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WO2015052173A1 - Composés tétrazole et triazole et leur utilisation en tant qu'herbicides - Google Patents

Composés tétrazole et triazole et leur utilisation en tant qu'herbicides Download PDF

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WO2015052173A1
WO2015052173A1 PCT/EP2014/071421 EP2014071421W WO2015052173A1 WO 2015052173 A1 WO2015052173 A1 WO 2015052173A1 EP 2014071421 W EP2014071421 W EP 2014071421W WO 2015052173 A1 WO2015052173 A1 WO 2015052173A1
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alkyl
alkoxy
group
compounds
formula
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PCT/EP2014/071421
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English (en)
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Frederick CALO
Markus Kordes
Helmut Kraus
Thomas Seitz
Trevor William Newton
Klaus Kreuz
Maciej Pasternak
Dario MASSA
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • Tetrazole and triazole compounds and their use as herbicides Description
  • the present invention relates to tetrazole and triazole compounds and compositions comprising the same.
  • the invention also relates to the use of the tetrazole and triazole compounds or the corresponding compositions for controlling unwanted vegetation.
  • the invention relates to methods of applying the tetrazole and triazole compounds or the corresponding compositions.
  • WO 201 1/035874 describes N-(1 ,2,5-oxadiazol-3-yl)benzamides carrying 3 substituents in the 2-, 3- and 4-positions of the phenyl ring and their use as herbicides.
  • WO 2012/028579 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 3- and 4-positions of the aryl ring and their use as herbicides.
  • WO 2013/104705 describes tetrazol-5-yl- and triazol-5-yl-aryl compounds and their use as herbicides.
  • the compounds of the prior art often suffer from insufficient herbicidal activity, in particular at low application rates, and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.
  • tetrazole and triazole compounds having a strong herbicidal activity, in particular even at low application rates, a suf- ficiently low toxicity for humans and animals and/or a high compatibility with crop plants.
  • the tetrazole and triazole compounds should also show a broad activity spectrum against a large number of different unwanted plants.
  • the present invention relates to a compound of formula I,
  • R is selected from the group consisting of halogen, d-Cs-alkyl, d-Cs-haloalkyl, nitro, C1-C4- alkoxy-Ci-C4-alkyl, cyano-Z 1 , C2-Cs-alkenyl, C2-Cs-alkynyl, C3-Cio-cycloalkyl-Z 1 , C2-C8- haloalkenyl, Cs-Cs-haloalkynyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Z 1 , C1-C4- alkylthio-Ci-C 4 -alkyl, Ci-C 4 -alkylthio-Ci-C 4 -alkylthio-Z 1 , C 2 -C 6 -alkenyloxy, C 2 -C 6 - alkynyloxy, Ci-C6-haloalkoxy
  • X is N or CR 2 ;
  • R 2 is selected from the group consisting of hydrogen, halogen, hydroxy-Z 2 , nitro, C1-C4- nitroalkyl, cyano, Ci-C4-cyanoalkyl, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, C3-C10- cycloalkyl-Z 2 , C3-Cio-cycloalkoxy-Z 2 , where the C3-Cio-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-Cs- haloalkyl, C2-C8-haloalkenyl, Cs-Cs-haloalkynyl, Ci-Cs-alkoxy-Z 2 , Ci-Cs-haloalkoxy-Z 2 , C3- Cio-cycloalkyl-Ci-C2-alkoxy, Ci-C4-alkoxy-Ci
  • heterocyclyl-Z 2a where heterocyclyl is a 3-, 4-, 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl- Z 2a and heterocyclyl-Z 2a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R 21 , which are identical or different,
  • R 11 , R 21 independently of each other are selected from the group consisting of halogen, NO2, CN, d-Ce-alkyl, C3-C 7 -cycloalkyl, C3-C 7 -halocycloalkyl, d-Ce-haloalkyl, C2 C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy- Ci-C4-alkoxy- Ci-C4-alkoxy, C3-C7-cycloalkoxy and Ci-C6-haloalkyloxy, or two radicals R', R 11
  • Z 1 , Z 2 independently of each other are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl;
  • Ci-C4-alkanediyl O-C1-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl;
  • R 1b , R 2b independently of each other are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloal
  • R 2c independently of each other are selected from the group consisting of hydrogen, Ci- C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely
  • Ci-C6-haloalkyl C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic
  • heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R 2d independently of each other are selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci- C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C4- alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C
  • R e , R f independently of each other are selected from the group consisting of hydrogen, Ci- C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely
  • Ci-C6-haloalkyl C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or
  • R f together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7- membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R 2e , R 2f independently of each other have the meanings given for R e , R f ;
  • R9 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-
  • C4-alkylsulfonyl Ci-C4-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R3 ⁇ 4, R 2h independently of each other have the meanings given for Rs, R h ;
  • R k has the meanings given for R c ;
  • R 22 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycl oa I ky l-C 1 -Ce-a I koxy-C 1 -Ce-a I ky I ,
  • R 23 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl and phenyl;
  • R 24 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl and phenyl;
  • R 25 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci- C6-a I koxy-C 1 -C6-a I ky I ,
  • R 26 is d-Ce-alkyl or Ci-C 4 -alkoxy-Ci-C 4 -alkyl
  • R 27 is selected from the group consisting of hydrogen, cyano and Ci-C 4 -haloalkylcarbonyl; R 28 , R 29 independently of each other are Ci-C6-alkyl, or
  • R 28 , R 29 together with the sulfur atom, to which they are bound may form a 5- or 6-membered saturated ring, which may carry as a ring member 1 oxygen atom; k is 0, 1 or 2;
  • n 0, 1 or 2;
  • s 0, 1 , 2 or 3;
  • the compounds of the present invention i.e. the compounds of formula I, their N-oxides or their salts, are particularly useful for controlling unwanted vegetation. Therefore, the present invention also relates to the use of a compound of formula I, an N-oxide or a salt thereof or a composition comprising at least one compound of formula I, an N-oxide or an agriculturally suit- able salt thereof for combating or controlling unwanted vegetation.
  • the invention also relates to a composition comprising at least one compound of the present invention, including an N-oxide or a salt thereof, and at least one auxiliary.
  • the invention relates to an agricultural composition comprising at least one compound of the present invention, including an N-oxide or an agriculturally suitable salt thereof, and at least one auxilia- ry customary for crop protection formulations.
  • the invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound of the present invention, including an N-oxide or a salt thereof, to act on unwanted plants, their seed and/or their habitat.
  • the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures.
  • Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the compounds of formula I may be present in the form of their tautomers.
  • the invention also relates to the tautomers of the formula I and the stereoisomers, salts and N-oxides of said tautomers.
  • N-oxide includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N-oxides in compounds of formula I can in particular be prepared by oxidizing the ring nitrogen atom(s) of the tetrazole (in the case of B being N), triazole (in the case of B being CH), isoxazole (in the case of Q being Q 2 ) or pyridine (in the case of X being N) ring with a suitable oxidizing agent, such as peroxo carbox- ylic acids or other peroxides, or the ring nitrogen atom(s) of a heterocyclic substituent R 1 , R 2 , R 3 , R 4 or R 5 .
  • a suitable oxidizing agent such as peroxo carbox- ylic acids or other peroxides
  • the present invention further relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably non- radioactive isotope (e.g. hydrogen by deuterium, 12 C by 13 C, 14 N by 15 N, 16 0 by 18 0) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom.
  • non- radioactive isotope e.g. hydrogen by deuterium, 12 C by 13 C, 14 N by 15 N, 16 0 by 18 0
  • these compounds contain more of the respective isotope than the isotope naturally occurs and thus is anyway present in the compounds of formula I.
  • the compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of formula I, their enantiomers or diastere- omers, mixtures of different crystalline states of the respective compound of formula I, its enan- tiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed by customary methods, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • Useful agriculturally suitable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, C1-C4- hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isoprop- ylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetrame- thylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensul- fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • weeds undesired vegetation
  • weeds are understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any).
  • Weeds, in the broadest sense, are plants considered undesirable in a particular location.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n - Cm indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
  • partially or completely halogenated means that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • a partially or completely halogenated radical is termed below also “halo- radical”.
  • partially or completely halogenated alkyl is also termed haloalkyi.
  • alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 car- bon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
  • Ci-C4-alkyl examples include methyl, ethyl, n-propyl, iso-propyl, n- butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl.
  • Ci-C6-alkyl are, apart from those mentioned for Ci-C4-alkyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methyl
  • Ci-Cio-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2- methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1 -ethylpentyl, 2-ethylpentyl, 3- ethylpentyl, n-octyl, 1 -methyloctyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl,
  • alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • haloalkyi as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms (“Ci-Cs-haloalkyl”), frequently from 1 to 6 carbon atoms (“C1-C6- haloalkyl”), more frequently 1 to 4 carbon atoms (“Ci-C4-haloalkyl”), wherein the hydrogen at- oms of this group are partially or totally replaced with halogen atoms.
  • haloalkyi as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi group, e.
  • haloalkyi moieties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halomethyl, in particular from Ci-C2-fluoroalkyl.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • Ci-C2-fluoroalkyl fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, pentafluoroethyl, and the like.
  • Ci-C2-haloalkyl are, apart those mentioned for Ci-C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 2-chloroethyl, 2,2,- dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-
  • Ci-C4-haloalkyl are, apart from those mentioned for Ci-C2-haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trifluoroprop-2-yl, 3-chloropropyl, 4-chlorobutyl and the like.
  • cycloalkyi as used herein (and in the cycloalkyi moieties of other groups comprising a cycloalkyi group, e.g. cycloalkoxy and cycloalkylalkyi) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C3-Cio-cycloalkyl”), preferably 3 to 7 carbon atoms (“C3-C7-cycloalkyl”) or in particular 3 to 6 carbon atoms (“C3-C6- cycloalkyl").
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1 ]octyl.
  • halocycloalkyl as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are
  • cycloalkyl-alkyl used herein denotes a cycloalkyi group, as defined above, which is bound to the remainder of the molecule via an alkylene group.
  • C3-C7- cycloalkyl-Ci-C4-alkyl refers to a C3-C7-cycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Examples are cyclo- propylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobu- tylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentyl propyl, cyclohexylmethyl, cyclo- hexylethyl, cyclohexylpropyl, and the like.
