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WO2015144657A1 - Utilisation de pyridyloxyalkylcarboxamides pour lutter contre des micro-organismes indésirables - Google Patents

Utilisation de pyridyloxyalkylcarboxamides pour lutter contre des micro-organismes indésirables Download PDF

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Publication number
WO2015144657A1
WO2015144657A1 PCT/EP2015/056181 EP2015056181W WO2015144657A1 WO 2015144657 A1 WO2015144657 A1 WO 2015144657A1 EP 2015056181 W EP2015056181 W EP 2015056181W WO 2015144657 A1 WO2015144657 A1 WO 2015144657A1
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WO
WIPO (PCT)
Prior art keywords
cio
alkyl
cycloalkyl
haloalkyl
poly
Prior art date
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PCT/EP2015/056181
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English (en)
Inventor
Hans-Georg Schwarz
Jörg GREUL
Peter Dahmen
Ulrike Wachendorff-Neumann
Jürgen BENTING
Pierre-Yves Coqueron
Philippe Rinolfi
Stéphane Brunet
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Bayer Cropscience Ag
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Publication of WO2015144657A1 publication Critical patent/WO2015144657A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present application relates to the use of known pyridyloxyalkylcarboxamides for controlling harmful microorganisms in plants, composition comprising these compounds and to processes for preparation of suitable compositions for the control of harmful microorganisms.
  • WO-A 2013/064460 and WO-A 2013/064461 describe pyridylethylcarboxamides and their use as nematicides.
  • WO-A 2013/ 076230 also claims phenyloxyethylcarboxamides and their use as medicaments for controlling endoparasites in animals or humans.
  • PCT/EP2013/073424 which will be published after the priority date of this application, describes the compounds as shown below as pesticides being active as endoparasiticides in the field of veterinary medicine and as nematicides in crop cultivation.
  • animal pests and harmful microorganisms are very different in many aspects such as physiology, genetics and lifestyle the skilled person would not expect that compounds showing pesticidal activity would also be active against unwanted microorganisms.
  • n for each Q is in each case as defined below:
  • Y represents hydrogen or represents optionally mono- or poly-M 2 -substituted (Ci-Cio)-alkyl, (C2- Cio)-alkenyl, (C 2 -Cio)-alkynyl, (Ci-Cio)-haloalkyl, (C 2 -Cio)-haloalkenyl, (C 2 -Cio)-haloalkynyl, (Ci-Cio)-alkoxy, (C2-Cio)-alkenyloxy, (C3-Cio)-alkynyloxy, (C3-Ci4)-cycloalkyl-(Ci-Cio)-alkyl or represents an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
  • W represents oxygen or sulphur
  • L 2 represents -C(R 21 , R 22 )-
  • L 3 represents -C(R 31 , R 32 )-
  • M 1 , M 2 and M 3 each independently of one another represent hydrogen, halogen, cyano, nitro, OH, (Ci- Cio)-alkyl, (Ci-Cio)-haloalkyl, (Ci-Cio)-alkoxy, (Ci-Cio)-haloalkoxy, (Ci-Cio)-alkylthio, (C1-C10)- haloalkylthio, (Ci-Cio)-alkylsulphonyl, (Ci-Cio)-haloalkylsulphonyl, (Ci-Cio)-alkylsulphanyl, (Ci- Cio)-haloalkylsulphanyl or (3- to 14-membered cyclic group)-0-;
  • M 4 represents hydrogen, halogen, cyano, nitro, OH, (Ci-Cio)-alkyl, (Ci-Cio)-haloalkyl, (Ci-Cio)-alkoxy, (Ci-Cio)-haloalkoxy, (Ci-Cio)-alkylthio, (Ci-Cio)-haloalkylthio, (Ci-Cio)-alkylsulphonyl, (C1-C10)- haloalkylsulphonyl, (Ci-Cio)-alkylsulphanyl, (Ci-Cio)-haloalkylsulphanyl or (3- to 14-membered cyclic group)-0-; k represents 1 , 2 or 3; R 21 , R 22 each independently of one another represent hydrogen, halogen or optionally mono- or poly- M 2 -substituted (Ci-Cio)-alkyl, (
  • R 21 , R 22 together represent an optionally mono- or poly-M 2 -substituted spiro-attached 3- to 14-membered carbo- or 3- to 10-membered heterocyclic group;
  • R 31 , R 32 each independently of one another represent hydrogen, halogen or optionally mono- or poly- M 2 -substituted (Ci-Cio)-alkyl, (C 2 -Cio)-alkenyl, (C 2 -Cio)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C10)- haloalkenyl, (C 2 -Cio)-haloalkynyl, (C3-Ci4)-cycloalkyl-(Ci-Cio)-alkyl or represent an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
  • R 31 , R 32 together represent an optionally mono- or poly-M 5 -substituted spiro-attached 3- to 14- membered carbo- or 3- to 10-membered heterocyclic group;
  • M 5 in each case independently of the others represents halogen, formyl, cyano, nitro, (Ci-Cio)-alkyl, (Ci-Cio)-haloalkyl, (C 2 -Cio)-alkenyl, (C 2 -Cio)-haloalkenyl, (C 2 -Cio)-alkynyl, (C 2 -Cio)-haloalkynyl,
  • a further embodiment provides the novel use of compounds of the formula (I)
  • n for each Q is in each case as defined below:
  • Y represents hydrogen or represents optionally mono- or poly-M -substituted (Ci-Cio)-alkyl, (C2- Cio)-alkenyl, (C 2 -Cio)-alkynyl, (Ci-Cio)-haloalkyl, (C 2 -Cio)-haloalkenyl, (C 2 -Cio)-haloalkynyl, (Ci-Cio)-alkoxy, (C2-Cio)-alkenyloxy, (C3-Cio)-alkynyloxy, (C3-Ci4)-cycloalkyl-(Ci-Cio)-alkyl or represents an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
  • W represents oxygen or sulphur
  • L 2 represents -C(R 21 , R 22 )-
  • L 3 represents -C(R 31 , R 32 )-
  • M 1 , M 2 and M 3 each independently of one another represent hydrogen, halogen, cyano, nitro, OH, (Ci- Cio)-alkyl, (Ci-Cio)-haloalkyl, (Ci-Cio)-alkoxy, (Ci-Cio)-haloalkoxy, (Ci-Cio)-alkylthio, (C1-C10)- haloalkylthio, (Ci-Cio)-alkylsulphonyl, (Ci-Cio)-haloalkylsulphonyl, (Ci-Cio)-alkylsulphanyl, (Ci- Cio)-haloalkylsulphanyl or (3- to 14-membered cyclic group)-0-;
  • M 4 represents hydrogen, halogen, cyano, nitro, OH, (Ci-Cio)-alkyl, (Ci-Cio)-haloalkyl, (Ci-Cio)-alkoxy, (Ci-Cio)-haloalkoxy, (Ci-Cio)-alkylthio, (Ci-Cio)-haloalkylthio, (Ci-Cio)-alkylsulphonyl, (C1-C10)- haloalkylsulphonyl, (Ci-Cio)-alkylsulphanyl, (Ci-Cio)-haloalkylsulphanyl or (3- to 14-membered cyclic group)-0-; k represents 1 , 2 or 3; R 21 , R 22 each independently of one another represent hydrogen, halogen or optionally mono- or poly- M 2 -substituted (Ci-Cio)-alkyl, (
  • R 21 , R 22 together represent an optionally mono- or poly-M 2 -substituted spiro-attached 3- to 14-membered carbo- or 3- to 10-membered heterocyclic group;
  • R 31 , R 32 each independently of one another represent hydrogen, halogen or optionally mono- or poly- M 2 -substituted (Ci-Cio)-alkyl, (C 2 -Cio)-alkenyl, (C 2 -Cio)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C10)- haloalkenyl, (C2-Cio)-haloalkynyl, (C3-Ci4)-cycloalkyl-(Ci-Cio)-alkyl or represent an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
  • R 31 , R 32 together represent an optionally mono- or poly-M 5 -substituted spiro-attached 3- to 14-membered carbo- or 3- to 10-membered heterocyclic group;
  • M 5 in each case independently of the others represents halogen, formyl, cyano, nitro, (Ci-Cio)-alkyl, (Ci-Cio)-haloalkyl, (C2-Cio)-alkenyl, (C2-Cio)-haloalkenyl, (C2-Cio)-alkynyl, (C2-Cio)-haloalkynyl, (Ci-Cio)-alkoxy, (Ci-Cio)-haloalkoxy, (C2-Cio)-alkenyloxy, (C2-Cio)-haloalkenyloxy, (C3-C10)- alkynyloxy, (C3-Cio)-haloalkynyloxy, (Ci-Cio)-alkylthio, (Ci-Cio)-haloalkynyloxy, (C2-C10)- alkenylthio, (C2-Cio)
  • the invention also comprises a method for preparing an agricultural composition comprising adding agriculturally suitable components such as suitable extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, thickeners, adjuvants or the like to the composition according to the invention. Furthermore the invention comprises a method for reducing damage of plants and plant parts or losses in harvested fruits or vegetables caused by harmful microorganisms by controlling such harmful microorganisms, comprising applying the compounds to the plant or the harmful microorganisms or the habitat of the plant or the habitat of the harmful microorganisms. In view of this, the problem underlying the present invention has been solved by using known compounds which exhibit fungicidal activity against harmful microorganisms in plants, in the protection of materials.
  • novel compositions according to the invention enable reduced application rates and broaden the activity spectrum of the fungicides.
  • new use of the known compounds provide improved activity harmful microorganisms and consequently provide efficient disease control for reducing damage of plants and plant parts or losses in harvested fruits or vegetables.
  • the compounds of the formula (I) may, where appropriate, depending on the nature of the substituents, be in the form of geometric and/or optically active isomers or corresponding isomer mixtures of varying composition.
  • the invention relates both to the pure isomers and to the isomer mixtures.
  • the compounds according to the invention can also be present as metal complexes. Definitions:
  • phytopathogenic means that the respective organism is capable of infesting plants or plant parts.
  • control of harmful microorganisms means a reduction in infestation by harmful microorganisms, compared with the untreated plant or plant part as defined below measured as fungicidal efficacy, preferably a reduction by 25-50 %, compared with the untreated plant (100 %), more preferably a reduction by 40-79 %, compared with the untreated plant (100 %); even more preferably, the infection by harmful microorganisms is entirely suppressed (by 70-100 %).
  • the control may be curative, i.e. for treatment of already infected plants, or protective, for protection of plants which have not yet been infected.
  • an "effective but non-phytotoxic amount” means an amount of the compounds according to formula (I) which is sufficient to control the fungal disease of the plant in a satisfactory manner or to eradicate the fungal disease completely, and which, at the same time, does not cause any significant symptoms of phytotoxicity. In general, this application rate may vary within a relatively wide range. It depends on several factors, for example on the fungus to be controlled, the plant, the climatic conditions and the ingredients of the inventive compositions.
  • the term "mono- or poly-" means preferably mono- to hexa-, particularly preferably mono- to terra-, very particularly preferably mono- to tri- and especially preferably mono- or di-.
  • Ci-Cio-structures Ci-Cio
  • an alkyl group of 1 to 10 carbon atoms corresponds to (Ci-Cio)-alkyl.
  • Ring structures of carbon atoms and heteroatoms are referred to as "3- to 14-membered" structures.
