EP3849975A1 - Heterocyclene derivatives as pest control agents - Google Patents

Heterocyclene derivatives as pest control agents

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Publication number
EP3849975A1
EP3849975A1 EP19765732.3A EP19765732A EP3849975A1 EP 3849975 A1 EP3849975 A1 EP 3849975A1 EP 19765732 A EP19765732 A EP 19765732A EP 3849975 A1 EP3849975 A1 EP 3849975A1
Authority
EP
European Patent Office
Prior art keywords
cycloalkyl
spp
alkyl
haloalkyl
formula
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Withdrawn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
EP19765732.3A
Other languages
German (de)
French (fr)
Inventor
Rüdiger Fischer
Matthieu WILLOT
Dominik HAGER
Laura HOFFMEISTER
Marc LINKA
Ulrich Görgens
Kerstin Ilg
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 AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP3849975A1 publication Critical patent/EP3849975A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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

Definitions

  • the present invention relates to heterocycle derivatives of the formula (I), their use as acaricides and / or insecticides for controlling animal pests, especially arthropods and in particular insects and arachnids, and processes and intermediates for their preparation.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects and / or improve their activity.
  • heterocycle derivatives have now been found which have advantages over the already known compounds, e.g. Examples of better biological or ecological properties, broader application methods, better insecticidal, acaricidal activity and good tolerance to useful plants are mentioned.
  • the heterocycle derivatives can be used in combination with other agents to improve the effectiveness, in particular against insects which are difficult to control.
  • the present invention therefore relates to new compounds of the formula (I) in which (configuration 1)
  • R 2 , R 3 independently of one another for hydrogen, halogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-Ce) alkoxy, (Ci-C6) haloalkoxy, (Ci-C6) haloalkylthio, (Ci C6) haloalkylsulfinyl, (Ci-C6) haloalkylsulfonyl or for (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cyanocycloalkyl, (Ci-C 6 )
  • C8 cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) halogenocycloalkyl, optionally mono- or polysubstituted by (Ci-C ö ) alkyl or halogen-substituted cyano (C 3 -C 6 ) cycloalkyl, optionally singly or multiply spiro (C3-C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl substituted with cyano or halogen or optionally (C 4 -Ci 2 ) bicycloalkyl mono- or polysubstituted with cyano or halogen, n represents 0, 1 or 2,
  • Q stands for a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1 to Q5,
  • Alkyl R 4 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci-C 4) hydroxyalkyl, (Ci C 4) alkoxy (Ci-C 4) , (Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) (4 Ci-C) alkyl Halogenalkenyloxy-, (C 2 -C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (C 4 ) alkyl, (C 2 -C 4 ) haloalkyn
  • R 5 is for (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) Haloalkynyl, (C 3 -Cs) cycloalkyl or halogen (C 3 -Cs) cycloalkyl,
  • R 6 for hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4 ) Alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 - C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl- (C 3 - C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C4) alkoxyimino, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci- C4 ) Alky
  • the compounds of the formula (1) have very good activity as pesticides, preferably as insecticides and / or acaricides, and moreover are generally very well tolerated by plants, in particular particularly against crop plants.
  • R 1 preferably represents (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 - C 6 ) haloalkynyl, (C 3 -Cs) cycloalkyl, halogen (C 3 -Cs) cycloalkyl, (C 3 - C6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6 ) cycloalkyl- (Ci-C haloalkyl 6), (Ci-C6) alkyl- (C3-Cs) cycloalkyl, (Ci-C 6) haloalkyl (C 3 -Cs) cycloalkyl, (Ci-C6) cyanoalkyl, (Ci- C6) hydroxyalkyl
  • R 2 , R 3 are preferably independently of one another hydrogen, halogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy, (Ci-C6) haloalkoxy, (Ci-C6) haloalkylthio, ( Ci-C6) haloalkylsulfmyl, (Ci-C6) haloalkylsulfonyl or for (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -Cs) cycloalkyl, (Ci C 6 ) haloalkyl- (C 3 -Cg) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) halocycloalkyl, optionally single or multiple cyano (C3-C
  • n is preferably 0, 1 or 2
  • Q preferably represents a heteroaromatic 9-membered or 12-membered anne lyated bicyclic or tricyclic ring system from the series Q1 to Q5,
  • R 4 preferably for (Ci-CQ-alkyl, (Ci-C 4 ) haloalkyl, (Ci-CQ-cyanoalkyl, (Ci-CQ hydroxy alkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy - (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) haloalkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) cyanoalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) alkynyloxy- (Ci-C 4 ) alky
  • R 5 preferably for (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C6) haloalkyl, (C 2 -
  • R 6 preferably represents hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -
  • R 1 particularly preferably represents (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C 3 -Cs) cycloalkyl
  • R 2 particularly preferably represents hydrogen, halogen, (Ci-C alkyl, (Ci-C 4) haloalkyl, (CI-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C4) haloalkylthio, (Ci-C4) haloalkylsulfinyl or (C i -C 4) haloalkylsulfonyl,
  • R 3 particularly preferably represents (Ci-C 4 ) haloalkyl- (C 3 -Cs) cycloalkyl, spiro- (C 3 -Cs) cycloalkyl- (C 3 -Cs) cycloalkyl, (C 4 -Ci 2 ) bicycloalkyl or optionally Cyano (C 3 -C 6 ) cycloalkyl substituted once or twice by (Ci-C 4 ) alkyl or halogen, n is particularly preferably 0, 1 or 2,
  • Q particularly preferably represents a heteroaromatic 9-membered or 12-membered anne lied bicyclic or tricyclic ring system from the series Q1 to Q5,
  • R 4 particularly preferably represents (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci C 4) alkoxy alkyl (Ci-C 4), (Ci-C 4 ) Haloalkoxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkynyl, (C 2 - C 4 ) alkynyloxy- (Ci-C 4 ) alkyl or (C 3 -
  • R 5 particularly preferably represents (Ci-C 6 ) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl or halogen (C 3 -C 8 ) cycloalkyl,
  • R 6 particularly preferably for hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 - C 6 ) cycloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) Haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfmyl, (Ci-C 4 ) alkylsulfonyl or (Ci-C 4 ) haloalkylsulfonyl and
  • Embodiment 4 very particularly preferably represents (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C 3 -Cs) cycloalkyl,
  • R 2 very particularly preferably represents hydrogen, (Ci-C 4 ) alkyl or halogen
  • R 3 very particularly preferably represents (Ci-C 4 ) haloalkyl- (C 3 -Cs) cycloalkyl, spiro- (C 3 - C 8 ) cycloalkyl- (C 3 -Cs) cycloalkyl or cyano (C 3 -C 6 ) cycloalkyl, n very particularly preferably represents 0, 1 or 2, Q very particularly preferably represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2, Q3 and Q5,
  • R 4 very particularly preferably represents (Ci-C 4 ) alkyl or (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl
  • R 5 very particularly preferably represents (Ci-C 6 ) haloalkyl
  • R 6 very particularly preferably represents hydrogen, methyl, ethyl, methoxy, cyano, halogen or (Ci-C2) haloalkyl and
  • R 1 stands for (Ci-CQ-alkyl
  • R 2 stands for hydrogen
  • R 3 stands for cyanocyclopropyl or cyanocyl cobutyl
  • n stands for 2
  • Q stands out for a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2 and Q5,
  • R 4 is highlighted for (Ci-CQalkyl
  • R 5 stands for (Ci-CQHalogenalkyl stands, R 6 stands for hydrogen and
  • A stands for N (nitrogen) or C (H).
  • Design 6- 1 R 1 stands especially for ethyl, R 2 stands especially for hydrogen, R 3 stands in particular for 1-cyanocyclopropyl, n stands in particular for 2,
  • Q in particular represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2 and Q5,
  • R 4 stands in particular for methyl
  • R 5 stands in particular for trifluoromethyl
  • R 6 in particular represents hydrogen
  • A is especially N (nitrogen) or C (H).
  • Design 6-2 R 1 stands in particular for ethyl
  • R 2 stands in particular for hydrogen
  • R 3 stands in particular for 1-cyanocyclopropyl
  • n stands in particular for 2
  • Q in particular represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2 and Q5, in which
  • R 4 is in particular methyl
  • R 5 is in particular trifluoromethyl or pentafluoroethyl
  • R 6 is in particular hydrogen
  • A is especially N (nitrogen) or C (H).
  • the invention comprises the following structure of formula (I-A)
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration ( 6) have the meanings described.
  • the present invention comprises the following structure of the formula (IB)
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration ( 6) have the meanings described.
  • the present invention comprises the following structure of the formula (I-C)
  • R 1 , R 2 , R 3 , R 4 , A and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration (6) to have.
  • the Bergiff formula (I) naturally also includes the formulas (I-A) to (I-C) falling under formula (I).
  • the invention relates to the compounds of the formula (I) in which n is 2 and where R 1 , R 2 , R 3 , Q, A, R 4 , R 5 and R 6 have the form ( 1) or configuration (2) or configuration (3) or configuration (4) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which
  • R 1 is (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C3-Cs) cycloalkyl and R 2 , R 3 , Q, A, R 4 , R 5 , R 6 and n are in the embodiment (1) or configuration (2) or configuration (5) or configuration (6) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which
  • R 1 stands for (Ci-C alkyl and R 2 , R 3 , Q, A, R 4 , R 5 , R 6 and n are those in embodiment (1) or embodiment (2) or embodiment (3) or embodiment (4th ) or configuration (6) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which R 1 stands for ethyl and R 2 , R 3 , Q, A, R 4 , R 5 , R 6 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration ( 5) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which at least one of the radicals R 2 or R 3 is cyano (C3-C6) cycloalkyl, preferably l-cyanocyclopropyl and the other radical is selected from hydrogen, (Ci-C4) alkyl or halogen and R 1 , Q, A, R 4 , R 5 , R 6 and n which are in the configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6) have meanings described.
  • the radicals R 2 or R 3 is cyano (C3-C6) cycloalkyl, preferably l-cyanocyclopropyl and the other radical is selected from hydrogen, (Ci-C4) alkyl or halogen and R 1 , Q, A, R 4 , R 5 , R 6 and n which are in the configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6) have meanings described.
  • the invention relates to the compounds of the formula (I) in which
  • R 2 represents hydrogen, (Ci-C4) alkyl or halogen and R 1 , R 3 , Q, A, R 4 , R 5 , R 6 and n are those in embodiment (1) or embodiment (2) or embodiment (3 ) or configuration (5) or configuration (6) meanings described.
  • the invention relates to the compounds of the formula (I) in which
  • R 2 stands for hydrogen and R 1 , R 3 , Q, A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) .
  • the invention relates to the compounds of the formula (I) in which
  • R 3 represents (Ci-C4) haloalkyl- (C3-C8) cycloalkyl, spiro- (C3-C8) cycloalkyl- (C3-Cs) cycloalkyl or cyano (C3-C6) cycloalkyl, and R 1 , R 2 , Q , A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6).
  • the invention relates to the compounds of the formula (I) in which
  • R 3 represents cyano (C3-C6) cycloal yl and R 1 , R 2 , Q, A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (6) .
  • the invention relates to the compounds of the formula (I) in which R 3 is 1-cyanocyclopropyl and R 1 , R 2 , Q, A, R 4 , R 5 , R 6 and n are those in Design (1) or design (2) or design (3) or design (4) or design (5) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is 1-cyanocyclopropyl and R 1 , Q, A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration (6).
  • the invention relates to the compounds of the formula (I) in which Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1 to Q5,
  • R 1 , R 2 , R 3 , A, R 4 , R 5 , R 6 and n have the meanings described in configuration (4) or configuration (5) or configuration (6).
  • the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered anne lyzed bicyclic or tricyclic ring system from the series Q 1, Q2, Q3 and Q5,
  • Q5 and R 1 , R 2 , R 3 , A, R 4 , R 5 , R 6 and n are those described in configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6) Have meanings.
  • the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5, and R 1 , R 2 , R 3 , A, R 4 , R 5 , R 6 and n in the configuration (1) or configuration (2) or configuration
  • the invention relates to the compounds of the formula (I) in which
  • R 5 represents (Ci-C 6 ) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl or halogen (C3-Cs) cycloalkyl, and Q, R 1 , R 2 , R 3 R 4 , R 6 , A and n in the configuration (1) or configuration (2) or configuration
  • the invention relates to the compounds of the formula (I) in which
  • R 5 stands for (Ci-C 6 ) haloalkyl, preferably for (Ci-C4) haloalkyl
  • Q, R 1 , R 2 , R 3 R 4 , R 6 , A and n are those in embodiment (1) or embodiment ( 2) or configuration (3) or configuration (4) or configuration (5) or configuration (6) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which R 4 represents (Ci-C4) alkyl or (Ci-C4) alkoxy- (Ci-C4) alkyl,
  • R 5 represents (Ci-C 6 ) haloalkyl
  • R 6 represents hydrogen, methyl, ethyl, methoxy, cyano, halogen or (Ci-C2) haloalkyl and A represents N (nitrogen) or C (H), and Q, R 1 , R 2 , R 3 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6).
  • the invention relates to the compounds of the formula (I) in which
  • R 4 represents (Ci-C4) alkyl
  • R 5 represents (Ci-C4) haloalkyl
  • R 6 represents hydrogen
  • R 1 , R 2 , R 3 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (6) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5, where
  • R 4 represents (Ci-C alkyl or (Ci-C4) alkoxy- (Ci-C4) alkyl
  • R 5 represents (Ci-C 6 ) haloalkyl
  • R 6 represents hydrogen, methyl, ethyl, methoxy, cyano, halogen or (Ci-C2) haloalkyl and A represents N (nitrogen) or C (H), and R 1 , R 2 , R 3 and n are in the embodiment (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6) have the meanings described.
  • the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5, in which
  • R 4 represents (Ci-C4) alkyl
  • R 5 represents (Ci-C4) haloalkyl
  • R 6 represents hydrogen
  • R 1 , R 2 , R 3 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (6) have the meanings described.
  • Halogen selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine.
  • alkyl either alone or in combination with other terms, such as haloalkyl, in the context of the present invention means a residue of a saturated, aliphatic hydrocarbon group with 1 to 12 carbon atoms, which can be branched or unbranched.
  • Ci-Ci2-alkyl radicals are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert.
  • Ci-CValkyl radicals are particularly preferred.
  • Ci-C4-alkyl radicals are particularly preferred.
  • alkenyl is a linear or branched C2-Ci2-alkenyl radical which has 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, understood.
  • C2-C6 alkenyl radicals are preferred, and C2-C4 alkenyl radicals are particularly preferred.
  • alkynyl is a linear or branched C2-Ci2-alkynyl radical which has at least one triple bond, for example ethynyl, 1-propynyl and propargyl, understood.
  • C3-C6-alkynyl radicals and are preferred C3-C4-alkynyl radicals are particularly preferred.
  • the alkynyl radical can also have at least one double bond.
  • cycloalkyl either alone or in combination with other terms, is understood according to the invention to mean a C3-C8 cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl . Of these, C3-C6-cycloalkyl radicals are preferred.
  • the term “bicycloalkyl”, either alone or in combination with other terms, is understood according to the invention to mean a bicyclus, the two rings of which have a common single bond.
  • the two cycles can have the same or a different number of carbon atoms.
  • Bicyclo [l.l.0] butane or Bicyclo [2. l.0] pentane is understood according to the invention to mean a bicyclus, the two rings of which have a common single bond.
  • the two cycles can have the same or a different number of carbon atoms.
  • Bicyclo [l.l.0] butane or Bicyclo [2. l.0] pentane for example, its called Bicyclo [l.l.0] butane or Bicyclo [2. l.0] pentane.
  • spiro-cycloalkyl-cycloalkyl is understood according to the invention to mean a compound in which two cycloalkyl rings are connected via a common carbon atom. The two cycles can have the same or a different number of carbon atoms. For example, its called spiro [2.2] pentane (spiro- (cyclopropyl) - (cyclopropyl)) or spiro [2.3] hexane (spiro- (cyclopropyl) - (cyclobutyl)).
  • alkoxy either alone or in combination with other terms, such as, for example, haloalkoxy, is understood here to mean an O-alkyl radical, the term “alkyl” having the meaning given above.
  • Halogen represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • optionally substituted radicals can be mono- or polysubstituted, in the case of multiple substitutions the substituents can be the same or different.
  • the compounds of the formula (I) can be present in different compositions as geometric and / or as optically active isomers or corresponding isomer mixtures.
  • These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus includes pure stereo isomers as well as any mixtures of these isomers.
  • the compounds of formula (I) can also be present as salts, in particular acid addition salts and metal salt complexes.
  • the compounds of formula (I) and their acid addition salts and metal salt complexes have good activity, in particular for combating animal pests.
  • Suitable non-toxic salts of the compounds of the general formula (I) which can be mentioned are customary non-toxic salts, ie salts with corresponding bases and salts with added acids.
  • radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n have the meanings described above, A 2 and A 3 represent CH or N and X 1 represents halogen.
  • the compounds of the formula (IV) can be prepared analogously to the process described in US5576335 by reacting compounds of the formula (II) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base.
  • Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible manufacturing routes are described in methods D and E.
  • the reaction of the compounds of formula (II) with carboxylic acids of formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane are preferred; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • Suitable bases are inorganic bases which are usually used in such reactions.
  • Bases which are selected by way of example from the group consisting of acetates, phosphates, carbonates and hydrogen carbonates of alkali or alkaline earth metals are preferably used.
  • Sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate are particularly preferred.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 180 ° C., the reaction is preferably carried out at atmospheric pressure and temperatures from 20 to 140 ° C.
  • the compounds of formula (V) can be prepared by condensing the compounds of formula (IV) e.g. analogous to the methods described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, W02015 / 000715 or WO 2015/121136.
  • the conversion to compounds of formula (V) can take place in bulk or in a solvent, the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • Prefers are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
  • suitable condensing agents are carbodiimides such as l- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as e.g. Diethylazodicarboxylic acid.
  • carbodiimides such as l- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
  • Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon
  • acids examples include sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and N, N
  • An example of a suitable chlorinating agent is phosphorus oxychloride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
  • the compounds of the formula (I), where n is 0, can be prepared by reacting the compounds of the formula (V) with the compounds of the formula (Via) in the presence of a base.
  • Mercaptan derivatives of the formula (Via) such as, for example, methyl mercaptan, ethyl mercaptan or isopropyl mercaptan are either commercially available or can be prepared by known methods, for example analogously to that in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), 1329.
  • the reaction to give the compound of formula (I), where n is 0, can be carried out in bulk or in a solvent; the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
  • suitable bases are inorganic bases from the group consisting of acetates, phosphates, hydrogen carbonates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate, potassium carbonate and sodium hydrogen carbonate are preferred. Other suitable bases are alkali metal hydrides such as e.g. Sodium hydride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
  • X 1 preferably represents a fluorine or chlorine atom.
  • XI is bromine
  • it can also be transmetallated with a suitable lithium base and then reacted with the corresponding commercially available disulfide. See also Bioorganic and Medicinal Chemistry Edinburghs, 20 (2010), 2770 - 2775.
  • Suitable lithium bases are, for example, n-butyllithium.
  • the reaction to give the compound of formula (I), where n is 0, can take place in bulk or in a solvent, the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert are preferred. -Butylmethyl lether
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
  • the reaction can be carried out in the microwave.
  • the compounds of the formula (I), where n is 1, can be prepared by oxidation of the compounds of the formula (I), where n is 0.
  • the oxidation is generally carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
  • the reaction can be carried out in vacuo, at normal pressure or under superatmospheric pressure and at temperatures from -20 ° C to 120 ° C. Steps)
  • the compounds of formula (I), where n is 2 can be prepared by oxidation of the compounds of formula (I), where n is 1.
  • the oxidation is generally carried out in a solvent.
  • Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at normal pressure or under superatmospheric pressure and at temperatures from -20 ° C to 120 ° C.
  • Step f) The compounds of the formula (I), where n is 2, can also be prepared in a one-step process by oxidation of the compounds of the formula (I), where n is 0.
  • the oxidation is generally carried out in a solvent.
  • Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at normal pressure or under superatmospheric pressure and at temperatures from -20 ° C to 120 ° C.
  • radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n have the meanings described above, A 2 and A 3 represent CH or N and X 1 represents halogen (preferably bromine or iodine).
  • M stands for an alkali metal (preferably sodium or potassium).
  • the reaction is generally catalyzed by the addition of a copper (I) salt such as copper (I) iodide.
  • Suitable sulfur reagents are salts of sulfinic acid.
  • reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from -20 ° C. to 120 ° C.
  • Compounds of the formula (VIII) can be prepared by cyanomethylating the compounds of the formula (VII) with a compound of the formula (M) in the presence of a catalyst, a ligand and a base, for example according to the method described in J. Am. Chem. Soc. (2002), 124, 9330, J. Am. Chem. Soc. (2005), 127, 15824 or W02016 / 041819.
  • the compound of formula (M) is commercially available.
  • the conversion to compounds of formula (VIII) is usually carried out in a solvent.
  • Aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide are preferred.
  • Palladium complexes such as tris (dibenzylidene acetone) dipalladium (0) or [l, l'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) can be used as the catalyst and organophosphane compounds such as bis are generally used as ligands (diphenylphosphine) -9,9-dimethylxanthene (Xanthphos).
  • a suitable base is, for example, zinc fluoride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
  • the cyanomethylation can also be carried out using a Suzuki coupling, for example according to the method described in J. Am. Chem. Soc. (2011), 133, 6948-6951.
  • the conversion to compounds of the formula (I), where n is 2, is generally carried out in a solvent.
  • Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene, aprotic polar solvents such as acetone, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such as ethyl acetate are preferred.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] - 7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] - 7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] - 7-undecene
  • tertiary amines such as triethylamine and N, N-diisopropyleth
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
  • Process D carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods, for example from pyridines of the formula (IX) analogously to the processes described in WO2011 / 15343, WO2014 / 14874 or WO2010 / 34738.
  • R 2 and R 3 have the meanings described above, X stands for a halide ion, preferably iodide, X 1 stands for halogen and R 14 stands for (Ci-C4) alkyl.
  • the compounds of the formula (X) can be reacted by reacting compounds of the formula (IX) with hydroxylamine-O-sulfonic acid in the presence of a base such as, for example, potassium carbonate N-iminopyridinium intermediate are converted, which is converted in a second step in the presence of an acid such as, for example, hydroiodic acid (HI) in a suitable solvent such as, for example, ethanol into the 1-amino-pyridinium derivative of the formula (X).
  • a base such as, for example, potassium carbonate
  • N-iminopyridinium intermediate are converted, which is converted in a second step in the presence of an acid such as, for example, hydroiodic acid (HI) in a suitable solvent such as, for example, ethanol into the 1-amino-pyridinium derivative of the formula (X).
  • a base such as, for example, potassium carbonate
  • N-iminopyridinium intermediate are converted, which is converted in a second step in the presence of
  • Cycloaddition can be prepared with an alkyne of the formula (XI). If isomers are formed, they can be separated into the individual isomers by chromatographic methods. In this way, the diester of formula (XII) can be obtained isomerically pure. By heating in a suitable acid such as, for example, aqueous sulfuric acid, compounds of the formula (XII) can be converted into acids of the formula (XIII) by decarboxylation and simultaneous saponification of the ester function. Step d)
  • Compounds of the formula (III) can be prepared by standard halogenation processes, for example analogously to the processes described in WO201 1/50284 or WO2016 / 12896, for example with N-chlorosuccinimide or N-bromosuccinimide as halogenating agent in a suitable solvent such as dichloromethane or 1, 2-dichloroethane.
  • carboxylic acids of the formula (III) can be prepared from 2-formylpyridine derivatives of the formula (XIV) analogously to that in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009 / 29625 procedures described.
  • the compounds of the formula (XVI) can be prepared in analogy to the processes described in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009 / 29625 by reacting compounds of the formula (XIV) with an alkyl azidoacetate derivative of formula (XV) in the presence of a suitable base such as sodium methoxide in a suitable solvent such as methanol.
  • a suitable base such as sodium methoxide
  • a suitable solvent such as methanol.
  • the compounds of formula (XIV) are commercially available or can be prepared by standard methods. Step b)
  • the ester of formula (XVII) can be converted to the acid of formula (XVIII) using standard methods, for example with an alkali hydroxide as a base such as sodium hydroxide or lithium hydroxide in an alcohol as a solvent such as e.g. Ethanol or a mixture of tetrahydrofuran and water.
  • an alkali hydroxide as a base such as sodium hydroxide or lithium hydroxide in an alcohol as a solvent
  • e.g. Ethanol e.g. Ethanol or a mixture of tetrahydrofuran and water.
  • R 2 , R 3 and R 4 have the meanings described above, A stands for CH or N, Y stands for a leaving group such as chlorine, bromine, iodine, O-triflate or O-mesyl and X 1 stands for halogen.
  • the compounds of the formula (XX) can be prepared in analogy to the process described in US5576335 by reacting compounds of the formula (XIX) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base.
  • Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible manufacturing routes are described in methods D and E.
  • the reaction of the compounds of the formula (XIX) with carboxylic acids of the formula (III) can be carried out in Substance or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane are preferred; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
  • Nitriles such as acetonitrile or propionitrile
  • aromatic hydrocarbons such as toluene or xylene
  • aprotic polar solvents such as N, N
  • Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • Suitable bases are inorganic bases which are usually used in such reactions.
  • Bases which are selected by way of example from the group consisting of acetates, phosphates, carbonates and hydrogen carbonates of alkali or alkaline earth metals are preferably used.
  • Sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate are particularly preferred.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 180 ° C., the reaction is preferably carried out at atmospheric pressure and temperatures from 20 to 140 ° C.
  • the compounds of formula (XXI) can be prepared by condensing the compounds of formula (XX) e.g. analogous to that in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404,
  • the reaction to give compounds of the formula (XXI) can be carried out in bulk or in a solvent; the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • the reaction can be carried out in the presence of a condensing agent, an acid, a base or a
  • suitable condensing agents are carbodiimides such as l- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as e.g. Diethylazodicarboxylic acid.
  • carbodiimides such as l- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
  • Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon
  • acids examples include sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and N, N
  • An example of a suitable chlorinating agent is phosphorus oxychloride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
  • the compounds of the formula (XXI) can be used using standard methods (see, for example, Heterocycles 1999, 50, 1081-1090; WO2009 / 70045 or Bioorganic and Medicinal Chemistrylitiss 2007, 17, 1369-1375) by reaction with electrophilic groups containing a leaving group
  • 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. Control of animal pests is preferably carried out in agriculture and forestry and in material protection. This preferably excludes methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.
  • pesticides always includes the term crop protection agents.
  • the compounds of formula (I) are suitable with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for protecting 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, especially insects, Arachnids, helminths, in particular nematodes, and mollusks, which occur in agriculture, horticulture, animal husbandry, aquaculture, in forests, in gardens and leisure facilities, in the protection of stored goods and materials, and in the hygiene sector.
  • the term “hygiene” is to be understood to mean any and all measures, regulations and procedures whose aim is to prevent diseases, in particular infectious diseases, and which serve the health of people and protect animals and / or protect the environment and / or maintain cleanliness. According to the invention, this includes, in particular, measures for cleaning, disinfection and sterilization, for example of textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal (s), in order to ensure that these are free from hygiene pests and / or their excretions.
  • surgical or therapeutic treatment instructions to be applied to the human body or the bodies of animals and diagnostic instructions which are carried out on the human body or the bodies of animals are preferably excluded from the scope of protection of the invention.
  • 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.
  • honeygiene pest should therefore be understood to mean one or more animal pests whose presence in the hygiene sector is problematic, particularly for health reasons. It is therefore a primary goal to avoid or minimize the presence of and / or exposure to hygiene pests in the hygiene sector. This can be achieved in particular by using a pesticide which is used both to prevent infestation and to prevent an already existing infestation leaves. Preparations that prevent or reduce exposure to pests can also be used.
  • hygiene pests include the organisms mentioned below.
  • the compounds of 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 pests mentioned above include:
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus.
  • Oligonychus coniferarum Oligonychus ilicis
  • Oligonychus indicus Oligonychus mangiferus
  • Oligonychus pratensis Oligonychus punicae
  • Oligonychus yothersi Omithodorus spp.
  • Omithonyssus spp. Panonychus.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp.
  • Rhipicephalus spp. Rhizoglyphes spp. Steneotarsonemus spinki, Tarsonemus spp.
  • Anoplophora glabripennis Anthonomus spp., E.g. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. B. Bruchus pisorum, Bruchus rufhnanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., E.g. B.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Ep., Ep. Spp.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus comutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegica, Hypususus, Hyposomusus, Hylotrup spp., e.g. B.
  • hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., Z. B.
  • Leucoptera coffeella, Limonius ectypus, Lissorhoptms oryzophilus, Listronotus ( Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., Z.
  • Tribolium audax Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. B. Zabrus tenebrioides; from the order of the Dermaptera z.
  • Aedes spp. E.g. B.
  • Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona plyaialis, Cochlipp. B.
  • B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., E.g. B. Dasineura brassicae, Delia spp., E.g. B.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., Z.
  • Amrasca bigutulla Amrasca devastans, Anuraphis cardui, Aonidiella spp., E.g. B.
  • Aspidiella spp. Aspidiella spp., Aspidiotus spp., E.g. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., e.g. B.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, z. Myzus spp. B.
  • Nephotettix cincticeps Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Z. B.
  • Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., E.g. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp.
  • E.g. B Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psylla spp., E.g. B.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., E.g. B.
  • 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. B.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Z. B.
  • Piezodorus guildinii Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera z.
  • Acromyrmex spp. Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., E.g. B.
  • Diprion similis, Hoplocampa spp. E.g. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Z. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. B.
  • Vespa crabro Wasmannia auropunctata, Xeris spp .; from the order of the Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera z. B. Coptotermes spp., E.g. B. Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., Z. B.
  • Reticulitermes flavipes Reticulitermes hesperus; from the order of the Lepidoptera 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. B.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., E.g. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., Z. B. Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., Z. B.
  • Leucoptera coffeella Lithocolletis spp., E.g. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., E.g. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., E.g. B.
  • Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Podesia spp., Z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. B.
  • Scirpophaga spp. E.g. B. Scirpophaga innotata, Ontario segetum, Sesamia spp., E.g. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. B.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., E.g. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. B. Locusta migratoria, Melanoplus spp., E.g. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of the Phthiraptera z. B.
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera z.
  • Anaphothrips obscurus Basothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuten, Enneothrips flavens, Frankliniella spp., Z.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of the Symphyla z.
  • B. Scutigerella spp. E.g. B. Scutigerella immaculata;
  • Pests from the Mollusca tribe e.g. B. from the class of Bivalvia, z. B. Dreissena spp .; as well as from the class of Gastropoda z. B. Arion spp., E.g. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
  • Plant pests from the Nematoda strain ie plant-parasitic nematodes, in particular Aglenchus spp., E.g. B. Aglenchus agricola, Anguina spp., E.g. B. Anguina tritici, Aphelenchoides spp., E.g. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., E.g. B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., E.g. B.
  • B. Cacopaurus pestis, Criconemella spp., E.g. B. Criconemella curvata, Criconemella onoensis, Criconemella omata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. B.
  • Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. B. Trichodorus obtusus, Trichodorus primitive, Tylenchorhynchus spp., e.g. B. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., E.g. B. Xiphinema index.
  • the compounds of the formula (I) can, if appropriate in certain concentrations or application rates, also as herbicides, safeners, growth regulators or agents for improving the plant properties, as microbicides or gametocides, for example as fungicides, antifungals, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • the present invention further relates to formulations and use forms prepared therefrom as pesticides such.
  • B. drench, drip and spray broths comprising at least one compound of formula (1).
  • the use forms contain further pesticides and / or adjuvants which improve the effect, such as penetration promoters, for.
  • B. vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rapeseed oil or soybean oil methyl esters or alkanol alkoxylates and / or spreading agents such as alkylsiloxanes and / or salts, e.g. B.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or the retention-promoting agents such.
  • B. glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizers.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS) ; these and other possible types of formulations are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576.
  • the formulations may contain, in addition to one or more compounds of the formula (I), further agrochemical active ingredients.
  • auxiliaries such as, for example, extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries such as, for example, adjuvants.
  • An adjuvant in this context is a component that is biological Effect of the formulation improved without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface or penetration.
  • formulations are prepared in a known manner, e.g. B. by mixing the compounds of formula (I) with auxiliaries such as extenders, solvents and / or solid carriers and / or other auxiliaries such as surfactants.
  • auxiliaries such as extenders, solvents and / or solid carriers and / or other auxiliaries such as surfactants.
  • the formulations are either produced in suitable plants or before or during use.
  • Auxiliaries which can be used are substances which are suitable, the formulation of the compounds of the formula (1) or the use forms prepared from these formulations (such as usable pesticides such as spray liquors or seed dressings) have special properties, such as certain physical, technical and / or to impart biological properties.
  • polar and non-polar organic chemical liquids z. B from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), the ketones (such as acetone, cyclohexanone ), Esters (also fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethyl sulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • organic solvents can also be used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B.
  • Suitable solvents are, for example, aromatic hydrocarbons such as. B. xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such as. B. cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as. B. methanol, ethanol, isopropanol, Butanol or glycol and their ethers and esters, ketones such as. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide and water.
  • aromatic hydrocarbons such as. B. xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as.
  • Suitable carriers for granules are: B.
  • broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • Liquefied gaseous extenders or solvents can also be used.
  • Particularly suitable extenders or carriers are those which are gaseous at normal temperature and pressure, e.g. B. aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • emulsifiers and / or foaming agents, dispersants or wetting agents with ionic or nonionic properties or mixtures of these surface-active substances 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 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.
  • B alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolyzates, lignin sulfite liquors and methyl cellulose.
  • a surface-active substance is advantageous if one of the compounds of the formula (I) and / or one of the inert carriers is not soluble in water and if the application is carried out in water.
  • dyes such as inorganic pigments, for.
  • iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrients and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and / or physical stability can also be present.
  • Foam-producing agents or defoamers can also be contained.
  • formulations and use forms derived therefrom can also contain adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids, as additional auxiliaries.
  • additional auxiliaries can be mineral and vegetable oils.
  • auxiliaries can be contained in the formulations and the use forms derived therefrom.
  • 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) can be combined with any solid or liquid additive that is commonly used for formulation purposes.
  • penetration promoters include all those substances that are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are defined in this context by the fact that they penetrate into the plant's cuticle from the (usually aqueous) application broth and / or from the spray coating and can thereby increase the mobility of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut fat ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil methyl esters, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • alcohol alkoxylates such as coconut fat ethoxylate (10) or isotridecyl ethoxylate (12)
  • fatty acid esters such as rapeseed oil or soybean oil methyl esters
  • fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I), particularly preferably between 0.01 and 95% by weight of the compound of the formula (I), very particularly 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 use forms (in particular pesticides) prepared from the formulations can vary within wide limits.
  • the concentration of the compound of the formula (I) in the use forms can 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 use form , lie.
  • the application takes place in a customary manner adapted to the application forms.
  • the compounds of formula (I) can also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, bird repellants, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators become so z.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, bird repellants, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators become so z.
  • B. to broaden the spectrum of activity, to prolong the duration of action, to increase the speed of action, to prevent repellency or to prevent the development of resistance.
  • active ingredient combinations can affect plant growth and / or tolerance to abiotic factors such as. B.
  • Flowering and fruiting behavior can also be improved, germination and rooting optimized, harvesting easier and crop yield increased, ripeness influenced, the quality and / or nutritional value of the crop products increased, the shelf life extended and / or the workability of the crop products improved.
  • the compounds of the formula (I) can furthermore be present in a mixture with further active compounds or semiochemicals, such as attractants and / or bird 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 use forms prepared from these formulations in a mixture with further compounds, preferably those as described below.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarban, Propoxuracam, Carbox XMC and xylylcarb or organophosphates, e.g. B.
  • AChE Acetylcholinesterase
  • GABA controlled chloride channel blockers such as cyclodiene organochlorine, e.g. B. Chlordan and Endosulfan or Phenylpyrazole (Fiprole), e.g. B. Ethiprol and Fipronil.
  • sodium channel modulators such as pyrethroids, e.g. B. acrinathrin, allethrin, d-cis-trans-allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambhalhrinothrin, lambda gammhalin , Cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans-isomer], deltamethrin, empenthrin [(EZ) - (lR) -isomer], esf
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. B. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • Allosteric modulators of the nicotinic acetylcholine receptor such as Spinosyne, e.g. B. Spinetoram and Spinosad.
  • Allosteric modulators of the glutamate-dependent chloride channel such as, for example, avermectine / milbemycine, e.g. B. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimetics such as juvenile hormone analogs, e.g. B. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Juvenile hormone mimetics such as juvenile hormone analogs, e.g. B. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Various non-specific (multi-site) inhibitors such as alkyl halides, e.g. B.
  • Methyl bromide and other alkyl halides or chloropicrin or sulfuryl fluoride or borax or Brechweinstein or methyl isocyanate producer, e.g. B. Diazomet and Metam.
  • mite growth inhibitors such as B. clofentezin, hexythiazox and diflovidazine or etoxazole.
  • Microbial disruptors of the insect intestinal membrane such as. B. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and B.t. Plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Abl / 35Abl.
  • Inhibitors of mitochondrial ATP synthase such as ATP disruptors, such as, for example, diafenthiuron or organotin compounds, e.g. B. azocyclotin, cyhexatin and fenbutatin oxide or
  • Blockers of the nicotinic acetylcholine receptor channel such as, for example, bensultap, cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Inhibitors of chitin biosynthesis type 0, such as, for example, bistrifluron, chlorofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • Type 1 chitin biosynthesis inhibitors such as buprofezin.
  • molting disruptor especially dipteras, i.e. two-wingers
  • cyromazine especially dipteras, i.e. two-wingers
  • Ecdysone receptor agonists such as chromafenozid, halofenozid, methoxyfenozid and tebufenozid.
  • Octopamine receptor agonists such as Amitraz.
  • Mitochondrial complex III electron transport inhibitors such as hydramethylnon or acequinocyl or fluacrypyrim.
  • Mitochondrial complex I electron transport inhibitors such as, for example, METI acaricides, e.g. B. Fenazaquin, Fenpyroximat, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenon (Derris).
  • Blockers of the voltage-dependent sodium channel such as. B. indoxacarb or metaflumizone.
  • Inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. B. spirodiclofen, spiromesifen and spirotetramat.
  • Mitochondrial complex IV electron transport inhibitors such as phosphines, e.g. B. aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides,
  • Inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g. B. Cyenopyrafen and Cyflumetofen and carboxanilides, such as pyflubumide.
  • Ryanodine receptor modulators such as diamides, e.g. B. chlorantraniliprole,
  • Cyanotraniliprole and flubendiamide, other active ingredients such as afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolit, cyclaniliprol, cycloxaprid, dyhalomoflutinolidilidolinilidolinilidolin, dolinomidolinilidolinilidolin, dolinomidolinilidolinilidolin, dolinomidolinilidolin, dolinomidolinoid, dichalomidylinophenol, dicylomonidolinolidolinidolin, dolinidolinidolinidolin, dolonidolidolin, dicylnomidylinidolin, pd Fluazaindolizine, fluensulfone, fluor flu
  • All of the above-mentioned mixing partners of classes (1) to (15) can, if they are capable of doing so on account of their functional groups, salts with suitable bases or acids form. All of the fungicidal mixture partners of classes (1) to (15) mentioned can optionally include tautomeric forms.
  • inhibitors of ergosterol biosynthesis for example (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidine, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1.009) flutriafol, (1.010) imazalil, (1.01 1) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothiocone , (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetraconazole,
  • Respiratory chain inhibitors 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 IR, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer IS, 4R, 9R), (2.012) isopyrazam (anti epimeric racemate lRS, 4SR, 9SR), (2,013) isopyrazam (mixture of the syn-epimeric racemate lRS, 4SR, 9RS and the anti-epimeric racemate lRS, 4SR, 9SR), (2,014) isopyrazam (syn-epimeric en
  • inhibitors of the respiratory chain on complex III for example (3,001) ametoctradine, (3,002)
  • inhibitors of mitosis and cell division for example (4,001) carbendazim, (4,002) diethofencarb,
  • Inhibitors of amino acid and / or protein biosynthesis for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline (7.005) pyrimethanil, (7.006) 3- (5-fluoro- 3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline.
  • 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) valifenalate, (9.008) (2E) -3 - (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -l- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) -3- (4-tert-Butylphenyl) -3- (2-chloropyridin-4-yl) -l- (morpholin-4-yl) prop-2-en-l-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).
  • 13) Inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
  • Oxathiapiproline (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphonic acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone) (15.028) tebufloquine, (15.029niflide) tecloft , (15.031) l- (4- ⁇ 4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole- 2-yl ⁇ piperidin-1 -yl) -2- [5-methyl-3- (trifluoromethyl) - 1H-pyrazol-l-yl] ethanone, (15.032) l- (4- ⁇ 4 - [(5S) - 5- (2,6-difluorophenyl)
  • the compounds of formula (I) can be combined with biological pesticides.
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products which have been formed by microorganisms, including proteins and secondary metabolic products.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that act as biological insecticides, fungicides, or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-l, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • B. thuringiensis subspecies israelensis serotype H-14
  • strain AM65-52 accesion No. ATCC 1276
  • B. thuringiensis subsp. aizawai especially strain ABTS-1857 (SD-1372)
  • B. thuringiensis subsp. kurstaki strain HD-l or B. thuringiensis subs
  • fungi and yeasts that can be used as biological pesticides are: Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular Strain KV01, metarhician anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Acc .ion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain Vl 17b, Trichoderma atroviride, in particular strain SC1 (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used as biological pesticides are:
  • Adoxophyes orana Apple Peel Wrapper
  • Granulosevirus GV
  • Cydia pomonella Apple Wrapper
  • Granulosevirus GV
  • Helicoverpa armigera Cotton Capsule Worm
  • Nuclear Polyhedrosis Virus NPV
  • Spodoptera exigua Sudugar Beet Owl
  • mNPV Spodopteraischerf Cottonworm
  • Bacteria and fungi are also included, which are added as 'inoculant' to plants or parts of plants or plant organs and which promote plant growth and plant health through their special properties. Examples are:
  • Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora spp., Or Gigaspora monospor.
  • plant extracts and products which have been formed from microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
  • the compounds of the formula (I) can be combined with safeners, such as, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -l-oxa -4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -1, 3-oxazolidine
  • Plants are understood to mean all plants and plant populations such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes , Bell pepper, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (e.g. cabbage) and other vegetables, cotton, tobacco, rape, and fruit plants (with the fruits apples, pears, Citrus and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soybeans
  • potatoes sugar beets
  • sugar cane tomatoes , Bell pepper, cucumber, melon, carrot, watermelon
  • onion lettuce
  • spinach leek
  • beans Brassica oleracea
  • Brassica oleracea e.g. cabbage
  • 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 cultivars which can or cannot be protected by plant breeders' rights.
  • Plants are to be understood to mean all stages of development such as seeds, cuttings, young (immature) plants and mature plants.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being 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 and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants according to the invention 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 by the customary treatment methods, for. B. by immersion, spraying, evaporation, misting, scattering, brushing, injecting and in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
  • plants and their parts can be treated according to the invention.
  • wild plant species or plant species or those obtained by conventional biological breeding methods such as crossing or protoplast fusion are used as well as their parts treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant varieties are plants with new properties (“traits”) that have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received 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 drought or water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the crop products , higher shelf life and / or workability of the harvest products. Further and particularly highlighted examples of such properties are an increased ability of the plants to defend themselves against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails. B.
  • microbial pests such as insects, arachnids, nematodes, mites, snails.
  • SAR systemically acquired resistance
  • systemin phytoalexins
  • elicitors resistance genes and correspondingly expressed proteins and toxins
  • an increased tolerance of the plants to certain herbicidal active ingredients for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT "-Gene).
  • PAT phosphinotricin
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soy, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed being particularly emphasized.
  • the properties (“traits”) that are particularly emphasized are the plants' increased resistance to insects, arachnids, nematodes and snails. Plant protection - types of treatment
  • the treatment of the plants and parts of plants with the compounds of the formula (I) is carried out directly or by acting on their surroundings, living space or storage space by the customary treatment methods, for. B. by dipping, spraying, spraying, sprinkling, evaporating, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, watering (drenching), drip irrigation and with propagation material, in particular in the case of seed, furthermore by dry pickling, wet pickling, slurry pickling, incrusting , single or multi-layer coating, etc. It is also possible to apply the compounds of the formula (I) according to the ultra-low-volume method or to inject the use form or the compound of the formula (I) into the soil itself.
  • a preferred direct treatment of the plants is leaf application, i.e. H. the compounds of formula (I) are applied to the foliage, the treatment sequence and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also get into the plants via the root system.
  • the plants are then treated by the action of the compounds of the formula (I) on the habitat of the plant.
  • This can be, for example, by drenching, mixing into the soil or the nutrient solution, i.e. 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 soil application, i.e. 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 the case of water rice crops, this can also be done by metering the compound of the formula (I) into a solid application form (for example as granules) into a flooded rice field.
  • the present invention therefore also relates in particular to a method for protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of the formula (1).
  • the method according to the invention for protecting seed and germinating plants from pest infestation further comprises a method in which the seed is treated simultaneously in one process or sequentially with a compound of the formula (1) and a mixture component. It also includes a method in which the seed is treated at different times with a compound of formula (1) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (1) for the treatment of seeds in order to protect the seeds and the plant resulting therefrom from animal pests.
  • the invention further relates to seeds which have been treated with a compound of the formula (1) according to the invention for protection against animal pests.
  • the invention also relates to seeds which have been treated at the same time with a compound of formula (1) and a mixture component.
  • the invention further relates to seeds which have been treated at different times with a compound of the formula (1) and a mixture component.
  • the individual substances can be present on the seed in different layers.
  • the layers which contain a compound of formula (1) and mixture components can optionally be separated by an intermediate layer.
  • the invention also relates to seeds in which a compound of the formula (1) and a mixture component are applied as part of a covering or as a further layer or further layers in addition to a covering.
  • the invention relates to seeds which, after treatment with a compound of the formula (1), are subjected to a film coating process in order to avoid dust abrasion on the seeds.
  • One of the advantages that arise when a compound of formula (1) acts systemically is that the treatment of the seed protects not only the seed itself, but also the plants which result therefrom after emergence from animal pests. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be omitted.
  • Another advantage can be seen in the fact that the treatment of the seed with a compound of the formula (I) can promote germination and emergence of the treated seed.
  • Compounds of the formula (I) can also be used in combination with signaling agents, as a result of which there is better colonization with symbionts, such as, for example, rhizobia, mycorrhiza and / or endophytic bacteria or fungi, and / or there is an optimized nitrogen fixation.
  • symbionts such as, for example, rhizobia, mycorrhiza and / or endophytic bacteria or fungi, and / or there is an optimized nitrogen fixation.
  • the compounds of the formula (I) are suitable for protecting seeds of any type of plant which is used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (e.g. wheat, barley, rye, millet and oats), corn, cotton, soybeans, rice, potatoes, sunflower, coffee, tobacco, canola, rapeseed, beet (e.g. Sugar beet and fodder beet), peanut, vegetables (e.g. tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, lawn and ornamental plants.
  • cereals e.g. wheat, barley, rye and oats
  • corn, soybeans, cotton, canola, rapeseed, vegetables and rice is of particular importance.
  • transgenic seeds with a compound of formula (I) are of particular importance.
  • the heterologous genes in transgenic seeds can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly suitable for the treatment of transgenic seeds which contain at least one heterologous gene which is derived from Bacillus sp. comes from. It is particularly preferably a heterologous gene which comes from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment.
  • the seed can be treated at any time between harvesting and sowing.
  • seeds are used that have been separated from the plant and freed of pistons, shells, stems, casings, wool or pulp.
  • seeds can be used that have been harvested, cleaned and dried to a storable moisture content.
  • seeds can also be used, which after drying z. B. was treated with water and then dried again, for example Priming.
  • 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 the person skilled in the art.
  • the compounds of the formula (I) can be converted into the customary mordant formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and also ULV formulations.
  • formulations are prepared in a known manner by mixing the compounds of the formula (I) with customary additives, such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberelline and also water.
  • customary additives such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberelline and also water.
  • Suitable dyes which can be present in the mordant formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples include those under the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which can be contained in the mordant formulations which can be used according to the invention are all wetting-promoting substances which are customary for the formulation of agrochemical active compounds.
  • Alkyl naphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates, can preferably be used.
  • Suitable dispersants and / or emulsifiers which may be present in the mordant formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of active agrochemicals.
  • Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used.
  • suitable nonionic dispersants are Ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-triyrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate formaldehyde condensates.
  • the mordant formulations which can be used according to the invention can contain, as defoamers, all of the foam-inhibiting substances which are customary for formulating active agrochemicals. Silicone defoamers and magnesium stearate can preferably be used.
  • All substances which can be used in agrochemical compositions for such purposes can be present as preservatives in the mordant formulations which can be used according to the invention.
  • Examples include dichlorophene and benzyl alcohol hemiform.
  • Secondary thickeners which can be contained in the mordant formulations which can be used according to the invention are all substances which can be used in agrochemical compositions for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silica are preferred.
  • Suitable adhesives which can be contained in the mordant formulations which can be used according to the invention are all binders customarily used in mordants.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose are preferred.
  • the gibberellins are known (see R. Wegler “Chemistry of Plant Protection and Pest Control”, 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 treating a wide variety of seeds.
  • 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, and the seeds of corn, rice, rapeseed, peas, beans, cotton, Sunflowers, soybeans and beets or vegetable seeds of all kinds.
  • the seed dressing formulations which can be used according to the invention or their dilute use forms can also be used for dressing seeds of transgenic plants.
  • the procedure for dressing is that the seeds are placed in a mixer in batch or continuous operation, the desired amount of dressing formulation is added either as such or after prior dilution with water and until the formulation is evenly distributed mixes the seeds. If necessary, a drying process follows.
  • the application rate of the mordant formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the respective content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound 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.
  • the compounds of the formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular, ectoparasites or endoparasites.
  • endoparasite includes, in particular, helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of the formula (I), which have a favorable toxicity to warm-blooded animals, are suitable for combating parasites which occur in animal breeding and animal husbandry in farm animals, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of the development of the parasites.
  • Agricultural animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer and in particular cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. B. in aquaculture, or possibly insects such as bees.
  • Pets include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and in particular dogs, cats, house birds; Reptiles, amphibians or aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely house birds or, in particular, poultry.
  • the use of the compounds of the formula (I) for combating animal parasites is said to reduce or prevent illness, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey and the like), so that animal husbandry can be carried out more economically and easily and a better well-being of the animals can be achieved.
  • the term “control” or “control” in the present context means that the compounds of the formula (I) are effective in the occurrence of the respective parasite in an animal which is infected with such parasites to a harmless extent , is reduced.
  • "combating" means that the compounds of the formula (I) kill the particular parasite, prevent its growth or prevent its multiplication.
  • the arthropods include, but are not limited to, the Anoplurida order, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the subordinates Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Wemeckiella spp; from the order Diptera and the subordinates Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyi
  • the following Akari are examples of the arthropods, but are not limited to them: From the subclass Akari (Acarina) and the order Metastigmata, for example from the Argasidae family, such as Argas spp., Omithodorus spp., Otobius spp., From the Ixodidae family, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora such as:
  • Metamonada from the order Vaccinia spp., Spironucleus spp.
  • Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
  • Euglenozoa from the order Trypanosomatida, for example Leishmania spp., Trypanosoma spp.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. B. Hartmanella sp.
  • Alveolata such as Apicomplexa (Sporozoa): e.g. B. 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.
  • Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
  • Helminths pathogenic to humans or animals include, for example, acanthocephala, nematodes, pentastomas and platyhelminths (e.g. Monogenea, Cestodes and Trematodes).
  • Exemplary helminths include, but are not limited to: Monogenea: e.g. E.g. Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
  • Cestodes from the order Pseudophyllidea, for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
  • Cyclophyllida for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp.
  • Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma
  • Trematodes from the Digenea class, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
  • Collyriclum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrcma spp., Fasciola spp., Fascioliol sppis ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opistppithchis spp.
  • Paragonimus spp. Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.
  • Nematodes from the order Trichinellida, for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
  • Rhabditina From the order Rhabditina, for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenathoma spp.
  • Cyclococercus spp. Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidpp., Graphid spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagumesus.
  • Ollulanus spp . Ollulanus spp .; Omithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongyl.
  • Spirurida for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp .; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp .; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp .; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida, for example: Moniliformis spp.,
  • Pentastoma from the order Porocephalida, for example Linguatula spp.
  • the compounds of the formula (I) are administered by generally known methods, such as enterally, parenterally, dermally or nasally, in the form of suitable preparations. Administration can be prophylactic; metaphylactic or therapeutic.
  • One embodiment of the present invention thus relates to the compounds of the formula (I) for use as a medicament.
  • Another aspect relates to the compounds of formula (I) for use as an anti-endoparasitic.
  • a further special aspect of the invention relates to the compounds of the formula (I) for use as an antihelminthic agent, in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.
  • Another specific aspect of the invention relates to the compounds of formula (I) for use as an antiprotozoal.
  • Another aspect relates to the compounds of the formula (I) for use as an antiectoparasitic, in particular an arthropodicide, very particularly an insecticide or an acaricide.
  • veterinary formulations which comprise an effective amount of at least one compound of the formula (I) and at least one of the following: a pharmaceutically acceptable excipient (for example solid or liquid diluents), a pharmaceutically acceptable auxiliary (for example surfactants), in particular one pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable excipient conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient for example solid or liquid diluents
  • auxiliary for example surfactants
  • a related aspect of the invention is a process for the preparation of 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 auxiliaries, in particular with pharmaceutically acceptable excipients and conventionally used in veterinary formulations / or comprises auxiliaries conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozolic and arthropodicidal formulations, very particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, insecticidal, and pentastomicidal, according to pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomici
  • Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by using an effective amount of a compound of the formula (I) in an animal, in particular a non-human Animal that needs it.
  • Another aspect relates to a method of treating a parasitic infection, in particular a parasite infection selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined here to an animal, in particular a non-human animal, the latter requirement.
  • Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasite 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 the formula (I) with other active compounds, in particular with endo- and ectoparasiticides, are hereby provided for the veterinary field.
  • blend not only means that two (or more) different active ingredients are formulated in a common formulation and used accordingly together, but also refers to products that contain separate formulations for each active ingredient. Accordingly, if more than two active ingredients are to be used, all active ingredients can be formulated in a common formulation or all active ingredients can be formulated in separate formulations; Mixed forms are also conceivable, in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow the active substances in question to be used separately or in succession.
  • Exemplary active ingredients from the group of ectoparasiticides as mixing partners include, but are not intended to be a limitation, the insecticides and accaricides listed in detail above.
  • Other active ingredients that can be used are listed below according to the classification mentioned above, which is 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 modulators of the nicotinic acetylcholine receptor (nAChR); (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) chordotonic organ modulators; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP
  • Active substances with unknown or non-specific mechanisms of action e.g. B. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlorodime form, flubenzimin, dicyclanil, amidoflumet, quinomethionate, Triarathes, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazon, gossyplur, flutenzin, bromopropylate, cryolite;
  • Organochlorine compounds e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. B. acetoprol, pyrafluprol, pyriprol, vaniliprol, sisapronil; or isoxazolines, e.g. B. Sarolans, Afoxolans, Lotilans, Fluralans;
  • Pyrethroids e.g. B. (cis-, trans-) metofluthrin, profluthrin, Flufenprox, flubrocythrinate, Fubfenprox, fenfluthrin, protrifen but, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, fenhrethrin, biopyrin, cethrin , Cyhalothrin (lambda), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs),
  • Neonicotinoids e.g. B. nithiazine
  • Dicloromezotiaz, triflumezopyrim macrocyclic lactones e.g. B. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime
  • Bios, hormones or pheromones for example natural products, e.g. Thuringiensin, Codlemon or Neem components
  • Dinitrophenols e.g. B. Dinocap, Dinobuton, Binapacryl;
  • Benzoyl ureas e.g. B. fluazuron, penfluron,
  • Amidine derivatives e.g. B. chloromebuform, cymiazole, demiditraz
  • Beehive varroa acaricides for example organic acids, eg formic acid, oxalic acid.
  • Exemplary active ingredients from the group of endoparasiticides, as mixing partners, include, but are not limited to, anthelmintic active ingredients and antiprotozoic active ingredients.
  • the anthelmintic active ingredients include, but are not limited to, the following nematicidal, trematicidal and / or cestocidal active ingredients: from the macrocyclic lactone class, for example: Eprinomectin, Abamectin, Nemadectin, Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbem Ivermectin, emamectin, milbemycin; from the class of the benzimidazoles and sample zimidazoles for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole sulfoxide, albendazo
  • Antiprotozoal active ingredients including but not limited to the following active ingredients: from the triazine class, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyletherionophore, for example: monensin, salinomycin, maduramicin, narasin; from the class of the macrocyclic lactones, for example: milbemycin, erythromycin; from the class of the quinolones, for example: enrofloxacin, pradofloxacin; from the quinine class, for example: chloroquine; from the class of pyrimidines, for example: pyrimethamine; from the class of the sulfonamides, for example: sulfachinoxaline, trimethoprim, sulfaclozin; from the class of the thiamines, for example: amprolium; from the class of lincosamides, for example: clindamycin; from
  • a vector in the sense of the present invention is an arthropod, in particular an insect or arachnid, which is capable of pathogens such as.
  • B. Viruses, worms, unicellular organisms and bacteria from a reservoir (plant, animal, human, etc.) to a host.
  • the pathogens can either be transferred mechanically (e.g. trachoma from non-stinging flies) to a host, or after injection (e.g. malaria parasites from mosquitoes) into a host.
  • Flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • Mites acariosis, epidemic typhus, rickettsi pock, tularemia, Saint-Louis encephalitis, early summer meningoencephalitis (TBE), Crimean-Congo fever, Lyme disease;
  • Ticks Borelliosis such as Borrelia bungdorferi sensu lato., Borrelia duttoni, early summer meningoencephalitis, Q fever (Coxiella bumetii), Babesia (Babesia canis canis), Ehrlichiosis.
  • vectors in the sense of the present invention are insects, for example aphids, flies, cicadas or thrips, which plant viruses can transmit to plants.
  • Other vectors that plant viruses can transmit are spider mites, lice, beetles and nematodes.
  • Further examples of vectors in the sense of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. BA gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.
  • Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens which are transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. B. in agriculture, horticulture, in forests, in gardens and leisure facilities as well as in storage and material protection.
  • the compounds of formula (I) are suitable for protecting industrial materials against attack or destruction by insects, for. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the use of the invention to protect wood is particularly preferred.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of the formula (I) are present as a ready-to-use pesticide, ie. that is, they can be applied to the corresponding material without further changes.
  • Other insecticides or fungicides in particular are those mentioned above.
  • the compounds of the formula (I) can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water, against fouling.
  • the compounds of formula (I) can be used alone or in combinations with other active ingredients as antifouling agents. Control of animal pests in the hygiene sector
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites that occur in closed rooms, such as, for example, apartments, factory halls, offices, vehicle cabins, animal husbandry systems.
  • the compounds of the formula (I) are used alone or in combination with other active compounds and / or auxiliaries. They are preferably used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests from the Arachnida class from the Scorpiones, Araneae and Opiliones orders, from the Chilopoda and Diplopoda classes, from the Insecta class the Blattodea order, from the Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera orders, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the Malacostraca class the order Isopoda.
  • the application takes place, for example, in aerosols, unpressurized sprays, e.g. B.
  • LC-MS3 Waters UPLC with SQD2 mass spectrometer and SampleManager sample changer.
  • LC-MS6 and LC-MS7 Agilent 1290 LC, Agilent MSD mass spectrometer, HTS PAL sample changer. Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow 1.0 ml / min).
  • LC-MS4 Waters IClass Acquity with QDA mass spectrometer and FTN sample changer (column Waters Acquity 1.7 pm 50 mm * 2.1 mm, column oven temperature 45 ° C). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow 0.7 mFmin.
  • LC-MS5 Agilent 1100 LC system with MSD mass spectrometer and HTS PAL sample changer (column: Zorbax XDB CI 8 1.8 pm 50 mm * 4.6 mm, column oven temperature 55 ° C). Linear gradient 0.0 to 4.25 minutes from 10% acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95% acetonitrile, flow 2.0 mFmin.
  • the retention time indices were determined from a calibration measurement of a homologous series of straight-chain alkan-2-ones with 3 to 16 carbons, the index of the first alkanone being set to 300, that of the last one to 1600 and linear between the values of successive alkanones was interpolated.
  • Spectrometer equipped with a 1.7 mm TCI probe head carried out with tetramethylsilane as standard (0.00 ppm) of solutions in the solvents CD3CN, CDCL or d ö -DMSO.
  • a Bruker Avance III 600 MHz spectrometer equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz spectrometer equipped with a 5 mm TCI probe head was used for the measurements.
  • the measurements were carried out at a probe head temperature of 298 K. If other measuring temperatures were used, this will be noted separately.
  • the 1 H-NMR data of selected examples are presented in the form of 1 H-NMR lists. For each signal peak, the d-value is shown in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated from each other by semicolons.
  • the peak list of an example therefore has the form: di (intensity ⁇ ; 62 (intensity2);.; D; (intensity ⁇ ;.; D h (intensity)
  • the intensity of sharp signals correlates with the height of the signals in a printed representation of a 1 H NMR spectrum in cm and shows the real relationships of the signal intensities. With wide 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.
  • Tetramethylsilane is used to calibrate the chemical shift of 1 H NMR spectroscopy or the chemical shift of the solvent if the sample does not contain tetramethylsilane. Therefore, the 1 H NMR pakaklistcn may contain the tetramethylsilane peak.
  • NMR solvent signals, the tetramethylsilane peak and the water signal in the respective solvent are excluded from the relative intensity calibration because the specified intensity values can be very high.
  • peaks of (stereo) isomers of the compounds according to the invention and / or peaks of impurities usually have a lower intensity on average than the peaks of the compounds according to the invention (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities can be typical of the respective production process. Your peaks can thus help to identify the reproduction of a manufacturing process using “by-product fingerprints”.
  • An expert who calculates the peaks of the compounds according to the invention using known methods can identify the peaks of the compounds according to the invention as required, additional intensity filters being used if necessary. This identification is equivalent to the relevant peak listing in the classic 1 H NMR interpretation.
  • the solvent used can be read from the JCAMP file with the parameter "solvent”, the measuring frequency of the spectrometer with "observe firequency” and the spectrometer model with "spectrometer / data system”.
  • 13 C-NMR data are given in analogy to the 1 H-NMR data as peak lists from broadband-decoupled 13 C-NMR spectra.
  • the NMR solvent signals and tetramethylsilane are excluded from the relative intensity calibration because these signals can have very high intensity values.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (CI 8) using the following methods:
  • a The logP value is determined by LC-UV measurement in the acidic range, with 0.9 ml / 1 formic acid in water and 1.0 ml / 1 formic acid in acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • h The logP value is determined by LC-UV measurement in the neutral range, with 79 mg / 1 ammonium carbonate in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • the calibration was carried out with a homologous series of straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known logP values. The values between successive alkanones are determined by linear regression.
  • the death rate is determined in%. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
  • Pre-swollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and a little water (5 seeds per cavity). The germinated wheat grains are sprayed with an active ingredient preparation of the desired concentration. Then each cavity is infected with 10-20 beetle larvae from Diabrotica balteata.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
  • Corn leaf disks (Zea mays) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are covered with caterpillars of the army worm (Spodoptera frugiperda).
  • the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
  • the following compounds of the preparation examples effect of 100% at a rate of 100g / ha: I-1, 1-2, 1-3, 1-4, 1-5.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • Solvent 100 parts by weight of acetone. To produce a suitable preparation of active compound, dissolve 1 part by weight of active compound with the specified parts by weight of solvent and make up to the desired concentration with water.
  • IPL41 insect medium (33% + 15% sugar) to a final volume of 200 m ⁇ . Then the plates are sealed with parafilm, through which a mixed population of greens
  • Peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce through and absorb the solution.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the following compounds of the preparation examples effect of 100% at an application rate of 4ppm: I-1, 1-2, 1-3, 1-4.
  • Emulsifier alkylaryl polyglycol ether
  • Test concentrations are diluted with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis), which are affected by all stages of the green peach aphid (Myzus persicae), are sprayed with an active ingredient preparation of the desired concentration. After 5 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier. If it is necessary to add Ammonium salts and / or penetration promoters are each added to the preparation solution in a concentration of 1000 ppm.
  • Paprika plants Capsicum annuum
  • Myzus persicae green peach aphid
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, taking into account the volume of soil into which it is threshed. It is important to ensure that a concentration of 40 ppm emulsifier in the soil is not exceeded. To prepare further test concentrations, dilute with water.
  • corn kernels are sown in pots filled with soil (Zea mays) and poured on the following day with the preparation of active compound of the desired concentration. After a day, approximately 25 L2 larvae of the corn rootworm (Diabrotica balteata) are added.

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Abstract

The invention relates to novel compounds of the formula (I), in which Q represents a heteroaromatic 9-membered or 12-membered annellated bicyclic or tricyclic ring system from the series Q1 to Q5 and R1, R2, R3, R4, R5, R6 and n have the meanings given above. The invention also relates to the use thereof as acaricides and/or insecticides for controlling animal pests.

Description

Heterocvclen-Derivate als Schädlingsbekämpfungsmittel  Heterocvclen derivatives as pesticides
Die vorliegende Erfindung betrifft Heterocyclen-Derivate der Formel (I), deren Verwendung als Akarizide und/oder Insektizide zur Bekämpfung tierischer Schädlinge, vor allem von Arthropoden und insbesondere von Insekten und Spinnentieren und Verfahren und Zwischenprodukte zu ihrer Herstellung. The present invention relates to heterocycle derivatives of the formula (I), their use as acaricides and / or insecticides for controlling animal pests, especially arthropods and in particular insects and arachnids, and processes and intermediates for their preparation.
Heterocyclen-Derivate mit insektiziden Eigenschaften sind in der Literatur bereits beschrieben, z.B. in, WO2016/129684, WO 2016/142327, WO2016/162318, W02017/001311, WO2017/061497,Heterocycle derivatives with insecticidal properties have already been described in the literature, e.g. in, WO2016 / 129684, WO 2016/142327, WO2016 / 162318, W02017 / 001311, WO2017 / 061497,
WO2017/093180, JP2018-024658, JP2018-024657, JP2018-70585, W02017/155103, W02018/050825 und EP17194731.0. Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Nützling- und Bestäuberschonung, der Umwelteigenschaften, der Aufwandmengen, der Kombinierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rolle sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss, ferner können Resistenzen auftreten, um nur einige Paramenter zu nennen. Schon aus all diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nicht als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. WO2017 / 093180, JP2018-024658, JP2018-024657, JP2018-70585, W02017 / 155103, W02018 / 050825 and EP17194731.0. Modern crop protection products have to meet many requirements, for example with regard to the amount, duration and breadth of their effects and possible use. Questions of toxicity, protection of beneficial organisms and pollinators, environmental properties, application rates, the ability to combine them with other active substances or formulation aids play a role, as well as the question of the effort that must be expended for the synthesis of an active substance, and resistances may also occur, but only by to name a few parameters. For all of these reasons alone, the search for new crop protection agents cannot be regarded as complete and there is a constant need for new compounds with properties which are improved compared to the known compounds, at least in relation to individual aspects.
Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert und/oder ihre Aktivität verbessert wird. The object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects and / or improve their activity.
Es wurden nun neue Heterocyclen-Derivate gefunden, welche gegenüber den bereits bekannten Verbindungen Vorteile aufweisen, z.B. seien bessere biologische oder ökologische Eigenschaften, breitere Anwendungsmethoden, eine bessere insektizide, akarizide Wirkung, sowie eine gute Verträglichkeit gegenüber Nutzpflanzen beispielhaft genannt. Die Heterocyclen-Derivate können in Kombination mit weiteren Mitteln zur Verbesserung der Wirksamkeit insbesondere gegen schwierig zu bekämpfende Insekten eingesetzt werden. New heterocycle derivatives have now been found which have advantages over the already known compounds, e.g. Examples of better biological or ecological properties, broader application methods, better insecticidal, acaricidal activity and good tolerance to useful plants are mentioned. The heterocycle derivatives can be used in combination with other agents to improve the effectiveness, in particular against insects which are difficult to control.
Gegenstand der vorliegenden Erfindung sind daher neue Verbindungen der Formel (I) in welcher (Ausgestaltung 1) The present invention therefore relates to new compounds of the formula (I) in which (configuration 1)
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2- C6)Alkinyl, (C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl, Halogen(C3-Cs)cycloalkyl, (C3- C6)Cycloalkyl-(Ci-C6)alkyl, (C3-C6)Cycloalkyl-(Ci-C6)halogenalkyl, (Ci-C6)Alkyl-(C3- Cs)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, (C3-C8)Cycloalkyl-(C3-Cs)cycloalkyl, Spiro-(C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C4-Ci2)Bicycloalkyl, (Ci-C6)Cyanoalkyl, (Ci- C6)Alkoxy-(Ci-C6)alkyl, (C2-C6)Cyanoalkenyl, (C3-C6)Cycloalkyl-(C2-C6)alkenyl, (C2- C6)Cyanoalkinyl, (C3-C6)Cycloalkyl-(C2-C6)alkinyl, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (C2- C6)Alkenyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkenyloxy-(Ci-C6)alkyl, (C2-C6)Alkinyloxy-(Ci- C4)alkyl, (C2-C6)Halogenalkinyloxy-(Ci-C6)alkyl, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci- C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkylthio-(Ci- Cö)alkyl, (Ci-C6)Halogenalkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkylsulfonyl-(Ci-C6)alkyl, oder Tri-(Ci-C6)alkylsilyl steht, R 1 for (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 - C6) alkynyl, (C 2 -C 6 ) Haloalkynyl, (C 3 -Cs) cycloalkyl, halogen (C 3 -Cs) cycloalkyl, (C 3 - C6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6 ) cycloalkyl- (Ci-C 6 ) haloalkyl , (Ci-C6) alkyl- (C3-Cs) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) cycloalkyl, (C 3 -C 8 ) cycloalkyl- (C 3 -Cs) cycloalkyl, spiro- (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, (C 4 -Ci 2 ) bicycloalkyl, (Ci-C6) cyanoalkyl, (Ci-C6) alkoxy- (Ci-C6) alkyl, (C 2 -C 6 ) cyanoalkenyl, (C 3 -C 6 ) cycloalkyl- (C 2 -C 6 ) alkenyl, (C 2 - C6) cyanoalkynyl, (C 3 -C 6 ) cycloalkyl- (C 2 -C 6 ) alkynyl , (Ci-C6) haloalkoxy- (Ci-C6) alkyl, (C 2 - C6) alkenyloxy- (Ci-C6) alkyl, (C 2 -C 6 ) haloalkenyloxy- (Ci-C 6 ) alkyl, (C 2 -C 6) alkynyloxy (Ci- C alkyl 4), (C 2 -C 6) Halogenalkinyloxy- (Ci-C 6) alkyl, (Ci-C6) alkylthio (Ci-C6) alkyl, (Ci- C6) Alkylsulfinyl- (Ci-C6) alkyl, (Ci-C6) alkylsulfonyl- (Ci-C6) alkyl, (Ci-C6) haloalkylthio- (Ci-C ö ) alkyl, (Ci-C6) halogen alkylsulfinyl- (Ci-C6) alkyl, (Ci-C6) haloalkylsulfonyl- (Ci-C6) alkyl, or tri- (Ci-C6) alkylsilyl,
R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci- Ce)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C6)Halogenalkylthio, (Ci-C6)Halogenalkylsulfinyl, (Ci- C6)Halogenalkylsulfonyl oder für (Ci-C6)Halogenalkyl-(C3-C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-C8)cycloalkyl, (Ci- C6)Halogenalkyl-(C3-C8)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-C8)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-Cö)Alkyl oder Halogen substituiertes Cyano(C3- C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes Spiro-(C3-C8)cycloalkyl-(C3-C8)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes (C4-Ci2)Bicycloalkyl stehen, wobei einer der Reste R2 oder R3 ausgewählt sein muss aus Ci-C6)Halogenalkyl-(C3- C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-C8)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-R 2 , R 3 independently of one another for hydrogen, halogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-Ce) alkoxy, (Ci-C6) haloalkoxy, (Ci-C6) haloalkylthio, (Ci C6) haloalkylsulfinyl, (Ci-C6) haloalkylsulfonyl or for (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) halocycloalkyl, optionally singly or multiply substituted by (Ci-C ö ) alkyl or halogen-substituted cyano (C3-C6 ) cycloalkyl, spiro (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, optionally mono- or polysubstituted with cyano or halogen, or optionally mono- or polysubstituted with cyano or halogen (C 4 -Ci 2 ) bicycloalkyl , where one of the radicals R 2 or R 3 must be selected from Ci-C6) haloalkyl- (C3- C8) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -C8) cycloalkyl, (Ci-C6) haloalkyl- (C3-
C8)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-C8)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-Cö)Alkyl oder Halogen substituiertem Cyano(C3-C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem Spiro-(C3- C8)cycloalkyl-(C3-C8)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem (C4-Ci2)Bicycloalkyl, n für 0, 1 oder 2 steht, C8) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) halogenocycloalkyl, optionally mono- or polysubstituted by (Ci-C ö ) alkyl or halogen-substituted cyano (C 3 -C 6 ) cycloalkyl, optionally singly or multiply spiro (C3-C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl substituted with cyano or halogen or optionally (C 4 -Ci 2 ) bicycloalkyl mono- or polysubstituted with cyano or halogen, n represents 0, 1 or 2,
Q für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql bis Q5 steht , Q stands for a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1 to Q5,
wobei in which
R4 für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Hydroxyalkyl, (Ci- C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci-C4)Alkylcarbonyl-(Ci-C4)alkyl steht, Alkyl R 4 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci-C 4) hydroxyalkyl, (Ci C 4) alkoxy (Ci-C 4) , (Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) (4 Ci-C) alkyl Halogenalkenyloxy-, (C 2 -C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (C 4 ) alkyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkylthio- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfinyl- (Ci-C 4 ) alkyl, ( Ci-C 4 ) alkylsulfonyl- (Ci-C 4 ) alkyl or (Ci-C 4 ) alkylcarbonyl- (Ci-C 4 ) alkyl,
R5 für (Ci-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (Ci-C6)Halogenalkyl, (C2-C6)Halogenalkenyl, (C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl oder Halogen(C3-Cs)cycloalkyl steht, R 5 is for (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) Haloalkynyl, (C 3 -Cs) cycloalkyl or halogen (C 3 -Cs) cycloalkyl,
R6 für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2- C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3- C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkoxyimino, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci- C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-R 6 for hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4 ) Alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 - C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl- (C 3 - C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C4) alkoxyimino, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci- C4 ) Alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci
C4)Halogenalkylsulfonyl, (Ci-C4)Alkylsulfonyloxy, (Ci-C4)Alkylcarbonyl, (Ci- C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl- aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci-C4)Alkylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl oder Di-(Ci-C4)alkylaminosulfonyl steht und A für N (Stickstoff) oder C(H) steht. C 4 ) haloalkylsulfonyl, (Ci-C 4 ) alkylsulfonyloxy, (Ci-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkylaminocarbonyl , (Ci-C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylamino, di- (Ci-C 4 ) alkylamino, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl or di- (Ci-C 4 ) alkylaminosulfonyl and A stands for N (nitrogen) or C (H).
Weiterhin wurde gefunden, dass die Verbindungen der Formel (1) eine sehr gute Wirksamkeit als Schädlingsbekämpfungsmittel, vorzugsweise als lnsektizide und/oder Akarizide aufweisen, darüber hinaus in der Regel insbesondere gegenüber Kulturpflanzen sehr gut pflanzenverträglich sind. It has furthermore been found that the compounds of the formula (1) have very good activity as pesticides, preferably as insecticides and / or acaricides, and moreover are generally very well tolerated by plants, in particular particularly against crop plants.