  • alkenyl denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 (“C2-C8-alkenyl”), preferably 2 to 6 carbon atoms (“C2-C6-alkenyl”), in particular 2 to 4 carbon atoms (“C2-C4-alkenyl”), and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 - methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 - methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl, 1 -methylethenyl,
  • haloalkenyl as used herein, which may also be expressed as "alkenyl which is substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 ("C2-C8-haloalkenyl") or 2 to 6 (“C2-C6-haloalkenyl”) or 2 to 4 (“C2-C4-haloalkenyl”) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlo- rovinyl, chloroallyl and the like.
  • alkynyl denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 (“C2-C8-alkynyl”), frequently 2 to 6 (“C2-C6-alkynyl”), pref- erably 2 to 4 carbon atoms (“C2-C4-alkynyl”) and a triple bond in any position, for example C2- C4-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentyn
  • haloalkynyl as used herein, which is also expressed as “alkynyl which is substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 carbon atoms (“C2-C8-haloalkynyl”), frequently 2 to 6 (“C2-C6-haloalkynyl”), preferabyl 2 to 4 carbon atoms (“C2-C4-haloalkynyl”), and a triple bond in any position (as men- tioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • C2-C8-haloalkynyl unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 carbon atoms
  • C2-C6-haloalkynyl frequently 2 to 6
  • C2-C4-haloalkynyl preferabyl 2 to 4 carbon atom
  • alkoxy denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms ("d-Cs-alkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-alkoxy”), preferably 1 to 4 carbon atoms (“Ci-C4-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom.
  • Ci-C2-alkoxy is methoxy or ethoxy.
  • Ci-C4-alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy).
  • Ci-C6-alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1 - dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 - methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2- dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,
  • Ci-Cs-alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • haloalkoxy denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms (“Ci-Cs-haloalkoxy”), frequent- ly from 1 to 6 carbon atoms (“Ci-C6-haloalkoxy”), preferably 1 to 4 carbon atoms (“C1-C4- haloalkoxy”), more preferably 1 to 3 carbon atoms (“Ci-C3-haloalkoxy”), wherein the hydrogen atoms of this group are partially or completely replaced by halogen atoms, in particular fluorine atoms.
  • Ci-C 2 -haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH2CI, OCHC , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5.
  • Ci-C4-haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH 2 F)-2-fluoroethoxy, 1 -(CH 2 CI)-2-chloroethoxy, 1 -(CH 2 Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C6-haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
  • alkoxyalkyl denotes in each case alkyl usually comprising 1 to
  • Ci-C6-alkoxy-Ci-C6-alkyl is a Ci-C6-alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above.
  • Examples are CH2OCH3, CH2- OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (l -methylpropoxy)-methyl, (2- methylpropoxy)methyl, CH2-OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2- (1 -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1 - methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1 -methylpropoxy)-propyl, 2-(2-methyl
  • haloalkoxy-alkyl denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Examples are fluoromethoxymethyl, difluoro- methoxymethyl, trifluoromethoxymethyl, 1 -fluoroethoxymethyl, 2-fluoroethoxymethyl, 1 ,1 - difluoroethoxymethyl, 1 ,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1 ,1 ,2- trifluoroethoxymethyl, 1 ,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethox- ymethyl, 1 -fluoroethoxy-1 -ethyl, 2-fluoroethoxy-1 -ethyl, 1 ,1 -difluoroethoxy-1 -ethyl, 1 ,2- difluoroethoxy-1 -ethyl, 2,2-difluoroethoxy-1 -ethyl, 1 ,1 ,2-trifluoroethoxy-1 -e
  • alkylthio (also alkylsulfanyl, “alkyl-S” or “alkyl-S(0) k “ (wherein k is 0)) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms (“Ci-Cs-alkylthio”), frequently comprising 1 to 6 carbon atoms (“Ci-C6-alkylthio”), preferably 1 to 4 carbon atoms (“Ci-C4-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group.
  • Ci-C2-alkylthio is methylthio or ethylthio.
  • Ci-C4-alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (iso- propylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 - dimethylethylthio (tert-butylthio).
  • Ci-C6-alkylthio is additionally, for example, pentylthio, 1 - methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
  • Ci-Cs-alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • haloalkylthio refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine.
  • Ci-C 2 -haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHCI 2 , SCC , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2- fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2 -fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2
  • Ci-C4-haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,
  • Ci-C6-haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
  • alkylsulfinyl and “alkyl-S(0)k” (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • alkylsulfinyl and “alkyl-S(0)k” (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • the term “Ci-C2-a I kylsu If i nyl " refers to a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-alkylsulfinyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • Ci-C4-alkylsulfinyl is additionally, for example, n-propylsulfinyl,
  • C1-C6- alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2- methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2- methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 ,1 -dimethylbutylsulfinyl,
  • alkylsulfonyl and “alkyl-S(0)k” (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-alkylsulfonyl refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C4-alkylsulfonyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C6-alkylsulfonyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-alkylsulfonyl is methyl- sulfonyl or ethylsulfonyl.
  • Ci-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec- butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert- butylsulfonyl).
  • Ci-C6-alkylsulfonyl is additionally, for example, pentylsulfonyl,
  • alkylamino denotes in each case a group R * HN-, wherein R * is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms ("C1-C6- alkylamino"), preferably 1 to 4 carbon atoms (“Ci-C4-alkylamino").
  • C1-C6- alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2- butylamino, iso-butylamino, tert-butylamino, and the like.
  • dialkylamino denotes in each case a group R * R°N-, wherein R * and R°, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms ("di-(Ci-C6-alkyl)-amino"), preferably 1 to 4 carbon atoms (“di- (Ci-C4-alkyl)-amino").
  • Examples of a di-(Ci-C6-alkyl)-amino group are dimethylamino, diethyla- mino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl- isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl- isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.
  • aryl refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.
  • heteroaryl refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrim- idyl and the like.
  • N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO2.
  • An unsaturated heterocyde contains at least one C-C and/or C-N and/or N-N double bond(s).
  • a fully unsaturated heterocyde contains as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the size(s) of the ring(s).
  • An aromatic monocyclic heterocyde is a fully unsaturated 5- or 6-membered monocyclic heterocyde.
  • An aromatic bicyclic heterocyde is an 8-, 9- or 10-membered bicyclic heterocyde consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring.
  • the heterocyde may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocyde include:
  • oxirane-2-yl aziridine-1 -yl, aziridine-2-yl, oxetan-2-yl, azetidine-1 -yl, azetidine-2-yl, azetidine-3- yl, thietane-1 -yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahy- drothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1 -yl, imidazolidin-2-yl, imidazo
  • Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-
  • Examples of a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1- pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4- thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1 -oxopyridin-2-yl, 1 -oxopyridin-3-yl, 1 -oxopyridin-4-yl,3- pyr
  • Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include: benzofuranyl, benzothienyl, indolyl, indazolyl, ben- zimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, iso- chinolinyl, purinyl, 1 ,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.
  • Preferred compounds according to the invention are compounds of formula I or a stereoisomer, salt or N-oxide thereof, wherein the salt is an agriculturally suitable salt. Further preferred compounds according to the invention are compounds of formula I or an N-oxide or salt thereof, especially an agriculturally suitable salt. Particularly preferred compounds according to the invention are compounds of formula I or a salt thereof, especially an agriculturally suitable salt thereof.
  • variable Q in the compounds of formula I is Q 2 :
  • variable X in the compounds of formula Ms N is variable X in the compounds of formula Ms N.
  • variable X in the compounds of formula I is CR 2 .
  • X is CR 2 and R 2 is hydrogen.
  • X is CR 2 and R 2 is not hydrogen.
  • variable B in the compounds of formula Ms N is variable B in the compounds of formula Ms N.
  • variable B in the compounds of formula I is CH.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 1 is selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2- C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z 1 , Ci-C4-alkylthio-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkylthio-Z 1 , C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, C1-C4- hal
  • R 1 is selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- haloalkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Z 1 , Ci-C 4 -alkylthio-Ci-C 4 -alkyl, C1-C4- alkylthio-Ci-C4-alkylthio-Z 1 , C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, C1-C
  • Z 1 is in particular a covalent bond. More preferably, R 1 is selected from the group consisting of halogen, CN, nitro, Ci-C4-alkyl, C3- C6-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Ci- C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C4-alkenyloxy, C3-C4-alkynyloxy, Ci-C4-alkoxy-Ci- C4-
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C3-C6- cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, specif- ically R 1 is F, CI, Br, N0 2 , CH 3 , cyclopropyl, CF 3 , OCH 3 , OCF 3 , SCF 3 , SO2CH3, CH2OCH3 or CH2OCH2CH2OCH3, and more specifically R 1 is CI, N0 2 , CH 3 , cyclopropyl,
  • variable R 2 in the com- pounds of formula I is hydrogen.
  • variable R 2 in the compounds of formula I has any one of the meanings given above for R 2 with the exception of hydrogen.
  • variable R 2 in the compounds of formula I is a 5- or 6-membered heterocyclyl, where heterocyclyl is a saturated, partially unsaturated or aromatic heterocyclic radical, which contains as a ring member 1 heteroatom selected from the group consisting of O, N and S and 0, 1 , 2 or 3 further nitrogen atoms, where heterocyclyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 , as defined herein, which are identical or different.
  • variable R 2 in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from the group consisting of isoxazolinyl (4,5-dihydroisoxazolyl), 1 ,2-dihydrotetrazolonyl, 1 ,4-dihydrotetrazolonyl, tetrahy- drofuryl, dioxolanyl, piperidinyl, morpholinyl, piperazinyl, isoxazolyl, pyrazolyl, thiazolyl, oxazolyl, furyl, pyridinyl, pyrimidinyl and pyrazinyl, where heterocyclyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 which are identical or different and selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-
  • variable R 2 in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from 4,5-dihydroisoxazol-3-yl, which is unsubstituted or substituted in position 5 with CH3, CH2F or CHF2, 4,5-dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH 3 , OCH 3 , CH2OCH3, CH2SCH3, 1 - methyl-5-oxo-1 ,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5-dihydrotetrazol-1 -yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3-methyl-isoxazol-5-yl, 1 -methyl-1 H-pyrazol- 3-yl, 2-methyl-2H-pyrazol-3
  • variable R 2 in the compounds of formula I is phenyl-Z 2a , where Z 2a is as defined herein, and where phenyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 which are identical or different and as defined above and which are in particular selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci- C 4 -alkyl and Ci-C 4 -alkoxy-Ci-C 4 -alkoxy, and preferably from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkyl and Ci-C2-alkoxy-Ci-C2-alkoxy.
