by one or more d-C4 alkyl;
R12 and R12' independently of one another represent hydrogen or d-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
Mpre preferably in this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, d-d alkyl, C2-C4 alkynyl, d-C4 alkoxy, d-C4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, d-C4 alkoxy, d-C4 alkyl and d-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen, halogen, d-C4 alkyl, C2-C8 alkynyl, d-C4 alkoxy or Ci-C4 alkylthio;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, d-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from d- alkyl;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000068_0001
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be -(G^p-G^G3;
G1, G2 and G3 represent methylene;
p represents 1;
each R4 and R5 independently of one another represent hydrogen or Ci-C2
alkoxycarbonyl;
each R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, C2-C4 alkenyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, CONH2, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, d-C4 alkoxy, benzyloxy, NH2, NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
Even more preferably in this group of compounds, D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, Ci-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy, Ci-C4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5; Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen, halogen, C1-C4 alkyl, C2-C4 alkynyl, Ci-C4 alkoxy, Ci-C4 alkylthio;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, C2-C8 alkynyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from C1-C4 alkyl;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may b
Figure imgf000069_0001
G1, G2 and G3 represent methylene;
p represents 1;
each R4, R5, R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, NH2/ NHCOphenyl, d-C, alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl. Yet more preferably in this group of compounds, each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, Ci-Q alkyl, C2-C4 alkynyl, Ci-C4 alkoxy or Ci-C4 alkylthio.
Yet more preferably again in this group of compounds, each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
Even more preferably again in this group of compounds each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
Most preferably in this group of compounds, each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4,
Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, methoxy or methylthio.
Most preferably in this group of compounds, R13 and R13' independently of one another represent hydrogen, methyl or ethynyl.
In another group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, hydrogen, Ci-C4 alkyl, C2-C4 alkynyl, CN, Ci-C4 alkylthio or d-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, d-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, d-C4 alkylthio, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms (e.g. a heterocycle as defined herein, preferably furanyl, thiophenyl or pyrazolyl), COR1, OR2, SH, d-C8 alkylthio, Ci-C8 alkylsulphinyl, d-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR^OR1 or C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, Ci-C4 alkyl and Ci-C4 haloalkyl;
X represents X-3, X-4 or X-5;
Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7;
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7; Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and
Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9';
each Y1, Y2, Y3, Y4', Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, G-C4 alkyl, C2-C4 alkynyl, Ci-C4 alkoxy, G-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
When Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7, Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, G-C4 haloalkyl, Q-G, alkoxy, Q-G, haloalkoxy and Q-G, alkylthio;
When Q' is Q-l', Q-2', Q-3', Q-4', Q-6' or Q-7', Y1' and Y2', Y2' and Y3', or Y3' and Y4' independently of the other, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R3), and wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, G-G, alkyl, Q-G, haloalkyl, G-C4 alkoxy, G-C4 haloalkoxy and G-C4 alkylthio;
When Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy, G-C4 haloalkoxy and G-C4 alkylthio;
When Q is Q-l', Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, OH, G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy, G-C4 haloalkoxy and G-C4 alkylthio;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000071_0001
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be -(G^p-G^G3' G1, G2 and G3 represent C(R21)2, wherein each R21 independently of one another represents hydrogen, halogen, d-C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy or Ci-C4 haloalkoxy;
Each p independently of one another represents 1 or 2;
each R1 independently of one another represents hydrogen, d-C4 alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups independently selected from halogen and Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy; each R2 independently of one another represents hydrogen, CrC8 alkyl, d-C8 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, d-C8 haloalkynyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, d- alkyl, d-d-haloalkyl, d-d alkoxy and d-d haloalkoxy;
each R3 independently of one another represents hydrogen or d-d alkyl; wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-l, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, CHO, Ci-d alkyl, C2-C4 alkenyl, C2-C4 alkynyl, d-C4 alkoxy, C3-C4 alkenyloxy, d-C4 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2, NR^OR1 or CR^-OR2, wherein the alkyl, alkenyl, alkynyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, Ci-d alkyl, Ci-d haloalkyl, Ci-d alkoxy, d-C4 haloalkoxy and NH2;
Each R6 and R7 independently of one another represent hydrogen, halogen, methyl or halomethyl;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-d alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci-d alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(d-C4 alkyl), CON(d-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from O and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-d haloalkyl, Ci-d alkoxy, benzyloxy, NH2, NHCO(Ci-d alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl and wherein the heterocycle is substituted by one or more d-C4 alkyl; each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl, Ci-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
R12 and R12' independently of one another represent hydrogen, C1-C3 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C3 cycloalkyi, phenyl, pyridyl, or (R20)carbonyl(d-C4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups , e.g. one to five groups, independently selected from halogen, CN, OR2, NH2, NH-Ci-Cs alkyl, N(d-C8 alkyl)2, Ci-C4 alkyl, d-G, haloalkyl, C3-C6 cycloalkyi and pyridyl;
R13 and R13' independently of one another represent Ci-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy.
More preferably in this group of compounds, D1, D2, D3 and D4 independently of one another represent hydrogen, Ci-C4 alkyl, C2-C4 alkynyl, CN, d-C4 alkylthio or Ci-C4 alkoxy;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy, Ci-C4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, d-C4 alkoxy, d-C4 alkyl and d-C4 haloalkyl;
X represents X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5 or C=CR6R7;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y\ Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, C2-C4 alkynyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups independently selected from d-C4 alkyl;
each Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
each Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from halogen, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l or Q-3 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q' is Q-Γ or Q-3' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached can form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups, e.g. one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may
Figure imgf000074_0001
G1, G2 and G3 represent C(R21)2;
each R21 independently of one another represents hydrogen or d-C4 alkyl;
Each p independently of one another represents 1 or 2;
each R4 and R5 independently of one another represent hydrogen, d-C4 alkyl or Ci-C4 alkoxycarbonyl;
each R6 and R7 represent hydrogen;
each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, CHO, d-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci-C4 alkoxycarbonyl, C3-C6 cycloalkyl, CONH2, CONH(Ci-C4 alkyl), CON(Ci-C4 alkyl)2, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl, CHN-OH, phenyl or 5-membered heterocycle containing two or four heteroatoms independently selected from O and N providing that the heterocycle does not contain adjacent oxygen atoms, wherein the alkyl are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy, benzyloxy, NH2, NHCO(Ci-C4 alkyl), NHCO(C2-C4 alkenyl), NHCO(C2-C4 alkynyl), NHCOphenyl and phenyl, and wherein the heterocycle is substituted by one or more d-C4 alkyl;
R12 and R12' independently of one another represent hydrogen or d-C4 alkyl; R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
Even more preferably in this group of compounds, D1, D2, D3 and D4 each represent hydrogen, halogen, Ci-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy or Ci-C4 alkylthio;
D5 and D6 independently of one another represent hydrogen, Ci-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy, Ci-C4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, Ci-C4 alkoxy, Ci-C4 alkyl and Ci-C4 haloalkyl;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q-2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q-2', Q-3' and Q-9';
each Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or Ci-C4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, Ci-C4 alkyl, C2-C4 alkynyl, Ci-C4 alkoxy, Ci-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from Ci-C4 alkyl;
when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring; When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12 and D4 together may b
Figure imgf000076_0001
G1, G2 and G3 represent methylene;
p represents 1;
each R4 and R5 independently of one another represent hydrogen or Ci-C2
alkoxycarbonyl;
each R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, G- G alkyl, C2-C4 alkenyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, G-G, alkoxycarbonyl, CONH2, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from OH, G-C4 alkoxy, benzyloxy, NH2, NHCOphenyl and phenyl and wherein the tetrazolyl is optionally substituted by G-C4 alkyl;
R12 and R12' independently of one another represent G-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, G-C4 alkyl or C3-C6 alkynyl.
More preferably again in this group of compounds, D1, D2, D3 and D4 each represent hydrogen, halogen, G-C4 alkyl, C2-C4 alkynyl, G-C4 alkoxy or G-C4 alkylthio;
D5 and D6 independently of one another represent hydrogen, halogen, G-C4 alkyl, C2-
C4 alkynyl, G-C4 alkoxy, G-C4 alkylthio, phenyl or a 5-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the phenyl and heterocycle are optionally substituted by one or more groups, independently selected from halogen, G-C4 alkoxy, G-C4 alkyl and G-C4 haloalkyi;
X is X-3 or X-5;
Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5;
Z4 and Z12 represent CR8R9 or C=CR6R7;
Q is selected from the group consisting of Q-l, Q2, Q-3 and Q-9;
Q' is selected from the group consisting of Q- , Q2', Q-3' and Q-9';
Y1, Y2, Y3, Y1', Y2' and Y3' independently of one another represent hydrogen or G-C4 alkyl;
each Y4 and Y4' independently of one another represent hydrogen, halogen, OH, G-C4 alkyl, C2-C4 alkynyl, G-C4 alkoxy, G-C4 alkylthio or phenyl, wherein the phenyl may be optionally substituted by one or more groups, e.g. one to five groups, independently selected from G-C4 alkyl; when Q is Q-2, Y2 and Y3, together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2 and Y3 is optionally substituted by one or more groups independently selected from d-C4 alkyl;
when Q' is Q-2', Y2' and Y3', together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y2' and Y3' is optionally substituted by one or more groups independently selected from d-C4 alkyl;
When Q is Q-3, Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q' is Q-3', Y1' and D4 together with the fragment to which they are attached can form a partially or fully unsaturated 6-membered carbocyclic ring;
When Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may b
Figure imgf000077_0001
G1, G2 and G3 represent methylene;
p represents 1;
each R4, R5, R6 and R7 represents hydrogen;
each R8 and R9 independently of one another represent hydrogen, CN, OH, CHO, d- C4 alkyl, Ci-C4 alkoxy, C3-C4 alkenyloxy, Ci-C4 alkoxycarbonyl, CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl are optionally substituted by one or more groups independently selected from, OH, CN, NH2, NHCOphenyl, d-G, alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, benzyloxyl and phenyl, and wherein the tetrazolyl is optionally substituted by Ci-C4 alkyl;
R12 and R12' independently of one another represent Ci-C4 alkyl;
R13 and R13' independently of one another represent hydrogen, Ci-C4 alkyl or C3-C6 alkynyl.
Yet more preferably in this group of compounds, each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, Ci-C4 alkyl, C2-C4 alkynyl, d-C4 alkoxy or Ci-C4 alkylthio.
Yet more preferably again in this group of compounds, each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.
Even more preferably again in this group of compounds each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, chloro, methyl, ethynyl, methoxy or methylthio.
Most preferably in this group of compounds, each D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4,
Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, methoxy or methylthio. Most preferably in this group of compounds, R13 and R13' independently of one another represent hydrogen, methyl or ethynyl.
Novel compounds of formula (I) also form part of the present invention. Accordingly, in a further aspect the invention provides a compound of formula I as defined as defined above, wherein X is X-3, X-4 or X-5 and the compound of formula I is not a compound of formul
Figure imgf000078_0001
wherein Ra is hydrogen or phenyl, Rb is primary alkyl and n is 4 or 5;
and the compound of formula I is not a compound of formula I"
Figure imgf000078_0002
wherein each Rc is independently hydrogen or methyl;
and the compound of formula I is not a compound of formula I"'a, I'"b or I'"c
Figure imgf000078_0003
Figure imgf000079_0001
Figure imgf000079_0002
and the com ound of formula I is not a compound of formula I"
Figure imgf000079_0003
wherein
n is 3, Rd and Re are both methyl, Rf and R9 are both hydrogen; or
n is 3, Rd and Re are both paramethoxyphenyl, Rf and R9 are both hydrogen; or n is 4, Rd and Re are both hydrogen, Rf and R9 are both hydrogen; or
n is 4 , Rd and Re are both paraformylphenyl, Rf and R9 are both hydrogen; or
d and Re are both
Figure imgf000079_0004
Rf and R9 are both hydrogen; or
n is 4, Rd and Re are both n-butyl, Rf and R9 are both hydrogen; or
n is 4, Rd and Re are both hydrogen, Rf and R9 are both hydrogen; or
n is 4, Rd and Re are both parahydroxyphenyl, Rf and R9 are both hydrogen; or n is 4, Rd and Re are both paramethoxyphenyl, Rf and R9 are both hydrogen; or n is 5, Rd and Re are both n-butyl, Rf and R9 are both hydrogen; or
n is 4, Rd and Re are both hydrogen, Rf and R9 are both paramethoxyphenyl
In one group of compounds of the invention, when Q is Q-4, Q-7 or Q-8 and L1 is C- D1, and Q is not Q-1, then Y1 and D1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, CrC4 alkyl, Ci-C4 haloalkyl, C1-C4 alkoxy and d-C4 haloalkoxy (i.e. Y1 and D1 do not together form a ring when Q is Q-1);
R8 represents hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce alkenyl, d- C6alkynyl, Ci-C6alkoxy, Ci-Ce alkenyloxy, Ci-C6alkynyloxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, C3-C6cycloalkyl, phenyl or 5- or 6-membered heterocycle containing one to three
heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, OH, CN, C1-C4 alkyl, Ci-G, haloalkyl, Ci-G, alkoxy, Ci-G, haloalkoxy, Ci-G, alkylthio and Ci-G, haloalkylthio;
when Q is Q-1 Y4 represents hydrogen, halogen, CN, N02, Ci-Q alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, COR1, OR2, SH, Ci-Ce alkylthio, Ci-Ce alkylsulphinyl, Ci-Cs alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, and phenyl are optionally substituted by one or more groups e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OR2, Ci-C4 alkyl, d-C4 haloalkyl and d- C4 alkylthio;
or Y4 together with Y3 and together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y3 and Y4 is optionally substituted by one or more groups e.g. one to five groups, independently selected from halogen, CN, NH2, N02, OH, d- C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio.
In one group of compounds one of Q and Q' together with the fragment to which it is attached is not phenanthroline. In one group of compounds R8 and R9 cannot both be alkoxycarbonyl. In one group of compounds when Q is Q-1 then Y4 is not a heterocyclic ring. In one group of compounds one of Q and Q' together with the fragment to which it is attached is not phenanthroline, R8 and R9 cannot both be alkoxycarbonyl, and when Q is Q-1 then Y4 is not a heterocyclic ring. The preferred substituent definitions of the novel compounds of the invention are the same as described above.
Compounds of formula Γ are diclosed in JP10113541. Compounds of formula I" are disclosed in Inorganic Chemistry, 1983, 22(1), 171-174. Compounds of formula Γ" are disclosed in Journal of Medicinal Chemistry, 1975, 18(11), 1088-94. Compounds of formula I"" are disclosed in Inorganic Chemistry, 2010, 49(9), 4023-4035; e-EROS Encyclopedia of Reagents for Organic Synthesis (2001), publisher: John Wiley and Sons, Ltd, Chichester, UK; Journal of the American Chemical Society, 1999, 121(15), 3684-3692; Chemistry Letters, 1997, 7, 615-616; Analytica Chemica Acta, 1996, 329(1-2), 57-64; Angewandte Chemie, International Edition in English, 1996, 35(8), 906-909; Journal of the American Chemical Society, 1996, 118(13), 3285-6; New Journal of Chemistry, 1995, 19(4), 409-26; Pure and Applied Chemistry 1995, 67(2), 233-40; Chemistry Letters, 1994, 3, 397-400; Journal of the American Chemical Society, 1993, 115(24), 11237-44; Journal of the Chemical Society, Chemical Communications, 1993, 9, 801-4; New Journal of Chemistry, 1992, 16(10), 931-42; Tetrahedron Letters, 1992, 33(25), 3625-8; Angewandte Chemie, 1989, 101(2), 192-4.
Optionally the invention may not include compounds in which L5 and at least one of L1 and L2 is nitrogen, and/or L6 is nitrogen and at least one of L3 and L4 is nitrogen, e.g. the 6-membered heterocycles either side of X may not include a =N-C=C-N= motif. Optionally the invention may not claim compounds of formula I"" in which Rd and Re are hydrogen or hydrocarbon and Rf and R9 are hydrogen. Optionally the invention may not claim compounds of formula I in which, when X is X-3, R8 and R9 together are not C=0. Reference is made here to US3498981, WO2009/047584 and JP10113541, however none of these documents disclose compounds of the invention.
Figure imgf000081_0001
(Int-1 )
wherein X' represents -CH=CH-CH2- or CH2-CH=CH- and Q, Q', L1, L2, L3 L4, L5 and L6 are as defined for compounds of formula (I) or a salt or N-oxide thereof. The preferred definitions of Q, Q', L1, L2, L3 L4, L5 and L6 defined in respect of compounds of formula (I) also apply to compounds of formula (Int-1).
In a further aspect, the invention provides a compound of formula Int-2
Figure imgf000082_0001
(lnt-2)
wherein L1, L2, L3 L4, L5, L6 and X are as defined herein for compounds of formula (I); or a salt or N-oxide thereof. The preferred definitions of L1, L2, L3 L4, L5, L6 and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-2). Particularly preferred are compounds of formula (int-2) where L1, L2, L3 L4, L5 and L6 are each C-H.
In a further aspect, the invention provides a compound of formula Int-3
Figure imgf000082_0002
(lnt-3)
wherein L1, L2, L3 L4, L5, L6 , Q and X are as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferred definitions of L1, L2, L3 L4, L5, L6 , Q and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-3).
In a further aspect, the invention provides a compound of formula Int-4
Figure imgf000082_0003
(lnt-4)
wherein L1, L2, L3 L4, L5, L6 , Q and X are as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferred definitions of L1, L2, L3 L4, L5, L6 , Q and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-4).
In a further aspect, the invention provides a compound of formula Int-5
Figure imgf000082_0004
(lnt-5) wherein L1, L2, L3 L4, L5, L6 , Q and X are as defined for compounds of formula (I) and R29 is is a halogen in particular chlorine, bromine or iodine; or a salt or N-oxide thereof. The preferred definitions of L1, L2, L3 L4, L5, L6 , Q and X defined in respect of compounds of formula (I) also apply to compounds of formula (Int-4).
The compounds of formula (I) may exist as different geometric or optical isomers or in different tautomeric forms. These may be separated and isolated by well-known (usually chromatographic) techniques, and all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms, such as deuterated compounds, are part of the present invention. The invention also includes salts and N-oxides of compounds of the invention.
Table 1 illustrates embodiments of
Figure imgf000083_0001
The compounds in table 2 illustrate compounds of formula (I).