  • a collective term for a substituent for example (Ci-Cio)-alkyl
  • a composite substituent such as, for example, (C3-Ci4)-cycloalkyl-(Ci-Cio)-alkyl
  • the component at the end of the composite substituent for example the (Ci-Cio)-alkyl
  • Halogen unless defined otherwise: elements of the 7th main group; preference is given to fluorine, chlorine, bromine and iodine.
  • (Ci-Cio)-Alkyl unless defined differently elsewhere: saturated straight-chain or branched hydrocarbon radicals having preferably (Ci-Ce)-, particularly preferably (C1-C4)- carbon atoms. Examples: methyl, ethyl, isopropyl, n-propyl, 1 -methylethyl, butyl, tert- butyl, etc.
  • (C 2 -Cio)-Alkenyl unless defined differently elsewhere: unsaturated straight-chain or branched hydrocarbon radicals having a double bond. Preference is given to (C2-Ce)- or (C2-C i)-alkenyl. Examples: ethenyl, 1 -propenyl, 3-butenyl, etc.
  • (C 2 -Cio)-Alkynyl unless defined differently elsewhere: unsaturated straight-chain or branched hydrocarbon radicals having a triple bond. Preference is given to (C2-Ce)- or (C2-C i)-alkynyl. Examples: ethynyl, 1 -propynyl, etc.
  • (Ci-Cio)-Alkoxy (alkyl radical-O-), unless defined differently elsewhere: an alkyl radical which is attached to the skeleton via an oxygen atom (-0-).
  • Preference is given to (Ci-Ce)- or (Ci-C i)-alkoxy Examples: methoxy, ethoxy, propoxy, 1-methylethoxy, etc.
  • (C2-Cio)-alkenyloxy and (C3-Cio)-alkynyloxy are alkenyl radicals and alkynyl radicals, respectively, which are attached to the skeleton via -0-.
  • Preference is given to (C2-Ce)- or (C2-C i)-alkenyloxy
  • Preference is given to (C3-Ce)- or (C3-C i)-alkynyloxy
  • the number of the carbon atoms refers to the alkyl radical in the alkylcarbonyl group.
  • Preference is given to (Ci-Ce)- or (Ci-C4)-alkylcarbonyloxy.
  • Preference is given to (C2-C6)- or (C2-C i)-alkenylcarbonyloxy
  • Preference is given to (C2-C6)- or (C2-C i)-alkynylcarbonyloxy
  • (Ci-Cio)-Alkylthio unless defined differently elsewhere: an alkyl radical which is attached to the skeleton via -S-.
  • Preference is given to (Ci-Ce)- or (Ci-C4)-alkylthio.
  • (C2-Cio)-alkenylthio and (C3-Cio)-alkynylthio are: alkenyl radicals and alkynyl radicals, respectively, which are attached to the skeleton via -S-.
  • Preference is given to (C2-C6)- or (C2-C4)-alkenylthio.
  • Preference is given to (C3-C6)- or (C3-C4)-alkynylthio.
  • Preference is given to (Ci-Ce)- or (Ci-C4)-alkylsulphinyl.
  • Preference is given to (C2-C6)- or (C2-C4)-alkenylsulphinyl.
  • Preference is given to (C3-C6)- or (C3-C4)-alkynylsulphinyl.
  • Preference is given to (C2-C6)- or (C2-C4)-alkenylsulphonyl.
  • Preference is given to (C3-C6)- or (C3-C4)-alkynylsulphonyl.
  • halogenated structures are, for example, chloromethyl, trichloromethyl, fluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 2,2-difluoroethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio.
  • (C3-Ci4)-Carbocyclic group unless defined differently elsewhere: (C3-Ci4)-cycloalkyl, (C3-C14)- cycloalkenyl, (C6-Ci 4 )-aryl, halogenated (C3-Ci 4 )-cycloalkyl, halogenated (C3-Ci 4 )-cycloalkenyl, halogenated (C6-Ci 4 )-aryl.
  • Cycloalkyl unless defined differently elsewhere: mono-, bi- or tricyclic saturated hydrocarbon groups preferably having (C3-C14)-, (C3-C8)- or (C3-C6)-ring atoms. Cycloalkyl may also be a spirocyclic group. Examples: cyclopropyl, -butyl, -pentyl, -hexyl, -heptyl, bicyclo[2.2.1]heptyl or adamantyl. "Cycloalkyl” preferably represents monocyclic groups of 3, 4, 5, 6 or 7 ring atoms.
  • (C3-Ci4)-cycloalkenyl is: a mono-, bi- or tricyclic, but partially unsaturated hydrocarbon group having at least one double bond, preferably having (C3-C8)- or (C3-C6)-ring atoms.
  • (Ce-Ci4)-Aryl unless defined differently elsewhere: mono-, bi- or tricyclic ring system group where at least one cycle is aromatic, preferably having (Ce-Cs)- or (C6)-ring atoms.
  • aryl is an aromatic C6-monocyclic ring system group; a bicyclic (C8-Ci4)-ring system group; or a tricyclic (Cio-Ci4)-ring system group.
  • Halogenated (C3-Ci4)-carbocyclic group, halogenated (C3-Ci4)-cycloalkyl, halogenated (C3-C14)- cycloalkenyl, halogenated (C6-Ci4)-aryl are in each case, unless defined differently, defined analogously to (C3-Ci 4 )-carbocyclic group, (C3-Ci 4 )-cycloalkyl, (C3-Ci 4 )-cycloalkenyl, (C6-Ci 4 )-aryl, where at least one hydrogen atom is replaced by a halogen atom as mentioned above. In one embodiment, all hydrogen atoms are replaced by halogen.
  • Examples of halogenated structures are 3-chlorophenyl, 2- bromocyclopentyl.
  • Heteroatom for example N, O, S, P, B, Si.
  • 3- to 10-membered heterocyclic group unless defined differently elsewhere: 3- to 9-membered heterocyclyl group or 5- to 10-membered heteroaryl group, halogenated 3- to 9-membered heterocyclyl group or halogenated 5- to 10-membered heteroaryl group.
  • 3- to 9-membered heterocyclyl unless defined differently elsewhere: 3- to 9-membered saturated or partially unsaturated mono-, bi- or tricyclic ring system group of carbon atoms and at least one heteroatom preferably selected from the group consisting of N, O and S.
  • the ring system is preferably a 3- to 6-membered ring system.
  • the ring system contains 1 , 2, 3 or 4 heteroatoms, particularly preferably 1 or 2 heteroatoms.
  • Preference is also given to a monocyclic ring system.
  • a monocyclic ring system is a partially unsaturated monocyclic ring system having a double bond.
  • Heterocyclyl may be a spirocyclic system.
  • 5- to 10-membered heteroaryl unless defined differently elsewhere: mono-, bi- or tricyclic 5- to 10- membered heterocyclic group of carbon atoms and at least one heteroatom, preferably selected from the group consisting of N, O and S, where at least one cycle is aromatic.
  • the ring system is preferably a 5- to 6-membered ring system.
  • heteroaryl is an aromatic monocyclic ring system of 5 or 6 ring atoms.
  • heteroaryl is an aromatic monocyclic ring system containing 1 to 4 heteroatoms from the group consisting of O, N and S.
  • heteroaryl may be a bicyclic ring system consisting of 8 to 14 ring atoms or a tricyclic ring system consisting of 13 or 14 ring atoms.
  • heteroaryl as component of a composite substituent such as, for example, 5- to 10- membered heteroaryl-(C5-Cio)-alkyl, unless defined differently elsewhere.
  • 5- and 6-membered heteroaryl groups are described in more detail below:
  • 5- membered heteroaryl unless defined differently elsewhere: heteroaryl group containing one to three or one to four nitrogen, oxygen and/or sulphur atom(s) as ring atoms. Examples: furanyl, thienyl, oxazolyl, thiazolyl.
  • a 5-membered heteroaryl group contains, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms as ring members. Examples: pyrrolyl, pyrazolyl, triazolyl, imidazolyl.
  • a 5-membered heteroaryl contains one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom. Examples: thiazolyl, oxazolyl, oxadiazolyl.
  • 6-membered heteroaryl unless defined differently elsewhere: heteroaryl group containing one to three or one to four nitrogen atom(s) as ring atoms.
  • a 6-membered heteroaryl group contains one to three nitrogen atoms. Examples: pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl.
  • Halogenated 3- to 9-membered heterocyclyl group or halogenated 5- to 10-membered heteroaryl group are defined analogously to 3- to 9-membered heterocyclyl group or 5- to 10-membered heteroaryl group, where at least one hydrogen atom is replaced by a halogen atom as mentioned above. In one embodiment, all hydrogen atoms are replaced by halogen.
  • Example of halogenated heterocyclic structures 3-chlorotetrahydrothiopyran-2-yl, 4-chloropyridin-2-yl.
  • Ring structures having three or more adjacent oxygen atoms, for example, are excluded.
  • the compounds according to the invention may be present in various polymorphic forms or as mixtures of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are provided by the invention and can be used in accordance with the invention.
