EP3429997A1 - N-(cyanobenzyl)-6-(cyclopropyl-carbonylamino)-4-(phenyl)-pyridine-2-carboxamide derivatives and related compounds as pesticides and plant protection agents - Google Patents

N-(cyanobenzyl)-6-(cyclopropyl-carbonylamino)-4-(phenyl)-pyridine-2-carboxamide derivatives and related compounds as pesticides and plant protection agents

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Publication number
EP3429997A1
EP3429997A1 EP17709464.6A EP17709464A EP3429997A1 EP 3429997 A1 EP3429997 A1 EP 3429997A1 EP 17709464 A EP17709464 A EP 17709464A EP 3429997 A1 EP3429997 A1 EP 3429997A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
cycloalkyl
cyclo
methyl
spp
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP17709464.6A
Other languages
German (de)
French (fr)
Inventor
David WILCKE
Roland Andree
Arnd Voerste
Silvia Cerezo-Galvez
Graham Holmwood
Kerstin Ilg
Daniela Portz
Ulrich Ebbinghaus-Kintscher
Ulrich Görgens
Cathleen BRADLER
Andreas Turberg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3429997A1 publication Critical patent/EP3429997A1/en
Withdrawn legal-status Critical Current

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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels

Definitions

  • the present invention relates to novel substituted pyridine compounds of the formula (I), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular insects and arachnids, and methods and intermediates for their preparation.
  • WO 2012/054510 A1 describes oxadiazole-substituted pyridines as inhibitors of beta-secretase activity in the 4-position, which can be used in particular for the treatment of Alzheimer's diseases.
  • WO 2012/069366 A1 discloses, inter alia, in Table F insecticidal and containing a pyridinyl group-containing compounds containing a fluoroalkyl-substituted pyrazole group (Q2), which is bound via the grouping -NH-CO- to the pyridinyl group.
  • the compounds according to the invention contain a substituent Q1 in position 4 on the pyridine ring, which is necessarily substituted or unsubstituted aryl, 1,3-benzodioxolyl, 2,3-dihydro-l, 4-benzodioxinyl, hetaryl or oxo-hetaryl.
  • a substituent is not present in the compounds disclosed in WO 2012/069366 Al.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity.
  • the present invention is therefore compounds of the general formula (I) in which
  • Q1 is each optionally mono- or polysubstituted by identical or different substituents aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl or oxo-hetaryl, where the substituents are selected from: cyano, carboxyl, Halogen, nitro, hydroxy, amino, SCN, SF5, tri (C 1 -C 6) alkylsilyl, (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 6) cyanoalkyl, (C 1 -C 6) hydroxyalkyl, hydroxycarbonyl - (C 1 -C 6) alkoxy, (C 1 -C 6) alkoxycarbonyl- (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy- (C 1 -C 6) alkyl, (C 1
  • Preferred (embodiment 2-1) are the compounds of the formula (I) in which Q1 is in each case optionally mono- or polysubstituted or differently substituted phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl or oxo-hetaryl, wherein the substituents are selected from cyano, halogen, nitro, amino, SF5, (C1-C4 ) Alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) cyanoalkyl, (C 1 -C 4) hydroxyalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) -alkyl, (C 2 -C 4)
  • Particularly preferred (embodiment 3-1) are the compounds of formula (I) in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1 , 4-benzodioxinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furanyl, oxazolyl, thiazolyl, imidazolyl or pyrazolyl, wherein the substituents are selected from cyano, halogen, nitro, SF 5 , (C 1 -C 4 ) Alkyl, (C 1 - C 4 ) Haloalkyl, (C 2 -C 4 ) Alkenyl, (C 2 -C 4 ) Haloalkenyl, (C 2 -C 4 ) Alkynyl, (C 2 C4) hal
  • Very particularly preferred range are the compounds of formula (I) in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents phenyl, 1,3-benzodioxolyl, 2,3-dihydro 1,4-benzodioxinyl, pyridyl, thienyl or pyrazol-1-yl or pyrazol-2-yl, wherein the substituents are selected from cyano, fluorine, chlorine, bromine, iodine, SF5, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluo
  • very particularly preferred are the compounds of formula (I) in which Q1 is in each case optionally mono-, di-, tri- or tetra, phenyl which is identical or differently substituted, 1,3-benzodioxolyl , 2,3-dihydro-1,4-benzodioxinyl, pyridyl, thienyl or pyrazol-1-yl or pyrazol-2-yl, wherein the substituents are selected from fluorine, chlorine, bromine, iodine, SF5, methyl, ethyl, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoroisopropyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,
  • very particularly preferred are the compounds of formula (I) in which Q1 for 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl, 2,2-difluoro-1,3-benzodioxol-5-yl, 2-chloro-4 (trifluoromethoxy) phenyl, 2-ethyl-6-methyl-4- (pentafluoroethyl) phenyl, 2-fluoro-4- (trifluoromethoxy) phenyl, 2-fluoro-6- (trifluoromethyl) pyridin-3-yl, 2-methyl 4- (trifluoromethoxy) phenyl, 3- (pentafluoroethyl) -1H-pyrazol-1-yl, 3- (trifluoromethoxy) phenyl, 3,5-difluoro-4- (trifluoromethoxy) phenyl, 3-
  • R5, R6 V independently of one another represent hydrogen, V1, V2 independently of one another represent oxygen or sulfur.
  • R5, R6 V independently of one another represent hydrogen, V1, V2 independently of one another represent oxygen or sulfur.
  • R5, R6 V independently of one another represent hydrogen, V1, V2 independently of one another represent oxygen or sulfur.
  • R5, R6 V independently of one another represent hydrogen, V1, V2 independently of one another represent oxygen or sulfur.
  • R5, R6 V independently of one another represent hydrogen
  • V1, V2 independently of one another represent oxygen or sulfur.
  • R5 is 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6 yl, 2,2-difluoro-1,3-benzodioxol-5-yl, 2-chloro-4- (trifluoromethoxy) phenyl, 2-ethyl-6-methyl-4- (pentafluoroethyl) phenyl, 2-fluoro-4- (trifluorome
  • R5, R6V independently of one another represent hydrogen
  • V1 is oxygen or sulfur
  • V2 stands for oxygen, sulfur or -NH. Further preferred, particularly preferred and very particularly preferred ranges: In a further preferred embodiment, the invention relates to the compounds of the general formulas (Ia)
  • R 1, R 4 and Q 1 have the meanings described above (R 5 and R 6 are hydrogen), in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2) or Embodiment (3-2) or Embodiment (4-2) or Embodiment (5-2 ) or embodiment (6-2) have described meanings.
  • the invention relates to the compounds of the general formulas (I-b)
  • R1, R2, R3, R4, V1 and V2 have the meanings described above (R5 and R6 are hydrogen), in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or Embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2) or Embodiment (3-2) or Embodiment (4-2) or (5-2) or (6-2) have the meanings described, and Q 1 is optionally mono-, di-, tri-, tetra- or tri-substituted phenyl, the substituents being selected from cyano, halogen, nitro, ( C1-C4) alkyl, (C1-C4) haloalkyl, (C2-C4) alkenyl, (C2-C4) haloalkenyl, (C2-C4) alkynyl, (C2-C4) haloalkynyl, (C1-C4) alkoxy, (C1 -C
  • R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above, in particular those in the embodiment (1-1) or the embodiment (2-1) or the embodiment (3-1) or the embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2) or Embodiment (3-2) or Embodiment (4-2) or Embodiment (5-2 ) or embodiment (6-2) have described meanings.
  • the invention relates to the compounds of formula (I) in which R3 and R4 are not together alkyl or alkenyl, so that no ring is formed, wherein R1, R2, R5, R6, Q1, V1 and V2 have the meanings described above, in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or embodiment (4-1) or configuration (5-1) or embodiment (6-1) or have the meanings described in embodiment (1-2) or design (2-2) or design (3-2) or design (4-2) or design (5-2) or design (6-2).
  • the invention relates to the compounds of the formula (I) in which R 1 is (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 3 -C 6) -cycloalkyl or (C 3 -C 6) -cycloalkyl- (Cl C 4 ) alkyl, particularly preferably (C 1 -C 4 ) alkyl or (C 3 -C 6 ) cycloalkyl, very particularly preferably (C 1
  • R 2, R 3, R 4, R 5, R 6 , Q 1, V and V 2 have the meanings described above, in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3 1) or embodiment (4-1) or design (5-1) or design (6-1) or in the embodiment (1-2) or design (2-2) or design (3-2) or design ( 4-2) or embodiment (5-2) or embodiment (6-2) have described meanings.
  • the invention relates to the compounds of the formula (I) in which R4 is methyl which is monosubstituted by phenyl, where phenyl is optionally mono-, di- or trisubstituted, identically or differently, by cyano, fluorine, chlorine, nitro, methyl, Trifluoromethyl, methoxy, methyloxycarbonyl, thiocarbamoyl, aminosulfonyl, methylpyrazolyl, oxazolyl or oxdiazolyl may be substituted, wherein R1, R2, R3, R5, R6, Q1, V1 and V2 have the meanings described above, in particular those in embodiment (1-1) or Embodiment (2-1) or Embodiment (3-1) or Embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2 ) or design (3-2) or design (4-2) or design (5-2) or design (
  • Also very particularly preferred compounds according to the invention are the compounds of the general formula (I) shown in Table 1.
  • Optionally substituted radicals may be monosubstituted or polysubstituted, wherein in a multiple substitution the substituents may be the same or different.
  • the general or preferred radical definitions or explanations given above apply correspondingly to the end products and to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges.
  • Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
  • Particular preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present.
  • Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.
  • Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings given above as being particularly particularly preferred.
  • Very particular preference is given according to the invention to compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.
  • the compounds of the formula (I) may also be present as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
  • the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
  • the invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.
  • the compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
  • the present compounds of the general formula (I) may optionally have a chiral carbon atom. According to the rules of Cahn, Ingold and Prelog (CIP rules), these substituents may have both an (R) and an (S) configuration.
  • the present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms is independently (1) an (R) -configuration; or (2) have an (S) configuration.
  • any combination of chiral center configurations is possible, ie, (1) one chiral center has the (R) configuration and the other chiral center has the (S) configuration; (2) one chiral center the (R) configuration and the other chiral center the (R) configuration; and (3) one chiral center may have the (S) configuration and the other chiral center may have the (S) configuration.
  • halogen is selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine, unless otherwise defined elsewhere the term "alkyl", either alone or in combination with other terms, such as haloalkyl, in the context of the present invention means a radical of a saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched.
  • C 1 -C 12 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl.
  • alkenyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkenyl radical having at least one double bond, for example vinyl, allyl, 1 Propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2 Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl.
  • alkynyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkynyl having at least one triple bond, for example ethynyl, 1-propynyl and propargyl, understood.
  • alkynyl radicals can also have at least one double bond.
  • cycloalkyl either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood , Preferred of these are C3-C6-cycloalkyl radicals.
  • alkoxy or “alkyloxy”, either alone or in combination with other terms such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term “alkyl” having the meaning given above.
  • Oxy means the group O-.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • aryl according to the invention is understood as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl.
  • arylalkyl means a combination of “aryl” and “alkyl” radicals as defined in the invention, the radical generally being attached via the alkyl group, examples being benzyl, phenylethyl or Methylbenzyl, with benzyl being particularly preferred.
  • hetaryl means a mono-, bi- or tricyclic heterocyclic group of C atoms and at least one heteroatom, wherein at least one cycle is aromatic.
  • the hetaryl group contains 3, 4, 5 or 6 carbon atoms.
  • hetaryl is pyridinyl or pyrimidinyl.
  • heterocyclyl means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring of C atoms and at least one heteroatom in the ring.
  • the heterocyclyl group contains 3, 4, 5 or 6 carbon atoms and 1 or 2 heteroatoms from the series oxygen, sulfur or nitrogen.
  • heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl.
  • oxotetrahydrofuranyl or pyrrolidinonyl may be mentioned.
  • the group "benzylimino” or “benzylimine” may also be referred to as phenylmethyleneamino.
  • the groups 4-cyanobenzylimine (R4 in Example No. I-252) or 3-fluoro-4- (trifluoromethyl) benzylimine (R4 in Example No. I-257) may also be described as (4-cyanophenyl) methyleneamino and [ 3-Fluoro-4- (trifluoromethyl) phenyl] methyleneamino.
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises both pure stereoisomers and any mixtures of these isomers.
  • Methods and uses The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, in particular nematodes, and mollusks found in agriculture, horticulture, livestock, aquaculture, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector.
  • the term "hygiene” is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and to protect animals and / or protect the environment, and / or maintain cleanliness. According to the invention this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramic, plastic or metal (s) to ensure that they are free from hygiene pests and / or their excretions are.
  • surgical or therapeutic treatment regimens to be applied to the human body or bodies of animals and diagnostic provisions made on the human body or bodies of animals.
  • honeygiene sector covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, Hospitals, stables, animal husbandry etc.
  • the term “hygiene pest” is therefore to be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, especially for health reasons. It is therefore a major objective to avoid or minimize the presence of hygiene pests and / or exposure to them in the sanitary sector. This can be achieved in particular by the use of a pesticide, which can be used both to prevent infestation and to prevent an already existing infestation. It is also possible to use preparations which prevent or reduce exposure to pests.
  • Hygiene pests include, for example, the organisms mentioned below.
  • the term “hygiene protection” thus covers all actions that maintain and / or improve such hygiene measures, rules and procedures.
  • the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above-mentioned pests include: pests from the strain of Arthropoda, in particular from the class of Arachnida z.
  • Acarus spp. E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g.
  • Eotetranychus hicoriae Epitrimerus pyri, Eutetranychus spp., E.g. Eutetranychus banksi, Eriophyes spp., E.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Z. B.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
  • Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
  • Anoplophora glabripennis Anthonomus spp., Z. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.
  • Melolontha melolontha Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g.
  • Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
  • Tribolium audax Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.
  • Icerya purchasi Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g.
  • B. Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma americanula, Macrosiphum spp., E.g.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. E.g. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g.
  • Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g.
  • Trioza spp. E.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
  • Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g.
  • Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., E.g. B. Dioryctria tremani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp. Homo. Spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., Z. B.
  • Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Z. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Podesia spp., E.g.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • Ctenocephalides spp. E.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata; Pests of the strain of Mollusca, z. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., Z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., Z. B.
  • Belonolaimus gracilis Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g.
  • Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g.
  • the compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as a remedy for MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism).
  • MLO Mycoplasma-like-organism
  • RLO Rosia-like-organism
  • Formulations The present invention furthermore relates to formulations and use forms prepared therefrom as pesticides, such as, for example, pesticides.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g.
  • oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such.
  • glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Typical 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). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties to the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, usable pesticides such as spray mixtures or seed dressing), such as certain physical, technical and / or to confer biological properties.
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), the ketones (such as acetone, cyclohexanone ), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • the ketones such as acetone, cyclohexanone
  • Esters including fat
  • Suitable liquid solvents are essentially: 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, eg.
  • Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such.
  • cyclohexane paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water. In principle, all suitable carriers can be used. As carriers are in particular question: z.
  • Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as fumed silica, alumina and natural or synthetic silicates, Resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: z. As broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corncobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic 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 sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g.
  • alkylaryl polyglycol ethers alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose.
  • a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
  • dyes such as inorganic pigments, eg.
  • iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional auxiliaries may be mineral and vegetable oils.
  • further auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestering agents, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Penetration promoters in the present context include all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be 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 application form , lie.
  • the application is done in a custom forms adapted to the application.
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, Semiochemicals and / or plant growth regulators are used to z. B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt.
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of formula (I) can be used to improve plant properties such as growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, e.g.
  • carbamates e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosul
  • GABA-controlled chloride channel blockers such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil.
  • sodium channel modulators such as pyrethroids, e.g.
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • allosteric modulators of the nicotinic acetylcholine receptor (nAChR) such as spinosyn, e.g. B. spinetoram and spinosad.
  • allosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Various non-specific (multi-site) inhibitors such as alkyl halides, e.g.
  • modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
  • mite growth inhibitors such as. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Microbial disruptors of insect intestinal membrane such.
  • inhibitors of mitochondrial ATP synthase such as ATP disruptors, such as diafenthiuron or organotin compounds, e.g.
  • azocyclotine cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • (123) Decoupling of oxidative phosphorylation by disruption of the proton gradient, such as chlorfenapyr, DNOC and sulfluramide.
  • Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Skinning disruptor especially in dipterans, ie, two-wingers), such as cyromazine.
  • ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • octopamine receptor agonists such as amitraz.
  • Mitochondrial Complex III Electron Transport Inhibitors such as hydramethylnone or acequinocyl or fluacrypyrim.
  • Mitochondrial Complex I Electron Transport Inhibitors such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • (22) blocker of the voltage-dependent sodium channel, such. Indoxacarb or metaflumizone.
  • inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g.
  • Cyenopyrafen and Cyflumetofen and carboxanilides such as Pyflubumid.
  • ryanodine receptor modulators such as diamides, e.g. B. chlorantraniliprole, cyanotriliprol and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon- Momfluthrin, Flometoquine, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin,
  • Fungicides The active ingredients specified here by their "common name” are known and described, for example, in the "Pesticide Manual” (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides) , All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally be salts with suitable bases or acids form. All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
  • inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetrac
  • inhibitors of the respiratory chain on complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr , (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R, 4
  • 3) respiratory chain inhibitors on complex III for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) enoxastrobin, (3,009) famoxadone, (3,010) fenamidone, (3,011) flufenoxystrobin, (3,012) fluoxastrobin, (3,013) kresoxime methyl, (3,014) metominostrobin, (3,015) orysastrobin, (3,016) picoxystrobin, (3,017) pyraclostrobin, (3,018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E) -2- ⁇ 2 - [( ⁇ [(1E)
  • inhibitors of mitosis and cell division for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3-Chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4.012) 4- (2-bromo 4-fluorophenyl) -N- (2,
  • Inhibitors of ATP production for example, (8,001) silthiofam.
  • inhibitors of cell wall synthesis for example, (9,001) benthiavalicarb, (9,002) dimethomorph, (9,003) flumorph, (9,004) iprovalicarb, (9,005) mandipropamide, (9,006) pyrimorph, (9,007) valproate, (9,008) (2E) -3 (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one.
  • Inhibitors of lipid and membrane synthesis for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) tolclofos-methyl.
  • Inhibitors of melanin biosynthesis for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate.
  • inhibitors of nucleic acid synthesis for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
  • inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
  • compounds which may act as decouplers for example (14.001) fluazinam, (14.002) meptyldinocap.
  • Bio Pesticides as Mixture Components
  • the compounds of formula (I) may be combined with biological pesticides.
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides. Examples of such bacteria which can be used as biological pesticides are: Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B.
  • thuringiensis subspecies israelensis (Serotype H-14), strain AM65 -52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are: Beauveria bassiana, especially strain ATCC 74040, Coniothyrium minitans, especially strain CON / M / 91-8 (Accession No.
  • Lecanicillium spp. in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new : Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P.
  • viruses that can be used as biological pesticides are: Adoxophyes orana (apple peel wrapper) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African cotton worm) NPV. It also includes bacteria and fungi that are added as "inoculant" plants or plant parts or plant organs and promote by their special properties, plant growth and plant health.
  • Examples include: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., Especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp.
  • Laccaria spp. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp. Examples of plant extracts and such products.
  • Safeners as Mixture Components The compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (- ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -1,3 oxazolidine (CAS 52
  • Plants and Plant Parts can be treated.
  • Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes).
  • 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 can not be protected by plant breeders' rights.
  • Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, nebulization, scattering, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping.
  • all plants and their parts can be treated.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, 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. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars.
  • Plant varieties are plants with new ones Traits obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • transgenic Plant, Seed Treatment and Integration Events Among the preferred transgenic (genetically engineered) plants or plant species to be treated according to the invention are any plants which have obtained genetic material through the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z.
  • microbial pests such as insects, arachnids, nematodes, mites, snails
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) are produced in the plants, also an increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
  • the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations are produced in the plants, also an increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
  • systemically acquired resistance SAR
  • systemin phytoalexins
  • elicitors elicitors
  • resistance genes and correspondingly expressed proteins and toxins as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • PAT phosphinotricin
  • transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • Crop protection treatments The treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg. By dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), Drip irrigation and in propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to apply the compounds of formula (I) by the ultra-low-volume method or to inject the use form or the compound of the formula (I) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, i. H. the compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, i. H.
  • the compounds of the formula (I) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In water rice crops this may also be by metered addition of the compound of formula (I) in a solid form (eg as granules) into a flooded paddy field.
  • Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to constant improvement. Nevertheless, the treatment of seeds presents a number of problems that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants.
  • seed treatment methods should also incorporate the intrinsic insecticidal or nematicidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with a minimum of pesticide use.
  • the present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from attack by pests further comprises a method in which the Seed simultaneously in one operation or sequentially treated with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention.
  • the invention also relates to seed treated at the same time with a compound of formula (I) and a mixture component.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component.
  • the individual substances may be present in different layers on the seed.
  • the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • One of the advantages that occurs when a compound of formula (I) acts systemically is that treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted. Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
  • Compounds of the formula (I) may also be used in combination with signal technology agents, whereby a better colonization with symbionts, such as rhizobia, Mycorrhiza and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation.
  • symbionts such as rhizobia, Mycorrhiza and / or endophytic bacteria or fungi.
  • the compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals eg wheat, barley, rye, millet and oats
  • corn eg wheat, barley, rye, millet and oats
  • corn cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet)
  • peanut eg tomato, cucumber, bean, cabbage, onions and lettuce
  • fruit plants turf and ornamental plants.
  • seeds of cereals such as wheat, barley, rye and oats
  • corn soybean, cotton, canola, oilseed rape, vegetables and rice.
  • the treatment of transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming.
  • the seeds In the case of rice seeds, it is also possible to use seeds that have been soaked, for example, in water to a certain stage of the rice embryo ("Pigeon Breast Stage"), which stimulates germination and a more uniform emergence. In general, when treating seed, care must be taken to ensure that the amount of compound of formula (I) and / or other additives applied to the seed is not such as to affect the germination of the seed or to damage the resulting plant becomes. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations. These formulations are prepared in a known manner by mixing the compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water. Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol.2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of maize, rice, rapeseed, peas, beans, cotton , Sunflower, soy and beet or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • all mixing devices which can usually be used for the dressing can be considered.
  • the seed is placed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates at the connection of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • Animal health In the field of animal health, d. H.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of formula (I) which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of formula (I) are administered to birds, namely caged birds or, in particular, poultry.
  • birds namely caged birds or, in particular, poultry.
  • the compounds of formula (I) for the control of animal parasites disease, deaths and reductions (in meat, milk, wool, hides, eggs, honey and the like) are to be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable.
  • the term "controlling” or “controlling” in the present context means that the compounds of formula (I) effectively affect the appearance of the respective parasite in an animal infected with such parasites to a harmless extent , is reduced.
  • the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles
  • Melophagus spp. Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonaptrida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests
  • the following Akari can be mentioned by way of example: From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp. , from the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • the family Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., I
  • Examples of parasitic protozoa include, but are not limited to: Mastigophora (Flagellata), such as: Metamonada: from the order Vaccinonadida for example Giardia spp., Spironucleus spp. Parabasala: from the order Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Euglenozoa: from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
  • Mastigophora Frallata
  • Metamonada from the order Vaccinia spp.
  • Parabasala from the order Trichomonadida for example Histomonas spp.
  • Pentatrichomonas spp. Tetratrichomonas spp.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp. Alveolata such as Apicomplexa (Sporozoa): z.
  • Cryptosporidium spp . from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; from the order Piroplasmida z.
  • Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes).
  • helminths include, but are not limited to, monogenea: e.g.
  • Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
  • Trematodes from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
  • Collyricum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Or
  • Nematodes from the order Trichinellida for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
  • Tylenchida Micronema spp., Parastrangyloides spp., Strongyloides spp.
  • Aelurostrongylus spp. Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp.
  • Cyclococercus spp. Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesoot
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp., From the order Polymorphida for example: Filicollis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. Pentastoma: from the order Porocephalida for example Linguatula spp.
  • the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
  • one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.
  • Another aspect relates to the compounds of formula (I) for use as antiendoparasitic.
  • Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic agents, in particular for use as nematicide, platelet minthicide, acanthocephalicide or pentastomicide.
  • Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic. Another aspect relates to the compounds of formula (I) for use as anti-topazarasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide.
  • Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of a pharmaceutically acceptable excipient (eg, solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg, surfactants), especially one Pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient eg, solid or liquid diluents
  • a pharmaceutically acceptable adjuvant eg, surfactants
  • a related aspect of the invention is a method of making a veterinary formulation as described herein which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, especially pharmaceutically acceptable excipients conventionally used in veterinary formulations; or conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, especially selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations according to the aspects mentioned, as well as processes for their preparation.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a non-human Animal that needs it.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, the same requirement.
  • Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
  • treatment includes prophylactic, metaphylactic and therapeutic treatment.
  • mixtures of at least one compound of formula (I) with other active ingredients, especially endo and ectoparasiticides, are provided herein for the veterinary field.
  • blending not only means that two (or more) different active ingredients are formulated in a single formulation and used together, but also refers to products comprising separate formulations for each active ingredient. Accordingly, if more than two drugs are to be used, all drugs can be formulated in a single formulation or all drugs can be formulated in separate formulations; Also conceivable are mixed forms in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow the separate or sequential use of the active substances in question.
  • the active ingredients specified herein by their "common name" are known and described, for example, in the "Pesticide Manual” (see above) or searchable on the Internet (e.g., http://www.alanwood.net/pesticides).
  • Exemplary agents from the group of ectoparasiticides as a mating agent include, but are not limited to, the insecticides and the acaricides detailed above one.
  • Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (1
  • Nithiazine Dicloromezotiaz, triflumezopyrim macrocyclic lactones e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime, triphene, epofenone, diofenolane; Biologicals, hormones or pheromones, for example natural products, e.g. Thuringiensin, codlemon or neem components dinitrophenols, e.g.
  • Benzoylureas eg. As fluazuron, penflurone, amidine derivatives, z. Chormorman, cymiazole, demiditraz hive varroa acaricides, for example organic acids, e.g. Formic acid, oxalic acid.
  • exemplary agents from the group of endoparasiticides, as a mixture partner include, but are not limited to, anthelmintic agents and antiprotozoal agents.
  • the anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestotic agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flu
  • Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides,
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
  • vectors and their transmitted diseases or pathogens are: 1) mosquitoes - anopheles: malaria, filariasis; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of other worms; - Aedes: yellow fever, dengue fever, other viral diseases, filariasis; - Simulia: transmission of worms, in particular Onchocerca volvulus; - Psychodidae: transmission of leishmaniasis 2) lice: skin infections, epidemic typhus; 3) fleas: plague, endemic typhus, tapeworms; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases; 5) mites: acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis; 6) Ticks: Borellioses such as Borrelia bungdorf
  • vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A.
  • compositions of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the protection of materials and materials. Protection of Technical Materials
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of formula (I) are present as a ready-to-use pest control agent, i. h., They can be applied to the appropriate material without further changes.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out for example in aerosols, non-pressurized sprays, z.
  • Process A The compounds of the formula (Ic) according to the invention indicated in Process A, in which V1 and V2 are oxygen, can be prepared by the sequence of literature methods according to the following scheme.
  • R1, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is C-linked to the rest of the molecule.
  • X is - unless further limited in the scheme - halogen, in particular chlorine, bromine or iodine.
  • R2 stands for hydrogen.
  • BOC tert-butyl-oxy-carbonyl.
  • the invention also relates to the intermediates of the general formulas (VII), (VIII), (IX) and (X), wherein R 1, R 3, R 4, R 5 and R 6 have the meanings described above, R 2 is hydrogen, X is halogen and Y for stands.
  • the hydroxy function of 4-hydroxypyridine-2,6-dicarboxylic acids (II) can be determined, for example, in analogy to the processes described in US Pat. No. 6,353,553 or US2004 / 29851 in the presence of phosphorus pentabromide in suitable inert solvents, eg. As carbon tetrachloride or chlorobenzene, in the corresponding Bromsubstituenten.
  • suitable inert solvents eg. As carbon tetrachloride or chlorobenzene, in the corresponding Bromsubstituenten.
  • Step 1a The hydroxy function of 4-hydroxypyridine-2,6-dicarboxylic acids (II) can be converted into the corresponding chlorine substituents similarly to step 1.
  • a suitable method for the reaction with thionyl chloride in a suitable inert solvent such as. As dimethylformamide, z. In US2014 / 336373.
  • step la may also be carried out by reacting (II) with phosphorus pentachloride in a suitable inert solvent, e.g. As carbon tetrachloride, and subsequent reaction with an alcohol, for.
  • methanol can be converted into the corresponding dialkyl ester of the formula (IIa) (compare, by analogy, for example, Tetrahedron, 2005, 61, 1755-1763).
  • 2,6-dialkyl-4-halopyridine-2,6-dicarboxylates of the formula (III) are known from the literature and can also be prepared from 4-amino- or 4-halopyridines by known methods.
  • Dialkyl esters of the formula (III) can be obtained by saponification with the aid of a base, such as potassium hydroxide, in suitable inert solvents or solvent mixtures, such as. B. methanol / dichloromethane 10: 1 in the corresponding monoalkyl esters of the formula (IV) convert (see EP 2017279).
  • Step 3 The acid function of the monoalkyl esters obtained in step 2 can furthermore be carried out by literature methods, for. B. according to EP 2017279, by Curtius rearrangement, for example by reaction with diphenyl phosphoryl azide in suitable inert solvents, such as.
  • Step 4 To convert the compounds of formula (V) into the analogous compounds of formula (VI), the BOC protecting group can be prepared by reacting (V) with an acid, eg trifluoroacetic acid, in a suitable inert solvent, e.g. As chloroform or dichloromethane, split (see EP 2017279).
  • Step 5 The acylation of the compounds of formula (VI) to give compounds of formula (VII) succeeds by literature methods, such as.
  • Example by the reaction of (VI) with a suitable acid chloride in the presence of suitable bases, for.
  • suitable bases for.
  • pyridine, triethylamine or potassium carbonate in a suitable inert solvent such.
  • dichloromethane or 2-butanone for example, dichloromethane or 2-butanone.
  • Analogous methods are z. As described in EP1714966, US5403816 or WO2004 / 35545.
  • compounds of formula (VII) may also be prepared by reacting (VI) with carboxylic acids in the presence of suitable coupling reagents, e.g.
  • HATU O- (7-azabenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate]
  • EDCI 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
  • Bases e.g. Triethylamine or N, N- Diisopropylethylamine
  • suitable inert solvents such as.
  • DMF dimethylformamide
  • dichloromethane obtained (compare in analogy, for example, US2011 / 301181 or WO2007 / 122258).
  • the carboxylic acids are either commercially available or can be prepared by known methods.
  • Step 6 The cleavage of the ester function in compounds of the formula (VII) for the preparation of (VIII) succeeds by reaction with a suitable base in accordance with methods known from the literature (cf., for example, US2007 / 213349, WO2015 / 150440 or US2011 / 301181) , z.
  • a suitable base in accordance with methods known from the literature (cf., for example, US2007 / 213349, WO2015 / 150440 or US2011 / 301181) , z.
  • lithium hydroxide or sodium hydroxide in suitable aqueous solvent mixtures, for.
  • water / THF water / methanol or water / dioxane, or water.
  • Step 7 The resulting carboxylic acids of formula (VIII) can be reacted with primary or secondary amines, alkoxyamines or hydrazines in the presence of suitable coupling reagents, e.g.
  • HATU or EDCI and suitable bases, e.g.
  • suitable bases e.g.
  • triethylamine or N, N-diisopropylethylamine in suitable inert solvents such.
  • DMF or dichloromethane to the corresponding amides (IX) implement (see in analogy, for example, US2011 / 301181 or WO2007 / 122258).
  • a reaction of pyridine-2-carboxylic acids to (IX) can also be carried out by methods known from the literature (cf., for example, in analogy to, for example, Bioorganic and Medicinal Chemistry Letters, 2006, Vol. 16, # 10, pages 2689-2692) Acid chloride, e.g. B.
  • Step 8 To obtain the corresponding boronic acids or dioxoborolane derivatives (X) from the halogenated compounds (IX), methods known from the literature can also be used. So can be z.
  • B 4-bromo-pyridine-2-carboxamides by reaction with bis (pinacolato) diboron [4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-1 , 3,2-dioxaborolane] in the presence of potassium acetate and suitable catalysts, such.
  • step 5 with the sequence from step 6 & 7 is optionally also exchangeable in the sequence.
  • Step 9 Dioxoborolan-pyridines or pyridinboronic acids of the formula (X) can be prepared by aryl or hetaryl halides, in particular chlorides, bromides or iodides, or by aryl or hetaryl triflates, according to known methods to aryl- or hetaryl-pyridines couple.
  • This reaction can be carried out in a suitable solvent, e.g. As dimethylformamide, or a suitable solvent mixture, such as.
  • Step 9a Halogenated pyridines of the formula (IX) can be coupled with aryl- and hetaryl-boronic acids or aryl- and hetarylboronic esters by known methods to aryl- or hetaryl-pyridines. This reaction can be carried out in a suitable solvent, e.g. As dimethylformamide, or a suitable solvent mixture, such as.
  • a suitable solvent e.g. As dimethylformamide, or a suitable solvent mixture, such as.
  • R1, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is C-N linked to the rest of the molecule.
  • X is halogen, preferably bromine or iodine.
  • R2 stands for hydrogen.
  • Step 1 A coupling of the halogenated pyridines of the formula (IX) with NH-containing heteroaromatics, such as. As pyrroles, imidazoles or pyrazoles, z.
  • R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above.
  • the invention also relates to the intermediates of general formulas (XVI), (XVII) and (XVIII), wherein R2, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is not unsubstituted phenyl and not substituted or unsubstituted pyrazole stands.
  • Step 1 A coupling of 2,6-dichloro-4-iodopyridine of the formula (XIII) at the position of the iodine with aromatic or heteroaromatic boronic acids, boronic acid esters or bisoxoborolanes to compounds of formula (XIV) can be prepared according to the known methods described in Method A, step 9a, using suitable catalysts, for. As tetrakis (triphenylphosphine) palladium (0) occur. Furthermore, compounds of the formula (XIV) can be prepared by coupling the 2,6-dichloro-4-iodopyridines at the position of the iodine with NH heterocycles in analogy to the known methods described in process B, step 1 [cf. B.
  • Step 2 The vinylation of the compounds of formula (XIV) to (XV) by reacting with z. B. 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolan or trivinylboroxine in analogy to the methods described in Method A, step 9a, known palladium-catalyzed methods [see in addition z. WO2011 / 54773 or WO2009 / 24905] feasible.
  • Step 3 The vinyl function of the obtained under step 2 compounds of formula (XV) can be prepared by literature methods, for. B. according to WO2009 / 24905, by suitable oxidizing agents, for. As potassium permanganate, in suitable solvents or mixtures, for. As water / acetone are converted into the corresponding carboxylic acid function, whereby compounds of formula (XVI) are obtained.
  • Step 4 The resulting carboxylic acids of formula (XVI) can be z. B.
  • Step 5 To obtain compounds of formula (XVIII) from the precursors (XVII), methods known from the literature can also be used. So z. B. according to WO2009 / 147190 the introduction of primary amines at the position of the chlorine in 2-chloropyridines by direct reaction of both reactants with heating in a suitable solvent, for. As water or dimethyl sulfoxide, optionally in the presence of another base such. As N, N-diisopropylethylamine and optionally under elevated pressure conditions.
  • This reaction can be carried out with aqueous ammonia [cf., for. US2007 / 66644], or with aqueous ammonia in a suitable solvent, e.g. B. isopropanol [see, for. WO2011 / 110575], optionally in the presence of copper salts, for. B. copper (II) sulfate [see, for. B. US2009 / 162453] and optionally under elevated pressure, take place.
  • compounds of formula (XVIII) may be obtained by reaction of (XVII) with primary amides or primary carbamates according to methods known in the literature. This reaction can be carried out in a suitable solvent, e.g. As 1,4-dioxane, by catalysis with tris (dibenzylideneaceton) dipalladium (0) [see, for. B. US2013 / 165464] or palladium (II) diacetate [cf., for.
  • a phosphine ligand for example xantphos (4,5-bis (diphenylphosphino) -9,9-dimethylxanthene) or Xphos (2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl ) and a suitable base, e.g. As cesium carbonate, take place.
  • a suitable base e.g. As cesium carbonate
  • pyridine, triethylamine or potassium carbonate in a suitable inert solvent such.
  • a suitable inert solvent such as dichloromethane.
  • compounds of formula (Ic) may also be prepared by reacting (XVIII) with carboxylic acids in the presence of suitable coupling reagents, e.g. HATU or EDCI, and suitable bases, e.g. For example, triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such.
  • suitable coupling reagents e.g. HATU or EDCI
  • suitable bases e.g.
  • triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such.
  • DMF or dichloromethane obtained (compare in analogy, for example, US2011 / 301181 or WO2007 / 122258).
  • Process D The compounds of the formula (Ic) according to the
  • R1, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is C-linked to the rest of the molecule.
  • X is halogen or trifluoromethanesulfonate.
  • R2 stands for hydrogen.
  • the invention also relates to the intermediates of general formulas (XIX) and (XX) wherein R 2 is hydrogen and R 3, R 4, R 5, R 6 and Q 1 have the meanings described above, with Q 1 being CC-linked to the rest of the molecule and not represents unsubstituted phenyl.
  • the pyridines of the formula (XIX) can be prepared for example by a Michael reaction of a 1- (cyanomethyl) pyridinium halide and a ⁇ , ⁇ -unsaturated ketone in the presence of ammonium acetate according to the so-called Kröhnke pyridine synthesis, as described in Synthesis 1976, 1-24 and Angew. Chem.196274, 811-817.
  • the required ⁇ , ⁇ -unsaturated ketones can be prepared by a number of known methods;
  • R 6 3-alkyl-2-oxo-4-aryl-but-3-enynoic acid
  • aromatic aldehydes as described in Tet.
  • compounds of formula (Ic) may also be prepared by reacting (XX) with carboxylic acids in the presence of suitable coupling reagents, e.g. HATU or EDCI, and suitable bases, e.g. For example, triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such.
  • suitable coupling reagents e.g. HATU or EDCI
  • suitable bases e.g.
  • suitable inert solvents such as DMF or dichloromethane obtained (compare in analogy, for example, US2011 / 301181 or WO2007 / 122258).
  • step 2 is replaceable with step 3 in the order.
  • Process E The compounds of the formula (Ic) according to the invention in which V1 and V2 are oxygen can be prepared by methods known from the literature in accordance with the following scheme.
  • Step 1 Thioamides of the formula (I) in which V1 or V2 or both (V1 and V2) represent sulfur can be prepared from amides of the formula (Ic) by reaction with a suitable sulfurizing reagent, for example Lawesson's reagent (cf. B. WO2005 / 9435) or P 4 S 10 (compare in analogy, for example, European Journal of Medicinal Chemistry 1995 30, 915-924), in suitable Solvents such as toluene or xylene produce.
  • a suitable sulfurizing reagent for example Lawesson's reagent (cf. B. WO2005 / 9435) or P 4 S 10 (compare in analogy, for example, European Journal of Medicinal Chemistry 1995 30, 915-924), in suitable Solvents such as toluene or xylene produce.
  • the thioamide synthesis can also be carried out from the intermediates (VII) or (XVII).
  • the further conversion to compounds of the formula (I) in which V1 or V2 or both (V1 and V2) are sulfur is then carried out analogously to the processes described in Processes A and C.
  • Process G The compounds of formula (I) according to the invention, in which R 2 or R 3 is C (O) -alkyl and the other is H or in which both (R 2 and R 3) are C (O) -alkyl , can be prepared by literature methods according to the following scheme.
  • Step 1 Carbamates of the formula (I) in which R 2 or R 3 is C (O) -alkyl and the other is H or in which both (R 2 and R 3) are C (O) -alkyl, can be prepared from amides of Formula (I) in which R2 and R3 are H, by reaction with chloroformates and a base, for example sodium hydride (compare in analogy, for example, EP1932836), in suitable solvents such as DMF or tetrahydrofuran produce.
  • a base for example sodium hydride
  • suitable solvents such as DMF or tetrahydrofuran produce.
  • Process H The compounds of the formula (Ic) according to the invention indicated in process H can also be prepared by the sequence of methods known from the literature in accordance with the following scheme.
  • the radicals R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above.
  • the radical G is alkoxy (especially methoxy and ethoxy) or NH 2 .
  • Step 1 The coupling of the 2,6-dichloro-4-iodopyridines of the formula (XIII) at the position of the iodine with aromatic or heteroaromatic boronic acids, boronic esters or bisoxoborolanes to give compounds of the formula (XIV) can be carried out according to the procedure A, step 9a described known methods using suitable catalysts, for. As tetrakis (triphenylphosphine) palladium (0) occur.
  • boronic acid derivatives or boronic acid ester derivatives are known and / or commercially available or can be prepared by generally known methods (cf Boronic Acids (Eds .: DG Hall), 2nd ed., Wiley-VCH, Weinheim, 2011).
  • the coupling of pyridine derivatives of the formula (XIII) with NH-containing heteroaromatics can be carried out analogously to the methods described under process B.
  • Step 2 To obtain compounds of the formula (XXI) from the precursors (XIV), methods known from the literature can also be used in accordance with process C, step 5.
  • So z. B. primary amines or ammonia (for R2 H) by direct reaction of both reactants by heating in a suitable solvent, eg.
  • Step 3 The preparation of the compounds of the formula (XXII) can be carried out in analogy to the processes described under Process A, Step 5 described methods by reacting (XXI) with a suitable acid chloride in the presence of suitable bases, for.
  • suitable bases for.
  • pyridine, triethylamine or potassium carbonate in a suitable inert solvent such.
  • suitable inert solvent such as dichloromethane
  • suitable coupling reagents for. HATU or EDCI
  • suitable bases e.g.
  • triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such as.
  • DMF or dichloromethane e.g.
  • Step 4 Chloropyridines of the general formula (XXII) can be converted by reaction with carbon monoxide by methods known from the literature into compounds of the formula (XXIII).
  • G alkoxy
  • this reaction can be carried out in a suitable alcohol (in particular methanol and ethanol), by catalysis with tris (dibenzylideneacetone) dipalladium (0) [cf., for example, US Pat. B. US2013 / 165464] or palladium (II) diacetate [cf., for.
  • WO2011 / 137342 or WO2014 / 114185 in the presence of a phosphine ligand, for example xantphos (4,5-bis (diphenylphosphino) -9,9-dimethylxanthene) or Xphos (2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl ) and a suitable organic or inorganic base, e.g. As triethylamine or cesium carbonate, take place.
  • a phosphine ligand for example xantphos (4,5-bis (diphenylphosphino) -9,9-dimethylxanthene) or Xphos (2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl ) and a suitable organic or inorganic base, e.g. As triethylamine or cesium carbonate
  • Step 1 The preparation of compounds of formula (XXIV) is possible by reacting esters of formula (XXIII) with hydrazine hydrate in a suitable inert solvent such.
  • a suitable inert solvent such as methanol, ethanol or dioxane, for example analogous to that described in WO2005 / 121152, European Journal of Medicinal Chemistry 2015, 93, 511-522 or Asian Journal of Chemistry 2015, 27, 4579-4582.
  • Step 2 Hydrazide derivatives of formula (XXIV) can be z. B.
  • Z is bromine, iodine or
  • Step 1 The coupling of the pyridine derivatives of the formula (XXV) with (het) aryl halides or with aromatic or heteroaromatic boronic acids, boronic esters or bisoxoborolanes to give compounds of the formula (XXVI) can be carried out according to the process described under Process A, step 9 and step 9a Methods using suitable catalysts, eg. As tetrakis (triphenylphosphine) palladium (0) occur.
  • suitable catalysts eg. As tetrakis (triphenylphosphine) palladium (0) occur.
  • boronic acid derivatives or boronic acid ester derivatives are known and / or commercially available or can be prepared by generally known methods (cf Boronic Acids (Eds .: DG Hall), 2nd ed., Wiley-VCH, Weinheim, 2011).
  • Step 2 Compounds of the formula (XXVI) can be converted by reaction with an oxidizing agent into compounds of the formula (XXVII).
  • Hydrogen peroxide in combination with an acid such as trifluoroacetic acid, acetic acid or formic acid (see WO2010 / 25451 or Organometallics 2011, 30, 6751-6765) or 3-chloroperbenzoic acid in an inert solvent, such as eg.
  • dichloromethane or chloroform see, WO2011 / 40629, WO2010 / 109005 or WO2011 / 25505).
  • Step 3 By reacting compounds of the formula (XXVII) with trimethylsilyl cyanide and an amine base, for example triethylamine in a suitable inert solvent such as acetonitrile in analogy to the processes described in, for example, WO2009 / 111337 or US2008 / 275057, compounds of the formula (XXVIII).
  • Step 4 Compounds of formula (XXVIII) can be prepared by reaction with a carboxamide using suitable catalysts, such as. B.
  • Step 5 The corresponding amidines of formula (Id) can be obtained by reaction of compounds of formula (XXIX) with amines in the presence of a Lewis acid such as titanium tetrachloride or tin tetrachloride, optionally in a suitable inert solvent such as tetrahydrofuran or dioxane in analogy to the methods described in, for example, Tetrahedron Letters 2013, 54, 343-346 or Journal of Fluorescence 2014, 24, 1563-1570.
  • the reaction can be carried out in the presence of sodium methoxide in methanol (see Journal of Heterocyclic Chemistry 2011, 48, 921-926 or European Journal of Medicinal Chemistry 2013, 59, 7-14).
  • the reaction mixture was added to about 100 ml of a 3% aqueous sodium dihydrogen phosphate solution.
  • the mixture was extracted three times with dichloromethane and the combined organic phases were dried over sodium sulfate and filtered.
  • the solvent was distilled off in vacuo and the residue was purified by column chromatography with a water / acetonitrile gradient as eluent. From this, 49 mg (18% of theory) of the target product (XX-2) were obtained.
  • the reaction mixture was added to about 100 ml of a 3% aqueous sodium dihydrogen phosphate solution.
  • the mixture was extracted three times with dichloromethane and the combined organic phases were dried over sodium sulfate and filtered.
  • the solvent was distilled off in vacuo and the residue was purified by column chromatography with a water / acetonitrile gradient as eluent. From this, 62 mg of the target product (XX-3) were obtained.
  • the aqueous phase was extracted several times with ethyl acetate.
  • the combined organic phases were washed successively with water, 1 N hydrochloric acid, brine and saturated sodium bicarbonate solution, dried over sodium sulfate and filtered.
  • the filtrate was evaporated in vacuo and the residue was purified by chromatography on a silica gel column (ethyl acetate / dichloromethane, 0 to 1:20). 14.0 g (70.0% of theory) of the title compound (IX-1) were obtained.
  • the batch was then heated to 150 ° C for 15 minutes in a Biotage initiator microwave. Thereafter, the reaction solution was cooled to room temperature, filtered through a silica gel / sodium sulfate cartridge and washed with acetonitrile and ethyl acetate. The filtrate was evaporated in vacuo and the residue was purified by chromatography using MPLC (reversed phase, water / acetonitrile).
  • the vial was flooded with argon and 17.4 mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. The batch was heated for 45 minutes at 130 ° C in an IR Discover microwave. Thereafter, the reaction solution was cooled to room temperature, filtered through a silica gel / sodium sulfate cartridge and washed with 1,4-dioxane. The filtrate was evaporated in vacuo and the residue purified by HPLC separation. 76 mg (100% purity, 32.7% of theory) of the title compound (I-123) were obtained.
  • the vial was flooded with argon and 8.7 mg (0.008 mmol) of tetrakis (triphenylphosphine) palladium (0) added.
  • the batch was heated for 45 minutes at 130 ° C in an IR Discover microwave. Thereafter, the reaction solution was cooled to room temperature, filtered through a silica gel / sodium sulfate cartridge and washed with 1,4-dioxane. The filtrate was evaporated in vacuo and the residue purified by HPLC separation. 29 mg (100% purity, 24.9% of theory) of the title compound (I-160) were obtained.
  • the vial was flooded with argon and 22.8 mg (0.02 mmol) of tetrakis (triphenylphosphine) palladium (0) added.
  • the batch was heated for 45 minutes at 130 ° C in an IR Discover microwave. Thereafter, the reaction solution was cooled to room temperature, diluted with ethyl acetate and filtered through a silica gel / sodium sulfate cartridge and washed with ethyl acetate. The filtrate was evaporated in vacuo and the residue was purified by MPLC (eluent cyclohexane: ethyl acetate 1: 8) by chromatography.
  • the vial was again flooded with argon and 7.7 mg (0.05 mmol) of trans-N, N'-dimethylcyclohexane-1,2-diamine (racemic) added.
  • the vessel was sealed and heated in an aluminum block overnight at 130 ° C.
  • the filtrate was evaporated in vacuo and the residue purified by MPLC separation (eluent dichloromethane: ethyl acetate, 7: 3) followed by a second separation (reversed phase, water eluant: acetonitrile + 0.1% formic acid). 56 mg (96% purity, 39.6% of theory) of the title compound (I-188) were obtained.
  • the second line in the autoclave contained ammonia and was additionally filled with CO.
  • the reaction mixture was kept under 10 bar CO at 80 ° C for 15 hours. After cooling, the solvent was removed under vacuum. The residue was suspended in acetonitrile, insolubles were removed by filtration. The resulting filtrate was freed of solvent under vacuum. This gave 1.07 g (86% pure, quantitative) of the title compound (XXIII-1).
  • a uor-4- (trifluoromethyl) phenyl W is (trifluoromethyl) amino] phenyl M rifluoromethoxy) phenyl L
  • the measurement of the logP values is carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 55 ° C.
  • the determination with the LC-MS in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.
  • logP HCOOH
  • the determination with the LC-MS in the neutral range is carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.
  • logP neutral
  • the calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
  • the NMR data of selected examples are listed either in classical form ( ⁇ values, multiplet splitting, number of H atoms) or as NMR peak lists. The solvent in which the NMR spectrum was recorded is given in each case.
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak first the ⁇ value in ppm and then the signal intensity in parentheses is listed. The ⁇ value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form:
  • 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. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • To calibrate the chemical shift of 1H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • the lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation.
  • 1H NMR prints can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.
  • our lists of 1H NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which are usually average have a high intensity.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity 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.
  • 250 ⁇ l of the solution are distributed homogeneously on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h swing rotation at 30 rpm).
  • a surface dose of 5 ⁇ g / cm2 is achieved with homogeneous distribution.
  • the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar.
  • Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck.
  • a substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / cm2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
  • the following compounds of the Preparation Examples show an effect of 100% at a rate of 5 ⁇ g / cm2 (500 g / ha): I-118, I-128, I-138, I-162, I-197, 216.
  • the following compounds of the preparation examples show an effect of 80% at an application rate of 5 ⁇ g / cm 2 (500 g / ha):
  • I-013 Boophilus microplus injection test Solvent: dimethylsulfoxide
  • 10 are mixed mg of active ingredient with 0.5 ml of solvent and dilute the concentrate with solvent to the desired concentration.
  • 1 ⁇ l of the drug solution is injected into the abdomen of 5 wet, adult, female bovine ticks (Boophilus microplus).
  • the animals are transferred to trays and kept in an air-conditioned room.
  • the effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching.
  • an effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
  • the following compounds of the preparation examples show an effect of 95% at an application rate of 20 ⁇ g / animal: I-104.
  • the following compounds of the preparation examples show an effect of 80% at an application rate of 20 ⁇ g / animal: I-151 Ctenocephalides felis Oral Test Solvent: Dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: I-004, I-005, I-008, I-013, I-026, I-027, I-028, I -030, I-036, I-043, I-044, I-051, I-052, I-073, I-074, I-075, I-076, I-077, I-078, I-079 , I-080, I-081, I-082, I-085, I-089, I-094, I-096, I-098, I-102, I-105, I-108, I-109, I -110, I-113, I-115, I-116, I-117, I-118, I-120, I-124, I-128, I-130, I-131, I-133, I-138 , I-141, I-142, I-149, I-151, I-152, I-154, I-155, I-159, I-160, I-162, I
  • the following compounds of the preparation examples show an effect of 98% at an application rate of 100 ppm: I-015, I-017, I-025, I-040, I-070
  • the following compounds show the preparation examples an effect of 95% at an application rate of 100 ppm: I-041, I-053, I-065, I-091, I-093, I-095, I-150, I-235.
  • the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: I-088, I-167.
  • the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: I-104, I-217.
  • Lucilia cuprina test Solvent dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Approximately Twenty L1 larvae of the Australian Goldfinch Sheep (Lucilia cuprina) are transferred to a test tube containing chopped horsemeat and the preparation of active compound of the desired concentration. After 2 days the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: I-005, I-013, I-015, I-026, I-040, I-043, I-044, I -048, I-052, I-053, I-070, I-073, I-074, I-077, I-078, I-079, I-080, I-081, I-082, I-085 , I-091, I-093, I-094, I-096, I-098, I-104, I-107, I-113, I-120, I-124, I-128, I-133, I -138, I-141, I-149, I-151, I-154, I-155, I-160, I-172, I-173, I-176, I-178, I-182, I-184 , I-190, I-195, I-196, I-197, I-213, I-217, I-224, I-225, I-228, I-247, I-249.
  • the following compounds of the preparation examples show an effect of 95% at an application rate of 100 ppm: I-008, I-089, I-117, I-250.
  • the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: I-027, I-030, I-108, I-115, I-142, I-152, I-159, I -192.
  • the following compounds of the preparation examples show an effect of 85% at an application rate of 100 ppm: I-021.
  • the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: I-216, I-245.
  • Musca domestica test Solvent Dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica). After 2 days the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: I-013, I-026, I-074, I-078, I-089, I-138, I-151, I -154, I-155, I-172, I-195.
  • the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: I-040, I-079, I-107, I-152.
  • the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: I-073, I-077, I-085, I-115, I-159, I-160, I-196, I -197.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 20 ppm: I-184, I-195, I-197.
  • Meloidogyne incognita test solvent 125.0 parts by weight of acetone
  • To prepare a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
  • Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots.
  • the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to the untreated control.
  • the following compounds of the preparation examples effect of 100% at a rate of 20ppm: I-025 In this test show z.
  • the following compounds of the Preparation Examples have an effect of 90% at an application rate of 20 ppm: I-028, I-038, I-104, I-138, I-162, I-177, I-257, I-259.
  • Myzus persicae - Spray Test Solvent 78 parts by weight of acetone
  • Emulsifier alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration. After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed. In this test, z.
  • the following compounds of the preparation examples effect of 90% at a rate of 500g / ha: I-028, I-175.
  • Phaedon cochleariae - Spray Test Solvent 78.0 parts by weight acetone
  • Emulsifier alkylaryl polyglycol ether
  • 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached.
  • dilute with emulsifier-containing water Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae). After 7 days, the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • the following compounds of the preparation examples have an effect of 100% at a rate of 500 g / ha: I-002, I-004, I-005, I-007, I-009, I-011, I-012, I-013 , I-015, I-017, I-018, I-019, I-020, I-021, I-022, I-024, I-025, I-026, I-027, I-028, I -030, I-031, I-035, I-039, I-040, I-041, I-042, I-043, I-044, I-048, I-051, I-052, I-053, I-055, I-056, I-060, I-061, I- 064, I-066, I-067, I-068, I-070, I-074, I-075, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-084, I-085, I-086,
  • the following compounds of the Preparation Examples have an effect of 83% at a rate of 500 g / ha: I-016, I-037, I-038, I-045, I-050, I-057, I-065, I-069 , I-071, I-087, I-095, I-101, I-108, I-135, I-155, I-191, I-194, I-210, I-217, I-237, I -238, I-258, I-259, I-261, I-268, I-271, I-272, I-277. In this test, z.
  • the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 g / ha: I-005, I-011, I-012, I-013, I-026, I-027, I-030, I-038 , I-039, I-040, I-041, I-042, I-044, I-045, I-051, I-052, I-068, I-074, I-076, I-080, I -082, I-085, I-089, I-093, I-094, I-096, I-098, I-099, I-102, I-105, I-106, I-107, I-110 , I-111, I-115, I-116, I-118, I-119, I-120, I-124, I-128, I-129, I-130, I-137, I-138, I -140, I-141, I-142, I-144, I-145, I-147, I-149, I-151, I-152, I-153, I-154
  • Emulsifier alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached.
  • dilute with emulsifier-containing water Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda). After 7 days, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed. In this test, z.
  • the following compounds of the Preparation Examples have an effect of 100% at a rate of 500 g / ha: I-004, I-005, I-006, I-008, I-009, I-010, I-011, I-012 , I-013, I-015, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-025, I-026, I-027, I -028, I-030, I-031, I-032, I-033, I-034, I-035, I-037, I-039, I-040, I-041, I-042, I-043 , I-044, I-045, I-048, I-051, I-052, I-053, I-054, I-055, I-056, I-057, I-058, I-059, I -060, I-061, I-062, I-063, I-064, I-065, I-066, I-067, I-068, I-071, I-
  • the following compounds of the preparation examples have an effect of 100% at a rate of 100 g / ha: I-005, I-008, I-013, I-015, I-022, I-025, I-026, I-027 , I-039, I-041, I-044, I-051, I-052, I-055, I-056, I-061, I-064, I-065, I-067, I-068, I -071, I-074, I-076, I-077, I-078, I-079, I-081, I-082, I-085, I-086, I-087, I-088, I-089 , I-091, I-096, I-098, I-099, I-108, I-110, I-111, I-115, I-117, I-118, I-119, I-120, I -122, I-124, I-125, I-128, I-129, I-131, I-132, I-133, I-137, I-138, I-109
  • the following compounds of the Preparation Examples have an effect of 80% at an application rate of 100 g / ha: I-106, I-221. Tetranychus urticae spray test, OP-resistant Solvent: 78.0 parts by weight of acetone
  • Emulsifier alkylaryl polyglycol ether
  • 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration. After 6 days, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, z.
  • Example the following compounds of the preparation examples, an effect of 100% at a rate of 500g / ha: I-105
  • the following compounds of the preparation examples have an effect of 90% at an application rate of 500 g / ha: I-036, I-091, I-101, I-104, I-182, I-185, I-194, I- 218, I-227, I-255.
  • the following compounds of the Preparation Examples have an effect of 90% at a rate of 100 g / ha: I-100, I-194, I-218, I-227.

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Abstract

The invention relates to novel substituted pyridine compounds of formula (I), in which R1, R2, R3, R4, R5, R6, V1, V2 and Q1 have the meanings given in the description and to their use as acaricides and insecticides for the control of animal pests above all arthropods, particularly insects and arachnids and to methods and intermediate products for the production thereof.

Description

N-(CYANBENZYL)-6-(CYCLOPROPYLCARBONYLAMINO)-4-(PHENYL)-PYRIDIN-2-CARBOXAMID-DERIVATE UND VERWANDTE VERBINDUNGEN ALS PESTIZIDE PFLANZENSCHUTZMITTEL  N- (CYANBENZYL) -6- (CYCLOPROPYLCARBONYLAMINO) -4- (PHENYL) -PYRIDINE-2-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS PESTICIDE PLANT PROTECTION AGENTS
Die vorliegende Erfindung betrifft neue substituierte Pyridinverbindungen der Formel (I), deren Anwendung als Akarizide und/oder Insektizide zur Bekämpfung tierischer Schädlinge, vor allem von Arthropoden und insbesondere von Insekten und Spinnentieren und Verfahren und Zwischenprodukte zu ihrer Herstellung. The present invention relates to novel substituted pyridine compounds of the formula (I), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular insects and arachnids, and methods and intermediates for their preparation.
In WO 2012/054510 AI werden in 4-Position durch Oxadiazol substituierte Pyridine als Inhibitoren der beta-Sekretaseaktivität beschrieben, die insbesondere für die Behandlung von Alzheimer-Erkrankungen eingesetzt werden können. WO 2012/054510 A1 describes oxadiazole-substituted pyridines as inhibitors of beta-secretase activity in the 4-position, which can be used in particular for the treatment of Alzheimer's diseases.
WO 2012/069366 AI offenbart unter anderem in Tabelle F insektizid wirksame und eine Pyridinyl- Gruppe enthaltende Verbindungen, die eine mit Fluoralkyl substituierte Pyrazolgruppe (Q2) enthalten, welche über die Gruppierung -NH-CO- an die Pyridinyl-Gruppe gebunden ist. WO 2012/069366 A1 discloses, inter alia, in Table F insecticidal and containing a pyridinyl group-containing compounds containing a fluoroalkyl-substituted pyrazole group (Q2), which is bound via the grouping -NH-CO- to the pyridinyl group.
Die erfindungsgemäßen Verbindungen enthalten dagegen einen Substituenten Ql in Position 4 am Pyridin-Ring, welcher zwingend ggf. substituiertes Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-l,4- benzodioxinyl, Hetaryl oder Oxo-Hetaryl ist. Ein solcher Substituent ist in den in WO 2012/069366 AI offenbarten Verbindungen jedoch nicht vorhanden. In contrast, the compounds according to the invention contain a substituent Q1 in position 4 on the pyridine ring, which is necessarily substituted or unsubstituted aryl, 1,3-benzodioxolyl, 2,3-dihydro-l, 4-benzodioxinyl, hetaryl or oxo-hetaryl. However, such a substituent is not present in the compounds disclosed in WO 2012/069366 Al.
Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Kombinierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rolle sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss. Ferner können Resistenzen auftreten. Schon aus all diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nicht als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. Modern plant protection products have to meet many requirements, for example with regard to the amount, duration and breadth of their effect and possible use. Issues of toxicity, of the ability to be combined with other active substances or formulation auxiliaries play a role, as well as the question of the effort that has to be spent on the synthesis of an active substance. Furthermore, resistances can occur. For all these reasons, the search for new pesticides can not be considered complete and there is a constant need for new compounds with improved properties compared with the known compounds, at least with regard to individual aspects.
Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert und/oder ihre Aktivität verbessert wird. The object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity.
Es wurde nun überraschend gefunden, dass bestimmte neue substituierte Pyridinverbindungen der Formel (I) sowie deren Salze starke Insektizide und akarizide Eigenschaften bei gleichzeitig guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit besitzen. It has now surprisingly been found that certain novel substituted pyridine compounds of the formula (I) and their salts have strong insecticidal and acaricidal properties with simultaneously good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility.
Gegenstand der vorliegenden Erfindung (Ausgestaltung 1-1) sind daher Verbindungen der allgemeinen Formel (I) in denen The present invention (embodiment 1-1) is therefore compounds of the general formula (I) in which
Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl oder Oxo-Hetaryl steht, wobei die Substituenten ausgewählt sind aus: Cyano, Carboxyl, Halogen, Nitro, Hydroxy, Amino, SCN, SF5, Tri-(C1-C6)alkylsilyl, (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1- C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, Hydroxycarbonyl-(C1-C6)-alkoxy, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Halogenalkinyl, (C2- C6)Cyanoalkinyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkoxy, (C1-C6)Cyanoalkoxy, (C1- C6)Alkoxycarbonyl-(C1-C6)alkoxy, (C1-C6)Alkoxy-(C1-C6)alkoxy, (C3-C8)Cycloalkyl, (C3- C8)Halogencycloalkyl, (C1-C6)Alkyl-(C3-C8)cycloalkyl, (C1-C6)Halogenalkyl-(C3- C8)cycloalkyl, (C1-C4)Halogenalkenoxy, (C1-C6)Alkylhydroxyimino, (C1-C6)Alkoxyimino, (C1- C6)Alkyl-(C1-C6)alkoxyimino, (C1-C6)Halogenalkyl-(C1-C6)alkoxyimino, (C1-C6)Alkylsulfanyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfanyl, (C1-C6)Alkylsulfanyl-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfinyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfonyl, (C1-C6)Alkoxy-(C1- C6)alkylsulfonyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyloxy, (C1- C6)Halogenalkylsulfanyl, (C3-C6)Cycloalkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C3- C6)Cycloalkylsulfonyl, (C3-C6)Halogencycloalkylsulfonyl, (C3-C6)Cycloalkylsulfinyl, (C3- C6)Halogencycloalkylsulfinyl, (C1-C6)Alkylcarbonyl, (C1-C6)Halogenalkylcarbonyl, (C1- C6)Alkylcarbonyloxy, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkoxycarbonyl, Aminocarbonyl, (C1-C6)Alkylaminocarbonyl, Di-(C1-C6)alkyl-aminocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-C6)-alkenylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, (C1- C6)Alkylsulfonylamino, (C1-C6)Alkylamino, Di-(C1-C6)Alkylamino, (C1- C6)Halogenalkylamino, Bis-(C1-C6)Halogenalkylamino, Aminosulfonyl, (C1- C6)Alkylaminosulfonyl, Di-(C1-C6)alkylaminosulfonyl, (C1-C6)Alkylsulfoximino, Aminothiocarbonyl, (C1-C6)Alkylaminothiocarbonyl, Di-(C1-C6)alkylaminothiocarbonyl, (C3- C8)Cycloalkylamino, R1 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C1-C6)alkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1- C6)Alkyl-(C3-C8)Cycloalkyl, (C1-C6)Halogenalkyl-(C3-C8)cycloalkyl, Halogen(C3- C8)cycloalkyl, Cyano(C3-C8)cycloalkyl, (C2-C6)Alkinyl-(C3-C8)cycloalkyl, (C1-C6)Alkoxy-(C3- C8)cycloalkyl, (C1-C6)Alkoxycarbonyl-(C3-C8)cycloalkyl, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C8)Cycloalkylamino, (C1-C6)Alkylcarbonyl-amino, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, (C1- C6)Alkylsulfonylamino, Aminosulfonyl-(C1-C6)alkyl, (C1-C6)Alkylaminosulfonyl-(C1-C6)alkyl, Di-(C1-C6)alkyl-aminosulfonyl-(C1-C6)alkyl, (C1-C4)Alkoxy, (C3-C6)Cycloalkoxy, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkylcarbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiertes (C1-C6)Alkyl, (C1- C6)Alkoxy, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C8)Cycloalkyl steht, wobei Aryl, Hetaryl, Oxo- Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkyl, (C1- C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1- C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino-(C2- C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl oder (C3-C6)Trialkylsilyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1- C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1- C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino-(C2- C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3- C6)Trialkylsilyl, R2 für Wasserstoff, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C8)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1- C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2- C6)Alkenyl, (C2-C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, Aminocarbonyl- (C1-C6)alkyl, (C1-C6)Alkylamino-(C1-C6)alkyl, Di-(C1-C6)alkylamino-(C1-C6)alkyl oder (C3- C8)Cycloalkylamino-(C1-C6)alkyl steht, R3 für Wasserstoff, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C8)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1- C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2- C6)Alkenyl, (C2-C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, Aminocarbonyl- (C1-C6)alkyl, (C1-C6)Alkylamino-(C1-C6)alkyl, Di-(C1-C6)alkylamino-(C1-C6)alkyl oder (C3- C8)Cycloalkylamino-(C1-C6)alkyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C1-C6)alkyl, Cyano(C3-C8)cycloalkyl-(C1-C6)alkyl, Halogen(C3-C8)cycloalkyl-(C1-C6)alkyl, (C1-C4)Halogenalkyl-(C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, (C1-C6)Halogenalkyl- (C3-C8)cycloalkyl, Halogen(C3-C8)cycloalkyl, Cyano(C3-C8)cycloalkyl, (C2-C6)Alkinyl-(C3- C8)cycloalkyl, (C1-C6)Alkoxy-(C3-C8)cycloalkyl, (C1-C6)Alkoxycarbonyl-(C3-C8)cycloalkyl, Carbamoyl-(C3-C8)cycloalkyl, Thiocarbamoyl-(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1- C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, (C1- C6)Alkylsulfonylamino, Aminosulfonyl-(C1-C6)alkyl, (C1-C6)Alkylaminosulfonyl-(C1-C6)alkyl Di-(C1-C6)alkyl-aminosulfonyl-(C1-C6)alkyl, Amino, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C8)Cycloalkylamino, N-(C1-C6)alkyl-(C3-C8)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Halogenbenzylamino, N-(C1-C6)alkyl-Benzylamino, N- (C1-C6)alkyl-Cyanobenzylamino, N-(C1-C6)alkyl-Nitrobenzylamino, N-(C1-C6)alkyl- Halogenbenzylamino, (C1-C6)Alkylcarbonyl-amino, (C3-C8)Cycloalkylcarbonylamino, Hydroxy, (C1-C6)Alkoxy, (C3-C8)Cycloalkoxy, (C3-C8)Cycloalkyl-(C1-C6)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Halogenbenzyloxy, (C1-C6)Alkylimino, (C3- C8)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino oder Halogenbenzylimino steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl substituiertes (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Alkoxy, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C8)Cycloalkyl, Oxy, Amino, N-(C1-C6)Alkylamino oder N-(C3- C8)Cycloalkylamino steht, wobei Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1- C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfinyl, (C1- C6)Halogenalkylsulfonyl, (C1-C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1- C6)Alkylsulfimino-(C2-C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino- (C1-C6)alkyl, (C1-C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1- C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Hetaryl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1- C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1- C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Halogenalkyl- sulfonyl, (C1-C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino- (C2-C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3- C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C6)-Alkyl oder für (C2-C6)Alkenyl stehen, wobei ein 3-7 gliedriger gegebenfalls durch Halogen, Cyano, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C6)Alkyl, (C3- C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio oder (C1-C6)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, (C1- C6)Alkylamino, Di-(C1-C6)Alkylamino, (C3-C6)Cycloalkyl, Halogen(C3-C6)cycloalkyl, (C1- C6)Alkyl, (C1-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Alkinyl, (C2- C6)Halogenalkinyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1- C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfonyl, stehen, V1, V2 unabhängig voneinander für Sauerstoff oder Schwefel stehen. Alternativ und ebenfalls Teil der vorliegenden Erfindung (Ausgestaltung 1-2) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl oder Oxo-Hetaryl steht, wobei die Substituenten ausgewählt sind aus: Cyano, Carboxyl, Halogen, Nitro, Hydroxy, Amino, SCN, SF5, Tri-(C1-C6)alkylsilyl, (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1- C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, Hydroxycarbonyl-(C1-C6)-alkoxy, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Halogenalkinyl, (C2- C6)Cyanoalkinyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkoxy, (C1-C6)Cyanoalkoxy, (C1- C6)Alkoxycarbonyl-(C1-C6)alkoxy, (C1-C6)Alkoxy-(C1-C6)alkoxy, (C3-C8)Cycloalkyl, (C3- C8)Halogencycloalkyl, (C1-C6)Alkyl-(C3-C8)cycloalkyl, (C1-C6)Halogenalkyl-(C3-C8)cycloalkyl, (C1-C4)Halogenalkenoxy, (C1-C6)Alkylhydroxyimino, (C1-C6)Alkoxyimino, (C1-C6)Alkyl-(C1- C6)alkoxyimino, (C1-C6)Halogenalkyl-(C1-C6)alkoxyimino, (C1-C6)Alkylsulfanyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfanyl, (C1-C6)Alkylsulfanyl-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl, (C1- C6)Halogenalkylsulfinyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfinyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfonyl, (C1-C6)Alkoxy-(C1- C6)alkylsulfonyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyloxy, (C1- C6)Halogenalkylsulfanyl, (C3-C6)Cycloalkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C3- C6)Cycloalkylsulfonyl, (C3-C6)Halogencycloalkylsulfonyl, (C3-C6)Cycloalkylsulfinyl, (C3- C6)Halogencycloalkylsulfinyl, (C1-C6)Alkylcarbonyl, (C1-C6)Halogenalkylcarbonyl, (C1- C6)Alkylcarbonyloxy, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkoxycarbonyl, Aminocarbonyl, (C1-C6)Alkylaminocarbonyl, Di-(C1-C6)alkyl-aminocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-C6)-alkenylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, (C1- C6)Alkylsulfonylamino, (C1-C6)Alkylamino, Di-(C1-C6)Alkylamino, (C1- C6)Halogenalkylamino, Bis-(C1-C6)Halogenalkylamino, Aminosulfonyl, (C1- C6)Alkylaminosulfonyl, Di-(C1-C6)alkylaminosulfonyl, (C1-C6)Alkylsulfoximino, Aminothiocarbonyl, (C1-C6)Alkylaminothiocarbonyl, Di-(C1-C6)alkylaminothiocarbonyl, (C3- C8)Cycloalkylamino, R1 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C1-C6)alkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1- C6)Alkyl-(C3-C8)Cycloalkyl, (C1-C6)Halogenalkyl-(C3-C8)cycloalkyl, Halogen(C3- C8)cycloalkyl, Cyano(C3-C8)cycloalkyl, (C2-C6)Alkinyl-(C3-C8)cycloalkyl, (C1-C6)Alkoxy-(C3- C8)cycloalkyl, (C1-C6)Alkoxycarbonyl-(C3-C8)cycloalkyl, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C8)Cycloalkylamino, (C1-C6)Alkylcarbonyl-amino, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, (C1- C6)Alkylsulfonylamino, Aminosulfonyl-(C1-C6)alkyl, (C1-C6)Alkylaminosulfonyl-(C1-C6)alkyl, Di-(C1-C6)alkyl-aminosulfonyl-(C1-C6)alkyl, (C1-C4)Alkoxy, (C3-C6)Cycloalkoxy, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkylcarbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiertes (C1-C6)Alkyl, (C1- C6)Alkoxy, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C8)Cycloalkyl steht, wobei Aryl, Hetaryl, Oxo- Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkyl, (C1- C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1- C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino-(C2- C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl oder (C3-C6)Trialkylsilyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1- C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1- C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino-(C2- C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3- C6)Trialkylsilyl, R2 für Wasserstoff, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C8)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1- C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2- C6)Alkenyl, (C2-C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, Aminocarbonyl- (C1-C6)alkyl, (C1-C6)Alkylamino-(C1-C6)alkyl, Di-(C1-C6)alkylamino-(C1-C6)alkyl oder (C3- C8)Cycloalkylamino-(C1-C6)alkyl steht, R3 für Wasserstoff, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C8)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1- C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2- C6)Alkenyl, (C2-C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, Aminocarbonyl- (C1-C6)alkyl, (C1-C6)Alkylamino-(C1-C6)alkyl, Di-(C1-C6)alkylamino-(C1-C6)alkyl oder (C3- C8)Cycloalkylamino-(C1-C6)alkyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C1-C6)alkyl, Cyano(C3-C8)cycloalkyl-(C1-C6)alkyl, Halogen(C3-C8)cycloalkyl-(C1-C6)alkyl, (C1-C4)Halogenalkyl-(C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, (C1-C6)Halogenalkyl- (C3-C8)cycloalkyl, Halogen(C3-C8)cycloalkyl, Cyano(C3-C8)cycloalkyl, (C2-C6)Alkinyl-(C3- C8)cycloalkyl, (C1-C6)Alkoxy-(C3-C8)cycloalkyl, (C1-C6)Alkoxycarbonyl-(C3-C8)cycloalkyl, Carbamoyl-(C3-C8)cycloalkyl, Thiocarbamoyl-(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1- C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, (C1- C6)Alkylsulfonylamino, Aminosulfonyl-(C1-C6)alkyl, (C1-C6)Alkylaminosulfonyl-(C1-C6)alkyl Di-(C1-C6)alkyl-aminosulfonyl-(C1-C6)alkyl, Amino, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C8)Cycloalkylamino, N-(C1-C6)alkyl-(C3-C8)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Halogenbenzylamino, N-(C1-C6)alkyl-Benzylamino, N- (C1-C6)alkyl-Cyanobenzylamino, N-(C1-C6)alkyl-Nitrobenzylamino, N-(C1-C6)alkyl- Halogenbenzylamino, (C1-C6)Alkylcarbonyl-amino, (C3-C8)Cycloalkylcarbonylamino, Hydroxy, (C1-C6)Alkoxy, (C3-C8)Cycloalkoxy, (C3-C8)Cycloalkyl-(C1-C6)Alkoxy, Cyano(C1- C6)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Halogenbenzyloxy, (C1- C6)Alkylimino, (C3-C8)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino, Halogenbenzylimino, (C1-C6)Halogenalkylbenzylimino, Halogen-[(C1- C6)Halogenalkyl]benzylimino, (C1-C6)Alkylcarbonyl, (C1-C6)Halogenalkylcarbonyl, (C3- C8)Cycloalkylcarbonyl oder (C3-C8)Cycloalkyl-(C1-C6)alkyl-carbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl substituiertes (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Alkoxy, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C8)Cycloalkyl, Oxy, Amino, N-(C1-C6)Alkylamino, N-(C3- C8)Cycloalkylamino oder Carbonyl steht, wobei Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4- benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C6)Alkyl, (C3- C6)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkyl- sulfinyl, (C1-C6)Halogenalkylsulfonyl, (C1-C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1- C6)alkyl, (C1-C6)Alkylsulfimino-(C2-C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1- C6)Alkylsulfoximino-(C1-C6)alkyl, (C1-C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Hetaryl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1- C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1- C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Halogenalkyl- sulfonyl, (C1-C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino- (C2-C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3- C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C6)-Alkyl oder für (C2-C6)Alkenyl stehen, wobei ein 3-7 gliedriger gegebenfalls durch Halogen, Cyano, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C6)Alkyl, (C3- C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio oder (C1-C6)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, (C1- C6)Alkylamino, Di-(C1-C6)Alkylamino, (C3-C6)Cycloalkyl, Halogen(C3-C6)cycloalkyl, (C1- C6)Alkyl, (C1-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Alkinyl, (C2- C6)Halogenalkinyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1- C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfonyl, stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. Weiterhin wurde gefunden, dass die Verbindungen der Formel (I) eine sehr gute Wirksamkeit als Schädlingsbekämpfungsmittel, vorzugsweise als Insektizide und/oder Akarizide aufweisen, darüber hinaus in der Regel insbesondere gegenüber Kulturpflanzen sehr gut pflanzenverträglich sind. Die erfindungsgemäßen Verbindungen sind durch die Formel (I) allgemein definiert. Bevorzugte Substituenten bzw. Bereiche der in der oben und nachstehend erwähnten Formeln aufgeführten Reste werden im Folgenden erläutert: Bevorzugter Bereich: Bevorzugt (Ausgestaltung 2-1) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl oder Oxo-Hetaryl steht, wobei die Substituenten ausgewählt sind aus Cyano, Halogen, Nitro, Amino, SF5, (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkoxy, (C1- C4)Cyanoalkoxy, (C1-C4)Alkoxy-(C1-C4)alkoxy, (C3-C6)Cycloalkyl, (C3-C6)Halogencycloalkyl, (C1-C4)Alkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, (C1- C4)Halogenalkenoxy, (C1-C4)Alkylhydroxyimino, (C1-C4)Alkoxyimino, (C1-C4)Alkyl-(C1- C4)alkoxyimino, (C1-C4)Halogenalkyl-(C1-C4)alkoxyimino, (C1-C4)Alkylsulfanyl, (C1- C4)Alkylsulfanyl-(C1-C4)alkyl, (C1-C4)Alkylsulfinyl, (C1-C4)Halogenalkylsulfinyl, (C1- C4)Alkylsulfinyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfonyl, (C1- C4)Alkylsulfonyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyloxy, (C1-C4)Halogenalkylsulfanyl, (C3- C6)Cycloalkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C3-C6)Cycloalkylsulfonyl, (C3- C6)Halogencycloalkylsulfonyl, (C3-C6)Cycloalkylsulfinyl, (C3-C6)Halogencycloalkylsulfinyl, (C1-C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, Aminocarbonyl, (C1- C4)Alkylaminocarbonyl, Di-(C1-C4)alkyl-aminocarbonyl, (C1-C4)Alkylsulfonylamino, (C1- C4)Alkylamino, Di-(C1-C4)Alkylamino, (C1-C6)Halogenalkylamino, Bis-(C1- C6)Halogenalkylamino, Aminosulfonyl, (C1-C4)Alkylaminosulfonyl, Di-(C1- C4)alkylaminosulfonyl, R1 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C6)alkyl, (C2- C4)Halogenalkinyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1- C4)Alkyl-(C3-C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3- C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C6)Cycloalkylamino, (C1-C4)Alkylthio-(C1-C6)alkyl, (C1-C4)Halogenalkylthio-(C1- C6)alkyl, (C1-C4)Alkylsulfinyl-(C1-C6)alkyl, (C1-C4)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1- C4)Alkylsulfonyl-(C1-C6)alkyl, (C1-C4)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1- C4)Alkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxy, (C3- C6)Cycloalkoxy, (C3-C6)Cycloalkylcarbonyl oder (C1-C4)Alkylcarbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiertes (C1-C4)Alkyl, (C1- C4)Alkoxy, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl steht, wobei Aryl, Hetaryl, Oxo- Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1- C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl oder (C3-C6)Trialkylsilyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1- C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl steht, R2 für Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C4)Halogenalkyl oder (C1-C4)Cyanoalkyl steht, R3 für Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C4)Halogenalkyl oder (C1-C4)Cyanoalkyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2- C4)Alkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C2- C4)Halogenalkinyloxy-(C1-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C6)alkyl, Cyano(C3-C6)cycloalkyl-(C1-C6)alkyl, Halogen(C3-C6)cycloalkyl-(C1-C6)alkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl-(C1-C6)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1-C6)Alkyl-(C3-C6)Cycloalkyl, (C1-C6)Halogenalkyl- (C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3- C6)cycloalkyl, (C1-C4)Alkoxy-(C3-C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, Carbamoyl-(C3-C6)cycloalkyl, Thiocarbamoyl-(C3-C6)cycloalkyl, (C1-C4)Alkylthio-(C1- C4)alkyl, (C1-C4)Halogenalkylthio-(C1-C4)alkyl, (C1-C4)Alkylsulfinyl-(C1-C4)alkyl, (C1- C4)Halogenalkylsulfinyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyl-(C1-C4)alkyl, (C1- C4)Halogenalkylsulfonyl-(C1-C4)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1- C4)Halogenalkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonylamino, Aminosulfonyl-(C1- C4)alkyl, (C1-C4)Alkylaminosulfonyl-(C1-C4)alkyl, oder Di-(C1-C4)alkyl-aminosulfonyl-(C1- C6)alkyl, Amino, (C1-C4)Alkylamino, Di-(C1-C4)alkyl-amino, (C3-C6)Cycloalkylamino, N-(C1- C4)alkyl-(C3-C6)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Halogenbenzylamino, N-(C1-C4)alkyl-Benzylamino, N-(C1-C4)alkyl-Cyanobenzylamino, N-(C1- C4)alkyl-Nitrobenzylamino, N-(C1-C4)alkyl-Halogenbenzylamino, (C1-C4)Alkylcarbonyl-amino, (C3-C6)Cycloalkylcarbonylamino, Hydroxy, (C1-C4)Alkoxy, (C3-C6)Cycloalkoxy, (C3- C6)Cycloalkyl-(C1-C4)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Halogenbenzyloxy, (C1-C4)Alkylimino, (C3-C6)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino oder Halogenbenzylimino steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl substituiertes (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Alkoxy, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl, Oxy, Amino, N-(C1-C4)Alkylamino oder N-(C3- C6)Cycloalkylamino steht, wobei Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1- C4)Halogenalkylsulfonyl, (C1-C4)Alkylsulfimino, (C1-C4)Alkylsulfimino-(C1-C4)alkyl, (C1- C4)Alkylsulfoximino, (C1-C4)Alkylsulfoximino-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl, (C1- C4)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Hetaryl substituiert sein können, oder oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1-C4)Halogenalkyl- sulfonyl, (C1-C4)Alkylsulfimino, (C1-C4)Alkylsulfimino-(C1-C4)alkyl, (C1-C4)Alkylsulfoximino, (C1-C4)Alkylsulfoximino-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Alkylcarbonyl, (C3- C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C6)-Alkyl oder für (C2-C6)Alkenyl stehen, wobei ein 3-7 gliedriger gegebenfalls durch Halogen, Cyano, Hydroxy, Amino, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)- Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio oder (C1-C4)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, (C3-C6)Cycloalkyl, (C1- C4)Alkyl, (C1-C4)Halogenalkyl oder (C1-C4)Halogenalkoxy stehen, V1, V2 unabhängig voneinander für Sauerstoff oder Schwefel stehen. Alternativ und ebenfalls bevorzugt (Ausgestaltung 2-2) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl oder Oxo-Hetaryl steht, wobei die Substituenten ausgewählt sind aus Cyano, Halogen, Nitro, Amino, SF5, (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkoxy, (C1- C4)Cyanoalkoxy, (C1-C4)Alkoxy-(C1-C4)alkoxy, (C3-C6)Cycloalkyl, (C3-C6)Halogencycloalkyl, (C1-C4)Alkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, (C1- C4)Halogenalkenoxy, (C1-C4)Alkylhydroxyimino, (C1-C4)Alkoxyimino, (C1-C4)Alkyl-(C1- C4)alkoxyimino, (C1-C4)Halogenalkyl-(C1-C4)alkoxyimino, (C1-C4)Alkylsulfanyl, (C1- C4)Alkylsulfanyl-(C1-C4)alkyl, (C1-C4)Alkylsulfinyl, (C1-C4)Halogenalkylsulfinyl, (C1- C4)Alkylsulfinyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfonyl, (C1- C4)Alkylsulfonyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyloxy, (C1-C4)Halogenalkylsulfanyl, (C3- C6)Cycloalkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C3-C6)Cycloalkylsulfonyl, (C3- C6)Halogencycloalkylsulfonyl, (C3-C6)Cycloalkylsulfinyl, (C3-C6)Halogencycloalkylsulfinyl, (C1-C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, Aminocarbonyl, (C1- C4)Alkylaminocarbonyl, Di-(C1-C4)alkyl-aminocarbonyl, (C1-C4)Alkylsulfonylamino, (C1- C4)Alkylamino, Di-(C1-C4)Alkylamino, (C1-C6)Halogenalkylamino, Bis-(C1- C6)Halogenalkylamino, Aminosulfonyl, (C1-C4)Alkylaminosulfonyl, Di-(C1- C4)alkylaminosulfonyl, R1 