83
Figure imgf000084_0001
84
Figure imgf000085_0001
85
Figure imgf000086_0001
Figure imgf000087_0001
Table 2
Compound X
Figure imgf000088_0001
001 Al-1 — CH2CH2CH2- Al-1
002 Al-1 — CH2CH2CH2- Al-2
003 Al-1 — CH2CH2CH2- Al-3
004 Al-1 — CH2CH2CH2- Al-4
005 Al-1 — CH2CH2CH2- Al-5
006 Al-1 — CH2CH2CH2- Al-6
007 Al-1 — CH2CH2CH2- Al-7
008 Al-1 — CH2CH2CH2- Al-8
009 Al-1 — CH2CH2CH2- Al-9
010 Al-1 — CH2CH2CH2- Al-10
Oil Al-1 — CH2CH2CH2- A2-1
012 Al-1 — CH2CH2CH2- A2-2
013 Al-1 — CH2CH2CH2- A3-1
014 Al-1 — CH2CH2CH2- A3-2
015 Al-1 — CH2CH2CH2- A3-3
016 Al-1 — CH2CH2CH2- A3-4
017 Al-1 — CH2CH2CH2- A3-5
018 Al-1 — CH2CH2CH2- A3-6
019 Al-1 — CH2CH2CH2- A3-7
020 Al-1 — CH2CH2CH2- A3-8
021 Al-1 — CH2CH2CH2- A3-9
022 Al-1 — CH2CH2CH2- A3-10
023 Al-1 — CH2CH2CH2- A3-11
024 Al-1 — CH2CH2CH2- A3-12
025 Al-1 — CH2CH2CH2- A3-13
026 Al-1 — CH2CH2CH2- A3-14
027 Al-1 — CH2CH2CH2- A3-15
028 Al-1 — CH2CH2CH2- A4-1
029 Al-1 — CH2CH2CH2- A4-2
030 Al-1 — CH2CH2CH2- A4-3
031 Al-1 — CH2CH2CH2- A4-4
032 Al-1 — CH2CH2CH2- A4-5
033 Al-1 — CH2CH2CH2- A4-6
034 Al-1 — CH2CH2CH2- A4-7
035 Al-1 — CH2CH2CH2- A4-8
036 Al-1 — CH2CH2CH2- A4-9 Compound X 1 | 4
037 Al-1 — CH2CH2CH2- A4-10
038 Al-1 — CH2CH2CH2- A4-11
039 Al-1 — CH2CH2CH2- A5-1
040 Al-1 — CH2CH2CH2- A5-2
041 Al-1 — CH2CH2CH2- A6-1
042 Al-1 — CH2CH2CH2- A6-2
043 Al-1 — CH2CH2CH2- A6-3
044 Al-1 — CH2CH2CH2- A6-4
045 Al-1 — CH2CH2CH2- A6-5
046 Al-1 — CH2CH2CH2- A7-1
047 Al-1 — CH2CH2CH2- A7-2
048 Al-1 — CH2CH2CH2- A8-1
049 Al-1 — CH2CH2CH2- A8-2
050 Al-1 — CH2CH2CH2- A8-3
051 Al-1 — CH2CH2CH2- A8-4
052 Al-1 — CH2CH2CH2- A8-5
053 Al-1 — CH2CH2CH2- A8-6
054 A2-1 — CH2CH2CH2- Al-2
055 A2-1 — CH2CH2CH2- Al-3
056 A2-1 — CH2CH2CH2- Al-4
057 A2-1 — CH2CH2CH2- Al-5
058 A2-1 — CH2CH2CH2- Al-6
059 A2-1 — CH2CH2CH2- Al-7
060 A2-1 — CH2CH2CH2- Al-8
061 A2-1 — CH2CH2CH2- Al-9
062 A2-1 — CH2CH2CH2- Al-10
063 A2-1 — CH2CH2CH2- A2-1
064 A2-1 — CH2CH2CH2- A2-2
065 A2-1 — CH2CH2CH2- A3-1
066 A2-1 — CH2CH2CH2- A3-2
067 A2-1 — CH2CH2CH2- A3-3
068 A2-1 — CH2CH2CH2- A3-4
069 A2-1 — CH2CH2CH2- A3-5
070 A2-1 — CH2CH2CH2- A3-6
071 A2-1 — CH2CH2CH2- A3-7
072 A2-1 — CH2CH2CH2- A3-8
073 A2-1 — CH2CH2CH2- A3-9 Compound X I | 4
074 A2-1 — CH2CH2CH2" A3-10
075 A2-1 — CH2CH2CH2" A3-11
076 A2-1 — CH2CH2CH2" A3-12
077 A2-1 — CH2CH2CH2" A3-13
078 A2-1 — CH2CH2CH2" A3-14
079 A2-1 — CH2CH2CH2" A3-15
080 A2-1 — CH2CH2CH2" A4-1
081 A2-1 — CH2CH2CH2" A4-2
082 A2-1 — CH2CH2CH2" A4-3
083 A2-1 — CH2CH2CH2" A4-4
084 A2-1 — CH2CH2CH2" A4-5
085 A2-1 — CH2CH2CH2" A4-6
086 A2-1 — CH2CH2CH2" A4-7
087 A2-1 — CH2CH2CH2" A4-8
088 A2-1 — CH2CH2CH2" A4-9
089 A2-1 — CH2CH2CH2" A4-10
090 A2-1 — CH2CH2CH2" A4-11
091 A2-1 — CH2CH2CH2" A5-1
092 A2-1 — CH2CH2CH2" A5-2
093 A2-1 — CH2CH2CH2" A6-1
094 A2-1 — CH2CH2CH2" A6-2
095 A2-1 — CH2CH2CH2" A6-3
096 A2-1 — CH2CH2CH2" A6-4
097 A2-1 — CH2CH2CH2" A6-5
098 A2-1 — CH2CH2CH2" A7-1
099 A2-1 — CH2CH2CH2" A7-2
100 A2-1 — CH2CH2CH2" A8-1
101 A2-1 — CH2CH2CH2" A8-2
102 A2-1 — CH2CH2CH2" A8-3
103 A2-1 — CH2CH2CH2" A8-4
104 A2-1 — CH2CH2CH2" A8-5
105 A2-1 — CH2CH2CH2" A8-6
106 A3-2 — CH2CH2CH2" Al-2
107 A3-2 — CH2CH2CH2" Al-3
108 A3-2 — CH2CH2CH2" Al-4
109 A3-2 — CH2CH2CH2" Al-5
110 A3-2 — CH2CH2CH2" Al-6 Compound X I | 4
111 A3-2 — CH2CH2CH2" Al-7
112 A3-2 — CH2CH2CH2" Al-8
113 A3-2 — CH2CH2CH2" Al-9
114 A3-2 — CH2CH2CH2" Al-10
115 A3-2 — CH2CH2CH2" A2-2
116 A3-2 — CH2CH2CH2" A3-1
117 A3-2 — CH2CH2CH2" A3-2
118 A3-2 — CH2CH2CH2" A3-3
119 A3-2 — CH2CH2CH2" A3-4
120 A3-2 — CH2CH2CH2" A3-5
121 A3-2 — CH2CH2CH2" A3-6
122 A3-2 — CH2CH2CH2" A3-7
123 A3-2 — CH2CH2CH2" A3-8
124 A3-2 — CH2CH2CH2" A3-9
125 A3-2 — CH2CH2CH2" A3-10
126 A3-2 — CH2CH2CH2" A3-11
127 A3-2 — CH2CH2CH2" A3-12
128 A3-2 — CH2CH2CH2" A3-13
129 A3-2 — CH2CH2CH2" A3-14
130 A3-2 — CH2CH2CH2" A3-15
131 A3-2 — CH2CH2CH2" A4-1
132 A3-2 — CH2CH2CH2" A4-2
133 A3-2 — CH2CH2CH2" A4-3
134 A3-2 — CH2CH2CH2" A4-4
135 A3-2 — CH2CH2CH2" A4-5
136 A3-2 — CH2CH2CH2" A4-6
137 A3-2 — CH2CH2CH2" A4-7
138 A3-2 — CH2CH2CH2" A4-8
139 A3-2 — CH2CH2CH2" A4-9
140 A3-2 — CH2CH2CH2" A4-10
141 A3-2 — CH2CH2CH2" A4-11
142 A3-2 — CH2CH2CH2" A5-1
143 A3-2 — CH2CH2CH2" A5-2
144 A3-2 — CH2CH2CH2" A6-1
145 A3-2 — CH2CH2CH2" A6-2
146 A3-2 — CH2CH2CH2" A6-3
147 A3-2 — CH2CH2CH2" A6-4 Compound X I | 4
148 A3-2 — CH2CH2CH2" A6-5
149 A3-2 — CH2CH2CH2" A7-1
150 A3-2 — CH2CH2CH2" A7-2
151 A3-2 — CH2CH2CH2" A8-1
152 A3-2 — CH2CH2CH2" A8-2
153 A3-2 — CH2CH2CH2" A8-3
154 A3-2 — CH2CH2CH2" A8-4
155 A3-2 — CH2CH2CH2" A8-5
156 A3-2 — CH2CH2CH2" A8-6
157 A4-2 — CH2CH2CH2" Al-2
158 A4-2 — CH2CH2CH2" Al-3
159 A4-2 — CH2CH2CH2" Al-4
160 A4-2 — CH2CH2CH2" Al-5
161 A4-2 — CH2CH2CH2" Al-6
162 A4-2 — CH2CH2CH2" Al-7
163 A4-2 — CH2CH2CH2" Al-8
164 A4-2 — CH2CH2CH2" Al-9
165 A4-2 — CH2CH2CH2" Al-10
166 A4-2 — CH2CH2CH2" A2-2
167 A4-2 — CH2CH2CH2" A3-1
168 A4-2 — CH2CH2CH2" A3-3
169 A4-2 — CH2CH2CH2" A3-4
170 A4-2 — CH2CH2CH2" A3-5
171 A4-2 — CH2CH2CH2" A3-6
172 A4-2 — CH2CH2CH2" A3-7
173 A4-2 — CH2CH2CH2" A3-8
174 A4-2 — CH2CH2CH2" A3-9
175 A4-2 — CH2CH2CH2" A3-10
176 A4-2 — CH2CH2CH2" A3-11
177 A4-2 — CH2CH2CH2" A3-12
178 A4-2 — CH2CH2CH2" A3-13
179 A4-2 — CH2CH2CH2" A3-14
180 A4-2 — CH2CH2CH2" A3-15
181 A4-2 — CH2CH2CH2" A4-1
182 A4-2 — CH2CH2CH2" A4-2
183 A4-2 — CH2CH2CH2" A4-3
184 A4-2 — CH2CH2CH2" A4-4 Compound X I | 4
185 A4-2 — CH2CH2CH2" A4-5
186 A4-2 — CH2CH2CH2" A4-6
187 A4-2 — CH2CH2CH2" A4-7
188 A4-2 — CH2CH2CH2" A4-8
189 A4-2 — CH2CH2CH2" A4-9
190 A4-2 — CH2CH2CH2" A4-10
191 A4-2 — CH2CH2CH2" A4-11
192 A4-2 — CH2CH2CH2" A5-1
193 A4-2 — CH2CH2CH2" A5-2
194 A4-2 — CH2CH2CH2" A6-1
195 A4-2 — CH2CH2CH2" A6-2
196 A4-2 — CH2CH2CH2" A6-3
197 A4-2 — CH2CH2CH2" A6-4
198 A4-2 — CH2CH2CH2" A6-5
199 A4-2 — CH2CH2CH2" A7-1
200 A4-2 — CH2CH2CH2" A7-2
201 A4-2 — CH2CH2CH2" A8-1
202 A4-2 — CH2CH2CH2" A8-2
203 A4-2 — CH2CH2CH2" A8-3
204 A4-2 — CH2CH2CH2" A8-4
205 A4-2 — CH2CH2CH2" A8-5
206 A4-2 — CH2CH2CH2" A8-6
207 A5-1 — CH2CH2CH2" Al-2
208 A5-1 — CH2CH2CH2" Al-3
209 A5-1 — CH2CH2CH2" Al-4
210 A5-1 — CH2CH2CH2" Al-5
211 A5-1 — CH2CH2CH2" Al-6
212 A5-1 — CH2CH2CH2" Al-7
213 A5-1 — CH2CH2CH2" Al-8
214 A5-1 — CH2CH2CH2" Al-9
215 A5-1 — CH2CH2CH2" Al-10
216 A5-1 — CH2CH2CH2" A2-2
217 A5-1 — CH2CH2CH2" A3-1
218 A5-1 — CH2CH2CH2" A3-3
219 A5-1 — CH2CH2CH2" A3-4
220 A5-1 — CH2CH2CH2" A3-5
221 A5-1 — CH2CH2CH2" A3-6 Compound X I | 4
222 A5-1 — CH2CH2CH2" A3-7
223 A5-1 — CH2CH2CH2" A3-8
224 A5-1 — CH2CH2CH2" A3-9
225 A5-1 — CH2CH2CH2" A3-10
226 A5-1 — CH2CH2CH2" A3-11
227 A5-1 — CH2CH2CH2" A3-12
228 A5-1 — CH2CH2CH2" A3-13
229 A5-1 — CH2CH2CH2" A3-14
230 A5-1 — CH2CH2CH2" A3-15
231 A5-1 — CH2CH2CH2" A4-1
232 A5-1 — CH2CH2CH2" A4-3
233 A5-1 — CH2CH2CH2" A4-4
234 A5-1 — CH2CH2CH2" A4-5
235 A5-1 — CH2CH2CH2" A4-6
236 A5-1 — CH2CH2CH2" A4-7
237 A5-1 — CH2CH2CH2" A4-8
238 A5-1 — CH2CH2CH2" A4-9
239 A5-1 — CH2CH2CH2" A4-10
240 A5-1 — CH2CH2CH2" A4-11
241 A5-1 — CH2CH2CH2" A5-1
242 A5-1 — CH2CH2CH2" A5-2
243 A5-1 — CH2CH2CH2" A6-1
244 A5-1 — CH2CH2CH2" A6-2
245 A5-1 — CH2CH2CH2" A6-3
246 A5-1 — CH2CH2CH2" A6-4
247 A5-1 — CH2CH2CH2" A6-5
248 A5-1 — CH2CH2CH2" A7-1
249 A5-1 — CH2CH2CH2" A7-2
250 A5-1 — CH2CH2CH2" A8-1
251 A5-1 — CH2CH2CH2" A8-2
252 A5-1 — CH2CH2CH2" A8-3
253 A5-1 — CH2CH2CH2" A8-4
254 A5-1 — CH2CH2CH2" A8-5
255 A5-1 — CH2CH2CH2" A8-6
256 A6-5 — CH2CH2CH2" Al-2
257 A6-5 — CH2CH2CH2" Al-3
258 A6-5 — CH2CH2CH2" Al-4 Compound X I | 4
259 A6-5 — CH2CH2CH2" Al-5
260 A6-5 — CH2CH2CH2" Al-6
261 A6-5 — CH2CH2CH2" Al-7
262 A6-5 — CH2CH2CH2" Al-8
263 A6-5 — CH2CH2CH2" Al-9
264 A6-5 — CH2CH2CH2" Al-10
265 A6-5 — CH2CH2CH2" A2-2
266 A6-5 — CH2CH2CH2" A3-1
267 A6-5 — CH2CH2CH2" A3-3
268 A6-5 — CH2CH2CH2" A3-4
269 A6-5 — CH2CH2CH2" A3-5
270 A6-5 — CH2CH2CH2" A3-6
271 A6-5 — CH2CH2CH2" A3-7
272 A6-5 — CH2CH2CH2" A3-8
273 A6-5 — CH2CH2CH2" A3-9
274 A6-5 — CH2CH2CH2" A3-10
275 A6-5 — CH2CH2CH2" A3-11
276 A6-5 — CH2CH2CH2" A3-12
277 A6-5 — CH2CH2CH2" A3-13
278 A6-5 — CH2CH2CH2" A3-14
279 A6-5 — CH2CH2CH2" A3-15
280 A6-5 — CH2CH2CH2" A4-1
281 A6-5 — CH2CH2CH2" A4-3
282 A6-5 — CH2CH2CH2" A4-4
283 A6-5 — CH2CH2CH2" A4-5
284 A6-5 — CH2CH2CH2" A4-6
285 A6-5 — CH2CH2CH2" A4-7
286 A6-5 — CH2CH2CH2" A4-8
287 A6-5 — CH2CH2CH2" A4-9
288 A6-5 — CH2CH2CH2" A4-10
289 A6-5 — CH2CH2CH2" A4-11
290 A6-5 — CH2CH2CH2" A5-2
291 A6-5 — CH2CH2CH2" A6-1
292 A6-5 — CH2CH2CH2" A6-2
293 A6-5 — CH2CH2CH2" A6-3
294 A6-5 — CH2CH2CH2" A6-4
295 A6-5 — CH2CH2CH2" A6-5 Compound X I | 4
296 A6-5 — CH2CH2CH2" A7-1
297 A6-5 — CH2CH2CH2" A7-2
298 A6-5 — CH2CH2CH2" A8-1
299 A6-5 — CH2CH2CH2" A8-2
300 A6-5 — CH2CH2CH2" A8-3
301 A6-5 — CH2CH2CH2" A8-4
302 A6-5 — CH2CH2CH2" A8-5
303 A6-5 — CH2CH2CH2" A8-6
304 A7-1 — CH2CH2CH2" Al-2
305 A7-1 — CH2CH2CH2" Al-3
306 A7-1 — CH2CH2CH2" Al-4
307 A7-1 — CH2CH2CH2" Al-5
308 A7-1 — CH2CH2CH2" Al-6
309 A7-1 — CH2CH2CH2" Al-7
310 A7-1 — CH2CH2CH2" Al-8
311 A7-1 — CH2CH2CH2" Al-9
312 A7-1 — CH2CH2CH2" Al-10
313 A7-1 — CH2CH2CH2" A2-2
314 A7-1 — CH2CH2CH2" A3-1
315 A7-1 — CH2CH2CH2" A3-3
316 A7-1 — CH2CH2CH2" A3-4
317 A7-1 — CH2CH2CH2" A3-5
318 A7-1 — CH2CH2CH2" A3-6
319 A7-1 — CH2CH2CH2" A3-7
320 A7-1 — CH2CH2CH2" A3-8
321 A7-1 — CH2CH2CH2" A3-9
322 A7-1 — CH2CH2CH2" A3-10
323 A7-1 — CH2CH2CH2" A3-11
324 A7-1 — CH2CH2CH2" A3-12
325 A7-1 — CH2CH2CH2" A3-13
326 A7-1 — CH2CH2CH2" A3-14
327 A7-1 — CH2CH2CH2" A3-15
328 A7-1 — CH2CH2CH2" A4-1
329 A7-1 — CH2CH2CH2" A4-3
330 A7-1 — CH2CH2CH2" A4-4
331 A7-1 — CH2CH2CH2" A4-5
332 A7-1 — CH2CH2CH2" A4-6 Compound X 1 | 4
333 A7-1 — CH2CH2CH2" A4-7
334 A7-1 — CH2CH2CH2" A4-8
335 A7-1 — CH2CH2CH2" A4-9
336 A7-1 — CH2CH2CH2" A4-10
337 A7-1 — CH2CH2CH2" A4-11
338 A7-1 — CH2CH2CH2" A5-2
339 A7-1 — CH2CH2CH2" A6-1
340 A7-1 — CH2CH2CH2" A6-2
341 A7-1 — CH2CH2CH2" A6-3
342 A7-1 — CH2CH2CH2" A6-4
343 A7-1 — CH2CH2CH2" A8-1
344 A7-1 — CH2CH2CH2" A8-2
345 A7-1 — CH2CH2CH2" A8-3
346 A7-1 — CH2CH2CH2" A8-4
347 A7-1 — CH2CH2CH2" A8-5
348 A7-1 — CH2CH2CH2" A8-6
349 Al-2 — CH2CH2CH2" Al-2
350 Al-3 — CH2CH2CH2" Al-3
351 Al-4 — CH2CH2CH2" Al-4
352 Al-5 — CH2CH2CH2" Al-5
353 Al-6 — CH2CH2CH2" Al-6
354 Al-7 — CH2CH2CH2" Al-7
355 Al-8 — CH2CH2CH2" Al-8
356 Al-9 — CH2CH2CH2" Al-9
357 Al-10 — CH2CH2CH2" Al-10
358 A2-2 — CH2CH2CH2" A2-2
359 A3-1 — CH2CH2CH2" A3-1
360 A3-3 — CH2CH2CH2" A3-3
361 A3-4 — CH2CH2CH2" A3-4
362 A3-5 — CH2CH2CH2" A3-5
363 A3-6 — CH2CH2CH2" A3-6
364 A3-7 — CH2CH2CH2" A3-7
365 A3-8 — CH2CH2CH2" A3-8
366 A3-9 — CH2CH2CH2" A3-9
367 A3-10 — CH2CH2CH2" A3-10
368 A3-11 — CH2CH2CH2" A3-11
369 A3-12 — CH2CH2CH2" A3-12 Compound X 1 | 4
370 A3-13 — CH2CH2CH2- A3-13
371 A3-14 — CH2CH2CH2- A3-14
372 A3-15 — CH2CH2CH2- A3-15
373 A4-1 — CH2CH2CH2- A4-1
374 A4-3 — CH2CH2CH2- A4-3
375 A4-4 — CH2CH2CH2- A4-4
376 A4-5 — CH2CH2CH2- A4-5
377 A4-6 — CH2CH2CH2- A4-6
378 A4-7 — CH2CH2CH2- A4-7
379 A4-8 — CH2CH2CH2- A4-8
380 A4-9 — CH2CH2CH2- A4-9
381 A4-10 — CH2CH2CH2- A4-10
382 A4-11 — CH2CH2CH2- A4-11
383 A5-2 — CH2CH2CH2- A5-2
384 A6-1 — CH2CH2CH2- A6-1
385 A6-2 — CH2CH2CH2- A6-2
386 A6-3 — CH2CH2CH2- A6-3
387 A6-4 — CH2CH2CH2- A6-4
388 A8-1 — CH2CH2CH2- A8-1
389 A8-2 — CH2CH2CH2- A8-2
390 A8-3 — CH2CH2CH2- A8-3
391 A8-4 — CH2CH2CH2- A8-4
392 A8-5 — CH2CH2CH2- A8-5
393 A8-6 — CH2CH2CH2- A8-6
394 A3-3 — CH2CH2CH2- A3-12
395 A3-3 — CH2CH2CH2- A4-10
396 A3-3 — CH2CH2CH2- A8-3
397 A3-3 — CH2CH2CH2- A8-4
398 A3-12 — CH2CH2CH2- A8-3
399 A3-12 — CH2CH2CH2- A8-4
400 A3-12 — CH2CH2CH2- A8-10
401 Al-1 — CH2CH2CH2- Al-11
402 Al-1 — CH2CH2CH2- Al-12
403 Al-1 — CH2CH2CH2- A2-3
404 Al-1 — CH2CH2CH2- A3-16
405 Al-1 — CH2CH2CH2- A3-17
406 Al-1 — CH2CH2CH2- A3-18 Compound X 1 | 4
407 Al-1 — CH2CH2CH2- A3-19
408 Al-1 — CH2CH2CH2- A3-20
409 Al-1 — CH2CH2CH2- A4-12
410 Al-1 — CH2CH2CH2- A4-13
411 Al-1 — CH2CH2CH2- A4-14
412 Al-1 — CH2CH2CH2- A4-15
413 Al-1 — CH2CH2CH2- A4-16
414 Al-1 — CH2CH2CH2- A8-7
415 Al-1 — CH2CH2CH2- A8-8
416 Al-1 — CH2CH2CH2- A8-9
417 Al-1 — CH2CH2CH2- A8-10
418 A2-1 — CH2CH2CH2- Al-11
419 A2-1 — CH2CH2CH2- Al-12
420 A2-1 — CH2CH2CH2- A2-3
421 A2-1 — CH2CH2CH2- A3-16
422 A2-1 — CH2CH2CH2- A3-17
423 A2-1 — CH2CH2CH2- A3-18
424 A2-1 — CH2CH2CH2- A3-19
425 A2-1 — CH2CH2CH2- A3-20
426 A2-1 — CH2CH2CH2- A4-12
427 A2-1 — CH2CH2CH2- A4-13
428 A2-1 — CH2CH2CH2- A4-14
429 A2-1 — CH2CH2CH2- A4-15
430 A2-1 — CH2CH2CH2- A4-16
431 A2-1 — CH2CH2CH2- A8-7
432 A2-1 — CH2CH2CH2- A8-8
433 A2-1 — CH2CH2CH2- A8-9
434 A2-1 — CH2CH2CH2- A8-10
435 A3-2 — CH2CH2CH2- Al-11
436 A3-2 — CH2CH2CH2- Al-12
437 A3-2 — CH2CH2CH2- A2-3
438 A3-2 — CH2CH2CH2- A3-16
439 A3-2 — CH2CH2CH2- A3-17
440 A3-2 — CH2CH2CH2- A3-18
441 A3-2 — CH2CH2CH2- A3-19
442 A3-2 — CH2CH2CH2- A3-20
443 — CH2CH2CH2- A4-12 Compound X I | 4
444 A3-2 — CH2CH2CH2" A4-13
445 A3-2 — CH2CH2CH2" A4-14
446 A3-2 — CH2CH2CH2" A4-15
447 A3-2 — CH2CH2CH2" A4-16
448 A3-2 — CH2CH2CH2" A8-7
449 A3-2 — CH2CH2CH2" A8-8
450 A3-2 — CH2CH2CH2" A8-9
451 A3-2 — CH2CH2CH2" A8-10
452 A4-2 — CH2CH2CH2" Al-11
453 A4-2 — CH2CH2CH2" Al-12
454 A4-2 — CH2CH2CH2" A2-3
455 A4-2 — CH2CH2CH2" A3-16
456 A4-2 — CH2CH2CH2" A3-17
457 A4-2 — CH2CH2CH2" A3-18
458 A4-2 — CH2CH2CH2" A3-19
459 A4-2 — CH2CH2CH2" A3-20
460 A4-2 — CH2CH2CH2" A4-12
461 A4-2 — CH2CH2CH2" A4-13
462 A4-2 — CH2CH2CH2" A4-14
463 A4-2 — CH2CH2CH2" A4-15
464 A4-2 — CH2CH2CH2" A4-16
465 A4-2 — CH2CH2CH2" A8-7
466 A4-2 — CH2CH2CH2" A8-8
467 A4-2 — CH2CH2CH2" A8-9
468 A4-2 — CH2CH2CH2" A8-10
469 A4-9 — CH2CH2CH2" Al-2
470 A4-9 — CH2CH2CH2" Al-3
471 A4-9 — CH2CH2CH2" Al-4
472 A4-9 — CH2CH2CH2" Al-5
473 A4-9 — CH2CH2CH2" Al-6
474 A4-9 — CH2CH2CH2" Al-7
475 A4-9 — CH2CH2CH2" Al-8
476 A4-9 — CH2CH2CH2" Al-9
477 A4-9 — CH2CH2CH2" Al-10
478 A4-9 — CH2CH2CH2" A2-2
479 A4-9 — CH2CH2CH2" A3-1
480 A4-9 — CH2CH2CH2" A3-3 Compound X I | 4
481 A4-9 — CH2CH2CH2" A3-4
482 A4-9 — CH2CH2CH2" A3-5
483 A4-9 — CH2CH2CH2" A3-6
484 A4-9 — CH2CH2CH2" A3-7
485 A4-9 — CH2CH2CH2" A3-8
486 A4-9 — CH2CH2CH2" A3-9
487 A4-9 — CH2CH2CH2" A3-10
488 A4-9 — CH2CH2CH2" A3-11
489 A4-9 — CH2CH2CH2" A3-12
490 A4-9 — CH2CH2CH2" A3-13
491 A4-9 — CH2CH2CH2" A3-14
492 A4-9 — CH2CH2CH2" A3-15
493 A4-9 — CH2CH2CH2" A4-1
494 A4-9 — CH2CH2CH2" A4-3
495 A4-9 — CH2CH2CH2" A4-4
496 A4-9 — CH2CH2CH2" A4-5
497 A4-9 — CH2CH2CH2" A4-6
498 A4-9 — CH2CH2CH2" A4-7
499 A4-9 — CH2CH2CH2" A4-8
500 A4-9 — CH2CH2CH2" A4-10
501 A4-9 — CH2CH2CH2" A4-11
502 A4-9 — CH2CH2CH2" A5-2
503 A4-9 — CH2CH2CH2" A6-1
504 A4-9 — CH2CH2CH2" A6-2
505 A4-9 — CH2CH2CH2" A6-3
506 A4-9 — CH2CH2CH2" A6-4
507 A4-9 — CH2CH2CH2" A7-2
508 A4-9 — CH2CH2CH2" A8-1
509 A4-9 — CH2CH2CH2" A8-2
510 A4-9 — CH2CH2CH2" A8-3
511 A4-9 — CH2CH2CH2" A8-4
512 A4-9 — CH2CH2CH2" A8-5
513 A4-9 — CH2CH2CH2" A8-6
514 A4-9 — CH2CH2CH2" Al-11
515 A4-9 — CH2CH2CH2" Al-12
516 A4-9 — CH2CH2CH2" A2-3
517 A4-9 — CH2CH2CH2" A3-16 Compound X I | 4
518 A4-9 — CH2CH2CH2" A3-17
519 A4-9 — CH2CH2CH2" A3-18
520 A4-9 — CH2CH2CH2" A3-19
521 A4-9 — CH2CH2CH2" A3-20
522 A4-9 — CH2CH2CH2" A4-12
523 A4-9 — CH2CH2CH2" A4-13
524 A4-9 — CH2CH2CH2" A4-14
525 A4-9 — CH2CH2CH2" A4-15
526 A4-9 — CH2CH2CH2" A4-16
527 A4-9 — CH2CH2CH2" A8-7
528 A4-9 — CH2CH2CH2" A8-8
529 A4-9 — CH2CH2CH2" A8-9
530 A4-9 — CH2CH2CH2" A8-10
531 A5-1 — CH2CH2CH2" Al-11
532 A5-1 — CH2CH2CH2" Al-12
533 A5-1 — CH2CH2CH2" A2-3
534 A5-1 — CH2CH2CH2" A3-16
535 A5-1 — CH2CH2CH2" A3-17
536 A5-1 — CH2CH2CH2" A3-18
537 A5-1 — CH2CH2CH2" A3-19
538 A5-1 — CH2CH2CH2" A3-20
539 A5-1 — CH2CH2CH2" A4-12
540 A5-1 — CH2CH2CH2" A4-13
541 A5-1 — CH2CH2CH2" A4-14
542 A5-1 — CH2CH2CH2" A4-15
543 A5-1 — CH2CH2CH2" A4-16
544 A5-1 — CH2CH2CH2" A8-7
545 A5-1 — CH2CH2CH2" A8-8
546 A5-1 — CH2CH2CH2" A8-9
547 A5-1 — CH2CH2CH2" A8-10
548 A6-5 — CH2CH2CH2" Al-11
549 A6-5 — CH2CH2CH2" Al-12
550 A6-5 — CH2CH2CH2" A2-3
551 A6-5 — CH2CH2CH2" A3-16
552 A6-5 — CH2CH2CH2" A3-17
553 A6-5 — CH2CH2CH2" A3-18
554 A6-5 — CH2CH2CH2" A3-19 Compound X I | 4
555 A6-5 — CH2CH2CH2" A3-20
556 A6-5 — CH2CH2CH2" A4-12
557 A6-5 — CH2CH2CH2" A4-13
558 A6-5 — CH2CH2CH2" A4-14
559 A6-5 — CH2CH2CH2" A4-15
560 A6-5 — CH2CH2CH2" A4-16
561 A6-5 — CH2CH2CH2" A8-7
562 A6-5 — CH2CH2CH2" A8-8
563 A6-5 — CH2CH2CH2" A8-9
564 A6-5 — CH2CH2CH2" A8-10
565 A7-1 — CH2CH2CH2" Al-11
566 A7-1 — CH2CH2CH2" Al-12
567 A7-1 — CH2CH2CH2" A2-3
568 A7-1 — CH2CH2CH2" A3-16
569 A7-1 — CH2CH2CH2" A3-17
570 A7-1 — CH2CH2CH2" A3-18
571 A7-1 — CH2CH2CH2" A3-19
572 A7-1 — CH2CH2CH2" A3-20
573 A7-1 — CH2CH2CH2" A4-12
574 A7-1 — CH2CH2CH2" A4-13
575 A7-1 — CH2CH2CH2" A4-14
576 A7-1 — CH2CH2CH2" A4-15
577 A7-1 — CH2CH2CH2" A4-16
578 A7-1 — CH2CH2CH2" A8-7
579 A7-1 — CH2CH2CH2" A8-8
580 A7-1 — CH2CH2CH2" A8-9
581 A7-1 — CH2CH2CH2" A8-10
582 A8-2 — CH2CH2CH2" Al-2
583 A8-2 — CH2CH2CH2" Al-3
584 A8-2 — CH2CH2CH2" Al-4
585 A8-2 — CH2CH2CH2" Al-5
586 A8-2 — CH2CH2CH2" Al-6
587 A8-2 — CH2CH2CH2" Al-7
588 A8-2 — CH2CH2CH2" Al-8
589 A8-2 — CH2CH2CH2" Al-9
590 A8-2 — CH2CH2CH2" Al-10
591 A8-2 — CH2CH2CH2" A3-1 Compound X I | 4
592 A8-2 — CH2CH2CH2" A3-3
593 A8-2 — CH2CH2CH2" A3-4
594 A8-2 — CH2CH2CH2" A3-5
595 A8-2 — CH2CH2CH2" A3-6
596 A8-2 — CH2CH2CH2" A3-7
597 A8-2 — CH2CH2CH2" A3-8
598 A8-2 — CH2CH2CH2" A3-9
599 A8-2 — CH2CH2CH2" A3-10
600 A8-2 — CH2CH2CH2" A3-11
601 A8-2 — CH2CH2CH2" A3-12
602 A8-2 — CH2CH2CH2" A3-13
603 A8-2 — CH2CH2CH2" A3-14
604 A8-2 — CH2CH2CH2" A3-15
605 A8-2 — CH2CH2CH2" A4-1
606 A8-2 — CH2CH2CH2" A4-3
607 A8-2 — CH2CH2CH2" A4-4
608 A8-2 — CH2CH2CH2" A4-5
609 A8-2 — CH2CH2CH2" A4-6
610 A8-2 — CH2CH2CH2" A4-7
611 A8-2 — CH2CH2CH2" A4-8
612 A8-2 — CH2CH2CH2" A4-10
613 A8-2 — CH2CH2CH2" A4-11
614 A8-2 — CH2CH2CH2" A5-2
615 A8-2 — CH2CH2CH2" A6-1
616 A8-2 — CH2CH2CH2" A6-2
617 A8-2 — CH2CH2CH2" A6-3
618 A8-2 — CH2CH2CH2" A6-4
619 A8-2 — CH2CH2CH2" A7-2
620 A8-2 — CH2CH2CH2" A8-1
621 A8-2 — CH2CH2CH2" A8-3
622 A8-2 — CH2CH2CH2" A8-4
623 A8-2 — CH2CH2CH2" A8-5
624 A8-2 — CH2CH2CH2" A8-6
625 A8-2 — CH2CH2CH2" Al-11
626 A8-2 — CH2CH2CH2" Al-12
627 A8-2 — CH2CH2CH2" A2-3
628 A8-2 — CH2CH2CH2" A3-16 Compound X 1 | 4
629 A8-2 — CH2CH2CH2- A3-17
630 A8-2 — CH2CH2CH2- A3-18
631 A8-2 — CH2CH2CH2- A3-19
632 A8-2 — CH2CH2CH2- A3-20
633 A8-2 — CH2CH2CH2- A4-12
634 A8-2 — CH2CH2CH2- A4-13
635 A8-2 — CH2CH2CH2- A4-14
636 A8-2 — CH2CH2CH2- A4-15
637 A8-2 — CH2CH2CH2- A4-16
638 A8-2 — CH2CH2CH2- A8-7
639 A8-2 — CH2CH2CH2- A8-8
640 A8-2 — CH2CH2CH2- A8-9
641 A8-2 — CH2CH2CH2- A8-10
642 Al-11 — CH2CH2CH2- A3-3
643 Al-11 — CH2CH2CH2- A3-12
644 Al-11 — CH2CH2CH2- A3-16
645 Al-11 — CH2CH2CH2- A3-18
646 Al-11 — CH2CH2CH2- A3-19
647 Al-11 — CH2CH2CH2- A3-20
648 Al-11 — CH2CH2CH2- A4-3
649 Al-11 — CH2CH2CH2- A4-10
650 Al-11 — CH2CH2CH2- A4-12
651 Al-11 — CH2CH2CH2- A4-13
652 Al-11 — CH2CH2CH2- A4-15
653 Al-11 — CH2CH2CH2- A8-3
654 Al-11 — CH2CH2CH2- A8-4
655 Al-11 — CH2CH2CH2- A8-7
656 Al-11 — CH2CH2CH2- A8-8
657 Al-11 — CH2CH2CH2- A8-9
658 Al-11 — CH2CH2CH2- A8-10
659 A3-16 — CH2CH2CH2- A3-3
660 A3-16 — CH2CH2CH2- A3-12
661 A3-16 — CH2CH2CH2- A3-16