  • Q preferably represents the structural elements below, where n for each Q is in each case as defined below:
  • n for each Q is in each d below:
  • n for each Q is in each case below:
  • n for each Q is in each case as defined below:
  • n very particularly preferably represents the structural elements below, where n for each Q is in each case as defined below:
  • n very particularly preferably represents the structural elements below, where n for each Q is in each case as defined below:
  • n for each Q is in each case as defined below:
  • Q in particular very particularly preferably represents 2-thienyl, 3-fluoro-2-thienyl, 3-chloro-2- thienyl, 3,4-dichloro-2-thienyl, 2,5-dichloro-3-thienyl, 3,4,5-trichloro-2-thienyl, 3-bromo-2- thienyl, 3-iodo-2-thienyl, 3-cyano-2-thienyl, 3-methyl-2-thienyl, 3-(trifluoromethyl)-2-thienyl, 3- methoxy-2-thienyl, 3-ethoxy-2-thienyl, 3-thienyl, 2-fluoro-3 -thienyl, 2-chloro-3 -thienyl, 2-bromo- 3 -thienyl, 2-iodo-3 -thienyl, 2-cyano-3 -thienyl, 2-methyl-3 -thienyl, 2-(trifluoromethyl)-3 -thienyl,
  • Y particularly preferably represents hydrogen or represents optionally mono- or poly-M 2 -substituted (Ci-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C4)- alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C 4 )-alkyl;
  • Y particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec -butyl, isobutyl, tert-butyl, cyanomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, allyl, butenyl, propargyl, butynyl, 3,3-dichloroprop-2-enyl, methoxy, ethoxy, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • Y very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec- butyl, isobutyl, tert-butyl, methoxy, ethoxy, cyclopropylmethyl, cyclopropyl, cyclobutyl;
  • Y very particularly preferably represents hydrogen, cyclopropyl
  • Y very particularly preferably represents hydrogen; W preferably represents oxygen;
  • W preferably represents sulphur
  • M 1 , M 2 and M 3 each independently of one another preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (Ci-C 6 )-alkoxy, (Ci-C 6 )-haloalkoxy, (Ci-C 6 )-alkylthio, (Ci- C6)-haloalkylthio, (Ci-C6)-alkylsulphonyl, (Ci-C6)-haloalkylsulphonyl, (Ci-C6)-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-Ci 4 )-cycloalkyl-0-, (C3-Ci 4 )-cycloalkenyl-0-, (C6-Ci 4 )-aryl-0-, halogenated (C3-Ci 4 )-cycloal
  • M 1 , M 2 and M 3 each independently of one another preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (Ci-C 6 )-alkoxy, (Ci-C 6 )-haloalkoxy, (Ci-C 6 )-alkylthio, (Ci- C6)-haloalkylthio, (Ci-C6)-alkylsulphonyl, (Ci-C6)-haloalkylsulphonyl, (Ci-C6)-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-Ci 4 )-cycloalkyl-0-, (C3-Ci 4 )-cycloalkenyl-0-, (C6-Ci 4 )-aryl-0-, halogenated (C3-Ci 4 )-cycloal
  • M 1 , M 2 and M 3 each independently of one another preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci- C 4 )-haloalkylthio, (Ci-C 4 )-alkylsulphonyl, (Ci-C 4 )-haloalkylsulphonyl, (Ci-C 4 )-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-Ci 4 )-cycloalkyl-0-, (C3-Ci 4 )-cycloalkenyl-0-, (C6-Ci 4 )-aryl-0-, halogenated (C3-C
  • M 1 , M 2 and M 3 each independently of one another preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci- C 4 )-haloalkylthio, (Ci-C 4 )-alkylsulphonyl, (Ci-C 4 )-haloalkylsulphonyl, (Ci-C 4 )-alkylsulphanyl,
  • (Ci-C6)-haloalkylsulphanyl (C3-Ci 4 )-cycloalkyl-0-, (C3-Ci 4 )-cycloalkenyl-0-, (C6-Ci 4 )-aryl-0-, halogenated (C3-Ci 4 )-cycloalkyl-0-, halogenated (C3-Ci 4 )-cycloalkenyl-0-, halogenated (Ce-Cu)- aryl-O-, where, if Q corresponds to Q 11 , M 3 is not (Ci-C 4 )-haloalkyl in position 4 at the pyridyl;
  • M 1 , M 2 and M 3 each independently of one another very particularly preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy,
  • M 1 , M 2 and M 3 each independently of one another very particularly preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )-haloalkylthio, (Ci-C 4 )-alkylsulphonyl, (Ci-C 4 )-haloalkylsulphonyl, (Ci-
  • M 1 , M 2 and M 3 each independently of one another very particularly preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C2)-alkyl, (Ci-C2)-haloalkyl, (Ci-C2)-alkoxy, (Ci-C2)-haloalkoxy, (Ci-C 2 )-alkylthio, (Ci-C 2 )-haloalkylthio, (Ci-C 2 )-alkylsulphonyl, (Ci-C 2 )-haloalkylsulphonyl, (Ci-
  • M 1 , M 2 and M 3 each independently of one another very particularly preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C2)-alkyl, (Ci-C2)-haloalkyl, (Ci-C2)-alkoxy, (Ci-C2)-haloalkoxy, (Ci-C 2 )-alkylthio, (Ci-C 2 )-haloalkylthio, (Ci-C 2 )-alkylsulphonyl, (Ci-C 2 )-haloalkylsulphonyl, (Ci- C2)-alkylsulphanyl, (Ci-C2)-haloalkylsulphanyl, (C6)-aryl-0-, halogenated (C6)-aryl-0-, where, if
  • Q corresponds to Q 11 , M 3 is not (Ci-C 2 )-haloalkyl in position 4 at the pyridyl;
  • M 1 , M 2 and M 3 each independently of one another very particularly preferably represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, OH, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec -butyl, tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, 2,2,2-trifluoroethylthio, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, 2,2,2-trifluoroethylsulphonyl, methylsulphanyl, ethylsulphany
  • M 1 , M 2 and M 3 each independently of one another very particularly preferably represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, OH, methyl, ethyl, isopropyl, teil-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, 2,2,2-trifluoroethylthio, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, 2,2,2-trifluoroethylsulphonyl, methylsulphanyl, ethylsulphanyl, trifluoromethylsulphanyl, 2,2,2-trifluoroethylsulphanyl or phenoxy;
  • M 1 , M 2 and M 3 each independently of one another very particularly preferably represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, OH, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, 2,2,2-trifluoroethylthio, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, 2,2,2-trifluoroethylsulphonyl, methylsulphanyl, ethylsulphanyl, trifluoromethylsulphanyl, 2,2,2-trifluoroethylsulphanyl or phenoxy, where, if Q corresponds to Q 11 , M 3 is not
  • M 1 , M 2 and M 3 each independently of one another in particular very particularly preferably represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, methyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy or phenoxy;
  • M 1 , M 2 and M 3 each independently of one another in particular very particularly preferably represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, methyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy or phenoxy, where, if Q corresponds to Q 11 , M 3 is not trifluoromethyl in position 4 at the pyridyl;
  • M 1 , M 2 and M 3 each independently of one another in particular very particularly preferably represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, trifluoromethyl, difluoromethyl;
  • M 1 , M 2 and M 3 each independently of one another in particular very particularly preferably represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, trifluoromethyl, difluoromethyl, where, if Q corresponds to Q 11 , M 3 is not trifluoromethyl in position 4 at
  • M 4 preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C6)-alkyl, (Ci-C6)-haloalkyl, (Ci-Ce)- alkoxy, (Ci-C6)-haloalkoxy, (Ci-C6)-alkylthio, (Ci-C6)-haloalkylthio, (Ci-C6)-alkylsulphonyl, (Ci-
  • C6)-haloalkylsulphonyl (Ci-C6)-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-Ci4)-cycloalkyl- 0-, (C3-Ci4)-cycloalkenyl-0-, (C6-Ci4)-aryl-0-, halogenated (C3-Ci4)-cycloalkyl-0-, halogenated (C3-Ci4)-cycloalkenyl-0-, halogenated (C6-Ci4)-aryl-0-;
  • M 4 preferably represents hydrogen, halogen, cyano, nitro, OH, (Ci-C6)-alkyl, (Ci-C6)-haloalkyl, (Ci-Ce)- alkoxy, (Ci-C 6 )-haloalkoxy, (Ci-C 6 )-alkylthio, (Ci-C 6 )-haloalkylthio, (Ci-C 6 )-alkylsulphonyl, (Ci-
  • M 4 very particularly preferably represents hydrogen, halogen, cyano, nitro, OH, (Ci-C4)-alkyl, (C1-C4)- haloalkyl, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )-haloalkylthio, (C1-C4)- alkylsulphonyl, (Ci-C4)-haloalkylsulphonyl, (Ci-C4)-alkylsulphanyl, (Ci-C4)-haloalkylsulphanyl, (C6-Ci4)-aryl-0-, halogenated (C6-Ci4)-aryl)-0-; M 4 very particularly preferably represents hydrogen, halogen, cyano, nitro, OH, (Ci-C4)-alkyl, (C1-C4)- haloalkyl, (
  • M 4 very particularly preferably represents hydrogen, halogen, cyano, nitro, OH, (Ci-C2)-alkyl, (C1-C2)- haloalkyl, (Ci-C 2 )-alkoxy, (Ci-C 2 )-haloalkoxy, (Ci-C 2 )-alkylthio, (Ci-C 2 )-haloalkylthio, (C1-C2)- alkylsulphonyl, (Ci-C 2 )-haloalkylsulphonyl, (Ci-C 2 )-alkylsulphanyl, (Ci-C 2 )-haloalkylsulphanyl,
  • M 4 very particularly preferably represents hydrogen, halogen, cyano, nitro, OH, (Ci-C 2 )-alkyl, (C1-C2)- haloalkyl, (Ci-C 2 )-alkoxy, (Ci-C 2 )-haloalkoxy, (Ci-C 2 )-alkylthio, (Ci-C 2 )-haloalkylthio, (C1-C2)- alkylsulphonyl, (Ci-C 2 )-haloalkylsulphonyl, (Ci-C 2 )-alkylsulphanyl, (Ci-C 2 )-haloalkylsulphanyl, (C 6 )-aryl-0-, halogenated (C 6 )-aryl-0-, where, if Q corresponds to Q 10 , M 4 is not (C1-C2)- haloalkyl;
  • M 4 very particularly preferably represents fluorine, bromine, chlorine, iodine, cyano, nitro, OH, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec -butyl, tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, 2,2,2- trifluoroethylthio, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, 2,2,2- trifluoroethylsulphonyl, methylsulphanyl, ethylsulphanyl, trifluoromethylsulphanyl, 2,2,
  • M 4 very particularly preferably represents hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, OH, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, 2,2,2-trifluoroethylthio, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, 2,2,2-trifluoroethylsulphonyl, methylsulphanyl, ethylsulphanyl, trifluoromethylsulphanyl, 2,
  • M 4 very particularly preferably represents hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, OH, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, 2,2,2-trifluoroethylthio, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, 2,2,2-trifluoroethylsulphonyl, methylsulphanyl, ethylsulphanyl, trifluoromethylsulphanyl, 2,2,2-trifluoroethylsulphanyl or phenoxy; M very particularly preferably represents hydrogen, fluorine, bromine, chlorine, iodine, cyano,
  • M 4 in particular very particularly preferably represents fluorine, bromine, chlorine, iodine, cyano, nitro, methyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethylsulphanyl, trifluoromethoxy, difluoromethoxy, ethoxy, isopropoxy or phenoxy;