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C6)alkyl, (C2- C4)Halogenalkinyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1- C4)Alkyl-(C3-C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3- C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C6)Cycloalkylamino, (C1-C4)Alkylthio-(C1-C6)alkyl, (C1-C4)Halogenalkylthio-(C1- C6)alkyl, (C1-C4)Alkylsulfinyl-(C1-C6)alkyl, (C1-C4)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1- C4)Alkylsulfonyl-(C1-C6)alkyl, (C1-C4)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1- C4)Alkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxy, (C3- C6)Cycloalkoxy, (C3-C6)Cycloalkylcarbonyl oder (C1-C4)Alkylcarbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiertes (C1-C4)Alkyl, (C1- C4)Alkoxy, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl steht, wobei Aryl, Hetaryl, Oxo- Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1- C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl oder (C3-C6)Trialkylsilyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1- C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl steht, R2 für Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C4)Halogenalkyl oder (C1-C4)Cyanoalkyl steht, R3 für Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C4)Halogenalkyl oder (C1-C4)Cyanoalkyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2- C4)Alkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C2- C4)Halogenalkinyloxy-(C1-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C6)alkyl, Cyano(C3-C6)cycloalkyl-(C1-C6)alkyl, Halogen(C3-C6)cycloalkyl-(C1-C6)alkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl-(C1-C6)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1-C6)Alkyl-(C3-C6)Cycloalkyl, (C1-C6)Halogenalkyl- (C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3- C6)cycloalkyl, (C1-C4)Alkoxy-(C3-C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, Carbamoyl-(C3-C6)cycloalkyl, Thiocarbamoyl-(C3-C6)cycloalkyl, (C1-C4)Alkylthio-(C1- C4)alkyl, (C1-C4)Halogenalkylthio-(C1-C4)alkyl, (C1-C4)Alkylsulfinyl-(C1-C4)alkyl, (C1- C4)Halogenalkylsulfinyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyl-(C1-C4)alkyl, (C1- C4)Halogenalkylsulfonyl-(C1-C4)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1- C4)Halogenalkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonylamino, Aminosulfonyl-(C1- C4)alkyl, (C1-C4)Alkylaminosulfonyl-(C1-C4)alkyl, oder Di-(C1-C4)alkyl-aminosulfonyl-(C1- C6)alkyl, Amino, (C1-C4)Alkylamino, Di-(C1-C4)alkyl-amino, (C3-C6)Cycloalkylamino, N-(C1- C4)alkyl-(C3-C6)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Halogenbenzylamino, N-(C1-C4)alkyl-Benzylamino, N-(C1-C4)alkyl-Cyanobenzylamino, N-(C1- C4)alkyl-Nitrobenzylamino, N-(C1-C4)alkyl-Halogenbenzylamino, (C1-C4)Alkylcarbonyl-amino, (C3-C6)Cycloalkylcarbonylamino, Hydroxy, (C1-C4)Alkoxy, (C3-C6)Cycloalkoxy, (C3- C6)Cycloalkyl-(C1-C4)Alkoxy, Cyano(C1-C4)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Halogenbenzyloxy, (C1-C4)Alkylimino, (C3-C6)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino, Halogenbenzylimino, (C1-C4)Halogenalkylbenzylimino, Halogen-[(C1-C4)Halogenalkyl]benzylimino, (C1-C4)Alkylcarbonyl, (C1- C4)Halogenalkylcarbonyl, (C3-C6)Cycloalkylcarbonyl oder (C3-C6)Cycloalkyl-(C1-C4)alkyl- carbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl substituiertes (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Alkoxy, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl, Oxy, Amino, N-(C1-C4)Alkylamino, N-(C3- C6)Cycloalkylamino oder Carbonyl steht, wobei Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4- benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1- C4)Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1- C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1-C4)Halogenalkylsulfonyl, (C1-C4)Alkylsulfimino, (C1-C4)Alkylsulfimino-(C1-C4)alkyl, (C1- C4)Alkylsulfoximino, (C1-C4)Alkylsulfoximino-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl, (C1- C4)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Hetaryl substituiert sein können, oder oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1-C4)Halogenalkyl- sulfonyl, (C1-C4)Alkylsulfimino, (C1-C4)Alkylsulfimino-(C1-C4)alkyl, (C1-C4)Alkylsulfoximino, (C1-C4)Alkylsulfoximino-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Alkylcarbonyl, (C3- C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C6)-Alkyl oder für (C2-C6)Alkenyl stehen, wobei ein 3-7 gliedriger gegebenfalls durch Halogen, Cyano, Hydroxy, Amino, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)- Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio oder (C1-C4)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, (C3-C6)Cycloalkyl, (C1- C4)Alkyl, (C1-C4)Halogenalkyl oder (C1-C4)Halogenalkoxy stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. Besonders bevorzugter Bereich: Besonders bevorzugt (Ausgestaltung 3-1) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyrimidyl, Pyridazinyl, Pyridyl, Thienyl, Furanyl, Oxazolyl, Thiazolyl, Imidazolyl oder Pyrazolyl steht, wobei die Substituenten ausgewählt sind aus Cyano, Halogen, Nitro, SF5, (C1-C4)Alkyl, (C1- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkoxy, (C3-C6)Cycloalkyl, (C3- C6)Halogencycloalkyl, (C1-C4)Alkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkenoxy, (C1-C4)Alkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C1- C4)Alkylsulfinyl, (C1-C4)Halogenalkylsulfinyl, (C3-C6)Cycloalkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfonyl, (C3-C6)Cycloalkylsulfonyl, (C1-C4)Halogenalkylsulfanyl, (C3- C6)Cycloalkylsulfanyl, (C1-C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, Bis-(C1- C4)Alkylamino, Di-(C1-C4)Halogenalkylamino, R1 für (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Hydroxyalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C2- C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1- C4)Alkyl-(C3-C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3- C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, (C1-C4)Alkylthio-(C1-C6)alkyl, (C1- C4)Alkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C6)alkyl oder (C1-C4)Alkoxy steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl oder Heterocyclyl substituiertes (C1-C4)Alkyl, (C3-C6)Cycloalkyl steht, wobei Aryl, Hetaryl oder Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio oder (C1-C6)Alkoxycarbonyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C6)Alkoxycarbonyl, R2 für Wasserstoff, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkoxycarbonyl steht, R3 für Wasserstoff, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkoxycarbonyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, Cyano(C3- C6)cycloalkyl-(C1-C4)alkyl, Halogen(C3-C6)cycloalkyl-(C1-C4)alkyl, (C1-C4)Halogenalkyl-(C3- C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1-C4)Alkyl-(C3- C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3- C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3-C6)cycloalkyl, (C1- C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, Carbamoyl-(C3-C6)cycloalkyl, Thiocarbamoyl-(C3- C6)cycloalkyl, (C1-C4)Alkylcarbonyl-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, Amino, (C1-C4)Alkylamino, Di-(C1-C4)alkyl-amino, (C3-C6)Cycloalkylamino, N-(C1-C4)alkyl- (C3-C6)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, N-(C1-C4)alkyl- Benzylamino, N-(C1-C4)alkyl-Cyanobenzylamino, N-(C1-C4)alkyl-Nitrobenzylamino, (C1- C4)Alkylcarbonyl-amino, (C3-C6)Cycloalkylcarbonylamino, Hydroxy, (C1-C4)Alkoxy, (C3- C6)Cycloalkoxy, (C3-C6)Cycloalkyl-(C1-C4)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, (C1-C4)Alkylimino, (C3-C6)Cycloalkylimino, Benzylimino, Cyanobenzylimino oder Nitrobenzylimino steht, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocycyl substituiertes (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C2-C4)Alkenyl, (C3-C6)Cycloalkyl, Oxy, Amino, N-(C1-C4)Alkylamino oder N-cyclo-Propylamino steht, wobei Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocycyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C4)Halogenalkylsulfinyl, (C1-C4)Halogenalkylsulfonyl, (C1-C4)Alkoxycarbonyl, (C1- C4)Alkylcarbonyl, Hetaryl oder Alkyl-Hetaryl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1- C4)Halogenalkylsulfonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Alkylcarbonyl, (C3-C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C5)-Alkyl oder für (C2-C5)Alkenyl stehen, wobei ein 3-6 gliedriger gegebenfalls durch Halogen, Cyano, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, oder (C1-C4)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trifluormethoxy stehen, V1, V2 unabhängig voneinander für Sauerstoff oder Schwefel stehen. Q1 is each optionally mono- or polysubstituted by identical or different substituents aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl or oxo-hetaryl, where the substituents are selected from: cyano, carboxyl, Halogen, nitro, hydroxy, amino, SCN, SF5, tri (C 1 -C 6) alkylsilyl, (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 6) cyanoalkyl, (C 1 -C 6) hydroxyalkyl, hydroxycarbonyl - (C 1 -C 6) alkoxy, (C 1 -C 6) alkoxycarbonyl- (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy- (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl , (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C1-C6) alkoxy, (C1-C6) haloalkoxy, (C1-C6) cyanoalkoxy, (C1-C6) alkoxycarbonyl- (C1-C6) alkoxy, (C1-C6) alkoxy- (C1-C6) alkoxy, (C3-C8) cycloalkyl, (C3-C8) halocycloalkyl, (C1-C6) alkyl- ( C3-C8) cycloalkyl, (C1-C6) haloalkyl- (C3-C8) cycloalkyl, (C1-C4) haloalkenoxy, (C1-C6) alkylhydroxyimino, (C1-C6) alkoxyimino, (C1-C6) alkyl- (C1 -C 6) alkoxyimino, (C 1 -C 6) haloalkyl- (C 1 -C 6) alkoxyimino, (C 1 -C 6) alk ylsulfanyl, (C1-C6) alkoxy- (C1-C6) alkylsulfanyl, (C1-C6) alkylsulfanyl- (C1-C6) alkyl, (C1-C6) alkylsulfinyl, (C1-C6) Haloalkylsulfinyl, (C1-C6) Alkoxy (C1-C6) alkylsulfinyl, (C1-C6) Alkylsulfinyl (C1- C6) alkyl, (C1-C6) Alkylsulfonyl, (C1-C6) Haloalkylsulfonyl, (C1-C6) Alkoxy (C1- C6) alkylsulfonyl, (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkylsulfonyloxy, (C1- C6) Haloalkylsulfanyl, (C3-C6) Cycloalkylsulfanyl, (C3-C6) Halocycloalkylsulfanyl, (C3- C6) Cycloalkylsulfonyl, (C3-C6) Halocycloalkylsulfonyl, (C3-C6) Cycloalkylsulfinyl, (C3- C6) Halocycloalkylsulfinyl, (C1-C6) Alkylcarbonyl, (C1-C6) Haloalkylcarbonyl, (C1- C6) Alkylcarbonyloxy, (C1-C6) Alkoxycarbonyl, (C1-C6) Haloalkoxycarbonyl, aminocarbonyl, (C1-C6) Alkylaminocarbonyl, di (C1-C6) alkylaminocarbonyl, (C2-C6) Alkenylaminocarbonyl, di (C2-C6) alkenylaminocarbonyl, (C3-C8th) Cycloalkylaminocarbonyl, (C1- C6) Alkylsulfonylamino, (C1-C6) Alkylamino, di (C1-C6) Alkylamino, (C1- C6) Haloalkylamino, bis (C1-C6) Haloalkylamino, aminosulfonyl, (C1- C6) Alkylaminosulfonyl, di (C1-C6) alkylaminosulfonyl, (C1-C6) Alkylsulfoximino, aminothiocarbonyl, (C1-C6) Alkylaminothiocarbonyl, di (C1-C6) alkylaminothiocarbonyl, (C3- C8th) Cycloalkylamino, R1 for (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1-C6) Cyanoalkyl, (C1-C6) Hydroxyalkyl, (C1-C6) Alkoxy (C1-C6) alkyl, (C1-C6) Haloalkoxy (C1-C6) alkyl, (C2-C6) Alkenyl, (C2- C6) Alkenyloxy (C1-C6) alkyl, (C2-C6) Halogenalkenyloxy- (C1-C6) alkyl, (C2-C6) Haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) alkynyloxy- (C1-C6) alkyl, (C2-  C6) haloalkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl- (C1-C6) -alkyl, (C3-C8 ) Cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) alkyl- (C3-C8) cycloalkyl, (C1-C6) haloalkyl- (C3-C8) cycloalkyl, halo (C3-C8) cycloalkyl, cyano (C3-C8) cycloalkyl- C8) cycloalkyl, (C2-C6) alkynyl- (C3-C8) cycloalkyl, (C1-C6) alkoxy- (C3-C8) cycloalkyl, (C1-C6) alkoxycarbonyl- (C3-C8) cycloalkyl, (C1-C6 ) Alkylamino, di (C 1 -C 6) alkylamino, (C 3 -C 8) cycloalkylamino, (C 1 -C 6) alkylcarbonylamino, (C 1 -C 6) alkylthio (C 1 -C 6) alkyl, (C 1 -C 6) haloalkylthio (C1-C6) alkyl, (C1-C6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) haloalkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) haloalkylsulfonyl- (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylthio (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfinyl- ( C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) alkylcarbonyl- (C1-C6) alkyl, (C1-C6) haloalkylcarbonyl- (C1 -C 6) alkyl, (C 1 -C 6) alkoxycarbonyl (C 1 -C 6) alkyl, (C 1 -C 6) haloalkoxy ruthenyl (C1-C6) alkyl, (C1-C6) alkylsulfonylamino, aminosulfonyl- (C1-C6) alkyl, (C1-C6) alkylaminosulfonyl- (C1-C6) alkyl, di- (C1-C6) alkyl-aminosulfonyl- (C 1 -C 6) alkyl, (C 1 -C 4) alkoxy, (C 3 -C 6) cycloalkoxy, (C 3 -C 6) cycloalkylcarbonyl or (C 1 -C 4) -alkylcarbonyl, or in each case optionally mono- or polysubstituted, identically or differently, by aryl, Hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl substituted (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 3 -C 8) cycloalkyl, wherein aryl , Hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, aminosulfonyl, (C1-C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C6) Alkoxy, (C1-C6) Haloalkyl, (C1- C6) Haloalkoxy, (C1-C6) Alkylthio, (C1-C6) Alkylsulfinyl, (C1-C6) Alkylsulfonyl, (C1- C6) Alkylsulfimino, (C1-C6) Alkylsulfimino- (C1-C6) alkyl, (C1-C6) Alkylsulfimino- (C2- C6) alkylcarbonyl, (C1-C6) Alkylsulfoximino, (C1-C6) Alkylsulfoximino- (C1-C6) alkyl, (C1- C6) Alkylsulfoximino- (C2-C6) alkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl or (C3-C6) Trialkylsilyl may be substituted, or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy , Carbamoyl, (C1- C6) Alkyl, (C3-C8th) Cycloalkyl, (C1-C6) -Alkoxy, (C1-C6) Haloalkyl, (C1-C6) Haloalkoxy, (C1-C6) alkylthio, (C1-C6) haloalkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, (C1-C6) Alkylsulfimino, (C1-C6) Alkylsulfimino- (C1-C6) alkyl, (C1-C6) Alkylsulfimino- (C2- C6) alkylcarbonyl, (C1-C6) Alkylsulfoximino, (C1-C6) Alkylsulfoximino- (C1-C6) alkyl, (C1- C6) Alkylsulfoximino- (C2-C6) alkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl, (C3- C6) Trialkylsilyl, R 2 is hydrogen, (C1-C6) Alkyl, (C3-C8th) Cycloalkyl, (C1-C6) Alkoxy, (C1-C6) Alkylcarbonyl, (C3-  C8) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, (C1-C6) alkoxy- (C1-C6) alkyl, (C1-C6 ) Haloalkoxy- (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkenyloxy- (C1-C6) alkyl, (C2-C6) haloalkenyloxy- (C1-C6) alkyl, (C2-C6) Haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) alkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyl , (C2-C6) cyanoalkynyl, (C3-C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) alkyl- (C3-C8) cycloalkyl, halo (C3-C8) cycloalkyl, (C1-C6) alkylthio (C1-C6) alkyl, (C1-C6) haloalkylthio (C1-C6) alkyl, (C1-C6) alkylsulfinyl (C1-C6) alkyl, (C1-C6) haloalkylsulfinyl (C1-C6) alkyl, (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) haloalkylsulfonyl- (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylthio (C1-C6) alkyl, ( C1-C6) alkoxy- (C1-C6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) alkylcarbonyl- (C1 -C 6) alkyl, (C 1 -C 6) haloalkylcarbonyl (C 1 -C 6) alkyl, (C 1 -C 6) alkoxycarbonyl (C1-C6) alkyl, (C1-C6) haloalkoxycarbonyl- (C1-C6) alkyl, aminocarbonyl- (C1-C6) alkyl, (C1-C6) alkylamino- (C1-C6) alkyl, di- (C1- C6) alkylamino- (C1-C6) alkyl or (C3-C8) cycloalkylamino- (C1-C6) alkyl, R3 represents hydrogen, (C1-C6) alkyl, (C3-C8) cycloalkyl, (C1-C6) alkoxy , (C1-C6) alkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, (C1-C6) alkoxy- (C1-C6) alkyl, (C1-C6) haloalkoxy- (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkenyloxy- (C1-C6) alkyl, (C2-C6) haloalkenyloxy- ( C1-C6) alkyl, (C2-C6) haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) alkynyloxy- (C1-C6) alkyl, (C2-C6) Halogenalkinyloxy- (C1-C6) alkyl, (C2-C6) Haloalkynyl, (C2-C6) Cyanoalkynyl, (C3- C8th) Cycloalkyl (C3-C8th) Cycloalkyl, (C1-C6) Alkyl (C3-C8th) Cycloalkyl, halogen (C3-C8th) cycloalkyl, (C1-C6) Alkylthio (C1-C6) alkyl, (C1-C6) Haloalkylthio (C1-C6) alkyl, (C1-C6) Alkylsulfinyl (C1- C6) alkyl, (C1-C6) Halogenalkylsulfinyl- (C1-C6) alkyl, (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1- C6) Haloalkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylthio (C1-C6) alkyl, (C1- C6) Alkoxy (C1-C6) Alkylsulfinyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkylcarbonyl (C1-C6) alkyl, (C1-C6) Haloalkylcarbonyl (C1-C6) alkyl, (C1- C6) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) Haloalkoxycarbonyl (C1-C6) alkyl, aminocarbonyl (C1-C6) alkyl, (C1-C6) Alkylamino (C1-C6) alkyl, di (C1-C6) Alkylamino (C1-C6) alkyl or (C3- C8th) Cycloalkylamino (C1-C6) alkyl, R4 is (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1-C6) Cyanoalkyl, (C1-C6) Hydroxyalkyl, (C 1 -C 6) alkoxy- (C 1 -C 6) alkyl, (C 1 -C 6) haloalkoxy- (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C6) Alkenyloxy (C1-C6) alkyl, (C2-C6) Halogenalkenyloxy- (C1-C6) alkyl, (C2-C6) Haloalkenyl, (C2-C6) Cyanoalkenyl, (C2-C6) Alkynyl, (C2-C6) Alkynyloxy (C1-C6) alkyl, (C2- C6) Halogenalkinyloxy- (C1-C6) alkyl, (C2-C6) Haloalkynyl, (C2-C6) Cyanoalkynyl, (C3- C8th) Cycloalkyl, (C3-C8th) Cycloalkyl (C1-C6) alkyl, cyano (C3-C8th) Cycloalkyl- (C1-C6) alkyl, halogen (C3-C8th) Cycloalkyl- (C1-C6) alkyl, (C1-C4) Haloalkyl (C3-C8th) Cycloalkyl- (C1-C6) alkyl, (C3-C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) alkyl- (C3-C8) cycloalkyl, (C1-C6) haloalkyl  (C3-C8) cycloalkyl, halo (C3-C8) cycloalkyl, cyano (C3-C8) cycloalkyl, (C2-C6) alkynyl (C3-C8) cycloalkyl, (C1-C6) alkoxy- (C3-C8) cycloalkyl , (C1-C6) alkoxycarbonyl- (C3-C8) -cycloalkyl, carbamoyl- (C3-C8) -cycloalkyl, thiocarbamoyl- (C3-C8) -cycloalkyl, (C1-C6) -alkylthio- (C1-C6) -alkyl, (C1- C6) haloalkylthio (C1-C6) alkyl, (C1-C6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) haloalkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkylsulfonyl- (C1-C6 ) alkyl, (C 1 -C 6) haloalkylsulfonyl (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy (C 1 -C 6) alkylthio (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy (C 1 -C 6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) alkylcarbonyl- (C1-C6) alkyl, (C1-C6) haloalkylcarbonyl (C1-C6) alkyl, (C1-C6) alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) haloalkoxycarbonyl- (C1-C6) alkyl, (C1-C6) alkylsulfonylamino, aminosulfonyl- (C1-C6) alkyl, (C 1 -C 6) alkylaminosulfonyl (C 1 -C 6) alkyl, di (C 1 -C 6) alkylaminosulfonyl (C 1 -C 6) alkyl, amino, (C 1 -C 6) alkylamino, di (C 1 -C 6) alkyl - amino, (C3-C8) cycloalkylamino, N- (C1-C6) alkyl- (C3-C 8) cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, halobenzylamino, N- (C 1 -C 6) alkylbenzylamino, N- (C 1 -C 6) alkyl-cyanobenzylamino, N- (C 1 -C 6) -alkyl-nitrobenzylamino, N- (C 1 -C 6) -alkyl C6) alkyl halobenzylamino, (C1-C6) alkylcarbonylamino, (C3-C8) cycloalkylcarbonylamino, hydroxy, (C1-C6) alkoxy, (C3-C8) cycloalkoxy, (C3-C8) cycloalkyl- (C1-C6) Alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, halobenzyloxy, (C 1 -C 6) alkylimino, (C 3 -C 8) cycloalkylimino, benzylimino, cyanobenzylimino, nitrobenzylimino or halobenzylimino, or in each case optionally mono- or polysubstituted, identically or differently, by aryl, 1,3 Benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl-substituted (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1-C6) Alkoxy, (C2-C6) Alkenyl, (C2-C6) Alkynyl, (C3-C8th) Cycloalkyl, oxy, amino, N- (C1-C6) Alkylamino or N- (C3- C8th) Cycloalkylamino, where aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, Nitro, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C1-C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C6) Alkoxy, (C1-C6) Haloalkyl, (C1-C6) Haloalkoxy, (C1-C6) Alkylthio, (C1-C6) Haloalkylthio, (C1- C6) Alkylsulfinyl, (C1-C6) Alkylsulfonyl, (C1-C6) Haloalkylsulfinyl, (C1- C6) Haloalkylsulfonyl, (C1-C6) Alkylsulfimino, (C1-C6) Alkylsulfimino- (C1-C6) alkyl, (C1C6) alkylsulfimino (C2-C6) alkylcarbonyl, (C1-C6) alkylsulfoximino, (C1-C6) alkylsulfoximino (C1-C6) alkyl, (C1-C6) Alkylsulfoximino- (C2-C6) alkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1- C6) Alkylcarbonyl, (C3-C6) Trialkylsilyl or hetaryl, or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl where the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C 1 -C 6) alkyl, (C 3 -C 8) cycloalkyl, (C 1 -C 6) -alkoxy,  C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) alkylthio, (C1-C6) haloalkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, (C1-C6) haloalkylsulfinyl, (C1-C6 ) Haloalkylsulfonyl, (C1-C6) alkylsulfimino, (C1-C6) alkylsulfimino (C1-C6) alkyl, (C1-C6) alkylsulfimino (C2-C6) alkylcarbonyl, (C1-C6) alkylsulfoximino, (C1- C6) alkylsulfoximino (C1-C6) alkyl, (C1-C6) alkylsulfoximino (C2-C6) alkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkylcarbonyl, (C3-C6) trialkylsilyl, or R3 and R4 together represent (C 2 -C 6) -alkyl or (C 2 -C 6) -alkenyl, where a 3-7 membered is optionally substituted by halogen, cyano, hydroxy, amino, carboxy, carbamoyl, (C 1 -C 6) alkyl, (C 3 -C 8 ) Cycloalkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) alkylthio or (C1-C6) haloalkylthio substituted ring is formed, optionally containing one to two double bonds R5, R6 can independently of one another denote hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, (C1-C6) alkylamino, di- ( C1-C6) alkylamino, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C1-C6) alkyl, (C1-C6) haloalkyl, (C2-C6) alkenyl, (C2-C6) haloalkenyl, ( C 2 -C 6) alkynyl, (C 2 -C 6) haloalkynyl, (C 1 -C 6) alkoxy, (C 1 -C 6) haloalkoxy, (C 1 -C 6) alkylthio, (C 1 -C 6) haloalkylthio, (C 1 -C 6) alkylsulfinyl, (Cl -C6) haloalkylsulfinyl, (C1-C6) alkylsulfonyl, (C1-C6) haloalkylsulfonyl, V1, V2 independently represent oxygen or sulfur. Alternatively, and also part of the present invention (embodiment 1-2) are the compounds of formula (I) in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents aryl, 1,3-benzodioxolyl, 2,3-dihydro- 1,4-benzodioxinyl, hetaryl or oxo-hetaryl, where the substituents are selected from: cyano, carboxyl, halogen, nitro, hydroxy, amino, SCN, SF5, Tri- (C1-C6) alkylsilyl, (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1- C6) Cyanoalkyl, (C1-C6) Hydroxyalkyl, hydroxycarbonyl- (C1-C6) -alkoxy, (C1- C6) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) alkyl, (C2-C6) Alkenyl, (C2- C6) Haloalkenyl, (C2-C6) Cyanoalkenyl, (C2-C6) Alkynyl, (C2-C6) Haloalkynyl, (C2- C6) Cyanoalkynyl, (C1-C6) Alkoxy, (C1-C6) Haloalkoxy, (C1-C6) Cyanoalkoxy, (C1- C6) Alkoxycarbonyl- (C1-C6) alkoxy, (C1-C6) Alkoxy (C1-C6) alkoxy, (C3-C8th) Cycloalkyl, (C3- C8th) Halocycloalkyl, (C1-C6) Alkyl (C3-C8th) cycloalkyl, (C1-C6) Haloalkyl (C3-C8th) cycloalkyl, (C1-C4) haloalkenoxy, (C1-C6) alkylhydroxyimino, (C1-C6) alkoxyimino, (C1-C6) alkyl- (C1-C6) alkoxyimino, (C1-C6) Haloalkyl (C1-C6) alkoxyimino, (C1-C6) Alkylsulfanyl, (C1- C6) Alkoxy (C1-C6) alkylsulfanyl, (C1-C6) Alkylsulfanyl (C1-C6) alkyl, (C1-C6) Alkylsulfinyl, (C1- C6) Haloalkylsulfinyl, (C1-C6) Alkoxy (C1-C6) alkylsulfinyl, (C1-C6) Alkylsulfinyl (C1-  C6) alkyl, (C1-C6) alkylsulfonyl, (C1-C6) haloalkylsulfonyl, (C1-C6) alkoxy- (C1-C6) alkylsulfonyl, (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6 ) Alkylsulfonyloxy, (C 1 -C 6) haloalkylsulfanyl, (C 3 -C 6) cycloalkylsulfanyl, (C 3 -C 6) -halocycloalkylsulfanyl, (C 3 -C 6) -cycloalkylsulfonyl, (C 3 -C 6) -halocycloalkylsulfonyl, (C 3 -C 6) -cycloalkylsulfinyl, (C 3 -C 6) Halocycloalkylsulfinyl, (C1-C6) alkylcarbonyl, (C1-C6) haloalkylcarbonyl, (C1-C6) alkylcarbonyloxy, (C1-C6) alkoxycarbonyl, (C1-C6) haloalkoxycarbonyl, aminocarbonyl, (C1-C6) alkylaminocarbonyl, di (C1 -C 6) alkylaminocarbonyl, (C 2 -C 6) alkenylaminocarbonyl, di- (C 2 -C 6) -alkenylaminocarbonyl, (C 3 -C 8) cycloalkylaminocarbonyl, (C 1 -C 6) alkylsulfonylamino, (C 1 -C 6) -alkylamino, di- (C 1 -C 6) -alkyl C6) alkylamino, (C1-C6) haloalkylamino, bis (C1-C6) haloalkylamino, aminosulfonyl, (C1-C6) alkylaminosulfonyl, di- (C1-C6) alkylaminosulfonyl, (C1-C6) alkylsulfoximino, aminothiocarbonyl, (C1- C6) alkylaminothiocarbonyl, di- (C1-C6) alkylaminothiocarbonyl, (C3-C8) cycloalkylamine o, R1 is (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, (C1-C6) alkoxy- (C1-C6) alkyl, (C1-C6 ) Haloalkoxy- (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkenyloxy- (C1-C6) alkyl, (C2-C6) haloalkenyloxy- (C1-C6) alkyl, (C2-C6) Haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) alkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyl , (C2-C6) cyanoalkynyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl- (C1-C6) alkyl, (C3-C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) Alkyl (C3-C8th) Cycloalkyl, (C1-C6) Haloalkyl (C3-C8th) cycloalkyl, halogen (C3- C8th) cycloalkyl, cyano (C3-C8th) cycloalkyl, (C2-C6) Alkynyl (C3-C8th) cycloalkyl, (C1-C6) Alkoxy (C3- C8th) cycloalkyl, (C1-C6) Alkoxycarbonyl- (C3-C8th) cycloalkyl, (C1-C6) Alkylamino, di (C1-C6) alkylamino, (C3-C8th) Cycloalkylamino, (C1-C6) Alkylcarbonylamino, (C1-C6) Alkylthio (C1-C6) alkyl, (C1-C6) Haloalkylthio (C1-C6) alkyl, (C1-C6) Alkylsulfinyl (C1-C6) alkyl, (C1- C6) Halogenalkylsulfinyl- (C1-C6) alkyl, (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1- C6) Haloalkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylthio (C1-C6) alkyl, (C1- C6) Alkoxy (C1-C6) Alkylsulfinyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkylcarbonyl (C1-C6) alkyl, (C1-C6) Haloalkylcarbonyl (C1-C6) alkyl, (C1- C6) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) Haloalkoxycarbonyl (C1-C6) alkyl, (C1- C6) Alkylsulfonylamino, aminosulfonyl (C1-C6) alkyl, (C1-C6) Alkylaminosulfonyl (C1-C6) alkyl, di (C 1 -C 6) alkyl-aminosulfonyl (C 1 -C 6) alkyl, (C 1 -C 4) alkoxy, (C 3 -C 6) cycloalkoxy, (C 3 -C6) Cycloalkylcarbonyl or (C1-C4) Alkylcarbonyl, or represents in each case optionally mono- or polysubstituted, identically or differently by aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl (C1-C6) Alkyl, (C1- C6) Alkoxy, (C2-C6) Alkenyl, (C2-C6) Alkynyl, (C3-C8th) Cycloalkyl, where aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl,  Aminosulfonyl, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 6) alkoxy, (C 1 -C 6) haloalkyl, (C 1 -C 6) haloalkoxy, (C 1 -C 6) alkylthio, (C 1 -C 6) alkylsulfinyl , (C1-C6) alkylsulfonyl, (C1-C6) alkylsulfimino, (C1-C6) alkylsulfimino (C1-C6) alkyl, (C1-C6) alkylsulfimino (C2-C6) alkylcarbonyl, (C1-C6) alkylsulfoximino, (C1-C6) alkylsulfoximino (C1-C6) alkyl, (C1-C6) alkylsulfoximino (C2-C6) alkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkylcarbonyl or (C3-C6) trialkylsilyl can be, or is in each case optionally monosubstituted or polysubstituted, identically or differently substituted aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, wherein the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, ( C1-C6) alkyl, (C3-C8) cycloalkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) alkylthio, (C1-C6) haloalkylthio, ( C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, (C1-C6) alkylsulfimino, (C1-C6) alkylsulfimino (C1-C6) alkyl, (C1-C6) alk ylsulfimino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkylsulfoximino, (C 1 -C 6) alkylsulfoximino (C 1 -C 6) alkyl, (C 1 -C 6) alkylsulfoximino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkoxycarbonyl , (C1-C6) alkylcarbonyl, (C3-C6) trialkylsilyl, R2 is hydrogen, (C1-C6) alkyl, (C3-C8) cycloalkyl, (C1-C6) alkoxy, (C1-C6) alkylcarbonyl, (C3-C6) C8) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, (C1-C6) alkoxy- (C1-C6) alkyl, (C1-C6 ) Haloalkoxy- (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkenyloxy- (C1-C6) alkyl, (C2-C6) haloalkenyloxy- (C1-C6) alkyl, (C2- C6) Haloalkenyl, (C2-C6) Cyanoalkenyl, (C2-C6) Alkynyl, (C2-C6) Alkynyloxy (C1-C6) alkyl, (C2- C6) Halogenalkinyloxy- (C1-C6) alkyl, (C2-C6) Haloalkynyl, (C2-C6) Cyanoalkynyl, (C3- C8th) Cycloalkyl (C3-C8th) Cycloalkyl, (C1-C6) Alkyl (C3-C8th) Cycloalkyl, halogen (C3-C8th) cycloalkyl, (C1-C6) Alkylthio (C1-C6) alkyl, (C1-C6) Haloalkylthio (C1-C6) alkyl, (C1-C6) Alkylsulfinyl (C1- C6) alkyl, (C1-C6) Halogenalkylsulfinyl- (C1-C6) alkyl, (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1- C6) Haloalkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylthio (C1-C6) alkyl, (C1- C6) Alkoxy (C1-C6) Alkylsulfinyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkylcarbonyl (C1-C6) alkyl, (C1-C6) Haloalkylcarbonyl (C1-C6) alkyl, (C1- C6) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) Haloalkoxycarbonyl (C1-C6) alkyl, aminocarbonyl (C1-C6) alkyl, (C1-C6) Alkylamino (C1-C6) alkyl, di (C1-C6) Alkylamino (C1-C6) alkyl or (C3- C8th) Cycloalkylamino (C1-C6) alkyl, R3 is hydrogen, (C1-C6) alkyl, (C3-C8) cycloalkyl, (C1-C6) alkoxy, (C1-C6) alkylcarbonyl, (C3-C8th) Cycloalkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C6) Haloalkyl, (C1-C6) Cyanoalkyl, (C1- C6) Hydroxyalkyl, (C1-C6) Alkoxy (C1-C6) alkyl, (C1-C6) Haloalkoxy (C1-C6) alkyl, (C2- C6) Alkenyl, (C2-C6) Alkenyloxy (C1-C6) alkyl, (C2-C6) Halogenalkenyloxy- (C1-C6) alkyl, (C2- C6) Haloalkenyl, (C2-C6) Cyanoalkenyl, (C2-C6) Alkynyl, (C2-C6) Alkynyloxy (C1-C6) alkyl, (C2- C6) Halogenalkinyloxy- (C1-C6) alkyl, (C2-C6) Haloalkynyl, (C2-C6) Cyanoalkynyl, (C3-  C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) alkyl- (C3-C8) cycloalkyl, halo (C3-C8) cycloalkyl, (C1-C6) alkylthio (C1-C6) alkyl, (C1- C6) haloalkylthio (C1-C6) alkyl, (C1-C6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) haloalkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkylsulfonyl- (C1-C6 ) alkyl, (C 1 -C 6) haloalkylsulfonyl (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy (C 1 -C 6) alkylthio (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy (C 1 -C 6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) alkylcarbonyl- (C1-C6) alkyl, (C1-C6) haloalkylcarbonyl (C1-C6) alkyl, (C1-C6) alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) haloalkoxycarbonyl- (C1-C6) alkyl, aminocarbonyl- (C1-C6) alkyl, (C1-C6) Alkylamino- (C 1 -C 6) -alkyl, di- (C 1 -C 6) -alkylamino- (C 1 -C 6) -alkyl or (C 3 -C 8) -cycloalkylamino- (C 1 -C 6) -alkyl, R 4 represents (C 1 -C 6) -alkyl, ( C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, (C1-C6) alkoxy- (C1-C6) alkyl, (C1-C6) haloalkoxy- (C1-C6) alkyl, (C2 -C6) alkenyl, (C 2 -C 6) alkenyloxy (C 1 -C 6) alkyl, (C 2 -C 6) haloalkenyloxy (C 1 -C 6) alkyl, (C 2 -C 4) 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6) alkynyloxy (C 1 -C 6) alkyl, (C 2 -C 6) haloalkynyloxy (C 1 -C 6) alkyl, (C 2 -C 6) ) Haloalkynyl, (C 2 -C 6) cyanoalkynyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl- (C 1 -C 6) -alkyl, cyano (C 3 -C 8) -cycloalkyl- (C 1 -C 6) -alkyl, halogen (C 3 -C 8) -cycloalkyl- C8) cycloalkyl- (C1-C6) alkyl, (C1-C4) haloalkyl- (C3-C8) cycloalkyl- (C1-C6) alkyl, (C3-C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6 ) Alkyl (C3-C8) cycloalkyl, (C1-C6) haloalkyl- (C3-C8) cycloalkyl, halo (C3-C8) cycloalkyl, cyano (C3-C8) cycloalkyl, (C2-C6) alkynyl (C3-C8) cycloalkyl C8) cycloalkyl, (C1-C6) alkoxy- (C3-C8) cycloalkyl, (C1-C6) alkoxycarbonyl- (C3-C8) cycloalkyl, carbamoyl- (C3-C8th) cycloalkyl, thiocarbamoyl (C3-C8th) cycloalkyl, (C1-C6) Alkylthio (C1- C6) alkyl, (C1-C6) Haloalkylthio (C1-C6) alkyl, (C1-C6) Alkylsulfinyl (C1-C6) alkyl, (C1- C6) Halogenalkylsulfinyl- (C1-C6) alkyl, (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1- C6) Haloalkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylthio (C1-C6) alkyl, (C1- C6) Alkoxy (C1-C6) Alkylsulfinyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkylcarbonyl (C1-C6) alkyl, (C1-C6) Haloalkylcarbonyl (C1-C6) alkyl, (C1- C6) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) Haloalkoxycarbonyl (C1-C6) alkyl, (C1- C6) Alkylsulfonylamino, aminosulfonyl (C1-C6) alkyl, (C1-C6) Alkylaminosulfonyl (C1-C6) alkyl di- (C1-C6) Alkyl-aminosulphonyl (C1-C6) alkyl, amino, (C1-C6) Alkylamino, di (C1-C6) alkylamino, (C3-C8th) Cycloalkylamino, N- (C1-C6) Alkyl (C3-C8th) Cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, halobenzylamino, N- (C1-C6) alkyl benzylamino, N- (C 1 -C 6) alkyl-cyanobenzylamino, N- (C 1 -C 6) alkyl-nitrobenzylamino, N- (C 1 -C 6) alkyl-halobenzylamino, (C1-C6) Alkylcarbonylamino, (C3-C8th) Cycloalkylcarbonylamino, hydroxy, (C1-C6) Alkoxy, (C3-C8th) Cycloalkoxy, (C3-C8th) Cycloalkyl (C1-C6) Alkoxy, cyano (C1- C6) Alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, halobenzyloxy, (C1- C6) Alkylimino, (C3-C8th) Cycloalkylimino, benzylimino, cyanobenzylimino, nitrobenzylimino, halobenzylimino, (C1-C6) Haloalkylbenzylimino, halogeno [(C1C6) haloalkyl] benzylimino, (C1-C6) alkylcarbonyl, (C1-C6) haloalkylcarbonyl, (C3-  C8) is cycloalkylcarbonyl or (C3-C8) cycloalkyl- (C1-C6) alkylcarbonyl, or in each case optionally monosubstituted or polysubstituted, identical or different, by aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4 benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl substituted (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) alkoxy, (C2-C6) alkenyl, (C2-C6) alkynyl, (C3-C8) cycloalkyl, oxy, amino, N- (C1-C6) alkylamino, N- (C3-C8) cycloalkylamino or carbonyl, wherein aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4 benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C 1 -C 6) -alkyl, C3-C6) cycloalkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) alkylthio, (C1-C6) haloalkylthio, (C1-C6) alkylsulfinyl, (C1 -C6) alkylsulfonyl, (C1-C6) haloalkylsulfinyl, (C1-C6) haloalkylsulfonyl, (C1-C 6) Alkylsulfimino, (C 1 -C 6) alkylsulfimino (C 1 -C 6) alkyl, (C 1 -C 6) alkylsulfimino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkylsulfoximino, (C 1 -C 6) alkylsulfoximino (C 1 -C 6 ) alkyl, (C 1 -C 6) alkylsulfoximino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) trialkylsilyl or hetaryl, or in each case optionally mono- or polysubstituted is identical or different substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, wherein the substituents are selected from halogen, cyano, nitro, hydroxy, Amino, carboxy, carbamoyl, (C1-C6) Alkyl, (C3-C8th) Cycloalkyl, (C1-C6) -Alkoxy, (C1- C6) Haloalkyl, (C1-C6) Haloalkoxy, (C1-C6) Alkylthio, (C1-C6) Haloalkylthio, (C1- C6) Alkylsulfinyl, (C1-C6) Alkylsulfonyl, (C1-C6) Haloalkylsulfinyl, (C1-C6) Haloalkylsulfonyl, (C1-C6) Alkylsulfimino, (C1-C6) Alkylsulfimino- (C1-C6) alkyl, (C1-C6) Alkylsulfimino (C2-C6) alkylcarbonyl, (C1-C6) Alkylsulfoximino, (C1-C6) Alkylsulfoximino- (C1-C6) alkyl, (C1- C6) Alkylsulfoximino- (C2-C6) alkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl, (C3- C6) Trialkylsilyl, or R3 and R4 together for (C2-C6) -Alkyl or for (C2-C6) Alkenyl, with a 3-7 membered, optionally substituted by halogen, cyano, hydroxy, amino, carboxy, carbamoyl, (C1-C6) Alkyl, (C3- C8th) Cycloalkyl, (C1-C6) -Alkoxy, (C1-C6) Haloalkyl, (C1-C6) Haloalkoxy, (C1-C6) Alkylthio or (C1-C6) Halogenoalkylthio substituted ring is formed, which may optionally contain one to two double bonds, R5, R6 independently of one another represent hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, (C1- C6) Alkylamino, di (C1-C6) Alkylamino, (C3-C6) Cycloalkyl, halogen (C3-C6) cycloalkyl, (C1- C6) Alkyl, (C1-C6) Haloalkyl, (C2-C6) Alkenyl, (C2-C6) Haloalkenyl, (C2-C6) Alkynyl, (C2- C6) Haloalkynyl, (C1-C6) Alkoxy, (C1-C6) Haloalkoxy, (C1-C6) Alkylthio, (C1-  C6) haloalkylthio, (C 1 -C 6) alkylsulfinyl, (C 1 -C 6) haloalkylsulfinyl, (C 1 -C 6) alkylsulfonyl, (C 1 -C 6) haloalkylsulfonyl, V 1 is oxygen or sulfur, V 2 is oxygen, sulfur or -NH , Furthermore, it has been found that the compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and / or acaricides, moreover, as a rule, are very well tolerated by plants, in particular with respect to crop plants. The compounds of the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below: Preferred range: Preferred (embodiment 2-1) are the compounds of the formula (I) in which Q1 is in each case optionally mono- or polysubstituted or differently substituted phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl or oxo-hetaryl, wherein the substituents are selected from cyano, halogen, nitro, amino, SF5, (C1-C4 ) Alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) cyanoalkyl, (C 1 -C 4) hydroxyalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) -alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) Haloalkenyl, (C 2 -C 4) cyano alkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) haloalkynyl, (C 2 -C 4) cyanoalkynyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) cyanoalkoxy , (C1-C4) alkoxy- (C1-C4) alkoxy, (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C1-C4) Alkyl (C3-C6) cycloalkyl, (C1-C4) Haloalkyl (C3-C6) cycloalkyl, (C1- C4) Haloalkenoxy, (C1-C4) Alkylhydroxyimino, (C1-C4) Alkoxyimino, (C1-C4) Alkyl (C1- C4) alkoxyimino, (C1-C4) Haloalkyl (C1-C4) alkoxyimino, (C1-C4) Alkylsulfanyl, (C1- C4) Alkylsulfanyl (C1-C4) alkyl, (C1-C4) Alkylsulfinyl, (C1-C4) Haloalkylsulfinyl, (C1- C4) Alkylsulfinyl (C1-C4) alkyl, (C1-C4) Alkylsulfonyl, (C1-C4) Haloalkylsulfonyl, (C1- C4) Alkylsulfonyl (C1-C4) alkyl, (C1-C4) Alkylsulfonyloxy, (C1-C4) Haloalkylsulfanyl, (C3- C6) Cycloalkylsulfanyl, (C3-C6) Halocycloalkylsulfanyl, (C3-C6) Cycloalkylsulfonyl, (C3- C6) Halocycloalkylsulfonyl, (C3-C6) Cycloalkylsulfinyl, (C3-C6) Halocycloalkylsulfinyl, (C1-C4) Alkylcarbonyl, (C1-C4) Haloalkylcarbonyl, aminocarbonyl, (C1- C4) Alkylaminocarbonyl, di (C1-C4) alkylaminocarbonyl, (C1-C4) Alkylsulfonylamino, (C1- C4) Alkylamino, di (C1-C4) Alkylamino, (C1-C6) Haloalkylamino, bis (C1C6) haloalkylamino, aminosulfonyl, (C1-C4) alkylaminosulfonyl, di- (C1-C4) Alkylaminosulfonyl,  R1 is (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, (C1-C4) alkoxy- (C1-C4) alkyl, (C1-C4) haloalkoxy (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkenyloxy (C1-C6) alkyl, (C2-C4) haloalkenyloxy (C1-C6) alkyl, (C2-C4) haloalkenyl, (C2-C4) cyanoalkenyl, (C2-C4) alkynyl, (C2-C4) alkynyloxy (C1-C6) alkyl, (C2-C4) haloalkynyloxy- (C1-C4) alkyl, (C2-C4) haloalkynyl, ( C2-C4) cyanoalkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C4) alkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (C1-C4) alkyl- (C3 -C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) alkynyl- (C3-C6) cycloalkyl, ( C1-C4) alkoxy- (C3-C6) cycloalkyl, (C1-C4) alkoxycarbonyl- (C3-C6) cycloalkyl, (C1-C6) alkylamino, di (C1-C6) alkylamino, (C3-C6) Cycloalkylamino, (C 1 -C 4) alkylthio (C 1 -C 6) alkyl, (C 1 -C 4) haloalkylthio (C 1 -C 6) alkyl, (C 1 -C 4) alkylsulfinyl (C 1 -C 6) alkyl, (C 1 -C 4) haloalkylsulfinyl - (C 1 -C 6) alkyl, (C 1 -C 4) alkylsulfonyl (C 1 -C 6) alkyl, (C 1 -C 4) haloalky isulfonyl- (C 1 -C 6) alkyl, (C 1 -C 4) alkylcarbonyl- (C 1 -C 6) alkyl, (C 1 -C 4) alkoxycarbonyl- (C 1 -C 6) alkyl, (C 1 -C 4) alkoxy, (C 3 -C 6) cycloalkoxy , (C 3 -C 6) cycloalkylcarbonyl or (C 1 -C 4) -alkylcarbonyl, or in each case optionally monosubstituted or polysubstituted by identical or different aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl (C 1 -C 4) -alkyl, ( C1-C4) alkoxy, (C2-C4) alkenyl, (C2-C4) alkynyl, (C3-C6) cycloalkyl, where aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identical or various by halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, aminosulfonyl, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C4) Haloalkyl, (C1- C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1- C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl or (C3-C6) Trialkylsilyl may be substituted, or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy , Carbamoyl, (C1- C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) -Alkoxy, (C1-C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1-C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1- C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl, (C3-C6) Trialkylsilyl, R2 is hydrogen, (C1-C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C6) Alkylcarbonyl, (C3- C6) Cycloalkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C4) Haloalkyl or (C1-C4) Cyanoalkyl, R3 is hydrogen, (C1-C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C6) Alkylcarbonyl, (C3- C6) Cycloalkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C4) Haloalkyl or (C1-C4) Cyanoalkyl, R4 is (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1-C6) Cyanoalkyl, (C1-C4) Hydroxyalkyl, (C1-  C4) alkoxy- (C1-C4) alkyl, (C1-C4) haloalkoxy- (C1-C4) alkyl, (C2-C6) alkenyl, (C2-C4) alkenyloxy- (C1-C6) alkyl, (C2-C4 ) Haloalkenyloxy- (C1-C4) alkyl, (C2-C4) haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C4) alkynyloxy- (C1-C4) alkyl, (C2-C4) Haloalkynyloxy- (C1-C4) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C6) -alkyl, cyano (C3-C6) cycloalkyl- (C1-C6) alkyl, halo (C3-C6) cycloalkyl- (C1-C6) alkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl- (C1-C6) -alkyl, (C3-C6) Cycloalkyl- (C3-C6) cycloalkyl, (C1-C6) alkyl- (C3-C6) cycloalkyl, (C1-C6) haloalkyl- (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, cyano (C3-C6 ) cycloalkyl, (C 2 -C 4) alkynyl- (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkoxy- (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkoxycarbonyl- (C 3 -C 6) -cycloalkyl, carbamoyl- (C 3 -C 4) -cycloalkyl, C6) cycloalkyl, thiocarbamoyl (C3-C6) cycloalkyl, (C1-C4) alkylthio (C1-C4) alkyl, (C1-C4) haloalkylthio (C1-C4) alkyl, (C1-C4) alkylsulfinyl (C1 -C4) alkyl, (C 1 -C 4) haloalkylsulfinyl- (C 1 -C 4) -alkyl, (C 1 -C 4) -alkylsulfony 1- (C 1 -C 4) alkyl, (C 1 -C 4) haloalkylsulfonyl (C 1 -C 4) alkyl, (C 1 -C 6) alkylcarbonyl (C 1 -C 6) alkyl, (C 1 -C 6) haloalkylcarbonyl (C 1 -C 6) alkyl , (C 1 -C 4) alkoxycarbonyl- (C 1 -C 4) -alkyl, (C 1 -C 4) -halogenalkoxycarbonyl- (C 1 -C 4) -alkyl, (C 1 -C 4) -alkylsulfonylamino, aminosulfonyl- (C 1 -C 4) -alkyl, (C 1 -C 4) Alkylaminosulfonyl- (C 1 -C 4) -alkyl, or di- (C 1 -C 4) -alkyl-aminosulfonyl- (C 1 -C 6) -alkyl, amino, (C 1 -C 4) -alkylamino, di- (C 1 -C 4) -alkyl-amino, (C3 -C6) cycloalkylamino, N- (C 1 -C 4) alkyl- (C 3 -C 6) cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, halobenzylamino, N- (C 1 -C 4) alkylbenzylamino, N- (C 1 -C 4) -alkyl-cyanobenzylamino , N- (C1-C4) alkyl-nitrobenzylamino, N- (C1-C4) alkyl-halobenzylamino, (C1-C4) Alkylcarbonylamino, (C3-C6) Cycloalkylcarbonylamino, hydroxy, (C1-C4) Alkoxy, (C3-C6) Cycloalkoxy, (C3- C6) Cycloalkyl (C1-C4) Alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, halobenzyloxy, (C1-C4) Alkylimino, (C3-C6) Cycloalkylimino, benzylimino, cyanobenzylimino, nitrobenzylimino or halobenzylimino, or in each case optionally mono- or polysubstituted, identically or differently, by aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, Heterocyclyl or oxo-heterocyclyl substituted (C1-C4) Alkyl, (C1-C4) Haloalkyl, (C1-C4) Alkoxy, (C2-C4) Alkenyl, (C2-C4) Alkynyl, (C3-C6) Cycloalkyl, oxy, amino, N- (C1-C4) Alkylamino or N- (C3- C6) Cycloalkylamino, where aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, Nitro, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1- C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1-C4) Haloalkylsulfinyl, (C1- C4) Haloalkylsulfonyl, (C1-C4) Alkylsulfimino, (C1-C4) Alkylsulfimino- (C1-C4) alkyl, (C1- C4) Alkylsulfoximino, (C1-C4) Alkylsulfoximino- (C1-C4) alkyl, (C1-C4) Alkoxycarbonyl, (C1- C4) alkylcarbonyl, (C3-C6) trialkylsilyl or hetaryl may be substituted, or  or for each optionally mono- or polysubstituted, identically or differently substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, wherein the substituents are selected from halogen , Cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -halogenoalkoxy, ( C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, (C1-C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfonyl, (C1-C4) alkylsulfimino, (C1-C4) alkylsulfimino (C1-C4) alkyl, (C1-C4) alkylsulfoximino, (C1-C4) alkylsulfoximino (C1-C4) alkyl, (C1-C4) alkoxycarbonyl, (C1-C4) alkylcarbonyl, ( C 3 -C 6) trialkylsilyl, or R 3 and R 4 together represent (C 2 -C 6) -alkyl or (C 2 -C 6) -alkenyl, where a 3-7-membered is optionally substituted by halogen, cyano, hydroxy, amino, (C 1 -C 4) Alkyl, (C3-C6) cycloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkyl, (C1-C4) haloalkoxy, (C1-C4) alkyl lthio or (C 1 -C 4) haloalkylthio-substituted ring which may optionally contain one or two double bonds, R 5, R 6 independently of one another represent hydrogen, cyano, halogen, nitro, (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkyl, (C1-C4) are haloalkyl or (C1-C4) haloalkoxy, V1, V2 independently of one another represent oxygen or sulfur. Alternatively and also preferred (embodiment 2-2) are the compounds of formula (I) in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4 benzodioxinyl, hetaryl or oxo-hetaryl, wherein the substituents are selected from cyano, halogen, nitro, amino, SF5, (C1-C4) Alkyl, (C1-C4) Haloalkyl, (C1-C4) Cyanoalkyl, (C1-C4) Hydroxyalkyl, (C1-C4) Alkoxy (C1-C4) alkyl, (C2-C4) Alkenyl, (C2-C4) Haloalkenyl, (C2-C4) Cyanoalkenyl, (C2-C4) Alkynyl, (C2- C4) Haloalkynyl, (C2-C4) Cyanoalkynyl, (C1-C4) Alkoxy, (C1-C4) Haloalkoxy, (C1- C4) Cyanoalkoxy, (C1-C4) Alkoxy (C1-C4) alkoxy, (C3-C6) Cycloalkyl, (C3-C6) Halocycloalkyl, (C1-C4) Alkyl (C3-C6) cycloalkyl, (C1-C4) Haloalkyl (C3-C6) cycloalkyl, (C1- C4) Haloalkenoxy, (C1-C4) Alkylhydroxyimino, (C1-C4) Alkoxyimino, (C1-C4) Alkyl (C1- C4) alkoxyimino, (C1-C4) Haloalkyl (C1-C4) alkoxyimino, (C1-C4) Alkylsulfanyl, (C1- C4) Alkylsulfanyl (C1-C4) alkyl, (C1-C4) Alkylsulfinyl, (C1-C4) Haloalkylsulfinyl, (C1- C4) Alkylsulfinyl (C1-C4) alkyl, (C1-C4) Alkylsulfonyl, (C1-C4) Haloalkylsulfonyl, (C1- C4) Alkylsulfonyl (C1-C4) alkyl, (C1-C4) Alkylsulfonyloxy, (C1-C4) Haloalkylsulfanyl, (C3- C6) cycloalkylsulfanyl, (C3-C6) halocycloalkylsulfanyl, (C3-C6) cycloalkylsulfonyl, (C3-C6) Halocycloalkylsulfonyl, (C3-C6) Cycloalkylsulfinyl, (C3-C6) Halocycloalkylsulfinyl, (C1-C4) Alkylcarbonyl, (C1-C4) Haloalkylcarbonyl, aminocarbonyl, (C1- C4) Alkylaminocarbonyl, di (C1-C4) alkylaminocarbonyl, (C1-C4) Alkylsulfonylamino, (C1-  C4) alkylamino, di (C1-C4) alkylamino, (C1-C6) haloalkylamino, bis (C1-C6) haloalkylamino, aminosulfonyl, (C1-C4) alkylaminosulfonyl, di- (C1-C4) alkylaminosulfonyl, R1 for ( C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, (C1-C4) alkoxy- (C1-C4) alkyl, (C1-C4) haloalkoxy- (C1 -C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkenyloxy (C 1 -C 6) alkyl, (C 2 -C 4) haloalkenyloxy (C 1 -C 6) alkyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) C4) cyano alkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (C 1 -C 6) alkyl, (C 2 -C 4) haloalkynyloxy (C 1 -C 4) alkyl, (C 2 -C 4) haloalkynyl, (C 2 -C 4) cyano alkenyl, (C 2 -C 4) alkynyl ) Cyanoalkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C4) alkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (C1-C4) alkyl- (C3-C6) Cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) alkynyl- (C3-C6) cycloalkyl, (C1-C4 ) Alkoxy- (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkoxycarbonyl- (C 3 -C 6) -cycloalkyl, (C 1 -C 6) -alkylamino, di (C 1 -C 6) -alkylamino, (C 3 -C 6) -cycloalkylamino, ( C1-C4) alkylthio (C1-C6) alkyl, (C1 -C4) haloalkylthio (C1-C6) alkyl, (C1-C4) alkylsulfinyl (C1-C6) alkyl, (C1-C4) haloalkylsulfinyl- (C1-C6) alkyl, (C1-C4) alkylsulfonyl- (C1- C6) alkyl, (C1-C4) haloalkylsulfonyl- (C1-C6) alkyl, (C1-C4) alkylcarbonyl- (C1-C6) alkyl, (C1-C4) alkoxycarbonyl- (C1-C6) alkyl, (C1-C4 ) Alkoxy, (C3-C6) cycloalkoxy, (C3-C6) cycloalkylcarbonyl or (C1-C4) alkylcarbonyl, or in each case optionally mono- or polysubstituted by identical or different aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl substituted (C1-C4) alkyl, (C1-C4) Alkoxy, (C2-C4) Alkenyl, (C2-C4) Alkynyl, (C3-C6) Cycloalkyl, wherein aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, aminosulfonyl, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C4) Haloalkyl, (C1- C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1- C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl or (C3-C6) Trialkylsilyl may be substituted, or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy , Carbamoyl, (C1- C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) -Alkoxy, (C1-C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1-C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1- C6) alkoxycarbonyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) trialkylsilyl, R 2 is hydrogen, (C1-C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C6) Alkylcarbonyl, (C3- C6) Cycloalkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C4) Haloalkyl or (C1-C4) Cyanoalkyl, R3 is hydrogen, (C1-C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C6) Alkylcarbonyl, (C3-  C6) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C4) haloalkyl or (C1-C4) cyanoalkyl, R4 represents (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, ( C1-C4) hydroxyalkyl, (C1-C4) alkoxy- (C1-C4) alkyl, (C1-C4) haloalkoxy- (C1-C4) alkyl, (C2-C6) alkenyl, (C2-C4) alkenyloxy- (C1 -C 6) alkyl, (C 2 -C 4) haloalkenyloxy (C 1 -C 4) alkyl, (C 2 -C 4) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 4) alkynyloxy (C 1 -C 4) C4) alkyl, (C2-C4) haloalkynyloxy- (C1-C4) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C6 ) alkyl, cyano (C3-C6) cycloalkyl- (C1-C6) alkyl, halo (C3-C6) cycloalkyl- (C1-C6) alkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl- (C1- C6) alkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (C1-C6) alkyl- (C3-C6) cycloalkyl, (C1-C6) haloalkyl- (C3-C6) cycloalkyl, halogen (C3-C6) C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) alkynyl (C3-C6) cycloalkyl, (C1-C4) alkoxy- (C3-C6) cycloalkyl, (C1-C4) alkoxycarbonyl- (C3- C6) cycloalkyl, carbamoyl (C3-C6) cycloalkyl, thiocarbamoyl (C 3-C6) cycloalkyl, (C 1 -C 4) alkylthio (C 1 -C 4) alkyl, (C 1 -C 4) haloalkylthio (C 1 -C 4) alkyl, (C 1 -C 4) alkylsulfinyl (C 1 -C 4) alkyl, (Cl C4) haloalkylsulfinyl- (C 1 -C 4) -alkyl, (C 1 -C 4) -alkylsulfonyl- (C 1 -C 4) -alkyl, (C 1 -C 4) -halogenoalkylsulfonyl- (C 1 -C 4) -alkyl, (C 1 -C 6) -alkylcarbonyl- (C 1 -C 4) -alkyl C6) alkyl, (C1-C6) haloalkylcarbonyl- (C1-C6) alkyl, (C1-C4) alkoxycarbonyl- (C1-C4) alkyl, (C1-C4) haloalkoxycarbonyl- (C1-C4) alkyl, (C1-C4 ) Alkylsulfonylamino, aminosulfonyl- (C 1 -C 4) -alkyl, (C 1 -C 4) -alkylaminosulfonyl- (C 1 -C 4) -alkyl, or di- (C 1 -C 4) -alkyl-aminosulfonyl- (C 1 -C 4) -alkyl6) alkyl, amino, (C1-C4) Alkylamino, di (C1-C4) alkyl-amino, (C3-C6) Cycloalkylamino, N- (C1- C4) Alkyl (C3-C6) Cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, halobenzylamino, N- (C1-C4) alkyl benzylamino, N- (C1-C4) alkyl-cyanobenzylamino, N- (C1- C4) alkyl-nitrobenzylamino, N- (C1-C4) alkyl-halobenzylamino, (C1-C4) Alkylcarbonylamino, (C3-C6) Cycloalkylcarbonylamino, hydroxy, (C1-C4) Alkoxy, (C3-C6) Cycloalkoxy, (C3- C6) Cycloalkyl (C1-C4) Alkoxy, cyano (C1-C4) Alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, halobenzyloxy, (C1-C4) Alkylimino, (C3-C6) Cycloalkylimino, benzylimino, cyanobenzylimino, nitrobenzylimino, halobenzylimino, (C1-C4) Haloalkylbenzylimino, halogeno [(C1-C4) Haloalkyl] benzylimino, (C1-C4) Alkylcarbonyl, (C1- C4) Haloalkylcarbonyl, (C3-C6) Cycloalkylcarbonyl or (C3-C6) Cycloalkyl (C1-C4) alkylcarbonyl, or for each optionally mono- or polysubstituted, identically or differently, by aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl (C1-C4) Alkyl, (C1-C4) Haloalkyl, (C1-C4) Alkoxy, (C2-C4) Alkenyl, (C2-C4) Alkynyl, (C3-C6) Cycloalkyl, oxy, amino, N- (C1-C4) Alkylamino, N- (C3- C6) Cycloalkylamino or carbonyl, where aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, Cyano, nitro, hydroxy, amino,  Carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C1-C4) alkyl, (C3-C6) cycloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkyl, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, (C1-C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfonyl, (C1-C4) alkylsulfimino, (C1-C4) alkylsulfimino ( C1-C4) alkyl, (C1-C4) alkylsulfoximino, (C1-C4) alkylsulfoximino (C1-C4) alkyl, (C1-C4) alkoxycarbonyl, (C1-C4) alkylcarbonyl, (C3-C6) trialkylsilyl or hetaryl may be, or or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halo, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkyl, (C 1 -C 4 ) Haloalkoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-C4) alkylsulfinyl, (C1-C4 ) Alkylsulfonyl, (C1-C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfonyl, (C1-C4) alkylsulfimino, (C1-C4) alkylsulfimino (C1-C4) alkyl, (C1-C4) alkylsulfoximino, (C1-4) C4) alkylsulfoximino (C1-C4) alkyl, (C1-C4) alkoxycarbonyl, (C1-C4) alkylcarbonyl, (C3-C6) trialkylsilyl, or R3 and R4 together for (C2-C6) -alkyl or for (C2-C6) -alkyl. C 6) alkenyl, where a 3-7 membered by halogen, cyano, hydroxy, amino, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkyl, (C1-C4) haloalkoxy, (C1-C4) alkylthio or (C1-C4) haloalkylthio substituted ring is formed, which may optionally contain one to two double bonds, R5, R6 independently of one another represent hydrogen, cyano, halogen, nitro, (C3-C6) Cycloalkyl, (C1- C4) Alkyl, (C1-C4) Haloalkyl or (C1-C4) Are halogenoalkoxy, V1 is oxygen or sulfur, V2 is oxygen, sulfur or -NH. Particularly preferred range: Particularly preferred (embodiment 3-1) are the compounds of formula (I) in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1 , 4-benzodioxinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furanyl, oxazolyl, thiazolyl, imidazolyl or pyrazolyl, wherein the substituents are selected from cyano, halogen, nitro, SF5, (C1-C4) Alkyl, (C1- C4) Haloalkyl, (C2-C4) Alkenyl, (C2-C4) Haloalkenyl, (C2-C4) Alkynyl, (C2C4) haloalkynyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C3-C6) cycloalkyl, (C3-C6) Halocycloalkyl, (C1-C4) Alkyl (C3-C6) cycloalkyl, (C1-C4) Haloalkyl (C3-C6) Cycloalkyl,  (C1-C4) haloalkeneoxy, (C1-C4) alkylsulfanyl, (C3-C6) halocycloalkylsulfanyl, (C1-C4) alkylsulfinyl, (C1-C4) haloalkylsulfinyl, (C3-C6) cycloalkylsulfinyl, (C1-C4) alkylsulfonyl, ( C1-C4) haloalkylsulfonyl, (C3-C6) cycloalkylsulfonyl, (C1-C4) haloalkylsulfanyl, (C3-C6) cycloalkylsulfanyl, (C1-C4) alkylcarbonyl, (C1-C4) haloalkylcarbonyl, bis (C1-C4) alkylamino, Di (C 1 -C 4) haloalkylamino, R 1 is (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) hydroxyalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) alkyl, (C 2 -C 4) ) Alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 3 -C 6) cycloalkyl (C 1 -C 4) alkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (C1-C4) alkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, halogen (C3-C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) alkynyl (C3-C6) cycloalkyl, (C1-C4) alkoxy- (C3-C6) cycloalkyl, (C1-C4) alkoxycarbonyl- (C3-C6) cycloalkyl, (C 1 -C 4) alkylthio (C 1 -C 6) alkyl, (C 1 -C 4) alkylcarbonyl (C 1 -C 6) alkyl, (C 1 -C 4) alkoxycarbonyl (C 1 -C 6) alkyl or (C 1 -C 4) alkoxy, or in each case optionally mono- or polysubstituted by identical or different aryl, hetaryl or heterocyclyl-substituted (C 1 -C 4) -alkyl, (C 3 -C 6) -cycloalkyl, where aryl, hetaryl or heterocyclyl are each, if appropriate mono- or polysubstituted by identical or different halogen, cyano, nitro, (C 1 -C 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -haloalkoxy, ( C1-C4) alkylthio or (C1-C6) alkoxycarbonyl may be substituted, or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, hetaryl, heterocyclyl or oxo-heterocyclyl, wherein the substituents are selected from halogen, cyano, nitro , (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) -Alkoxy, (C1- C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1- C6) Alkoxycarbonyl, R2 for hydrogen, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C4) Alkylcarbonyl, (C3- C6) Cycloalkylcarbonyl or (C1-C4) Alkoxycarbonyl, R3 is hydrogen, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C4) Alkylcarbonyl, (C3- C6) Cycloalkylcarbonyl or (C1-C4) Alkoxycarbonyl, R4 is (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1-C6) Cyanoalkyl, (C1-C4) Hydroxyalkyl, (C1- C4) Alkoxy (C1-C4) alkyl, (C1-C4) Haloalkoxy (C1-C4) alkyl, (C2-C4) Alkenyl, (C2- C4) Alkenyloxy (C1-C4) alkyl, (C2-C4) Halogenalkenyloxy- (C1-C4) alkyl, (C2-C4) Haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (C 1 -C 4) alkyl, (C 2 -C 6) haloalkynyl, (C2-C6) Cyanoalkynyl, (C3-C6) Cycloalkyl, (C3-C6) Cycloalkyl (C1-C4) alkyl, cyano (C3- C6) Cycloalkyl- (C1-C4) alkyl, halogen (C3-C6) Cycloalkyl- (C1-C4) alkyl, (C1-C4) Haloalkyl (C3- C6) Cycloalkyl- (C1-C4) alkyl, (C3-C6) Cycloalkyl (C3-C6) Cycloalkyl, (C1-C4) Alkyl (C3-  C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) alkynyl- (C3-C6) cycloalkyl, (C1 -C 4) alkoxy- (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkoxycarbonyl- (C 3 -C 6) -cycloalkyl, carbamoyl- (C 3 -C 6) -cycloalkyl, thiocarbamoyl- (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkylcarbonyl - (C 1 -C 4) alkyl, (C 1 -C 4) alkoxycarbonyl (C 1 -C 4) alkyl, amino, (C 1 -C 4) alkylamino, di (C 1 -C 4) alkylamino, (C 3 -C 6) cycloalkylamino, N (C1-C4) alkyl- (C3-C6) cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, N- (C1-C4) alkylbenzylamino, N- (C1-C4) alkyl-cyanobenzylamino, N- (C1-C4) alkyl-nitrobenzylamino, (C1-C4) alkylcarbonyl-amino, (C3-C6) cycloalkylcarbonylamino, hydroxy, (C1-C4) alkoxy, (C3-C6) cycloalkoxy, (C3-C6) cycloalkyl- (C1-C4) alkoxy, Benzyloxy, cyanobenzyloxy, nitrobenzyloxy, (C 1 -C 4) alkylimino, (C 3 -C 6) cycloalkylimino, benzylimino, cyanobenzylimino or nitrobenzylimino, or in each case optionally mono- or disubstituted by identical or different substituents, by aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocycyl-substituted (C1-C4) alkyl, (C1-C4) haloalkyl, (C2-C4) alkenyl, (C3-C6) Cycloalkyl, oxy, amino, N- (C1-C4) alkylamino or N-cyclo-propylamino, wherein aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocycyl each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C 1 -C 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C 1 -C 4) ) Alkoxy, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1-C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1- C4) Haloalkylsulfinyl, (C1-C4) Haloalkylsulfonyl, (C1-C4) Alkoxycarbonyl, (C1- C4) Alkylcarbonyl, hetaryl or alkyl-hetaryl, or for each optionally mono- or polysubstituted, identically or differently substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl, oxo-hetaryl, heterocyclyl or Oxo-heterocyclyl, wherein the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) -Alkoxy, (C1- C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1- C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1-C4) Haloalkylsulfinyl, (C1- C4) Haloalkylsulfonyl, (C1-C4) Alkoxycarbonyl, (C1-C4) Alkylcarbonyl, (C3-C6) Trialkylsilyl, or R3 and R4 together for (C2-C5) -Alkyl or for (C2-C5) Alkenyl, wherein a 3-6 membered by halogen, cyano, (C1-C4) alkyl, (C3-C6) cycloalkyl, (C1-C4) alkoxy, (C1-C4) Haloalkyl, (C1-C4) Haloalkoxy, or (C1-C4Haloalkylthio substituted ring is formed, which may optionally contain one to two double bonds, R5, R6 independently of one another represent hydrogen, cyano, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl or trifluoromethoxy,  V1, V2 independently of one another represent oxygen or sulfur.
Alternativ und ebenfalls besonders bevorzugt (Ausgestaltung 3-2) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyrimidyl, Pyridazinyl, Pyridyl, Thienyl, Furanyl, Oxazolyl, Thiazolyl, Imidazolyl oder Pyrazolyl steht, wobei die Substituenten ausgewählt sind aus Cyano, Halogen, Nitro, SF5, (C1-C4)Alkyl, (C1- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkoxy, (C3-C6)Cycloalkyl, (C3- C6)Halogencycloalkyl, (C1-C4)Alkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkenoxy, (C1-C4)Alkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C1- C4)Alkylsulfinyl, (C1-C4)Halogenalkylsulfinyl, (C3-C6)Cycloalkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfonyl, (C3-C6)Cycloalkylsulfonyl, (C1-C4)Halogenalkylsulfanyl, (C3- C6)Cycloalkylsulfanyl, (C1-C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, Bis-(C1- C4)Alkylamino, Di-(C1-C4)Halogenalkylamino, R1 für (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Hydroxyalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C2- C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1- C4)Alkyl-(C3-C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3- C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, (C1-C4)Alkylthio-(C1-C6)alkyl, (C1- C4)Alkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C6)alkyl oder (C1-C4)Alkoxy steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl oder Heterocyclyl substituiertes (C1-C4)Alkyl, (C3-C6)Cycloalkyl steht, wobei Aryl, Hetaryl oder Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio oder (C1-C6)Alkoxycarbonyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C6)Alkoxycarbonyl, R2 für Wasserstoff, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkoxycarbonyl steht, R3 für Wasserstoff, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkoxycarbonyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, Cyano(C3- C6)cycloalkyl-(C1-C4)alkyl, Halogen(C3-C6)cycloalkyl-(C1-C4)alkyl, (C1-C4)Halogenalkyl-(C3- C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1-C4)Alkyl-(C3- C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3- C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3-C6)cycloalkyl, (C1- C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, Carbamoyl-(C3-C6)cycloalkyl, Thiocarbamoyl-(C3- C6)cycloalkyl, (C1-C4)Alkylcarbonyl-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, Amino, (C1-C4)Alkylamino, Di-(C1-C4)alkyl-amino, (C3-C6)Cycloalkylamino, N-(C1-C4)alkyl- (C3-C6)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, N-(C1-C4)alkyl- Benzylamino, N-(C1-C4)alkyl-Cyanobenzylamino, N-(C1-C4)alkyl-Nitrobenzylamino, (C1- C4)Alkylcarbonyl-amino, (C3-C6)Cycloalkylcarbonylamino, Hydroxy, (C1-C4)Alkoxy, (C3- C6)Cycloalkoxy, (C3-C6)Cycloalkyl-(C1-C4)Alkoxy, Cyano(C1-C4)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, (C1-C4)Alkylimino, (C3-C6)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Halogenbenzylimino, (C1-C4)Halogenalkylbenzylimino, Halogen-[(C1- C4)Halogenalkyl]benzylimino, Nitrobenzylimino, (C1-C4)Alkylsulfonyl-(C1-C4)alkyl, (C1- C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, (C3-C6)Cycloalkylcarbonyl oder (C3- C6)Cycloalkyl-(C1-C4)alkyl-carbonyl steht, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocycyl substituiertes (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C2-C4)Alkenyl, (C3-C6)Cycloalkyl, Oxy, Amino, N-(C1-C4)Alkylamino, N-cyclo-Propylamino oder Carbonyl steht, wobei Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocycyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C4)Halogenalkylsulfinyl, (C1-C4)Halogenalkylsulfonyl, (C1-C4)Alkoxycarbonyl, (C1- C4)Alkylcarbonyl, Hetaryl, Alkyl-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1- C4)Halogenalkylsulfonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Alkylcarbonyl, (C3-C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C5)-Alkyl oder für (C2-C5)Alkenyl stehen, wobei ein 3-6 gliedriger gegebenfalls durch Halogen, Cyano, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, oder (C1-C4)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trifluormethoxy stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. Ganz besonders bevorzugter Bereich: Ganz besonders bevorzugt (Ausgestaltung 4-1) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyridyl, Thienyl oder Pyrazol-1-yl oder Pyrazol-2-yl steht, wobei die Substituenten ausgewählt sind aus Cyano, Fluor, Chlor, Brom, Iod, SF5, Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, Heptafluorisopropyl, Fluorcyclopropyl, Difluorcyclopropyl, Tetrafluorcyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy, Pentafluorethoxy, Tetrafluorethoxy, Trifluorethoxy, Chlortetrafluorethoxy, Dichlortrifluorethoxy, Trichlordifluorethoxy, Chlortrifluorethoxy, Chlordifluorethoxy, Trifluorethenoxy, Trifluormethylsulfonyl, Difluormethylsulfonyl, Trifluormethylsulfinyl, Trifluormethylsulfanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Pentafluorethylsulfanyl, Trifluorethylsulfanyl, Difluorethylsulfanyl, Pentafluorethylsulfonyl, Tetrafluorethylsulfonyl, Trifluorethylsulfonyl, Difluorethylsulfonyl, Pentafluorethylsulfinyl, Tetrafluorethylsulfinyl, Trifluorethylsulfinyl, Difluorethylsulfinyl, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, Trifluormethylcyclopropyl, Trifluormethylcarbonyl, Bis-Trifluormethylamino, (Trifluorvinyl)oxy, R1 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Methyl-cyclo-Propyl, cyclo-Propyl-Methyl, Cyano-cyclo-Propyl, Chlor-cyclo-Propyl, Fluor-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, cyclo-Propyl-cyclo-Propyl, Methoxymethyl, Methoxyethyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo- Butyl, Difluorcyclobutyl, cyclo-Pentyl, Fluormethyl, Difluormethyl oder Trifluormethyl steht, oder für einfach durch Phenyl substituiertes Methyl, Ethyl, i-Propyl oder cyclo-Propyl steht, wobei Phenyl jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy substituiert sein kann, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy substituiertes Phenyl, Pyridyl, Oxazolyl, Thiazolyl, Thienyl, Oxetanyl oder Thietanyl steht, R2 für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Methoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, i-Propylcarbonyl, cyclo-Propylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, n-Propoxycarbonyl oder i-Propoxycarbonyl steht, R3 für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Methoxy, Ethoxy, n-Propyloxy, i-Propyloxy, n-Butyloxy, i-Butyloxy, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, i-Propylcarbonyl, cyclo-Propylcarbonyl, Methyloxycarbonyl, Ethyloxycarbonyl, n-Propyloxycarbonyl oder i-Propyloxycarbonyl steht, R4 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Fluormethyl, Difluormethyl, Trifluormethyl, Difluorethyl, Trifluorethyl, Pentafluorethyl, Trifluorpropyl, Pentafluorpropyl, Cyanomethyl, Cyanoethyl, Cyanopropyl, Cyanobutyl, Cyanopentyl, Cyanohexyl, Methyloxymethyl, Ethyloxymethyl, Methyloxyethyl, Ethyloxyethyl, Methyloxypropyl, Ethyloxypropyl, Propinyl, Butinyl, cyclo-Propyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, cyclo-Propyl-methyl, cyclo-Butyl-methyl, cyclo-Pentyl-methyl, cyclo-Hexyl- methyl, cyclo-Propyl-ethyl, cyclo-Butyl-ethyl, cyclo-Pentyl-ethyl, cyclo-Hexyl-ethyl, Cyano- cyclo-Propyl-methyl, Cyano-cyclo-Butyl-methyl, Cyano-cyclo-Pentyl-methyl, Cyano-cyclo- Hexyl-methyl, Trifluormethyl-cyclo-Propyl-methyl, Trifluormethyl-cyclo-Hexyl-methyl, cyclo- Propyl-cyclo-Propyl, Methyl-cyclo-Propyl, Ethyl-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, Trifluormethyl-cyclo-Butyl, Trifluormethyl-cyclo-Pentyl, Trifluormethyl-cyclo-Hexyl, Fluor- cyclo-Propyl, Difluor-cyclo-Propyl, Tetrafluor-cyclo-Propyl, Cyano-cyclo-Propyl, Cyano-cyclo- Butyl, Cyano-cyclo-Pentyl, Cyano-cyclo-Hexyl, Ethinyl-cyclo-Propyl, Methyloxy-cyclo-Propyl, Ethyloxy-cyclo-Propyl, Methyloxycarbonyl-cyclo-Propyl, Ethyloxycarbonyl-cyclo-Propyl, Thiocarbamoyl-cyclo-Propyl, Methyloxycarbonylmethyl, Ethyloxycarbonylmethyl, Methyloxycarbonylethyl, Ethyloxycarbonylethyl, Methylamino, Ethylamino, n-Propylamino, iso-Propylamino, cyclo-Propylamino, cyclo-Butylamino, cyclo-Pentylamino, cyclo- Hexylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Di-Methylamino, N- Methylethylamino, N-Methyl-n-Propylamino, N-Methyl-iso-Propylamino, N-Methyl-cyclo- Propylamino, N-Methyl-cyclo-Butylamino, N-Methyl-cyclo-Pentylamino, N-Methyl-cyclo- Hexylamino, N-Methyl-Benzylamino, N-Methyl-Cyanobenzylamino, N-Methyl- Nitrobenzylamino, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, cyclo-Propyloxy, cyclo- Propyl-methyloxy, cyclo-Butyloxy, cyclo-Pentyloxy, cyclo-Hexyloxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Methylimino, Ethylimino, n-Propylimino, iso-Propylimino, iso-Butylimino, cyclo-Pentylimino, cyclo-Hexylimino, Benzylimino, Cyanobenzylimino oder Nitrobenzylimino steht, oder für einfach durch Phenyl, Pyridyl, Pyrimidyl, Furanyl, Thiophenyl, Oxazolyl, Thiazolyl, Indolyl, Aza-indolyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl oder 2,3-Dihydro-1,4- benzodioxinyl substituiertes Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, Oxy, Amino, N-Methylamino oder N- Ethylamino steht, wobei Phenyl, Pyridyl, Pyrimidyl, Furanyl, Thiophenyl, Oxazolyl, Thiazolyl, Indolyl, Aza-indolyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Cyano, Fluor, Chlor, Brom, Iod, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, Trifluormethyl, Pentafluorethyl, Methoxy, Ethoxy, Trifluormethoxy, Pentafluorethoxy, Trifluormethylthio, Methyloxycarbonyl, Ethyloxycarbonyl, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, Pyrazolyl, Imidazolyl, Methylpyrazolyl, Oxazolyl, Oxdiazolyl, oder Thiazolyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden substituiertes Phenyl, Pyridyl, Pyrimidyl, Thiophenyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl, Oxetanyl, Thietanyl, Tetrahydrofuranyl, Oxotetrahydrofuranyl, Tetrahydrothiophenyl, Oxidotetrahydrothiophenyl, Dioxidotetrahydrothiophenyl, Tetrahydro-2H-pyranyl, Oxotetrahydro-2H-pyranyl, Tetrahydro-2H-thiopyranyl, Oxotetrahydro-2H-thiopyranyl, 2,3- Dihydro-1H-indenyl steht, wobei die Substituenten ausgewählt sind aus Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy, Trifluormethylthio, Methyloxycarbonyl oder Ethyloxycarbonyl, oder R3 und R4 gemeinsam für (C3-C5)-Alkyl stehen, wobei ein 4-6 gliedriger gegebenfalls durch Halogen, Cyano, Trifluormethyl oder Trifluormethoxy substituierter- Ring gebildet wird, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trifluormethoxy stehen, V1, V2 unabhängig voneinander für Sauerstoff oder Schwefel stehen. Alternativ und ebenfalls ganz besonders bevorzugt (Ausgestaltung 4-2) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyridyl, Thienyl oder Pyrazol-1-yl oder Pyrazol-2-yl steht, wobei die Substituenten ausgewählt sind aus Cyano, Fluor, Chlor, Brom, Iod, SF5, Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, Heptafluorisopropyl, Fluorcyclopropyl, Difluorcyclopropyl, Tetrafluorcyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy, Pentafluorethoxy, Tetrafluorethoxy, Trifluorethoxy, Chlortetrafluorethoxy, Dichlortrifluorethoxy, Trichlordifluorethoxy, Chlortrifluorethoxy, Chlordifluorethoxy, Trifluorethenoxy, Trifluormethylsulfonyl, Difluormethylsulfonyl, Trifluormethylsulfinyl, Trifluormethylsulfanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Pentafluorethylsulfanyl, Trifluorethylsulfanyl, Difluorethylsulfanyl, Pentafluorethylsulfonyl, Tetrafluorethylsulfonyl, Trifluorethylsulfonyl, Difluorethylsulfonyl, Pentafluorethylsulfinyl, Tetrafluorethylsulfinyl, Trifluorethylsulfinyl, Difluorethylsulfinyl, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, Trifluormethylcyclopropyl, Trifluormethylcarbonyl, Bis-Trifluormethylamino, (Trifluorvinyl)oxy, Heptafluorpropoxy oder Hexafluorpropoxy R1 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Methyl-cyclo-Propyl, cyclo-Propyl-Methyl, Cyano-cyclo-Propyl, Chlor-cyclo-Propyl, Fluor-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, cyclo-Propyl-cyclo-Propyl, Methoxymethyl, Methoxyethyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo- Butyl, Difluorcyclobutyl, cyclo-Pentyl, Fluormethyl, Difluormethyl, Trifluormethyl oder Trifluorethyl steht, oder für einfach durch Phenyl substituiertes Methyl, Ethyl, i-Propyl oder cyclo-Propyl steht, wobei Phenyl jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy substituiert sein kann, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy substituiertes Phenyl, Pyridyl, Oxazolyl, Thiazolyl, Thienyl, Oxetanyl oder Thietanyl steht, R2 für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Methoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, i-Propylcarbonyl, cyclo-Propylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, n-Propoxycarbonyl oder i-Propoxycarbonyl steht, R3 für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Methoxy, Ethoxy, n-Propyloxy, i-Propyloxy, n-Butyloxy, i-Butyloxy, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, i-Propylcarbonyl, cyclo-Propylcarbonyl, Methyloxycarbonyl, Ethyloxycarbonyl, n-Propyloxycarbonyl oder i-Propyloxycarbonyl steht, R4 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Fluormethyl, Difluormethyl, Trifluormethyl, Difluorethyl, Trifluorethyl, Pentafluorethyl, Trifluorpropyl, Pentafluorpropyl, Cyanomethyl, Cyanoethyl, Cyanopropyl, Cyanobutyl, Cyanopentyl, Cyanohexyl, Methyloxymethyl, Ethyloxymethyl, Methyloxyethyl, Ethyloxyethyl, Methyloxypropyl, Ethyloxypropyl, Propinyl, Butinyl, cyclo-Propyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, cyclo-Propyl-methyl, cyclo-Butyl-methyl, cyclo-Pentyl-methyl, cyclo-Hexyl- methyl, cyclo-Propyl-ethyl, cyclo-Butyl-ethyl, cyclo-Pentyl-ethyl, cyclo-Hexyl-ethyl, Cyano- cyclo-Propyl-methyl, Cyano-cyclo-Butyl-methyl, Cyano-cyclo-Pentyl-methyl, Cyano-cyclo- Hexyl-methyl, Trifluormethyl-cyclo-Propyl-methyl, Trifluormethyl-cyclo-Hexyl-methyl, cyclo- Propyl-cyclo-Propyl, Methyl-cyclo-Propyl, Ethyl-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, Trifluormethyl-cyclo-Butyl, Trifluormethyl-cyclo-Pentyl, Trifluormethyl-cyclo-Hexyl, Fluor- cyclo-Propyl, Difluor-cyclo-Propyl, Tetrafluor-cyclo-Propyl, Cyano-cyclo-Propyl, Cyano-cyclo- Butyl, Cyano-cyclo-Pentyl, Cyano-cyclo-Hexyl, Ethinyl-cyclo-Propyl, Methyloxy-cyclo-Propyl, Ethyloxy-cyclo-Propyl, Methyloxycarbonyl-cyclo-Propyl, Ethyloxycarbonyl-cyclo-Propyl, Thiocarbamoyl-cyclo-Propyl, Methyloxycarbonylmethyl, Ethyloxycarbonylmethyl, Methyloxycarbonylethyl, Ethyloxycarbonylethyl, Methylamino, Ethylamino, n-Propylamino, iso-Propylamino, cyclo-Propylamino, cyclo-Butylamino, cyclo-Pentylamino, cyclo- Hexylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Di-Methylamino, N- Methylethylamino, N-Methyl-n-Propylamino, N-Methyl-iso-Propylamino, N-Methyl-cyclo- Propylamino, N-Methyl-cyclo-Butylamino, N-Methyl-cyclo-Pentylamino, N-Methyl-cyclo- Hexylamino, N-Methyl-Benzylamino, N-Methyl-Cyanobenzylamino, N-Methyl- Nitrobenzylamino, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, cyclo-Propyloxy, cyclo- Propyl-methyloxy, cyclo-Butyloxy, cyclo-Pentyloxy, cyclo-Hexyloxy, Cyanomethyloxy, Cyanoethyloxy, Cyanopropyloxy, Cyanobutyloxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Methylimino, Ethylimino, n-Propylimino, iso-Propylimino, iso-Butylimino, cyclo-Pentylimino, cyclo-Hexylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino, Fluorbenzylimino, Chlorbenzylimino,Trifluormethylbenzylimino, Chlor- (Trifluormethyl)benzylimino, Fluor-(Trifluormethyl)benzylimino, Methylsulfonylmethyl, Methylsulfonylethyl, Methylsulfonylpropyl, Methylsulfonylbutyl, Methylcarbonyl, Ethylcarbonyl, Propylcarbonyl, iso-Propylcarbonyl, cyclo-Propylcarbonyl, cyclo-Propyl- methylcarbonyl, cyclo-Butyl-methylcarbonyl, Butylcarbonyl, iso-Butylcarbonyl, tert- Butylcarbonyl, cyclo-Butylcarbonyl, cyclo-Pentylcarbonyl, cyclo-Hexylcarbonyl oder Trifluormethylcarbonyl steht, oder für einfach durch Phenyl, Pyridyl, Pyrimidyl, Furanyl, Thiophenyl, Oxazolyl, Thiazolyl, Indolyl, Aza-indolyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl oder 2,3-Dihydro-1,4- benzodioxinyl substituiertes Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, Oxy, Amino, N-Methylamino, N-Ethylamino oder Carbonyl steht, wobei Phenyl, Pyridyl, Pyrimidyl, Furanyl, Thiophenyl, Oxazolyl, Thiazolyl, Indolyl, Aza-indolyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Cyano, Fluor, Chlor, Brom, Iod, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, Trifluormethyl, Pentafluorethyl, Methoxy, Ethoxy, Trifluormethoxy, Pentafluorethoxy, Trifluormethylthio, Methyloxycarbonyl, Ethyloxycarbonyl, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, Pyrazolyl, Imidazolyl, Methylpyrazolyl, Oxazolyl, Oxdiazolyl, Thiazolyl, Pyrrolyl, Pyrrolidinyl oder Pyrrolidinonyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden substituiertes Phenyl, Pyridyl, Pyrimidyl, Thiophenyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl, Oxetanyl, Thietanyl, Tetrahydrofuranyl, Oxotetrahydrofuranyl, Tetrahydrothiophenyl, Oxidotetrahydrothiophenyl, Dioxidotetrahydrothiophenyl, Tetrahydro-2H-pyranyl, Oxotetrahydro-2H-pyranyl, Tetrahydro-2H-thiopyranyl, Oxotetrahydro-2H-thiopyranyl, 2,3- Dihydro-1H-indenyl steht, wobei die Substituenten ausgewählt sind aus Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy, Trifluormethylthio, Methyloxycarbonyl oder Ethyloxycarbonyl, oder R3 und R4 gemeinsam für (C3-C5)-Alkyl stehen, wobei ein 4-6 gliedriger gegebenfalls durch Halogen, Cyano, Trifluormethyl oder Trifluormethoxy substituierter- Ring gebildet wird, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trifluormethoxy stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. Insbesondere ganz besonders bevorzugter Bereich: Insbesondere ganz besonders bevorzugt (Ausgestaltung 5-1) sind die Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach, zweifach, dreifach oder vierfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyridyl, Thienyl oder Pyrazol-1-yl oder Pyrazol-2-yl steht, wobei die Substituenten ausgewählt sind aus Fluor, Chlor, Brom, Iod, SF5, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, Heptafluorisopropyl, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Pentafluorethoxy, Tetrafluorethoxy, Chlortrifluorethoxy, Trifluorethenoxy, Trifluormethylsulfonyl, Trifluormethylsulfinyl, Trifluormethylsulfanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Trifluormethylcyclopropyl, Bis-Trifluormethylamino, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, (Trifluorvinyl)oxy, R1 für Methyl, Ethyl, i-Propyl, cyclo-Propyl, Methyl-cyclo-Propyl, Cyclo-Propyl-Methyl, Cyano- cyclo-Propyl, Chlor-cyclo-Propyl, cyclo-Propyl-cyclo-Propyl, Methoxyethyl, tert.-Butyl, cyclo- Butyl, Difluorcyclobutyl oder cyclo-Pentyl steht, oder für einfach durch Phenyl substituiertes Methyl steht, wobei Phenyl gegebenenfalls einfach durch Chlor, Brom, Nitro, Trifluormethyl substituiert sein kann, oder für gegebenenfalls einfach durch Chlor substituiertes Phenyl oder für Oxazolyl steht, R2 für Wasserstoff, Methyl, Ethyl, cyclo-Propylcarbonyl oder Methoxycarbonyl steht, R3 für Wasserstoff, Methyl, Methoxy oder Methoxycarbonyl steht, R4 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, cyclo-Butyl, Trifluorethyl, Trifluorpropyl, Cyanomethyl, Cyanoethyl, Cyanopropyl, Cyanobutyl, Cyanopentyl, Methyloxyethyl, Propinyl, Butinyl, cyclo-Propyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, cyclo- Propyl-methyl, cyclo-Butyl-methyl, cyclo-Pentyl-methyl, cyclo-Hexyl-methyl, cyclo-Propyl- ethyl, Cyano-cyclo-Hexyl-methyl, Trifluormethyl-cyclo-Hexyl-methyl, cyclo-Propyl-cyclo- Propyl, Methyl-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, Trifluormethyl-cyclo-Hexyl, Difluor-cyclo-Propyl, Cyano-cyclo-Propyl, Cyano-cyclo-Butyl, Cyano-cyclo-Hexyl, Ethinyl- cyclo-Propyl, Methyloxy-cyclo-Propyl, Methyloxycarbonyl-cyclo-Propyl, Thiocarbamoyl- cyclo-Propyl oder Methyloxycarbonylethyl steht, oder für einfach durch Phenyl, Pyridyl, Indazolyl, Aza-indazolyl oder 1,3-Benzodioxolyl substituiertes Methyl, Ethyl, n-Propyl oder cyclo-Propyl steht, wobei Phenyl, Pyridyl, Indazolyl, Aza-indazolyl, oder 1,3-Benzodioxolyl jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Cyano, Fluor, Chlor, Nitro, Methyl, Trifluormethyl, Methoxy, Methyloxycarbonyl, Thiocarbamoyl, Aminosulfonyl, Methylpyrazolyl, Oxazolyl oder Oxadiazolyl substituiert sein können, oder für jeweils gegebenenfalls einfach substituiertes Phenyl, Pyridyl, Indazolyl, Oxetanyl, Thietanyl, Tetrahydrofuranyl, Oxotetrahydrofuranyl, Dioxidotetrahydrothiophenyl, Tetrahydro- 2H-pyranyl oder 2,3-Dihydro-1H-indenyl steht, wobei die Substituenten ausgewählt sind aus Chlor, Cyano, Methyl oder Methyloxycarbonyl, oder R3 und R4 gemeinsam für (C3-C5)-Alkyl stehen, wobei ein 4-6 gliedriger gegebenfalls durch Cyano substituierter Ring gebildet wird, R5, R6 unabhängig voneinander für Wasserstoff stehen V1, V2 unabhängig voneinander für Sauerstoff oder Schwefel stehen. Alternativ und ebenfalls insbesondere ganz besonders bevorzugt (Ausgestaltung 5-2) sind die Alternatively and also particularly preferred (embodiment 3-2) are the compounds of the formula (I) in which Q 1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents, phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1, 4-benzodioxinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furanyl, oxazolyl, thiazolyl, imidazolyl or pyrazolyl, wherein the substituents are selected from cyano, halo, nitro, SF5, (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl , (C2-C4) alkenyl, (C2-C4) haloalkenyl, (C2-C4) alkynyl, (C2-C4) haloalkynyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C1-C4) alkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkenoxy, (C1-C4) alkylsulfanyl, ( C3-C6) halocycloalkylsulfanyl, (C1-C4) alkylsulfinyl, (C1-C4) haloalkylsulfinyl, (C3-C6) cycloalkylsulfinyl, (C1-C4) alkylsulfonyl, (C1-C4) haloalkylsulfonyl, (C3-C6) cycloalkylsulfonyl, (C1 -C4) haloalkylsulfanyl, (C3-C6) cycloalkylsulfane yl, (C1-C4) alkylcarbonyl, (C1-C4) haloalkylcarbonyl, bis (C1-C4) alkylamino, di (C1-C4) haloalkylamino, R1 for (C1-C4) alkyl, (C1-C4) haloalkyl, (C1-C4) hydroxyalkyl, (C1-C4) alkoxy- (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) haloalkenyl, (C2-C4) alkynyl, (C2-C4) alkynyloxy- ( C1-C4) alkyl, (C3- C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C4) alkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (C1-C4) alkyl- ( C 3 -C 6) cycloalkyl, (C 1 -C 4) haloalkyl (C 3 -C 6) cycloalkyl, halo (C 3 - C 6) cycloalkyl, cyano (C 3 -C 6) cycloalkyl, (C 2 - C 4) alkynyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy (C 3 - C 6) cycloalkyl, (C 1 -C 4) alkoxycarbonyl (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkylthio (C 1 -C 6) alkyl, (C 1 - C 4) alkylcarbonyl (C 1 -C 6) alkyl, (C 1 -C 4) alkoxycarbonyl (C 1 -C 6 ) is alkyl or (C 1 -C 4 ) alkoxy, or in each case optionally monosubstituted or polysubstituted by identical or different aryl, hetaryl or heterocyclyl (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl , where Ary l, hetaryl or heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 - C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio or (C 1 -C 6 ) alkoxycarbonyl may be substituted, or for each optionally mono- or polysubstituted by identical or different substituted aryl , Hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halogen, cyano, nitro, (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 - C4) haloalkyl, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-C6) alkoxycarbonyl, R2 represents hydrogen, (C1-C4) alkyl, (C3-C6) cycloalkyl, (C1-C4) alkoxy, (C1-C4) alkylcarbonyl, (C3-C6) cycloalkylcarbonyl or (C1-C4) alkoxycarbonyl, R3 represents hydrogen, (C1-C4) alkyl, (C3-C6) cycloalkyl, (C1-4) C4) alkoxy, (C1-C4) alkylcarbonyl, (C3-C6) cycloalkylcarbonyl or (C1-C4) alkoxycarbonyl, R4 represents (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, ( C1-C4) hydroxyalkyl, (C1-C4) alkoxy- (C1-C4) alkyl, (C1-C4) haloalkoxy- (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkenyloxy- (C1 C4) alkyl, (C2-C4) haloalkenyloxy- (C1-C4) alkyl, (C2-C4) haloalkenyl, (C2-C4) cyanoalkenyl, (C2-C4) alkynyl, (C2-C4) alkynyloxy- (C1- C4) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C4) alkyl, cyano (C3-C6) cycloalkyl- (C1- C4) alkyl, halo (C3-C6) cycloalkyl- (C1-C4) alkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl- (C1-C4) -alkyl, (C3-C6) cycloalkyl- (C3-C6) -alkyl C6) cycloalkyl, ( C1-C4) alkyl (C3-C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) alkynyl (C3-C6) cycloalkyl, (C1-C4) alkoxy- (C3-C6) cycloalkyl, (C1-C4) alkoxycarbonyl- (C3-C6) cycloalkyl, carbamoyl- (C3-C6) cycloalkyl, thiocarbamoyl- (C3-C6 ) cycloalkyl, (C 1 -C 4) alkylcarbonyl (C 1 -C 4) alkyl, (C 1 -C 4) alkoxycarbonyl (C 1 -C 4) alkyl, amino, (C 1 -C 4) alkylamino, di (C 1 -C 4) alkylamino , (C3-C6) cycloalkylamino, N- (C1-C4) alkyl- (C3-C6) cycloalkylamino, benzylamino, Cyanobenzylamino, nitrobenzylamino, N- (C1-C4) alkyl-benzylamino, N- (C 1 -C 4) alkyl-Cyanobenzylamino, N- (C 1 -C 4) alkyl-nitrobenzylamino, (C 1 - C 4) alkylcarbonyl-amino, (C 3 -C 6) cycloalkylcarbonylamino, hydroxy, (C 1 -C 4) alkoxy, (C 3 -C 6 ) cycloalkoxy, (C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkoxy, cyano (C 1 -C 4 ) alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, (C 1 -C 4 ) alkylimino, (C 3 -C 6 ) cycloalkylimino, benzylimino, cyanobenzylimino, halobenzylimino, (C 1 -C 4 ) haloalkylbenzylimino, Ha lied - [(C 1 - C 4) haloalkyl] benzylimino, Nitrobenzylimino, (C 1 -C 4) alkylsulfonyl (C 1 -C 4) alkyl, (C 1 - C 4) alkylcarbonyl, (C 1 -C 4) Haloalkylcarbonyl, (C 3 -C 6 ) cycloalkylcarbonyl or (C 3 -C 6 ) -cycloalkyl- (C 1 -C 4 ) -alkyl-carbonyl, or in each case optionally monosubstituted or disubstituted, identical or different, by aryl, Benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocycyl substituted (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) Alkenyl, (C 3 -C 6 ) cycloalkyl, oxy, amino, N- (C 1 -C 4 ) alkylamino, N-cyclopropylamino or carbonyl, wherein aryl, 1,3-benzodioxolyl, 2,3-dihydro-1 , 4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocycyl each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C 1 -C 4) ) Alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl , (C 1 -C 4 ) haloalkoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, (C1-C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfonyl, (C1-C4) alkoxycarbonyl, ( C1-C4) alkylcarbonyl, hetaryl, alkyl-hetaryl, heterocyclyl or oxo-heterocyclyl may be substituted, or for each optionally mono- or polysubstituted, identically or differently substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl , Hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, wherein the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (Cl -C4) alkoxy, (C1-C4) haloalkyl, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, (C1 -C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfonyl, (C1-C4) alkoxycarbonyl, (C1-C4) alkylcarbonyl, (C3-C6) trialkylsilyl, or R3 and R4 together for (C2-C5) -alkyl or for (C2 -C5) alkenyl, with a 3-6 membered g optionally substituted by halogen, cyano, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, or (C 1 -C 4) haloalkylthio R5, R6 are each independently hydrogen, cyano, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl or trifluoromethoxy, V1 is oxygen or sulfur, V2 is oxygen, sulfur or - is formed ring, which may optionally contain one to two double bonds NH stands. Very particularly preferred range: Very particularly preferred (embodiment 4-1) are the compounds of formula (I) in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents phenyl, 1,3-benzodioxolyl, 2,3-dihydro 1,4-benzodioxinyl, pyridyl, thienyl or pyrazol-1-yl or pyrazol-2-yl, wherein the substituents are selected from cyano, fluorine, chlorine, bromine, iodine, SF5, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoroisopropyl, fluorocyclopropyl, difluorocyclopropyl, tetrafluorocyclopropyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, pentafluoroethoxy, tetrafluoroethoxy, trifluoroethoxy, chlorotetrafluoroethoxy, Dichlorotrifluoroethoxy, trichlorodifluoroethoxy, chlorotrifluoroethoxy, chlorodifluoroethoxy, trifluoroethenoxy, trifluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromet hylsulfinyl, Trifluoromethylsulphanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Pentafluorethylsulfanyl, Trifluorethylsulfanyl, Difluorethylsulfanyl, pentafluoroethylsulfonyl, Tetrafluorethylsulfonyl, trifluoroethylsulfonyl, Difluorethylsulfonyl, Pentafluorethylsulfinyl, Tetrafluorethylsulfinyl, trifluoroethylsulfinyl, Difluorethylsulfinyl, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, Trifluormethylcyclopropyl, trifluoromethylcarbonyl, bis-trifluoromethylamino, (trifluorovinyl) oxy, R1 is methyl, ethyl , n-propyl, i-propyl, cyclo-propyl, methyl-cyclo-propyl, cyclo-propyl-methyl, cyano-cyclo-propyl, chloro-cyclo-propyl, fluoro-cyclo-propyl, trifluoromethyl-cyclo-propyl, cyclo Propylcyclopropyl, methoxymethyl, methoxyethyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, difluorocyclobutyl, cyclo-pentyl, fluoromethyl, difluoromethyl or trifluoromethyl, or methyl which is monosubstituted by phenyl, ethyl , i-propyl or cyclo-propyl, wherein each phenyl optionally single or double , identical or different, may be substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, or in each case optionally monosubstituted or disubstituted by identical or variously substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, trifluoromethyl, methoxy, trifluoromethoxy phenyl, pyridyl, oxazolyl, thiazolyl, thienyl, oxetanyl or thietanyl, R2 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclo-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n- Butoxy, i-butoxy, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, cyclo-propylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl or i-propoxycarbonyl, R3 is hydrogen, methyl, ethyl, n-propyl, i-propyl , cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-but yloxy, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, cyclopropylcarbonyl, methyloxycarbonyl, ethyloxycarbonyl, n-propyloxycarbonyl or i-propyloxycarbonyl, R4 represents methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n Butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoroethyl, pentafluoroethyl, trifluoropropyl, pentafluoropropyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, cyanohexyl, methyloxymethyl, ethyloxymethyl, methyloxyethyl, Ethyloxyethyl, methyloxypropyl, ethyloxypropyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclo-pentyl, cyclohexyl, cyclopropylmethyl, cyclo-butylmethyl, cyclo-pentylmethyl, cyclohexylmethyl, cyclo-propyl-ethyl, cyclo-butyl-ethyl, cyclo-pentyl-ethyl, cyclo-hexyl-ethyl, cyano-cyclo-propyl-methyl, cyano-cyclo-butyl-methyl, cyano-cyclo-pentyl-methyl, cyano- cyclo Hexyl-methyl, trifluoromethyl-cyclo-propyl-methyl, trifluoromethyl-cyclo-hexyl-methyl, cyclo-propyl-cyclo-propyl, methyl-cyclo-propyl, ethyl-cyclo-propyl, trifluoromethyl-cyclo-propyl, trifluoromethyl-cyclo Butyl, trifluoromethyl-cyclo-pentyl, trifluoromethyl-cyclo-hexyl, fluorocyclobutyl, difluorocyclopentyl, tetrafluoro-cyclo-propyl, cyano-cyclo-propyl, cyano-cyclo-butyl, cyano-cyclo-pentyl, Cyano-cyclo-hexyl, ethynyl-cyclo-propyl, methyloxy-cyclo-propyl, ethyloxy-cyclo-propyl, methyloxycarbonyl-cyclo-propyl, ethyloxycarbonyl-cyclo-propyl, thiocarbamoyl-cyclo-propyl, methyloxycarbonylmethyl, ethyloxycarbonylmethyl, methyloxycarbonylethyl, ethyloxycarbonylethyl, Methylamino, ethylamino, n-propylamino, isopropylamino, cyclopropylamino, cyclo-butylamino, cyclo-pentylamino, cyclohexylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, di-methylamino, N-methylethylamino, N-methyl-n-propylamino, N-methylisopropylamino, N-methylcyclopropylamino, N-methylcyclobutylamino, N-met hyl-cyclo-pentylamino, N-methylcyclohexylamino, N-methylbenzylamino, N-methyl-cyanobenzylamino, N-methyl-nitrobenzylamino, methoxy, ethoxy, n-propyloxy, iso-propyloxy, cyclopropyloxy, cyclo- Propylmethyloxy, cyclobutyloxy, cyclo-pentyloxy, cyclo-hexyloxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, methylimino, ethylimino, n-propylimino, iso-propylimino, iso-butylimino, cyclo-pentylimino, cyclo-hexylimino, benzylimino, cyanobenzylimino or Nitrobenzylimino, or is simply phenyl, pyridyl, pyrimidyl, furanyl, thiophenyl, oxazolyl, thiazolyl, indolyl, aza-indolyl, indazolyl, aza-indazolyl, 1,3-benzodioxolyl or 2,3-dihydro-1,4-benzodioxinyl substituted methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, cyclo-pentyl, cyclo-hexyl, oxy, amino, N-methylamino or N-ethylamino, wherein phenyl, pyridyl, pyrimidyl, furanyl, thiophenyl, oxazolyl, thiazolyl, indolyl, aza-indolyl, indazolyl, aza-indazolyl, 1,3-benzodioxolyl each optionally mono- or polysubstituted, identically or differently, by cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, pentafluoroethoxy, trifluoromethylthio, Methyloxycarbonyl, ethyloxycarbonyl, carbamoyl, thiocarbamoyl, aminosulfonyl, pyrazolyl, imidazolyl, methylpyrazolyl, oxazolyl, oxdiazolyl, or thiazolyl, or represents phenyl, pyridyl, pyrimidyl, thiophenyl, indazolyl, azidyl, which is optionally monosubstituted or disubstituted by identical or different substituents. indazolyl, 1,3-benzodioxolyl, oxetanyl, thietanyl, tetrahydrofuranyl, oxotetrahydrofuranyl, tetrahydrothiophenyl, oxidotetrahydrothiophenyl, dioxotetrahydrothiophenyl, tetrahydro-2H-pyranyl, oxotetrahydro-2H-pyranyl, tetrahydro-2H-thiopyranyl, oxotetrahydro-2H-thiopyranyl, 2,3- Dihydro-1H-indenyl, wherein the substituents are selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl , n-propyl, i-propyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, trifluoromethylthio, methyloxycarbonyl or ethyloxycarbonyl, or R 3 and R 4 together represent (C 3 -C 5) -alkyl, forming a 4-6 membered ring optionally substituted by halogen, cyano, trifluoromethyl or trifluoromethoxy, R 5, R 6 independently of one another represent hydrogen, cyano, fluorine, chlorine, Bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trifluoromethoxy, V1, V2 independently represent oxygen or sulfur. Alternatively and also very particularly preferred (embodiment 4-2) are the compounds of formula (I) in which Q1 is in each case optionally mono- or polysubstituted by identical or different substituents phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1 , 4-benzodioxinyl, pyridyl, thienyl or pyrazol-1-yl or pyrazol-2-yl, wherein the substituents are selected from cyano, fluorine, chlorine, bromine, iodine, SF5, methyl, ethyl, n-propyl, i- Propyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoroisopropyl, fluorocyclopropyl, difluorocyclopropyl, tetrafluorocyclopropyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, pentafluoroethoxy, tetrafluoroethoxy, trifluoroethoxy, chlorotetrafluoroethoxy, dichlorotrifluoroethoxy, Trichlorodifluoroethoxy, chlorotrifluoroethoxy, chlorodifluoroethoxy, trifluoroethenoxy, trifluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfinyl , Trifluoromethylsulphanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Pentafluorethylsulfanyl, Trifluorethylsulfanyl, Difluorethylsulfanyl, pentafluoroethylsulfonyl, Tetrafluorethylsulfonyl, trifluoroethylsulfonyl, Difluorethylsulfonyl, Pentafluorethylsulfinyl, Tetrafluorethylsulfinyl, trifluoroethylsulfinyl, Difluorethylsulfinyl, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, Trifluormethylcyclopropyl, trifluoromethylcarbonyl, bis-trifluoromethylamino, (trifluorovinyl) oxy, heptafluoropropoxy or hexafluoropropoxy R1 for methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, methyl-cyclo-propyl, cyclo-propyl-methyl, cyano-cyclo-propyl, chloro-cyclo-propyl, fluoro-cyclo-propyl, trifluoromethyl-cyclo Propyl, cyclo-propyl-cyclo-propyl, methoxymethyl, methoxyethyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, difluorocyclobutyl, cyclo-pentyl, fluoromethyl, difluoromethyl, trifluoromethyl or trifluoroethyl, or simply phenyl substituted methyl, ethyl, i-propyl or cyclopropyl, where each phenyl may optionally be monosubstituted or disubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, or phenyl optionally substituted once or twice, identically or differently, by phenyl, pyridyl, oxazolyl, substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, Thiazolyl, thienyl, oxetanyl or thietanyl, R 2 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclo-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, cyclopropylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl or i-propoxycarbonyl, R3 is hydrogen, methyl , Ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i- Butyloxy, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, cyclopropylcarbonyl, methyloxycarbonyl, ethyloxycarbonyl, n-propyloxycarbonyl or i-propyloxycarbonyl st e, R4 is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoroethyl, pentafluoroethyl, trifluoropropyl , Pentafluoropropyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, cyanohexyl, methyloxymethyl, ethyloxymethyl, methyloxyethyl, ethyloxyethyl, methyloxypropyl, ethyloxypropyl, propynyl, butynyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclohexyl, cyclopropyl -methyl, cyclo-butyl-methyl, cyclo-pentyl-methyl, cyclo-hexyl-methyl, cyclo-propyl-ethyl, cyclo-butyl-ethyl, cyclo-pentyl-ethyl, cyclo-hexyl-ethyl, cyano-cyclo-propyl -methyl, cyano-cyclo-butyl-methyl, cyano-cyclo-pentyl-methyl, cyano-cyclo-hexyl-methyl, trifluoromethyl-cyclo-propyl-methyl, trifluoromethyl-cyclo-hexyl-methyl, cyclo-propyl-cyclo-propyl , Methyl-cyclo-propyl, ethyl-cyclo-propyl, trifluoromethyl-cyclo-propyl, trifluoromethyl-cyclo-butyl, trifluoromethyl-cyclo-pentyl, trifluoromethyl-cyclo-hexyl, Fl cyclohepropyl, difluoro-cyclo-propyl, tetrafluoro-cyclo-propyl, cyano-cyclo-propyl, cyano-cyclo-butyl, cyano-cyclo-pentyl, cyano-cyclo-hexyl, ethynyl-cyclo-propyl, methyloxy- cyclopropyl, ethyloxycyclopropyl, methyloxycarbonylcyclopropyl, ethyloxycarbonylcyclopropyl, thiocarbamoylcyclopropyl, methyloxycarbonylmethyl, ethyloxycarbonylmethyl, methyloxycarbonylethyl, ethyloxycarbonylethyl, methylamino, ethylamino, n-propylamino, isopropylamino, cyclopropyl Propylamino, cyclo-butylamino, cyclo-pentylamino, cyclohexylamino, benzylamino, Cyanobenzylamino, nitrobenzylamino, di-methylamino, N-methylethylamino, N-methyl-n-propylamino, N-methyl-iso-propylamino, N-methyl-cyclo Propylamino, N-methyl-cyclo-butylamino, N-methyl-cyclo-pentylamino, N-methyl-cyclo-hexylamino, N-methyl-benzylamino, N-methyl-cyanobenzylamino, N-methyl-nitrobenzylamino, methoxy, ethoxy, n- Propyloxy, iso-propyloxy, cyclopropyloxy, cyclopropylmethyloxy, cyclobutyloxy, cyclo-pentyloxy, cyclohexyloxy, cyanom ethyloxy, cyanoethyloxy, cyanopropyloxy, cyanobutyloxy, benzyloxy, cyanobenzyloxy, Nitrobenzyloxy, methylimino, ethylimino, n -propylimino, iso -propylimino, iso-butylimino, cyclo-pentylimino, cyclohexylimino, benzylimino, cyanobenzylimino, nitrobenzylimino, fluorobenzylimino, chlorobenzylimino, trifluoromethylbenzylimino, chloro (trifluoromethyl) benzylimino, fluoro (trifluoromethyl) benzylimino, methylsulfonylmethyl, methylsulfonylethyl, methylsulfonylpropyl, methylsulfonylbutyl, methylcarbonyl, ethylcarbonyl, propylcarbonyl, iso-propylcarbonyl, cyclopropylcarbonyl, cyclopropylmethylcarbonyl, cyclo-butylmethylcarbonyl, butylcarbonyl, isobutylcarbonyl, tert-butylcarbonyl, cyclo-butylcarbonyl, cyclo-pentylcarbonyl, cyclohexylcarbonyl or trifluoromethylcarbonyl, or is simply phenyl, pyridyl, pyrimidyl, furanyl, thiophenyl, oxazolyl, thiazolyl, indolyl, aza-indolyl, indazolyl, aza-indazolyl, 1,3-benzodioxolyl or 2,3 Dihydro-1,4-benzodioxinyl substituted methyl, ethyl, n -propyl, i -propyl, cyclopropyl, n -butyl, i -butyl, tert -butyl, cyclobutyl, cy cyclo-pentyl, cyclohexyl, oxy, amino, N -methylamino, N -ethylamino or carbonyl, wherein phenyl, pyridyl, pyrimidyl, furanyl, thiophenyl, oxazolyl, thiazolyl, indolyl, aza-indolyl, indazolyl, aza-indazolyl, 1,3-benzodioxolyl each optionally mono- or polysubstituted by identical or different cyano, fluoro, chloro, bromo, iodo, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy , Pentafluoroethoxy, trifluoromethylthio, methyloxycarbonyl, ethyloxycarbonyl, carbamoyl, thiocarbamoyl, aminosulfonyl, pyrazolyl, imidazolyl, methylpyrazolyl, oxazolyl, oxdiazolyl, thiazolyl, pyrrolyl, pyrrolidinyl or pyrrolidinonyl, or for in each case optionally monosubstituted or disubstituted by identical or different substituents, Pyridyl, pyrimidyl, thiophenyl, indazolyl, aza-indazolyl, 1,3-benzodioxolyl, oxetanyl, thietanyl, tetrahydrofuranyl, oxotetrahydrofuranyl, tetrahydrothiophenyl, oxidotetrahydrothio phenyl, dioxotetrahydrothiophenyl, tetrahydro-2H-pyranyl, oxo-tetrahydro-2H-pyranyl, tetrahydro-2H-thiopyranyl, oxo-tetrahydro-2H-thiopyranyl, 2,3-dihydro-1H-indenyl, wherein the substituents are selected from fluoro, chloro, bromo , Cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, trifluoromethylthio, methyloxycarbonyl or ethyloxycarbonyl, or R 3 and R 4 together represent (C 3 -C 5 ) -alkyl, wherein a 4-6 membered ring optionally substituted by halo, cyano, trifluoromethyl or trifluoromethoxy is formed; R5, R6 are independently hydrogen, cyano, fluoro, chloro, bromo, methyl, ethyl, difluoromethyl, trifluoromethyl or trifluoromethoxy, V1 is Oxygen or sulfur, V2 is oxygen, sulfur or -NH. In particular, very particularly preferred range: In particular, very particularly preferred (embodiment 5-1) are the compounds of formula (I) in which Q1 is in each case optionally mono-, di-, tri- or tetra, phenyl which is identical or differently substituted, 1,3-benzodioxolyl , 2,3-dihydro-1,4-benzodioxinyl, pyridyl, thienyl or pyrazol-1-yl or pyrazol-2-yl, wherein the substituents are selected from fluorine, chlorine, bromine, iodine, SF5, methyl, ethyl, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoroisopropyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, tetrafluoroethoxy, Chlortrifluorethoxy, Trifluorethenoxy, trifluoromethylsulfonyl, trifluoromethylsulfinyl, trifluoromethylsulphanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Trifluormethylcyclopropyl, bis-trifluoromethylamino, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, (trifluorovinyl ) oxy, R1 is methyl, ethyl, i-propyl, cyclopropyl , Methyl-cyclo-propyl, cyclo-propyl-methyl, cyano-cyclo-propyl, chloro-cyclo-propyl, cyclo-propyl-cyclo-propyl, methoxyethyl, tert-butyl, cyclo-butyl, difluorocyclobutyl or cyclo-pentyl , or is phenyl which is monosubstituted by phenyl, where phenyl may optionally be monosubstituted by chlorine, bromine, nitro, trifluoromethyl, or phenyl which is optionally monosubstituted by chlorine or oxazolyl, R 2 is hydrogen, methyl, ethyl, cyclopropylcarbonyl or methoxycarbonyl, R3 is hydrogen, methyl, methoxy or methoxycarbonyl, R4 is methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, cyclo-butyl, trifluoroethyl, trifluoropropyl, cyanomethyl , Cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, methyloxyethyl, propynyl, butynyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclo-hexyl, cyclopropyl-methyl, cyclo-butyl-methyl, cyclo-pentyl-methyl, cyclo -Hexyl-methyl, cyclo-propyl-ethyl, cyano-cyclo-hexyl-methyl, Trifluoromethylcyclohexylmethyl, cyclopropylcyclopropyl, methylcyclopropyl, trifluoromethylcyclopropyl, trifluoromethylcyclohexyl, difluoro-cyclopropyl, cyano-cyclopropyl, cyano-cyclopropyl Butyl, cyano-cyclo-hexyl, ethynyl-cyclo-propyl, methyloxy-cyclo-propyl, methyloxycarbonyl-cyclo-propyl, thiocarbamoyl-cyclo-propyl or methyloxycarbonylethyl, or represents simply by phenyl, pyridyl, indazolyl, aza-indazolyl or 1 , 3-benzodioxolyl is substituted methyl, ethyl, n-propyl or cyclopropyl, where phenyl, pyridyl, indazolyl, Aza-indazolyl, or 1,3-benzodioxolyl each optionally optionally mono-, di- or trisubstituted by the same or different cyano, fluoro, chloro, nitro, methyl, trifluoromethyl, methoxy, methyloxycarbonyl, thiocarbamoyl, aminosulfonyl, methylpyrazolyl, oxazolyl or oxadiazolyl , or represents in each case optionally monosubstituted phenyl, pyridyl, indazolyl, oxetanyl, thietanyl, tetrahydrofuranyl, oxotetrahydrofuranyl, dioctotetrahydrothiophenyl, tetrahydro-2H-pyranyl or 2,3-dihydro-1H-indenyl, where the substituents are selected from chlorine, cyano, Methyl or methyloxycarbonyl, or R3 and R4 together represent (C3-C5) -alkyl, forming a 4-6 membered optionally cyano-substituted ring, R5, R6 independently of one another represent hydrogen V1, V2 independently of one another oxygen or sulfur stand. Alternatively and also particularly particularly preferred (embodiment 5-2) are the