662 A3-16 — CH2CH2CH2- A3-18
663 A3-16 — CH2CH2CH2- A3-19
664 A3-16 — CH2CH2CH2- A3-20
665 A3-16 — CH2CH2CH2- A4-3 Compound X I | 4
666 A3-16 — CH2CH2CH2" A4-10
667 A3-16 — CH2CH2CH2" A4-12
668 A3-16 — CH2CH2CH2" A4-13
669 A3-16 — CH2CH2CH2" A4-15
670 A3-16 — CH2CH2CH2" A8-3
671 A3-16 — CH2CH2CH2" A8-4
672 A3-16 — CH2CH2CH2" A8-7
673 A3-16 — CH2CH2CH2" A8-8
674 A3-16 — CH2CH2CH2" A8-9
675 A3-16 — CH2CH2CH2" A8-10
676 A3-17 — CH2CH2CH2" A3-3
677 A3-17 — CH2CH2CH2" A3-12
678 A3-17 — CH2CH2CH2" A3-16
679 A3-17 — CH2CH2CH2" A3-18
680 A3-17 — CH2CH2CH2" A3-19
681 A3-17 — CH2CH2CH2" A3-20
682 A3-17 — CH2CH2CH2" A4-3
683 A3-17 — CH2CH2CH2" A4-10
684 A3-17 — CH2CH2CH2" A4-12
685 A3-17 — CH2CH2CH2" A4-13
686 A3-17 — CH2CH2CH2" A4-15
687 A3-17 — CH2CH2CH2" A8-3
688 A3-17 — CH2CH2CH2" A8-4
689 A3-17 — CH2CH2CH2" A8-7
690 A3-17 — CH2CH2CH2" A8-8
691 A3-17 — CH2CH2CH2" A8-9
692 A3-17 — CH2CH2CH2" A8-10
693 A3-18 — CH2CH2CH2" A3-3
694 A3-18 — CH2CH2CH2" A3-12
695 A3-18 — CH2CH2CH2" A3-16
696 A3-18 — CH2CH2CH2" A3-18
697 A3-18 — CH2CH2CH2" A3-19
698 A3-18 — CH2CH2CH2" A3-20
699 A3-18 — CH2CH2CH2" A4-3
700 A3-18 — CH2CH2CH2" A4-10
701 A3-18 — CH2CH2CH2" A4-12
702 A3-18 — CH2CH2CH2" A4-13 Compound X I | 4
703 A3-18 — CH2CH2CH2" A4-15
704 A3-18 — CH2CH2CH2" A8-3
705 A3-18 — CH2CH2CH2" A8-4
706 A3-18 — CH2CH2CH2" A8-7
707 A3-18 — CH2CH2CH2" A8-8
708 A3-18 — CH2CH2CH2" A8-9
709 A3-18 — CH2CH2CH2" A8-10
710 A3-19 — CH2CH2CH2" A3-3
711 A3-19 — CH2CH2CH2" A3-12
712 A3-19 — CH2CH2CH2" A3-20
713 A3-19 — CH2CH2CH2" A4-3
714 A3-19 — CH2CH2CH2" A4-10
715 A3-19 — CH2CH2CH2" A4-13
716 A3-19 — CH2CH2CH2" A4-15
717 A3-19 — CH2CH2CH2" A8-3
718 A3-19 — CH2CH2CH2" A8-4
719 A3-19 — CH2CH2CH2" A8-7
720 A3-19 — CH2CH2CH2" A8-8
721 A3-19 — CH2CH2CH2" A8-9
722 A3-19 — CH2CH2CH2" A8-10
723 A4-12 — CH2CH2CH2" A3-3
724 A4-12 — CH2CH2CH2" A3-12
725 A4-12 — CH2CH2CH2" A3-20
726 A4-12 — CH2CH2CH2" A4-3
727 A4-12 — CH2CH2CH2" A4-10
728 A4-12 — CH2CH2CH2" A4-13
729 A4-12 — CH2CH2CH2" A4-15
730 A4-12 — CH2CH2CH2" A8-3
731 A4-12 — CH2CH2CH2" A8-4
732 A4-12 — CH2CH2CH2" A8-7
733 A4-12 — CH2CH2CH2" A8-8
734 A4-12 — CH2CH2CH2" A8-9
735 A4-12 — CH2CH2CH2" A8-10
736 A4-13 — CH2CH2CH2" A3-3
737 A4-13 — CH2CH2CH2" A3-12
738 A4-13 — CH2CH2CH2" A3-20
739 A4-13 — CH2CH2CH2" A4-3 Compound X I | 4
740 A4-13 — CH2CH2CH2" A4-10
741 A4-13 — CH2CH2CH2" A4-15
742 A4-13 — CH2CH2CH2" A8-3
743 A4-13 — CH2CH2CH2" A8-4
744 A4-13 — CH2CH2CH2" A8-7
745 A4-13 — CH2CH2CH2" A8-8
746 A4-13 — CH2CH2CH2" A8-9
747 A4-13 — CH2CH2CH2" A8-10
748 A4-14 — CH2CH2CH2" A3-3
749 A4-14 — CH2CH2CH2" A3-12
750 A4-14 — CH2CH2CH2" A3-20
751 A4-14 — CH2CH2CH2" A4-3
752 A4-14 — CH2CH2CH2" A4-10
753 A4-14 — CH2CH2CH2" A4-13
754 A4-14 — CH2CH2CH2" A4-15
755 A4-14 — CH2CH2CH2" A8-3
756 A4-14 — CH2CH2CH2" A8-4
757 A4-14 — CH2CH2CH2" A8-7
758 A4-14 — CH2CH2CH2" A8-8
759 A4-14 — CH2CH2CH2" A8-9
760 A4-14 — CH2CH2CH2" A8-10
761 A4-15 — CH2CH2CH2" A3-3
762 A4-15 — CH2CH2CH2" A3-12
763 A4-15 — CH2CH2CH2" A3-20
764 A4-15 — CH2CH2CH2" A4-3
765 A4-15 — CH2CH2CH2" A4-10
766 A4-15 — CH2CH2CH2" A4-13
767 A4-15 — CH2CH2CH2" A8-3
768 A4-15 — CH2CH2CH2" A8-4
769 A4-15 — CH2CH2CH2" A8-7
770 A4-15 — CH2CH2CH2" A8-8
771 A4-15 — CH2CH2CH2" A8-9
772 A4-15 — CH2CH2CH2" A8-10
773 A8-7 — CH2CH2CH2" A3-3
774 A8-7 — CH2CH2CH2" A3-12
775 A8-7 — CH2CH2CH2" A3-20
776 A8-7 — CH2CH2CH2" A4-3 Compound X I | 4
111 A8-7 — CH2 H2 H2" A4-10
778 A8-7 — CH2 H2 H2" A4-13
779 A8-7 — CH2 H2 H2" A4-15
780 A8-7 — CH2 H2 H2" A8-3
781 A8-7 — CH2 H2 H2" A8-4
782 A8-7 — CH2 H2 H2" A8-8
783 A8-7 — CH2 H2 H2" A8-9
784 A8-7 — CH2 H2 H2" A8-10
The compounds in Table 2 include all isomers, tautomers and mixtures thereof. In one embodiment the invention provides compounds of formula IA
Figure imgf000109_0001
wherein Q, Q', D1, D2, D3, D4, D5, D6 and X are as defined for compounds of formula
I. The preferred definitions of Q, Q', D1, D2, D3, D4, D5, D6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formula IB
Figure imgf000109_0002
wherein L1, L2, L3, L4, L5, L6, R12, R12', R13, R13' and X are as defined for compounds of formula I. The preferred definitions of L1, L2, L3, L4, L5, L6, R12, R12', R13, R13' and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formula IC
Figure imgf000109_0003
wherein R12, R12, R13, R13', D1, D2, D3, D4, D5, D6 and X are as defined for compounds of formula I. The preferred definitions of R12, R12', R13, R13', D1, D2, D3, D4, D5, D6 and X are the same as for the corresponding substituents of formula I.
In one embodiment, the invention provides compounds of the formula ID
Figure imgf000110_0001
wherein L1, L2, L3, L4, L5, L6, Y1, Y1', Y2, Y2', Y3, Y3', Y4, Y4' and X are as defined for compounds of formula I. The preferred definitions of L1, L2, L3, L4, L5, L6, Y1, Y1', Y2, Y2', Y3, Y3', Y4, Y4' and X are the same as for the corresponding substituents of formula I.
In one embodiment, the invention provides compounds of the formula IE
Figure imgf000110_0002
(IE)
wherein Y1, Y1', Y2, Y2', Y3, Y3', Y4, Y4', D1, D2, D3, D4, D5, D6 and X are as defined for compounds of formula I. The preferred definitions of Y1, Y1', Y2, Y2', Y3, Y3', Y4, Y4', D1, D2, D3, D4, D5, D6 and X are the same as for the corresponding substituents of formula I.
In one embodiment, the invention provides compounds of the formula IF
Figure imgf000110_0003
(IF)
wherein Y1, Y2, Y3, Y4, R12', R13', L1, L2, L3, L4, L5, L6 and X are as defined for compounds of formula I. The preferred definitions of Y1, Y2, Y3, Y4, R12', R13', L1, L2, L3, L4, L5, L6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formual IG
Figure imgf000111_0001
wherein Y1, Y2, Y3, Y4, R12, R13', D1, D2, D3, D4, D5, D6 and X are as defined for compounds of formula I. The preferred definitions of Y1, Y1', Y2, Y2', R12', R13', D1, D2, D3, D4, D5, D6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formual IH
Figure imgf000111_0002
wherein Y2, Y2', Y3, Y3', Y4, Y4', L1, L2, L3, L4, L5, L6 and X are as defined for compounds of formula I. The preferred definitions of Y2, Y2', Y3, Y3', Y4, Y4', L1, L2, L3, L4, L5, L6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formual IJ
Figure imgf000111_0003
wherein Y2, Y2', Y3, Y3', Y4, Y4', D1, D2, D3, D4, D5, D6 and X are as defined for compounds of formula I. The preferred definitions of Y2, Y2', Y3, Y3', Y4, Y4', D1, D2, D3, D4, D5, D6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formula IK
Figure imgf000112_0001
wherein Q, Q', D2, D3, D5, D6 and X are as defined for compounds of formula I. The preferred definitions of Q, Q', D2, D3, D5, D6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formula IL
Figure imgf000112_0002
wherein Q, Q', D2, D3, D4,D5, D6 and X are as defined for compounds of formula I. The preferred definitions of Q, Q', D2, D3, D4,D5, D6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formual IM
wherein Y1, Y2, Y3, Y4, D2, D3, D4, D5, D6, Q' and X are as defined for compounds of formula I. The preferred definitions of Y1, Y1', Y2, Y2', D2, D3, D4, D5, D6, Q' and X are the same as for the corresponding substituents of formula I.
In one embodiment, the invention provides compounds of the formula IN
Figure imgf000112_0004
(IN) wherein Y1, Y2, Y2 Y3, Y3', Y4, Y4, L1, L2, L3, L4, L5, L6 and X are as defined for compounds of formula I. The preferred definitions of Y1, Y2, Y2' Y3, Y3', Y4, Y4', L1, L2, L3, L4, L5, L6 and X are the same as for the corresponding substituents of formula I.
In one embodiment the invention provides compounds of formual 10
Figure imgf000113_0001
wherein Y1, Y2, Y2', Y3, Y3', Y4, Y4', D1, D2, D3, D4, D5, D6 and X are as defined for compounds of formula I. The preferred definitions of Y2, Y2', Y3, Y3', Y4, Y4', D1, D2, D3, D4, D5, D6 and X are the same as for the corresponding substituents of formula I. The compounds of the invention may be made by a variety of methods, illustrated in schemes 1-16. The compounds depicted in the schemes also indicate any isomers and tautomers, in particular the geometric isomers arising from the oxime and oxime ether moieties.
Scheme 1
Figure imgf000113_0002
(V) (VI) a'
(1) Compounds of formula (la) that is a compound of formula (I) wherein Z1, Z3, Z6 and Z10 are methylene and X'" represents X"'-l, X"'-2, and X"'-3 and X"'-4
#— z— # #— z— z— # #— z— z— z— # #— z— z— z— z— # γπ, Λ X"'-9 X"'-3
Λ - 1 X"'-4 may be obtained from compounds of formula (V) wherein Q, L1, L2 and L5 are as defined herein for compounds of formula (I) and compounds of formula (VI) wherein Q', L3, L4 and L6 are as defined herein for compounds of formula (I) and R28 is a halogen, in particular chlorine, bromine or iodine, or a sulfonic acid ester group, such as mesylate, tosylate, triflate, a phenylsulfonic acid ester, a nitro-phenylsulfonic acid ester, or a nonafluorobutylsulfonic acid ester. The reaction is carried out in the presence of a base such as for example n-butyllithium, sec-butyllithium, lithium diisopropylamide, sodiumamide or sodiumhydride. Examples of such substitution reactions may be found in Synthesis, (6), 519-521; 1992; Journal of the American Chemical Society, 127(43), 15151-15160; 2005; Angewandte Chemie, International Edition, 45(6), 932-935; 2006 or in Synthesis, (19), 3253-3256; 2005.
Scheme 2
L1^L2 L1^L2 L
R29^ .R29 2-L
X"
Q N Q N l\T Q
(V) ( ii) (lb)
(2) Compounds of formula (lb) that is a compound of formula (I) wherein Q and Q' are identical (both Q and Q' are represented in Scheme 2 as Q), Z3, Z5, Z6, Z9, Z10 and Z14 are methylene and X" represents X"-l, X"-2 and X"-3
#— z— # #— z— z— # #_Z1^Z12_Z13_#
X"-1 X"-2 X"-3
may be obtained from compounds of formula (V) wherein Q, L1, L2 and L5 are as defined herein for compounds of formula (I), and compounds of formula (VII) wherein X" is as defined herein for the compounds of formula (lb) and R29 is a halogen, in particular chlorine, bromine or iodine. The reaction is carried out in the presence of a base such as for example n-butyllithium, sec-butyllithium, lithium diisopropylamide, sodiumamide or sodiumhydride. Examples of such substitution reactions may be found in Journal of
Organometallic Chemistry, 607(1-2), 194-202; 2000; Chemistry-A European Journal, 14(2), 682-696; 2008 or in Inorganic Chemistry, 49(9), 4023-4035; 2010.
Scheme 3
Figure imgf000114_0001
(VIM)
(V) (lc)
Figure imgf000114_0002
(Id) (IX)
(3) Compounds of formula (Id), that is a compound of formula (I) wherein Q and Q' are identical (both Q and Q' are represented in Scheme 3 as Q), L1 and L4 are identical (both L1 and L4 are represented in Scheme 3 as L1), L2 and L3 are identical (both L2 and L3 are represented in Scheme 3 as L2), L5 and L6 are identical (both L5 and L6 are represented in Scheme 3 as L5) and X is CH2-CH2-CH2 may be prepared from compound (IX) wherein Q, L1, L2 and L5 are as defined herein for compounds of formula (I) by catalytic hydrogenation in the presence of a metal catalyst, for example palladium, nickel or platinum. The reaction is usually carried out in the presence of a solvent under a hydrogen atmosphere. In some cases it is necessary to apply pressure in the range of 1 to 100 bar. Suitable solvents for such reactions are alcohols, such as methanol or ethanol, cyclic ethers, such as dioxane or tetrahydrofuran or esters such as ethyl acetate. The reaction is usually carried out at a reaction temperature ranging from 0°C to the boiling point of the solvent. Examples for the hydrogenation in the presence of a nickel catalyst can be found in Journal of Organic Chemistry, 69(6), 1959-1966; 2004. Examples for the hydrogenation in the presence of a palladium catalyst can be found in Journal of Organic Chemistry, 74(16), 6072-6076; 2009. Examples for hydrogenation in the presence of a platinum catalyst can be found in
Organometallics, 5(2), 348-55; 1986.
(4) Compounds of formula (IX) may be prepared by elimination of water from compounds of formula (Ic), that is a compound of formula (I) wherein Q and Q' are identical (both Q and Q' are represented in Scheme 3 as Q), L1 and L4 are identical (both L1 and L4 are represented in Scheme 3 as L1), L2 and L3 are identical (both L2 and L3 are represented in Scheme 3 as L2), L5 and L6 are identical (both L5 and L6 are represented in Scheme 3 as L5) and X is CH2-CH(OH)-CH2. This can be done using one of several techniques well known to the person skilled in the art including procedures wherein the hydroxyl group is converted into a more activated leaving group such as for example a halogen, in particular chlorine, bromine or iodine, or a sulfonic acid ester group, such as mesylate, tosylate, triflate, a phenylsulfonic acid ester, a nitro-phenylsulfonic acid ester, or a nonafluorobutylsulfonic acid ester and this leaving group is then eliminated in the presence of an appropriate base such as for example sodium or potassium hydroxide, triethylamine, diisopropylamine, DBU (l,8-diazabicyclo[5.4.0]undec-7-ene) or pyridine. Examples for such elimination can be found in Bioorganic & Medicinal Chemistry Letters, 14(14), 3635-3638; 2004; Journal of the American Chemical Society, 129(48), 14836- 14837; 2007. Alternative elimination procedures are known and are described for example in March's Advanced Organic Chemistry: Reaction, Mechanisms and Structure, Sixth Edition, 2007 and references therein.
(5) Compounds of formula (Ic) may be prepared by reacting compounds of formula (V) wherein Q, L1, L2 and L5 are as defined herein for compounds of formula (I) and compounds of formula (VIII) wherein R30 is d-C4 alkyl in the presence of a base such as for example n-butyllithium, sec-butyllithium, lithium diisopropylamide, sodiumamide or sodiumhydride. The reaction is usually carried out at a reaction temperature ranging from - 100°C to 50°C. Suitable solvents for such reactions are for example cyclic ethers, such as dioxane or tetrahydrofuran or hydrocarbons such as pentane, hexane, cyclohexane or toluene. Similar examples and conditions for reactions of anionic or organometallic compounds with formiates of formula (VIII) can be found in WO 2008088538; Tetrahedron, 66(33), 6445-6449; 2010; Synthesis, (7), 1123-1140; 2010 or in Organic Letters, 10(23), 5321-5324; 2008. A specific example can be found in the experimental part herein.
Compounds of formula (Ic) are especially useful as intermediates to a number of other compounds, wherein the hydroxy group formed is transformed into other functional groups, such as for example carbonyl, fluorine or chlorine. Such transformations can be effected using a number of conditions well known to the person skilled in the art.
Scheme 4
Figure imgf000116_0001
(X) (le)
(6) Compounds of formula (Ie) that is a compound of formula (I) wherein Q and Q' are Q-2 and Q-2' respectively may be prepared from dinitriles of formula (X) wherein L1, L2, L3, L4, L5, L6 and X are as described herein for compounds of formula (I) using the procedures 23-24 described herein. A specific example wherein Q-2 and Q-2' are quinazolin-2-yl is described in the experimental part herein.
(7) Dinitriles of formula (X) may be prepared using the procedure 25 described herein. A more specific example is shown in scheme 5.
Scheme 5
Figure imgf000116_0002
(Xa)
(8) Dinitriles of formula (Xa), that is a compound of formula (X) wherein L1 is C-D1,
L2 is C-D2, L3 is C-D3, L4 is C-D4, L5 is C-D5, L6 is C-D6, and each of D1, D2, D3, D4, D5 and D6are hydrogen, may be prepared from pyridine N-oxides of formula (XI) wherein X is as described herein for compounds of formula (I) in the presence of a cyanide such as trimethylsilylcyanide, potassium- or sodium-cyanide. Such transformations are well known to the person skilled in the art. Examples and specific conditions can be found in Journal of Organic Chemistry, 48(8), 1375-7; 1983; Journal of the American Chemical Society, 130(8), 2414-2415; 2008 ; Inorganic Chemistry, 45(10), 4088-4096; 2006.
(9) Pyridine N-oxides of formula (XI) may be prepared by oxidation from compound (XII) wherein X is as defined herein for compounds of formula (I) in the presence of an oxidating agent such as mCPBA, oxone or hydrogen peroxide. Examples and specific conditions can be found in Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 5937 - 5941; Tetrahedron Letters, 51(43), 5690-5693; 2010; PCT Int. Appl., 2010027500, 11 Mar 2010.
The following schemes illustrate preparation of various intermediates:
Scheme 6 (Examples for the preparation of compounds of formula (VI))
Figure imgf000117_0001
(Via)
(10) Compounds of formula (Via), that is a compound of formula (VI) wherein X'" is X"-2, and each of Z4 and Z5 are methylene, may be prepared from compounds of formula
(XIII) wherein L3, L4, L6 and Q' are as defined herein for compounds of formula (I). Such transformations can be effected using a number of conditions well known to the person skilled in the art. A specific example is given in the experimental part herein.
(11) Compounds of formula (XIII) may be prepared from compounds of formula
(XIV) wherein L3, L4, L6 and Q' are as defined herein for compounds of formula (I) and R30 is Ci-C4 alkyl by reduction with a metal hydride, for example lithium aluminium hydride or diisobutyl aluminium hydride. Examples for such reductions can found in Journal of
Combinatorial Chemistry, 7(6), 958-967; 2005. The reaction is usually carried out at temperatures between -100 to 20°C in the presence of a solvent. (12) Compounds of formula (XIV) may be prepared by reacting compounds of formula (XLI) wherein L3, L4, L6 and Q' are as defined herein for compounds of formula (I) and compounds of formula (XV) wherein R30 is d-Q alkyl in the presence of a base such as for example n-butyl lithium, sec-butyl lithium, lithium diisopropylamide, sodium amide or sodium hydride. The reaction is usually carried out at a reaction temperature ranging from - 100°C to 50°C. Suitable solvents for such reactions are for example cyclic ethers, such as dioxane or tetrahydrofuran or hydrocarbons such as pentane, hexane, cyclohexane or toluene.
(13) Compounds of formula (VIb), that is a compound of formula (VI) wherein X'" is X"'-l wherein Z2 is methylene may be prepared from compounds of formula (XLI). This can be done using several methods known to the person skilled in the art among them halogenations with chloro-, bromo or iodo-succinimide. Examples and specific conditions can be found in Tetrahedron, 64(27), 6358-6363; 2008; Organic Letters, 12(11), 2551- 2553; 2010; Organic & Biomolecular Chemistry, 7(24), 5074-5077; 2009 or in Journal of Organic Chemistry, 75(19), 6540-6548; 2010.