  • M 4 in particular very particularly preferably represents hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, methyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethylsulphanyl, trifluoromethoxy, difluoromethoxy, ethoxy, isopropoxy or phenoxy, where, if Q corresponds to Q 10 , M 4 is not trifluoromethyl; M 4 in particular very particularly preferably represents fluorine, bromine, chlorine, iodine, cyano, nitro, trifluoromethyl, difluoromethyl, methoxy, trifluoromethylsulphanyl, trifluoromethoxy, difluoromethoxy;
  • M 4 in particular very particularly preferably represents hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, trifluoromethyl, difluoromethyl, methoxy, trifluoromethylsulphanyl, trifluoromethoxy, difluoromethoxy, where, if Q corresponds to Q 10 , M 4 is not trifluoromethyl;
  • M 4 in particular very particularly preferably represents fluorine, bromine, chlorine, iodine, cyano, nitro, methyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy or phenoxy;
  • M 4 in particular very particularly preferably represents hydrogen, fluorine, bromine, chlorine, iodine, cyano, nitro, methyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy or phenoxy, where, if Q corresponds to Q 10 , M 4 is not trifluoromethyl; k preferably represents 1 or 2; k particularly preferably represents 1 ;
  • R 21 , R 22 preferably each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )- haloalkenyl, (C2-C6)-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C6)-haloalkoxy, (C2-C6)-alkenyloxy, (C3- C6)-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl or represent an optionally mono- or poly-M - substituted (C3-Ci4)-carbocyclic grouop;
  • R 22 preferably each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C 2 -C 4 )- haloalkenyl, (C2-C 4 )-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C 4 )-haloalkoxy, (C2-C 4 )-alkenyloxy, (C3- C 4 )-alkynyloxy, (C3-C 4 )-cycloalkyl-(Ci-C 4 )-alkyl, (C3-Cg)-cycloalkyl or halogenated (C3-C8)- cycloalkyl;
  • R 22 preferably represent C(R 21 , R 22 ) as spiro-C(CH 2 -CH 2 );
  • R 22 particularly preferably each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C1-C4)- haloalkyl, (Ci-C6)-alkoxy, (C 2 -C 4 )-alkenyloxy, (C3-C 4 )-alkynyloxy, (C3-C 4 )-cycloalkyl-(Ci-C 4 )- alkyl, (C3-C6)-cycloalkyl;
  • R 22 preferably each independently of one another represent hydrogen, fluorine, methyl, ethyl, n- propyl, isopropyl, tert-butyl, butyl, allyl, propargyl, chloromethyl, trichloromethyl, fluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 2,2-difluoroethyl, difluoromethyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl;
  • R 22 preferably each independently of one another represent hydrogen, fluorine, methyl, ethyl, n- propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl;
  • R 22 very particularly preferably each independently of one another represent hydrogen, fluorine or (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl;
  • R 22 in particular very particularly preferably represent hydrogen, methyl or ethyl
  • R 32 preferably each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )- haloalkenyl, (C 2 -C6)-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C6)-haloalkoxy, (C 2 -C6)-alkenyloxy, (C3- Ce)-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl or represent an optionally mono- or poly-M 2 - substituted (C3-Ci 4 )-carbocyclic group;
  • R 32 preferably each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C2-C4)- haloalkenyl, (C 2 -C 4 )-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C 4 )-haloalkoxy, (C 2 -C 4 )-alkenyloxy, (C3- C4)-alkynyloxy, (C3-C i)-cycloalkyl-(Ci-C4)-alkyl or represent an optionally mono- or poly-M - substituted (C3-Cg)-cycloalkyl or halogenated (C3-Cg)-cycloalkyl;
  • R 32 preferably represents C(R 31 , R 32 ) as spiro-C(CH 2 -CH 2 );
  • R 32 particularly preferably represents C(R 31 , R 32 ) as 1 , 1 -cyclopropyl
  • R 32 particularly preferably each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C i)-alkyl, (Ci-C4)-haloalkyl, (C 2 -C4)-haloalkenyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (Ci-C6)-alkoxy, (C2-C4)-alkenyloxy, (C3-C4)-alkynyloxy, (C3- C4)-cycloalkyl-(C3-C4)-alkyl, (C3-C6)-cycloalkyl;
  • R 32 particularly preferably each independently of one another represent hydrogen, methyl, ethyl, n- propyl, isopropyl, tert-butyl, allyl, propargyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl;
  • R 32 very particularly preferably each independently of one another represent hydrogen, fluorine or (Ci-C 4 )-alkyl
  • R 32 in particular very particularly preferably each independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl; preferably in each case independently of the others represents halogen, formyl, cyano, nitro, (Ci- C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )- haloalkynyl, (Ci-C6)-alkoxy, (Ci-C6)-haloalkoxy, (C2-C6)-alkenyloxy, (C2-C6)-haloalkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 3 -C 6 )-haloalkynyloxy, (C
  • halogen formyl, cyano, nitro, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C 2 - C4)-haloalkynyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (C2-C4)-alkenyloxy, (C2-C4)- haloalkenyloxy, (C3-C4)-alkynyloxy, (C3-C4)-haloalkynyloxy, (Ci-C4)-alkylthio, (C1-C4)- haloalkylthio, (C 2 -C 4 )-alkenylthio, (C 2 -C 4 )-alkenylthio, (C 2
  • M 5 very particularly preferably in each case independently of the others represents chlorine, fluorine, formyl, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci- C 4 )-alkylthio, (Ci-C 4 )-haloalkylthio, (Ci-C 4 )-alkylsulphonyl, (Ci-C 4 )-haloalkylsulphonyl, (C1-C4)- alkylsulphanyl, (Ci-C4)-haloalkylsulphanyl, (Ci-C4)-alkylcarbonyl, (Ci-C4)-haloalkylcarbonyl or (C3-C6)-cycloalkyl.
  • M 5 very particularly preferably in each case independently of the others represents fluorine, bromine, chlorine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, 2,2,2-trifluoroethylthio, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, 2,2,2-trifluoroethylsulphonyl, methylsulphanyl, ethylsulphanyl, trifluoromethylsulphanyl, 2,2,2-trifluoroethylsulphanyl, cyclopropyl, cyclobutyl or cyclopentyl.
  • M , M , M J , M , M , k, L , V, W and Y are as defined above and
  • Q preferably represents the structural elements below, where n for each Q is in each case as defined below:
  • Q preferably represents the structural elements below, where n for each Q is in each case as defined below:
  • n 1-2 preferably represents the structural elements below, where n for each Q is in each case as defined below:
  • n for each Q is in each case as defined below:
  • Q particularly preferably represents 2-thienyl, 3-fluoro-2-thienyl, 3-chloro-2-thienyl, 3,4-dichloro-2- thienyl, 3,4,5-trichloro-2-thienyl, 3-bromo-2-thienyl, 3-iodo-2-thienyl, 3-cyano-2-thienyl, 3- methyl-2-thienyl, 3-(trifluoromethyl)-2-thienyl, 3-methoxy-2-thienyl, 3-ethoxy-2-thienyl, 3- thienyl, 2-fluoro-3 -thienyl, 2-chloro-3 -thienyl, 2-bromo-3 -thienyl, 2-iodo-3 -thienyl, 2-cyano-3- thienyl, 2-methyl-3 -thienyl, 2-(trifluoromethyl)-3-thienyl, 2-ethoxy-3- thienyl, 2-ethoxy-3- thi
  • M 1 , M 2 , M 3 , M 4 , M 5 , k, L 2 , L 3 , Q and W are as defined above and preferably represents hydrogen or represents optionally mono- or poly-M -substituted (Ci-C 4 )- alkyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C 2 -C 4 )-haloalkenyl, (C3-C4)- haloalkynyl, (Ci-C 4 )-alkoxy, (C2-C 4 )-alkenyloxy, (C3-C 4 )-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C 4 )- alkyl or represents an optionally substituted C3- to C6-membered carbocyclic group; particularly
  • M 1 , M 2 , M 3 , M 4 , M 5 , k, L 2 , L 3 , Q and Y are as defined above and
  • W preferably represents oxygen
  • M 1 , M 2 , M 3 , M 4 , M 5 , k, L 3 , Q, W and Y are as defined above and
  • L preferably represents C(R , R ), where R and R each independently of one another represent hydrogen hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C 4 )-alkyl, (C3-C4)- alkenyl, (C 3 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C 3 -C 4 )-haloalkenyl, (C 3 -C 4 )-haloalkynyl, (C 1 -C4)- alkoxy, (C3-C 4 )-alkenyloxy, (C3-C 4 )-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C 4 )-alkyl or represents an optionally substituted C3- to C6-membered carbocyclic group, or where R 21 and R 22 together represent an optionally substituted spiro-linked 3- to 6-membered
  • M 1 , M 2 , M 3 , M 4 , M 5 , k, L 2 , Q, W and Y are as defined above and
  • L 3 preferably represents C(R 31 , R 32 ), where R 31 and R 32 each independently of one another represent hydrogen hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C i)-alkyl, (C3-C4)- alkenyl, (C 3 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C 3 -C 4 )-haloalkenyl, (C 3 -C 4 )-haloalkynyl, (C1-C4)- alkoxy, (C3-C 4 )-alkenyloxy, (C3-C 4 )-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C 4 )-alkyl or represents an optionally substituted C3- to C6-membered carbocyclic group, or where R 31 and R 32 together represent an optionally substituted spiro-linked 3- to 6-
  • L 3 particularly preferably represents C(R 31 , R 32 ) where R 31 and R 32 each independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl, or where C(R 31 , R 32 ) represents spiro-
  • Q represents 2-thienyl, 3-fluoro-2-thienyl, 3-chloro-2-thienyl, 3,4-dichloro-2-thienyl, 3,4,5-trichloro- 2-thienyl, 3-bromo-2-thienyl, 3-iodo-2-thienyl, 3-cyano-2-thienyl, 3-methyl-2-thienyl, 3- (trifluoromethyl)-2-thienyl, 3-methoxy-2-thienyl, 3-ethoxy-2-thienyl, 3-thienyl, 2-fluoro-3- thienyl, 2-chloro-3-thienyl, 2-bromo-3-thienyl, 2-iodo-3-thienyl, 2-cyano-3-thienyl, 2-methyl-3- thienyl, 2-(trifluoromethyl)-3-thienyl, 2-methoxy-3-thienyl, 2-ethoxy-3-thienyl, 2-furanyl, 3- fluor
  • Y represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyanomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, allyl, butenyl, propargyl, butynyl, 3,3- dichloroprop-2-enyl, methoxy, ethoxy, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • W represents oxygen
  • L 2 represents C(R 21 , R 22 ) where R 21 and R 22 each independently of one another represent hydrogen, fluorine, methyl, ethyl, n-propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl, or where C(R 21 , R 22 ) represents spiro-C(CH2- CH 2 );
  • L 3 represents C(R 31 , R 32 ) where R 31 and R 32 each independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl, or where C(R 31 , R 32 ) represents spiro-C(CH2-CH2); k represents 1 and
  • M 1 and M 2 each independently of one another represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, methyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy or phenoxy; and salts, N-oxides and tautomeric forms of the compounds of the formula (I).