  • variable R 2 in the compounds of formula I is a radical of the following formula:
  • R P1 is hydrogen or halogen, preferably hydrogen, F, CI or Br, and in particular H or F;
  • R P2 is hydrogen, halogen or Ci-C2-alkoxy, preferably hydrogen, F, CI, Br, OCH3 or OCH2CH3, and in particular H, F, CI or OCH3; and
  • R P3 is hydrogen, halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-alkoxy-Ci-C2- alkoxy, preferably hydrogen, F, CI, Br, CH 3 , C 2 H 5 , CF 3 , CHF 2 , CH 2 F, CCI 2 F, CF 2 CI, CH2CF3, CH2CHF2, CF2CF3, OCH3, OCH2CH3, OCH2OCH3, OCH2CH2OCH2CH3,
  • variable R 2 in the compounds of formula I is phenyl which is unsubstituted or carries one radical R 21 , where R 21 is preferably attached to position 4 of the phenyl group and is as defined above and in particular selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkyl and Ci-C2-alkoxy-Ci-C2-alkoxy, preferably from CH3, C 2 H 5 , OCH3, OC 2 H 5 , CHF 2 , CF 3 , OCH2OCH3 and OCH 2 CH 2 OCH 3 , and specifically from OCH 3
  • variable R 2 in the compounds of formula I is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C3-C6- cycloalkyl-Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6- haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy, Ci-C 4 -alkoxycarbonyl, C1-C4- alkyl-S(0)
  • variable R 2 in the com- pounds of formula I is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci- C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkenyloxy, C3-C6- haloalkynyloxy, Ci-C 4 -alkoxycarbonyl, Ci-C 4 -alkyl-S(0)k and Ci-C 4 -haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the
  • variable R 2 in the compounds of formula I is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C 4 -alkoxy- Ci-C 4 -alkyl, Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C 4 -alkoxy, C1-C4- haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may
  • variable R 2 in the compounds of formula I is selected from the group consisting of hydrogen, 4,5-dihydroisoxazol- 3-yl, which is unsubstituted or substituted in position 5 with CH3, CH2F or CHF2, 4,5- dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH3, OCH3, CH2OCH3, CH2SCH3, 1 -methyl-5-oxo-1 ,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5- dihydrotetrazol-1 -yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3- methyl-isoxazol-5-yl, 1 -methyl-1 H-pyrazol-3-yl, 2-methyl-2H-pyrazol-3-yl, thiazol-2-
  • variable R 2 in the compounds of formula I is
  • R 26 is selected from the group consisting of methyl, ethyl and methoxyethyl,
  • R 27 is selected from the group consisting of hydrogen, cyano and trifluoroacetyl
  • t is O or l ;
  • R 28 is ethyl and R 29 is ethyl, or R 28 and R 29 together are -(CH 2 ) 5 - or -(CH 2 )2-0-(CH 2 )2-.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C4-alkenyloxy, C3- C4-alkynyloxy or R 2b -S(0)k, where k and R 2b have one of the herein defined meanings.
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C4-alkenyloxy, C3- C4-alkynyloxy or R 2b -S(0)k, where k is 0, 1 or 2 and where R 2b is selected from Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C 4 -alkyl-S(0) 2 and Ci-C 4 -haloalkyl-S(0) 2 .
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro,
  • Preferred compounds according to the invention are compounds of formula I, wherein R 4 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C2-alkyl and C1-C2- haloalkyl, in particular from the group consisting of hydrogen, CHF2, CF3, CN, NO2, CH3 and halogen, and specifically from hydrogen, CHF2, CF3, CN, NO2, CH3, F, CI and Br.
  • R 4 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C2-alkyl and C1-C2- haloalkyl, in particular from the group consisting of hydrogen, CHF2, CF3, CN, NO2, CH3 and halogen, and specifically from hydrogen, CHF2, CF3, CN, NO2, CH3, F, CI and Br.
  • R 4 is hydrogen, chlorine or fluorine.
  • R 4 is chlorine or fluorine.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 5 is selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, and in particular from the group consisting of CHF2, CF3 and halogen.
  • R 5 is chlorine or fluorine.
  • R 4 is hydrogen, chlorine or fluorine and R 5 is chlorine or fluorine.
  • R 4 is hydrogen and R 5 is chlorine or fluorine.
  • R c is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R d is Ci-C 4 -alkyl
  • R e is hydrogen or Ci-C4-alkyl
  • R f is hydrogen or Ci-C4-alkyl
  • R e , R f together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a fur- ther heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 methyl groups,
  • R k is Ci-C 4 -alkyl.
  • More preferred compounds according to the invention are compounds of formula I, where- in R 6 is selected from the group consisting of Ci-C4-alkyl, C3-C7-cycloalkyl, Ci-C4-haloalkyl, C2- C6-alkenyl, C2-C6-alkynyl and Ci-C4-alkoxy-Ci-C4-alkyl.
  • R 6 is selected from the group consisting of Ci-C4-alkyl and Ci-C2-alkoxy-Ci-C2-alkyl, particularly from methyl, ethyl, n-propyl, methoxymethyl, ethoxymethyl and methoxyethyl.
  • Particularly preferred compounds according to the invention are compounds of formula I, wherein R 6 is selected from the group consisting of methyl, ethyl, n-propyl and methoxyethyl.
  • R', R 11 , R 21 independently of each other are selected from halogen, Ci-C4-alkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy and Ci-C6-haloalkyloxy; and more preferably from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.
  • R', R 11 , R 21 independently of each other are selected from halogen
  • Z, Z 1 , Z 2 independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.
  • Z 2a is selected from a covalent bond, Ci-C2-alkanediyl, 0-Ci-C2-alkanediyl, C1-C2- alkanediyl-0 and Ci-C2-alkanediyl-0-Ci-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyI, O-ethanediyI, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.
  • R b , R 1 b , R 2b independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy.
  • R b , R 1 b , R 2b independently of each other are selected from Ci-C4-alkyl, C2-C4- alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring mem- bers, which are selected from the group consisting of O, N and S.
  • R b , R 1 b , R 2b independently of each other are selected from Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • R c , R 2c , R k independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the
  • R c , R 2c , R k independently of each other are selected from hydrogen, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C-alkenyl, C2-C-haloalkenyl, C2-C-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
  • R c , R 2c , R k independently of each other are selected from hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • R d , R 2d independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.
  • R d , R 2d independently of each other are selected from Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7- cycloalkyl, which is unsubstituted or partially or completely halogenated; and in particular from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6- cycloalkyl.
  • R e , R f , R 2e , R 2f independently of each other are selected from hydrogen, Ci-C6-alkyl, C3- C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, or R e and R f or R 2e and R 2f together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocycl
  • R e , R f , R 2e , R 2f independently of each other are selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and benzyl, or R e and R f or R 2e and R 2f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N- bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R e , R f , R 2e , R 2f independently of each other are selected from hydrogen and
  • Ci-C4-alkyl, or R e and R f or R 2e and R 2f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.
  • R9, R3 ⁇ 4 independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl and benzyl.
  • R3 ⁇ 4 independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated; and in particular from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6- cycloalkyl.
  • R h , R 2h independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated; and in particular from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6- cycloalkyl; or
  • R9 and R h or R3 ⁇ 4 and R 2h together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is
  • unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of 0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy;
  • R h or R3 ⁇ 4 and R 2h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl;
  • n and k independently of each other are 0 or 2, and in particular 2.
  • R 22 is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6- alkoxy-Ci-C6-alkyl, phenyl, phenyl-Ci-C6-alkyl, heteroaryl, heteroaryl-Ci-C6-alkyl, heterocyclyl, heterocyclyl-Ci-C6-alkyl, phenyl-0-Ci-C6-alkyl, heteroaryl-0-Ci-C6-alkyl, heterocyclyl-0-Ci-C6-alkyl, where the 9 aforementioned radicals are substituted by s residues selected from the group consisting
  • R 22 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-
  • Ci-C4-alkyl C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, phenyl and phenyl-Ci-C2-alkyl.
  • R 22 is hydrogen or Ci-C4-alkyl.
  • R 23 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and C3-C6-cycloalkyl. In particular, R 23 is hydrogen or Ci-C4-alkyl.
  • R 24 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl and C3-C6-cycloalkyl. In particular, R 24 is
  • Ci-C 4 -alkyl Ci-C 4 -alkyl
  • R 25 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6- alkyl, phenyl, phenyl-Ci-C6-alkyl, heteroaryl, heteroaryl-Ci-C6-alkyl, heterocyclyl, heterocyclyl- Ci-C6-alkyl, phenyl-0-Ci-C6-alkyl, heteroaryl-0-Ci-C6-alkyl, heterocyclyl-0-Ci-C6-alkyl, where the 9 aforementioned radicals are substituted by s residues selected from the group consisting of nitro,
  • R 25 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, phenyl and phenyl-Ci-C2-alkyl.
  • R 25 is Ci-C 4 -alkyl.
  • R 26 is selected from the group consisting of methyl, ethyl and methoxyethyl.
  • R 27 is selected from the group consisting of hydrogen, cyano and trifluoroacetyl.
  • R 28 is ethyl and R 29 is ethyl, or R 28 and R 29 together are -(CH 2 ) 5 - or -(CH 2 )2-0-(CH 2 )2-.
  • s is 0, 1 , 2 or 3. In one particular embodiment of the invention, s is 0. In another particular embodiment of the invention, s is 1 , 2 or 3.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; and
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-
  • R 1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and C1-C4- alkyl-S(0) 2 ;
  • R 2 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-haloalkoxy, C3-C6-cycloalkyl-Ci-C2-alkoxy, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy- Ci-C 2 -alkyl, Ci-C 2 -alkoxy-Ci-C 2 -alkoxy, Ci-C 4 -alkyl-S(0) k , where k is 0, 1 or 2, N(Ci-C 4 - alkyl)S02(Ci-C4-alkyl), isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci- C 4 -haloalkyl and Ci-C 4 -alkyl-S(0) 2 ;
  • R 4 is selected from the group consisting of hydrogen, cyano, methyl and halogen
  • R 5 is selected from the group consisting of halogen, CHF2 and CF3;
  • R 6 is selected from the group consisting of Ci-C4-alkyl and Ci-C2-alkoxy-Ci-C2-alkyl.
