EP3429997A1 - Dérivés de n-(cyanobenzyl)-6-(cyclopropylcarbonylamino)-4-(phényl)-pyridine-2-carboxamide et composes apparentés utilisés comme agents phytosanitaires pesticides - Google Patents

Dérivés de n-(cyanobenzyl)-6-(cyclopropylcarbonylamino)-4-(phényl)-pyridine-2-carboxamide et composes apparentés utilisés comme agents phytosanitaires pesticides

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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Withdrawn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)
English (en)
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/fr
Withdrawn legal-status Critical Current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

La présente invention concerne de nouveaux composés de pyridine substitués, de formule (I) dans laquelle R1, R2, R3, R4, R5, R6, V1, V2 et Q1 ont la signification indiquée dans la description, ainsi que leur utilisation comme acaricides et insecticides pour lutter contre les bioagresseurs animaux, principalement les arthropodes et notamment les insectes et les arachnides. L'invention concerne également des procédés et des produits intermédiaires pour la préparation desdits composés.
EP17709464.6A 2016-03-16 2017-03-14 Dérivés de n-(cyanobenzyl)-6-(cyclopropylcarbonylamino)-4-(phényl)-pyridine-2-carboxamide et composes apparentés utilisés comme agents phytosanitaires pesticides Withdrawn EP3429997A1 (fr)

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WO2017157885A1 (fr) 2017-09-21
UY37154A (es) 2017-10-31
JP2019513700A (ja) 2019-05-30
TW201808906A (zh) 2018-03-16
US20190053492A1 (en) 2019-02-21
BR112018068681A2 (pt) 2019-01-15

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