  • n for each Q is in each case as defined below:
  • Y represents hydrogen or represents optionally mono- or poly-M -substituted (Ci-Cio)-alkyl, (C2- Cio)-alkenyl, (C 2 -Cio)-alkynyl, (Ci-Cio)-haloalkyl, (C 2 -Cio)-haloalkenyl, (C 2 -Cio)-haloalkynyl, (Ci-Cio)-alkoxy, (C2-Cio)-alkenyloxy, (C3-Cio)-alkynyloxy, (C3-Ci4)-cycloalkyl-(Ci-Cio)-alkyl or represents an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
  • W represents oxygen or sulphur
  • L 2 represents -C(R 21 , R 22 )-
  • L 3 represents -C(R 31 , R 32 )-
  • M 1 , M 2 and M 3 each independently of one another represent hydrogen, halogen, cyano, nitro, OH, (Ci- Cio)-alkyl, (Ci-Cio)-haloalkyl, (Ci-Cio)-alkoxy, (Ci-Cio)-haloalkoxy, (Ci-Cio)-alkylthio, (C1-C10)- haloalkylthio, (Ci-Cio)-alkylsulphonyl, (Ci-Cio)-haloalkylsulphonyl, (Ci-Cio)-alkylsulphanyl, (Ci- Cio)-haloalkylsulphanyl or (3- to 14-membered cyclic group)-0-, where, if Q corresponds to Q 11 , M 3 is not (Ci-C i)-haloalkyl in position 4 at the pyridyl;
  • M 4 represents hydrogen, halogen, cyano, nitro, OH, (Ci-Cio)-alkyl, (Ci-Cio)-haloalkyl, (C1-C10)- alkoxy, (Ci-Cio)-haloalkoxy, (Ci-Cio)-alkylthio, (Ci-Cio)-haloalkylthio, (Ci-Cio)-alkylsulphonyl, (Ci-Cio)-haloalkylsulphonyl, (Ci-Cio)-alkylsulphanyl, (Ci-Cio)-haloalkylsulphanyl, or (3- to 14- membered cyclic group)-0-, where, if Q corresponds to Q 10 , M 4 is not (Ci-C i)-haloalkyl; k represents 1 , 2 or 3; R 21 , R 22 each independently of one another represent hydrogen, halogen
  • R 21 , R 22 together represent an optionally mono- or poly-M 2 -substituted spiro-attached 3- to 14-membered carbo- or 3- to 10-membered heterocyclic group;
  • R 31 , R 32 each independently of one another represent hydrogen, halogen or optionally mono- or poly- M 2 -substituted (Ci-Cio)-alkyl, (C 2 -Cio)-alkenyl, (C 2 -Cio)-alkynyl, (Ci-Cio)-haloalkyl, (C2-C10)- haloalkenyl, (C2-Cio)-haloalkynyl, (C3-Ci4)-cycloalkyl-(Ci-Cio)-alkyl or represent an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
  • R 31 , R 32 together represent an optionally mono- or poly-M 5 -substituted spiro-attached 3- to 14- membered carbo- or 3- to 10-membered heterocyclic group;
  • M 5 in each case independently of the others represents halogen, formyl, cyano, nitro, (Ci-Cio)-alkyl, (Ci-Cio)-haloalkyl, (C2-Cio)-alkenyl, (C2-Cio)-haloalkenyl, (C2-Cio)-alkynyl, (C2-Cio)-haloalkynyl, (Ci-Cio)-alkoxy, (Ci-Cio)-haloalkoxy, (C2-Cio)-alkenyloxy, (C2-Cio)-haloalkenyloxy, (C3-C10)- alkynyloxy, (C3-Cio)-haloalkynyloxy, (Ci-Cio)-alkylthio, (Ci-Cio)-haloalkynyloxy, (C2-C10)- alkenylthio, (C2-Cio)
  • Q represents 2-thienyl, 3-fluoro-2-thienyl, 3-chloro-2-thienyl, 3,4-dichloro-2-thienyl, 2,5-dichloro-3- thienyl, 3,4,5-trichloro-2-thienyl, 3-bromo-2-thienyl, 3-iodo-2-thienyl, 3-cyano-2-thienyl, 3- methyl-2-thienyl, 3-(trifluoromethyl)-2-thienyl, 3-methoxy-2-thienyl, 3-ethoxy-2-thienyl, 3- thienyl, 2-fluoro-3-thienyl, 2-chloro-3-thienyl, 2-bromo-3-thienyl, 2-iodo-3-thienyl, 2-cyano-3- thienyl, 2-methyl-3-thienyl, 2-(trifluoromethyl)-3-thienyl, 2-methoxy-3-thienyl, 2-eth
  • Y represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyanomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, allyl, butenyl, propargyl, butynyl, 3,3- dichloroprop-2-enyl, methoxy, ethoxy, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • W represents oxygen
  • L 2 represents C(R 21 , R 22 ) where R 21 and R 22 each independently of one another represent hydrogen, fluorine, methyl, ethyl, n-propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl, or where C(R 21 , R 22 ) represents spiro-C(CH2-
  • L 3 represents C(R 31 , R 32 ) where R 31 and R 32 each independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy, propargyloxy, cyclopropylmethyl, cyclopropyl, or where C(R 31 , R 32 ) represents spiro-C(CH2-CH2); k represents 1 and
  • M 1 and M 2 each independently of one another represent hydrogen, fluorine, bromine, chlorine, iodine, cyano, methyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy or phenoxy; and salts, N-oxides and tautomeric forms of the compounds of the formula (I).
  • Q represents 2-thienyl, 3-fluoro-2-thienyl, 3-chloro-2-thienyl, 3,4-dichloro-2-thienyl, 2,5-dichloro-3- thienyl, 3,4,5-trichloro-2-thienyl, 3-bromo-2-thienyl, 3-iodo-2-thienyl, 3-cyano-2-thienyl, 3- methyl-2-thienyl, 3-(trifluoromethyl)-2-thienyl, 3-methoxy-2-thienyl, 3-ethoxy-2-thienyl, 3- thienyl, 2-fluoro-3-thienyl, 2-chloro-3-thienyl, 2-bromo-3-thienyl, 2-iodo-3-thienyl, 2-cyano-3- thienyl, 2-methyl-3-thienyl, 2-(trifluoromethyl)-3-thienyl, 2-methoxy-3-thienyl, 2-eth
  • Y represents hydrogen
  • W represents oxygen
  • L 2 represents C(R 21 , R 22 ), where R 21 and R 22 each independently of one another represent hydrogen, methyl, cyclopropyl
  • L 3 represents C(R 31 , R 32 ), where R 31 and R 32 each independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, or where C(R 31 , R 32 ) represents 1 , 1 -cyclopropyl
  • k represents 1 and
  • M 1 and M 2 each independently of one another represent hydrogen, fluorine, bromine, chlorine, cyano, trifluoromethyl, difluoromethyl or nitro; and salts, N-oxides and tautomeric forms of the compounds of the formula (I).
  • n for each Q is in each case as defined below:
  • Y represents hydrogen or represents optionally mono- or poly-M -substituted (Ci-C6)-alkyl, (d-Ce)- alkenyl, (C 2 -C 6 )-alkynyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkynyl, (Ci-C 6 )- alkoxy, (C2-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C3-Cio)-cycloalkyl-(Ci-C6)-alkyl or represents an optionally mono- or poly-M 2 -substituted 3- to 10-membered cyclic group;
  • W represents oxygen
  • M 1 , M 2 and M 3 each independently of one another preferably represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (Ci-C 6 )-alkoxy, (Ci-C 6 )-haloalkoxy, (Ci-C 6 )-alkylthio, (Ci- C6)-haloalkylthio, (Ci-C6)-alkylsulphonyl, (Ci-C6)-haloalkylsulphonyl, (Ci-C6)-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-Ci4)-cycloalkyl-0-, (C3-Ci4)-cycloalkenyl-0-, (C6-Ci4)-aryl-0-, halogenated (C3-Ci4)-cycloalkyl-0-, halogen
  • M 4 represents hydrogen, halogen, cyano, nitro, OH, (Ci-C6)-alkyl, (Ci-C6)-haloalkyl, (Ci-C6)-alkoxy, (Ci-C 6 )-haloalkoxy, (Ci-C 6 )-alkylthio, (Ci-C 6 )-haloalkylthio, (Ci-C 6 )-alkylsulphonyl, (Ci-C 6 )- haloalkylsulphonyl, (Ci-C6)-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-Ci4)-cycloalkyl-0-, (C3-Ci4)-cycloalkenyl-0-, (C6-Ci4)-aryl-0-, halogenated (C3-Ci4)-cycloalkyl-0-, halogenated (C3- Ci4)-cycloalkeny
  • M 5 in each case independently of the others represents halogen, formyl, cyano, nitro, (Ci-C6)-alkyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C6)-haloalkoxy, (C 2 -C4)-alkenyloxy, (C 2 -C6)-haloalkenyloxy, (C3-C6)- alkynyloxy, (C3-C6)-haloalkynyloxy, (Ci-C6)-alkylthio, (Ci-C6)-haloalkylthio, (C 2 -C6)-alkenylthio, (C 2 -C6)-halo
  • R 21 , R 22 each independently of one another represent hydrogen, fluorine or optionally mono- or poly- M 2 -substituted (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )- haloalkenyl, (C 2 -C6)-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C6)-haloalkoxy, (C 2 -C6)-alkenyloxy, (C3- Ce)-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl or represent an optionally mono- or poly-M 2 - substituted (C3-Ci4)-carbocyclic group; or
  • R 21 , R 22 represents C(R 21 , R 22 ) as spiro-C(CH 2 -CH 2 );
  • R 31 , R 32 each independently of one another represent hydrogen, fluorine or optionally mono- or poly- M 2 -substituted (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )- haloalkenyl, (C 2 -C6)-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C6)-haloalkoxy, (C 2 -C6)-alkenyloxy, (C3- Ce)-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl or represent an optionally mono- or poly-M 2 - substituted (
  • M 5 in each case independently of the others represents halogen, formyl, cyano, nitro, (Ci-C6)-alkyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C6)-haloalkoxy, (C2-C4)-alkenyloxy, (C2-C6)-haloalkenyloxy, (C3-C6)- alkynyloxy, (C3-C6)-haloalkynyloxy, (Ci-C6)-alkylthio, (Ci-C6)-haloalkylthio, (C2-C6)-alkenylthio, (C2-C6)-haloalkenylthio, (
  • n for each Q is in each case as defined below:
  • Y represents hydrogen or represents optionally mono- or poly-M -substituted (Ci-C i)-alkyl, (C2-C4)- alkenyl, (C 3 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C 2 -C 4 )-haloalkenyl, (C 3 -C 4 )-haloalkynyl, (C 1 -C4)- alkoxy, (C2-C 4 )-alkenyloxy, (C3-C 4 )-alkynyloxy, (C3-C6)-cycloalkyl-(Ci-C 4 )-alkyl or represents an optionally mono- or poly-M 2 -substituted C3- to C6-membered carbocyclic group;
  • M 1 , M 2 and M 3 represent hydrogen, halogen, cyano, nitro, OH, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (Ci- C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )-haloalkylthio, (Ci-C 4 )-alkylsulphonyl, (Ci-C 4 )-haloalkylsulphonyl, (Ci-C 4 )-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-C14)- cycloalkyl-O-, (C3-Ci 4 )-cycloalkenyl-0-, (C6-Ci 4 )-aryl-0-, halogenated (C3-Ci 4 )-cyclo
  • M 4 represents hydrogen, halogen, cyano, nitro, OH, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )-haloalkylthio, (Ci-C 4 )-alkylsulphonyl, (C1-C4)- haloalkylsulphonyl, (Ci-C 4 )-alkylsulphanyl, (Ci-C6)-haloalkylsulphanyl, (C3-Ci 4 )-cycloalkyl-0-, (C3-Ci 4 )-cycloalkenyl-0-, (C6-Ci 4 )-aryl-0-, halogenated (C3-Ci 4 )-cycloalkyl-0-, hal
  • R 21 , R 22 each independently of one another represent hydrogen, fluorine or optionally mono- or poly- M 2 -substituted (Ci-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C 2 -C 4 )- haloalkenyl, (C2-C4)-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C4)-haloalkoxy, (C2-C4)-alkenyloxy, (C3- C4)-alkynyloxy, (C3-C4)-cycloalkyl-(Ci-C4)-alkyl, (C3-Cg)-cycloalkyl or halogenated (C3-C8)- cycloalkyl;
  • R 31 , R 32 preferably each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (Ci-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (Ci-C 4 )-haloalkyl, (C2-C4)- haloalkenyl, (C2-C4)-haloalkynyl, (Ci-C6)-alkoxy, (Ci-C4)-haloalkoxy, (C2-C4)-alkenyloxy, (C3- C4)-alkynyloxy, (C3-C4)-cycloalkyl-(Ci-C4)-alkyl or represent an optionally mono- or poly-M 2 - substituted (C3-C8)-cycloalkyl or halogenated (C3-C8)-cycloalkyl;
  • M 5 represents in each case independently of the others halogen, formyl, cyano, nitro, (Ci-C4)-alkyl, (Ci-C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl,
  • the compounds of the formula (I) can be obtained by the processes described in PCT/EP2013/073424.
  • the production processes for obtaining the compounds according to formula (I) is outlined below reparation Process A
  • the radicals M 1 , M 2 , L 2 , L 3 , Q and Y and k have the meanings described above. W in this case represents oxygen.
  • Compounds of the general formula (I-a) according to the invention can be prepared proceeding from amines of the formula (al) and carboxylic acids of the formula (a2) or halides thereof of the formula (a3) by generally known processes as described, for example, in WO-A 2009/012998.