  • R 1 is selected from the group consisting of chlorine, nitro, methyl, cyclopropyl, trifluoromethyl, methoxymethyl, CH2OCH2CH2OCH3 and methylsulfonyl;
  • R 2 is selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methoxy, ethoxy, OCH 2 (cyclo-C3H 5 ), OCHF 2 , OCH2CF3, OCH2CH2OCH3, methoxymethyl,
  • CH2OCH2CF3 methylsulfonyl, ethylsulfonyl, methylsulfinyl, ethylsulfinyl, methylsulfanyl, ethylsulfanyl, NCH3SO2CH3, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 5-isoxazolinyl, 3- methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5- isoxazolyl;
  • R 3 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl and methylsulfonyl;
  • R 4 is selected from the group consisting of hydrogen, cyano, methyl, chlorine and fluorine
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of methyl, ethyl, propyl, methoxymethyl, methoxy- ethyl and ethoxymethyl.
  • X is N and the variables R 1 , R 3 , R 4 , R 5 and R 6 have the following meanings:
  • R 1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C 4 -alkyl-S(0) 2 ;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl,
  • R 4 is selected from the group consisting of hydrogen, cyano, methyl and halogen
  • R 5 is selected from the group consisting of halogen, CHF2 and CF3;
  • R 6 is selected from the group consisting of Ci-C4-alkyl and Ci-C2-alkoxy-Ci-C2-alkyl.
  • R 1 is selected from the group consisting of chlorine, nitro, methyl, cyclopropyl, trifluo- romethyl, methoxymethyl, CH2OCH2CH2OCH3 and methylsulfonyl;
  • R 3 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl and methylsulfonyl;
  • R 4 is selected from the group consisting of hydrogen, cyano, methyl, chlorine and fluorine;
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of methyl, ethyl, propyl, methoxymethyl, meth- oxyethyl and ethoxymethyl.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and C1-C4- alkyl-S(0)2; and in particular selected from the group consisting of chlorine, nitro, methyl, cyclopropyl, trifluoromethyl, methoxymethyl, CH2OCH2CH2OCH3 and methylsulfonyl;
  • R 2 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-haloalkoxy-Ci-C2- alkyl, Ci-C4-alkyl-S(0)k, where k is 0 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl; and in particular selected from the group consisting of hydrogen, methyl, CH2OCH2CF3, methylsulfonyl, ethylsulfonyl, methylsulfanyl, ethylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl and 3- methyl-5-isoxazolyl;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci- C4-haloalkyl and Ci-C4-alkyl-S(0)2; and in particular selected from the group consisting of hydrogen, chlorine, fluorine, cyano, nitro, methyl, trifluoromethyl and methylsulfonyl;
  • R 4 is selected from the group consisting of hydrogen, cyano, Ci-C4-alkyl and halogen; and in particular selected from the group consisting of hydrogen, cyano, methyl, chlorine and fluorine;
  • R 5 is halogen; and in particular chlorine or fluorine;
  • R 6 is Ci-C4-alkyl; and in particular methyl or ethyl.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and C1-C4- alkyl-S(0)2; and in particular selected from the group consisting of chlorine, nitro, methyl, cyclopropyl, trifluoromethyl, methoxymethyl, CH2OCH2CH2OCH3 and methylsulfonyl;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci- C4-haloalkyl and Ci-C4-alkyl-S(0)2; and in particular selected from the group consisting of hydrogen, chlorine, fluorine, cyano, nitro, methyl, trifluoromethyl and methylsulfonyl;
  • R 4 is selected from the group consisting of hydrogen, cyano, Ci-C4-alkyl and halogen; and in particular selected from the group consisting of hydrogen, cyano, methyl, chlorine and fluorine;
  • R 5 is halogen; and in particular chlorine or fluorine;
  • R 6 is Ci-C4-alkyl; and in particular methyl or ethyl.
  • X is CR 2 and the variable R 3 is not hydrogen.
  • X is CR 2 and the variables R 2 and R 3 are not hydrogen.
  • variables R 1 , R 2 , R 3 , R 4 and R 5 together form one of the following substitution patterns on the phenyl ring of the com- pounds of formula I, provided that position 1 is the attachment point of the phenyl ring to the remainder of the molecule:
  • Examples of preferred compounds I.A, where X is N, are the individual compounds compiled in Tables 1 to 20 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
  • Table 1 Compounds of formu a I.A (I.A-1 .1 - I.A-1 .576) in which B is CH, R 4 is H and R 5 is F and the combination of R 1 , R 3 R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 8 Compounds of formu a I.A (I.A-8.1 - I.A-8.576) in which B is CH, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 9 Compounds of formula I .A (I.A-9.1 - I.A-9.576) in which B is CH, R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 Compounds of formula I.A (I.A-1 1.1 - I.A-1 1 .576) in which B is N, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 12 Compounds of formula I.A (I.A-12.1 - I.A-12.576) in which B is N, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 14 Compounds of formula I.A (I.A-14.1 - I.A-14.576) in which B is N, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 15 Compounds of formula I.A (I.A-15.1 - I.A-15.576) in which B is N, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 17 Compounds of formula I.A (I.A-17.1 - I.A-17.576) in which B is N, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Examples of preferred compounds I.B, where X is CR 2 are the individual compounds compiled in Tables 21 to 480 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a par- ticularly preferred embodiment of the substituents in question.
  • Table 21 Compounds of formula I.B1 (I.B1 -1 .1 - I.B1 -1 .576) in which B is CH, R 2 is SCH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 25 Compounds of formula I.B1 (I.B1 -5.1 - I.B1 -5.576) in which B is CH, R 2 is SCH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 28 Compounds of formula I.B1 (I.B1 -8.1 - I.B1 -8.576) in which B is CH, R 2 is SCH 3 , R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 29 Compounds of formula I.B1 (I.B1 -9.1 - I.B1 -9.576) in which B is CH, R 2 is SCH 3 , R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound cor- responds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 51 Compounds of formula I.B4 (I.B4-1 .1 - I.B4-1 .576) in which B is CH, R 2 is SOCH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 53 Compounds of formula I.B4 (I.B4-3.1 - I.B4-3.576) in which B is CH, R 2 is SOCH 3 , R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 54 Compounds of formula I.B4 (I.B4-4.1 - I.B4-4.576) in which B is CH, R 2 is SOCH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 55 Compounds of formula I.B4 (I.B4-5.1 - I.B4-5.576) in which B is CH, R 2 is SOCH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 70 Compounds of formula I.B5 (I.B5-10.1 - I.B5-10.576) in which B is CH, R 2 is SOCH2CH3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 71 Compounds of formula I.B6 (I.B6-1 .1 - I.B6-1 .576) in which B is CH, R 2 is OCH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 72 Compounds of formula I.B6 (I.B6-2.1 - I.B6-2.576) in which B is CH, R 2 is OCH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 74 Compounds of formula I.B6 (I.B6-4.1 - I.B6-4.576) in which B is CH, R 2 is OCH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 76 Compounds of formula I.B6 (I.B6-6.1 - I.B6-6.576) in which B is CH, R 2 is OCH 3 , R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 79 Compounds of formula I.B6 (I.B6-9.1 - I.B6-9.576) in which B is CH, R 2 is OCH 3 , R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 80 Compounds of formula I.B6 (I.B6-10.1 - I.B6-10.576) in which B is CH, R 2 is OCH 3 , R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 81 Compounds of formula I.B7 (I.B7-1 .1 - I.B7-1 .576) in which B is CH, R 2 is
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 90 Compounds of formula I.B7 (I.B7-10.1 - I.B7-10.576) in which B is CH, R 2 is OCH2CH3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 91 Compounds of formula I.B8 (I.B8-1 .1 - I.B8-1 .576) in which B is CH, R 2 is OCHF 2 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 92 Compounds of formula I.B8 (I.B8-2.1 - I.B8-2.576) in which B is CH, R 2 is OCHF 2 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 1 10 Compounds of formula I.B9 (I.B9-10.1 - I.B9-10.576) in which B is CH, R 2 is OCH2CF3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 1 1 Compounds of formula I.B10 (I.B10-1 .1 - I.B10-1 .576) in which B is CH, R 2 is
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 12 Compounds of formula I.B10 (I.B10-2.1 - I.B10-2.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 13 Compounds of formula I.B10 (I.B10-3.1 - I.B10-3.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 14 Compounds of formula I.B10 (I.B10-4.1 - I.B10-4.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 15 Compounds of formula I.B10 (I.B10-5.1 - I.B10-5.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 17 Compounds of formula I.B10 (I.B10-7.1 - I.B10-7.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 18 Compounds of formula I.B10 (I.B10-8.1 - I.B10-8.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 1 19 Compounds of formula I.B10 (I.B10-9.1 - I.B10-9.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 120 Compounds of formula I.B10 (I.B10-10.1 - I.B10-10.576) in which B is CH, R 2 is OCH2CH2OCH3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 121 Compounds of formula I.B1 1 (I.B1 1 -1 .1 - I.B1 1 -1 .576) in which B is CH, R 2 is H, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 122 Compounds of formula I.B1 1 (I. B1 1 -2.1 - 1. B1 1 -2.576) in which B is CH, R 2 is H, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 128 Compounds of formula I.B1 1 (I. B1 1 -8.1 - 1. B1 1 -8.576) in which B is CH, R 2 is H, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 129 Compounds of formula I.B1 1 (I. B1 1 -9.1 - 1. B1 1 -9.576) in which B is CH, R 2 is H, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 130 Compounds of formula I.B1 1 (I. B1 1 -10.1 - 1. B1 1 -10.576) in which B is CH, R 2 is H, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 131 Compounds of formula I.B12 (I.B12-1 .1 - I.B12-1 .576) in which B is CH, R 2 is SO2CH3, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 132 Compounds of formula I.B12 (I.B12-2.1 - I.B12-2.576) in which B is CH, R 2 is SO2CH3, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 133 Compounds of formula I.B12 (I.B12-3.1 - I.B12-3.576) in which B is CH, R 2 is SO2CH3, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 135 Compounds of formula I.B12 (I.B12-5.1 - I.B12-5.576) in which B is CH, R 2 is SO2CH3, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 138 Compounds of formula I.B12 (I.B12-8.1 - I.B12-8.576) in which B is CH, R 2 is SO2CH3, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 140 Compounds of formula I.B12 (I.B12-10.1 - I.B12-10.576) in which B is CH, R 2 is SO2CH3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 141 Compounds of formula I.B13 (I.B13-1 .1 - I.B13-1 .576) in which B is CH, R 2 is CH2OCH2CF3, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 142 Compounds of formula I.B13 (I.B13-2.1 - I.B13-2.576) in which B is CH, R 2 is CH2OCH2CF3, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 143 Compounds of formula I.B13 (I.B13-3.1 - I.B13-3.576) in which B is CH, R 2 is CH2OCH2CF3, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound cor- responds in each case to one row of Table A;