Die erfindungsgemäßen Verbindungen sind durch die Formel (1) allgemein definiert. Bevorzugte Substituenten bzw. Bereiche der in der oben und nachstehend erwähnten Formeln aufgeführten Reste werden im Folgenden erläutert: The compounds according to the invention are generally defined by the formula (1). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
Ausgestaltung 2 Design 2
R1 steht bevorzugt für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Alkinyl, (C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl, Halogen(C3-Cs)cycloalkyl, (C3- C6)Cycloalkyl-(Ci-C6)alkyl, (C3-C6)Cycloalkyl-(Ci-C6)halogenalkyl, (Ci-C6)Alkyl-(C3- Cs)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, (Ci-C6)Cyanoalkyl, (Ci- C6)Hydroxyalkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (Ci- C6)Alkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfmyl-(Ci-C6)alkyl oder (Ci-C6)Alkylsulfonyl-(Ci- C6)alkyl, R 1 preferably represents (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 - C 6 ) haloalkynyl, (C 3 -Cs) cycloalkyl, halogen (C 3 -Cs) cycloalkyl, (C 3 - C6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6 ) cycloalkyl- (Ci-C haloalkyl 6), (Ci-C6) alkyl- (C3-Cs) cycloalkyl, (Ci-C 6) haloalkyl (C 3 -Cs) cycloalkyl, (Ci-C6) cyanoalkyl, (Ci- C6) hydroxyalkyl, (C -C6) alkoxy- (Ci-C6) alkyl, (Ci-C6) haloalkoxy- (Ci-C6) alkyl, (Ci- C6) alkylthio- (Ci-C6) alkyl, (Ci-C6) alkylsulfmyl- (Ci C6) alkyl or (Ci-C6) alkylsulfonyl- (Ci-C6) alkyl,
R2, R3 stehen bevorzugt unabhängig voneinander für Wasserstoff, Halogen, (Ci-C6)Alkyl, (Ci- C6)Halogenalkyl, (Ci-C6)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C6)Halogenalkylthio, (Ci- C6)Halogenalkylsulfmyl, (Ci-C6)Halogenalkylsulfonyl oder für (Ci-C6)Halogenalkyl-(C3-C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-Cs)cycloalkyl, (Ci- C6)Halogenalkyl-(C3-Cg)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-C4)Alkyl oder Halogen substituiertes Cyano(C3- C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes Spiro-(C3-C8)cycloalkyl-(C3-C8)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes (C4-Ci2)Bicycloalkyl, wobei einer der Reste R2 oder R3 ausgewählt sein muss aus (Ci-C6)Halogenalkyl-(C3- C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-C8)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-R 2 , R 3 are preferably independently of one another hydrogen, halogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy, (Ci-C6) haloalkoxy, (Ci-C6) haloalkylthio, ( Ci-C6) haloalkylsulfmyl, (Ci-C6) haloalkylsulfonyl or for (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -Cs) cycloalkyl, (Ci C 6 ) haloalkyl- (C 3 -Cg) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) halocycloalkyl, optionally single or multiple cyano (C3-C6) substituted by (Ci-C 4 ) alkyl or halogen cycloalkyl, spiro (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, optionally mono- or polysubstituted with cyano or halogen, or optionally mono- or polysubstituted with cyano or halogen (C 4 -Ci 2 ) bicycloalkyl, where one of the radicals R 2 or R 3 must be selected from (Ci-C6) haloalkyl- (C3- C8) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -C8) cycloalkyl, (Ci-C6) haloalkyl- ( C3-
C8)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-C8)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-C4)Alkyl oder Halogen substituiertem Cyano(C3-C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem Spiro-(C3- C8)cycloalkyl-(C3-C8)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem (C4-Ci2)Bicycloalkyl, n steht bevorzugt für 0, 1 oder 2, Q steht bevorzugt für ein heteroaromatisches 9-gliedriges oder l2-gliedriges anne liiertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql bis Q5, C8) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) halogenocycloalkyl, optionally singly or multiply by (Ci-C 4 ) alkyl or halogen-substituted cyano (C 3 -C 6 ) cycloalkyl, optionally singly or multiply spiro (C3-C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl substituted with cyano or halogen or optionally (C 4 -Ci 2 ) bicycloalkyl mono- or polysubstituted with cyano or halogen, n is preferably 0, 1 or 2, Q preferably represents a heteroaromatic 9-membered or 12-membered anne lyated bicyclic or tricyclic ring system from the series Q1 to Q5,
wobei in which
R4 bevorzugt für (Ci-CQAlkyl, (Ci-C4)Halogenalkyl, (Ci-CQCyanoalkyl, (Ci-CQHydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci-C4)Alkylcarbonyl-(Ci-C4)alkyl steht, R 4 preferably for (Ci-CQ-alkyl, (Ci-C 4 ) haloalkyl, (Ci-CQ-cyanoalkyl, (Ci-CQ hydroxy alkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy - (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) haloalkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) cyanoalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) alkynyloxy- (Ci-C 4 ) alkyl, (C 2 - C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkylthio- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfinyl- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfonyl- ( Ci-C 4 ) alkyl or (Ci-C 4 ) alkylcarbonyl- (Ci-C 4 ) alkyl,
R5 bevorzugt für (Ci-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (Ci-C6)Halogenalkyl, (C2-R 5 preferably for (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C6) haloalkyl, (C 2 -
C6)Halogenalkenyl, (C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl oder Halogen(C3-Cs)cycloalkyl steht, C6) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (C 3 -Cs) cycloalkyl or halogen (C 3 -Cs) cycloalkyl,
R6 bevorzugt für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C2-R 6 preferably represents hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -
C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkoxyimino, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci- C4)Alkylsulfmyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C4) alkoxyimino, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfmyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci
C4)Halogenalkylsulfonyl, (Ci-C4)Alkylsulfonyloxy, (Ci-C4)Alkylcarbonyl, (Ci- C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl- aminocarbonyl, (Ci-C4)Alkylsulfonylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl oder Di-(Ci-C4)alkylaminosulfonyl steht und A bevorzugt für N (Stickstoff) oder C(H) steht. C 4 ) haloalkylsulfonyl, (Ci-C 4 ) alkylsulfonyloxy, (Ci-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkylaminocarbonyl , (Ci-C 4 ) alkylsulfonylamino, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl or di- (Ci-C 4 ) alkylaminosulfonyl and A preferably represents N (nitrogen) or C (H).
Ausgestaltung 3 Design 3
R1 steht besonders bevorzugt für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl oder (C3-Cs)Cycloalkyl, R2 steht besonders bevorzugt für Wasserstoff, Halogen, (Ci-C Alkyl, (Ci-C4)Halogenalkyl, (Ci- C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Halogenalkylthio, (Ci-C4)Halogenalkylsulfinyl oder (C i -C4)Halogenalkylsulfonyl, R 1 particularly preferably represents (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C 3 -Cs) cycloalkyl, R 2 particularly preferably represents hydrogen, halogen, (Ci-C alkyl, (Ci-C 4) haloalkyl, (CI-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C4) haloalkylthio, (Ci-C4) haloalkylsulfinyl or (C i -C 4) haloalkylsulfonyl,
R3 steht besonders bevorzugt für (Ci-C4)Halogenalkyl-(C3-Cs)cycloalkyl, Spiro-(C3-Cs)cycloalkyl- (C3-Cs)cycloalkyl, (C4-Ci2)Bicycloalkyl oder gegebenfalls einfach oder zweifach durch (Ci- C4)Alkyl oder Halogen substituiertes Cyano(C3-C6)cycloalkyl, n steht besonders bevorzugt für 0, 1 oder 2, R 3 particularly preferably represents (Ci-C 4 ) haloalkyl- (C 3 -Cs) cycloalkyl, spiro- (C 3 -Cs) cycloalkyl- (C 3 -Cs) cycloalkyl, (C 4 -Ci 2 ) bicycloalkyl or optionally Cyano (C 3 -C 6 ) cycloalkyl substituted once or twice by (Ci-C 4 ) alkyl or halogen, n is particularly preferably 0, 1 or 2,
Q steht besonders bevorzugt für ein heteroaromatisches 9-gliedriges oder 12-gliedriges anne liiertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql bis Q5, Q particularly preferably represents a heteroaromatic 9-membered or 12-membered anne lied bicyclic or tricyclic ring system from the series Q1 to Q5,
wobei in which
R4 besonders bevorzugt für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci- C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl oder (C3-R 4 particularly preferably represents (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci C 4) alkoxy alkyl (Ci-C 4), (Ci-C 4 ) Haloalkoxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkynyl, (C 2 - C 4 ) alkynyloxy- (Ci-C 4 ) alkyl or (C 3 -
C6)Cycloalkyl steht, R5 besonders bevorzugt für (Ci-C6)Halogenalkyl, (C2-C6)Halogenalkenyl, (C2-C6)Halogenalkinyl oder Halogen(C3-C8)cycloalkyl steht, C 6 ) cycloalkyl, R 5 particularly preferably represents (Ci-C 6 ) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl or halogen (C 3 -C 8 ) cycloalkyl,
R6 besonders bevorzugt für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3- C6)Cycloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Alkylthio, (Ci- C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfmyl, (Ci-C4)Alkylsulfonyl oder (Ci-C4)Halogenalkylsulfonyl steht und R 6 particularly preferably for hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 - C 6 ) cycloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) Haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfmyl, (Ci-C 4 ) alkylsulfonyl or (Ci-C 4 ) haloalkylsulfonyl and
A besonders bevorzugt für N (Stickstoff) oder C(H) steht. A particularly preferably represents N (nitrogen) or C (H).
Ausgestaltung 4 R1 steht ganz besonders bevorzugt für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl oder (C3-Cs)Cycloalkyl, Embodiment 4 R 1 very particularly preferably represents (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C 3 -Cs) cycloalkyl,
R2 steht ganz besonders bevorzugt für Wasserstoff, (Ci-C4)Alkyl oder Halogen, R 2 very particularly preferably represents hydrogen, (Ci-C 4 ) alkyl or halogen,
R3 steht ganz besonders bevorzugt für (Ci-C4)Halogenalkyl-(C3-Cs)cycloalkyl, Spiro-(C3- C8)cycloalkyl-(C3-Cs)cycloalkyl oder Cyano(C3-C6)cycloalkyl, n steht ganz besonders bevorzugt für 0, 1 oder 2, Q steht ganz besonders bevorzugt für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql, Q2, Q3 und Q5, R 3 very particularly preferably represents (Ci-C 4 ) haloalkyl- (C 3 -Cs) cycloalkyl, spiro- (C 3 - C 8 ) cycloalkyl- (C 3 -Cs) cycloalkyl or cyano (C 3 -C 6 ) cycloalkyl, n very particularly preferably represents 0, 1 or 2, Q very particularly preferably represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2, Q3 and Q5,
Q5 wobei  Q5 where
R4 ganz besonders bevorzugt für (Ci-C4)Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl steht, R5 ganz besonders bevorzugt für (Ci-C6)Halogenalkyl steht, R6 ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Methoxy, Cyano, Halogen oder (Ci- C2)Halogenalkyl steht und R 4 very particularly preferably represents (Ci-C 4 ) alkyl or (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, R 5 very particularly preferably represents (Ci-C 6 ) haloalkyl, R 6 very particularly preferably represents hydrogen, methyl, ethyl, methoxy, cyano, halogen or (Ci-C2) haloalkyl and
A ganz besonders bevorzugt für N (Stickstoff) oder C(H) steht. A very particularly preferably represents N (nitrogen) or C (H).
Ausgestaltung 5 Design 5
R1 steht hervorgehoben für (Ci-CQAlkyl, R 1 stands for (Ci-CQ-alkyl,
R2 steht hervorgehoben für Wasserstoff, R 2 stands for hydrogen,
R3 steht hervorgehoben für Cyanocyclopropyl oder Cyanocylcobutyl, n steht hervorgehoben für 2, R 3 stands for cyanocyclopropyl or cyanocyl cobutyl, n stands for 2,
Q steht hervorgehoben für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql, Q2 und Q5, Q stands out for a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2 and Q5,
wobei in which
R4 hervorgehoben für (Ci-CQAlkyl steht, R 4 is highlighted for (Ci-CQalkyl,
R5 steht hervorgehoben für (Ci-CQHalogenalkyl steht, R6 hervorgehoben für Wasserstoff steht und R 5 stands for (Ci-CQHalogenalkyl stands, R 6 stands for hydrogen and
A hervorgehoben für N (Stickstoff) oder C(H) steht. A stands for N (nitrogen) or C (H).
Ausgestaltung 6- 1 R1 steht insbesonders für Ethyl, R2 steht insbesonders für Wasserstoff, R3 steht insbesonders für 1 -Cyanocyclopropyl, n steht insbesonders für 2, Design 6- 1 R 1 stands especially for ethyl, R 2 stands especially for hydrogen, R 3 stands in particular for 1-cyanocyclopropyl, n stands in particular for 2,
Q steht insbesonders für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql, Q2 und Q5, Q in particular represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2 and Q5,
wobei in which
R4 insbesonders für Methyl steht, R5 insbesonders für Trifluormethyl steht, R 4 stands in particular for methyl, R 5 stands in particular for trifluoromethyl,
R6 insbesonders für Wasserstoff steht und R 6 in particular represents hydrogen and
A insbesonders für N (Stickstoff) oder C(H) steht. A is especially N (nitrogen) or C (H).
Ausgestaltung 6-2 R1 steht insbesonders für Ethyl, Design 6-2 R 1 stands in particular for ethyl,
R2 steht insbesonders für Wasserstoff, R 2 stands in particular for hydrogen,
R3 steht insbesonders für 1 -Cyanocyclopropyl, n steht insbesonders für 2, R 3 stands in particular for 1-cyanocyclopropyl, n stands in particular for 2,
Q steht insbesonders für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql, Q2 und Q5, wobei Q in particular represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2 and Q5, in which
R4 insbesonders für Methyl steht, R5 insbesonders für Trifluormethyl oder Pentafluorethyl steht, R6 insbesonders für Wasserstoff steht und R 4 is in particular methyl, R 5 is in particular trifluoromethyl or pentafluoroethyl, R 6 is in particular hydrogen and
A insbesonders für N (Stickstoff) oder C(H) steht. A is especially N (nitrogen) or C (H).
Im speziellen umfasst die Erfindung folgende Struktur der Formel (I-A) In particular, the invention comprises the following structure of formula (I-A)
in welcher R1, R2, R3, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. Im speziellen umfasst die vorliegende Erfindung folgende Struktur der Formel (I-B) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration ( 6) have the meanings described. In particular, the present invention comprises the following structure of the formula (IB)
in welcher R1, R2, R3, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration ( 6) have the meanings described.
Im speziellen umfasst die vorliegende Erfindung folgende Struktur der Formel (I-C) In particular, the present invention comprises the following structure of the formula (I-C)
in welcher R1, R2, R3, R4, A und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. in which R 1 , R 2 , R 3 , R 4 , A and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration (6) to have.
Der Bergiff Formel (I) umfasst im folgenden selbstverständlich auch die unter Formel (I) fallenden Formeln (I-A) bis (I-C). In the following, the Bergiff formula (I) naturally also includes the formulas (I-A) to (I-C) falling under formula (I).
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, n für 2 steht und wobei R1, R2, R3, Q, A, R4, R5 und R6 die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) beschriebenen Bedeutungen haben. In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which n is 2 and where R 1 , R 2 , R 3 , Q, A, R 4 , R 5 and R 6 have the form ( 1) or configuration (2) or configuration (3) or configuration (4) have the meanings described.
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl oder (C3-Cs)Cycloalkyl steht und R2, R3, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 1 is (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C3-Cs) cycloalkyl and R 2 , R 3 , Q, A, R 4 , R 5 , R 6 and n are in the embodiment (1) or configuration (2) or configuration (5) or configuration (6) have the meanings described.
In einer besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, In a particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which
R1 für (Ci-C Alkyl steht und R2, R3, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 1 stands for (Ci-C alkyl and R 2 , R 3 , Q, A, R 4 , R 5 , R 6 and n are those in embodiment (1) or embodiment (2) or embodiment (3) or embodiment (4th ) or configuration (6) have the meanings described.
In einer ganz besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, R1 für Ethyl steht und R2, R3, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) beschriebenen Bedeutungen haben. In a very particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which R 1 stands for ethyl and R 2 , R 3 , Q, A, R 4 , R 5 , R 6 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration ( 5) have the meanings described.
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, wenigstens einer der Reste R2 oder R3 für Cyano(C3-C6)cycloalkyl, bevorzugt für l-Cyanocyclopropyl steht und der jeweils andere Rest ausgewählt ist aus Wasserstoff, (Ci-C4)Alkyl oder Halogen und R1, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which at least one of the radicals R 2 or R 3 is cyano (C3-C6) cycloalkyl, preferably l-cyanocyclopropyl and the other radical is selected from hydrogen, (Ci-C4) alkyl or halogen and R 1 , Q, A, R 4 , R 5 , R 6 and n which are in the configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6) have meanings described.
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which
R2 für Wasserstoff, (Ci-C4)Alkyl oder Halogen steht und R1, R3, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 2 represents hydrogen, (Ci-C4) alkyl or halogen and R 1 , R 3 , Q, A, R 4 , R 5 , R 6 and n are those in embodiment (1) or embodiment (2) or embodiment (3 ) or configuration (5) or configuration (6) meanings described.
In einer besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, In a particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which
R2 für Wasserstoff steht und R1, R3, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) beschriebenen Bedeutungen haben. R 2 stands for hydrogen and R 1 , R 3 , Q, A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) .
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which
R3 für (Ci-C4)Halogenalkyl-(C3-C8)cycloalkyl, Spiro-(C3-C8)cycloalkyl-(C3-Cs)cycloalkyl oder Cyano(C3-C6)cycloalkyl steht, und R1, R2, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 3 represents (Ci-C4) haloalkyl- (C3-C8) cycloalkyl, spiro- (C3-C8) cycloalkyl- (C3-Cs) cycloalkyl or cyano (C3-C6) cycloalkyl, and R 1 , R 2 , Q , A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6).
In einer besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, In a particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which
R3 für Cyano(C3-C6)cycloal yl steht und R1, R2, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 3 represents cyano (C3-C6) cycloal yl and R 1 , R 2 , Q, A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (6) .
In einer ganz besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, R3 für l-Cyanocyclopropyl steht und R1, R2, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) beschriebenen Bedeutungen haben. In a very particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which R 3 is 1-cyanocyclopropyl and R 1 , R 2 , Q, A, R 4 , R 5 , R 6 and n are those in Design (1) or design (2) or design (3) or design (4) or design (5) have the meanings described.
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, R2 für Wasserstoff steht und R3 für 1 -Cyanocyclopropyl steht und R1, Q, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is 1-cyanocyclopropyl and R 1 , Q, A, R 4 , R 5 , R 6 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (5) or configuration (6).
Erfindungsgemäß insbesondere bevorzugt sind Verbindungen der Formel (G) According to the invention, particular preference is given to compounds of the formula (G)
(O, wobei Q, R4, R5 und R6 die in Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. (O, where Q, R 4 , R 5 and R 6 have the meanings described in configuration (3) or configuration (4) or configuration (5) or configuration (6).
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, Q für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 bis Q5 steht , In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1 to Q5,
und R1, R2, R3, A, R4, R5, R6 und n die in Ausgestaltung (4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. and R 1 , R 2 , R 3 , A, R 4 , R 5 , R 6 and n have the meanings described in configuration (4) or configuration (5) or configuration (6).
In einer besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, Q für ein heteroaromatisches 9-gliedriges oder l2-gliedriges anne liiertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 , Q2, Q3 und Q5 steht , In a particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered anne lyzed bicyclic or tricyclic ring system from the series Q 1, Q2, Q3 and Q5,
Q5 und R1, R2, R3, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. Q5 and R 1 , R 2 , R 3 , A, R 4 , R 5 , R 6 and n are those described in configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6) Have meanings.
In einer ganz besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, Q für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 , Q2 und Q5 steht , und R1, R2, R3, A, R4, R5, R6 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder AusgestaltungIn a very particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5, and R 1 , R 2 , R 3 , A, R 4 , R 5 , R 6 and n in the configuration (1) or configuration (2) or configuration
(3) oder Ausgestaltung (4) beschriebenen Bedeutungen haben. (3) or configuration (4) have the meanings described.
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which
R5 für (Ci-C6)Halogenalkyl, (C2-C6)Halogenalkenyl, (C2-C6)Halogenalkinyl oder Halogen(C3- Cs)cycloalkyl steht,, und Q, R1, R2, R3 R4, R6, A und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder AusgestaltungR 5 represents (Ci-C 6 ) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl or halogen (C3-Cs) cycloalkyl, and Q, R 1 , R 2 , R 3 R 4 , R 6 , A and n in the configuration (1) or configuration (2) or configuration
(4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. (4) or configuration (5) or configuration (6) have the meanings described.
In einer besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher In a particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which
R5 für (Ci-C6)Halogenalkyl, bevorzugt für (Ci-C4)Halogenalkyl steht, und Q, R1, R2, R3 R4, R6, A und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 5 stands for (Ci-C 6 ) haloalkyl, preferably for (Ci-C4) haloalkyl, and Q, R 1 , R 2 , R 3 R 4 , R 6 , A and n are those in embodiment (1) or embodiment ( 2) or configuration (3) or configuration (4) or configuration (5) or configuration (6) have the meanings described.
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher R4 für (Ci-C4)Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl steht, In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which R 4 represents (Ci-C4) alkyl or (Ci-C4) alkoxy- (Ci-C4) alkyl,
R5 für (Ci-C6)Halogenalkyl steht, R 5 represents (Ci-C 6 ) haloalkyl,
R6 für Wasserstoff, Methyl, Ethyl, Methoxy, Cyano, Halogen oder (Ci-C2)Halogenalkyl steht und A für N (Stickstoff) oder C(H) steht, und Q, R1, R2, R3 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 6 represents hydrogen, methyl, ethyl, methoxy, cyano, halogen or (Ci-C2) haloalkyl and A represents N (nitrogen) or C (H), and Q, R 1 , R 2 , R 3 and n have the meanings described in configuration (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6).
In einer besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher In a particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which
R4 für (Ci-C4)Alkyl steht, R 4 represents (Ci-C4) alkyl,
R5 für (Ci-C4)Halogenalkyl steht, R 5 represents (Ci-C4) haloalkyl,
R6 für Wasserstoff steht und R 6 represents hydrogen and
A für N (Stickstoff) oder C(H) steht, und R1, R2, R3 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. A stands for N (nitrogen) or C (H), and R 1 , R 2 , R 3 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (6) have the meanings described.
In einer ganz besonders bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, Q für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 , Q2 und Q5 steht, wobei In a very particularly preferred embodiment, the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5, where
R4 für (Ci-C Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl steht, R 4 represents (Ci-C alkyl or (Ci-C4) alkoxy- (Ci-C4) alkyl,
R5 für (Ci-C6)Halogenalkyl steht, R 5 represents (Ci-C 6 ) haloalkyl,
R6 für Wasserstoff, Methyl, Ethyl, Methoxy, Cyano, Halogen oder (Ci-C2)Halogenalkyl steht und A für N (Stickstoff) oder C(H) steht, und R1, R2, R3 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (5) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. R 6 represents hydrogen, methyl, ethyl, methoxy, cyano, halogen or (Ci-C2) haloalkyl and A represents N (nitrogen) or C (H), and R 1 , R 2 , R 3 and n are in the embodiment (1) or configuration (2) or configuration (3) or configuration (5) or configuration (6) have the meanings described.
In einer hervorgehobenen Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I), in welcher, Q für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 , Q2 und Q5 steht, wobei In a highlighted embodiment, the invention relates to the compounds of the formula (I) in which Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5, in which
R4 für (Ci-C4)Alkyl steht, R 4 represents (Ci-C4) alkyl,
R5 für (Ci-C4)Halogenalkyl steht, R 5 represents (Ci-C4) haloalkyl,
R6 für Wasserstoff steht und R 6 represents hydrogen and
A für N (Stickstoff) oder C(H) steht, und R1, R2, R3 und n die in Ausgestaltung (1) oder Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (6) beschriebenen Bedeutungen haben. A stands for N (nitrogen) or C (H), and R 1 , R 2 , R 3 and n are those in configuration (1) or configuration (2) or configuration (3) or configuration (4) or configuration (6) have the meanings described.
In den bevorzugten Definitionen ist, sofern nichts anderes angegeben ist, Unless otherwise stated, in the preferred definitions
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom. Halogen selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkyl, im Rahmen der vorliegenden Erfindung ein Rest einer gesättigten, aliphatischen Kohlenwasserstoffgruppe mit 1 bis 12 Kohlenstoffatomen verstanden, die verzweigt oder unverzweigt sein kann. Beispiele für Ci- Ci2-Alkylreste sind Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sek.-Butyl, tert.-Butyl, n- Pentyl, iso-Pentyl, Neopentyl, tert.-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 1 -Ethylpropyl, 1,2- Dimethylpropyl, Hexyl n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl und n-Dodecyl. Von diesen Alkylresten sind Ci-CVAlkylrcstc besonders bevorzugt. Insbesondere bevorzugt sind Ci-C4-Alkylreste. 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 residue of a saturated, aliphatic hydrocarbon group with 1 to 12 carbon atoms, which can be branched or unbranched. Examples of Ci-Ci2-alkyl radicals are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert. -Pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Of these alkyl radicals, Ci-CValkyl radicals are particularly preferred. Ci-C4-alkyl radicals are particularly preferred.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkenyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-Ci2-Alkenylrest, welcher mindestens eine Doppelbindung aufweist, beispielsweise Vinyl, Allyl, 1-Propenyl, Isopropenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1,3-Butadienyl, 1-Pentenyl, 2- Pentenyl, 3-Pentenyl, 4-Pentenyl, 1,3-Pentadienyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl und 1 ,4-Hexadienyl, verstanden. Bevorzugt hiervon sind C2-C6-Alkenylreste und besonders bevorzugt sind C2-C4-Alkenylreste. Unless otherwise defined elsewhere, the term “alkenyl”, either alone or in combination with other terms, according to the invention is a linear or branched C2-Ci2-alkenyl radical which has 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, understood. Of these, C2-C6 alkenyl radicals are preferred, and C2-C4 alkenyl radicals are particularly preferred.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkinyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-Ci2-Alkinylrest, welcher mindestens eine Dreifachbindung aufweist, beispielsweise Ethinyl, 1-Propinyl und Propargyl, verstanden. Bevorzugt hiervon sind C3-C6-Alkinylreste und besonders bevorzugt sind C3-C4-Alkinylreste. Der Alkinylrest kann dabei auch mindestens eine Doppelbindung aufweisen. Unless otherwise defined elsewhere, the term “alkynyl”, either alone or in combination with other terms, according to the invention is a linear or branched C2-Ci2-alkynyl radical which has at least one triple bond, for example ethynyl, 1-propynyl and propargyl, understood. Of these, C3-C6-alkynyl radicals and are preferred C3-C4-alkynyl radicals are particularly preferred. The alkynyl radical can also have at least one double bond.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Cycloalkyl“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein C3-C8- Cycloalkylrest verstanden, beispielsweise Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl und Cyclooctyl, verstanden. Bevorzugt hiervon sind C3-C6-Cycloalkylreste. Unless otherwise defined elsewhere, the term “cycloalkyl”, either alone or in combination with other terms, is understood according to the invention to mean a C3-C8 cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl . Of these, C3-C6-cycloalkyl radicals are preferred.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Bicycloalkyl” entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein Bicyclus verstanden, dessen beide Ringe über eine gemeinsame Einfachbindung verfügen. Die beiden Cyclen können dabei die gleiche oder eine unterschiedliche Anzahl an Kohlenstoffatomen aufweisen. Beispielsweise seinen genannt Bicyclo[l.l.0]butan oder Bicyclo[2. l.0]pentan. Unless otherwise defined elsewhere, the term “bicycloalkyl”, either alone or in combination with other terms, is understood according to the invention to mean a bicyclus, the two rings of which have a common single bond. The two cycles can have the same or a different number of carbon atoms. For example, its called Bicyclo [l.l.0] butane or Bicyclo [2. l.0] pentane.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff„Spiro-Cycloalkyl-Cycloalkyl” entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß eine Verbindung verstanden, bei welcher zwei Cycloalkyl-Ringe über ein gemeinsames Kohlenstoffatom verbunden sind. Die beiden Cyclen können dabei die gleiche oder eine unterschiedliche Anzahl an Kohlenstoffatomen aufweisen. Beispielsweise seinen genannt Spiro[2.2]pentan (Spiro-(Cyclopropyl)-(Cyclopropyl)) oder Spiro[2.3]hexan (Spiro-(Cyclopropyl)- (Cyclobutyl)). Unless otherwise defined elsewhere, the term “spiro-cycloalkyl-cycloalkyl”, either alone or in combination with other terms, is understood according to the invention to mean a compound in which two cycloalkyl rings are connected via a common carbon atom. The two cycles can have the same or a different number of carbon atoms. For example, its called spiro [2.2] pentane (spiro- (cyclopropyl) - (cyclopropyl)) or spiro [2.3] hexane (spiro- (cyclopropyl) - (cyclobutyl)).
Unter dem Begriff „Alkoxy“, entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkoxy, wird vorliegend ein Rest O-Alkyl verstanden, wobei der Begriff„Alkyl“ die oben stehende Bedeutung aufweist. The term “alkoxy”, either alone or in combination with other terms, such as, for example, haloalkoxy, is understood here to mean an O-alkyl radical, the term “alkyl” having the meaning given above.
Durch Halogen substituierte Reste, z.B. Halogenalkyl (=Haloalkyl), sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halo genatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder Iod, insbesondere für Fluor, Chlor oder Brom. Halogen substituted residues e.g. Haloalkyl (= haloalkyl), are halogenated once or several times to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be the same or different. Halogen represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Gegebenenfalls substituierte Reste können, wenn nichts anderes erwähnt ist, einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. Unless otherwise stated, optionally substituted radicals can be mono- or polysubstituted, in the case of multiple substitutions the substituents can be the same or different.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. Erfindungsgemäß bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt. The general definitions or explanations of residues or explanations given above or in preferred areas apply accordingly to the end products and to the starting products and intermediate products. These residual definitions can be combined with one another, i.e. also between the respective preferred areas. According to the invention, preference is given to using compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.
Erfindungsgemäß besonders bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. According to the invention, particular preference is given to using compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
Erfindungsgemäß ganz besonders bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. According to the invention, very particular preference is given to using compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
Erfindungsgemäß hervorgehoben verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als hervorgehoben aufgeführten Bedeutungen vorliegt. Compounds of the formula (I) in which a combination of the meanings listed above as highlighted are present are used according to the invention.
Erfindungsgemäß insbesonders verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als insbesonders aufgeführten Bedeutungen vorliegt. According to the invention, particular use is made of compounds of the formula (I) in which there is a combination of the meanings given above as particularly mentioned.
Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit reine Stereo isomere als auch beliebige Gemische dieser Isomere. Depending on the nature of the substituents, the compounds of the formula (I) can be present in different compositions as geometric and / or as optically active isomers or corresponding isomer mixtures. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus includes pure stereo isomers as well as any mixtures of these isomers.
Die Verbindungen der Formel (I) können auch als Salze, insbesondere Säureadditionssalze und Metall salzkomplexe, vorliegen. Die Verbindungen der Formel (I) und deren Säureadditionssalze und Metall salzkomplexe besitzen gute Wirksamkeit, insbesondere zur Bekämpfung von tierischen Schädlingen. The compounds of formula (I) can also be present as salts, in particular acid addition salts and metal salt complexes. The compounds of formula (I) and their acid addition salts and metal salt complexes have good activity, in particular for combating animal pests.
Als geeignete Salze der Verbindungen der allgemeinen Formel (I) können übliche nicht toxische Salze, d. h. Salze mit entsprechenden Basen und Salze mit zugesetzten Säuren genannt werden. Vorzugsweise sind Salze mit anorganischen Basen, wie Alkalimetallsalze, beispielsweise Natrium-, Kalium- oder Cäsiumsalze, Erdalkalimetallsalze, beispielsweise Calzium- oder Magnesiumsalze, Ammoniumsalze, Salze mit organischen Basen sowie mit anorganischen Aminen, beispielsweise Triethylammonium-, Dicyclohexylammonium-, N,N‘-Dibenzylethylendiammonium-, Pyridinium-, Picolinium- oder Ethanolammoniumsalze, Salze mit anorganischen Säuren, beispielsweise Hydrochloride, Hydrobromide, Dihydrosulfate, Trihydrosulfate, oder Phosphate, Salze mit organischen Carbonsäuren oder organischen Sulfosäure, beispielsweise Formiate, Acetate, Trifluoracetate, Maleate, Tartrate, Methansulfonate, Benzolsulfonate oder para-Toluolsulfonate, Salze mit basischen Aminosäuren, beispielsweise Arginate, Aspartate oder Glutamate und Ähnliches zu nennen. Die erfindungsgemäßen Verbindungen der Formel (I) können durch die in den folgenden Schemata dargestellten Verfahren erhalten werden: Suitable non-toxic salts of the compounds of the general formula (I) which can be mentioned are customary non-toxic salts, ie salts with corresponding bases and salts with added acids. Preferred are salts with inorganic bases, such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases and with inorganic amines, for example triethylammonium, dicyclohexylammonium, N, N'- Dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, or phosphates, salts with organic carboxylic acids or organic sulfonic acid, for example formates, acetates, trifluoroacetates, benzol sulfates, maleates, metheates sulfates or para-toluenesulfonates, salts with basic amino acids, for example arginates, aspartates or glutamates and the like. The compounds of the formula (I) according to the invention can be obtained by the processes shown in the following schemes:
Verfahren A Procedure A
Die Reste R1, R2, R3, R4, R5, R6 und n haben die oben beschriebenen Bedeutungen, A2 und A3 stehen für CH oder N und X1 steht für Halogen. The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n have the meanings described above, A 2 and A 3 represent CH or N and X 1 represents halogen.
Schritt a) Step a)
Die Verbindungen der Formel (IV) können in Analogie zu dem in US5576335 beschriebenen Verfahren durch die Umsetzung von Verbindungen der Formel (II) mit Carbonsäuren der Formel (III) in Gegenwart eines Kondensationsmittels bzw. einer Base hergestellt werden. The compounds of the formula (IV) can be prepared analogously to the process described in US5576335 by reacting compounds of the formula (II) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base.
Verbindungen der Formel (II) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2014/171528, Journal of Medicinal Chemistry, 54(24), 8541-8554; 2011, WO2012/057269, European Journal, 22(15), 5102-5106; 2016, Chemistry - A European Journal, 22(15), 5102-5106; 2016 oder Organic Leiters, 18(18), 4570-4573 2016 beschriebenen Verfahren. Compounds of the formula (II) are either commercially available or can be prepared by known methods, for example analogously to that in WO2014 / 171528, Journal of Medicinal Chemistry, 54 (24), 8541-8554; 2011, WO2012 / 057269, European Journal, 22 (15), 5102-5106; 2016, Chemistry - A European Journal, 22 (15), 5102-5106; 2016 or Organic Leiters, 18 (18), 4570-4573 2016.
Carbonsäuren der Formel (III) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Mögliche Herstellungswege werden in den Verfahren D und E beschrieben. Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible manufacturing routes are described in methods D and E.
Die Umsetzung der Verbindungen der Formel (II) mit Carbonsäuren der Formel (III) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol, oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N- Methylpyrrolidon oder Stickstoffhaltige Verbindungen wie beispielsweise Pyridin. The reaction of the compounds of formula (II) with carboxylic acids of formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane are preferred; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
Geeignete Kondensationsmittel sind beispielsweise Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder 1,3-Dicyclohexylcarbodiimid. Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
Geeignete Basen sind anorganische Basen, die üblicherweise in solchen Reaktionen verwendet werden. Vorzugsweise werden Basen verwendet, die beispielhaft ausgewählt sind aus der Gruppe bestehend aus Acetaten, Phosphaten, Carbonaten und Hydrogencarbonaten von Alkali- oder Erdalkalimetallen. Besonders bevorzugt sind dabei Natriumacetat, Natriumphosphat, Kaliumphosphat, Caesiumcarbonat, Natriumcarbonat, Kaliumcarbonat, Natriumhydrogencarbonat, Kaliumhydrogencarbonat. Suitable bases are inorganic bases which are usually used in such reactions. Bases which are selected by way of example from the group consisting of acetates, phosphates, carbonates and hydrogen carbonates of alkali or alkaline earth metals are preferably used. Sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate are particularly preferred.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 180 °C durchgeführt werden, vorzugsweise erfolgt die Reaktion bei Normaldruck und Temperaturen von 20 bis 140 °C. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 180 ° C., the reaction is preferably carried out at atmospheric pressure and temperatures from 20 to 140 ° C.
Schritt b) Step b)
Die Verbindungen der Formel (V) lassen sich hersteilen durch Kondensation der Verbindungen der Formel (IV) z.B. analog der in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629, WO2012/086848, WO2013/018928, W02015/000715 oder WO 2015/121136 beschriebenen Verfahren. The compounds of formula (V) can be prepared by condensing the compounds of formula (IV) e.g. analogous to the methods described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, W02015 / 000715 or WO 2015/121136.
Die Umsetzung zu Verbindungen der Formel (V) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan, tert.- Butylmethylether; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N-Methylpyrrolidon oder stickstoffhaltige Verbindungen wie beispielsweise Pyridin. The conversion to compounds of formula (V) can take place in bulk or in a solvent, the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Prefers are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
Die Reaktion lässt sich durchführen in Gegenwart eines Kondensationsmittels, einer Säure, einer Base oder eines Chlorierungsmittels. The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
Beispiele für geeignete Kondensationsmittel sind Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder 1,3-Dicyclohexylcarbodiimid; Anhydride wie Essigsäureanhydrid, Trifluoressigsäureanhydrid; eine Mischung aus Triphenylphosphin, einer Base und Tetrachlorkohlenstoff oder eine Mischung aus Triphenylphosphin und einem Azodiester wie z.B. Diethylazodicarbonsäure. Examples of suitable condensing agents are carbodiimides such as l- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as e.g. Diethylazodicarboxylic acid.