Verbindungen der Formel (I), in denen Q1 für jeweils gegebenenfalls einfach, zweifach, dreifach oder vierfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyridyl, Thienyl oder Pyrazol-1-yl oder Pyrazol-2-yl steht, wobei die Substituenten ausgewählt sind aus Fluor, Chlor, Brom, Iod, SF5, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, Heptafluorisopropyl, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Pentafluorethoxy, Tetrafluorethoxy, Chlortrifluorethoxy, Trifluorethenoxy, Trifluormethylsulfonyl, Trifluormethylsulfinyl, Trifluormethylsulfanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Trifluormethylcyclopropyl, Bis-Trifluormethylamino, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, (Trifluorvinyl)oxy oder Hexafluorpropoxy R1 für Methyl, Ethyl, i-Propyl, cyclo-Propyl, Methyl-cyclo-Propyl, Cyclo-Propyl-Methyl, Cyano- cyclo-Propyl, Chlor-cyclo-Propyl, cyclo-Propyl-cyclo-Propyl, Methoxyethyl, tert.-Butyl, cyclo- Butyl, Difluorcyclobutyl, cyclo-Pentyl, Trifluorethyl oder Trifluormethyl-cyclo-Propyl steht, oder für einfach durch Phenyl substituiertes Methyl steht, wobei Phenyl gegebenenfalls einfach durch Chlor, Brom, Nitro, Trifluormethyl substituiert sein kann, oder für gegebenenfalls einfach durch Chlor substituiertes Phenyl oder Pyridyl oder für Oxazolyl steht, R2 für Wasserstoff, Methyl, Ethyl, cyclo-Propylcarbonyl oder Methoxycarbonyl steht, R3 für Wasserstoff, Methyl, Methoxy oder Methoxycarbonyl steht, R4 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, cyclo-Butyl, Trifluorethyl, Trifluorpropyl, Cyanomethyl, Cyanoethyl, Cyanopropyl, Cyanobutyl, Cyanopentyl, Methyloxyethyl, Propinyl, Butinyl, cyclo-Propyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, cyclo- Propyl-methyl, cyclo-Butyl-methyl, cyclo-Pentyl-methyl, cyclo-Hexyl-methyl, cyclo-Propyl- ethyl, Cyano-cyclo-Hexyl-methyl, Trifluormethyl-cyclo-Hexyl-methyl, cyclo-Propyl-cyclo- Propyl, Methyl-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, Trifluormethyl-cyclo-Hexyl, Difluor-cyclo-Propyl, Cyano-cyclo-Propyl, Cyano-cyclo-Butyl, Cyano-cyclo-Hexyl, Ethinyl- cyclo-Propyl, Methyloxy-cyclo-Propyl, Methyloxycarbonyl-cyclo-Propyl, Thiocarbamoyl- cyclo-Propyl, Methyloxycarbonylethyl, Cyanbenzylimino, Fluor-(Trifluormethyl)benzylimino, Methylsulfonylbutyl, Methoxy, Ethoxy, cyclo-Propyl-methyloxy, iso-Propyloxy, Cyanpropyloxy, Cyanphenyloxy, cyclo-Propylcarbonyl steht, oder für einfach durch Phenyl, Pyridyl, Indazolyl, Aza-indazolyl, Thiophenyl oder 1,3- Benzodioxolyl substituiertes Methyl, Ethyl, n-Propyl, cyclo-Propyl oder Carbonyl steht, wobei Phenyl, Pyridyl, Indazolyl, Aza-indazolyl, Thiophenyl oder 1,3-Benzodioxolyl jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Cyano, Fluor, Chlor, Nitro, Methyl, Trifluormethyl, Methoxy, Methyloxycarbonyl, Thiocarbamoyl, Aminosulfonyl, Methylpyrazolyl, Oxazolyl, Oxadiazolyl oder Pyrrolidinonyl substituiert sein können, oder für jeweils gegebenenfalls einfach substituiertes Phenyl, Pyridyl, Indazolyl, Oxetanyl, Thietanyl, Tetrahydrofuranyl, Oxotetrahydrofuranyl, Dioxidotetrahydrothiophenyl, Tetrahydro- 2H-pyranyl oder 2,3-Dihydro-1H-indenyl steht, wobei die Substituenten ausgewählt sind aus Chlor, Cyano, Methyl oder Methyloxycarbonyl, oder R3 und R4 gemeinsam für (C3-C5)-Alkyl stehen, wobei ein 4-6 gliedriger gegebenfalls durch Cyano substituierter Ring gebildet wird, R5, R6 unabhängig voneinander für Wasserstoff stehen V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. Hervorgehoben ganz besonders bevorzugter Bereich: Hervorgehoben ganz besonders bevorzugt (Ausgestaltung 6-1) sind die Verbindungen der Formel (I), in denen Q1 für 2,2,3,3-Tetrafluor-2,3-dihydro-1,4-benzodioxin-6-yl, 2,2-Difluor-1,3-benzodioxol-5-yl, 2- Chlor-4-(trifluormethoxy)phenyl, 2-Ethyl-6-methyl-4-(pentafluorethyl)phenyl, 2-Fluor-4- (trifluormethoxy)phenyl, 2-Fluor-6-(trifluormethyl)pyridin-3-yl, 2-Methyl-4- (trifluormethoxy)phenyl, 3-(Pentafluorethyl)-1H-pyrazol-1-yl, 3-(Trifluormethoxy)phenyl, 3,5- Difluor-4-(trifluormethoxy)phenyl, 3-Chlor-4-(trifluormethoxy)phenyl, 3-Chlor-5- (trifluormethyl)pyridin-2-yl, 3-Fluor-4-(pentafluorethyl)phenyl, 3-Fluor-4- (trifluormethoxy)phenyl, 3-Fluor-4-(trifluormethyl)phenyl, 3-Methyl-4-(trifluormethoxy)phenyl, 4-(1,1,1,2,3,3,3-Heptafluorpropan-2-yl)phenyl, 4-(1,1,2,2-Tetrafluorethoxy)phenyl, 4-(1,1- Difluorethyl)phenyl, 4-(2,2,2-Trifluorethyl)phenyl, 4-(2-Chlor-1,1,2-trifluorethoxy)phenyl, 4- (Cyclopropylsulfanyl)phenyl, 4-(Difluormethoxy)-3,5-difluorphenyl, 4- (Difluormethoxy)phenyl, 4-(Difluormethyl)-3-fluorphenyl, 4-(Pentafluorethoxy)phenyl, 4- (Pentafluorethyl)phenyl, 4-SF5-phenyl, 4-(Trifluormethoxy)phenyl, 4-(Trifluormethyl)phenyl, 4- [(1,1,2,2-Tetrafluorethyl)sulfanyl]phenyl, 4-[(Difluormethyl)sulfanyl]phenyl, 4- [(Difluormethyl)sulfinyl]phenyl, 4-[(Trifluormethyl)sulfanyl]phenyl, 4- [(Trifluormethyl)sulfinyl]phenyl, 4-[(Trifluormethyl)sulfonyl]phenyl, 4- [(Trifluorvinyl)oxy]phenyl, 4-[1-(Trifluormethyl)cyclopropyl]phenyl, 4- [Bis(trifluormethyl)amino]phenyl, 4-[Chlor(difluor)methoxy]phenyl, 4-Bromphenyl,4- Chlorphenyl, 4-Fluorphenyl, 4-Iodphenyl, 5-(Trifluormethyl)-2-thienyl, 5- (Trifluormethyl)pyridin-2-yl, 6-(Trifluormethyl)pyridin-3-yl steht, R1 für Cyclobutyl, Cyclopentyl, Cyclopropyl, Cyclopropylmethyl, Ethyl, Isopropyl, Methyl, tert- Butyl, 1,3-Oxazol-5-yl, 1-Chlorcyclopropyl, 1-Cyancyclopropyl, 1-Cyclopropyl-cyclopropyl, 1- Methoxyethyl, 1-Methylcyclopropyl, 2-Chlorphenyl, 3,3-Difluorcyclobutyl, 4- (Trifluormethyl)benzyl, 4-Brombenzyl, 4-Chlorphenyl oder 4-Nitrobenzyl steht, R2 für Wasserstoff, Methyl, Ethyl, Cyclopropylcarbonyl oder Methoxycarbonyl steht, R3 für Wasserstoff, Methyl, Methoxy oder Methoxycarbonyl steht, R4 für (1-Methyl-1H-indazol-7-yl)methyl, (1-Methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl, (1S)- 1-[4-(Trifluormethyl)phenyl]ethyl, (1S)-1-[4-(Trifluormethyl)phenyl]ethyl, (2,2-Difluor-1,3- benzodioxol-5-yl)methyl, (4-Cyancyclohexyl)methyl, (5-Cyanpyridin-2-yl)methyl, (6- Chlorpyridin-3-yl)methyl, (6-Cyanpyridin-3-yl)methyl, (trans-4-Cyancyclohexyl)methyl, [cis-4- (Trifluormethyl)cyclohexyl]methyl, 1-(4-Cyanphenyl)cyclopropyl, 1-(4-Cyanphenyl)ethyl, 1-(4- Nitrophenyl)cyclopropyl, 1-(4-Nitrophenyl)ethyl, 1-(Methoxycarbonyl)cyclopropyl, 1- (Trifluormethyl)cyclopropyl, 1,1-Dioxidotetrahydrothiophen-3-yl, 1-[4- (Trifluormethyl)phenyl]ethyl, 1-Thiocarbamoylcyclopropyl, 1-Cyancyclobutyl, 1- Cyancyclopropyl, 1-Cyanethyl, 1-Cyclopropyl-cyclopropyl, 1-Cyclopropylethyl, 1- Ethinylcyclopropyl, 1-Methoxycarbonylethyl, 1-Methoxycyclopropyl, 1-Methylcyclopropyl, 2- (3-Cyanphenyl)ethyl, 2-(4-Cyanphenyl)ethyl, 2,2,2-Trifluorethyl, 2,2-Difluorcyclopropyl, 2,4- Dichlor-5-fluorbenzyl, 2,4-Dichlorbenzyl, 2-Cyanpropan-2-yl, 2-Fluor-4-(trifluormethyl)benzyl, 2-Fluor-4-nitrobenzyl, 2-Methoxyethyl, 2-Oxotetrahydrofuran-3-yl, 3- (Methoxycarbonyl)oxetan-3-yl, 3,3,3-Trifluorpropyl, 3-[4-(Trifluormethyl)phenyl]propyl, 3- Chlorbenzyl, 3-Cyanbenzyl, 3-Cyanpentan-3-yl, 3-Fluor-4-(trifluormethyl)benzyl, 3- Fluorbenzyl, 3-Methylthietan-3-yl, 4-(1,2,4-Oxadiazol-3-yl)benzyl, 4-(1,3,4-Oxadiazol-2- yl)benzyl, 4-(1,3-Oxazol-5-yl)benzyl, 4-(1-Methyl-1H-pyrazol-3-yl)benzyl, 4-(1-Methyl-1H- pyrazol-5-yl)benzyl, 4-(Methoxycarbonyl)benzyl, 4-(Trifluormethyl)benzyl, 4- Thiocarbamoylbenzyl, 4-Chlor-2-fluorbenzyl, 4-Chlor-3-fluorbenzyl, 4-Chlorbenzyl, 4- Chlorphenyl, 4-Cyan-2,5-difluorbenzyl, 4-Cyan-2,6-difluorbenzyl, 4-Cyan-2-fluorbenzyl, 4- Cyan-3,5-difluorbenzyl, 4-Cyan-3-fluorbenzyl, 4-Cyanbenzyl, 4-Cyanbutyl, 4-Cyancyclohexyl, 4-Cyanphenyl, 4-Cyantetrahydro-2H-pyran-4-yl, 4-Fluor-3-(trifluormethyl)benzyl, 4- Methoxybenzyl, 4-Nitrobenzyl, 4-Aminosulfonylbenzyl, 5-Cyan-1H-indazol-3-yl, 5-Cyan-2,3- dihydro-1H-inden-1-yl, 5-Cyanpentyl, Benzyl, But-3-in-2-yl, n-Butyl, cis-4- (Trifluormethyl)cyclohexyl, Cyanmethyl, Cyclobutyl, Cyclobutylmethyl, Cyclohexyl, Cyclohexylmethyl, Cyclopentyl, Cyclopentylmethyl, Cyclopropyl, Cyclopropylmethyl, Ethyl, Isobutyl, Isopropyl, Methyl, Oxetan-3-yl, Prop-2-in-1-yl, n-Propyl, Pyridin-2-ylmethyl, Pyridin- 3-yl, Thietan-3-yl oder trans-4-(Trifluormethyl)cyclohexyl steht, oder R3 und R4 gemeinsam für einen der folgenden Ringe stehen: Compounds of the formula (I) in which Q 1 is in each case optionally monosubstituted, disubstituted, trisubstituted or trisubstituted by identical or different substituents, phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, pyridyl, thienyl or pyrazole 1-yl or pyrazol-2-yl, wherein the substituents are selected from fluorine, chlorine, bromine, iodine, SF5, methyl, ethyl, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoroisopropyl, trifluoromethoxy, difluoromethoxy, Difluorochloromethoxy, pentafluoroethoxy, tetrafluoroethoxy, chlorotrifluoroethoxy, trifluoroethenoxy, trifluoromethylsulfonyl, trifluoromethylsulfinyl, trifluoromethylsulfanyl, difluoromethylsulfinyl, difluoromethylsulfanyl, trifluoromethylcyclopropyl, bis-trifluoromethylamino, tetrafluoroethylsulfanyl, cyclopropylsulfanyl, (trifluorovinyl) oxy or hexafluoropropoxy R 1 for methyl, ethyl, i-propyl, cyclopropyl, Methyl-cyclo-propyl, cyclo-propyl-methyl, cyano-cyclo-propyl, chloro-cyclo-propyl, cyclo-prop yl-cyclo-propyl, methoxyethyl, tert-butyl, cyclo-butyl, difluorocyclobutyl, cyclo-pentyl, trifluoroethyl or trifluoromethyl-cyclo-propyl, or is methyl which is monosubstituted by phenyl, where phenyl is optionally monosubstituted by chlorine, bromine, Nitro, trifluoromethyl, or represents optionally monosubstituted chlorine or phenyl or pyridyl or oxazolyl, R 2 is hydrogen, methyl, ethyl, cyclopropylcarbonyl or methoxycarbonyl, R 3 is hydrogen, methyl, methoxy or methoxycarbonyl, R 4 is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, Butyl, cyclo-butyl, trifluoroethyl, trifluoropropyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, methyloxyethyl, propynyl, butynyl, cyclo-propyl, cyclo-butyl, cyclo-pentyl, cyclo-hexyl, cyclopropyl-methyl, cyclo- Butyl-methyl, cyclo-pentyl-methyl, cyclo-hexyl-methyl, cyclo-propyl-ethyl, cyano-cyclo-hexyl-methyl, trifluoromethyl-cyclo-hexyl-methyl, cyclo-propyl-cyclo-propyl, methyl-cyclo Propyl, trifluoromethyl-cyclo-propyl, trifluoromethyl-cyclo-hexyl, difluoro-cyclo-propyl, cyano-cyclo-propyl, cyano-cyclo-butyl, cyano-cyclo-hexyl, ethynyl-cyclo-propyl, methyloxy-cyclo-propyl, Methyloxycarbonylcyclopropyl, thiocarbamoylcyclopropyl, methyloxycarbonylethyl, cyanobenzylimino, fluoro (trifluoromethyl) benzylimino, methylsulfonylbutyl, methoxy, ethoxy, cyclopropyl Propylmethyloxy, iso-propyloxy, Cyanpropyloxy, Cyanphenyloxy, cyclo-Propylcarbonyl, or is phenyl, pyridyl, indazolyl, aza-indazolyl, thiophenyl or 1,3-benzodioxolyl substituted methyl, ethyl, n-propyl, cyclo-propyl or carbonyl, where phenyl, pyridyl, indazolyl, aza-indazolyl, thiophenyl or 1,3-benzodioxolyl are each optionally mono-, di- or trisubstituted, identically or differently, by cyano, fluorine, chlorine, nitro, methyl, trifluoromethyl, methoxy, methyloxycarbonyl, Thiocarbamoyl, aminosulfonyl, methylpyrazolyl, oxazolyl, oxadiazolyl or pyrrolidinonyl, or for each optionally monosubstituted phenyl, pyridyl, indazolyl, oxetanyl, thietanyl, tetrahydrofuranyl, oxotetrahydrofuranyl, Dioxidotetrahydrothiophenyl, tetrahydro-2H-pyranyl or 2,3-dihydro-1H -indenyl, where the substituents are selected from chlorine, cyano, methyl or methyloxycarbonyl, or R3 and R4 together for (C 3 -C 5 ) -Alk yl to form a 4-6 membered ring optionally substituted by cyano, R5, R6 independently of one another are hydrogen, V1 is oxygen or sulfur, V2 is oxygen, sulfur or -NH. Emphasized very particularly preferred range: highlighted very particularly preferred (embodiment 6-1) are the compounds of formula (I) in which Q1 for 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl, 2,2-difluoro-1,3-benzodioxol-5-yl, 2-chloro-4 (trifluoromethoxy) phenyl, 2-ethyl-6-methyl-4- (pentafluoroethyl) phenyl, 2-fluoro-4- (trifluoromethoxy) phenyl, 2-fluoro-6- (trifluoromethyl) pyridin-3-yl, 2-methyl 4- (trifluoromethoxy) phenyl, 3- (pentafluoroethyl) -1H-pyrazol-1-yl, 3- (trifluoromethoxy) phenyl, 3,5-difluoro-4- (trifluoromethoxy) phenyl, 3-chloro-4- (trifluoromethoxy) phenyl, 3-chloro-5- (trifluoromethyl) pyridin-2-yl, 3-fluoro-4- (pentafluoroethyl) phenyl, 3-fluoro-4- (trifluoromethoxy) phenyl, 3-fluoro-4- (trifluoromethyl) phenyl, 3-methyl-4- (trifluoromethoxy) phenyl, 4- (1,1,1,2,3,3,3-heptafluoropropan-2-yl) -phenyl, 4- (1,1,2,2-tetrafluoroethoxy) -phenyl , 4- (1,1-Difluoroethyl) phenyl, 4- (2,2,2-trifluoroethyl) phenyl, 4- (2-chloro-1,1,2-trifluoroethoxy) phenyl, 4- (cyclopropylsulfanyl) phenyl, 4 (Difluoromethoxy) -3,5-difluorophenyl, 4- (difluoromethoxy) phenyl, 4- (difluoromethyl) -3-fluorophenyl, 4- (pentafluoroethoxy) phenyl, 4- (pentafluoroethyl) phenyl, 4-SF5-phenyl, 4- (Trifl uormethoxy) phenyl, 4- (trifluoromethyl) phenyl, 4- [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenyl, 4 - [(difluoromethyl) sulfanyl] phenyl, 4- [(difluoromethyl) sulfinyl] phenyl, 4 - [(trifluoromethyl) sulfanyl] phenyl, 4- [(trifluoromethyl) sulfinyl] phenyl, 4 - [(trifluoromethyl) sulfonyl] phenyl, 4- [(trifluorovinyl) oxy] phenyl, 4- [1- (trifluoromethyl) cyclopropyl] phenyl , 4- [bis (trifluoromethyl) amino] phenyl, 4- [chloro (difluoro) methoxy] phenyl, 4-bromophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-iodophenyl, 5- (trifluoromethyl) -2-thienyl, 5 - (trifluoromethyl) pyridin-2-yl, 6- (trifluoromethyl) pyridin-3-yl, R 1 is cyclobutyl, cyclopentyl, cyclopropyl, cyclopropylmethyl, ethyl, isopropyl, methyl, tert-butyl, 1,3-oxazol-5 yl, 1-chlorocyclopropyl, 1-cyanocyclopropyl, 1-cyclopropylcyclopropyl, 1-methoxyethyl, 1-methylcyclopropyl, 2-chlorophenyl, 3,3-difluorocyclobutyl, 4- (trifluoromethyl) benzyl, 4-bromobenzyl, 4-chlorophenyl or 4 Nitrobenzyl, R2 is hydrogen, methyl, ethyl, cyclopropylcarbonyl or methoxycarbonyl, R 3 is hydrogen, methyl, methoxy or methoxycarbonyl, R4 is (1-methyl-1H-indazol-7-yl) methyl, (1-methyl-1H-pyrazolo [3,4-b] pyridin-5-yl) methyl , (1S) - 1- [4- (trifluoromethyl) phenyl] ethyl, (1S) -1- [4- (trifluoromethyl) phenyl] ethyl, (2,2-difluoro-1,3-benzodioxol-5-yl) methyl, (4-cyanyclohexyl) methyl, (5-cyanopyridin-2-yl) methyl, (6-chloropyridin-3-yl) methyl, (6-cyanopyridin-3-yl) methyl, (trans-4-cyancyclohexyl) methyl , [cis -4- (trifluoromethyl) cyclohexyl] methyl, 1- (4-cyanophenyl) cyclopropyl, 1- (4-cyanophenyl) ethyl, 1- (4-nitrophenyl) cyclopropyl, 1- (4-nitrophenyl) ethyl, 1 - (methoxycarbonyl) cyclopropyl, 1- (trifluoromethyl) cyclopropyl, 1,1-dioxotetrahydrothiophen-3-yl, 1- [4- (trifluoromethyl) phenyl] ethyl, 1-thiocarbamoylcyclopropyl, 1-cyancyclobutyl, 1-cyancyclopropyl, 1-cyanoethyl , 1-cyclopropylcyclopropyl, 1-cyclopropylethyl, 1-ethynylcyclopropyl, 1-methoxycarbonylethyl, 1-methoxycyclopropyl, 1-methylcyclopropyl, 2- (3-cyanophenyl) ethyl, 2- (4-cyanophenyl) ethyl, 2,2,2-trifluoroethyl, 2,2-difluorocyclopropyl, 2,4-dichloro-5-fluorobenzyl, 2,4-dichlorobenzyl, 2-cyanopropane 2-yl, 2-fluoro-4- (trifluoromethyl) benzyl, 2-fluoro-4-nitrobenzyl, 2-methoxyethyl, 2-oxotetrahydrofuran-3-yl, 3- (methoxycarbonyl) oxetan-3-yl, 3,3, 3-trifluoropropyl, 3- [4- (trifluoromethyl) phenyl] propyl, 3-chlorobenzyl, 3-cyanobenzyl, 3-cyanopentan-3-yl, 3-fluoro-4- (trifluoromethyl) benzyl, 3-fluorobenzyl, 3-methylthietane 3-yl, 4- (1,2,4-oxadiazol-3-yl) benzyl, 4- (1,3,4-oxadiazol-2-yl) benzyl, 4- (1,3-oxazole-5- yl) benzyl, 4- (1-methyl-1H-pyrazol-3-yl) benzyl, 4- (1-methyl-1H-pyrazol-5-yl) benzyl, 4- (methoxycarbonyl) benzyl, 4- (trifluoromethyl) benzyl, 4-thiocarbamoylbenzyl, 4-chloro-2-fluorobenzyl, 4-chloro-3-fluorobenzyl, 4-chlorobenzyl, 4-chlorophenyl, 4-cyano-2,5-difluorobenzyl, 4-cyano-2,6-difluorobenzyl, 4-cyano-2-fluorobenzyl, 4-cyano-3,5-difluorobenzyl, 4-cyano-3-fluorobenzyl, 4-cyanobenzyl, 4-cyanobutyl, 4-cyano-cyclohexyl, 4-cyano-phenyl, 4-cyano-tetrahydro-2H-pyranyl 4-yl, 4-Fluoro-3- (trifluoromethyl) benzyl, 4-methoxybenzyl, 4-nitrobenzyl, 4-aminosulfonylbenzyl, 5-cyano-1H-indazol-3-yl, 5-cyano-2,3-dihydro-1H-indene-1 -yl, 5-cyanopentyl, benzyl, but-3-yn-2-yl, n-butyl, cis-4- (trifluoromethyl) cyclohexyl, cyanomethyl, cyclobutyl, cyclobutylmethyl, cyclohexyl, cyclohexylmethyl, cyclopentyl, cyclopentylmethyl, cyclopropyl, cyclopropylmethyl, Ethyl, isobutyl, isopropyl, methyl, oxetan-3-yl, prop-2-yn-1-yl, n-propyl, pyridin-2-ylmethyl, pyridin-3-yl, thietan-3-yl or trans-4- (Trifluoromethyl) cyclohexyl, or R3 and R4 together represent one of the following rings:
R5, R6 V unabhängig voneinander für Wasserstoff stehen, V1, V2 unabhängig voneinander für Sauerstoff oder Schwefel stehen. Alternativ und ebenfalls hervorgehoben ganz besonders bevorzugt (Ausgestaltung 6-2) sind die Verbindungen der Formel (I), in denen Q1 für 2,2,3,3-Tetrafluor-2,3-dihydro-1,4-benzodioxin-6-yl, 2,2-Difluor-1,3-benzodioxol-5-yl, 2- Chlor-4-(trifluormethoxy)phenyl, 2-Ethyl-6-methyl-4-(pentafluorethyl)phenyl, 2-Fluor-4- (trifluormethoxy)phenyl, 2-Fluor-6-(trifluormethyl)pyridin-3-yl, 2-Methyl-4- (trifluormethoxy)phenyl, 3-(Pentafluorethyl)-1H-pyrazol-1-yl, 3-(Trifluormethoxy)phenyl, 3,5- Difluor-4-(trifluormethoxy)phenyl, 3-Chlor-4-(trifluormethoxy)phenyl, 3-Chlor-5- (trifluormethyl)pyridin-2-yl, 3-Fluor-4-(pentafluorethyl)phenyl, 3-Fluor-4- (trifluormethoxy)phenyl, 3-Fluor-4-(trifluormethyl)phenyl, 3-Methyl-4-(trifluormethoxy)phenyl, 4-(1,1,1,2,3,3,3-Heptafluorpropan-2-yl)phenyl, 4-(1,1,2,2-Tetrafluorethoxy)phenyl, 4-(1,1- Difluorethyl)phenyl, 4-(2,2,2-Trifluorethyl)phenyl, 4-(2-Chlor-1,1,2-trifluorethoxy)phenyl, 4- (Cyclopropylsulfanyl)phenyl, 4-(Difluormethoxy)-3,5-difluorphenyl, 4- (Difluormethoxy)phenyl, 4-(Difluormethyl)-3-fluorphenyl, 4-(Pentafluorethoxy)phenyl, 4- (Pentafluorethyl)phenyl, 4-SF5-phenyl, 4-(Trifluormethoxy)phenyl, 4-(Trifluormethyl)phenyl, 4- [(1,1,2,2-Tetrafluorethyl)sulfanyl]phenyl, 4-[(Difluormethyl)sulfanyl]phenyl, 4- [(Difluormethyl)sulfinyl]phenyl, 4-[(Trifluormethyl)sulfanyl]phenyl, 4- [(Trifluormethyl)sulfinyl]phenyl, 4-[(Trifluormethyl)sulfonyl]phenyl, 4- [(Trifluorvinyl)oxy]phenyl, 4-[1-(Trifluormethyl)cyclopropyl]phenyl, 4- [Bis(trifluormethyl)amino]phenyl, 4-[Chlor(difluor)methoxy]phenyl, 4-Bromphenyl,4- Chlorphenyl, 4-Fluorphenyl, 4-Iodphenyl, 5-(Trifluormethyl)-2-thienyl, 5- (Trifluormethyl)pyridin-2-yl, 6-(Trifluormethyl)pyridin-3-yl, 4-Brom-3-fluorphenyl, 4- (1,1,2,3,3,3-Hexafluorpropoxy)phenyl, 2,6-Dichlor-4-(pentafluorethyl)phenyl, 2-Chlor-3-fluor- 4-(pentafluorethyl)phenyl, 3-Fluor-5-methyl-4-(pentafluorethyl)phenyl, 2,6-Difluor-4- (pentafluorethyl)phenyl, 2-Chlor-5-fluor-4-(pentafluorethyl)phenyl, 3-Methyl-4- (pentafluorethyl)phenyl, 3,5-Difluor-4-(pentafluorethyl)phenyl, 2,3-Difluor-4- (pentafluorethyl)phenyl, 3-Chlor-4-(pentafluorethyl)phenyl, 2,3,5-Trifluor-4- (pentafluorethyl)phenyl, 2,5-Difluor-4-(pentafluorethyl)phenyl, 2,6-Dichlor-3-fluor-4- (pentafluorethyl)phenyl oder 3-Chlor-5-fluor-4-(pentafluorethyl)phenyl steht, R1 für Cyclobutyl, Cyclopentyl, Cyclopropyl, Cyclopropylmethyl, Ethyl, Isopropyl, Methyl, tert- Butyl, 1,3-Oxazol-5-yl, 1-Chlorcyclopropyl, 1-Cyancyclopropyl, 1-Cyclopropyl-cyclopropyl, 1- Methoxyethyl, 1-Methylcyclopropyl, 2-Chlorphenyl, 3,3-Difluorcyclobutyl, 4- (Trifluormethyl)benzyl, 4-Brombenzyl, 4-Chlorphenyl, 4-Nitrobenzyl, 2,2,2-Trifluorethyl, 1- (Trifluormethyl)cyclopropyl oder 6-Chlorpyridin-3-yl steht, R2 für Wasserstoff, Methyl, Ethyl, Cyclopropylcarbonyl oder Methoxycarbonyl steht, R3 für Wasserstoff, Methyl, Methoxy oder Methoxycarbonyl steht, R4 für (1-Methyl-1H-indazol-7-yl)methyl, (1-Methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl, (1S)- 1-[4-(Trifluormethyl)phenyl]ethyl, (1S)-1-[4-(Trifluormethyl)phenyl]ethyl, (2,2-Difluor-1,3- benzodioxol-5-yl)methyl, (4-Cyancyclohexyl)methyl, (5-Cyanpyridin-2-yl)methyl, (6- Chlorpyridin-3-yl)methyl, (6-Cyanpyridin-3-yl)methyl, (trans-4-Cyancyclohexyl)methyl, [cis-4- (Trifluormethyl)cyclohexyl]methyl, 1-(4-Cyanphenyl)cyclopropyl, 1-(4-Cyanphenyl)ethyl, 1-(4- Nitrophenyl)cyclopropyl, 1-(4-Nitrophenyl)ethyl, 1-(Methoxycarbonyl)cyclopropyl, 1- (Trifluormethyl)cyclopropyl, 1,1-Dioxidotetrahydrothiophen-3-yl, 1-[4- (Trifluormethyl)phenyl]ethyl, 1-Thiocarbamoylcyclopropyl, 1-Cyancyclobutyl, 1- Cyancyclopropyl, 1-Cyanethyl, 1-Cyclopropyl-cyclopropyl, 1-Cyclopropylethyl, 1- Ethinylcyclopropyl, 1-Methoxycarbonylethyl, 1-Methoxycyclopropyl, 1-Methylcyclopropyl, 2- (3-Cyanphenyl)ethyl, 2-(4-Cyanphenyl)ethyl, 2,2,2-Trifluorethyl, 2,2-Difluorcyclopropyl, 2,4- Dichlor-5-fluorbenzyl, 2,4-Dichlorbenzyl, 2-Cyanpropan-2-yl, 2-Fluor-4-(trifluormethyl)benzyl, 2-Fluor-4-nitrobenzyl, 2-Methoxyethyl, 2-Oxotetrahydrofuran-3-yl, 3- (Methoxycarbonyl)oxetan-3-yl, 3,3,3-Trifluorpropyl, 3-[4-(Trifluormethyl)phenyl]propyl, 3- Chlorbenzyl, 3-Cyanbenzyl, 3-Cyanpentan-3-yl, 3-Fluor-4-(trifluormethyl)benzyl, 3- Fluorbenzyl, 3-Methylthietan-3-yl, 4-(1,2,4-Oxadiazol-3-yl)benzyl, 4-(1,3,4-Oxadiazol-2- yl)benzyl, 4-(1,3-Oxazol-5-yl)benzyl, 4-(1-Methyl-1H-pyrazol-3-yl)benzyl, 4-(1-Methyl-1H- pyrazol-5-yl)benzyl, 4-(Methoxycarbonyl)benzyl, 4-(Trifluormethyl)benzyl, 4- Thiocarbamoylbenzyl, 4-Chlor-2-fluorbenzyl, 4-Chlor-3-fluorbenzyl, 4-Chlorbenzyl, 4- Chlorphenyl, 4-Cyan-2,5-difluorbenzyl, 4-Cyan-2,6-difluorbenzyl, 4-Cyan-2-fluorbenzyl, 4- Cyan-3,5-difluorbenzyl, 4-Cyan-3-fluorbenzyl, 4-Cyanbenzyl, 4-Cyanbutyl, 4-Cyancyclohexyl, 4-Cyanphenyl, 4-Cyantetrahydro-2H-pyran-4-yl, 4-Fluor-3-(trifluormethyl)benzyl, 4- Methoxybenzyl, 4-Nitrobenzyl, 4-Aminosulfonylbenzyl, 5-Cyan-1H-indazol-3-yl, 5-Cyan-2,3- dihydro-1H-inden-1-yl, 5-Cyanpentyl, Benzyl, But-3-in-2-yl, n-Butyl, cis-4- (Trifluormethyl)cyclohexyl, Cyanmethyl, Cyclobutyl, Cyclobutylmethyl, Cyclohexyl, Cyclohexylmethyl, Cyclopentyl, Cyclopentylmethyl, Cyclopropyl, Cyclopropylmethyl, Ethyl, Isobutyl, Isopropyl, Methyl, Oxetan-3-yl, Prop-2-in-1-yl, n-Propyl, Pyridin-2-ylmethyl, Pyridin- 3-yl, Thietan-3-yl, trans-4-(Trifluormethyl)cyclohexyl, (5-Nitro-2-thienyl)methyl, (5-Cyan-2- thienyl)methyl, 4-Cyanbenzylimin, 3-Fluor-4-(trifluormethyl)benzylimin, [4-(2-Oxopyrrolidin- 1-yl)phenyl]methyl, 2-Methyl-1-methylsulfonylpropan-2-yl, (Pyridin-4-yl)methyl, Methoxy, Ethoxy, Cyclopropylmethyloxy, Isopropyloxy, 3-Cyanpropyloxy, 4-Cyanphenyloxy, Cyclopropylcarbonyl oder 4-Nitrobenzoyl steht, oder R3 und R4 gemeinsam für einen der folgenden Ringe stehen: R5, R6 V independently of one another represent hydrogen, V1, V2 independently of one another represent oxygen or sulfur. Alternatively and also particularly emphasized (embodiment 6-2) are the compounds of the formula (I) in which Q1 is 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6 yl, 2,2-difluoro-1,3-benzodioxol-5-yl, 2-chloro-4- (trifluoromethoxy) phenyl, 2-ethyl-6-methyl-4- (pentafluoroethyl) phenyl, 2-fluoro-4- (trifluoromethoxy) phenyl, 2-fluoro-6- (trifluoromethyl) pyridin-3-yl, 2-methyl-4- (trifluoromethoxy) phenyl, 3- (pentafluoroethyl) -1H-pyrazol-1-yl, 3- (trifluoromethoxy) phenyl, 3,5-difluoro-4- (trifluoromethoxy) phenyl, 3-chloro-4- (trifluoromethoxy) phenyl, 3-chloro-5- (trifluoromethyl) pyridin-2-yl, 3-fluoro-4- (pentafluoroethyl) phenyl, 3-fluoro-4- (trifluoromethoxy) phenyl, 3-fluoro-4- (trifluoromethyl) phenyl, 3-methyl-4- (trifluoromethoxy) phenyl, 4- (1,1,1,2,3,3, 3-heptafluoropropan-2-yl) phenyl, 4- (1,1,2,2-tetrafluoroethoxy) phenyl, 4- (1,1- Difluoroethyl) phenyl, 4- (2,2,2-trifluoroethyl) phenyl, 4- (2-chloro-1,1,2-trifluoroethoxy) phenyl, 4- (cyclopropylsulfanyl) phenyl, 4- (difluoromethoxy) -3.5 -difluorophenyl, 4- (difluoromethoxy) phenyl, 4- (difluoromethyl) -3-fluorophenyl, 4- (pentafluoroethoxy) phenyl, 4- (pentafluoroethyl) phenyl, 4-SF5-phenyl, 4- (trifluoromethoxy) phenyl, 4- ( Trifluoromethyl) phenyl, 4- [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenyl, 4 - [(difluoromethyl) sulfanyl] phenyl, 4- [(difluoromethyl) sulfinyl] phenyl, 4 - [(trifluoromethyl) sulfanyl] phenyl, 4- [(trifluoromethyl) sulfinyl] phenyl, 4 - [(trifluoromethyl) sulfonyl] phenyl, 4- [(trifluorovinyl) oxy] phenyl, 4- [1- (trifluoromethyl) cyclopropyl] phenyl, 4- [bis (trifluoromethyl ) amino] phenyl, 4- [chloro (difluoro) methoxy] phenyl, 4-bromophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-iodophenyl, 5- (trifluoromethyl) -2-thienyl, 5- (trifluoromethyl) pyridine-2 -yl, 6- (trifluoromethyl) pyridin-3-yl, 4-bromo-3-fluorophenyl, 4- (1,1,2,3,3,3-hexafluoropropoxy) phenyl, 2,6-dichloro-4- ( pentafluoroethyl) phenyl, 2-chloro-3-fluoro-4- (pentafluoroeth yl) phenyl, 3-fluoro-5-methyl-4- (pentafluoroethyl) phenyl, 2,6-difluoro-4- (pentafluoroethyl) phenyl, 2-chloro-5-fluoro-4- (pentafluoroethyl) phenyl, 3-methyl -4- (pentafluoroethyl) phenyl, 3,5-difluoro-4- (pentafluoroethyl) phenyl, 2,3-difluoro-4- (pentafluoroethyl) phenyl, 3-chloro-4- (pentafluoroethyl) phenyl, 2,3,5 Trifluoro-4- (pentafluoroethyl) phenyl, 2,5-difluoro-4- (pentafluoroethyl) phenyl, 2,6-dichloro-3-fluoro-4- (pentafluoroethyl) phenyl or 3-chloro-5-fluoro-4- (pentafluoroethyl) phenyl, R 1 is cyclobutyl, cyclopentyl, cyclopropyl, cyclopropylmethyl, ethyl, isopropyl, methyl, tert-butyl, 1,3-oxazol-5-yl, 1-chlorocyclopropyl, 1-cyancyclopropyl, 1-cyclopropyl-cyclopropyl, 1-methoxyethyl, 1-methylcyclopropyl, 2-chlorophenyl, 3,3-difluorocyclobutyl, 4- (trifluoromethyl) benzyl, 4-bromobenzyl, 4-chlorophenyl, 4-nitrobenzyl, 2,2,2-trifluoroethyl, 1- (trifluoromethyl) cyclopropyl or 6-chloropyridin-3-yl, R 2 is hydrogen, methyl, ethyl, cyclopropylcarbonyl or methoxycarbonyl, R 3 is hydrogen, methyl l, methoxy or methoxycarbonyl, R4 is (1-methyl-1H-indazol-7-yl) methyl, (1-methyl-1H-pyrazolo [3,4-b] pyridin-5-yl) methyl, (1S) - 1- [4- (trifluoromethyl) phenyl] ethyl, (1S) -1- [4- (trifluoromethyl) phenyl] ethyl, (2,2-difluoro-1,3-benzodioxol-5-yl) methyl, (4 -Cyanocyclohexyl) methyl, (5-cyanopyridin-2-yl) methyl, (6-chloropyridin-3-yl) methyl, (6-cyanopyridin-3-yl) methyl, (trans-4-cyancyclohexyl) methyl, [cis- 4- (trifluoromethyl) cyclohexyl] methyl, 1- (4-cyanophenyl) cyclopropyl, 1- (4-cyanophenyl) ethyl, 1- (4-nitrophenyl) cyclopropyl, 1- (4-nitrophenyl) ethyl, 1- (methoxycarbonyl) cyclopropyl, 1- (trifluoromethyl) cyclopropyl, 1,1-dioxotetrahydrothiophen-3-yl, 1- [4- (trifluoromethyl) phenyl] ethyl, 1-thiocarbamoylcyclopropyl, 1-cyancyclobutyl, 1-cyancyclopropyl, 1-cyanoethyl, 1-cyclopropyl cyclopropyl, 1-cyclopropylethyl, 1-ethynylcyclopropyl, 1-methoxycarbonylethyl, 1-methoxycyclopropyl, 1-methylcyclopropyl, 2- (3-cyanophenyl) ethyl, 2- (4-cyanophenyl) ethyl, 2,2,2-trifluoroethyl, 2,2-difluorocyclopropyl, 2,4-dichloro-5-fluorobenzyl, 2,4-dichlorobenzyl, 2-cyanopropane 2-yl, 2-fluoro-4- (trifluoromethyl) benzyl, 2-fluoro-4-nitrobenzyl, 2-methoxyethyl, 2-oxotetrahydrofuran-3-yl, 3- (methoxycarbonyl) oxetan-3-yl, 3,3, 3-trifluoropropyl, 3- [4- (trifluoromethyl) phenyl] propyl, 3-chlorobenzyl, 3-cyanobenzyl, 3-cyanopentan-3-yl, 3-fluoro-4- (trifluoromethyl) benzyl, 3-fluorobenzyl, 3-methylthietane 3-yl, 4- (1,2,4-oxadiazol-3-yl) benzyl, 4- (1,3,4-oxadiazol-2-yl) benzyl, 4- (1,3-oxazole-5- yl) benzyl, 4- (1-methyl-1H-pyrazol-3-yl) benzyl, 4- (1-methyl-1H-pyrazol-5-yl) benzyl, 4- (methoxycarbonyl) benzyl, 4- (trifluoromethyl) benzyl, 4-thiocarbamoylbenzyl, 4-chloro-2-fluorobenzyl, 4-chloro-3-fluorobenzyl, 4-chlorobenzyl, 4-chlorophenyl, 4-cyano-2,5-difluorobenzyl, 4-cyano-2,6-difluorobenzyl, 4-cyano-2-fluorobenzyl, 4-cyano-3,5-difluorobenzyl, 4-cyano-3-fluorobenzyl, 4-cyanobenzyl, 4-cyanobutyl, 4-cyano-cyclohexyl, 4-cyano-phenyl, 4-cyano-tetrahydro-2H-pyranyl 4-yl, 4-Fluoro-3- (trifluoromethyl) benzyl, 4-methoxybenzyl, 4-nitrobenzyl, 4-aminosulfonylbenzyl, 5-cyano-1H-indazol-3-yl, 5-cyano-2,3-dihydro-1H-indene-1 -yl, 5-cyanopentyl, benzyl, but-3-yn-2-yl, n-butyl, cis-4- (trifluoromethyl) cyclohexyl, cyanomethyl, cyclobutyl, cyclobutylmethyl, cyclohexyl, cyclohexylmethyl, cyclopentyl, cyclopentylmethyl, cyclopropyl, cyclopropylmethyl, Ethyl, isobutyl, isopropyl, methyl, oxetan-3-yl, prop-2-yn-1-yl, n-propyl, pyridin-2-ylmethyl, pyridin-3-yl, thietan-3-yl, trans-4- (Trifluoromethyl) cyclohexyl, (5-nitro-2-thienyl) methyl, (5-cyano-2-thienyl) methyl, 4-cyanobenzylimine, 3-fluoro-4- (trifluoromethyl) benzylimine, [4- (2-oxopyrrolidine) 1-yl) phenyl] methyl, 2-methyl-1-methylsulfonylpropan-2-yl, (pyridin-4-yl) methyl, methoxy, ethoxy, cyclopropylmethyloxy, isopropyloxy, 3-cyano-propyloxy, 4-cyano-phenyloxy, cyclopropylcarbonyl or 4-nitrobenzoyl or R3 and R4 together represent one of the following rings:
R5, R6V unabhängig voneinander für Wasserstoff stehen, R5, R6V independently of one another represent hydrogen,
V1 für Sauerstoff oder Schwefel steht, V1 is oxygen or sulfur,
V2 für Sauerstoff, Schwefel oder -NH steht. Weitere bevorzugte, besonders bevorzugte und ganz besonders bevorzugte Bereiche: In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der allgemeinen Formeln (I-a) V2 stands for oxygen, sulfur or -NH. Further preferred, particularly preferred and very particularly preferred ranges: In a further preferred embodiment, the invention relates to the compounds of the general formulas (Ia)
wobei R1, R4 und Q1 die oben beschriebenen Bedeutungen haben (R5 und R6 stehen für Wasserstoff), insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (4-1) oder Ausgestaltung (5-1) oder Ausgestaltung (6-1) oder die in Ausgestaltung (1-2) oder Ausgestaltung (2-2) oder Ausgestaltung (3-2) oder Ausgestaltung (4-2) oder Ausgestaltung (5-2) oder Ausgestaltung (6-2) beschriebenen Bedeutungen haben. In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der allgemeinen Formeln (I-b) wherein R 1, R 4 and Q 1 have the meanings described above (R 5 and R 6 are hydrogen), in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2) or Embodiment (3-2) or Embodiment (4-2) or Embodiment (5-2 ) or embodiment (6-2) have described meanings. In a further preferred embodiment, the invention relates to the compounds of the general formulas (I-b)
wobei R1, R2, R3, R4, V1 und V2 die oben beschriebenen Bedeutungen haben (R5 und R6 stehen für Wasserstoff), insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3- 1) oder Ausgestaltung (4-1) oder Ausgestaltung (5-1) oder Ausgestaltung (6-1) oder die in Ausgestaltung (1-2) oder Ausgestaltung (2-2) oder Ausgestaltung (3-2) oder Ausgestaltung (4-2) oder Ausgestaltung (5-2) oder Ausgestaltung (6-2) beschriebenen Bedeutungen haben, und Q1 für gegebenenfalls einfach, zweifach, dreifach oder vierfach, gleich oder verschieden substituiertes Phenyl steht, wobei die Substituenten ausgewählt sind aus Cyano, Halogen, Nitro, (C1-C4)Alkyl, (C1- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C1- C4)Alkoxy, (C1-C4)Halogenalkoxy, (C3-C6)Cycloalkyl, (C3-C6)Halogencycloalkyl, (C1-C4)Alkyl-(C3- C6)cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkenoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C3-C6)Cycloalkylthio, (C3-C6)Halogencycloalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Halogenalkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfonyl, (C1- C4)Halogenalkylsulfanyl, (C3-C6)Cycloalkylsulfanyl, (C1-C4)Alkylcarbonyl, (C1- C4)Halogenalkylcarbonyl, Di-(C1-C4)Alkylamino, Di-(C1-C4)Halogenalkylamino. In einer besonders bevorzugten Ausführungsform sind die Substituenten ausgewählt wie in Ausgestaltung (5-1) oder (5-2), insbesondere wie in Ausgestaltung (5-2) beschrieben. In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der allgemeinen Formel (I-c), wherein R1, R2, R3, R4, V1 and V2 have the meanings described above (R5 and R6 are hydrogen), in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or Embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2) or Embodiment (3-2) or Embodiment (4-2) or (5-2) or (6-2) have the meanings described, and Q 1 is optionally mono-, di-, tri-, tetra- or tri-substituted phenyl, the substituents being selected from cyano, halogen, nitro, ( C1-C4) alkyl, (C1-C4) haloalkyl, (C2-C4) alkenyl, (C2-C4) haloalkenyl, (C2-C4) alkynyl, (C2-C4) haloalkynyl, (C1-C4) alkoxy, (C1 -C4) haloalkoxy, (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C1-C4) alkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, (C1-4) C4) haloalkenoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C3-C6) Cycloalkylthio, (C3-C6) halocycloalkylthio, (C1-C4) alkylsulfinyl, (C1-C4) haloalkylsulfinyl, (C1-C4) alkylsulfonyl, (C1-C4) haloalkylsulfonyl, (C1-C4) haloalkylsulfanyl, (C3-C6) cycloalkylsulfanyl , (C1-C4) alkylcarbonyl, (C1-C4) haloalkylcarbonyl, di- (C 1 -C 4) alkylamino, di- (C 1 -C 4) Halogenalkylamino. In a particularly preferred embodiment, the substituents are selected as in embodiment (5-1) or (5-2), in particular as described in embodiment (5-2). In a further preferred embodiment, the invention relates to the compounds of general formula (Ic),
wobei R1, R2, R3, R4, R5, R6 und Q1 die oben beschriebenen Bedeutungen haben, insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (4-1) oder Ausgestaltung (5-1) oder Ausgestaltung (6-1) oder die in Ausgestaltung (1-2) oder Ausgestaltung (2-2) oder Ausgestaltung (3-2) oder Ausgestaltung (4-2) oder Ausgestaltung (5-2) oder Ausgestaltung (6-2) beschriebenen Bedeutungen haben. In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in denen R3 und R4 nicht gemeinsam für Alkyl oder Alkenyl stehen, so dass kein Ring gebildet wird, wobei R1, R2, R5, R6, Q1, V1 und V2 die oben beschriebenen Bedeutungen haben, insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (4-1) oder Ausgestaltung (5-1) oder Ausgestaltung (6-1) oder die in Ausgestaltung (1-2) oder Ausgestaltung (2-2) oder Ausgestaltung (3-2) oder Ausgestaltung (4-2) oder Ausgestaltung (5-2) oder Ausgestaltung (6-2) beschriebenen Bedeutungen haben. In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in denen R1 für (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(C1- C4)alkyl, besonders bevorzugt für (C1-C4)Alkyl oder (C3-C6)Cycloalkyl steht, ganz besonders bevorzugt für (C 1wherein R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above, in particular those in the embodiment (1-1) or the embodiment (2-1) or the embodiment (3-1) or the embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2) or Embodiment (3-2) or Embodiment (4-2) or Embodiment (5-2 ) or embodiment (6-2) have described meanings. In a further preferred embodiment, the invention relates to the compounds of formula (I) in which R3 and R4 are not together alkyl or alkenyl, so that no ring is formed, wherein R1, R2, R5, R6, Q1, V1 and V2 have the meanings described above, in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or embodiment (4-1) or configuration (5-1) or embodiment (6-1) or have the meanings described in embodiment (1-2) or design (2-2) or design (3-2) or design (4-2) or design (5-2) or design (6-2). In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which R 1 is (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 3 -C 6) -cycloalkyl or (C 3 -C 6) -cycloalkyl- (Cl C 4 ) alkyl, particularly preferably (C 1 -C 4 ) alkyl or (C 3 -C 6 ) cycloalkyl, very particularly preferably (C 1
3-C6)Cycloalkyl steht, wobei R2, R3, R4, R5, R6, Q1, V und V2 die oben beschriebenen Bedeutungen haben, insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (4-1) oder Ausgestaltung (5-1) oder Ausgestaltung (6-1) oder die in Ausgestaltung (1-2) oder Ausgestaltung (2-2) oder Ausgestaltung (3-2) oder Ausgestaltung (4-2) oder Ausgestaltung (5-2) oder Ausgestaltung (6-2) beschriebenen Bedeutungen haben. In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in denen R4 für einfach durch Phenyl substituiertes Methyl steht, wobei Phenyl gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Cyano, Fluor, Chlor, Nitro, Methyl, Trifluormethyl, Methoxy, Methyloxycarbonyl, Thiocarbamoyl, Aminosulfonyl, Methylpyrazolyl, Oxazolyl oder Oxdiazolyl substituiert sein kann, wobei R1, R2, R3, R5, R6, Q1, V1 und V2 die oben beschriebenen Bedeutungen haben, insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (4-1) oder Ausgestaltung (5-1) oder Ausgestaltung (6-1) oder die in Ausgestaltung (1-2) oder Ausgestaltung (2-2) oder Ausgestaltung (3-2) oder Ausgestaltung (4-2) oder Ausgestaltung (5-2) oder Ausgestaltung (6-2) beschriebenen Bedeutungen haben. Ebenfalls ganz besonders bevorzugte erfindungsgemäße Verbindungen sind die in Tabelle 1 gezeigten Verbindungen der allgemeinen Formel (I). Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei einer Mehrfachsubstitution die Substituenten gleich oder verschieden sein können. Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. Erfindungsgemäß bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt. Erfindungsgemäß besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. Erfindungsgemäß ganz besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. Erfindungsgemäß insbesondere ganz besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als insbesondere ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. Erfindungsgemäß hervorgehoben ganz besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als hervorgehoben ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. Die Verbindungen der Formel (I) können gegebenenfalls auch in Abhängigkeit von der Art der Substituenten als Stereoisomere, d.h. als geometrische und/oder als optische Isomere oder Isomerengemische in unterschiedlichen Zusammensetzungen vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Sowohl die reinen Stereoisomeren als auch beliebige Gemische dieser Isomeren sind Gegenstand dieser Erfindung, auch wenn hier im Allgemeinen nur von Verbindungen der Formel (I) die Rede ist. Vorzugsweise werden jedoch die optisch aktiven, stereoisomeren Formen der Verbindungen der Formel (I) und deren Salze erfindungsgemäß verwendet. Die Erfindung betrifft daher sowohl die reinen Enantiomeren und Diastereomeren, als auch deren Gemische zur Bekämpfung von tierischen Schädlingen, zu denen Arthropoden und insbesondere Insekten zählen. Die Verbindungen der Formel (I) können gegebenenfalls in verschiedenen polymorphen Formen oder als Mischung verschiedener polymorpher Formen vorliegen. Sowohl die reinen Polymorphe als auch die Polymorphgemische sind Gegenstand der Erfindung und können erfindungsgemäß verwendet werden. Die vorliegenden Verbindungen der allgemeinen Formel (I) können gegebenenfalls ein chirales Kohlenstoffatom aufweisen. Gemäß den Regeln nach Cahn, Ingold und Prelog (CIP-Regeln) können diese Substituenten sowohl eine (R)- als auch eine (S)-Konfiguration aufweisen. Von der vorliegenden Erfindung werden Verbindungen der allgemeinen Formel (I) sowohl mit (S)- als auch mit (R)-Konfiguration an den jeweiligen chiralen Kohlenstoffatomen umfasst, d.h., dass die vorliegende Erfindung die Verbindungen der allgemeinen Formel (I) erfasst, in welchen die betreffenden Kohlenstoffatome jeweils unabhängig voneinander (1) eine (R)-Konfiguration; oder (2) eine (S)-Konfiguration aufweisen. Wenn mehrere Chiralitätszentren in den Verbindungen der allgemeinen Formel (I) vorliegen, sind beliebige Kombinationen der Konfigurationen der Chiralitätszentren möglich, d.h. dass (1) ein Chiralitätszentrum die (R)-Konfiguration und das andere Chiralitätszentrum die (S)- Konfiguration; (2) ein Chiralitätszentrum die (R)-Konfiguration und das andere Chiralitätszentrum die (R)- Konfiguration; und (3) ein Chiralitätszentrum die (S)-Konfiguration und das andere Chiralitätszentrum die (S)- Konfiguration aufweisen kann. In den allgemeinen oder in Vorzugsbereichen aufgeführten Definitionen ist, sofern nichts anderes angegeben ist, Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom, Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkyl, im Rahmen der vorliegenden Erfindung ein Rest einer gesättigten, aliphatischen Kohlenwasserstoffgruppe mit 1 bis 12 Kohlenstoffatomen verstanden, die verzweigt oder unverzweigt sein kann. Beispiele für C1- C12-Alkylreste sind Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sek.-Butyl, tert.-Butyl, n- Pentyl, iso-Pentyl, Neopentyl, tert.-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 1-Ethylpropyl, 1,2- Dimethylpropyl, Hexyl n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl und n-Dodecyl. Von diesen Alkylresten sind C1-C6-Alkylreste besonders bevorzugt. Insbesondere bevorzugt sind C1-C4-Alkylreste. Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkenyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-C12-Alkenylrest, welcher mindestens eine Doppelbindung aufweist, beispielsweise Vinyl, Allyl, 1-Propenyl, Isopropenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1,3-Butadienyl, 1-Pentenyl, 2- Pentenyl, 3-Pentenyl, 4-Pentenyl, 1,3-Pentadienyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl und 1,4-Hexadienyl, verstanden. Bevorzugt hiervon sind C2-C6-Alkenylreste und besonders bevorzugt sind C2-C4-Alkenylreste. Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkinyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-C12-Alkinylrest, welcher mindestens eine Dreifachbindung aufweist, beispielsweise Ethinyl, 1-Propinyl und Propargyl, verstanden. Bevorzugt hiervon sind C3-C6-Alkinylreste und besonders bevorzugt sind C3-C4-Alkinylreste. Der Alkinylrest kann dabei auch mindestens eine Doppelbindung aufweisen. Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Cycloalkyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein C3-C8- Cycloalkylrest verstanden, beispielsweise Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl und Cyclooctyl, verstanden. Bevorzugt hiervon sind C3-C6-Cycloalkylreste. Unter dem Begriff„Alkoxy“ oder„Alkyloxy“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkoxy, wird vorliegend ein Rest O-Alkyl verstanden, wobei der Begriff„Alkyl“ die oben stehende Bedeutung aufweist. Sofern nicht an anderer Stelle anders definiert, bedeutet„Oxy“ die Gruppe–O–. Durch Halogen substituierte Reste, z.B. Halogenalkyl (=Haloalkyl), sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halo- genatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder Iod, insbesondere für Fluor, Chlor oder Brom. Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff„Aryl“ erfindungsgemäß ein aromatischer Rest mit 6 bis 14 Kohlenstoffatomen, vorzugsweise Phenyl, verstanden. Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff„Arylalkyl“ eine Kombination von erfindungsgemäß definierten Resten „Aryl“ und „Alkyl“ verstanden, wobei der Rest im Allgemeinen über die Alkylgrupe gebunden wird, Beispiele hierfür sind Benzyl, Phenylethyl oder ^- Methylbenzyl, wobei Benzyl besonders bevorzugt ist. Sofern nicht an anderer Stelle anders definiert, bedeutet„Hetaryl“ eine mono-, bi- oder tricyclische heterocyclische Gruppe aus C-Atomen und mindestens einem Heteroatom, wobei mindestens ein Zyklus aromatisch ist. Bevorzugt enthält die Hetaryl-Gruppe 3, 4, 5 oder 6 C-Atome. Bevorzugt steht Hetaryl für Pyridinyl oder Pyrimidinyl. Sofern nicht an anderer Stelle anders definiert, bedeutet„Heterocyclyl“ einen monocyclischen, gesättigten oder teilgesättigten 4-, 5-, 6- oder 7-gliedrigen Ring aus C-Atomen und mindestens einem Heteroatom im Ring. Bevorzugt enthält die Heterocyclyl-Gruppe 3, 4, 5 oder 6 C-Atome und 1 oder 2 Heteroatome aus der Reihe Sauerstoff, Schwefel oder Stickstoff. Beispiele für Heterocyclyl sind Azetidinyl, Azolidinyl, Azinanyl, Oxetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl, Tetrahydrofuryl. Sofern nicht an anderer Stelle anders definiert, bedeutet„Oxo-Hetaryl“ ein Hetaryl, das an mindestens einer Position im Ring ein Ring-Kohlenstoffatom enthält, das mit einer (=O)–Gruppe substituiert ist, wobei sich dann die Gruppe–C(=O)- ergibt, wobei das C-Atom Bestandteil des Rings ist. Sofern nicht an anderer Stelle anders definiert, bedeutet„Oxo-Heterocyclyl“ ein Heterocyclyl, das an mindestens einer Position im Ring ein Ring-Kohlenstoffatom enthält, das mit einer (=O)–Gruppe substituiert ist, wobei sich dann die Gruppe–C(=O)- ergibt, wobei das C-Atom Bestandteil des Rings ist. Bevorzugt enthält Oxo-Heterocyclyl eine oder zwei –C(=O)- Gruppen. Als Beispiel sei Oxotetrahydrofuranyl oder Pyrrolidinonyl genannt. Die Gruppe„Benzylimino“ oder„Benzylimin“ kann auch als Phenylmethylenamino bezeichnet werden. So können beispielsweise die Gruppen 4-Cyanbenzylimin (R4 in Beispiel Nr. I-252) oder 3- Fluor-4-(trifluormethyl)benzylimin (R4 in Beispiel Nr. I-257) auch als (4-Cyanphenyl)methylenamino bzw. [3-Fluor-4-(trifluormethyl)phenyl]methylenamino bezeichnet werden. Maßgeblich für die Bedeutung des Begriffs„Benzylimino“ oder„Benzylimin“ ist in jedem Fall die zu Grunde liegende chemische Struktur, d.h. . 3-C 6 ) cycloalkyl, where R 2, R 3, R 4, R 5, R 6 , Q 1, V and V 2 have the meanings described above, in particular those in embodiment (1-1) or embodiment (2-1) or embodiment (3 1) or embodiment (4-1) or design (5-1) or design (6-1) or in the embodiment (1-2) or design (2-2) or design (3-2) or design ( 4-2) or embodiment (5-2) or embodiment (6-2) have described meanings. In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which R4 is methyl which is monosubstituted by phenyl, where phenyl is optionally mono-, di- or trisubstituted, identically or differently, by cyano, fluorine, chlorine, nitro, methyl, Trifluoromethyl, methoxy, methyloxycarbonyl, thiocarbamoyl, aminosulfonyl, methylpyrazolyl, oxazolyl or oxdiazolyl may be substituted, wherein R1, R2, R3, R5, R6, Q1, V1 and V2 have the meanings described above, in particular those in embodiment (1-1) or Embodiment (2-1) or Embodiment (3-1) or Embodiment (4-1) or Embodiment (5-1) or Embodiment (6-1) or Embodiment (1-2) or Embodiment (2-2 ) or design (3-2) or design (4-2) or design (5-2) or design (6-2) have described meanings. Also very particularly preferred compounds according to the invention are the compounds of the general formula (I) shown in Table 1. Optionally substituted radicals may be monosubstituted or polysubstituted, wherein in a multiple substitution the substituents may be the same or different. The general or preferred radical definitions or explanations given above apply correspondingly to the end products and to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges. Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred. Particular preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present. Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred. Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings given above as being particularly particularly preferred. Very particular preference is given according to the invention to compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred. Depending on the nature of the substituents, the compounds of the formula (I) may also be present as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here. Preferably, however, the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention. The invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects. The compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention. The present compounds of the general formula (I) may optionally have a chiral carbon atom. According to the rules of Cahn, Ingold and Prelog (CIP rules), these substituents may have both an (R) and an (S) configuration. The present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms is independently (1) an (R) -configuration; or (2) have an (S) configuration. When multiple chiral centers are present in the compounds of general formula (I), any combination of chiral center configurations is possible, ie, (1) one chiral center has the (R) configuration and the other chiral center has the (S) configuration; (2) one chiral center the (R) configuration and the other chiral center the (R) configuration; and (3) one chiral center may have the (S) configuration and the other chiral center may have the (S) configuration. In the general or preferred ranges given definitions, unless otherwise indicated, halogen is selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine, unless otherwise defined elsewhere the term "alkyl", either alone or in combination with other terms, such as haloalkyl, in the context of the present invention means a radical of a saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched. Examples of C 1 -C 12 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Of these alkyl radicals, C 1 -C 6 -alkyl radicals are particularly preferred. Particular preference is given to C 1 -C 4 -alkyl radicals. Unless otherwise defined elsewhere, the term "alkenyl", either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkenyl radical having at least one double bond, for example vinyl, allyl, 1 Propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2 Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl. Preferred of these are C 2 -C 6 -alkenyl radicals and particularly preferred are C 2 -C 4 -alkenyl radicals. Unless otherwise defined elsewhere, the term "alkynyl", either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkynyl having at least one triple bond, for example ethynyl, 1-propynyl and propargyl, understood. Preferred of these are C 3 -C 6 -alkynyl radicals and particularly preferred are C 3 -C 4 -alkynyl radicals. The alkynyl radical can also have at least one double bond. Unless otherwise defined elsewhere, the term "cycloalkyl", either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood , Preferred of these are C3-C6-cycloalkyl radicals. The term "alkoxy" or "alkyloxy", either alone or in combination with other terms such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term "alkyl" having the meaning given above. Unless otherwise defined elsewhere, "Oxy" means the group O-. Halo-substituted radicals, for example haloalkyl (= haloalkyl), are halogenated once or several times up to the maximum possible number of substituents. With multiple halogenation, the halogen atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine. Unless otherwise defined elsewhere, the term "aryl" according to the invention is understood as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl. Unless otherwise defined elsewhere, the term "arylalkyl" means a combination of "aryl" and "alkyl" radicals as defined in the invention, the radical generally being attached via the alkyl group, examples being benzyl, phenylethyl or Methylbenzyl, with benzyl being particularly preferred. Unless otherwise defined elsewhere, "hetaryl" means a mono-, bi- or tricyclic heterocyclic group of C atoms and at least one heteroatom, wherein at least one cycle is aromatic. Preferably, the hetaryl group contains 3, 4, 5 or 6 carbon atoms. Preferably hetaryl is pyridinyl or pyrimidinyl. Unless otherwise defined elsewhere, "heterocyclyl" means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring of C atoms and at least one heteroatom in the ring. Preferably, the heterocyclyl group contains 3, 4, 5 or 6 carbon atoms and 1 or 2 heteroatoms from the series oxygen, sulfur or nitrogen. Examples of heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl. Unless otherwise defined elsewhere, "oxo-hetaryl" means a hetaryl containing, at at least one position in the ring, a ring carbon atom substituted by an (= O) group, and then the group-C ( = O) -, where the C atom is part of the ring. Unless otherwise defined elsewhere, "oxo-heterocyclyl" means a heterocyclyl containing, at at least one position in the ring, a ring carbon atom substituted with an (= O) group, and then the group-C ( = O) -, where the C atom is part of the ring. Preferably, oxo-heterocyclyl contains one or two -C (= O) groups. As an example, oxotetrahydrofuranyl or pyrrolidinonyl may be mentioned. The group "benzylimino" or "benzylimine" may also be referred to as phenylmethyleneamino. For example, the groups 4-cyanobenzylimine (R4 in Example No. I-252) or 3-fluoro-4- (trifluoromethyl) benzylimine (R4 in Example No. I-257) may also be described as (4-cyanophenyl) methyleneamino and [ 3-Fluoro-4- (trifluoromethyl) phenyl] methyleneamino. Decisive for the meaning of the term "benzylimino" or "benzylimine" is in each case the underlying chemical structure, ie ,
Isomere Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit sowohl reine Stereoisomere als auch beliebige Gemische dieser Isomere. Verfahren und Verwendungen Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Hierunter vorzugsweise ausgeschlossen sind Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden. Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel jeweils immer auch den Begriff Pflanzenschutzmittel. Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, insbesondere Nematoden, und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Im Rahmen der vorliegenden Patentanmeldung ist der Begriff„Hygiene“ so zu verstehen, dass damit jegliche und alle Maßnahmen, Vorschriften und Verfahrensweisen gemeint sind, deren Ziel es ist, Krankheiten, insbesondere Infektionskrankheiten, zu verhindern, und die dazu dienen, die Gesundheit von Menschen und Tieren zu schützen und/oder die Umwelt zu schützen, und/oder die Sauberkeit aufrechterhalten. Erfindungsgemäß schließt dies insbesondere Maßnahmen zur Reinigung, Desinfektion und Sterilisation beispielsweise von Textilien oder harten Oberflächen, insbesondere Oberflächen aus Glas, Holz, Zement, Porzellan, Keramik, Kunststoff oder auch Metall(en) ein, um sicherzustellen, dass diese frei von Hygieneschädlingen und/oder ihren Ausscheidungen sind. Vorzugsweise ausgeschlossen vom Schutzbereich der Erfindung sind in dieser Hinsicht chirurgische oder therapeutische, auf den menschlichen Körper oder die Körper von Tieren anzuwendende Behandlungsvorschriften und diagnostische Vorschriften, die am menschlichen Körper oder den Körpern von Tieren durchgeführt werden. Der Begriff„Hygienesektor“ deckt alle Gebiete, technischen Felder und industriellen Anwendungen ab, bei denen diese Hygienemaßnahmen, -vorschriften und -verfahrensweisen wichtig sind, zum Beispiel im Hinblick auf Hygiene in Küchen, Bäckereien, Flughäfen, Badezimmern, Schwimmbecken, Kaufhäusern, Hotels, Krankenhäusern, Ställen, Tierhaltungen usw. Der Begriff„Hygieneschädling“ ist daher so zu verstehen, dass damit ein oder mehrere Tierschädlinge gemeint sind, deren Gegenwart im Hygienesektor problematisch ist, insbesondere aus Gesundheitsgründen. Es ist daher ein Hauptziel, das Vorhandensein von Hygieneschädlingen und/oder das Ausgesetztsein ihnen gegenüber im Hygienesektor zu vermeiden oder auf ein Mindestmaß zu begrenzen. Dies lässt sich insbesondere durch die Anwendung eines Pestizids erreichen, das sich sowohl zum Verhindern eines Befalls als auch zum Verhindern eines bereits vorhandenen Befalls einsetzen lässt. Man kann auch Zubereitungen verwenden, die eine Exposition gegenüber Schädlingen verhindern oder reduzieren. Hygieneschädlinge schließen zum Beispiel die unten erwähnten Organismen ein. Der Begriff „Hygieneschutz“ deckt somit alle Handlungen ab, mit denen diese Hygienemaßnahmen, -vorschriften und–verfahrensweisen aufrechterhalten und/oder verbessert werden. Die Verbindungen der Formel (I) können vorzugsweise als Schädlingsbekämpfungsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z. B. Acarus spp., z. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z. B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z. B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z. B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z. B. Eutetranychus banksi, Eriophyes spp., z. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z. B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z. B. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., z. B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; aus der Klasse der Chilopoda z. B. Geophilus spp., Scutigera spp.; aus der Ordnung oder der Klasse der Collembola z. B. Onychiurus armatus; Sminthurus viridis; aus der Klasse der Diplopoda z. B. Blaniulus guttulatus; aus der Klasse der Insecta, z. B. aus der Ordnung der Blattodea z. B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., z. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; aus der Ordnung der Coleoptera z. B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., z. B. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., z. B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., z. B. Anoplophora glabripennis, Anthonomus spp., z. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z. B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z. B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dendroctonus spp., z. B. Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., z. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., z. B. Epilachna borealis, Epilachna varivestis, Epitrix spp., z. B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z. B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., z. B. Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., z. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., z. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z. B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., z. B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z. B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z. B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Scolytus spp., z. B. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., z. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., z. B. Sternechus paludatus, Symphyletes spp., Tanymecus spp., z. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z. B. Zabrus tenebrioides; aus der Ordnung der Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; aus der Ordnung der Diptera z. B. Aedes spp., z. B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z. B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., z. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z. B. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z. B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z. B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z. B. Dasineura brassicae, Delia spp., z. B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., z. B. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z. B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya oder Pegomyia spp., z. B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., z. B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., z. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; aus der Ordnung der Hemiptera z. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z. B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., z. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z. B. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z. B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., z. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., z. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z. B. Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., z. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., z. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z. B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., z. B. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., z. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z. B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., z. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., z. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., z. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z. B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z. B. Lygocoris pabulinus, Lygus spp., z. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., z. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; aus der Ordnung der Hymenoptera z. B. Acromyrmex spp., Athalia spp., z. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., z. B. Diprion similis, Hoplocampa spp., z. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., z. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., z. B. Vespa crabro, Wasmannia auropunctata, Xeris spp.; aus der Ordnung der Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z. B. Coptotermes spp., z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., z. B. Reticulitermes flavipes, Reticulitermes hesperus; aus der Ordnung der Lepidoptera z. B. Achroia grisella, Acronicta major, Adoxophyes spp., z. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., z. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., z. B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z. B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., z. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z. B. Heliothis virescens , Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., z. B. Leucoptera coffeella, Lithocolletis spp., z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z. B. Lymantria dispar, Lyonetia spp., z. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z. B. Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., z. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Podesia spp., z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z. B. Schoenobius bipunctifer, Scirpophaga spp., z. B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z. B. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z. B. Locusta migratoria, Melanoplus spp., z. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; Isomers Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus comprises both pure stereoisomers and any mixtures of these isomers. Methods and uses The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body. The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides. In the context of the present application, the term pest control always always includes the term pesticides. The compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, in particular nematodes, and mollusks found in agriculture, horticulture, livestock, aquaculture, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. In the context of the present patent application, the term "hygiene" is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and to protect animals and / or protect the environment, and / or maintain cleanliness. According to the invention this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramic, plastic or metal (s) to ensure that they are free from hygiene pests and / or their excretions are. Preferably excluded from the scope of the invention in this regard are surgical or therapeutic treatment regimens to be applied to the human body or bodies of animals and diagnostic provisions made on the human body or bodies of animals. The term "hygiene sector" covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, Hospitals, stables, animal husbandry etc. The term "hygiene pest" is therefore to be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, especially for health reasons. It is therefore a major objective to avoid or minimize the presence of hygiene pests and / or exposure to them in the sanitary sector. This can be achieved in particular by the use of a pesticide, which can be used both to prevent infestation and to prevent an already existing infestation. It is also possible to use preparations which prevent or reduce exposure to pests. Hygiene pests include, for example, the organisms mentioned below. The term "hygiene protection" thus covers all actions that maintain and / or improve such hygiene measures, rules and procedures. The compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above-mentioned pests include: pests from the strain of Arthropoda, in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B. Brevipalpus phenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., E.g. Eutetranychus banksi, Eriophyes spp., E.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Z. B. Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Z. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g. Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the class of Chilopoda z. Geophilus spp., Scutigera spp .; from the order or class of Collembola z. B. Onychiurus armatus; Sminthurus viridis; from the class of Diplopoda z. B. Blaniulus guttulatus; from the class of the Insecta, z. B. from the order of Blattodea z. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., E.g. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., E.g. B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Z. B. Anoplophora glabripennis, Anthonomus spp., Z. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., E.g. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., E.g. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., E.g. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dendroctonus spp., E.g. Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., E.g. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. B. leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp. Megacyllene robiniae, Megascelis spp., Melanotus spp., E.g. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferruginus, Rhynchophorus palmarum, Scolytus spp., E.g. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., E.g. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Stemus spp., E.g. Starchus paludatus, Symphyletes spp., Tanymecus spp., E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of Diptera z. B. Aedes spp., Z. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., E.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., E.g. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., E.g. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., E.g. Contarinia johnsoni, Contarina nasturtii, Contarina pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., E.g. B. Dasineura brassicae, Delia spp. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., E.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., E.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., E.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., E.g. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., E.g. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., Z. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of Hemiptera z. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., E.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., E.g. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli , Coccus spp., Z. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp. Drosicha spp., Dysaphis spp., Z. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., E.g. Empaasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., E.g. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g. B. Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., E.g. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., E.g. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., E.g. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., E.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoidus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., E.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g. Eustistus heros, Euschistus servus, Eustistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp , Lygocoris pabulinus, Lygus spp., E.g. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of Hymenoptera z. Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., Z. B. Diprion similis, Hoplocampa spp., Z. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of Isoptera z. B. Coptotermes spp., Z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., E.g. B. Reticulitermes flavipes, Reticulitermes hesperus; from the order of Lepidoptera z. Achroia grisella, Acronica major, Adoxophyes spp., E.g. Adoxophytes orana, Aedia leucomelas, Agrotis spp., E.g. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., Z. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., E.g. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata , Chilo spp., Z. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., E.g. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., E.g. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Efoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., E.g. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp. Homo. Spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp. Orthaga spp., Ostrinia spp. Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., E.g. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Z. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Podesia spp., E.g. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g. Scirpophaga innotata, Scotia segetum, Sesamia spp., E.g. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp ., Trichophaga tapetzella, Trichoplusia spp. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., Z. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. Locusta migratoria, melanoplus spp., E.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria;
aus der Ordnung der Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; from the order of Phthiraptera z. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .;
aus der Ordnung der Psocoptera z. B. Lepinotus spp., Liposcelis spp.; from the order of Psocoptera z. Lepinotus spp., Liposcelis spp .;
aus der Ordnung der Siphonaptera z. B. Ceratophyllus spp., Ctenocephalides spp., z. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z. B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z. B. Scutigerella spp., z. B. Scutigerella immaculata; Schädlinge aus dem Stamm der Mollusca, z. B. aus der Klasse der Bivalvia, z. B. Dreissena spp.; sowie aus der Klasse der Gastropoda z. B. Arion spp., z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pflanzenschädlinge aus dem Stamm der Nematoda, d. h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z. B. Aglenchus agricola, Anguina spp., z. B. Anguina tritici, Aphelenchoides spp., z. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z. B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z. B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., z. B. Cacopaurus pestis, Criconemella spp., z. B. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z. B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., z. B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., z. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z. B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z. B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., z. B. Longidorus africanus, Meloidogyne spp., z. B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., z. B. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., z. B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z. B. Tylenchorhynchus annulatus, Tylenchulus spp., z. B. Tylenchulus semipenetrans, Xiphinema spp., z. B. Xiphinema index. Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma- like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. Formulierungen Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungsformen als Schädlingsbekämpfungsmittel wie z. B. Drench-, Drip- und Spritzbrühen, umfassend mindestens eine Verbindung der Formel (I). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wie Penetrationsförderer, z. B. pflanzliche Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester pflanzlicher Fettsäuren wie beispielsweise Rapsöl- oder Sojaölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze, z. B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention fördernde Mittel wie z. B. Dioctylsulfosuccinat oder Hydroxypropyl-guar-Polymere und/oder Humectants wie z. B. Glycerin und/oder Dünger wie beispielsweise Ammonium, Kalium oder Phosphor enthaltende Dünger. Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser dispergierbare Granulate (WG), Granulate (GR) und Kapselkonzentrate (CS); diese und weitere mögliche Formuliertypen sind beispielsweise durch Crop Life International und 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 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einer oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Verdicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fördern. Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Verbindungen der Formel (I) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktiven Stoffen. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (I) oder den aus diesen Formulierungen bereiteten Anwendungsformen (wie z. B. gebrauchsfähigen Schädlingsbekämpfungsmitteln wie Spritzbrühen oder Saatgutbeizen) besondere Eigenschaften, wie bestimmte physikalische, technische und/oder biologische Eigenschaften zu verleihen. Als Streckmittel eignen sich z. B. Wasser, polare und unpolare organische chemische Flüssigkeiten z. B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsulfoxid). Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z. B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder chlorierte aliphatische Kohlenwasserstoffe wie z. B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z. B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z. B. Methanol, Ethanol, iso-Propanol, Butanol oder Glykol sowie deren Ether und Ester, Ketone wie z. B. Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylsulfoxid sowie Wasser. Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z. B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und/oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen infrage: z. B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Papier, Kokosnussschalen, Maiskolben und Tabakstängel. Auch verflüssigte gasförmige Streckmittel oder Lösemittel können eingesetzt werden. Insbesondere eignen sich solche Streckmittel oder Trägerstoffe, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgase wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulfonsäure, Salze von Phenolsulfonsäure oder Naphthalinsulfonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulfobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenolen, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulfate, Sulfonate und Phosphate, z. B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und/oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und pflanzliche Öle sein. Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsförderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Feuchthaltemittel, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welcher für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar-Polymere. Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Be- tracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Beweglichkeit der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51, 131-152) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettaminalkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.-% der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung. Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (I), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. Mischungen Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbiziden, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, Semiochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z. B. das Wirkungsspektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repellenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Des Weiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteertrag steigern, die Reife beeinflussen, die Qualität und/oder der Ernährungswert der Ernteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Ernteprodukte verbessern. Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. Wenn eine der im Folgenden genannten Verbindungen in verschiedenen tautomeren Formen vorkommen kann, sind auch diese Formen mit umfasst, auch wenn sie sie nicht in jedem Fall explizit genannt wurden. Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Insektizide/Akarizide/Nematizide Die hier mit ihrem„Common Name“ genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch („The Pesticide Manual“ 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z. B. http://www.alanwood.net/pesticides). Die Klassifizierung basiert auf dem zum Zeitpunkt der Einreichung dieser Patentanmeldung gültigen IRAC Mode of Action Classification Scheme. (1) Acetylcholinesterase(AChE)-Inhibitoren, wie beispielsweise Carbamate, z. B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder Organophosphate, z. B. Acephat, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoat, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Heptenophos, Imicyafos, Isofenphos, Isopropyl-O-(methoxyaminothio-phosphoryl)salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion-methyl, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (2) GABA-gesteuerte Chlorid-Kanal-Blocker, wie beispielsweise Cyclodien-organochlorine, z. B. Chlordan und Endosulfan oder Phenylpyrazole (Fiprole), z. B. Ethiprol und Fipronil. (3) Natrium-Kanal-Modulatoren, wie beispielsweise Pyrethroide, z. B. Acrinathrin, Allethrin, d-cis- trans-Allethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma- Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta- Cypermethrin, Cyphenothrin [(1R)-trans-Isomer], Deltamethrin, Empenthrin [(EZ)-(1R)-Isomer], Esfenvalerat, Etofenprox, Fenpropathrin, Fenvalerat, Flucythrinat, Flumethrin, tau-Fluvalinat, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(1R)-trans-Isomer], Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-Isomer], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. (4) Kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Neonicotinoide, z. B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nicotin oder Sulfoxaflor oder Flupyradifurone. (5) Allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Spinosyne, z. B. Spinetoram und Spinosad. (6) Allosterische Modulatoren des Glutamat-abhängigen Chloridkanals(GluCl), wie beispielsweise Avermectine/Milbemycine, z. B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (7) Juvenilhormon-Mimetika, wie beispielsweise Juvenilhormon-Analoge, z. B. Hydropren, Kinopren und Methopren oder Fenoxycarb oder Pyriproxyfen. (8) Verschiedene nicht spezifische (multi-site) Inhibitoren, wie beispielsweise Alkylhalogenide, z. B. Methylbromid und andere Alkylhalogenide; oder Chloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein oder Methylisocyanaterzeuger, z. B. Diazomet und Metam. (9) Modulatoren chordotonaler Organe, z. B. Pymetrozin oder Flonicamid. (10) Milbenwachstumsinhibitoren, wie z. B. Clofentezin, Hexythiazox und Diflovidazin oder Etoxazol. (11) Mikrobielle Disruptoren der Insektendarmmembran, wie z. B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und B.t.-Pflanzenproteine: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1. (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinnverbindungen, z. B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargit oder Tetradifon. (13) Entkoppler der oxidativen Phoshorylierung durch Störung des Protonengradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. (14) Blocker des nicotinischen Acetylcholinrezeptorkanals, wie beispielsweise Bensultap, Cartap- hydrochlorid, Thiocyclam und Thiosultap-Natrium. (15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin. (17) Häutungsdisruptor (insbesondere bei Dipteren, d. h. Zweiflüglern), wie beispielsweise Cyromazin. (18) Ecdyson-Rezeptor-Agonisten, wie beispielsweise Chromafenozid, Halofenozid, Methoxyfenozid und Tebufenozid. (19) Oktopamin-Rezeptor-Agonisten, wie beispielsweise Amitraz. (20) Mitochondriale Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim. (21) Mitochondriale Komplex-I-Elektronentransportinhibitoren, wie beispielsweise METI-Akarizide, z. B. Fenazaquin, Fenpyroximat, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenon (Derris). (22) Blocker des spannungsabhängigen Natriumkanals, wie z. B. Indoxacarb oder Metaflumizone. (23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z. B. Spirodiclofen, Spiromesifen und Spirotetramat. (24) Inhibitoren des mitochondrialen Komplex-IV-Elektronentransports, wie beispielsweise Phosphine, z. B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanide, Calciumcyanid, Kaliumcyanid und Natriumcyanid. (25) Inhibitoren des mitochondrialen Komplex-II-Elektronentransports, wie beispielsweise beta- Ketonitrilderivate, z. B. Cyenopyrafen und Cyflumetofen und Carboxanilide, wie beispielsweise Pyflubumid. (28) Ryanodinrezeptor-Modulatoren, wie beispielsweise Diamide, z. B. Chlorantraniliprol, Cyantraniliprol und Flubendiamid, weitere Wirkstoffe wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximat, Bifenazat, Broflanilid, Bromopropylat, Chinomethionat, Chloroprallethrin, Cryolit, Cyclaniliprol, Cycloxaprid, Cyhalodiamid, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizin, Fluensulfon, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxametamid, Fufenozid, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprol, Tetrachlorantraniliprol, Tioxazafen, Thiofluoximat, Triflumezopyrim und Iodmethan; des Weiteren Präparate auf Basis von Bacillus firmus (I-1582, BioNeem, Votivo), sowie folgende Verbindungen: 1- {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-3-(trifluormethyl)-1H-1,2,4-triazol-5-amin (bekannt aus WO2006/043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-Chlorphenyl)prop-2-en-1-yl]-5- fluorspiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chlorpyridin-4-yl)methanon (bekannt aus WO2003/106457) (CAS 637360-23-7), 2-Chlor-N-[2-{1-[(2E)-3-(4-chlorphenyl)prop-2-en-1-yl]piperidin-4-yl}-4- (trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494) (CAS 872999-66-1), 3-(4-Chlor- 2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO 2010052161) (CAS 1225292-17-0), 3-(4-Chlor-2, 6-dimethylphenyl)-8-methoxy-2-oxo-1,8- diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus EP 2647626) (CAS-1440516-42-6), 4-(But-2- in-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluorpyrimidin (bekannt aus WO2004/099160) (CAS 792914-58-0), PF1364 (bekannt aus JP2010/018586) (CAS-Reg.No. 1204776-60-2), N-[(2E)-1-[(6- Chlorpyridin-3-yl)methyl]pyridin-2(1H)-yliden]-2,2,2-trifluoracetamid (bekannt aus WO2012/029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-Chlor-3-pyridyl)methyl]-2-pyridyliden]-1,1,1-trifluorpropan-2-on (bekannt aus WO2013/144213) (CAS 1461743-15-6), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-1- methyl-3-(pentafluorethyl)-4-(trifluormethyl)-1H-pyrazol-5-carboxamid (bekannt aus WO2010/051926) (CAS 1226889-14-0), 5-Brom-4-chlor-N-[4-chlor-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chlor-2- pyridyl)pyrazol-3-carboxamid (bekannt aus CN103232431) (CAS 1449220-44-3), 4-[5-(3,5- Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3- thietanyl)benzamid, 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N- (trans-1-oxido-3-thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)- 3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamid (bekannt aus WO 2013/050317 A1) (CAS 1332628-83-7), N-[3-Chlor-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- trifluorpropyl)sulfinyl]propanamid, (+)-N-[3-Chlor-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- trifluorpropyl)sulfinyl]propanamid und (-)-N-[3-Chlor-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3- [(3,3,3-trifluorpropyl)sulfinyl]propanamid (bekannt aus WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-Chlor-2-propen-1-yl]amino]-1-[2,6-dichlor-4- (trifluormethyl)phenyl]-4-[(trifluormethyl)sulfinyl]-1H-pyrazol-3-carbonitrile (bekannt aus CN 101337937 A) (CAS 1105672-77-2), 3-Brom-N-[4-chlor-2-methyl-6- [(methylamino)thioxomethyl]phenyl]-1-(3-chlor-2-pyridinyl)-1H-pyrazol-5-carboxamid, from the order of Siphonaptera z. Ceratophyllus spp., Ctenocephalides spp., E.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp , B. Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata; Pests of the strain of Mollusca, z. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., Z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., Z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .; Plant pests from the strain of Nematoda, ie plant parasitic nematodes, in particular Aglenchus spp., Z. Aglenchus agricola, Anguina spp., E.g. Anguina tritici, Aphelenchoides spp., E.g. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., E.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., Z. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., E.g. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index. The compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as a remedy for MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients. Formulations The present invention furthermore relates to formulations and use forms prepared therefrom as pesticides, such as, for example, pesticides. B. drench, drip and spray liquors, comprising at least one compound of formula (I). Optionally, the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g. As vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg. As organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such. As dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such. As glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer. Typical 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 other 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. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances. They are preferably formulations or use forms which contain auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants. An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration. These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants. The preparation of the formulations is carried out either in suitable systems or before or during use. Excipients which can be used are those which are suitable for imparting special properties to the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, usable pesticides such as spray mixtures or seed dressing), such as certain physical, technical and / or to confer biological properties. Suitable extenders z. As water, polar and nonpolar organic chemical liquids such. B. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), the ketones (such as acetone, cyclohexanone ), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide). In the case of using water as an extender z. As well as organic solvents can be used as an auxiliary solvent. Suitable liquid solvents are essentially: 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, eg. As petroleum 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, strong polar solvents such as dimethylformamide and dimethyl sulfoxide and water. In principle, all suitable solvents can be used. Suitable solvents are, for example, 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, iso-propanol, butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water. In principle, all suitable carriers can be used. As carriers are in particular question: z. Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as fumed silica, alumina and natural or synthetic silicates, Resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: z. As broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corncobs and tobacco stems. Also, liquefied gaseous diluents or solvents can be used. In particular, are such extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for. As aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic 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 sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g. As alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water. As further auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg. For example, iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present. Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers. In addition, the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils. Optionally, further auxiliaries may be present in the formulations and in the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestering agents, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes. As retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers. Penetration promoters in the present context include all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients 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 oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, Fettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate. The formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation. The content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of the compound of the formula (I) in the use forms may usually be 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 application form , lie. The application is done in a custom forms adapted to the application. Mixtures The compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, Semiochemicals and / or plant growth regulators are used to z. B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting benefits can be facilitated, crop yield and yield, maturity, crop quality and / or nutritional value increased, shelf life extended, and / or crop productivity improved. Furthermore, the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of formula (I) can be used to improve plant properties such as growth, yield and quality of the crop. In a particular embodiment of the invention, the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below. If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case. In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners can optionally form salts with suitable bases or acids. Insecticides / Acaricides / Nematicides The active substances mentioned here with their "Common Name" are known and are described, for example, in the Pesticide Handbook ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or searchable on the Internet (eg http: // /www.alanwood.net/pesticides). The classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application. (1) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, e.g. Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, Demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfone, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthione, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl-O- (methoxyaminothio-phosphoryl ) salicylate, isoxathione, malathion, mecarbam, methamidophos, methidathione, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidone, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos , Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon and Vamidothion. (2) GABA-controlled chloride channel blockers, such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil. (3) sodium channel modulators, such as pyrethroids, e.g. A-crinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma Cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R) -trans isomer], deltamethrin, empenthrin [(EZ) (1R) isomer], esfenvalerate, etofenprox, Fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R) -trans-isomer], prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [ (1R) -isomer], tralomethrin and transfluthrin or DDT or methoxychlor. (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as neonicotinoids, e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone. (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as spinosyn, e.g. B. spinetoram and spinosad. (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl), such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin. (7) Juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen. (8) Various non-specific (multi-site) inhibitors, such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam. (9) modulators of chordotonic organs, e.g. As pymetrozine or flonicamide. (10) mite growth inhibitors, such as. Clofentezine, hexythiazox and diflovidazine or etoxazole. (11) Microbial disruptors of insect intestinal membrane such. B. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and Bt plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1. (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors, such as diafenthiuron or organotin compounds, e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone. (13) Decoupling of oxidative phosphorylation by disruption of the proton gradient, such as chlorfenapyr, DNOC and sulfluramide. (14) Blockers of the nicotinic acetylcholine receptor channel, such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium. (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron. (16) inhibitors of chitin biosynthesis, type 1, such as buprofezin. (17) Skinning disruptor (especially in dipterans, ie, two-wingers), such as cyromazine. (18) ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide. (19) octopamine receptor agonists, such as amitraz. (20) Mitochondrial Complex III Electron Transport Inhibitors such as hydramethylnone or acequinocyl or fluacrypyrim. (21) Mitochondrial Complex I Electron Transport Inhibitors, such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris). (22) blocker of the voltage-dependent sodium channel, such. Indoxacarb or metaflumizone. (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat. (24) inhibitors of mitochondrial complex IV electron transport, such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide. (25) inhibitors of mitochondrial complex II electron transport, such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyflumetofen and carboxanilides such as Pyflubumid. (28) ryanodine receptor modulators, such as diamides, e.g. B. chlorantraniliprole, cyanotriliprol and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon- Momfluthrin, Flometoquine, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozid, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazone, Pyriminostrobin, spirobudiclofen, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and the following compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} - 3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), {1 '- [(2E) -3- (4-chlorophenyl ) prop-2-en-1-yl] -5-fluorospiro [indole-3,4'-piperidin] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from WO2003 / 106457) (CAS 637360-23-7), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) -prop-2-en-1-yl] -piperidin-4-yl} - 4- (trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3- (4-chloro-2,6-dimethylphenyl) -4-hydroxy-8-methoxy-1,8- diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2, 6-dimethylphenyl) -8-methoxy-2-oxo 1,8-diazaspiro [4.5] dec-3-en-4-yl ethyl carbonate (known from EP 2647626) (CAS-1440516-42-6), 4- (but-2-yn-1-yloxy) -6 - (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP20 10/018586) (CAS Reg. No. 1204776-60-2), N - [(2E) -1 - [(6-chloropyridin-3-yl) methyl] pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from WO2012 / 029672) (CAS 1363400-41-2), (3E) -3- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1,1-trifluoropropan-2-one ( known from WO2013 / 144213) (CAS 1461743-15-6), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5 carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N- [4-chloro-2-methyl-6- (methylcarbamoyl) phenyl] -2- (3 chloro-2-pyridyl) pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4- [5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) - 3-isoxazolyl] -2-methyl-N- (cis-1-oxido-3-thietanyl) -benzamide, 4- [5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) -3 -isoxazolyl] -2-methyl-N- (trans-1-oxido-3-thietanyl) benzamide and 4 - [(5S) -5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl ) - 3-isoxazolyl] -2-methyl-N- (cis-1-oxido-3-thietanyl) benzamide (known from WO 2013/050317 A1) (CAS 1332628-83-7), N- [3-chloro-1 (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) sulfinyl] propanamide, (+) - N- [3-chloro-1- (3 -pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) sulfinyl] propanamide and (-) - N- [3-chloro-1- (3-pyridinyl ) -1H-pyrazol-4-yl] -N-ethyl-3- [(3,3,3-trifluoropropyl) sulfinyl] propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1 ) (CAS 1477923-37-7), 5 - [[(2E) -3-chloro-2-propen-1-yl] amino] -1- [2,6-dichloro-4- (trifluoromethyl) phenyl] - 4 - [(trifluoromethyl) sulfinyl] -1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N- [4-chloro-2-methyl-6- [ (methylamino) thioxomethyl] phenyl] -1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide,
(Liudaibenjiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9); N-[4-Chlor-2-[[(1,1- dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chlor-2-pyridinyl)-3-(fluormethoxy)-1H-pyrazol- 5-carboxamid (bekannt aus WO 2012/034403 A1) (CAS 1268277-22-0), N-[2-(5-Amino-1,3,4- thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-1-(3-chlor-2-pyridinyl)-1H-pyrazol-5-carboxamid (bekannt aus WO 2011/085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-Dichlor-4-[(3,3-dichlor-2-propen-1- yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN 101337940 A) (CAS 1108184-52-6); (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-1-[3-(trifluormethyl)phenyl]ethyliden]-N-[4- (difluormethoxy)phenyl]hydrazincarboxamid (bekannt aus CN 101715774 A) (CAS 1232543-85-9); Cyclopropancarbonsäure-3-(2,2-dichlorethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylester (bekannt aus CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-Chlor-2,5-dihydro-2- [[(methoxycarbonyl)[4-[(trifluormethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazin- 4a(3H)-carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2); 6-Desoxy-3-O- ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluorethoxy)phenyl]-1H-1,2,4-triazol-3- yl]phenyl]carbamat]-α-L-mannopyranose (bekannt aus US 2014/0275503 A1) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3- azabicyclo[3.2.1]octan (CAS 1253850-56-4), (8-anti)-8-(2-Cyclopropylmethoxy-4- trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octan (CAS 933798-27- 7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3- azabicyclo[3.2.1]octan (bekannt aus WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) und N-[3-Chlor-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)thio]-propanamid (bekannt aus WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9). Fungizide Die hier mit ihrem“Common Name” spezifizierten Wirkstoffe sind bekannt und beispielsweise im “Pesticide Manual” (16. Aufl. British Crop Protection Council) oder im Internet recherchierbar (beispielsweise: http://www.alanwood.net/pesticides) beschrieben. Alle genannten Mischungspartner der Klassen (1) bis (15) können, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Alle genannten fungiziden Mischungspartner der Klassen (1) bis (15) können gegebenenfalls tautomere Formen einschließen. 1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenoconazol, (1.003) Epoxiconazol, (1.004) Fenhexamid, (1.005) Fenpropidin, (1.006) Fenpropimorph, (1.007) Fenpyrazamin, (1.008) Fluquinconazol, (1.009) Flutriafol, (1.010) Imazalil, (1.011) Imazalil Sulfat, (1.012) Ipconazol, (1.013) Metconazol, (1.014) Myclobutanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.017) Propiconazol, (1.018) Prothioconazol, (1.019) Pyrisoxazol, (1.020) Spiroxamin, (1.021) Tebuconazol, (1.022) Tetraconazol, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazol, (1.026) (1R,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1- ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4- triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-Chlorcyclopropyl)-4-[(1R)-2,2-dichlorcyclopropyl]- 1-(1H-1,2,4-triazol-1-yl)butan-2-ol (1.029) (2R)-2-(1-Chlorcyclopropyl)-4-[(1S)-2,2- dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-Chlorphenoxy)-2- (trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-Chlorcyclopropyl)-4- [(1R)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-Chlorcyclopropyl)- 4-[(1S)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-Chlor- 2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-Chlor-2- fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-Chlor-2- fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2- Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazol, (1.038) 1- ({(2S,4S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazol, (1.039) 1-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl- thiocyanat, (1.040) 1-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H- 1,2,4-triazol-5-yl-thiocyanat, (1.041) 1-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yl]methyl}-1H-1,2,4-triazol-5-yl-thiocyanat, (1.042) 2-[(2R,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy- 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.043) 2-[(2R,4R,5S)-1-(2,4- Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.044) 2- [(2R,4S,5R)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4- triazol-3-thion, (1.045) 2-[(2R,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-1,2,4-triazol-3-thion, (1.046) 2-[(2S,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.047) 2-[(2S,4R,5S)-1-(2,4- Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.048) 2- [(2S,4S,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol- 3-thion, (1.049) 2-[(2S,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-1,2,4-triazol-3-thion, (1.050) 2-[1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.051) 2-[2-Chlor-4-(2,4-dichlorophenoxy)phenyl]-1-(1H- 1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-1-(1H-1,2,4-triazol-1- yl)butan-2-ol, (1.053) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan- 2-ol, (1.054) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.056) 2-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.057) 2-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H- 1,2,4-triazol-3-thion, (1.058) 2-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.059) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl- 1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(Allylsulfanyl)-1-{[3-(2-chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.061) 5-(Allylsulfanyl)-1-{[rel(2R,3R)-3-(2- chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.062) 5-(Allylsulfanyl)-1- {[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.063) N'- (2,5-Dimethyl-4-{[3-(1,1,2,2-tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N- methylimidoformamid, (1.064) N'-(2,5-Dimethyl-4-{[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)- N-ethyl-N-methylimidoformamid, (1.065) N'-(2,5-Dimethyl-4-{[3-(2,2,3,3- tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.066) N'-(2,5-Dimethyl- 4-{[3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.067) N'-(2,5- Dimethyl-4-{3-[(1,1,2,2-tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.068) N'-(2,5-Dimethyl-4-{3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamid, (1.069) N'-(2,5-Dimethyl-4-{3-[(2,2,3,3- tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.070) N'-(2,5-Dimethyl- 4-{3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.071) N'-(2,5- Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamid, (1.072) N'-(4-{[3- (Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.073) N'- (4-{3-[(Difluormethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.074) N'-[5-Brom-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N- methylimidoformamid, (1.075) N'-{4-[(4,5-Dichlor-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl- N-methylimidoformamid, (1.076) N'-{5-Brom-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin- 3-yl}-N-ethyl-N-methylimidoformamid, (1.077) N'-{5-Brom-6-[(1S)-1-(3,5-difluorphenyl)ethoxy]-2- methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.078) N'-{5-Brom-6-[(cis-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.079) N'-{5- Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.080) N'-{5-Bromo-6-[1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N- methylimidoformamid. 2) Inhibitoren der Atmungskette am Komplex I oder II beispielsweise (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, (2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isofetamid, (2.010) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.011) Isopyrazam (anti-epimeres Enantiomer 1S,4R,9R), (2.012) Isopyrazam (anti- epimeres Racemat 1RS,4SR,9SR), (2.013) Isopyrazam (Mischung des syn-epimeren Razemates 1RS,4SR,9RS und des anti-epimeren Razemates 1RS,4SR,9SR), (2.014) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.015) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.016) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (2.020) Pyraziflumid, (2.021) Sedaxane, (2.022) 1,3-Dimethyl-N-(1,1,3-trimethyl-2,3- dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.023) 1,3-Dimethyl-N-[(3R)-1,1,3-trimethyl-2,3- dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.024) 1,3-Dimethyl-N-[(3S)-1,1,3-trimethyl-2,3- dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.025) 1-Methyl-3-(trifluormethyl)-N-[2'- (trifluormethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.026) 2-Fluor-6-(trifluoromethyl)-N-(1,1,3- trimethyl-2,3-dihydro-1H-inden-4-yl)benzamid, (2.027) 3-(Difluormethyl)-1-methyl-N-(1,1,3-trimethyl- 2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.028) 3-(Difluormethyl)-1-methyl-N-[(3R)- 1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.029) 3-(Difluormethyl)-1- methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.030) 3- (Difluormethyl)-N-(7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazol-4- carboxamid, (2.031) 3-(Difluormethyl)-N-[(3R)-7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1- methyl-1H-pyrazol-4-carboxamid, (2.032) 3-(Difluoromethyl)-N-[(3S)-7-fluor-1,1,3-trimethyl-2,3- dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.033) 5,8-Difluor-N-[2-(2-fluor-4-{[4- (trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amin, (2.034) N-(2-Cyclopentyl-5- fluorbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.035) N- (2-tert-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4- carboxamid, (2.036) N-(2-tert-Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H- pyrazol-4-carboxamid, (2.037) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1- methyl-1H-pyrazol-4-carboxamid, (2.038) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3- (difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.039) N-[(1R,4S)-9-(Dichlormethylen)- 1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.040) N-[(1S,4R)-9-(Dichlormethylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3- (difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.041) N-[1-(2,4-Dichlorphenyl)-1- methoxypropan-2-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.042) N-[2-Chlor-6- (trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.043) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1- methyl-1H-pyrazol-4-carboxamid, (2.044) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3- (difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.045) N-Cyclopropyl-3-(difluormethyl)- 5-fluor-1-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-1H-pyrazol-4-carboxamid, (2.046) N- Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-1-methyl-1H-pyrazol-4- carboxamid, (2.047) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-1- methyl-1H-pyrazol-4-carboxamid, (2.048) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2- isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamid, (2.049) N-Cyclopropyl-3-(difluoromethyl)-5- fluor-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.050) N-Cyclopropyl-3- (difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.051) N- Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-1-methyl-1H-pyrazol-4- carboxamid, (2.052) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-1-methyl-1H- pyrazol-4-carboxamid, (2.053) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-1- methyl-1H-pyrazole-4-carboxamid, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3- (difluormethyl)-5-fluor-1-methyl-1H-pyrazole-4-carboxamid, (2.055) N-Cyclopropyl-N-(2-cyclopropyl- 5-methylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazole-4-carboxamid, (2.056) N- Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazole-4-carboxamid. 3) Inhibitoren der Atmungskette am Komplex III, beispielsweise (3.001) Ametoctradin, (3.002) Amisulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.011) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-Methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-Fluor-2- phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamid, (3.022) (2E,3Z)-5-{[1-(4-Chlorphenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3- enamid, (3.023) (2R)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.024) (2S)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.025) (3S,6S,7R,8R)-8-Benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6- methyl-4,9-dioxo-1,5-dioxonan-7-yl-2-methylpropanoat, (3.026) 2-{2-[(2,5- Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.027) N-(3-Ethyl-3,5,5- trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.028) (2E,3Z)-5-{[1-(4-Chlor-2-fluorphenyl)- 1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid. 4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Pencycuron, (4.006) Thiabendazol, (4.007) Thiophanat-Methyl, (4.008) Zoxamid, (4.009) 3-Chlor-4-(2,6-difluorphenyl)-6-methyl-5- phenylpyridazin, (4.010) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (4.011) 3- Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin, (4.012) 4-(2-Brom-4- fluorphenyl)-N-(2,6-difluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.013) 4-(2-Brom-4- fluorphenyl)-N-(2-brom-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.014) 4-(2-Brom-4- fluorphenyl)-N-(2-bromphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.015) 4-(2-Brom-4-fluorphenyl)-N- (2-chlor-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.016) 4-(2-Brom-4-fluorphenyl)-N-(2- chlorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.017) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)- 1,3-dimethyl-1H-pyrazol-5-amin, (4.018) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)-1,3- dimethyl-1H-pyrazol-5-amin, (4.019) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-1,3- dimethyl-1H-pyrazol-5-amin, (4.020) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-1,3-dimethyl-1H- pyrazol-5-amin, (4.021) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.022) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (4.023) N-(2-Brom-6- fluorphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.024) N-(2-Bromphenyl)-4- (2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.025) N-(4-Chlor-2,6-difluorphenyl)-4-(2- chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin. 5) Verbindungen mit Befähigung zu Multisite-Aktivität, beispielsweise (5.001) Bordeauxmischung, (5.002) Captafol, (5.003) Captan, (5.004) Chlorthalonil, (5.005) Kupferhydroxid, (5.006) Kupfernaphthenat, (5.007) Kupferoxid, (5.008) Kupferoxychlorid, (5.009) Kupfer(2+)-sulfat, (5.010) Dithianon, (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Zinkmetiram, (5.017) Kupfer-Oxin, (5.018) Propineb, (5.019) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram. 6) Verbindungen, die zum Auslösen einer Wirtsabwehr befähigt sind, beispielsweise (6.001) Acibenzolar-S-Methyl, (6.002) Isotianil, (6.003) Probenazol, (6.004) Tiadinil. 7) Inhibitoren der Aminosäure- und/oder Protein-Biosynthese, beispielsweise (7.001) Cyprodinil, (7.002) Kasugamycin, (7.003) Kasugamycinhydrochlorid-hydrat, (7.004) Oxytetracyclin (7.005) Pyrimethanil, (7.006) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-1-yl)chinolin. (8) Inhibitoren der ATP-Produktion, beispielsweise (8.001) Silthiofam. 9) Inhibitoren der Zellwandsynthese, beispielsweise (9.001) Benthiavalicarb, (9.002) Dimethomorph, (9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamid, (9.006) Pyrimorph, (9.007) Valifenalat, (9.008) (2E)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-1-(morpholin-4-yl)prop-2-en- 1-on, (9.009) (2Z)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-on. 10) Inhibitoren der Lipid- und Membran-Synthese, beispielsweise (10.001) Propamocarb, (10.002) Propamocarbhydrochlorid, (10.003) Tolclofos-Methyl. 11) Inhibitoren der Melanin-Biosynthese, beispielsweise (11.001) Tricyclazol, (11.002) 2,2,2- Trifluorethyl-{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamat. 12) Inhibitoren der Nukleinsäuresynthese, beispielsweise (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam). 13) Inhibitoren der Signaltransduktion, beispielsweise (13.001) Fludioxonil, (13.002) Iprodion, (13.003) Procymidon, (13.004) Proquinazid, (13.005) Quinoxyfen, (13.006) Vinclozolin. 14) Verbindungen, die als Entkoppler wirken können, beispielsweise (14.001) Fluazinam, (14.002) Meptyldinocap. 15) Weitere Verbindungen, beispielsweise (15.001) Abscisinsäure, (15.002) Benthiazol, (15.003) Bethoxazin, (15.004) Capsimycin, (15.005) Carvon, (15.006) Chinomethionat, (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.011) Flutianil, (15.012) Fosetyl-Aluminium, (15.013) Fosetyl-Calcium, (15.014) Fosetyl-Natrium, (15.015) Methylisothiocyanat, (15.016) Metrafenon, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel-Dimethyldithiocarbamat, (15.020) Nitrothal-Isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiprolin, (15.023) Oxyfenthiin, (15.024) Pentachlorphenol und Salze, (15.025) Phosphonsäure und deren Salze, (15.026) Propamocarb-fosetylat, (15.027) Pyriofenone (Chlazafenone) (15.028) Tebufloquin, (15.029) Tecloftalam, (15.030) Tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-Difluorphenyl)- 4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluormethyl)-1H- pyrazol-1-yl]ethanon, (15.032) 1-(4-{4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3- thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]ethanon, (15.033) 2-(6- Benzylpyridin-2-yl)quinazolin, (15.034) 2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol- 1,3,5,7(2H,6H)-tetron, (15.035) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-in-1- yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.036) 2-[3,5- Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2- oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.037) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1- yl]-1-[4-(4-{5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2- yl)piperidin-1-yl]ethanon, (15.038) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolin, (15.039) 2-{(5R)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4- yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenyl methanesulfonat, (15.040) 2-{(5S)-3-[2-(1-{[3,5- Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5- yl}-3-chlorphenyl methanesulfonat, (15.041) 2-{2-[(7,8-Difluor-2-methylquinolin-3-yl)oxy]-6- fluorphenyl}propan-2-ol, (15.042) 2-{2-Fluor-6-[(8-fluor-2-methylquinolin-3-yl)oxy]phenyl}propan-2- ol, (15.043) 2-{3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4- yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenyl-methansulfonat, (15.044) 2-{3-[2-(1-{[3,5- Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5- yl}phenyl methanesulfonat, (15.045) 2-Phenylphenol und deren Salze, (15.046) 3-(4,4,5-Trifluor-3,3- dimethyl-3,4-dihydroisoquinolin-1-yl)quinolin, (15.047) 3-(4,4-Difluor-3,3-dimethyl-3,4- dihydroisoquinolin-1-yl)quinolin, (15.048) 4-Amino-5-fluorpyrimidin-2-ol (Tautomere Form: 4-Amino- 5-fluorpyrimidin-2(1H)-on), (15.049) 4-Oxo-4-[(2-phenylethyl)amino]buttersäure, (15.050) 5-Amino- 1,3,4-thiadiazol-2-thiol, (15.051) 5-Chlor-N'-phenyl-N'-(prop-2-yn-1-yl)thiophen-2-sulfonohydrazid, (15.052) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.053) 5-Fluor-2-[(4- methylbenzyl)oxy]pyrimidin-4-amin, (15.054) 9-Fluor-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4- benzoxazepin, (15.055) But-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5- yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.056) Ethyl (2Z)-3-amino-2-cyano- 3-phenylacrylat, (15.057) Phenazin-1-carbonsäure, (15.058) Propyl 3,4,5-trihydroxybenzoat, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfat (2:1), (15.061) tert-Butyl {6-[({[(1-methyl-1H-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamat. Biologische Schädlingsbekämpfungsmittel als Mischungskomponenten Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte. Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Bacillus amyloliquefaciens, Stamm FZB42 (DSM 231179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM I-1562 oder Bacillus firmus, Stamm I-1582 (Accession number CNCM I-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. NRRL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD-1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, insbesondere B. thuringiensis Subspezies israelensis (Serotyp H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder B. thuringiensis subsp. aizawai, insbesondere Stamm ABTS-1857 (SD-1372), oder B. thuringiensis subsp. kurstaki Stamm HD-1, oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232). Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm HRO LEC 12, Lecanicillium lecanii (ehemals bekannt als Verticillium lecanii), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (neu: Isaria fumosorosea), insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, insbesondere P. lilacinus Stamm 251 (AGAL 89/030550), Talaromyces flavus, insbesondere Stamm V117b, Trichoderma atroviride, insbesondere Stamm SC1 (Accession Number CBS 122089), Trichoderma harzianum, insbesondere T. harzianum rifai T39. (Accession Number CNCM I-952). Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV. Es sind auch Bakterien und Pilze umfasst, die als‚Inokulant‘ Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.. Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrine, Quassia amara, Quercus, Quillaja, Regalia,„Requiem™ Insecticide“, Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver. Safener als Mischungskomponenten Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid (CAS 129531-12-0), 4-(Dichloracetyl)-1-oxa-4-azaspiro[4.5]decan (CAS 71526-07-3), 2,2,5-Trimethyl-3- (dichloracetyl)-1,3-oxazolidin (CAS 52836-31-4). Pflanzen und Pflanzenteile Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Paprika, Gurke, Melone, Möhre, Wassermelone, Zwiebel, Salat, Spinat, Porree, Bohnen, Brassica oleracea (z. B. Kohl) und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzen sollen alle Entwicklungsstadien wie Saatgut, Stecklinge, junge (unausgereifte) Pflanzen bis hin zu ausgereiften Pflanzen verstanden werden. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehören auch geerntete Pflanzen oder geerntete Pflanzenteile sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung der Verbindungen auf die Umgebung, den Lebensraum oder den Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Eintauchen, Spritzen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff„Teile“ bzw.„Teile von Pflanzen“ oder„Pflanzenteile“ wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits“), die durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schädlinge, wie Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z. B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z. B. durch die Gene CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CryIF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z. B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinone, Sulfonylharnstoffe, Glyphosat oder Phosphinotricin (z. B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. Pflanzenschutz– Behandlungsarten Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Tauchen, Spritzen, Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, Verstreuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low-Volume-Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) selbst in den Boden zu injizieren. Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d. h. die Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. Bei systemisch wirksamen Wirkstoffen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d. h. der Standort der Pflanze (z. B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d. h. die erfindungsgemäßen Verbindungen der Formel (I) werden in fester Form (z. B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z. B. als Granulat) in ein überflutetes Reisfeld sein. Saatgutbehandlung Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Be- handlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Schädlingsbekämpfungsmitteln bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw.–toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und auch der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer erfindungsgemäßen Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut vorhanden sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungskomponenten enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und eine Mischungskomponente als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) einem Filmcoating-Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. Einer der auftretenden Vorteile, wenn eine Verbindung der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können. Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können. Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baumwolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z. B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola, Raps, Gemüse und Reis zu. Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hüllen, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z. B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Fall von Reis-Saatgut ist es auch möglich, Saatgut zu verwenden, das getränkt wurde, zum Beispiel in Wasser bis zu einem bestimmten Stadium des Reisembryos („Pigeon Breast Stage“), wodurch die Keimung und ein einheitlicheres Auflaufen stimuliert wird. Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. Diese Formulierungen werden in bekannter Weise hergestellt, indem man die Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe. Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalinsulfonate, wie Diisopropyl- oder Diisobutylnaphthalinsulfonate. Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor-zugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tri- stryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat- Formaldehydkondensate. Als Entschäumer können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formu- lierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln ein- setzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline A1, A3 (= Gibberellinsäure), A4 und A7 infrage, be- sonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel“, Bd.2, Springer Verlag, 1970, S.401- 412). Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen können entweder direkt oder nach vorherigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art eingesetzt werden. So lassen sich die Konzentrate oder die daraus durch Verdünnen mit Wasser erhältlichen Zu- bereitungen einsetzen zur Beizung des Saatgutes von Getreide, wie Weizen, Gerste, Roggen, Hafer und Triticale, sowie des Saatgutes von Mais, Reis, Raps, Erbsen, Bohnen, Baumwolle, Sonnenblumen, Soja und Rüben oder auch von Gemüsesaatgut der verschiedensten Natur. Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder deren verdünnte Anwendungsformen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden. Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder dem daraus durch Zugabe von Wasser hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im Einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichen oder kontinuierlichen Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an. Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) liegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut. Tiergesundheit Auf dem Gebiet der Tiergesundheit, d. h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasit umfasst insbesondere Helminthen und Protozoen wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten oder Akariden. Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I), die eine günstige Toxizität gegenüber Warmblütern aufweisen, für die Bekämpfung von Parasiten, die in der Tierzucht und Tierhaltung bei Nutztieren, Zuchttieren, Zootieren, Laboratoriumstieren, Versuchstieren und Haustieren auftreten. Sie sind gegen alle oder einzelne Entwicklungsstadien der Parasiten wirksam. Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; oder Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; oder Fische oder Krustentiere, z. B. in der Aquakultur, oder gegebenenfalls Insekten wie Bienen. Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel; Reptilien, Amphibien oder Aquariumfische. Gemäß einer bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. Gemäß einer weiteren bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel oder insbesondere Geflügel, verabreicht. Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erzielbar ist. In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen" im vorliegenden Zusammenhang, dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert wird. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindungen der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern. Zu den Arthropoden zählen beispielsweise, ohne hierauf beschränkt zu sein, aus der Ordnung Anoplurida zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina und Ischnocerina, zum Beispiel Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; aus der Ordnung Siphonapterida, zum Beispiel Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. Weiterhin sind bei den Arthropoden beispielhaft, ohne hierauf beschränkt zu sein, die folgenden Akari zu nennen: Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Ornithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.; und aus der Ordung der Acaridida (Astigmata), zum Beispiel Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp. Zu Beispielen für parasitäre Protozoen zählen, ohne hierauf beschränkt zu sein: Mastigophora (Flagellata), wie: Metamonada: aus der Ordnung Diplomonadida zum Beispiel Giardia spp., Spironucleus spp. Parabasala: aus der Ordnung Trichomonadida zum Beispiel Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Euglenozoa: aus der Ordnung Trypanosomatida zum Beispiel Leishmania spp., Trypanosoma spp. Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba spp., Centramoebidae, zum Beispiel Acanthamoeba sp., Euamoebidae, z. B. Hartmanella sp. Alveolata wie Apicomplexa (Sporozoa): z. B. Cryptosporidium spp.; aus der Ordnung Eimeriida zum Beispiel Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; aus der Ordnung Adeleida z. B. Hepatozoon spp., Klossiella spp.; aus der Ordnung Haemosporida z. B. Leucocytozoon spp., Plasmodium spp.; aus der Ordnung Piroplasmida z. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; aus der Ordnung Vesibuliferida z. B. Balantidium spp., Buxtonella spp. Microspora wie Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., und außerdem z. B. Myxozoa spp. Zu den für Menschen oder Tiere pathogenen Helminthen zählen zum Beispiel Acanthocephala, Nematoden, Pentastoma und Platyhelminthen (z.B. Monogenea, Cestodes und Trematodes). Zu beispielhaften Helminthen zählen, ohne hierauf beschränkt zu sein: Monogenea: z. B.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.; Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. Aus der Ordnung Cyclophyllida zum Beispiel: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp. Trematodes: aus der Klasse Digenea zum Beispiel: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp. Nematoden: aus der Ordnung Trichinellida zum Beispiel: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. Aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Parastrangyloides spp., Strongyloides spp. Aus der Ordnung Rhabditina zum Beispiel: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp. Aus der Ordnung Spirurida zum Beispiel: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp., Aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp. Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch; metaphylaktisch oder therapeutisch erfolgen. So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verbindungen der Formel (I) zur Verwendung als Arzneimittel. Ein weiterer Aspekt bezieht sich auf die Verbindungen der Formel (I) zur Verwendung als Antiendoparasitikum. Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwendung als Antihelminthikum, insbesondere zur Verwendung als Nematizid, Platymelminthizid, Acanthocephalizid oder Pentastomizid. Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwendung als Antiprotozoikum. Ein weiterer Aspekt betrifft die Verbindungen der Formel (I) zur Verwendung als Antiektoparasitikum, insbesondere ein Arthropodizid, ganz besonders ein Insektizid oder ein Akarizid. Weitere Aspekte der Erfindung sind veterinärmedizinische Formulierungen, die eine wirksame Menge mindestens einer Verbindung der Formel (I) und mindestens einen der folgenden umfassen: einen pharmazeutisch unbedenklichen Exzipienten (z.B. feste oder flüssige Verdünnungsmittel), ein pharmazeutisch unbedenkliches Hilfsmittel (z.B. Tenside), insbesondere einen herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder ein herkömmlicherweise in veterinärmedizinischen Formulierungen verwendetes pharmazeutisch unbedenkliches Hilfsmittel. Ein verwandter Aspekt der Erfindung ist ein Verfahren zur Herstellung einer wie hier beschriebenen veterinärmedizinischen Formulierung, welches den Schritt des Mischens mindestens einer Verbindung der Formel (I) mit pharmazeutisch unbedenklichen Exzipienten und/oder Hilfsmitteln, insbesondere mit herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten Hilfsmitteln umfasst. Ein anderer spezieller Aspekt der Erfindung sind veterinärmedizinische Formulierungen ausgewählt aus der Gruppe ektoparasitizider und endoparasitizider Formulierungen, insbesondere ausgewählt aus der Gruppe anthelmintischer, antiprotozolischer und arthropodizider Formulierungen, ganz besonders ausgewählt aus der Gruppe nematizider, platyhelminthizider, acanthocephalizider, pentastomizider, insektizider und akkarizider Formulierungen, gemäß den erwähnten Aspekten, sowie Verfahren zu ihrer Herstellung. Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wirksamen Menge einer Verbindung der Formel (I) bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wie hier definierten veterinärmedizinischen Formulierung bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Ein anderer Aspekt bezieht sich auf die Verwendung der Verbindungen der Formel (I) bei der Behandlung einer Parasiteninfektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, bei einem Tier, insbesondere einem nichthumanen Tier. Im vorliegenden tiergesundheitlichen oder veterinärmedizinischen Zusammenhang schließt der Begriff „Behandlung“ die prophylaktische, die metaphylaktische und die therapeutische Behandlung ein. Bei einer bestimmten Ausführungsform werden hiermit Mischungen mindestens einer Verbindung der Formel (I) mit anderen Wirkstoffen, insbesondere mit Endo- und Ektoparasitiziden, für das veterinärmedizinische Gebiet bereitgestellt. Auf dem Gebiet der Tiergesundheit bedeutet„Mischung“ nicht nur, dass zwei (oder mehr) verschiedene Wirkstoffe in einer gemeinsamen Formulierung formuliert werden und entsprechend zusammen angewendet werden, sondern bezieht sich auch auf Produkte, die für jeden Wirkstoff getrennte Formulierungen umfassen. Dementsprechend können, wenn mehr als zwei Wirkstoffe angewendet werden sollen, alle Wirkstoffe in einer gemeinsamen Formulierung formuliert werden oder alle Wirkstoffe in getrennten Formulierungen formuliert werden; ebenfalls denkbar sind gemischte Formen, bei denen einige der Wirkstoffe gemeinsam formuliert und einige der Wirkstoffe getrennt formuliert sind. Getrennte Formulierungen erlauben die getrennte oder aufeinanderfolgende Anwendung der in Rede stehenden Wirkstoffe. Die hier mit ihrem„Common Name“ spezifizierten Wirkstoffe sind bekannt und beispielsweise im „Pesticide Manual“ (siehe oben) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticides). Beispielhafte Wirkstoffe aus der Gruppe der Ektoparasitizide als Mischungspartner schließen, ohne dass dies eine Einschränkung darstellen soll, die oben ausführlich aufgelisteten Insektizide und Akkarizide ein. Weitere verwendbare Wirkstoffe sind unten gemäß der oben erwähnten Klassifikation, die auf dem aktuellen IRAC Mode of Action Classification Scheme beruht, aufgeführt: (1) Acetylcholinesterase (AChE)-Inhibitoren; (2) GABA-gesteuerte Chlorid-Kanal-Blocker; (3) Natrium-Kanal-Modulatoren; (4) kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (5) allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (6) allosterische Modulatoren des Glutamat-abhängigen Chloridkanals (GluCl); (7) Juvenilhormon-Mimetika; (8) verschiedene nichtspezifische (Multi-Site) Inhibitoren; (9) Modulatoren Chordotonaler Organe; (10) Milbenwachstumsinhibitoren; (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP- Disruptoren; (13) Entkoppler der oxidativen Phosphorylierung durch Störung des Protonengradienten; (14) Blocker des nicotinischen Acetylcholinrezeptorkanals; (15) Inhibitoren der Chitinbiosynthese, Typ 0; (16) Inhibitoren der Chitinbiosynthese, Typ 1; (17) Häutungsdisruptor (insbesondere bei Dipteren, d.h. Zweiflüglern); (18) Ecdyson-Rezeptor-Agonisten; (19) Octopamin-Rezeptor-Agonisten; (21) mitochondriale Komplex-I-Elektronentransportinhibitoren; (25) mitochondriale Komplex-II- Elektronentransportinhibitoren; (20) mitochondriale Komplex-III-Elektronentransportinhibitoren; (22) Blocker des spannungsabhängigen Natriumkanals; (23) Inhibitoren der Acetyl-CoA-Carboxylase; (28) Ryanodinrezeptor-Modulatoren; Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, z. B. Fentrifanil, Fenoxacrim, Cyclopren, Chlorobenzilat, Chlordimeform, Flubenzimin, Dicyclanil, Amidoflumet, Quinomethionat, Triarathen, Clothiazoben, Tetrasul, Kaliumoleat, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Brompropylat, Cryolit; Verbindungen aus anderen Klassen, z.B. Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos(- ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylat, Trichlorfon, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoat, Dichlofenthion, Demeton-S-methylsulfon, Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpyrifos(- ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos; Organochlorverbindungen, z. B. Camphechlor, Lindan, Heptachlor; oder Phenylpyrazole, z. B. Acetoprol, Pyrafluprol, Pyriprol, Vaniliprol, Sisapronil; oder Isoxazoline, z. B. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Pyrethroide, z. B. (cis-, trans-)Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis-Permethrin, Clocythrin, Cyhalothrin (lambda-), Chlovaporthrin, oder halogenierte Kohlenwasserstoffverbindungen (HCHs), Neonicotinoide, z. B. Nithiazin Dicloromezotiaz, Triflumezopyrim makrocyclische Lactone, z. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprinomectin, Doramectin, Emamectinbenzoat; Milbemycinoxim Tripren, Epofenonan, Diofenolan; Biologicals, Hormone oder Pheromone, zum Beispiel natürliche Produkte, z.B. Thuringiensin, Codlemon oder Neem-Komponenten Dinitrophenole, z. B. Dinocap, Dinobuton, Binapacryl; Benzoylharnstoffe, z. B. Fluazuron, Penfluron, Amidinderivate, z. B. Chlormebuform, Cymiazol, Demiditraz Bienenstockvarroa-Akarizide, zum Beispiel organische Säuren, z.B. Ameisensäure, Oxalsäure. Zu beispielhaften Wirkstoffen aus der Gruppe der Endoparasitizide, als Mischungspartner, zählen, ohne hierauf beschränkt zu sein, anthelmintische Wirkstoffe und antiprotozoische Wirkstoffe. Zu den anthelmintischen Wirkstoffen zählen, ohne hierauf beschränkt zu sein, die folgenden nematiziden, trematiziden und/oder cestoziden Wirkstoffe: aus der Klasse der makrocyclischen Lactone zum Beispiel: Eprinomectin, Abamectin, Nemadectin, Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbemectin, Ivermectin, Emamectin, Milbemycin; aus der Klasse der Benzimidazole und Probenzimidazole zum Beispiel: Oxibendazol, Mebendazol, Triclabendazol, Thiophanat, Parbendazol, Oxfendazol, Netobimin, Fenbendazol, Febantel, Thiabendazol, Cyclobendazol, Cambendazol, Albendazol-sulfoxid, Albendazol, Flubendazol; aus der Klasse der Depsipeptide, vorzugsweise cyclischen Depsipetide, insbesondere 24-gliedrigen cyclischen Depsipeptide, zum Beispiel: Emodepsid, PF1022A; aus der Klasse der Tetrahydropyrimidine zum Beispiel: Morantel, Pyrantel, Oxantel; aus der Klasse der Imidazothiazole zum Beispiel: Butamisol, Levamisol, Tetramisol; aus der Klasse der Aminophenylamidine zum Beispiel: Amidantel, deacyliertes Amidantel (dAMD), Tribendimidin; aus der Klasse der Aminoacetonitrile zum Beispiel: Monepantel; aus der Klasse der Paraherquamide zum Beispiel: Paraherquamid, Derquantel; aus der Klasse der Salicylanilide zum Beispiel: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; aus der Klasse der substituierten Phenole zum Beispiel: Nitroxynil, Bithionol, Disophenol, Hexachlorophen, Niclofolan, Meniclopholan; aus der Klasse der Organophosphate zum Beispiel: Trichlorfon, Naphthalofos, Dichlorvos/DDVP, Crufomat, Coumaphos, Haloxon; aus der Klasse der Piperazinone/Chinoline zum Beispiel: Praziquantel, Epsiprantel; aus der Klasse der Piperazine zum Beispiel: Piperazin, Hydroxyzin; aus der Klasse der Tetracycline zum Beispiel: Tetracyclin, Chlorotetracyclin, Doxycyclin, Oxytetracyclin, Rolitetracyclin; aus diversen anderen Klassen zum Beispiel: Bunamidin, Niridazol, Resorantel, Omphalotin, Oltipraz, Nitroscanat, Nitroxynil, Oxamniquin, Mirasan, Miracil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazin, Dichlorophen, Diamfenetid, Clonazepam, Bephenium, Amoscanat, Clorsulon. Antiprotozoische Wirkstoffe, darunter, ohne hierauf beschränkt zu sein, die folgenden Wirkstoffe: aus der Klasse der Triazine zum Beispiel: Diclazuril, Ponazuril, Letrazuril, Toltrazuril; aus der Klasse Polyletherionophor zum Beispiel: Monensin, Salinomycin, Maduramicin, Narasin; aus der Klasse der makrocyclischen Lactone zum Beispiel: Milbemycin, Erythromycin; aus der Klasse der Chinolone zum Beispiel: Enrofloxacin, Pradofloxacin; aus der Klasse der Chinine zum Beispiel: Chloroquin; aus der Klasse der Pyrimidine zum Beispiel: Pyrimethamin; aus der Klasse der Sulfonamide zum Beispiel: Sulfachinoxalin, Trimethoprim, Sulfaclozin; aus der Klasse der Thiamine zum Beispiel: Amprolium; aus der Klasse der Lincosamide zum Beispiel: Clindamycin; aus der Klasse der Carbanilide zum Beispiel: Imidocarb; aus der Klasse der Nitrofurane zum Beispiel: Nifurtimox; aus der Klasse der Chinazolinonalkaloide zum Beispiel: Halofuginon; aus diversen anderen Klassen zum Beispiel: Oxamniquin, Paromomycin; aus der Klasse der Vakzine oder Antigene aus Mikroorganismen zum Beispiel: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus. Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Vektorbekämpfung Die Verbindungen der Formel (I) können auch in der Vektorbekämpfung eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z. B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z. B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: 1) Mücken - Anopheles: Malaria, Filariose; - Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von anderen Würmern; - Aedes: Gelbfieber, Dengue-Fieber, weitere virale Erkrankungen, Filariasis; - Simulien: Übertragung von Würmern, insbesondere Onchocerca volvulus; - Psychodidae: Übertragung von Leishmaniose 2) Läuse: Hautinfektionen, epidemisches Fleckfieber; 3) Flöhe: Pest, endemisches Fleckfieber, Bandwürmer; 4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 5) Milben: Acariose, epidemisches Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, Frühsommer-Meningoenzephalitis (FSME), Krim-Kongo-Fieber, Borreliose; 6) Zecken: Borelliosen wie Borrelia bungdorferi sensu lato., Borrelia duttoni, Frühsommer- Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis), Ehrlichiose. Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten, zum Beispiel Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Psychodide wie Phlebotomus, Lutzomyia, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Eine Vektorbekämpfung ist auch möglich, wenn die Verbindungen der Formel (I) Resistenz-brechend sind. Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten und/oder Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorbekämpfung, z. B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorrats- und Materialschutz. Schutz von technischen Materialen Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z. B. aus den Ordnungen Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d. h., sie können ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder Fungizide kommen insbesondere die oben genannten in Frage. Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren, Zecken und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen, Tierzuchtanlagen vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z. B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. Erläuterung der Verfahren und Zwischenprodukte: Die erfindungsgemäßen Verbindungen der Formel (I) können durch die in den folgenden Schemata dargestellten Verfahren erhalten werden: Verfahren A Die in Verfahren A angegebenen erfindungsgemäßen Verbindungen der Formel (I-c), in welchen V1 und V2 für Sauerstoff stehen, können durch die Abfolge literaturbekannter Methoden gemäß folgendem Schema hergestellt werden. (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N- [4-chloro-2 - [[(1,1-dimethylethyl) amino] carbonyl] -6-methylphenyl] -1- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -1H-pyrazole 5-carboxamide (known from WO 2012/034403 A1) (CAS 1268277-22-0), N- [2- (5-amino-1,3,4-thiadiazol-2-yl) -4-chloro-6- methylphenyl] -3-bromo-1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4- [3- [ 2,6-dichloro-4 - [(3,3-dichloro-2-propen-1-yl) oxy] phenoxy] propoxy] -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E) - and 2 (Z) -2- [2- (4-cyanophenyl) -1- [3- (trifluoromethyl) phenyl] ethylidene] -N- [4- (difluoromethoxy) phenyl] hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); Cyclopropanecarboxylic acid 3- (2,2-dichloroethenyl) -2,2-dimethyl-4- (1H-benzimidazol-2-yl) phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS) -7-chloro-2,5-dihydro-2- [[(methoxycarbonyl) [4 - [(trifluoromethyl) thio] phenyl] amino] carbonyl] indeno [1,2-e] [1,3,4 ] oxadiazine-4a (3H) -carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-Deoxy-3-O-ethyl-2,4-di-O-methyl-1- [N- [4- [1- [4- (1,1,2,2,2-pentafluoroethoxy) phenyl] - 1H-1,2,4-triazol-3-yl] phenyl] carbamate] -α-L-mannopyranose (known from US 2014/0275503 A1) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 1253850-56-4), (8-anti) -8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 933798-27-7), (8-syn) -8- (2 -Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) and N - [3-Chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) thio] -propanamide (known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9). Fungicides The active ingredients specified here by their "common name" are known and described, for example, in the "Pesticide Manual" (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides) , All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally be salts with suitable bases or acids  form. All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms. 1) inhibitors of ergosterol biosynthesis, for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetraconazole, (1,023) triadimenol, (1,024) tridemorph, (1,025) triticonazole, (1,026) (1R, 2S, 5S) -5- (4 -Chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.027) (1S, 2R, 5R) -5- (4-chlorobenzyl ) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.028) (2R) -2- (1-chlorocyclopropyl) -4 - [( 1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol (1.029) (2R) -2- (1-chlorocyclopropyl) -4- [ (1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-t riazol-1-yl) butan-2-ol, (1030) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazole -1-yl) propan-2-ol, (1.031) (2S) -2- (1-chlorocyclopropyl) -4- [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4 -triazol-1-yl) butan-2-ol, (1.032) (2S) -2- (1-chlorocyclopropyl) -4 - [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2 , 4-triazol-1-yl) butan-2-ol, (1.033) (2S) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2, 4-triazol-1-yl) propan-2-ol, (1034) (R) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazole 4-yl] (pyridin-3-yl) methanol, (1.035) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazole-4 -yl] (pyridin-3-yl) methanol, (1.036) [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridine 3-yl) methanol, (1.037) 1 - ({(2R, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolan-2-yl } methyl) -1H-1,2,4-triazole, (1038) 1- ({(2S, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1, 3-dioxolan-2-yl} methyl) -1H-1,2,4-triazole, (1.039) 1 - {[3- (2-chlorophenyl) -2- (2,4-dif luorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2 - (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1 - {[rel (2R, 3S) -3- ( 2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl-thiocyanate, (1.042) 2 - [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1 , 2,4-triazole-3-thione, (1.044) 2- [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl ] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2 - [(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy 2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2 - [(2S, 4R, 5R) -1- ( 2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1047) 2- [ (2S, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydr o-3H-1,2,4-triazole-3-thione, (1048) 2- [(2S, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6- trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2 - [(2S, 4S, 5S) -1- (2,4-dichlorophenyl) 5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1050) 2- [1- (2,4 -Dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2- [2-chloro -4- (2,4-dichlorophenoxy) phenyl] -1- (1H-  1,2,4-triazol-1-yl) propan-2-ol, (1.052) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1H-1,2,4-triazole -1-yl) butan-2-ol, (1.053) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.054) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) -pentan-2-ol , (1.055) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1056) 2 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione, 1.057) 2 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2 , 4-triazole-3-thione, (1.058) 2 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2 , 4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4 -triazol-1-ylmethyl) cyclopentanol, (1.060) 5- (allylsulfanyl) -1 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H- 1,2,4-triazole, (1.061) 5- (allylsulfanyl) -1 - {[rel (2R, 3R) -3- (2- chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (1.062) 5- (allylsulfanyl) -1- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (1.063) N '- (2,5-dimethyl-) 4 - {[3- (1,1,2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.064) N '- (2,5-dimethyl-4 - {[3 - (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) - N -ethyl-N-methylimidoformamide, (1.065) N '- (2,5-dimethyl-4 - {[3- (2,2,3 , 3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.066) N '- (2,5-dimethyl-4 - {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N ethyl N-methylimidoformamide, (1.067) N '- (2,5-dimethyl-4- {3 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N- methylimidoformamide, (1.068) N '- (2,5-dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.069) N' - (2,5-Dimethyl-4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.070) N '- (2.5 Dimethyl 4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.071) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (1.072) N '- (4 - {[3- (Difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1073) N' - (4- {3 - [(Difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide; (1.074) N '- [5-bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridine 3-yl] -N-ethyl-N-methylimidoformamide, (1.075) N '- {4 - [(4,5-dichloro-1,3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} N-ethyl-N-methylimidoformamide, (1.076) N '- {5-bromo-6 - [(1R) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N- ethyl N -methylimidoformamide, (1.077) N '- {5-bromo-6 - [(1S) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N -methylimidoformamide, (1.078) N '- {5-bromo-6 - [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.079) N'- {5-Bromo-6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methyl-pyridin-3-yl} -N-ethyl-N-methylimidoformamide , (1080) N '- {5-Bromo-6- [1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide. 2) inhibitors of the respiratory chain on complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr , (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer  1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.016) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyrazolium, (2.021) sedaxanes, (2.022) 1,3-dimethyl- N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N - [(3R) - 1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N - [(3S) -1,1 , 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3- (trifluoromethyl) -N- [2'- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6- (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-indene-4 -yl) benzamide, (2.027) 3- (D. ifluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.028) 3- (difluoromethyl) - 1-methyl-N - [(3R) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.029) 3- (difluoromethyl) 1-methyl-N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.030) 3- (difluoromethyl ) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.031) 3- ( Difluoromethyl) -N - [(3R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide, ( 2.032) 3- (difluoromethyl) -N - [(3S) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole 4-carboxamide, (2.033) 5,8-difluoro-N- [2- (2-fluoro-4 - {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2.034) N - (2-Cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N- (2-tert butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazol-4- carboxamide, (2.036) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N- (5-chloro 2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.039) N - [(1R, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro -1,4-methanonaphthalene-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.040) N - [(1S, 4R) -9- (dichloromethylene) -1, 2,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.041) N- [1- (2,4-) Dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.042) N- [2-chloro-6- (trifluoromethyl) benzyl] -N- cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl 3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N- [5-chloro-2- (tri fluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1 methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6 -isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl -3- (difluoromethyl) -5-  fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,050) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) 1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-1H- pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N- (2- cyclopropyl-5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H pyrazoles-4-carboxamide. 3) respiratory chain inhibitors on complex III, for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) enoxastrobin, (3,009) famoxadone, (3,010) fenamidone, (3,011) flufenoxystrobin, (3,012) fluoxastrobin, (3,013) kresoxime methyl, (3,014) metominostrobin, (3,015) orysastrobin, (3,016) picoxystrobin, (3,017) pyraclostrobin, (3,018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E) -2- {2 - [({[(1E) -1- (3 - {[(E) -1-Fluoro-2-phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.022) (2E, 3Z) -5 - {[1- (4-chlorophenyl) -1H-pyrazole] 3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3.023) (2R) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2- methoxy-N-methylacetamide, (3.024) (2S) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.025) (3S, 6S, 7R, 8R ) -8-benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-m ethoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl-2-methylpropanoate, (3.026) 2- {2 - [(2,5-dimethylphenoxy ) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.027) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamido-2-hydroxybenzamide, (3.028) (2E, 3Z) - 5 - {[1- (4-Chloro-2-fluorophenyl) -1H-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide. 4) inhibitors of mitosis and cell division, for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3-Chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4.012) 4- (2-bromo 4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4- (2-bromo-4-fluorophenyl) -N- (2- bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1,3-dimethyl- 1H-pyrazol-5-amine, (4.015) 4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, ( 4.016) 4- (2-bromo-4-fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,017) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4- (2-chloro-4-fl uorphenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4- (2-chloro-4-fluorophenyl) -N- (2-chloro-6 -fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4- (2-chloro-4-fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H-  pyrazol-5-amine, (4.021) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4- (4 -Chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (4.023) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3 -dimethyl-1H-pyrazol-5-amine, (4.024) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.025 ) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine. 5) Compounds capable of multisite activity, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride , (5.009) copper (2+) sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017) Copper-oxine, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram. 6) Compounds capable of inducing host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil. 7) inhibitors of amino acid and / or protein biosynthesis, for example, (7,001) cyprodinil, (7,002) kasugamycin, (7,003) kasugamycin hydrochloride hydrate, (7,004) oxytetracycline (7,005) pyrimethanil, (7,006) 3- (5-fluoro) 3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl) quinoline. (8) Inhibitors of ATP production, for example, (8,001) silthiofam. 9) inhibitors of cell wall synthesis, for example, (9,001) benthiavalicarb, (9,002) dimethomorph, (9,003) flumorph, (9,004) iprovalicarb, (9,005) mandipropamide, (9,006) pyrimorph, (9,007) valproate, (9,008) (2E) -3 (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one. 10) Inhibitors of lipid and membrane synthesis, for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) tolclofos-methyl. 11) Inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl} carbamate. 12) inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam). 13) inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin. 14) compounds which may act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap. 15) Further compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) Cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil , (15,010) Cyprosulfamide, (15,011) Flutianil, (15,012) Fosetyl-aluminum, (15,013) Fosetyl-calcium, (15,014) Fosetyl-sodium, (15,015) Methylisothiocyanate, (15,016) Metrafenone, (15,017) Mildiomycin, (15,018) Natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphonic acid and its salts, (15.026) propamocarb -fosetylate, (15.027) pyriofenone (Chlazafenone) (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1- (4- {4 - [(5R) -5- (2,6-difluorophenyl) - 4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H- pyrazol-1-yl] ethanone, (15.032) 1- (4- {4 - [(5S) -5- (2,6-diflu orphenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) - 1H-pyrazol-1-yl] ethanone, (15.033) 2- (6-benzylpyridin-2-yl) quinazoline, (15.034) 2,6-dimethyl-1H, 5H- [1,4] dithiino [2,3- c: 5,6-c '] dipyrrol-1,3,5,7 (2H, 6H) -tetrone, (15,035) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] - 1- [4- (4- {5- [2- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazole -2-yl) piperidin-1-yl] ethanone, (15.036) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2 -chloro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine-1 yl] ethanone, (15.037) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2-fluoro-6- (prop-2 -in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.038) 2- [6- (3-Fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (15.039) 2 - {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl ) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl mead hanesulfonate, (15.040) 2 - {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -1, 3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (15.041) 2- {2 - [(7,8-Difluoro-2-methylquinoline 3-yl) oxy] -6-fluorophenyl} propan-2-ol, (15.042) 2- {2-Fluoro-6 - [(8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propane 2-ol, (15.043) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -1,3- thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (15.044) 2- {3- [2- (1 - {[3,5- Bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} phenyl methanesulfonate, (15.045) 2-phenylphenol and its salts, (15.046) 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.047) 3- ( 4,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.048) 4-Amino-5-fluoropyrimidin-2-ol (Tautomeric form: 4-amino-5-fluoropyrimidine) 2 (1H) -one), (15.049) 4-oxo-4 - [(2-phenylethyl) amino] butadiene acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2 sulfonohydrazide, (15.052) 5-Fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, (15.053) 5-Fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, ( 15.054) 9-Fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro-1,4-benzoxazepine, (15,055) but-3-yn-1-yl {6- [ ({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.056) ethyl (2Z) -3-amino -2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059)  Quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2: 1), (15.061) tert -butyl {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate. Biological Pesticides as Mixture Components The compounds of formula (I) may be combined with biological pesticides. Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites. Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides. Examples of such bacteria which can be used as biological pesticides are: Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus, strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus, especially strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397 ), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (Serotype H-14), strain AM65 -52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232). Examples of fungi and yeasts which can be used as biological pesticides are: Beauveria bassiana, especially strain ATCC 74040, Coniothyrium minitans, especially strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new : Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC  20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain V117b, Trichoderma atroviride, in particular strain SC1 (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM I-952). Examples of viruses that can be used as biological pesticides are: Adoxophyes orana (apple peel wrapper) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African cotton worm) NPV. It also includes bacteria and fungi that are added as "inoculant" plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples include: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., Especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp. , Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp. Examples of plant extracts and such products. which are formed by microorganisms, including proteins and secondary metabolites that can be used as biological pest control agents are: Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen , Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Sa pontine extract), pyrethrum / pyrethrin, Quassia amara, Quercus, Quillaja, Regalia, "Requiem ™ insecticide", rotenone, Ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, veratrine, Viscum album, Brassicacaeen extract, in particular rapeseed or mustard powder. Safeners as Mixture Components The compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (- ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS  129531-12-0), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -1,3 oxazolidine (CAS 52836-31-4). Plants and Plant Parts According to the invention, all plants and plant parts can be treated. Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes). 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 can not be protected by plant breeders' rights. Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants. Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, nebulization, scattering, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping. As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, 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. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are plants with new ones  Traits obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes. Transgenic Plant, Seed Treatment and Integration Events Among the preferred transgenic (genetically engineered) plants or plant species to be treated according to the invention are any plants which have obtained genetic material through the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z. By toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) are produced in the plants, also an increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z. For example, systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails. Crop protection treatments The treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg. By dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen),  Drip irrigation and in propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to apply the compounds of formula (I) by the ultra-low-volume method or to inject the use form or the compound of the formula (I) itself into the soil. A preferred direct treatment of the plants is foliar application, i. H. the compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest. In the case of systemically active substances, the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, i. H. the compounds of the formula (I) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In water rice crops this may also be by metered addition of the compound of formula (I) in a solid form (eg as granules) into a flooded paddy field. Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to constant improvement. Nevertheless, the treatment of seeds presents a number of problems that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also incorporate the intrinsic insecticidal or nematicidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with a minimum of pesticide use. The present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I). The method according to the invention for the protection of seeds and germinating plants from attack by pests further comprises a method in which the  Seed simultaneously in one operation or sequentially treated with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component. The invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention. The invention also relates to seed treated at the same time with a compound of formula (I) and a mixture component. The invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component. For seeds which have been treated at different times with a compound of formula (I) and a mixture component, the individual substances may be present in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed. One of the advantages that occurs when a compound of formula (I) acts systemically is that treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted. Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed. Compounds of the formula (I) may also be used in combination with signal technology agents, whereby a better colonization with symbionts, such as rhizobia,  Mycorrhiza and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation. The compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of seeds of cereals (such as wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice. As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) is also of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide having in particular insecticidal or nematicidal properties. The heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis. In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp. For example, seed may be used that has been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming. In the case of rice seeds, it is also possible to use seeds that have been soaked, for example, in water to a certain stage of the rice embryo ("Pigeon Breast Stage"), which stimulates germination and a more uniform emergence. In general, when treating seed, care must be taken to ensure that the amount of compound of formula (I) and / or other additives applied to the seed is not such as to affect the germination of the seed or to damage the resulting plant becomes. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.  The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art. The compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations. These formulations are prepared in a known manner by mixing the compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water. Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes. Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates. Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates. Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate.  Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica. Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. Gibberellins which may be present in the seed dressing formulations which can be used according to the invention are preferably the gibberellins A1, A3 (= gibberellic acid), A4 and A7, the gibberellic acid is particularly preferably used. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol.2, Springer Verlag, 1970, pp. 401-412). The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds. Thus, the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of maize, rice, rapeseed, peas, beans, cotton , Sunflower, soy and beet or vegetable seed of various nature. The seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants. For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom by the addition of water, all mixing devices which can usually be used for the dressing can be considered. Specifically, in the pickling process, the seed is placed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed. Optionally, a drying process follows. The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed. The application rates at the connection  of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed. Animal health In the field of animal health, d. H. In the veterinary field, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects or acarids. In the field of veterinary medicine, the compounds of formula (I), which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development. Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees. The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish. In a particular embodiment, the compounds of formula (I) are administered to mammals. According to another specific embodiment, the compounds of formula (I) are administered to birds, namely caged birds or, in particular, poultry. By using the compounds of formula (I) for the control of animal parasites disease, deaths and reductions (in meat, milk, wool, hides, eggs, honey and the like) are to be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable. With regard to the field of animal health, the term "controlling" or "controlling" in the present context means that the compounds of formula (I) effectively affect the appearance of the respective parasite in an animal infected with such parasites to a harmless extent , is reduced. More specifically, "combating" in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its replication.  For example, the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium Spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp. , Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests and hygiene pests from the order Blattarida. Furthermore, in the arthropods, the following Akari can be mentioned by way of example: From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp. , from the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp , Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp. Examples of parasitic protozoa include, but are not limited to: Mastigophora (Flagellata), such as:  Metamonada: from the order Diplomonadida for example Giardia spp., Spironucleus spp. Parabasala: from the order Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Euglenozoa: from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp. Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp. Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; from the order Piroplasmida z. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida z. Balantidium spp., Buxtonella spp. Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp. Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes). Exemplary helminths include, but are not limited to, monogenea: e.g. For example: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .; Cestodes: from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. For example, from the order Cyclophyllida: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp. , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp. Trematodes: from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyricum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp.,  Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp , Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp. Nematodes: from the order Trichinellida for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. For example, from the order Tylenchida: Micronema spp., Parastrangyloides spp., Strongyloides spp. From the order Rhabditina for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp. , Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp. , Ollulanus spp .; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp , Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp. For example, from the order Spirurida: Acanthocheilonema spp., Anisakis spp., Ascaridia spp .; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp .; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp .; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp , Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp., From the order Polymorphida for example: Filicollis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. Pentastoma: from the order Porocephalida for example Linguatula spp.  In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically. Thus, one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals. Another aspect relates to the compounds of formula (I) for use as antiendoparasitic. Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic agents, in particular for use as nematicide, platelet minthicide, acanthocephalicide or pentastomicide. Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic. Another aspect relates to the compounds of formula (I) for use as anti-topazarasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide. Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of a pharmaceutically acceptable excipient (eg, solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg, surfactants), especially one Pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations. A related aspect of the invention is a method of making a veterinary formulation as described herein which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, especially pharmaceutically acceptable excipients conventionally used in veterinary formulations; or conventionally used in veterinary formulations. Another special aspect of the invention are veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, especially selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal,  insecticidal and acaricidal formulations according to the aspects mentioned, as well as processes for their preparation. Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a non-human Animal that needs it. Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, the same requirement. Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal. In the present veterinary or veterinary context, the term "treatment" includes prophylactic, metaphylactic and therapeutic treatment. In a particular embodiment, mixtures of at least one compound of formula (I) with other active ingredients, especially endo and ectoparasiticides, are provided herein for the veterinary field. In the animal health field, "blending" not only means that two (or more) different active ingredients are formulated in a single formulation and used together, but also refers to products comprising separate formulations for each active ingredient. Accordingly, if more than two drugs are to be used, all drugs can be formulated in a single formulation or all drugs can be formulated in separate formulations; Also conceivable are mixed forms in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow the separate or sequential use of the active substances in question. The active ingredients specified herein by their "common name" are known and described, for example, in the "Pesticide Manual" (see above) or searchable on the Internet (e.g., http://www.alanwood.net/pesticides). Exemplary agents from the group of ectoparasiticides as a mating agent include, but are not limited to, the insecticides and the acaricides detailed above  one. Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of oxidative phosphorylation by disrupting the proton gradient; (14) blocker of the nicotinic acetylcholine receptor channel; (15) inhibitors of chitin biosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1; (17) molting disruptor (especially in dipterans, i.e., two-winged); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) blocker of the voltage-dependent sodium channel; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators; Active substances with unknown or non-specific mechanisms of action, eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite; Compounds from other classes, e.g. Butacarb, dimetilane, cloethocarb, phosphocarb, pirimiphos (- ethyl), parathion (-ethyl), methacrifos, isopropyl-o-salicylate, trichlorofon, sulprofos, propaphos, sebufos, pyridathione, prothoate, dichlorofenthione, demeton-S-methylsulfone, isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autothiofos, Aromfenvinfos (-methyl), Azinphos (-ethyl), Chlorpyrifos (- ethyl), Fosmethilane, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos; Organochlorine compounds, e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Pyrethroids, e.g. G. (Cis, trans) metofluthrin, profuthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin, clocythrin , Cyhalothrin (lambda), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs), neonicotinoids, e.g. B. Nithiazine  Dicloromezotiaz, triflumezopyrim macrocyclic lactones, e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime, triphene, epofenone, diofenolane; Biologicals, hormones or pheromones, for example natural products, e.g. Thuringiensin, codlemon or neem components dinitrophenols, e.g. Dinocap, dinobuton, binapacryl; Benzoylureas, eg. As fluazuron, penflurone, amidine derivatives, z. Chormorman, cymiazole, demiditraz hive varroa acaricides, for example organic acids, e.g. Formic acid, oxalic acid. Exemplary agents from the group of endoparasiticides, as a mixture partner, include, but are not limited to, anthelmintic agents and antiprotozoal agents. The anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestotic agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably cyclic depsipetides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of tetrahydropyrimidines for example: Morantel, Pyrantel, Oxantel; from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of aminophenylamidines, for example: amide shell, deacylated amide shell (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: Monepantel;  from the class of the Paraherquamide, for example: Paraherquamid, Derquantel; from the class of salicylanilides for example: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, nicolofolane, meniclopholan; from the class of organophosphates, for example: trichlorophone, naphthalofos, dichlorvos / DDVP, crufomat, coumaphos, haloxone; from the class of piperazinones / quinolines for example: praziquantel, epsiprantel; from the class of piperazines for example: piperazine, hydroxyzine; from the class of tetracyclines for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes, for example: bunamidine, niridazole, resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetoline, emetine, diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium, amoscanate, clorsulon. Antiprotozoal agents, including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides, for example: imidocarb; from the class of nitrofurans, for example: nifurtimox;  from the class of quinazolinone alkaloids, for example: halofuginone; from various other classes for example: oxamniquine, paromomycin; from the class of vaccines or antigens from microorganisms for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus , In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners can optionally form salts with suitable bases or acids. Vector Control The compounds of formula (I) can also be used in vector control. A vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes). Examples of vectors and their transmitted diseases or pathogens are: 1) mosquitoes - anopheles: malaria, filariasis; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of other worms; - Aedes: yellow fever, dengue fever, other viral diseases, filariasis; - Simulia: transmission of worms, in particular Onchocerca volvulus; - Psychodidae: transmission of leishmaniasis 2) lice: skin infections, epidemic typhus; 3) fleas: plague, endemic typhus, tapeworms; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases; 5) mites: acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis;  6) Ticks: Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis. Examples of vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes. Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans. Vector control is also possible when the compounds of formula (I) are resistance-disrupting. Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the protection of materials and materials. Protection of Technical Materials The compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma. Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred. In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide. In a further embodiment, the compounds of formula (I) are present as a ready-to-use pest control agent, i. h., They can be applied to the appropriate material without further changes. As further insecticides or fungicides, in particular those mentioned above come into question. Surprisingly, it has also been found that the compounds of formula (I) for protection against fouling of objects, in particular of hulls, sieves, nets, structures, quays  and signaling equipment, which come in contact with sea or brackish water, can be used. Likewise, the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents. Control of animal pests in the hygiene sector The compounds of formula (I) are useful in the control of animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry. To combat animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. Preferably, they are used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development. These pests include, for example, pests of the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda. The application is carried out for example in aerosols, non-pressurized sprays, z. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations. Explanation of the Processes and Intermediates: The compounds of the formula (I) according to the invention can be obtained by the processes shown in the following Schemes: Process A The compounds of the formula (Ic) according to the invention indicated in Process A, in which V1 and V2 are oxygen, can be prepared by the sequence of literature methods according to the following scheme.
(II) (III) (IV)  (II) (III) (IV)
Schritt 3 step 3
Schritt 6 Step 6
Y = Y =
Die Reste R1, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen, wobei Q1 zum Rest des Moleküls C-C-verknüpft ist. X steht - sofern im Schema nicht weiter eingeschränkt - für Halogen, insbesondere für Chlor, Brom oder Iod. R2 steht für Wasserstoff. BOC = tert-Butyl-oxy-carbonyl. Die Erfindung betrifft auch die Zwischenprodukte der allgemeinen Formeln (VII), (VIII), (IX) und (X), wobei R1, R3, R4, R5 und R6 die oben beschriebenen Bedeutungen haben, R2 für Wasserstoff steht, X für Halogen steht und Y für steht. Schritt 1: 4-Hydroxypyridin-2,6-dicarbonsäuren der allgemeinen Formel (II) eignen sich als Ausgangsstoffe für die Herstellung der Dialkylester der Formel (III) nach literaturbekannten Methoden. Sie sind teilweise kommerziell erhältlich, z.B. 4-Hydroxypyridin-2,6-dicarbonsäure (R5 = R6 = Wasserstoff), oder lassen sich nach bekannten Methoden aus kommerziell verfügbaren Synthonen darstellen, wie beispielsweise aus entsprechenden substituierten 4-Chlorpyridinen für 3,5-Dichlor-4-hydroxypyridin-2,6-dicarbonsäure (R5 = R6 = Chlor) nach der in US3651070 beschrieben Synthese. Die Hydroxyfunktion der 4-Hydroxypyridin-2,6-dicarbonsäuren (II) lässt sich beispielsweise in Analogie zu den in US6355653 oder US2004/29851 beschriebenen Verfahren in Gegenwart von Phosphorpentabromid in geeigneten inerten Lösungsmitteln, z. B. Tetrachlorkohlenstoff oder Chlorbenzol, in den entsprechenden Bromsubstituenten überführen. Durch Quenchen des Reaktionsgemisches mit einem Alkohol, z. B. Methanol im Falle des Verfahrens nach US2004/29851, wird hierbei direkt der Dialkyl-ester der Formel (III) erzeugt. Schritt 1a: Die Hydroxyfunktion der 4-Hydroxypyridin-2,6-dicarbonsäuren (II) lässt sich ähnlich zu Schritt 1 auch in den entsprechenden Chlorsubstituenten überführen. Ein geeignetes Verfahren für die Umsetzung mit Thionylchlorid in einem geeigneten inerten Lösungsmittel, wie z. B. Dimethylformamid, findet sich z. B. in US2014/336373. Alternativ kann Schritt 1a auch durch Umsetzung von (II) mit Phosphorpentachlorid in einem geeigneten inerten Lösungsmittel, z. B. Tetrachlorkohlenstoff, und anschließender Umsetzung mit einem Alkohol, z. B. Methanol in den entsprechenden Dialkyl-ester der Formel (IIa) überführt werden (vergleiche in Analogie z. B. Tetrahedron, 2005, 61, 1755-1763). Schritt 1b: Eine Überführung des Chlorsubstituenten der Verbindung (IIa) in Iod, resultierend in der entsprechenden Verbindung der Formel (III) mit X = I, gelingt nach literaturbekannten Methoden (vergleiche in Analogie z. B. Tetrahedron, 2005, 61, 1755-1763) beispielsweise durch Umsetzung von (IIa) mit Natriumiodid in geeigneten inerten Lösungsmitteln, z. B. Acetonitril. Einige 2,6-Dialkyl-4-halopyridin-2,6-dicarboxylate der Formel (III) sind literatur bekannt und können auch aus 4-Amino- oder 4-Halopyridinen nach bekannten Methoden hergestellt werden. Literatur bekannt sind z.B. Diethyl-3,5-dichlor-4-iodpyridin-2,6-dicarboxylat (X = Iod, Alkyl = Ethyl, R5 = R6 = Chlor) in DE579225 und Dimethyl-3,4,5-trichlorpyridin-2,6-dicarboxylat (X = Chlor, Alkyl = Methyl, R5 = R6 = Chlor) in US3637716. Beispielsweise eignet sich Dimethyl-4-amino-3-cyanopyridin-2,6- dicarboxylat (Alkyl = Methyl, R5 = Cyano, R6 = Wasserstoff) für die Herstellung verschiedener Dimethyl-3-cyano-4-halogenpyridin-2,6-dicarboxylaten (X = Halogen, Alkyl = Methyl, R5 = Cyano, R6 = Wasserstoff), z. B. nach ACS Med. Chem. Lett.2014, 5(8), 921-926, WO2007/093901 oder Tet. Let. 2011, 52(44), 5728-5732. Schritt 2: Dialkyl-ester der Formel (III) lassen sich durch Verseifung mit Hilfe einer Base, wie z.B. Kaliumhydroxid, in geeigneten inerten Lösungsmitteln oder Lösungsmittelgemischen, wie z. B. Methanol/Dichlormethan 10:1 in die entsprechenden Monoalkylester der Formel (IV) überführen (vergleiche hierzu EP 2017279). Schritt 3: Die Säurefunktion der unter Schritt 2 erhaltenen Monoalkylester kann weiterhin nach literaturbekannten Verfahren, z. B. gemäß EP 2017279, durch Curtius-Umlagerung, beispielsweise durch Umsetzung mit Diphenyl-phosphorylazid in geeigneten inerten Lösungsmitteln, wie z. B. Dioxan, und unter Anwesenheit von t-Butanol und Triethylamin, in eine t-Butyl-oxy-carbonyl-(BOC)-geschützte Aminogruppe überführt werden, wodurch Verbindungen der Formel (V) erhalten werden. Schritt 4: Zur Überführung der Verbindungen der Formel (V) in die analogen Verbindungen der Formel (VI) lässt sich die BOC-Schutzgruppe durch Umsetzung von (V) mit einer Säure, z.B. Trifluoressigsäure in einem geeigneten inerten Lösungsmittel, z. B. Chloroform oder Dichlormethan, abspalten (vergleiche hierzu EP 2017279). Schritt 5: Die Acylierung der Verbindungen der Formel (VI) zu Verbindungen der Formel (VII) gelingt nach literaturbekannten Verfahren, wie z. B. durch die Umsetzung von (VI) mit einem geeigneten Säurechlorid in Anwesenheit geeigneter Basen, z. B. Pyridin, Triethylamin oder Kaliumcarbonat, in einem geeigneten inerten Lösungsmittel, wie z. B. Dichlormethan oder 2-Butanon. Analoge Verfahren werden z. B. beschrieben in EP1714966, US5403816 oder WO2004/35545. Alternativ lassen sich Verbindungen der Formel (VII) auch durch Umsetzung von (VI) mit Carbonsäuren in Anwesenheit geeigneter Kupplungsreagenzien, z. B. HATU (O-(7-Azabenzotriazol-1- yl)-N,N,N′,N′-tetramethyluronium-hexafluorphosphat]) oder EDCI (1-Ethyl-3-(3- dimethylaminopropyl)carbodiimid), und geeigneter Basen, z. B. Triethylamin oder N,N- Diisopropylethylamin, in geeigneten inerten Lösungsmitteln wie z. B. DMF (Dimethylformamid) oder Dichlormethan, erhalten (vergleiche in Analogie z. B. US2011/301181 oder WO2007/122258). Die Carbonsäuren sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Schritt 6: Die Spaltung der Esterfunktion in Verbindungen der Formel (VII) zur Herstellung von (VIII) gelingt gemäß literaturbekannter Methoden (vergleiche in Analogie z. B. US2007/213349, WO2015/150440 oder US2011/301181) durch Umsetzung mit einer geeigneten Base, z. B. Lithiumhydroxid oder Natriumhydroxid, in geeigneten wässrigen Lösungsmittelgemischen, z. B. Wasser/THF, Wasser/Methanol oder Wasser/Dioxan, oder Wasser. Schritt 7: Die erhaltenen Carbonsäuren der Formel (VIII) lassen sich mit primären oder sekundären Aminen, Alkoxyaminen oder Hydrazinen in Anwesenheit geeigneter Kupplungsreagenzien, z. B. HATU oder EDCI, und geeigneter Basen, z. B. Triethylamin oder N,N-Diisopropylethylamin, in geeigneten inerten Lösungsmitteln wie z. B. DMF oder Dichlormethan, zu den entsprechenden Amiden (IX) umsetzen (vergleiche in Analogie z. B. US2011/301181 oder WO2007/122258). Alternativ kann eine Umsetzung von Pyridin-2-carbonsäuren zu (IX) auch nach literaturbekannten Methoden (vergleiche in Analogie z. B. Bioorganic and Medicinal Chemistry Letters, 2006, Vol. 16, #10, Seiten 2689 - 2692) auch durch Aktivierung zum Säurechlorid, z. B. durch Reaktion mit Oxalyldichlorid oder Thionylchlorid, in einem inerten Lösungsmittel wie z. B. Dichlormethan (ggf. mit katalytischen Mengen DMF) und anschließender Umsetzung mit dem entsprechenden Amin in Anwesenheit einer Base, z. B. Triethylamin oder N,N-Diisopropylethylamin , in einem geeigneten inerten Lösungsmittel, wie z. B. Dichlormethan, erfolgen. Die Amine, Alkoxyamine und Hydrazine sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Schritt 8: Zum Erhalt der entsprechenden Boronsäuren oder Dioxoborolan-Derivate (X) aus den halogenierten Verbindungen (IX) können ebenfalls literaturbekannte Methoden angewendet werden. So lassen sich z. B. 4-Brom-pyridin-2-carboxamide durch Umsetzung mit Bis(pinacolato)diboron [4,4,4',4',5,5,5',5'- Octamethyl-2,2'-bis-1,3,2-dioxaborolan] in Anwesenheit von Kaliumacetat und geeigneten Katalysatoren, wie z. B. Dichlor(1,1'-bis(diphenylphosphanyl)ferrocen)-palladium(II) [ggf. als Dichlormethan-Addukt] oder Dichlor-bis(triphenylphosphin)-palladium(II), in geeigneten inerten Lösungsmitteln, z. B. Dimethylformamid, Dioxan oder Toluol und unter Inertatmosphäre in die entsprechenden Boronsäure- oder Dioxoborolan-Verbindungen überführen (vergleiche in Analogie z. B. US2004/67982, US2007/197553 oder WO2011/159554). Um Verbindungen der Formel (IX) oder (X) zu erhalten, ist der Schritt 5 mit der Sequenz aus Schritt 6 & 7 ggf. auch in der Reihenfolge austauschbar. Schritt 9: Dioxoborolan-pyridine oder Pyridinboronsäuren der Formel (X) lassen sich mit Aryl- oder Hetaryl- halogeniden, insbesondere Chloriden, Bromiden oder Iodiden, oder mit Aryl- oder Hetaryl-triflaten, nach bekannten Methoden zu Aryl- bzw. Hetaryl-pyridinen kuppeln. Diese Umsetzung kann in einem geeigneten Lösungsmittel, z. B. Dimethylformamid, oder einem geeigneten Lösungsmittelgemisch, wie z. B. Dimethylformamid/Wasser, 1,4-Dioxan/Wasser oder Isopropanol/Toluol/Wasser, durch Palladium- Katalyse, z.B. mit Tetrakis(triphenylphosphin)-palladium(0) [vergleiche z. B. WO2014/170821], Tris- (dibenzylideneaceton)-dipalladium(0) [vergleiche z. B. WO2013/61081] oder (1,1'-Bis(diphenyl- phosphino)-ferrocene)-palladium(II)-dichlorid [vergleiche z. B. US2011/9410] als Palladium-Quelle und in Anwesenheit einer geeigneten Base, z. B. Kaliumcarbonat oder Natriumcarbonat, erfolgen. Auf diese Weise lassen sich auch Verbindungen der Formel (I-c) erhalten. Schritt 9a: Halogenierte Pyridine der Formel (IX) lassen sich mit Aryl- und Hetaryl-boronsäuren oder Aryl- und Hetarylboronestern nach bekannten Methoden zu Aryl- bzw. Hetaryl-pyridinen kuppeln. Diese Umsetzung kann in einem geeigneten Lösungsmittel, z. B. Dimethylformamid, oder einem geeigneten Lösungsmittelgemisch, wie z. B. Dimethylformamid/Wasser, 1,4-Dioxan/Wasser oder Isopropanol/Toluol/Wasser, durch Palladium-Katalyse, z.B. mit Tetrakis(triphenylphosphin)- palladium(0) [vergleiche z. B. US2015/210671], Tris-(dibenzylideneaceton)-dipalladium(0) [vergleiche z. B. WO2013/61081] oder (1,1'-Bis(diphenyl-phosphino)-ferrocene)-palladium(II)-dichlorid [vergleiche z. B. US2011/9410] als Palladium-Quelle und in Anwesenheit einer geeigneten Base, z. B. Kaliumcarbonat oder Natriumcarbonat, erfolgen. Auf diese Weise lassen sich auch Verbindungen der Formel (I-c) erhalten. Verfahren B Die in Verfahren B angegebenen erfindungsgemäßen Verbindungen der Formel (I-c), in welchen V1 und V2 für Sauerstoff stehen, können durch die Abfolge literaturbekannter Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is C-linked to the rest of the molecule. X is - unless further limited in the scheme - halogen, in particular chlorine, bromine or iodine. R2 stands for hydrogen. BOC = tert-butyl-oxy-carbonyl. The invention also relates to the intermediates of the general formulas (VII), (VIII), (IX) and (X), wherein R 1, R 3, R 4, R 5 and R 6 have the meanings described above, R 2 is hydrogen, X is halogen and Y for stands. Step 1: 4-hydroxypyridine-2,6-dicarboxylic acids of the general formula (II) are suitable as starting materials for the preparation of the dialkyl esters of the formula (III) by methods known from the literature. They are partially commercially available, for example 4-hydroxypyridine-2,6-dicarboxylic acid (R5 = R6 = hydrogen), or can be prepared by known methods from commercially available synthons, such as corresponding substituted 4-chloropyridines for 3,5-dichloro 4-hydroxypyridine-2,6-dicarboxylic acid (R5 = R6 = chlorine) according to the synthesis described in US3651070. The hydroxy function of 4-hydroxypyridine-2,6-dicarboxylic acids (II) can be determined, for example, in analogy to the processes described in US Pat. No. 6,353,553 or US2004 / 29851 in the presence of phosphorus pentabromide in suitable inert solvents, eg. As carbon tetrachloride or chlorobenzene, in the corresponding Bromsubstituenten. By quenching the reaction mixture with an alcohol, for. As methanol in the case of the method according to US2004 / 29851, in this case directly the dialkyl ester of the formula (III) is produced. Step 1a: The hydroxy function of 4-hydroxypyridine-2,6-dicarboxylic acids (II) can be converted into the corresponding chlorine substituents similarly to step 1. A suitable method for the reaction with thionyl chloride in a suitable inert solvent, such as. As dimethylformamide, z. In US2014 / 336373. Alternatively, step la may also be carried out by reacting (II) with phosphorus pentachloride in a suitable inert solvent, e.g. As carbon tetrachloride, and subsequent reaction with an alcohol, for. For example, methanol can be converted into the corresponding dialkyl ester of the formula (IIa) (compare, by analogy, for example, Tetrahedron, 2005, 61, 1755-1763). Step 1b: A conversion of the chlorine substituent of the compound (IIa) into iodine, resulting in the corresponding compound of the formula (III) where X = I, is possible by methods known from the literature (compare in analogy eg Tetrahedron, 2005, 61, 1755- 1763), for example by reaction of (IIa) with sodium iodide in suitable inert solvents, for. For example acetonitrile. Some 2,6-dialkyl-4-halopyridine-2,6-dicarboxylates of the formula (III) are known from the literature and can also be prepared from 4-amino- or 4-halopyridines by known methods. For example, diethyl 3,5-dichloro-4-iodopyridine-2,6-dicarboxylate (X = iodine, alkyl = ethyl, R 5 = R 6 = Chlorine) in DE579225 and dimethyl 3,4,5-trichloropyridine-2,6-dicarboxylate (X = chlorine, alkyl = methyl, R5 = R6 = chlorine) in US3637716. For example, dimethyl 4-amino-3-cyanopyridine-2,6-dicarboxylate (alkyl = methyl, R 5 = cyano, R 6 = hydrogen) is suitable for the preparation of various dimethyl-3-cyano-4-halopyridine-2,6-dicarboxylates (X = halogen, alkyl = methyl, R5 = cyano, R6 = hydrogen), for. B. after ACS Med. Chem. Lett.2014, 5 (8), 921-926, WO2007 / 093901 or Tet. Let. 2011, 52 (44), 5728-5732. Step 2: Dialkyl esters of the formula (III) can be obtained by saponification with the aid of a base, such as potassium hydroxide, in suitable inert solvents or solvent mixtures, such as. B. methanol / dichloromethane 10: 1 in the corresponding monoalkyl esters of the formula (IV) convert (see EP 2017279). Step 3: The acid function of the monoalkyl esters obtained in step 2 can furthermore be carried out by literature methods, for. B. according to EP 2017279, by Curtius rearrangement, for example by reaction with diphenyl phosphoryl azide in suitable inert solvents, such as. As dioxane, and in the presence of t-butanol and triethylamine, in a t-butyl-oxy-carbonyl (BOC) -protected amino group are converted, whereby compounds of formula (V) are obtained. Step 4: To convert the compounds of formula (V) into the analogous compounds of formula (VI), the BOC protecting group can be prepared by reacting (V) with an acid, eg trifluoroacetic acid, in a suitable inert solvent, e.g. As chloroform or dichloromethane, split (see EP 2017279). Step 5: The acylation of the compounds of formula (VI) to give compounds of formula (VII) succeeds by literature methods, such as. Example, by the reaction of (VI) with a suitable acid chloride in the presence of suitable bases, for. For example, pyridine, triethylamine or potassium carbonate, in a suitable inert solvent such. For example, dichloromethane or 2-butanone. Analogous methods are z. As described in EP1714966, US5403816 or WO2004 / 35545. Alternatively, compounds of formula (VII) may also be prepared by reacting (VI) with carboxylic acids in the presence of suitable coupling reagents, e.g. HATU (O- (7-azabenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate]) or EDCI (1-ethyl-3- (3-dimethylaminopropyl) carbodiimide), and more appropriate Bases, e.g. Triethylamine or N, N- Diisopropylethylamine, in suitable inert solvents such as. As DMF (dimethylformamide) or dichloromethane, obtained (compare in analogy, for example, US2011 / 301181 or WO2007 / 122258). The carboxylic acids are either commercially available or can be prepared by known methods. Step 6: The cleavage of the ester function in compounds of the formula (VII) for the preparation of (VIII) succeeds by reaction with a suitable base in accordance with methods known from the literature (cf., for example, US2007 / 213349, WO2015 / 150440 or US2011 / 301181) , z. As lithium hydroxide or sodium hydroxide, in suitable aqueous solvent mixtures, for. As water / THF, water / methanol or water / dioxane, or water. Step 7: The resulting carboxylic acids of formula (VIII) can be reacted with primary or secondary amines, alkoxyamines or hydrazines in the presence of suitable coupling reagents, e.g. HATU or EDCI, and suitable bases, e.g. For example, triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such. As DMF or dichloromethane, to the corresponding amides (IX) implement (see in analogy, for example, US2011 / 301181 or WO2007 / 122258). Alternatively, a reaction of pyridine-2-carboxylic acids to (IX) can also be carried out by methods known from the literature (cf., for example, in analogy to, for example, Bioorganic and Medicinal Chemistry Letters, 2006, Vol. 16, # 10, pages 2689-2692) Acid chloride, e.g. B. by reaction with oxalyl or thionyl chloride, in an inert solvent such as. For example, dichloromethane (optionally with catalytic amounts of DMF) and subsequent reaction with the corresponding amine in the presence of a base, for. For example, triethylamine or N, N-diisopropylethylamine, in a suitable inert solvent such. For example, dichloromethane. The amines, alkoxyamines and hydrazines are either commercially available or can be prepared by known methods. Step 8: To obtain the corresponding boronic acids or dioxoborolane derivatives (X) from the halogenated compounds (IX), methods known from the literature can also be used. So can be z. B. 4-bromo-pyridine-2-carboxamides by reaction with bis (pinacolato) diboron [4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-1 , 3,2-dioxaborolane] in the presence of potassium acetate and suitable catalysts, such. B. dichloro (1,1'-bis (diphenylphosphanyl) ferrocene) palladium (II) [possibly as dichloromethane adduct] or dichloro-bis (triphenylphosphine) palladium (II), in suitable inert Solvents, eg. B. dimethylformamide, dioxane or toluene and under an inert atmosphere in the corresponding Boronsäure- or Dioxoborolan compounds convert (compare in analogy, for example, US2004 / 67982, US2007 / 197553 or WO2011 / 159554). In order to obtain compounds of the formula (IX) or (X), the step 5 with the sequence from step 6 & 7 is optionally also exchangeable in the sequence. Step 9: Dioxoborolan-pyridines or pyridinboronic acids of the formula (X) can be prepared by aryl or hetaryl halides, in particular chlorides, bromides or iodides, or by aryl or hetaryl triflates, according to known methods to aryl- or hetaryl-pyridines couple. This reaction can be carried out in a suitable solvent, e.g. As dimethylformamide, or a suitable solvent mixture, such as. As dimethylformamide / water, 1,4-dioxane / water or isopropanol / toluene / water, by palladium catalysis, eg with tetrakis (triphenylphosphine) palladium (0) [see, for. WO2014 / 170821], tris (dibenzylideneacetone) dipalladium (0) [see, e.g. WO2013 / 61081] or (1,1'-bis (diphenylphosphino) -ferrocenes) -palladium (II) dichloride [cf., for. US2011 / 9410] as a palladium source and in the presence of a suitable base, e.g. As potassium carbonate or sodium carbonate, take place. In this way, compounds of formula (Ic) can be obtained. Step 9a: Halogenated pyridines of the formula (IX) can be coupled with aryl- and hetaryl-boronic acids or aryl- and hetarylboronic esters by known methods to aryl- or hetaryl-pyridines. This reaction can be carried out in a suitable solvent, e.g. As dimethylformamide, or a suitable solvent mixture, such as. As dimethylformamide / water, 1,4-dioxane / water or isopropanol / toluene / water, by palladium catalysis, eg with tetrakis (triphenylphosphine) - palladium (0) [see, for. US2015 / 210671], tris (dibenzylideneacetone) dipalladium (0) [see, e.g. WO2013 / 61081] or (1,1'-bis (diphenylphosphino) ferrocenes) palladium (II) dichloride [see, e.g. US2011 / 9410] as a palladium source and in the presence of a suitable base, e.g. As potassium carbonate or sodium carbonate, take place. In this way, compounds of formula (Ic) can be obtained. Process B The compounds of the formula (Ic) according to the invention in which V1 and V2 represent oxygen can be prepared by the sequence of methods known from the literature in accordance with the following scheme.