  • Table 144 Compounds of formula I.B13 (I.B13-4.1 - I.B13-4.576) in which B is CH, R 2 is CH2OCH2CF3, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 145 Compounds of formula I.B13 (I.B13-5.1 - I.B13-5.576) in which B is CH, R 2 is CH2OCH2CF3, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 149 Compounds of formula I.B13 (I.B13-9.1 - I.B13-9.576) in which B is CH, R 2 is CH2OCH2CF3, R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 150 Compounds of formula I.B13 (I.B13-10.1 - I.B13-10.576) in which B is CH, R 2 is CH2OCH2CF3, R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 151 Compounds of formula I.B14 (I.B14-1 .1 - I.B14-1 .576) in which B is CH, R 2 is isox- azolin-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 152 Compounds of formula I.B14 (I.B14-2.1 - I.B14-2.576) in which B is CH, R 2 is isox- azolin-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 154 Compounds of formula I.B14 (I.B14-4.1 - I.B14-4.576) in which B is CH, R 2 is isox- azolin-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 156 Compounds of formula I.B14 (I.B14-6.1 - I.B14-6.576) in which B is CH, R 2 is isox- azolin-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 157 Compounds of formula I.B14 (I.B14-7.1 - I.B14-7.576) in which B is CH, R 2 is isox- azolin-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 158 Compounds of formula I.B14 (I.B14-8.1 - I.B14-8.576) in which B is CH, R 2 is isox- azolin-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 159 Compounds of formula I.B14 (I.B14-9.1 - I.B14-9.576) in which B is CH, R 2 is isox- azolin-3-yl, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 160 Compounds of formula I.B14 (I.B14-10.1 - I.B14-10.576) in which B is CH, R 2 is isoxazolin-3-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 161 Compounds of formula I.B15 (I.B15-1 .1 - I.B15-1 .576) in which B is CH, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 162 Compounds of formula I.B15 (I.B15-2.1 - I.B15-2.576) in which B is CH, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 164 Compounds of formula I.B15 (I.B15-4.1 - I.B15-4.576) in which B is CH, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 165 Compounds of formula I.B15 (I.B15-5.1 - I.B15-5.576) in which B is CH, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 166 Compounds of formula I.B15 (I.B15-6.1 - I.B15-6.576) in which B is CH, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 169 Compounds of formula I.B15 (I.B15-9.1 - I.B15-9.576) in which B is CH, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 170 Compounds of formula I.B15 (I.B15-10.1 - I.B15-10.576) in which B is CH, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 171 Compounds of formula I.B16 (I.B16-1 .1 - I.B16-1 .576) in which B is CH, R 2 is isox- azol-3-yl, R
  • Table 172 Compounds of formula I.B16 (I.B16-2.1 - I.B16-2.576) in which B is CH, R 2 is isox- azol-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 173 Compounds of formula I.B16 (I.B16-3.1 - I.B16-3.576) in which B is CH, R 2 is isox- azol-3-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 175 Compounds of formula I.B16 (I.B16-5.1 - I.B16-5.576) in which B is CH, R 2 is isox- azol-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 176 Compounds of formula I.B16 (I.B16-6.1 - I.B16-6.576) in which B is CH, R 2 is isox- azol-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 177 Compounds of formula I.B16 (I.B16-7.1 - I.B16-7.576) in which B is CH, R 2 is isox- azol-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 178 Compounds of formula I.B16 (I.B16-8.1 - I.B16-8.576) in which B is CH, R 2 is isox- azol-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 180 Compounds of formula I.B16 (I.B16-10.1 - I.B16-10.576) in which B is CH, R 2 is isoxazol-3-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 181 Compounds of formula I.B17 (I.B17-1 .1 - I.B17-1 .576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 182 Compounds of formula I.B17 (I.B17-2.1 - I.B17-2.576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 184 Compounds of formula I.B17 (I.B17-4.1 - I.B17-4.576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 185 Compounds of formula I.B17 (I.B17-5.1 - I.B17-5.576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 186 Compounds of formula I.B17 (I.B17-6.1 - I.B17-6.576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 188 Compounds of formula I.B17 (I.B17-8.1 - I.B17-8.576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 189 Compounds of formula I.B17 (I.B17-9.1 - I.B17-9.576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 190 Compounds of formula I.B17 (I.B17-10.1 - I.B17-10.576) in which B is CH, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 191 Compounds of formula I.B18 (I.B18-1 .1 - I.B18-1 .576) in which B is CH, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 192 Compounds of formula I.B18 (I.B18-2.1 - I.B18-2.576) in which B is CH, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 194 Compounds of formula I.B18 (I.B18-4.1 - I.B18-4.576) in which B is CH, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 195 Compounds of formula I.B18 (I.B18-5.1 - I.B18-5.576) in which B is CH, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 196 Compounds of formula I.B18 (I.B18-6.1 - I.B18-6.576) in which B is CH, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 200 Compounds of formula I.B18 (I.B18-10.1 - I.B18-10.576) in which B is CH, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 201 Compounds of formula I.B19 (I.B19-1 .1 - I.B19-1 .576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 202 Compounds of formula I.B19 (I.B19-2.1 - I.B19-2.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 203 Compounds of formula I.B19 (I.B19-3.1 - I.B19-3.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 204 Compounds of formula I.B19 (I.B19-4.1 - I.B19-4.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 205 Compounds of formula I.B19 (I.B19-5.1 - I.B19-5.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 206 Compounds of formula I.B19 (I.B19-6.1 - I.B19-6.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 207 Compounds of formula I.B19 (I.B19-7.1 - I.B19-7.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 208 Compounds of formula I.B19 (I.B19-8.1 - I.B19-8.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 209 Compounds of formula I.B19 (I.B19-9.1 - I.B19-9.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 210 Compounds of formula I.B19 (I.B19-10.1 - I.B19-10.576) in which B is CH, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 21 1 Compounds of formula I.B20 (I.B20-1 .1 - I.B20-1 .576) in which B is CH, R 2 is CH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 212 Compounds of formula I.B20 (I.B20-2.1 - I.B20-2.576) in which B is CH, R 2 is CH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 214 Compounds of formula I.B20 (I.B20-4.1 - I.B20-4.576) in which B is CH, R 2 is CH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 215 Compounds of formula I.B20 (I.B20-5.1 - I.B20-5.576) in which B is CH, R 2 is CH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 216 Compounds of formula I.B20 (I.B20-6.1 - I.B20-6.576) in which B is CH, R 2 is CH 3 , R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 217 Compounds of formula I.B20 (I.B20-7.1 - I.B20-7.576) in which B is CH, R 2 is CH 3 , R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 218 Compounds of formula I.B20 (I.B20-8.1 - I.B20-8.576) in which B is CH, R 2 is CH 3 , R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 220 Compounds of formula I.B20 (I.B20-10.1 - I.B20-10.576) in which B is CH, R 2 is CH 3 , R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 221 Compounds of formula I.B21 (I.B21 -1 .1 - I.B21 -1 .576) in which B is CH, R 2 is CH2OCH3, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 222 Compounds of formula I.B21 (I.B21 -2.1 - I.B21 -2.576) in which B is CH, R 2 is CH2OCH3, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 225 Compounds of formula I.B21 (I.B21 -5.1 - I.B21 -5.576) in which B is CH, R 2 is CH2OCH3, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 226 Compounds of formula I.B21 (I.B21 -6.1 - I.B21 -6.576) in which B is CH, R 2 is CH2OCH3, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 230 Compounds of formula I.B21 (I.B21 -10.1 - I.B21 -10.576) in which B is CH, R 2 is CH2OCH3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound cor- responds in each case to one row of Table A;
  • Table 231 Compounds of formula I.B22 (I.B22-1 .1 - I.B22-1 .576) in which B is CH, R 2 is OCH 2 CH(CH 2 )2, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 233 Compounds of formula I.B22 (I.B22-3.1 - I.B22-3.576) in which B is CH, R 2 is OCH 2 CH(CH 2 )2, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 234 Compounds of formula I.B22 (I.B22-4.1 - I.B22-4.576) in which B is CH, R 2 is OCH 2 CH(CH 2 )2, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 236 Compounds of formula I.B22 (I.B22-6.1 - I.B22-6.576) in which B is CH, R 2 is OCH 2 CH(CH 2 )2, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 239 Compounds of formula I.B22 (I.B22-9.1 - I.B22-9.576) in which B is CH, R 2 is OCH 2 CH(CH 2 ) 2 , R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 240 Compounds of formula I.B22 (I.B22-10.1 - I.B22-10.576) in which B is CH, R 2 is OCH 2 CH(CH 2 ) 2 , R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 241 Compounds of formula I.B23 (I.B23-1 .1 - I.B23-1 .576) in which B is CH, R 2 is NCH 3 S0 2 CH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound cor- responds in each case to one row of Table A;