Beispiele für geeignete Säuren, die in der beschriebenen Reaktion eingesetzt werden können, sind Sulfonsäuren wie para-Toluolsulfonsäure; Carbonsäuren wie Essigsäure oder Polyphosphorsäuren. Examples of suitable acids that can be used in the reaction described are sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
Beispiele für geeignete Basen sind stickstoffhaltige Heterocyclen wie Pyridin, Picolin, 2,6-Lutidin, 1,8- Diazabicyclo[5.4.0]-7-undecen (DBU); tertiäre Amine wie Triethylamin und N,N- Diisopropylethylamin; anorganische Basen wie Kaliumphosphat, Kaliumcarbonat und Natriumhydrid. Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
Ein Beispiel für ein geeignetes Chlorierungsmittel ist Phosphoroxychlorid. An example of a suitable chlorinating agent is phosphorus oxychloride.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 200 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
Schritt c) Step c)
Die Verbindungen der Formel (I), wobei n für 0 steht, lassen sich hersteilen durch Umsetzung der Verbindungen der Formel (V) mit den Verbindungen der Formel (Via) in Gegenwart einer Base. The compounds of the formula (I), where n is 0, can be prepared by reacting the compounds of the formula (V) with the compounds of the formula (Via) in the presence of a base.
Mercaptanderivate der Formel (Via) wie beispielsweise Methylmercaptan, Ethylmercaptan oder Isopropylmercaptan sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in US2006/25633, US2006/111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 oder Journal of the American Chemical Society, 44 (1922), 1329 beschriebenen Verfahren. Mercaptan derivatives of the formula (Via) such as, for example, methyl mercaptan, ethyl mercaptan or isopropyl mercaptan are either commercially available or can be prepared by known methods, for example analogously to that in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), 1329.
Die Umsetzung zu Verbindung der Formel (I), wobei n für 0 steht, kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1,2- Dimethoxyethan, tert.-Butylmethylether; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid, N-Methylpyrrolidon oder Dimethylsulfoxid. The reaction to give the compound of formula (I), where n is 0, can be carried out in bulk or in a solvent; the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preferred are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
Beispiele für geeignete Basen sind anorganische Basen aus der Gruppe bestehend aus Acetaten, Phosphaten Hydrogencarbonaten und Carbonaten von Alkali- oder Erdalkalimetallen. Bevorzugt sind dabei Caesiumcarbonat, Natriumcarbonat Kaliumcarbonat und Natriumhydrogencarbonat. Weitere geeignete Basen sind Alkalimetallhydride wie z.B. Natriumhydrid. Examples of suitable bases are inorganic bases from the group consisting of acetates, phosphates, hydrogen carbonates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate, potassium carbonate and sodium hydrogen carbonate are preferred. Other suitable bases are alkali metal hydrides such as e.g. Sodium hydride.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 200 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
In der beschriebenen Reaktion steht X1 bevorzugt für ein Fluor- oder Chloratom. In the reaction described, X 1 preferably represents a fluorine or chlorine atom.
Alternativ kann für den Fall dass XI für Brom steht auch mit einer geeigneten Lithiumbase transmetalliert und anschließend mit dem entsprechenden kommerziell erhältlichen Disulfid umgesetzt werden. Siehe hierzu Bioorganic and Medicinal Chemistry Leiters, 20 (2010), 2770 - 2775. Alternatively, if XI is bromine, it can also be transmetallated with a suitable lithium base and then reacted with the corresponding commercially available disulfide. See also Bioorganic and Medicinal Chemistry Leiters, 20 (2010), 2770 - 2775.
Geeignete Lithiumbasen sind zum Beispiel n-Butyllithium. Suitable lithium bases are, for example, n-butyllithium.
Die Umsetzung zu Verbindung der Formel (I), wobei n für 0 steht, kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1,2- Dimethoxyethan, tert. -Butylmethy lether The reaction to give the compound of formula (I), where n is 0, can take place in bulk or in a solvent, the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert are preferred. -Butylmethyl lether
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 200 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
Die Reaktion kann in der Mikrowelle durchgeführt werden. The reaction can be carried out in the microwave.
Schritt d) Step d)
Die Verbindungen der Formel (I), wobei n für 1 steht, lassen sich hersteilen durch Oxidation der Verbindungen der Formel (I), wobei n für 0 steht. Die Oxidation wird generell in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure, Propionsäure oder Wasser. Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid, meta-Chlorperbenzoesäure oder Natriumperiodat. The compounds of the formula (I), where n is 1, can be prepared by oxidation of the compounds of the formula (I), where n is 0. The oxidation is generally carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water. Examples of suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von - 20°C °C bis 120 °C durchgeführt werden. Schritt e) The reaction can be carried out in vacuo, at normal pressure or under superatmospheric pressure and at temperatures from -20 ° C to 120 ° C. Steps)
Die Verbindungen der Formel (I), wobei n für 2 steht, lassen sich hersteilen durch Oxidation der Verbindungen der Formel (I), wobei n für 1 steht. Die Oxidation wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure, Propionsäure oder Wasser. The compounds of formula (I), where n is 2, can be prepared by oxidation of the compounds of formula (I), where n is 1. The oxidation is generally carried out in a solvent. Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid und meta-Chlorperbenzoesäure. Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von - 20°C °C bis 120 °C durchgeführt werden. The reaction can be carried out in vacuo, at normal pressure or under superatmospheric pressure and at temperatures from -20 ° C to 120 ° C.
Schritt f) Die Verbindungen der Formel (I), wobei n für 2 steht, lassen sich auch in einem einstufigen Prozess hersteilen durch Oxidation der Verbindungen der Formel (I), wobei n für 0 steht. Die Oxidation wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure, Propionsäure oder Wasser. Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid und meta-Chlorperbenzoesäure. Step f) The compounds of the formula (I), where n is 2, can also be prepared in a one-step process by oxidation of the compounds of the formula (I), where n is 0. The oxidation is generally carried out in a solvent. Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water. Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von - 20°C °C bis 120 °C durchgeführt werden. The reaction can be carried out in vacuo, at normal pressure or under superatmospheric pressure and at temperatures from -20 ° C to 120 ° C.
Verfahren B Procedure B
Verbindungen der Formel (I), wobei n für 2 steht, können alternativ in einem einstufigen Prozess hergestellt werden aus Verbindungen der Formel (V). Das Verfahren wird anhand der Umsetzung vonCompounds of formula (I), where n is 2, can alternatively be prepared in a one-step process from compounds of formula (V). The procedure is based on the implementation of
Verbindungen der Formel (V) zu Verbindungen der Formel (I) aus Verfahren A beschrieben. Compounds of formula (V) to compounds of formula (I) described in process A.
Die Reste R1, R2, R3, R4, R5, R6 und n haben die oben beschriebenen Bedeutungen, A2 und A3 stehen für CH oder N und X1 steht für Halogen (bevorzugt Brom oder Iod). M steht für ein Alkalimetall (bevorzugt für Natrium oder Kalium). The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n have the meanings described above, A 2 and A 3 represent CH or N and X 1 represents halogen (preferably bromine or iodine). M stands for an alkali metal (preferably sodium or potassium).
Verbindungen der Formel (I), wobei n für 2 steht, können in einem einstufigen Prozess hergestellt werden aus Verbindungen der Formel (V) beispielsweise in Analogie zu den in Journal of Organic Chemistry 70 (2005) 2696-2700 beschriebenen Verfahren durch einen Halogen- Sulfon- Austausch mit einer Verbindung der Formel (VIb). Der Austausch wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden polar aprotische Lösungsmittel wie beispielsweise Dimethylsulfoxid und N,N- Dimethylformamid eingesetzt. Compounds of the formula (I), where n is 2, can be prepared in a one-step process from compounds of the formula (V), for example in analogy to the processes described in Journal of Organic Chemistry 70 (2005) 2696-2700 by a halogen Sulphone exchange with a compound of formula (VIb). The exchange is generally carried out in a solvent. Polar aprotic solvents such as dimethyl sulfoxide and N, N-dimethylformamide are preferably used.
Die Reaktion wird generell durch Zusatz eines Kupfer(I)-Salzes katalysiert wie beispielsweise Kupfer(I) iodid. The reaction is generally catalyzed by the addition of a copper (I) salt such as copper (I) iodide.
Verbindungen der Formel (VIb) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Organic Synthesis 57 (1977) 88-92; Tetrahedron Leiters 9 (1979) 821-824 sowie Bulletin de la Societe Chimique de France 4 (1958) 447- 450 beschriebenen Verfahren. Compounds of the formula (VIb) are either commercially available or can be prepared by known methods, for example analogously to that in Organic Synthesis 57 (1977) 88-92; Tetrahedron Leiters 9 (1979) 821-824 and Bulletin de la Societe Chimique de France 4 (1958) 447- 450.
Beispiele für geeignete Schwefel-Reagenzien sind Salze der Sulfinsäure. Examples of suitable sulfur reagents are salts of sulfinic acid.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von -20°C °C bis 120 °C durchgeführt werden. Verfahren C The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from -20 ° C. to 120 ° C. Procedure C
q = 1 oder 2  q = 1 or 2
(I) n = 2  (I) n = 2
Die Reste R1, R2, R4, R5, R6 und n haben die oben beschriebenen Bedeutungen, A2 und A3 stehen für CH oder N, q für 1 oder 2 und X und X1 stehen für Halogen. Schritt a) The radicals R 1 , R 2 , R 4 , R 5 , R 6 and n have the meanings described above, A 2 and A 3 represent CH or N, q represents 1 or 2 and X and X 1 represent halogen. Step a)
Verbindungen der Formel (VIII) können hergestellt werden durch Cyanomethylierung der Verbindungen der Formel (VII) mit Verbindung der Formel (M) in Gegenwart eines Katalysators, eines Liganden und einer Base, beispielsweise nach den in J. Am. Chem. Soc. (2002), 124, 9330, J. Am. Chem. Soc. (2005), 127, 15824 oder W02016/041819 beschriebenen Verfahren. Die Verbindung der Formel (M) ist kommerziell erhältlich. Compounds of the formula (VIII) can be prepared by cyanomethylating the compounds of the formula (VII) with a compound of the formula (M) in the presence of a catalyst, a ligand and a base, for example according to the method described in J. Am. Chem. Soc. (2002), 124, 9330, J. Am. Chem. Soc. (2005), 127, 15824 or W02016 / 041819. The compound of formula (M) is commercially available.
Die Umsetzung zu Verbindungen der Formel (VIII) erfolgt in der Regel in einem Lösungsmittel. Bevorzugt werden aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid, N- Methylpyrrolidon, oder Dimethylsulfoxid. The conversion to compounds of formula (VIII) is usually carried out in a solvent. Aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide are preferred.
Als Katalysator lassen sich Palladiumkomplexe einsetzen, wie beispielsweise Tris(dibenzylidenaceton)dipalladium(0) oder [l,l‘-Bis(diphenylphosphino)ferrocene]- dichlorpalladium(II) und als Liganden werden in der Regel Organophosphan-Verbindungen verwendet, wie beispielsweise Bis(diphenylphosphin)-9,9-dimethylxanthen (Xanthphos). Palladium complexes such as tris (dibenzylidene acetone) dipalladium (0) or [l, l'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) can be used as the catalyst and organophosphane compounds such as bis are generally used as ligands (diphenylphosphine) -9,9-dimethylxanthene (Xanthphos).
Eine geeignete Base ist beispielsweise Zinkfluorid. A suitable base is, for example, zinc fluoride.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0°C bis 200 °C durchgeführt werden. Alternativ kann die Cyanomethylierung auch mit Hilfe einer Suzuki-Kupplung durchgeführt werden, beispielsweise nach dem in J. Am. Chem. Soc. (2011), 133, 6948-6951 beschriebenen Verfahren. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C. Alternatively, the cyanomethylation can also be carried out using a Suzuki coupling, for example according to the method described in J. Am. Chem. Soc. (2011), 133, 6948-6951.
Schritt b) Step b)
Verbindungen der Formel (I), wobei n für 2 steht, können hergestellt werden durch Umsetzung der Verbindungen der Formel (VIII) mit Verbindungen der Formel (O) in Gegenwart einer Base, beispielsweise nach den in W02016/041819 beschriebenen Verfahren. Compounds of the formula (I), where n is 2, can be prepared by reacting the compounds of the formula (VIII) with compounds of the formula (O) in the presence of a base, for example by the processes described in WO2016 / 041819.
Die Verbindungen der Formel (O) sind kommerziell erhältlich, The compounds of the formula (O) are commercially available
Die Umsetzung zu Verbindungen der Formel (I), wobei n für 2 steht, erfolgt in der Regel in einem Lösungsmittel. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol, aprotische polare Lösungsmittel wie beispielsweise Aceton, N,N-Dimethylformamid, N-Methylpyrrolidon, Dimethylsulfoxid, Nitrile wie beispielsweise Acetonitril, oder Ester wie beispielsweise Essigsäureethylester. The conversion to compounds of the formula (I), where n is 2, is generally carried out in a solvent. Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene, aprotic polar solvents such as acetone, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such as ethyl acetate are preferred.
Beispiele für geeignete Basen sind stickstoffhaltige Heterocyclen wie Pyridin, 1,8-Diazabicyclo[5.4.0]- 7-undecen (DBU); tertiäre Amine wie Triethylamin und N,N-Diisopropylethylamin; anorganische Basen wie Kaliumphosphat, Cäsiumcarbonat, Kaliumcarbonat und Natriumhydrid. Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] - 7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0°C bis 200 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
Die entsprechenden Verbindungen mit n=0 oder n=l lassen sich analog herstellen. The corresponding compounds with n = 0 or n = 1 can be produced analogously.
Verfahren D Carbonsäuren der Formel (III) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise aus Pyridinen der Formel (IX) analog der in WO2011/15343, WO2014/14874 oder WO2010/34738 beschriebenen Verfahren. Process D carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods, for example from pyridines of the formula (IX) analogously to the processes described in WO2011 / 15343, WO2014 / 14874 or WO2010 / 34738.
Die Reste R2 und R3 haben die oben beschriebenen Bedeutungen, X steht für ein Halogenid Ion bevorzugt Iodid, X1 steht für Halogen und R14 steht für (Ci-C4)Alkyl. Schritt a) The radicals R 2 and R 3 have the meanings described above, X stands for a halide ion, preferably iodide, X 1 stands for halogen and R 14 stands for (Ci-C4) alkyl. Step a)
Die Verbindungen der Formel (X) können in Analogie zu den in WO2011/15343, WO2014/14874 oder WO2010/34738 beschriebenen Verfahren durch Umsetzung von Verbindungen der Formel (IX) mit Hydroxylamin-O-sulfonsäure in Gegenwart einer Base wie beispielsweise Kaliumcarbonat in ein N- Iminopyridinium Intermediat überführt werden, das in einem zweiten Schrit in Gegenwart einer Säure wie beispielsweise Iodwasserstoffsäure (HI) in einem geeigneten Lösungsmitel wie beispielsweise Ethanol in das 1 -Amino-pyridinium Derivat der Formel (X) überführt wird. Die Pyridin-Derivate der Formel (IX) sind kommerziell erhältlich. In analogy to the processes described in WO2011 / 15343, WO2014 / 14874 or WO2010 / 34738, the compounds of the formula (X) can be reacted by reacting compounds of the formula (IX) with hydroxylamine-O-sulfonic acid in the presence of a base such as, for example, potassium carbonate N-iminopyridinium intermediate are converted, which is converted in a second step in the presence of an acid such as, for example, hydroiodic acid (HI) in a suitable solvent such as, for example, ethanol into the 1-amino-pyridinium derivative of the formula (X). The pyridine derivatives of the formula (IX) are commercially available.
Schritt b) und c) Step b) and c)
Verbindungen der Formel (XII) können in Analogie zu den in WO2011/15343, WO2014/14874 oder WO2010/34738 beschriebenen Verfahren aus Verbindungen der Formel (X) in einer 1,3-dipolarenCompounds of the formula (XII) can be prepared in a 1,3-dipolar manner in analogy to the processes described in WO2011 / 15343, WO2014 / 14874 or WO2010 / 34738 from compounds of the formula (X)
Cycloaddition mit einem Alkin der Formel (XI) hergestellt werden. Für den Fall dass Isomere entstehen lassen sich diese durch chromatographische Methoden in die Einzelisomere trennen. Auf diese Weise lässt sich der Diester der Formel (XII) isomerenrein erhalten. Durch Erhitzen in einer geeigneten Säure wie beispielsweise wäßriger Schwefelsäure lässen sich Verbindungen der Formel (XII) in Säuren der Formel (XIII) überführen durch Decarboxylierung und gleichzeitige Verseifung der Esterfunktion. Schritt d) Cycloaddition can be prepared with an alkyne of the formula (XI). If isomers are formed, they can be separated into the individual isomers by chromatographic methods. In this way, the diester of formula (XII) can be obtained isomerically pure. By heating in a suitable acid such as, for example, aqueous sulfuric acid, compounds of the formula (XII) can be converted into acids of the formula (XIII) by decarboxylation and simultaneous saponification of the ester function. Step d)
Verbindungen der Formel (III) können nach Standardverfahren über eine Halogenierung hergestellt werden beispielsweise in Analogie zu den in WO201 1/50284 oder WO2016/12896 beschriebenen Verfahren, beispielsweise mit N-Chlorsuccinimid oder N-Bromsuccinimid als Halogenierungsmittel in einem geeigneten Lösungsmittel wie beispielsweise Dichlormethan oder 1 ,2-Dichlorethan. Compounds of the formula (III) can be prepared by standard halogenation processes, for example analogously to the processes described in WO201 1/50284 or WO2016 / 12896, for example with N-chlorosuccinimide or N-bromosuccinimide as halogenating agent in a suitable solvent such as dichloromethane or 1, 2-dichloroethane.
Verfahren E Procedure E
In einem weiteren Verfahren lassen sich Carbonsäuren der Formel (III) hersteilen aus 2-Formylpyridin Derivaten der Formel (XIV) analog der in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 oder WO2009/29625 beschriebenen Verfahren. In a further process, carboxylic acids of the formula (III) can be prepared from 2-formylpyridine derivatives of the formula (XIV) analogously to that in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009 / 29625 procedures described.
Die Reste R2 und R3 haben die oben beschriebenen Bedeutungen, X1 steht für Halogen und R14 steht für (Ci-C4)Alkyl. Schritt a) The radicals R 2 and R 3 have the meanings described above, X 1 represents halogen and R 14 represents (Ci-C 4 ) alkyl. Step a)
Die Verbindungen der Formel (XVI) können in Analogie zu den in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 oder WO2009/29625 beschriebenen Verfahren durch Umsetzung von Verbindungen der Formel (XIV) mit einem Azidoessigsäurealkylester Derivat der Formel (XV) in Gegenwart einer geeigneten Base wie beispielsweise Natriummethanolat in einem geeigneten Lösungsmittel wie beispielsweise Methanol hergestellt werden. Die Verbindungen der Formel (XIV) sind kommerziell erhältlich oder können nach Standardverfahren hergestellt werden. Schritt b) The compounds of the formula (XVI) can be prepared in analogy to the processes described in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009 / 29625 by reacting compounds of the formula (XIV) with an alkyl azidoacetate derivative of formula (XV) in the presence of a suitable base such as sodium methoxide in a suitable solvent such as methanol. The compounds of formula (XIV) are commercially available or can be prepared by standard methods. Step b)
Verbindungen der Formel (XVII) können in Analogie zu den in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 oder WO2009/29625 beschriebenen Verfahren durch Zyklisierung von Verbindungen der Formel (XVI) in einem geeigneten Lösungsmittel wie beispielsweise Xylol hergestellt werden. Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei erhöhten Temperaturen durchgeführt werden. Bevorzugt ist eine Temperatur größer als l00°C. Compounds of the formula (XVII) can be prepared in analogy to the processes described in Jounal of Medicinal Chemistry 56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009 / 29625 by cyclization of compounds of the formula (XVI) in a suitable solvent such as xylene. The reaction can be carried out in vacuo, at atmospheric pressure or under elevated pressure and at elevated temperatures. A temperature greater than 100 ° C. is preferred.
Schritt c und d) Step c and d)
Der Ester der Formel (XVII) kann unter Verwendung von Standardmethoden in die Säure der Formel (XVIII) überführt werden beispielsweise mit einem Alkalihydroxid als Base wie Natriumhydroxid oder Lithiumhydroxid in einem Alkohol als Lösungsmittel wie z.B. Ethanol oder einem Gemisch aus Tetrahydrofuran und Wasser. The ester of formula (XVII) can be converted to the acid of formula (XVIII) using standard methods, for example with an alkali hydroxide as a base such as sodium hydroxide or lithium hydroxide in an alcohol as a solvent such as e.g. Ethanol or a mixture of tetrahydrofuran and water.
Die weitere Umsetzung zu Verbindungen der Formel (III) erfolgt nach Standardverfahren über eine Halogenierung analog wie in Verfahren D beschrieben. The further conversion to compounds of formula (III) is carried out according to standard methods by halogenation analogously to that described in method D.
Verfahren F Procedure F
Die Reste R2, R3 und R4 haben die oben beschriebenen Bedeutungen, A steht für CH oder N, Y steht für eine Abgangsgruppe wie z.B. Chlor, Brom, Iod, O-Triflat oder O-Mesyl und X1 steht für Halogen. Schritt a) The radicals R 2 , R 3 and R 4 have the meanings described above, A stands for CH or N, Y stands for a leaving group such as chlorine, bromine, iodine, O-triflate or O-mesyl and X 1 stands for halogen. Step a)
Die Verbindungen der Formel (XX) können in Analogie zu dem in US5576335 beschriebenen Verfahren durch die Umsetzung von Verbindungen der Formel (XIX) mit Carbonsäuren der Formel (III) in Gegenwart eines Kondensationsmittels bzw. einer Base hergestellt werden. The compounds of the formula (XX) can be prepared in analogy to the process described in US5576335 by reacting compounds of the formula (XIX) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base.
Verbindungen der Formel (XIX) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Journal of Medicinal Chemistry, 57(19), 7933-7946; 2014 oder WO2014/001464 beschriebenen Verfahren. Compounds of the formula (XIX) are either commercially available or can be prepared by known methods, for example analogously to that in Journal of Medicinal Chemistry, 57 (19), 7933-7946; 2014 or WO2014 / 001464 described methods.
Carbonsäuren der Formel (III) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Mögliche Herstellungswege werden in den Verfahren D und E beschrieben. Die Umsetzung der Verbindungen der Formel (XIX) mit Carbonsäuren der Formel (III) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol, oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N- Methylpyrrolidon oder Stickstoffhaltige Verbindungen wie beispielsweise Pyridin. Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible manufacturing routes are described in methods D and E. The reaction of the compounds of the formula (XIX) with carboxylic acids of the formula (III) can be carried out in Substance or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane are preferred; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
Geeignete Kondensationsmittel sind beispielsweise Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder l,3-Dicyclohexylcarbodiimid. Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
Geeignete Basen sind anorganische Basen, die üblicherweise in solchen Reaktionen verwendet werden. Vorzugsweise werden Basen verwendet, die beispielhaft ausgewählt sind aus der Gruppe bestehend aus Acetaten, Phosphaten, Carbonaten und Hydrogencarbonaten von Alkali- oder Erdalkalimetallen. Besonders bevorzugt sind dabei Natriumacetat, Natriumphosphat, Kaliumphosphat, Caesiumcarbonat, Natriumcarbonat, Kaliumcarbonat, Natriumhydrogencarbonat, Kaliumhydrogencarbonat. Suitable bases are inorganic bases which are usually used in such reactions. Bases which are selected by way of example from the group consisting of acetates, phosphates, carbonates and hydrogen carbonates of alkali or alkaline earth metals are preferably used. Sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate are particularly preferred.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 180 °C durchgeführt werden, vorzugsweise erfolgt die Reaktion bei Normaldruck und Temperaturen von 20 bis 140 °C. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 180 ° C., the reaction is preferably carried out at atmospheric pressure and temperatures from 20 to 140 ° C.
Schritt b) Step b)
Die Verbindungen der Formel (XXI) lassen sich hersteilen durch Kondensation der Verbindungen der Formel (XX) z.B. analog der in WO2009/131237, WO2010/125985, WO2011/043404,The compounds of formula (XXI) can be prepared by condensing the compounds of formula (XX) e.g. analogous to that in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404,
WO2011/040629, WO2012/086848, WO2013/018928, W02015/000715 oder WO 2015/121136 beschriebenen Verfahren. Methods described in WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, W02015 / 000715 or WO 2015/121136.
Die Umsetzung zu Verbindungen der Formel (XXI) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan, tert.- Butylmethylether; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N-Methylpyrrolidon oder stickstoffhaltige Verbindungen wie beispielsweise Pyridin. Die Reaktion lässt sich durchführen in Gegenwart eines Kondensationsmittels, einer Säure, einer Base oder eines Chlorierungsmittels. The reaction to give compounds of the formula (XXI) can be carried out in bulk or in a solvent; the reaction is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preferred are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine. The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
Beispiele für geeignete Kondensationsmittel sind Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder l,3-Dicyclohexylcarbodiimid; Anhydride wie Essigsäureanhydrid, Trifluoressigsäureanhydrid; eine Mischung aus Triphenylphosphin, einer Base und Tetrachlorkohlenstoff oder eine Mischung aus Triphenylphosphin und einem Azodiester wie z.B. Diethylazodicarbonsäure. Examples of suitable condensing agents are carbodiimides such as l- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as e.g. Diethylazodicarboxylic acid.
Beispiele für geeignete Säuren, die in der beschriebenen Reaktion eingesetzt werden können, sind Sulfonsäuren wie para-Toluolsulfonsäure; Carbonsäuren wie Essigsäure oder Polyphosphorsäuren. Examples of suitable acids that can be used in the reaction described are sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
Beispiele für geeignete Basen sind stickstoffhaltige Heterocyclen wie Pyridin, Picolin, 2,6-Lutidin, 1,8- Diazabicyclo[5.4.0]-7-undecen (DBU); tertiäre Amine wie Triethylamin und N,N- Diisopropylethylamin; anorganische Basen wie Kaliumphosphat, Kaliumcarbonat und Natriumhydrid. Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
Ein Beispiel für ein geeignetes Chlorierungsmittel ist Phosphoroxychlorid. An example of a suitable chlorinating agent is phosphorus oxychloride.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 200 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under superatmospheric pressure and at temperatures from 0 ° C. to 200 ° C.
Schritt c) Step c)
Die Verbindungen der Formel (XXI) können unter Verwendung von Standardmethoden (vgl. z.B. Heterocycles 1999, 50, 1081-1090; W02009/70045 oder Bioorganic and Medicinal Chemistry Leiters 2007, 17, 1369-1375) durch Umsetzung mit elektrophilen, eine Abgangsgruppe enthaltenden Verbindungen (Y = Chlor, Brom, Iod, O-Triflat, O-Mesyl) in N-substituierte Imidazolderivate der Formel (XXIII) überführt werden, beispielsweise mit einem Carbonat als Base wie Kaliumcarbonat in einem Keton als Lösungsmittel, wie z.B. Aceton. The compounds of the formula (XXI) can be used using standard methods (see, for example, Heterocycles 1999, 50, 1081-1090; WO2009 / 70045 or Bioorganic and Medicinal Chemistry Leiters 2007, 17, 1369-1375) by reaction with electrophilic groups containing a leaving group Compounds (Y = chlorine, bromine, iodine, O-triflate, O-mesyl) are converted into N-substituted imidazole derivatives of the formula (XXIII), for example with a carbonate as base such as potassium carbonate in a ketone as solvent, for example Acetone.
Die weitere Umsetzung zu Verbindungen der Formel (I) erfolgt analog der in Verfahren A und B beschriebenen Methoden. The further conversion to compounds of formula (I) is carried out analogously to the methods described in processes A and B.
Verfahren und Verwendungen Procedures and uses
Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Hierunter vorzugsweise ausgeschlossen sind Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden. Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. 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. Control of animal pests is preferably carried out in agriculture and forestry and in material protection. This preferably excludes methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body. The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.
Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel jeweils immer auch den Begriff Pflanzenschutzmittel. In the context of the present application, the term pesticides always includes the term crop protection agents.
Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Emteerträge, Verbesserung der Qualität des Emtegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, insbesondere Nematoden, und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor Vorkommen. The compounds of formula (I) are suitable with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for protecting 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, especially insects, Arachnids, helminths, in particular nematodes, and mollusks, which occur in agriculture, horticulture, animal husbandry, aquaculture, in forests, in gardens and leisure facilities, in the protection of stored goods and materials, and in the hygiene sector.
Im Rahmen der vorliegenden Patentanmeldung ist der Begriff„Hygiene“ so zu verstehen, dass damit jegliche und alle Maßnahmen, Vorschriften und Verfahrensweisen gemeint sind, deren Ziel es ist, Krankheiten, insbesondere Infektionskrankheiten, zu verhindern, und die dazu dienen, die Gesundheit von Menschen und Tieren zu schützen und/oder die Umwelt zu schützen, und/oder die Sauberkeit aufrechterhalten. Erfindungsgemäß schließt dies insbesondere Maßnahmen zur Reinigung, Desinfektion und Sterilisation beispielsweise von Textilien oder harten Oberflächen, insbesondere Oberflächen aus Glas, Holz, Zement, Porzellan, Keramik, Kunststoff oder auch Metall(en) ein, um sicherzustellen, dass diese frei von Hygieneschädlingen und/oder ihren Ausscheidungen sind. Vorzugsweise ausgeschlossen vom Schutzbereich der Erfindung sind in dieser Hinsicht chirurgische oder therapeutische, auf den menschlichen Körper oder die Körper von Tieren anzuwendende Behandlungsvorschriften und diagnostische Vorschriften, die am menschlichen Körper oder den Körpern von Tieren durchgeführt werden. In the context of the present patent application, the term “hygiene” is to be understood to mean any and all measures, regulations and procedures whose aim is to prevent diseases, in particular infectious diseases, and which serve the health of people and protect animals and / or protect the environment and / or maintain cleanliness. According to the invention, this includes, in particular, measures for cleaning, disinfection and sterilization, for example of textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal (s), in order to ensure that these are free from hygiene pests and / or their excretions. In this regard, surgical or therapeutic treatment instructions to be applied to the human body or the bodies of animals and diagnostic instructions which are carried out on the human body or the bodies of animals are preferably excluded from the scope of protection of the invention.
Der Begriff„Hygienesektor“ deckt alle Gebiete, technischen Felder und industriellen Anwendungen ab, bei denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen wichtig sind, zum Beispiel im Hinblick auf Hygiene in Küchen, Bäckereien, Flughäfen, Badezimmern, Schwimmbecken, Kaufhäusern, Hotels, Krankenhäusern, Ställen, Tierhaltungen usw. The term "hygiene sector" covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, Hospitals, stables, animal husbandry, etc.
Der Begriff„Hygieneschädling“ ist daher so zu verstehen, dass damit ein oder mehrere Tierschädlinge gemeint sind, deren Gegenwart im Hygienesektor problematisch ist, insbesondere aus Gesundheitsgründen. Es ist daher ein Hauptziel, das Vorhandensein von Hygieneschädlingen und/oder das Ausgesetztsein ihnen gegenüber im Hygienesektor zu vermeiden oder auf ein Mindestmaß zu begrenzen. Dies lässt sich insbesondere durch die Anwendung eines Pestizids erreichen, das sich sowohl zum Verhindern eines Befalls als auch zum Verhindern eines bereits vorhandenen Befalls einsetzen lässt. Man kann auch Zubereitungen verwenden, die eine Exposition gegenüber Schädlingen verhindern oder reduzieren. Hygieneschädlinge schließen zum Beispiel die unten erwähnten Organismen ein. The term “hygiene pest” should therefore be understood to mean one or more animal pests whose presence in the hygiene sector is problematic, particularly for health reasons. It is therefore a primary goal to avoid or minimize the presence of and / or exposure to hygiene pests in the hygiene sector. This can be achieved in particular by using a pesticide which is used both to prevent infestation and to prevent an already existing infestation leaves. Preparations that prevent or reduce exposure to pests can also be used. For example, hygiene pests include the organisms mentioned below.
Der Begriff „Hygieneschutz“ deckt somit alle Handlungen ab, mit denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen aufrechterhalten und/oder verbessert werden. The term “hygiene protection” thus covers all actions with which these hygiene measures, regulations and procedures are maintained and / or improved.
Die Verbindungen der Formel (I) können vorzugsweise als Schädlingsbekämpfungsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: The compounds of 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 pests mentioned above include:
Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z. B. Acarus spp., z. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z. B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z. B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z. B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z. B. Eutetranychus banksi, Eriophyes spp., z. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z. B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z. B. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus spp., z. B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; aus der Klasse der Chilopoda z. B. Geophilus spp., Scutigera spp.; aus der Ordnung oder der Klasse der Collembola z. B. Onychiurus armatus; Sminthurus viridis; aus der Klasse der Diplopoda z. B. Blaniulus guttulatus; aus der Klasse der Insecta, z. B. aus der Ordnung der Blattodea z. B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., z. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; aus der Ordnung der Coleoptera z. B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., z. B. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., z. B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., z. B. Anoplophora glabripennis, Anthonomus spp., z. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z. B. Bruchus pisorum, Bruchus rufhnanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z. B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z. B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus fumissi, Dendroctonus spp., z. B. Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., z. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., z. B. Epilachna borealis, Epilachna varivestis, Epitrix spp., z. B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus comutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z. B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., z. B. Leucoptera coffeella, Limonius ectypus, Lissorhoptms oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., z. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., z. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z. B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., z. B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z. B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z. B. Psylliodes affmis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophoms fermgineus, Rhynchophorus palmarum, Scolytus spp., z. B. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., z. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Stemechus spp., z. B. Stemechus paludatus, Symphyletes spp., Tanymecus spp., z. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z. B. Zabrus tenebrioides; aus der Ordnung der Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; aus der Ordnung der Diptera z. B. Aedes spp., z. B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z. B. Agromyza frontella, Agromyza parvicomis, Anastrepha spp., Anopheles spp., z. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z. B. Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z. B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z. B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z. B. Dasineura brassicae, Delia spp., z. B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., z. B. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z. B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterbomiella subcincta, Pegomya oder Pegomyia spp., z. B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., z. B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., z. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; aus der Ordnung der Hemiptera z. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z. B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inomata, Aphanostigma piri, Aphis spp., z. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis vibumiphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z. B. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Cameocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon firagaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halb, Coccus spp., z. B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoncossa spp., Ctcnarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., z. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., z. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroncura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z. B. Lecanium comi (=Parthenolecanium comi), Lepidosaphes spp., z. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., z. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z. B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus omatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., z. B. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., z. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z. B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psylla spp., z. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., z. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., z. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z. B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicomis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z. B. Lygocoris pabulinus, Lygus spp., z. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., z. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; aus der Ordnung der Hymenoptera z. B. Acromyrmex spp., Athalia spp., z. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., z. B. Diprion similis, Hoplocampa spp., z. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., z. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., z. B. Vespa crabro, Wasmannia auropunctata, Xeris spp.; aus der Ordnung der Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z. B. Coptotermes spp., z. B. Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., z. B. Reticulitermes flavipes, Reticulitermes hesperus; aus der Ordnung der Lepidoptera z. B. Achroia grisella, Acronicta major, Adoxophyes spp., z. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., z. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., z. B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z. B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., z. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z. B. Heliothis virescens , Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., z. B. Leucoptera coffeella, Lithocolletis spp., z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z. B. Lymantria dispar, Lyonetia spp., z. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z. B. Ostrinia nubilalis, Panolis flammea, Pamara spp., Pectinophora spp., z. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Podesia spp., z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z. B. Schoenobius bipunctifer, Scirpophaga spp., z. B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z. B. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z. B. Locusta migratoria, Melanoplus spp., z. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; aus der Ordnung der Psocoptera z. B. Lepinotus spp., Liposcelis spp.; aus der Ordnung der Siphonaptera z. B. Ceratophyllus spp., Ctenocephalides spp., z. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuten, Enneothrips flavens, Frankliniella spp., z. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z. B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z. B. Scutigerella spp., z. B. Scutigerella immaculata; Pests from the Arthropoda tribe, especially from the Arachnida z. B. Acarus spp., E.g. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. B. Aculus fockeui, Aculus badtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Z. B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., E.g. B. Eutetranychus banksi, Eriophyes spp., E.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., E.g. B. Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Z. B. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus. B. Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphes spp. Steneotarsonemus spinki, Tarsonemus spp., E.g. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the class of Chilopoda z. B. Geophilus spp., Scutigera spp .; from the order or class of the Collembola z. B. Onychiurus armatus; Sminthurus viridis; from the class of the Diplopoda z. B. Blaniulus guttulatus; from the Insecta class, e.g. B. from the order of the Blattodea z. B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., Z. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of the Coleoptera z. B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., E.g. B. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., E.g. B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., E.g. B. Anoplophora glabripennis, Anthonomus spp., E.g. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. B. Bruchus pisorum, Bruchus rufhnanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., E.g. B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., E.g. B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., E.g. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., E.g. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus spp., Spp. B. Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., E.g. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Ep., Ep. Spp. B. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g. B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus comutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegica, Hypususus, Hyposomusus, Hylotrup spp., e.g. B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., Z. B. Leucoptera coffeella, Limonius ectypus, Lissorhoptms oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., Z. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., E.g. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., E.g. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagpp orychusus. Otior. B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g. B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., Z. B. Psylliodes affmis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophoms fermgineus, Rhynchophorus palmarum, Scolytus spp., Z. B. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., E.g. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Stemechus spp., E.g. B. Stemechus paludatus, Symphyletes spp., Tanymecus spp., e.g. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. B. Zabrus tenebrioides; from the order of the Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of the Diptera z. B. Aedes spp., E.g. B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., E.g. B. Agromyza frontella, Agromyza parvicomis, Anastrepha spp., Anopheles spp., E.g. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., E.g. B. Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona plyaialis, Cochlipp. B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., Z. B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., E.g. B. Dasineura brassicae, Delia spp., E.g. B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippoboderma spp., Hypoboderma spp. Liriomyza spp., E.g. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., E.g. B. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., E.g. B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterbomiella subcincta, Pegomya or Pegomyia spp., E.g. B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., Z. B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., Z. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., E.g. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of the Hemiptera z. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., E.g. B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., Z. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., E.g. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inomata, Aphanostigma piri, Aphis spp., E.g. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecidia, Aphis spiraecola, Aphis spiraecola. , Aspidiella spp., Aspidiotus spp., E.g. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., e.g. B. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Cameocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon firagaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosus, Chralomomususicicususalicususalicususalicus, Chrolaphonidusomiculomusiculomicus, Chroma, Chromatomisusulica, Chromaphisidophilica, Chromaphonidusumulica, Chromaphisidulomiculomicuscola, Chromaphonidia fom , Coccus spp., E.g. B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoncossa spp., Ctcnarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspaphis spp.,. Drosicha spp., Dysaphis spp., E.g. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., E.g. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., E.g. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroncura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspiseterlappa, Glycaspiseterlapp. Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., E.g. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g. B. Lecanium comi (= Parthenolecanium comi), Lepidosaphes spp., E.g. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., E.g. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, z. Myzus spp. B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus omatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., Z. B. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Z. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., E.g. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., E.g. B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psylla spp., E.g. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., E.g. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., E.g. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., E.g. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata sppo spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., E.g. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., E.g. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g. B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Z. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicomisis, Leptogyllususid . B. Lygocoris pabulinus, Lygus spp., E.g. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., Z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera z. Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., E.g. B. Diprion similis, Hoplocampa spp., E.g. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Z. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. B. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of the Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera z. B. Coptotermes spp., E.g. B. Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., Z. B. Reticulitermes flavipes, Reticulitermes hesperus; from the order of the Lepidoptera z. B. Achroia grisella, Acronicta major, Adoxophyes spp., E.g. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., E.g. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., E.g. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., E.g. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Carua retaulinaiponumonapasumata, Carapa reticulomonaella, Carpoca reticulomonata, Carpa reticulonomonaella, Carpua reticulomapellaella, Carpoca reticulomataella, Carpa reticulomata, Cara , Chilo spp., E.g. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., E.g. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., E.g. B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Schwieroviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Z. B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., E.g. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., Z. B. Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., Z. B. Leucoptera coffeella, Lithocolletis spp., E.g. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., E.g. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., E.g. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Orophia Orthaga spp., Ostrinia spp., E.g. B. Ostrinia nubilalis, Panolis flammea, Pamara spp., Pectinophora spp., E.g. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., E.g. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Podesia spp., Z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. B. Schoenobius bipunctifer, Scirpophaga spp., E.g. B. Scirpophaga innotata, Scotia segetum, Sesamia spp., E.g. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. B. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea polaellellaella, Tinea polaellella ., Trichophaga tapetzella, Trichoplusia spp., E.g. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., E.g. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. B. Locusta migratoria, Melanoplus spp., E.g. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of the Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of the Psocoptera z. B. Lepinotus spp., Liposcelis spp .; from the order of the Siphonaptera z. B. Ceratophyllus spp., Ctenocephalides spp., E.g. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuten, Enneothrips flavens, Frankliniella spp., Z. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothripshripshripshrips . B. Thrips palmi, Thrips tabaci; from the order of the Zygentoma (= Thysanura), e.g. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of the Symphyla z. B. Scutigerella spp., E.g. B. Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, z. B. aus der Klasse der Bivalvia, z. B. Dreissena spp.; sowie aus der Klasse der Gastropoda z. B. Arion spp., z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pests from the Mollusca tribe, e.g. B. from the class of Bivalvia, z. B. Dreissena spp .; as well as from the class of Gastropoda z. B. Arion spp., E.g. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
Pflanzenschädlinge aus dem Stamm der Nematoda, d. h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z. B. Aglenchus agricola, Anguina spp., z. B. Anguina tritici, Aphelenchoides spp., z. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z. B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z. B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., z. B. Cacopaurus pestis, Criconemella spp., z. B. Criconemella curvata, Criconemella onoensis, Criconemella omata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z. B. Criconemoides femiae, Criconemoides onoense, Criconemoides omatum, Ditylenchus spp., z. B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., z. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z. B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z. B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., z. B. Longidorus africanus, Meloidogyne spp., z. B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., z. B. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., z. B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z. B. Tylenchorhynchus annulatus, Tylenchulus spp., z. B. Tylenchulus semipenetrans, Xiphinema spp., z. B. Xiphinema index. Plant pests from the Nematoda strain, ie plant-parasitic nematodes, in particular Aglenchus spp., E.g. B. Aglenchus agricola, Anguina spp., E.g. B. Anguina tritici, Aphelenchoides spp., E.g. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., E.g. B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., E.g. B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Z. B. Cacopaurus pestis, Criconemella spp., E.g. B. Criconemella curvata, Criconemella onoensis, Criconemella omata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., E.g. B. Criconemoides femiae, Criconemoides onoense, Criconemoides omatum, Ditylenchus spp., E.g. B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., E.g. B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., E.g. B. Longidorus africanus, Meloidogyne spp., E.g. B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., Z. B. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g. B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. B. Trichodorus obtusus, Trichodorus primitive, Tylenchorhynchus spp., e.g. B. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., E.g. B. Xiphinema index.
Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma- like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. The compounds of the formula (I) can, if appropriate in certain concentrations or application rates, also as herbicides, safeners, growth regulators or agents for improving the plant properties, as microbicides or gametocides, for example as fungicides, antifungals, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
Formulierungen Wording
Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungsformen als Schädlingsbekämpfungsmittel wie z. B. Drench-, Drip- und Spritzbrühen, umfassend mindestens eine Verbindung der Formel (1). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wie Penetrationsförderer, z. B. pflanzliche Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester pflanzlicher Fettsäuren wie beispielsweise Rapsöl- oder Sojaölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze, z. B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention fördernde Mittel wie z. B. Dioctylsulfosuccinat oder Hydroxypropyl-guar-Polymere und/oder Humectants wie z. B. Glycerin und/oder Dünger wie beispielsweise Ammonium, Kalium oder Phosphor enthaltende Dünger. The present invention further relates to formulations and use forms prepared therefrom as pesticides such. B. drench, drip and spray broths comprising at least one compound of formula (1). If appropriate, the use forms contain further pesticides and / or adjuvants which improve the effect, such as penetration promoters, for. B. vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rapeseed oil or soybean oil methyl esters or alkanol alkoxylates and / or spreading agents such as alkylsiloxanes and / or salts, e.g. B. organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or the retention-promoting agents such. B. dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such as. B. glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizers.
Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser dispergierbare Granulate (WG), Granulate (GR) und Kapselkonzentrate (CS); diese und weitere mögliche Formuliertypen sind beispielsweise durch Crop Life International und in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einer oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS) ; these and other possible types of formulations are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. The formulations may contain, in addition to one or more compounds of the formula (I), further agrochemical active ingredients.
Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Verdicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fördern. These are preferably formulations or use forms which contain auxiliaries such as, for example, extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries such as, for example, adjuvants. An adjuvant in this context is a component that is biological Effect of the formulation improved without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface or penetration.
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Verbindungen der Formel (I) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktiven Stoffen. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. These formulations are prepared in a known manner, e.g. B. by mixing the compounds of formula (I) with auxiliaries such as extenders, solvents and / or solid carriers and / or other auxiliaries such as surfactants. The formulations are either produced in suitable plants or before or during use.
Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (1) oder den aus diesen Formulierungen bereiteten Anwendungsformen (wie z. B. gebrauchsfähigen Schädlingsbekämpfungsmitteln wie Spritzbrühen oder Saatgutbeizen) besondere Eigenschaften, wie bestimmte physikalische, technische und/oder biologische Eigenschaften zu verleihen. Auxiliaries which can be used are substances which are suitable, the formulation of the compounds of the formula (1) or the use forms prepared from these formulations (such as usable pesticides such as spray liquors or seed dressings) have special properties, such as certain physical, technical and / or to impart biological properties.
Als Streckmittel eignen sich z. B. Wasser, polare und unpolare organische chemische Flüssigkeiten z. B. aus den Klassen der aromatischen und nicht- aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsulfoxid). lm Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. As an extender z. B. water, polar and non-polar organic chemical liquids z. B. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), the ketones (such as acetone, cyclohexanone ), Esters (also fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethyl sulfoxide). If water is used as an extender, e.g. B. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z. B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder chlorierte aliphatische Kohlenwasserstoffe wie z. B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z. B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z. B. Methanol, Ethanol, iso-Propanol, Butanol oder Glykol sowie deren Ether und Ester, Ketone wie z. B. Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylsulfoxid sowie Wasser. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons such as. B. xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such as. B. cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as. B. methanol, ethanol, isopropanol, Butanol or glycol and their ethers and esters, ketones such as. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide and water.
Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z. B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und/oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen infrage: z. B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Papier, Kokosnussschalen, Maiskolben und Tabakstängel. In principle, all suitable carriers can be used. The following are particularly suitable as carriers: B. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
Auch verflüssigte gasförmige Streckmittel oder Lösemittel können eingesetzt werden. Insbesondere eignen sich solche Streckmittel oder Trägerstoffe, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgase wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Liquefied gaseous extenders or solvents can also be used. Particularly suitable extenders or carriers are those which are gaseous at normal temperature and pressure, e.g. B. aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulfonsäure, Salze von Phenolsulfonsäure oder Naphthalinsulfonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulfobemsteinsäureestem, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenolen, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulfate, Sulfonate und Phosphate, z. B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. Examples of emulsifiers and / or foaming agents, dispersants or wetting agents with ionic or nonionic properties or mixtures of these surface-active substances 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 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. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolyzates, lignin sulfite liquors and methyl cellulose. The presence of a surface-active substance is advantageous if one of the compounds of the formula (I) and / or one of the inert carriers is not soluble in water and if the application is carried out in water.
Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und/oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. As additional auxiliaries in the formulations and the application forms derived therefrom, dyes such as inorganic pigments, for. As iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrients and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be present. Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and / or physical stability can also be present. Foam-producing agents or defoamers can also be contained.
Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und pflanzliche Öle sein. Furthermore, the formulations and use forms derived therefrom can also contain adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids, as additional auxiliaries. Other auxiliaries can be mineral and vegetable oils.
Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsförderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Feuchthaltemittel, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welcher für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. If appropriate, further auxiliaries can be contained in the formulations and the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestering agents, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) can be combined with any solid or liquid additive that is commonly used for formulation purposes.
Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar-Polymere. All those substances which reduce the dynamic surface tension, for example dioctyl sulfosuccinate or which increase the visco-elasticity, for example hydroxypropyl guar polymers, are suitable as retention promoters.
Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Be tracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Beweglichkeit der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51, 131-152) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettaminalkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. In the present context, penetration promoters include all those substances that are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are defined in this context by the fact that they penetrate into the plant's cuticle from the (usually aqueous) application broth and / or from the spray coating and can thereby increase the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut fat ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil methyl esters, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.-% der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung. Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (I), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. The formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I), particularly preferably between 0.01 and 95% by weight of the compound of the formula (I), very particularly 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 use forms (in particular pesticides) prepared from the formulations can vary within wide limits. The concentration of the compound of the formula (I) in the use forms can 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 use form , lie. The application takes place in a customary manner adapted to the application forms.
Mischungen Mixtures
Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbiziden, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, Semiochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z. B. das Wirkungsspektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repellenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Des Weiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Emteertrag steigern, die Reife beeinflussen, die Qualität und/oder der Emährungswert der Emteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Emteprodukte verbessern. The compounds of formula (I) can also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, bird repellants, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators become so z. B. to broaden the spectrum of activity, to prolong the duration of action, to increase the speed of action, to prevent repellency or to prevent the development of resistance. Furthermore, such active ingredient combinations can affect plant growth and / or tolerance to abiotic factors such as. B. high or low temperatures, against dryness or against increased water or soil salt content. Flowering and fruiting behavior can also be improved, germination and rooting optimized, harvesting easier and crop yield increased, ripeness influenced, the quality and / or nutritional value of the crop products increased, the shelf life extended and / or the workability of the crop products improved.
Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Emtegutes eingesetzt werden. The compounds of the formula (I) can furthermore be present in a mixture with further active compounds or semiochemicals, such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of formula (I) can be used to improve plant properties, such as growth, yield and quality of the crop.
In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. In a particular embodiment of the invention, the compounds of the formula (I) are present in formulations or in the use forms prepared from these formulations in a mixture with further compounds, preferably those as described below.
Wenn eine der im Folgenden genannten Verbindungen in verschiedenen tautomeren Formen Vorkommen kann, sind auch diese Formen mit umfasst, auch wenn sie sie nicht in jedem Fall explizit genannt wurden. Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Insektizide/Akarizide/Nematizide If one of the compounds mentioned below can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in every case. All of the mixture partners mentioned can, if they are capable of doing so on account of their functional groups, optionally form salts with suitable bases or acids. Insecticides / acaricides / nematicides
Die hier mit ihrem„Common Name“ genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch („The Pesticide Manual“ 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z. B. http://www.alanwood.net/pesticides). Die Klassifizierung basiert auf dem zum Zeitpunkt der Einreichung dieser Patentanmeldung gültigen IRAC Mode of Action Classification Scheme. The active ingredients mentioned here with their "Common Name" are known and described, for example, in the Pesticide Manual ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or can be researched on the Internet (e.g. http: //www.alanwood. net / pesticides). The classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application.
(1) Acetylcholinesterase(AChE)-Inhibitoren, wie beispielsweise Carbamate, z. B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder Organophosphate, z. B. Acephat, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoat, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Heptenophos, Imicyafos, Isofenphos, Isopropyl-0-(methoxyaminothio-phosphoryl)salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion-methyl, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, e.g. B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarban, Propoxuracam, Carbox XMC and xylylcarb or organophosphates, e.g. B. Acephat, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimvinphosat, Dimethonatos EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Heptenophos, Imicyafos, Isofenphos, Isopropyl-0- (methoxyaminothio-phosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathosate, Midathos, Monid , Oxydemeton-methyl, Parathion-methyl, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Tefos, Tefos, Tefos, Tefos, Tefos , Triclorfon and vamidothion.
(2) GABA-gesteuerte Chlorid-Kanal-Blocker, wie beispielsweise Cyclodien-organochlorine, z. B. Chlordan und Endosulfan oder Phenylpyrazole (Fiprole), z. B. Ethiprol und Fipronil. (2) GABA controlled chloride channel blockers, such as cyclodiene organochlorine, e.g. B. Chlordan and Endosulfan or Phenylpyrazole (Fiprole), e.g. B. Ethiprol and Fipronil.
(3) Natrium-Kanal-Modulatoren, wie beispielsweise Pyrethroide, z. B. Acrinathrin, Allethrin, d-cis- trans-Allethrin, d-trans Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma- Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta- Cypermethrin, Cyphenothrin [(lR)-trans-Isomer], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomer], Esfenvalerat, Etofenprox, Fenpropathrin, Fenvalerat, Flucythrinat, Flumethrin, tau-Fluvalinat, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer], Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(lR)-Isomer], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. (4) Kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Neonicotinoide, z. B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nicotin oder Sulfoxaflor oder Flupyradifurone. (3) sodium channel modulators such as pyrethroids, e.g. B. acrinathrin, allethrin, d-cis-trans-allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambhalhrinothrin, lambda gammhalin , Cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans-isomer], deltamethrin, empenthrin [(EZ) - (lR) -isomer], esfen valerate, fenprohrin , Fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, Halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(IR) -trans-isomer], prallethrin, pyrethrine (pyrethrum), resmethrin, tetramhrhrinine, silafhrinine, silafhrinine, IR) isomer], tralomethrin and transfluthrin or DDT or methoxychlor. (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as neonicotinoids, e.g. B. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
(5) Allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Spinosyne, z. B. Spinetoram und Spinosad. (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as Spinosyne, e.g. B. Spinetoram and Spinosad.
(6) Allosterische Modulatoren des Glutamat-abhängigen Chloridkanals(GluCl), wie beispielsweise Avermectine/Milbemycine, z. B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) Allosteric modulators of the glutamate-dependent chloride channel (GluCl), such as, for example, avermectine / milbemycine, e.g. B. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
(7) Juvenilhormon-Mimetika, wie beispielsweise Juvenilhormon- Analoge, z. B. Hydropren, Kinopren und Methopren oder Fenoxycarb oder Pyriproxyfen. (8) Verschiedene nicht spezifische (multi-site) Inhibitoren, wie beispielsweise Alkylhalogenide, z. B.(7) Juvenile hormone mimetics, such as juvenile hormone analogs, e.g. B. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen. (8) Various non-specific (multi-site) inhibitors, such as alkyl halides, e.g. B.
Methylbromid und andere Alkylhalogenide; oder Chloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein oder Methylisocyanaterzeuger, z. B. Diazomet und Metam. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or Brechweinstein or methyl isocyanate producer, e.g. B. Diazomet and Metam.
(9) Modulatoren chordotonaler Organe, z. B. Pymetrozin oder Flonicamid. (9) Modulators of chordotonic organs, e.g. B. pymetrozine or flonicamide.
(10) Milbenwachstumsinhibitoren, wie z. B. Clofentezin, Hexythiazox und Diflovidazin oder Etoxazol. (11) Mikrobielle Disruptoren der Insektendarmmembran, wie z. B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und B.t. -Pflanzenproteine: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Abl/35Abl. (10) mite growth inhibitors such as B. clofentezin, hexythiazox and diflovidazine or etoxazole. (11) Microbial disruptors of the insect intestinal membrane, such as. B. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and B.t. Plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Abl / 35Abl.
(12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinnverbindungen, z. B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder(12) Inhibitors of mitochondrial ATP synthase, such as ATP disruptors, such as, for example, diafenthiuron or organotin compounds, e.g. B. azocyclotin, cyhexatin and fenbutatin oxide or
Propargit oder Tetradifon. Propargite or tetradifon.
(13) Entkoppler der oxidativen Phoshorylierung durch Störung des Protonengradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. (13) Decouplers of oxidative phosphorylation by disturbing the proton gradient, such as chlorfenapyr, DNOC and sulfluramide.
(14) Blocker des nicotinischen Acetylcholinrezeptorkanals, wie beispielsweise Bensultap, Cartap- hydrochlorid, Thiocyclam und Thiosultap-Natrium. (14) Blockers of the nicotinic acetylcholine receptor channel, such as, for example, bensultap, cartap hydrochloride, thiocyclam and thiosultap sodium.
(15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin. (15) Inhibitors of chitin biosynthesis, type 0, such as, for example, bistrifluron, chlorofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron. (16) Type 1 chitin biosynthesis inhibitors such as buprofezin.
(17) Häutungsdisruptor (insbesondere bei Dipteren, d. h. Zweiflüglern), wie beispielsweise Cyromazin. (17) molting disruptor (especially dipteras, i.e. two-wingers) such as cyromazine.
(18) Ecdyson- Rezeptor- Agonisten, wie beispielsweise Chromafenozid, Halofenozid, Methoxyfenozid und Tebufenozid. (19) Oktopamin-Rezeptor- Agonisten, wie beispielsweise Amitraz. (18) Ecdysone receptor agonists such as chromafenozid, halofenozid, methoxyfenozid and tebufenozid. (19) Octopamine receptor agonists such as Amitraz.
(20) Mitochondriale Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim. (20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnon or acequinocyl or fluacrypyrim.
(21) Mitochondriale Komplex-I-Elektronentransportinhibitoren, wie beispielsweise METI- Akarizide, z. B. Fenazaquin, Fenpyroximat, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenon (Derris). (21) Mitochondrial complex I electron transport inhibitors, such as, for example, METI acaricides, e.g. B. Fenazaquin, Fenpyroximat, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenon (Derris).
(22) Blocker des spannungsabhängigen Natriumkanals, wie z. B. Indoxacarb oder Metaflumizone. (22) Blockers of the voltage-dependent sodium channel, such as. B. indoxacarb or metaflumizone.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z. B. Spirodiclofen, Spiromesifen und Spirotetramat. (23) Inhibitors of acetyl-CoA carboxylase, such as tetronic and tetramic acid derivatives, e.g. B. spirodiclofen, spiromesifen and spirotetramat.
(24) Inhibitoren des mitochondrialen Komplex-IV-Elektronentransports, wie beispielsweise Phosphine, z. B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanide,(24) Mitochondrial complex IV electron transport inhibitors, such as phosphines, e.g. B. aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides,
Calciumcyanid, Kaliumcyanid und Natriumcyanid. Calcium cyanide, potassium cyanide and sodium cyanide.
(25) Inhibitoren des mitochondrialen Komplex-II-Elektronentransports, wie beispielsweise beta- Ketonitrilderivate, z. B. Cyenopyrafen und Cyflumetofen und Carboxanilide, wie beispielsweise Pyflubumid. (28) Ryanodinrezeptor-Modulatoren, wie beispielsweise Diamide, z. B. Chlorantraniliprol,(25) Inhibitors of mitochondrial complex II electron transport, such as beta-ketonitrile derivatives, e.g. B. Cyenopyrafen and Cyflumetofen and carboxanilides, such as pyflubumide. (28) Ryanodine receptor modulators, such as diamides, e.g. B. chlorantraniliprole,
Cyantraniliprol und Flubendiamid, weitere Wirkstoffe wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximat, Bifenazat, Broflanilid, Bromopropylat, Chinomethionat, Chloroprallethrin, Cryolit, Cyclaniliprol, Cycloxaprid, Cyhalodiamid, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizin, Fluensulfon, Flufenerim, Flufenoxystrobin, Flufiprol,Cyanotraniliprole and flubendiamide, other active ingredients such as afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolit, cyclaniliprol, cycloxaprid, dyhalomoflutinolidilidolinilidolinilidolinilidolin, dolinomidolinilidolinilidolin, dolinomidolinilidolinilidolin, dolinomidolinilidolin, dolinomidolinoid, dichalomidylinophenol, dicylomonidolinolidolinidolin, dolinidolinidolinidolin, dolonidolidolin, dicylnomidylinidolin, pd Fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprol,
Fluhexafon, Fluopyram, Fluralaner, Fluxametamid, Fufenozid, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprol, Tetrachlorantraniliprol, Tigolaner, Tioxazafen, Thiofluoximat, Triflumezopyrim und Iodmethan; des Weiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo), sowie folgende Verbindungen: l- {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfmyl]phenyl}-3-(trifluormethyl)-lH- l,2,4-triazol-5-amin (bekannt aus W02006/043635) (CAS 885026-50-6), { 1 '-[(2E)-3-(4-Fluhexafon, Fluopyram, Fluralaner, Fluxametamid, Fufenozid, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrol, Tichludin, Titrated, Titrated, Tungsten, Tetranidium, Trichlorodiphenyl Thiofluoximate, triflumezopyrim and iodomethane; of Other preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), as well as the following compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfmyl] phenyl} -3 - (trifluoromethyl) -lH- l, 2,4-triazol-5-amine (known from W02006 / 043635) (CAS 885026-50-6), {1 '- [(2E) -3- (4-
Chlorphenyl)prop-2-en- 1 -yl]-5-fluorspiro[indol-3,4'-piperidin]- 1 (2H)-yl) (2-chlorpyridin-4-yl)methanon (bekannt aus W02003/106457) (CAS 637360-23-7), 2-Chlor-N-[2- { l-[(2E)-3-(4-chlorphenyl)prop-2- en- l-yl]piperidin-4-yl}-4-(trifluormethyl)phenyl]isonicotinamid (bekannt aus W02006/003494) (CAS 872999-66- 1), 3-(4-Chlor-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO 2010052161) (CAS 1225292-17-0), 3-(4-Chlor-2, 6-dimethylphenyl)-8-methoxy-2- oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus EP 2647626) (CAS- 1440516-42-6), 4- (But-2-in-l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluorpyrimidin (bekannt aus W02004/099160) (CAS 792914-58-0), PF1364 (bekannt aus JP2010/018586) (CAS-Reg.No. 1204776-60-2), N-[(2E)- l- [(6-Chlorpyridin-3-yl)methyl]pyridin-2(lH)-yliden]-2,2,2-trifluoracetamid (bekannt ausChlorphenyl) prop-2-en-1-yl] -5-fluorspiro [indol-3,4'-piperidine] - 1 (2H) -yl) (2-chloropyridin-4-yl) methanone (known from WO2003 / 106457 ) (CAS 637360-23-7), 2-chloro-N- [2- {l - [(2E) -3- (4-chlorophenyl) prop-2- en-l-yl] piperidin-4-yl} -4- (trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3- (4-chloro-2,6-dimethylphenyl) -4-hydroxy-8-methoxy-1,8 -diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2, 6-dimethylphenyl) -8-methoxy-2-oxo -l, 8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from EP 2647626) (CAS-1440516-42-6), 4- (but-2-in-l-yloxy) - 6- (3,5-dimethylpiperidin-l-yl) -5-fluoropyrimidine (known from W02004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS-Reg.No. 1204776- 60-2), N - [(2E) - l- [(6-chloropyridin-3-yl) methyl] pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from
WO2012/029672) (CAS 1363400-41-2), (3E)-3-[l-[(6-Chlor-3-pyridyl)methyl]-2-pyridyliden]-l,l, l- trifluorpropan-2-on (bekannt aus WO2013/144213) (CAS 1461743- 15-6), N-[3-(Benzylcarbamoyl)-4- chlorphenyl]- 1 -methyl-3-(pentafluorethyl)-4-(trifluormethyl)- lH-pyrazol-5-carboxamid (bekannt aus WO2010/051926) (CAS 1226889-14-0), 5-Brom-4-chlor-N-[4-chlor-2-methyl-6-WO2012 / 029672) (CAS 1363400-41-2), (3E) -3- [l - [(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -l, l, l-trifluoropropane-2- on (known from WO2013 / 144213) (CAS 1461743-15-6), N- [3- (benzylcarbamoyl) -4-chlorophenyl] - 1 -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) - 1H-pyrazole -5-carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N- [4-chloro-2-methyl-6-
(methylcarbamoyl)phenyl]-2-(3-chlor-2-pyridyl)pyrazol-3 -carboxamid (bekannt aus CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl- N-(cis-l-oxido-3-thietanyl)benzamid, 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3- isoxazolyl]-2-methyl-N-(trans- l-oxido-3-thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5- dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis- 1 -oxido-3-thietanyl)benzamid (bekannt aus WO 2013/050317 Al) (CAS 1332628-83-7), N-[3-Chlor- l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3- [(3,3,3-trifluorpropyl)sulfmyl]propanamid, (+)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3- [(3,3,3-trifluorpropyl)sulfinyl]propanamid und (-)-N-[3-Chlor-l -(3-pyridinyl)- lH-pyrazol-4-yl]-N-ethyl- 3-[(3,3,3-trifluorpropyl)sulfinyl]propanamid (bekannt aus WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 Al) (CAS 1477923-37-7), 5-[[(2E)-3-Chlor-2-propen-l-yl]amino]-l-[2,6-dichlor-4- (trifluormethyl)phenyl]-4-[(trifluormethyl)sulfinyl]-lH-pyrazol-3-carbonitrile (bekannt aus CN 101337937 A) (CAS 1 105672-77-2), 3-Brom-N-[4-chlor-2-methyl-6-(methylcarbamoyl) phenyl] -2- (3-chloro-2-pyridyl) pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4- [5- (3,5-dichlorophenyl) -4 , 5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis-l-oxido-3-thietanyl) benzamide, 4- [5- (3,5-dichlorophenyl) -4, 5-dihydro-5- (trifluoromethyl) -3- isoxazolyl] -2-methyl-N- (trans-l-oxido-3-thietanyl) benzamide and 4 - [(5S) -5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis- 1 -oxido-3-thietanyl) benzamide (known from WO 2013/050317 Al) (CAS 1332628-83 -7), N- [3-chloro-l- (3-pyridinyl) -lH-pyrazol-4-yl] -N-ethyl-3- [(3,3,3-trifluoropropyl) sulfmyl] propanamide, (+ ) -N- [3-chloro-l- (3-pyridinyl) -lH-pyrazol-4-yl] -N-ethyl-3- [(3,3,3-trifluoropropyl) sulfinyl] propanamide and (-) - N- [3-chloro-1 - (3-pyridinyl) - 1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) sulfinyl] propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 Al) (CAS 1477923-37-7), 5 - [[(2E) -3-chloro-2-propen-l-yl] amino] -l- [2 , 6-dichloro-4- (trifluoromethyl ) phenyl] -4 - [(trifluoromethyl) sulfinyl] -lH-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1 105672-77-2), 3-bromo-N- [4-chloro-2- methyl-6-
[(methylamino)thioxomethyl]phenyl]-l-(3-chlor-2-pyridinyl)- lH-pyrazol-5-carboxamid, [(methylamino) thioxomethyl] phenyl] -1- (3-chloro-2-pyridinyl) - 1H-pyrazole-5-carboxamide,
(Liudaibenjiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9); N-[4-Chlor-2-[[(l,l- dimethylethyl)amino]carbonyl]-6-methylphenyl]-l-(3-chlor-2-pyridinyl)-3-(fluormethoxy)-lH-pyrazol- 5-carboxamid (bekannt aus WO 2012/034403 Al) (CAS 1268277-22-0), N-[2-(5-Amino-l,3,4- thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5-carboxamid (bekannt aus WO 201 1/085575 Al) (CAS 1233882-22-8), 4-[3-[2,6-Dichlor-4-[(3,3-dichlor-2-propen-l- yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN 101337940 A) (CAS 1 108184-52-6); (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-l-[3-(trifluormethyl)phenyl]ethyliden]-N-[4-(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N- [4-chloro-2 - [[(l, l-dimethylethyl) amino] carbonyl] -6-methylphenyl] -l- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -lH-pyrazole- 5-carboxamide (known from WO 2012/034403 Al) (CAS 1268277-22-0), N- [2- (5-amino-l, 3,4-thiadiazol-2-yl) -4-chloro-6- methylphenyl] -3-bromo-1- (3-chloro-2-pyridinyl) -lH-pyrazole-5-carboxamide (known from WO 201 1/085575 Al) (CAS 1233882-22-8), 4- [3- [2,6-dichloro-4 - [(3,3-dichloro-2-propen-l-yl) oxy] phenoxy] propoxy] -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN 101337940 A) ( CAS 1 108184-52-6); (2E) - and 2 (Z) -2- [2- (4-cyanophenyl) -l- [3- (trifluoromethyl) phenyl] ethylidene] -N- [4-
(difluormethoxy)phenyl]hydrazincarboxamid (bekannt aus CN 101715774 A) (CAS 1232543-85-9); Cyclopropancarbonsäure-3-(2,2-dichlorethenyl)-2,2-dimethyl-4-(lH-benzimidazol-2-yl)phenylester (bekannt aus CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-Chlor-2,5-dihydro-2- [[(methoxycarbonyl)[4-[(trifluormethyl)thio]phenyl]amino]carbonyl]indeno[l,2-e][l,3,4]oxadiazin- 4a(3H)-carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2); 6-Desoxy-3-0- ethyl-2,4-di-0-methyl- 1 - [N- [4- [ 1 - [4-( 1 , 1 ,2,2,2-pentafluorethoxy)phenyl] - 1 H- 1 ,2,4-triazol-3 - yl]phenyl]carbamat]-a-L-mannopyranose (bekannt aus US 2014/0275503 Al) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluonnethylpyridazm-3-yl)-3- azabicyclo[3.2.l]octan (CAS 1253850-56-4), (8-anti)-8-(2-Cyclopropylmethoxy-4- trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2.l]octan (CAS 933798-27- 7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3- azabicyclo[3.2.1 ]octan (bekannt aus WO 2007040280 Al, WO 2007040282 Al) (CAS 934001-66-8), N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)thio]-propanamid (difluoromethoxy) phenyl] hydrazine carboxamide (known from CN 101715774 A) (CAS 1232543-85-9); Cyclopropanecarboxylic acid 3- (2,2-dichloroethenyl) -2,2-dimethyl-4- (1H-benzimidazol-2-yl) phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS) -7-chloro-2,5-dihydro-2- [[(methoxycarbonyl) [4 - [(trifluoromethyl) thio] phenyl] amino] carbonyl] indeno [1,2-e] [1,3,4 ] oxadiazine-4a (3H) -carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-0-ethyl-2,4-di-0-methyl-1 - [N- [4- [1 - [4- (1, 1, 2,2,2-pentafluoroethoxy) phenyl] - 1 H-1, 2,4-triazol-3-yl] phenyl] carbamate] aL mannopyranose (known from US 2014/0275503 Al) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluonomethylpyridazm-3-yl) -3- azabicyclo [3.2.l] octane (CAS 1253850-56-4), (8-anti) -8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.l] octane (CAS 933798-27- 7), (8-syn) -8- (2nd -Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3- azabicyclo [3.2.1] octane (known from WO 2007040280 Al, WO 2007040282 Al) (CAS 934001-66-8), N - [3-Chloro-l- (3-pyridinyl) -lH-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) thio] propanamide
(bekannt aus WO 2015/058021 Al, WO 2015/058028 Al) (CAS 1477919-27-9) und N-[4- (Aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-l-(3-chloro-2-pyridinyl)- lii-pyrazol-5-carboxamid (bekannt aus CN 103265527 A) (CAS 1452877-50-7), 5-(l,3-Dioxan-2-yl)-4- [[4-(trifluormethyl)phenyl]methoxy]-pyrimidin (bekannt aus WO 2013/115391 Al) (CAS 1449021-97- 9), 3-(4-Chlor-2,6-dimethylphenyl)-4-hydroxy-8-methoxy- 1 -methyl- 1 ,8-diazaspiro[4.5]dec-3-en-2-on(known from WO 2015/058021 Al, WO 2015/058028 Al) (CAS 1477919-27-9) and N- [4- (aminothioxomethyl) -2-methyl-6 - [(methylamino) carbonyl] phenyl] -3- bromo-l- (3-chloro-2-pyridinyl) - lii-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5- (l, 3-dioxan-2-yl) -4- [[4- (trifluoromethyl) phenyl] methoxy] pyrimidine (known from WO 2013/115391 Al) (CAS 1449021-97- 9), 3- (4-chloro-2,6-dimethylphenyl) -4- hydroxy-8-methoxy-1-methyl-1,8-diazaspiro [4.5] dec-3-en-2-one
(bekannt aus WO 2010/066780 Al, WO 2011/151146 Al) (CAS 1229023-34-0), 3-(4-Chlor-2,6- dimethylphenyl)-8-methoxy-l -methyl- l,8-diazaspiro[4.5]decane-2,4-dion (bekannt aus WO 2014/187846 Al) (CAS 1638765-58-8), 3-(4-Chlor-2,6-dimethylphenyl)-8-methoxy-l-methyl-2-oxo-l, 8-diazaspiro[4.5]dec-3-en-4-yl-carbonsäureethylester (bekannt aus WO 2010/066780 Al, WO 2011151146 Al) (CAS 1229023-00-0), N-[l-[(6-chlor-3-pyridinyl)methyl]-2(ltf)-pyridinylidene]-2,2, 2-trifluor-acetamide (bekannt aus DE 3639877 Al, WO 2012029672 Al) (CAS 1363400-41-2), [N(£)]- N-[l-[(6-chlor-3-pyridinyl)methyl]-2(li7)-pyridinylidene]-2,2,2-trifluor-acetamide (bekannt aus WO 2016005276 Al) (CAS 1689566-03-7), [N(Z)]-N-[l-[(6-chlor-3-pyridinyl)methyl]-2(lfl)- pyridinylidene]-2,2,2-trifluor- acetamide (CAS 1702305-40-5), 3-e«<io-3-[2-Propoxy-4-(trifluormethyl) phenoxy]-9-[[5-(trifluormethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.l]nonan (bekannt aus WO 2011/105506 Al, WO 2016/133011 Al) (CAS 1332838-17-1). (known from WO 2010/066780 A1, WO 2011/151146 A1) (CAS 1229023-34-0), 3- (4-chloro-2,6-dimethylphenyl) -8-methoxy-1-methyl-1, 8- diazaspiro [4.5] decane-2,4-dione (known from WO 2014/187846 Al) (CAS 1638765-58-8), 3- (4-chloro-2,6-dimethylphenyl) -8-methoxy-l-methyl -2-oxo-1,8-diazaspiro [4.5] dec-3-en-4-yl-carboxylic acid ethyl ester (known from WO 2010/066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N- [l - [(6-chloro-3-pyridinyl) methyl] -2 (ltf) pyridinylidenes] -2,2, 2-trifluoroacetamide (known from DE 3639877 Al, WO 2012029672 Al) (CAS 1363400-41-2) , [N (£)] - N- [l - [(6-chloro-3-pyridinyl) methyl] -2 (li7) pyridinylidenes] -2,2,2-trifluoroacetamide (known from WO 2016005276 Al) (CAS 1689566-03-7), [N (Z)] - N- [l - [(6-chloro-3-pyridinyl) methyl] -2 (lfl) - pyridinylidenes] -2,2,2-trifluoro- acetamide (CAS 1702305-40-5), 3-e « < io-3- [2-propoxy-4- (trifluoromethyl) phenoxy] -9 - [[5- (trifluoromethyl) -2-pyridinyl] oxy] -9 -azabicyclo [3.3.1] nonane (known from WO 2011/105506 A1, WO 2016/133011 A1) (CAS 1332838-17-1).
Fungizide Fungicides
Die hier mit ihrem“Common Name” spezifizierten Wirkstoffe sind bekannt und beispielsweise im “Pesticide Manual” (16. Aufl. British Crop Protection Council) oder im Internet recherchierbar (beispielsweise: http://www.alanwood.net/nesticidesi beschrieben. The active ingredients specified here with their “Common Name” are known and can be researched, for example, in the “Pesticide Manual” (16th edition of the British Crop Protection Council) or on the Internet (for example: http://www.alanwood.net/nesticidesi).
Alle genannten Mischungspartner der Klassen (1) bis (15) können, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Alle genannten fungiziden Mischungspartner der Klassen (1) bis (15) können gegebenenfalls tautomere Formen einschließen. All of the above-mentioned mixing partners of classes (1) to (15) can, if they are capable of doing so on account of their functional groups, salts with suitable bases or acids form. All of the fungicidal mixture partners of classes (1) to (15) mentioned can optionally include tautomeric forms.