  • the amines of the formula (al) and carboxylic acids of the formula (a2) and their halides of the formula (a3) are commercially available.
  • the halides of the formula (a3) can be prepared by generally known methods from carboxylic acids of the formula (a2) using appropriate halogenating agents, for example phosphoryl chloride, phosphoryl bromide, thionyl chloride, oxalyl chloride or phosgene.
  • reaction auxiliaries are all customary inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogencarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogencarbonate or ammonium carbonate, and also tertiary amines, such as, for example, trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline
  • the compounds of the general formula (I-a) according to the invention are prepared in the presence of a condensing agent.
  • the carboxylic acids are commercially available.
  • Suitable condensing agents are especially dehydrating chemicals.
  • DCC ⁇ , ⁇ '-dicyclohexylcarbodiimide
  • EDC-HC1 1- ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
  • the compounds of the general formula (I-a) according to the invention are optionally prepared using one or more diluents.
  • Suitable diluents are especially inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran, dioxane, acetonitrile or dimethylformamide.
  • reaction temperatures can be varied within a relatively wide range.
  • the process is carried out at temperatures between 0°C and 150°C, preferably between 10°C and 120°C.
  • Process A is generally carried out under atmospheric pressure. However, it is also possible to carry out process A under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the radicals M 1 , M 2 , L 2 , L 3 and Q and k have the meanings described above. W in this case represents oxygen.
  • Compounds of the general formula (I-a) according to the invention can be prepared from amines of the formula (bl) and carboxylic acids of the formula (a2) or halides thereof of the formula (a3) by generally known processes as described, for example, in WO-A 2009/012998.
  • the amines of the formula (bl) and carboxylic acids of the formula (a2) and their halides of the formula (a3) are commercially available.
  • the halides of the formula (a3) can be prepared by generally known methods from carboxylic acids of the formula (a2) using appropriate halogenating agents, for example phosphoryl chloride, phosphoryl bromide, thionyl chloride, oxalyl chloride or phosgene.
  • W represents oxygen and AG represents a leaving group, for example halogens or alkyl- or arylsulphonates such as, for example, tolylsulphonates or benzenesulphonates.
  • Compounds of the general formula (I) according to the invention and their embodiment (I-c) can be prepared from compounds of the formula (I-a) and appropriate sulphurizing agents, for example tetraphosphorus decasulphide ("phosphorus pentasulphide”) or 2,4-bis[4-methoxyphenyl]-2,4-dithiono- 1,2,3,4-dithiadiphosphetane ("Lawesson's reagent”), by generally known processes. Process examples are known inter alia from Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], E5, 1255 (Thieme Verlag, Stuttgart, 1985).
  • Formulations The present invention further relates to formulations and use forms prepared therefrom as compositions controlling unwanted microorganisms, for example drench, drip and spray liquors, comprising at least one compound of the formula (I).
  • the use forms comprise further fungicides and/or adjuvants which improve action, such as penetrants, e.g.
  • vegetable oils for example rapeseed oil, sunflower oil, mineral oils, for example paraffin oils, alkyl esters of vegetable fatty acids, for example rapeseed oil methyl ester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders, for example alkylsiloxanes and/or salts, for example organic or inorganic ammonium or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate and/or retention promoters, for example dioctyl sulphosuccinate or hydroxypropyl guar polymers and/or humectants, for example glycerol and/or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.
  • alkylsiloxanes and/or salts for example organic or inorganic ammonium or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate and/or retention promoter
  • Customary formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and further possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576.
  • auxiliaries for example extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and/or further auxiliaries, for example adjuvants.
  • An adjuvant in this context is a component which enhances the biological effect of the formulation, without the component itself having any biological effect.
  • Examples of adjuvants are agents which promote retention, spreading, attachment to the leaf surface or penetration.
  • formulations are prepared in a known way, for example by mixing the compounds of the formula (I) with auxiliaries such as, for example, extenders, solvents and/or solid carriers and/or other auxiliaries such as, for example, surfactants.
  • auxiliaries such as, for example, extenders, solvents and/or solid carriers and/or other auxiliaries such as, for example, surfactants.
  • the formulations are prepared either in suitable facilities or else before or during application.
  • auxiliaries used may be substances suitable for imparting special properties, such as certain physical, technical and/or biological properties, to the formulation of the compounds of the formula (I), or to the use forms prepared from these formulations (for example ready-to-use fungicides such as spray liquors or seed dressing products).
  • Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N- alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • the alcohols and polyols
  • suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and also water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons
  • suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulphoxide, and also water.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride
  • Useful carriers include especially: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers can likewise be used.
  • Useful carriers for granules include: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stalks.
  • Liquefied gaseous extenders or solvents can also be used.
  • Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellant gases, such as halohydrocarbons, and also butane, propane, nitrogen and carbon dioxide.
  • emulsifiers and/or foam- formers, dispersants or wetting agents with ionic or nonionic properties, or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lig
  • a surfactant is advantageous if one of the compounds of the formula (I) and/or one of the inert carriers is insoluble in water and when the application takes place in water.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc as further auxiliaries in the formulations and the use forms derived therefrom.
  • Additional components may be stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability. Foam formers or antifoams may also be present.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids may also be present as additional auxiliaries in the formulations and the use forms derived therefrom. Further possible auxiliaries are mineral and vegetable oils.
  • auxiliaries may be present in the formulations and the use forms derived therefrom.
  • additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreaders.
  • the compounds of the formula (I) can be combined with any solid or liquid additive commonly used for formulation purposes.
  • Useful retention promoters include all those substances which reduce the dynamic surface tension, for example dioctyl sulphosuccinate, or increase the viscoelasticity, for example hydroxypropylguar polymers.
  • Suitable penetrants in the present context are all those substances which are usually used for improving the penetration of agrochemical active compounds into plants. Penetrants are defined in this context by their ability to penetrate from the (generally aqueous) application liquor and/or from the spray coating into the cuticle of the plant and thereby increase the mobility of active compounds in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, for example rapeseed oil methyl ester or soya oil methyl ester, fatty amine alkoxylates, for example tallowamine ethoxylate (15), or ammonium and/or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate.
  • alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12)
  • fatty acid esters for example rapeseed oil methyl ester or soya oil methyl ester
  • fatty amine alkoxylates for example tallowamine ethoxylate (15)
  • ammonium and/or phosphonium salts for example ammonium sulphate or diammonium hydrogenphosphate.
  • the formulations preferably comprise between 0.00000001 and 98% by weight of the compound of the formula (I) or, with particular preference, between 0.01% and 95% by weight of the compound of the formula (I), more preferably between 0.5% and 90% by weight of the compound of the formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the use forms prepared from the formulations (in particular fungicides) may vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms is usually between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the use form.
  • the compounds are employed in a customary manner appropriate for the use forms. Plant/Crop Protection
  • the compounds according to the invention have potent microbicidal activity and can be used for control of harmful microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • the invention also relates to a method for controlling harmful microorganisms, characterized in that the compounds according to the invention are applied to the harmful microorganims and/or their habitat.
  • the compounds according to the invention can be used in crop protection for control of phytopathogenic fungi. They are characterized by an outstanding efficacy against a broad spectrum of phytopathogenic fungi, including soilborne pathogens, which are in particular members of the classes Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti). Some fungicides are systemically active and ca be used in plant protection as foliar, seed dressing or soil fungicide. Furthermore, they are suitable for controlling fungi, which inter alia infest wood or roots of plant.
  • the compounds according to the invention can be used in crop protection for control of phytopathogenic bacteria. They are characterized by an outstanding efficacy against a broad spectrum of phytopathogenic bacteria, including Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, for example Puccinia recondite, P.
  • diseases caused by powdery mildew pathogens for example Blumeria species, for example Blumeria graminis
  • Uromyces species for example Uromyces appendiculatus
  • diseases caused by pathogens from the group of the Oomycetes for example Albugo species, for example Algubo Candida
  • Bremia species for example Bremia lactucae
  • Peronospora species for example Peronospora pisi or P.
  • Urocystis species for example Urocystis occulta
  • Ustilago species for example Ustilago nuda, U. nuda tritici
  • Botrytis species for example Botrytis cinerea
  • Penicillium species for example Penicillium expansum and P.
  • Sclerotinia species for example Sclerotinia sclerotiorum
  • Verticilium species for example Verticilium alboatrum
  • seed and soilborne decay, mould, wilt, rot and damping-off diseases caused, for example, by Alternaria species, caused for example by Alternaria brassicicola
  • Aphanomyces species caused for example by Aphanomyces euteiches
  • Ascochyta species caused for example by Ascochyta lentis
  • Aspergillus species caused for example by Aspergillus flavus
  • Cladosporium species caused for example by Cladosporium herbarum
  • Cochliobolus species caused for example by Cochliobolus sativus
  • Taphrina species for example Taphrina deformans
  • decline diseases of wooden plants caused, for example, by Esca disease caused for example by Phaemoniella clamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea
  • Eutypa dyeback caused for example by Eutypa lata
  • Ganoderma diseases caused for example by Ganoderma boninense
  • Rigidoporus diseases caused for example by Rigidoporus lignosus
  • diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea
  • diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani
  • Helminthosporium species for example Helminthosporium solani
  • Helminthosporium species for example Helminthosporium solani
  • Plasmodiophora species for example Plamodiophora brassicae
  • diseases caused by bacterial pathogens for example Xanthomonas species, for example Xanthomonas cam-pestris pv. oryzae
  • Pseudomonas species for example Pseudomonas syringae pv. lachrymans
  • Erwinia species for example Erwinia amylovora.
  • the following diseases of soya beans can be controlled with preference:
  • compositions comprising these compounds are suitable for controlling the following plant diseases:
  • Albugo spp. (white rust) on ornamental plants, vegetable crops (e.g. A. Candida) and sunflowers (e.g. A. tragopogonis); Alternaria spp. (black spot disease, black blotch) on vegetables, oilseed rape (e.g. A. brassicola or A. brassicae), sugar beet (e.g. A. tenuis), fruit, rice, soybeans and also on potatoes (e.g. A. solani or A. alternata) and tomatoes (e.g. A. solani or A. alternata) and Alternaria spp. (black head) on wheat; Aphanomyces spp. on sugar beet and vegetables; Ascochyta spp.
  • Alternaria spp. black spot disease, black blotch
  • oilseed rape e.g. A. brassicola or A. brassicae
  • sugar beet e.g. A. tenuis
  • fruit e.g. A.
  • Botrytis cinerea teleomorph: Botryotinia fuckeliana: gray mold, gray rot
  • soft fruit and pomaceous fruit inter alia strawberries
  • vegetables inter alia lettuce, carrots, celeriac and cabbage
  • oilseed rape flowers, grapevines, forest crops and wheat (ear mold)
  • Bremia lactucae downy mildew
  • Ceratocystis syn. Ophiostoma
  • spp. blue stain fungus
  • Cercospora spp. (Cereospora leat spot) on corn (e.g. C. zeae-maydis), rice, sugar beet (e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. C. sojina or C. kikuchil) and rice; Cladosporium spp. on tomato (e.g. C. fulvum: tomato leaf mold) and cereals, e.g. C.