Scheme 7
Figure imgf000118_0001
Figure imgf000118_0002
(ig)
(14) Compounds of formula (Ig), that is a compound of formula (I) wherein Q and Q' are identical (both Q and Q' are represented in Scheme 7 as Q7), L1 and L4 are identical (both L1 and L4 are represented in Scheme 7 as L4), L2 and L3 are identical (both L2 and L3 are represented in Scheme 7 as L3), L5 and L6 are identical (L5 and L6 are represented in Scheme 7 as L6), X is X-3 or X-5 wherein Z3, Z5, Z10, Z11, Z13 and Z14 are methylene
(represented by X"" in the scheme) and Z4 and Z12 are CR8R9, wherein R8 is H and R9 is COOR2 wherein R2 is d-Q alkyl may be prepared from compounds of formula (If) that is a compound of formula (I) wherein Q and Q' are identical (both Q and Q' are represented in Scheme 7 as Q'), L1 and L4 are identical (both L1 and L4 are represented in Scheme 7 as L4), L2 and L3 are identical (both L2 and L3 are represented in Scheme 7 as L3), L5 and L6 are identical (L5 and L6 are represented in Scheme 7 as L6),X is X-3 or X-5 wherein Z3, Z5, Z10, 5 Z11, Z13 and Z14 are methylene (represented by X"" in the scheme) and Z4 and Z12 are
CR8R9, wherein R8 and R9 are each COOR2 wherein R2 is Ci-C4 alkyl. Such transformations are well known to the person skilled in the art. Examples and conditions for such reactions can be found in Tetrahedron, 65(39), 8283-8296; 2009; European Journal of Organic Chemistry, (32), 5376-5385; 2007; Journal of the American Chemical Society, 126(12),
10 3700-3701; 2004; Bioorganic & Medicinal Chemistry Letters, 14(9), 2141-2145; 2004 and in Journal of Heterocyclic Chemistry, 39(6), 1167-1171; 2002.
Compounds of formula (Ig) are especially useful as intermediates to a number of other compounds, wherein the carboxyl group is transformed into other functional groups. Such transformations are well known to the person skilled in the art.
15 (15) Compounds of formula (If) may be prepared from compounds of formula (VI), and a dialkyl malonate of formula (XXXIII) wherein R2 is Ci-C4 alkyl in the presence of a base such as for example potassium or sodium carbonate, sodium amid or sodium hydride.
Two compounds of formula (If) are known and are given in the table below. Their preparation has been published in Inorganic Chemistry, 1983, 22, 171-174. Analogous
20 protocols can be used for the preparation of other compounds of formula (If)
Figure imgf000119_0001
Scheme 8
Figure imgf000120_0001
Figure imgf000120_0002
(XXXVI)
(U)
(16) Compounds of formula (Ij), that is a compound of formula (I) wherein X is X-3 and each of Z3, Z4 and Z5 are methylene may be prepared from compounds of formula (Ih), that is a compound of formula (I) wherein X is X-3, Z4 and Z5 are each methylene, and Z3 is CR4R5 wherein R5 is hydrogen and R4 is C02R2, wherein R2 is d-Q alkyl. Such a
decarboxylation can be affected using a number of conditions well known to the person skilled. Specific conditions can found for example in Journal of Heterocyclic Chemistry, 20(3), 623-8; 1983; Journal of Heterocyclic Chemistry, 45(5), 1451-1456; 2008 and in Synthesis, (18), 3027-3031; 2011.
(17) Compounds of formula (Ih) can be prepared from compounds of formula
(XXXV) wherein L3, L4, L6 and Q' are as defined herein for a compound of formula (I) and compounds of formula (XIV) wherein R2 is d-Q alkyl and Q, L1, L2 and L5 are as defined herein for compounds of formula (I). Such additions reactions can be carried out in the presence of a base, for example sodium hydride or sodium methylate, in a solvent (for example tetrahydrofuran). Similar reactions are known and conditions can be found for example in Organic & Biomolecular Chemistry (2010), 8(12), 2777-2783 or in Acta Chemica Scandinavica, 53(4), 269-279; 1999.
(18) Compounds of formula (XXXV) might be prepared from compounds of formula (XXXVI) wherein Q', L3, L4, and L6 are as defined herein for compounds of formula (I) and R29 is a halogen, in particular chlorine, bromine or iodine. Such transformation are well known. Examples and specific conditions can be found for example in Journal of Organic Chemistry, 70(5), 1698-1703; 2005 or in Tetrahedron, 62(42), 10005-10010; 2006 It is well known to the person skilled in the art that the reactions described in schemes 1-4, 6-8 and 14-16 can also be done with appropriate precursors of Q and Q' and these precursors can be transformed to Q or Q' at any stage of the reaction depending on possible side reactions. Some examples for the preparation of such precursors and their 5 transformations to Q are given in scheme 9-16. It will be clear to the person skilled in the art that all the reactions in schemes 9-15 can also be performed simultaneously or successively to build Q and Q' depending on possible side reactions.
Scheme 9
Figure imgf000121_0001
10 (19) Alternatively, as seen in scheme 9, compounds of formula (Im) wherein Q is
Q-9 may be prepared by reacting a compound of formula (II), wherein L1, L2, L3, L4, L5, L6, Q', X and R12 are as defined herein for compounds of formula (I) and T1 and T2 are Ci-Cs alkoxy, or T1 and T2 together with the carbon they are attached to form a carbonyl group or an acetal or ketal function of the form C(0-Ci-C6-alkylidene-0) whereby the alkylidene
15 fragment may optionally be mono- to tetra-substituted by Ci-Ce alkyl, and a compound of formula (XVI), wherein R13 is as defined herein for compounds of formula (I) by a condensation reaction. Typical reaction conditions for this type of reaction may be found in Journal of Organic Chemistry, 52(22), 4978-84; 1987; Chemical & Pharmaceutical Bulletin, 51(2), 138-151; 2003; Organic Letters, 10(2), 285-288; 2008; Journal of the American
20 Chemical Society, 130(12), 4196-4201; 2008; Chemistry & Biology, 9(1), 113-129; 2002;
Organic Preparations and Procedures International, 32(2), 153-159; 2000; Scientia
Pharmaceutica, 66(1), 9-21; 1998, Journal of Medicinal Chemistry, 49(17), 5177-5186; 2006, Journal of Agricultural and Food Chemistry, 38(3), 839-44; 1990; Tetrahedron:
Asymmetry, 8(2), 253-263; 1997; Journal of Medicinal Chemistry, 44(21), 3339-3342;
25 2001; Bioorganic & Medicinal Chemistry Letters, 12(3), 341-344; 2002; US 2007032470;
WO 07/058504; Journal of Organic Chemistry, 73(5), 2007-2010; 2008; Bioorganic & Medicinal Chemistry Letters, 19(10), 2683-2687; 2009; and Bioorganic & Medicinal
Chemistry Letters, 19(10), 2654-2660; 2009. (20) Alternatively, as seen in scheme 9, compounds of formula (Im) may be prepared by reacting a compound of formula (Ik), that is a compound of formula (I) wherein R13 is hydrogen, and a compound of formula (XVII), wherein R13 is as defined herein for compounds of formula (I) and R28 is a halogen, in particular chlorine, bromine or 5 iodine, or a sulfonic acid ester group, such as mesylate, tosylate, triflate, phenylsulfonic acid ester, nitro-phenylsulfonic acid ester, or nonafluorobutylsulfonic acid ester.
Typical reaction conditions for alkylation reactions such as this may be found in Chinese Journal of Chemistry, 27(1), 33-42; 2009; WO 09/049846; Journal of Antibiotics, 61(10), 603-614; 2008; Bioorganic & Medicinal Chemistry Letters, 18(24), 6471-6475;
10 2008; Journal of Medicinal Chemistry, 51(15), 4601-4608; 2008; WO 06/123145, Archiv der Pharmazie (Weinheim, Germany), 340(4), 202-208; 2007; Synthetic Communications, 37(7), 1155-1165; 2007; Russian Journal of Organic Chemistry, 42(5), 735-738; 2006; Bioinorganic Chemistry and Applications, 1(3-4), 299-308; 2003; Synthetic Communications, 28(14), 2621-2633; 1998; Synthetic Communications, 19(18), 3129-38; 1989.
15 (21) Oximes of formula (Ik) may be obtained by a condensation reaction, whereby a compound of formula (II) is reacted with hydroxylamine, or, alternatively, with a salt of hydroxylamine. Typical conditions for this reaction is found in Journal of Heterocyclic Chemistry, 46(1), 116-118; 2009; Journal of Medicinal Chemistry, 20(5), 718-21; 1977; Journal of Organic Chemistry, 73(11), 4017-4026; 2008; EJEAFChe, Electronic Journal of
20 Environmental, Agricultural and Food Chemistry, 5(5), 1515-1521; 2006; Advanced
Synthesis & Catalysis, 346(13-15), 1798-1811; 2004.
Scheme 10
Figure imgf000122_0001
(III)
25 (22) Alternatively as seen in scheme 10 compounds of formula (I) may be
prepared by reacting compounds of formula (III) wherein L1, L2, L3, L4, L5, L6, Q', X are as defined herein for compounds of formula (I) and R29 is a halogen, in particular chlorine, bromine or iodine, with a compound of formula (XVIII) wherein Q is as defined herein for compounds of formula (I) and M is an organometallic residue. This can be done using one
30 of several techniques well known to the person skilled in the art, including Suzuki, Stille and Negishi cross coupling reactions.
Examples and specific conditions for the Stille reaction may be found in Bioorganic & Medicinal Chemistry Letters, 19(19), 5689-5692; 2009; Journal of Organic Chemistry, 73(12), 4491-4495; 2008; Journal of the American Chemical Society, 129(3), 490-491; 2007 or in Journal of Organic Chemistry, 75(2), 424-433; 2010. Examples and specific conditions for the Negishi reaction may be found in European Journal of Inorganic
Chemistry, (26), 4101-4110; 2008; Tetrahedron Letters, 50(38), 5329-5331; 2009;
Tetrahedron Letters, 51(2), 357-359; 2010 or in Tetrahedron Letters, 51(19), 2657-2659; 2010. Examples and specific conditions for the Suzuki reaction may be found in Organic Letters, 11(2), 345-347; 2009; Journal of the American Chemical Society, 131(20), 6961- 6963; 2009; Synthesis, (1), 85-90; 2010 or in Heterocycles, 80(1), 359-368.
Scheme 11
Figure imgf000123_0001
(23) Compounds of formula (In), that is a compound of formula (I) wherein Q is Q- 2, may be obtained from amidines of formula (XIX) wherein L1, L2, L3, L4, L5, L6, Q' and X are as defined herein for compounds of formula (I). Such transformations can be effected using a number of conditions well known to the person skilled in the art. Specific examples and conditions can be found in Chemistry-A European Journal, 16(1), 89-94, S89/1-S89/10; 2010; Tetrahedron Letters, 50(49), 6818-6822; 2009; Bioorganic & Medicinal Chemistry Letters, 15(12), 2990-2993; 2005; Synthetic Communications, 27(14), 2521-2526; 1997; Journal of Combinatorial Chemistry, 7(4), 517-519; 2005 and in Bioorganic & Medicinal Chemistry Letters, 15(12), 2990-2993; 2005.
(24) Amidines of formula (XIX) may be prepared from nitriles of formula (IV) wherein L1, L2, L3, L4, L5, L6, Q' and X are as defined herein for compounds of formula (I). Typical conditions for such transformations can be found in Bioorganic & Medicinal Chemistry, 17(18), 6651-6658; 2009; Bioorganic & Medicinal Chemistry Letters, 19(8), 2277-2281; 2009; Journal of Medicinal Chemistry, 51(6), 1719-1729; 2008 or in Journal of Medicinal Chemistry, 50(26), 6535-6544; 2007.
(25) Nitriles of formula (IV) may be prepared from compounds of formula (III) wherein R29 is a halogen, in particular chlorine, bromine or iodine. Such transformation can be done under many different conditions well known to the person skilled in the art.
Examples and specifc conditions may be found in Journal of Organic Chemistry (2011), 76(2), 665-668; Journal of Medicinal Chemistry, 53(16), 6129-6152; 2010; Organic Letters, 9(9), 1711-1714; 2007; Journal of the American Chemical Society, 131(3), 1305-1313; 5 2009; Synthesis, (20), 3351-3355; 2008 and in Chemistry-A European Journal, 13(21), 6249-6254; 2007.
Scheme 12:
Figure imgf000124_0001
(26) Compounds of formula (Ip) that is a compound of formula (I) wherein Q is Q-20 and Y2 and Y3 together with the fragment to which they are attached form an aromatic carbocycle which is optionally substituted by one or more groups independently selected from halogen, d-Q alkyl, d-Q haloalkyl, d-C4 alkoxy and Ci-C4 haloalkoxy and Y4 is hydrogen or alkyl, may be prepared by oxidation from compound (XX) wherein L1, L2, L3, L4, L5, L6, Q' and X are as defined herein for compounds of formula (I) with an oxidation agent,5 such as 2,3-dichloro-5,6-dicycano-p-benzoquinone, oxygen, manganese(IV) oxide or ammonium cerium(IV) nitrate in various solvents such as methylene chloride,
tetrahydrofurane, acetonitrile or toluene. The reaction is usually carried out at a reaction temperature ranging from 0°C to the boiling point of the solvent or alternatively it can be run under microwave conditions.
0 (27) Compounds of formula (XX) wherein L1, L2, L3, L4, L5, L6, Q' and X are as defined herein for compounds of formula (I) and wherein Y2 and Y3 together with the fragment to which they are attached form an aromatic carbocycle which is optionally substituted by one or more groups independently selected from halogen, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy and Y4 is hydrogen or alkyl, can be prepared using one of several techniques well known to the person skilled in the art. As an example, (XX) may be obtained by reaction of a compound of formula (IV) with a compound of formula (XXI) wherein Y2 and Y3 together with the fragment to which they are attached form an aromatic carbocycle which is optionally substituted by one or more groups independently 5 selected from halogen, d-C4 alkyl, Ci-C4 haloalkyi, Ci-C4 alkoxy and Ci-C4 haloalkoxy and Y4 is hydrogen or alkyl, in the presence of thiourea or a metal alcoholate in solvent such as alcohols. The reaction is usually carried out at a reaction temperature ranging from 0°C to the boiling point of the solvent or alternatively it can be run under microwave conditions.
(28) Compounds of formula (XXI) are known compounds or may be obtained readily 10 from known compounds using processes that are well known to the person skilled in the art.
A specific example for such transformation is given in the experimental part herein. Scheme 13
Figure imgf000125_0001
15 (29) Compounds of formula (Iq), that is a compound of formula (I) wherein Q is Q-
3 and Y1 is hydrogen, may be obtained from compounds of formula (XXV) wherein L1, L2, L3, L4, L5, L6, Q', X and Y2 are as defined herein for compounds of formula (I) and amidines of formula (XXVI) wherein Y4 is as defined herein for compounds of formula (I). Typical conditions for such transformations can be found in Tetrahedron Letters, 50(49), 6818-
20 6822; 2009; Chemistry-A European Journal, 15(20), 5006-5011; 2009; Journal of Organic Chemistry (2009), 74(12), 4646-4649 or in Synlett, (19), 3036-3040; 2008. Amidines of formula (XXVI) are commercially available or can be prepared by methods well known to the person skilled in the art.
(30) Compounds of formula (XXV) may be prepared by oxidation from compounds of
25 formula (XXIV), wherein L1, L2, L3, L4, L5, L6, Q', X and Y2 are as defined herein for compounds of formula (I). Such oxidations can be done using a number of conditions well known to the person skilled in the art. Specific reaction conditions may be found in Journal of the American Chemical Society, 132(8), 2532-2533; 2010; Journal of Organic Chemistry, 74(15), 5750-5753; 2009 or in Tetrahedron, 64(29), 7008-7014; 2008.
(31) Compounds of formula (XXIV) may be prepared from aldehydes of formula
(XXII) wherein L1, L2, L3, L4, L5, L6, Q', and X are as defined herein for compounds of formula (I) and compounds of formula (XXIII) wherein Y2 is as defined herein for compounds of formula (I). Typical conditions for such transformations can be found in Tetrahedron, 64(29), 7008-7014; 2008; Journal of Organic Chemistry, 72(20), 7783-7786; 2007 or in Organic Letters, 9(6), 1169-1171; 2007.
Scheme 14:
Figure imgf000126_0001
(32) Compounds of formula (Ir) wherein Q is Q-l and Y3 is H can be prepared from compounds of formula (XXIX) wherein L1, L2, L3, L4, L5, L6, Q', and X are as defined herein for compounds of formula (I), Y1 is hydrogen or methyl, Y4 is methyl or ethyl. Such transformations can be effected using a number of conditions well known to the person skilled in the art.
(33) Compounds of formula (XXIX) can be prepared from compounds of formula (XXVIII) wherein L1, L2, L3, L4, L5, L6, Q', and X are as defined herein for compounds of formula (I), Y4 is methyl or ethyl and Y1 is hydrogen or methyl by reaction with trimethylsilyl triflate and Hiinig's base in 1,2-dichloroethane at reflux temperature as described in Chem. Eur. J. 2009, 15, 6811-6814.
(34) Compounds of formula (XXVIII) can be prepared from compounds of formula (XXVII) wherein L1, L2, L3, L4, L5, L6, Q', and X are as defined herein for compounds of formula (I). Such transformations can be effected using a number of conditions well known to the person skilled in the art.
Scheme 15
Figure imgf000127_0001
Compounds of formula (Is) that is a compound of formula (I) wherein Q is Q-l may be prepared from compounds of formula (XXX) wherein L1, L2, L3, L4, L5, L6, Q', X, Y1, Y2, Y3 and Y4 are as defined herein for compounds of formula (I). Such transformations can be effected using a number of conditions well known to the person skilled in the art. Specific examples and conditions may be found in Journal of the Chemical Society, Perkin
Transactions 1, (24), 3258-3264; 2001; Tetrahedron Letters, 46(14), 2361-2363; 2005; Synthesis, (10), 1664-1672; 2006 or in Journal of Medicinal Chemistry, 53(15), 5400-5421; 2010.
(36) Dicarbonyl compounds of formula (XXX) may be prepared by several methods well known to the person skilled in the art, among them the reaction of compounds of formula (XXXII) wherein L1, L2, L3, L4, L5, L6, Q', X, and Y are as defined herein for compounds of formula (I) with compounds of formula (XXXI) wherein Y2, Y3 and Y4 are as defined herein for compounds of formula (I) in the presence of a base. Specific examples and conditions for this transformation can be found in Journal of Medicinal Chemistry, 33(1), 52-60; 1990; Chemistry~A European Journal, 13(16), 4548-4559; 2007; Tetrahedron Letters, 46(14), 2361-2363; 2005 and in Journal of the Chemical Society, Perkin
Transactions 1, (24), 3258-3264; 2001 Scheme 16
Figure imgf000128_0001
(XXXVII) (It)
(37) Compounds of formula (It), that is a compound of formula (I) wherein Q and Q' are identical (both Q and Q' are shown as Q in Scheme 16), L1 and L4 are N and D5 and D6 are identical (both D5 and D6 are shown as D5 in Scheme 16) may be obtained from compounds of formula (XXXIX) wherein X and D5 are as defined herein for compounds of formula (I) and amidines of formula (XL) wherein Q is as defined herein for compounds of formula (I).Typical conditions for such transformations can be found in Synthesis (2003), (18), 2815-2826, Tetrahedron Letters, 50(49), 6818-6822; 2009; Chemistry-A European Journal, 15(20), 5006-5011; 2009; Journal of Organic Chemistry (2009), 74(12), 4646-4649 or in Synlett, (19), 3036-3040; 2008. Amidines of formula (XL) are commercially available or can be prepared by methods well known to the person skilled in the art.
(38) Compounds of formula (XXXIX) may be prepared from a compound of formula (XXXVIII) wherein R29 is a halogen, in particular chlorine, bromine or iodine and D5 is as defined herein for compounds of formula (I) and compounds of formula (XXXVII) wherein X is as defined herein for compounds of formula (I). Typical conditions for such
transformations can be found for example in Synthesis (2003), (18), 2815-2826. It has now been found that the compounds of formula (I) according to the invention have, for practical purposes, a very advantageous spectrum of activities for protecting useful plants against diseases that are caused by phytopathogenic microorganisms, such as fungi, bacteria or viruses.
The invention therefore also relates to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a compound of formula (I) is applied as active ingredient to the plants, to parts thereof or the locus thereof. The compounds of formula (I) according to the invention are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous useful plants. The compounds of formula (I) can be used to inhibit or destroy the diseases that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
It is also possible to use compounds of formula (I) as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
Furthermore the compounds of formula (I) according to the invention may be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage or in hygiene management.
The compounds of formula (I) are, for example, effective against the
phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara). Within the scope of the invention, useful plants to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.
The term "useful plants" is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® , Herculex I® and
LibertyLink®.
The term "useful plants" is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus. Examples of such plants are: YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylllB(bl) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a CrylllB(bl) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin); Bollgard I® (cotton variety that expresses a CrylA(c) toxin); Bollgard II® (cotton variety that expresses a CrylA(c) and a CryllA(b) toxin); VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CrylllA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Btll corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.
The term "useful plants" is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
The term "locus" of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil. An example for such a locus is a field, on which crop plants are growing.
The term "plant propagation material" is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion.
Preferably "plant propagation material" is understood to denote seeds.
The compounds of formula (I) can be used in unmodified form or, preferably, together with carriers and adjuvants conventionally employed in the art of formulation.
Therefore the invention also relates to compositions for controlling and protecting against phytopathogenic microorganisms, comprising a compound of formula (I) and an inert carrier, and to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a composition, comprising a compound of formula (I) as active ingredient and an inert carrier, is applied to the plants, to parts thereof or the locus thereof.
To this end compounds of formula (I) and inert carriers are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
Suitable carriers and adjuvants (auxiliaries) can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
The compounds of formula (I) or compositions, comprising a compound of formula
(I) as active ingredient and an inert carrier, can be applied to the locus of the plant or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
A preferred method of applying a compound of formula (I), or a composition, comprising a compound of formula (I) as active ingredient and an inert carrier, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen. However, the compounds of formula (I) may also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
A formulation, i.e. a composition comprising the compound of formula (I) and, if desired, a solid or liquid adjuvant, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface-active compounds (surfactants).
The agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula (I), 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from lOg to 1kg a.i./ha, most preferably from 20g to 600g a.i./ha. When used as seed drenching agent, convenient rates of application are from lOmg to lg of active substance per kg of seeds. The rate of application for the desired action can be determined by experiments. It depends for example on the type of action, the developmental stage of the useful plant, and on the application (location, timing, application method) and can, owing to these parameters, vary within wide limits.
The compounds of formula (I), or a pharmaceutical salt thereof, described above may also have an advantageous spectrum of activity for the treatment and/or prevention of microbial infection in an animal. "Animal" can be any animal, for example, insect, mammal, reptile, fish, amphibian, preferably mammal, most preferably human. "Treatment" means the use on an animal which has microbial infection in order to reduce or slow or stop the increase or spread of the infection, or to reduce the infection or to cure the infection.
"Prevention" means the use on an animal which has no apparent signs of microbial infection in order to prevent any future infection, or to reduce or slow the increase or spread of any future infection.
According to the present invention there is provided the use of a compound of formula (I) in the manufacture of a medicament for use in the treatment and/or prevention of microbial infection in an animal. There is also provided the use of a compound of formula (I) as a pharmaceutical agent. There is also provided the use of a compound of formula (I) as an antimicrobial agent in the treatment of an animal. According to the present invention there is also provided a pharmaceutical composition comprising as an active ingredient a compound of formula (I), or a pharmaceutically acceptable salt thereof, and a
pharmaceutically acceptable diluent or carrier. This composition can be used for the treatment and/or prevention of antimicrobial infection in an animal. This pharmaceutical composition can be in a form suitable for oral administration, such as tablet, lozenges, hard capsules, aqueous suspensions, oily suspensions, emulsions dispersible powders, dispersible granules, syrups and elixirs. Alternatively this pharmaceutical composition can be in a form suitable for topical application, such as a spray, a cream or lotion. Alternatively this pharmaceutical composition can be in a form suitable for parenteral administration, for example injection. Alternatively this pharmaceutical composition can be in inhalable form, such as an aerosol spray.
The compounds of formula (I) may be effective against various microbial species able to cause a microbial infection in an animal. Examples of such microbial species are those causing Aspergillosis such as Aspergillus fumigatus, A. flavus, A. terrus, A. nidulans and A. niger; those causing Blastomycosis such as Blastomyces dermatitidis; those causing Candidiasis such as Candida albicans, C. glabrata, C. tropicalis, C. parapsilosis, C. krusei and C. lusitaniae; those causing Coccidioidomycosis such as Coccidioides immitis; those causing Cryptococcosis such as Cryptococcus neoformans; those causing Histoplasmosis such as Histoplasma capsulatum and those causing Zygomycosis such as Absidia corymbifera, Rhizomucor pusillus and Rhizopus arrhizus. Further examples are Fusarium Spp such as Fusarium oxysporum and Fusarium solani and Scedosporium Spp such as Scedosporium apiospermum and Scedosporium prolificans. Still further examples are Microsporum Spp, Trichophyton Spp, Epidermophyton Spp, Mucor Spp, Sporothorix Spp, Phialophora Spp, Cladosporium Spp, Petriellidium spp, Paracoccidioides Spp and Histoplasma Spp.