1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenoconazol, (1.003) Epoxiconazol, (1.004) Fenhexamid, (1.005) Fenpropidin, (1.006) Fenpropimorph, (1.007) Fenpyrazamin, (1.008) Fluquinconazol, (1.009) Flutriafol, (1.010) Imazalil, (1.01 1) Imazalil Sulfat, (1.012) Ipconazol, (1.013) Metconazol, (1.014) Myclobutanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.017) Propiconazol, (1.018) Prothioconazol, (1.019) Pyrisoxazol, (1.020) Spiroxamin, (1.021) Tebuconazol, (1.022) Tetraconazol, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazol, (1.026) (lR,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l -(lFl-l,2,4-triazol- l- ylmethyl)cyclopentanol, (1.027) (l S,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l-(lH- 1,2,4- triazol- 1 -ylmethyl)cyclopentanol, (1.028) (2R)-2-( 1 -Chlorcyclopropyl)-4-[( 1 R)-2,2-dichlorcyclopropyl]- 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol ( 1.029) (2R)-2-( 1 -Chlorcyclopropyl)-4- [( 1 S)-2,2- dichlorcyclopropyl]- 1 -(1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.030) (2R)-2-[4-(4-Chlorphenoxy)-2-1) inhibitors of ergosterol biosynthesis, for example (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidine, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1.009) flutriafol, (1.010) imazalil, (1.01 1) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothiocone , (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetraconazole, (1,023) triadimenol, (1,024) tridemorph, (1,025) triticonazole, (1,026) (lR, 2S, 5S) -5- ( 4-chlorobenzyl) -2- (chloromethyl) -2-methyl-l - (lFl-l, 2,4-triazol-l-ylmethyl) cyclopentanol, (1,027) (l S, 2R, 5R) -5- (4th -Chlorobenzyl) -2- (chloromethyl) -2-methyl-l- (lH- 1,2,4-triazole-1-ylmethyl) cyclopentanol, (1,028) (2R) -2- (1-chlorocyclopropyl) -4- [(1 R) -2,2-dichlorocyclopropyl] - 1 - (1 H-1, 2,4-triazol-1-yl) butan-2-ol (1,029) (2R) -2- (1-chlorocyclopropyl) -4- [(1 S) -2,2- dichlorc yclopropyl] - 1 - (1H- 1, 2,4-triazol-1-yl) butan-2-ol, (1,030) (2R) -2- [4- (4-chlorophenoxy) -2-
(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, (1.031) (2S)-2-(l -Chlorcyclopropyl)-4-(trifluoromethyl) phenyl] - 1 - (1 H-1, 2,4-triazol-1-yl) propan-2-ol, (1,031) (2S) -2- (1-chlorocyclopropyl) -4-
[( 1 R)-2,2-dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.032) (2S)-2-( 1 -Chlorcyclopropyl)- 4-[(l S)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-[(1 R) -2,2-dichlorocyclopropyl] -1 - (1 H-1, 2,4-triazol-1-yl) butan-2-ol, (1,032) (2S) -2- (1-chlorocyclopropyl ) - 4 - [(l S) -2,2-dichlorocyclopropyl] -l- (lH-l, 2,4-triazol-l-yl) butan-2-ol, (1.033) (2S) -2- [ 4- (4-
Chlorphenoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol- l-yl)propan-2-ol, (1.034) (R)-[3-(4-Chlor-Chlorophenoxy) -2- (trifluoromethyl) phenyl] -l- (lH-l, 2,4-triazol-l-yl) propan-2-ol, (1,034) (R) - [3- (4-chloro-
2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-Chlor-2- fluorphenyl)-5-(2,4-difluorphenyl)- 1 ,2-oxazol-4-yl] (pyridin-3 -yl)methanol, (1.036) [3 -(4-Chlor-2- fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) l-({(2R,4S)-2-[2- Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl- l,3-dioxolan-2-yl}methyl)- lH-l,2,4-triazol, (1.038) 1-2-fluorophenyl) -5- (2,4-difluorophenyl) -1, 2-oxazol-4-yl] (pyridin-3-yl) methanol, (1,035) (S) - [3- (4-chloro-2 - fluorophenyl) -5- (2,4-difluorophenyl) - 1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (1,036) [3 - (4-chloro-2-fluorophenyl) -5 - (2,4-difluorophenyl) -1, 2-oxazol-4-yl] (pyridin-3-yl) methanol, (1,037) l - ({(2R, 4S) -2- [2- chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-l, 3-dioxolan-2-yl} methyl) - lH-l, 2,4-triazole, (1,038) 1-
( {(2S,4S)-2- [2-Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl- 1 ,3-dioxolan-2-yl}methyl)- 1 H- 1 ,2,4-triazol, (1.039) l- {[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}- lH-l,2,4-triazol-5-yl- thiocyanat, (1.040) l- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH- l,2,4-triazol-5-yl-thiocyanat, (1.041) l- {[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-yl-thiocyanat, (1.042) 2-[(2R,4R,5R)- l-(2,4-Dichlorphenyl)-5-hydroxy- 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- l,2,4-triazol-3-thion, (1.043) 2-[(2R,4R,5S)-l-(2,4-({(2S, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1, 3-dioxolan-2-yl} methyl) - 1 H-1, 2.4 -triazol, (1,039) l- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} - lH-l, 2,4-triazol-5-yl- thiocyanate, (1,040) l- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -lH- l, 2,4- triazol-5-yl-thiocyanate, (1,041) l- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -lH- l, 2,4-triazol-5-yl-thiocyanate, (1,042) 2 - [(2R, 4R, 5R) - l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane 4-yl] -2,4-dihydro-3H-l, 2,4-triazol-3-thione, (1,043) 2 - [(2R, 4R, 5S) -l- (2,4-
Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.044) 2- [(2R,4S,5R)- 1 -(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- 1 ,2,4- triazol-3-thion, (1.045) 2-[(2R,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.046) 2-[(2S,4R,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H- l,2,4-triazol-3-thion, (1.047) 2-[(2S,4R,5S)-l-(2,4-Dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazol-3-thione, (1,044) 2- [(2R, 4S , 5R) - 1 - (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2,4-triazol-3-thione , (1,045) 2 - [(2R, 4S, 5S) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- l, 2,4-triazol-3-thione, (1,046) 2 - [(2S, 4R, 5R) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4- yl] -2,4-dihydro-3H- l, 2,4-triazol-3-thione, (1,047) 2 - [(2S, 4R, 5S) -l- (2,4-
Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.048) 2- [(2S,4S,5R)- 1 -(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- 1 ,2,4-triazol-Dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazol-3-thione, (1,048) 2- [(2S, 4S , 5R) - 1 - (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- 1, 2,4-triazole-
3-thion, (1.049) 2-[(2S,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.050) 2-[l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H- l,2,4-triazol-3-thion, (1.051) 2-[2-Chlor-4-(2,4-dichlorophenoxy)phenyl]-l-(lH- 1.2.4-triazol- 1 -yl)propan-2-ol, (1.052) 2-[2-Chlor-4-(4-chlorphenoxy)phenyl]- 1 -(1 H- 1 ,2,4-triazol- 1 - yl)butan-2-ol, (1.053) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]- l-(lH-l,2,4-triazol-l-yl)butan- 2-ol, ( 1.054) 2- [4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]- 1 -( 1H- 1 ,2,4-triazol- 1 -yl)pentan-2-ol,3-thione, (1,049) 2 - [(2S, 4S, 5S) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro -3H-l, 2,4-triazol-3-thione, (1,050) 2- [l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2, 4-dihydro-3H-l, 2,4-triazol-3-thione, (1,051) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -l- (lH- 1,2.4-triazol-1-yl) propan-2-ol, (1,052) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1 - (1 H-1, 2,4-triazole- 1-yl) butan-2-ol, (1,053) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (lH-l, 2,4-triazol-l-yl) butane - 2-ol, (1,054) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1 - (1H-1, 2,4-triazol-1-yl) pentan-2-ol,
(1.055) 2- [4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, (1.056)(1,055) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1 - (1 H- 1, 2,4-triazol-1-yl) propan-2-ol, (1,056)
2- {[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.057) 2- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3F[-2- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-l, 2,4-triazol-3-thione, (1,057) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3F [-
1.2.4-triazol-3-thion, (1.058) 2- {[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yljmcthyl [ -2,4-dihydro-3H- 1 ,2,4-triazol-3-thion, (1.059) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl- 1 -( 1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, ( 1.060) 5-(Allylsulfanyl)- 1 - { [3 -(2-chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol, (1.061) 5-(Allylsulfanyl)- 1 - { [rel(2R,3R)-3 -(2- chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} - 1H- 1 ,2,4-triazol, ( 1.062) 5-(Allylsulfanyl)- 1 - {[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}- lH-l,2,4-triazol, (1.063) N'- (2,5-Dimethyl-4- {[3-(l,l,2,2-tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N- methylimidoformamid, (1.064) N'-(2,5-Dimethyl-4- {[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)- N-ethyl-N-methylimidoformamid, (1.065) N'-(2,5-Dimethyl-4- { [3-(2, 2,3,3- tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidofonnamid, (1.066) N'-(2,5-Dimethyl- 4- {[3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.067) N'-(2,5-1,2.4-triazol-3-thione, (1,058) 2- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-ylmethyl; -2, 4-dihydro-3H-1, 2,4-triazol-3-thione, (1,059) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1 - (1 H-1, 2,4 -triazol- 1 -ylmethyl) cyclopentanol, (1,060) 5- (allylsulfanyl) - 1 - {[3 - (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} - 1 H - 1, 2,4-triazole, (1,061) 5- (allylsulfanyl) - 1 - {[rel (2R, 3R) -3 - (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2- yl] methyl} - 1H- 1, 2,4-triazole, (1,062) 5- (allylsulfanyl) - 1 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4- difluorophenyl) oxiran-2-yl] methyl} - 1H-1,2,4-triazole, (1,063) N'- (2,5-dimethyl-4- {[3- (1,1,2,2-tetrafluoroethoxy ) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1,064) N '- (2,5-dimethyl-4- {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) - N-ethyl-N-methylimidoformamide, (1,065) N '- (2,5-dimethyl-4- {[3- (2, 2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl- N-methylimidofonnamide, (1,066) N '- (2,5-dimethyl- 4- {[3- ( pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1,067) N '- (2,5-
Dimethyl-4- {3-[(l , 1 ,2,2-tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid,Dimethyl-4- {3 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide,
(1.068) N'-(2,5-Dimethyl-4- {3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamid, (1.069) N'-(2,5-Dimethyl-4- {3-[(2, 2,3,3- tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.070) N'-(2,5-Dimethyl- 4- {3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.071) N'-(2,5-(1,068) N '- (2,5-dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1,069) N' - ( 2,5-Dimethyl-4- {3 - [(2, 2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1,070) N '- (2,5-dimethyl - 4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1,071) N '- (2,5-
Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamid, ( 1.072) N'-(4- { [3-Dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (1,072) N '- (4- {[3-
(Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.073) N'- (4- {3-[(Difluormethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid,(Difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1,073) N'- (4- {3 - [(difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide,
(1.074) N'-[5-Brom-6-(2,3-dihydro- lH-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N- methylimidoformamid, (1.075) N'- {4-[(4,5-Dichlor-l,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl- N-methylimidoformamid, (1.076) N'- {5-Brom-6-[(lR)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-(1,074) N '- [5-bromo-6- (2,3-dihydro-lH-inden-2-yloxy) -2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamide, (1,075) N '- {4 - [(4,5-dichloro-l, 3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, (1,076) N'- {5- Bromine-6 - [(IR) -l- (3,5-difluorophenyl) ethoxy] -2-methylpyridine-
3-yl}-N-ethyl-N-methylimidoformamid, (1.077) N'- {5-Brom-6-[(l S)- l-(3,5-difluorphenyl)ethoxy]-2- methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, (1.078) N'- {5-Brom-6-[(cis-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, ( 1.079) N'- {5-3-yl} -N-ethyl-N-methylimidoformamide, (1,077) N'- {5-bromo-6 - [(IS) - 1- (3,5-difluorophenyl) ethoxy] -2-methylpyridine-3- yl} -N-ethyl-N-methylimidoformamide, (1,078) N'- {5-bromo-6 - [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamide, (1,079) N'- {5-
Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, (1.080) N'- {5-Bromo-6-[l -(3, 5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamid, (1.081) Mefentrifluconazole, (1.082) Ipfentrifluconazole. Bromo-6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1,080) N'- {5-bromo-6- [l - (3rd , 5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1,081) mefentrifluconazole, (1,082) apple trifluconazole.
2) Inhibitoren der Atmungskette am Komplex I oder II beispielsweise (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, (2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isofetamid, (2.010) Isopyrazam (anti-epimeres Enantiomer lR,4S,9S), (2.011) Isopyrazam (anti-epimeres Enantiomer lS,4R,9R), (2.012) Isopyrazam (anti epimeres Racemat lRS,4SR,9SR), (2.013) Isopyrazam (Mischung des syn-epimeren Razemates lRS,4SR,9RS und des anti-epimeren Razemates lRS,4SR,9SR), (2.014) Isopyrazam (syn-epimeres Enantiomer lR,4S,9R), (2.015) Isopyrazam (syn-epimeres Enantiomer lS,4R,9S), (2.016) Isopyrazam (syn-epimeres Racemat lRS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (2.020) Pyraziflumid, (2.021) Sedaxane, (2.022) l,3-Dimethyl-N-(l,l,3-trimethyl-2,3- dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, (2.023) 1 ,3-Dimethyl-N- [(3R)- 1 , 1 ,3-trimethyl-2,3- dihydro- lH-inden-4-yl]- lH-pyrazol-4-carboxamid, (2.024) 1 ,3-Dimethyl-N-[(3S)- 1 , 1 ,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.025) l-Methyl-3-(trifluormethyl)-N-[2'- (trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.026) 2-Fluor-6-(trifluoromethyl)-N-(l,l,3- trimethyl-2,3-dihydro-lH-inden-4-yl)benzamid, (2.027) 3-(Difluormethyl)-l-methyl-N-(l,l,3-trimethyl-2) Respiratory chain inhibitors 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 IR, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer IS, 4R, 9R), (2.012) isopyrazam (anti epimeric racemate lRS, 4SR, 9SR), (2,013) isopyrazam (mixture of the syn-epimeric racemate lRS, 4SR, 9RS and the anti-epimeric racemate lRS, 4SR, 9SR), (2,014) isopyrazam (syn-epimeric enantiomer lR, 4S , 9R), (2,015) isopyrazam (syn-epimeric enantiomer lS, 4R, 9S), (2,016) isopyrazam (syn-epimeric racemat lRS, 4SR, 9RS), (2,017) Penflufen, (2,018) penthiopyrad, (2,019) pydiflumetofen , (2,020) pyraziflumide, (2,021) sedaxane, (2,022) l, 3-dimethyl-N- (l, l, 3-trimethyl-2,3-dihydro-1 H-inden-4-yl) - 1 H- pyrazol-4-carboxamide, (2.023) 1, 3-dimethyl-N- [(3R) - 1, 1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] - 1H-pyrazole-4 -carboxamide, (2,024) 1, 3-dimethyl-N - [(3S) - 1, 1, 3-trimethyl-2,3-dihydro-lH-inden-4-yl] -lH-pyrazole-4-carboxamide, (2,025) l-Methyl-3- (trifluoromethyl) -N- [2'- (trifluoromethyl) biphenyl-2-yl] -lH-pyrazol-4-c arboxamide, (2,026) 2-fluoro-6- (trifluoromethyl) -N- (l, l, 3-trimethyl-2,3-dihydro-lH-inden-4-yl) benzamide, (2.027) 3- (difluoromethyl) -l-methyl-N- (l, l, 3-trimethyl-
2.3-dihydro-lH-inden-4-yl)-lH-pyrazol-4-carboxamid, (2.028) 3-(Difluormethyl)-l-methyl-N-[(3R)-2,3-dihydro-lH-inden-4-yl) -lH-pyrazole-4-carboxamide, (2,028) 3- (difluoromethyl) -l-methyl-N - [(3R) -
1.1.3-trimethyl-2,3-dihydro- lH-inden-4-yl]- lH-pyrazol-4-carboxamid, (2.029) 3-(Difluormethyl)- 1 - methyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.030) 3-1.1.3-trimethyl-2,3-dihydro-1H-inden-4-yl] - 1H-pyrazole-4-carboxamide, (2,029) 3- (difluoromethyl) - 1-methyl-N - [(3S) -l , l, 3-trimethyl-2,3-dihydro-lH-inden-4-yl] -lH-pyrazole-4-carboxamide, (2,030) 3-
(Difluormethyl)-N-(7-fluor- 1 , 1 ,3-trimethyl-2,3-dihydro- lH-inden-4-yl)- 1 -methyl- lFFpyrazol-4- carboxamid, (2.031) 3-(Difluormethyl)-N-[(3R)-7-fluor-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l- methyl-lH-pyrazol-4-carboxamid, (2.032) 3-(Difluoromethyl)-N-[(3S)-7-fluor-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-l -methyl- lH-pyrazol-4-carboxamid, (2.033) 5,8-Difluor-N-[2-(2-fluor-4- {[4- (trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amin, (2.034) N-(2-Cyclopentyl-5- fluorbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl- lH-pyrazol-4-carboxamid, (2.035) N- (2-tert-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluomiethyl)-5-fluor-l -methyl- lH-pyrazol-4- carboxamid, (2.036) N-(2-tert-Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor- 1 -methyl- 1H- pyrazol-4-carboxamid, (2.037) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor- 1 - methyl- lH-pyrazol-4-carboxamid, (2.038) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3- (difluormethyl)-5-fluor-l -methyl- lH-pyrazol-4-carboxamid, (2.039) N-[(lR,4S)-9-(Dichlormethylen)- 1 ,2,3,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl]-3-(difluormethyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.040) N-[(l S,4R)-9-(Dichlormethylen)- 1,2,3, 4-tetrahydro-l, 4-methanonaphthalen-5-yl]-3-(Difluoromethyl) -N- (7-fluoro-1, 1, 3-trimethyl-2,3-dihydro-lH-inden-4-yl) - 1 -methyl-lFFpyrazole-4-carboxamide, (2,031) 3- ( Difluoromethyl) -N - [(3R) -7-fluoro-l, l, 3-trimethyl-2,3-dihydro-lH-inden-4-yl] -l-methyl-lH-pyrazole-4-carboxamide, ( 2,032) 3- (difluoromethyl) -N - [(3S) -7-fluoro-l, l, 3-trimethyl-2,3-dihydro-lH-inden-4-yl] -l -methyl- lH-pyrazole- 4-carboxamide, (2,033) 5,8-difluoro-N- [2- (2-fluoro-4- {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2,034) N- (2-cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,035) N- (2-tert -Butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluomiethyl) -5-fluoro-l -methyl-lH-pyrazole-4-carboxamide, (2,036) N- (2-tert-butylbenzyl) -N-cyclopropyl -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,037) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5- fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,038) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-l -methyl- 1H-pyrazole-4-carboxamide, (2,039) N - [(IR, 4S) -9- (dichloromethylene) - 1, 2,3,4-tetrahydro-1, 4-methanonaphthalene-5-yl] - 3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,040) N - [(1S, 4R) -9- (dichloromethylene) - 1,2,3,4-tetrahydro-1,4 -methanonaphthalene-5-yl] -3-
(difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.041 ) N- [ 1 -(2,4-Dichlorphenyl)- 1 - methoxypropan-2-yl]-3-(difluormethyl)-l -methyl- lH-pyrazol-4-carboxamid, (2.042) N-[2-Chlor-6-(difluoromethyl) - 1-methyl-1 H -pyrazole-4-carboxamide, (2,041) N- [1 - (2,4-dichlorophenyl) - 1 - methoxypropan-2-yl] -3- (difluoromethyl) -l - methyl-1H-pyrazole-4-carboxamide, (2,042) N- [2-chloro-6-
(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl- lFFpyrazol-4-carboxamid, (2.043) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l- methyl-lH-pyrazol-4-carboxamid, (2.044) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3- (difluormethyl)-5-fluor-l -methyl- lH-pyrazol-4-carboxamid, (2.045) N-Cyclopropyl-3-(difluormethyl)- 5-fluor-l-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-lH-pyrazol-4-carboxamid, (2.046) N- Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-l -methyl- lH-pyrazol-4- carboxamid, (2.047) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)- 1 - methyl-lH-pyrazol-4-carboxamid, (2.048) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2- isopropylbenzyl)-l-methyl-lH-pyrazol-4-carbothioamid, (2.049) N-Cyclopropyl-3-(difluoromethyl)-5- fluor-N-(2-isopropylbenzyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.050) N-Cyclopropyl-3-(trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-l -methyl-IFFpyrazole-4-carboxamide, (2,043) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl ] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-l-methyl-1H-pyrazole-4-carboxamide, (2,044) N- [5-chloro-2- (trifluoromethyl) benzyl] -N-cyclopropyl- 3- (difluoromethyl) -5-fluoro-l-methyl-1H-pyrazole-4-carboxamide, (2,045) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-l-methyl-N- [5-methyl- 2- (trifluoromethyl) benzyl] -lH-pyrazole-4-carboxamide, (2,046) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -l -methyl-1H -pyrazole-4-carboxamide, (2,047) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) - 1 - methyl-1H-pyrazole-4-carboxamide, (2,048) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carbothioamide, (2,049) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) - 1-methyl-1H-pyrazole-4-carboxamide, (2,050) N-cyclopropyl-3-
(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.051) N- Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-l -methyl- lH-pyrazol-4- carboxamid, (2.052) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l -methyl- 1H- pyrazol-4-carboxamid, (2.053) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor- 1 - methyl- lH-pyrazole-4-carboxamid, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3- (difluormethyl)-5-fluor-l -methyl- lH-pyrazole-4-carboxamid, (2.055) N-Cyclopropyl-N-(2-cyclopropyl- 5 -methylbenzyl)-3-(difluormethyl)-5-fluor-l -methyl- lH-pyrazole-4-carboxamid, (2.056) N-(difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (2,051) N-cyclopropyl-3- (difluoromethyl) -N- (2- ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,052) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) - 5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,053) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H -pyrazole-4-carboxamide, (2,054) N-cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,055 ) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2,056) N-
Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluonnethyl)-5-fluor-l -methyl- lH-pyrazole-4-carboxamid. Cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluonomethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.
3) Inhibitoren der Atmungskette am Komplex III, beispielsweise (3.001) Ametoctradin, (3.002)3) inhibitors of the respiratory chain on complex III, for example (3,001) ametoctradine, (3,002)
Amisulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.011) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-Methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-Fluor-2- phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamid, (3.022) (2E,3Z)-5-{[l-(4-Chlorphenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3- enamid, (3.023) (2R)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.024) (2S)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.025) (3S,6S,7R,8R)-8-Benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6- methyl-4,9-dioxo-l,5-dioxonan-7-yl-2-methylpropanoat, (3.026) 2-{2-[(2,5-Amisulbromine, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) enoxastrobin, (3,009) famoxadone, (3,010) fenamidox, (3,011), (3,011), (3,011) Fluoxastrobin, (3.013) Kresoxim-Methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E 2- {2 - [({[(IE) -l- (3 - {[(E) -l-fluoro-2-phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- ( methoxyimino) -N-methylacetamide, (3.022) (2E, 3Z) -5 - {[l- (4-chlorophenyl) -lH-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent -3- enamide, (3.023) (2R) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.024) (2S) -2- {2- [(2,5-Dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3,025) (3S, 6S, 7R, 8R) -8-benzyl-3 - [({3 - [(isobutyryloxy) methoxy ] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-l, 5-dioxonan-7-yl-2-methylpropanoate, ( 3.026) 2- {2 - [(2.5-
Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.027) N-(3-Ethyl-3,5,5- trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.028) (2E,3Z)-5-{[l-(4-Chlor-2-fluorphenyl)- lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid, (3.029) Methyl {5-[3-(2,4- dimethylphenyl)- 1 H-pyrazol- 1 -yl]-2-methylbenzyl} carbamate. Dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3,027) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamido-2-hydroxybenzamide, (3,028) (2E, 3Z) -5 - {[l- (4-Chloro-2-fluorophenyl) - 1H-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3,029) methyl {5 - [3- (2,4-dimethylphenyl) -1 H-pyrazol-1-yl] -2-methylbenzyl} carbamate.
4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofencarb,4) inhibitors of mitosis and cell division, for example (4,001) carbendazim, (4,002) diethofencarb,
(4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Pencycuron, (4.006) Thiabendazol, (4.007) Thiophanat-Methyl, (4.008) Zoxamid, , (4.009) 3-Chlor-4-(2,6-difluorphenyl)-6-methyl-5- phenylpyridazin, (4.010) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (4.011) 3- Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin, (4.012) 4-(2-Brom-4- fluorphenyl)-N-(2,6-difluorphenyl)- 1 ,3-dimethyl- lH-pyrazol-5-amin, (4.013) 4-(2-Brom-4- fluorphenyl)-N-(2-brom-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.014) 4-(2-Brom-4- fluorphenyl)-N-(2-bromphenyl)- 1 ,3-dimethyl- lH-pyrazol-5-amin, (4.015) 4-(2-Brom-4-fluorphenyl)-N- (2-chlor-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.016) 4-(2-Brom-4-fluorphenyl)-N-(2- chlorphenyl)- 1 ,3-dimethyl- lH-pyrazol-5-amin, (4.017) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)- 1 ,3-dimethyl- lH-pyrazol-5-amin, (4.018) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)- 1 ,3- dimethyl- lH-pyrazol-5-amin, (4.019) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)- 1 ,3- dimethyl- lH-pyrazol-5-amin, (4.020) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-l,3-dimethyl-lH- pyrazol-5-amin, (4.021) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.022) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (4.023) N-(2-Brom-6- fluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.024) N-(2-Bromphenyl)-4- (2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.025) N-(4-Chlor-2,6-difluorphenyl)-4-(2- chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin. (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-chloropyridine -3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4,012) 4- (2-bromo-4-fluorophenyl) -N- (2,6-difluorophenyl) -1, 3-dimethyl-1H-pyrazole-5-amine, (4.013) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -l, 3-dimethyl-1H-pyrazole-5 -amine, (4.014) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) - 1, 3-dimethyl-1H-pyrazole-5-amine, (4.015) 4- (2-bromo- 4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.016) 4- (2-bromo-4-fluorophenyl) -N- (2 - chlorophenyl) - 1, 3-dimethyl-1H-pyrazole-5-amine, (4.017) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) - 1, 3-dimethyl-1H-pyrazole- 5-amine, (4.018) 4- (2-chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (4.019) 4- (2 -Chlor-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) - 1,3-dimethyl-1H-pyrazole-5-amine, (4,020) 4- (2-chloro-4-fluorophenyl) -N - (2-chlorophenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.021) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -l, 3-dimethyl- 1H-pyrazol-5-amine, (4,022) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (4.023) N- (2-bromo-6-fluorophenyl) - 4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-1H-pyrazole-5-amine, (4,024) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1 , 3-dimethyl-lH-pyrazol-5-amine, (4.025) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -l, 3-dimethyl-lH- pyrazole-5-amine.
5) Verbindungen mit Befähigung zu Multisite-Aktivität, beispielsweise (5.001) Bordeauxmischung, (5.002) Captafol, (5.003) Captan, (5.004) Chlorthalonil, (5.005) Kupferhydroxid, (5.006) Kupfemaphthenat, (5.007) Kupferoxid, (5.008) Kupferoxychlorid, (5.009) Kupfer(2+)-sulfat, (5.010) Dithianon, (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Zinkmetiram, (5.017) Kupfer-Oxin, (5.018) Propineb, (5.019) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram, (5.023) 6-Ethyl-5,7- dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][l,4]dithiino[2,3-c][l,2]thiazole-3-carbonitrile. 5) Compounds capable of multisite activity, for example (5,001) Bordeaux mixture, (5,002) captafol, (5,003) captan, (5,004) chlorothalonil, (5,005) copper hydroxide, (5,006) copper phthalate, (5,007) copper oxide, (5,008) copper oxychloride , (5.009) copper (2 +) - sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017) Copper oxyne, (5,018) propineb, (5,019) sulfur and sulfur preparations including calcium polysulfide, (5,020) thiram, (5,021) zineb, (5,022) ziram, (5,023) 6-ethyl-5,7-dioxo-6,7- dihydro-5H-pyrrolo [3 ', 4': 5,6] [1,4] dithiino [2,3-c] [1,2] thiazole-3-carbonitrile.
6) Verbindungen, die zum Auslösen einer Wirtsabwehr befähigt sind, beispielsweise (6.001) Acibenzolar-S-Methyl, (6.002) Isotianil, (6.003) Probenazol, (6.004) Tiadinil. 6) Compounds capable of triggering host defense, for example (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.
7) Inhibitoren der Aminosäure- und/oder Protein-Biosynthese, beispielsweise (7.001) Cyprodinil, (7.002) Kasugamycin, (7.003) Kasugamycinhydrochlorid-hydrat, (7.004) Oxytetracyclin (7.005) Pyrimethanil, (7.006) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin- 1 -yl)chinolin. 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline (7.005) pyrimethanil, (7.006) 3- (5-fluoro- 3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline.
(8) Inhibitoren der ATP-Produktion, beispielsweise (8.001) Silthiofam. (8) inhibitors of ATP production, for example (8.001) silthiofam.
9) Inhibitoren der Zellwandsynthese, beispielsweise (9.001) Benthiavalicarb, (9.002) Dimethomorph, (9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamid, (9.006) Pyrimorph, (9.007) Valifenalat, (9.008) (2E)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en- 1-on, (9.009) (2Z)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on. 9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E) -3 - (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -l- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) -3- (4-tert-Butylphenyl) -3- (2-chloropyridin-4-yl) -l- (morpholin-4-yl) prop-2-en-l-one.
10) Inhibitoren der Lipid- und Membran-Synthese, beispielsweise (10.001) Propamocarb, (10.002) Propamocarbhydrochlorid, (10.003) Tolclofos-Methyl. 10) Inhibitors of lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.
11) Inhibitoren der Melanin-Biosynthese, beispielsweise (11.001) Tricyclazol, (11.002) 2,2,2- Trifluorethyl-{3-methyl-l-[(4-methylbenzoyl)amino]butan-2-yl}carbamat. 11) Inhibitors of melanin biosynthesis, for example (11,001) tricyclazole, (11,002) 2,2,2-trifluoroethyl- {3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl} carbamate.
12) Inhibitoren der Nukleinsäuresynthese, beispielsweise (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam). 13) Inhibitoren der Signaltransduktion, beispielsweise (13.001) Fludioxonil, (13.002) Iprodion, (13.003) Procymidon, (13.004) Proquinazid, (13.005) Quinoxyfen, (13.006) Vinclozolin. 12) Inhibitors of nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam). 13) Inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
14) Verbindungen, die als Entkoppler wirken können, beispielsweise (14.001) Fluazinam, (14.002) Meptyldinocap. 14) Compounds that can act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.
15) Weitere Verbindungen, beispielsweise (15.001) Abscisinsäure, (15.002) Benthiazol, (15.003)15) Other compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003)
Bethoxazin, (15.004) Capsimycin, (15.005) Carvon, (15.006) Chinomethionat, (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.01 1) Flutianil, (15.012) Fosetyl-Aluminium, (15.013) Fosetyl-Calcium, (15.014) Fosetyl-Natrium, (15.015) Methylisothiocyanat, (15.016) Metrafenon, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel-Dimethyldithiocarbamat, (15.020) Nitrothal-Isopropyl, (15.021) Oxamocarb, (15.022)Bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.01 1) flutianil, (15.012) fosetyl aluminum, (15.013) fosetyl calcium, (15.014) fosetyl sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal isopropyl, (15.020) ) Oxamocarb, (15.022)
Oxathiapiprolin, (15.023) Oxyfenthiin, (15.024) Pentachlorphenol und Salze, (15.025) Phosphonsäure und deren Salze, (15.026) Propamocarb-fosetylat, (15.027) Pyriofenone (Chlazafenone) (15.028) Tebufloquin, (15.029) Tecloftalam, (15.030) Tolnifanide, (15.031) l-(4- {4-[(5R)-5-(2,6-Difluorphenyl)- 4,5-dihydro- 1 ,2-oxazol-3-yl]- 1 ,3-thiazol-2-yl}piperidin- 1 -yl)-2-[5-methyl-3-(trifluormethyl)- 1H- pyrazol-l-yl]ethanon, (15.032) l-(4- {4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3- thiazol-2-yl}piperidin- 1 -yl)-2-[5-methyl-3-(trifluormethyl)- lH-pyrazol- 1 -yl]ethanon, ( 15.033) 2-(6-Oxathiapiproline, (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphonic acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone) (15.028) tebufloquine, (15.029niflide) tecloft , (15.031) l- (4- {4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole- 2-yl} piperidin-1 -yl) -2- [5-methyl-3- (trifluoromethyl) - 1H-pyrazol-l-yl] ethanone, (15.032) l- (4- {4 - [(5S) - 5- (2,6-difluorophenyl) -4,5-dihydro-l, 2-oxazol-3-yl] -l, 3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl -3- (trifluoromethyl) - lH-pyrazol-1-yl] ethanone, (15.033) 2- (6-
Benzylpyridin-2-yl)quinazolin, (15.034) 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrol- l,3,5,7(2H,6H)-tetron, (15.035) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]- l-[4-(4- {5-[2-(prop-2-in-l- yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.036) 2-[3,5- Bis(difluormethyl)- 1 H-pyrazol- 1 -yl]-l - [4-(4- {5- [2-chlor-6-(prop-2-in- 1 -yloxy)phenyl]-4,5-dihydro- 1 ,2- oxazol-3 -yl} - 1 ,3 -thiazol-2-yl)piperidin- 1 -yl] ethanon, (15.037) 2- [3 ,5-Bis(difluormethyl)- 1 H-pyrazol- 1 - yl]-l-[4-(4- {5-[2-fluor-6-(prop-2-in- l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}- l,3-thiazol-2- yl)piperidin- 1 -yl] ethanon, (15.038) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolin, (15.039) 2- {(5R)-3-[2-(l- {[3,5-Bis(difluormethyl)- lH-pyrazol- l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4- yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenyl methanesulfonat, (15.040) 2- {(5S)-3-[2-(l- {[3,5-Benzylpyridin-2-yl) quinazoline, (15,034) 2,6-dimethyl-1H, 5H- [1,4] dithiino [2,3-c: 5,6-c '] dipyrrol-l, 3,5,7 (2H, 6H) tetron, (15.035) 2- [3,5-bis (difluoromethyl) -lH-pyrazol-l-yl] - l- [4- (4- {5- [2- (prop-2 -in-l-yloxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -l, 3-thiazol-2-yl) piperidin-l-yl] ethanone, (15.036) 2- [3,5- bis (difluoromethyl) -1 H -pyrazol-1-yl] -1 - [4- (4- {5- [2-chloro-6- (prop-2-yn-1-yloxy) phenyl ] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.037) 2- [3,5-bis (difluoromethyl ) - 1 H-pyrazol-1 - yl] -l- [4- (4- {5- [2-fluoro-6- (prop-2-in-l-yloxy) phenyl] -4,5-dihydro- 1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15,038) 2- [6- (3-fluoro-4-methoxyphenyl) -5-methylpyridine -2-yl] quinazoline, (15,039) 2- {(5R) -3- [2- (l- {[3,5-bis (difluoromethyl) - lH-pyrazol-l-yl] acetyl} piperidine-4- yl) -l, 3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (15.040) 2- {(5S) -3- [2 - (l- {[3,5-
Bis(difluormethyl)- 1 H-pyrazol- 1 -yl]acetyl}piperidin-4-yl)- 1 ,3-thiazol-4-yl]-4,5-dihydro- 1 ,2-oxazol-5- yl}-3-chlorphenyl methanesulfonat, (15.041) 2- {2-[(7,8-Difluor-2-methylquinolin-3-yl)oxy]-6- fluorphenyl}propan-2-ol, (15.042) 2- {2-Fluor-6-[(8-fluor-2-methylquinolin-3-yl)oxy]phenyl}propan-2- ol, (15.043) 2- {3-[2-(l- {[3,5-Bis(difluormethyl)- lH-pyrazol-l-yl]acetyl}piperidin-4-yl)- l,3-thiazol-4- yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenyl-methansulfonat, (15.044) 2- {3-[2-(l- {[3,5-Bis (difluoromethyl) - 1 H-pyrazol-1-yl] acetyl} piperidin-4-yl) - 1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (15,041) 2- {2 - [(7,8-difluoro-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} propan-2-ol, (15.042) 2- {2 -Fluoro-6 - [(8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propan-2-ol, (15.043) 2- {3- [2- (l- {[3,5-bis (difluoromethyl) - lH-pyrazol-l-yl] acetyl} piperidin-4-yl) - 1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3 -chlorophenyl methanesulfonate, (15.044) 2- {3- [2- (l- {[3,5-
Bis(difluormethyl)- 1 H-pyrazol- 1 -yl]acetyl}piperidin-4-yl)- 1 ,3-thiazol-4-yl]-4,5-dihydro- 1 ,2-oxazol-5- yl [ phcnyl methanesulfonat, (15.045) 2-Phenylphenol und deren Salze, (15.046) 3-(4,4,5-Trifluor-3,3- dimethyl-3,4-dihydroisoquinolin- 1 -yl)quinolin, (15.047) 3-(4,4-Difluor-3,3-dimethyl-3,4- dihydroisoquinolin- 1 -yl)quinolin, (15.048) 4-Amino-5-fluorpyrimidin-2-ol (Tautomere Form: 4-Amino- 5-fluorpyrimidin-2(lH)-on), (15.049) 4-Oxo-4-[(2-phenylethyl)amino]buttersäure, (15.050) 5-Amino- 1 ,3 ,4-thiadiazol-2-thiol, ( 15.051 ) 5-Chlor-N'-phenyl-N'-(prop-2-yn- 1 -yl)thiophen-2-sulfonohydrazid, (15.052) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.053) 5-Fluor-2-[(4- methylbenzyl)oxy]pyrimidin-4-amin, ( 15.054) 9-Fluor-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro- 1 ,4- benzoxazepin, (15.055) But-3-yn-l-yl {6-[({[(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.056) Ethyl (2Z)-3-amino-2-cyano- 3-phenylacrylat, (15.057) Phenazin- 1 -carbonsäure, (15.058) Propyl 3,4,5-trihydroxybenzoat, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfat (2: 1), (15.061) tert-Butyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino} oxy)methyl]pyridin-2-yl}carbamat, ( 15.062) 5-Fluor-4-imino-3-methyl- 1 - [(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(lH)-one. Bis (difluoromethyl) - 1 H-pyrazol-1-yl] acetyl} piperidin-4-yl) - 1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl [ phcnyl methanesulfonate, (15.045) 2-phenylphenol and its salts, (15.046) 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.047) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15,048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidine -2 (1H) -one), (15.049) 4-oxo-4 - [(2-phenylethyl) amino] butyric acid, (15.050) 5-amino-1, 3, 4-thiadiazol-2-thiol, (15.051) 5-chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, (15.053) 5-fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.054) 9 -Fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro-1,4-benzoxazepine, (15,055) but-3-yn-l-yl {6 - [({[ (Z) - (l-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.056) ethyl (2Z) -3-amino-2- cyano-3-phenyl acrylate, (15.057) phenazin-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2: 1) , (15,061) tert-butyl {6 - [({[(l-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.062) 5 -Fluoro-4-imino-3-methyl-1 - [(4-methylphenyl) sulfonyl] -3,4-dihydropyrimidin-2 (1H) -one.