  • herbarum ear rot
  • Claviceps purpurea ergot
  • Cochliobolus anamorph: Helminthosporium or Bipolaris
  • spp. leaf spot
  • corn e.g. C. carbonum
  • cereals e.g. C. sativus, anamorph: B. sorokiniana: glume blotch
  • rice tor example C. miyabeanus, anamorph: H. oryzae
  • graminicola stem rot and anthracnosis
  • soft fruit e.g. C. coccodes: wilt disease
  • beans e.g. C. lindemuthianum
  • soybeans e.g. C. truncatum
  • Corticium spp. e.g. C. sasakii (sheath blight) on rice
  • Corynespora cassiicola leaf spot
  • Cycloconium spp. e.g. C. oleaginum on olives
  • Cylindrocarpon spp. e.g.
  • fruit tree cancer or black foot disease of grapevine teleomorph: Nectria or Neonectria spp.) on fruit trees, grapevines (e.g. C. liriodendn; teleomorph: Neonectria liriodendri, black foot disease) and many ornamental trees; Dematophora (teleomorph: Rosellinia) necatrix (root/stem rot) on soybeans; Diaporthe spp. e.g. D. phaseolorum (stem disease) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. D.
  • Drechslera teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on grapevines; Macrophomina phaseolina (syn. phaseoli) (root/stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e.g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e.g. M.
  • Phakopsora pachyrhizi and P. meibomiae on soybeans
  • Phialophora spp. e.g. on grapevines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g. P. gregata: stem disease); Phoma lingam (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spot) on sugar beet
  • phaseoli, teleomorph Diaporthe phaseolorum
  • Physoderma maydis brown spot
  • Phytophthora spp. wilt disease, root, leaf, stem and fruit rot
  • various plants such as on bell peppers and cucumber species (e.g. P. capsici), soybeans (e.g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e.g. P. infestans. late blight and brown rot) and deciduous trees (e.g. P. ramorum sudden oak death); Plasmodiophora brassicae (club-root) on cabbage, oilseed rape, radish and other plants; Plasmopara spp., e.g.
  • P. viticola peronospora of grapevines, downy mildew
  • grapevines and P. halstedii on sunflowers
  • Podosphaera spp. pronospora of grapevines, downy mildew
  • Podosphaera spp. prowdery mildew
  • Rosaceae hops, pomaceaus fruit and soft fruit, e.g. P. leucotricha on apple
  • Polymyxa spp. e.g. on cereals, such as barley and wheat (P. graminis) and sugar beet (P. betae) and the viral diseases transmitted thereby
  • Pseudocercosporella herpotrichoides eyespot/stem break, teleomorph: Tapesia yallundae
  • wheat or barley Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis on cucumber species or P. humili on hops; Pseudopezicula tracheiphila (angular leaf scorch, anamorph Phialophora) on grapevines; Puccinia spp. (rust disease) on various plants, e.g. P. triticina (brown rust of wheat), P. striiformis (yellow rust). P. hordei (dwarf leaf rust), P. graminis (black rust) or P.
  • P. triticina brown rust of wheat
  • P. striiformis yellow rust
  • P. hordei dwarf leaf rust
  • P. graminis black rust
  • recondita brown rust of rye
  • cereals such as e.g. wheat, barley or rye.
  • P. kuehnii on sugar cane and, e.g., on asparagus (e.g. P. asparagi); Pyrenophora (anamorph: Drechslera) tritici-repentis (speckled leaf blotch) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea. rice blast) on rice and P. grisea on lawn and cereals; Pythium spp.
  • Drechslera tritici-repentis
  • P. teres net blotch
  • Pyricularia spp. e.g. P. oryzae (teleomorph: Magnaporthe grisea. rice blast) on rice and P. grisea on lawn and
  • cerealis (sharp eyespot) on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevines and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem or white rot) on vegetable and field crops, such as oilseed rape, sunflowers (e.g. Sclerotinia sclerotiorum) and soybeans (e.g. S. rolfsii),* Septoria spp. on various plants, e.g. S.
  • glycines leaf spot
  • S. tritici Septoria leaf blotch
  • S. (syn. Stagonospora) nodorum leaf blotch and glume blotch
  • Uncinula Syn. Erysiphe
  • necator prowdery mildew, anamorph: Oidium tuckeri
  • Setospaeria spp. (leaf spot) on corn (e.g. S. turcicum, syn. Helminthosporium turcicum) and lawn
  • Sphacelotheca spp. head smut
  • Thielaviopsis spp. black root rot
  • tobacco, pome fruit, vegetable crops, soybeans and cotton e.g. T. basicola (syn. Chalara elegans)
  • Tilletia spp. bunt or stinking smut
  • cereals such as e.g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat
  • Typhula incarnata (gray snow mold) on barley or wheat
  • Urocystis spp. e.g. U.
  • occulta flag smut
  • Uromyces spp. rust
  • vegetable plants such as beans (e.g. U. appendiculatus, syn. U. phaseoll) and sugar beet (e.g. U. betae);
  • Ustilago spp. loose smut) on cereals (e.g. U. nuda and U. avaenae), corn (e.g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears and Verticillium spp.
  • the compounds according to the invention can be used for curative or protective/preventive control of harmful microorganisms.
  • the invention therefore also relates to curative and protective methods for controlling harmful microorganisms by the use of the compounds according to the invention , which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.
  • the fact that the compounds according to the invention are well tolerated by plants at the concentrations required for controlling harmful microorganisms allows the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • plants are to be understood to mean all plants and plant parts such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), maize, soya bean, potato, sugar beet, sugar cane, tomatoes, peas and other vegetable species, cotton, tobacco, oilseed rape, and also fruit plants (with the fruits apples, pears, citrus fruits and grapevines).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by varietal property rights.
  • Plant parts should be understood to mean all parts and organs of the plants above and below ground, such as shoot, leaf, flower and root, examples given being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also tubers, roots and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
  • Treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by allowing the compounds to act on the surroundings, environment or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
  • plants and their parts are treated.
  • wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above.
  • the invention is used with particular preference to treat plants of the respective commercially customary cultivars or those that are in use.
  • Plant cultivars are to be understood as meaning plants having new properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • the compounds to be used in accordance with the invention can preferably be employed in the following plants, the enumeration which follows not being limiting.
  • Preferred plants are those from the group of the useful plants, ornamentals, turfs, generally used trees which are employed as ornamentals in the public and domestic sectors, and forestry trees.
  • Forestry trees comprise trees for the production of timber, cellulose, paper and products made from parts of the trees.
  • useful plants refers to crop plants which are employed as plants for obtaining foodstuffs, feedstuffs, fuels or for industrial purposes.
  • the useful plants include, for example, the following types of plants: turf, vines, cereals, for example wheat, barley, rye, oats, triticale, rice, maize and millet/sorghum; beet, for example sugar beet and fodder beet; fruits, for example pome fruit, stone fruit and soft fruit, for example apples, pears, plums, peaches, almonds, cherries and berries, for example strawberries, raspberries, blackberries; legumes, for example beans, lentils, peas and soya beans; oil crops, for example oilseed rape, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cacao beans and peanuts; cucurbits, for example pumpkin/squash, cucumbers and melons; fibre plants, for example cotton, flax, hemp and jute; citrus fruit, for example
  • Particularly suitable target crops are the plants below: cotton, aubergine, turf, pome fruit, stone fruit, soft fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soya beans, oilseed rape, tomato, bell pepper, melons, cabbage, potatoes and apples.
  • trees examples include: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.
  • Preferred trees which may be mentioned are: from the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus.
  • Particularly preferred trees which may be mentioned are: from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis.
  • Very particularly preferred trees which may be mentioned are: horse chestnut, Platanaceae, linden tree, maple tree.
  • the present invention can also be applied to any turfgrasses, including cool-season turfgrasses and warm-season turfgrasses.
  • cool-season turfgrasses are bluegrasses ⁇ Poa spp.), such as Kentucky bluegrass ⁇ Poa pratensis L.), rough bluegrass ⁇ Poa trivialis L.), Canada bluegrass ⁇ Poa compressa L.), annual bluegrass ⁇ Poa annua L.), upland bluegrass ⁇ Poa glaucantha Gaudin), wood bluegrass ⁇ Poa nemoralis L.) and bulbous bluegrass ⁇ Poa bulbosa L.); bentgrasses ⁇ Agrostis spp.) such as creeping bentgrass ⁇ Agrostis palustris Huds.), colonial bentgrass ⁇ Agrostis tenuis Sibth.), velvet bentgrass ⁇ Agrostis canina L.), South German Mixed Bentgrass ⁇ Agrostis spp.
  • Agrostis tenius Sibth. including Agrostis tenius Sibth., Agrostis canina L., and Agrostis palustris Huds.), and redtop ⁇ Agrostis alba L.); fescues ⁇ Festuca spp.), such as red fescue ⁇ Festuca rubra L. spp.
  • ryegrasses ⁇ Lolium spp. such as annual ryegrass ⁇ Lolium multiflorum Lam.), perennial ryegrass ⁇ Lolium perenne L.) and Italian ryegrass ⁇ Lolium multiflorum Lam.
  • wheatgrasses ⁇ Agropyron spp. such as fairway wheatgrass ⁇ Agropyron cristatum (L.) Gaertn.), crested wheatgrass ⁇ A
  • Examples of further cool-season turfgrasses are beachgrass ⁇ Ammophila breviligulata Fern.), smooth bromegrass ⁇ Bromus inermis Leyss.), cattails such as Timothy ⁇ Phleum pratense L.), sand cattail ⁇ Phleum subulatum L.), orchard grass ⁇ Dactylis glomerata L.), weeping alkaligrass ⁇ Puccinellia distans (L.) Pari.) and crested dog's-tail ⁇ Cynosurus cristatus L.).
  • Examples of warm-season turfgrasses are Bermuda grass ⁇ Cynodon spp. L. C. Rich), zoysia grass ⁇ Zoysia spp. Willd.), St. Augustine grass ⁇ Stenotaphrum secundatum Walt Kuntze), centipede grass ⁇ Eremochloa ophiuroides Munrohack.), carpet grass ⁇ Axonopus aflinis Chase), Bahia grass ⁇ Paspalum notatum Flugge), Kikuyu grass ⁇ Pennisetum dandestinum Hochst.
  • Cool-season turfgrasses are generally preferred for the use in accordance with the invention. Particular preference is given to bluegrass, bentgrass and redtop, fescues and ryegrasses. Bentgrass is especially preferred.
  • Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or a combination of transformation events, and that are listed for example in the databases for various national or regional regulatory agencies including Event 531/ PV- GHBK04 (cotton, insect control, described in WO 2002/040677), Event 1143-14A (cotton, insect control, not deposited, described in WO 06/128569); Event 1143-51B (cotton, insect control, not deposited, described in WO 06/128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO 02/034946Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO 10/117737); Event 17314 (rice, herbicide tolerance, deposited as PTA- 9844, described in WO 10/117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO 05/103266 or US-A 2005
  • Event BLR1 (oilseed rape, restoration of male sterility, deposited as NCIMB 41193, described in WO 2005/074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO 06/128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A 2010- 0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO 06/128571); Event CE46-02A (cotton, insect control, not deposited, described in WO 06/128572); Event COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO 04/039986); Event COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO 05/054479); Event COT203 (cotton, insect control, not deposited,
  • the treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by action on their surroundings, habitat or storage space using customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, injecting, watering (drenching), drip irrigating and, in the case of propagation material, in particular in the case of seed, furthermore as a powder for dry seed treatment, a solution for liquid seed treatment, a water-soluble powder for slurry treatment, by incrusting, by coating with one or more coats, etc. It is furthermore possible to apply the compounds of the formula (I) by the ultra-low volume method or to inject the application form or the compound of the formula (I) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, i.e. the compounds of the formula (I) are applied to the foliage, where treatment frequency and the application rate should be adjusted according to the level of infestation with the harmful microorganism in question.