The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
The present invention provides a fungicidal composition comprising a fungicidally effective amount of a compound of formula (I), optionally comprising an additional active ingredient. The compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as an insecticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. The further, other biocidally active ingredient are known for example from "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition (New edition (02 Nov 2003)); Editor: C. D. S. Tomlin; The British Crop Protection Council, ISBN-10: 1901396134; ISBN-13: 978-1901396133] or its electronic version "e-Pesticide Manual V4.2" or from the website http://www.alanwood.net/pesticides/ or preferably one of the further pesticides listed below.
The following mixtures of the compounds of TX with a further active ingredient (B) are preferred (the abbreviation "TX" means a compound encompassed by the compounds of formula I, or preferably the term "TX" refers to a compound selected from the Table 2):
(B)
(Bl) a strobilurin fungicide + TX,
(B2) an azole fungicide + TX,
(B3) a morpholine fungicide + TX,
(B4) an anilinopyrimidine fungicide + TX,
(B5) a fungicide selected from the group consisting of
Fluconazole + TX, Fluconazole-cis + TX, Fluxapyroxad + TX, Ametoctradin + TX, Flutianil + TX, Isotianil + TX, Valiphenal + TX, Anilazine + TX, arsenates + TX, benalaxyl + TX, benalaxyl-M + TX, benodanil + TX, benomyl + TX, benthiavalicarb + TX,
benthiavalicarb-isopropyl + TX, biphenyl + TX, bitertanol + TX, blasticidin-S + TX, bordeaux mixture + TX, boscalid + TX, bupirimate + TX, cadmium chloride + TX, captafol + TX, captan + TX, carbendazim + TX, carbon disulfide + TX, carboxin + TX, carpropamid + TX, cedar leaf oil + TX, chinomethionat + TX, chlorine + TX, chloroneb + TX, chlorothalonil + TX, chlozolinate + TX, cinnamaldehyde + TX, copper + TX, copper ammoniumcarbonate + TX, copper hydroxide + TX, copper octanoate + TX, copper oleate + TX, copper sulphate + TX, cyazofamid + TX, cycloheximide + TX, cymoxanil + TX, dichlofluanid + TX, dichlone + TX, dichloropropene + TX, diclocymet + TX, diclomezine + TX, dicloran + TX, diethofencarb + TX, diflumetorim + TX, dimethirimol + TX,
dimethomorph + TX, dinocap + TX, dithianon + TX, dodine + TX, edifenphos + TX, ethaboxam + TX, ethirimol + TX, etridiazole + TX, famoxadone + TX, fenamidone + TX, fenaminosulf + TX, fenamiphos + TX, fenarimol + TX, fenfuram + TX, fenhexamid + TX, fenoxanil + TX, fenpiclonil + TX, fentin acetate + TX, fentin chloride + TX, fentin hydroxide + TX, ferbam + TX, ferimzone + TX, fluazinam + TX, fludioxonil + TX, flusulfamide + TX, flusulfamide + TX, flutolanil + TX, folpet + TX, formaldehyde + TX, fosetyl-aluminium + TX, fthalide + TX, fuberidazole + TX, furalaxyl + TX, furametpyr + TX, flyodin + TX, fuazatine + TX, hexachlorobenzene + TX, hymexazole + TX, iminoctadine + TX, iodocarb + TX, iprobenfos + TX, iprodione + TX, iprovalicarb + TX, isoprothiolane + TX, kasugamycin + TX, mancozeb + TX, maneb + TX, manganous di methyl dithiocarba mate + TX, mefenoxam + TX, mepronil + TX, mercuric chloride + TX, mercury + TX, metalaxyl + TX, methasulfocarb + TX, metiram + TX, metrafenone + TX, nabam + TX, neem oil (hydrophobic extract) + TX, nuarimol + TX, octhilinone + TX, ofurace + TX, oxadixyl + TX, oxine copper + TX, oxolinic acid + TX, oxycarboxin + TX, oxytetracycline + TX,
paclobutrazole + TX, paraffin oil + TX, paraformaldehyde + TX, pencycuron + TX, pentachloronitrobenzene + TX, pentachlorophenol + TX, penthiopyrad + TX, perfurazoate + TX, phosphoric acid + TX, polyoxin + TX, polyoxin D zinc salt + TX, potassium bicarbonate + TX, probenazole + TX, procymidone + TX, propamocarb + TX, propineb + TX, proquinazid + TX, prothiocarb + TX, pyrazophos + TX, pyrifenox + TX, pyroquilon + TX, quinoxyfen + TX, quintozene + TX, silthiofam + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, streptomycin + TX, sulphur + TX, TCMTB + TX, tecloftalam + TX, tecnazene + TX, thiabendazole + TX, thifluzamide + TX, thiophanate + TX, thiophanate-methyl + TX, thiram + TX, tolclofos-methyl + TX, tolyfluanid + TX, triazoxide + TX, trichoderma harzianum + TX, tricyclazole + TX, triforine + TX, triphenyltin hydroxide + TX, validamycin + TX, vinclozolin + TX, zineb + TX, ziram + TX, zoxamide + TX, 1 + TX,l-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2 + TX,4-dichlorophenyl benzenesulfonate + TX, 2-fluoro-/V-methyl-/V-l-naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX,
a compound of formula B-5.1 + TX
Figure imgf000135_0001
a compound of formula B-5.2 + TX
Figure imgf000135_0002
a compound of formula B-5.4 + TX
Figure imgf000136_0001
a com ound of formula B-5.5 + TX
Figure imgf000136_0002
a compound of formula B-5.6 + TX
Figure imgf000136_0003
a compound of formula B-5.7 + TX
Figure imgf000136_0004
3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl- phenyl)-amide (compound B-5.8) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (9-isopropyp-l,2,3,4-tetrahydro-l,4-methano-naphthalen-5-yl)-amide (compound B- 5.9) + TX, l,3-dimethyl-5-fluoro-lH-pyrazole-4-carboxylic acid [2-(l,3- dimethylbutyl)phenyl]-amide (compound B-5.10) + TX, 3-difluoromethyl-l-methyl-lH- pyrazole-4-carboxylic acid (3',4'-dichloro-5-fluoro-l,l'-biphenyl-2-yl)-amide (compound B- 5.11) + TX, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2- (trifluoromethyl)benzamid (compound B-5.12) + TX, 3-difluoromethyl-l-methyl-lH- pyrazole-4-carboxylic acid N-[2-(l,l,2,2-tetrafluoroethoxy)phenyl]-amide (compound B- 5.13) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid N-[2-(l, 1,2,3,3,3- hexafluoropropoxy)phenyl]-amide (compound B-5.14), 3-difluoromethyl-l-methyl-lH- pyrazole-4-carboxylic acid N-[2-(2-chloro-l + T ,l,2-trifluoroethoxy)phenyl]-amide
(compound B-5.15) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid N-(4'- trifluoromethyl-biphen-2-yl)-amide (compound B-5.16) + TX, 3-difluoromethyl-l-methyl-lH- pyrazole-4-carboxylic acid N-(2'-trifluoromethyl-biphen-2-yl)-amide (compound B-5.17) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid N-(2'-trifluoromethyl-biphen-2- yl)-amide (compound B-5.18) + TX; 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-amide (compound B-5.19) + TX, 3-difluoromethyl-l- methyl-lH-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-l-methyl-indan-4-yl)- amide (compound B-5.20) + TX
a compound of formula B-5.21 + TX
Figure imgf000137_0001
(B6) a plant-bioregulator selected from the group consisting of
Acibenzolar + TX, 1-methyl-cyclopropene + TX, acibenzolar-S-methyl + TX, chlormequat chloride + TX, ethephon + TX, mepiquat chloride and trinexapc-ethyl;
(B7) an insecticide selected from the group consisting of
abamectin + TX, clothianidin + TX, emamectin benzoate + TX, imidacloprid + TX, tefluthrin + TX, thiamethoxam + TX,
and a compound of formula C + TX
Figure imgf000137_0002
wherein X is a bivalent group selected from
Figure imgf000137_0003
Figure imgf000138_0001
wherein a) Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R2 is bromine, R3 is methyl, R4 is CN and X is Xi;
b) Ri is methyl substituted by cyclopropyl, R2 is CF3, R3 is methyl, R4 is CI and X is c) Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R2 is CF3, R3 is methyl, R4 is CI and X is Xi;
d) Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R2 is CF3, R3 is methyl, R4 is CN and X is Xi;
e) Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R2 is OCH2CF3, R3 is methyl, R4 is CN and X is Xi;
f) Ri is isopropyl, R2 is methoxy; R3 is methyl, R4 is hydrogen and X is X8 ;
g) Ri is isopropyl, R2 is trifluoromethyl, R3 is chlorine, R4 is hydrogen and X is X8; h) Ri is isopropyl, R2 is trifluoromethyl, R3 is methyl, R4 is hydrogen and X is X8; i) Ri is methyl, R2 is bromine, R3 is methyl, R4 is CN and X is Xi ;
j) Ri is methyl, R2 is bromine, R3 is methyl, R4 is CI and X is Xi;
and (B8) glyphosate + TX, glyphosate diammonium +TX, glyphosate
dimethylammonium + TX, glyphosate isopropylammonium +TX, glyphosate
monoammonium + TX, glyphosate potassium + TX, glyphosate sesquisodium + TX, glyphosate trimesium +TX, (5-chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl- phenyl)-methanone +TX, (5-bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6- methyl-phenyl)-methanone + TX, 2-{2-[(E)-3-(2,6-Dichloro-phenyl)-l-methyl-prop-2-en- (E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide + TX, 3-[5- (4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine + TX
a compound of formula D + TX
Figure imgf000139_0001
fomesafen + TX, Glufosinate and its salts TX, and (B9) Isopyrazam + TX, Sedaxane a compound of formula (E) + TX
Figure imgf000140_0001
a compound of formula (F) + TX
Figure imgf000140_0002
Preferred compositions comprising a compound of formula TX and
(B) a compound selected from the group consisting of
(Bl) a strobilurin fungicide + TX, (B2) an azole fungicide + TX, (B3) a morpholine fungicide + TX, (B4) an anilinopyrimidine fungicide + TX, (B5) a fungicide selected from the group consisting of
anilazine (878) + TX, arsenates + TX, benalaxyl (56) + TX, benalaxyl-M + TX, benodanil (896) + TX, benomyl (62) + TX, benthiavalicarb + TX, benthiavalicarb-isopropyl (68) + TX, biphenyl (81) + TX, bitertanol (84) + TX, blasticidin-S (85) + TX, bordeaux mixture (87) + TX, boscalid (88) + TX, bupirimate (98) + TX, cadmium chloride + TX, captafol (113) + TX,
captan (114) + TX, carbendazim (116) + TX, carbon disulfide (945) + TX, carboxin
(120) + TX, carpropamid (122) + TX, cedar leaf oil + TX, chinomethionat (126) + TX, chlorine + TX, chloroneb (139) + TX, chlorothalonil (142) + TX, chlozolinate (149) + TX, cinnamaldehyde + TX, copper + TX, copper ammoniumcarbonate + TX, copper hydroxide (169) + TX, copper octanoate (170) + TX, copper oleate + TX, copper sulphate (87) + TX, cyazofamid (185) + TX, cycloheximide (1022) + TX, cymoxanil (200) + TX, dichlofluanid (230) + TX, dichlone (1052) + TX, dichloropropene (233) + TX, diclocymet (237) + TX, diclomezine (239) + TX, dicloran (240) + TX, diethofencarb (245) + TX, diflumetorim (253) + TX, dimethirimol (1082) + TX, dimethomorph (263) + TX, dinocap (270) + TX, dithianon (279) + TX, dodine (289) + TX, edifenphos (290) + TX, ethaboxam (304) + TX, ethirimol (1133) + TX, etridiazole (321) + TX, famoxadone (322) + TX, fenamidone (325) + TX, fenaminosulf (1144) + TX, fenamiphos (326) + TX, fenarimol (327) + TX, fenfuram (333) + TX, fenhexamid (334) + TX, fenoxanil (338) + TX, fenpiclonil (341) + TX, fentin acetate (347) + TX, fentin chloride + TX, fentin hydroxide (347) + TX, ferbam (350) + TX, ferimzone (351) + TX, fluazinam (363) + TX, fludioxonil (368) + TX, flusulfamide (394) + TX, flutolanil (396) + TX, folpet (400) + TX, formaldehyde (404) + TX, fosetyl-aluminium (407) + TX, fthalide (643) + TX, fuberidazole (419) + TX, furalaxyl (410) + TX, furametpyr (411) + TX, flyodin (1205) + TX, fuazatine (422) + TX, hexachlorobenzene (434) + TX, hymexazole + TX, iminoctadine (459) + TX, iodocarb (3-Iodo-2-propynyl butyl carbamate) + TX, iprobenfos (IBP) (469) + TX, iprodione (470) + TX, iprovalicarb (471) + TX, isoprothiolane (474) + TX, kasugamycin (483) + TX, mancozeb (496) + TX, maneb (497) + TX, manganous dimethyldithiocarbamate + TX, mefenoxam (Metalaxyl-M) (517) + TX, mepronil (510) + TX, mercuric chloride (511) + TX, mercury + TX, metalaxyl (516) + TX, methasulfocarb (528) + TX, metiram (546) + TX, metrafenone + TX, nabam (566) + TX, neem oil (hydrophobic extract) + TX, nuarimol (587) + TX, octhilinone (590) + TX, ofurace (592) + TX, oxadixyl (601) + TX, oxine copper (605) + TX, oxolinic acid (606) + TX, oxycarboxin (608) + TX, oxytetracycline (611) + TX, paclobutrazole (612) + TX, paraffin oil (628) + TX, paraformaldehyde + TX, pencycuron (620) + TX, pentachloronitrobenzene (716) + TX, pentachlorophenol (623) + TX, penthiopyrad + TX, perfurazoate + TX, phosphoric acid + TX, polyoxin (654) + TX, polyoxin D zinc salt (654) + TX, potassium bicarbonate + TX, probenazole (658) + TX, procymidone (660) + TX, propamocarb (668) + TX, propineb (676) + TX, proquinazid (682) + TX, prothiocarb (1361) + TX, pyrazophos (693) + TX, pyrifenox (703) + TX, pyroquilon (710) + TX, quinoxyfen (715) + TX, quintozene (PCNB) (716) + TX, silthiofam (729) + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, streptomycin (744) + TX, sulphur (754) + TX, TCMTB + TX, tecloftalam + TX, tecnazene (TCNB) (767) + TX, thiabendazole (790) + TX, thifluzamide (796) + TX, thiophanate (1435) + TX, thiophanate-methyl (802) + TX, thiram (804) + TX, tolclofos-methyl (808) + TX, tolylfluanid (810) + TX, triazoxide (821) + TX, trichoderma harzianum (825) + TX, tricyclazole (828) + TX, triforine (838) + TX, triphenyltin hydroxide (347) + TX, validamycin (846) + TX, vinclozolin (849) + TX, zineb (855) + TX, ziram (856) + TX, zoxamide (857) + TX, l,l-bis(4-chlorophenyl)-2- ethoxyethanol (IUPAC-Name) (910) + TX, 2 + TX, 4-dichlorophenyl benzenesulfonate (IUPAC- / Chemical Abstracts-Name) (1059) + TX, 2-fluoro-/V-methyl-/V-l- naphthylacetamide (IUPAC-Name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC- Name) (981) + TX,
a compound of formula B-5.1 + TX
Figure imgf000142_0001
a compound of formula B-5.2 + TX
Figure imgf000142_0002
a compound of formula B-5.3 +TX
Figure imgf000142_0003
a com ound of formula B-5.4 +TX
Figure imgf000142_0004
mpound of formula B-5.5 +TX
Figure imgf000142_0005
compound of formula B-5.6 +TX
Figure imgf000142_0006
a compound of formula B-5.7 +TX
Figure imgf000143_0001
3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl- phenyl)-amide (compound B-5.8) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (9-isopropyp-l,2,3,4-tetrahydro-l,4-methano-naphthalen-5-yl)-amide (compound B- 5.9) + TX, l,3-dimethyl-5-fluoro-lH-pyrazole-4-carboxylic acid [2-(l,3- dimethylbutyl)phenyl]-amide (compound B-5.10) + TX, 3-difluoromethyl-l-methyl-lH- pyrazole-4-carboxylic acid (3',4'-dichloro-5-fluoro-l,l'-biphenyl-2-yl)-amide (compound B- 5.11) + TX, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2- (trifluoromethyl)benzamid (compound B-5.12) + TX, 3-difluoromethyl-l-methyl-lH- pyrazole-4-carboxylic acid N-[2-(l,l,2,2-tetrafluoroethoxy)phenyl]-amide (compound B- 5.13) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid N-[2-(l, 1,2,3,3,3- hexafluoropropoxy)phenyl]-amide (compound B-5.14) + TX, 3-difluoromethyl-l-methyl-lH- pyrazole-4-carboxylic acid N-[2-(2-chloro-l,l,2-trifluoroethoxy)phenyl]-amide (compound B- 5.15) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid N-(4'-trifluoromethyl- biphen-2-yl)-amide (compound B-5.16) + TX, 3-difluoromethyl-l-methyl-lH-pyrazole-4- carboxylic acid N-(2'-trifluoromethyl-biphen-2-yl)-amide (compound B-5.17) + TX, and 3- difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid N-(2'-trifluoromethyl-biphen-2-yl)- amide (compound B-5.18) + TX
(B6) a plant-bioregulator selected from the group consisting of
acibenzolar-S-methyl (6) + TX, chlormequat chloride (137) + TX, ethephon (307) +
TX, mepiquat chloride (509) and trinexapc-ethyl (841);
(B7) an insecticide selected from the group consisting of
abamectin (1) + TX, clothianidin (165) + TX, emamectin benzoate (291) + TX, imidacloprid (458) + TX, tefluthrin (769) + TX, thiamethoxam (792) + TX, a compound of formula B-7.1 +TX
Figure imgf000144_0001
and a compound of formula B-7.2 +TX;
Figure imgf000144_0002
and (B8) glyphosate (419) +TX.
Examples of especially suitable mixtures selected from the following group P:
Group P: especially suitable mixtures according to the invention:
a strobilurin fungicide selected from azoxystrobin (47) + TX, dimoxystrobin (226) +
TX, fluoxastrobin (382) + TX, kresoxim-methyl (485) + TX, metominostrobin (551) + TX, orysastrobin + TX, picoxystrobin (647) + TX, pyraclostrobin (690); trifloxystrobin (832) +
TX, a compound of formula B-1.1 +TX
Figure imgf000144_0003
an azole fungicide selected from azaconazole (40) + TX, bromuconazole (96) + TX, cyproconazole (207) + TX, difenoconazole (247) + TX, diniconazole (267) + TX, diniconazole-M (267) + TX, epoxiconazole (298) + TX, fenbuconazole (329) + TX, fluquinconazole (385) + TX, flusilazole (393) + TX, flutriafol (397) + TX, hexaconazole (435) + TX, imazalil (449) + TX, imibenconazole (457) + TX, ipconazole (468) + TX, metconazole (525) + TX, myclobutanil (564) + TX, oxpoconazole (607) + TX, pefurazoate (618) + TX, penconazole (619) + TX, prochloraz (659) + TX, propiconazole (675) + TX, prothioconazole (685) + TX, simeconazole (731) + TX, tebuconazole (761) + TX, tetraconazole (778) + TX, triadimefon (814) + TX, triadimenol (815) + TX, triflumizole (834) + TX, triticonazole (842) + TX, diclobutrazol (1068) + TX, etaconazole (1129) + TX, furconazole (1198) + TX, furconazole-cis (1199) and quinconazole (1378); a morpholine fungicide mixture selected from aldimorph + TX, dodemorph (288) + TX, fenpropimorph (344) + TX, tridemorph (830) + TX, fenpropidin (343) + TX, spiroxa d a compound of formula B-3.1 +TX
Figure imgf000145_0001
an anilino-pyrimidine fungicide selected from cyprodinil (208) + TX, mepanipyrim
(508) and pyrimethanil (705);
a fungicide mixture selected from the group consisting of
anilazine (878) + TX, arsenates + TX, benalaxyl (56) + TX, benalaxyl-M + TX, benodanil (896) + TX, benomyl (62) + TX, benthiavalicarb + TX, benthiavalicarb-isopropyl (68) + TX, biphenyl (81) + TX, bitertanol (84) + TX, blasticidin-S (85) + TX, bordeaux mixture (87) + TX, boscalid (88) + TX, bupirimate (98) + TX, cadmium chloride + TX, captafol (113) + TX,
captan (114) + TX, carbendazim (116) + TX, carbon disulfide (945) + TX, carboxin (120) + TX, carpropamid (122) + TX, cedar leaf oil + TX, chinomethionat (126) + TX, chlorine + TX, chloroneb (139) + TX, chlorothalonil (142) + TX, chlozolinate (149) + TX, cinnamaldehyde + TX, copper + TX, copper ammoniumcarbonate + TX, copper hydroxide (169) + TX, copper octanoate (170) + TX, copper oleate + TX, copper sulphate (87) + TX, cyazofamid (185) + TX, cycloheximide (1022) + TX, cymoxanil (200) + TX, dichlofluanid (230) + TX, dichlone (1052) + TX, dichloropropene (233) + TX, diclocymet (237) + TX, diclomezine (239) + TX, dicloran (240) + TX, diethofencarb (245) + TX, diflumetorim (253) + TX, dimethirimol (1082) + TX, dimethomorph (263) + TX, dinocap (270) + TX, dithianon (279) + TX, dodine (289) + TX, edifenphos (290) + TX, ethaboxam (304) + TX, ethirimol (1133) + TX, etridiazole (321) + TX, famoxadone (322) + TX, fenamidone (325) + TX, fenaminosulf (1144) + TX, fenamiphos (326) + TX, fenarimol (327) + TX, fenfuram (333) + TX, fenhexamid (334) + TX, fenoxanil (338) + TX, fenpiclonil (341) + TX, fentin acetate (347) + TX, fentin chloride + TX, fentin hydroxide (347) + TX, ferbam (350) + TX, ferimzone (351) + TX, fluazinam (363) + TX, fludioxonil (368) + TX, flusulfamide (394) + TX, flutolanil (396) + TX, folpet (400) + TX, formaldehyde (404) + TX, fosetyl-aluminium (407) + TX, fthalide (643) + TX, fuberidazole (419) + TX, furalaxyl (410) + TX, furametpyr (411) + TX, flyodin (1205) + TX, fuazatine (422) + TX, hexachlorobenzene (434) + TX, hymexazole + TX, iminoctadine (459) + TX, iodocarb (3-Iodo-2-propynyl butyl carbamate) + TX, iprobenfos (IBP) (469) + TX, iprodione (470) + TX, iprovalicarb (471) + TX, isoprothiolane (474) + TX, kasugamycin (483) + TX, mancozeb (496) + TX, maneb (497) + TX, manganous dimethyldithiocarbamate + TX, mefenoxam (Metalaxyl-M) (517) + TX, mepronil (510) + TX, mercuric chloride (511) + TX, mercury + TX, metalaxyl (516) + TX, methasulfocarb (528) + TX, metiram (546) + TX, metrafenone + TX, nabam (566) + TX, neem oil (hydrophobic extract) + TX, nuarimol (587) + TX, octhilinone (590) + TX, ofurace (592) + TX, oxadixyl (601) + TX, oxine copper (605) + TX, oxolinic acid (606) + TX, oxycarboxin (608) + TX, oxytetracycline (611) + TX, paclobutrazole (612) + TX, paraffin oil (628) + TX, paraformaldehyde + TX, pencycuron (620) + TX, pentachloronitrobenzene (716) + TX, pentachlorophenol (623) + TX, penthiopyrad + TX, perfurazoate + TX, phosphoric acid + TX, polyoxin (654) + TX, polyoxin D zinc salt (654) + TX, potassium bicarbonate + TX, probenazole (658) + TX, procymidone (660) + TX, propamocarb (668) + TX, propineb (676) + TX, proquinazid (682) + TX, prothiocarb (1361) + TX, pyrazophos (693) + TX, pyrifenox (703) + TX, pyroquilon (710) + TX, quinoxyfen (715) + TX, quintozene (PCNB) (716) + TX, silthiofam (729) + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, streptomycin (744) + TX, sulphur (754) + TX, TCMTB + TX, tecloftalam + TX, tecnazene (TCNB) (767) + TX, thiabendazole (790) + TX, thifluzamide (796) + TX, thiophanate (1435) + TX, thiophanate-methyl (802) + TX, thiram (804) + TX, tolclofos-methyl (808) + TX, tolylfluanid (810) + TX, triazoxide (821) + TX, trichoderma harzianum (825) + TX, tricyclazole (828) + TX, triforine (838) + TX, triphenyltin hydroxide (347) + TX, validamycin (846) + TX, vinclozolin (849) + TX, zineb (855) + TX, ziram (856) + TX, zoxamide (857) + TX, 1 + TX,l-bis(4-chlorophenyl)-2- ethoxyethanol (IUPAC-Name) (910) + TX, 2 + TX,4-dichlorophenyl benzenesulfonate (IUPAC- / Chemical Abstracts-Name) (1059) + TX, 2-fluoro-/V-methyl-/V-l- naphthylacetamide (IUPAC-Name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC- Name) (981) + TX,
a compound of formula B-5.1 + TX, a compound of formula B-5.2 + TX, a compound of formula B-5.3 + TX, a compound of formula B-5.4 + TX, a compound of formula B-5.5 + TX, a compound of formula B-5.6 + TX, a compound of formula B-5.7 + TX, compound B-5.8 + TX, compound B-5.9 + TX, compound B-5.10 + TX, compound B- 5.11 + TX, compound B-5.12 + TX, compound B-5.13 + TX, compound B-5.14 + TX, compound B-5.15 + TX, compound B-5.16 + TX, compound B-5.17 and compound B-5.18; a plant-bioregulator selected from the group consisting of
acibenzolar-S-methyl (6) + TX, chlormequat chloride (137) + TX, ethephon (307) + TX, mepiquat chloride (509) and trinexapc-ethyl (841);
an insecticide selected from the group consisting of abamectin (1) + TX, clothianidin (165) + TX, emamectin benzoate (291) + TX, imidadoprid (458) + TX, tefluthrin (769) + TX, thiamethoxam (792) + TX, and glyphosate (419) + TX, a compound of formula D) + TX
Figure imgf000147_0001
fomesafen + TX, and (B9) Isopyrazam + TX, Sedaxane + TX,
a compound of formula (E) + TX
Figure imgf000147_0002
compound of formula (F) + TX
Figure imgf000147_0003
Further examples of especially suitable mixtures selected from the following group
Q:
Group Q: especially suitable compositions according to the invention:
a strobilurin fungicide selected from the group consisting of azoxystrobin + TX, dimoxystrobin + TX, fluoxastrobin + TX, kresoxim-methyl + TX, metominostrobin + TX, orysastrobin + TX, picoxystrobin + TX, pyraclostrobin; trifloxystrobin and a compound of formula B-l.l;
an azole fungicide selected from the group consisting of azaconazole + TX, bromuconazole + TX, cyproconazole + TX, difenoconazole + TX, diniconazole + TX, diniconazole-M + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafol + TX, hexaconazole + TX, imazalil + TX, imibenconazole + TX, ipconazole + TX, metconazole + TX, myclobutanil + TX, oxpoconazole + TX, pefurazoate + TX, penconazole + TX, prochloraz + TX, propiconazole + TX, prothioconazole + TX, simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, diclobutrazol + TX, etaconazole + TX, furconazole + TX, furconazole-cis + TX and quinconazole + TX;
a morpholine fungicide selected from the group consisting of aldimorph + TX, dodemorph + TX, fenpropimorph + TX, tridemorph + TX, fenpropidin + TX, spiroxamine + TX, piperalin and a compound of formula B-3.1;
an anilino-pyrimidine fungicide selected from the group consisting of cyprodinil + TX, mepanipyrim and pyrimethanil;
a fungicide selected from the group consisting of benalaxyl + TX, benalaxyl-M + TX, benomyl + TX, bitertanol + TX, boscalid + TX, captan + TX, carboxin + TX, carpropamid + TX, chlorothalonil + TX, copper + TX, cyazofamid + TX, cymoxanil + TX, diethofencarb + TX, dithianon + TX, famoxadone + TX, fenamidone + TX, fenhexamide + TX, fenoxycarb + TX, fenpiclonil + TX, fluazinam + TX, fludioxonil + TX, flutolanil + TX, folpet + TX, guazatine + TX, hymexazole + TX, iprodione + TX, lufenuron + TX, mancozeb + TX, metalaxyl + TX, mefenoxam + TX, metrafenone + TX, nuarimol + TX, paclobutrazol + TX, pencycuron + TX, penthiopyrad + TX, procymidone + TX, proquinazid + TX, pyroquilon + TX, quinoxyfen + TX, silthiofam + TX, sulfur + TX, thiabendazole + TX, thiram + TX, triazoxide + TX, tricyclazole + TX, a compound of formula B-5.1 + TX, a compound of formula B-5.2 + TX, a compound of formula B-5.3 + TX, a compound of formula B-5.4 + TX, a compound of formula B-5.5 + TX, a compound of formula B-5.6 + TX, a compound of formula B-5.7 + TX, a compound of formula B-5.8 + TX, a compound of formula B-5.9 + TX, a compound of formula B-5.10 and a compound of formula B-5.12;
a plant-bioregulator selected from acibenzolar-S-methyl + TX, chlormequat chloride + TX, ethephon + TX, mepiquat chloride and trinexapc-ethyl;
an insecticide selected from abamectin + TX, emamectin benzoate + TX, tefluthrin + TX, thiamethoxam + TX, and glyphosate + TX, a compound of formula D
Figure imgf000148_0001
fomesafen + TX, and (B9) Isopyrazam + TX, Sedaxane + TX,
a compound of formula (E) + TX
Figure imgf000149_0001
a compound of formula (F) + TX
Figure imgf000149_0002
It has been found that the use of component (B) in combination with component TX surprisingly and substantially may enhance the effectiveness of the latter against fungi, and vice versa. Additionally, the method of the invention is effective against a wider spectrum of such fungi that can be combated with the active ingredients of this method, when used solely.