Biologische Schädlingsbekämpfungsmittel als Mischungskomponenten Biological pesticides as mixture components
Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. The compounds of formula (I) can be combined with biological pesticides.
Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte. Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products which have been formed by microorganisms, including proteins and secondary metabolic products.
Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that act as biological insecticides, fungicides, or nematicides.
Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind:  Examples of such bacteria that can be used as biological pesticides are:
Bacillus amyloliquefaciens , Stamm FZB42 (DSM 231179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM 1-1562 oder Bacillus firmus, Stamm 1-1582 (Accession number CNCM 1-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. NRRL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD-1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, insbesondere B. thuringiensis Subspezies israelensis (Serotyp H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder B. thuringiensis subsp. aizawai, insbesondere Stamm ABTS- 1857 (SD- 1372), oder B. thuringiensis subsp. kurstaki Stamm HD-l, oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232).  Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-l, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Acession Number NRRL 30232).
Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm HRO LEC 12, Lecanicillium lecanii (ehemals bekannt als Verticillium lecanii ), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (heu: Isaria fumosorosea), insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, insbesondere P. lilacinus Stamm 251 (AGAL 89/030550), Talaromyces flavus, insbesondere Stamm Vl l7b, Trichoderma atroviride, insbesondere Stamm SC1 (Accession Number CBS 122089), Trichoderma harzianum, insbesondere T. harzianum rifai T39. (Accession Number CNCM 1-952). Examples of fungi and yeasts that can be used as biological pesticides are: Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular Strain KV01, metarhician anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Acc .ion No. ATCC 2087 ), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain Vl 17b, Trichoderma atroviride, in particular strain SC1 (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind:  Examples of viruses that can be used as biological pesticides are:
Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV.  Adoxophyes orana (Apple Peel Wrapper) Granulosevirus (GV), Cydia pomonella (Apple Wrapper) Granulosevirus (GV), Helicoverpa armigera (Cotton Capsule Worm) Nuclear Polyhedrosis Virus (NPV), Spodoptera exigua (Sugar Beet Owl) mNPV, Spodopteraischerf Cottonworm) NPV.
Es sind auch Bakterien und Pilze umfasst, die als ,Inokulant‘ Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt:  Bacteria and fungi are also included, which are added as 'inoculant' to plants or parts of plants or plant organs and which promote plant growth and plant health through their special properties. Examples are:
Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp..  Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora spp., Or Gigaspora monospor. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp ..
Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind:  Examples of plant extracts and products which have been formed from microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrine, Quassia amara, Quercus, Quillaja, Regalia,„Requiem™ Insecticide“, Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen- Extrakt, insbesondere Raps- oder Senfpulver. Safener als Mischungskomponenten Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quxhrum / Sap Pyrethrine, Quassia amara, Quercus, Quillaja, Regalia, "Requiem ™ Insecticide", Rotenon, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract , especially rapeseed or mustard powder. Safener as a mixture component
Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid (CAS 129531-12-0), 4-(Dichloracetyl)-l-oxa-4-azaspiro[4.5]decan (CAS 71526-07-3), 2,2,5-Trimethyl-3- (dichloracetyl)-l,3-oxazo lidin (CAS 52836-31-4). The compounds of the formula (I) can be combined with safeners, such as, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -l-oxa -4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -1, 3-oxazolidine (CAS 52836-31-4).
Pflanzen und Pflanzenteile Plants and parts of plants
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Paprika, Gurke, Melone, Möhre, Wassermelone, Zwiebel, Salat, Spinat, Porree, Bohnen, Brassica oleracea (z. B. Kohl) und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzen sollen alle Entwicklungsstadien wie Saatgut, Stecklinge, junge (unausgereifte) Pflanzen bis hin zu ausgereiften Pflanzen verstanden werden. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehören auch geerntete Pflanzen oder geerntete Pflanzenteile sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. According to the invention, all plants and parts of plants can be treated. Plants are understood to mean all plants and plant populations such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes , Bell pepper, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (e.g. cabbage) and other vegetables, cotton, tobacco, rape, and fruit plants (with the fruits apples, pears, Citrus 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 cultivars which can or cannot be protected by plant breeders' rights. Plants are to be understood to mean all stages of development such as seeds, cuttings, young (immature) plants and mature plants. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being 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 and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung der Verbindungen auf die Umgebung, den Lebensraum oder den Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Eintauchen, Spritzen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. The treatment of the plants and parts of plants according to the invention 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 by the customary treatment methods, for. B. by immersion, spraying, evaporation, misting, scattering, brushing, injecting and in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff„Teile“ bzw.„Teile von Pflanzen“ oder„Pflanzenteile“ wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits“), die durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species or plant species or those obtained by conventional biological breeding methods such as crossing or protoplast fusion are used as well as their parts treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The term “parts” or “parts of plants” or “parts of plants” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant varieties are plants with new properties (“traits”) that have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Transgenic plant, seed treatment and integration events
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Emteerträge, höhere Qualität und/oder höherer Emährungswert der Emteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Emteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schädlinge, wie Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z. B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z. B. durch die Gene CrylA(a), CryIA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z. B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinone, Sulfonylharnstoffe, Glyphosat oder Phosphinotricin (z. B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen Vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. Pflanzenschutz - Behandlungsarten The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received 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 drought or water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the crop products , higher shelf life and / or workability of the harvest products. Further and particularly highlighted examples of such properties are an increased ability of the plants to defend themselves against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails. B. by toxins arising in the plants, especially those caused by the genetic material from Bacillus thuringiensis (e.g. by the genes CrylA (a), CryIA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants, furthermore an increased ability of the plants to defend themselves against phytopathogenic fungi, bacteria and / or viruses. B. by systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as an increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT "-Gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soy, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed being particularly emphasized. The properties ("traits") that are particularly emphasized are the plants' increased resistance to insects, arachnids, nematodes and snails. Plant protection - types of treatment
Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Tauchen, Spritzen, Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, Verstreuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low-Volume-V erfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) selbst in den Boden zu injizieren. The treatment of the plants and parts of plants with the compounds of the formula (I) is carried out directly or by acting on their surroundings, living space or storage space by the customary treatment methods, for. B. by dipping, spraying, spraying, sprinkling, evaporating, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, watering (drenching), drip irrigation and with propagation material, in particular in the case of seed, furthermore by dry pickling, wet pickling, slurry pickling, incrusting , single or multi-layer coating, etc. It is also possible to apply the compounds of the formula (I) according to the ultra-low-volume method or to inject the use form or the compound of the formula (I) into the soil itself.
Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d. h. die Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfirequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. A preferred direct treatment of the plants is leaf application, i.e. H. the compounds of formula (I) are applied to the foliage, the treatment sequence and the application rate should be matched to the infestation pressure of the respective pest.
Bei systemisch wirksamen Wirkstoffen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d. h. der Standort der Pflanze (z. B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d. h. die erfindungsgemäßen Verbindungen der Formel (I) werden in fester Form (z. B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z. B. als Granulat) in ein überflutetes Reisfeld sein. In the case of systemically active substances, the compounds of the formula (I) also get into the plants via the root system. The plants are then treated by the action of the compounds of the formula (I) on the habitat of the plant. This can be, for example, by drenching, mixing into the soil or the nutrient solution, i.e. 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 soil application, i.e. 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 the case of water rice crops, this can also be done by metering the compound of the formula (I) into a solid application form (for example as granules) into a flooded rice field.
Saatgutbehandlung Seed treatment
Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Be handlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Schädlingsbekämpfungsmitteln bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw. -toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und auch der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. The control of animal pests by treating the seeds of plants has been known for a long time and is the subject of constant improvements. Nevertheless, there are a number of problems with the treatment of seeds that cannot always be solved satisfactorily. It is therefore desirable to develop methods for protecting the seeds and the germinating plant which make the additional application of pesticides superfluous during storage, after sowing or after emergence of the plants, or at least significantly reduce them. It is also desirable to optimize the amount of the active ingredient used so that the seeds and the germinating plant are optimally protected from infestation by animal pests, but without damaging the plant itself by the active ingredient used. In particular, methods of treating seeds should include intrinsic insecticides or nematicides Include properties of pest-resistant or tolerant transgenic plants in order to achieve optimal protection of the seed and the germinating plant with a minimum of pesticides.
Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (1) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (1) und einer Mischungskomponente behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (1) und einer Mischungskomponente behandelt wird. The present invention therefore also relates in particular to a method for protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of the formula (1). The method according to the invention for protecting seed and germinating plants from pest infestation further comprises a method in which the seed is treated simultaneously in one process or sequentially with a compound of the formula (1) and a mixture component. It also includes a method in which the seed is treated at different times with a compound of formula (1) and a mixture component.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (1) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. The invention also relates to the use of the compounds of the formula (1) for the treatment of seeds in order to protect the seeds and the plant resulting therefrom from animal pests.
Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer erfindungsgemäßen Verbindung der Formel (1) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (1) und einer Mischungskomponente behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (1) und einer Mischungskomponente behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (1) und einer Mischungskomponente behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut vorhanden sein. Dabei können die Schichten, die eine Verbindung der Formel (1) und Mischungskomponenten enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (1) und eine Mischungskomponente als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. The invention further relates to seeds which have been treated with a compound of the formula (1) according to the invention for protection against animal pests. The invention also relates to seeds which have been treated at the same time with a compound of formula (1) and a mixture component. The invention further relates to seeds which have been treated at different times with a compound of the formula (1) and a mixture component. In the case of seed which has been treated at different times with a compound of the formula (1) and a mixture component, the individual substances can be present on the seed in different layers. The layers which contain a compound of formula (1) and mixture components can optionally be separated by an intermediate layer. The invention also relates to seeds in which a compound of the formula (1) and a mixture component are applied as part of a covering or as a further layer or further layers in addition to a covering.
Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (1) einem Filmcoating-Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. Furthermore, the invention relates to seeds which, after treatment with a compound of the formula (1), are subjected to a film coating process in order to avoid dust abrasion on the seeds.
Einer der auftretenden Vorteile, wenn eine Verbindung der Formel (1) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können. One of the advantages that arise when a compound of formula (1) acts systemically is that the treatment of the seed protects not only the seed itself, but also the plants which result therefrom after emergence from animal pests. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be omitted. Another advantage can be seen in the fact that the treatment of the seed with a compound of the formula (I) can promote germination and emergence of the treated seed.
Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können. It is also to be regarded as advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seeds.
Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. Compounds of the formula (I) can also be used in combination with signaling agents, as a result of which there is better colonization with symbionts, such as, for example, rhizobia, mycorrhiza and / or endophytic bacteria or fungi, and / or there is an optimized nitrogen fixation.
Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baumwolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z. B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola, Raps, Gemüse und Reis zu. The compounds of the formula (I) are suitable for protecting seeds of any type of plant which is used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are seeds of cereals (e.g. wheat, barley, rye, millet and oats), corn, cotton, soybeans, rice, potatoes, sunflower, coffee, tobacco, canola, rapeseed, beet (e.g. Sugar beet and fodder beet), peanut, vegetables (e.g. tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, lawn and ornamental plants. The treatment of the seeds of cereals (such as wheat, barley, rye and oats), corn, soybeans, cotton, canola, rapeseed, vegetables and rice is of particular importance.
Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. As already mentioned above, the treatment of transgenic seeds with a compound of formula (I) is of particular importance. These are the seeds of plants which generally contain at least one heterologous gene which controls the expression of a polypeptide with, in particular, insecticidal or nematicidal properties. The heterologous genes in transgenic seeds can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seeds which contain at least one heterologous gene which is derived from Bacillus sp. comes from. It is particularly preferably a heterologous gene which comes from Bacillus thuringiensis.
Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hüllen, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z. B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Fall von Reis-Saatgut ist es auch möglich, Saatgut zu verwenden, das getränkt wurde, zum Beispiel in Wasser bis zu einem bestimmten Stadium des Reisembryos („Pigeon Breast Stage“), wodurch die Keimung und ein einheitlicheres Auflaufen stimuliert wird. In the context of the present invention, the compound of the formula (I) is applied to the seed. The seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment. In general, the seed can be treated at any time between harvesting and sowing. Usually, seeds are used that have been separated from the plant and freed of pistons, shells, stems, casings, wool or pulp. For example, seeds can be used that have been harvested, cleaned and dried to a storable moisture content. Alternatively, seeds can also be used, which after drying z. B. was treated with water and then dried again, for example Priming. In the case of rice seeds, it is also possible to use seeds that have been soaked, for example in water up to a certain stage of the rice embryo (“pigeon breast stage”), which stimulates germination and a more uniform emergence.
Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. In general, care must be taken when treating the seed that the amount of the compound of the formula (I) and / or other additives applied to the seed is selected so that the germination of the seed does not impair or the resulting plant is not damaged becomes. This is particularly important for active substances that can show phytotoxic effects at certain application rates.
Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. 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 the person skilled in the art.
Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. The compounds of the formula (I) can be converted into the customary mordant formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and also ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man die Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. These formulations are prepared in a known manner by mixing the compounds of the formula (I) with customary additives, such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberelline and also water.
Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe. Suitable dyes which can be present in the mordant formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples include those under the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalinsulfonate, wie Diisopropyl- oder Diisobutylnaphthalinsulfonate. Suitable wetting agents which can be contained in the mordant formulations which can be used according to the invention are all wetting-promoting substances which are customary for the formulation of agrochemical active compounds. Alkyl naphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates, can preferably be used.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor-zugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tri- stiyrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat- F ormaldehydkondensate . Suitable dispersants and / or emulsifiers which may be present in the mordant formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of active agrochemicals. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used. In particular, suitable nonionic dispersants are Ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-triyrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. The mordant formulations which can be used according to the invention can contain, as defoamers, all of the foam-inhibiting substances which are customary for formulating active agrochemicals. Silicone defoamers and magnesium stearate can preferably be used.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. All substances which can be used in agrochemical compositions for such purposes can be present as preservatives in the mordant formulations which can be used according to the invention. Examples include dichlorophene and benzyl alcohol hemiform.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formu- lierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln ein setzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Secondary thickeners which can be contained in the mordant formulations which can be used according to the invention are all substances which can be used in agrochemical compositions for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silica are preferred.
Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Suitable adhesives which can be contained in the mordant formulations which can be used according to the invention are all binders customarily used in mordants. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose are preferred.
Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline Al, A3 (= Gibberellinsäure), A4 und A7 infrage, be sonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel“, Bd. 2, Springer Verlag, 1970, S. 401- 412). The gibberellins A1, A3 (= gibberellic acid), A4 and A7 are preferably gibberellins which may be present in the mordant formulations which can be used according to the invention, and gibberellic acid is particularly preferably used. The gibberellins are known (see R. Wegler “Chemistry of Plant Protection and Pest Control”, Vol. 2, Springer Verlag, 1970, pp. 401-412).
Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen können entweder direkt oder nach vorherigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art eingesetzt werden. So lassen sich die Konzentrate oder die daraus durch Verdünnen mit Wasser erhältlichen Zu bereitungen einsetzen zur Beizung des Saatgutes von Getreide, wie Weizen, Gerste, Roggen, Hafer und Triticale, sowie des Saatgutes von Mais, Reis, Raps, Erbsen, Bohnen, Baumwolle, Sonnenblumen, Soja und Rüben oder auch von Gemüsesaatgut der verschiedensten Natur. Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder deren verdünnte Anwendungsformen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden. The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for treating a wide variety of seeds. 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, and the seeds of corn, rice, rapeseed, peas, beans, cotton, Sunflowers, soybeans and beets or vegetable seeds of all kinds. The seed dressing formulations which can be used according to the invention or their dilute use forms can also be used for dressing seeds of transgenic plants.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder dem daraus durch Zugabe von Wasser hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im Einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichen oder kontinuierlichen Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an. For the treatment of seeds with the seed dressing formulations which can be used according to the invention or with the use forms prepared therefrom by adding water, all are usually suitable for the pickling mixers that can be used. In detail, the procedure for dressing is that the seeds are placed in a mixer in batch or continuous operation, the desired amount of dressing formulation is added either as such or after prior dilution with water and until the formulation is evenly distributed mixes the seeds. If necessary, a drying process follows.
Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) liegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut. The application rate of the mordant formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the respective content of the compounds of the formula (I) in the formulations and on the seed. The application rates for the compound 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.
Tiergesundheit Animal health
Auf dem Gebiet der Tiergesundheit, d. h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasit umfasst insbesondere Helminthen und Protozoen wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten oder Akariden. In the field of animal health, i.e. H. in the field of veterinary medicine, the compounds of the 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.
Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I), die eine günstige Toxizität gegenüber Warmblütern aufweisen, für die Bekämpfung von Parasiten, die in der Tierzucht und Tierhaltung bei Nutztieren, Zuchttieren, Zootieren, Laboratoriumstieren, Versuchstieren und Haustieren auftreten. Sie sind gegen alle oder einzelne Entwicklungsstadien der Parasiten wirksam. In the field of veterinary medicine, the compounds of the formula (I), which have a favorable toxicity to warm-blooded animals, are suitable for combating parasites which occur in animal breeding and animal husbandry in farm animals, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of the development of the parasites.
Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; oder Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; oder Fische oder Krustentiere, z. B. in der Aquakultur, oder gegebenenfalls Insekten wie Bienen. Agricultural animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer and in particular cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. B. in aquaculture, or possibly insects such as bees.
Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel; Reptilien, Amphibien oder Aquariumfische. Pets include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and in particular dogs, cats, house birds; Reptiles, amphibians or aquarium fish.
Gemäß einer bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. In a particular embodiment, the compounds of formula (I) are administered to mammals.
Gemäß einer weiteren bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel oder insbesondere Geflügel, verabreicht. Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erzielbar ist. In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen" im vorliegenden Zusammenhang, dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert wird. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindungen der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine V ermehrung verhindern. According to a further specific embodiment, the compounds of the formula (I) are administered to birds, namely house birds or, in particular, poultry. The use of the compounds of the formula (I) for combating animal parasites is said to reduce or prevent illness, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey and the like), so that animal husbandry can be carried out more economically and easily and a better well-being of the animals can be achieved. With regard to the field of animal health, the term “control” or “control” in the present context means that the compounds of the formula (I) are effective in the occurrence of the respective parasite in an animal which is infected with such parasites to a harmless extent , is reduced. More specifically, in the present context, "combating" means that the compounds of the formula (I) kill the particular parasite, prevent its growth or prevent its multiplication.
Zu den Arthropoden zählen beispielsweise, ohne hierauf beschränkt zu sein, aus der Ordnung Anoplurida zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina und Ischnocerina, zum Beispiel Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Wemeckiella spp; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; aus der Ordnung Siphonapterida, zum Beispiel Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. The arthropods include, but are not limited to, the Anoplurida order, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the subordinates Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Wemeckiella spp; from the order Diptera and the subordinates Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp. , Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests and hygiene pests from the Blattarida order.
Weiterhin sind bei den Arthropoden beispielhaft, ohne hierauf beschränkt zu sein, die folgenden Akari zu nennen: Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Omithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Stemostoma spp., Tropilaelaps spp., Varroa spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Omithocheyletia spp., Psorergates spp., Trombicula spp.; und aus der Ordung der Acaridida (Astigmata), zum Beispiel Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp. Furthermore, the following Akari are examples of the arthropods, but are not limited to them: From the subclass Akari (Acarina) and the order Metastigmata, for example from the Argasidae family, such as Argas spp., Omithodorus spp., Otobius spp., From the Ixodidae family, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-host ticks); from the order Mesostigmata, such as Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Stemostoma spp., Tropilaelaps spp., Varroa spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Omithocheyletia spp., Psorergates spp., Trombicula spp .; and from the order of the Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp ., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.
Zu Beispielen für parasitäre Protozoen zählen, ohne hierauf beschränkt zu sein: Examples of parasitic protozoa include, but are not limited to:
Mastigophora (Flagellata), wie: Mastigophora (Flagellata), such as:
Metamonada: aus der Ordnung Diplomonadida zum Beispiel Giardia spp., Spironucleus spp. Metamonada: from the order Diplomonadida, for example Giardia spp., Spironucleus spp.
Parabasala: aus der Ordnung Trichomonadida zum Beispiel Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Parabasala: from the order Trichomonadida, for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
Euglenozoa: aus der Ordnung Trypanosomatida zum Beispiel Leishmania spp., Trypanosoma spp. Euglenozoa: from the order Trypanosomatida, for example Leishmania spp., Trypanosoma spp.
Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba spp., Centramoebidae, zum Beispiel Acanthamoeba sp., Euamoebidae, z. B. Hartmanella sp. Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. B. Hartmanella sp.
Alveolata wie Apicomplexa (Sporozoa): z. B. Cryptosporidium spp.; aus der Ordnung Eimeriida zum Beispiel Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; aus der Ordnung Adeleida z. B. Hepatozoon spp., Klossiella spp.; aus der Ordnung Haemosporida z. B. Leucocytozoon spp., Plasmodium spp.; aus der Ordnung Piroplasmida z. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; aus der Ordnung Vesibuliferida z. B. Balantidium spp., Buxtonella spp. Alveolata such as Apicomplexa (Sporozoa): e.g. B. 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. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida z. B. Balantidium spp., Buxtonella spp.
Microspora wie Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., und außerdem z. B. Myxozoa spp. Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
Zu den für Menschen oder Tiere pathogenen Helminthen zählen zum Beispiel Acanthocephala, Nematoden, Pentastoma und Platyhelminthen (z.B. Monogenea, Cestodes und Trematodes). Helminths pathogenic to humans or animals include, for example, acanthocephala, nematodes, pentastomas and platyhelminths (e.g. Monogenea, Cestodes and Trematodes).
Zu beispielhaften Helminthen zählen, ohne hierauf beschränkt zu sein: Monogenea: z. B.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.; Exemplary helminths include, but are not limited to: Monogenea: e.g. E.g. Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. Cestodes: from the order Pseudophyllidea, for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
Aus der Ordnung Cyclophyllida zum Beispiel: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp. From the order Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp. , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma
Trematodes: aus der Klasse Digenea zum Beispiel: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrcma 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., Omithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp. Trematodes: from the Digenea class, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrcma spp., Fasciola spp., Fascioliol sppis ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opistppithchis spp. Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.
Nematoden: aus der Ordnung Trichinellida zum Beispiel: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. Nematodes: from the order Trichinellida, for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
Aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Parastrangyloides spp., Strongyloides spp. From the order Tylenchida, for example: Micronema spp., Parastrangyloides spp., Strongyloides spp.
Aus der Ordnung Rhabditina zum Beispiel: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Omithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp. From the order Rhabditina, for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenathoma spp. , Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidpp., Graphid spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagumesus. , Ollulanus spp .; Omithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongyl. Spp., Protostrongyl ., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.
Aus der Ordnung Spirurida zum Beispiel: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. From the order Spirurida, for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp .; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp .; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp .; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabin ., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.
Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp., Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida, for example: Moniliformis spp.,
Aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. From the order Polymorphida, for example: Filicollis spp .; from the order Echinorhynchida, for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp. Pentastoma: from the order Porocephalida, for example Linguatula spp.
Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch; metaphylaktisch oder therapeutisch erfolgen. In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by generally known methods, such as enterally, parenterally, dermally or nasally, in the form of suitable preparations. Administration can be prophylactic; metaphylactic or therapeutic.
So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verbindungen der Formel (I) zur Verwendung als Arzneimittel. One embodiment of the present invention thus relates to the compounds of the formula (I) for use as a medicament.
Ein weiterer Aspekt bezieht sich auf die Verbindungen der Formel (I) zur Verwendung als Antiendoparasitikum. Another aspect relates to the compounds of formula (I) for use as an anti-endoparasitic.
Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwendung als Antihelminthikum, insbesondere zur Verwendung als Nematizid, Platymelminthizid, Acanthocephalizid oder Pentastomizid. A further special aspect of the invention relates to the compounds of the formula (I) for use as an antihelminthic agent, in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.
Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwendung als Antiprotozoikum. Another specific aspect of the invention relates to the compounds of formula (I) for use as an antiprotozoal.
Ein weiterer Aspekt betrifft die Verbindungen der Formel (I) zur Verwendung als Antiektoparasitikum, insbesondere ein Arthropodizid, ganz besonders ein Insektizid oder ein Akarizid. Weitere Aspekte der Erfindung sind veterinärmedizinische Formulierungen, die eine wirksame Menge mindestens einer Verbindung der Formel (I) und mindestens einen der folgenden umfassen: einen pharmazeutisch unbedenklichen Exzipienten (z.B. feste oder flüssige Verdünnungsmittel), ein pharmazeutisch unbedenkliches Hilfsmittel (z.B. Tenside), insbesondere einen herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder ein herkömmlicherweise in veterinärmedizinischen Formulierungen verwendetes pharmazeutisch unbedenkliches Hilfsmittel. Another aspect relates to the compounds of the formula (I) for use as an antiectoparasitic, in particular an arthropodicide, very particularly an insecticide or an acaricide. Further aspects of the invention are veterinary formulations which comprise an effective amount of at least one compound of the formula (I) and at least one of the following: a pharmaceutically acceptable excipient (for example solid or liquid diluents), a pharmaceutically acceptable auxiliary (for example surfactants), in particular one pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable excipient conventionally used in veterinary formulations.
Ein verwandter Aspekt der Erfindung ist ein Verfahren zur Herstellung einer wie hier beschriebenen veterinärmedizinischen Formulierung, welches den Schritt des Mischens mindestens einer Verbindung der Formel (I) mit pharmazeutisch unbedenklichen Exzipienten und/oder Hilfsmitteln, insbesondere mit herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten Hilfsmitteln umfasst. A related aspect of the invention is a process for the preparation of 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 auxiliaries, in particular with pharmaceutically acceptable excipients and conventionally used in veterinary formulations / or comprises auxiliaries conventionally used in veterinary formulations.
Ein anderer spezieller Aspekt der Erfindung sind veterinärmedizinische Formulierungen ausgewählt aus der Gruppe ektoparasitizider und endoparasitizider Formulierungen, insbesondere ausgewählt aus der Gruppe anthelmintischer, antiprotozolischer und arthropodizider Formulierungen, ganz besonders ausgewählt aus der Gruppe nematizider, platyhelminthizider, acanthocephalizider, pentastomizider, insektizider und akkarizider Formulierungen, gemäß den erwähnten Aspekten, sowie Verfahren zu ihrer Herstellung. Another special aspect of the invention are veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozolic and arthropodicidal formulations, very particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, insecticidal, and pentastomicidal, according to pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pentastomicidal, pentastomicidal, and pesticidal formulations, respectively the mentioned aspects, as well as processes for their production.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wirksamen Menge einer Verbindung der Formel (I) bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by using an effective amount of a compound of the formula (I) in an animal, in particular a non-human Animal that needs it.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wie hier definierten veterinärmedizinischen Formulierung bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method of treating a parasitic infection, in particular a parasite infection selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined here to an animal, in particular a non-human animal, the latter requirement.
Ein anderer Aspekt bezieht sich auf die Verwendung der Verbindungen der Formel (I) bei der Behandlung einer Parasiteninfektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, bei einem Tier, insbesondere einem nichthumanen Tier. Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasite 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.
Im vorliegenden tiergesundheitlichen oder veterinärmedizinischen Zusammenhang schließt der Begriff „Behandlung“ die prophylaktische, die metaphylaktische und die therapeutische Behandlung ein. Bei einer bestimmten Ausführungsform werden hiermit Mischungen mindestens einer Verbindung der Formel (I) mit anderen Wirkstoffen, insbesondere mit Endo- und Ektoparasitiziden, für das veterinärmedizinische Gebiet bereitgestellt. In the present animal health or veterinary context, the term “treatment” includes prophylactic, metaphylactic and therapeutic treatment. In a specific embodiment, mixtures of at least one compound of the formula (I) with other active compounds, in particular with endo- and ectoparasiticides, are hereby provided for the veterinary field.
Auf dem Gebiet der Tiergesundheit bedeutet„Mischung“ nicht nur, dass zwei (oder mehr) verschiedene Wirkstoffe in einer gemeinsamen Formulierung formuliert werden und entsprechend zusammen angewendet werden, sondern bezieht sich auch auf Produkte, die für jeden Wirkstoff getrennte Formulierungen umfassen. Dementsprechend können, wenn mehr als zwei Wirkstoffe angewendet werden sollen, alle Wirkstoffe in einer gemeinsamen Formulierung formuliert werden oder alle Wirkstoffe in getrennten Formulierungen formuliert werden; ebenfalls denkbar sind gemischte Formen, bei denen einige der Wirkstoffe gemeinsam formuliert und einige der Wirkstoffe getrennt formuliert sind. Getrennte Formulierungen erlauben die getrennte oder aufeinanderfolgende Anwendung der in Rede stehenden Wirkstoffe. In the field of animal health, "blend" not only means that two (or more) different active ingredients are formulated in a common formulation and used accordingly together, but also refers to products that contain separate formulations for each active ingredient. Accordingly, if more than two active ingredients are to be used, all active ingredients can be formulated in a common formulation or all active ingredients can be formulated in separate formulations; Mixed forms are also conceivable, in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow the active substances in question to be used separately or in succession.
Die hier mit ihrem„Common Name“ spezifizierten Wirkstoffe sind bekannt und beispielsweise im „Pesticide Manual“ (siehe oben) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticidesi. The active ingredients specified here with their "Common Name" are known and described, for example, in the "Pesticide Manual" (see above) or can be researched on the Internet (e.g. http://www.alanwood.net/pesticidesi.
Beispielhafte Wirkstoffe aus der Gruppe der Ektoparasitizide als Mischungspartner schließen, ohne dass dies eine Einschränkung darstellen soll, die oben ausführlich aufgelisteten Insektizide und Akkarizide ein. Weitere verwendbare Wirkstoffe sind unten gemäß der oben erwähnten Klassifikation, die auf dem aktuellen IRAC Mode of Action Classification Scheme beruht, aufgeführt: (1) Acetylcholinesterase (AChE)-Inhibitoren; (2) GABA-gesteuerte Chlorid-Kanal-Blocker; (3) Natrium-Kanal-Modulatoren; (4) kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (5) allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (6) allosterische Modulatoren des Glutamat- abhängigen Chloridkanals (GluCl); (7) Juvenilhormon-Mimetika; (8) verschiedene nichtspezifische (Multi-Site) Inhibitoren; (9) Modulatoren Chordotonaler Organe; (10) Milbenwachstumsinhibitoren; (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP- Disruptoren; (13) Entkoppler der oxidativen Phosphorylierung durch Störung des Protonengradienten; (14) Blocker des nicotinischen Acetylcholinrezeptorkanals; (15) Inhibitoren der Chitinbiosynthese, Typ 0; (16) Inhibitoren der Chitinbiosynthese, Typ 1; (17) Häutungsdisruptor (insbesondere bei Dipteren, d.h. Zweiflüglern); (18) Ecdyson- Rezeptor- Agonisten; (19) Octopamin- Rezeptor- Agonisten; (21) mitochondriale Komplex-I-Elektronentransportinhibitoren; (25) mitochondriale Komplex-II- Elektronentransportinhibitoren; (20) mitochondriale Komplex-III-Elektronentransportinhibitoren; (22) Blocker des spannungsabhängigen Natriumkanals; (23) Inhibitoren der Acetyl-CoA-Carboxylase; (28) Ryanodinrezeptor-Modulatoren; Exemplary active ingredients from the group of ectoparasiticides as mixing partners include, but are not intended to be a limitation, the insecticides and accaricides listed in detail above. Other active ingredients that can be used are listed below according to the classification mentioned above, which is 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 modulators of the nicotinic acetylcholine receptor (nAChR); (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) chordotonic organ modulators; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decouplers of oxidative phosphorylation by disturbance of the proton gradient; (14) nicotinic acetylcholine receptor channel blocker; (15) chitin biosynthesis inhibitors, type 0; (16) chitin biosynthesis inhibitors, type 1; (17) molting disruptor (especially with dipteras, i.e. two-wingers); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) voltage-dependent sodium channel blocker; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators;
Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, z. B. Fentrifanil, Fenoxacrim, Cyclopren, Chlorobenzilat, Chlordimeform, Flubenzimin, Dicyclanil, Amidoflumet, Quinomethionat, Triarathen, Clothiazoben, Tetrasul, Kaliumoleat, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Brompropylat, Cryolit; Active substances with unknown or non-specific mechanisms of action, e.g. B. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlorodime form, flubenzimin, dicyclanil, amidoflumet, quinomethionate, Triarathes, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazon, gossyplur, flutenzin, bromopropylate, cryolite;
Verbindungen aus anderen Klassen, z.B. Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos(- ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylat, Trichlorfon, Tigolaner, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoat, Dichlofenthion, Demeton-S-methylsulfon, Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpyrifos(-ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos; Connections from other classes, e.g. Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos (- ethyl), Parathion (-ethyl), Methacrifos, Isopropyl-o-salicylate, Trichlorfon, Tigolaner, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoat, Dichlofenthions, Demeton-S-Sulfon-S Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos (-methyl), Azinphos (-ethyl), Chlorpyrifos (-ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensimfothion;
Organochlorverbindungen, z. B. Camphechlor, Lindan, Heptachlor; oder Phenylpyrazole, z. B. Acetoprol, Pyrafluprol, Pyriprol, Vaniliprol, Sisapronil; oder Isoxazoline, z. B. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Organochlorine compounds, e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. B. acetoprol, pyrafluprol, pyriprol, vaniliprol, sisapronil; or isoxazolines, e.g. B. Sarolans, Afoxolans, Lotilans, Fluralans;
Pyrethroide, z. B. (cis-, trans-)Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis-Permethrin, Clocythrin, Cyhalothrin (lambda-), Chlovaporthrin, oder halogenierte Kohlenwasserstoffverbindungen (HCHs), Pyrethroids, e.g. B. (cis-, trans-) metofluthrin, profluthrin, Flufenprox, flubrocythrinate, Fubfenprox, fenfluthrin, protrifen but, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, fenhrethrin, biopyrin, cethrin , Cyhalothrin (lambda), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs),
Neonicotinoide, z. B. Nithiazin Neonicotinoids, e.g. B. nithiazine
Dicloromezotiaz, Triflumezopyrim makrocyclische Lactone, z. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprinomectin, Doramectin, Emamectinbenzoat; Milbemycinoxim Dicloromezotiaz, triflumezopyrim macrocyclic lactones, e.g. B. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime
Tripren, Epofenonan, Diofenolan; Tripren, epofenonan, diofenolan;
Biologicals, Hormone oder Pheromone, zum Beispiel natürliche Produkte, z.B. Thuringiensin, Codlemon oder Neem- Komponenten Biologicals, hormones or pheromones, for example natural products, e.g. Thuringiensin, Codlemon or Neem components
Dinitrophenole, z. B. Dinocap, Dinobuton, Binapacryl; Dinitrophenols, e.g. B. Dinocap, Dinobuton, Binapacryl;
Benzoylhamstoffe, z. B. Fluazuron, Penfluron, Benzoyl ureas, e.g. B. fluazuron, penfluron,
Amidinderivate, z. B. Chlormebuform, Cymiazol, Demiditraz Amidine derivatives, e.g. B. chloromebuform, cymiazole, demiditraz
Bienenstockvarroa- Akarizide, zum Beispiel organische Säuren, z.B. Ameisensäure, Oxalsäure. Zu beispielhaften Wirkstoffen aus der Gruppe der Endoparasitizide, als Mischungspartner, zählen, ohne hierauf beschränkt zu sein, anthelmintische Wirkstoffe und antiprotozoische Wirkstoffe. Beehive varroa acaricides, for example organic acids, eg formic acid, oxalic acid. Exemplary active ingredients from the group of endoparasiticides, as mixing partners, include, but are not limited to, anthelmintic active ingredients and antiprotozoic active ingredients.
Zu den anthelmintischen Wirkstoffen zählen, ohne hierauf beschränkt zu sein, die folgenden nematiziden, trematiziden und/oder cestoziden Wirkstoffe: aus der Klasse der makrocyclischen Lactone zum Beispiel: Eprinomectin, Abamectin, Nemadectin, Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbemectin, Ivermectin, Emamectin, Milbemycin; aus der Klasse der Benzimidazole und Probenzimidazole zum Beispiel: Oxibendazol, Mebendazol, Triclabendazol, Thiophanat, Parbendazol, Oxfendazol, Netobimin, Fenbendazol, Febantel, Thiabendazol, Cyclobendazol, Cambendazol, Albendazol-sulfoxid, Albendazol, Flubendazol; aus der Klasse der Depsipeptide, vorzugsweise cyclischen Depsipetide, insbesondere 24-gliedrigen cyclischen Depsipeptide, zum Beispiel: Emodepsid, PF 1022A; aus der Klasse der Tetrahydropyrimidine zum Beispiel: Morantel, Pyrantel, Oxantel; aus der Klasse der Imidazothiazole zum Beispiel: Butamisol, Levamisol, Tetramisol; aus der Klasse der Aminophenylamidine zum Beispiel: Amidantel, deacyliertes Amidantel (dAMD), Tribendimidin; aus der Klasse der Aminoacetonitrile zum Beispiel: Monepantel; aus der Klasse der Paraherquamide zum Beispiel: Paraherquamid, Derquantel; aus der Klasse der Salicylanilide zum Beispiel: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; aus der Klasse der substituierten Phenole zum Beispiel: Nitroxynil, Bithionol, Disophenol, Hexachlorophen, Niclofolan, Meniclopholan; aus der Klasse der Organophosphate zum Beispiel: Trichlorfon, Naphthalofos, Dichlorvos/DDVP, Crufomat, Coumaphos, Haloxon; aus der Klasse der Piperazinone/Chinoline zum Beispiel: Praziquantel, Epsiprantel; aus der Klasse der Piperazine zum Beispiel: Piperazin, Hydroxyzin; aus der Klasse der Tetracycline zum Beispiel: Tetracyclin, Chlorotetracyclin, Doxycyclin, Oxytetracyclin, Rolitetracyclin; aus diversen anderen Klassen zum Beispiel: Bunamidin, Niridazol, Resorantel, Omphalotin, Oltipraz, Nitroscanat, Nitroxynil, Oxamniquin, Mirasan, Miraeil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazin, Dichlorophen, Diamfenetid, Clonazepam, Bephenium, Amoscanat, Clorsulon. The anthelmintic active ingredients include, but are not limited to, the following nematicidal, trematicidal and / or cestocidal active ingredients: from the macrocyclic lactone class, for example: Eprinomectin, Abamectin, Nemadectin, Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbem Ivermectin, emamectin, milbemycin; from the class of the benzimidazoles and sample zimidazoles for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole sulfoxide, albendazole sulfoxide, albendazole sulfoxide, from the class of depsipeptides, preferably cyclic depsipeptides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF 1022A; from the class of tetrahydropyrimidines, for example: morantel, pyrantel, oxantel; from the class of the imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of the aminophenylamidines, for example: amidantel, deacylated amidantel (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: monepantel; from the class of paraherquamides, for example: paraherquamide, derquantel; from the class of salicylanilides, for example: tribromosalan, bromoxanide, breadianid, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide; from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan; from the class of organophosphates, for example: Trichlorfon, Naphthalofos, Dichlorvos / DDVP, Crufomat, Coumaphos, Haloxon; from the class of the piperazinones / quinolines, for example: praziquantel, epsi prantel; from the piperazine class, for example: piperazine, hydroxyzine; from the class of the tetracyclines, for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes, for example: Bunamidin, Niridazol, Resorantel, Omphalotin, Oltipraz, Nitroscanat, Nitroxynil, Oxamniquin, Mirasan, Miraeil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazin, Dichlorophen, Diamfenetid, Clonazepamonphenon, Bephen.