Die Reste R1, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen, wobei Q1 zum Rest des Moleküls C-N-verknüpft ist. X steht für Halogen, bevorzugt für Brom oder Iod. R2 steht für Wasserstoff. Schritt 1: Eine Kupplung der halogenierten Pyridine der Formel (IX) mit NH-haltigen Heteroaromaten, wie z. B. Pyrrole, Imidazole oder Pyrazole, kann z. B. in Analogie zu US2013/165464 oder WO2012/64815 unter Inertgasatmosphäre durch Katalyse mit Kupfer(I)salzen, beispielsweise Kupfer(I)iodid, in Anwesenheit eines geeigneten Liganden, z. B. (trans)-N,N’-Dimethylcyclohexan-1,2-diamin oder R-(+)-Prolin, und einer geeigneten Base, z. B. Kaliumcarbonat, in einem geeigneten Lösungsmittel, wie z. B.1,4-Dioxan oder Dimethylsulfoxid, erfolgen, wodurch Verbindungen der Formel (I-c) erhalten werden. Verfahren C Die in Verfahren C angegebenen erfindungsgemäßen Verbindungen der Formel (I-c), in welchen V1 und V2 für Sauerstoff stehen, können durch die Abfolge literaturbekannter Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is C-N linked to the rest of the molecule. X is halogen, preferably bromine or iodine. R2 stands for hydrogen. Step 1: A coupling of the halogenated pyridines of the formula (IX) with NH-containing heteroaromatics, such as. As pyrroles, imidazoles or pyrazoles, z. Example, in analogy to US2013 / 165464 or WO2012 / 64815 under inert gas atmosphere by catalysis with copper (I) salts, such as copper (I) iodide, in the presence of a suitable ligand, for. B. (trans) -N, N'-dimethylcyclohexane-1,2-diamine or R - (+) - proline, and a suitable base, for. As potassium carbonate, in a suitable solvent, such as. B, 1,4-dioxane or dimethylsulfoxide, to give compounds of formula (I-c). Process C The compounds of the formula (I-c) according to the invention in which C 1 and V 2 are oxygen can be prepared by the sequence of methods known from the literature in accordance with the following scheme.
Die Reste R1, R2, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen. Die Erfindung betrifft auch die Zwischenprodukte der allgemeinen Formeln (XVI), (XVII) und (XVIII), wobei R2, R3, R4, R5, R6 und Q1 die oben beschriebenen Bedeutungen haben, wobei Q1 nicht für unsubstituiertes Phenyl und nicht für substituiertes oder unsubstituiertes Pyrazol steht. Schritt 1: Eine Kupplung der 2,6-Dichlor-4-iodpyridine der Formel (XIII) an der Position des Iods mit aromatischen oder heteroaromatischen Boronsäuren, Boronsäureestern bzw. Bisoxoborolanen zu Verbindungen der Formel (XIV) kann gemäß der unter Verfahren A, Schritt 9a, beschriebenen bekannten Methoden unter Verwendung geeigneter Katalysatoren, z. B. Tetrakis(triphenylphosphin)palladium(0), erfolgen. Weiterhin können Verbindungen der Formel (XIV) durch eine Kupplung der 2,6-Dichlor-4-iodpyridine an der Position des Iods mit NH-Heterozyklen in Analogie zu den unter Verfahren B, Schritt 1, beschriebenen bekannten Methoden [vergleiche dort z. B. US2013/165464] hergestellt werden, wobei die Bindung über den Stickstoff des Heterozyklus erfolgt. 2,6-Dichlor-4-iodpyridine der allgemeinen Formel (XIII) sind teilweise kommerziell erhältlich, wie z.B. 2,6-Dichlor-4-iodpyridin (R5 = R6 = Wasserstoff), 2,3,5,6-Tetrachlor-4-iodpyridin (R5 = R6 = Chlor) oder literaturbekannt oder können nach bekannten Methoden hergestellt werden. Beispielsweise kann das 2,6-Dichlor-5-fluor-4-iodnicotinonitril (R5 = Fluor, R6 = Cyano) nach der in WO2006/082392 beschriebenen Methode synthetisiert werden. Das 2,6-Dichlor-4-iod-3-methylpyridin (R5 = Methyl, R6 = Wasserstoff) kann beispielsweise aus 2,6-Dichlor-3-methylpyridin nach dem Protokoll in J. Med. Chem. 2011, 54(19), 6691-6703 hergestellt werden. Schritt 2: Die Vinylierung der Verbindungen der Formel (XIV) zu (XV) ist durch deren Umsetzung mit z. B. 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolan oder Trivinylboroxin in Analogie zu den unter Verfahren A, Schritt 9a, beschriebenen bekannten Palladium-katalysierten Methoden [vergleiche zusätzlich z. B. WO2011/54773 oder WO2009/24905] durchführbar. Auch ein Einsatz von Tributyl- vinyl-zinn als Vinyldonor ist literaturbekannt [vgl. z. B. Journal of Heterocyclic Chemistry, 2001, Vol. 38, # 5, Seiten 1039 - 1044]. Schritt 3: Die Vinylfunktion der unter Schritt 2 erhaltenen Verbindungen der Formel (XV) kann nach literaturbekannten Verfahren, z. B. gemäß WO2009/24905, durch geeignete Oxidationsmittel, z. B. Kaliumpermanganat, in geeigneten Lösungsmitteln bzw.–gemischen, z. B. Wasser/Aceton, in die entsprechende Carbonsäurefunktion überführt werden, wodurch Verbindungen der Formel (XVI) erhalten werden. Schritt 4: Die erhaltenen Carbonsäuren der Formel (XVI) lassen sich z. B. in Analogie zu den unter Verfahren A, Schritt 7, beschriebenen Methoden durch Kupplungsreagenzien oder nach Aktivierung, z. B. zum Carbonsäurechlorid, in die entsprechenden Amide der Formel (XVII) transformieren. Schritt 5: Zum Erhalt von Verbindungen der Formel (XVIII) aus den Vorstufen (XVII) können ebenfalls literaturbekannte Methoden verwendet werden. So erfolgt z. B. gemäß WO2009/147190 die Einführung von primären Aminen an der Position des Chlors in 2-Chlorpyridinen durch direkte Umsetzung beider Reaktionspartner unter Erhitzen in einem geeigneten Lösungsmittel, z. B. Wasser oder Dimethylsulfoxid, ggf. in Anwesenheit einer weiteren Base wie z. B. N,N-Diisopropylethylamin und ggf. unter erhöhten Druckbedingungen. Weiterhin können Verbindungen der Formel (XVIII) mit R2 = H durch Umsetzung von (XVII) mit Ammoniak nach literaturbekannten Verfahren erhalten werden. Diese Umsetzung kann mit wässrigem Ammoniak [vergleiche z. B. US2007/66644], oder mit wässrigem Ammoniak in einem geeigneten Lösungsmittel, z. B. Isopropanol [vergleiche z. B. WO2011/110575], ggf. in Anwesenheit von Kupfersalzen, z. B. Kupfer(II)sulfat [vergleiche z. B. US2009/162453] und ggf. unter erhöhtem Druck, erfolgen. Alternativ können Verbindungen der Formel (XVIII) durch Umsetzung von (XVII) mit primären Amiden oder primären Carbamaten nach literaturbekannten Verfahren erhalten werden. Diese Umsetzung kann in einem geeigneten Lösungsmittel, z. B. 1,4-Dioxan, durch Katalyse mit Tris- (dibenzylideneaceton)-dipalladium(0) [vergleiche z. B. US2013/165464] oder Palladium(II)-diacetat [vergleiche z. B. WO2011/137342 oder WO2014/114185] in Anwesenheit eines Phosphinliganden, z.B. Xantphos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene) oder Xphos (2-Dicyclohexylphosphino- 2′,4′,6′-triisopropylbiphenyl) und einer geeigneten Base, z. B. Cäsiumcarbonat, erfolgen. Schritt 6: Die Herstellung der Verbindungen der Formel (I-c) gelingt in Analogie zu den unter Verfahren A, Schritt 5, beschriebenen Methoden durch Umsetzung von (XVIII) mit einem geeigneten Säurechlorid in Anwesenheit geeigneter Basen, z. B. Pyridin, Triethylamin oder Kaliumcarbonat, in einem geeigneten inerten Lösungsmittel, wie z. B. Dichlormethan. Alternativ lassen sich Verbindungen der Formel (I-c) auch durch Umsetzung von (XVIII) mit Carbonsäuren in Anwesenheit geeigneter Kupplungsreagenzien, z. B. HATU oder EDCI, und geeigneter Basen, z. B. Triethylamin oder N,N-Diisopropylethylamin, in geeigneten inerten Lösungsmitteln wie z. B. DMF oder Dichlormethan, erhalten (vergleiche in Analogie z. B. US2011/301181 oder WO2007/122258). Verfahren D Die in Verfahren D angegebenen erfindungsgemäßen Verbindungen der Formel (I-c), in welchen V1 und V2 für Sauerstoff stehen, können durch die Abfolge literaturbekannter Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above. The invention also relates to the intermediates of general formulas (XVI), (XVII) and (XVIII), wherein R2, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is not unsubstituted phenyl and not substituted or unsubstituted pyrazole stands. Step 1: A coupling of 2,6-dichloro-4-iodopyridine of the formula (XIII) at the position of the iodine with aromatic or heteroaromatic boronic acids, boronic acid esters or bisoxoborolanes to compounds of formula (XIV) can be prepared according to the known methods described in Method A, step 9a, using suitable catalysts, for. As tetrakis (triphenylphosphine) palladium (0) occur. Furthermore, compounds of the formula (XIV) can be prepared by coupling the 2,6-dichloro-4-iodopyridines at the position of the iodine with NH heterocycles in analogy to the known methods described in process B, step 1 [cf. B. US2013 / 165464] are produced, wherein the binding is via the nitrogen of the heterocycle. 2,6-Dichloro-4-iodopyridines of the general formula (XIII) are in some cases commercially available, for example 2,6-dichloro-4-iodopyridine (R 5 = R 6 = hydrogen), 2,3,5,6-tetrachloro-4 -iodopyridine (R5 = R6 = chlorine) or known from the literature or can be prepared by known methods. For example, the 2,6-dichloro-5-fluoro-4-iodonicotinonitrile (R5 = fluorine, R6 = cyano) can be synthesized according to the method described in WO2006 / 082392. The 2,6-dichloro-4-iodo-3-methylpyridine (R5 = methyl, R6 = hydrogen) can be prepared, for example, from 2,6-dichloro-3-methylpyridine according to the protocol in J. Med. Chem. 2011, 54 (19 ), 6691-6703. Step 2: The vinylation of the compounds of formula (XIV) to (XV) by reacting with z. B. 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolan or trivinylboroxine in analogy to the methods described in Method A, step 9a, known palladium-catalyzed methods [see in addition z. WO2011 / 54773 or WO2009 / 24905] feasible. A use of tributyl vinyl tin as vinyl donor is also known from the literature [cf. z. Journal of Heterocyclic Chemistry, 2001, Vol. 38, # 5, pp. 1039-1044]. Step 3: The vinyl function of the obtained under step 2 compounds of formula (XV) can be prepared by literature methods, for. B. according to WO2009 / 24905, by suitable oxidizing agents, for. As potassium permanganate, in suitable solvents or mixtures, for. As water / acetone are converted into the corresponding carboxylic acid function, whereby compounds of formula (XVI) are obtained. Step 4: The resulting carboxylic acids of formula (XVI) can be z. B. in analogy to the methods described in Method A, step 7, by coupling reagents or after activation, for. To the carboxylic acid chloride, into the corresponding amides of formula (XVII). Step 5: To obtain compounds of formula (XVIII) from the precursors (XVII), methods known from the literature can also be used. So z. B. according to WO2009 / 147190 the introduction of primary amines at the position of the chlorine in 2-chloropyridines by direct reaction of both reactants with heating in a suitable solvent, for. As water or dimethyl sulfoxide, optionally in the presence of another base such. As N, N-diisopropylethylamine and optionally under elevated pressure conditions. Furthermore, compounds of the formula (XVIII) with R 2 = H can be obtained by reacting (XVII) with ammonia by methods known from the literature. This reaction can be carried out with aqueous ammonia [cf., for. US2007 / 66644], or with aqueous ammonia in a suitable solvent, e.g. B. isopropanol [see, for. WO2011 / 110575], optionally in the presence of copper salts, for. B. copper (II) sulfate [see, for. B. US2009 / 162453] and optionally under elevated pressure, take place. Alternatively, compounds of formula (XVIII) may be obtained by reaction of (XVII) with primary amides or primary carbamates according to methods known in the literature. This reaction can be carried out in a suitable solvent, e.g. As 1,4-dioxane, by catalysis with tris (dibenzylideneaceton) dipalladium (0) [see, for. B. US2013 / 165464] or palladium (II) diacetate [cf., for. WO2011 / 137342 or WO2014 / 114185] in the presence of a phosphine ligand, for example xantphos (4,5-bis (diphenylphosphino) -9,9-dimethylxanthene) or Xphos (2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl ) and a suitable base, e.g. As cesium carbonate, take place. Step 6: The preparation of the compounds of formula (Ic) is possible in analogy to the methods described in Method A, step 5, by reacting (XVIII) with a suitable acid chloride in the presence of suitable bases, for. For example, pyridine, triethylamine or potassium carbonate, in a suitable inert solvent such. For example, dichloromethane. Alternatively, compounds of formula (Ic) may also be prepared by reacting (XVIII) with carboxylic acids in the presence of suitable coupling reagents, e.g. HATU or EDCI, and suitable bases, e.g. For example, triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such. As DMF or dichloromethane obtained (compare in analogy, for example, US2011 / 301181 or WO2007 / 122258). Process D The compounds of the formula (Ic) according to the invention, in which V1 and V2 are oxygen, can be prepared by the sequence of methods known from the literature in accordance with the following: Scheme to be made.
(I-c) Die Reste R1, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen, wobei Q1 zum Rest des Moleküls C-C-verknüpft ist. X steht für Halogen oder für Trifluormethansulfonat. R2 steht für Wasserstoff. Die Erfindung betrifft auch die Zwischenprodukte der allgemeinen Formeln (XIX) und (XX), wobei R2 für Wasserstoff steht und R3, R4, R5, R6 und Q1 die oben beschriebenen Bedeutungen haben, wobei Q1 zum Rest des Moleküls C-C-verknüpft ist und nicht für unsubstituiertes Phenyl steht. Schritt 1 Die Pyridine der Formel (XIX) lassen sich beispielsweise über eine Michael-Reaktion von einem 1- (Cyanomethyl)pyridiniumhalogenid und einem ^, ^-ungesättigten Keton in Anwesenheit von Ammoniumacetat nach der sogenannten Kröhnke Pyridin-Synthese herstellen, wie sie in Synthesis 1976, 1-24 und Angew. Chem.196274, 811-817, beschrieben wird. Die literaturbekannte 6-Amino-3,5- dicyano-4-phenylpyridin-2-carbonsäure der Formel (XIX) (R2 = Wasserstoff; R5 = R6 = Cyano; Q1 = Phenyl) ist in Synth. Comm.1992, 22(14), 2053-2056 beschrieben. Die Ausgangsstoffe für die Kröhnke Synthese sind kommerziell erhältlich oder lassen sich leicht herstellen. 1-(Cyanomethyl)pyridiniumhalogenide sind in der Literatur bekannt; z.B. kann das 1- Cyanmethylpyridiniumiodid (X = Iod, R5 = R6 = Wasserstoff) durch Umsetzung von Pyridin, Chloracetonitril und Kaliumiodid hergestellt werden, wie in Helv. Chim. Act. 1996 79, 1192-1202, beschrieben; das 1-(1-Cyanethyl)pyridiniumtrifluoromethansulfonat (X = Trifluormethansulfonat (Triflat), R5 = R6 = Wasserstoff) kann aus Cyanhydrintriflat hergestellt werden, nach Eur. J. Org. Chem. 2012, 24, 4555-4564; die Synthese von 1-(Dicyanmethyl)pyridinium-Salzen ist in Chem. Ber. 1963, 96(11), 3044-3049 und J. Am. Chem. Soc.1965, 87/16), 3651-3656 beschrieben. Die benötigten ^, ^-ungesättigten Ketone können nach einer Reihe bekannter Methoden dargestellt werden; z.B. können 2-Oxo-4-arylbut-3-ensäuren (R6 = Wasserstoff) aus den entsprechenden Aldehyden durch Kondensation mit Ethylpyruvat in einem basischen Medium, wie beispielsweise in US2006/0020010 beschrieben, mit Hilfe von Natronlauge isoliert werden; für die Synthese von 3-Alkyl- 2-oxo-4-arylbut-3-ensäuren (R6 = Alkyl) können 2-Oxoalkansäuren (z.B. 2-Oxobutansäure für R6 = Methyl) mit aromatischen Aldehyden umgesetzt werden, wie in Tet. 1991, 47(43), 9019-9034, beschrieben wird. Schritt 2 Die erhaltenen Carbonsäuren der Formel (XIX) lassen sich z. B. in Analogie zu den unter Verfahren A, Schritt 7, beschriebenen Methoden durch Kupplungsreagenzien oder nach Aktivierung, z. B. zum Carbonsäurechlorid, in die entsprechenden Amide der Formel (XX) transformieren. Schritt 3 Die Herstellung der Verbindungen der Formel (I-c) gelingt in Analogie zu den unter Verfahren A, Schritt 5, beschriebenen Methoden durch Umsetzung von (XX) mit einem geeigneten Säurechlorid in Anwesenheit geeigneter Basen, z. B. Pyridin, Triethylamin oder Kaliumcarbonat, in einem geeigneten inerten Lösungsmittel, wie z. B. Dichlormethan. Alternativ lassen sich Verbindungen der Formel (I-c) auch durch Umsetzung von (XX) mit Carbonsäuren in Anwesenheit geeigneter Kupplungsreagenzien, z. B. HATU oder EDCI, und geeigneter Basen, z. B. Triethylamin oder N,N-Diisopropylethylamin, in geeigneten inerten Lösungsmitteln wie z. B. DMF oder Dichlormethan, erhalten (vergleiche in Analogie z. B. US2011/301181 oder WO2007/122258). Um Verbindungen der Formel (I-c) zu erhalten, ist alternativ Schritt 2 mit Schritt 3 in der Reihenfolge austauschbar. Verfahren E Die in Verfahren E angegebenen erfindungsgemäßen Verbindungen der Formel (I-c), in welchen V1 und V2 für Sauerstoff stehen, können durch literaturbekannte Methoden gemäß folgendem Schema hergestellt werden. (Ic) The radicals R1, R3, R4, R5, R6 and Q1 have the meanings described above, wherein Q1 is C-linked to the rest of the molecule. X is halogen or trifluoromethanesulfonate. R2 stands for hydrogen. The invention also relates to the intermediates of general formulas (XIX) and (XX) wherein R 2 is hydrogen and R 3, R 4, R 5, R 6 and Q 1 have the meanings described above, with Q 1 being CC-linked to the rest of the molecule and not represents unsubstituted phenyl. Step 1 The pyridines of the formula (XIX) can be prepared for example by a Michael reaction of a 1- (cyanomethyl) pyridinium halide and a ^, ^ -unsaturated ketone in the presence of ammonium acetate according to the so-called Kröhnke pyridine synthesis, as described in Synthesis 1976, 1-24 and Angew. Chem.196274, 811-817. The literature-known 6-amino-3,5-dicyano-4-phenylpyridine-2-carboxylic acid of the formula (XIX) (R 2 = hydrogen, R 5 = R 6 = cyano, Q 1 = phenyl) is described in Synth. Comm.1992, 22 (14), 2053-2056. The starting materials for the Kröhnke synthesis are commercially available or can be easily prepared. 1- (cyanomethyl) pyridinium halides are known in the literature; for example, the 1-cyanomethylpyridinium iodide (X = iodine, R5 = R6 = hydrogen) can be prepared by reacting pyridine, chloroacetonitrile and potassium iodide as described in Helv. Chim. Act. 1996 79, 1192-1202; the 1- (1-cyanoethyl) pyridinium trifluoromethanesulfonate (X = trifluoromethanesulfonate (triflate), R5 = R6 = hydrogen) can be prepared from cyanohydrin triflate, according to Eur. J. Org. Chem. 2012, 24, 4555-4564; the synthesis of 1- (dicyanomethyl) pyridinium salts is described in Chem. Ber. 1963, 96 (11), 3044-3049 and J. Am. Chem. Soc. 1965, 87/16), 3651-3656. The required ^, ^ -unsaturated ketones can be prepared by a number of known methods; For example, 2-oxo-4-arylbut-3-enoic acids (R6 = hydrogen) can be isolated from the corresponding aldehydes by condensation with ethyl pyruvate in a basic medium, as described for example in US2006 / 0020010, with the aid of sodium hydroxide solution; for the synthesis of 3-alkyl-2-oxo-4-aryl-but-3-enynoic acid (R 6 = alkyl), 2-oxoalkanoic acids (eg 2-oxobutanoic acid for R 6 = methyl) can be reacted with aromatic aldehydes, as described in Tet. 1991, 47 (43), 9019-9034. Step 2 The resulting carboxylic acids of formula (XIX) can be z. B. in analogy to the methods described in Method A, step 7, by coupling reagents or after activation, for. To the carboxylic acid chloride, into the corresponding amides of formula (XX). Step 3 The preparation of the compounds of the formula (Ic) is possible in analogy to the methods described under process A, step 5, by reacting (XX) with a suitable acid chloride in the presence of suitable bases, for. For example, pyridine, triethylamine or potassium carbonate, in a suitable inert solvent such. For example, dichloromethane. Alternatively, compounds of formula (Ic) may also be prepared by reacting (XX) with carboxylic acids in the presence of suitable coupling reagents, e.g. HATU or EDCI, and suitable bases, e.g. For example, triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such. As DMF or dichloromethane obtained (compare in analogy, for example, US2011 / 301181 or WO2007 / 122258). Alternatively, to obtain compounds of formula (Ic), step 2 is replaceable with step 3 in the order. Process E The compounds of the formula (Ic) according to the invention in which V1 and V2 are oxygen can be prepared by methods known from the literature in accordance with the following scheme.
Die Reste R1, R3, R4 und Q1 haben die oben beschriebenen Bedeutungen. R5 und R6 stehen für Wasserstoff. R2 hat die im Schema angegebene Bedeutung. Schritt 1 Die Herstellung der Verbindungen der Formel (I-c) gelingt in Analogie zu den unter Verfahren A, Schritt 5, beschriebenen Methoden durch Umsetzung von (XX) mit einem geeigneten Säurechlorid in Anwesenheit geeigneter Basen, z. B. Pyridin, Triethylamin oder Kaliumcarbonat, in einem geeigneten inerten Lösungsmittel, wie z. B. Dichlormethan. Verfahren F Die in Verfahren E angegebenen erfindungsgemäßen Verbindungen der Formel (I), in denen V1 oder V2 oder beide (V1 und V2) für Schwefel stehen, können durch literaturbekannte Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R3, R4 and Q1 have the meanings described above. R5 and R6 are hydrogen. R2 has the meaning given in the scheme. Step 1 The preparation of the compounds of formula (I-c) succeeds in analogy to the methods described in Method A, step 5, by reacting (XX) with a suitable acid chloride in the presence of suitable bases, for. For example, pyridine, triethylamine or potassium carbonate, in a suitable inert solvent such. For example, dichloromethane. Process F The compounds of the formula (I) according to the invention, in which V1 or V2 or both (V1 and V2) are sulfur, can be prepared by methods known from the literature in accordance with the following scheme.
Die Reste R1, R2, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen. V1 und V2 haben die im Schema angegebenen Bedeutungen. Schritt 1 Thioamide der Formel (I), in denen V1 oder V2 oder beide (V1 und V2) für Schwefel stehen, lassen sich aus Amiden der Formel (I-c) durch Umsetzung mit einem geeigneten Schwefelungsreagenz, beispielsweise Lawessons Reagenz (vergleiche in Analogie z. B. WO2005/9435) oder P4S10 (vergleiche in Analogie z. B. European Journal of Medicinal Chemistry 1995 30, 915– 924), in geeigneten Lösungsmitteln wie z.B. Toluol oder Xylol, herstellen. Alternativ kann die Thioamidsynthese auch aus den Intermediaten (VII) oder (XVII) erfolgen. Die weitere Umsetzung zu Verbindungen der Formel (I), in denen V1 oder V2 oder beide (V1 und V2) für Schwefel stehen, erfolgt dann analog zu den in Verfahren A und C beschriebenen Verfahren. Verfahren G Die in Verfahren G angegebenen erfindungsgemäßen Verbindungen der Formel (I), in denen R2 oder R3 für C(O)OAlkyl steht und der jeweils andere für H steht oder in denen beide (R2 und R3) für C(O)OAlkyl stehen, können durch literaturbekannte Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above. V1 and V2 have the meanings given in the scheme. Step 1 Thioamides of the formula (I) in which V1 or V2 or both (V1 and V2) represent sulfur can be prepared from amides of the formula (Ic) by reaction with a suitable sulfurizing reagent, for example Lawesson's reagent (cf. B. WO2005 / 9435) or P 4 S 10 (compare in analogy, for example, European Journal of Medicinal Chemistry 1995 30, 915-924), in suitable Solvents such as toluene or xylene produce. Alternatively, the thioamide synthesis can also be carried out from the intermediates (VII) or (XVII). The further conversion to compounds of the formula (I) in which V1 or V2 or both (V1 and V2) are sulfur is then carried out analogously to the processes described in Processes A and C. Process G The compounds of formula (I) according to the invention, in which R 2 or R 3 is C (O) -alkyl and the other is H or in which both (R 2 and R 3) are C (O) -alkyl , can be prepared by literature methods according to the following scheme.
Die Reste R1, R4, R5, R6, V1, V2 und Q1 haben die oben beschriebenen Bedeutungen. R2 und R3 haben die im Schema angegebenen Bedeutungen. Schritt 1 Carbamate der Formel (I), in denen R2 oder R3 für C(O)OAlkyl steht und der jeweils andere für H steht oder in denen beide (R2 und R3) für C(O)OAlkyl stehen, lassen sich aus Amiden der Formel (I), in denen R2 und R3 für H stehen, durch Umsetzung mit Chlorameisensäureestern und einer Base, beispielsweise Natriumhydrid (vergleiche in Analogie z. B. EP1932836), in geeigneten Lösungsmitteln wie z.B. DMF oder Tetrahydrofuran, herstellen. Verfahren H Die in Verfahren H angegebenen erfindungsgemäßen Verbindungen der Formel (I-c) können auch durch die Abfolge literaturbekannter Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R4, R5, R6, V1, V2 and Q1 have the meanings described above. R2 and R3 have the meanings given in the scheme. Step 1 Carbamates of the formula (I) in which R 2 or R 3 is C (O) -alkyl and the other is H or in which both (R 2 and R 3) are C (O) -alkyl, can be prepared from amides of Formula (I) in which R2 and R3 are H, by reaction with chloroformates and a base, for example sodium hydride (compare in analogy, for example, EP1932836), in suitable solvents such as DMF or tetrahydrofuran produce. Process H The compounds of the formula (Ic) according to the invention indicated in process H can also be prepared by the sequence of methods known from the literature in accordance with the following scheme.
Die Reste R1, R2, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen. Der Rest G steht für Alkoxy (insbesondere Methoxy und Ethoxy) oder NH2. Schritt 1: Die Kupplung der 2,6-Dichlor-4-iodpyridine der Formel (XIII) an der Position des Iods mit aromatischen oder heteroaromatischen Boronsäuren, Boronsäureestern oder Bisoxoborolanen zu Verbindungen der Formel (XIV) kann gemäß der unter Verfahren A, Schritt 9a beschriebenen bekannten Methoden unter Verwendung geeigneter Katalysatoren, z. B. Tetrakis(triphenylphosphin)palladium(0), erfolgen. Die benötigten Boronsäurederivate bzw. Boronsäureesterderivate sind teilweise bekannt und/oder kommerziell erhältlich bzw. können nach allgemein bekannten Methoden hergestellt werden (vgl. Boronic Acids (Eds.: D. G. Hall), 2nd ed., Wiley-VCH, Weinheim, 2011). Die Kupplung von Pyridinderivaten der Formel (XIII) mit NH-haltigen Heteroaromaten kann analog der der unter Verfahren B beschriebenen Methoden erfolgen. Schritt 2: Zum Erhalt von Verbindungen der Formel (XXI) aus den Vorstufen (XIV) können gemäß Verfahren C, Schritt 5, ebenfalls literaturbekannte Methoden verwendet werden. So können z. B. primäre Amine oder Ammoniak (für R2 = H) durch direkte Umsetzung beider Reaktionspartner durch Erhitzen in einem geeigneten Lösungsmittel, z. B. Wasser oder Dimethylsulfoxid, eingeführt werden. Schritt 3: Die Herstellung der Verbindungen der Formel (XXII) gelingt in Analogie zu den unter Verfahren A, Schritt 5 beschriebenen Methoden durch Umsetzung von (XXI) mit einem geeigneten Säurechlorid in Anwesenheit geeigneter Basen, z. B. Pyridin, Triethylamin oder Kaliumcarbonat, in einem geeigneten inerten Lösungsmittel, wie z. B. Dichlormethan, oder mit Carbonsäuren in Anwesenheit geeigneter Kupplungsreagenzien, z. B. HATU oder EDCI, und geeigneter Basen, z. B. Triethylamin oder N,N- Diisopropylethylamin, in geeigneten inerten Lösungsmitteln wie z. B. DMF oder Dichlormethan. Schritt 4: Chlorpyridine der allgemeinen Formel (XXII) können durch Umsetzung mit Kohlenmonoxid nach literaturbekannten Verfahren in Verbindungen der Formel (XXIII) überführt werden. Für G = Alkoxy kann diese Umsetzung in einem geeigneten Alkohol (insbesondere Methanol und Ethanol), durch Katalyse mit Tris-(dibenzylideneaceton)-dipalladium(0) [vergleiche z. B. US2013/165464] oder Palladium(II)-diacetat [vergleiche z. B. WO2011/137342 oder WO2014/114185] in Anwesenheit eines Phosphinliganden, z.B. Xantphos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene) oder Xphos (2- Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) und einer geeigneten organischen oder anorganischen Base, z. B. Triethylamin oder Cäsiumcarbonat, erfolgen. Für G = NH2 kann die Reaktion in Anwesenheit von Ammoniak, Ammoniak-Lösung in Wasser oder einem organischen Lösungsmittel, z.B. Dioxan, auch unter Übergangsmetall-Katalyse durchgeführt werden [vergleiche z.B. WO2000/037428; Chem. Eur. J.2010, 16(32), 9750-9753]. Schritt 5: Die erhaltenen Ester der Formel (XXIII) (G = Alkoxy) lassen sich z. B. in Analogie zu den unter Verfahren A, Schritte 6 und 7, beschriebenen Methoden durch Verseifung und Aktivierung der Carbonsäure durch Kupplungsreagenzien oder Umwandlung zum entsprechenden Carbonsäurechlorid, in die entsprechenden Amide der Formel (I-c) transformieren. Aus den primären Amiden der Formel (XXIII) (G = NH2) lassen sich in Analogie zu den unter Verfahren A, Schritt 5, beschriebenen Methoden durch Umsetzung mit einem geeigneten Säurechlorid in Anwesenheit geeigneter Basen, z. B. Pyridin, Triethylamin oder Kaliumcarbonat, in einem geeigneten inerten Lösungsmittel, wie z. B. Dichlormethan, oder mit Carbonsäuren in Anwesenheit geeigneter Kupplungsreagenzien, z. B. HATU oder EDCI, und geeigneter Basen, z. B. Triethylamin oder N,N- Diisopropylethylamin, in geeigneten inerten Lösungsmitteln wie z. B. DMF oder Dichlormethan, die entsprechenden Imide der Formel (I-c) herstellen. Verfahren I Die in Verfahren I angegebenen erfindungsgemäßen Verbindungen der Formel (I-c) können auch durch die Abfolge literaturbekannter Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above. The radical G is alkoxy (especially methoxy and ethoxy) or NH 2 . Step 1: The coupling of the 2,6-dichloro-4-iodopyridines of the formula (XIII) at the position of the iodine with aromatic or heteroaromatic boronic acids, boronic esters or bisoxoborolanes to give compounds of the formula (XIV) can be carried out according to the procedure A, step 9a described known methods using suitable catalysts, for. As tetrakis (triphenylphosphine) palladium (0) occur. The required boronic acid derivatives or boronic acid ester derivatives are known and / or commercially available or can be prepared by generally known methods (cf Boronic Acids (Eds .: DG Hall), 2nd ed., Wiley-VCH, Weinheim, 2011). The coupling of pyridine derivatives of the formula (XIII) with NH-containing heteroaromatics can be carried out analogously to the methods described under process B. Step 2: To obtain compounds of the formula (XXI) from the precursors (XIV), methods known from the literature can also be used in accordance with process C, step 5. So z. B. primary amines or ammonia (for R2 = H) by direct reaction of both reactants by heating in a suitable solvent, eg. As water or dimethyl sulfoxide, are introduced. Step 3: The preparation of the compounds of the formula (XXII) can be carried out in analogy to the processes described under Process A, Step 5 described methods by reacting (XXI) with a suitable acid chloride in the presence of suitable bases, for. For example, pyridine, triethylamine or potassium carbonate, in a suitable inert solvent such. As dichloromethane, or with carboxylic acids in the presence of suitable coupling reagents, for. HATU or EDCI, and suitable bases, e.g. For example, triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such as. As DMF or dichloromethane. Step 4: Chloropyridines of the general formula (XXII) can be converted by reaction with carbon monoxide by methods known from the literature into compounds of the formula (XXIII). For G = alkoxy, this reaction can be carried out in a suitable alcohol (in particular methanol and ethanol), by catalysis with tris (dibenzylideneacetone) dipalladium (0) [cf., for example, US Pat. B. US2013 / 165464] or palladium (II) diacetate [cf., for. WO2011 / 137342 or WO2014 / 114185] in the presence of a phosphine ligand, for example xantphos (4,5-bis (diphenylphosphino) -9,9-dimethylxanthene) or Xphos (2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl ) and a suitable organic or inorganic base, e.g. As triethylamine or cesium carbonate, take place. For G = NH 2, the reaction in the presence of ammonia, ammonia solution in water or an organic solvent, for example dioxane, can also be carried out under transition metal catalysis [compare, for example, WO 2000/037428; Chem. Eur. J.2010, 16 (32), 9750-9753]. Step 5: The resulting esters of formula (XXIII) (G = alkoxy) can be z. B. in analogy to the methods described in Method A, Steps 6 and 7, by saponification and activation of the carboxylic acid by coupling reagents or conversion to the corresponding carboxylic acid chloride, in the corresponding amides of the formula (Ic) transform. From the primary amides of the formula (XXIII) (G = NH 2 ) can be prepared in analogy to the methods described in Method A, step 5, by reaction with a suitable acid chloride in the presence of suitable bases, for. For example, pyridine, triethylamine or potassium carbonate, in a suitable inert solvent such. As dichloromethane, or with carboxylic acids in the presence of suitable coupling reagents, for. HATU or EDCI, and suitable bases, e.g. For example, triethylamine or N, N-diisopropylethylamine, in suitable inert solvents such as. As DMF or dichloromethane, the corresponding imides of formula (Ic) produce. Process I The compounds of the formula (Ic) according to the invention indicated in Process I can also be prepared by the sequence of methods known from the literature in accordance with the following scheme.
Die Reste R1, R2, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen. Der Rest G steht für Alkoxy (insbesondere Methoxy). Schritt 1: Die Herstellung von Verbindungen der Formel (XXIV) gelingt durch Umsetzung von Estern der Formel (XXIII) mit Hydrazinhydrat in einem geeigneten, inerten Lösungsmittel, wie z. B. Methanol, Ethanol oder Dioxan, beispielsweise analog der in WO2005/121152, European Journal of Medicinal Chemistry 2015, 93, 511– 522 oder Asian Journal of Chemistry 2015, 27, 4579 - 4582 beschriebenen Verfahren. Schritt 2: Hydrazidderivate der Formel (XXIV) lassen sich z. B. in Analogie zu den in WO2010/72781 oder Bioorganic and Medicinal Chemistry 2011, 19, 6400 - 6408 beschriebenen Verfahren durch Kondensation mit einem Aldehyd in einem alkoholischen Lösungsmittel, wie z. B. Methanol oder Ethanol oder in einem Lösungsmittelgemisch mit Wasser, in die entsprechenden Imine der Formel (I-c) überführen. Für die Kondensation wird meist eine Säure, wie z.B. Schwefelsäure, Salzsäure oder Essigsäure verwendet. Verfahren J Die in Verfahren J angegebenen erfindungsgemäßen Verbindungen der Formel (I-d), in welchen V1 für Sauerstoff steht und V2 für NH steht, können durch die Abfolge literaturbekannter Methoden gemäß folgendem Schema hergestellt werden. The radicals R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above. The radical G is alkoxy (especially methoxy). Step 1: The preparation of compounds of formula (XXIV) is possible by reacting esters of formula (XXIII) with hydrazine hydrate in a suitable inert solvent such. As methanol, ethanol or dioxane, for example analogous to that described in WO2005 / 121152, European Journal of Medicinal Chemistry 2015, 93, 511-522 or Asian Journal of Chemistry 2015, 27, 4579-4582. Step 2: Hydrazide derivatives of formula (XXIV) can be z. B. in analogy to the method described in WO2010 / 72781 or Bioorganic and Medicinal Chemistry 2011, 19, 6400 - 6408 by condensation with an aldehyde in an alcoholic solvent, such as. As methanol or ethanol or in a solvent mixture with water, in the corresponding imines of the formula (Ic) convert. For the condensation usually an acid, such as sulfuric acid, hydrochloric acid or acetic acid is used. Method J The compounds of the formula (Id) according to the invention, in which V1 is oxygen and V2 is NH, can be prepared by the sequence of methods known from the literature in accordance with the following scheme.
Die Reste R1, R2, R3, R4, R5, R6 und Q1 haben die oben beschriebenen Bedeutungen.  The radicals R1, R2, R3, R4, R5, R6 and Q1 have the meanings described above.
Z steht für Brom, Iod oderZ is bromine, iodine or
Schritt 1: Die Kupplung der Pyridinderivate der Formel (XXV) mit (Het)arylhalogeniden bzw. mit aromatischen oder heteroaromatischen Boronsäuren, Boronsäureestern oder Bisoxoborolanen zu Verbindungen der Formel (XXVI) kann gemäß der unter Verfahren A, Schritt 9 und Schritt 9a, beschriebenen bekannten Methoden unter Verwendung geeigneter Katalysatoren, z. B. Tetrakis(triphenylphosphin)palladium(0), erfolgen. Die benötigten Boronsäurederivate bzw. Boronsäureesterderivate sind teilweise bekannt und/oder kommerziell erhältlich bzw. können nach allgemein bekannten Methoden hergestellt werden (vgl. Boronic Acids (Eds.: D. G. Hall), 2nd ed., Wiley-VCH, Weinheim, 2011). Die Kupplung von Pyridinderivaten der Formel (XXV) (Z = Iod) mit NH-haltigen Heteroaromaten kann analog der der unter Verfahren B beschriebenen Methoden erfolgen. Pyridinderivate der Formel (XXV) sind kommerziell erhältlich, wie z.B. 4-Brom-2-Chlorpyridin (R5 = R6 = Wasserstoff), 2-Chlor-4-iodpyridin (R5 = R6 = Wasserstoff), 2-Chlor-4-iod-5-trifluormethylpyridin (R5 = Wasserstoff, R6 = Trifluormethyl), 2,5-Dichlor-4-iodpyridin (R5 = Wasserstoff, R6 = Chlor), 2- Chlor-5-cyano-4-iodpyridin (R5 = Wasserstoff, R6 = Cyano), 2,3-Dichlor-4-iodpyridin (R5 = Chlor, R6 = Wasserstoff), 2-Chlor-3-cyano-4-iodpyridin (R5 = Cyano, R6 = Wasserstoff) oder literaturbekannt oder lassen sich nach bekannten Verfahren herstellen (vgl. WO2015/52264, Journal of Medicinal Chemistry 2012, 55, 4286 - 4296 oder Tetrahedron 2002, 58, 4369– 4373). Schritt 2: Verbindungen der Formel (XXVI) lassen sich durch Reaktion mit einem Oxidationsmittel in Verbindungen der Formel (XXVII) überführen. Als Oxidationsmittel wird häufig Wasserstoffperoxid in Kombination mit einer Säure, wie z.B. Trifluoressigsäure, Essigsäure oder Ameisensäure (vgl. WO2010/25451 oder Organometallics 2011, 30, 6751 - 6765) oder 3-Chlorperbenzoesäure in einem inerten Lösungsmittel, wie z. B. Dichlormethan oder Chloroform (vgl. WO2011/40629, WO2010/109005 oder WO2011/25505) verwendet. Schritt 3: Durch Umsetzung von Verbindungen der Formel (XXVII) mit Trimethylsilylcyanid und einer Aminbase, beispielsweise Triethylamin in einem geeigneten, inerten Lösungsmittel wie z.B. Acetonitril in Analogie zu den in z.B. WO2009/111337 oder US2008/275057 beschriebenen Verfahren, lassen sich Verbindungen der Formel (XXVIII) erhalten. Schritt 4: Verbindungen der Formel (XXVIII) können durch Umsetzung mit einem Carboxamid unter Verwendung geeigneter Katalysatoren, wie z. B. Palladium(II)acetat oder Tris- (dibenzylidenaceton)dipalladium(0), einem Phosphinliganden wie z.B. Xantphos und einer anorganischen Base wie z.B. Cäsiumcarbonat oder Kaliumphosphat in einem geeigneten, inerten Lösungsmittel, wie z.B. Dioxan in Analogie zu den in z.B. WO2011/137342, US2012/15943 oder Bioorganic and Medicinal Chemistry Letters 2014, 24, 1148 - 1153 beschriebenen Verfahren in Verbindungen der Formel (XXIX) überführen. Schritt 5: Die entsprechenden Amidine der Formel (I-d) können erhalten werden durch Reaktion von Verbindungen der Formel (XXIX) mit Aminen in Gegenwart einer Lewis-Säure, wie z.B. Titantetrachlorid oder Zinntetrachlorid, ggf. in einem geeigneten, inerten Lösungsmittel, wie z.B. Tetrahydrofuran oder Dioxan in Analogie zu den in z.B. Tetrahedron Letters 2013, 54, 343 - 346 oder Journal of Fluorescence 2014, 24, 1563 - 1570 beschriebenen Verfahren. Alternativ kann die Umsetzung in Gegenwart von Natriummethanolat in Methanol durchgeführt werden (vgl. Journal of Heterocyclic Chemistry 2011, 48, 921 - 926 oder European Journal of Medicinal Chemistry 2013, 59, 7 - 14). Herstellungsbeispiele Step 1: The coupling of the pyridine derivatives of the formula (XXV) with (het) aryl halides or with aromatic or heteroaromatic boronic acids, boronic esters or bisoxoborolanes to give compounds of the formula (XXVI) can be carried out according to the process described under Process A, step 9 and step 9a Methods using suitable catalysts, eg. As tetrakis (triphenylphosphine) palladium (0) occur. The required boronic acid derivatives or boronic acid ester derivatives are known and / or commercially available or can be prepared by generally known methods (cf Boronic Acids (Eds .: DG Hall), 2nd ed., Wiley-VCH, Weinheim, 2011). The coupling of pyridine derivatives of the formula (XXV) (Z = iodine) with NH-containing heteroaromatics can be carried out analogously to the methods described under process B. Pyridine derivatives of the formula (XXV) are commercially available, such as 4-bromo-2-chloropyridine (R5 = R6 = hydrogen), 2-chloro-4-iodopyridine (R5 = R6 = hydrogen), 2-chloro-4-iodo 5-trifluoromethylpyridine (R5 = hydrogen, R6 = trifluoromethyl), 2,5-dichloro-4-iodopyridine (R5 = hydrogen, R6 = chlorine), 2-chloro-5-cyano-4-iodopyridine (R5 = hydrogen, R6 = Cyano), 2,3-dichloro-4-iodopyridine (R5 = chlorine, R6 = hydrogen), 2-chloro-3-cyano-4-iodopyridine (R5 = cyano, R6 = hydrogen) or known from the literature or can be prepared by known methods (see WO2015 / 52264, Journal of Medicinal Chemistry 2012, 55, 4286-4266 or Tetrahedron 2002, 58, 4369-4373). Step 2: Compounds of the formula (XXVI) can be converted by reaction with an oxidizing agent into compounds of the formula (XXVII). Hydrogen peroxide in combination with an acid such as trifluoroacetic acid, acetic acid or formic acid (see WO2010 / 25451 or Organometallics 2011, 30, 6751-6765) or 3-chloroperbenzoic acid in an inert solvent, such as eg. For example, dichloromethane or chloroform (see, WO2011 / 40629, WO2010 / 109005 or WO2011 / 25505). Step 3: By reacting compounds of the formula (XXVII) with trimethylsilyl cyanide and an amine base, for example triethylamine in a suitable inert solvent such as acetonitrile in analogy to the processes described in, for example, WO2009 / 111337 or US2008 / 275057, compounds of the formula (XXVIII). Step 4: Compounds of formula (XXVIII) can be prepared by reaction with a carboxamide using suitable catalysts, such as. B. palladium (II) acetate or tris (dibenzylidenaceton) dipalladium (0), a phosphine ligands such as xantphos and an inorganic base such as cesium carbonate or potassium phosphate in a suitable inert solvent such as dioxane in analogy to those in, for example, WO2011 / 137342, US2012 / 15943 or Bioorganic and Medicinal Chemistry Letters 2014, 24, 1148-1153, into compounds of formula (XXIX). Step 5: The corresponding amidines of formula (Id) can be obtained by reaction of compounds of formula (XXIX) with amines in the presence of a Lewis acid such as titanium tetrachloride or tin tetrachloride, optionally in a suitable inert solvent such as tetrahydrofuran or dioxane in analogy to the methods described in, for example, Tetrahedron Letters 2013, 54, 343-346 or Journal of Fluorescence 2014, 24, 1563-1570. Alternatively, the reaction can be carried out in the presence of sodium methoxide in methanol (see Journal of Heterocyclic Chemistry 2011, 48, 921-926 or European Journal of Medicinal Chemistry 2013, 59, 7-14). Preparation Examples
Nach Verfahren D: Natrium-4-(4-chlorphenyl)-2-oxobut-3-enoat By Method D: Sodium 4- (4-chlorophenyl) -2-oxobut-3-enoate
5 g (35,57 mmol) 4-Chlorbenzaldehyd, 4,13 g (35,57 mmol) Ethyl-2-oxopropanoat wurden unter Schutzgas vorgelegt, dann unter Kühlung auf 6-8° C eine Lösung von 3,13 g (78,25 mmol) Natriumhydroxyd gelöst in 33 ml Wasser zugetropft. Es wurde eine Stunde nachgerührt, das Reaktionsgemisch anschliessend auf 300 ml Ethanol gegeben und der erhaltene Feststoff über einen Faltenfilter abfiltriert. Es wurden 7,130 g (86% d.Th.) Rohprodukt erhalten, das ohne weitere Reinigung im Folgeschritt umgesetzt wurde. 6-Amino-4-(4-chlorphenyl)pyridin-2-carbonsäure (XIX-1) 5 g (35.57 mmol) of 4-chlorobenzaldehyde, 4.13 g (35.57 mmol) of ethyl 2-oxopropanoate were initially introduced under protective gas, then with cooling to 6-8 ° C, a solution of 3.13 g (78 , 25 mmol) of sodium hydroxide dissolved in 33 ml of water was added dropwise. The mixture was stirred for one hour, the reaction mixture was then added to 300 ml of ethanol and the resulting solid was filtered through a pleated filter. There were obtained 7.130 g (86% of theory) of crude product, which was reacted without further purification in the subsequent step. 6-Amino-4- (4-chlorophenyl) pyridine-2-carboxylic acid (XIX-1)
7,13 g (30,65 mmol) Natrium-4-(4-chlorphenyl)-2-oxobut-3-enoat und 4,74 g (30,65 mmol) 1- (Cyanomethyl)-Pyridiniumchlorid wurden in 160 ml Eisessig gegeben, mit 5,06 g (65,6 mmol) Ammoniumacetat versetzt und über zwei Stunden bei 80°C gerührt. Nach dem Abkühlen wurde auf Wasser gegeben das Reaktionsprodukt als Feststoff über einen Faltenfilter abfiltriert. Es wurden 5,70 g (68,8 % d.Th.) 6-Amino-4-(4-chlorphenyl)-pyridin-2-carbonsäure (XIX-1) erhalten. logP (sauer): 1.02; MH+: 249; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 6,55 (breit, 2H), 6,93 (d, 1H), 7,43 (d, 1H), 7,57 (d, 2H), 7,72 (d, 2H). 6-Amino-4-(4-chlorphenyl)-N-(4-cyanbenzyl)pyridin-2-carboxamid (XX-1) 7.13 g (30.65 mmol) of sodium 4- (4-chlorophenyl) -2-oxobut-3-enoate and 4.74 g (30.65 mmol) of 1- (cyanomethyl) -pyridinium chloride were dissolved in 160 ml of glacial acetic acid added, mixed with 5.06 g (65.6 mmol) of ammonium acetate and stirred at 80 ° C for two hours. After cooling, water was added to the reaction product as a solid filtered through a pleated filter. There were obtained 5.70 g (68.8% of theory) of 6-amino-4- (4-chlorophenyl) -pyridine-2-carboxylic acid (XIX-1). logP (acid): 1.02; MH +: 249; 1 H-NMR (400 MHz, D 6 -DMSO) ppm ppm: 6.55 (broad, 2H), 6.93 (d, 1H), 7.43 (d, 1H), 7.57 (d, 2H) , 7.72 (d, 2H). 6-Amino-4- (4-chlorophenyl) -N- (4-cyanobenzyl) pyridine-2-carboxamide (XX-1)
200 mg (0,80 mmol) 6-Amino-4-(4-chlorphenyl)pyridin-2-carbonsäure (XIX-1), 295 mg (2,41 mmol) 4- Dimethylaminopyridin und 446,6 mg (2,41 mmol) EDC-Hydrochlorid wurden in 65 ml Dichlormethan über 15 Minuten bei Raumtemperatur gerührt, dann 106 mg (0,80 mmol) 4-(Amino-methyl)benzonitril hinzugegeben und weitere 18 Stunden bei Raumtemperatur gerührt. Zur Aufarbeitung wurde das Reaktionsgemisch auf etwa 100 ml einer 3%igen wässrigen Natriumdihydrogenphosphatlösung gegeben. Das Gemisch wurde dreimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen über Natriumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand durch säulenchromatographische Aufreinigung mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. Es wurden daraus 40 mg (13,7 % d.Th.) des Zielproduktes (XX-1) erhalten. logP (neutral): 2,82; MH+: 363; 1H-NMR(600 MHz, D6-DMSO) ^ ppm: 4,57 (d, 2H), 6,24 (breit, 2H), 6,91 (d, 1H), 7,44 (d, 1H), 7,50 (d, 2H), 7,58 (d, 2H), 7,70 (d, 2H), 7,80 (d, 2H), 8,96 (m, 1H). 4-(4-Chlorphenyl)-N-(4-cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]pyridin-2-carboxamid (I-020) 200 mg (0.80 mmol) 6-amino-4- (4-chlorophenyl) pyridine-2-carboxylic acid (XIX-1), 295 mg (2.41 mmol) 4-dimethylaminopyridine and 446.6 mg (2.41 mmol) of EDC hydrochloride were stirred in 65 ml of dichloromethane for 15 minutes at room temperature, then 106 mg (0.80 mmol) of 4- (amino-methyl) benzonitrile added and stirred for a further 18 hours at room temperature. For work-up, the reaction mixture was added to about 100 ml of a 3% aqueous sodium dihydrogen phosphate solution. The mixture was extracted three times with dichloromethane and the combined organic phases were dried over sodium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography with a water / acetonitrile gradient as eluent. From this, 40 mg (13.7% of theory) of the target product (XX-1) were obtained. logP (neutral): 2.82; MH +: 363; 1 H NMR (600 MHz, D 6 -DMSO) ppm ppm: 4.57 (d, 2H), 6.24 (broad, 2H), 6.91 (d, 1H), 7.44 (d, 1H) , 7.50 (d, 2H), 7.58 (d, 2H), 7.70 (d, 2H), 7.80 (d, 2H), 8.96 (m, 1H). 4- (4-chlorophenyl) -N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxamide (I-020)
30 mg (0,08 mmol) 6-Amino-4-(4-chlorphenyl)-N-(4-cyanbenzyl)pyridin-2-carboxamid (XX-1) wurden zunächst in ein Gemisch aus 5 ml Dichlormethan und 5 ml Pyridin gegeben und dann nach Kühlung auf 0°C mit 35 mg (0,33 mmol) Cyclopropancarbonsäurechlorid versetzt. Das Reaktionsgemisch wurde 48 Stunden bei Raumtemperatur gerührt und direkt auf Polygoprep 100-50 C18 aufgezogen. Nach der säulenchromatographischen Aufreinigung mit einem Wasser / Acetonitril Gradienten als Laufmittel wurden daraus 17 mg (46,5 % d.Th.) des 4-(4-Chlorphenyl)-N-(4-cyanbenzyl)-6- [(cyclopropylcarbonyl)amino]pyridin-2-carboxamid (I-020) erhalten. logP (neutral): 3,54; MH+: 431; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,86 (m, 4H), 2,05 (m, 1H), 4,64 (d, 2H), 7,56 (d, 2H), 7,61 (d, 2H), 7,80 (m, 4H), 7,96 (d, 1H), 8,25 (d, 1H), 8,95 (tr, 1H), 10,96 (s, 1H) . 6-Amino-N-cyclopropyl-N-methyl-4-[4-(trifluormethyl)phenyl]pyridin-2-carboxamid (XX-2) 30 mg (0.08 mmol) of 6-amino-4- (4-chlorophenyl) -N- (4-cyanobenzyl) pyridine-2-carboxamide (XX-1) were first added to a mixture of 5 ml of dichloromethane and 5 ml of pyridine and then after cooling to 0 ° C with 35 mg (0.33 mmol) cyclopropanecarboxylic acid chloride. The reaction mixture was stirred for 48 hours at room temperature and applied directly to Polygoprep 100-50 C18. After purification by column chromatography with a water / acetonitrile gradient as eluent, 17 mg (46.5% of theory) of 4- (4-chlorophenyl) -N- (4-cyanobenzyl) -6- [(cyclopropylcarbonyl) amino ] pyridine-2-carboxamide (I-020). logP (neutral): 3.54; MH +: 431; 1 H-NMR (400 MHz, D 6 -DMSO) ppm ppm: 0.86 (m, 4H), 2.05 (m, 1H), 4.64 (d, 2H), 7.56 (d, 2H) , 7.61 (d, 2H), 7.80 (m, 4H), 7.96 (d, 1H), 8.25 (d, 1H), 8.95 (tr, 1H), 10.96 ( s, 1H). 6-Amino-N-cyclopropyl-N-methyl-4- [4- (trifluoromethyl) phenyl] pyridine-2-carboxamide (XX-2)
200 mg (0,71 mmol) 6-Amino-4-[4-(trifluormethyl)phenyl]pyridin-2-carbonsäure [Synthese analog zu 6-Amino-4-(4-chlorphenyl)pyridin-2-carbonsäure (XIX-1)], 260 mg (2,13 mmol) 4- Dimethylaminopyridin und 407,6 mg (2,13 mmol) EDC-Hydrochlorid wurden in 80 ml Dichlormethan über 15 Minuten bei Raumtemperatur gerührt, dann 50,4 mg (0,71 mmol) N-Methylcyclopropanamin hinzugegeben und weitere 18 Stunden bei Raumtemperatur gerührt. Zur Aufarbeitung wurde das Reaktionsgemisch auf etwa 100 ml einer 3%igen wässrigen Natriumdihydrogenphosphatlösung gegeben. Das Gemisch wurde dreimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen über Natriumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand durch säulenchromatographische Aufreinigung mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. Es wurden daraus 49 mg (18 % d.Th.) des Zielproduktes (XX-2) erhalten. logP (neutral): 2,40; MH+: 336; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,48 (s br, 4H), 2,8-2,98 (m br, 4H), 6,30 (breit, 2H), 6,77 (s, 1H), 6,92 (s, 1H), 7,87 (m, 4H). N-Cyclopropyl-6-[(cyclopropylcarbonyl)amino]-N-methyl-4-[4-(trifluormethyl)phenyl]pyridin-2- carboxamid (I-036) 200 mg (0.71 mmol) 6-amino-4- [4- (trifluoromethyl) phenyl] pyridine-2-carboxylic acid [Synthesis analogous to 6-amino-4- (4-chlorophenyl) pyridine-2-carboxylic acid (XIX 1)], 260 mg (2.13 mmol) of 4-dimethylaminopyridine and 407.6 mg (2.13 mmol) of EDC hydrochloride were stirred in 80 ml of dichloromethane for 15 minutes at room temperature, then 50.4 mg (0.71 mmol) of N-methylcyclopropanamine and stirred at room temperature for a further 18 hours. For work-up, the reaction mixture was added to about 100 ml of a 3% aqueous sodium dihydrogen phosphate solution. The mixture was extracted three times with dichloromethane and the combined organic phases were dried over sodium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography with a water / acetonitrile gradient as eluent. From this, 49 mg (18% of theory) of the target product (XX-2) were obtained. logP (neutral): 2.40; MH +: 336; 1 H NMR (400 MHz, D 6 -DMSO) ppm ppm: 0.48 (s br, 4H), 2.8-2.98 (mbr, 4H), 6.30 (broad, 2H), 6, 77 (s, 1H), 6.92 (s, 1H), 7.87 (m, 4H). N-cyclopropyl-6 - [(cyclopropylcarbonyl) amino] -N-methyl-4- [4- (trifluoromethyl) phenyl] pyridine-2-carboxamide (I-036)
63 mg (0,19 mmol) 6-Amino-N-cyclopropyl-N-methyl-4-[4-(trifluormethyl)phenyl]pyridin-2- carboxamid wurden zunächst in ein Gemisch aus 5 ml Dichlormethan und 5 ml Pyridin gegeben und dann nach Kühlung auf 0°C mit 79 mg (0,75 mmol) Cyclopropancarbonsäurechlorid versetzt. Das Reaktionsgemisch wurde 48 Stunden bei Raumtemperatur gerührt und direkt auf Polygoprep 100-50 C18 aufgezogen. Nach der säulenchromatographischen Aufreinigung mit einem Wasser / Acetonitril Gradienten als Laufmittel wurden daraus 50 mg (65 % d.Th.) des N-Cyclopropyl-6- [(cyclopropylcarbonyl)amino]-N-methyl-4-[4-(trifluormethyl)phenyl]-pyridin-2-carboxamid (I-036) erhalten. logP (neutral): 3,21; MH+: 404; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,47 (m, 4H), 0,86 (m, 4H), 2,03 ( m, 1H), 2,8-3,1 (m, 4H), 7,59 (s, 1H), 7,90 (d, 2H), 7,98 (d, 2H), 8,49 (s, 1H), 11,10 (s, 1H). 6-Amino-N-(4-cyan-3-fluorbenzyl)-4-[4-(trifluormethyl)phenyl]pyridin-2-carboxamid (XX-3) 63 mg (0.19 mmol) of 6-amino-N-cyclopropyl-N-methyl-4- [4- (trifluoromethyl) phenyl] pyridine-2-carboxamide were first added to a mixture of 5 ml of dichloromethane and 5 ml of pyridine, and then, after cooling to 0 ° C., 79 mg (0.75 mmol) of cyclopropanecarboxylic acid chloride are added. The reaction mixture was stirred for 48 hours at room temperature and applied directly to Polygoprep 100-50 C 18 . After purification by column chromatography with a water / acetonitrile gradient as the eluent, 50 mg (65% of theory) of N-cyclopropyl-6 were obtained therefrom. [(cyclopropylcarbonyl) amino] -N-methyl-4- [4- (trifluoromethyl) phenyl] -pyridine-2-carboxamide (I-036). logP (neutral): 3.21; MH +: 404; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 0.47 (m, 4H), 0.86 (m, 4H), 2.03 (m, 1H), 2.8-3.1 (m , 4H), 7.59 (s, 1H), 7.90 (d, 2H), 7.98 (d, 2H), 8.49 (s, 1H), 11.10 (s, 1H). 6-amino-N- (4-cyano-3-fluorobenzyl) -4- [4- (trifluoromethyl) phenyl] pyridine-2-carboxamide (XX-3)
200 mg (0,71 mmol) 6-Amino-4-[4-(trifluormethyl)phenyl]pyridin-2-carbonsäure [Synthese analog zu 6-Amino-4-(4-chlorphenyl)pyridin-2-carbonsäure (XIX-1)], 260 mg (2,13 mmol) 4- Dimethylaminopyridin und 409 mg (2,13 mmol) EDC-Hydrochlorid wurden in 65 ml Dichlormethan über 15 Minuten bei Raumtemperatur gerührt, dann 106,4 mg (0,71 mmol) 4-(Aminomethyl)-2- fluorbenzonitril hinzugegeben und weitere 18 Stunden bei Raumtemperatur gerührt. Zur Aufarbeitung wurde das Reaktionsgemisch auf etwa 100 ml einer 3%igen wässrigen Natriumdihydrogenphosphatlösung gegeben. Das Gemisch wurde dreimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen über Natriumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand durch säulenchromatographische Aufreinigung mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. Es wurden daraus 62 mg des Zielproduktes (XX-3) erhalten. logP (neutral): 3,19; MH+: 415; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 4,59 (d, 2H), 6,3 (breit, 2H), 6,99 (s, 1H), 7,35 (d, 1H), 7,44 (d, 1H), 7,49 (s, 1H), 7,9 (m, 5H), 9,05 (tr, 1H). Nach Verfahren E: 6-[Bis(cyclopropylcarbonyl)amino]-N-(4-cyan-3-fluorbenzyl)-4-[4-(trifluormethyl)phenyl]- pyridin-2-carboxamid (I-028) 200 mg (0.71 mmol) 6-amino-4- [4- (trifluoromethyl) phenyl] pyridine-2-carboxylic acid [Synthesis analogous to 6-amino-4- (4-chlorophenyl) pyridine-2-carboxylic acid (XIX 1)], 260 mg (2.13 mmol) of 4-dimethylaminopyridine and 409 mg (2.13 mmol) of EDC hydrochloride were stirred in 65 ml of dichloromethane for 15 minutes at room temperature, then 106.4 mg (0.71 mmol). Added 4- (aminomethyl) -2-fluorobenzonitrile and stirred for a further 18 hours at room temperature. For work-up, the reaction mixture was added to about 100 ml of a 3% aqueous sodium dihydrogen phosphate solution. The mixture was extracted three times with dichloromethane and the combined organic phases were dried over sodium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography with a water / acetonitrile gradient as eluent. From this, 62 mg of the target product (XX-3) were obtained. logP (neutral): 3.19; MH +: 415; 1 H-NMR (400 MHz, D 6 -DMSO) ppm ppm: 4.59 (d, 2H), 6.3 (broad, 2H), 6.99 (s, 1H), 7.35 (d, 1H) , 7.44 (d, 1H), 7.49 (s, 1H), 7.9 (m, 5H), 9.05 (tr, 1H). By Method E: 6- [Bis (cyclopropylcarbonyl) amino] -N- (4-cyano-3-fluorobenzyl) -4- [4- (trifluoromethyl) phenyl] -pyridine-2-carboxamide (I-028)
41,8 mg (0,1 mmol) 6-Amino-N-(4-cyan-3-fluorbenzyl)-4-[4-(trifluormethyl)phenyl]pyridin-2- carboxamid (XX-3) wurden zunächst in ein Gemisch aus 5 ml Dichlormethan und 5 ml Pyridin gegeben und dann nach Kühlung auf 0°C mit 42 mg (0,4 mmol) Cyclopropancarbonsäurechlorid versetzt. Das Reaktionsgemisch wurde 5 Tage bei Raumtemperatur gerührt und direkt auf Polygoprep 100-50 C18 aufgezogen. Nach der säulenchromatographischen Aufreinigung mit einem Wasser / Acetonitril Gradienten als Laufmittel wurden daraus 14 mg (24 % d.Th.) des 6-[Bis(cyclopropylcarbonyl)amino]- N-(4-cyan-3-fluorbenzyl)-4-[4-(trifluormethyl)-phenyl]pyridin-2-carboxamid (I-028) erhalten. logP (neutral/sauer): 4,18/4,27; MH+: 551; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,91 (m, 4H), 1,04 (m, 4H), 2,05 (m, 2H), 4,61 (d, 2H), 7,37 (d, 1H), 7,45 (d, 1H), 7,9 (m, 3H), 8,15 (d, 2H), 8,23 (d, 1H), 8,42 (d, 1H), 9,51 (tr, 1H). Nach Verfahren A: Dimethyl-4-brompyridin-2,6-dicarboxylat (III-1) 41.8 mg (0.1 mmol) of 6-amino-N- (4-cyano-3-fluorobenzyl) -4- [4- (trifluoromethyl) phenyl] pyridine-2-carboxamide (XX-3) were initially in Added mixture of 5 ml of dichloromethane and 5 ml of pyridine and then after cooling to 0 ° C with 42 mg (0.4 mmol) of cyclopropanecarboxylic acid chloride. The reaction mixture was stirred for 5 days at room temperature and applied directly to Polygoprep 100-50 C18. After purification by column chromatography with a water / acetonitrile gradient as eluant, 14 mg (24% of theory) of the 6- [bis (cyclopropylcarbonyl) amino] - N- (4-cyano-3-fluorobenzyl) -4- [ 4- (trifluoromethyl) -phenyl] pyridine-2-carboxamide (I-028). logP (neutral / acidic): 4.18 / 4.27; MH +: 551; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 0.91 (m, 4H), 1.04 (m, 4H), 2.05 (m, 2H), 4.61 (d, 2H), 7.37 (d, 1H), 7.45 (d, 1H), 7.9 (m, 3H), 8.15 (d, 2H), 8.23 (d, 1H), 8.42 (i.e. , 1H), 9.51 (tr, 1H). By Method A: Dimethyl 4-bromopyridine-2,6-dicarboxylate (III-1)
Zu einer gerührten Suspension von 80,0 g (437 mmol) 4-Hydroxy-pyridin-2,6-dicarbonsäure (II-1) in 1400 ml Tetrachlorkohlenstoff wurden 752,0 g (1748 mmol) Phosphorpentabromid gegeben. Die resultierende Mischung wurde für 16 h unter Rückfluss erhitzt und anschließend vorsichtig und tropfenweise bei einer Temperatur < 80 °C mit 350 ml Methanol gequencht. Der Ansatz wurde noch 1 h bei 80 °C gerührt, auf Raumtemperatur abgekühlt und im Vakuum eingedampft. Der Rückstand wurde mit Eiswasser versetzt und noch eine Stunde gerührt. Der ausfallende Feststoff wurde abfiltriert, mit Wasser gewaschen und durch Ko-evaporation mit Toluol getrocknet. Man erhielt 70,0 g (60,0% d. Th.) der Titelverbindung (III-1). 1H-NMR (400,0 MHz, CDCl3): ^ = 8,46 (s, 2 H), 4,03 (s, 6 H) 4-Brom-6-(methoxycarbonyl)pyridin-2-carbonsäure (IV-1) To a stirred suspension of 80.0 g (437 mmol) of 4-hydroxy-pyridine-2,6-dicarboxylic acid (II-1) in 1400 mL of carbon tetrachloride was added 752.0 g (1748 mmol) of phosphorus pentabromide. The resulting mixture was refluxed for 16 h and then quenched cautiously and dropwise at a temperature <80 ° C with 350 mL of methanol. The mixture was stirred for a further 1 h at 80 ° C, cooled to room temperature and evaporated in vacuo. The residue was mixed with ice-water and stirred for one more hour. The precipitated solid was filtered off, washed with water and dried by co-evaporation with toluene. 70.0 g (60.0% of theory) of the title compound (III-1) were obtained. 1 H NMR (400.0 MHz, CDCl 3 ): = 8.46 (s, 2 H), 4.03 (s, 6 H) 4-Bromo-6- (methoxycarbonyl) pyridine-2-carboxylic acid (IV-1)
101,0 g (368 mmol) Dimethyl-4-brompyridin-2,6-dicarboxylat (III-1) wurden in 1000 ml einer 10:1- Mischung (V/V) Methanol:Dichlormethan suspendiert und 16,5 g (295 mmol) Kaliumhydroxid zugegeben. Die Reaktionsmischung wurde für 6 h bei Raumtemperatur gerührt. Anschließend wurde der Ansatz mit 1500 ml Diethylether versetzt und weitere 30 Minuten gerührt. Der ausfallende Feststoff wurde abfiltriert und mit Diethylether gewaschen. Anschließend wurde der Filterrückstand resuspendiert und mit 2 N HCl auf pH 3 angesäuert. Der ausfallende Feststoff wurde abfiltriert, mit Wasser und Diethylether gewaschen und im Vakuum getrocknet. Das Filtrat wurde viermal mit je 200 ml Chloroform extrahiert, die vereinigten organischen Phasen mit Brine gewaschen, über Natriumsulfat getrocknet, filtriert und im Vakuum eingedampft. Der Rückstand wurde mit dem vorher erhaltenen Feststoff vereinigt und alles durch Ko-evaporation mit Toluol getrocknet. Man erhielt 70,0 g (65,0% d. Th.) der Titelverbindung (IV-1). 1H-NMR (400,0 MHz, d6-DMSO): ^ = 13,83 (s, broad, 1 H), 8,38 (d, 2 H), 3,92 (s, 3 H) Methyl-4-brom-6-[(cyclopropylcarbonyl)amino]pyridin-2-carboxylat (VII-1) a) Methyl-4-brom-6-[(tert-butoxycarbonyl)amino]pyridin-2-carboxylat (V-1) 101.0 g (368 mmol) of dimethyl 4-bromopyridine-2,6-dicarboxylate (III-1) were suspended in 1000 ml of a 10: 1 mixture (v / v) methanol: dichloromethane and 16.5 g (295 mmol) of potassium hydroxide. The reaction mixture was stirred for 6 h at room temperature. Subsequently, the batch was mixed with 1500 ml of diethyl ether and stirred for a further 30 minutes. The precipitated solid was filtered off and washed with diethyl ether. The filter residue was then resuspended and acidified to pH 3 with 2N HCl. The precipitated solid was filtered off, washed with water and diethyl ether and dried in vacuo. The filtrate was extracted four times with 200 ml of chloroform, the combined organic phases washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was combined with the previously obtained solid and everything dried by co-evaporation with toluene. 70.0 g (65.0% of theory) of the title compound (IV-1) were obtained. 1H-NMR (400.0 MHz, d6-DMSO): ^ = 13.83 (s, broad, 1H), 8.38 (d, 2H), 3.92 (s, 3H) methyl-4 Bromo-6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxylate (VII-1) a) Methyl 4-bromo-6 - [(tert-butoxycarbonyl) amino] pyridine-2-carboxylate (V-1)
Zu einer Mischung von 21,0 g (80,8 mmol) 4-Brom-6-(methoxycarbonyl)pyridin-2-carbonsäure (IV-1) und 13,1 g (129 mmol) Triethylamin in 280 ml eines Gemisches aus t-Butanol und 1,4-Dioxan (Verhältnis 1:3, V/V) wurden 31,0 g (105 mmol) Diphenylphosphorylazid bei Raumtemperatur zugegeben. Die Reaktionsmischung wurde anschließend für 2 Stunden unter Rückfluss erhitzt und danach auf Raumtemperatur abgekühlt. Wasser wurde zugesetzt und der Ansatz mit Ethylacetat mehrfach extrahiert. Die vereinigten organischen Phasen wurden nacheinander mit Wasser und Brine gewaschen, über Natriumsulfat getrocknet, filtriert und eingedampft. Man erhielt 29 g einer Rohfraktion der Titelverbindung (V-1), die ohne weitere Aufreinigung direkt weiter umgesetzt wurden gemäß b) zu (VI-1). b) Methyl-6-amino-4-brompyridin-2-carboxylat (VI-1) To a mixture of 21.0 g (80.8 mmol) of 4-bromo-6- (methoxycarbonyl) pyridine-2-carboxylic acid (IV-1) and 13.1 g (129 mmol) of triethylamine in 280 ml of a mixture of t Butanol and 1,4-dioxane (ratio 1: 3, V / V) were added 31.0 g (105 mmol) of diphenylphosphoryl azide at room temperature. The reaction mixture was then refluxed for 2 hours and then cooled to room temperature. Water was added and the reaction extracted several times with ethyl acetate. The combined organic phases were washed successively with water and brine, dried over sodium sulfate, filtered and evaporated. This gave 29 g of a crude fraction of the title compound (V-1), which were directly reacted further without further purification according to b) to (VI-1). b) Methyl 6-amino-4-bromopyridine-2-carboxylate (VI-1)
Eine Lösung von 70 g (angenommene Reinheit ca. 80% nach DC, ca. 165 mmol) einer hergestellten Rohfraktion von Methyl-4-brom-6-[(tert-butoxycarbonyl)amino]pyridin-2-carboxylat (V-1) in 400 ml Dichlormethan wurde im Eisbad gekühlt und 200 ml Trifluoressigsäure langsam und tropfenweise zugesetzt. Nach Beendigung der Zugabe wurde der Ansatz für 3 h bei Raumtemperatur gerührt. Anschließend wurde die Reaktionsmischung im Vakuum eingedampft. Der Rückstand wurde mit Ethylacetat verdünnt, mit gesättigter Natriumhydrogencarbonatlösung auf pH 11 eingestellt, nacheinander mit Wasser und Brine gewaschen, über Natriumsulfat getrocknet und filtriert. Das Filtrat wurde im Vakuum eingedampft. Man erhielt 40 g einer Rohfraktion der Titelverbindung (VI-1), die ohne weitere Aufreinigung direkt weiter umgesetzt wurde gemäß c) zu (VII-1). c) Methyl-4-brom-6-[(cyclopropylcarbonyl)amino]pyridin-2-carboxylat (VII-1) A solution of 70 g (assumed purity about 80% after TLC, about 165 mmol) of a prepared crude fraction of methyl 4-bromo-6 - [(tert-butoxycarbonyl) amino] pyridine-2-carboxylate (V-1) in 400 ml of dichloromethane was cooled in an ice bath and 200 ml of trifluoroacetic acid was added slowly and dropwise. After completion of the addition, the reaction was stirred for 3 h at room temperature. Subsequently, the reaction mixture was evaporated in vacuo. The residue was diluted with ethyl acetate, adjusted to pH 11 with saturated sodium bicarbonate solution, washed successively with water and brine, dried over sodium sulfate and filtered. The filtrate was evaporated in vacuo. This gave 40 g of a crude fraction of the title compound (VI-1), which was further reacted directly without further purification according to c) to (VII-1). c) Methyl 4-bromo-6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxylate (VII-1)
Zu einer gerührte Lösung von 29,0 g (angenommene Reinheit 100%, 126 mmol) einer Rohfraktion von Methyl-6-amino-4-brompyridin-2-carboxylat (VI-1) in 300 ml trockenem Dichlormethan wurden 20,0 g (251 mmol) Pyridin gegeben. Nach zehnminütigem Rühren bei Raumtemperatur wurde der Ansatz im Eisbad abgekühlt und 16,0 g (151 mmol) Cyclopropancarbonsäurechlorid zugegeben. Die Reaktionsmischung wurde weitere drei Stunden bei Raumtemperatur gerührt. Anschließend wurde der Ansatz mit Wasser verdünnt und die Phasen separiert. Die wässrige Phase wurde noch mehrmals mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden nacheinander mit Wasser und Brine gewaschen, übre Natriumsulfat getrocknet, filtriert und im Vakuum eingedampft. Der Rückstand wurde über eine Kieselgelsäule chromatographisch gereinigt (Ethylacetat in Hexan, 2%– 15%). Man erhielt 20,0 g (54,0% d. Th. über die drei Stufen a bis c) der Titelverbindung (VII-1). 1H-NMR (400,0 MHz, CDCl3): ^ = 8,69 (s, 1 H), 8,47 (s, 1 H), 7,99 (s, 1 H), 4,01 (s, 3 H), 1,52 (m, 1 H), 1,12 (m, 2 H), 0,95 (m, 2 H) 4-Brom-6-[(cyclopropylcarbonyl)amino]pyridin-2-carbonsäure (VIII-1) To a stirred solution of 29.0 g (assumed purity 100%, 126 mmol) of a crude fraction of methyl 6-amino-4-bromopyridine-2-carboxylate (VI-1) in 300 mL of dry dichloromethane was added 20.0 g ( 251 mmol) of pyridine. After stirring for ten minutes at room temperature, the reaction was cooled in an ice bath and 16.0 g (151 mmol) of cyclopropanecarboxylic acid chloride added. The reaction mixture was stirred for a further three hours at room temperature. The mixture was then diluted with water and the phases were separated. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were washed successively with water and brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by chromatography on a silica gel column (ethyl acetate in hexane, 2% -15%). 20.0 g (54.0% of theory) of the three steps a to c) of the title compound (VII-1) were obtained. 1H-NMR (400.0 MHz, CDCl 3): ^ = 8.69 (s, 1 H), 8.47 (s, 1 H), 7.99 (s, 1 H), 4.01 (s , 3H), 1.52 (m, 1H), 1.12 (m, 2H), 0.95 (m, 2H) 4-bromo-6 - [(cyclopropylcarbonyl) amino] pyridine-2 carboxylic acid (VIII-1)
Zu einer gerührten Lösung von 18,0 g (60,2 mmol) Methyl-4-brom-6-[(cyclopropylcarbonyl)amino]- pyridin-2-carboxylat (VII-1) in einer Mischung aus 100 ml THF und 100 ml Wasser wurden 7,6 g (181 mmol) Lithiumhydroxid-Monohydrat gegeben. Der Ansatz wurde 4 h bei Raumtemperatur gerührt. Anschließend wurde im Vakuum das THF aus der Reaktionsmischung entfernt. Die wässrige Phase wurde mit 4 N Salzsäure angesäuert und der ausfallende Niederschlag abfiltriert. Der Feststoff wurde mit Wasser gewaschen und durch Ko-evaporation mit Toluol getrocknet. Man erhielt 16,5 g (95,0% d. Th.) der Titelverbindung (VIII-1). 1H-NMR (400,0 MHz, d6-DMSO): ^ = 8,43 (s, 1 H), 8,25 (s, 1 H), 7,79 (s, 1 H), 2,28 (m, 1 H), 0,88 (d, 4 H) 4-Brom-N-(4-cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]pyridin-2-carboxamid (IX-1) To a stirred solution of 18.0 g (60.2 mmol) of methyl 4-bromo-6 - [(cyclopropylcarbonyl) amino] -pyridine-2-carboxylate (VII-1) in a mixture of 100 ml of THF and 100 ml Water was added to 7.6 g (181 mmol) of lithium hydroxide monohydrate. The batch was stirred for 4 h at room temperature. Subsequently, the THF was removed from the reaction mixture in vacuo. The aqueous phase was acidified with 4 N hydrochloric acid and the precipitate was filtered off. The solid was washed with water and dried by co-evaporation with toluene. 16.5 g (95.0% of theory) of the title compound (VIII-1) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): = 8.43 (s, 1 H), 8.25 (s, 1 H), 7.79 (s, 1 H), 2.28 (m, 1H), 0.88 (d, 4H) 4-bromo-N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxamide (IX-1)
Zu einer gerührten Lösung von 17,0 g (43,8 mmol) 4-Brom-6-[(cyclopropylcarbonyl)amino]pyridin-2- carbonsäure (VIII-1) in 200 ml trockenem Dimethylformamid wurden bei Raumtemperatur 43,0 g (110 mmol) HATU gegeben. Nach zehnminütigem Rühren wurden 8,1 g (48,2 mmol) 4- (Aminomethyl)benzonitril-Hydrochlorid sowie im Anschluss 17,0 g (132 mmol) N,N- Diisopropylethylamin hinzugefügt. Der Ansatz wurde noch 15 h bei Raumtemperatur gerührt. Anschließend wurde mit Wasser und Ethylacetat verdünnt und die Phasen separiert. Die wässrige Phase wurde mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden nacheinandert mit Wasser, 1 N Salzsäure, Brine und gesättigter Natriumhydrogencarbonatlösung gewaschen, über Natriumsulfat getrocknet und filtriert. Das Filtrat wurde im Vakuum eingedampft und der Rückstand über eine Kieselgelsäule chromatographisch gereinigt (Ethylacetat/Dichlormethan, 0 bis 1:20). Man erhielt 14,0 g (70,0% d. Th.) der Titelverbindung (IX-1). 1H-NMR (400,0 MHz, CDCl3): ^ = 8,61 (s, 1 H), 8,11 (s, broad, 2 H), 8,08 (s, 1 H), 7,62 (m, 2 H), 7,44 (m, 2 H), 4,69 (d, 2 H), 1,54 (m, 1 H), 1,13 (m, 2 H), 0,93 (m, 2 H) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)pyridin-2-carboxamid (X-1) To a stirred solution of 17.0 g (43.8 mmol) of 4-bromo-6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxylic acid (VIII-1) in 200 ml of dry dimethylformamide was added 43.0 g ( 110 mmol) HATU. After stirring for 10 minutes, 8.1 g (48.2 mmol) of 4- (aminomethyl) benzonitrile hydrochloride were added followed by 17.0 g (132 mmol) of N, N-diisopropylethylamine. The mixture was stirred for a further 15 h at room temperature. It was then diluted with water and ethyl acetate and the phases were separated. The aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed successively with water, 1 N hydrochloric acid, brine and saturated sodium bicarbonate solution, dried over sodium sulfate and filtered. The filtrate was evaporated in vacuo and the residue was purified by chromatography on a silica gel column (ethyl acetate / dichloromethane, 0 to 1:20). 14.0 g (70.0% of theory) of the title compound (IX-1) were obtained. 1H-NMR (400.0 MHz, CDCl3): = = 8.61 (s, 1H), 8.11 (s, broad, 2H), 8.08 (s, 1H), 7.62 ( m, 2H), 7.44 (m, 2H), 4.69 (d, 2H), 1.54 (m, 1H), 1.13 (m, 2H), 0.93 ( m, 2H) N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine-2-carboxamide (X- 1)