The active ingredient mixture of component TX to component (B) comprises compounds of formula I and a further, other biocidally active ingredients or compositions or if desired, a solid or liquid adjuvant preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, special preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2: 1 being likewise preferred, above all in a ratio of 1:1, or 5: 1, or 5:2, or 5:3, or 5:4, or 4: 1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1: 150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1: 1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
It has been found, surprisingly, that certain weight ratios of component TX to component (B) are able to give rise to synergistic activity. Therefore, a further aspect of the invention are compositions, wherein component TX and component (B) are present in the composition in amounts producing a synergistic effect. This synergistic activity is apparent from the fact that the fungicidal activity of the composition comprising component TX and component (B) is greater than the sum of the fungicidal activities of component TX and of component (B). This synergistic activity extends the range of action of component TX and component (B) in two ways. Firstly, the rates of application of component TX and component (B) are lowered whilst the action remains equally good, meaning that the active ingredient mixture still achieves a high degree of phytopathogen control even where the two individual components have become totally ineffective in such a low application rate range. Secondly, there is a substantial broadening of the spectrum of phytopathogens that can be controlled.
A synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components. The action to be expected E for a given active ingredient combination obeys the so-called COLBY formula and can be calculated as follows (COLBY, S.R. "Calculating synergistic and antagonistic responses of herbicide combination". Weeds, Vol. 15, pages 20-22; 1967):
ppm = milligrams of active ingredient (= a.i.) per liter of spray mixture
X = % action by active ingredient A) using p ppm of active ingredient
Y = % action by active ingredient B) using q ppm of active ingredient.
According to COLBY, the expected (additive) action of active ingredients A)+B) using
X · Y
p+q ppm of active ingredient is E = X + Y -
If the action actually observed (0) is greater than the expected action (E), then the action of the combination is super-additive, i.e. there is a synergistic effect. In
mathematical terms, synergism corresponds to a positive value for the difference of (O-E). In the case of purely complementary addition of activities (expected activity), said difference (O-E) is zero. A negative value of said difference (O-E) signals a loss of activity compared to the expected activity.
However, besides the actual synergistic action with respect to fungicidal activity, the compositions according to the invention can also have further surprising advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageuos degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination.
Some compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment fungicides. With the compositions according to the invention it is possible to inhibit or destroy the phytopathogenic microorganisms which occur in plants or in parts of plants (fruit, blossoms, leaves, stems, tubers, roots) in different useful plants, while at the same time the parts of plants which grow later are also protected from attack by phytopathogenic microorganisms.
The compositions according to the invention can be applied to the phytopathogenic microorganisms, the useful plants, the locus thereof, the propagation material thereof, storage goods or technical materials threatened by microorganism attack.
The compositions according to the invention may be applied before or after infection of the useful plants, the propagation material thereof, storage goods or technical materials by the microorganisms.
A further aspect of the present invention is a method of controlling diseases on useful plants or on propagation material thereof caused by phytopathogens, which comprises applying to the useful plants, the locus thereof or propagation material thereof a composition according to the invention. Preferred is a method, which comprises applying to the useful plants or to the locus thereof a composition according to the invention, more preferably to the useful plants. Further preferred is a method, which comprises applying to the propagation material of the useful plants a composition according to the invention.
The components (B) are known. Where the components (B) are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. Tomlin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular component (B); for example, the compound "abamectin" is described under entry number (1). Most of the components (B) are referred to hereinabove by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in round brackets for the particular component (B); in that case, the IUPAC name, the IUPAC/Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "development code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed.
The following components B) are registered under a CAS-Reg. No.
Fluconazole (86386-73-4), Fluconazole-cis (112839-32-4), Fluxapyroxad (907204- 31-3), Ametoctradin (865318-97-4), Flutianil (958647-10-4), Isotianil (224049-04-1), Valiphenal (283159-90-0), Acibenzolar (126448-41-7), 1-methyl-cyclopropene (3100-04-7), glyphosate diammonium (69254-40-6) , glyphosate dimethylammonium (34494-04-7) , glyphosate isopropylammonium (38641-94-0) , glyphosate monoammonium (40465-66-5) , glyphosate potassium (70901-20-1) , glyphosate sesquisodium (70393-85-0) , glyphosate trimesium (81591-81-3), Glufosinate and its salts (51276-47-2, 35597-44-5 (S-isomer)), aldimorph (CAS 91315-15-0); arsenates (CAS 1327-53-3); benalaxyl -M (CAS 98243-83-5); benthiavalicarb (CAS 413615-35-7); cadmium chloride (CAS 10108-64-2); cedar leaf oil (CAS 8007-20-3); chlorine (CAS 7782-50-5); cinnamaldehyde (CAS: 104-55-2); copper ammoniumcarbonate (CAS 33113-08-5); copper oleate (CAS 1120-44-1); iodocarb (3-Iodo- 2-propynyl butyl carbamate) (CAS 55406-53-6); hymexazole (CAS 10004-44-1); manganous dimethyldithiocarbamate (CAS 15339-36-3); mercury (CAS 7487-94-7; 21908-53-2; 7546- 30-7); metrafenone (CAS 220899-03-6); neem oil (hydrophobic extract) (CAS 8002-65-1); orysastrobin CAS 248593-16-0); paraformaldehyde (CAS 30525-89-4); penthiopyrad (CAS 183675-82-3); phosphoric acid (CAS 7664-38-2); potassium bicarbonate (CAS 298-14-6); sodium bicarbonate (CAS 144-55-8); sodium diacetate (CAS 127-09-3); sodium propionate (CAS 137-40-6);TCMTB (CAS 21564-17-0); and tolyfluanid (CAS 731-27-1).
Compound B-l.l ("enestrobin") is described in EP-0-936-213; compound B-3.1 ("flumorph") in US-6,020,332, CN-1-167-568, CN-1-155-977 and in EP-0-860-438;
compound B-5.1 ("mandipropamid") in WO 01/87822; compound B-5.2 in WO 98/46607; compound B-5.3 ("fluopicolide") in WO 99/42447; compound B-5.4 ("cyflufenamid") in WO 96/19442; compound B-5.5 in WO 99/14187; compound B-5.6 ("pyribencarb") is registered under CAS-Reg. No. 325156-49-8; compound B-5.7 ("amisulbrom" or "ambromdole") is registered under CAS-Reg. No. 348635-87-0; compound B-5.8 (3-difluoromethyl-l-methyl- lH-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl-phenyl)-amide) is described in WO 03/74491; compound B-5.9 (3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (9- isopropyp-l,2,3,4-tetrahydro-l,4-methano-naphthalen-5-yl)-amide) is described in
WO 04/35589 and in WO 06/37632; compound B-5.10 (l,3-dimethyl-5-fluoro-lH-pyrazole- 4-carboxylic acid [2-(l,3-dimethylbutyl)phenyl]-amide) is described in WO 03/10149;
compound B-5.11 (3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (3',4'-dichloro- 5-fluoro-l,l'-biphenyl-2-yl)-amide; "bixafen") is registered under CAS-Reg. No.: 581809-46- 3 and described in WO 03/70705; compound B-5.12 (N-{2-[3-Chloro-5- (trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamid; "fluopyram") is registered under CAS-Reg. No: 658066-35-4 and described in WO 04/16088; compounds B-5.13, B- 5.14 and B-5.15 are described in WO 2007/17450; compounds B-5.16, B-5.17 and B-5.18 are described in WO 2006/120219; The compounds of formula IV are for example described in WO 04/067528, WO 2005/085234, WO 2006/111341 , WO 03/015519, WO 2007/020050, WO 2006/040113, and WO 2007/093402; The compound of formula V is described in WO 2001/094339; compound B-21 is described in WO 2010/123791.
Isopyrazam (3-(difluoromethyl)-l-methyl-/V-[l,2,3,4-tetrahydro-9-(l-methylethyl)-l,4- methanonaphthalen-5-yl]-lH-pyrazole-4-carboxamide) is described in WO 2004/035589, in
WO 2006/037632 and in EP1556385B1 and is registered under the CAS-Reg. 881685-58-1.
Sedaxane (/V-[2-[l, -bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4- carboxamide) is described in WO 2003/074491 and is registered under the CAS-Reg.
874967-67-6; The compound of formula (VI) is described in WO 2008/014870; and the compounds of formula (VII) is described in WO 2007/048556. Fomesafen is registered under the CAS-Reg. No. 72178-02-0.
3-Difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (4'-methylsulfanyl- biphenyl-2-yl)-amide (compound B-5.19) is registered under CAS number 1021864-46-9, 3- difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-l- methyl-indan-4-yl)-amide (compound B-5.20) is registered under CAS number
The compositions according to the invention may also comprise more than one of the active components (B), if, for example, a broadening of the spectrum of disease control is desired. For instance, it may be advantageous in the agricultural practice to combine two or three components (B) with component TX. An example is a composition comprising a compound of formula (I), azoxystrobin and cyproconazole.
In the above different lists of active ingredients to be mixed with a TX, the compound of the formula I is preferably a compound of Table 2.
In the above-mentioned mixtures of compounds of formula I, in particular a compound selected from said Table 2, with other insecticides, fungicides, herbicides, safeners, adjuvants and the like, the mixing ratios can vary over a large range and are, preferably 100:1 to 1:6000, especially 50:1 to 1:50, more especially 20:1 to 1:20, even more especially 10:1 to 1:10. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
The mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient" relates to the respective mixture of TX with the mixing partner).
Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation. The mixtures comprising a TX selected from Table 1 and one or more active ingredients as described above can be applied, for example, in a single "ready-mix" form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula I selected from Table 1 and the active ingredients as described above is not essential for working the present invention
The following non-limiting Examples illustrate the above-described invention in greater detail without limiting it. Those skilled in the art will promptly recognise appropriate variations from the procedures both as to reactants and as to reaction conditions and techniques. All references mentioned herein are incorporated by reference in their entirety.
Preparatory examples:
Throughout these examples, the isomer drawn is in excess in the reaction mixture and/or product.
Example 1: Preparation of P2
Figure imgf000154_0001
To a solution of 1.1 (39 mg) in ethanol (2 mL) were added O-methoxyhydroxylamine hydrochloride (31 mg) and HCI (2N; 1 mL). After stirring for 2h at reflux, the ethanol was evaporated under vacuum. The residue was treated with sodium bicarbonate until pH 9 and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, evaporated and urified over silica gel to give a colourless oil (30 mg).
Figure imgf000154_0002
Preparation of II: To a solution of 19 (114 mg) in ethanol (10 mL) was added palladium over charcoal (5%; lOmg). The reaction mixture was stirred for 3h30min under an atmosphere of hydrogen. Then it was filtered and evaporated to give a yellow oil (104 mg).
Figure imgf000155_0001
Preparation of 19: To a solution of 12 (117 mg) in dichloromethane (5 mL) was added triethylamine (37 μΙ_). The reaction mixture was cooled to 0-5°C using an ice bath, and then methanesulfonyl chloride (21 μΙ_) was added. After stirring for 30min at 0-5°C, the reaction mixture was further stirred for 4 days at ambient temperature. It was quenched with a saturated sodium bicarbonate solution and extracted with dichloromethane. The organic phase was washed with water, dried over magnesium sulphate and then concentrated. The residue was dissolved in tetrahydrofuran and 1,8- Diazabicyclo[5.4.0]undec-7-ene (3eq) was added. The reaction mixture was stirred for 5 days at ambient temperature and then overnight at 50°C. The reaction mixture was extracted with ethyl acetate, washed with water, dried over magnesium sulphate and concentrated to give a yellow oil (114 mg). This material was used in the next step without further urification.
Figure imgf000155_0002
Preparation of 12: To a solution of 13 (4 g) in dry tetrahydrofuran (20 mL) cooled to
-40°C was added a freshly prepared lithium diisopropylamide solution (0.7M; 30 mL). After stirring for lh at -20°C, the reaction mixture was cooled to -40°C and formic ester (0.785 mL) in THF (10 mL) was added dropwise. After stirring for 2h at -20°C, the reaction mixture was allowed to warm at ambient temperature, quenched with an ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulphate, concentrated and purified over silica gel to give an orange oil (2.6 g).
Figure imgf000155_0003
Preparation of 13: To a solution of 2-methyl-6,7-dihydro-5H-quinolin-8-one (10 g) in toluene (150 mL) were added ethylene glycol (6.24 mL) and paratoluenesulfonic acid (1.07 g). The reaction mixture was stirred for 3h at reflux with a Dean-Stark apparatus. A sodium hydroxide solution (0.5M) was added and it was extracted with tert-butylmethylether. The organic phase was dried over magnesium sulphate, concentrated and purified over silica gel to give a brown oil (7.35 g).
Example 2: Preparation of P9
Figure imgf000156_0001
To a solution of e^-dimethyl-^^bipyridinyl (250 mg) in dry THF (6 mL) was added a freshly prepared LDA solution (8 mL; 0.18M solution in THF) at -65°C. After stirring for 45min at -65°C, methylene iodide (55 pL) dissolved in dry THF (3 mL) was slowly added. The reaction mixture was stirred for lh at -65°C then was allowed to warm up slowly until -30°C for lh. The reaction was then quenched with ammonium chloride solution and further stirred until ambient temperature was reached. The reaction mixture was extracted with ethyl acetate. The organic phase was washed with ammonium chloride solution, dried over magnesium sulphate, purified over silica gel to give white-yellow crystals (126 mg).
Example 3: Preparation of P7
Figure imgf000156_0002
To a solution of 14 (90 mg) in ethanol (2 mL) and HCI (2N; 1 mL) was added O- methylhydroxylamine hydrochloride (47 mg). After stirring for 2h at reflux, the solvent was evaporated. The residue was treated with a bicarbonate solution to reach pH 9 and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulphate and purified over silica gel to ive a colourless solid (38 mg).
Figure imgf000156_0003
Preparation of 14: To a solution of 6-methyl-[2,2']bipyridinyl (170 mg) in dry THF was added a freshly prepared LDA solution (1.05 mL; 1M in THF). After stirring for 30min at -20°C this mixture was added to a solution of 2-(2-bromo-ethyl)-6-(2-methyl-[l,3]dioxolan- 2-yl)-pyridine (272 mg) in dry THF (5 mL) at -20°C. The reaction mixture was stirred at - 20°C for further 45min and 30min at ambient temperature then it was quenched with an ammonium chloride solution at 0°C. It was extracted with dichloromethane the organic phase was dried over magnesium sulfate, concentrated and purified over silica gel to give a yellow oil (90 mg). LC-MS (OA_5min_45V) : 1.04min, 362 ([M+l]+)
Figure imgf000157_0001
Preparation of 2-(2-bromo-ethyl)-6-(2-methyl-[l,3]dioxolan-2-yl)-pyridine: To a solution of 2-[6-(2-methyl-[l,3]dioxolan-2-yl)-pyridin-2-yl]-ethanol (3.4 g) in
dichloromethane (170 mL) was added tetrabromomethane (10.78 g) and then a solution of triphenylphosphine (8.51 g) in dichloromethane (80 mL) was added dropwise. After stirring for 2h at ambient temperature the reaction was quenched with an ammonium chloride solution at 0°C. It was extracted with dichloromethane, dried over magnesium sulphate, concentrated and purified over silica gel to give a yellow oil (3.83 g). ^-NMR (CDCI3, 400 MHz): 7.65(t, IH), 7.45(d, IH), 7.15(d, IH), 4.15(m, 2H), 3.95(m, 2H), 3.8(t, 2H), 3.4(t, 2H), 1.75 S, 3H).
Figure imgf000157_0002
Preparation of 2-[6-(2-methyl-[l,3]dioxolan-2-yl)-pyridin-2-yl]-ethanol: To a solution of [6-(2-methyl-[l,3]dioxolan-2-yl)-pyridin-2-yl]-acetic acid ethyl ester (5 g) in THF (100 mL) was added a lithium aluminium hydride solution (50 mL; 1M THF solution) dropwise at 0°C. After stirring for 30min at 0°C then 2h at ambient temperature, the reaction was quenched with water then sodium hydroxide solution (0.5M) at 0°C. The suspension was filtered and rinsed with THF. The filtrate was concentrated under vacuum then purified over silica gel to give 2-[6-(2-methyl-[l,3]dioxolan-2-yl)-pyridin-2-yl]-ethanol (3.4 g). ^-NMR (CDCI3, 400 MHz): 7.65(t, IH), 7.45(d, IH), 7.1 (d, IH), 4.1(m, 2H),4.05(t, 2H), 3.9(m, 2H), 3.05 t, 2H), 1.75(s, 3H).
Figure imgf000157_0003
Preparation of [6-(2-methyl-[l,3]dioxolan-2-yl)-pyridin-2-yl]-acetic acid ethyl ester: To a solution of 2-methyl-6-(2-methyl-[l,3]dioxolan-2-yl)-pyridine (4 g) in THF (20 mL) cooled to -60°C was added dropwise a freshly prepared LDA solution (20 mL; 2.35M THF solution). After stirring for 20min at -60°C, for lh at -40°C and for lh more at -30°C, the reaction mixture was cooled to -60°C and diethylcarbonate (12 g) dissolved in THF (8 mL) was added. The reaction mixture was stirred for 20min at -40°C and it was allowed to warm up slowly to ambient temperature for overnight. The reaction was then quenched with an ammonium chloride solution at 0°C, extracted with ethyl acetate, washed with water, dried over magnesium sulphate, concentrated under vacuum and purified over silica gel to give a yellow liquid (3.4 g). ^-NMR (CDCI3, 400 MHz): 7.7(t, 1H), 7.45(d, 1H), 7.25 (d, 1H), 4.2 m, 2H), 4.1(m, 2H), 3.9(m, 2H), 1.75(s, 3H), 1.25(t, 3H).
Figure imgf000158_0001
Preparation of 2-methyl-6-(2-methyl-[l,3]dioxolan-2-yl)-pyridine: To a solution of 1-
(6-methyl-pyridin-2-yl)-ethanone (20 g) in toluene (400 mL) were added ethylene glycol (55 g) and paratoluene sulfonic acid (2.55 g). The reaction mixture was heated for 24h at reflux with a Dean-Stark apparatus. It was allowed to come back at ambient temperature and sodium hydroxide solution (150 mL; 0.5M) was added. It was extracted with dichloromethane, washed with water, dried over magnesium sulphate, concentrated under vacuum to give a yellow liquid (22 g). ^-NMR (CDCI3, 400 MHz):7.55(t, 1H), 7.35(d, 1H), 7.05(d, 1H), 4.1(m, 2H), 3.9(d, 1H), 2.55(s, 3H), 1.75(s, 3H).
Ex mple 4: Preparation of P13
Figure imgf000158_0002
To a solution of 15 (20 g) in chloroform (600 mL) was added manganese dioxide
(37.92 g). The reaction mixture was stirred for 72h at 60°C. Presence of starting material indicated that the reaction had not gone to completion, and so more manganese dioxide (75.8 g) was added and the reaction mixture further stirred at 60°C for 24h. The reaction mixture was filtered and rinsed with dichloromethane. The filtrate was concentrated under vacuum purified over silica gel to give a beige solid (15.10 g).
Figure imgf000158_0003
Preparation of 15: To a solution of 16 (1 g) in isopropanol (15 mL) were added thiourea (0.92 g) and 2-aminobenzylamine (2.46 g). The reaction mixture was heated in microwave for 30min at 165°C. It was then poured into a saturated bicarbonate solution, extracted with ethyl acetate and washed with brine. The organic phase was dried over sodium sulphate and concentrated under vacuum to give an orange solid (2.8 g pure at 55%). The material was used in the next ste without further purification.
Figure imgf000158_0004
Preparation of 16: A solution of 17 (27.3 g from the crude described below) in dichloromethane was stirred overnight at ambient temperature. Dimethylcarbamyl chloride (30.6 g) was added and trimethylsilyl cyanide (35.6 mL) was added portionwise (caution: exothermic). The reaction mixture was stirred overnight at ambient temperature, then the reaction was quenched with a carbonate solution and extracted at pH9 with
dichloromethane, then washed with brine. The organic phase was dried over sodium sulphate, concentrated under vacuum and purified over silica gel to give a beige solid (9.5 g)-
Figure imgf000159_0001
Preparation of 17: To a solution of 18 (54.2 g from the crude described below) in chloroform (700 mL) was added mCPBA (129.7 g) portionwise. The reaction mixture was stirred for 2h at 45°C, then the reaction was carefully quenched at 0-5°C with a sodium hydroxide solution (10M) until basic pH was reached and then with sodium thiosulfate. It was extracted with dichloromethane (three times) and washed with brine. The organic phase was dried over sodium sulphate and concentrated under vacuum to give a beige solid (27.3 g; ~60% pure). The material was used in the next ste without further purification.
Figure imgf000159_0002
Preparation of 18: To a solution of 2-methyl pyridine in THF (400 mL) cooled at -20°C under an argon atmosphere was added nBuLi (100 mL; 2.5M in hexane) dropwise. The reaction mixture was stirred for lh at -20°C and a solution of 2-vinylpyridine in THF (100 mL) was added dropwise via canula at -20°C. The reaction mixture was stirred overnight and allowed to warm up slowly to ambient temperature. It was further heated for 3h at 50°C and the reaction was quenched with an ammonium chloride solution at ambient temperature and stirred for 30min. The reaction mixture was extracted with ethyl acetate and washed with brine. The organic phase was dried over sodium sulphate, concentrated under vacuum and purified over silica gel to give an orange liquid (54.2 g; 55% purity). The material was used in the next step without further purification.