  • Table 242 Compounds of formula I.B23 (I.B23-2.1 - I.B23-2.576) in which B is CH, R 2 is NCH 3 S0 2 CH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 243 Compounds of formula I.B23 (I.B23-3.1 - I.B23-3.576) in which B is CH, R 2 is NCH 3 S0 2 CH 3 , R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 244 Compounds of formula I.B23 (I.B23-4.1 - I.B23-4.576) in which B is CH, R 2 is NCH 3 S0 2 CH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 245 Compounds of formula I.B23 (I.B23-5.1 - I.B23-5.576) in which B is CH, R 2 is NCH 3 S0 2 CH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 246 Compounds of formula I.B23 (I.B23-6.1 - I.B23-6.576) in which B is CH, R 2 is NCH 3 S0 2 CH 3 , R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 247 Compounds of formula I.B23 (I.B23-7.1 - I.B23-7.576) in which B is CH, R 2 is NCH3SO2CH3, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 248 Compounds of formula I.B23 (I.B23-8.1 - I.B23-8.576) in which B is CH, R 2 is NCH3SO2CH3, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 249 Compounds of formula I.B23 (I.B23-9.1 - I.B23-9.576) in which B is CH, R 2 is NCH3SO2CH3, R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 250 Compounds of formula I.B23 (I.B23-10.1 - I.B23-10.576) in which B is CH, R 2 is NCH3SO2CH3, R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 251 Compounds of formula I.B1 (I.B1 -1 1 .1 - I.B1 -1 1 .576) in which B is N, R 2 is SCH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 252 Compounds of formula I.B1 (I.B1 -12.1 - I.B1 -12.576) in which B is N, R 2 is SCH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 253 Compounds of formula I.B1 (I.B1 -13.1 - I.B1 -13.576) in which B is N, R 2 is SCH 3 , R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 254 Compounds of formula I.B1 (I.B1 -14.1 - I.B1 -14.576) in which B is N, R 2 is SCH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 255 Compounds of formula I.B1 (I.B1 -15.1 - I.B1 -15.576) in which B is N, R 2 is SCH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 257 Compounds of formula I.B1 (I.B1 -17.1 - I.B1 -17.576) in which B is N, R 2 is SCH 3 , R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 258 Compounds of formula I.B1 (I.B1 -18.1 - I.B1 -18.576) in which B is N, R 2 is SCH 3 , R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 259 Compounds of formula I.B1 (I.B1 -19.1 - I.B1 -19.576) in which B is N, R 2 is SCH 3 , R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 260 Compounds of formula I.B1 (I.B1 -20.1 - I.B1 -20.576) in which B is N, R 2 is SCH 3 , R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 261 Compounds of formula I.B2 (I.B2-1 1 .1 - I.B2-1 1 .576) in which B is N, R 2 is
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound cor- responds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 281 Compounds of formula I.B4 (I.B4-1 1 .1 - I.B4-1 1 .576) in which B is N, R 2 is SOCH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 282 Compounds of formula I.B4 (I.B4-12.1 - I.B4-12.576) in which B is N, R 2 is SOCH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 284 Compounds of formula I.B4 (I.B4-14.1 - I.B4-14.576) in which B is N, R 2 is SOCH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 285 Compounds of formula I.B4 (I.B4-15.1 - I.B4-15.576) in which B is N, R 2 is SOCH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 286 Compounds of formula I.B4 (I.B4-16.1 - I.B4-16.576) in which B is N, R 2 is SOCH 3 , R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 287 Compounds of formula I.B4 (I.B4-17.1 - I.B4-17.576) in which B is N, R 2 is SOCH 3 , R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 290 Compounds of formula I.B4 (I.B4-20.1 - I.B4-20.576) in which B is N, R 2 is SOCH 3 , R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 291 Compounds of formula I.B5 (I.B5-1 1 .1 - I.B5-1 1 .576) in which B is N, R 2 is
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 301 Compounds of formula I.B6 (I.B6-1 1 .1 - I.B6-1 1 .576) in which B is N, R 2 is OCH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 302 Compounds of formula I.B6 (I.B6-12.1 - I.B6-12.576) in which B is N, R 2 is OCH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 304 Compounds of formula I.B6 (I.B6-14.1 - I.B6-14.576) in which B is N, R 2 is OCH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 305 Compounds of formula I.B6 (I.B6-15.1 - I.B6-15.576) in which B is N, R 2 is OCH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 306 Compounds of formula I.B6 (I.B6-16.1 - I.B6-16.576) in which B is N, R 2 is OCH 3 , R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 307 Compounds of formula I.B6 (I.B6-17.1 - I.B6-17.576) in which B is N, R 2 is OCH 3 , R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 308 Compounds of formula I.B6 (I.B6-18.1 - I.B6-18.576) in which B is N, R 2 is OCH 3 , R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 309 Compounds of formula I.B6 (I.B6-19.1 - I.B6-19.576) in which B is N, R 2 is OCH 3 , R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 310 Compounds of formula I.B6 (I.B6-20.1 - I.B6-20.576) in which B is N, R 2 is OCH 3 , R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 31 1 Compounds of formula I.B7 (I.B7-1 1 .1 - I.B7-1 1 .576) in which B is N, R 2 is
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is Ch and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is Ch and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound cor- responds in each case to one row of Table A;
  • Table 322 Compounds of formula I.B8 (I.B8-12.1 - I.B8-12.576) in which B is N, R 2 is OCHF 2 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 323 Compounds of formula I.B8 (I.B8-13.1 - I.B8-13.576) in which B is N, R 2 is OCHF 2 , R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 324 Compounds of formula I.B8 (I.B8-14.1 - I.B8-14.576) in which B is N, R 2 is OCHF 2 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 328 Compounds of formula I.B8 (I.B8-18.1 - I.B8-18.576) in which B is N, R 2 is OCHF 2 , R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 329 Compounds of formula I.B8 (I.B8-19.1 - I.B8-19.576) in which B is N, R 2 is OCHF 2 , R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 330 Compounds of formula I.B8 (I.B8-20.1 - I.B8-20.576) in which B is N, R 2 is OCHF 2 , R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is Ch and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is Ch and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 341 Compounds of formula I.B10 (I.B10-1 1 .1 - I.B10-1 1 .576) in which B is N, R 2 is OCH2CH2OCH3, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 342 Compounds of formula I.B10 (I.B10-12.1 - I.B10-12.576) in which B is N, R 2 is OCH2CH2OCH3, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 344 Compounds of formula I.B10 (I.B10-14.1 - I.B10-14.576) in which B is N, R 2 is OCH2CH2OCH3, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 345 Compounds of formula I.B10 (I.B10-15.1 - I.B10-15.576) in which B is N, R 2 is OCH2CH2OCH3, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 346 Compounds of formula I.B10 (I.B10-16.1 - I.B10-16.576) in which B is N, R 2 is OCH2CH2OCH3, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 349 Compounds of formula I.B10 (I.B10-19.1 - I.B10-19.576) in which B is N, R 2 is OCH2CH2OCH3, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 350 Compounds of formula I.B10 (I.B10-20.1 - I.B10-20.576) in which B is N, R 2 is OCH2CH2OCH3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 351 Compounds of formula I.B1 1 (I.
  • Table 352 Compounds of formula I.B1 1 (I. B1 1 -12.1 - 1. B1 1 -12.576) in which B is N, R 2 is H, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 353 Compounds of formula I.B1 1 (I. B1 1 -13.1 - 1. B1 1 -13.576) in which B is N, R 2 is H, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 354 Compounds of formula I.B1 1 (I. B1 1 -14.1 - 1. B1 1 -14.576) in which B is N, R 2 is H, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 355 Compounds of formula I.B1 1 (I. B1 1 -15.1 - 1. B1 1 -15.576) in which B is N, R 2 is H, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 356 Compounds of formula I.B1 1 (I. B1 1 -16.1 - 1. B1 1 -16.576) in which B is N, R 2 is H, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 358 Compounds of formula I.B1 1 (I. B1 1 -18.1 - 1. B1 1 -18.576) in which B is N, R 2 is H, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 360 Compounds of formula I.B1 1 (I. B1 1 -20.1 - 1. B1 1 -20.576) in which B is N, R 2 is H, R 4 is Ch and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 361 Compounds of formula I.B12 (I.B12-1 1 .1 - I.B12-1 1 .576) in which B is N, R 2 is SO2CH3, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 362 Compounds of formula I.B12 (I.B12-12.1 - I.B12-12.576) in which B is N, R 2 is SO2CH3, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 366 Compounds of formula I.B12 (I.B12-16.1 - I.B12-16.576) in which B is N, R 2 is SO2CH3, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 368 Compounds of formula I.B12 (I.B12-18.1 - I.B12-18.576) in which B is N, R 2 is SO2CH3, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 369 Compounds of formula I.B12 (I.B12-19.1 - I.B12-19.576) in which B is N, R 2 is SO2CH3, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is Ch and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 371 Compounds of formula I.B13 (I.B13-1 1 .1 - I.B13-1 1 .576) in which B is N, R 2 is CH2OCH2CF3, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 374 Compounds of formula I.B13 (I.B13-14.1 - I.B13-14.576) in which B is N, R 2 is CH2OCH2CF3, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 375 Compounds of formula I.B13 (I.B13-15.1 - I.B13-15.576) in which B is N, R 2 is CH2OCH2CF3, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 376 Compounds of formula I.B13 (I.B13-16.1 - I.B13-16.576) in which B is N, R 2 is CH2OCH2CF3, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 378 Compounds of formula I.B13 (I.B13-18.1 - I.B13-18.576) in which B is N, R 2 is CH2OCH2CF3, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 379 Compounds of formula I.B13 (I.B13-19.1 - I.B13-19.576) in which B is N, R 2 is CH2OCH2CF3, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 380 Compounds of formula I.B13 (I.B13-20.1 - I.B13-20.576) in which B is N, R 2 is CH2OCH2CF3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 381 Compounds of formula I.B14 (I.B14-1 1 .1 - I.B14-1 1 .576) in which B is N, R 2 is isox- azolin-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 382 Compounds of formula I.B14 (I.B14-12.1 - I.B14-12.576) in which B is N, R 2 is isox- azolin-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 384 Compounds of formula I.B14 (I.B14-14.1 - I.B14-14.576) in which B is N, R 2 is isox- azolin-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 386 Compounds of formula I.B14 (I.B14-16.1 - I.B14-16.576) in which B is N, R 2 is isox- azolin-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 387 Compounds of formula I.B14 (I.B14-17.1 - I.B14-17.576) in which B is N, R 2 is isox- azolin-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 388 Compounds of formula I.B14 (I.B14-18.1 - I.B14-18.576) in which B is N, R 2 is isox- azolin-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 391 Compounds of formula I.B15 (I.B15-1 1 .1 - I.B15-1 1 .576) in which B is N, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 392 Compounds of formula I.B15 (I.B15-12.1 - I.B15-12.576) in which B is N, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 397 Compounds of formula I.B15 (I.B15-17.1 - I.B15-17.576) in which B is N, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 400 Compounds of formula I.B15 (I.B15-20.1 - I.B15-20.576) in which B is N, R 2 is 5- methyl-isoxazolin-3-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 401 Compounds of formula I.B16 (I.B16-1 1 .1 - I.B16-1 1 .576) in which B is N, R 2 is isox- azol-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 402 Compounds of formula I.B16 (I.B16-12.1 - I.B16-12.