Alternative 1: Zu einer gerührten und entgasten Lösung von 9,2 g (23,1 mmol) 4-Brom-N-(4- cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]pyridin-2-carboxamid (IX-1), 7,3 g (28,8 mmol) Bis(pinacolato)-diboron und 6,64 g (69,0 mmol) Kaliumacetat in 100 ml trockenem 1,4-Dioxan wurden unter Argonatmosphäre 920 mg (1,28 mmol) [1,1′-Bis(diphenylphosphino)ferrocen]- palladium(II)dichlorid gegeben. Anschließend wurde der Ansatz für 16 h bei 85 °C unter Argonatmosphäre gerührt. Danach wurde die Reaktionslösung auf Raumtemperatur abgekühlt, über Celite filtriert und mit Dichlormethan nachgewaschen. Das Filtrat wurde im Vakuum eingedampft und der Rückstand aus einer Mischung von Hexan:Dichlormethan (5:1, V/V) umkristallisiert. Man erhielt 9,0 g (87,0% d. Th.) der Titelverbindung (X-1). 1H-NMR (400,0 MHz, CDCl3): ^ = 8,69 (s, 1 H), 8,29 (s, 1 H), 8,16 (broad, 1 H), 8,06 (broad, 1 H), 7,63 (d, 2 H), 7,45 (d, 2 H), 4,71 (d, 2 H), 1,55 (m, 1 H), 1,32 (s, 12 H), 1,13 (m, 2 H), 0,92 (m, 2 H) Alternative 2: Zu einer gerührten und entgasten Lösung von 250 mg (0,62 mmol) 4-Brom-N-(4- cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]pyridin-2-carboxamid (IX-1), 191 mg (0,75 mmol) Bis(pinacolato)-diboron und 184 mg (1,87 mmol) Kaliumacetat in 4 ml Acetonitril wurden in einem Mikrowellen-Reaktionsgefäß unter Argonatmosphäre 23 mg (0,03 mmol) [1,1′- Bis(diphenylphosphino)ferrocen]palladium(II)-dichlorid gegeben. Anschließend wurde der Ansatz für 15 Minuten in einer Biotage Initiator Mikrowelle auf 150 °C erhitzt. Danach wurde die Reaktionslösung auf Raumtemperatur abgekühlt, über eine Kieselgel/Natriumsulfat-Kartusche filtriert und mit Acetonitril und Ethylacetat nachgewaschen. Das Filtrat wurde im Vakuum eingedampft und der Rückstand mittels MPLC (reversed Phase; Fließmittel Wasser/Acetonitril) sauer chromatographisch getrennt. Man erhielt 190 mg (75,0% d. Th.) {2-[(4-Cyanbenzyl)carbamoyl]-6-[(cyclopropylcarbonyl)amino]pyridin-4- yl}borsäure (X-1b) als Hydrolyseprodukt der Titelverbindung (X-1). Weitere Umsetzung nach dieser Vorschrift resultierten regelmäßig in Gemischen von (X-1) mit dem Borsäurederivat (X-Ib) in variierendem Verhältnis. {2-[(4-Cyanbenzyl)carbamoyl]-6-[(cyclopropylcarbonyl)amino]pyridin-4-yl}borsäure (X-1b) Alternative 1: To a stirred and degassed solution of 9.2 g (23.1 mmol) of 4-bromo-N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxamide (IX-1). , 7.3 g (28.8 mmol) of bis (pinacolato) -diborone and 6.64 g (69.0 mmol) of potassium acetate in 100 ml of dry 1,4-dioxane under an argon atmosphere were added 920 mg (1.28 mmol) [ 1,1'-bis (diphenylphosphino) ferrocene] - palladium (II) dichloride. The mixture was then stirred for 16 h at 85 ° C under an argon atmosphere. Thereafter, the reaction solution was cooled to room temperature, filtered through Celite and washed with dichloromethane. The filtrate was evaporated in vacuo and the residue recrystallized from a mixture of hexane: dichloromethane (5: 1, v / v). This gave 9.0 g (87.0% of theory) of the title compound (X-1). 1H-NMR (400.0 MHz, CDCl3): ^ = 8.69 (s, 1H), 8.29 (s, 1H), 8.16 (broad, 1H), 8.06 (broad, 1 H), 7.63 (d, 2H), 7.45 (d, 2H), 4.71 (d, 2H), 1.55 (m, 1H), 1.32 (s, 12 H), 1.13 (m, 2 H), 0.92 (m, 2 H). Alternative 2: To a stirred and degassed solution of 250 mg (0.62 mmol) 4-bromo-N- (4- cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxamide (IX-1), 191 mg (0.75 mmol) of bis (pinacolato) diboron and 184 mg (1.87 mmol) of potassium acetate in 4 mL of acetonitrile 23 mg (0.03 mmol) of [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride were added in a microwave reaction vessel under argon atmosphere. The batch was then heated to 150 ° C for 15 minutes in a Biotage initiator microwave. Thereafter, the reaction solution was cooled to room temperature, filtered through a silica gel / sodium sulfate cartridge and washed with acetonitrile and ethyl acetate. The filtrate was evaporated in vacuo and the residue was purified by chromatography using MPLC (reversed phase, water / acetonitrile). There was obtained 190 mg (75.0% of theory) of {2 - [(4-cyanobenzyl) carbamoyl] -6 - [(cyclopropylcarbonyl) amino] pyridin-4-yl} boric acid (X-1b) as the hydrolysis product of the title compound (X-1). Further reaction according to this procedure resulted regularly in mixtures of (X-1) with the boric acid derivative (X-Ib) in varying proportions. {2 - [(4-Cyanobenzyl) carbamoyl] -6 - [(cyclopropylcarbonyl) amino] pyridin-4-yl} boric acid (X-1b)
logP (neutral / sauer): 1,25 / 1,58; MH+: 365; 1H-NMR (400,0 MHz, d6-DMSO): ^ ^= 10,679 (0,9); 8,843 (0,5); 8,559 (0,4); 8,496 (1,3); 8,090 (1,3); 7,829 (1,2); 7,809 (1,5); 7,532 (1,2); 7,512 (1,1); 4,631 (1,0); 4,616 (1,0); 3,569 (16,0); 3,362 (0,6); 2,507 (14,0); 2,503 (18,4); 2,499 (13,9); 1,987 (0,4); 1,355 (0,3); 1,320 (0,5); 0,834 (2,0); 0,823 (1,2); 0,814 (1,0); 0,000 (5,3) N-(4-Cyanobenzyl)-6'-[(cyclopropylcarbonyl)amino]-6-(trifluoromethyl)-3,4'-bipyridin-2'- carboxamid (I-123) logP (neutral / acid): 1.25 / 1.58; MH +: 365; 1H-NMR (400.0 MHz, d6-DMSO): ^^ = 10.679 (0.9); 8,843 (0.5); 8,559 (0.4); 8.496 (1.3); 8.090 (1.3); 7.829 (1.2); 7,809 (1.5); 7,532 (1.2); 7,512 (1,1); 4,631 (1.0); 4.616 (1.0); 3,569 (16.0); 3.362 (0.6); 2,507 (14.0); 2,503 (18,4); 2,499 (13.9); 1,987 (0.4); 1.355 (0.3); 1.320 (0.5); 0.834 (2.0); 0.823 (1.2); 0.814 (1.0); 0.000 (5.3) N- (4-cyanobenzyl) -6 '- [(cyclopropylcarbonyl) amino] -6- (trifluoromethyl) -3,4'-bipyridine-2'-carboxamide (I-123)
200 mg (angenommene Reinheit 100%, 0,55 mmol) der nach Alternative 2 erhaltenen {2-[(4- Cyanbenzyl)carbamoyl]-6-[(cyclopropylcarbonyl)amino]pyridin-4-yl}borsäure (X-1b), 113 mg (0,50 mmol) 5-Brom-2-(trifluormethyl)pyridin und 106 mg (1,0 mmol) Natriumcarbonat wurden in ein Mikrowellengefäß eingewogen. Anschließend wurden 8 ml 1,4-Dioxan und 1,5 ml Wasser hinzugefügt und die Mischung entgast. Das Vial wurde mit Argon geflutet und 17,4 mg (0,01 mmol) Tetrakis(triphenylphosphin)palladium(0) hinzugegeben. Der Ansatz wurde für 45 Minuten bei 130 °C in einer IR Discover Mikrowelle erhitzt. Danach wurde die Reaktionslösung auf Raumtemperatur abgekühlt, über eine Kieselgel/Natriumsulfat-Kartusche filtriert und mit 1,4-Dioxan nachgewaschen. Das Filtrat wurde im Vakuum eingedampft und der Rückstand mittels HPLC-Trennung aufgereinigt. Man erhielt 76 mg (100% Reinheit, 32,7% d. Th.) der Titelverbindung (I-123). logP (sauer): 3,02; MH+: 466; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 11,059 (5,6); 9,159 (4,8); 9,154 (4,9); 9,006 (1,5); 8,990 (3,2); 8,975 (1,6); 8,585 (7,7); 8,581 (7,9); 8,483 (2,4); 8,478 (2,4); 8,463 (2,6); 8,458 (2,7); 8,317 (4,9); 8,092 (8,6); 8,088 (8,7); 8,081 (5,4); 8,060 (4,6); 7,843 (8,8); 7,822 (10,3); 7,561 (8,8); 7,540 (7,6); 4,663 (6,3); 4,648 (6,4); 3,429 (0,3); 3,387 (0,5); 3,378 (0,6); 3,369 (0,7); 3,331 (645,6); 3,307 (2,7); 3,278 (0,5); 2,695 (0,3); 2,676 (3,7); 2,671 (5,2); 2,667 (3,9); 2,662 (2,0); 2,641 (0,4); 2,602 (0,4); 2,550 (1,2); 2,525 (13,1); 2,520 (20,4); 2,511 (287,6); 2,507 (600,0); 2,502 (797,7); 2,498 (587,3); 2,493 (292,3); 2,414 (0,5); 2,334 (3,7); 2,329 (5,2); 2,325 (3,8); 2,083 (0,6); 2,068 (1,6); 2,052 (2,3); 2,037 (1,8); 2,021 (0,7); 1,989 (0,9); 1,398 (1,4); 1,175 (0,5); 1,148 (0,6); 0,879 (16,0); 0,866 (8,7); 0,862 (8,5); 0,146 (5,0); 0,056 (0,4); 0,047 (0,5); 0,043 (0,4); 0,038 (0,4); 0,027 (0,7); 0,020 (1,5); 0,008 (38,1); 0,000 (1148,9); -0,008 (52,0); -0,023 (2,0); -0,031 (1,3); -0,033 (1,3); -0,041 (0,6); - 0,045 (0,4); -0,052 (0,8); -0,150 (5,1) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-[5-(trifluormethyl)-2-thienyl]pyridin-2- carboxamid (I-160) 200 mg (assumed purity 100%, 0.55 mmol) of {2 - [(4-cyanobenzyl) carbamoyl] -6 - [(cyclopropylcarbonyl) amino] pyridin-4-yl} boric acid (X-1b) obtained in Alternative 2 , 113 mg (0.50 mmol) of 5-bromo-2- (trifluoromethyl) pyridine and 106 mg (1.0 mmol) of sodium carbonate were weighed into a microwave vessel. Then 8 ml of 1,4-dioxane and 1.5 ml of water were added and the mixture was degassed. The vial was flooded with argon and 17.4 mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. The batch was heated for 45 minutes at 130 ° C in an IR Discover microwave. Thereafter, the reaction solution was cooled to room temperature, filtered through a silica gel / sodium sulfate cartridge and washed with 1,4-dioxane. The filtrate was evaporated in vacuo and the residue purified by HPLC separation. 76 mg (100% purity, 32.7% of theory) of the title compound (I-123) were obtained. logP (acid): 3.02; MH +: 466; 1H-NMR (400.0 MHz, d6-DMSO): ^ = 11.059 (5.6); 9,159 (4,8); 9.154 (4.9); 9.006 (1.5); 8,990 (3.2); 8.975 (1.6); 8,585 (7.7); 8,581 (7.9); 8.483 (2.4); 8.478 (2.4); 8.463 (2.6); 8.458 (2.7); 8.317 (4.9); 8.092 (8.6); 8.088 (8.7); 8,081 (5.4); 8.060 (4.6); 7,843 (8.8); 7,822 (10.3); 7,561 (8.8); 7,540 (7.6); 4,663 (6.3); 4,648 (6.4); 3,429 (0.3); 3.387 (0.5); 3.378 (0.6); 3.369 (0.7); 3,331 (645.6); 3,307 (2.7); 3,278 (0.5); 2,695 (0.3); 2,676 (3.7); 2,671 (5.2); 2,667 (3.9); 2,662 (2.0); 2.641 (0.4); 2.602 (0.4); 2,550 (1.2); 2,525 (13.1); 2,520 (20.4); 2,511 (287.6); 2,507 (600.0); 2,502 (797,7); 2,498 (587.3); 2,493 (292.3); 2,414 (0.5); 2,334 (3.7); 2,329 (5.2); 2.325 (3.8); 2,083 (0.6); 2,068 (1.6); 2.052 (2.3); 2.037 (1.8); 2.021 (0.7); 1,989 (0.9); 1,398 (1.4); 1,175 (0.5); 1,148 (0.6); 0.879 (16.0); 0.866 (8.7); 0.862 (8.5); 0.146 (5.0); 0.056 (0.4); 0.047 (0.5); 0.043 (0.4); 0.038 (0.4); 0.027 (0.7); 0.020 (1.5); 0.008 (38.1); 0.000 (1148.9); -0.008 (52.0); -0.023 (2.0); -0.031 (1.3); -0.033 (1.3); -0.041 (0.6); - 0.045 (0.4); -0.052 (0.8); -0.150 (5.1) N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- [5- (trifluoromethyl) -2-thienyl] pyridine-2-carboxamide (I-160)
100 mg (angenommene Reinheit 100%, 0,27 mmol) der nach Alternative 2 erhaltenen {2-[(4- Cyanbenzyl)carbamoyl]-6-[(cyclopropylcarbonyl)amino]pyridin-4-yl}borsäure (X-1b), 58 mg (0,25 mmol) 2-Brom-5-(trifluormethyl)thiophen und 53 mmg (0,5 mmol) Natriumcarbonat wurden in ein Mikrowellengefäß eingewogen. Anschließend wurden 4,5 ml 1,4-Dioxan und 0,9 ml Wasser hinzugefügt und die Mischung entgast. Das Vial wurde mit Argon geflutet und 8,7 mg (0,008 mmol) Tetrakis(triphenylphosphin)palladium(0) hinzugegeben. Der Ansatz wurde für 45 Minuten bei 130 °C in einer IR Discover Mikrowelle erhitzt. Danach wurde die Reaktionslösung auf Raumtemperatur abgekühlt, über eine Kieselgel/Natriumsulfat-Kartusche filtriert und mit 1,4-Dioxan nachgewaschen. Das Filtrat wurde im Vakuum eingedampft und der Rückstand mittels HPLC-Trennung aufgereinigt. Man erhielt 29 mg (100% Reinheit, 24,9% d. Th.) der Titelverbindung (I-160). logP (neutral / sauer): - / 3,73; MH+: 471; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 11,030 (7,7); 10,929 (0,4); 8,948(2,2); 8,932(4,6); 8,916(2,2); 8,589 (0,6); 8,551 (9,4); 8,548 (10,0); 8,511 (0,6); 8,266 (0,5); 8,059 (0,6); 8,024 (10,0); 8,020 (10,4); 7,941 (4,3); 7,933 (5,0); 7,838 (15,6); 7,817 (14,1); 7,553 (12,7); 7,532 (11,0); 4,650 (9,8); 4,634 (9,8); 3,469 (0,4); 3,453 (0,4); 3,432 (0,6); 3,426 (0,5); 3,398 (0,9); 3,326 (1198,6); 3,284(0,8); 3,271 (0,7); 3,260 (0,6); 3,237 (0,4); 2,711 (0,7); 2,675 (3,1); 2,671 (4,2); 2,667 (3,2); 2,606 (0,4); 2,541 (145,4); 2,524 (12,7); 2,506 (496,4); 2,502 (656,3); 2,498 (502,1); 2,408 (0,3); 2,367 (0,7); 2,333 (3,0); 2,328 (4,1); 2,324 (3,2); 2,067 (0,7); 2,049 (2,0); 2,044 (1,7); 2,036 (3,3); 2,023 (2,1); 2,005 (0,9); 1,298 (0,4); 1,259 (0,6); 1,235 (1,2); 1,187 (0,4); 0,904 (0,5); 0,879 (16,0); 0,872 (12,3); 0,860 (8,9); 0,837 (0,7); 0,008 (1,5); 0,000 (45,1) N-(4-cyanobenzyl)-6'-[(cyclopropylcarbonyl)amino]-5-(trifluoromethyl)-2,4'-bipyridin-2'- carboxamid (I-174) 100 mg (assumed purity 100%, 0.27 mmol) of {2 - [(4-cyanobenzyl) carbamoyl] -6 - [(cyclopropylcarbonyl) amino] pyridin-4-yl} boric acid (X-1b) obtained in Alternative 2 , 58 mg (0.25 mmol) of 2-bromo-5- (trifluoromethyl) thiophene and 53 mmg (0.5 mmol) of sodium carbonate were weighed into a microwave vessel. Subsequently, 4.5 ml of 1,4-dioxane and 0.9 ml of water were added and the mixture was degassed. The vial was flooded with argon and 8.7 mg (0.008 mmol) of tetrakis (triphenylphosphine) palladium (0) added. The batch was heated for 45 minutes at 130 ° C in an IR Discover microwave. Thereafter, the reaction solution was cooled to room temperature, filtered through a silica gel / sodium sulfate cartridge and washed with 1,4-dioxane. The filtrate was evaporated in vacuo and the residue purified by HPLC separation. 29 mg (100% purity, 24.9% of theory) of the title compound (I-160) were obtained. logP (neutral / acid): - / 3.73; MH +: 471; 1H-NMR (400.0 MHz, d6-DMSO): ^ = 11.030 (7.7); 10.929 (0.4); 8,948 (2.2); 8,932 (4.6); 8.916 (2.2); 8,589 (0.6); 8,551 (9.4); 8,548 (10.0); 8,511 (0.6); 8.266 (0.5); 8,059 (0.6); 8.024 (10.0); 8.020 (10.4); 7,941 (4.3); 7,933 (5.0); 7.838 (15.6); 7,817 (14,1); 7,553 (12,7); 7,532 (11.0); 4,650 (9.8); 4,634 (9.8); 3.469 (0.4); 3,453 (0.4); 3,432 (0.6); 3,426 (0.5); 3,398 (0.9); 3,326 (1198.6); 3,284 (0.8); 3,271 (0.7); 3,260 (0.6); 3,237 (0.4); 2,711 (0.7); 2,675 (3.1); 2,671 (4.2); 2,667 (3.2); 2,606 (0.4); 2,541 (145.4); 2,524 (12.7); 2,506 (496.4); 2,502 (656.3); 2,498 (502.1); 2.408 (0.3); 2.367 (0.7); 2.333 (3.0); 2,328 (4,1); 2.324 (3.2); 2.067 (0.7); 2,049 (2.0); 2.044 (1.7); 2.036 (3.3); 2.023 (2.1); 2.005 (0.9); 1,298 (0.4); 1,259 (0.6); 1.235 (1.2); 1.187 (0.4); 0.904 (0.5); 0.879 (16.0); 0.872 (12.3); 0.860 (8.9); 0.837 (0.7); 0.008 (1.5); 0,000 (45.1) N- (4-cyano-benzyl) -6 '- [(cyclopropylcarbonyl) amino] -5- (trifluoromethyl) -2,4'-bipyridine-2'-carboxamide (I-174)
240 mg (angenommene Reinheit 100%, 0,65 mmol) der nach Alternative 2 erhaltenen {2-[(4- Cyanbenzyl)carbamoyl]-6-[(cyclopropylcarbonyl)amino]pyridin-4-yl}borsäure (X-1b) und 179 mg (0,79 mmol) 2-Brom-5-(trifluormethyl)pyridin wurden in ein Mikrowellengefäß eingewogen. Anschließend wurden 4 ml 1,4-Dioxan sowie 0,75 ml einer zweimolaren wässrigen Natriumcarbonatlösung hinzugefügt und die Mischung entgast. Das Vial wurde mit Argon geflutet und 22,8 mg (0,02 mmol) Tetrakis(triphenylphosphin)palladium(0) hinzugegeben. Der Ansatz wurde für 45 Minuten bei 130 °C in einer IR Discover Mikrowelle erhitzt. Danach wurde die Reaktionslösung auf Raumtemperatur abgekühlt, mit Ethylacetat verdünnt und über eine Kieselgel/Natriumsulfat-Kartusche filtriert und mit Ethylacetat nachgewaschen. Das Filtrat wurde im Vakuum eingedampft und der Rückstand mittels MPLC (Fließmittel Cyclohexan:Ethylacetat 1:8) chromatographisch aufgereinigt. Man erhielt 110 mg (95,0% Reinheit, 34,1% d. Th.) der Titelverbindung (I-174). logP (neutral / sauer): 3,22 / 3,25; MH+: 466; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 11,012 (8,2); 9,164 (7,4); 8,994 (11,4); 8,991 (11,9); 8,970 (2,2); 8,955 (4,6); 8,939 (2,2); 8,409 (3,0); 8,398 (12,9); 8,394 (13,3); 8,389 (5,7); 8,383 (5,3); 8,339 (7,9); 8,318 (4,4); 7,842 (13,3); 7,821 (15,9); 7,808 (0,6); 7,565 (13,7); 7,544 (11,9); 7,514 (0,4); 4,671 (10,3); 4,655 (10,3); 4,626 (0,3); 4,613 (0,4); 3,410 (12,1); 3,356 (18,0); 2,676 (0,9); 2,672 (1,3); 2,668 (1,0); 2,525 (3,0); 2,507 (166,3); 2,503 (222,3); 2,499 (162,9); 2,334 (0,9); 2,330 (1,3); 2,325 (1,0); 2,081 (0,8); 2,068 (1,8); 2,063 (2,1); 2,058 (1,7); 2,051 (3,6); 2,038 (2,2); 2,033 (2,1); 2,020 (1,0); 1,070 (1,8); 0,912 (0,6); 0,888 (11,5); 0,879 (16,0); 0,860 (8,6); 0,840 (1,0); 0,824 (0,3); 0,008 (0,7); 0,000 (21,9); -0,008 (0,8) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-[2-ethyl-6-methyl-4- (pentafluorethyl)phenyl]pyridin-2-carboxamid (I-148) 240 mg (assumed purity 100%, 0.65 mmol) of {2 - [(4-cyanobenzyl) carbamoyl] -6 - [(cyclopropylcarbonyl) amino] pyridin-4-yl} boric acid (X-1b) obtained in Alternative 2 and 179 mg (0.79 mmol) of 2-bromo-5- (trifluoromethyl) pyridine were weighed into a microwave vessel. Then 4 ml of 1,4-dioxane and 0.75 ml of a two-molar aqueous sodium carbonate solution were added and the mixture was degassed. The vial was flooded with argon and 22.8 mg (0.02 mmol) of tetrakis (triphenylphosphine) palladium (0) added. The batch was heated for 45 minutes at 130 ° C in an IR Discover microwave. Thereafter, the reaction solution was cooled to room temperature, diluted with ethyl acetate and filtered through a silica gel / sodium sulfate cartridge and washed with ethyl acetate. The filtrate was evaporated in vacuo and the residue was purified by MPLC (eluent cyclohexane: ethyl acetate 1: 8) by chromatography. 110 mg (95.0% purity, 34.1% of theory) of the title compound (I-174) were obtained. logP (neutral / acid): 3.22 / 3.25; MH +: 466; 1H-NMR (400.0 MHz, d6-DMSO): ^ = 11.012 (8.2); 9.164 (7.4); 8,994 (11.4); 8,991 (11.9); 8,970 (2.2); 8,955 (4.6); 8.939 (2.2); 8,409 (3.0); 8,398 (12.9); 8,394 (13.3); 8,389 (5.7); 8,383 (5.3); 8,339 (7.9); 8,318 (4,4); 7,842 (13.3); 7,821 (15.9); 7,808 (0.6); 7,565 (13.7); 7,544 (11.9); 7,514 (0.4); 4,671 (10.3); 4,655 (10.3); 4,626 (0.3); 4,613 (0.4); 3,410 (12.1); 3.356 (18.0); 2,676 (0.9); 2,672 (1.3); 2,668 (1.0); 2,525 (3.0); 2,507 (166,3); 2,503 (222,3); 2,499 (162.9); 2,334 (0.9); 2,330 (1,3); 2.325 (1.0); 2.081 (0.8); 2,068 (1.8); 2,063 (2.1); 2.058 (1.7); 2,051 (3.6); 2.038 (2.2); 2.033 (2.1); 2,020 (1.0); 1,070 (1.8); 0.912 (0.6); 0,888 (11.5); 0.879 (16.0); 0.860 (8.6); 0.840 (1.0); 0.824 (0.3); 0.008 (0.7); 0.000 (21.9); -0.008 (0.8) N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- [2-ethyl-6-methyl-4- (pentafluoroethyl) phenyl] pyridine-2-carboxamide (I) 148)
152 mg (0,34 mmol) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridin-2-carboxamid (X-1), 108 mg (0,34 mmol) 2-Brom-1-ethyl-3-methyl-5- (pentafluorethyl)benzol (Synthese z.B. analog 4-Brom-2-fluor-1-(pentafluorethyl)benzol in WO2012010573) und 12 mg (0,01 mmol) Tetrakis(triphenylphosphin)palladium(0) wurden in einem Gemisch aus entgastem Dioxan (3,8 mL) und entgaster Natriumcarbonatlösung (1M, 1,4 mL) vorgelegt und 14 h bei 92° C gerührt. Anschließend wurde auf Raumtemperatur abgekühlt, das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde in Dichlormethan und Wasser aufgenommen. Die Phasen wurden getrennt, die wässrige Phase wurde zweimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Aufreinigung mit einem Cyclohexan / Ethylacetat Gradienten als Laufmittel gereinigt. Man erhielt 38 mg (97% Reinheit, 20% d. Th.) der Titelverbindung (I-148). logP (neutral/sauer): 4,72 / 4,85; MH+: 557; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,82-0,84 (m, 4H), 0,99 (t, 3H), 1,99-2,08 (m, 4H), 2,32-2,42 (m, 2H), 4,64 (d, 2H), 7,49-7,57 (m, 5H), 7,82-7,84 (m, 2H), 8,04 (d, 1H), 8,92 (t, 1H), 11,00 (s, 1H). N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin-2- carboxamid (I-149) 152 mg (0.34 mmol) of N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine-2-carboxamide (X-1), 108 mg (0.34 mmol) of 2-bromo-1-ethyl-3-methyl-5- (pentafluoroethyl) benzene (synthesis, for example, analogously to 4-bromo-2-fluoro-1 - (pentafluoroethyl) benzene in WO2012010573) and 12 mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium (0) were placed in a mixture of degassed dioxane (3.8 mL) and degassed sodium carbonate solution (1M, 1.4 mL) and stirred at 92 ° C for 14 h. It was then cooled to room temperature, the reaction mixture was concentrated in vacuo and the residue was taken up in dichloromethane and water. The phases were separated, the aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography purification with a cyclohexane / ethyl acetate gradient as eluent. 38 mg (97% purity, 20% of theory) of the title compound (I-148) were obtained. logP (neutral / acid): 4.72 / 4.85; MH +: 557; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 0.82-0.84 (m, 4H), 0.99 (t, 3H), 1.99-2.08 (m, 4H), 2 , 32-2.42 (m, 2H), 4.64 (d, 2H), 7.49-7.57 (m, 5H), 7.82-7.84 (m, 2H), 8.04 (d, 1H), 8.92 (t, 1H), 11.00 (s, 1H). N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridine-2-carboxamide (I-149)
150 mg (0,34 mmol) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridin-2-carboxamid (X-1), 99 mg (0,34 mmol) 4-Brom-2-fluor-1- (pentafluorethyl)benzol (Synthese: siehe z.B. WO2012010573) und 12 mg (0,01 mmol) Tetrakis(triphenylphosphin)palladium(0) wurden in einem Gemisch aus entgastem Dioxan (3,8 mL) und entgaster Natriumcarbonatlösung (1M, 1,3 mL) vorgelegt und 14 h bei 92° C gerührt. Anschließend wurde auf Raumtemperatur abgekühlt, das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde in Dichlormethan und Wasser aufgenommen. Die Phasen wurden getrennt, die wässrige Phase wurde zweimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Aufreinigung mit einem Cyclohexan / Ethylacetat Gradienten als Laufmittel gereinigt. Man erhielt 53 mg (99% Reinheit, 29% d. Th.) der Titelverbindung (I-149). logP (neutral/sauer): 4,14 / 4,25; MH+: 533; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,86-0,88 (m, 4H), 2,03-2,06 (m, 1H), 4,65 (d, 2H), 7,54-7,56 (m, 2H), 7,82-8,00 (m, 5H), 8,05 (d, 1H), 8,56 (d, 1H), 8,97 (t, 1H), 11,03 (s, 1H). 4-[(1,1,2,2-Tetrafluorethyl)sulfanyl]phenyl-trifluormethansulfonat 150 mg (0.34 mmol) of N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine-2-carboxamide (X-1), 99 mg (0.34 mmol) of 4-bromo-2-fluoro-1- (pentafluoroethyl) benzene (synthesis: see, for example, WO2012010573) and 12 mg (0.01 mmol) of tetrakis (Triphenylphosphine) palladium (0) were placed in a mixture of degassed dioxane (3.8 mL) and degassed sodium carbonate solution (1M, 1.3 mL) and stirred at 92 ° C for 14 h. Subsequently was cooled to room temperature, the reaction mixture was concentrated in vacuo and the residue was taken up in dichloromethane and water. The phases were separated, the aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography purification with a cyclohexane / ethyl acetate gradient as eluent. 53 mg (99% purity, 29% of theory) of the title compound (I-149) were obtained. logP (neutral / acid): 4.14 / 4.25; MH +: 533; 1 H NMR (400 MHz, D 6 -DMSO) ppm ppm: 0.86-0.88 (m, 4H), 2.03-2.06 (m, 1H), 4.65 (d, 2H), 7.54-7.56 (m, 2H), 7.82-8.00 (m, 5H), 8.05 (d, 1H), 8.56 (d, 1H), 8.97 (t, 1H), 11.03 (s, 1H). 4 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenyl trifluoromethanesulfonate
150 mg (0,66 mmol) 4-[(1,1,2,2-Tetrafluorethyl)sulfanyl]phenol und 81 mg (0,79 mmol) Triethylamin wurden in Dichlormethan bei 0° C vorgelegt und mit 225 mg (0,79 mmol) Trifluormethansulfonsäureanhydrid versetzt. Die Mischung wurde 14 h bei Raumtemperatur gerührt und anschließend mit Wasser versetzt. Die Phasen wurden getrennt, die wässrige Phase wurde zweimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert. Das Rohprodukt wurde ohne weitere Reinigung in der nächsten Stufe eingesetzt. N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-{4-[(1,1,2,2-tetrafluorethyl)- sulfanyl]phenyl}pyridin-2-carboxamid (I-178) 150 mg (0.66 mmol) of 4 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenol and 81 mg (0.79 mmol) of triethylamine were initially charged in dichloromethane at 0 ° C. and treated with 225 mg (0, 79 mmol) Trifluormethansulfonsäureanhydrid added. The mixture was stirred for 14 h at room temperature and then treated with water. The phases were separated, the aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo. The crude product was used without further purification in the next step. N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- {4 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenyl} pyridine-2-carboxamide (I-178)
150 mg (0,34 mmol) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridin-2-carboxamid (X-1), 120 mg (0,34 mmol) 4-[(1,1,2,2- Tetrafluorethyl)sulfanyl]phenyl-trifluormethansulfonat und 12 mg (0,01 mmol) Tetrakis(triphenylphosphin)palladium(0) wurden in einem Gemisch aus entgastem Dioxan (3,8 mL) und entgaster Natriumcarbonatlösung (1M, 1,3 mL) vorgelegt und 14 h bei 92° C gerührt. Anschließend wurde auf Raumtemperatur abgekühlt, das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde in Dichlormethan und Wasser aufgenommen. Die Phasen wurden getrennt, die wässrige Phase wurde zweimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Aufreinigung mit einem Cyclohexan / Ethylacetat Gradienten als Laufmittel gereinigt. Man erhielt 69 mg (98% Reinheit, 38% d. Th.) der Titelverbindung (I-178). logP (sauer): 3,81; MH+: 529; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,85-0,87 (m, 4H), 2,01-2,07 (m, 1H), 4,65 (d, 2H), 6,62-6,90 (m, 1H), 7,54-7,56 (m, 2H), 7,82-7,91 (m, 6H), 8,00 (d, 1H), 8,56 (d, 1H), 8,94 (t, 1H), 10,97 (s, 1H). N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2- carboxamid (I-044) 150 mg (0.34 mmol) of N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine-2-carboxamide (X-1), 120 mg (0.34 mmol) of 4 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenyl trifluoromethanesulfonate and 12 mg (0.01 mmol) of tetrakis (triphenylphosphine ) Palladium (0) were placed in a mixture of degassed dioxane (3.8 mL) and degassed sodium carbonate solution (1M, 1.3 mL) and stirred at 92 ° C for 14 h. It was then cooled to room temperature, the reaction mixture was concentrated in vacuo and the residue was taken up in dichloromethane and water. The phases were separated, the aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography purification with a cyclohexane / ethyl acetate gradient as eluent. 69 mg (98% purity, 38% of theory) of the title compound (I-178) were obtained. logP (acid): 3.81; MH +: 529; 1 H-NMR (400 MHz, D 6 -DMSO) ppm ppm: 0.85-0.87 (m, 4H), 2.01-2.07 (m, 1H), 4.65 (d, 2H), 6.62-6.90 (m, 1H), 7.54-7.56 (m, 2H), 7.82-7.91 (m, 6H), 8.00 (d, 1H), 8, 56 (d, 1H), 8.94 (t, 1H), 10.97 (s, 1H). N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (I-044)
500 mg (1,25 mmol) 4-Brom-N-(4-cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]pyridin-2-carboxamid (IX-1), 258 mg (1,25 mmol) 4-(Trifluormethoxy)phenylboronsäure und 43 mg (0,04 mmol) Tetrakis(triphenylphosphin)palladium(0) wurden in einem Gemisch aus entgastem Dioxan (12 mL) und entgaster Natriumcarbonatlösung (1M, 5 mL) vorgelegt und 14 h bei 96° C gerührt. Anschließend wurde auf Raumtemperatur abgekühlt, das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde in Dichlormethan und Wasser aufgenommen. Die Phasen wurden getrennt, die wässrige Phase wurde zweimal mit Dichlormethan extrahiert und die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Aufreinigung mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. Man erhielt 193 mg (100% Reinheit, 32% d. Th.) der Titelverbindung (I-044). logP (neutral/sauer): 3,76/3,90; MH+: 481; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,85-0,87 (m, 4H), 2,01-2,07 (m, 1H), 4,65 (d, 2H), 7,52-7,56 (m, 4H), 7,82-7,84 (m, 2H), 7,89-7,92 (m, 2H), 7,98 (d, 1H), 8,53 (d, 1H), 8,94 (t, 1H), 10,97 (s, 1H). Dimethyl-4-chlorpyridin-2,6-dicarboxylat (IIa-1) 500 mg (1.25 mmol) of 4-bromo-N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] pyridine-2-carboxamide (IX-1), 258 mg (1.25 mmol) of 4- ( Trifluoromethoxy) phenylboronic acid and 43 mg (0.04 mmol) of tetrakis (triphenylphosphine) palladium (0) were placed in a mixture of degassed dioxane (12 mL) and degassed sodium carbonate solution (1M, 5 mL) and stirred at 96 ° C for 14 h. It was then cooled to room temperature, the reaction mixture was concentrated in vacuo and the residue was taken up in dichloromethane and water. The phases were separated, the aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography with a water / acetonitrile gradient as eluent. 193 mg (100% purity, 32% of theory) of the title compound (I-044) were obtained. logP (neutral / acid): 3.76 / 3.90; MH +: 481; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 0.85-0.87 (m, 4H), 2.01-2.07 (m, 1H), 4.65 (d, 2H), 7 , 52-7.56 (m, 4H), 7.82-7.84 (m, 2H), 7.89-7.92 (m, 2H), 7.98 (d, 1H), 8.53 (d, 1H), 8.94 (t, 1H), 10.97 (s, 1H). Dimethyl 4-chloropyridine-2,6-dicarboxylate (IIa-1)
Zu einer gerührten Suspension von 100,0 g (546 mmol) 4-Hydroxy-pyridin-2,6-dicarbonsäure (II-1) in 1500 ml Tetrachlorkohlenstoff wurden 455,0 g (2184 mmol) Phosphorpentachlorid gegeben. Die resultierende Mischung wurde für 16 h unter Rückfluss erhitzt und anschließend vorsichtig und tropfenweise bei einer Temperatur < 80 °C mit 375 ml Methanol gequencht. Der Ansatz wurde noch 1 h unter Rückfluss gerührt, auf Raumtemperatur abgekühlt und im Vakuum eingedampft. Der Rückstand wurde mit Eiswasser versetzt und noch eine Stunde gerührt. Der ausfallende Feststoff wurde abfiltriert, mit Wasser gewaschen und im Vakuum getrocknet. Man erhielt 72,0 g (57,0% d. Th.) der Titelverbindung (IIa-1). 1H-NMR (400,0 MHz, CDCl3): ^ = 8,30 (s, 2 H), 4,04 (s, 6 H) Dimethyl-4-iodpyridin-2,6-dicarboxylat (III-2) To a stirred suspension of 100.0 g (546 mmol) of 4-hydroxy-pyridine-2,6-dicarboxylic acid (II-1) in 1500 mL of carbon tetrachloride was added 455.0 g (2184 mmol) of phosphorus pentachloride. The resulting mixture was refluxed for 16 h and then quenched cautiously and dropwise at a temperature <80 ° C with 375 mL of methanol. The mixture was stirred for a further 1 h under reflux, cooled to room temperature and evaporated in vacuo. The residue was mixed with ice-water and stirred for one more hour. The precipitated solid was filtered off, washed with water and dried in vacuo. 72.0 g (57.0% of theory) of the title compound (IIa-1) were obtained. 1H-NMR (400.0 MHz, CDCl 3): ^ = 8.30 (s, 2 H), 4.04 (s, 6 H) dimethyl-4-iodopyridine-2,6-dicarboxylate (III-2)
Zu einer gerührten Mischung von 72,0 g (314 mmol) Dimethyl-4-chlorpyridin-2,6-dicarboxylat (II-1) und 310 g Natriumiodid in 1500 ml Acetonitril wurden bei 0 °C 66,0 ml (941 mmol) Acetylchlorid gegeben. Die resultierende Mischung wurde für 4 h auf 50 °C erhitzt und anschließend im Vakuum das Acetonitril entfernt. Der Rückstand wurde vorsichtig in gesättigte Natriumcarbonatlösung eingetragen und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden nacheinander mit gesättigter Natriumthiosulfatlösung und Wasser gewaschen, über Natriumsulfat getrocknet und eingedampft. Man erhielt 100,0 g (99,0% d. Th.) der Titelverbindung (III-2). 1H-NMR (400,0 MHz, CDCl3): ^ = 8,67 (s, 2 H), 4,02 (s, 6 H) 4-Iod-6-(methoxycarbonyl)pyridin-2-carbonsäure (IV-2) To a stirred mixture of 72.0 g (314 mmol) of dimethyl 4-chloropyridine-2,6-dicarboxylate (II-1) and 310 g of sodium iodide in 1500 mL of acetonitrile was added 66.0 mL (941 mmol) at 0 ° C. Given acetyl chloride. The resulting mixture was heated at 50 ° C for 4 h and then the acetonitrile was removed in vacuo. The residue was carefully added to saturated sodium carbonate solution and extracted with dichloromethane. The combined organic phases were washed successively with saturated sodium thiosulfate solution and water, dried over sodium sulfate and evaporated. 100.0 g (99.0% of theory) of the title compound (III-2) were obtained. 1 H-NMR (400.0 MHz, CDCl 3 ): ^ = 8.67 (s, 2H), 4.02 (s, 6H) 4-iodo-6- (methoxycarbonyl) pyridine-2-carboxylic acid (IV -2)
100,0 g (312 mmol) Dimethyl-4-iodpyridin-2,6-dicarboxylat (III-2) wurden in 1000 ml einer 10:1- Mischung (V/V) Methanol:Dichlormethan suspendiert und 14,8 g (265 mmol) Kaliumhydroxid zugegeben. Die Reaktionsmischung wurde für 6 h bei Raumtemperatur gerührt. Anschließend wurde der Ansatz mit 1500 ml Diethylether versetzt und weitere 30 Minuten gerührt. Der ausfallende Feststoff wurde abfiltriert und mit Diethylether gewaschen. Anschließend wurde der Filterrückstand resuspendiert und mit 3 N HCl auf pH 3 angesäuert. Der ausfallende Feststoff wurde abfiltriert, nacheinander mit Dichlormethan und Diethylether gewaschen und im Vakuum getrocknet. Man erhielt 56,0 g (58,0% d. Th.) der Titelverbindung (IV-2). 1H-NMR (400,0 MHz, d6-DMSO): ^ = 8,47 (s, 1 H), 8,40 (s, 1 H), 3,90 (s, 3 H) Methyl-6-[(cyclopropylcarbonyl)amino]-4-iodpyridin-2-carboxylat (VII-2) a) Methyl-6-[(tert-butoxycarbonyl)amino]-4-iodpyridin-2-carboxylat (V-2) 100.0 g (312 mmol) of dimethyl 4-iodopyridine-2,6-dicarboxylate (III-2) was suspended in 1000 ml of a 10: 1 (v / v) methanol: dichloromethane (14.8 g, 265 mmol) of potassium hydroxide. The reaction mixture was stirred for 6 h at room temperature. Subsequently, the batch was mixed with 1500 ml of diethyl ether and stirred for a further 30 minutes. The precipitated solid was filtered off and washed with diethyl ether. The filter residue was then resuspended and acidified to pH 3 with 3N HCl. The precipitated solid was filtered off, washed successively with dichloromethane and diethyl ether and dried in vacuo. 56.0 g (58.0% of theory) of the title compound (IV-2) were obtained. 1 H-NMR (400.0 MHz, d 6 -DMSO): = 8.47 (s, 1 H), 8.40 (s, 1 H), 3.90 (s, 3 H) methyl-6 [(cyclopropylcarbonyl) amino] -4-iodopyridine-2-carboxylate (VII-2) a) Methyl 6 - [(tert-butoxycarbonyl) amino] -4-iodopyridine-2-carboxylate (V-2)
Zu einer Mischung von 50,0 g (163 mmol) 4-Iod-6-(methoxycarbonyl)pyridin-2-carbonsäure (IV-2) und 34 ml (244 mmol) Triethylamin in 600 ml eines Gemisches aus t-Butanol und 1,4-Dioxan (Verhältnis 1:3, V/V) wurden 54,0 g (195 mmol) Diphenylphosphorylazid bei Raumtemperatur zugegeben. Die Reaktionsmischung wurde anschließend für 1 h bei Raumtemperatur gerührt, anschließend noch 2 Stunden unter Rückfluss erhitzt und danach auf Raumtemperatur abgekühlt. Ausfallender Feststoff wurde abfiltriert. Dem Filtrat wurde Wasser zugesetzt und diese wässrige Phase mit Ethylacetat mehrfach extrahiert. Die vereinigten organischen Phasen wurden nacheinander mit Wasser gewaschen, über Natriumsulfat getrocknet, filtriert und eingedampft. Man erhielt 70 g einer Rohfraktion der Titelverbindung (V-2), die ohne weitere Aufreinigung direkt weiter umgesetzt wurden gemäß b) zu (VI- 2). b) Methyl-6-amino-4-iodpyridin-2-carboxylat (VI-2) To a mixture of 50.0 g (163 mmol) of 4-iodo-6- (methoxycarbonyl) pyridine-2-carboxylic acid (IV-2) and 34 ml (244 mmol) of triethylamine in 600 ml of a mixture of t-butanol and 1 , 4-dioxane (ratio 1: 3, v / v), 54.0 g (195 mmol) of diphenylphosphoryl azide were added at room temperature. The reaction mixture was then stirred for 1 h at room temperature, then heated under reflux for a further 2 hours and then cooled to room temperature. Dropping solid was filtered off. Water was added to the filtrate and this aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed successively with water, dried over sodium sulfate, filtered and evaporated. This gave 70 g of a crude fraction of the title compound (V-2), which were directly reacted further without further purification according to b) to (VI-2). b) Methyl 6-amino-4-iodopyridine-2-carboxylate (VI-2)
Eine Lösung von 70 g der nach a) hergestellten Rohfraktion von Methyl-4-brom-6-[(tert- butoxycarbonyl)amino]pyridin-2-carboxylat (V-2) in 400 ml Dichlormethan wurde im Eisbad gekühlt und 200 ml Trifluoressigsäure langsam und tropfenweise zugesetzt. Nach Beendigung der Zugabe wurde der Ansatz für 6 h bei Raumtemperatur gerührt. Anschließend wurde die Reaktionsmischung im Vakuum eingedampft. Der Rückstand wurde mit Ethylacetat verdünnt und in gesättigte Natriumcarbonatlösung eingetragen. Nach Phasentrennung wurde die organische Phase nacheinander mit Wasser und Brine gewaschen, über Natriumsulfat getrocknet und filtriert. Das Filtrat wurde im Vakuum eingedampft. Man erhielt 40 g einer Rohfraktion der Titelverbindung (VI-2), die ohne weitere Aufreinigung direkt weiter umgesetzt wurde gemäß c) zu (VII-2). c) Methyl-6-[(cyclopropylcarbonyl)amino]-4-iodpyridin-2-carboxylat (VII-2) A solution of 70 g of the crude fraction of methyl 4-bromo-6 - [(tert-butoxycarbonyl) amino] pyridine-2-carboxylate (V-2) prepared in a) in 400 ml of dichloromethane was cooled in an ice bath and 200 ml of trifluoroacetic acid added slowly and dropwise. After completion of the addition, the reaction was stirred for 6 h at room temperature. Subsequently, the reaction mixture was evaporated in vacuo. The residue was diluted with ethyl acetate and added to saturated sodium carbonate solution. After phase separation, the organic phase was washed successively with water and brine, dried over sodium sulfate and filtered. The filtrate was evaporated in vacuo. This gave 40 g of a crude fraction of the title compound (VI-2), which was directly reacted further without further purification according to c) to (VII-2). c) Methyl 6 - [(cyclopropylcarbonyl) amino] -4-iodopyridine-2-carboxylate (VII-2)
Zu einer gerührten Lösung von 40,0 g der nach b) hergestellten Rohfraktion von Methyl-6-amino-4- iodpyridin-2-carboxylat (VI-2) in 400 ml trockenem Dichlormethan wurden 26 ml (322 mmol) Pyridin gegeben. Nach zehnminütigem Rühren bei Raumtemperatur wurde der Ansatz im Eisbad abgekühlt und 14,6 ml (161 mmol) Cyclopropancarbonsäurechlorid zugegeben. Die Reaktionsmischung wurde weitere 16 h bei Raumtemperatur gerührt. Anschließend wurde der Ansatz mit Wasser verdünnt und die Phasen separiert. Die wässrige Phase wurde noch mehrmals mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden nacheinander mit Wasser und Brine gewaschen, übre Natriumsulfat getrocknet, filtriert und im Vakuum eingedampft. Der Rückstand wurde über eine Kieselgelsäule chromatographisch gereinigt (Ethylacetat in Hexan, 0%– 30%), gefolgt von einer Umkristallisation aus Ethylacetat:Hexan (1:10, V/V). Man erhielt 35,0 g (64,0% d. Th. über die drei Stufen a bis c) der Titelverbindung (VII-2). 1H-NMR (400,0 MHz, d6-DMSO): ^ ^ = 11,32 (s, 1 H), 8,77 (s, 1 H), 8,04 (s, 1 H), 3,87 (s, 3 H), 2,07 (m, 1 H), 0,83 (d, 4 H) 6-[(Cyclopropylcarbonyl)amino]-4-iodpyridin-2-carbonsäure (VIII-2) To a stirred solution of 40.0 g of the crude fraction of methyl 6-amino-4-iodo-pyridine-2-carboxylate (VI-2) prepared in b) in 400 ml of dry dichloromethane was added 26 ml (322 mmol) of pyridine. After stirring for ten minutes at room temperature, the reaction was cooled in an ice bath and 14.6 ml (161 mmol) of cyclopropanecarboxylic acid chloride added. The reaction mixture was stirred at room temperature for a further 16 h. The mixture was then diluted with water and the phases were separated. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were washed successively with water and brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by chromatography on a silica gel column (ethyl acetate in hexane, 0% -30%), followed by recrystallization from ethyl acetate: hexane (1:10, v / v). This gave 35.0 g (64.0% of theory over the three stages a to c) of the title compound (VII-2). 1H-NMR (400.0 MHz, d 6 -DMSO): ^^ = 11.32 (s, 1H), 8.77 (s, 1H), 8.04 (s, 1H), 3, 87 (s, 3H), 2.07 (m, 1H), 0.83 (d, 4H) 6 - [(Cyclopropylcarbonyl) amino] -4-iodopyridine-2-carboxylic acid (VIII-2)
Zu einer Suspension von 23,0 g (66,5 mmol) Methyl-6-[(cyclopropylcarbonyl)amino]-4-iodpyridin-2- carboxylat (VII-2) in einer Mischung aus 150 ml THF und 150 ml Wasser wurden bei 25 °C 8,40 g (199 mmol) Lithiumhydroxid-Monohydrat gegeben. Die Mischung wurde noch 16 h bei 25 °C gerührt. Anschließend wurde das THF im Vakuum entfernt und die wässrige Phase mittels 6 N Salzsäure auf pH 3 eingestellt. Der ausfallende Niederschlag wurde abfiltriert und im Vakuum getrocknet. Man erhielt 19,0 g (90,0% d. Th.) der Titelverbindung (VIII-2). 1H-NMR (400,0 MHz, d6-DMSO): ^ = 12,63 ppm (broad, 1H), 8,62 (s, 1 H), 7,98 (s, 1 H), 2,34 (m, 1 H), 0,89 (d, 4 H) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-iodpyridin-2-carboxamid (IX-2) To a suspension of 23.0 g (66.5 mmol) of methyl 6 - [(cyclopropylcarbonyl) amino] -4-iodopyridine-2-carboxylate (VII-2) in a mixture of 150 ml of THF and 150 ml of water were added 25 ° C 8.40 g (199 mmol) of lithium hydroxide monohydrate. The mixture was stirred for a further 16 h at 25 ° C. Subsequently, the THF was removed in vacuo and the aqueous phase adjusted to pH 3 by means of 6 N hydrochloric acid. The precipitate was filtered off and dried in vacuo. 19.0 g (90.0% of theory) of the title compound (VIII-2) were obtained. 1 H NMR (400.0 MHz, d 6 -DMSO): = = 12.63 ppm (broad, 1H), 8.62 (s, 1H), 7.98 (s, 1H), 2.34 (m, 1H), 0.89 (d, 4H) N - (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4-iodopyridine-2-carboxamide (IX-2)
Zu einer gerührten Lösung von 9,5 g (28,6 mmol) 6-[(Cyclopropylcarbonyl)amino]-4-iodpyridin-2- carbonsäure (VIII-2) in 80 ml trockenem Dimethylformamid wurden bei Raumtemperatur 19,6 g (51,5 mmol) HATU gegeben. Nach weiterem einstündigem Rühren bei Raumtemperatur wurden 5,3 g (31,5 mmol) 4-(Aminomethyl)benzonitril-Hydrochlorid sowie im Anschluss 14,0 ml (100 mmol) Triethylamin hinzugefügt. Der Ansatz wurde noch 16 h bei Raumtemperatur gerührt und anschließend langsam in Eiswasser gegossen. Der entstehende Niederschlag wurde abfiltriert, mit Diethylether gewaschen und über eine Kieselgelsäule chromatographisch gereinigt (Fließmittel Ethylacetat:Dichlormethan:Hexan 1:1:2). Man erhielt 9,3 g (73,0% d. Th.) der Titelverbindung (IX-2). 1H-NMR (400,0 MHz, CDCl3): ^ = 8,82 (s, 1 H), 8,29 ppm (s, 1 H), 8,08 (m, broad, 2 H), 7,63 (m, 2 H), 7,44 (m, 2 H), 4,69 (d, 2 H), 1,53 (m, 1 H), 1,13 (m, 2 H), 0,95 (m, 2 H) Nach Verfahren B: N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-[3-(pentafluorethyl)-1H-pyrazol-1- yl]pyridin-2-carboxamid (I-188) To a stirred solution of 9.5 g (28.6 mmol) of 6 - [(cyclopropylcarbonyl) amino] -4-iodopyridine-2-carboxylic acid (VIII-2) in 80 ml of dry dimethylformamide at room temperature was added 19.6 g (51 , 5 mmol) HATU. After further stirring at room temperature for 1 hour, 5.3 g (31.5 mmol) of 4- (aminomethyl) benzonitrile hydrochloride and then 14.0 ml (100 mmol) of triethylamine were added. The mixture was stirred for a further 16 h at room temperature and then poured slowly into ice-water. The resulting precipitate was filtered off, washed with diethyl ether and purified by chromatography on a silica gel column (eluent ethyl acetate: dichloromethane: hexane 1: 1: 2). This gave 9.3 g (73.0% of theory) of the title compound (IX-2). 1H-NMR (400.0 MHz, CDCl3): = = 8.82 (s, 1H), 8.29 ppm (s, 1H), 8.08 (m, broad, 2H), 7.63 (m, 2H), 7.44 (m, 2H), 4.69 (d, 2H), 1.53 (m, 1H), 1.13 (m, 2H), 0.95 (m, 2H) According to Method B: N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- [3- (pentafluoroethyl) -1H-pyrazol-1-yl] pyridine-2-carboxamide ( I-188)
120 mg (0,26 mmol) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-iodpyridin-2-carboxamid (IX-2) wurden in 5 ml entgastem 1,4-Dioxan unter Argon in einem Rollrandgefäß vorgelegt und mit 70,0 mg (0,37 mmol) 3-(Pentafluorethyl)-1H-pyrazol, 5,2 mg (0,02 mmol) Kupfer(I)iodid und 13,4 mg (0,08 mmol) Kaliumiodid versetzt. Das Vial wurde erneut mit Argon geflutet und 7,7 mg (0,05 mmol) trans-N,N`-Dimethylcyclohexan-1,2-diamin (racemisch) zugegeben. Das Gefäß wurde verschlossen und in einem Aluminiumblock über Nacht auf 130 °C erhitzt. Das Filtrat wurde im Vakuum eingedampft und der Rückstand mittels MPLC-Trennung (Fließmittel Dichlormethan:Ethylacetat, 7:3), gefolgt von einer zweiten Trennung (Reversed Phase, Fließmittel Wasser:Acetonitril + 0.1% Ameisensäure) aufgereinigt. Man erhielt 56 mg (96% Reinheit, 39,6% d. Th.) der Titelverbindung (I-188). logP (neutral / sauer): 3,57 / 3,70; MH+: 505; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 11,092 (9,1); 9,085 (6,7); 9,081 (6,3); 9,078 (6,9); 8,963 (2,4); 8,947 (5,2); 8,931 (2,5); 8,784 (11,4); 8,779 (11,8); 8,314 (0,8); 8,213 (11,9); 8,208 (11,9); 7,842 (13,6); 7,821 (16,0); 7,561 (13,5); 7,540 (11,8); 7,162 (8,7); 7,155 (8,8); 4,662 (10,2); 4,646 (10,2); 3,320 (172,1); 2,945 (1,7); 2,892 (0,4); 2,785 (1,3); 2,732 (0,3); 2,676 (0,9); 2,672 (1,3); 2,667 (1,0); 2,525 (3,5); 2,512 (74,7); 2,507 (152,9); 2,503 (203,1); 2,498 (149,5); 2,494 (74,3); 2,334 (0,9); 2,330 (1,2); 2,325 (0,9); 2,075 (7,9); 2,062 (1,9); 2,057 (2,2); 2,052 (1,8); 2,045 (3,7); 2,032 (2,2); 2,027 (2,1); 2,013 (1,0); 1,958 (1,4); 0,917 (0,6); 0,894 (11,6); 0,885 (15,7); 0,866 (8,6); 0,845 (0,8); 0,146 (0,9); 0,008 (7,5); 0,000 (195,9); -0,008 (8,2); -0,150 (0,9) Nach Verfahren C: 2,6-Dichlor-4-[4-(trifluormethoxy)phenyl]pyridin (XIV-1) 120 mg (0.26 mmol) of N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4-iodopyridine-2-carboxamide (IX-2) were dissolved in 5 ml of degassed 1,4-dioxane under argon in vacuo a roll edge vessel and with 70.0 mg (0.37 mmol) of 3- (pentafluoroethyl) -1H-pyrazole, 5.2 mg (0.02 mmol) of copper (I) iodide and 13.4 mg (0.08 mmol ) Potassium iodide added. The vial was again flooded with argon and 7.7 mg (0.05 mmol) of trans-N, N'-dimethylcyclohexane-1,2-diamine (racemic) added. The vessel was sealed and heated in an aluminum block overnight at 130 ° C. The filtrate was evaporated in vacuo and the residue purified by MPLC separation (eluent dichloromethane: ethyl acetate, 7: 3) followed by a second separation (reversed phase, water eluant: acetonitrile + 0.1% formic acid). 56 mg (96% purity, 39.6% of theory) of the title compound (I-188) were obtained. logP (neutral / acid): 3.57 / 3.70; MH +: 505; 1 H NMR (400.0 MHz, d 6 -DMSO): = = 11.092 (9.1); 9.085 (6.7); 9.081 (6.3); 9.078 (6.9); 8.963 (2.4); 8,947 (5.2); 8,931 (2.5); 8,784 (11,4); 8,779 (11,8); 8,314 (0.8); 8.213 (11.9); 8,208 (11,9); 7,842 (13.6); 7,821 (16.0); 7,561 (13.5); 7,540 (11.8); 7,162 (8,7); 7,155 (8,8); 4,662 (10,2); 4,646 (10,2); 3,320 (172,1); 2,945 (1.7); 2,892 (0.4); 2,785 (1.3); 2,732 (0.3); 2,676 (0.9); 2,672 (1.3); 2,667 (1.0); 2,525 (3.5); 2,512 (74,7); 2,507 (152.9); 2,503 (203,1); 2,498 (149.5); 2,494 (74.3); 2,334 (0.9); 2,330 (1.2); 2.325 (0.9); 2.075 (7.9); 2.062 (1.9); 2,057 (2,2); 2,052 (1.8); 2.045 (3.7); 2.032 (2.2); 2,027 (2,1); 2.013 (1.0); 1,958 (1.4); 0.917 (0.6); 0.894 (11.6); 0.885 (15.7); 0.866 (8.6); 0.845 (0.8); 0.146 (0.9); 0.008 (7.5); 0.000 (195.9); -0.008 (8.2); -0.150 (0.9) By Method C: 2,6-dichloro-4- [4- (trifluoromethoxy) phenyl] pyridine (XIV-1)
Unter Argon wurden 15,0 g (54,7 mmol) 2,6-Dichlor-4-iod-pyridin (XIII-1), 12,4 g (60,2 mmol) [4- (Trifluormethoxy)phenyl]borsäure und 3,2 g (2,73 mmol) Tetrakis(triphenylphosphin)palladium(0) in 350 ml 1,4-Dioxan gegeben. Anschließend wurden 55 ml einer zweimolaren Natriumcarbonatlösung hinzugefügt und der Ansatz 18 h unter Rückfluss und unter Argon gerührt. Das abgekühlte Reaktionsgemisch wurde dann mit 200 ml Ethylacetat versetzt und über Celite filtriert. Das Filtrat wurde eingedampft, in Dichlormethan aufgenommen und mit Wasser gewaschen. Die Reinigung erfolgte mittels MPLC (Fließmittel Cyclohexan:Dichlormethan, 85:15). Man erhielt 12,2 g (99% Reinheit, 71,6% d. Th.) der Titelverbindung (XIV-1). logP (neutral / sauer): 4,62 / 4,63; MH+: 308; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 8,067 (0,4); 8,059 (4,4); 8,054 (1,4); 8,042 (1,4); 8,037 (5,0); 8,029 (0,5); 7,975 (16,0); 7,544 (2,6); 7,523 (2,4); 3,320 (33,3); 2,525 (0,4); 2,521 (0,6); 2,512 (9,7); 2,507 (20,9); 2,503 (29,5); 2,498 (21,8); 2,494 (10,3); 0,008 (0,3); 0,000 (11,5); -0,008 (0,4) 2-Chlor-4-[4-(trifluormethoxy)phenyl]-6-vinylpyridin (XV-1) Under argon, 15.0 g (54.7 mmol) of 2,6-dichloro-4-iodo-pyridine (XIII-1), 12.4 g (60.2 mmol) of [4- (trifluoromethoxy) phenyl] boric acid and Add 3.2 g (2.73 mmol) of tetrakis (triphenylphosphine) palladium (0) in 350 mL of 1,4-dioxane. Subsequently, 55 ml of a sodium bicarbonate sodium solution were added and the reaction was stirred under reflux for 18 h and under argon. The cooled reaction mixture was then added with 200 ml of ethyl acetate and filtered through Celite. The filtrate was evaporated, taken up in dichloromethane and washed with water. The purification was carried out by means of MPLC (mobile phase cyclohexane: dichloromethane, 85:15). 12.2 g (99% purity, 71.6% of theory) of the title compound (XIV-1) were obtained. logP (neutral / acid): 4.62 / 4.63; MH +: 308; 1H-NMR (400.0 MHz, d6-DMSO): = = 8.067 (0.4); 8,059 (4.4); 8,054 (1.4); 8,042 (1.4); 8,037 (5.0); 8.029 (0.5); 7,975 (16.0); 7,544 (2.6); 7,523 (2,4); 3,320 (33.3); 2,525 (0.4); 2,521 (0.6); 2,512 (9.7); 2,507 (20.9); 2,503 (29.5); 2,498 (21.8); 2,494 (10.3); 0.008 (0.3); 0.000 (11.5); -0.008 (0.4) 2-Chloro-4- [4- (trifluoromethoxy) phenyl] -6-vinylpyridine (XV-1)
Unter Argon wurden 9,0 g (29,2 mmol) 2,6-Dichlor-4-[4-(trifluormethoxy)phenyl]pyridin (XIV-1) und 5,2 g (33,5 mmol) 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolan in 84 ml 1,4-Dioxan vorgelegt und 37 ml einer zweimolaren Natriumcarbonatlösung hinzugegeben. Unter Argon wurden anschließend 6,8 g (5,84 mmol) Tetrakis(triphenylphosphin)palladium(0) hinzugefügt und der Ansatz in einer IR Discover Mikrowelle für 60 Minuten auf 120 °C erhitzt. Nach Abkühlung wurde mit Methanol verdünnt und das Reaktionsgemisch über Celite filtriert. Das Filtrat wurde eingeengt und der Rückstand mittels MPLC (Fließmittel Cyclohexan:Dichlormethan, 4:1) gereinigt. Man erhielt 3,6 g (97% Reinheit, 40,0% d. Th.) der Titelverbindung (XV-1). logP (neutral / sauer): 4,72 / 4,77; MH+: 300; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 8,060 (0,4); 8,030 (14,9); 8,009 (16,0); 7,976 (0,9); 7,883 (15,1); 7,768 (15,8); 7,544 (12,7); 7,522 (11,9); 6,891 (4,0); 6,864 (4,5); 6,848 (5,1); 6,821 (5,1); 6,392 (8,1); 6,348 (6,8); 5,623 (7,7); 5,596 (7,3); 3,321 (131,5); 2,673 (0,9); 2,503 (158,4); 2,331 (0,9); 0,147 (0,4); 0,002 (73,0); 0,000 (78,1); -0,149 (0,4) 6-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin-2-carbonsäure (XVI-1) Under argon, 9.0 g (29.2 mmol) of 2,6-dichloro-4- [4- (trifluoromethoxy) phenyl] pyridine (XIV-1) and 5.2 g (33.5 mmol) of 4.4, 5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolan presented in 84 ml of 1,4-dioxane and added 37 ml of a two molar sodium carbonate solution. Subsequently, under argon, 6.8 g (5.84 mmol) of tetrakis (triphenylphosphine) palladium (0) were added and the batch heated in an IR Discover microwave for 60 minutes at 120 ° C. After cooling, it was diluted with methanol and the reaction mixture was filtered through Celite. The filtrate was concentrated and the residue was MPLC (mobile phase cyclohexane: dichloromethane, 4: 1). This gave 3.6 g (97% purity, 40.0% of theory) of the title compound (XV-1). logP (neutral / acid): 4.72 / 4.77; MH +: 300; 1H-NMR (400.0 MHz, d6-DMSO): = = 8.060 (0.4); 8,030 (14.9); 8,009 (16,0); 7.976 (0.9); 7,883 (15.1); 7,768 (15.8); 7,544 (12.7); 7,522 (11.9); 6.891 (4.0); 6,864 (4,5); 6,848 (5.1); 6,821 (5.1); 6,392 (8,1); 6,348 (6.8); 5,623 (7,7); 5.596 (7.3); 3,321 (131.5); 2,673 (0.9); 2,503 (158.4); 2.331 (0.9); 0.147 (0.4); 0.002 (73.0); 0,000 (78.1); -0.149 (0.4) 6-Chloro-4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxylic acid (XVI-1)
Zu einer Lösung von 3,6 g (12,0 mmol) 2-Chlor-4-[4-(trifluormethoxy)phenyl]-6-vinylpyridin (XV-1) in 200 ml Aceton und 200 ml Wasser wurden vorsichtig 9,5 g (60 mmol) Kaliumpermanganat gegeben. Die Mischung erwärmte sich auf ca. 40 °C und wurde anschließend für 3 h weitergerührt. Nach Reaktionsende wurde der Ansatz über einen Sinterglasfilter filtriert. Das Aceton im Filtrat wurde im Vakuum entfernt und die alkalische wässrige Phase anschließend mit Ethylacetat gewaschen. Danach wurde der pH-Wert der wässrigen Phase auf pH4 eingestellt, die Wasserphase mit Ethylacetat extrahiert und die organische Phase eingedampft. Man erhielt 3,0 g (98% Reinheit, 77,0% d. Th.) der Titelverbindung (XVI-1). logP (neutral / sauer): 1,17 / 3,00; MH+: 318; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 8,291 (10,7); 8,287 (11,4); 8,138 (11,4); 8,134 (11,1); 8,079 (1,4); 8,071 (12,4); 8,066 (4,1); 8,054 (4,2); 8,049 (13,8); 8,042 (1,5); 7,550 (8,2); 7,530 (7,5); 4,092 (1,0); 3,325 (15,8); 3,170 (16,0); 2,677 (0,5); 2,672 (0,6); 2,668 (0,5); 2,526 (1,6); 2,512 (36,7); 2,508 (76,9); 2,503 (107,3); 2,499 (80,3); 2,495 (38,7); 2,482 (2,1); 2,335 (0,5); 2,330 (0,6); 2,326 (0,5); 2,118 (2,7); 1,990 (0,4); 1,910 (8,6); 1,142 (5,8); 0,008 (1,1); 0,000 (31,7); -0,008 (1,1) 6-Chlor-N-(4-cyanbenzyl)-4-[4-(trifluormethoxy)phenyl]pyridin-2-carboxamid (XVII-1) To a solution of 3.6 g (12.0 mmol) of 2-chloro-4- [4- (trifluoromethoxy) phenyl] -6-vinylpyridine (XV-1) in 200 ml of acetone and 200 ml of water was carefully added 9.5 g (60 mmol) of potassium permanganate. The mixture warmed to about 40 ° C and was then further stirred for 3 h. After the end of the reaction, the batch was filtered through a sintered glass filter. The acetone in the filtrate was removed in vacuo and the alkaline aqueous phase was then washed with ethyl acetate. Thereafter, the pH of the aqueous phase was adjusted to pH4, the water phase was extracted with ethyl acetate and the organic phase was evaporated. 3.0 g (98% purity, 77.0% of theory) of the title compound (XVI-1) were obtained. logP (neutral / acid): 1.17 / 3.00; MH +: 318; 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 8.291 (10.7); 8,287 (11.4); 8,138 (11,4); 8,134 (11,1); 8.079 (1.4); 8.071 (12.4); 8.066 (4.1); 8,054 (4.2); 8.049 (13.8); 8.042 (1.5); 7,550 (8.2); 7,530 (7.5); 4,092 (1.0); 3,325 (15.8); 3,170 (16.0); 2,677 (0.5); 2,672 (0.6); 2,668 (0.5); 2,526 (1.6); 2,512 (36,7); 2,508 (76.9); 2,503 (107,3); 2,499 (80.3); 2,495 (38.7); 2,482 (2,1); 2.335 (0.5); 2,330 (0.6); 2,326 (0.5); 2,118 (2,7); 1,990 (0.4); 1,910 (8.6); 1,142 (5.8); 0.008 (1.1); 0.000 (31.7); -0.008 (1,1) 6-Chloro-N- (4-cyanobenzyl) -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (XVII-1)
Zu einer Lösung von 5,2 g (16,3 mmol) 6-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin-2-carbonsäure (XVI-1) in 15 ml Toluol wurden 1,3 ml (18,0 mmol) Thionylchlorid, gelöst in 5 ml Toluol, vorsichtig zugegeben. Der Ansatz wurde 2 h unter Rückfluss erhitzt und anschließend nach dem Abkühlen im Vakuum eingedampft. Der Rückstand wurde in 7 ml Acetonitril gelöst und in eine Lösung von 2,6 g (19,6 mmol) 4-(Aminomethyl)benzonitril und 6,6 g (65,4 mmol) Triethylamin in 15 ml Acetonitril eingetragen. Diese Mischung wurde anschließend über Nacht unter Rückfluss erhitzt. Nach dem Abkühlen wurde der Ansatz im Vakuum eingedampft, der Rückstand mit Wasser und Dichlormethan versetzt und die organische Phase abgetrennt. Diese wurde nach Trocknung und Eindampfen mittels MPLC über eine Kieselkartusche aufgereinigt (Fließmittel Cyclohexan:Ethylacetat, 1:9). Man erhielt 4,1 g (99% Reinheit, 57,4% d. Th.) der Titelverbindung (XVII-1). logP (neutral / sauer): 4,19 / 4,23; MH+: 432; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 9,503 (2,4); 9,487 (5,0); 9,471 (2,4); 8,287 (12,1); 8,283 (12,9); 8,137 (12,9); 8,133 (12,4); 8,085 (0,8); 8,078 (1,5); 8,071 (14,0); 8,066 (4,8); 8,054 (4,8); 8,049 (15,6); 8,042 (1,7); 7,811 (13,4); 7,791 (16,0); 7,550 (9,9); 7,541 (14,9); 7,530 (9,8); 7,521 (12,7); 5,755 (1,6); 4,598 (9,8); 4,582 (9,9); 3,325 (196,7); 2,678 (0,6); 2,673 (0,8); 2,669 (0,6); 2,526 (2,1); 2,513 (44,6); 2,508 (91,9); 2,504 (126,9); 2,499 (95,6); 2,495 (47,0); 2,335 (0,5); 2,331 (0,7); 2,326 (0,6); 0,146 (0,7); 0,008 (5,2); 0,000 (147,0); -0,008 (5,7); -0,150 (0,7) N-(4-Cyanbenzyl)-6-(methylamino)-4-[4-(trifluormethoxy)phenyl]pyridin-2-carboxamid (XVIII-1) To a solution of 5.2 g (16.3 mmol) of 6-chloro-4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxylic acid (XVI-1) in 15 ml of toluene was added 1.3 ml (18, 0 mmol) of thionyl chloride, dissolved in 5 ml of toluene, carefully added. The batch was refluxed for 2 h and then, after cooling, evaporated in vacuo. The residue was dissolved in 7 ml of acetonitrile and added to a solution of 2.6 g (19.6 mmol) of 4- (aminomethyl) benzonitrile and 6.6 g (65.4 mmol) of triethylamine in 15 ml of acetonitrile. This mixture was then refluxed overnight. After cooling, the batch was evaporated in vacuo, the residue was combined with water and dichloromethane and the organic phase separated. After drying and evaporation by means of MPLC, this was purified by means of a silica cartridge (mobile phase cyclohexane: ethyl acetate, 1: 9). This gave 4.1 g (99% purity, 57.4% of theory) of the title compound (XVII-1). logP (neutral / acidic): 4.19 / 4.23; MH +: 432; 1 H NMR (400.0 MHz, d 6 -DMSO): = = 9.503 (2.4); 9,487 (5.0); 9.471 (2.4); 8,287 (12: 1); 8,283 (12.9); 8.137 (12.9); 8,133 (12,4); 8.085 (0.8); 8.078 (1.5); 8.071 (14.0); 8.066 (4.8); 8,054 (4.8); 8.049 (15.6); 8.042 (1.7); 7,811 (13.4); 7,791 (16.0); 7,550 (9.9); 7,541 (14.9); 7,530 (9.8); 7,521 (12,7); 5,755 (1.6); 4,598 (9.8); 4,582 (9.9); 3,325 (196.7); 2,678 (0.6); 2,673 (0.8); 2,669 (0.6); 2,526 (2,1); 2,513 (44.6); 2,508 (91.9); 2,504 (126.9); 2,499 (95.6); 2,495 (47.0); 2.335 (0.5); 2.331 (0.7); 2,326 (0.6); 0.146 (0.7); 0.008 (5.2); 0,000 (147,0); -0.008 (5.7); -0.150 (0.7) N- (4-cyanobenzyl) -6- (methylamino) -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (XVIII-1)
600 mg (1,4 mmol) 6-Chlor-N-(4-cyanbenzyl)-4-[4-(trifluormethoxy)phenyl]pyridin-2-carboxamid (XVII-1) und 21 ml (41,6 mmol) einer zweimolaren Lösung von Methanamin in THF wurden in einem 300-ml-Autoklaven vorgelegt, 10 bar Argon aufgedrückt und der Ansatz 75 h bei 140 °C gerührt (800 U/min.). Der Ansatz wurde nach dem Abkühlen eingedampft und der Rückstand mittels MPLC über eine Kieselgelkartusche gereinigt (Fließmittel Cyclohexan:Ethylacetat, 1:1). Man erhielt 400 mg (98% Reinheit, 66,2% d. Th.) der Titelverbindung (XVIII-1). logP (neutral / sauer): 3,63 / 3,63; MH+: 427; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 9,163 (1,6); 9,147 (3,4); 9,131 (1,6); 8,314 (0,7); 7,836 (1,1); 7,829 (9,7); 7,824 (3,6); 7,813 (12,2); 7,807 (12,7); 7,793 (11,8); 7,523 (9,7); 7,502 (15,4); 7,482 (6,3); 7,435 (8,6); 7,431 (9,0); 6,895 (8,4); 6,892 (8,5); 6,880 (1,0); 6,868 (2,4); 6,856 (2,4); 5,754 (2,8); 4,608 (6,8); 4,592 (6,9); 4,057 (1,2); 4,039 (3,7); 4,021 (3,8); 4,003 (1,3); 3,321 (164,4); 2,949 (15,3); 2,937 (15,4); 2,676 (0,6); 2,672 (0,9); 2,667 (0,7); 2,525 (2,3); 2,511 (50,4); 2,507 (103,9); 2,503 (143,4); 2,498 (107,9); 2,494 (52,7); 2,334 (0,6); 2,329 (0,9); 2,325 (0,6); 1,989 (16,0); 1,194 (4,2); 1,176 (8,3); 1,158 (4,1); 0,146 (0,7); 0,008 (5,6); 0,000 (161,2); -0,008 (6,0); -0,150 (0,7) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)(methyl)amino]-4-[4-(trifluormethoxy)phenyl]- pyridin-2-carboxamid (I-215) 600 mg (1.4 mmol) of 6-chloro-N- (4-cyanobenzyl) -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (XVII-1) and 21 ml (41.6 mmol) of a two molar solution of methanamine in THF were placed in a 300 ml autoclave, 10 bar argon and the mixture for 75 h at 140 ° C stirred (800 U / min.). The batch was evaporated after cooling and the residue was purified by MPLC over a silica gel cartridge (eluting agent cyclohexane: ethyl acetate, 1: 1). 400 mg (98% purity, 66.2% of theory) of the title compound (XVIII-1) were obtained. logP (neutral / acid): 3.63 / 3.63; MH +: 427; 1 H NMR (400.0 MHz, d 6 -DMSO): = = 9.163 (1.6); 9.147 (3.4); 9.131 (1.6); 8.314 (0.7); 7.836 (1.1); 7,829 (9.7); 7,824 (3.6); 7,813 (12.2); 7,807 (12.7); 7,793 (11,8); 7,523 (9.7); 7,502 (15.4); 7,482 (6,3); 7.435 (8.6); 7,431 (9.0); 6,895 (8.4); 6,892 (8.5); 6,880 (1.0); 6,868 (2,4); 6,856 (2,4); 5,754 (2.8); 4,608 (6.8); 4,592 (6.9); 4.057 (1.2); 4,039 (3.7); 4,021 (3.8); 4.003 (1.3); 3,321 (164.4); 2,949 (15.3); 2,937 (15.4); 2,676 (0.6); 2,672 (0.9); 2,667 (0.7); 2.525 (2.3); 2,511 (50.4); 2,507 (103.9); 2,503 (143.4); 2,498 (107.9); 2,494 (52.7); 2.334 (0.6); 2,329 (0.9); 2.325 (0.6); 1,989 (16.0); 1,194 (4,2); 1.176 (8.3); 1,158 (4,1); 0.146 (0.7); 0.008 (5.6); 0,000 (161,2); -0.008 (6.0); -0.150 (0.7) N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) (methyl) amino] -4- [4- (trifluoromethoxy) phenyl] -pyridine-2-carboxamide (I-215)
142 mg (0,33 mmol) N-(4-Cyanbenzyl)-6-(methylamino)-4-[4-(trifluormethoxy)phenyl]pyridin-2- carboxamid (XVIII-1) wurden in 7 ml absolutem Dichlormethan gelöst und anschließend mit 108 mg (0,83 mmol) N,N-Diisopropylethylamin sowie 38 mg (0,36 mmol) Cyclopropancarbonsäure-chlorid versetzt. Der Ansatz wurde dann über Nacht bei Raumtemperatur gerührt. Anschließend wurden 4 ml Wasser zugesetzt und die organische Phase wurde abgetrennt und eingeengt. Der Rückstand wurde mittels MPLC über eine Kieselgelkartusche gereinigt (Fließmittel Cyclohexan:Ethylacetat, 1:1). Man erhielt 150 mg (98% Reinheit, 89,3% d. Th.) der Titelverbindung (I-215). logP (neutral / sauer): 3,84 / 3,85; MH+: 495; 1H-NMR (400,0 MHz, d6-DMSO): ^ = 9,424 (2,3); 9,408 (5,1); 9,392 (2,4); 8,315 (0,3); 8,183 (11,4); 8,179 (12,2); 8,055 (11,8); 8,051 (11,2); 8,026 (1,5); 8,018 (13,2); 8,013 (4,5); 8,001 (4,8); 7,996 (14,9); 7,989 (1,7); 7,816 (13,2); 7,795 (16,0); 7,554 (10,3); 7,548 (15,3); 7,532 (11,0); 7,527 (12,7); 5,755 (0,9); 4,629 (9,0); 4,613 (9,0); 3,487 (39,9); 3,320 (112,3); 3,178 (0,5); 3,164 (0,5); 2,677 (0,6); 2,672 (0,9); 2,668 (0,6); 2,526 (2,2); 2,512 (49,6); 2,508 (103,7); 2,503 (143,8); 2,498 (106,8); 2,494 (50,7); 2,334 (0,6); 2,330 (0,8); 2,325 (0,6); 1,843 (0,6); 1,831 (1,4); 1,823 (1,7); 1,812 (2,5); 1,802 (1,8); 1,793 (1,4); 1,781 (0,7); 1,233 (0,4); 0,939 (2,0); 0,929 (5,6); 0,921 (7,9); 0,910 (6,2); 0,903 (2,5); 0,796 (2,4); 0,788 (5,6); 0,780 (5,0); 0,769 (5,9); 0,760 (4,5); 0,751 (1,7); 0,146 (0,4); 0,008 (3,3); 0,000 (101,4); -0,009 (3,2); -0,150 (0,4) Nach Verfahren F: N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonothioyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2- carbothioamid (I-181) 142 mg (0.33 mmol) of N- (4-cyanobenzyl) -6- (methylamino) -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (XVIII-1) were dissolved in 7 ml of absolute dichloromethane and then admixed with 108 mg (0.83 mmol) of N, N-diisopropylethylamine and 38 mg (0.36 mmol) of cyclopropanecarboxylic acid chloride. The reaction was then stirred overnight at room temperature. Subsequently, 4 ml of water were added and the organic phase was separated and concentrated. The residue was purified by MPLC over a silica gel cartridge (eluting with cyclohexane: ethyl acetate, 1: 1). 150 mg (98% purity, 89.3% of theory) of the title compound (I-215) were obtained. logP (neutral / acid): 3.84 / 3.85; MH +: 495; 1H-NMR (400.0 MHz, d6-DMSO): = = 9.424 (2.3); 9,408 (5.1); 9,392 (2,4); 8.315 (0.3); 8,183 (11,4); 8,179 (12,2); 8.055 (11.8); 8,051 (11.2); 8,026 (1.5); 8.018 (13.2); 8.013 (4.5); 8,001 (4,8); 7.996 (14.9); 7.989 (1.7); 7,816 (13,2); 7,795 (16.0); 7,554 (10.3); 7,548 (15.3); 7,532 (11.0); 7,527 (12,7); 5,755 (0.9); 4,629 (9.0); 4,613 (9.0); 3,487 (39.9); 3,320 (112.3); 3.178 (0.5); 3.164 (0.5); 2,677 (0.6); 2,672 (0.9); 2,668 (0.6); 2.526 (2.2); 2,512 (49.6); 2,508 (103.7); 2,503 (143,8); 2,498 (106.8); 2,494 (50.7); 2.334 (0.6); 2,330 (0.8); 2.325 (0.6); 1,843 (0.6); 1,831 (1.4); 1,823 (1.7); 1,812 (2.5); 1,802 (1.8); 1,793 (1.4); 1,781 (0.7); 1,233 (0.4); 0.939 (2.0); 0.929 (5.6); 0.921 (7.9); 0.910 (6.2); 0.903 (2.5); 0.796 (2.4); 0.788 (5.6); 0.780 (5.0); 0.769 (5.9); 0.760 (4.5); 0.751 (1.7); 0.146 (0.4); 0.008 (3.3); 0.000 (101.4); -0.009 (3.2); -0.150 (0.4) By Method F: N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonothioyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carbothioamide (I-181)
51 mg (0,11 mmol) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-[4- (trifluormethoxy)phenyl]pyridin-2-carboxamid (I-044) wurden in Toluol (3 mL) vorgelegt und mit 86 mg (0,21 mmol) 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfid (Lawesson Reagenz) versetzt. Die Mischung wurde 2 h bei 100° C gerührt. Anschließend wurde auf Raumtemperatur abgekühlt, das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde durch säulenchromatographische Aufreinigung mit einem Cyclohexan / Ethylacetat Gradienten als Laufmittel gereinigt. Man erhielt 18 mg (100% Reinheit, 33% d. Th.) der Titelverbindung (I-181). logP (neutral/sauer): 5,43/5,54; MH+: 513; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 1,03-1,08 (m, 2H), 1,17-1,23 (m, 2H), 2,50-2,55 (m, 1H), 5,13 (d, 2H), 7,56-7,58 (m, 4H), 7,82-7,84 (m, 2H), 7,91-7,94 (m, 2H), 8,50 (s, 1H), 8,89 (s, 1H), 11,19 (s, 1H), 12,37 (s, 1H). Nach Verfahren G: Methyl-(4-cyanbenzyl)({6-[(cyclopropylcarbonyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2- yl}carbonyl)carbamat (I-231) 51 mg (0.11 mmol) of N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (I-044) were dissolved in toluene (3 mL) and treated with 86 mg (0.21 mmol) of 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetan-2,4-disulfide (Lawesson reagent). The mixture was stirred for 2 h at 100 ° C. It was then cooled to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography with a cyclohexane / ethyl acetate gradient as eluent. 18 mg (100% pure, 33% of theory) of the title compound (I-181) were obtained. logP (neutral / acid): 5.43 / 5.54; MH +: 513; 1 H NMR (400 MHz, D 6 -DMSO) ppm ppm: 1.03-1.08 (m, 2H), 1.17-1.23 (m, 2H), 2.50-2.55 (m , 1H), 5.13 (d, 2H), 7.56-7.58 (m, 4H), 7.82-7.84 (m, 2H), 7.91-7.94 (m, 2H ), 8.50 (s, 1H), 8.89 (s, 1H), 11.19 (s, 1H), 12.37 (s, 1H). By Method G: Methyl (4-cyanobenzyl) ({6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} carbonyl) carbamate (I-231)
Methyl-(4-cyanbenzyl)({6-[(cyclopropylcarbonyl)(methoxycarbonyl)amino]-4-[4- (trifluormethoxy)phenyl]pyridin-2-yl}carbonyl)carbamat (I-232) Methyl (4-cyanobenzyl) ({6 - [(cyclopropylcarbonyl) (methoxycarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} carbonyl) carbamate (I-232)
Methyl-{6-[(4-cyanbenzyl)carbamoyl]-4-[4-(trifluormethoxy)phenyl]pyridin-2- yl}(cyclopropylcarbonyl)carbamat (I-233) Methyl {6 - [(4-cyanobenzyl) carbamoyl] -4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} (cyclopropylcarbonyl) carbamate (I-233)
166 mg (0,35 mmol) N-(4-Cyanbenzyl)-6-[(cyclopropylcarbonyl)amino]-4-[4- (trifluormethoxy)phenyl]pyridin-2-carboxamid (I-044) wurden in DMF (4 mL) gelöst und bei 0 °C mit 55 mg (1,38 mmol, 60% Reinheit) Natriumhydrid versetzt. Die Mischung wurde 15 min bei Raumtemperatur gerührt. Anschließend wurden 65 mg (0,69 mmol) Chlorameisensäuremethylester zugegeben und die Mischung wurde 14 h bei Raumtemperatur gerührt. Dann wurde Wasser zugegeben und dreimal mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit ges. NaCl- Lösung gewaschen, über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum entfernt und der Rückstand wurde durch säulenchromatographische Aufreinigung mit einem Cyclohexan / Ethylacetat Gradienten als Laufmittel gereinigt. Man erhielt 8 mg (68% Reinheit, 3% d. Th.) der Titelverbindung (I-231), 63 mg (93% Reinheit, 29% d. Th.) der Titelverbindung (I-232) und 23 mg (90% Reinheit, 11% d. Th.) der Titelverbindung (I-233). (I-231): logP (neutral/sauer): 4,43/4,41; MH+: 539; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,85-0,87 (m, 4H), 2,09-2,12 (m, 1H), 3,54 (s, 3H), 5,06 (s, 2H), 7,52-7,63 (m, 4H), 7,76 (d, 1H), 7,86-7,94 (m, 4H), 8,56 (d, 1H), 11,04 (s, 1H). (I-232): logP (neutral/sauer): 4,31/4,30; MH+: 597; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 0,97-1,07 (m, 4H), 2,77-2,81 (m, 1H), 3,45 (s, 3H), 3,73 (s, 3H), 5,07 (s, 2H), 7,54-7,57 (m, 4H), 7,82-7,84 (m, 2H), 8,07-8,11 (m, 3H), 8,20 (d, 1H). (I-233): logP (neutral/sauer): 3,91/3,90; MH+: 539; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 1,00-1,06 (m, 4H), 2,81-2,84 (m, 1H), 3,73 (s, 3H), 4,57 (d, 2H), 7,51-7,55 (m, 4H), 7,79-7,82 (m, 2H), 8,02-8,06 (m, 2H), 8,11 (d, 1H), 8,35 (d, 1H), 9,43 (t, 1H). Nach Verfahren H: 2-[3-Fluor-4-(pentafluorethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolan 166 mg (0.35 mmol) of N- (4-cyanobenzyl) -6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (I-044) were dissolved in DMF (4 mL) and treated at 0 ° C with 55 mg (1.38 mmol, 60% purity) of sodium hydride. The mixture was stirred for 15 minutes at room temperature. Subsequently, 65 mg (0.69 mmol) of methyl chloroformate were added and the mixture was stirred for 14 h at room temperature. Then, water was added and extracted three times with ethyl acetate. The combined organic phases were washed with sat. NaCl solution, dried over magnesium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography with a cyclohexane / ethyl acetate gradient as eluent. 8 mg (68% purity, 3% of theory) were obtained. Th.) Of the title compound (I-231), 63 mg (93% purity, 29% of theory) of the title compound (I-232) and 23 mg (90% purity, 11% of theory) of the title compound ( I-233). (I-231): logP (neutral / acid): 4.43 / 4.41; MH +: 539; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 0.85-0.87 (m, 4H), 2.09-2.12 (m, 1H), 3.54 (s, 3H), 5 , 06 (s, 2H), 7.52-7.63 (m, 4H), 7.76 (d, 1H), 7.86-7.94 (m, 4H), 8.56 (d, 1H ), 11.04 (s, 1H). (I-232): logP (neutral / acid): 4.31 / 4.30; MH +: 597; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 0.97-1.07 (m, 4H), 2.77-2.81 (m, 1H), 3.45 (s, 3H), 3 , 73 (s, 3H), 5.07 (s, 2H), 7.54-7.57 (m, 4H), 7.82-7.84 (m, 2H), 8.07-8.11 (m, 3H), 8.20 (d, 1H). (I-233): logP (neutral / acid): 3.91 / 3.90; MH +: 539; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 1.00-1.06 (m, 4H), 2.81-2.84 (m, 1H), 3.73 (s, 3H), 4 , 57 (d, 2H), 7.51-7.55 (m, 4H), 7.79-7.82 (m, 2H), 8.02-8.06 (m, 2H), 8.11 (d, 1H), 8.35 (d, 1H), 9.43 (t, 1H). By Method H: 2- [3-Fluoro-4- (pentafluoroethyl) phenyl] -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Unter Argon wurden 2,64 g (10,4 mmol) Bis(pinacolato)-diboron in 50 ml entgastem Dioxan aufgenommen und mit 2,90 g (9,90 mmol) 4-Brom-2-fluor-1-(pentafluorethyl)benzol, 0,81 g (0,99 mmol) [1,1′-Bis(diphenylphosphino)ferrocen]-palladium(II)dichlorid und 2,91 g (29,7 mmol) Kaliumacetat versetzt. Anschließend wurde der Ansatz über Nacht bei 80 °C gerührt. Nach Abkühlung wurde das Reaktionsgemisch von Lösungsmittel befreit, der Rückstand wurde dann in Acetonitril aufgenommen und über Kieselgel filtriert. Die Kieselgelschicht wurde mit Acetonitril und Dichlormethan nachgewaschen, die organischen Phasen wurden vereint und unter Vakuum eingedampft. Man erhielt 3,10 g (92,0% d. Th.) der Titelverbindung. Under argon, 2.64 g (10.4 mmol) of bis (pinacolato) -diborone were taken up in 50 ml of degassed dioxane and 2.90 g (9.90 mmol) of 4-bromo-2-fluoro-1- (pentafluoroethyl) benzene, 0.81 g (0.99 mmol) of [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride and 2.91 g (29.7 mmol) of potassium acetate. The mixture was then stirred overnight at 80 ° C. After cooling, the reaction mixture was freed of solvent, the residue was then taken up in acetonitrile and filtered through silica gel. The silica gel layer was washed with acetonitrile and dichloromethane, the organic phases were combined and evaporated under vacuum. 3.10 g (92.0% of theory) of the title compound were obtained.