Example 5: Preparation of P20
Figure imgf000159_0003
A solution of P19 (92 mg; 0.224 mmol) in dimethylformamide (5 mL) was cooled to 0°C with an ice-water bath. Sodium hydride (11 mg; 0.269 mmol) was added and the obtained mixture was stirred for 1 hour at this temperature. The reaction mixture was allowed to come back at ambient temperature and methyl iodide (0.015 mL; 0.235 mmol) was added and the resulting solution was stirred for overnight at ambient temperature. The course of the reaction was followed by LC-MS, which indicated that starting material was left at this time. The reaction mixture was then cooled again to 0°C, further amount of sodium hydride (11 mg; 0.269 mmol) and methyl iodide (0.015 mL; 0.235 mmol) were added and the reaction mixture was stirred again overnight at ambient temperature. This was repeated twice as reaction control showed remaining starting material. The reaction mixture was carefully poured onto water and extraction was carried out using ethyl acetate. The organic phases were washed with water, dried over magnesium sulfate, concentrated under vacuum and purified over silica gel to give a colorless oil (42 mg).
Figure imgf000160_0001
Preparation of P19: A solution of P18 (0.279 g; 0.616 mmol) in tetrahydrofuran (5 mL) was cooled to -78°C. Lithium aluminium hydride (1M in THF, 0.74 mL; 0.74 mmol) was added dropwise and the reaction mixture was stirred for 3 hours at that temperature.
Reaction control showed remaining starting material then further lithium aluminium hydride (1M in THF; 0.308 mL; 0.308 mmol) was added. After 30 minutes, reaction control indicated all starting material was consumed. The reaction mixture was allowed to come back at 0°C and quenched with a saturated sodium bicarbonate solution (1.2 mL), filtered and concentrated under vacuum. The residue was redissolved in ethyl acetate, washed with a saturated potassium carbonate solution, dried over magnesium sulfate, filtered and concentrated under vacuum to give a colorless oil (265 mg). This intermediate was used in the next step without purification.
Figure imgf000160_0002
Preparation of P18: P17 (0.398 mg; 0.759 mmol) and water (0.12 mL) were added in a suspension of sodium chloride (67 mg; 1.138 mmol) in dimethylsulfoxide (5 mL) placed under argon. The resulting mixture was stirred at reflux for overnight. As reaction control showed no remaining starting material, the reaction mixture was poured onto brine (10 and extraction was carried out using ethyl acetate (3x10 mL). The organic phases were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude material was purified b chromatography on silica gel to give a colorless oil (295 mg).
Figure imgf000161_0001
Preparation of P17: This was prepared following a literature procedure (Inorganic Chemistry, 1983, 22, 171-174). Under an argon atmosphere, sodium hydride (180 mg; 4 mmol) was added to a cooled solution of diethyl malonate (240 mg; 2 mmol) in dry tetrahydrofuran (5 mL). This mixture was allowed to come back at ambient temperature and stirred for 30 minutes. The reaction mixture was then cooled with an ice bath to 0°C and a solution of 6'-chloromethyl-6-methyl-[2,2']bipyridinyl (943 mg; 4 mmol) in dry tetrahydrofuran (5 mL) was added dropwise, followed by the addition of sodium iodide (593 mg; 4 mmol). The resulting mixture was stirred at ambient temperature for overnight. The reaction mixture was then poured in ice-water and acidified using an aqueous 2N HCI solution. After stirring for 10 minutes, pH was adjusted to 7 by using an aqueous 2N NaOH solution and extraction was carried out using dichloromethane. The organic phases were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude material was purified by chromatography on silica gel to give white crystals (418 mg).
Figure imgf000161_0002
Preparation of chloromethyl-6-methyl-[2,2']bipyridinyl: Under an argon atmosphere, 6,6'-dimethyl-[2,2']bipyridinyl (1.88 g; 10 mmol) was dissolved in tetrachloromethane (50 mL). N-Chlorosuccinimide (1.36 g; 10 mmol) and benzoyl peroxide (50 mg; 0.67 mmol) were added. The reaction mixture was stirred at reflux for overnight. The mixture was cooled with an ice bath, filtered, and the filtrate was concentrated under vacuum. The crude material was purified by chromatography on silica gel to give white crystals (950 mg).
Example 6: Preparation of P15
Figure imgf000161_0003
MeMgBr (4.87 mL; 1M in THF) was added dropwise at 0°C to a solution of 110 (510 mg). After stirring for 30min at 0°C ethanol (16 mL) was added. Then O-methyl- hydroxylamine hydrochloride (217 mg) was added and the reaction mixture was heated to 55°C for 30min. The solvent was then removed and the residue was diluted with ethyl acetate. The organic phase was then washed with brine, dried over sodium sulfate, filtered and concentrated and purified over silica to ive a yellow oil (480 mg).
Figure imgf000162_0001
Preparation of 110: Lithium chloride (219 mg) was added to a solution of 111 (400 mg) in dimethyl sulfoxide. After stirring for 15h at 180°C the reaction mixture was poured on water and extracted with ethyl acetate. The organic phases were washed with water, dried over magnesium sulfate, concentrated and purified over silica gel to give a colorless oil (190 mg).
Figure imgf000162_0002
Preparation of 111: Sodium hydride (103 mg; 60% in oil) was added to a solution of 112 (1.1 g) in tetrahydrofurane (15 mL). After stirring for lh at ambient temperature a solution of 6-vinylpyridine-2-carbonitrile (310 mg) in tetrahydrofuran (5 mL) was slowly added. After stirring for 2h at ambient temperature the reaction mixture was poured on water and extracted with ethyl acetate. The organic phases were washed with water, dried over magnesium sulfate, concentrated and purified over silica gel to give ethyl 4-(6-cyano-2- pyridyl)-2- 6-(6-methyl-2-pyridyl)-2-pyridyl]butanoate as a yellow oil (740mg).
Figure imgf000162_0003
Preparation of 112: Lithium diisopropyl amide (310 mL; 2M solution in
tetrahydrofuran) was added under an argon atmosphere within lh at -60°C to a mixture of 6,6'-dimethyl-2,2'-dipyridyl (53.00 g) and diethyl carbonate (102 mL) in tetrahydrofuran (27 mL). After stirring for further 15min at -60°C a solution of ammonium chloride (50 mL; 25% in water) was carefully added. The reaction mixture was then poured on water and extracted with ethyl acetate. The organic phases were washed with water, dried over magnesium sulfate, concentrated and purified over silica gel to give 44 g of yellow liquid.
Example 7: Preparation of P46
Figure imgf000163_0001
Acetylacetone (0.33 g) was added to 113 (500 mg) in pyridine (4.8 ml_). After stirring for 16h at 70°C acetylacetone (0.66 g) was added und the reaction mixture was stirred for further 4h at 80°C. Then the reaction mixture was concentrated and the residue was purified over silica gel to give a yellow oil (150 mg)
Figure imgf000163_0002
Preparation of 113: Sodium methylate (2 ml_; 5.4M in methanol) was added to a solution of 6-[3-[6-(6-methyl-2-pyridyl)-2-pyridyl]propyl]pyridine-2-carbonitrile (1.35 g). After stirring for lh at ambient temperature ammoniumchloride (0.804 g) was added and after further stirring for 20h the reaction mixture was concentrated and the residue was suspended in diethylether and filtrated to give the product as a hydrochloride salt (2.15 g) together with the excess of ammonium chloride. This material was used in the next step without further purification.
Example 8: Preparation of P23
Figure imgf000163_0003
Na2CO3 -10 H20 (2.35 g, 8.13 mmol) and 6-methyl-pyridine-2-carboxamidine hydrochloride (670 mg, 3.90 mmol) were added successively to a brown solution of 114(547 mg, 1.63 mmol) in THF (25 ml_). The reaction mixture was heated to reflux temperature and stirred for 3 hours. After cooling to r.t., the crude product was directly purified by chromatography on silica gel (dichloromethane-methanol, 100:0 to 90:10) to give a brown oil (168 mg). LC-MS (Method ZCQ) Rt = 1.68 min., MS: (M++l) = 571. ^-NMR (CDCI3, 400 MHz): 2.49 (m, 2H); 2.72 (s, 6H); 3.13 (m, 4H); 7.16 (dd, 2H); 7.28 (s,2H); 7.32 (t, 2H); 7.48 (m,2H); 7.74 (m,4H); 8.34 (m,4H).
Figure imgf000163_0004
Preparation of 114: Pd(PPh3)2Cl2 (45.8 mg, 0.065 mmol) and Cul (24.9 mg, 0.13 mmol) were dissolved in degassed THF (15ml_) under argon at room temperature. Then Et3N (0.41 g, 4.07 mmol) as well as 2-fluoro-benzoyl chloride (0.39 ml_, 3.26 mmol) and hepta-l,6-diyne (150 mg, 1.63 mmol) were added successively to the solution. The dark brown mixture was stirred overnight. This intermediate (in solution) was used in the next step without purification.
Example 9: Preparation of 115
Figure imgf000164_0001
A mixture of 116 (0.2 g, 0.98 mmol), vinyltributylstannane (0.32 ml_, 1.08 mmol), cesium fluoride (0.3 g, 1.95 mmol), tetrakis(triphenylphosphine)palladium(0) (57 mg, 0.05 mmol) and copper(I) iodide (19 mg, 0.10 mmol) in dimethylformamide (4 mL) was stirred at 85°C overnight. After addition of ethyl acetate and water the suspension was filtered over Hyflo. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated in vacuo. The remainder was purified on silica gel, using heptane/ethyl acetate 19:1, then dichloromethane/ethanol 99:1 as eluent to deliver 6-methyl-6'-vinyl- (2,2')bipyridinyl as a beige powder, m.p. 62-63°C.
Figure imgf000164_0002
Preparation of 116: To the suspension of 6,6'-dichloro-(2,2')bipyridinyl (10 g, 44.4 mmol; J. Chem. Soc. Perkin I 1980, 2527; Org. Lett. 2000, 803) and iron(III)
acetylacetonate (1.57 g, 4.44 mmol) in tetrahydrofuran (200 mL) and l-methyl-2- pyrrolidinone (25 mL) was added dropwise methyl magnesium bromide (34.1 mL, 102 mmol; 3.0 M in diethyl ether) within 2.5 h and stirring was continued for another 30 min. at room temperature. After addition of ethyl acetate and water the suspension was filtered over Hyflo. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated in vacuo. The remainder was purified on silica gel, using
dichloromethane/ethanol 98:2 as eluent to deliver 6-chloro-6'-methyl-(2,2')bipyridinyl as a white powder, m.p. 135-136°C.
Example 10: Preparation of 117
Figure imgf000165_0001
Triethylamine (1.09 g) and palladium (50 mg; 10% on charcoal) were added to a solution of 118 (1.15 g) in tetrahydrofuran (20 mL). After stirring for 6h under an atmosphere of hydrogen the reaction mixture was filtered, concentrated and purified by chromatography over silica to give an orange oil (0.78 g).
Figure imgf000165_0002
Preparation of 118: Phosphorus oxychloride (2.67 g) was added slowly to 119 (3.14 g) in toluene (25 mL). The green suspension was stirred at 70°C for 90min. The reaction mixture was cooled to ambient temperature and poured into sodium bicarbonate solution (100 mL; 20% in water). After stirring for 15min at room temperature the reaction mixture was extracted with ethylacetate, the combined organic phases were washed with water, dried over MgS04, filtered and concentrated to give a brown solid (3.29g).
Figure imgf000165_0003
Preparation of 119: 6-Methylpyridine-2-carboxamidine hydrochloride (15 g) was suspended in ethanol (200 mL). Potassium tert-butylate (11.149 g) was added slowly at ambient temperature. Then dimethyl-l,3-acetone dicarboxylate (16.742 g) was added dropwise and the reaction mixture was heated to reflux for 18h. The reaction mixture was concentrated and the green residue was taken up in ethyl acetate and water. Hydrochloric acid (2N in water) was added until pH 7, then the water phase was extracted with ethyl acetate. The combined organic phases were dried over MgS04, filtered and concentrated. The solid residue was suspended in heptane, filtered and dried to give a green solid (20.7 g)- Example 11: Preparation of 129
Figure imgf000166_0001
To the suspension of 75 mg (1.88 mmol) sodium hydride (60%) in 6 ml 5 dimethylformamide is added 0.14 ml (1.88 mmol) acetone in 2 ml dimethylformamide dropwise at 0°C. After 0.5 h 0.4 g (1.57 mmol) l-(6-bromo-pyridin-2-yl)-3-dimethylamino- propenone (Tetrahedron Lett. 2003, 6305) in 2 ml dimethylformamide is added dropwise at 0°C and the solution is stirred for 1 h. Another 40 mg sodium hydride (60%) is added and stirring continued for 1 h. Then 145 mg (1.88 mmol) ammonium acetate is added at 0°C. 6
10 ml acetic acid is added dropwise and the reaction mixture is heated to 125°C for 5 min..
After cooling the reaction mixture is poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulfate and evaporated in vacuo. The remainder is purified on silica gel, using heptane/ethyl acetate 9: 1 as eluent to deliver 6-bromo-6'-methyl-(2,2')bipyridinyl as a white powder, m.p.
15 148-149°C.
Example 12: Preparation of 130
Figure imgf000166_0002
118 (4.3 g, 15 mmol) was dissolved in methanol (80 mL) and sodium methoxide (8.3 g, 8.5 20 mL, 38 mmol) was added (orange-red solution). After stirring for 4h at room temperature HCI 6N (6mL, 6N in water) were added and volatiles were removed. The residue was dissolved in ethylacetate and neutralized with sodium hydroxide (2N in water). The mixture was extracted with ethylacetate and the combined organic phases were washed with water dried over magnesium sulfate, filtered and concentrated to give an orange oil (3.11g).
25 Example 13: Preparation of 131
Figure imgf000167_0001
118 (4.3 g, 15 mmol) was dissolved in tetrahydrofurane (78 mL) and l-methyl-2- pyrrolidone (11 mL) and ferric acetylacetonate (0.52 g, 1.5 mmol) were added. Methyl magnesiumbromide 3M in diethylether (12 g, 11 mL, 34 mmol) was added dropwise over lh (temperature increased until 33°C). After stirring for 45min at ambient temperature methyl magnesiumbromide 3M in diethylether (6mL) was added dropwise over lOmin.The reaction mixture was stirred for 2h at ambient temperature, quenched with water and diluted with ethylacetate. This mixture was filtrated, the organic phase was separated dried over magnesium sulfate, filtered and concentrated. The residue was purified over silica gel to give an orange liquid-oil (3.3g)
Example 14: Preparation of 140
Figure imgf000167_0002
Sodium methoxide (0.207g) was added to a solution of 4,6-dibromo-2-(6-methyl-2- pyridyl)pyrimidine (139, 0.300g) in tetrahydrofurane. After stirring for 5min at room temperature hydrochloric acid (1M in water) was added and the reaction mixture was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated to give a yellow oil (0.230g) which was used in next steps without further purification.
Figure imgf000167_0003
Preparation of 139: Phosphorus (V) oxybromide (4.2g) was added to a suspension of 2-(6- Methyl pyr id in-2-yl) pyrimidine-4,6-diol (CAS NO 1001915-36-l)(1.0g) in toluene (2.5ml). After stirring for 3h at 120°C the reaction mixture was cooled diluted with dichloromethane, carefully quenched with sodium bicarbonate solution (20% in water) and extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated to give a dark brown oil (1.15g) which was used in next steps without further purification.
Example 15: Preparation of P65
Figure imgf000168_0001
Sodium hydride (0.32g, 60% in oil) was added in one portion to a solution of 112 (3.57g) in tetrahydrofuran (60ml_). After stirring for lh at ambient temperature a solution of 120 (1.4g) in tetrahydrofuran (20ml_)was added dropwise within 20min. After stirring for 2h at ambient temperature the reaction mixture was quenched with sodium bicarbonate solution in water (20%) and extracted with ethylacetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated and the residue was purified over silica to give a beige solid (2.4g).
Figure imgf000168_0002
Preparation of 112: A mixture of 124 (2.3g), vinyltributylstannane (3.037 g, 2.799 ml_), and tetrakis (triphenylphosphine) palladium(O) (400mg) in toluene (30 mL) was stirred at 100°C overnight. The reaction mixture was cooled to room temperature and sodium hydroxide (20ml, 1M in water) was added. The mixture was stirred vigorously for 3h and then diluted with ethylacetate. The organic phase was separated dried over magnesium sulfate, filtered and concentrated. The residue was purified over silica to give a yellow oil (l-7g).
Figure imgf000168_0003
HCI Preparation of 124: A mixture of 6-bromopyridine-2-carboxamidine hydrochloride (CAS 122918-17-6) (6.0 g), acetylacetone (7.8 mL, 7.6 g) and pyridine (51 mL) was stirred overnight at 70°C. The reaction mixture was concentrated and the residue was purified over silica to give a white solid (4.3g)
Table 3: NMR data for compounds of formula (I)
Structure 1H-NMR (CDC , 400 MHz)
PI 7.7 (d, 2H), 7.55 (t, 2H), 7.1 (d, 2H), 4
(s, 6H), 2.85 (t, 4H), 2.3 (s, 6H), 2.2 (q, 2H)
?
P2 7.4 (d, 2H), 7.15(d, 2H), 4.15 (s, 6H),
2.95(t, 4H), 2.85(t, 4H), 2.75 (t, 4H), 2.2 (q, 2H), 1.85 (q, 4H)
? ?
P3 7.4(d, 2H), 7.35(d, 2H), 4.15(s, 6H),
3.35 (s, 3H), 3.1 (d, 4H), 2.85 (t, 4H), 2.75 (t, 4H), 1.85 (q, 4H)
? ?
P4 7.4 (d, 2H), 7.35(d, 2H), 6.8 8m, 1H),
5.2 (d, 1H), 5.05 (d, 1H), 4.3 (q, 1H), 4.15(s, 6H), 4 (d, 2H), 3.1 (m, 4H), 2.85 (t, 4H), 2.75 (t, 4H), 1.85 (q, 4H)
?
P5 7.65(d, 2H), 7.55(t, 2H), 7.05(d, 2H),
4(s, 6H), 2.8(t, 4H), 2.3(s, 6H), 1.75(q, 4H), 1.45 (q, 2H)
? °
P6 7.7(d, 2H), 7.55(t, 2H), 7.1(d, 2H),
4.8(s, 2H), 4(s, 6H), 2.95(t, 4H), 2.55(t, 4H), 2.3(S, 6H)
P7 8.7(dd, 1H), 8.5(d, 1H), 8.25(d, 1H),
7.8(t, 1H), 7.75(d, 1H), 7.7(m, 1H), 7.55(t, 1H), 7.3(m, 1H), 7.2(d, 1H),
0 7.15(d, 1H), 4.05(s, 3H), 2.95(q, 4H),
2.35(s, 3H), 2.3(m,2H)
Figure imgf000170_0001
Figure imgf000171_0001
Table 4: LC-MS data for compounds of formula (Ϊ)
Figure imgf000172_0001
Figure imgf000173_0001
Figure imgf000174_0001
P26 1.30 599 ([M + l]+)
(UPLCl)
P27 1.36 595 ([M + l]+)
(UPLCl)
P28 1.52 607 ([M + l]+)
(UPLCl)
P29 1.50 563 ([M + l]+)
(UPLCl)
P30 1.13 515 ([M + l]+)
(UPLCl)
ΝΙ" Ί f iN
Figure imgf000176_0001
Figure imgf000178_0001
Figure imgf000179_0001
Figure imgf000180_0001
Figure imgf000181_0001
Figure imgf000182_0001
Table 5: NMR data for intermediates of compounds of formula (Ϊ)
Figure imgf000183_0001
Figure imgf000184_0001
Table 6: LC-MS data for intermediates of compounds of formula (Ϊ)
Figure imgf000185_0001
Figure imgf000186_0001
Figure imgf000187_0001
Figure imgf000188_0001
Figure imgf000189_0001
Figure imgf000190_0001
LC-MS methods used
Method ZDQ
ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer):
lonisation method: Electrospray; Polarity: positive and negative ions; Capillary (kV)
3.00; Cone (V) 30.00; Extractor (V) 2.00; Source Temperature (°C) 150; Desolvation Temperature (°C) 250; Cone Gas Flow (L/Hr) 50; Desolvation Gas Flow (L/Hr) 400; Mass range: 100 to 900 Da
HP 1100 H PLC from Agilent:
solvent degasser, binary pump, heated column compartment and diode-array detector; Column: Phenomenex Gemini C18, 3 μιτι, 30 x 3 mm; Temp: 60 °C; DAD Wavelength range (nm): 210 to 500
Solvent Gradient:
A = water + 5% MeOH + 0.05 % HCOOH
B= Acetonitrile + 0.05 % HCOOH
Time A% B% Flow (mL/min)
0.00 100 0 1.700
2.00 0 100 1.700
2.80 0 100 1.700
2.90 100 0 1.700
3.00 100 0 1.700 Method ZCQ
ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer)
Instrument Parameter:
Ionisation method: Electrospray
5 Polarity: positive ions
Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 100, Desolvation Temperature (°C) 250, Cone Gas Flow (L/Hr) 50, Desolvation Gas Flow (L/Hr) 400
Mass range: 100 to 900 Da
10 HP 1100 HPLC from Agilent: solvent degasser, quaternary pump (ZCQ) / binary pump (ZDQ), heated column compartment and diode-array detector.
Column: Phenomenex Gemini C18, 3 mm particle size, 110 A, 30 x 3 mm,
Temp: 60 °C
DAD Wavelength range (nm): 200 to 500
15 Solvent Gradient:
A = water + 0.05 % HCOOH
B= Acetonitril/Methanol (4: 1, v:v) + 0.04 % HCOOH
Time A% B% Flow (ml/min)
0.00 95.0 5.0 1.700
20 2.00 0.0 100.0 1.700
2.80 0.0 100.0 1.700
2.90 95.0 5.0 1.700
3.00 95.0 5.0 1.700
25 OA_2min_30V
SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer): Ionization method: Electrospray; Polarity: positive and negative ions; Capillary (kV): 3.00; Cone (V): 30.00; Extractor (V): 2.00; Source Temperature (°C): 150; Desolvation Temperature (°C): 250; Cone Gas Flow (L/Hr): 0; Desolvation Gas Flow (L/Hr): 650; Mass 30 range: 100 to 900 Da
Acquity UPLC from Waters:
Binary pump, heated column compartment and diode-array detector; Solvent degasser, binary pump, heated column compartment and diode-array detector; Column: Phenomenex Gemini C18, 3 - m, 30 x 2 mm; Temp: 60 °C; DAD Wavelength range (nm): 35 210 to 500
Solvent Gradient: A = H20 + 5% MeOH + 0.05 % HCOOH
B= Acetonitril + 0.05 % HCOOH
Time A% B% Flow (mL/min)
0.00 100 0 0.850
1.20 0 100 0.850
1.50 0 100 0.850
OA_2min_45V
SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer): Ionization method: Electrospray; Polarity: positive and negative ions; Capillary (kV):
3.00; Cone (V): 45.00; Extractor (V): 2.00 ; Source Temperature (°C): 150; Desolvation Temperature (°C): 250; Cone Gas Flow (L/Hr): 0; Desolvation Gas Flow (L/Hr): 650; Mass range: 100 to 900 Da
Acquity UPLC from Waters:
Binary pump, heated column compartment and diode-array detector; Solvent degasser, binary pump, heated column compartment and diode-array detector; Column: Phenomenex Gemini C18, 3 - m, 30 x 2 mm; Temp: 60°C; DAD Wavelength range (nm): 210 to 500
Solvent Gradient:
A = H20 + 5% MeOH + 0.05 % HCOOH
B= Acetonitril + 0.05 % HCOOH
Time A% B% Flow (mL/min)
0.00 100 0 0.850
1.20 0 100 0.850
1.50 0 100 0.850
OA_3min_30V
ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer):
Ionization method: Electrospray; Polarity: positive and negative ions; Capillary (kV): 3.00; Cone (V): 30.00; Extractor (V): 2.00; Source Temperature (°C): 100; Desolvation
Temperature (°C): 250; Cone Gas Flow (L/Hr): 50; Desolvation Gas Flow (L/Hr): 400; Mass range: 100 to 900 Da
HP 1100 H PLC from Agilent:
Solvent degasser, binary pump, heated column compartment and diode-array detector; Column: Phenomenex Gemini C18, 3 - m, 30 x 3 mm; Temp: 60°C; DAD
Wavelength range (nm): 210 to 500; Solvent Gradient:
A = water + 5% MeOH + 0.05 % HCOOH
B= Acetonitrile + 0.05 % HCOOH
Time A% B% Flow (mL/min)
0.00 100 0 1.700
2.00 0 100 1.700
2.80 0 100 1.700
2.90 100 0 1.700
3.00 100 0 1.700
OA_5min_45V
SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Ionization method: Electrospray; Polarity: positive and negative ions; Capillary (kV):
3.00; Cone (V): 45.00; Extractor (V): 2.00; Source Temperature (°C): 150; Desolvation Temperature (°C): 250; Cone Gas Flow (L/Hr): 0; Desolvation Gas Flow (L/Hr): 650; Mass range: 100 to 900 Da
Acquity UPLC from Waters:
Binary pump, heated column compartment and diode-array detector; Solvent degasser, binary pump, heated column compartment and diode-array detector; Column: Phenomenex Gemini C18, 3 - m, 30 x 2 mm; Temp: 60°C; DAD Wavelength range (nm): 210 to 500
Solvent Gradient:
A = water + 5% MeOH + 0.05 % HCOOH
B= Acetonitrile + 0.05 % HCOOH
Time A% B% Flow (mL/min)
0.00 100 0 0.850
3.40 0 100 0.850
4.10 0 100 0.850
4.20 100 0 0.850
4.60 100 0 0.850
OA_8min_Pol_30V
ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Ionization method: Electrospray; Polarity: positive and negative ions; Capillary (kV): 3.00; Cone (V): 30.00; Extractor (V): 2.00; Source Temperature (°C): 100; Desolvation Temperature (°C): 250; Cone Gas Flow (L/Hr): 50; Desolvation Gas Flow (L/Hr): 400; Mass range: 100 to 900 Da
HP 1100 H PLC from Agilent:
Solvent degasser, binary pump, heated column compartment and diode-array detector; Column: HyperCarb, 3 - m, 30 x 3 mm; Temp: 60°C; DAD Wavelength range (nm): 210 to 500
Solvent Gradient:
A = water + 5% MeOH + 0.05 % HCOOH
B= Acetonitrile + 0.05 % HCOOH
Time A% B% Flow (mL/min)
0.00 100 0 1.700
6.00 0 100 1.700
7.70 0 100 1.700
7.80 100 0 1.700
8.00 100 0 1.700
Method U and UPLC1
ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Ionisation method: Electrospray
Polarity: positive ions
Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700
Mass range: 100 to 800 Da
DAD Wavelength range (nm): 210 to 400
Method Waters ACQUITY UPLC with the following HPLC gradient conditions
Solvent Gradient:
A: Water/Methanol (9:1, v:v) + 0.1% HCOOH
B: Acetonitrile +0.1% HCOOH
Time A% B% Flow (mL/min)
0 100 0 0.75
2.5 0 100 0.75
2.8 0 100 0.75
3.0 100 0 0.75
Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C OA_Standard
ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer)
Instrument Parameter:
Ionization method: Electrospray
Polarity: positive and negative ions
Capillary: 3.00 kV
Cone: 30 V
Extractor: 2.00 V
Source Temperature: 150°C,
Desolvation Temperature: 350C
Cone Gas Flow: 50 L/Hr
Desolvation Gas Flow: 400 L/Hr
Mass range: 100 to 900 Da
Acquity UPLC from Waters:
Binary pump, heated column compartment and diode-array detector.