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 403 Compounds of formula I.B16 (I.B16-13.1 - I.B16-13.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 404 Compounds of formula I.B16 (I.B16-14.1 - I.B16-14.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 405 Compounds of formula I.B16 (I.B16-15.1 - I.B16-15.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 406 Compounds of formula I.B16 (I.B16-16.1 - I.B16-16.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 407 Compounds of formula I.B16 (I.B16-17.1 - I.B16-17.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 408 Compounds of formula I.B16 (I.B16-18.1 - I.B16-18.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 409 Compounds of formula I.B16 (I.B16-19.1 - I.B16-19.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is Ch and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 410 Compounds of formula I.B16 (I.B16-20.1 - I.B16-20.576) in which B is N, R 2 is isox- azol-3-yl, R 4 is Ch and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 41 1 Compounds of formula I.B17 (I.B17-1 1 .1 - I.B17-1 1 .576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 412 Compounds of formula I.B17 (I.B17-12.1 - I.B17-12.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 413 Compounds of formula I.B17 (I.B17-13.1 - I.B17-13.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 414 Compounds of formula I.B17 (I.B17-14.1 - I.B17-14.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 415 Compounds of formula I.B17 (I.B17-15.1 - I.B17-15.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 416 Compounds of formula I.B17 (I.B17-16.1 - I.B17-16.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 417 Compounds of formula I.B17 (I.B17-17.1 - I.B17-17.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 418 Compounds of formula I.B17 (I.B17-18.1 - I.B17-18.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 419 Compounds of formula I.B17 (I.B17-19.1 - I.B17-19.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 420 Compounds of formula I.B17 (I.B17-20.1 - I.B17-20.576) in which B is N, R 2 is 5- methyl-isoxazol-3-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 421 Compounds of formula I.B18 (I.B18-1 1 .1 - I.B18-1 1 .576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 422 Compounds of formula I.B18 (I.B18-12.1 - I.B18-12.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 423 Compounds of formula I.B18 (I.B18-13.1 - I.B18-13.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 424 Compounds of formula I.B18 (I.B18-14.1 - I.B18-14.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 425 Compounds of formula I.B18 (I.B18-15.1 - I.B18-15.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 426 Compounds of formula I.B18 (I.B18-16.1 - I.B18-16.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 427 Compounds of formula I.B18 (I.B18-17.1 - I.B18-17.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 428 Compounds of formula I.B18 (I.B18-18.1 - I.B18-18.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 429 Compounds of formula I.B18 (I.B18-19.1 - I.B18-19.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 430 Compounds of formula I.B18 (I.B18-20.1 - I.B18-20.576) in which B is N, R 2 is 3- methyl-isoxazolin-5-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 431 Compounds of formula I.B19 (I.B19-1 1 .1 - I.B19-1 1 .576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 432 Compounds of formula I.B19 (I.B19-12.1 - I.B19-12.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 433 Compounds of formula I.B19 (I.B19-13.1 - I.B19-13.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 434 Compounds of formula I.B19 (I.B19-14.1 - I.B19-14.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 435 Compounds of formula I.B19 (I.B19-15.1 - I.B19-15.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 436 Compounds of formula I.B19 (I.B19-16.1 - I.B19-16.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 437 Compounds of formula I.B19 (I.B19-17.1 - I.B19-17.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 438 Compounds of formula I.B19 (I.B19-18.1 - I.B19-18.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 439 Compounds of formula I.B19 (I.B19-19.1 - I.B19-19.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a com- pound corresponds in each case to one row of Table A;
  • Table 440 Compounds of formula I.B19 (I.B19-20.1 - I.B19-20.576) in which B is N, R 2 is 3- methyl-isoxazol-5-yl, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 441 Compounds of formula I.B20 (I.B20-1 1 .1 - I.B20-1 1 .576) in which B is N, R 2 is CH 3 , R 4 is H and R 5 is F
  • Table 442 Compounds of formula I.B20 (I.B20-12.1 - I.B20-12.576) in which B is N, R 2 is CH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 444 Compounds of formula I.B20 (I.B20-14.1 - I.B20-14.576) in which B is N, R 2 is CH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 445 Compounds of formula I.B20 (I.B20-15.1 - I.B20-15.576) in which B is N, R 2 is CH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 446 Compounds of formula I.B20 (I.B20-16.1 - I.B20-16.576) in which B is N, R 2 is CH 3 , R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 447 Compounds of formula I.B20 (I.B20-17.1 - I.B20-17.576) in which B is N, R 2 is CH 3 , R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 448 Compounds of formula I.B20 (I.B20-18.1 - I.B20-18.576) in which B is N, R 2 is CH 3 , R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 449 Compounds of formula I.B20 (I.B20-19.1 - I.B20-19.576) in which B is N, R 2 is CH 3 , R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 450 Compounds of formula I.B20 (I.B20-20.1 - I.B20-20.576) in which B is N, R 2 is CH 3 , R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 451 Compounds of formula I.B21 (I.B21 -1 1 .1 - I.B21 -1 1 .576) in which B is N, R 2 is CH20CH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 452 Compounds of formula I.B21 (I.B21 -12.1 - I.B21 -12.576) in which B is N, R 2 is CH2OCH3, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 453 Compounds of formula I.B21 (I.B21 -13.1 - I.B21 -13.576) in which B is N, R 2 is CH2OCH3, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 454 Compounds of formula I.B21 (I.B21 -14.1 - I.B21 -14.576) in which B is N, R 2 is CH2OCH3, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 456 Compounds of formula I.B21 (I.B21 -16.1 - I.B21 -16.576) in which B is N, R 2 is CH2OCH3, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corre- sponds in each case to one row of Table A;
  • Table 457 Compounds of formula I.B21 (I.B21 -17.1 - I.B21 -17.576) in which B is N, R 2 is CH2OCH3, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 458 Compounds of formula I.B21 (I.B21 -18.1 - I.B21 -18.576) in which B is N, R 2 is CH2OCH3, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is Ch and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 461 Compounds of formula I.B22 (I.B22-1 1 .1 - I.B22-1 1 .576) in which B is N, R 2 is OCH 2 CH(CH 2 )2, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 462 Compounds of formula I.B22 (I.B22-12.1 - I.B22-12.576) in which B is N, R 2 is OCH 2 CH(CH 2 )2, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 464 Compounds of formula I.B22 (I.B22-14.1 - I.B22-14.576) in which B is N, R 2 is OCH 2 CH(CH 2 )2, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 465 Compounds of formula I.B22 (I.B22-15.1 - I.B22-15.576) in which B is N, R 2 is OCH 2 CH(CH 2 )2, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 466 Compounds of formula I.B22 (I.B22-16.1 - I.B22-16.576) in which B is N, R 2 is OCH 2 CH(CH 2 )2, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 469 Compounds of formula I.B22 (I.B22-19.1 - I.B22-19.576) in which B is N, R 2 is OCH 2 CH(CH 2 ) 2 , R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 470 Compounds of formula I.B22 (I.B22-20.1 - I.B22-20.576) in which B is N, R 2 is OCH 2 CH(CH 2 ) 2 , R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 471 Compounds of formula I.B23 (I.B23-1 1 .1 - I.B23-1 1 .576) in which B is N, R 2 is
  • NCH 3 S0 2 CH 3 , R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 472 Compounds of formula I.B23 (I.B23-12.1 - I.B23-12.576) in which B is N, R 2 is NCH 3 S0 2 CH 3 , R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 474 Compounds of formula I.B23 (I.B23-14.1 - I.B23-14.576) in which B is N, R 2 is NCH 3 S0 2 CH 3 , R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 475 Compounds of formula I.B23 (I.B23-15.1 - I.B23-15.576) in which B is N, R 2 is NCH 3 S0 2 CH 3 , R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 476 Compounds of formula I.B23 (I.B23-16.1 - I.B23-16.576) in which B is N, R 2 is NCH 3 S0 2 CH 3 , R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 477 Compounds of formula I.B23 (I.B23-17.1 - I.B23-17.576) in which B is N, R 2 is NCH 3 S0 2 CH 3 , R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 478 Compounds of formula I.B23 (I.B23-18.1 - I.B23-18.576) in which B is N, R 2 is NCH3SO2CH3, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 479 Compounds of formula I.B23 (I.B23-19.1 - I.B23-19.576) in which B is N, R 2 is NCH3SO2CH3, R 4 is CHs and R 5 is F and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • Table 480 Compounds of formula I.B23 (I.B23-20.1 - I.B23-20.576) in which B is N, R 2 is NCH3SO2CH3, R 4 is CHs and R 5 is CI and the combination of R 1 , R 3 , R 6 and Q for a compound corresponds in each case to one row of Table A;
  • the compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described in schemes 1 to 5.
  • the substituents, variables and indices used in schemes 1 to 5 are as defined above for the compounds of formula I, if not specified otherwise.
  • Suitable bases are, for example, amines, such as trimethylamine or triethylamine, or alkoxides such as potassium methoxide, sodium methoxide, potassium ethoxide, sodium ethox- ide, potassium tert-butoxide or sodium tert-butoxide.
  • Sodium hydroxide, potassium hydroxide or sodium hydride can also be used.
  • the base can be used in stoichiometric amounts, in excess or in catalytic amounts. Preferably, the base is used in stoichiometric amounts or in excess, e.g.
  • Suitable solvents are, for example, protic solvents, such as n-butanol, isopropanol, ethanol, methanol or water, preferably methanol or ethanol, or aprotic solvents, such as 1 ,4-dioxane, THF, diethyl ether or methylene chloride, in particular THF or methylene chloride.
  • the reaction is usually carried out at temperatures in the range of from 0°C to 100°C, preferably carried out at temperatures in the range of from 0°C to 40°C.