1H-NMR(400 MHz, D6-DMSO) ^ ppm: 7,91(dd,1H), 7,77-7,71(m,1H), 7,61(d,1H), 1,32(s,12H) 2,6-Dichlor-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin (XIV-2) 1 H-NMR (400 MHz, D 6 -DMSO) ppmppm: 7.91 (dd, 1H), 7.77-7.71 (m, 1H), 7.61 (d, 1H), 1.32 ( s, 12H) 2,6-dichloro-4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridine (XIV-2)
2,30 g (8,40 mmol) 2,6-Dichlor-4-iodpyridin (XIII-1) und 3,00 g (8,82 mmol) 2-[3-Fluor-4- (pentafluorethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolan wurden in entgastem Dioxan (30 ml) vorgelegt und unter Argon mit 8,4 ml einer 2M-Natriumcarbonatlösung versetzt. Anschließend wurden 97 mg (0,08 mmol) Tetrakis(triphenylphosphin)palladium(0) dazu gegeben und das Reaktionsgemisch wurde über Nacht bei 115 °C gerührt. Das abgekühlte Reaktionsgemisch wurde unter Vakuum von Lösungsmittel befreit, dann in Acetonitril aufgenommen und über Kieselgel filtriert. Das Kieselgel wurde mit Acetonitril nachgewaschen. Die Filtrate wurden vereint und das Lösungsmittel wurde unter Vakuum entfernt. Die Reinigung erfolgte mittels MPLC über eine RP-18 Kartusche mit Gradienten Acetonitril / Wasser / 0,1% Ameisensäure. Man erhielt 2,13 g (93% Reinheit, 65,5% d. Th.) der Titelverbindung (XIV-2). logP (neutral/sauer): 4,97/4,92; MH+: 360; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 8,16(d,1H), 8,09(s,2H), 8,01(d,1H), 7,91(dd,1H) 6-Chlor-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin-2-amin (XXI-1) 2.30 g (8.40 mmol) of 2,6-dichloro-4-iodopyridine (XIII-1) and 3.00 g (8.82 mmol) of 2- [3-fluoro-4- (pentafluoroethyl) phenyl] - 4,4,5,5-tetramethyl-1,3,2-dioxaborolan were placed in degassed dioxane (30 ml) and treated under argon with 8.4 ml of a 2M sodium carbonate solution. Then, 97 mg (0.08 mmol) of tetrakis (triphenylphosphine) palladium (0) was added thereto, and the reaction mixture was stirred at 115 ° C overnight. The cooled reaction mixture was freed of solvent under vacuum, then taken up in acetonitrile and filtered through silica gel. The silica gel was washed with acetonitrile. The filtrates were combined and the solvent was removed in vacuo. The purification was carried out by means of MPLC via an RP-18 cartridge with gradients acetonitrile / water / 0.1% formic acid. This gave 2.13 g (93% purity, 65.5% of theory) of the title compound (XIV-2). logP (neutral / acid): 4.97 / 4.92; MH +: 360; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 8.16 (d, 1H), 8.09 (s, 2H), 8.01 (d, 1H), 7.91 (dd, 1H) 6 Chloro-4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridin-2-amine (XXI-1)
2,10 g (5,83 mmol) 2,6-Dichlor-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin (XIV-2) wurden in Dioxan (30 ml) vorgelegt und mit 30 ml einer 35%igen wäßrigen Ammoniak-Lösung versetzt. Das Autoklavengefäß wurde mit Argon gespült und die Reaktion wurde darin 16 Stunden unter 10 bar Argon-Druck bei 150 °C gerührt. Nach der erneuten Zugabe von 30 ml Ammoniak-Lösung wurde das Reaktionsgemisch über Nacht unter 10 bar Argon-Druck bei 150 °C gerührt. Nach Abkühlen wurde das Lsöungsmittel unter Vakuum entfernt. Der Rückstand wurde in Acetonitril verrührt und die unlöslichen Bestandteile wurden durch Filtration entfernt. Das Filtrat wurde unter Vakuum von Lösungsmittel befreit, bevor es mittels Säulenchromatographie über RP-18 aufgereinigt wurde. Es konnten zwei Fraktionen mit der Titelverbindung (XXI-1) isoliert werden: 850 mg (92% Reinheit, 39% d. Th.) und 497 mg (88% Reinheit, 22% d. Th.). logP (neutral/sauer): 3,83/3,85; MH+: 341; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 7,87-7,83(m,2H), 7,74-7,72(m,1H), 6,94(d,1H), 6,70(d,1H), 6,61(bs,2H) N-{6-Chlor-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin-2-yl}cyclopropancarboxamid (XXII-1) 2.10 g (5.83 mmol) of 2,6-dichloro-4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridine (XIV-2) were initially charged in dioxane (30 ml) and treated with 30 ml of a 35 % aqueous ammonia solution. The autoclave vessel was purged with argon and the reaction was stirred therein at 150 ° C for 16 hours under 10 bar argon pressure. After re-addition of 30 ml of ammonia solution, the reaction mixture was stirred overnight under 10 bar argon pressure at 150 ° C. After cooling, the solvent was removed under vacuum. The residue was stirred in acetonitrile and the insolubles were removed by filtration. The filtrate was freed of solvent under vacuum before being purified by column chromatography over RP-18. There were two Fractions with the title compound (XXI-1): 850 mg (92% purity, 39% of theory) and 497 mg (88% purity, 22% of theory). logP (neutral / acid): 3.83 / 3.85; MH +: 341; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 7.87-7.83 (m, 2H), 7.74-7.72 (m, 1H), 6.94 (d, 1H), 6 , 70 (d, 1H), 6.61 (bs, 2H) N- {6-chloro-4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridin-2-yl} cyclopropanecarboxamide (XXII-1)
800 mg (2,11 mmol) 6-Chlor-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin-2-amin (XXI-1) wurden in Dichlormethan (35 ml) vorgelegt und mit 1,15 ml (8,22 mmol) Triethylamin versetzt. Nach 10 Min bei Raumtemperatur wurden 0,26 ml (2,82 mmol) Cyclopropancarbonsäurechlorid in Dichlormethan (5 ml) gelöst hinzugetropft. Das Reaktionsgemisch wurde über Nacht bei Raumtemperatur gerührt. Anschließend wurde das Lösungsmittel unter Vakuum entfernt und der Rückstand wurde in Toluol (15 ml) aufgenommen. Nach der Zugabe von 0,38 ml (4,70 mmol) Pyridin und 0,26 ml (2,82 mmol) Cyclopropancarbonsäurechlorid wurde das Gemisch bei 100 °C für 5 h gerührt. Nach Abkühlen wurde das Lösungsmittel unter Vakuum entfernt. Der Rückstand wurde in Dichlormethan aufgenommen und mit gesättigter Natriumchlorid-Lösung mehrmals gewaschen. Die organische Phase wurde getrennt, über Natriumsulfat getrocknet, filtriert und unter Vakuum von Lösungsmittel befreit. 1,02 g (96% Reinheit, quantitativ) der Titelverbindung (XXII-1) wurden erhalten. logP (neutral/sauer): 4,64/4,76; MH+: 409; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 12,04+11,30(2xs, 1H), 8,42(d,1H), 7,98-7,88(m,2H), 7,82-7,80(m,1H), 7,66(s,1H), 2,05-1,99(m,1H), 0,87-0,85(m,4H) 6-[(Cyclopropylcarbonyl)amino]-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin-2-carboxamid (XXIII-1) 800 mg (2.11 mmol) 6-chloro-4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridin-2-amine (XXI-1) were initially charged in dichloromethane (35 ml) and treated with 1.15 ml (8.22 mmol) of triethylamine. After 10 min at room temperature, 0.26 ml (2.82 mmol) of cyclopropanecarbonyl chloride dissolved in dichloromethane (5 ml) were added dropwise. The reaction mixture was stirred at room temperature overnight. Then the solvent was removed in vacuo and the residue was taken up in toluene (15 ml). After the addition of 0.38 ml (4.70 mmol) of pyridine and 0.26 ml (2.82 mmol) of cyclopropanecarboxylic acid chloride, the mixture was stirred at 100 ° C for 5 h. After cooling, the solvent was removed under vacuum. The residue was taken up in dichloromethane and washed several times with saturated sodium chloride solution. The organic phase was separated, dried over sodium sulfate, filtered and freed of solvent under vacuum. 1.02 g (96% purity, quantitative) of the title compound (XXII-1) was obtained. logP (neutral / acid): 4.64 / 4.76; MH +: 409; 1 H-NMR (400 MHz, D 6 -DMSO) ppm ppm: 12.04 + 11.30 (2xs, 1H), 8.42 (d, 1H), 7.98-7.88 (m, 2H), 7.82-7.80 (m, 1H), 7.66 (s, 1H), 2.05-1.99 (m, 1H), 0.87-0.85 (m, 4H) 6- [ (Cyclopropylcarbonyl) amino] -4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridine-2-carboxamide (XXIII-1)
900 mg (2,11 mmol) N-{6-Chlor-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin-2- yl}cyclopropancarboxamid (XXII-1) und 260 g (3,17 mmol) Natriumacetat wurden in Methanol (20 ml) in einem 50 ml-Autoklavengefäß vorgelegt. Dann wurden 167 mg (0,21 mmol) Dichlor[(bisdiphenylphosphino)ferrocenyl]palladium(II)aceton-Addukte dazu gegeben und das Gefäß wurde mit 10 bar Argon gespült. Die zweite Leitung im Autoklav enthielt Ammoniak und wurde zusätzlich mit CO gefüllt. Das Reaktionsgemisch wurde unter 10 bar CO 15 Stunden bei 80 °C gehalten. Nach Abkühlen wurde das Lösungsmittel unter Vakuum entfernt. Der Rückstand wurde in Acetonitril suspendiert, unlösliche Bestandteile wurden durch Filtration entfernt. Das resultierende Filtrat wurde unter Vakuum vom Lösungsmittel befreit. Man erhielt 1,07 g (86% Reinheit, quantitativ) der Titelverbindung (XXIII-1). logP (neutral/sauer): 3,17/3,18; MH+: 418; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 12,05(bs,1H), 11,06(s,1H), 8,56(s,1H), 8,03(s,1H), 7,99-7,83(m,3H), 5,40(bs,1H), 2,08-2,02(m,1H), 0,89-0,87(m,4H) N-(Cyclopropylcarbonyl)-6-[(cyclopropylcarbonyl)amino]-4-[3-fluor-4-(pentafluorethyl)- phenyl]pyridin-2-carboxamid (I-264) 900 mg (2.11 mmol) of N- {6-chloro-4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridin-2-yl} cyclopropanecarboxamide (XXII-1) and 260 g (3.17 mmol) Sodium acetate was placed in methanol (20 ml) in a 50 ml autoclave vessel. Then, 167 mg (0.21 mmol) of dichloro [(bisdiphenylphosphino) ferrocenyl] palladium (II) acetone adduct was added and the vessel was purged with 10 bar of argon. The second line in the autoclave contained ammonia and was additionally filled with CO. The reaction mixture was kept under 10 bar CO at 80 ° C for 15 hours. After cooling, the solvent was removed under vacuum. The residue was suspended in acetonitrile, insolubles were removed by filtration. The resulting filtrate was freed of solvent under vacuum. This gave 1.07 g (86% pure, quantitative) of the title compound (XXIII-1). logP (neutral / acidic): 3.17 / 3.18; MH +: 418; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 12.05 (bs, 1H), 11.06 (s, 1H), 8.56 (s, 1H), 8.03 (s, 1H), 7.99-7.83 (m, 3H), 5.40 (bs, 1H), 2.08-2.02 (m, 1H), 0.89-0.87 (m, 4H) N- ( Cyclopropylcarbonyl) -6 - [(cyclopropylcarbonyl) amino] -4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridine-2-carboxamide (I-264)
100 mg (0,21 mmol) 6-[(Cyclopropylcarbonyl)amino]-4-[3-fluor-4-(pentafluorethyl)phenyl]pyridin-2- carboxamid (XXIII-1) wurden in trockenem Tetrahydrofuran (5 mL) gelöst und bei Raumtemperatur mit 7,5 mg (0,31 mmol) Natriumhydrid versetzt. Die Mischung wurde 15 min bei Raumtemperatur gerührt. Anschließend wurden 22 mg (0,21 mmol) Cyclopropancarbonsäurechlorid zugegeben und die Mischung wurde 2 h bei 40 °C gerührt. Nach Abkühlen wurde das Lösungsmittel im Vakuum entfernt und der Rückstand wurde durch säulenchromatographische Aufreinigung über RP-18 mit einem Acetonitril / Wasser Gradienten als Laufmittel gereinigt. Man erhielt 38 mg (100% Reinheit, 38% d. Th.) der Titelverbindung (I-264). logP (neutral/sauer): 4,53/4,62; MH+: 486; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 11,28(s,1H), 10,72(s,1H), 8,68(d,1H), 8,14(d,1H), 8,02(d,1H), 7,94-7,85(m,2H), 2,82-2,76(m,1H), 2,08-1,99(m,1H), 1,07-0,99(m,4H), 0,91-0,89(m,4H) Methyl-6-[(cyclopropylcarbonyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2-carboxylat (XXIII-2) 100 mg (0.21 mmol) of 6 - [(cyclopropylcarbonyl) amino] -4- [3-fluoro-4- (pentafluoroethyl) phenyl] pyridine-2-carboxamide (XXIII-1) were dissolved in dry tetrahydrofuran (5 mL) and at room temperature with 7.5 mg (0.31 mmol) of sodium hydride. The mixture was stirred for 15 minutes at room temperature. Subsequently, 22 mg (0.21 mmol) of cyclopropanecarboxylic acid chloride were added and the mixture was stirred at 40 ° C for 2 h. After cooling, the solvent was removed in vacuo and the residue was purified by column chromatographic purification over RP-18 with an acetonitrile / water gradient as eluent. 38 mg (100% purity, 38% of theory) were obtained. Th.) Of the title compound (I-264). logP (neutral / acid): 4.53 / 4.62; MH +: 486; 1H-NMR (400 MHz, D6-DMSO) ppmppm: 11.28 (s, 1H), 10.72 (s, 1H), 8.68 (d, 1H), 8.14 (d, 1H), 8.02 (d, 1H), 7.94-7.85 (m, 2H), 2.82-2.76 (m, 1H), 2.08-1.99 (m, 1H), 1, 07-0.99 (m, 4H), 0.91-0.89 (m, 4H) Methyl 6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxylate ( XXIII-2)
5,43 g (15,2 mmol) N-{6-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin-2-yl}cyclopropancarboxamid (XXII-2; Synthese analog XXII-1) und 1,87 g (22,8 mmol) Natriumacetat wurden in Methanol (137 ml) in einem 300 ml-Autoklavengefäß vorgelegt. Dann wurden 601 mg (0,76 mmol) Dichlor[(bisdiphenylphosphino)ferrocenyl]palladium(II)aceton-Addukte dazu gegeben. Das Reaktionsgemisch wurde unter 10 bar CO 15 Stunden bei 80 °C carbonyliert. Nach Abkühlen auf Raumtemperatur wurde das Gemisch mit ges. Natriumchloridlösung versetzt und es wurde mehrmals mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum entfernt. Man erhielt 5,75 g (100% Reinheit, 99% d. Th.) der Titelverbindung (XXIII-2). logP (neutral/sauer): 3,54/3,63; MH+: 381; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 11,33 (s,1H), 8,64 (d,1H), 8,02 (d,1H), 7,88-7,92 (m,2H), 7,52-7,54 (m,2H), 3,92 (s, 3H), 2,10-2,14 (m,1H), 0,84-0,86 (m,4H) 6-[(Cyclopropylcarbonyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2-carbonsäure 5.43 g (15.2 mmol) of N- {6-chloro-4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} cyclopropanecarboxamide (XXII-2; Synthesis analogous to XXII-1) and 1.87 g (22.8 mmol) of sodium acetate were placed in methanol (137 ml) in a 300 ml autoclave vessel. Then, 601 mg (0.76 mmol) of dichloro [(bis-diphenylphosphino) ferrocenyl] palladium (II) acetone adduct was added thereto. The reaction mixture was carbonylated under 10 bar CO for 15 hours at 80 ° C. After cooling to room temperature, the mixture was washed with sat. Sodium chloride solution was added and it was extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and filtered. The solvent was removed in vacuo. 5.75 g (100% pure, 99% of theory) of the title compound (XXIII-2) were obtained. logP (neutral / acid): 3.54 / 3.63; MH +: 381; 1 H-NMR (400 MHz, D 6 -DMSO) ppm ppm: 11.33 (s, 1H), 8.64 (d, 1H), 8.02 (d, 1H), 7.88-7.92 ( m, 2H), 7.52-7.54 (m, 2H), 3.92 (s, 3H), 2.10-2.14 (m, 1H), 0.84-0.86 (m, 4H) 6 - [(Cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxylic acid
4,00 g (10,5 mmol) Methyl-6-[(cyclopropylcarbonyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2- carboxylat (XXIII-2) wurden in Methanol (105 ml) gelöst. Dann wurden 14,1 mL (14,1 mmol) 1N Natronlauge zugegeben. Das Reaktionsgemisch wurde über Nacht bei Raumtemperatur gerührt und mit 1N Salzsäure auf pH = 3 eingestellt. Der Methanol wurde im Vakuum entfernt. Der ausgefallene Feststoff wurde abgesaugt, mit Wasser gewaschen und getrocknet. Man erhielt 2,68 g (88% Reinheit, 62% d. Th.) der Titelverbindung. logP (neutral/sauer): 1,25/2,72; MH+: 367; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 13,37 (s,1H), 11,26 (s, 1H), 8,60 (d,1H), 8,00 (d,1H), 7,89-7,91 (m,2H), 7,49-7,54 (m,2H), 2,08-2,15 (m,1H), 0,84-0,86 (m,4H) 6-[(Cyclopropylcarbonyl)amino]-N-isopropoxy-4-[4-(trifluormethoxy)phenyl]pyridin-2- carboxamid (I-237) 4.00 g (10.5 mmol) of methyl 6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxylate (XXIII-2) was dissolved in methanol (105 ml). Then, 14.1 mL (14.1 mmol) of 1N sodium hydroxide solution was added. The reaction mixture was stirred at room temperature overnight and adjusted to pH = 3 with 1N hydrochloric acid. The methanol was removed in vacuo. The precipitated solid was filtered off with suction, washed with water and dried. This gave 2.68 g (88% purity, 62% of theory) of the title compound. logP (neutral / acid): 1.25 / 2.72; MH +: 367; 1 H-NMR (400 MHz, D 6 -DMSO) ppm ppm: 13.37 (s, 1H), 11.26 (s, 1H), 8.60 (d, 1H), 8.00 (d, 1H) , 7.89-7.91 (m, 2H), 7.49-7.54 (m, 2H), 2.08-2.15 (m, 1H), 0.84-0.86 (m, 4H) 6 - [(Cyclopropylcarbonyl) amino] -N-isopropoxy-4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxamide (I-237)
150 mg (0,41 mmol) 6-[(Cyclopropylcarbonyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2- carbonsäure wurden in Dioxan (7 mL) vorgelegt und es wurden 94,2 mg (0,49 mmol) EDC- Hydrochlorid zugegeben. Die Mischung wurde eine Stunde bei Raumtemperatur gerührt. Dann wurden 45,7 mg (0,41 mmol) 2-(Aminooxy)propanhydrochlorid hinzugegeben und die Mischung wurde über Nacht bei Raumtemperatur gerührt. Das Gemisch wurde eingeengt und mit Wasser versetzt. Dann wurde mit Dichlormethan extrahiert und die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Reinigung mit einem Cyclohexan/Ethylacetat Gradienten als Laufmittel gereinigt. Man erhielt 42,7 mg (100% Reinheit, 25% d. Th.) der Titelverbindung (I-237). logP (neutral/sauer): 3,45/3,50; MH+: 424; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 11,23 (s,1H), 10,93 (s, 1H), 8,50 (d,1H), 7,88-7,92 (m,2H), 7,83 (d,1H), 7,53-7,55 (m,2H), 4,15-4,21 (m,1H), 2,06-2,09 (m,1H), 1,23 (d,6H), 0,85-0,87 (m,4H) Nach Verfahren I: N-{6-(Hydrazinocarbonyl)-4-[4-(trifluormethoxy)phenyl]pyridin-2-yl}cyclopropancarboxamid (XXIV-1) 150 mg (0.41 mmol) of 6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxylic acid were initially charged in dioxane (7 mL) and 94.2 mg (0, 49 mmol) of EDC hydrochloride was added. The mixture was stirred for one hour at room temperature. Then, 45.7 mg (0.41 mmol) of 2- (aminooxy) propane hydrochloride was added and the mixture was stirred at room temperature overnight. The mixture was concentrated and water was added. It was then extracted with dichloromethane and the combined organic phases were dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography with a cyclohexane / ethyl acetate gradient as eluent. 42.7 mg (100% pure, 25% of theory) of the title compound (I-237) were obtained. logP (neutral / acid): 3.45 / 3.50; MH +: 424; 1 H NMR (400 MHz, D 6 -DMSO) ppmppm: 11.23 (s, 1H), 10.93 (s, 1H), 8.50 (d, 1H), 7.88-7.92 ( m, 2H), 7.83 (d, 1H), 7.53-7.55 (m, 2H), 4.15-4.21 (m, 1H), 2.06-2.09 (m, 1H), 1.23 (d, 6H), 0.85-0.87 (m, 4H) By Method I: N- {6- (hydrazinocarbonyl) -4- [4- (trifluoromethoxy) phenyl] pyridine-2 -yl} cyclopropanecarboxamide (XXIV-1)
1,50 g (3,94 mmol) Methyl-6-[(cyclopropylcarbonyl)amino]-4-[4-(trifluormethoxy)phenyl]pyridin-2- carboxylat (XXIII-2) wurden in Dioxan (90 ml) gelöst. Dann wurden 1,10 mL (7,88 mmol, 35 Gew.% in Wasser) Hydrazinhydrat langsam zugetropft. Das Reaktionsgemisch wurde zunächst zwei Stunden bei Raumtemperatur gerührt, dann zwei Stunden zum Sieden erhitzt, auf Raumtemperatur abgekühlt und schließlich im Vakuum zur Trockne eingeengt. Man erhielt 2 g der Titelverbindung als Rohprodukt (Reinheit 76%), das ohne weitere Reinigung in der nächsten Stufe verwendet wurde. logP (neutral/sauer): 2,55/2,57; MH+: 381 N-(6-{[(2E)-2-(4-Cyanbenzyliden)hydrazino]carbonyl}-4-[4-(trifluormethoxy)phenyl]pyridin-2- yl)cyclopropancarboxamid (I-252) 1.50 g (3.94 mmol) of methyl 6 - [(cyclopropylcarbonyl) amino] -4- [4- (trifluoromethoxy) phenyl] pyridine-2-carboxylate (XXIII-2) was dissolved in dioxane (90 ml). Then, 1.10 mL (7.88 mmol, 35 wt% in water) of hydrazine hydrate was slowly added dropwise. The reaction mixture was initially stirred for two hours at room temperature, then heated to boiling for two hours, cooled to room temperature and finally concentrated to dryness in vacuo. This gave 2 g of the title compound as a crude product (purity 76%), which was used without further purification in the next stage. logP (neutral / acid): 2.55 / 2.57; MH +: 381 N- (6 - {[(2E) -2- (4-cyanobenzylidene) hydrazino] carbonyl} -4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl) cyclopropanecarboxamide (I-252)
50 mg (0,13 mmol) N-{6-(Hydrazinocarbonyl)-4-[4-(trifluormethoxy)phenyl]pyridin-2- yl}cyclopropancarboxamid (XXIV-1) wurden in Wasser (10 ml) vorgelegt, mit zwei Tropfen konzentrierter Schwefelsäure versetzt und auf 65 °C erwärmt. Dann wurden 57 mg (0,43 mmol) 4-Cyanobenzaldehyd, gelöst in Ethanol (10 mL), zugegeben. Das Reaktionsgemisch wurde 48 Stunden bei 74 °C gerührt, auf Raumtemperatur abgekühlt, auf Eiswasser gegossen und mit 10%iger Natriumcarbonatlösung neutralisiert. Die ausgefallenen Kristalle wurden abgesaugt und durch säulenchromatographische Reinigung mit einem Cyclohexan/Ethylacetat Gradienten als Laufmittel weiter gereinigt. Man erhielt 18 mg (94% Reinheit, 26% d. Th.) der Titelverbindung (I-252). logP (neutral/sauer): 3,83/3,88; MH+: 494; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 11,95 (s,1H), 11,07 (s, 1H), 8,55-8,57 (m,2H), 8,01 (d,1H), 7,92-7,95 (m,6H), 7,54-7,56 (m,2H), 2,07-2,10 (m,1H), 0,85- 0,89 (m,4H) Nach Verfahren J: 2-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin-1-oxid (XXVII-1) 50 mg (0.13 mmol) of N- {6- (hydrazinocarbonyl) -4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} cyclopropanecarboxamide (XXIV-1) were initially charged in water (10 ml), containing two Drops of concentrated sulfuric acid and heated to 65 ° C. Then, 57 mg (0.43 mmol) of 4-cyanobenzaldehyde dissolved in ethanol (10 mL) was added. The reaction mixture was stirred at 74 ° C for 48 hours, cooled to room temperature, poured onto ice-water and neutralized with 10% sodium carbonate solution. The precipitated crystals were filtered off with suction and further purified by column chromatography with a cyclohexane / ethyl acetate gradient as eluent. 18 mg (94% purity, 26% of theory) of the title compound (I-252) were obtained. logP (neutral / acid): 3.83 / 3.88; MH +: 494; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 11.95 (s, 1H), 11.07 (s, 1H), 8.55-8.57 (m, 2H), 8.01 (i.e. , 1H), 7.92-7.95 (m, 6H), 7.54-7.56 (m, 2H), 2.07-2.10 (m, 1H), 0.85-0.89 (m, 4H) By Method J: 2-Chloro-4- [4- (trifluoromethoxy) phenyl] pyridine-1-oxide (XXVII-1)
30 g (109 mmol) 2-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin (XXVI-1, Synthese analog XIV-1 und XIV-2 aus XIII-1) wurden in Dichlormethan (500 ml) vorgelegt und mit 56,9 g (329 mmol) 3- Chlorperbenzoesäure (mCPBA) versetzt. Die Mischung wurde über Nacht bei 50 °C gerührt, auf Raumtemperatur abgekühlt und mit ges. Natriumhydrogencarbonatlösung gewaschen. Das Lösungsmittel wurde im Vakuum entfernt und der Rückstand wurde durch säulenchromatographische Reinigung mit einem Dichlormethan/Methanol Gradienten als Laufmittel gereinigt. Man erhielt 20 g (63% d. Th.) der Titelverbindung (XXVII-1). MH+: 290 6-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin-2-carbonitril (XXVIII-1) 30 g (109 mmol) of 2-chloro-4- [4- (trifluoromethoxy) phenyl] pyridine (XXVI-1, synthesis analogous to XIV-1 and XIV-2 from XIII-1) were initially charged in dichloromethane (500 ml) and washed with 56.9 g (329 mmol) of 3-chloroperbenzoic acid (mCPBA) were added. The mixture was stirred overnight at 50 ° C, cooled to room temperature and washed with sat. Washed sodium bicarbonate solution. The solvent was removed in vacuo and the residue was purified by column chromatography eluting with a dichloromethane / methanol gradient. 20 g (63% of theory) of the title compound (XXVII-1) were obtained. MH +: 290 6-Chloro-4- [4- (trifluoromethoxy) phenyl] pyridine-2-carbonitrile (XXVIII-1)
20 g (69,1 mmol) 2-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin-1-oxid (XXVII-1) wurden in Acetonitril (300 ml) vorgelegt und mit 41,1 g (414 mmol) Trimethylsilylcyanid (TMSCN) und 14 g (138 mmol) Triethylamin versetzt. Die Mischung wurde über Nacht bei 100 °C gerührt und auf Raumtemperatur abgekühlt. Die flüchtigen Bestandteile wurden im Vakuum entfernt und der Rückstand wurde durch säulenchromatographische Reinigung mit einem Ethylacetat/Petrolether Gradienten als Laufmittel gereinigt. Man erhielt 14 g (68% d. Th.) der Titelverbindung (XXVIII-1). MH+: 299; 1H-NMR(300 MHz, CDCl3) ^ ppm: 7.82 (s, 1H), 7.74 (s, 1H), 7.66-7.70 (m, 2H), 7.40-7.42 (m, 2H). N-{6-Cyan-4-[4-(trifluormethoxy)phenyl]pyridin-2-yl}cyclopropancarboxamid (XXIX-1) 20 g (69.1 mmol) of 2-chloro-4- [4- (trifluoromethoxy) phenyl] pyridine-1-oxide (XXVII-1) were initially charged in acetonitrile (300 ml) and treated with 41.1 g (414 mmol). Trimethylsilyl cyanide (TMSCN) and 14 g (138 mmol) of triethylamine were added. The mixture was stirred overnight at 100 ° C and cooled to room temperature. The volatiles were removed in vacuo and the residue was purified by column chromatography with an ethyl acetate / petroleum gradient gradient. 14 g (68% of theory) of the title compound (XXVIII-1) were obtained. MH +: 299; 1H-NMR (300 MHz, CDCl3) ^ ppm: 7.82 (s, 1H), 7.74 (s, 1H), 7.66-7.70 (m, 2H), 7.40-7.42 (m, 2H). N- {6-cyano-4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} cyclopropanecarboxamide (XXIX-1)
Eine Mischung aus 5 g (16,7 mmol) 6-Chlor-4-[4-(trifluormethoxy)phenyl]pyridin-2-carbonitril (XXVIII-1), 2,85 g (33,5 mmol) Cyclopropancarboxamid, 2 g (3,46 mmol) XantPhos, 16,4 g (50,3 mmol) Cäsiumcarbonat und 1 g (1,09 mmol) Pd2(dba)3 in Dioxan (200 ml) wurde unter Stickstoffatmosphäre über Nacht bei 100 °C gerührt und anschließend auf Raumtemperatur abgekühlt. Die festen Bestandteile wurden abfiltriert und das Filtrat wurde im Vakuum eingeengt. Der Rückstand wurde durch säulenchromatographische Reinigung mit einem Ethylacetat/Petrolether Gradienten als Laufmittel gereinigt. Man erhielt 3,15 g (54% d. Th., Reinheit 97%) der Titelverbindung (XXIX-1). logP (neutral/sauer): 3,89/3,85; MH+: 348; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 11,38 (s,1H), 8,68 (d,1H), 8,14 (d,1H), 7,91-7,95 (m,2H), 7,54-7,56 (m,2H), 1,99-2,06 (m,1H), 0,87-0,89 (m,4H). N-{6-[N-(4-Cyanbenzyl)carbamimidoyl]-4-[4-(trifluormethoxy)phenyl]pyridin-2- yl}cyclopropancarboxamid (I-258) A mixture of 5 g (16.7 mmol) of 6-chloro-4- [4- (trifluoromethoxy) phenyl] pyridine-2-carbonitrile (XXVIII-1), 2.85 g (33.5 mmol) of cyclopropanecarboxamide, 2 g (3.46 mmol) of XantPhos, 16.4 g (50.3 mmol) of cesium carbonate and 1 g (1.09 mmol) of Pd 2 (dba) 3 in dioxane (200 ml) was stirred under nitrogen atmosphere at 100 ° C overnight and then cooled to room temperature. The solid was filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography with an ethyl acetate / petroleum gradient gradient. 3.15 g (54% of theory, purity 97%) of the title compound (XXIX-1) were obtained. logP (neutral / acid): 3.89 / 3.85; MH +: 348; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 11.38 (s, 1H), 8.68 (d, 1H), 8.14 (d, 1H), 7.91-7.95 (m , 2H), 7.54-7.56 (m, 2H), 1.99-2.06 (m, 1H), 0.87-0.89 (m, 4H). N- {6- [N- (4-cyanobenzyl) carbamimidoyl] -4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} cyclopropanecarboxamide (I-258)
Eine Mischung aus 150 mg (0,43 mmol) N-{6-Cyan-4-[4-(trifluormethoxy)phenyl]pyridin-2- yl}cyclopropancarboxamid (XXIX-1) und 57 mg (0,43 mmol) 4-(Aminomethyl)benzonitril in Dioxan (0,5 mL) wurde auf 90 °C erhitzt, mit 0,07 mL (0,51 mmol) Zinn(IV)tetrachlorid versetzt und vier Stunden bei 95 °C gerührt. Nach dem Abkühlen auf Raumtemperatur wurde die Mischung mit ges. Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die organische Phase wurde abgetrennt und das Lösungsmittel wurde im Vakuum entfernt. Ein weiterer Ansatz mit identischer Ansatzgröße wurde nach der oben beschriebenen Vorschrift durchgeführt. Die beiden Rohprodukte wurden zusammen durch säulenchromatographische Reinigung mit einem Cyclohexan/Aceton/Methanol Gradienten als Laufmittel gereinigt. Man erhielt 7,3 mg (2% d. Th.) der Titelverbindung (I-258). logP (neutral/sauer): 4,24/2,08; MH+: 480; 1H-NMR(400 MHz, D6-DMSO) ^ ppm: 11,07 (s,1H), 9,27 (bs, 1H), 8,58 (s,1H), 8,21 (s,1H), 7,93-7,95 (m,2H), 7,87-7,89 (m,2H), 7,64-7,66 (m,2H), 7,55-7,57 (m,2H), 7,37 (bs, 1H), 4,77 (s, 2H) 2,04-2,10 (m,1H), 0,85-0,89 (m,4H). In Analogie zu den Beispielen und gemäß den oben beschriebenen Herstellverfahren lassen sich folgende Verbindungen der Formel (I) erhalten, wobei die Substituenten R1, R2, R3, R4, R5, R6, Q1, V1 und V2 die in der folgenden Tabelle 1 angegebenen Bedeutungen haben: A mixture of 150 mg (0.43 mmol) of N- {6-cyano-4- [4- (trifluoromethoxy) phenyl] pyridin-2-yl} cyclopropanecarboxamide (XXIX-1) and 57 mg (0.43 mmol) of 4 - (Aminomethyl) benzonitrile in dioxane (0.5 mL) was heated to 90 ° C, treated with 0.07 mL (0.51 mmol) of tin (IV) tetrachloride and stirred at 95 ° C for four hours. After cooling to room temperature, the mixture was washed with sat. Sodium bicarbonate solution and dichloromethane. The organic phase was separated and the solvent was removed in vacuo. Another approach with identical batch size was carried out according to the procedure described above. The two crude products were purified together by column chromatography purification with a cyclohexane / acetone / methanol gradient as eluent. This gave 7.3 mg (2% of theory) of the title compound (I-258). logP (neutral / acid): 4.24 / 2.08; MH +: 480; 1H-NMR (400 MHz, D6-DMSO) ^ ppm: 11.07 (s, 1H), 9.27 (bs, 1H), 8.58 (s, 1H), 8.21 (s, 1H), 7.93-7.95 (m, 2H), 7.87-7.89 (m, 2H), 7.64-7.66 (m, 2H), 7.55-7.57 (m, 2H), 7.37 (bs, 1H), 4.77 (s, 2H) 2.04-2.10 (m, 1H), 0.85-0.89 (m, 4H). In analogy to the examples and according to the preparation process described above, the following compounds of the formula (I) can be obtained, wherein the substituents R 1, R 2, R 3, R 4, R 5, R 6, Q 1, V 1 and V 2 have the meanings given in Table 1 below to have:
(I) (I)
BB
C C
S S
61 3 Q1 Weiterer 01  61 3 Q1 Other 01
Deskriptor 4 Descriptor 4
-A uorphenyl W uorphenyl M rifluormethyl)phenyl L - A uorphenyl W uorphenyl M rifluoromethyl) phenyl L
-A rifluormethyl)phenyl N rifluormethyl)phenyl 20 rifluormethyl)phenyl 17 rifluormethyl)phenyl - 10 rifluormethyl)phenyl - 81 rifluormethyl)phenyl 1 - rifluormethyl)phenyl 83- A rifluoromethyl) phenyl N, rifluoromethyl) phenyl 2 0 rifluoromethyl) phenyl 17 rifluoromethyl) phenyl - 1 0 rifluoromethyl) phenyl - 8 1 rifluoromethyl) phenyl 1 - rifluoromethyl) phenyl 83
- rifluormethyl)phenyl - Rifluoromethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl  rifluormethyl) phenyl
I rifluormethyl)phenyl I rifluoromethyl) phenyl
I rifluormethyl)phenylI rifluoromethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
lorphenyl lorphenyl
rifluormethyl)phenyl rifluormethyl) phenyl
lorphenyl lorphenyl
rifluormethyl)phenyl rifluormethyl) phenyl
lorphenyl lorphenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl  rifluormethyl) phenyl
B rifluormethyl)phenyl C B rifluoromethyl) phenyl C
S S
ifluormethoxy)phenyl 61 ifluoromethoxy) phenyl 61
3 ifluormethoxy)phenyl 01 rifluormethyl)phenyl 4 3 isluoromethoxy) phenyl 01 rifluoromethyl) phenyl 4
-A rifluormethyl)phenyl W rifluormethyl)phenyl M rifluormethyl)phenyl L - A rifluoromethyl) phenyl W rifluoromethyl) phenyl M rifluoromethyl) phenyl L
-A dphenyl N rifluormethyl)phenyl 20 rifluormethyl)phenyl 17 rifluormethyl)phenyl - 10 rifluormethyl)phenyl - 81 rifluormethyl)phenyl -1 rifluormethyl)phenyl 39 rifluormethyl)phenyl - rifluormethyl)phenyl- A dphenyl N, rifluoromethyl) phenyl 2 0 rifluoromethyl) phenyl 17 rifluoromethyl) phenyl - 1 0 rifluoromethyl) phenyl - 8 1 rifluoromethyl) phenyl - 1 rifluoromethyl) phenyl 39 rifluoromethyl) phenyl - rifluoromethyl) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
dphenyl dphenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethyl)sulfanyl]phenyl rifluormethyl) sulfanyl] phenyl
omphenyl omphenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethyl)phenyl  rifluormethyl) phenyl
B rifluormethyl)phenyl C B rifluoromethyl) phenyl C
S S
rifluormethyl)phenyl 61 rifluoromethyl) phenyl 61
3 rifluormethoxy)phenyl 10 rifluormethoxy)phenyl 4 3 rifluoromethoxy) phenyl 10 rifluoromethoxy) phenyl 4
-A rifluormethoxy)phenyl W rifluormethyl)phenyl M rifluormethoxy)phenyl L - A rifluoromethoxy) phenyl W rifluoromethyl) phenyl M rifluoromethoxy) phenyl L
-A rifluormethyl)phenyl N rifluormethoxy)phenyl 20 rifluormethyl)phenyl 17 I rifluormethyl)phenyl - 10 I rifluormethoxy)phenyl - 81 I rifluormethyl)phenyl -1 I rifluormethyl)phenyl 40 I rifluormethoxy)phenyl - rifluormethyl)phenyl - A rifluormethyl) phenyl N rifluormethoxy) phenyl 2 0 rifluormethyl) phenyl 17 I rifluormethyl) phenyl - 1 0 I rifluormethoxy) phenyl - 8 1 I rifluormethyl) phenyl - 1 I rifluormethyl) phenyl 40 I rifluormethoxy) phenyl - rifluormethyl) phenyl
I rifluormethoxy)phenylI rifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethyl)phenyl  rifluormethyl) phenyl
I rifluormethyl)phenylI rifluoromethyl) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
I rifluormethoxy)phenylI rifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
I rifluormethyl)phenylI rifluoromethyl) phenyl
rifluormethyl)phenyl rifluormethyl) phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
B rifluormethyl)sulfanyl]phenyl C B rifluoromethyl) sulfanyl] phenyl C
S S
rifluormethoxy)phenyl 1 trifluoromethoxy) phenyl 1
36 10 4 -A W M36 10 4 - A W M
L  L
-A N- A N
rifluormethoxy)phenyl 20 rifluormethyl)sulfanyl]phenyl 17 rifluormethoxy)phenyl - 10 - 81 rifluormethoxy)phenyl rifluoromethoxy) phenyl 2 0 rifluoromethyl) sulfanyl] phenyl 17 rifluoromethoxy) phenyl - 1 0 - 8 1 rifluoromethoxy) phenyl
- rifluormethyl)sulfonyl]phenyl 1 - Rifluoromethyl) sulfonyl] phenyl 1
14 rifluormethyl)sulfonyl]phenyl - ethyl-4-(trifluormethoxy)phenyl 14 rifluoromethyl) sulfonyl] phenyl - ethyl-4- (trifluoromethoxy) phenyl
ethyl-4-(trifluormethoxy)phenyl rifluormethoxy)phenyl ethyl-4- (trifluoromethoxy) phenylrifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethyl)sulfonyl]phenyl  rifluormethyl) sulfonyl] phenyl
I rifluormethoxy)phenylI rifluoromethoxy) phenyl
rifluormethyl)sulfanyl]phenyl rifluormethyl) sulfanyl] phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
B B
C C
S S
61 03 41 -A W 61 03 41 - A W
M M
rifluormethoxy)phenyl L rifluormethoxy)phenyl -A rifluoromethoxy) phenyl L rifluoromethoxy) phenyl - A
N N
rifluormethoxy)phenyl 2 I rifluormethoxy)phenyl 10Rifluoromethoxy) phenyl 2 I rifluoromethoxy) phenyl 10
7 rifluormethoxy)phenyl - 10 rifluormethoxy)phenyl -1 rifluormethoxy)phenyl 87 rifluoromethoxy) phenyl - 1 0 rifluoromethoxy) phenyl - 1 rifluoromethoxy) phenyl 8
1 - 24 - rifluormethoxy)phenyl 1 - 24 - rifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
lor-5-(trifluormethyl)pyridin-2-yl lor-5- (trifluoromethyl) pyridin-2-yl
rifluormethyl)sulfonyl]phenyl rifluormethyl) sulfonyl] phenyl
uor-4-(trifluormethoxy)phenyl fluoro-4- (trifluoromethoxy) phenyl
lor-4-(trifluormethoxy)phenyl lor-4- (trifluoromethoxy) phenyl
rifluormethyl)pyridin-3-yl rifluormethyl) pyridin-3-yl
uor-4-(trifluormethoxy)phenyl fluoro-4- (trifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
B rifluormethoxy)phenyl C B rifluoromethoxy) phenyl C
S S
rifluormethoxy)phenyl 1 trifluoromethoxy) phenyl 1
36 rifluormethoxy)phenyl 10 rifluormethoxy)phenyl 4 36 rifluoromethoxy) phenyl 10 rifluoromethoxy) phenyl 4
-A rifluormethoxy)phenyl W rifluormethoxy)phenyl M rifluormethoxy)phenyl L - A rifluoromethoxy) phenyl W rifluoromethoxy) phenyl M rifluoromethoxy) phenyl L
-A rifluormethoxy)phenyl N - A rifluoromethoxy) phenyl N
2 10 7 - 10 rifluormethoxy)phenyl 1- 8 rifluormethoxy)phenyl -1 rifluormethoxy)phenyl 342 10 7 - 1 0 rifluoromethoxy) phenyl 1 - 8 rifluoromethoxy) phenyl - 1 rifluoromethoxy) phenyl 34
- rifluormethoxy)phenyl - Rifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
yclopropylsulfanyl)phenyl yclopropylsulfanyl) phenyl
uor-6-(trifluormethyl)pyridin-3-yl fluoro-6- (trifluoromethyl) pyridin-3-yl
,2,2-Trifluorethyl)phenyl , 2,2-trifluoroethyl) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
hyl-6-methyl-4- tafluorethyl)phenyl hyl-6-methyl-4-tafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
,1,1,2,3,3,3-Heptafluorpropan- phenyl , 1,1,2,3,3,3-heptafluoropropane-phenyl
rifluormethyl)sulfinyl]phenyl rifluormethyl) sulfinyl] phenyl
Difluor-4- uormethoxy)phenyl Difluoro-4-normethoxy) phenyl
,1,2,2-Tetrafluorethoxy)phenyl  , 1,2,2-tetrafluoroethoxy) phenyl
B B
Difluor-1,3-benzodioxol-5-yl C Difluoro-1,3-benzodioxol-5-yl C
S S
ifluormethoxy)-3,5-difluorphenyl 1 ifluoromethoxy) -3,5-difluorophenyl 1
36 0 rifluormethoxy)phenyl 14 36 0 rifluoromethoxy) phenyl 14
-A rifluormethoxy)phenyl- A rifluoromethoxy) phenyl
rifluormethoxy)phenyl Racemat W rifluoromethoxy) phenyl racemate W
M M
rifluormethoxy)phenyl L rifluormethyl)-2-thienyl -A rifluoromethoxy) phenyl L-rifluoromethyl) -2-thienyl- A
N N
rifluormethoxy)phenyl 2 rifluormethoxy)phenyl 01 rifluormethoxy)phenyl 7rifluoromethoxy) phenyl 2 rifluoromethoxy) phenyl 01 rifluoromethoxy) phenyl 7
0- rifluormethoxy)phenyl 1 0-rifluoromethoxy) phenyl 1
- 81 1 - 44 rifluormethoxy)phenyl - rifluormethoxy)phenyl- 8 1 1 - 44 rifluoromethoxy) phenyl - rifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluorvinyl)oxy]phenyl rifluorvinyl) oxy] phenyl
3,3-Tetrafluor-2,3-dihydro-1,4- zodioxin-6-yl  3,3-tetrafluoro-2,3-dihydro-1,4-zodioxin-6-yl
5-phenyl 5-phenyl
B rifluormethyl)pyridin-2-yl C B rifluoromethyl) pyridin-2-yl C
S S
rifluormethoxy)phenyl 61 rifluoromethoxy) phenyl 61
3 rifluormethoxy)phenyl 10 rifluormethoxy)phenyl 4 3 rifluoromethoxy) phenyl 10 rifluoromethoxy) phenyl 4
-A ,1,2,2- afluorethyl)sulfanyl]phenyl W - A , 1,2,2-Afluoroethyl) sulfanyl] phenyl W
M M
ifluormethyl)sulfinyl]phenyl L ifluormethyl)sulfanyl]phenyl -A ifluoromethyl) sulfinyl] phenyl L-fluoromethyl) sulfanyl] phenyl- A
N N
rifluormethoxy)phenyl 2 entafluorethyl)phenyl 10 rifluormethoxy)phenyl 7rifluoromethoxy) phenyl 2 entafluoroethyl) phenyl 10 rifluoromethoxy) phenyl 7
-0 rifluormethoxy)phenyl 1- 0 rifluoromethoxy) phenyl 1
1- uor-4-(pentafluorethyl)phenyl 8 rifluormethoxy)phenyl - 41 5 rifluormethoxy)phenyl - entafluorethyl)-1H-pyrazol-1-yl 1-uor-4- (pentafluoroethyl) phenyl 8-rifluoromethoxy) phenyl-4 1 5 -rifluoromethoxy) phenyl-entafluoroethyl) -1H-pyrazol-1-yl
F F NNN....../12.4  F F NNN ...... / 12.4
F -/ F - /
rifluormethoxy)phenyl rifluormethoxy) phenyl
hlor(difluor)methoxy]phenyl hlor (difluoro) methoxy] phenyl
entafluorethoxy)phenyl entafluorethoxy) phenyl
,1-Difluorethyl)phenyl , 1-difluoroethyl) phenyl
- luormethyl)cyclopropyl]phenyl - luomethyl) cyclopropyl] phenyl
-Chlor-1,1,2- orethoxy)phenyl -Chloro-1,1,2-orethoxy) phenyl
entafluorethyl)phenyl entafluorethyl) phenyl
entafluorethyl)phenyl entafluorethyl) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
B B
C C
1S 36 0 rifluormethoxy)phenyl 14 1S 36 0 rifluoromethoxy) phenyl 14
-A rifluormethoxy)phenyl - A rifluoromethoxy) phenyl
W M W M
L  L
-A rifluormethoxy)phenyl N - A rifluoromethoxy) phenyl N
2 10 7 - 10 - 81 rifluormethoxy)phenyl - 41 -6 rifluormethoxy)phenyl2 10 7 - 1 0 - 8 1 rifluoromethoxy) phenyl - 4 1 -6 -trifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
t rifluormethoxy)phenylt rifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl  rifluormethoxy) phenyl
I rifluormethoxy)phenylI rifluoromethoxy) phenyl
rifluormethoxy)phenyl ( ^)-Enantiomer rifluormethoxy)phenyl ( ^)-Enantiomer  rifluoromethoxy) phenyl (^) enantiomer, rifluoromethoxy) phenyl (^) enantiomer
B rifluormethoxy)phenyl C B rifluoromethoxy) phenyl C
S  S
I rifluormethoxy)phenyl 61I rifluoromethoxy) phenyl 61
3 ifluormethyl)-3-fluorphenyl 01 rifluormethoxy)phenyl 4 3-fluoromethyl) -3-fluorophenyl 01-rifluoromethoxy) -phenyl 4
-A uor-4-(trifluormethyl)phenyl W is(trifluormethyl)amino]phenyl M rifluormethoxy)phenyl L - A uor-4- (trifluoromethyl) phenyl W is (trifluoromethyl) amino] phenyl M rifluoromethoxy) phenyl L
-A rifluormethoxy)phenyl N rifluormethoxy)phenyl 02 rifluormethoxy)phenyl 71 lor-4-(trifluormethoxy)phenyl - 10 -1 rifluormethoxy)phenyl 8 - A rifluoromethoxy) phenyl N rifluoromethoxy) phenyl 0 2 rifluoromethoxy) phenyl 71 lor-4- (trifluoromethoxy) phenyl - 1 0 - 1 rifluoromethoxy) phenyl 8
- 41 rifluormethoxy)phenyl 7- rifluormethoxy)phenyl- 4 1 rifluoromethoxy) phenyl-7-rifluoromethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl  fluoro-4- (pentafluoroethyl) phenyl
B uor-4-(pentafluorethyl)phenyl C B uor-4- (pentafluoroethyl) phenyl C
S S
61 03 41 -A W M61 03 41 - A W M
L  L
-A N- A N
rifluormethoxy)phenyl 02 uor-4-(pentafluorethyl)phenyl 71 ,1,2,3,3,3- -0 afluorpropoxy)phenyl 1Rifluoromethoxy) phenyl 0 2 uor-4- (pentafluoroethyl) phenyl 71, 1,2,3,3,3- - 0 afluoropropoxy) phenyl 1
-1 rifluormethoxy)phenyl 8 rifluormethoxy)phenyl - 841 - - 1 rifluoromethoxy) phenyl 8 rifluoromethoxy) phenyl - 84 1 -
rifluormethoxy)phenylrifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
rifluormethoxy)phenyl rifluormethoxy) phenyl
om-3-fluorphenyl om-3-fluorophenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
Dichlor-4- tafluorethyl)phenyl  Dichloro-4-tafluoroethyl) phenyl
B lor-3-fluor-4- C tafluorethyl)phenyl S1 uor-5-methyl-4- 63 tafluorethyl)phenyl 0 B lor-3-fluoro-4-C tafluoroethyl) phenyl S1 -or-5-methyl-4-63 tafluoroethyl) phenyl 0
41 Difluor-4- -A tafluorethyl)phenyl41 difluoro-4- ( a tafluoroethyl) phenyl
lor-5-fluor-4- W tafluorethyl)phenyl MLor-5-fluoro-4- W tafluoroethyl) phenyl M
L L
ethyl-4-(pentafluorethyl)phenyl -A Difluor-4- N tafluorethyl)phenyl 2 Difluor-4- 10 tafluorethyl)phenyl 7ethyl-4- (pentafluoroethyl) phenyl- A difluoro-4-N-tafluoroethyl) phenyl 2- difluoro-4-10-tafluoroethyl) phenyl 7
-0 lor-4-(pentafluorethyl)phenyl 1 0 -Lor-4- (pentafluoroethyl) phenyl 1
-1 5-Trifluor-4- 8 tafluorethyl)phenyl -1 Difluor-4- 49 tafluorethyl)phenyl - Dichlor-3-fluor-4- tafluorethyl)phenyl- 1 5-trifluoro-4-8 tafluoroethyl) phenyl - 1 difluoro-4-49 tafluoroethyl) phenyl - dichloro-3-fluoro-4-tafluoroethyl) phenyl
uor-4-(pentafluorethyl)phenyl fluoro-4- (pentafluoroethyl) phenyl
lor-5-fluor-4- tafluorethyl)phenyl  Lor-5-fluoro-4-tafluoroethyl) phenyl
Die Messung der logP Werte erfolgt gemäß EEC Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18). Temperatur: 55°C. Die Bestimmung mit der LC-MS im sauren Bereich erfolgt bei pH 2,7 mit 0,1 % wässriger Ameisensäure und Acetonitril (enthält 0,1% Ameisensäure) als Eluenten; linearer Gradient von 10% Acetonitril bis 95% Acetonitril. In der Tabelle logP (HCOOH) genannt. Die Bestimmung mit der LC-MS im neutralen Bereich erfolgt bei pH 7.8 mit 0,001 molarer wässriger Ammoniumhydrogencarbonat-Lösung und Acetonitril als Eluenten; linearer Gradient von 10 % Acetonitril bis 95 % Acetonitril. In der Tabelle logP (neutral) genannt. Die Eichung erfolgt mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP- Werte bekannt sind (Bestimmung der logP-Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinander folgenden Alkanonen). Die NMR-Daten ausgewählter Beispiele werden entweder in klassischer Form ( ^-Werte, Multiplettaufspaltung, Anzahl der H-Atome) oder als NMR-Peak-Listen aufgeführt. Das Lösungsmittel, in welchem das NMR-Spektrum aufgenommen wurde ist jeweils angegeben. NMR-Peak-Listenverfahren Die 1H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der ^-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die ^-Wert– Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste eines Beispieles hat daher die Form: The measurement of the logP values is carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 55 ° C. The determination with the LC-MS in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile. In the table called logP (HCOOH). The determination with the LC-MS in the neutral range is carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile. In the table called logP (neutral). The calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones). The NMR data of selected examples are listed either in classical form (^ values, multiplet splitting, number of H atoms) or as NMR peak lists. The solvent in which the NMR spectrum was recorded is given in each case. NMR Peak List Method The 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak first the ^ value in ppm and then the signal intensity in parentheses is listed. The ^ value signal intensity number pairs of different signal peaks are listed separated by semicolons. The peak list of an example therefore has the form:
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Die Listen der 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR-Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. Darüber hinaus können sie wie klassische 1H-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von“Nebenprodukt-Fingerabdrücken” zu erkennen. Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. Weitere Details zu 1H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Anwendungsbeispiele Ctenocephalides felis– in-vitro Kontakttests mit adulten Katzenflöhen Für die Beschichtung der Teströhrchen werden zunächst 9 mg Wirkstoff in 1 ml Aceton p.a. gelöst und anschließend mit Aceton p.a. auf die gewünschte Konzentration verdünnt. 250 µl der Lösung werden durch Drehen und Kippen auf einem Rotationsschüttler (2 h Schaukelrotation bei 30 rpm) homogen auf den Innenwänden und dem Boden eines 25ml Glasröhrchens verteilt. Bei 900 ppm Wirkstofflösung und 44,7 cm² Innenoberfläche wird bei homogener Verteilung eine Flächendosis von 5 µg/cm² erreicht. Nach Abdampfen des Lösungsmittels werden die Gläschen mit 5-10 adulten Katzenflöhen (Ctenocephalides felis) besetzt, mit einem gelochten Kunststoffdeckel verschlossen und liegend bei Raumtemperatur und Umgebungsfeuchte inkubiert. Nach 48 h wird die Wirksamkeit bestimmt. Hierzu werden die Gläschen aufrecht gestellt und die Flöhe auf den Boden des Gläschens geklopft. Flöhe, die unbeweglich auf dem Boden verbleiben oder sich unkoordiniert bewegen, gelten als tot bzw. angeschlagen. Eine Substanz zeigt gute Wirkung gegen Ctenocephalides felis, wenn in diesem Test bei einer Aufwandmenge von 5 µg/cm² mindestens 80% Wirkung erzielt wurde. Dabei bedeutet 100% Wirkung, dass alle Flöhe angeschlagen oder tot waren. 0% Wirkung bedeutet, dass keine Flöhe geschädigt wurden. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 5 µg/cm² (500 g/ha): I-118, I-128, I-138, I-162, I-197, 216. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 5 µg/cm² (500 g/ha): I-013 Boophilus microplus–Injektionstest Lösungsmittel: Dimethylsulfoxid Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Lösungsmittel und verdünnt das Konzentrat mit Lösungsmittel auf die gewünschte Konzentration. 1µl der Wirkstofflösung wird in das Abdomen von 5 vollgesogenen, adulten, weiblichen Rinderzecken (Boophilus microplus) injiziert. Die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. Die Wirkungskontrolle erfolgt nach 7 Tagen auf Ablage fertiler Eier. Eier, deren Fertilität nicht äußerlich sichtbar ist, werden bis zum Larvenschlupf nach etwa 42 Tagen im Klimaschrank aufbewahrt. Eine Wirkung von 100 % bedeutet, dass keine der Zecken fertile Eier gelegt hat, 0% bedeutet, dass alle Eier fertil sind. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 95% bei einer Aufwandmenge von 20µg/Tier: I-104. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 20µg/Tier: I-151 Ctenocephalides felis - Oraltest Lösungsmittel: Dimethylsulfoxid Zwecks Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid. Durch Verdünnen mit citriertem Rinderblut erhält man die gewünschte Konzentration. Ca. 20 nüchterne adulte Katzenflöhe (Ctenocephalides felis) werden in eine Kammer eingesetzt, die oben und unten mit Gaze verschlossen ist. Auf die Kammer wird ein Metallzylinder gestellt, dessen Unterseite mit Parafilm verschlossen ist. Der Zylinder enthält die Blut-Wirkstoffzubereitung, die von den Flöhen durch die Parafilmmembran aufgenommen werden kann. Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Flöhe abgetötet wurden; 0 % bedeutet, dass keiner der Flöhe abgetötet wurde. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 100ppm: I-004, I-005, I-008, I-013, I-026, I-027, I-028, I-030, I- 036, I-043, I-044, I-051, I-052, I-073, I-074, I-075, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-085, I-089, I-094, I-096, I-098, I-102, I-105, I-108, I-109, I-110, I-113, I-115, I-116, I-117, I-118, I-120, I- 124, I-128, I-130, I-131, I-133, I-138, I-141, I-142, I-149, I-151, I-152, I-154, I-155, I-159, I-160, I-162, I-172, I-173, I-176, I-178, I-179, I-182, I-184, I-189, I-190, I-192, I-195, I-196, I-197, I-213, I-216, I- 224, I-225, I-226, I-228, I-232, I-233, I-245, I-247, I-249, I-250. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 98% bei einer Aufwandmenge von 100ppm: I-015, I-017, I-025, I-040, I-070 Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 95% bei einer Aufwandmenge von 100ppm: I-041, I-053, I-065, I-091, I-093, I-095, I-150, I-235. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 100ppm: I-088, I-167. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 100ppm: I-104, I-217. Lucilia cuprina– Test Lösungsmittel: Dimethylsulfoxid Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Ca. 20 L1-Larven der Australischen Schafgoldfliege (Lucilia cuprina) werden in ein Testgefäß überführt, welches gehacktes Pferdefleisch und die Wirkstoffzubereitung der gewünschten Konzentration enthält. Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 100ppm: I-005, I-013, I-015, I-026, I-040, I-043, I-044, I-048, I- 052, I-053, I-070, I-073, I-074, I-077, I-078, I-079, I-080, I-081, I-082, I-085, I-091, I-093, I-094, I-096, I-098, I-104, I-107, I-113, I-120, I-124, I-128, I-133, I-138, I-141, I-149, I-151, I-154, I-155, I-160, I- 172, I-173, I-176, I-178, I-182, I-184, I-190, I-195, I-196, I-197, I-213, I-217, I-224, I-225, I-228, I-247, I-249. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 95% bei einer Aufwandmenge von 100ppm: I-008, I-089, I-117, I-250. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 100ppm: I-027, I-030, I-108, I-115, I-142, I-152, I-159, I-192. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 85% bei einer Aufwandmenge von 100ppm: I-021. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 100ppm: I-216, I-245. Musca domestica–Test Lösungsmittel: Dimethylsulfoxid Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Gefäße, die einen Schwamm enthalten, der mit Zuckerlösung und der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit 10 adulten Stubenfliegen (Musca domestica) besetzt. Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Fliegen abgetötet wurden; 0 % bedeutet, dass keine der Fliegen abgetötet wurde. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 100ppm: I-013, I-026, I-074, I-078, I-089, I-138, I-151, I-154, I- 155, I-172, I-195. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 100ppm: I-040, I-079, I-107, I-152. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 100ppm: I-073, I-077, I-085, I-115, I-159, I-160, I-196, I-197. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 20ppm: I-184, I-195, I-197. Meloidogyne incognita- Test Lösungsmittel: 125,0 Gewichtsteile Aceton Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Gefäße werden mit Sand, Wirkstofflösung, einer Ei-Larven-Suspension des südlichen Wurzelgallenälchens (Meloidogyne incognita) und Salatsamen gefüllt. Die Salatsamen keimen und die Pflänzchen entwickeln sich. An den Wurzeln entwickeln sich die Gallen. Nach 14 Tagen wird die nematizide Wirkung anhand der Gallenbildung in % bestimmt. Dabei bedeutet 100 %, dass keine Gallen gefunden wurden; 0 % bedeutet, dass die Zahl der Gallen an den behandelten Pflanzen der unbehandelten Kontrolle entspricht. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 20ppm: I-025 Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 20ppm: I-028, I-038, I-104, I-138, I-162, I-177, I-257, I-259. Myzus persicae - Sprühtest Lösungsmittel: 78 Gewichtsteile Aceton 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. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum. To calibrate the chemical shift of 1H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to. The lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. In addition, like classical 1H NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities. When indicating compound signals in the delta range of solvents and / or water, our lists of 1H NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which are usually average have a high intensity. The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity 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 identify the reproduction of our manufacturing process by "by-product fingerprints." An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation. Further details on 1H NMR peaks can be found in Research Disclosure Database Number 564025. Examples of use Ctenocephalides felis in vitro contact tests with adult cat fleas For the coating of the test tubes, 9 mg of active ingredient are first dissolved in 1 ml of acetone pa and then diluted with acetone pa to the desired concentration. 250 μl of the solution are distributed homogeneously on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h swing rotation at 30 rpm). At 900 ppm of active substance solution and 44.7 cm² of internal surface, a surface dose of 5 μg / cm² is achieved with homogeneous distribution. After evaporation of the solvent, the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck. A substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 μg / cm² at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed. In this test, for example, the following compounds of the Preparation Examples show an effect of 100% at a rate of 5 μg / cm² (500 g / ha): I-118, I-128, I-138, I-162, I-197, 216. In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 5 μg / cm 2 (500 g / ha): I-013 Boophilus microplus injection test Solvent: dimethylsulfoxide To prepare a suitable preparation of active compound, 10 are mixed mg of active ingredient with 0.5 ml of solvent and dilute the concentrate with solvent to the desired concentration. 1μl of the drug solution is injected into the abdomen of 5 wet, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room. The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile. In this test, for example, the following compounds of the preparation examples show an effect of 95% at an application rate of 20 μg / animal: I-104. In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 20 μg / animal: I-151 Ctenocephalides felis Oral Test Solvent: Dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane. After 2 days the kill is determined in%. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: I-004, I-005, I-008, I-013, I-026, I-027, I-028, I -030, I-036, I-043, I-044, I-051, I-052, I-073, I-074, I-075, I-076, I-077, I-078, I-079 , I-080, I-081, I-082, I-085, I-089, I-094, I-096, I-098, I-102, I-105, I-108, I-109, I -110, I-113, I-115, I-116, I-117, I-118, I-120, I-124, I-128, I-130, I-131, I-133, I-138 , I-141, I-142, I-149, I-151, I-152, I-154, I-155, I-159, I-160, I-162, I-172, I-173, I -176, I-178, I-179, I-182, I-184, I-189, I-190, I-192, I-195, I-196, I-197, I-213, I-216 , I-224, I-225, I-226, I-228, I-232, I-233, I-245, I-247, I-249, I-250. In this test, for example, the following compounds of the preparation examples show an effect of 98% at an application rate of 100 ppm: I-015, I-017, I-025, I-040, I-070 In this test, for example, the following compounds show the preparation examples an effect of 95% at an application rate of 100 ppm: I-041, I-053, I-065, I-091, I-093, I-095, I-150, I-235. In this test, for example, the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: I-088, I-167. In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: I-104, I-217. Lucilia cuprina test Solvent: dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Approximately Twenty L1 larvae of the Australian Goldfinch Sheep (Lucilia cuprina) are transferred to a test tube containing chopped horsemeat and the preparation of active compound of the desired concentration. After 2 days the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: I-005, I-013, I-015, I-026, I-040, I-043, I-044, I -048, I-052, I-053, I-070, I-073, I-074, I-077, I-078, I-079, I-080, I-081, I-082, I-085 , I-091, I-093, I-094, I-096, I-098, I-104, I-107, I-113, I-120, I-124, I-128, I-133, I -138, I-141, I-149, I-151, I-154, I-155, I-160, I-172, I-173, I-176, I-178, I-182, I-184 , I-190, I-195, I-196, I-197, I-213, I-217, I-224, I-225, I-228, I-247, I-249. In this test, for example, the following compounds of the preparation examples show an effect of 95% at an application rate of 100 ppm: I-008, I-089, I-117, I-250. In this test, for example, the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: I-027, I-030, I-108, I-115, I-142, I-152, I-159, I -192. In this test, for example, the following compounds of the preparation examples show an effect of 85% at an application rate of 100 ppm: I-021. In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: I-216, I-245. Musca domestica test Solvent: Dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica). After 2 days the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: I-013, I-026, I-074, I-078, I-089, I-138, I-151, I -154, I-155, I-172, I-195. In this test, for example, the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: I-040, I-079, I-107, I-152. In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: I-073, I-077, I-085, I-115, I-159, I-160, I-196, I -197. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 20 ppm: I-184, I-195, I-197. Meloidogyne incognita test solvent: 125.0 parts by weight of acetone To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration. Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots. After 14 days, the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to the untreated control. In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 20ppm: I-025 In this test show z. For example, the following compounds of the Preparation Examples have an effect of 90% at an application rate of 20 ppm: I-028, I-038, I-104, I-138, I-162, I-177, I-257, I-259. Myzus persicae - Spray Test Solvent: 78 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 500g/ha: I-028, I-175. Phaedon cochleariae - Sprühtest Lösungsmittel: 78,0 Gewichtsteile Aceton Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration. After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed. In this test, z. Example, the following compounds of the preparation examples effect of 90% at a rate of 500g / ha: I-028, I-175. Phaedon cochleariae - Spray Test Solvent: 78.0 parts by weight acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Chinakohlblattscheiben (Brassica pekinensis) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt. Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Käferlarven abgetötet wurden; 0 % bedeutet, dass keine Käferlarven abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 500g/ha: I-002, I-004, I-005, I-007, I-009, I-011, I-012, I-013, I-015, I- 017, I-018, I-019, I-020, I-021, I-022, I-024, I-025, I-026, I-027, I-028, I-030, I-031, I-035, I-039, I-040, I-041, I-042, I-043, I-044, I-048, I-051, I-052, I-053, I-055, I-056, I-060, I-061, I-064, I-066, I-067, I- 068, I-070, I-074, I-075, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-084, I-085, I-086, I-089, I-090, I-091, I-093, I-094, I-096, I-097, I-098, I-099, I-102, I-103, I-105, I-107, I-109, I-110, I-111, I-112, I- 113, I-114, I-115, I-116, I-117, I-118, I-119, I-120, I-123, I-124, I-125, I-126, I-127, I-128, I-129, I-130, I-131, I-132, I-137, I-138, I-140, I-141, I-142, I-144, I-145, I-146, I-147, I-149, I-151, I-152, I-153, I- 154, I-157, I-158, I-160, I-161, I-162, I-172, I-173, I-174, I-176, I-178, I-179, I-180, I-182, I-184, I-185, I-186, I-188, I-189, I-190, I-192, I-195, I-196, I-197, I-201, I-204, I-205, I-206, I-208, I-213, I-216, I- 218, I-222, I-224, I-225, I-226, I-227, I-228, I-233, I-234 , I-235, I-236, I-240, I-241, I-243, I-244, I-245, I-246, I-247, I-248, I-249, I-250, I-251, I-252, I-253, I-254, I-262, I-263, I-264, I-265, I-270, I-274, I- 276 Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 500g/ha: I-016, I-037, I-038, I-045, I-050, I-057, I-065, I-069, I-071, I- 087, I-095, I-101, I-108, I-135, I-155, I-191, I-194, I-210, I-217, I-237, I-238, I-258, I-259, I-261, I-268, I-271, I-272, I-277. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: I-005, I-011, I-012, I-013, I-026, I-027, I-030, I-038, I-039, I- 040, I-041, I-042, I-044, I-045, I-051, I-052, I-068, I-074, I-076, I-080, I-082, I-085, I-089, I-093, I-094, I-096, I-098, I-099, I-102, I-105, I-106, I-107, I-110, I-111, I-115, I-116, I-118, I-119, I-120, I-124, I- 128, I-129, I-130, I-137, I-138, I-140, I-141, I-142, I-144, I-145, I-147, I-149, I-151, I-152, I-153, I-154, I-160, I-162, I-173, I-174, I-176, I-178, I-180, I-182, I-184, I-185, I-188, I-189, I-190, I-192, I-195, I- 196, I-204, I-208, I-209, I-213, I-215, I-216, I-218, I-222, I-224, I-225, I-243, I-244, I-245, I-247, I-248, I-249, I-250, I-253, I-254, I-262, I-264. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 100g/ha: I-015, I-022, I-077, I-081, I-158, I-161, I-179, I-197, I-210, I- 214, I-230, I-239, I-246, I-251, I-268. Spodoptera frugiperda - Sprühtest Lösungsmittel: 78,0 Gewichtsteile Aceton Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water. Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae). After 7 days, the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed. In this test, z. For example, the following compounds of the preparation examples have an effect of 100% at a rate of 500 g / ha: I-002, I-004, I-005, I-007, I-009, I-011, I-012, I-013 , I-015, I-017, I-018, I-019, I-020, I-021, I-022, I-024, I-025, I-026, I-027, I-028, I -030, I-031, I-035, I-039, I-040, I-041, I-042, I-043, I-044, I-048, I-051, I-052, I-053, I-055, I-056, I-060, I-061, I- 064, I-066, I-067, I-068, I-070, I-074, I-075, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-084, I-085, I-086, I-089, I-090, I-091, I-093, I-094, I-096, I-097, I-098, I- 099, I-102, I-103, I-105, I-107, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-116, I-117, I-118, I-119, I-120, I-123, I-124, I-125, I-126, I-127, I-128, I-129, I-130, I- 131, I-132, I-137, I-138, I-140, I-141, I-142, I-144, I-145, I-146, I-147, I-149, I-151, I-152, I-153, I-154, I-157, I-158, I-160, I-161, I-162, I-172, I-173, I-174, I-176, I- 178, I-179, I-180, I-182, I-184, I-185, I-186, I-188, I-189, I-190, I-192, I-195, I-196, I-197, I-201, I-204, I-205, I-206, I-208, I-213, I-216, I-218, I-222, I-224, I-225, I- 226, I-227, I-228, I-233, I-234, I-235, I-236, I-240, I-241, I-243, I-244, I-245, I-246, I-247, I-248, I-249, I-250, I-251, I-252, I-253, I-254, I-262, I-263, I-264, I-265, I- 270, I-274, I-276 in this test show z. For example, the following compounds of the Preparation Examples have an effect of 83% at a rate of 500 g / ha: I-016, I-037, I-038, I-045, I-050, I-057, I-065, I-069 , I-071, I-087, I-095, I-101, I-108, I-135, I-155, I-191, I-194, I-210, I-217, I-237, I -238, I-258, I-259, I-261, I-268, I-271, I-272, I-277. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 g / ha: I-005, I-011, I-012, I-013, I-026, I-027, I-030, I-038 , I-039, I-040, I-041, I-042, I-044, I-045, I-051, I-052, I-068, I-074, I-076, I-080, I -082, I-085, I-089, I-093, I-094, I-096, I-098, I-099, I-102, I-105, I-106, I-107, I-110 , I-111, I-115, I-116, I-118, I-119, I-120, I-124, I-128, I-129, I-130, I-137, I-138, I -140, I-141, I-142, I-144, I-145, I-147, I-149, I-151, I-152, I-153, I-154, I-160, I-162 , I-173, I-174, I-176, I-178, I-180, I-182, I-184, I-185, I-188, I-189, I-190, I-192, I -195, I-196, I-204, I-208, I-209, I-213, I-215, I-216, I-218, I-222, I-224, I-225, I-243 , I-244, I-245, I-247, I-248, I-249, I-250, I-253, I-254, I-262, I-264. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 83% at an application rate of 100 g / ha: I-015, I-022, I-077, I-081, I-158, I-161, I-179, I-197 , I-210, I-214, I-230, I-239, I-246, I-251, I-268. Spodoptera frugiperda - spray test solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms (Spodoptera frugiperda) besetzt. Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 500g/ha: I-004, I-005, I-006, I-008, I-009, I-010, I-011, I-012, I-013, I- 015, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-025, I-026, I-027, I-028, I-030, I-031, I-032, I-033, I-034, I-035, I-037, I-039, I-040, I-041, I-042, I-043, I-044, I-045, I-048, I-051, I-052, I-053, I-054, I- 055, I-056, I-057, I-058, I-059, I-060, I-061, I-062, I-063, I-064, I-065, I-066, I-067, I-068, I-071, I-073, I-074, I-075, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-083, I-085, I-087, I-089, I-090, I-091, I- 092, I-093, I-094, I-095, I-096, I-098, I-099, I-102, I-103, I-105, I-106, I-107, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-116, I-117, I-118, I-119, I-120, I-121, I-122, I-123, I-124, I-125, I-126, I-127, I- 128, I-129, I-130, I-131, I-132, I-133, I-134, I-135, I-136, I-137, I-138, I-139, I-140, I-141, I-144, I-145, I-147, I-148, I-149, I-150, I-151, I-152, I-153, I-154, I-155, I-156, I-158, I-159, I-160, I-161, I-162, I- 163, I-164, I-169, I-170, I-172, I-173, I-174, I-176, I-178, I-181, I-182, I-184, I-185, I-189, I-190, I-191, I-192, I-193, I-195, I-196, I-197, I-198, I-200, I-204, I-205, I-206, I-207, I-211, I-212, I-214, I-216, I- 217, I-218, I-220, I-223, I-224, I-225, I-226, I-227, I-228, I-229, I-231, I-232, I-233, I-237, I-240, I-241, I-242, I-243, I-244, I-245, I-246, I-247, I-248, I-249, I-250, I-251, I-252, I-253, I-254, I-255, I-256, I- 257, I-259, I-260, I-261, I-262, I-263, I-264, I-265, I-268, I-270, I-271, I-273, I-274, I-277. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 500g/ha: I-003, I-007, I-023, I-029, I-036, I-038, I-046, I-047, I-049, I- 070, I-086, I-088, I-100, I-108, I-146, I-157, I-166, I-179, I-187, I-215, I-219, I-239, I-258, I-269, I-276. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 80% bei einer Aufwandmenge von 500g/ha: I-014 Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: I-005, I-008, I-013, I-015, I-022, I-025, I-026, I-027, I-039, I- 041, I-044, I-051, I-052, I-055, I-056, I-061, I-064, I-065, I-067, I-068, I-071, I-074, I-076, I-077, I-078, I-079, I-081, I-082, I-085, I-086, I-087, I-088, I-089, I-091, I-096, I-098, I-099, I-108, I-110, I-111, I- 115, I-117, I-118, I-119, I-120, I-122, I-124, I-125, I-128, I-129, I-131, I-132, I-133, I-137, I-138, I-140, I-143, I-144, I-145, I-147, I-149, I-150, I-151, I-152, I-153, I-155, I-156, I-157, I-158, I-159, I-160, I- 161, I-162, I-164, I-169, I-172, I-173, I-176, I-178, I-181, I-182, I-185, I-189, I-190, I-192, I-195, I-196, I-197, I-198, I-200, I-204, I-205, I-206, I-208, I-213, I-214, I-215, I-216, I-217, I-218, I-224, I-225, I- 231, I-232, I-233, I-241, I-243, I-244, I-245, I-246, I-247, I-248, I-249, I-250, I-251, I-253, I-260, I-261, I-262, I-264, I-268, I-277. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 100g/ha: I-018, I-028, I-030, I-037, I-040, I-042, I-048, I-060, I-062, I- 073, I-080, I-083, I-090, I-102, I-105, I-112, I-113, I-114, I-121, I-126, I-127, I-130, I-134, I-141, I-154, I-170, I-211, I-226, I-228, I-240, I-252, I-254, I-255. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 80% bei einer Aufwandmenge von 100g/ha: I-106, I-221. Tetranychus urticae– Sprühtest, OP-resistent Lösungsmittel: 78,0 GewichtsteileAceton Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water. Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda). After 7 days, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 100% at a rate of 500 g / ha: I-004, I-005, I-006, I-008, I-009, I-010, I-011, I-012 , I-013, I-015, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-025, I-026, I-027, I -028, I-030, I-031, I-032, I-033, I-034, I-035, I-037, I-039, I-040, I-041, I-042, I-043 , I-044, I-045, I-048, I-051, I-052, I-053, I-054, I-055, I-056, I-057, I-058, I-059, I -060, I-061, I-062, I-063, I-064, I-065, I-066, I-067, I-068, I-071, I-073, I-074, I-075 , I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-083, I-085, I-087, I-089, I-090, I -091, I-092, I-093, I-094, I-095, I-096, I-098, I-099, I-102, I-103, I-105, I-106, I-107 , I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-116, I-117, I-118, I-119, I-120, I -121, I-122, I-123, I-124, I-125, I-126, I-127, I-128, I-129, I-130, I-131, I-132, I-133 , I-134, I-135, I-136, I-137, I-138, I-139, I-140, I-141, I-144, I-145, I-147, I-148, I -149, I-150, I-151, I-152, I-153, I-154, I-155 , I-156, I-158, I-159, I-160, I-161, I-162, I-163, I-164, I-169, I-170, I-172, I-173, I -174, I-176, I-178, I-181, I-182, I-184, I-185, I-189, I-190, I-191, I-192, I-193, I-195 , I-196, I-197, I-198, I-200, I-204, I-205, I-206, I-207, I-211, I-212, I-214, I-216, I - 217, I-218, I-220, I-223, I-224, I-225, I-226, I-227, I-228, I-229, I-231, I-232, I-233 , I-237, I-240, I-241, I-242, I-243, I-244, I-245, I-246, I-247, I-248, I-249, I-250, I -251, I-252, I-253, I-254, I-255, I-256, I-257, I-259, I-260, I-261, I-262, I-263, I-264 , I-265, I-268, I-270, I-271, I-273, I-274, I-277. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 83% at a rate of 500 g / ha: I-003, I-007, I-023, I-029, I-036, I-038, I-046, I-047 , I-049, I-070, I-086, I-088, I-100, I-108, I-146, I-157, I-166, I-179, I-187, I-215, I -219, I-239, I-258, I-269, I-276. In this test, z. Example, the following compounds of the preparation examples effect of 80% at a rate of 500g / ha: I-014 In this test, for. For example, the following compounds of the preparation examples have an effect of 100% at a rate of 100 g / ha: I-005, I-008, I-013, I-015, I-022, I-025, I-026, I-027 , I-039, I-041, I-044, I-051, I-052, I-055, I-056, I-061, I-064, I-065, I-067, I-068, I -071, I-074, I-076, I-077, I-078, I-079, I-081, I-082, I-085, I-086, I-087, I-088, I-089 , I-091, I-096, I-098, I-099, I-108, I-110, I-111, I-115, I-117, I-118, I-119, I-120, I -122, I-124, I-125, I-128, I-129, I-131, I-132, I-133, I-137, I-138, I-140, I-143, I-144 , I-145, I-147, I-149, I-150, I-151, I-152, I-153, I-155, I-156, I-157, I-158, I-159, I -160, I-161, I-162, I-164, I-169, I-172, I-173, I-176, I-178, I-181, I-182, I-185, I-189 , I-190, I-192, I-195, I-196, I-197, I-198, I-200, I-204, I-205, I-206, I-208, I-213, I -214, I-215, I-216, I-217, I-218, I-224, I-225, I-231, I-232, I-233, I-241, I-243, I-244 , I-245, I-246, I-247, I-248, I-249, I-250, I-251, I-253, I-260, I-261, I-262, I-264, I -268, I-277. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 83% at a rate of 100 g / ha: I-018, I-028, I-030, I-037, I-040, I-042, I-048, I-060 , I-062, I-073, I-080, I-083, I-090, I-102, I-105, I-112, I-113, I-114, I-121, I-126, I -127, I-130, I-134, I-141, I-154, I-170, I-211, I-226, I-228, I-240, I-252, I-254, I-255 , In this test, z. For example, the following compounds of the Preparation Examples have an effect of 80% at an application rate of 100 g / ha: I-106, I-221. Tetranychus urticae spray test, OP-resistant Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator : Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 500g/ha: I-105 Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 500g/ha: I-036, I-091, I-101, I-104, I-182, I-185, I-194, I-218, I-227, I-255. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 100g/ha: I-100, I-194, I-218, I-227. Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration. After 6 days, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, z. Example, the following compounds of the preparation examples, an effect of 100% at a rate of 500g / ha: I-105 In this test, for. For example, the following compounds of the preparation examples have an effect of 90% at an application rate of 500 g / ha: I-036, I-091, I-101, I-104, I-182, I-185, I-194, I- 218, I-227, I-255. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 90% at a rate of 100 g / ha: I-100, I-194, I-218, I-227.