Solvent degasser, binary pump, heated column compartment and diode-array detector.
Column: Waters UPLC HSS T3 , 1.8 - m, 30 x 2.1 mm,
Temp: 60 °C
DAD Wavelength range (nm): 210 to 500
Solvent Gradient:
A = H20 + 5% MeOH + 0.05 % HCOOH
B= Acetonit ril + 0.05 % HCOOH
Time A% B% Flow (ml/min)
0.00 90 10 0.85
2.70 0 100.0 0.85
3.00 0 100.0 0.85
Biological examples:
Phytophthora infestans I tomato / leaf disc preventative (late blight)
Tomato leaf disks were placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks were incubated at 16°C and 75% relative humidity under a light regime of 24 h darkness followed by 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5 - 7 days after application). The following compounds gave at least 80% control of Phytophthora infestans: P08; P02; P22; P34; P38; P40; P47; P48; P49; P.54; P.60; P.61; P69; P73
Plasmopara viticola I grape / leaf disc preventative (late blight')
Grape vine leaf disks were placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks were incubated at 19°C and 80% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (6 - 8 days after application). The following compounds gave at least 80% control of Plasmopara viticola: P12; P08; P09; P03; P04; P15; P20; P22; P27; P35; P36; P41; P42; P44; P47; P48; P.66; P.67; P74; P75
Puccinia recondita f. sp tritici I wheat / leaf disc preventative (Brown rust):
Wheat leaf segments cultivated variety (cv) Kanzler were placed on agar in 24-well plates and sprayed with formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 - 9 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sP tritici: P12; P14; P01; P08; P09; P07; P02; P03; P04: P16; P18;,P19; P20; P22; P23; P27; P30; P31; P32; P33; P34; P37; P38; P39; P40; P41; P42; P43; P44; P45; P47; P48; P49; P50; P51; P.54; P.59; P.60; P.61; P.62; P.67; P69; P70; P71; P72; P73; P74; P75
Puccinia recondita f. sp tritici I wheat / leaf disc curative (Brown rust):
Wheat leaf segments cv Kanzler were placed on agar in 24-well plates. The leaf segments were inoculated with a spore suspension of the fungus. The plates were stored in darkness at 19°C and 75% relative humidity. The formulated test compound diluted in water was applied at an application rate of 200ppm 1 day after inoculation. The leaf segments were incubated at 19°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 - 8 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sP tritici: P14; P01; P08; P07; P09; P02; P03; P16; P18; P19; P20; P22; P23; P30; P33; P34; P38; P39; P40; P41; P42; P44; P45; P47; P48; P49; P50; P51; P.54; P.59; P.60; P.61; P.62; P.66; P.67; P69; P70; P71; P72; P73; P74; P75
Phaeosphaeria nodorum (Septoria nodorum) / wheat / leaf disc preventative (Glume blotch"): Wheat leaf segments cv Kanzler were placed on agar in a 24-well plate and sprayed with formulated test compound diluted in water at an application rate of 200ppm. The leaf disks are inoculated with a spore suspension of the fungus 2 days after application. The inoculated test leaf disks are incubated at 20°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5 - 7 days after application). The following compounds gave at least 80% control of Phaeosphaeria nodorum: P12; P13; P14; P01; P08; P09; P10; P02; P03; P04; P15; P16; P17; P18; P19; P20; P21; P22 P23; P24; P25; P26;P27; P28; P29; P31; P32; P33; P34; P37; P38; P39; P40; P41; P42; P43; P44; P45; P47; P48; P49; P50; P51; P.53; P.54; P.59; P.60; P.61; P.62; P.66; P.67; P69; P70; P71; P72; P73; P74; P75
Pyrenophora teres I barley / leaf disc preventative (Net blotch):
Barley leaf segments cv Hasso are placed on agar in a 24-well plate and sprayed with formulated test compound diluted in water at an application rate of 200ppm. The leaf segments are inoculated with a spore suspension of the fungus two days after application of the test solution. The inoculated leaf segments are incubated at 20°C and 65% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 - 7 days after application). The following compounds gave at least 80% control of Pyrenophora teres: P12; P14; P01; P08; P09; P02; P15; P16; P17; P18; P19; P20; P22; P23; P25; P27; P30; P31; P32; P33; P34; P37; P38; P39; P40; P41; P42; P43; P44; P45; P47; P48; P49; P50; P51; P.53; P.54; P.58; P.59; P.61; P.62; P.66; P.67; P69; P72; P74
Botryotinia fuckeliana (Botrytis cinerea) I liquid culture (Gray mould):
Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (Vogels broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Botryotinia fuckeliana: P12; P13; P14; P08; P09; P10; P07; P02; P03; P04; P15; P16; P17; P18; P19; P20; P21; P22; P23; P25; P26; P27;P28; P29; P30; P32; P33; P34; P35; P36; P37; P38; P39; P40; P41; P42; P43; P44; P45; P47; P48; P49; P50; P51; P.54; P.55; P.58; P.59; P.60; P.61; P.62; P.66; P.67; P69; P70; P71; P72; P73; P74; P75
Glomerella lagenarium (Colletotrichum lagenarium) I liquid culture (Anthracnose): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth is measured photometrically 3-4 days after application. The following compounds gave at least 80% control of Glomerella lagenarium: P14; P08; P09; P10; P07; P02; P04; P15; P16; P17; P18; P22; P24; P28; P29; P30; P32; P33; P36; P39; P40; P41; P42; P45; P47; P48; P49; P50; P51; P.53; P.54; P.55; P.58; P.59; P.61; P.62; P.66; P.67; P69; P70; P72; P73; P74; P75
Mycosphaerella arachidis (Cercospora arachidicola) I liquid culture (early leaf spot): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates are incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Mycosphaerella arachidis: P12; P14; P01; P08; P09; P10; P07; P02; P03; P04; P15; P16; P17; P18; P21; P22; P23; P24; P25; P26;P28; P29; P30; P32; P33; P34; P36; P37; P38; P39; P40; P41; P42; P43; P44; P45; P47; P48; P49; P51; P.53; P.54; P.58; P.59; P.62; P.66; P.67; P69; P70; P71; P72; P73; P74; P75
Mycosphaerella graminicola (Septoria tritici) I liquid culture (Septoria blotch):
Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Mycosphaerella graminicola: P13; P14; P01; P08; P06; P09; P10; P07; P02; P03; P04; P15; P16; P17; P18; P19; P20; P21; P22; P23; P24; P25; P26; P27;P28; P29; P30; P32; P34; P36; P37; P38; P39; P40; P41; P42; P43; P44; P45; P47; P48; P49; P50; P51; P54; P62; P67; P69; P70; P71; P72; P73; P74; P75
Gaeumannomyces graminis I liquid culture (Take-all of cereals):
Mycelial fragments of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth CP33, containing the fungal spores is added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Gaeumannomyces graminis: P12; P14; P08; P09; P10; P15; P17; P18; P19; P20; P21; P22; P23; P25; P27;P28; P29; P30; P31; P34; P36; P37; P38; P39; P40; P41; P42; P43; P44; P45; P48; P49 P51; P54; P55; P62; P67; P70; P71; P72; P73; P74; P75
Thanatephorus cucumeris (Rhizoctonia solani) I liquid culture (foot rot, dampinq- off):
Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compounds into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal material was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Thanatephorus cucumeris: P14; P10; P07; P02; P03; P04; P15; P16; P17; P18; P21; P22; P25; P28; P30; P31; P32; P33; P34; P36; P37; P39; P40; P41; P42; P43; P44; P45; P47; P48; P49; P50; P51; P62; P677; P70; P71; P72; P73; P74; P75
Monographella nivalis (Microdochium nivale) I liquid culture (foot rot cereals):
Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Monographella nivalis: P12; P08; P10; P07; P02; P15; P16; P19; P23; P24; P25; P28; P29; P30; P32; P40; P41; P42; P43; P44; P45; P47; P48; P49; P50; P51; P59; P62; P66; P6767; P71; P72; P73; P75
Blumeria graminis f. sP tritici (Erysiphe graminis f. sP tritici) I wheat / leaf disc preventative (Powdery mildew on wheat):
Wheat leaf segments cv. Kanzler were placed on agar in a 24-well plate and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks were incubated at 20°C and 60% relative humidity under a light regime of 24 h darkness followed by 12h/12h (dark/light) in a climate chamber and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application). The following compounds gave at least 80% control of Blumeria graminis: P12; P14; P01; P08; P09; P07; P02; P03; P04; P15; P16; P17; P18; P19; P20; P22; P23; P27;P28; P30; P32; P33; P34; P37; P38; P39; P40; P41; P42; P44; P45; P47; P48; P49; P50; P51; P54; P59; P60; P61; P62; P66; P67; P69; P70; P71; P72; P73; P74; P75
5 Pythium ultimum I liquid culture (seedling damping off)
Mycelia fragments and oospores of a newly grown liquid culture of the fungus were directly mixed into nutrient broth (potato dextrose broth). After placing a DMSO solution of test compound into a 96-well format microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal mycelia/spore mixture was added. The test plates were
10 incubated at 24°C and the inhibition of growth was determined photometrically 2-3 days after application. The following compounds gave at least 80% control of Pythium ultimum: P13; P14; P08; P09; P02; P03; P04; P15; P16; P18; P20; P22; P24; P31; P33; P39; P40; P41; P44; P45; P47; P48; P49; P50; P60; P61; P69; P70; P72; P73; P74; P75
Magnaporthe grisea (Pyricularia oryzae) I rice / leaf disc preventative (Rice Blast):
15 Rice leaf segments cv. Ballila were placed on agar in multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf segments were inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments were incubated at 22°C and 80% rh under a light regime of 24 h darkness followed by 12/12 h (light/dark) in a climate cabinet and the
20 activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 - 7 days after application). The following compounds gave at least 80% control of
Magnaporthe grisea: P14; P08; P09; P07; P02; P03; P04; P15; P16; P18; P19; P20; P22; P23; P30; P32; P33; P38; P39; P40; P41; P42; P43; P45; P51; P53; P54; P60; P61; P62;
25 P66; P67; P68; P69; P70; P71; P72; P73; P74; P75
Alternaria solani I tomato / leaf disc (early blight):
Tomato leaf disks cv. Baby were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 2 days after application. The inoculated
30 leaf disks were incubated at 23°C/21 °C (day/night) and 80% rh under a light regime of 12/12h (light/dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check disk leaf disks (5 - 7 days after application). The following compounds gave at least 80% control of Alternaria solani at an application rate of
35 200ppm or less: P07; P02; PI 5; P38; P40; P69

Claims

Claims:
1. A method comprising applying to useful plants, the locus thereof or propagation material thereof a compound of formula (I)
Figure imgf000201_0001
(I)
wherein
L1 is N or C-D1;
L2 is N or C-D2;
L3 is N or C-D3;
L4 is N or C-D4;
L5 is N or C-D5;
L6 is N or C-D6;
D1, D2, D3, D4, D5 and D6 independently of one another represent hydrogen, halogen, CN, N02, Ci-C8 alkyl, C3-C8 cycloalkyi, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6- membered heterocycle containing one to four heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR1, OR2, SH, d-C8 alkylthio, d-C8 alkylsulphinyl, Ci-C8 alkylsulphonyl, phenylthio, phenylsulphinyl,
phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl and d-C4 haloalkyl;
or D1 and D5, D2 and D5, D3 and D6, or D4 and D6 independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7- membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and D5, D2 and D5, D3 and D6, or D4 and D6 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
X represents X-2, X-3, X-4 or X-5: #—∑—∑—# #— z— z— z— # #—∑—∑—∑—∑—#
X-2 X-3 X-4
„ -.10 -.11 -.12 -.13 -.14 „
#— z— z— z— z— z— #
X-5
Z1, Z2, Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent CR4R5, C=0 or C=CR6R7;
Z4 and Z12 represent CR8R9, SiR^R11, C=0 or C=CR6R7;
wherein the groupings X-2, X-3, X-4 and X-5 contain at most one ring which contains either only one of the radicals Z1 to Z14 or two radicals Z1 to Z14 or three radicals Z1 to Z14 or four radicals Z1 to Z14 as ring members; and wherein none of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13 and Z14 represent a carbon atom substituted by two OH;
Q is selected from the group consisting of Q-l, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9
Figure imgf000202_0001
Q-6 Q-7 Q-8 Q-9 each Y1, Y2, Y3 and Y4 independently of one another represent hydrogen, halogen, CN, N02, Ci-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, benzyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR1, OR2, SH, d-C8 alkylthio, d-C8 alkylsulphinyl, Ci-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, OCCOJR1, CON(R3)2, NR^OR1, C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, benzyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OR2, Ci-C4 alkyl and Ci-C4 haloalkyl; when Q is Q-l, Q-2, Q-3, Q-4, Q-6 or Q-7 then Y1 and Y2, Y2 and Y3, or Y3 and Y4 independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y1 and Y2, Y2 and Y3, or Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, G-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q is Q-l, Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, then Y1 and D1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, C1-C4 alkyl, Q-G, haloalkyl, Q-G, alkoxy, Q-G, haloalkoxy and G-C4 alkylthio;
when Q is Q-9 and L1 is C-D1 then R12 and D1 together may be
Figure imgf000203_0001
Q' is selected from the group consisting of Q-Γ, Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q- 8' and Q-9'
Figure imgf000203_0002
Q-6' Q-7' Q-8' Q-9' each Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen,
CN, N02, G-Cs alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, benzyl, phenyl, a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR1, OR2, SH, G-C8 alkylthio, G-C8 alkylsulphinyl, G-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, benzyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OR2, Ci-C4 alkyl and Ci-C4 haloalkyl; when Q' is Q-Γ, Q-2', Q-3', Q-4', Q-6' or Q-7' then Y1' and Y2, Y2' and Y3', or Y3' and Y4' independently of the other, together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y1' and Y2', Y2' and Y3', or Y3' and Y4' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, G-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy and Ci-C4 alkylthio;
when Q' is Q-Γ, Q-3', Q-4', Q-7' or Q-8' and L4 is C-D4, then Y1' and D4 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D4 and Y1' is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, C1-C4 alkyl, Q-G, haloalkyl, Q-G, alkoxy, Q-G, haloalkoxy and Q-G, alkylthio;
when Q' is Q-9' and L4 is C-D4, then R12' and D4 together may be
Figure imgf000204_0001
each G1 and G2 independently of one another represent -C(R14R15)-;
each G3 independently of one another represents -C(R14R15)-, 0, N(R16) or S;
or each combination of G1 and G2, or G2 and G3, or G1 and G1 may independently of one another together represent -CR14=CR15-;
each p independently of one another represents 0, 1 or 2;
each R1 independently of one another represents hydrogen, G-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, G-C4 alkyl, G-C4 haloalkyl, G-C4 alkoxy and G-C4 haloalkoxy;
each R2 independently of one another represents hydrogen, G-C8 alkyl, C3-C8 cycloalkyl, C3-C8 alkenyl, C3-C8 alkynyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Q-G, alkyl, G-C4-haloalkyl, Q-G, alkoxy, Q-G, haloalkoxy and CrC4-alkoxy-Ci-C4-alkyl;
each R3 independently of one another represents hydrogen, OH, G-C8 alkyl, G-C8 alkoxy, G-C8-alkoxy-Ci-C4-alkyl, C3-C8 alkenyl, C3-C8 alkynyl or COR1, wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen;
wherein when two radicals R3 are attached to the same nitrogen atom, these radicals can be identical or different;
wherein when two radicals R3 are attached to the same nitrogen atom, both of these radicals cannot be OH, G-C4 alkoxy or G-C4 haloalkoxy;
and wherein when two radicals R3 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4, B-5, B-6, B-7 or B-8:
Figure imgf000205_0001
wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, G-C4 alkyl, G-C4 haloalkyi, G-C4 alkoxy and G-C4 haloalkoxy;
each R4 and R5 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6alkynyl, G-C6alkoxy, C3-C6 alkenyloxy, Cr
C6alkynyloxy, G-C6 alkylthio, G-C6 alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2,
NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocycle containing one to four heteroatoms independently selected from O, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, OR2, CN, G- G alkyl, G-C4 haloalkyi, G-G alkoxy, G-C4 haloalkoxy, G-C4 alkylthio, G-G haloalkylthio, CON(R3)2, NH2, NR^OR1 and phenyl;
or R4 and R5 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;
each R6 and R7 independently of one another represent hydrogen, halogen, G-G alkyl or G-C4 haloalkyi; each R8 and R9 independently of one another represent hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6alkynyl, d-C6alkoxy, C3-C6 alkenyloxy, C3- C6alkynyloxy, Ci-Ce alkylthio, Ci-Ce alkoxycarbonyl, C3-C6cycloalkyl, CON(R3)2, NH2,
NR3COR\ CR^-OR2, phenyl or 5- or 6-membered heterocycle containing one to four heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, OR2, CN, d- C4 alkyl, Ci-C4 haloalkyl, d-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, d-C4 haloalkylthio, CON(R3)2, NH2, NR^OR1 and phenyl;
or R8 and R9 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyi group or a C3-C6 halocycloalkyl group;
each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, Ci-C4 alkyl, C2-C4 alkenyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, C2-C4 alkenyloxy or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
R12 and R12' independently of one another represent hydrogen, halogen, CN, SH, d- C8 alkylthio, Ci-C8 alkylsulphinyl, d-C8 alkylsulphonyl, NH2, Ci-Cio alkyl, C3-C8 cycloalkyi, C2- C8 alkenyl, C2-C8 alkynyl, (R20)carbonyl(Ci-C4 alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, NH-Ci-C8 alkyl, N(Ci-C8 alkyl)2, N02, OR2, Ci-C4 alkyl, d-C4 haloalkyl, C3-C6 cycloalkyi and a 5- or 6- membered heterocycle containing one to three heteroatoms independently selected from O, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms;
R13 and R13' independently of one another represent hydrogen, Ci-C8 alkyl, C3-C8 cycloalkyi, C3-C8 alkenyl, C3-C8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy;
each R14 and R15 independently of one another represents hydrogen, halogen, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy or d-C4 haloalkoxy;
each R16 indepenently of one another represents hydrogen, OH, d-C4 alkyl, Ci-C4 alkoxy, C3-C6 cycloalkyi, d-C8 alkylcarbonyl or d-C8 haloalkylcarbonyl;
or a salt or N-oxide thereof.
2. A method according to claim 1, wherein X is X-3.
3. A method according to claim 1 or claim 2, wherein Q is Ql, Q2, Q-3 or Q9 and Q' is Ql', Q2', Q-3'or Q9'.
4. A method according to any one of claims 1 to 3, wherein L1 is C-D1, L2 is C-D2 and L5 is C-D5.
5. A method according to any one of claims 1 to 4, wherein L1 is C-D1, L2 is C-D2, L3 is C-D3, L4 is C-D4, L5 is C-D5 and L6 is C-D6.
6. A method according to any one of claims 1 to 3, wherein L1 is C-D1, L2 is N, and L5 is C-D5. 7. A method according to any one of claims 1 to 3, wherein L1 is C-D1, L2 and L3 are N, L4 is C-D4, L5 is C-D5 and L6 is C-D6.
8. A method according to any one of claims 1-3, wherein L1 is N, L2 is C-D2 and L5 is C- D5.
9. A method according to any one of claims 1-3, wherein L1 and L4 are N, L2 is C-D2, L3 is C-D3, L5 is C-D5 and L6 is C-D6.
10. A method according to any one of claims 1 to 9, wherein L1 is the same as L4, L5 is the same as L6, L2 is the same as L3, Q is the same as Q'.
11. A method according to any one of claims 1-10 wherein D1, D2, D3, D4, D5, D6, Y1, Y2, Y3, Y4, Y1', Y2', Y3' and Y4' independently of one another represent hydrogen, halogen, Ci-C8 alkyl, C2-C8 alkynyl, Ci-Cs alkoxy or Ci-Cs alkylthio.
12. A method according to any one of claims 1-11 wherein R13 and R13' independently of one another represent hydrogen, d-Q alkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from d-Q alkyl, d-C4 haloalkyl, halogen, CN, Ci-C4 alkoxy and d-C4 haloalkoxy.
13. A method according to any one of claims 1-12, wherein the method is a method of controlling or preventing phytopathogenic diseases on useful plants or on propagation material thereof. 14. A compound of formula I as defined in any one of claims 1 to 12, wherein X is X-3, X-4 or -5 and the compound of formula I is not a compound of formula Γ
Figure imgf000208_0001
wherein Ra is hydrogen or phenyl, Rb is primary alkyl and n is 4 or 5;
and the compound of formula I is not a compound of formula I"
Figure imgf000208_0002
wherein each Rc is independently hydrogen or methyl;
and the compound of formula I is not a compound of formula I'"a, I'"b or I'"c
Figure imgf000208_0003
(I'"a)
Figure imgf000209_0001
Figure imgf000209_0002
and the com ound of formula I is not a compound of formula I"
Figure imgf000209_0003
wherein
n is 3, Rd and Re are both methyl, Rf and R9 are both hydrogen; or
n is 3, Rd and Re are both paramethoxyphenyl, Rf and R9 are both hydrogen; or n is 4, Rd and Re are both hydrogen, Rf and R9 are both hydrogen; or n is 4 , Rd and Re are both paraformylphenyl, Rf and R9 are both hydrogen; or d and Re are both
Figure imgf000209_0004
Rf and R9 are both hydrogen; or
n is 4, Rd and Re are both n-butyl, Rf and R9 are both hydrogen; or
n is 4, Rd and Re are both hydrogen, Rf and R9 are both hydrogen; or n is 4, Rd and Re are both parahydroxyphenyl, Rf and R9 are both hydrogen; or n is 4, Rd and Re are both paramethoxyphenyl, Rf and R9 are both hydrogen; or n is 5, Rd and Re are both n-butyl, Rf and R9 are both hydrogen; or
n is 4, Rd and Re are both hydrogen, Rf and R9 are both paramethoxyphenyl
15. A compound of formula I according to claim 14, wherein when Q is Q-3, Q-4, Q-7 or Q-8 and L1 is C-D1, and Q is not Q-l, then Y1 and D1 together with the fragment to which they are attached can form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7- membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by D1 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, d-C4 haloalkyl, Ci-C4 alkoxy and d- C4 haloalkoxy;
R8 represents hydrogen, halogen, CN, OH, SH, CHO, Ci-Ce alkyl, Ci-Ce alkenyl, d- dalkynyl, d-dalkoxy, Ci-Ce alkenyloxy, Ci-Cealkynyloxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, C3-C6cycloalkyl, phenyl or 5- or 6-membered heterocycle containing one to three
heteroatoms independently selected from 0, S and N providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups independently selected from halogen, OH, CN, d-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy, d-C4 haloalkoxy, Ci-C4 alkylthio and d-C4 haloalkylthio; when Q is Q-l Y4 represents hydrogen, halogen, CN, N02, d-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, COR1, OR2, SH, Ci-C8 alkylthio, Ci-C8 alkylsulphinyl, Ci-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R3)2, C02R2, 0(CO)R\ CON(R3)2, NR3COR\ C^N-OR2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OR2, d-C4 alkyl, d-C4 haloalkyl and d-C4 alkylthio;
or Y4 together with Y3 and together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R3), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y3 and Y4 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, N02, OH, Ci-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy and Ci-C4 haloalkoxy.
A compound of formula Int-1
Figure imgf000211_0001
(lnt-1 )
wherein X' represents -CH=CH-CH2- or CH2-CH=CH- and Q, Q', L1, L2, L3 L4, L5 and L6 are as defined for compounds of formula (I) in any one of claims 1 to 13, or a salt or N- oxide thereof; or a compound of formula Int-2
Figure imgf000211_0002
(lnt-2)
wherein L1, L2, L3 L4, L5, L6 and X are as defined for compounds of formula (I) in any one of claims 1 to 13, or a salt or N-oxide thereof. a compound of formula Int-3
Figure imgf000211_0003
(lnt-3)
wherein L1, L2, L3 L4, L5, L6 , Q and X are as defined for compounds of formula (I) in any one of claims 1 to 13, or a salt or N-oxide thereof. a compound of formula Int-4
Figure imgf000211_0004
(lnt-4)
wherein L1, L2, L3 L4, L5, L6 , Q and X are as defined for compounds of formula (I) in any one of claims 1 to 13, or a salt or N-oxide thereof. a compound of formula Int-5
Figure imgf000212_0001
(lnt-5)
wherein L1, L2, L3 L4, L5, L6 , Q and X are as defined for compounds of formula (I) in any one of claims 1 to 13 and R28 is is a halogen in particular chlorine, bromine or iodine, or a salt or N-oxide thereof.
17. A composition comprising a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 15, optionally comprising at least one additional active ingredient.
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