  • the compounds of formula l-Q 1 can be prepared by reaction of a compound of formula II with a compound of formula III, preferably in the presence of a base, as illustrated in scheme 2.
  • L is a leaving group, such as halogen, in particular CI, an anhydride residue or an activated ester or activated amide residue.
  • X being halogen the reaction is preferably carried out in the presence of a base.
  • bases are, for example, carbonates, such as lithium, sodium or potassium carbonate, amines, such as trimethylamine or triethylamine, and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or 2,4,6-trimethylpyridine.
  • Suitable solvents are in particular aprotic solvents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1 ,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trime- thylbenzene, pyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1 ,4-dioxane, N,N-dimethyl formamide, N-methyl pyrrolidinone or mixtures thereof.
  • the compounds of formulae II and III are generally reacted with one another in equimolar or nearly equimolar amounts at temperatures usually in the range of from
  • the compounds of formula l-Q 1 can be prepared by reaction of a compound of formula II with a compound of formula IV using an activating agent, as illustrated in scheme 3.
  • Compounds of formula II can be reacted with compounds of formula IV using an activating agent to give compounds of formula l-Q 1 .
  • the activating agent converts carboxylic acid IV into an activated carboxylic acid derivative.
  • activating agents known in the art such as 1 ,1 '-carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1 -ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC), 2,4,6-tripropyl-1 ,3,5,2,4,6-trioxatriphosphorinane- 2,4,6-trioxide (T3P) or 1 -propanephosphonic acid cyclic anhydride (PPAA) can be employed.
  • CDI 1 ,1 '-carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • EDC 1 -ethyl-3-(3- dimethylamino
  • the activated carboxylic acid derivative can be formed, depending in particular on the specific activating agent used, either in situ by contacting the compound of formula IV with the activating agent in the presence of the compound of formula II, or in a separate step prior to the reaction with the compound of formula II. It may be advantageous, especially in cases where DCC, EDC and PPAA are employed as activating agents, to use further additives, such as hydroxyben- zotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4,5-trichlorophenol, N-hydroxysuccinimide or 4-dimethylaminopyridine (DMAP).
  • HOBt hydroxyben- zotriazole
  • nitrophenol pentafluorophenol
  • 2,4,5-trichlorophenol 2,4,5-trichlorophenol
  • N-hydroxysuccinimide 4-dimethylaminopyridine
  • the activated carboxylic acid derivative is reacted with the compound of formula II either in situ or subsequently to give the compound of formula l-Q 1 .
  • the reaction is normally carried out in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. dichloromethane or dichloroethane, ethers, e.g. tetrahydrofuran or 1 ,4-dioxane or carboxamides, e.g. ⁇ , ⁇ -dimethylformamide, N,N- dimethylacetamide or N-methylpyrrolidone.
  • the reaction is preferably carried out at temperatures in the range from -20°C to +25°C.
  • the compounds of formula l-Q 2 can be prepared, for example, by the sequence illustrated in scheme 4.
  • Suitable bases for the use in the first step include, for example, n-butyllithium, s- butyllithium, t-butyllithium or potassium tert-butoxide. In one particular embodiment, n- butyllithium is used as the base in the first step.
  • Suitable methylating agents include, for example, methyl bromide, methyl iodide or methyl triflate. In one particular embodiment, methyl io- dide is used as the methylating agent.
  • Preferred esters of formula V are, for example, C1-C6- alkyl esters, i.e. compounds of formula V wherein R is Ci-C6-alkyl.
  • Suitable bases for the use in the second step include, for example, n-butyllithium, s-butyllithium, t- butyllithium or potassium tert-butoxide. In one particular embodiment, n-butyllithium is used as the base in the second step.
  • the first step can be carried out in analogy to the method described in Journal of Heterocyclic Chemistry (1986), 23(4), 1257-1262; the second step can be carried out in analogy to the method described in US 4659718; the last two steps can be carried out in analogy to the method described in WO 201 1/012248.
  • the compounds of formula II can be prepared, for example, by the sequence illustrated in scheme 5.
  • the first step can be carried out in analogy to the method described in WO 2010/25407; the second step can be carried in analogy to the method described in Journal of Antibiotics (1993), 46(12), 1866-1882; the third step can be carried out in analogy to the method described in US 2003/69257.
  • the compounds of formula I can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds of formula I or the respective precursors or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
  • the reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperatures. If the intermediates and end products are obtained as solids, they may be purified by recrystalliza- tion or trituration.
  • the present invention also relates to a composition comprising at least one compound of formula I, an N-oxide or an agriculturally suitable salt thereof and at least one auxiliary, which is customary for formulating crop protection compounds.
  • the invention also relates to the use of a compound of formula I, an N-oxide or an agriculturally suitable salt thereof or a composition of the present invention for controlling unwanted vegetation.
  • the invention also relates to a method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one compound of formula I, an N- oxide or an agriculturally suitable salt thereof or a composition of the present invention to act on plants, their seed and/or their habitat.
  • the compounds of formula I and their agriculturally suitable salts are useful as herbicides. They are useful as such or as an appropriately formulated composition.
  • the herbicidal compositions comprising the compound I in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • the compounds of formula I, in particu- lar the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted plants.
  • suitable crops are the following:
  • crop plants also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information).
  • genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information).
  • one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.
  • crop plants also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, US 5,013,659) or imidazolinones (see, for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as, for example, glypho- sate (see, for example, WO WO glypho-
  • Crop plants for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (muta- genesis).
  • Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady ® (glypho- sate) and Liberty Link ® (glufosinate) have been generated with the aid of genetic engineering methods.
  • crop plants also includes plants which, with the aid of genetic en- gineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp.
  • Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B.
  • VI Ps vegetative insecticidal proteins
  • VI Ps vegetative insecticidal proteins
  • toxins of animal organisms for example wasp, spider or scorpion toxins
  • fungal toxins for example from Strep- tomycetes
  • plant lectins for example from peas or barley
  • agglutinins proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribo- some-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin
  • steroid-metabolizing enzymes for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase
  • ion channel blockers for example inhibitors of sodium channels or calcium channels
  • juvenile hormone esterase for example from Bacillus subtilis, Xenorhabdus spp.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1 ), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1 F and the PAT enzyme).
  • crop plants also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • resistance proteins for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum
  • T4 lysozyme for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora.
  • crop plants also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
  • potential yield for example biomass, grain yield, starch, oil or protein content
  • tolerance to drought for example drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
  • crop plants also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for example by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsatu- rated omega 9 fatty acids (for example Nexera ® oilseed rape).
  • crop plants also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora ® potato).
  • the compounds of formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • compositions for the desiccation and/or defoliation of plants processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.
  • the compounds of formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • the compounds of formula I, or the herbicidal compositions comprising the compounds of formula I can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed.
  • the use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.
  • the herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.
  • auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.
  • surfactants such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers
  • organic and inorganic thickeners such as bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.
  • thickeners i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion
  • polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).
  • antifoams examples include silicone emulsions (such as, for example, Silikon ® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides can be added for stabilizing the aqueous herbicidal formulation.
  • bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1 , and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • Suitable inert auxiliaries are, for example, the following:
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
  • paraffin tetrahydronaphthalene
  • alkylated naphthalenes and their derivatives alkylated benzenes and their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclohexanone or strongly polar
  • Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea
  • Suitable surfactants adjuvants, wetting agents, tackifiers, dispersants and also
  • emulsifiers are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard),
  • dibutylnaphthalenesulfonic acid Nakal types, BASF SE
  • fatty acids alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, iso
  • methylcellulose methylcellulose
  • hydrophobically modified starches polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the compounds of formula I or la, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
  • concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
  • concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges.
  • the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound.
  • the active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.
  • the compounds of formula I of the invention can for example be formulated as follows: 1 . Products for dilution with water
  • active compound 10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.
  • active compound 20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexa- none with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.
  • a dispersant for example polyvinylpyrrolidone.
  • the active compound content is 20% by weight.
  • active compound 15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion.
  • the formulation has an active compound content of 15% by weight.
  • active compound 25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • organic solvent e.g. alkylaromatics
  • calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight.
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • emulsifier e.g. Ultraturrax
  • active compound 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.
  • the active compound content in the formulation is 20% by weight.
  • active compound 50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
  • the formulation has an active compound content of 50% by weight.
  • Water-dispersible powders and water-soluble powders 75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.
  • the active compound content of the formulation is 75% by weight.
  • the compounds of formula I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • the compounds of formula I or the herbicidal compositions can be applied by treating seed.
  • the treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula I according to the invention or the compositions prepared therefrom.
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting
  • the herbicidal compositions can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tu- bers, cuttings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • the rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
  • the compounds of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • Safeners are chemical compounds which prevent or reduce damage to useful plants without substantially affecting the herbicidal action of the compounds of formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cuttings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of formula I can be used simultaneously or in succession.
  • Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H- 1 ,2,4-triazole-3-carboxylic acids, 1 -phenyl-4,5-dihydro-5-alkyl-1 H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha- oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4- (aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)- 5-thiazolecarboxylic acids, phosphorothiolates and O-phenyl N-alkylcarba
  • the compounds of the formula I can be mixed and jointly applied with numerous representatives of other herbicidal or growth-regulating groups of active compounds or with safeners.
  • Suitable mixing partners are, for example, 1 ,2,4-thiadiazoles, 1 ,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1 ,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic
  • herbicides which can be used in combination with the compounds of formula I according to the present invention are: b1 ) from the group of the lipid biosynthesis inhibitors:
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, bu- tafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraf I uf en-ethyl, saflufenacil,
  • glyphosate glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);
  • bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;
  • amiprophos amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlor- propham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;
  • acetochlor alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dime- thenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

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  • Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract

La présente invention concerne un composé de formule (I), un N-oxyde ou un sel acceptable en agriculture dudit oxyde, les variables étant telles que définies dans la description, et leur utilisation en tant qu'herbicides.
PCT/EP2014/071421 2013-10-10 2014-10-07 Composés tétrazole et triazole et leur utilisation en tant qu'herbicides WO2015052173A1 (fr)

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US10167297B2 (en) 2014-10-24 2019-01-01 Basf Se Substituted pyridine compounds having herbicidal activity
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