Claims

Patentansprüche: 1. Verbindungen der allgemeinen Formel (I)  Claims: 1. Compounds of the general formula (I)
in denenin which
Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl oder Oxo-Hetaryl steht, wobei die Substituenten ausgewählt sind aus: Cyano, Carboxyl, Halogen, Nitro, Hydroxy, Amino, SCN, SF5, Tri-(C1-C6)alkylsilyl, (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1- C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, Hydroxycarbonyl-(C1-C6)-alkoxy, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Halogenalkinyl, (C2- C6)Cyanoalkinyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkoxy, (C1-C6)Cyanoalkoxy, (C1- C6)Alkoxycarbonyl-(C1-C6)alkoxy, (C1-C6)Alkoxy-(C1-C6)alkoxy, (C3-C8)Cycloalkyl, (C3- C8)Halogencycloalkyl, (C1-C6)Alkyl-(C3-C8)cycloalkyl, (C1-C6)Halogenalkyl-(C3- C8)cycloalkyl, (C1-C4)Halogenalkenoxy, (C1-C6)Alkylhydroxyimino, (C1-C6)Alkoxyimino, (C1- C6)Alkyl-(C1-C6)alkoxyimino, (C1-C6)Halogenalkyl-(C1-C6)alkoxyimino, (C1-C6)Alkylsulfanyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfanyl, (C1-C6)Alkylsulfanyl-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfinyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfonyl, (C1-C6)Alkoxy-(C1- C6)alkylsulfonyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyloxy, (C1- C6)Halogenalkylsulfanyl, (C3-C6)Cycloalkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C3- C6)Cycloalkylsulfonyl, (C3-C6)Halogencycloalkylsulfonyl, (C3-C6)Cycloalkylsulfinyl, (C3- C6)Halogencycloalkylsulfinyl, (C1-C6)Alkylcarbonyl, (C1-C6)Halogenalkylcarbonyl, (C1- C6)Alkylcarbonyloxy, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkoxycarbonyl, Aminocarbonyl, (C1-C6)Alkylaminocarbonyl, Di-(C1-C6)alkyl-aminocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-C6)-alkenylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, (C1- C6)Alkylsulfonylamino, (C1-C6)Alkylamino, Di-(C1-C6)Alkylamino, (C1- C6)Halogenalkylamino, Bis-(C1-C6)Halogenalkylamino, Aminosulfonyl, (C1- C6)Alkylaminosulfonyl, Di-(C1-C6)alkylaminosulfonyl, (C1-C6)Alkylsulfoximino, Aminothiocarbonyl, (C1-C6)Alkylaminothiocarbonyl, Di-(C1-C6)alkylaminothiocarbonyl, (C3- C8)Cycloalkylamino, R1 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C1-C6)alkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1- C6)Alkyl-(C3-C8)Cycloalkyl, (C1-C6)Halogenalkyl-(C3-C8)cycloalkyl, Halogen(C3- C8)cycloalkyl, Cyano(C3-C8)cycloalkyl, (C2-C6)Alkinyl-(C3-C8)cycloalkyl, (C1-C6)Alkoxy-(C3- C8)cycloalkyl, (C1-C6)Alkoxycarbonyl-(C3-C8)cycloalkyl, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C8)Cycloalkylamino, (C1-C6)Alkylcarbonyl-amino, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, (C1- C6)Alkylsulfonylamino, Aminosulfonyl-(C1-C6)alkyl, (C1-C6)Alkylaminosulfonyl-(C1-C6)alkyl, Di-(C1-C6)alkyl-aminosulfonyl-(C1-C6)alkyl, (C1-C4)Alkoxy, (C3-C6)Cycloalkoxy, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkylcarbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiertes (C1-C6)Alkyl, (C1- C6)Alkoxy, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C8)Cycloalkyl steht, wobei Aryl, Hetaryl, Oxo- Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkyl, (C1- C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1- C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino-(C2- C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl oder (C3-C6)Trialkylsilyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1- C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1- C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino-(C2- C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3- C6)Trialkylsilyl, R2 für Wasserstoff, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C8)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1- C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2- C6)Alkenyl, (C2-C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl- (C1-C6)alkyl, (C1-C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, Aminocarbonyl- (C1-C6)alkyl, (C1-C6)Alkylamino-(C1-C6)alkyl, Di-(C1-C6)alkylamino-(C1-C6)alkyl oder (C3- C8)Cycloalkylamino-(C1-C6)alkyl steht, R3 für Wasserstoff, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C8)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1- C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2- C6)Alkenyl, (C2-C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1-C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1- C6)alkyl, (C1-C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, Aminocarbonyl- (C1-C6)alkyl, (C1-C6)Alkylamino-(C1-C6)alkyl, Di-(C1-C6)alkylamino-(C1-C6)alkyl oder (C3- C8)Cycloalkylamino-(C1-C6)alkyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1-C6)Alkoxy-(C1-C6)alkyl, (C1-C6)Halogenalkoxy-(C1-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Alkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(C1-C6)alkyl, (C2- C6)Halogenalkinyloxy-(C1-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C1-C6)alkyl, Cyano(C3-C8)cycloalkyl-(C1-C6)alkyl, Halogen(C3-C8)cycloalkyl-(C1-C6)alkyl, (C1-C4)Halogenalkyl-(C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (C1-C6)Alkyl-(C3-C8)Cycloalkyl, (C1-C6)Halogenalkyl- (C3-C8)cycloalkyl, Halogen(C3-C8)cycloalkyl, Cyano(C3-C8)cycloalkyl, (C2-C6)Alkinyl-(C3- C8)cycloalkyl, (C1-C6)Alkoxy-(C3-C8)cycloalkyl, (C1-C6)Alkoxycarbonyl-(C3-C8)cycloalkyl, Carbamoyl-(C3-C8)cycloalkyl, Thiocarbamoyl-(C3-C8)cycloalkyl, (C1-C6)Alkylthio-(C1- C6)alkyl, (C1-C6)Halogenalkylthio-(C1-C6)alkyl, (C1-C6)Alkylsulfinyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkylsulfonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1- C6)Alkoxy-(C1-C6)alkylsulfinyl-(C1-C6)alkyl, (C1-C6)Alkoxy-(C1-C6)alkylsulfonyl-(C1-C6)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1- C6)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)Halogenalkoxycarbonyl-(C1-C6)alkyl, (C1- C6)Alkylsulfonylamino, Aminosulfonyl-(C1-C6)alkyl, (C1-C6)Alkylaminosulfonyl-(C1-C6)alkyl Di-(C1-C6)alkyl-aminosulfonyl-(C1-C6)alkyl, Amino, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C8)Cycloalkylamino, N-(C1-C6)alkyl-(C3-C8)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Halogenbenzylamino, N-(C1-C6)alkyl-Benzylamino, N- (C1-C6)alkyl-Cyanobenzylamino, N-(C1-C6)alkyl-Nitrobenzylamino, N-(C1-C6)alkyl- Halogenbenzylamino, (C1-C6)Alkylcarbonyl-amino, (C3-C8)Cycloalkylcarbonylamino, Hydroxy, (C1-C6)Alkoxy, (C3-C8)Cycloalkoxy, (C3-C8)Cycloalkyl-(C1-C6)Alkoxy, Cyano(C1- C6)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Halogenbenzyloxy, (C1- C6)Alkylimino, (C3-C8)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino, Halogenbenzylimino, (C1-C6)Halogenalkylbenzylimino, Halogen-[(C1- C6)Halogenalkyl]benzylimino, (C1-C6)Alkylcarbonyl, (C1-C6)Halogenalkylcarbonyl, (C3- C8)Cycloalkylcarbonyl oder (C3-C8)Cycloalkyl-(C1-C6)alkyl-carbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl substituiertes (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Alkoxy, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C8)Cycloalkyl, Oxy, Amino, N-(C1-C6)Alkylamino, N-(C3- C8)Cycloalkylamino oder Carbonyl steht, wobei Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4- benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C6)Alkyl, (C3- C6)Cycloalkyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkyl- sulfinyl, (C1-C6)Halogenalkylsulfonyl, (C1-C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1- C6)alkyl, (C1-C6)Alkylsulfimino-(C2-C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1- C6)Alkylsulfoximino-(C1-C6)alkyl, (C1-C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Hetaryl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C6)Alkyl, (C3-C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1- C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1-C6)Halogenalkylthio, (C1- C6)Alkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Halogenalkyl- sulfonyl, (C1-C6)Alkylsulfimino, (C1-C6)Alkylsulfimino-(C1-C6)alkyl, (C1-C6)Alkylsulfimino- (C2-C6)alkylcarbonyl, (C1-C6)Alkylsulfoximino, (C1-C6)Alkylsulfoximino-(C1-C6)alkyl, (C1- C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3- C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C6)-Alkyl oder für (C2-C6)Alkenyl stehen, wobei ein 3-7 gliedriger gegebenfalls durch Halogen, Cyano, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C6)Alkyl, (C3- C8)Cycloalkyl, (C1-C6)-Alkoxy, (C1-C6)Halogenalkyl, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio oder (C1-C6)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, (C1- C6)Alkylamino, Di-(C1-C6)Alkylamino, (C3-C6)Cycloalkyl, Halogen(C3-C6)cycloalkyl, (C1- C6)Alkyl, (C1-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Alkinyl, (C2- C6)Halogenalkinyl, (C1-C6)Alkoxy, (C1-C6)Halogenalkoxy, (C1-C6)Alkylthio, (C1- C6)Halogenalkylthio, (C1-C6)Alkylsulfinyl, (C1-C6)Halogenalkylsulfinyl, (C1-C6)Alkylsulfonyl, (C1-C6)Halogenalkylsulfonyl, stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. 2. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1, in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl oder Oxo-Hetaryl steht, wobei die Substituenten ausgewählt sind aus Cyano, Halogen, Nitro, Amino, SF5, (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkoxy, (C1- C4)Cyanoalkoxy, (C1-C4)Alkoxy-(C1-C4)alkoxy, (C3-C6)Cycloalkyl, (C3-C6)Halogencycloalkyl, (C1-C4)Alkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, (C1- C4)Halogenalkenoxy, (C1-C4)Alkylhydroxyimino, (C1-C4)Alkoxyimino, (C1-C4)Alkyl-(C1- C4)alkoxyimino, (C1-C4)Halogenalkyl-(C1-C4)alkoxyimino, (C1-C4)Alkylsulfanyl, (C1- C4)Alkylsulfanyl-(C1-C4)alkyl, (C1-C4)Alkylsulfinyl, (C1-C4)Halogenalkylsulfinyl, (C1- C4)Alkylsulfinyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfonyl, (C1- C4)Alkylsulfonyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyloxy, (C1-C4)Halogenalkylsulfanyl, (C3- C6)Cycloalkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C3-C6)Cycloalkylsulfonyl, (C3- C6)Halogencycloalkylsulfonyl, (C3-C6)Cycloalkylsulfinyl, (C3-C6)Halogencycloalkylsulfinyl, (C1-C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, Aminocarbonyl, (C1- C4)Alkylaminocarbonyl, Di-(C1-C4)alkyl-aminocarbonyl, (C1-C4)Alkylsulfonylamino, (C1- C4)Alkylamino, Di-(C1-C4)Alkylamino, (C1-C6)Halogenalkylamino, Bis-(C1- C6)Halogenalkylamino, Aminosulfonyl, (C1-C4)Alkylaminosulfonyl, Di-(C1- C4)alkylaminosulfonyl, R1 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C6)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C6)alkyl, (C2- C4)Halogenalkinyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1- C4)Alkyl-(C3-C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3- C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, (C1-C6)Alkylamino, Di-(C1-C6)alkyl- amino, (C3-C6)Cycloalkylamino, (C1-C4)Alkylthio-(C1-C6)alkyl, (C1-C4)Halogenalkylthio-(C1- C6)alkyl, (C1-C4)Alkylsulfinyl-(C1-C6)alkyl, (C1-C4)Halogenalkylsulfinyl-(C1-C6)alkyl, (C1- C4)Alkylsulfonyl-(C1-C6)alkyl, (C1-C4)Halogenalkylsulfonyl-(C1-C6)alkyl, (C1- C4)Alkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxy, (C3- C6)Cycloalkoxy, (C3-C6)Cycloalkylcarbonyl oder (C1-C4)Alkylcarbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiertes (C1-C4)Alkyl, (C1- C4)Alkoxy, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl steht, wobei Aryl, Hetaryl, Oxo- Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1- C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl oder (C3-C6)Trialkylsilyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1- C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C6)Alkoxycarbonyl, (C1-C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl steht, R2 für Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C4)Halogenalkyl oder (C1-C4)Cyanoalkyl steht, R3 für Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C6)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl, (C1-C6)Alkoxycarbonyl, (C1-C4)Halogenalkyl oder (C1-C4)Cyanoalkyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2- C4)Alkenyloxy-(C1-C6)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C2- C4)Halogenalkinyloxy-(C1-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C6)alkyl, Cyano(C3-C6)cycloalkyl-(C1-C6)alkyl, Halogen(C3-C6)cycloalkyl-(C1-C6)alkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl-(C1-C6)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1-C6)Alkyl-(C3-C6)Cycloalkyl, (C1-C6)Halogenalkyl- (C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3- C6)cycloalkyl, (C1-C4)Alkoxy-(C3-C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, Carbamoyl-(C3-C6)cycloalkyl, Thiocarbamoyl-(C3-C6)cycloalkyl, (C1-C4)Alkylthio-(C1- C4)alkyl, (C1-C4)Halogenalkylthio-(C1-C4)alkyl, (C1-C4)Alkylsulfinyl-(C1-C4)alkyl, (C1- C4)Halogenalkylsulfinyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonyl-(C1-C4)alkyl, (C1- C4)Halogenalkylsulfonyl-(C1-C4)alkyl, (C1-C6)Alkylcarbonyl-(C1-C6)alkyl, (C1- C6)Halogenalkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1- C4)Halogenalkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylsulfonylamino, Aminosulfonyl-(C1- C4)alkyl, (C1-C4)Alkylaminosulfonyl-(C1-C4)alkyl, oder Di-(C1-C4)alkyl-aminosulfonyl-(C1- C6)alkyl, Amino, (C1-C4)Alkylamino, Di-(C1-C4)alkyl-amino, (C3-C6)Cycloalkylamino, N-(C1- C4)alkyl-(C3-C6)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Halogenbenzylamino, N-(C1-C4)alkyl-Benzylamino, N-(C1-C4)alkyl-Cyanobenzylamino, N-(C1- C4)alkyl-Nitrobenzylamino, N-(C1-C4)alkyl-Halogenbenzylamino, (C1-C4)Alkylcarbonyl-amino, (C3-C6)Cycloalkylcarbonylamino, Hydroxy, (C1-C4)Alkoxy, (C3-C6)Cycloalkoxy, (C3- C6)Cycloalkyl-(C1-C4)Alkoxy, Cyano(C1-C4)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Halogenbenzyloxy, (C1-C4)Alkylimino, (C3-C6)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino, Halogenbenzylimino, (C1- C4)Halogenalkylbenzylimino, Halogen-[(C1-C4)Halogenalkyl]benzylimino, (C1- C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, (C3-C6)Cycloalkylcarbonyl oder (C3- C6)Cycloalkyl-(C1-C4)alkyl-carbonyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl substituiertes (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Alkoxy, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl, Oxy, Amino, N-(C1-C4)Alkylamino, N-(C3- C6)Cycloalkylamino oder Carbonyl steht, wobei Aryl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4- benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3- C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkyl- sulfinyl, (C1-C4)Halogenalkylsulfonyl, (C1-C4)Alkylsulfimino, (C1-C4)Alkylsulfimino-(C1- C4)alkyl, (C1-C4)Alkylsulfoximino, (C1-C4)Alkylsulfoximino-(C1-C4)alkyl, (C1- C4)Alkoxycarbonyl, (C1-C4)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Hetaryl substituiert sein können, oder oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1-C4)Halogenalkyl- sulfonyl, (C1-C4)Alkylsulfimino, (C1-C4)Alkylsulfimino-(C1-C4)alkyl, (C1- C4)Alkylsulfoximino, (C1-C4)Alkylsulfoximino-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl, (C1- C4)Alkylcarbonyl, (C3-C6)Trialkylsilyl, oder R3 und R4 gemeinsam für (C2-C6)-Alkyl oder für (C2-C6)Alkenyl stehen, wobei ein 3-7 gliedriger gegebenfalls durch Halogen, Cyano, Hydroxy, Amino, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)- Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio oder (C1-C4)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, (C3-C6)Cycloalkyl, (C1- C4)Alkyl, (C1-C4)Halogenalkyl oder (C1-C4)Halogenalkoxy stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. 3. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 oder 2, in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyrimidyl, Pyridazinyl, Pyridyl, Thienyl, Furanyl, Oxazolyl, Thiazolyl, Imidazolyl oder Pyrazolyl steht, wobei die Substituenten ausgewählt sind aus Cyano, Halogen, Nitro, SF5, (C1-C4)Alkyl, (C1- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkoxy, (C3-C6)Cycloalkyl, (C3- C6)Halogencycloalkyl, (C1-C4)Alkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, (C1-C4)Halogenalkenoxy, (C1-C4)Alkylsulfanyl, (C3-C6)Halogencycloalkylsulfanyl, (C1- C4)Alkylsulfinyl, (C1-C4)Halogenalkylsulfinyl, (C3-C6)Cycloalkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Halogenalkylsulfonyl, (C3-C6)Cycloalkylsulfonyl, (C1-C4)Halogenalkylsulfanyl, (C3- C6)Cycloalkylsulfanyl, (C1-C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, Bis-(C1- C4)Alkylamino, Di-(C1-C4)Halogenalkylamino, R1 für (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C1-C4)Hydroxyalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C2- C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1- C4)Alkyl-(C3-C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3- C6)cycloalkyl, (C1-C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, (C1-C4)Alkylthio-(C1-C6)alkyl, (C1- C4)Alkylcarbonyl-(C1-C6)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C6)alkyl oder (C1-C4)Alkoxy steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl oder Heterocyclyl substituiertes (C1-C4)Alkyl, (C3-C6)Cycloalkyl steht, wobei Aryl, Hetaryl oder Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio oder (C1-C6)Alkoxycarbonyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C6)Alkoxycarbonyl, R2 für Wasserstoff, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkoxycarbonyl steht, R3 für Wasserstoff, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylcarbonyl, (C3- C6)Cycloalkylcarbonyl oder (C1-C4)Alkoxycarbonyl steht, R4 für (C1-C6)Alkyl, (C1-C6)Halogenalkyl, (C1-C6)Cyanoalkyl, (C1-C4)Hydroxyalkyl, (C1- C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Halogenalkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyloxy-(C1-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(C1-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, Cyano(C3- C6)cycloalkyl-(C1-C4)alkyl, Halogen(C3-C6)cycloalkyl-(C1-C4)alkyl, (C1-C4)Halogenalkyl-(C3- C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (C1-C4)Alkyl-(C3- C6)Cycloalkyl, (C1-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3- C6)cycloalkyl, (C2-C4)Alkinyl-(C3-C6)cycloalkyl, (C1-C4)Alkoxy-(C3-C6)cycloalkyl, (C1- C4)Alkoxycarbonyl-(C3-C6)cycloalkyl, Carbamoyl-(C3-C6)cycloalkyl, Thiocarbamoyl-(C3- C6)cycloalkyl, (C1-C4)Alkylcarbonyl-(C1-C4)alkyl, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, Amino, (C1-C4)Alkylamino, Di-(C1-C4)alkyl-amino, (C3-C6)Cycloalkylamino, N-(C1-C4)alkyl- (C3-C6)Cycloalkylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, N-(C1-C4)alkyl- Benzylamino, N-(C1-C4)alkyl-Cyanobenzylamino, N-(C1-C4)alkyl-Nitrobenzylamino, (C1- C4)Alkylcarbonyl-amino, (C3-C6)Cycloalkylcarbonylamino, Hydroxy, (C1-C4)Alkoxy, (C3- C6)Cycloalkoxy, (C3-C6)Cycloalkyl-(C1-C4)Alkoxy, Cyano(C1-C4)Alkoxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, (C1-C4)Alkylimino, (C3-C6)Cycloalkylimino, Benzylimino, Cyanobenzylimino, Halogenbenzylimino, (C1-C4)Halogenalkylbenzylimino, Halogen-[(C1- C4)Halogenalkyl]benzylimino, Nitrobenzylimino, (C1-C4)Alkylsulfonyl-(C1-C4)alkyl, (C1- C4)Alkylcarbonyl, (C1-C4)Halogenalkylcarbonyl, (C3-C6)Cycloalkylcarbonyl oder (C3- C6)Cycloalkyl-(C1-C4)alkyl-carbonyl steht, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocycyl substituiertes (C1-C4)Alkyl, (C1-C4)Halogenalkyl, (C2-C4)Alkenyl, (C3-C6)Cycloalkyl, Oxy, Amino, N-(C1-C4)Alkylamino, N-cyclo-Propylamino oder Carbonyl steht, wobei Aryl, 1,3- Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo- Heterocycyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C1-C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1- C4)Halogenalkylsulfinyl, (C1-C4)Halogenalkylsulfonyl, (C1-C4)Alkoxycarbonyl, (C1- C4)Alkylcarbonyl, Hetaryl, Alkyl-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, 2,3-Dihydro-1H-indenyl, 1,3-Benzodioxolyl, Hetaryl, Oxo-Hetaryl, Heterocyclyl oder Oxo-Heterocyclyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, (C1-C4)Alkylthio, (C1-C4)Halogenalkylthio, (C1- C4 )Alkylsulfinyl, (C 1 -C 4 )Alkylsulfonyl, (C1-C4)Halogenalkylsulfinyl, (C1- C4)Halogenalkylsulfonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Alkylcarbonyl, (C3-C6)Trialkyl- silyl, oder R3 und R4 gemeinsam für (C2-C5)-Alkyl oder für (C2-C5)Alkenyl stehen, wobei ein 3-6 gliedriger gegebenfalls durch Halogen, Cyano, (C1-C4)Alkyl, (C3-C6)Cycloalkyl, (C1-C4)-Alkoxy, (C1- C4)Halogenalkyl, (C1-C4)Halogenalkoxy, oder (C1-C4)Halogenalkylthio substituierter Ring gebildet wird, der gegebenenfalls ein bis zwei Doppelbindungen enthalten kann, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trifluormethoxy stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. 4. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1, 2 oder 3, in denen Q1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyridyl, Thienyl oder Pyrazol-1-yl oder Pyrazol-2-yl steht, wobei die Substituenten ausgewählt sind aus Cyano, Fluor, Chlor, Brom, Iod, SF5, Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, Heptafluorisopropyl, Fluorcyclopropyl, Difluorcyclopropyl, Tetrafluorcyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy, Pentafluorethoxy, Tetrafluorethoxy, Trifluorethoxy, Chlortetrafluorethoxy, Dichlortrifluorethoxy, Trichlordifluorethoxy, Chlortrifluorethoxy, Chlordifluorethoxy, Trifluorethenoxy, Trifluormethylsulfonyl, Difluormethylsulfonyl, Trifluormethylsulfinyl, Trifluormethylsulfanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Pentafluorethylsulfanyl, Trifluorethylsulfanyl, Difluorethylsulfanyl, Pentafluorethylsulfonyl, Tetrafluorethylsulfonyl, Trifluorethylsulfonyl, Difluorethylsulfonyl, Pentafluorethylsulfinyl, Tetrafluorethylsulfinyl, Trifluorethylsulfinyl, Difluorethylsulfinyl, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, Trifluormethylcyclopropyl, Trifluormethylcarbonyl, Bis-Trifluormethylamino, (Trifluorvinyl)oxy, Heptafluorpropoxy oder Hexafluorpropoxy R1 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Methyl-cyclo-Propyl, cyclo-Propyl-Methyl, Cyano-cyclo-Propyl, Chlor-cyclo-Propyl, Fluor-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, cyclo-Propyl-cyclo-Propyl, Methoxymethyl, Methoxyethyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo- Butyl, Difluorcyclobutyl, cyclo-Pentyl, Fluormethyl, Difluormethyl, Trifluormethyl oder Trifluorethyl steht, oder für einfach durch Phenyl substituiertes Methyl, Ethyl, i-Propyl oder cyclo-Propyl steht, wobei Phenyl jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy substituiert sein kann, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy substituiertes Phenyl, Pyridyl, Oxazolyl, Thiazolyl, Thienyl, Oxetanyl oder Thietanyl steht, R2 für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Methoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, i-Propylcarbonyl, cyclo-Propylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, n-Propoxycarbonyl oder i-Propoxycarbonyl steht, R3 für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Methoxy, Ethoxy, n-Propyloxy, i-Propyloxy, n-Butyloxy, i-Butyloxy, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, i-Propylcarbonyl, cyclo-Propylcarbonyl, Methyloxycarbonyl, Ethyloxycarbonyl, n-Propyloxycarbonyl oder i-Propyloxycarbonyl steht, R4 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Fluormethyl, Difluormethyl, Trifluormethyl, Difluorethyl, Trifluorethyl, Pentafluorethyl, Trifluorpropyl, Pentafluorpropyl, Cyanomethyl, Cyanoethyl, Cyanopropyl, Cyanobutyl, Cyanopentyl, Cyanohexyl, Methyloxymethyl, Ethyloxymethyl, Methyloxyethyl, Ethyloxyethyl, Methyloxypropyl, Ethyloxypropyl, Propinyl, Butinyl, cyclo-Propyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, cyclo-Propyl-methyl, cyclo-Butyl-methyl, cyclo-Pentyl-methyl, cyclo-Hexyl- methyl, cyclo-Propyl-ethyl, cyclo-Butyl-ethyl, cyclo-Pentyl-ethyl, cyclo-Hexyl-ethyl, Cyano- cyclo-Propyl-methyl, Cyano-cyclo-Butyl-methyl, Cyano-cyclo-Pentyl-methyl, Cyano-cyclo- Hexyl-methyl, Trifluormethyl-cyclo-Propyl-methyl, Trifluormethyl-cyclo-Hexyl-methyl, cyclo- Propyl-cyclo-Propyl, Methyl-cyclo-Propyl, Ethyl-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, Trifluormethyl-cyclo-Butyl, Trifluormethyl-cyclo-Pentyl, Trifluormethyl-cyclo-Hexyl, Fluor- cyclo-Propyl, Difluor-cyclo-Propyl, Tetrafluor-cyclo-Propyl, Cyano-cyclo-Propyl, Cyano-cyclo- Butyl, Cyano-cyclo-Pentyl, Cyano-cyclo-Hexyl, Ethinyl-cyclo-Propyl, Methyloxy-cyclo-Propyl, Ethyloxy-cyclo-Propyl, Methyloxycarbonyl-cyclo-Propyl, Ethyloxycarbonyl-cyclo-Propyl, Thiocarbamoyl-cyclo-Propyl, Methyloxycarbonylmethyl, Ethyloxycarbonylmethyl, Methyloxycarbonylethyl, Ethyloxycarbonylethyl, Methylamino, Ethylamino, n-Propylamino, iso-Propylamino, cyclo-Propylamino, cyclo-Butylamino, cyclo-Pentylamino, cyclo- Hexylamino, Benzylamino, Cyanobenzylamino, Nitrobenzylamino, Di-Methylamino, N- Methylethylamino, N-Methyl-n-Propylamino, N-Methyl-iso-Propylamino, N-Methyl-cyclo- Propylamino, N-Methyl-cyclo-Butylamino, N-Methyl-cyclo-Pentylamino, N-Methyl-cyclo- Hexylamino, N-Methyl-Benzylamino, N-Methyl-Cyanobenzylamino, N-Methyl- Nitrobenzylamino, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, cyclo-Propyloxy, cyclo- Propyl-methyloxy, cyclo-Butyloxy, cyclo-Pentyloxy, cyclo-Hexyloxy, Cyanomethyloxy, Cyanoethyloxy, Cyanopropyloxy, Cyanobutyloxy, Benzyloxy, Cyanobenzyloxy, Nitrobenzyloxy, Methylimino, Ethylimino, n-Propylimino, iso-Propylimino, iso-Butylimino, cyclo-Pentylimino, cyclo-Hexylimino, Benzylimino, Cyanobenzylimino, Nitrobenzylimino, Fluorbenzylimino, Chlorbenzylimino,Trifluormethylbenzylimino, Chlor- (Trifluormethyl)benzylimino, Fluor-(Trifluormethyl)benzylimino, Methylsulfonylmethyl, Methylsulfonylethyl, Methylsulfonylpropyl, Methylsulfonylbutyl, Methylcarbonyl, Ethylcarbonyl, Propylcarbonyl, iso-Propylcarbonyl, cyclo-Propylcarbonyl, cyclo-Propyl- methylcarbonyl, cyclo-Butyl-methylcarbonyl, Butylcarbonyl, iso-Butylcarbonyl, tert- Butylcarbonyl, cyclo-Butylcarbonyl, cyclo-Pentylcarbonyl, cyclo-Hexylcarbonyl oder Trifluormethylcarbonyl steht, oder für einfach durch Phenyl, Pyridyl, Pyrimidyl, Furanyl, Thiophenyl, Oxazolyl, Thiazolyl, Indolyl, Aza-indolyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl oder 2,3-Dihydro-1,4- benzodioxinyl substituiertes Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, Oxy, Amino, N-Methylamino, N-Ethylamino oder Carbonyl steht, wobei Phenyl, Pyridyl, Pyrimidyl, Furanyl, Thiophenyl, Oxazolyl, Thiazolyl, Indolyl, Aza-indolyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Cyano, Fluor, Chlor, Brom, Iod, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, Trifluormethyl, Pentafluorethyl, Methoxy, Ethoxy, Trifluormethoxy, Pentafluorethoxy, Trifluormethylthio, Methyloxycarbonyl, Ethyloxycarbonyl, Carbamoyl, Thiocarbamoyl, Aminosulfonyl, Pyrazolyl, Imidazolyl, Methylpyrazolyl, Oxazolyl, Oxdiazolyl, Thiazolyl, Pyrrolyl, Pyrrolidinyl oder Pyrrolidinonyl substituiert sein können, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden substituiertes Phenyl, Pyridyl, Pyrimidyl, Thiophenyl, Indazolyl, Aza-indazolyl, 1,3-Benzodioxolyl, Oxetanyl, Thietanyl, Tetrahydrofuranyl, Oxotetrahydrofuranyl, Tetrahydrothiophenyl, Oxidotetrahydrothiophenyl, Dioxidotetrahydrothiophenyl, Tetrahydro-2H-pyranyl, Oxotetrahydro-2H-pyranyl, Tetrahydro-2H-thiopyranyl, Oxotetrahydro-2H-thiopyranyl, 2,3- Dihydro-1H-indenyl steht, wobei die Substituenten ausgewählt sind aus Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Trifluormethyl, Methoxy, Trifluormethoxy, Trifluormethylthio, Methyloxycarbonyl oder Ethyloxycarbonyl, oder R3 und R4 gemeinsam für (C3-C5)-Alkyl stehen, wobei ein 4-6 gliedriger gegebenfalls durch Halogen, Cyano, Trifluormethyl oder Trifluormethoxy substituierter- Ring gebildet wird, R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trifluormethoxy stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. 5. Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 4, in denen Q1 für jeweils gegebenenfalls einfach, zweifach, dreifach oder vierfach, gleich oder verschieden substituiertes Phenyl, 1,3-Benzodioxolyl, 2,3-Dihydro-1,4-benzodioxinyl, Pyridyl, Thienyl oder Pyrazol-1-yl oder Pyrazol-2-yl steht, wobei die Substituenten ausgewählt sind aus Fluor, Chlor, Brom, Iod, SF5, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, Heptafluorisopropyl, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Pentafluorethoxy, Tetrafluorethoxy, Chlortrifluorethoxy, Trifluorethenoxy, Trifluormethylsulfonyl, Trifluormethylsulfinyl, Trifluormethylsulfanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Trifluormethylcyclopropyl, Bis-Trifluormethylamino, Tetrafluorethylsulfanyl, Cyclopropylsulfanyl, (Trifluorvinyl)oxy oder Hexafluorpropoxy R1 für Methyl, Ethyl, i-Propyl, cyclo-Propyl, Methyl-cyclo-Propyl, Cyclo-Propyl-Methyl, Cyano- cyclo-Propyl, Chlor-cyclo-Propyl, cyclo-Propyl-cyclo-Propyl, Methoxyethyl, tert.-Butyl, cyclo- Butyl, Difluorcyclobutyl, cyclo-Pentyl, Trifluorethyl oder Trifluormethyl-cyclo-Propyl steht, oder für einfach durch Phenyl substituiertes Methyl steht, wobei Phenyl gegebenenfalls einfach durch Chlor, Brom, Nitro, Trifluormethyl substituiert sein kann, oder für gegebenenfalls einfach durch Chlor substituiertes Phenyl oder Pyridyl oder für Oxazolyl steht, R2 für Wasserstoff, Methyl, Ethyl, cyclo-Propylcarbonyl oder Methoxycarbonyl steht, R3 für Wasserstoff, Methyl, Methoxy oder Methoxycarbonyl steht, R4 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, cyclo-Butyl, Trifluorethyl, Trifluorpropyl, Cyanomethyl, Cyanoethyl, Cyanopropyl, Cyanobutyl, Cyanopentyl, Methyloxyethyl, Propinyl, Butinyl, cyclo-Propyl, cyclo-Butyl, cyclo-Pentyl, cyclo-Hexyl, cyclo- Propyl-methyl, cyclo-Butyl-methyl, cyclo-Pentyl-methyl, cyclo-Hexyl-methyl, cyclo-Propyl- ethyl, Cyano-cyclo-Hexyl-methyl, Trifluormethyl-cyclo-Hexyl-methyl, cyclo-Propyl-cyclo- Propyl, Methyl-cyclo-Propyl, Trifluormethyl-cyclo-Propyl, Trifluormethyl-cyclo-Hexyl, Difluor-cyclo-Propyl, Cyano-cyclo-Propyl, Cyano-cyclo-Butyl, Cyano-cyclo-Hexyl, Ethinyl- cyclo-Propyl, Methyloxy-cyclo-Propyl, Methyloxycarbonyl-cyclo-Propyl, Thiocarbamoyl- cyclo-Propyl, Methyloxycarbonylethyl, Cyanbenzylimino, Fluor-(Trifluormethyl)benzylimino, Methylsulfonylbutyl, Methoxy, Ethoxy, cyclo-Propyl-methyloxy, iso-Propyloxy, Cyanpropyloxy, Cyanphenyloxy, cyclo-Propylcarbonyl steht, oder für einfach durch Phenyl, Pyridyl, Indazolyl, Aza-indazolyl, Thiophenyl oder 1,3- Benzodioxolyl substituiertes Methyl, Ethyl, n-Propyl, cyclo-Propyl oder Carbonyl steht, wobei Phenyl, Pyridyl, Indazolyl, Aza-indazolyl, Thiophenyl oder 1,3-Benzodioxolyl jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Cyano, Fluor, Chlor, Nitro, Methyl, Trifluormethyl, Methoxy, Methyloxycarbonyl, Thiocarbamoyl, Aminosulfonyl, Methylpyrazolyl, Oxazolyl, Oxadiazolyl oder Pyrrolidinonyl substituiert sein können, oder für jeweils gegebenenfalls einfach substituiertes Phenyl, Pyridyl, Indazolyl, Oxetanyl, Thietanyl, Tetrahydrofuranyl, Oxotetrahydrofuranyl, Dioxidotetrahydrothiophenyl, Tetrahydro- 2H-pyranyl oder 2,3-Dihydro-1H-indenyl steht, wobei die Substituenten ausgewählt sind aus Chlor, Cyano, Methyl oder Methyloxycarbonyl, oder R3 und R4 gemeinsam für (C3-C5)-Alkyl stehen, wobei ein 4-6 gliedriger gegebenfalls durch Cyano substituierter Ring gebildet wird, R5, R6 unabhängig voneinander für Wasserstoff stehen V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. 6. Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 5, in denen Q1 für 2,2,3,3-Tetrafluor-2,3-dihydro-1,4-benzodioxin-6-yl, 2,2-Difluor-1,3-benzodioxol-5-yl, 2- Chlor-4-(trifluormethoxy)phenyl, 2-Ethyl-6-methyl-4-(pentafluorethyl)phenyl, 2-Fluor-4- (trifluormethoxy)phenyl, 2-Fluor-6-(trifluormethyl)pyridin-3-yl, 2-Methyl-4- (trifluormethoxy)phenyl, 3-(Pentafluorethyl)-1H-pyrazol-1-yl, 3-(Trifluormethoxy)phenyl, 3,5- Difluor-4-(trifluormethoxy)phenyl, 3-Chlor-4-(trifluormethoxy)phenyl, 3-Chlor-5- (trifluormethyl)pyridin-2-yl, 3-Fluor-4-(pentafluorethyl)phenyl, 3-Fluor-4- (trifluormethoxy)phenyl, 3-Fluor-4-(trifluormethyl)phenyl, 3-Methyl-4-(trifluormethoxy)phenyl, 4-(1,1,1,2,3,3,3-Heptafluorpropan-2-yl)phenyl, 4-(1,1,2,2-Tetrafluorethoxy)phenyl, 4-(1,1- Difluorethyl)phenyl, 4-(2,2,2-Trifluorethyl)phenyl, 4-(2-Chlor-1,1,2-trifluorethoxy)phenyl, 4- (Cyclopropylsulfanyl)phenyl, 4-(Difluormethoxy)-3,5-difluorphenyl, 4- (Difluormethoxy)phenyl, 4-(Difluormethyl)-3-fluorphenyl, 4-(Pentafluorethoxy)phenyl, 4- (Pentafluorethyl)phenyl, 4-SF5-phenyl, 4-(Trifluormethoxy)phenyl, 4-(Trifluormethyl)phenyl, 4- [(1,1,2,2-Tetrafluorethyl)sulfanyl]phenyl, 4-[(Difluormethyl)sulfanyl]phenyl, 4- [(Difluormethyl)sulfinyl]phenyl, 4-[(Trifluormethyl)sulfanyl]phenyl, 4- [(Trifluormethyl)sulfinyl]phenyl, 4-[(Trifluormethyl)sulfonyl]phenyl, 4- [(Trifluorvinyl)oxy]phenyl, 4-[1-(Trifluormethyl)cyclopropyl]phenyl, 4- [Bis(trifluormethyl)amino]phenyl, 4-[Chlor(difluor)methoxy]phenyl, 4-Bromphenyl,4- Chlorphenyl, 4-Fluorphenyl, 4-Iodphenyl, 5-(Trifluormethyl)-2-thienyl, 5- (Trifluormethyl)pyridin-2-yl, 6-(Trifluormethyl)pyridin-3-yl, 4-Brom-3-fluorphenyl, 4- (1,1,2,3,3,3-Hexafluorpropoxy)phenyl, 2,6-Dichlor-4-(pentafluorethyl)phenyl, 2-Chlor-3-fluor- 4-(pentafluorethyl)phenyl, 3-Fluor-5-methyl-4-(pentafluorethyl)phenyl, 2,6-Difluor-4- (pentafluorethyl)phenyl, 2-Chlor-5-fluor-4-(pentafluorethyl)phenyl, 3-Methyl-4- (pentafluorethyl)phenyl, 3,5-Difluor-4-(pentafluorethyl)phenyl, 2,3-Difluor-4- (pentafluorethyl)phenyl, 3-Chlor-4-(pentafluorethyl)phenyl, 2,3,5-Trifluor-4- (pentafluorethyl)phenyl, 2,5-Difluor-4-(pentafluorethyl)phenyl, 2,6-Dichlor-3-fluor-4- (pentafluorethyl)phenyl oder 3-Chlor-5-fluor-4-(pentafluorethyl)phenyl steht, R1 für Cyclobutyl, Cyclopentyl, Cyclopropyl, Cyclopropylmethyl, Ethyl, Isopropyl, Methyl, tert- Butyl, 1,3-Oxazol-5-yl, 1-Chlorcyclopropyl, 1-Cyancyclopropyl, 1-Cyclopropyl-cyclopropyl, 1- Methoxyethyl, 1-Methylcyclopropyl, 2-Chlorphenyl, 3,3-Difluorcyclobutyl, 4- (Trifluormethyl)benzyl, 4-Brombenzyl, 4-Chlorphenyl, 4-Nitrobenzyl, 2,2,2-Trifluorethyl, 1- (Trifluormethyl)cyclopropyl oder 6-Chlorpyridin-3-yl steht, R2 für Wasserstoff, Methyl, Ethyl, Cyclopropylcarbonyl oder Methoxycarbonyl steht, R3 für Wasserstoff, Methyl, Methoxy oder Methoxycarbonyl steht, R4 für (1-Methyl-1H-indazol-7-yl)methyl, (1-Methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl, (1S)- 1-[4-(Trifluormethyl)phenyl]ethyl, (1S)-1-[4-(Trifluormethyl)phenyl]ethyl, (2,2-Difluor-1,3- benzodioxol-5-yl)methyl, (4-Cyancyclohexyl)methyl, (5-Cyanpyridin-2-yl)methyl, (6- Chlorpyridin-3-yl)methyl, (6-Cyanpyridin-3-yl)methyl, (trans-4-Cyancyclohexyl)methyl, [cis-4- (Trifluormethyl)cyclohexyl]methyl, 1-(4-Cyanphenyl)cyclopropyl, 1-(4-Cyanphenyl)ethyl, 1-(4- Nitrophenyl)cyclopropyl, 1-(4-Nitrophenyl)ethyl, 1-(Methoxycarbonyl)cyclopropyl, 1- (Trifluormethyl)cyclopropyl, 1,1-Dioxidotetrahydrothiophen-3-yl, 1-[4- (Trifluormethyl)phenyl]ethyl, 1-Thiocarbamoylcyclopropyl, 1-Cyancyclobutyl, 1- Cyancyclopropyl, 1-Cyanethyl, 1-Cyclopropyl-cyclopropyl, 1-Cyclopropylethyl, 1- Ethinylcyclopropyl, 1-Methoxycarbonylethyl, 1-Methoxycyclopropyl, 1-Methylcyclopropyl, 2- (3-Cyanphenyl)ethyl, 2-(4-Cyanphenyl)ethyl, 2,2,2-Trifluorethyl, 2,2-Difluorcyclopropyl, 2,4- Dichlor-5-fluorbenzyl, 2,4-Dichlorbenzyl, 2-Cyanpropan-2-yl, 2-Fluor-4-(trifluormethyl)benzyl, 2-Fluor-4-nitrobenzyl, 2-Methoxyethyl, 2-Oxotetrahydrofuran-3-yl, 3- (Methoxycarbonyl)oxetan-3-yl, 3,3,3-Trifluorpropyl, 3-[4-(Trifluormethyl)phenyl]propyl, 3- Chlorbenzyl, 3-Cyanbenzyl, 3-Cyanpentan-3-yl, 3-Fluor-4-(trifluormethyl)benzyl, 3- Fluorbenzyl, 3-Methylthietan-3-yl, 4-(1,2,4-Oxadiazol-3-yl)benzyl, 4-(1,3,4-Oxadiazol-2- yl)benzyl, 4-(1,3-Oxazol-5-yl)benzyl, 4-(1-Methyl-1H-pyrazol-3-yl)benzyl, 4-(1-Methyl-1H- pyrazol-5-yl)benzyl, 4-(Methoxycarbonyl)benzyl, 4-(Trifluormethyl)benzyl, 4- Thiocarbamoylbenzyl, 4-Chlor-2-fluorbenzyl, 4-Chlor-3-fluorbenzyl, 4-Chlorbenzyl, 4- Chlorphenyl, 4-Cyan-2,5-difluorbenzyl, 4-Cyan-2,6-difluorbenzyl, 4-Cyan-2-fluorbenzyl, 4- Cyan-3,5-difluorbenzyl, 4-Cyan-3-fluorbenzyl, 4-Cyanbenzyl, 4-Cyanbutyl, 4-Cyancyclohexyl, 4-Cyanphenyl, 4-Cyantetrahydro-2H-pyran-4-yl, 4-Fluor-3-(trifluormethyl)benzyl, 4- Methoxybenzyl, 4-Nitrobenzyl, 4-Aminosulfonylbenzyl, 5-Cyan-1H-indazol-3-yl, 5-Cyan-2,3- dihydro-1H-inden-1-yl, 5-Cyanpentyl, Benzyl, But-3-in-2-yl, n-Butyl, cis-4- (Trifluormethyl)cyclohexyl, Cyanmethyl, Cyclobutyl, Cyclobutylmethyl, Cyclohexyl, Cyclohexylmethyl, Cyclopentyl, Cyclopentylmethyl, Cyclopropyl, Cyclopropylmethyl, Ethyl, Isobutyl, Isopropyl, Methyl, Oxetan-3-yl, Prop-2-in-1-yl, n-Propyl, Pyridin-2-ylmethyl, Pyridin- 3-yl, Thietan-3-yl, trans-4-(Trifluormethyl)cyclohexyl, (5-Nitro-2-thienyl)methyl, (5-Cyan-2- thienyl)methyl, 4-Cyanbenzylimin, 3-Fluor-4-(trifluormethyl)benzylimin, [4-(2-Oxopyrrolidin- 1-yl)phenyl]methyl, 2-Methyl-1-methylsulfonylpropan-2-yl, (Pyridin-4-yl)methyl, Methoxy, Ethoxy, Cyclopropylmethyloxy, Isopropyloxy, 3-Cyanpropyloxy, 4-Cyanphenyloxy, Cyclopropylcarbonyl oder 4-Nitrobenzoyl steht, oder R3 und R4 gemeinsam für einen der folgenden Ringe stehen: Q1 is each optionally mono- or polysubstituted by identical or different substituents aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl or oxo-hetaryl, where the substituents are selected from: cyano, carboxyl, Halogen, nitro, hydroxy, amino, SCN, SF5, tri (C1-C6) alkylsilyl, (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) Cyanoalkyl, (C1-C6) Hydroxyalkyl, hydroxycarbonyl- (C1-C6) -alkoxy, (C1- C6) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) alkyl, (C2-C6) Alkenyl, (C2- C6) Haloalkenyl, (C2-C6) Cyanoalkenyl, (C2-C6) Alkynyl, (C2-C6) Haloalkynyl, (C2- C6) Cyanoalkynyl, (C1-C6) Alkoxy, (C1-C6) Haloalkoxy, (C1-C6) Cyanoalkoxy, (C1- C6) Alkoxycarbonyl- (C1-C6) alkoxy, (C1-C6) Alkoxy (C1-C6) alkoxy, (C3-C8th) Cycloalkyl, (C3- C8th) Halocycloalkyl, (C1-C6) Alkyl (C3-C8th) cycloalkyl, (C1-C6) Haloalkyl (C3- C8th) cycloalkyl, (C1-C4) Haloalkenoxy, (C1-C6) Alkylhydroxyimino, (C1-C6) Alkoxyimino, (C1- C6) Alkyl (C1-C6) alkoxyimino, (C1-C6) Haloalkyl (C1-C6) alkoxyimino, (C1-C6) Alkylsulfanyl, (C1-C6) Alkoxy (C1-C6) alkylsulfanyl, (C1-C6) Alkylsulfanyl (C1-C6) alkyl, (C1-C6) Alkylsulfinyl, (C1-C6) Haloalkylsulfinyl, (C1-C6) Alkoxy (C1-C6) alkylsulfinyl, (C1-C6) Alkylsulfinyl (C1- C6) alkyl, (C1-C6) Alkylsulfonyl, (C1-C6) Haloalkylsulfonyl, (C1-C6) Alkoxy (C1- C6) alkylsulfonyl, (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkylsulfonyloxy, (C1- C6) Haloalkylsulfanyl, (C3-C6) Cycloalkylsulfanyl, (C3-C6) Halocycloalkylsulfanyl, (C3- C6) Cycloalkylsulfonyl, (C3-C6) Halocycloalkylsulfonyl, (C3-C6) Cycloalkylsulfinyl, (C3- C6) Halocycloalkylsulfinyl, (C1-C6) Alkylcarbonyl, (C1-C6) Haloalkylcarbonyl, (C1- C6) Alkylcarbonyloxy, (C1-C6) Alkoxycarbonyl, (C1-C6) Haloalkoxycarbonyl, aminocarbonyl, (C1-C6) Alkylaminocarbonyl, di (C1-C6) alkylaminocarbonyl, (C2-C6) Alkenylaminocarbonyl, di- (C2-C6) alkenylaminocarbonyl, (C3-C8) cycloalkylaminocarbonyl, (C1-C6) alkylsulfonylamino, (C1-C6) alkylamino, di (C1-C6) alkylamino, (C1-C6) haloalkylamino, Bis (C1-C6) haloalkylamino, aminosulfonyl, (C1-C6) alkylaminosulfonyl, di- (C1-C6) alkylaminosulfonyl, (C1-C6) alkylsulfoximino, aminothiocarbonyl, (C1-C6) alkylaminothiocarbonyl, di- (C1-C6) alkylaminothiocarbonyl, (C3-C8) cycloalkylamino, R1 is (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl,  (C1-C6) alkoxy- (C1-C6) alkyl, (C1-C6) haloalkoxy- (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkenyloxy- (C1-C6) alkyl, ( C2-C6) haloalkenyloxy- (C1-C6) alkyl, (C2-C6) haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) alkynyloxy- (C1-C6) alkyl, (C2 C6) haloalkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl- (C1-C6) -alkyl, (C3- C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) alkyl- (C3-C8) cycloalkyl, (C1-C6) haloalkyl- (C3-C8) cycloalkyl, halo (C3-C8) cycloalkyl, cyano (C3 -C8) cycloalkyl, (C 2 -C 6) alkynyl- (C 3 -C 8) -cycloalkyl, (C 1 -C 6) -alkoxy- (C 3 -C 8) -cycloalkyl, (C 1 -C 6) -alkoxycarbonyl- (C 3 -C 8) -cycloalkyl, (C 1 -C 6) -cycloalkyl, C6) alkylamino, di- (C1-C6) alkylamino, (C3-C8) cycloalkylamino, (C1-C6) alkylcarbonylamino, (C1-C6) alkylthio (C1-C6) alkyl, (C1-C6) Haloalkylthio (C 1 -C 6) alkyl, (C 1 -C 6) alkylsulfinyl (C 1 -C 6) alkyl, (C 1 -C 6) haloalkylsulfinyl (C 1 -C 6) alkyl, (C 1 -C 6) alkylsulfonyl (C 1 -C 6) alkyl , (C 1 -C 6) haloalkylsulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkylthio ( C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1 -C6) alkylcarbonyl- (C1-C6) alkyl, (C1-C6) haloalkylcarbonyl- (C1-C6) alkyl, (C1-C6) alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) haloalkoxycarbonyl- (C1- C6) alkyl, (C1-C6) alkylsulfonylamino, aminosulfonyl- (C1-C6) alkyl, (C1-C6) alkylaminosulfonyl- (C1-C6) alkyl, di- (C1-C6) alkyl-aminosulfonyl- (C1-C6) alkyl, (C 1 -C 4) alkoxy, (C 3 -C 6) cycloalkoxy, (C 3 -C 6) cycloalkylcarbonyl or (C 1 -C 4) -alkylcarbonyl, or in each case optionally monosubstituted or polysubstituted, identical or different, by aryl, hetaryl, oxo-hetaryl , Heterocyclyl or oxo-heterocyclyl substituted (C1-C6) Alkyl, (C1- C6) Alkoxy, (C2-C6) Alkenyl, (C2-C6) Alkynyl, (C3-C8th) Cycloalkyl, wherein aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, aminosulfonyl, (C1-C6) Alkyl, (C3-C6) Cycloalkyl, (C1-C6) Alkoxy, (C1-C6) Haloalkyl, (C1- C6) Haloalkoxy, (C1-C6) Alkylthio, (C1-C6) Alkylsulfinyl, (C1-C6) Alkylsulfonyl, (C1- C6) Alkylsulfimino, (C1-C6) Alkylsulfimino- (C1-C6) alkyl, (C1-C6) Alkylsulfimino- (C2- C6) alkylcarbonyl, (C1-C6) Alkylsulfoximino, (C1-C6) Alkylsulfoximino- (C1-C6) alkyl, (C1- C6) Alkylsulfoximino- (C2-C6) alkylcarbonyl, (C1-C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl or (C3-C6) Trialkylsilyl may be substituted, or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy , Carbamoyl, (C1- C6) Alkyl, (C3-C8th) Cycloalkyl, (C1-C6) -Alkoxy, (C1-C6) Haloalkyl, (C1-C6) Haloalkoxy, (C1-C6) Alkylthio, (C1-C6) Haloalkylthio, (C1-C6) Alkylsulfinyl, (C1-C6) Alkylsulfonyl, (C1- C6) Alkylsulfimino, (C1-C6) Alkylsulfimino- (C1-C6) alkyl, (C1-C6) Alkylsulfimino- (C2- C6) alkylcarbonyl, (C1-C6) Alkylsulfoximino, (C1-C6) Alkylsulfoximino- (C1-C6) alkyl, (C1-  C6) alkylsulfoximino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) trialkylsilyl, R 2 is hydrogen, (C 1 -C 6) -alkyl, (C 3 -C 8) -cycloalkyl, (C1-C6) alkoxy, (C1-C6) alkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) hydroxyalkyl, ( C1-C6) alkoxy- (C1-C6) alkyl, (C1-C6) haloalkoxy- (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkenyloxy- (C1-C6) alkyl, (C2 -C6) haloalkenyloxy- (C1-C6) alkyl, (C2-C6) haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) alkynyloxy- (C1-C6) alkyl, (C2- C6) haloalkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) alkyl- (C3-C8 ) Cycloalkyl, halo (C3-C8) cycloalkyl, (C1-C6) alkylthio (C1-C6) alkyl, (C1-C6) haloalkylthio (C1-C6) alkyl, (C1-C6) alkylsulfinyl (C1-C6 ) alkyl, (C 1 -C 6) haloalkylsulfinyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylsulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkylsulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) alkoxy (C1-C6) alkylthio (C1-C6 ) alkyl, (C 1 -C 6) alkoxy (C 1 -C 6) alkylsulfinyl (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy (C 1 -C 6) alkylsulfonyl (C 1 -C 6) alkyl, (C 1 -C 6) Alkylcarbonyl (C 1 -C 6) alkyl, (C 1 -C 6) haloalkylcarbonyl (C 1 -C 6) alkyl, (C 1 -C 6) alkoxycarbonyl (C 1 -C 6) alkyl, (C 1 -C 6) haloalkoxycarbonyl (C 1 -C 6) alkyl , Aminocarbonyl (C 1 -C 6) alkyl, (C 1 -C 6) alkylamino (C 1 -C 6) alkyl, di (C 1 -C 6) alkylamino (C 1 -C 6) alkyl or (C 3 -C 8) cycloalkylamino (C 1 -C 6) alkyl). C6) alkyl, R3 is hydrogen, (C1-C6) alkyl, (C3-C8) cycloalkyl, (C1-C6) alkoxy, (C1-C6) alkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl , (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C6) Hydroxyalkyl, (C1-C6) Alkoxy (C1-C6) alkyl, (C1-C6) Haloalkoxy (C1-C6) alkyl, (C2- C6) Alkenyl, (C2-C6) Alkenyloxy (C1-C6) alkyl, (C2-C6) Halogenalkenyloxy- (C1-C6) alkyl, (C2- C6) Haloalkenyl, (C2-C6) Cyanoalkenyl, (C2-C6) Alkynyl, (C2-C6) Alkynyloxy (C1-C6) alkyl, (C2- C6) Halogenalkinyloxy- (C1-C6) alkyl, (C2-C6) Haloalkynyl, (C2-C6) Cyanoalkynyl, (C3- C8th) Cycloalkyl (C3-C8th) Cycloalkyl, (C1-C6) Alkyl (C3-C8th) Cycloalkyl, halogen (C3-C8th) cycloalkyl, (C1-C6) Alkylthio (C1-C6) alkyl, (C1-C6) Haloalkylthio (C1-C6) alkyl, (C1-C6) Alkylsulfinyl (C1- C6) alkyl, (C1-C6) Halogenalkylsulfinyl- (C1-C6) alkyl, (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1- C6) Haloalkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylthio (C1-C6) alkyl, (C1- C6) Alkoxy (C1-C6) Alkylsulfinyl (C1-C6) alkyl, (C1-C6) Alkoxy (C1-C6) Alkylsulfonyl (C1-C6) alkyl, (C1-C6) Alkylcarbonyl (C1-C6) alkyl, (C1-C6) Haloalkylcarbonyl (C1-C6) alkyl, (C1- C6) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) Haloalkoxycarbonyl (C1-C6) alkyl, aminocarbonyl (C1-C6) alkyl, (C1-C6) alkylamino (C1-C6) alkyl, di (C1-C6) alkylamino (C1-C6) alkyl or (C3-C8th) Cycloalkylamino (C1-C6) alkyl, R4 is (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1-C6) Cyanoalkyl, (C1-C6) Hydroxyalkyl, (C1-C6) Alkoxy (C1-C6) alkyl, (C1-C6) Haloalkoxy (C1-C6) alkyl, (C2-C6) Alkenyl, (C2- C6) Alkenyloxy (C1-C6) alkyl, (C2-C6) Halogenalkenyloxy- (C1-C6) alkyl, (C2-C6) Haloalkenyl, (C2-C6) Cyanoalkenyl, (C2-C6) Alkynyl, (C2-C6) Alkynyloxy (C1-C6) alkyl, (C2-  C6) haloalkynyloxy- (C1-C6) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl- (C1-C6) -alkyl, cyano (C3-C6) C8) cycloalkyl- (C1-C6) alkyl, halo (C3-C8) cycloalkyl- (C1-C6) alkyl, (C1-C4) haloalkyl- (C3-C8) cycloalkyl- (C1-C6) alkyl, (C3-C8) C8) cycloalkyl- (C3-C8) cycloalkyl, (C1-C6) alkyl- (C3-C8) cycloalkyl, (C1-C6) haloalkyl- (C3-C8) cycloalkyl, halo (C3-C8) cycloalkyl, cyano (C3 -C8) cycloalkyl, (C 2 -C 6) alkynyl- (C 3 -C 8) -cycloalkyl, (C 1 -C 6) -alkoxy- (C 3 -C 8) -cycloalkyl, (C 1 -C 6) -alkoxycarbonyl- (C 3 -C 8) -cycloalkyl, carbamoyl- C3-C8) cycloalkyl, thiocarbamoyl (C3-C8) cycloalkyl, (C1-C6) alkylthio (C1-C6) alkyl, (C1-C6) haloalkylthio (C1-C6) alkyl, (C1-C6) alkylsulfinyl (C1-C6) alkyl, (C1-C6) haloalkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) haloalkylsulfonyl- (C1-C6) alkyl, ( C1-C6) alkoxy- (C1-C6) alkylthio (C1-C6) alkyl, (C1-C6) alkoxy- (C1-C6) alkylsulfinyl- (C1-C6) alkyl, (C1-C6) alkoxy- (C1 -C6) alkylsulfonyl- (C1-C6) alkyl, (C1-C6) alkylcarbonyl- (C1-C6) alkyl, (C1-C6 ) Haloalkylcarbonyl (C1-C6) alkyl, (C1-C6) alkoxycarbonyl- (C1-C6) alkyl, (C1-C6) haloalkoxycarbonyl- (C1-C6) alkyl, (C1-C6) alkylsulfonylamino, aminosulfonyl- (C1- C6) alkyl, (C1-C6) alkylaminosulphonyl (C1-C6) alkyl di (C1-C6) alkylaminosulphonyl (C1-C6) alkyl, amino, (C1-C6) alkylamino, di (C1-C6 ) alkylamino, (C3-C8) cycloalkylamino, N- (C1-C6) alkyl- (C3-C8) cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, halobenzylamino, N- (C1-C6) alkylbenzylamino, N- ( C1-C6) alkyl-cyanobenzylamino, N- (C1-C6) alkyl-nitrobenzylamino, N- (C1-C6) alkyl-halobenzylamino, (C1-C6) alkylcarbonyl-amino, (C3-C8) cycloalkylcarbonylamino, hydroxy, (C1-C6) Alkoxy, (C3-C8th) Cycloalkoxy, (C3-C8th) Cycloalkyl (C1-C6) Alkoxy, cyano (C1- C6) Alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, halobenzyloxy, (C1- C6) Alkylimino, (C3-C8th) Cycloalkylimino, benzylimino, cyanobenzylimino, nitrobenzylimino, halobenzylimino, (C1-C6) Haloalkylbenzylimino, halogeno [(C1- C6) Haloalkyl] benzylimino, (C1-C6) Alkylcarbonyl, (C1-C6) Haloalkylcarbonyl, (C3- C8th) Cycloalkylcarbonyl or (C3-C8th) Cycloalkyl (C1-C6) Alkyl-carbonyl, or represents in each case optionally mono- or polysubstituted, identically or differently by aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl (C1-C6) Alkyl, (C1-C6) Haloalkyl, (C1-C6) Alkoxy, (C2-C6) Alkenyl, (C2-C6) Alkynyl, (C3-C8th) Cycloalkyl, oxy, amino, N- (C1-C6) Alkylamino, N- (C3- C8th) Cycloalkylamino or carbonyl, where aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identically or differently, by halogen, Cyano, nitro, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C1-C6) Alkyl, (C3- C6) Cycloalkyl, (C1-C6) Alkoxy, (C1-C6) Haloalkyl, (C1-C6) Haloalkoxy, (C1-C6) Alkylthio, (C1-C6) Haloalkylthio, (C1-C6) Alkylsulfinyl, (C1-C6) Alkylsulfonyl, (C1-C6) Haloalkylsulfinyl, (C1-C6) Haloalkylsulfonyl, (C1-C6) Alkylsulfimino, (C1-C6) Alkylsulfimino- (C1C6) alkyl, (C1-C6) alkylsulfimino (C2-C6) alkylcarbonyl, (C1-C6) alkylsulfoximino, (C1-  C 6) alkylsulfoximino (C 1 -C 6) alkyl, (C 1 -C 6) alkylsulfoximino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) trialkylsilyl or hetaryl or for each optionally mono- or polysubstituted, identically or differently substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from Halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C 1 -C 6) alkyl, (C 3 -C 8) cycloalkyl, (C 1 -C 6) -alkoxy, (C 1 -C 6) -haloalkyl, (C 1 -C 6) -halogenoalkoxy, (C1-C6) alkylthio, (C1-C6) haloalkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, (C1-C6) haloalkylsulfinyl, (C1-C6) haloalkylsulfonyl, (C1-C6) alkylsulfimino , (C1-C6) alkylsulfimino (C1-C6) alkyl, (C1-C6) alkylsulfimino (C2-C6) alkylcarbonyl, (C1-C6) alkylsulfoximino, (C1-C6) alkylsulfoximino (C1-C6) alkyl, (C1-C6) alkylsulfoximino (C2-C6) alkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkylcarbonyl, (C 3 -C 6) trialkylsilyl, or R 3 and R 4 together represent (C 2 -C 6) -alkyl or (C 2 -C 6) -alkenyl, where a 3-7-membered is optionally substituted by halogen, cyano, hydroxyl, amino, carboxy, carbamoyl, (C1-C6) alkyl, (C3-C8) cycloalkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) alkylthio or (C1-C6) haloalkylthio Ring is formed, which may optionally contain one to two double bonds, R5, R6 independently of each other for hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, (C1-C6) Alkylamino, di (C1-C6) Alkylamino, (C3-C6) Cycloalkyl, halogen (C3-C6) cycloalkyl, (C1- C6) Alkyl, (C1-C6) Haloalkyl, (C2-C6) Alkenyl, (C2-C6) Haloalkenyl, (C2-C6) Alkynyl, (C2- C6) Haloalkynyl, (C1-C6) Alkoxy, (C1-C6) Haloalkoxy, (C1-C6) Alkylthio, (C1- C6) Haloalkylthio, (C1-C6) Alkylsulfinyl, (C1-C6) Haloalkylsulfinyl, (C1-C6) Alkylsulfonyl, (C 1 -C 6) haloalkylsulfonyl, V 1 is oxygen or sulfur, V 2 is oxygen, sulfur or -NH. 2. Compounds of general formula (I) according to claim 1, in which Q1 is in each case optionally mono- or polysubstituted by identical or different substituents phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl or oxo -Hetaryl, wherein the substituents are selected from cyano, halogen, nitro, amino, SF5, (C1-C4) alkyl, (C1-C4) haloalkyl, (C1-C4) cyanoalkyl, (C1-C4) hydroxyalkyl, (C1 -C4) alkoxy- (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) haloalkenyl, (C2-C4) cyanoalkenyl, (C2-C4) alkynyl, (C2-C4) haloalkynyl, (C2-4) C4) cyanoalkynyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-  C4) cyanoalkoxy, (C1-C4) alkoxy- (C1-C4) alkoxy, (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C1-C4) alkyl- (C3-C6) cycloalkyl, (C1-C4 ) Haloalkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkenoxy, (C1-C4) alkylhydroxyimino, (C1-C4) alkoxyimino, (C1-C4) alkyl- (C1-C4) alkoxyimino, (C1-C4) Haloalkyl- (C1-C4) alkoxyimino, (C1-C4) alkylsulfanyl, (C1-C4) alkylsulfanyl- (C1-C4) alkyl, (C1-C4) alkylsulfinyl, (C1-C4) haloalkylsulfinyl, (C1-C4) alkylsulfinyl (C1-C4) alkyl, (C1-C4) alkylsulfonyl, (C1-C4) haloalkylsulfonyl, (C1-C4) alkylsulfonyl- (C1-C4) alkyl, (C1-C4) alkylsulfonyloxy, (C1-C4) haloalkylsulfanyl, (C3-C6) cycloalkylsulfanyl, (C3-C6) halocycloalkylsulfanyl, (C3-C6) cycloalkylsulfonyl, (C3-C6) halocycloalkylsulfonyl, (C3-C6) cycloalkylsulfinyl, (C3-C6) halocycloalkylsulfinyl, (C1-C4) alkylcarbonyl, ( C1-C4) haloalkylcarbonyl, aminocarbonyl, (C1-C4) alkylaminocarbonyl, di (C1-C4) alkylaminocarbonyl, (C1-C4) alkylsulfonylamino, (C1-C4) alkylamino, di (C1-C4) alkylamino, ( C1-C6) haloalkylamino, bis (C1-C6) haloalkylamino, aminosulfonyl, (C1-C4) alkylaminosulfonyl, di (C1-C4) alkylaminosulfonyl, R1 for (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, ( C1-C6) hydroxyalkyl, (C1-C4) alkoxy- (C1-C4) alkyl, (C1-C4) haloalkoxy- (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkenyloxy- (C1 -C 6) alkyl, (C 2 -C 4) haloalkenyloxy (C 1 -C 6) alkyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (C 1 -C 4) C6) alkyl, (C2-C4) haloalkynyloxy- (C1-C4) alkyl, (C2-C4) haloalkynyl, (C2-C4) cyanoalkynyl, (C3-C6) Cycloalkyl, (C3-C6) Cycloalkyl (C1-C4) alkyl, (C3-C6) Cycloalkyl (C3-C6) Cycloalkyl, (C1- C4) Alkyl (C3-C6) Cycloalkyl, (C1-C4) Haloalkyl (C3-C6) cycloalkyl, halogen (C3- C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) Alkynyl (C3-C6) cycloalkyl, (C1-C4) Alkoxy (C3- C6) cycloalkyl, (C1-C4) Alkoxycarbonyl- (C3-C6) cycloalkyl, (C1-C6) Alkylamino, di (C1-C6) alkylamino, (C3-C6) Cycloalkylamino, (C1-C4) Alkylthio (C1-C6) alkyl, (C1-C4) Haloalkylthio (C1- C6) alkyl, (C1-C4) Alkylsulfinyl (C1-C6) alkyl, (C1-C4) Halogenalkylsulfinyl- (C1-C6) alkyl, (C1- C4) Alkylsulfonyl (C1-C6) alkyl, (C1-C4) Haloalkylsulfonyl (C1-C6) alkyl, (C1- C4) Alkylcarbonyl (C1-C6) alkyl, (C1-C4) Alkoxycarbonyl- (C1-C6) alkyl, (C1-C4) Alkoxy, (C3- C6) Cycloalkoxy, (C3-C6) Cycloalkylcarbonyl or (C1-C4) Alkylcarbonyl, or represents in each case optionally mono- or polysubstituted, identically or differently by aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl (C1-C4) Alkyl, (C1- C4) alkoxy, (C2-C4) alkenyl, (C2-C4) alkynyl, (C3-C6) cycloalkyl, where aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl in each case optionally mono- or polysubstituted, identical or different by halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, aminosulfonyl, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C4) Haloalkyl, (C1- C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1- C6) Alkoxycarbonyl, (C1-C6) Alkylcarbonyl or (C3-C6) Trialkylsilyl can be substituted,  or represents in each case optionally mono- or polysubstituted by identical or different substituents aryl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C1- C6) alkyl, (C3-C6) cycloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkyl, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-4) C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkylcarbonyl, (C3-C6) trialkylsilyl, R2 represents hydrogen, (C1-C6) alkyl, (C3-C6) cycloalkyl , (C1-C4) alkoxy, (C1-C6) alkylcarbonyl, (C3-C6) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C4) haloalkyl or (C1-C4) cyanoalkyl, R3 represents hydrogen, (C1 -C6) alkyl, (C3-C6) cycloalkyl, (C1-C4) alkoxy, (C1-C6) alkylcarbonyl, (C3-C6) cycloalkylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C4) haloalkyl or (C1- C4) cyanoalkyl, R4 is (C1-C6) alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C4) hydroxyalkyl, (C1-C4) Al koxy- (C1-C4) alkyl, (C1-C4) haloalkoxy- (C1-C4) alkyl, (C2-C6) alkenyl, (C2-C4) alkenyloxy- (C1-C6) alkyl, (C2-C4) haloalkenyloxy (C1-C4) alkyl, (C2-C4) haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C4) alkynyloxy (C1-C4) alkyl, (C2-C4) haloalkynyloxy (C1-C4) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C6) -alkyl, cyano (C3-C6) cycloalkyl- (C1-C6) alkyl, halo (C3-C6) cycloalkyl- (C1-C6) alkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl- (C1-C6) alkyl, (C3-C6) Cycloalkyl (C3-C6) Cycloalkyl, (C1-C6) Alkyl (C3-C6) Cycloalkyl, (C1-C6) Haloalkyl (C3-C6) cycloalkyl, halogen (C3-C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) Alkynyl (C3- C6) cycloalkyl, (C1-C4) Alkoxy (C3-C6) cycloalkyl, (C1-C4) Alkoxycarbonyl- (C3-C6) cycloalkyl, carbamoyl (C3-C6) cycloalkyl, thiocarbamoyl (C3-C6) cycloalkyl, (C1-C4) Alkylthio (C1- C4) alkyl, (C1-C4) Haloalkylthio (C1-C4) alkyl, (C1-C4) Alkylsulfinyl (C1-C4) alkyl, (C1- C4) Halogenalkylsulfinyl- (C1-C4) alkyl, (C1-C4) Alkylsulfonyl (C1-C4) alkyl, (C1- C4) Haloalkylsulfonyl (C1-C4) alkyl, (C1-C6) Alkylcarbonyl (C1-C6) alkyl, (C1- C6) Haloalkylcarbonyl (C1-C6) alkyl, (C1-C4) Alkoxycarbonyl- (C1-C4) alkyl, (C1- C4) Haloalkoxycarbonyl (C1-C4) alkyl, (C1-C4) Alkylsulfonylamino, aminosulfonyl (C1- C4) alkyl, (C1-C4) Alkylaminosulfonyl (C1-C4) alkyl, or di- (C1-C4) Alkyl-aminosulphonyl (C1- C6) alkyl, amino, (C1-C4) Alkylamino, di (C1-C4) alkyl-amino, (C3-C6) Cycloalkylamino, N- (C1C4) alkyl (C3-C6) cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, halobenzylamino, N- (C1-C4) alkyl benzylamino, N- (C1-C4) alkyl-cyanobenzylamino, N- (C1- C4) alkyl-nitrobenzylamino, N- (C1-C4) alkyl-halobenzylamino, (C1-C4) Alkylcarbonylamino, (C3-C6) Cycloalkylcarbonylamino, hydroxy, (C1-C4) Alkoxy, (C3-C6) Cycloalkoxy, (C3- C6) Cycloalkyl (C1-C4) Alkoxy, cyano (C1-C4) Alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, halobenzyloxy, (C1-C4) Alkylimino, (C3-C6) Cycloalkylimino,  Benzylimino, cyanobenzylimino, nitrobenzylimino, halobenzylimino, (C 1 -C 4) haloalkylbenzylimino, halo [(C 1 -C 4) haloalkyl] benzylimino, (C 1 -C 4) alkylcarbonyl, (C 1 -C 4) haloalkylcarbonyl, (C 3 -C 6) cycloalkylcarbonyl or (C 3 - C6) cycloalkyl- (C 1 -C 4) -alkyl-carbonyl, or in each case optionally mono- or polysubstituted, identically or differently, by aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo -Hetaryl, heterocyclyl or oxo-heterocyclyl substituted (C1-C4) alkyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C2-C4) alkenyl, (C2-C4) alkynyl, (C3-C6) cycloalkyl , Oxy, amino, N- (C 1 -C 4) alkylamino, N- (C 3 -C 6) cycloalkylamino or carbonyl, wherein aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo -Hetaryl, heterocyclyl or oxo-heterocyclyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C 1 -C 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C1-C4) A lkoxy, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkylthio, (C 1 -C 4) haloalkylthio, (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) haloalkyl - sulfinyl, (C1-C4) haloalkylsulfonyl, (C1-C4) alkylsulfimino, (C1-C4) alkylsulfimino (C1-C4) alkyl, (C1-C4) alkylsulfoximino, (C1-C4) alkylsulfoximino (C1-C4) alkyl, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkylcarbonyl, (C 3 -C 6) trialkylsilyl or hetaryl be substituted, or or for each optionally mono- or polysubstituted by identical or different substituted aryl, 2,3-dihydro-1H indenyl, 1,3-benzodioxolyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, wherein the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) -Alkoxy, (C1- C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1- C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1-C4) Haloalkylsulfinyl, (C1-C4) Haloalkylsulfonyl, (C1-C4) Alkylsulfimino, (C1-C4) Alkylsulfimino- (C1-C4) alkyl, (C1- C4) Alkylsulfoximino, (C1-C4) Alkylsulfoximino- (C1-C4) alkyl, (C1-C4) Alkoxycarbonyl, (C1- C4) Alkylcarbonyl, (C3-C6) Trialkylsilyl, or R3 and R4 together for (C2-C6) -Alkyl or for (C2-C6) Alkenyl, with a 3-7 membered, optionally substituted by halogen, cyano, hydroxy, amino, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) - alkoxy, (C1-C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio or (C1-C4) Halogenoalkylthio substituted ring is formed, which may optionally contain one to two double bonds, R5, R6 independently of one another represent hydrogen, cyano, halogen, nitro, (C3-C6) Cycloalkyl, (C1C4) alkyl, (C1-C4) haloalkyl or (C1-C4) haloalkoxy, V1 represents oxygen or sulfur,  V2 stands for oxygen, sulfur or -NH. 3. Compounds of general formula (I) according to claim 1 or 2, in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents, phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, pyrimidyl , Pyridazinyl, pyridyl, thienyl, furanyl, oxazolyl, thiazolyl, imidazolyl or pyrazolyl, wherein the substituents are selected from cyano, halogen, nitro, SF5, (C1-C4) Alkyl, (C1C4) haloalkyl, (C2-C4) alkenyl, (C2-C4) haloalkenyl, (C2-C4) alkynyl, (C2-C4) haloalkynyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C3-C4) C6) cycloalkyl, (C3-C6) halocycloalkyl, (C1-C4) alkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkenoxy, (C1-C4 ) Alkylsulfanyl, (C3-C6) halocycloalkylsulfanyl, (C1-C4) Alkylsulfinyl, (C1-C4) Haloalkylsulfinyl, (C3-C6) Cycloalkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1-C4) Haloalkylsulfonyl, (C3-C6) Cycloalkylsulfonyl, (C1-C4) Haloalkylsulfanyl, (C3C6) cycloalkylsulfanyl, (C1-C4) alkylcarbonyl, (C1-C4) haloalkylcarbonyl, bis (C1-C4) alkylamino, di- (C1-C4) haloalkylamino, R1 for (C1-C4) alkyl, (C1-C4 ) Haloalkyl, (C 1 -C 4) hydroxyalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) -alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -halogenoalkenyl, (C 2 -C 4) -alkynyl, (C 2 -C 4) Alkynyloxy (C1-C4) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C4) alkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (C1-C4) alkyl - (C3-C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, cyano (C3-C6) cycloalkyl, (C2-C4) alkynyl- (C3-C6) cycloalkyl, (C 1 -C 4) alkoxy- (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxycarbonyl- (C 3 -C 6) -cycloalkyl, (C 1 -C 4) -alkylthio (C 1 -C 6) -alkyl, (C 1 -C 4) -alkylcarbonyl - (C1-C6) alkyl, (C1-C4) alkoxycarbonyl (C1-C6) alkyl or (C1-C4) alkoxy, or represents in each case optionally mono- or polysubstituted by identical or different aryl, hetaryl or heterocyclyl (C1 C4) alkyl, (C3-C6) cycloalkyl, where aryl, hetaryl or heterocyclyl in each case optionally simply o which is the same or different halogen, cyano, nitro, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (Cl -C4) alkylthio or (C1-C6) alkoxycarbonyl, or is in each case optionally mono- or polysubstituted, identically or differently substituted aryl, hetaryl, heterocyclyl or oxo-heterocyclyl, where the substituents are selected from halogen, cyano, nitro, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -halogenoalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -halogenoalkylthio, (C1-C6) alkoxycarbonyl,  R 2 is hydrogen, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylcarbonyl, (C 3 -C 6) cycloalkylcarbonyl or (C 1 -C 4) alkoxycarbonyl, R 3 is hydrogen , (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylcarbonyl, (C 3 -C 6) cycloalkylcarbonyl or (C 1 -C 4) alkoxycarbonyl, R 4 represents (C 1 -C 6) ) Alkyl, (C1-C6) haloalkyl, (C1-C6) cyanoalkyl, (C1-C4) hydroxyalkyl, (C1-C4) alkoxy- (C1-C4) alkyl, (C1-C4) haloalkoxy- (C1-C4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkenyloxy (C 1 -C 4) alkyl, (C 2 -C 4) haloalkenyloxy (C 1 -C 4) alkyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl , (C2-C4) alkynyl, (C2-C4) alkynyloxy- (C1-C4) alkyl, (C2-C6) haloalkynyl, (C2-C6) cyanoalkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (C1-C4) alkyl, cyano (C3-C6) cycloalkyl- (C1-C4) alkyl, halo (C3-C6) cycloalkyl- (C1-C4) alkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl (C1-C4) alkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (C1-C4) alkyl- (C3-C6) cycloalkyl, (C1-C4) haloalkyl- (C3-C6) cycloalkyl, Halogen (C3-C6) cycloalkyl, cyano (C3- C6) cycloalkyl, (C2-C4) alkynyl- (C3-C6) cycloalkyl, (C1-C4) alkoxy- (C3-C6) cycloalkyl, (C1-C4) alkoxycarbonyl- (C3-C6) cycloalkyl, carbamoyl- (C3 -C6) cycloalkyl, thiocarbamoyl- (C3-C6) cycloalkyl, (C1-C4) alkylcarbonyl- (C1-C4) alkyl, (C1-C4) alkoxycarbonyl- (C1-C4) alkyl, amino, (C1-C4) alkylamino , Di (C1-C4) alkylamino, (C3-C6) cycloalkylamino, N- (C1-C4) alkyl- (C3-C6) cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, N- (C1-C4) alkyl- Benzylamino, N- (C 1 -C 4) alkyl-cyanobenzylamino, N- (C 1 -C 4) -alkyl-nitrobenzylamino, (C 1 -C 4) -alkylcarbonyl-amino, (C 3 -C 6) -cycloalkylcarbonylamino, hydroxy, (C 1 -C 4) -alkoxy, ( C3-C6) Cycloalkoxy, (C3-C6) Cycloalkyl (C1-C4) Alkoxy, cyano (C1-C4) Alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, (C1-C4) Alkylimino, (C3-C6) Cycloalkylimino, benzylimino, cyanobenzylimino, halobenzylimino, (C1-C4) Haloalkylbenzylimino, halogeno [(C1- C4) Haloalkyl] benzylimino, nitrobenzylimino, (C1-C4) Alkylsulfonyl (C1-C4) alkyl, (C1- C4) Alkylcarbonyl, (C1-C4) Haloalkylcarbonyl, (C3-C6) Cycloalkylcarbonyl or (C3- C6) Cycloalkyl (C1-C4) Alkyl-carbonyl, or represents in each case optionally mono- or disubstituted by identical or different substituents aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocycyl (C1-C4) Alkyl, (C1-C4) Haloalkyl, (C2-C4) Alkenyl, (C3-C6) Cycloalkyl, oxy, amino, N- (C1-C4) Is alkylamino, N-cyclo-propylamino or carbonyl, where aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxo-hetaryl, heterocyclyl or oxo-heterocycyl, in each case optionally monosubstituted or polysubstituted, identically or differently by halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, aminosulfonyl, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) Alkoxy, (C1-C4) Haloalkyl, (C1-C4) Haloalkoxy, (C1-C4) Alkylthio, (C1-C4) Haloalkylthio, (C1-C4) Alkylsulfinyl, (C1-C4) Alkylsulfonyl, (C1- C4) Haloalkylsulfinyl, (C1-C4) Haloalkylsulfonyl, (C1-C4) Alkoxycarbonyl, (C1-  C4) alkylcarbonyl, hetaryl, alkyl-hetaryl, heterocyclyl or oxo-heterocyclyl may be substituted, or for each optionally mono- or polysubstituted by identical or different substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl , Oxo-hetaryl, heterocyclyl or oxo-heterocyclyl, wherein the substituents are selected from halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C 1 -C 4) alkyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) ) Alkoxy, (C1-C4) haloalkyl, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) haloalkylthio, (C1-C4 ) Alkylsulfinyl, (C 1 -C 4 ) Alkylsulfonyl, (C1-C4) haloalkylsulfinyl, (C1- C4) Haloalkylsulfonyl, (C1-C4) Alkoxycarbonyl, (C1-C4) Alkylcarbonyl, (C3-C6) Trialkylsilyl, or R3 and R4 together for (C2-C5) -Alkyl or for (C2-C5) Alkenyl, with a 3-6 membered, optionally substituted by halogen, cyano, (C1-C4) Alkyl, (C3-C6) Cycloalkyl, (C1-C4) -Alkoxy, (C1- C4) Haloalkyl, (C1-C4) Haloalkoxy, or (C1-C4Haloalkylthio substituted ring is formed, which may optionally contain one to two double bonds, R5, R6 independently of one another are hydrogen, cyano, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl or trifluoromethoxy, V1 is oxygen or sulfur, V2 is oxygen, Sulfur or -NH stands. 4. Compounds of general formula (I) according to claim 1, 2 or 3, in which Q1 is in each case optionally monosubstituted or polysubstituted by identical or different substituents, phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl , Pyridyl, thienyl or pyrazol-1-yl or pyrazol-2-yl, wherein the substituents are selected from cyano, fluorine, chlorine, bromine, iodine, SF5, Methyl, ethyl, n -propyl, i -propyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoroisopropyl, fluorocyclopropyl, difluorocyclopropyl, tetrafluorocyclopropyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy , pentafluoroethoxy, tetrafluoroethoxy, trifluoroethoxy, Chlortetrafluorethoxy, Dichlortrifluorethoxy, Trichlordifluorethoxy, Chlortrifluorethoxy, Chlordifluorethoxy, Trifluorethenoxy, trifluoromethylsulphonyl, difluoromethylsulphonyl, trifluoromethylsulphinyl, trifluoromethylsulphanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Pentafluorethylsulfanyl, Trifluorethylsulfanyl, Difluorethylsulfanyl, pentafluoroethylsulfonyl, Tetrafluorethylsulfonyl,  Trifluoroethylsulfonyl, difluoroethylsulfonyl, pentafluoroethylsulfinyl, tetrafluoroethylsulfinyl, trifluoroethylsulfinyl, difluoroethylsulfinyl, tetrafluoroethylsulfanyl, cyclopropylsulfanyl, trifluoromethylcyclopropyl, trifluoromethylcarbonyl, bis-trifluoromethylamino, (trifluorovinyl) oxy, heptafluoropropoxy or hexafluoropropoxy R 1 is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, Methyl-cyclo-propyl, cyclo-propyl-methyl, cyano-cyclo-propyl, chloro-cyclo-propyl, fluoro-cyclo-propyl, trifluoromethyl-cyclo-propyl, cyclo-propyl-cyclo-propyl, methoxymethyl, methoxyethyl, n- Butyl, i-butyl, tert-butyl, cyclo-butyl, difluorocyclobutyl, cyclo-pentyl, fluoromethyl, difluoromethyl, trifluoromethyl or trifluoroethyl, or is monosubstituted by phenyl methyl, ethyl, i-propyl or cyclo-propyl, wherein Each optionally optionally mono- or disubstituted by phenyl, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, meth oxy, trifluoromethoxy may be substituted, or in each case optionally mono- or disubstituted by identical or different fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, trifluoromethyl, methoxy, trifluoromethoxy substituted phenyl, pyridyl, oxazolyl, thiazolyl, thienyl, oxetanyl or thietanyl, R 2 is hydrogen, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo Butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, cyclo-propylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl or i-propoxycarbonyl R3 is hydrogen, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, methoxy, ethoxy, n-propyloxy, i-propyloxy , n-butyloxy, i-butyloxy, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, cyclopropylcarbonyl, methyloxycarbonyl, ethyloxycarbonyl, n- Propyloxycarbonyl or i-propyloxycarbonyl, R4 is methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, difluoroethyl, Trifluoroethyl, pentafluoroethyl, trifluoropropyl, pentafluoropropyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, cyanohexyl, methyloxymethyl, ethyloxymethyl, methyloxyethyl, ethyloxyethyl, methyloxypropyl, ethyloxypropyl, propynyl, butynyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclo- Hexyl, cyclo-propyl-methyl, cyclo-butyl-methyl, cyclo-pentyl-methyl, cyclo-hexyl-methyl, cyclo-propyl-ethyl, cyclo-butyl-ethyl, cyclo-pentyl-ethyl, cyclo-hexyl-ethyl, Cyano-cyclo-propyl-methyl, cyano-cyclo-butyl-methyl, cyano-cyclo-pentyl-methyl, cyano-cyclo-hexyl-methyl, trifluoromethyl-cyclo-propyl-methyl, trifluoromethyl-cyclo-hexyl-methyl, cyclo-  Propylcyclopropyl, methylcyclopropyl, ethylcyclopropyl, trifluoromethylcyclopropyl, trifluoromethylcyclobutyl, trifluoromethylcyclopentyl, trifluoromethylcyclohexyl, fluorocyclopropyl, difluoro- cyclopropyl, tetrafluoro-cyclo-propyl, cyano-cyclo-propyl, cyano-cyclo-butyl, cyano-cyclo-pentyl, cyano-cyclo-hexyl, ethynyl-cyclo-propyl, methyloxy-cyclo-propyl, ethyloxy-cyclo Propyl, methyloxycarbonylcyclopropyl, ethyloxycarbonylcyclopropyl, thiocarbamoylcyclopropyl, methyloxycarbonylmethyl, ethyloxycarbonylmethyl, methyloxycarbonylethyl, ethyloxycarbonylethyl, methylamino, ethylamino, n-propylamino, isopropylamino, cyclopropylamino, cyclobutylamino, cyclopropylamino Pentylamino, cyclohexylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, di-methylamino, N-methylethylamino, N-methyl-n-propylamino, N-methylisopropylamino, N-methylcyclopropylamino, N-methylcyclo- Butylamino, N-methyl-cyclo-pentylamino, N-methyl-cyclo-hexylamino, N-methyl-benzylamino, N-methyl-cyanobenzy lamino, N-methyl-nitrobenzylamino, methoxy, ethoxy, n-propyloxy, iso-propyloxy, cyclopropyloxy, cyclopropylmethyloxy, cyclobutyloxy, cyclo-pentyloxy, cyclohexyloxy, cyanomethyloxy, cyanoethyloxy, cyanopropyloxy, cyanobutyloxy, Benzyloxy, cyanobenzyloxy, nitrobenzyloxy, methylimino, ethylimino, n -propylimino, iso -propylimino, iso -butylimino, cyclo-pentylimino, cyclohexylimino, benzylimino, cyanobenzylimino, nitrobenzylimino, fluorobenzylimino, chlorobenzylimino, trifluoromethylbenzylimino, chloro (trifluoromethyl) benzylimino, fluoro (Trifluoromethyl) benzylimino, methylsulfonylmethyl, methylsulfonylethyl, methylsulfonylpropyl, methylsulfonylbutyl, methylcarbonyl, ethylcarbonyl, propylcarbonyl, isopropylphenyl, cyclopropylcarbonyl, cyclopropylmethylcarbonyl, cyclo-butylmethylcarbonyl, butylcarbonyl, isobutylcarbonyl, tert-butylcarbonyl, cyclo-butylcarbonyl, cyclo-pentylcarbonyl, cyclohexylcarbonyl or trifluoromethylcarbonyl, or simply by phenyl, pyridyl, pyri midyl, furanyl, thiophenyl, oxazolyl, thiazolyl, indolyl, azaindolyl, indazolyl, azaindazolyl, 1,3-benzodioxolyl or 2,3-dihydro-1,4-benzodioxinyl substituted methyl, ethyl, n -propyl, i- Propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, cyclo-pentyl, cyclo-hexyl, oxy, amino, N-methylamino, N-ethylamino or carbonyl, wherein phenyl, pyridyl , Pyrimidyl, furanyl, thiophenyl, oxazolyl, thiazolyl, indolyl, aza-indolyl, indazolyl, aza-indazolyl, 1,3-benzodioxolyl in each case optionally mono- or polysubstituted, identically or differently, by cyano, fluorine, chlorine, bromine, iodine, nitro, Methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, pentafluoroethoxy, trifluoromethylthio, methyloxycarbonyl, ethyloxycarbonyl, carbamoyl, thiocarbamoyl, aminosulfonyl, pyrazolyl, imidazolyl, methylpyrazolyl, oxazolyl, oxdiazolyl, thiazolyl, Pyrrolyl, pyrrolidinyl or pyrrolidinonyl, or for each gege optionally monosubstituted or disubstituted by identical or different substituents, phenyl, pyridyl, pyrimidyl, thiophenyl, indazolyl, aza-indazolyl, 1,3-benzodioxolyl, oxetanyl,  Thietanyl, tetrahydrofuranyl, oxotetrahydrofuranyl, tetrahydrothiophenyl, oxidotetrahydrothiophenyl, dioxotetrahydrothiophenyl, tetrahydro-2H-pyranyl, oxotetrahydro-2H-pyranyl, tetrahydro-2H-thiopyranyl, oxotetrahydro-2H-thiopyranyl, 2,3-dihydro-1H-indenyl, wherein the substituents are selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, trifluoromethylthio, methyloxycarbonyl or ethyloxycarbonyl, or R3 and R4 together for (C3- C5) alkyl to form a 4-6 membered ring optionally substituted by halo, cyano, trifluoromethyl or trifluoromethoxy; R5, R6 independently represent hydrogen, cyano, fluoro, chloro, bromo, methyl, ethyl, difluoromethyl, trifluoromethyl or trifluoromethoxy, V1 is oxygen or sulfur, V2 is oxygen, sulfur or -NH. 5. Compounds of general formula (I) according to one of claims 1 to 4, in which Q1 is in each case optionally monosubstituted, disubstituted, trisubstituted or trisubstituted by identical or different substituents, phenyl, 1,3-benzodioxolyl, 2,3-dihydro-1 , 4-benzodioxinyl, pyridyl, thienyl or pyrazol-1-yl or pyrazol-2-yl, wherein the substituents are selected from fluorine, chlorine, bromine, iodine, SF5, Methyl, ethyl, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoroisopropyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, tetrafluoroethoxy, Chlortrifluorethoxy, Trifluorethenoxy, trifluoromethylsulfonyl, trifluoromethylsulfinyl, trifluoromethylsulphanyl, Difluormethylsulfinyl, Difluormethylsulfanyl, Trifluormethylcyclopropyl, bis-trifluoromethylamino, Tetrafluorethylsulfanyl , Cyclopropylsulfanyl, (trifluorovinyl) oxy or hexafluoropropoxy R 1 is methyl, ethyl, i-propyl, cyclopropyl, methylcyclopropyl, cyclopropylmethyl, cyanocyclopropyl, chloro-cyclopropyl, cyclopropyl -cyclo-propyl, methoxyethyl, tert-butyl, cyclo-butyl, difluorocyclobutyl, cyclo-pentyl, trifluoroethyl or trifluoromethyl-cyclo-propyl, or represents methyl which is monosubstituted by phenyl, where phenyl is optionally monosubstituted by chlorine, bromine, nitro , Trifluoromethyl may be substituted, or optionally simply by dur ch is chlorine-substituted phenyl or pyridyl or is oxazolyl,  R 2 is hydrogen, methyl, ethyl, cyclopropylcarbonyl or methoxycarbonyl, R 3 is hydrogen, methyl, methoxy or methoxycarbonyl, R 4 is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, Butyl, cyclo-butyl, trifluoroethyl, trifluoropropyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, methyloxyethyl, propynyl, butynyl, cyclo-propyl, cyclo-butyl, cyclo-pentyl, cyclo-hexyl, cyclopropyl-methyl, cyclo- Butyl-methyl, cyclo-pentyl-methyl, cyclo-hexyl-methyl, cyclo-propyl-ethyl, cyano-cyclo-hexyl-methyl, trifluoromethyl-cyclo-hexyl-methyl, cyclo-propyl-cyclo-propyl, methyl-cyclo Propyl, trifluoromethyl-cyclo-propyl, trifluoromethyl-cyclo-hexyl, difluoro-cyclo-propyl, cyano-cyclo-propyl, cyano-cyclo-butyl, cyano-cyclo-hexyl, ethynyl-cyclo-propyl, methyloxy-cyclo-propyl, Methyloxycarbonylcyclopropyl, thiocarbamoylcyclopropyl, methyloxycarbonylethyl, cyanobenzylimino, fluoro (trifluoromethyl) benzylimino, methylsulfonylbutyl, methoxy, ethoxy, cyclopropyl Propylmethyloxy, iso-propyloxy, Cyanpropyloxy, Cyanphenyloxy, cyclo-Propylcarbonyl, or is phenyl, pyridyl, indazolyl, aza-indazolyl, thiophenyl or 1,3-benzodioxolyl substituted methyl, ethyl, n-propyl, cyclo-propyl or carbonyl, where phenyl, pyridyl, indazolyl, aza-indazolyl, thiophenyl or 1,3-benzodioxolyl are each optionally mono-, di- or trisubstituted, identically or differently, by cyano, fluorine, chlorine, nitro, methyl, trifluoromethyl, methoxy, methyloxycarbonyl, Thiocarbamoyl, aminosulfonyl, methylpyrazolyl, oxazolyl, oxadiazolyl or pyrrolidinonyl, or for each optionally monosubstituted phenyl, pyridyl, indazolyl, oxetanyl, thietanyl, tetrahydrofuranyl, oxotetrahydrofuranyl, Dioxidotetrahydrothiophenyl, tetrahydro-2H-pyranyl or 2,3-dihydro-1H -indenyl, where the substituents are selected from chloro, cyano, methyl or methyloxycarbonyl, or R3 and R4 together for (C3-C5) -alkyl s to form a 4-6 membered ring optionally substituted by cyano, R5, R6 are independently hydrogen, V1 is oxygen or sulfur, V2 is oxygen, sulfur or -NH. 6. Compounds of the general formula (I) according to one of claims 1 to 5, in which Q1 is 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl, 2,2 Difluoro-1,3-benzodioxol-5-yl, 2-  Chloro-4- (trifluoromethoxy) phenyl, 2-ethyl-6-methyl-4- (pentafluoroethyl) phenyl, 2-fluoro-4- (trifluoromethoxy) phenyl, 2-fluoro-6- (trifluoromethyl) pyridin-3-yl, 2-methyl-4- (trifluoromethoxy) phenyl, 3- (pentafluoroethyl) -1H-pyrazol-1-yl, 3- (trifluoromethoxy) phenyl, 3,5-difluoro-4- (trifluoromethoxy) phenyl, 3-chloro-4 - (trifluoromethoxy) phenyl, 3-chloro-5- (trifluoromethyl) pyridin-2-yl, 3-fluoro-4- (pentafluoroethyl) phenyl, 3-fluoro-4- (trifluoromethoxy) phenyl, 3-fluoro-4- ( trifluoromethyl) phenyl, 3-methyl-4- (trifluoromethoxy) phenyl, 4- (1,1,1,2,3,3,3-heptafluoropropan-2-yl) phenyl, 4- (1,1,2,2 Tetrafluoroethoxy) phenyl, 4- (1,1-difluoroethyl) phenyl, 4- (2,2,2-trifluoroethyl) phenyl, 4- (2-chloro-1,1,2-trifluoroethoxy) phenyl, 4- (cyclopropylsulfanyl ) phenyl, 4- (difluoromethoxy) -3,5-difluorophenyl, 4- (difluoromethoxy) phenyl, 4- (difluoromethyl) -3-fluorophenyl, 4- (pentafluoroethoxy) phenyl, 4- (pentafluoroethyl) phenyl, 4-SF5- phenyl, 4- (trifluoromethoxy) phenyl, 4- (trifluoromethyl) phenyl, 4- [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenyl, 4 - [(Dif luormethyl) sulfanyl] phenyl, 4- [(difluoromethyl) sulfinyl] phenyl, 4 - [(trifluoromethyl) sulfanyl] phenyl, 4- [(trifluoromethyl) sulfinyl] phenyl, 4 - [(trifluoromethyl) sulfonyl] phenyl, 4- [( Trifluorovinyl) oxy] phenyl, 4- [1- (trifluoromethyl) cyclopropyl] phenyl, 4- [bis (trifluoromethyl) amino] phenyl, 4- [chloro (difluoro) methoxy] phenyl, 4-bromophenyl, 4-chlorophenyl, 4- Fluorophenyl, 4-iodophenyl, 5- (trifluoromethyl) -2-thienyl, 5- (trifluoromethyl) pyridin-2-yl, 6- (trifluoromethyl) pyridin-3-yl, 4-bromo-3-fluorophenyl, 4- (1 , 1,2,3,3,3-hexafluoropropoxy) phenyl, 2,6-dichloro-4- (pentafluoroethyl) phenyl, 2-chloro-3-fluoro-4- (pentafluoroethyl) phenyl, 3-fluoro-5-methyl -4- (pentafluoroethyl) phenyl, 2,6-difluoro-4- (pentafluoroethyl) phenyl, 2-chloro-5-fluoro-4- (pentafluoroethyl) phenyl, 3-methyl-4- (pentafluoroethyl) phenyl, 3.5 Difluoro-4- (pentafluoroethyl) phenyl, 2,3-difluoro-4- (pentafluoroethyl) phenyl, 3-chloro-4- (pentafluoroethyl) phenyl, 2,3,5-trifluoro-4- (pentafluoroethyl) phenyl, 2 , 5-Difluoro-4- (pentafluoroethyl) phenyl, 2,6-dichloro-3-fluoro-4- (pen tafluoroethyl) phenyl or 3-chloro-5-fluoro-4- (pentafluoroethyl) phenyl, R 1 is cyclobutyl, cyclopentyl, cyclopropyl, cyclopropylmethyl, ethyl, isopropyl, methyl, tert-butyl, 1,3-oxazol-5-yl, 1-Chlorocyclopropyl, 1-Cyancyclopropyl, 1-cyclopropylcyclopropyl, 1-methoxyethyl, 1-methylcyclopropyl, 2-chlorophenyl, 3,3-difluorocyclobutyl, 4- (trifluoromethyl) benzyl, 4-bromobenzyl, 4-chlorophenyl, 4-nitrobenzyl , 2,2,2-trifluoroethyl, 1- (trifluoromethyl) cyclopropyl or 6-chloropyridin-3-yl, R 2 is hydrogen, methyl, ethyl, cyclopropylcarbonyl or methoxycarbonyl, R 3 is hydrogen, methyl, methoxy or methoxycarbonyl, R 4 for (1-methyl-1H-indazol-7-yl) methyl, (1-methyl-1H-pyrazolo [3,4-b] pyridin-5-yl) methyl, (1S) -1- [4- (trifluoromethyl ) phenyl] ethyl, (1S) -1- [4- (trifluoromethyl) phenyl] ethyl, (2,2-difluoro-1,3-benzodioxol-5-yl) methyl, (4-cyanocyclohexyl) methyl, (5- Cyanopyridin-2-yl) methyl, (6  Chloropyridin-3-yl) methyl, (6-cyanopyridin-3-yl) methyl, (trans-4-cyanocyclohexyl) methyl, [cis-4- (trifluoromethyl) cyclohexyl] methyl, 1- (4-cyanophenyl) cyclopropyl, 1 (4-cyanophenyl) ethyl, 1- (4-nitrophenyl) cyclopropyl, 1- (4-nitrophenyl) ethyl, 1- (methoxycarbonyl) cyclopropyl, 1- (trifluoromethyl) cyclopropyl, 1,1-dioxotetrahydrothiophene-3-yl, 1- [4- (trifluoromethyl) phenyl] ethyl, 1-thiocarbamoylcyclopropyl, 1-cyancyclobutyl, 1-cyancyclopropyl, 1-cyanoethyl, 1-cyclopropylcyclopropyl, 1-cyclopropylethyl, 1-ethynylcyclopropyl, 1-methoxycarbonylethyl, 1-methoxycyclopropyl, 1-methylcyclopropyl, 2- (3-cyanophenyl) ethyl, 2- (4-cyanophenyl) ethyl, 2,2,2-trifluoroethyl, 2,2-difluorocyclopropyl, 2,4-dichloro-5-fluorobenzyl, 2,4- Dichlorobenzyl, 2-cyanopropan-2-yl, 2-fluoro-4- (trifluoromethyl) benzyl, 2-fluoro-4-nitrobenzyl, 2-methoxyethyl, 2-oxotetrahydrofuran-3-yl, 3- (methoxycarbonyl) oxetan-3 yl, 3,3,3-trifluoropropyl, 3- [4- (trifluoromethyl) phenyl] propyl, 3-chlorobenzyl, 3-cyanobenzyl, 3-cyanopentan-3-yl, 3-fluoro-4- (tri fluoromethyl) benzyl, 3-fluorobenzyl, 3-methylthietan-3-yl, 4- (1,2,4-oxadiazol-3-yl) benzyl, 4- (1,3,4-oxadiazol-2-yl) benzyl, 4- (1,3-oxazol-5-yl) benzyl, 4- (1-methyl-1H-pyrazol-3-yl) benzyl, 4- (1-methyl-1H-pyrazol-5-yl) benzyl, 4 - (methoxycarbonyl) benzyl, 4- (trifluoromethyl) benzyl, 4-thiocarbamoylbenzyl, 4-chloro-2-fluorobenzyl, 4-chloro-3-fluorobenzyl, 4-chlorobenzyl, 4-chlorophenyl, 4-cyano-2,5-difluorobenzyl , 4-cyano-2,6-difluorobenzyl, 4-cyano-2-fluorobenzyl, 4-cyano-3,5-difluorobenzyl, 4-cyano-3-fluorobenzyl, 4-cyanobenzyl, 4-cyano-butyl, 4-cyano-cyclohexyl, 4 Cyanophenyl, 4-cyantetrahydro-2H-pyran-4-yl, 4-fluoro-3- (trifluoromethyl) benzyl, 4-methoxybenzyl, 4-nitrobenzyl, 4-aminosulfonylbenzyl, 5-cyano-1H-indazol-3-yl, 5-cyano-2,3-dihydro-1H-inden-1-yl, 5-cyanopentyl, benzyl, but-3-yn-2-yl, n-butyl, cis-4- (trifluoromethyl) cyclohexyl, cyanomethyl, cyclobutyl , Cyclobutylmethyl, cyclohexyl, cyclohexylmethyl, cyclopentyl, cyclopentylmethyl, cyclopropyl, cyclopropylmethyl, ethyl, isobutyl, isopropyl, methyl, oxetane 3-yl, prop-2-yn-1-yl, n-propyl, pyridin-2-ylmethyl, pyridin-3-yl, thietan-3-yl, trans-4- (trifluoromethyl) cyclohexyl, (5-nitro) 2-thienyl) methyl, (5-cyano-2-thienyl) methyl, 4-cyanobenzylimine, 3-fluoro-4- (trifluoromethyl) benzylimine, [4- (2-oxopyrrolidin-1-yl) phenyl] methyl, 2 Methyl-1-methylsulfonylpropan-2-yl, (pyridin-4-yl) methyl, methoxy, ethoxy, cyclopropylmethyloxy, isopropyloxy, 3-cyanopropyloxy, 4-cyanophenyloxy, cyclopropylcarbonyl or 4-nitrobenzoyl, or R3 and R4 together for one of following rings are:
))
R5, R v6 unabhängig voneinander für Wasserstoff stehen, V1 für Sauerstoff oder Schwefel steht, V2 für Sauerstoff, Schwefel oder -NH steht. 7. Agrochemische Formulierung enthaltend Verbindungen der allgemeinen Formel (I) und / oder deren Salze gemäß einem der Ansprüche 1 bis 6 in biologisch wirksamen Gehalten von zwischen 0,00000001 und 98 Gew.-%, bezogen auf das Gewicht der agrochemischen Formulierung, sowie Streckmittel und/oder oberflächenaktive Stoffe. 8. Agrochemische Formulierung gemäß Anspruch 7 zusätzlich enthaltend einen weiteren agrochemischen Wirkstoff. 9. Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der allgemeinen Formel (I) und / oder deren Salze gemäß einem der Ansprüche 1 bis 6 auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt, wobei Verfahren zur Behandlung des menschlichen oder tierischen Körpers ausgeschlossen sind. 10. Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 6 zur Bekämpfung von tierischen Schädlingen, wobei die Behandlung des menschlichen oder tierischen Körpers ausgeschlossen ist. 11. Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 6 zum Schutz des Vermehrungsmaterials von Pflanzen. R 5, R v 6 independently of one another represent hydrogen, V 1 represents oxygen or sulfur, V2 stands for oxygen, sulfur or -NH. 7. An agrochemical formulation comprising compounds of general formula (I) and / or salts thereof according to any one of claims 1 to 6 in biologically active contents of between 0.00000001 and 98 wt .-%, based on the weight of the agrochemical formulation, and extenders and / or surfactants. 8. Agrochemical formulation according to claim 7 additionally containing a further agrochemical active ingredient. 9. A method for controlling animal pests, which comprises allowing compounds of general formula (I) and / or salts thereof according to any one of claims 1 to 6 to act on animal pests and / or their habitat, wherein methods for the treatment of human or animal Body are excluded. 10. Use of compounds of general formula (I) according to one of claims 1 to 6 for controlling animal pests, wherein the treatment of the human or animal body is excluded. 11. Use of compounds of the general formula (I) according to one of claims 1 to 6 for the protection of the propagation material of plants.
EP17709464.6A 2016-03-16 2017-03-14 N-(cyanobenzyl)-6-(cyclopropyl-carbonylamino)-4-(phenyl)-pyridine-2-carboxamide derivatives and related compounds as pesticides and plant protection agents Withdrawn EP3429997A1 (en)

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