  • the compounds of the formula (I) also access the plants via the root system.
  • the plants are then treated by the action of the compounds of the formula (I) on the habitat of the plant.
  • This may be done, for example, by drenching, or by mixing into the soil or the nutrient solution, i.e. the locus of the plant (e.g. soil or hydroponic systems) is impregnated with a liquid form of the compounds of the formula (I), or by soil application, i.e. the compounds of the formula (I) according to the invention are introduced in solid form (e.g. in the form of granules) into the locus of the plants.
  • this can also be done by metering the compound of the formula (I) in a solid application form (for example as granules) into a flooded paddy field.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the application rate of the compounds according to the invention is
  • leaves from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 10 to 800 g/ha, even more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used);
  • ⁇ in the case of seed treatment from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed;
  • the compounds according to the invention can thus be used to protect plants from attack by the pathogens mentioned for a certain period of time after treatment.
  • the period for which protection is provided extends generally for 1 to 28 days, preferably for 1 to 14 days, more preferably for 1 to 10 days, most preferably for 1 to 7 days, after the treatment of the plants with the active ingredients, or for up to 200 days after a seed treatment.
  • the inventive treatment can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom.
  • Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2 -toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec, such as F.
  • verticillioides etc. and also by Aspergillus spec, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec, such as C. purpurea, C. fusiformis, C. paspali,
  • the compounds according to the invention can also be used in the protection of materials, for protection of industrial materials against attack and destruction by unwanted microorganisms, for example fungi, and insects.
  • inventive compounds can be used as antifouling compositions, alone or in combinations with other active ingredients.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • industrial materials which are to be protected by compoundsaccording to the invention from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms.
  • Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
  • the compoundsaccording to the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • the compounds/compositions according to the invention may also be used against fungal diseases liable to grow on or inside timber.
  • the term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high density wood, laminated wood, and plywood.
  • the method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention or a compoundsaccording to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.
  • inventive compounds can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
  • inventive method for controlling unwanted microorganisms can also be employed for protecting storage goods.
  • Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
  • Storage goods of vegetable origin for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting.
  • Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture.
  • Storage goods of animal origin are, for example, hides, leather, furs and hairs.
  • the compositions according to the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compoundsaccording to the invention preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae.
  • Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporas, such as Polyporas versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichuras spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp.
  • the 3 ⁇ 4 NMR data were determined with a Bruker Avance 400 equipped with a flow probe head (volume 60 ⁇ ), with tetramethylsilane as a reference (0.0) and the solvents CD3CN, CDCI3 or D6-DMSO.
  • NMR data for selected examples are listed either in conventional form ( ⁇ values, multiplet splitting, number of hydrogen atoms) or as NMR peak lists. NMR peak list method
  • the 3 ⁇ 4 NMR data of selected examples are stated in the form of 3 ⁇ 4 NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ value - signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.
  • the peak list for one example therefore takes the form of: ⁇ (intensityi); 82 (intensity2); ; ⁇ ; (intensity); ; ⁇ ⁇ (intensity ⁇
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and their relative intensities may be shown in comparison to the most intense signal in the spectrum.
  • the tetramethylsilane peak may but need not occur in the NMR peak lists.
  • stereoisomers of the target compounds which likewise form part of the subject matter of the invention, and/or peaks of impurities.
  • the peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of > 90%).
  • Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help to identify reproduction of our preparation process with reference to "by-product fingerprints”.
  • An expert calculating the peaks of the target compounds by known methods can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 3 ⁇ 4 NMR interpretation.
  • Example 1 In vivo preventive test on Alternaria brassicae (leaf spot on radish)
  • the tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/Tween ® 80, and then diluted with water to obtain the desired active material concentration.
  • the young plants of radish are treated by spraying the active ingredient prepared as described above.
  • Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween ® 80.
  • the plants are contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores.
  • the contaminated radish plants are incubated for 6 days at 20°C and at 100% relative humidity.
  • the test is evaluated 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
  • the tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/Tween® 80, and then diluted with water to obtain the desired active material concentration.
  • the young plants of radish are treated by spraying the active ingredient prepared as described above.
  • Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween® 80.
  • the plants are contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores.
  • the contaminated gherkin plants are incubated for 4 to 5 days at 17°C and at 90%) relative humidity.
  • the tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/Tween® 80, and then diluted with water to obtain the desired active material concentration.
  • the young plants of radish are treated by spraying the active ingredient prepared as described above.
  • Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween® 80.
  • the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores.
  • the contaminated wheat plants are incubated for 24 hours at 20°C and at 100% relative humidity and then for 10 days at 20°C and at 70-80% relative humidity.
  • the tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/Tween® 80, and then diluted with water to obtain the desired active material concentration.
  • the young plants of radish are treated by spraying the active ingredient prepared as described above.
  • Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween® 80.
  • the plants are contaminated by spraying the leaves with an aqueous suspension of Pyrenophora teres spores.
  • the contaminated barley plants are incubated for 48 hours at 20°C and at 100%) relative humidity and then for 12 days at 20°C and at 70-80%) relative humidity.
  • Example5 In vivo preventive test on Pyricularia oryzae (rice blast)
  • the tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/Tween® 80, and then diluted with water to obtain the desired active material concentration.
  • the young plants of radish are treated by spraying the active ingredient prepared as described above.
  • Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween® 80.
  • the plants are contaminated by spraying the leaves with an aqueous suspension of Pyricularia oryzae spores.
  • the contaminated rice plants are incubated at 25°C and at 80% relative humidity.
  • Example 6 In vivo preventive test on Septoria tritici (leaf spot on wheat)
  • the tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/Tween® 80, and then diluted with water to obtain the desired active material concentration.
  • the young plants of radish are treated by spraying the active ingredient prepared as described above.
  • Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween® 80.
  • the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores.
  • the contaminated wheat plants are incubated for 72 hours at 18°C and at 100%) relative humidity and then for 21 days at 20°C and at 90%> relative humidity.
  • Example 7 in vivo preventive test on Sphaerotheca fuliginea (powdery mildew on cucurbits)
  • the tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/Tween® 80, and then diluted with water to obtain the desired active material concentration.
  • the young plants of radish are treated by spraying the active ingredient prepared as described above.
  • Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween® 80.
  • the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores.
  • the contaminated gherkin plants are incubated for 72 hours at 18°C and at 100% relative humidity and then for 12 days at 20°C and at 70-80% relative humidity.
  • the test is evaluated 15 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.
  • Example 8 Blumeria test (barley) / preventive
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are dusted with spores of Blumeria graminis f.sp. hordei. The plants are placed in the greenhouse at a temperature of approximately 18 °C and a relative atmospheric humidity of approximately 80%> to promote the development of mildew pustules.
  • the test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%> means that no disease is observed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of approximately 100%.
  • the plants are placed in the greenhouse at a temperature of approximately 20 °C and a relative atmospheric humidity of approximately 80%.
  • the test is evaluated 8 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%> means that no disease is observed.
  • Example 10 Venturia test (apples) / preventive
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of 100%). The plants are then placed in a greenhouse at approximately 21 °C and a relative atmospheric humidity of approximately 90%>. The test is evaluated 10 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%> means that no disease is observed.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne l'utilisation de pyridyloxyalkylcarboxamides de formule (I) pour lutter contre des micro-organismes nuisibles chez les végétaux, une composition contenant ces composés et des procédés pour la préparation de ces compositions fongicides.
PCT/EP2015/056181 2014-03-27 2015-03-24 Utilisation de pyridyloxyalkylcarboxamides pour lutter contre des micro-organismes indésirables WO2015144657A1 (fr)

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WO2018235851A1 (fr) 2017-06-20 2018-12-27 Raqualia Pharma Inc. Dérivés d'amide utilisés en tant que bloqueurs de nav1,7 et de nav1,8
WO2019185413A1 (fr) 2018-03-27 2019-10-03 Basf Se Dérivés de cyclopropyle substitués pesticides
CN115772122A (zh) * 2022-12-02 2023-03-10 浙江工业大学 一种苯甲酰胺类化合物及其制备方法和应用

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WO2008003746A1 (fr) * 2006-07-06 2008-01-10 Bayer Cropscience Sa Nouveaux dérivés de n-(4-pyridin-2-ylbutyle) carboxamide, procédé de préparation et utilisation comme fongicides
WO2009012998A1 (fr) * 2007-07-26 2009-01-29 Syngenta Participations Ag Nouveaux microbiocides
WO2010015681A1 (fr) * 2008-08-07 2010-02-11 Bayer Cropscience Sa Dérivés de n-(2-pyridylpropyl) carboxamide fongicides et leurs analogues oxa, aza et thia
WO2011151370A1 (fr) * 2010-06-03 2011-12-08 Bayer Cropscience Ag N-[(het)arylalkyl)]pyrazole(thio)carboxamides et leurs analogues hétérosubstitués
WO2014076015A1 (fr) * 2012-11-13 2014-05-22 Bayer Cropscience Ag Pyridyloxyalkylcarboxamides et utilisation des pyridyloxyalkylcarboxamides comme agents endoparasiticides et nématicides

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WO2008003746A1 (fr) * 2006-07-06 2008-01-10 Bayer Cropscience Sa Nouveaux dérivés de n-(4-pyridin-2-ylbutyle) carboxamide, procédé de préparation et utilisation comme fongicides
WO2009012998A1 (fr) * 2007-07-26 2009-01-29 Syngenta Participations Ag Nouveaux microbiocides
WO2010015681A1 (fr) * 2008-08-07 2010-02-11 Bayer Cropscience Sa Dérivés de n-(2-pyridylpropyl) carboxamide fongicides et leurs analogues oxa, aza et thia
WO2011151370A1 (fr) * 2010-06-03 2011-12-08 Bayer Cropscience Ag N-[(het)arylalkyl)]pyrazole(thio)carboxamides et leurs analogues hétérosubstitués
WO2014076015A1 (fr) * 2012-11-13 2014-05-22 Bayer Cropscience Ag Pyridyloxyalkylcarboxamides et utilisation des pyridyloxyalkylcarboxamides comme agents endoparasiticides et nématicides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018235851A1 (fr) 2017-06-20 2018-12-27 Raqualia Pharma Inc. Dérivés d'amide utilisés en tant que bloqueurs de nav1,7 et de nav1,8
CN110612285A (zh) * 2017-06-20 2019-12-24 拉夸里亚创药株式会社 作为Nav1.7及Nav1.8阻断剂的酰胺衍生物
US11154544B2 (en) 2017-06-20 2021-10-26 Raqualia Pharma Inc. Amide derivatives as Nav1.7 and Nav1.8 blockers
CN110612285B (zh) * 2017-06-20 2023-04-04 拉夸里亚创药株式会社 作为Nav1.7及Nav1.8阻断剂的酰胺衍生物
WO2019185413A1 (fr) 2018-03-27 2019-10-03 Basf Se Dérivés de cyclopropyle substitués pesticides
CN115772122A (zh) * 2022-12-02 2023-03-10 浙江工业大学 一种苯甲酰胺类化合物及其制备方法和应用

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