Antiprotozoische Wirkstoffe, darunter, ohne hierauf beschränkt zu sein, die folgenden Wirkstoffe: aus der Klasse der Triazine zum Beispiel: Diclazuril, Ponazuril, Letrazuril, Toltrazuril; aus der Klasse Polyletherionophor zum Beispiel: Monensin, Salinomycin, Maduramicin, Narasin; aus der Klasse der makrocyclischen Lactone zum Beispiel: Milbemycin, Erythromycin; aus der Klasse der Chinolone zum Beispiel: Enrofloxacin, Pradofloxacin; aus der Klasse der Chinine zum Beispiel: Chloroquin; aus der Klasse der Pyrimidine zum Beispiel: Pyrimethamin; aus der Klasse der Sulfonamide zum Beispiel: Sulfachinoxalin, Trimethoprim, Sulfaclozin; aus der Klasse der Thiamine zum Beispiel: Amprolium; aus der Klasse der Lincosamide zum Beispiel: Clindamycin; aus der Klasse der Carbanilide zum Beispiel: Imidocarb; aus der Klasse der Nitrofurane zum Beispiel: Nifurtimox; aus der Klasse der Chinazolinonalkaloide zum Beispiel: Halofuginon; aus diversen anderen Klassen zum Beispiel: Oxamniquin, Paromomycin; aus der Klasse der Vakzine oder Antigene aus Mikroorganismen zum Beispiel: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus. Antiprotozoal active ingredients, including but not limited to the following active ingredients: from the triazine class, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyletherionophore, for example: monensin, salinomycin, maduramicin, narasin; from the class of the macrocyclic lactones, for example: milbemycin, erythromycin; from the class of the quinolones, for example: enrofloxacin, pradofloxacin; from the quinine class, for example: chloroquine; from the class of pyrimidines, for example: pyrimethamine; from the class of the sulfonamides, for example: sulfachinoxaline, trimethoprim, sulfaclozin; from the class of the thiamines, for example: amprolium; from the class of lincosamides, for example: clindamycin; from the class of carbanilides, for example: imidocarb; from the class of nitrofurans, for example: nifurtimox; from the class of quinazolinone alkaloids, for example: halofuginone; from various other classes, for example: oxamniquin, paromomycin; from the class of vaccines or antigens from microorganisms, for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Diviparus .
Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Vektorbekämpfung All of the mixture partners mentioned can, if they are capable of doing so on account of their functional groups, optionally form salts with suitable bases or acids. Combat vector
Die Verbindungen der Formel (I) können auch in der Vektorbekämpfung eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z. B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z. B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. The compounds of formula (I) can also be used in vector control. A vector in the sense of the present invention is an arthropod, in particular an insect or arachnid, which is capable of pathogens such as. B. Viruses, worms, unicellular organisms and bacteria from a reservoir (plant, animal, human, etc.) to a host. The pathogens can either be transferred mechanically (e.g. trachoma from non-stinging flies) to a host, or after injection (e.g. malaria parasites from mosquitoes) into a host.
Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: Examples of vectors and the diseases or pathogens they transmit are:
1) Mücken - Anopheles: Malaria, Filariose; 1) Mosquitoes - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von anderen Würmern; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of other worms;
- Aedes: Gelbfieber, Dengue-Fieber, weitere virale Erkrankungen, Filariasis; - Aedes: yellow fever, dengue, other viral diseases, filariasis;
- Simulien: Übertragung von Würmern, insbesondere Onchocerca volvulus; - Psychodidae: Übertragung von Leishmaniose - Simulations: transmission of worms, especially Onchocerca volvulus; - Psychodidae: transmission of leishmaniasis
2) Läuse: Hautinfektionen, epidemisches Fleckfieber; 2) lice: skin infections, epidemic typhus;
3) Flöhe: Pest, endemisches Fleckfieber, Bandwürmer; 3) Fleas: plague, endemic typhus, tapeworms;
4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 4) Flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
5) Milben: Acariose, epidemisches Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, Frühsommer-Meningoenzephalitis (FSME), Krim-Kongo-Fieber, Borreliose; 5) Mites: acariosis, epidemic typhus, rickettsi pock, tularemia, Saint-Louis encephalitis, early summer meningoencephalitis (TBE), Crimean-Congo fever, Lyme disease;
6) Zecken: Borelliosen wie Borrelia bungdorferi sensu lato., Borrelia duttoni, Frühsommer- Meningoenzephalitis, Q-Fieber (Coxiella bumetii), Babesien (Babesia canis canis), Ehrlichiose. 6) Ticks: Borelliosis such as Borrelia bungdorferi sensu lato., Borrelia duttoni, early summer meningoencephalitis, Q fever (Coxiella bumetii), Babesia (Babesia canis canis), Ehrlichiosis.
Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten, zum Beispiel Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Psychodide wie Phlebotomus, Lutzomyia, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Examples of vectors in the sense of the present invention are insects, for example aphids, flies, cicadas or thrips, which plant viruses can transmit to plants. Other vectors that plant viruses can transmit are spider mites, lice, beetles and nematodes. Further examples of vectors in the sense of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. BA gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.
Eine Vektorbekämpfung ist auch möglich, wenn die Verbindungen der Formel (I) Resistenz-brechend sind. Vector control is also possible if the compounds of the formula (I) are resistance-breaking.
Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten und/oder Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorbekämpfung, z. B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorrats und Materialschutz. Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens which are transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. B. in agriculture, horticulture, in forests, in gardens and leisure facilities as well as in storage and material protection.
Schutz von technischen Materialen Protection of technical materials
Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z. B. aus den Ordnungen Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. The compounds of formula (I) are suitable for protecting industrial materials against attack or destruction by insects, for. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. In the present context, technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints. The use of the invention to protect wood is particularly preferred.
In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d. h., sie können ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder Fungizide kommen insbesondere die oben genannten in Frage. In a further embodiment, the compounds of the formula (I) are present as a ready-to-use pesticide, ie. that is, they can be applied to the corresponding material without further changes. Other insecticides or fungicides in particular are those mentioned above.
Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Surprisingly, it has also been found that the compounds of the formula (I) can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water, against fouling. Likewise, the compounds of formula (I) can be used alone or in combinations with other active ingredients as antifouling agents. Control of animal pests in the hygiene sector
Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren, Zecken und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen, Tierzuchtanlagen Vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z. B. Pump- und Zerstäubersprays, Nebelautomaten, Foggem, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfem, Gel- und Membranverdampfem, propellergetriebenen Verdampfern, energielosen bzw. passivenThe compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites that occur in closed rooms, such as, for example, apartments, factory halls, offices, vehicle cabins, animal husbandry systems. To control animal pests, the compounds of the formula (I) are used alone or in combination with other active compounds and / or auxiliaries. They are preferably used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development. These pests include, for example, pests from the Arachnida class, from the Scorpiones, Araneae and Opiliones orders, from the Chilopoda and Diplopoda classes, from the Insecta class the Blattodea order, from the Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera orders, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the Malacostraca class the order Isopoda. The application takes place, for example, in aerosols, unpressurized sprays, e.g. B. pump and atomizer sprays, fog machines, fogg, foams, gels, evaporator products with evaporator plates made of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free or passive
Verdampfüngssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködem oder Köderstationen. Evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in litter edema or bait stations.
Herstellungsbeispiele: Manufacturing examples:
Analytische Bestimmungen Analytical determinations
Die nachstehend beschriebenen Durchführungen der analytischen Bestimmungen beziehen sich auf alle Angaben im gesamten Dokument, sofern die Durchführung der jeweiligen analytischen Bestimmung an der jeweiligen Textstelle nicht gesondert beschrieben ist. The implementation of the analytical provisions described below refers to all information in the entire document, unless the implementation of the respective analytical determination is not described separately at the relevant text.
Massenspektrometrie Mass spectrometry
Die Bestimmung von [M+H]+ oder M mittels LC-MS unter sauren chromatographischen Bedingungen wurde mit 1 ml Ameisensäure pro Liter Acetonitril und 0.9 ml Ameisensäure pro Liter Millipore- Wasser als Eluenten durchgeführt. Es wurde die Säule Zorbax Eclipse Plus C18 50 mm * 2.1 mm, 1.8 pm verwendet, bei einer Temperatur des Säulenofens von 55°C. The determination of [M + H] + or M by means of LC-MS under acidic chromatographic conditions was carried out with 1 ml of formic acid per liter of acetonitrile and 0.9 ml of formic acid per liter of Millipore water as eluents. The Zorbax Eclipse Plus C18 50 mm * 2.1 mm, 1.8 pm column was used at a column oven temperature of 55 ° C.
Instrumente: Instruments:
LC-MS3: Waters UPLC mit SQD2 Massenspektrometer und SampleManager Probenwechsler. LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManager sample changer.
Linearer Gradient 0.0 bis 1.70 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 1.70 bis 2.40 Minuten konstant 95 % Acetonitril, Fluss 0.85 ml/min. LC-MS6 und LC-MS7: Agilent 1290 LC, Agilent MSD Massenspektrometer, HTS PAL Probenwechsler. Linearer Gradient 0.0 bis 1.80 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 1.80 bis 2.50 Minuten konstant 95 % Acetonitril, Fluss 1.0 ml/min). Linear gradient 0.0 to 1.70 minutes from 10% acetonitrile to 95% acetonitrile, from 1.70 to 2.40 minutes constant 95% acetonitrile, flow 0.85 ml / min. LC-MS6 and LC-MS7: Agilent 1290 LC, Agilent MSD mass spectrometer, HTS PAL sample changer. Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow 1.0 ml / min).
Die Bestimmung von [M+H]+ mittels LC-MS unter neutralen chromatographischen Bedingungen wurde mit Acetonitril und Millipore-Wasser mit 79 mg/1 Ammoniumcarbonat als Eluenten durchgeführt. The determination of [M + H] + by means of LC-MS under neutral chromatographic conditions was carried out with acetonitrile and Millipore water with 79 mg / 1 ammonium carbonate as eluent.
Instrumente: Instruments:
LC-MS4: Waters IClass Acquity mit QDA Massenspektrometer und FTN Probenwechsler (Säule Waters Acquity 1.7 pm 50 mm * 2.1 mm, Säulenofentemperatur 45°C). Linearer Gradient 0.0 bis 2.10 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 2.10 bis 3.00 Minuten konstant 95 % Acetonitril, Fluss 0.7 mFmin. LC-MS4: Waters IClass Acquity with QDA mass spectrometer and FTN sample changer (column Waters Acquity 1.7 pm 50 mm * 2.1 mm, column oven temperature 45 ° C). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow 0.7 mFmin.
LC-MS5: Agilent 1100 LC System mit MSD Massenspektrometer und HTS PAL Probenwechsler (Säule: Zorbax XDB CI 8 1.8 pm 50 mm * 4.6 mm, Säulenofentemperatur 55°C). Linearer Gradient 0.0 bis 4.25 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 4.25 bis 5.80 Minuten konstant 95 % Acetonitril, Fluss 2.0 mFmin. Die Retentionzeit-Indizes wurden in allen Fällen aus einer Kalibrierungsmessung einer homologen Serie von geradkettigen Alkan-2-onen mit 3 bis 16 Kohlenstoffen bestimmt, wobei der Index des ersten Alkanons auf 300, der des letzten auf 1600 gesetzt und zwischen den Werten aufeinanderfolgender Alkanone linear interpoliert wurde. LC-MS5: Agilent 1100 LC system with MSD mass spectrometer and HTS PAL sample changer (column: Zorbax XDB CI 8 1.8 pm 50 mm * 4.6 mm, column oven temperature 55 ° C). Linear gradient 0.0 to 4.25 minutes from 10% acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95% acetonitrile, flow 2.0 mFmin. In all cases, the retention time indices were determined from a calibration measurement of a homologous series of straight-chain alkan-2-ones with 3 to 16 carbons, the index of the first alkanone being set to 300, that of the last one to 1600 and linear between the values of successive alkanones was interpolated.
Die Messungen der *H-NMR Spektren wurden mit einem Bruker Avance III 400 MHz The * H-NMR spectra were measured with a Bruker Avance III 400 MHz
Spektrometer, ausgestattet mit einem 1.7 mm TCI Probenkopf, mit Tetramethylsilan als Standard (0.00 ppm) von Lösungen in den Lösungsmitteln CD3CN, CDCL oder dö-DMSO durchgeführt. Alternativ wurde ein Bruker Avance III 600 MHz Spektrometer ausgestattet mit einem 5 mm CPNMP Probenkopf oder ein Bruker Avance NEO 600 MHz Spektrometer ausgestattet mit einem 5 mm TCI Probenkopf für die Messungen verwendet. In der Regel wurden die Messungen bei einer Probenkopftemperatur von 298 K durchgeführt. Sofern andere Messtemperaturen verwendet wurden, wird dies gesondert vermerkt. Spectrometer equipped with a 1.7 mm TCI probe head, carried out with tetramethylsilane as standard (0.00 ppm) of solutions in the solvents CD3CN, CDCL or d ö -DMSO. Alternatively, a Bruker Avance III 600 MHz spectrometer equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz spectrometer equipped with a 5 mm TCI probe head was used for the measurements. As a rule, the measurements were carried out at a probe head temperature of 298 K. If other measuring temperatures were used, this will be noted separately.
NMR-Peaklisten-V erfahren NMR peak list experience
Die 1 H-NMR-Datcn ausgewählter Beispiele werden in Form von 1 H-NMR-Pcaklistcn dargestellt. Zu jedem Signalpeak wird erst der d-Wert in ppm und dann die Signalintensität in runden Klammem aufgeführt. Die d-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. The 1 H-NMR data of selected examples are presented in the form of 1 H-NMR lists. For each signal peak, the d-value is shown in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated from each other by semicolons.
Die Peakliste eines Beispiels hat daher die Form: di (Intensität^; 62 (Intensität2); . ; d; (Intensität^; . ; dh (Intensität) The peak list of an example therefore has the form: di (intensity ^; 62 (intensity2);.; D; (intensity ^;.; D h (intensity)
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einer gedruckten Darstellung eines 1 H-NMR-Spcktrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. The intensity of sharp signals correlates with the height of the signals in a printed representation of a 1 H NMR spectrum in cm and shows the real relationships of the signal intensities. With wide 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.
Zur Kalibrierung der chemischen Verschiebung von 1 H-NMR-Spcktrcn wird Tetramethylsilan genutzt oder die chemische Verschiebung des Lösungsmittels, falls die Probe kein Tetramethylsilan enthält. Daher können die 1 H-NMR-Pcaklistcn unter Umständen den Tetramethylsilan-Peak enthalten. Tetramethylsilane is used to calibrate the chemical shift of 1 H NMR spectroscopy or the chemical shift of the solvent if the sample does not contain tetramethylsilane. Therefore, the 1 H NMR pakaklistcn may contain the tetramethylsilane peak.
Die Listen der 1 H-NMR-Pcaks sind äquivalent zu den klassischen 1 H-NMR-Darstcllungcn und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen 1 H-NMR-Intcrprctation aufgeführt werden. The lists of the 1 H-NMR pakaks are equivalent to the classic 1 H-NMR diagrams and thus usually contain all the peaks that are listed in a classic 1 H-NMR specification.
Darüber hinaus können sie wie klassische 1 H-NMR-Darstcllungcn Lösungsmittelsignale, Signale von Stereoisomeren der erfindungsgemäßen Verbindungen, die gegebenenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. NMR-Lösungsmittelsignale, der Tetramethylsilan-Peak und das Wassersignal im jeweiligen Lösungsmittel sind von der relativen Intensitätskalibrierung ausgenommen, weil die dafür angegebenen Intensitätswerte sehr hoch sein können. In addition, like classic 1 H-NMR representations, they can show solvent signals, signals of stereoisomers of the compounds according to the invention, which may be the subject of the invention, and / or peaks of impurities. NMR solvent signals, the tetramethylsilane peak and the water signal in the respective solvent are excluded from the relative intensity calibration because the specified intensity values can be very high.
Die Peaks von (Stereo)Isomeren der erfindungsgemäßen Verbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der erfindungsgemäßen Verbindungen (zum Beispiel bei einer Reinheit von >90%). The peaks of (stereo) isomers of the compounds according to the invention and / or peaks of impurities usually have a lower intensity on average than the peaks of the compounds according to the invention (for example with a purity of> 90%).
Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion eines Herstellungsverfahrens anhand von“Nebenprodukt-Fingerabdrücken” zu erkennen. Such stereoisomers and / or impurities can be typical of the respective production process. Your peaks can thus help to identify the reproduction of a manufacturing process using “by-product fingerprints”.
Einem Experten, der die Peaks der erfindungsgemäßen Verbindungen mit bekannten Verfahren (MestreC, ACD-Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der erfindungsgemäßen Verbindungen identifizieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Identifizierung ist äquivalent zur betreffenden Peak- Auflistung bei der klassischen lH-NMR-Interpretation. An expert who calculates the peaks of the compounds according to the invention using known methods (MestreC, ACD simulation, but also using empirically evaluated expected values) can identify the peaks of the compounds according to the invention as required, additional intensity filters being used if necessary. This identification is equivalent to the relevant peak listing in the classic 1 H NMR interpretation.
Das benutzte Lösungsmittel kann aus der JCAMP-Datei mit dem Parameter„solvent“ ausgelesen werden, die Messfrequenz des Spektrometers mit„observe firequency“ und das Spektrometermodell mit „spectrometer/data System“. The solvent used can be read from the JCAMP file with the parameter "solvent", the measuring frequency of the spectrometer with "observe firequency" and the spectrometer model with "spectrometer / data system".
13C-NMR-Daten werden analog zu den 1 H-NMR Daten als Peaklisten aus breitbandentkoppelten 13C- NMR- Spektren angegeben. Auch hier sind die NMR-Lösungsmittelsignale und Tetramethylsilan aus der relativen Intensitätskalibrierung herausgenommen, weil diese Signale sehr hohe Intensitätswerte haben können. 13 C-NMR data are given in analogy to the 1 H-NMR data as peak lists from broadband-decoupled 13 C-NMR spectra. Here, too, the NMR solvent signals and tetramethylsilane are excluded from the relative intensity calibration because these signals can have very high intensity values.
Weitere Details zu 1 H-NMR-Pcaklistcn können entnommen werden aus:“Citation of NMR Peaklist Data within Patent Applications” in der Research Disclosure Database Number 564025. logP- Werte Further details on 1 H-NMR lists can be found in: “Citation of NMR Peaklist Data within Patent Applications” in Research Disclosure Database Number 564025. logP values
Die Bestimmung der logP-Werte erfolgte gemäß EEC Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (CI 8) mit Hilfe folgender Methoden: The logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (CI 8) using the following methods:
|a Der logP Wert wird durch LC-UV Messung im sauren Bereich bestimmt, mit 0.9 ml/1 Ameisensäure in Wasser und 1.0 ml/1 Ameisensäure in Acetonitril als Eluenten (linearer Gradient von 10% Acetonitrile bis 95% Acetonitril). |h Der logP Wert wird durch LC-UV Messung im neutralen Bereich bestimmt, mit 79 mg/1 Ammoniumcarbonat in Wasser und Acetonitril als Eluenten (linearer Gradient von 10% Acetonitril bis 95% Acetonitril). | a The logP value is determined by LC-UV measurement in the acidic range, with 0.9 ml / 1 formic acid in water and 1.0 ml / 1 formic acid in acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile). | h The logP value is determined by LC-UV measurement in the neutral range, with 79 mg / 1 ammonium carbonate in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).
Die Kalibrierung wurde mit einer homologen Reihe geradkettiger Alkan-2-one (mit 3 bis 16 Kohlenstoffatomen) mit bekannten logP Werten durchgeführt. Die Werte zwischen aufeinanderfolgender Alkanone werden durch lineare Regression bestimmt. The calibration was carried out with a homologous series of straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known logP values. The values between successive alkanones are determined by linear regression.
1- [3-Ethylsulfonyl-2- [3-methyl-6-(trifluormethoxy)imidazo [4,5-b] pyridin-2-yl] pyrazolo [1,5- a]pyridin-6-yl] cyclopropancarbonitril (1-1) 1- [3-Ethylsulfonyl-2- [3-methyl-6- (trifluoromethoxy) imidazo [4,5-b] pyridin-2-yl] pyrazolo [1,5-a] pyridin-6-yl] cyclopropanecarbonitrile (1st -1)
350,0 mg (0,73 mmol) l-[3-Brom-2-[3-methyl-6-(trifluormethoxy)imidazo[4,5-b]pyridin-2- yl]pyrazolo[l,5-a]pyridin-6-yl]cyclopropancarbonitril, 851,6 mg (7,33 mmol) Natriumethansulfinat und 21,0 mg (0,11 mmol) Kupfer(I)iodid wurden in 16 ml N,N-Dimethylformamid in einem Mikrowellen Synthesegerät (Anton Paar, Monowave 400) 12 h bei 120°C gerührt. Anschließend wurde das Reaktionsgemisch mit einer Natriumchlorid Lösung versetzt und dreimal mit Essigester extrahiert. Die organische Phase wurde über Natriumsulfat getrocknet und anschließend das Lösungsmittel im Vakuum abdestilliert. Der Rückstand wurde durch säulenchromatographische Aufreinigung über präparative HPLC mit einem Wasser / Acetonitril Gradienten als Laufimittel gereinigt. logP (sauer): 3,18; MH+: 491; ^-NMR^OO MHz, D6-DMSO) d ppm: 9.12 (s, 1H), 8.64 (s, 1H), 8.44 (s, 1 H), 8,18 (d, 1H), 7.86 (d, 1H), 4,00 (s, 3H), 3.81 (q, 2H), 1.81-1.85 (m, 2H), 1.72-1.75 (m, 2H), 1.23350.0 mg (0.73 mmol) of l- [3-bromo-2- [3-methyl-6- (trifluoromethoxy) imidazo [4,5-b] pyridin-2-yl] pyrazolo [1,5-a ] pyridin-6-yl] cyclopropanecarbonitrile, 851.6 mg (7.33 mmol) sodium ethanesulfinate and 21.0 mg (0.11 mmol) copper (I) iodide in 16 ml N, N-dimethylformamide in a microwave synthesizer ( Anton Paar, Monowave 400) stirred at 120 ° C for 12 h. The reaction mixture was then mixed with a sodium chloride solution and extracted three times with ethyl acetate. The organic phase was dried over sodium sulfate and then the solvent was distilled off in vacuo. The residue was purified by column chromatography purification using preparative HPLC using a water / acetonitrile gradient as the eluent. logP (acidic): 3.18; MH + : 491; ^ -NMR ^ OO MHz, D 6 -DMSO) d ppm: 9.12 (s, 1H), 8.64 (s, 1H), 8.44 (s, 1 H), 8.18 (d, 1H), 7.86 (d, 1H), 4.00 (s, 3H), 3.81 (q, 2H), 1.81-1.85 (m, 2H), 1.72-1.75 (m, 2H), 1.23
(t, 3H). (t, 3H).
1- [3-Brom-2- [3-methyl-6-(trifluormethoxy)imidazo [4,5-b] pyridin-2-yl] pyrazolo [1 ,5-a] pyridin-6- yl] cyclopropancarbonitril 1- [3-bromo-2- [3-methyl-6- (trifluoromethoxy) imidazo [4,5-b] pyridin-2-yl] pyrazolo [1,5-a] pyridin-6-yl] cyclopropanecarbonitrile
200 mg (0,96 mmol) N2-Methyl-5-(trifluormethoxy)pyridin-2,3-diamin und 369 mg (1,20 mmol) 3- Brom-6-(l-cyanocyclopropyl)pyrazolo[l,5-a]pyridin-2-carbonsäure wurden in Pyridin (5 mL) vorgelegt. 185 mg (0,96 mmol) EDCI wurden zugegeben und das Gemisch für 16 h bei Raumtemperatur gerührt. Das Lösungsmittel wurde abdestilliert, der Rückstand mit Wasser verdünnt und mit Essigester extrahiert. Die organische Phase wurde über Natriumsulfat getrocknet und unter vermindertem Druck vom Lösungsmittel befreit. Der Rückstand wurde in 5 ml Essigsäure für 8 h bei lOO°C gerührt. Anschließend wurde das Lösungsmittel abdestiliert, der Rückstand mit Wasser verdünnt, ab filtriert und mit Wasser gewaschen. logP (sauer): 3,90; MH+: 477; ^-NMR^OO MHz, D6-DMSO) d ppm: 8.96 (s, 1H), 8.59 (s, 1H), 8.42 (s, 1 H), 7,80 (d, 1H), 7.56 (d, 1H), 4,16 (s, 3H), 1.78-1.82 (m, 2H), 1.69-1.72 (m, 2H). 200 mg (0.96 mmol) of N2-methyl-5- (trifluoromethoxy) pyridine-2,3-diamine and 369 mg (1.20 mmol) of 3-bromo-6- (l-cyanocyclopropyl) pyrazolo [l, 5- a] pyridine-2-carboxylic acid were placed in pyridine (5 mL). 185 mg (0.96 mmol) EDCI were added and the mixture was stirred for 16 h at room temperature. The solvent was distilled off, the residue was diluted with water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and freed from the solvent under reduced pressure. The residue was stirred in 5 ml of acetic acid for 8 h at 100 ° C. The solvent was then distilled off, the residue diluted with water, filtered off and washed with water. logP (acidic): 3.90; MH + : 477; ^ -NMR ^ OO MHz, D 6 -DMSO) d ppm: 8.96 (s, 1H), 8.59 (s, 1H), 8.42 (s, 1 H), 7.80 (d, 1H), 7.56 (d, 1H), 4.16 (s, 3H), 1.78-1.82 (m, 2H), 1.69-1.72 (m, 2H).
3-Brom-6-(l-cyanocyclopropyl)pyrazolo[l,5-a]pyridin-2-carbonsäure 3-bromo-6- (l-cyanocyclopropyl) pyrazolo [1,5-a] pyridine-2-carboxylic acid
1,00 g (4,40 mmol) 6-(l-Cyanocyclopropyl)pyrazolo[l,5-a]pyridin-2-carbonsäure und 0,862 g (4,84 mmol) N-Bromsuccinimid wurden unter Argon bei 0°C in 200 ml Chloroform gelöst und 1 h bei 0°C gerührt. Anschließend wurde das Reaktionsgemisch mit Wasser versetzt, die organische Phase abgetrennt, über Natriumsulfat getrocknet, filtriert und das Lösungsmittel im Vakuum abdestilliert. logP (sauer): 1,55; MH+: 306; 'H-NMR (400 MHz, DMSO-d6): d 13,48 (s, 1H), 8,86 (s, 1H), 7,72 (d, 1H), 7,49 (d, 1H), 1,76-1,79 (m, 2H), 1,64-1,67 (m, 2H). 1.00 g (4.40 mmol) of 6- (l-cyanocyclopropyl) pyrazolo [l, 5-a] pyridine-2-carboxylic acid and 0.862 g (4.84 mmol) of N-bromosuccinimide were added under argon at 0 ° C 200 ml of chloroform dissolved and stirred at 0 ° C for 1 h. Water was then added to the reaction mixture, the organic phase was separated off, dried over sodium sulfate, filtered and the solvent was distilled off in vacuo. logP (acidic): 1.55; MH + : 306; 'H NMR (400 MHz, DMSO-d 6 ): d 13.48 (s, 1H), 8.86 (s, 1H), 7.72 (d, 1H), 7.49 (d, 1H) , 1.76-1.79 (m, 2H), 1.64-1.67 (m, 2H).
6-(l-Cyanocyclopropyl)pyrazolo[l,5-a]pyridin-2-carbonsäure 6- (l-Cyanocyclopropyl) pyrazolo [1,5-a] pyridine-2-carboxylic acid
9,00 g (37,3 mmol) Methyl 6-(l-Cyanocyclopropyl)pyrazolo[l,5-a]pyridin-2-carboxylat und 1,49 g (35,4 mmol) Lithiumhydroxid Monohydrat wurden in einem Tetrahydrofuran / Wasser Gemisch (100 m 1/150 ml) 16 h bei Raumtemperatur gerührt. Anschließend wurde das organsiche Lösungsmittel im Vakuum abdestilliert, die wäßrige Phase mit 100 ml Essigester gewaschen und mit 1 N Salzsäure auf pH = 4 gestellt. Der ausgefallen Feststoff wurde ab filtriert und im Vakkum getrocknet. 9.00 g (37.3 mmol) of methyl 6- (l-cyanocyclopropyl) pyrazolo [1,5-a] pyridine-2-carboxylate and 1.49 g (35.4 mmol) of lithium hydroxide monohydrate were dissolved in a tetrahydrofuran / water Mixture (100 m 1/150 ml) stirred for 16 h at room temperature. The organic solvent was then distilled off in vacuo, the aqueous phase was washed with 100 ml of ethyl acetate and adjusted to pH = 4 with 1N hydrochloric acid. The precipitated solid was filtered off and dried in vacuo.
'H-NMR (400 MHz, DMSO-dö): d 13,00 (br. s, 1H), 8,78 (s, 1H), 7,79 (d, 1H), 7,32 (d, 1H), 7,07 (s, 1H), 1,74 (m, 2H), 1,62 (m, 2H). 'H NMR (400 MHz, DMSO-d ö ): d 13.00 (br. S, 1H), 8.78 (s, 1H), 7.79 (d, 1H), 7.32 (d, 1H), 7.07 (s, 1H), 1.74 (m, 2H), 1.62 (m, 2H).
Methyl 6-(l-Cyanocyclopropyl)pyrazolo[l,5-a]pyridin-2-carboxylat Methyl 6- (l-cyanocyclopropyl) pyrazolo [1,5-a] pyridine-2-carboxylate
30 g (111 mmol) einer 0,4 molaren Lösung von Methyl (E)-2-azido-3-[5-(l-cyanocyclopropyl)-2- pyridyl]prop-2-enoat in Mesitylen wurde 1 h zum Rückfluß erhitzt, abkühlen gelassen und anschließend für 1 h auf 0°C gekühlt. Das ausgefallene kristalline Produkt wurde abfiltriert, über Nacht in einer Essigester / Hexan Mischung (1 :20) gerührt, abfiltriert und im Vakuum getrocknet. Das Produkt wurde ohne weitere Reinigung in die nächste Stufe eingesetzt. 30 g (111 mmol) of a 0.4 molar solution of methyl (E) -2-azido-3- [5- (l-cyanocyclopropyl) -2-pyridyl] prop-2-enoate in mesitylene was heated to reflux for 1 h , allowed to cool and then cooled to 0 ° C for 1 h. The precipitated crystalline product was filtered off, stirred overnight in an ethyl acetate / hexane mixture (1:20), filtered off and dried in vacuo. The product was used in the next step without further purification.
Methyl (E)-2-azido-3- [5-(l-cyanocyclopropyl)-2-pyridyl] prop-2-enoat Methyl (E) -2-azido-3- [5- (l-cyanocyclopropyl) -2-pyridyl] prop-2-enoate
Zu einer auf -10 bis -l5°C gekühlten Lösung aus 50,0 g (290 mmol) 6-Formyl-3- pyridyl)cyclopropancarbonitril und 36,8 g (320 mmol) Azido-essigsäure-methylester in 350 ml Methanol wurde eine Lösung von 17,6 g (326 mmol) Natriummethylat in 200 ml Methanol über 30 min langsam zugetropft, wobei die Reaktionstemperatur bei - 10°C gehalten wurde. Nach der Zugabe ließ man die Temperatur langsam auf 0°C kommen und hielt den Ansatz für weitere 2 h bei dieser Temperatur. Während dieser Zeit begann das Produkt als feiner Niederschlag auszufallen. Ein Blasenzäher wurde auf den Reaktionskolben gesetzt und der Ansatz über Nacht unter Eisbadkühlung gerührt. Die entstandene Suspension wurde anschließend zu einer Mischung aus 2 kg Eis und 400 g festem Ammoniumchlorid gegeben, gerührt bis das Eis geschmolzen war und abfiltriert. Der Filterkuchen wurde mit kaltem Wasser gewaschen, im Vakuum getrocknet und in 600 ml Dichlormethan gelöst. Die organische Phase wurde über Magnesiumsulfat getrocknet, über Kieselgel filtriert und der Rückstand mit 200 ml Dichlormethan nachgewaschen. Die vereinigten organischen Phasen wurden eingeengt und der Rückstand ohne weitere Reinigung in die nächste Stufe eingesetzt. A solution of 50.0 g (290 mmol) of 6-formyl-3-pyridyl) cyclopropanecarbonitrile and 36.8 g (320 mmol) of methyl azidoacetate in 350 ml of methanol was added to a solution cooled to -10 to -15 ° C. Solution of 17.6 g (326 mmol) of sodium methylate in 200 ml of methanol was slowly added dropwise over 30 minutes, the reaction temperature being kept at -10 ° C. After the addition, the temperature was allowed to slowly come to 0 ° C. and the batch was kept at this temperature for a further 2 h. During this time the product started to precipitate out as a fine precipitate. A bubble counter was placed on the reaction flask and the mixture was stirred overnight with ice bath cooling. The resulting suspension was then added to a mixture of 2 kg of ice and 400 g of solid ammonium chloride, stirred until the ice had melted and filtered off. The filter cake was washed with cold water, dried in vacuo and dissolved in 600 ml dichloromethane. The organic phase was dried over magnesium sulfate, filtered through silica gel and the residue was washed with 200 ml of dichloromethane. The combined organic phases were concentrated and the residue was used in the next step without further purification.
In Analogie zu Beispiel (1-1) und gemäß den oben beschriebenen Herstellverfahren läßt lassen sich die folgenden Verbindungen der Formel (I) hersteilen: l-[3-Ethylsulfonyl-2-[l-methyl-5-(trifluormethoxy)benzimidazol-2-yl]pyrazolo[l,5-a]pyridin-6- yl]cyclopropancarbonitril (1-2) The following compounds of the formula (I) can be prepared analogously to Example (1-1) and in accordance with the preparation processes described above: l- [3-ethylsulfonyl-2- [l-methyl-5- (trifluoromethoxy) benzimidazole-2 -yl] pyrazolo [1,5-a] pyridin-6-yl] cyclopropanecarbonitrile (1-2)
logP (sauer): 3,29; MH+: 490; ^-NMR^OO MHz, D6-DMSO) d ppm: 9.10 (s, 1H), 8, 17 (d, 1H), 7.79 (s, 1H), 7,82-7,86 (m, 2H), 7,42 (d, 1H), 3,97 (s, 3H), 3.81 (q, 2H), 1.81-1.84 (m, 2H), 1.71-1.75 (m, 2H), 1.22 (t, 3H). l-[3-Ethylsulfonyl-2-[3-methyl-6-(l, 1,2,2, 2-pentafluorethoxy)imidazo[4, 5-b]pyridin-2- yl]pyrazolo[l,5-a]pyridin-6-yl]cyclopropancarbonitril (1-5) logP (acidic): 3.29; MH + : 490; ^ -NMR ^ OO MHz, D 6 -DMSO) d ppm: 9.10 (s, 1H), 8, 17 (d, 1H), 7.79 (s, 1H), 7.82-7.86 (m, 2H) , 7.42 (d, 1H), 3.97 (s, 3H), 3.81 (q, 2H), 1.81-1.84 (m, 2H), 1.71-1.75 (m, 2H), 1.22 (t, 3H) . l- [3-Ethylsulfonyl-2- [3-methyl-6- (l, 1,2,2, 2-pentafluoroethoxy) imidazo [4, 5-b] pyridin-2-yl] pyrazolo [1,5-a ] pyridin-6-yl] cyclopropanecarbonitrile (1-5)
logP (sauer): 3,76; MH+: 541 ; 1H-NMR(400 MHz, D6-DMSO) d ppm: 9.10 (s, 1H), 8,62 (s, 1H), 8,44 (s, 1H), 8,20 (d, 1H), 7,85 (d, 1H), 4,00 (s, 3H), 3.81 (q, 2H), 1.82-1.85 (m, 2H), 1.72-1.75 (m, 2H), 1.23 (t, 3H). 1- [2-(2,2-Difluor-7-methyl- [1 ,3] dioxolo [4,5-f] benzimidazol-6-yl)-3-ethylsulfonyl-pyrazolo [1 ,5- a]pyridin-6-yl] cyclopropancarbonitril (1-3) logP (acidic): 3.76; MH +: 541; 1H-NMR (400 MHz, D6-DMSO) d ppm: 9.10 (s, 1H), 8.62 (s, 1H), 8.44 (s, 1H), 8.20 (d, 1H), 7, 85 (d, 1H), 4.00 (s, 3H), 3.81 (q, 2H), 1.82-1.85 (m, 2H), 1.72-1.75 (m, 2H), 1.23 (t, 3H). 1- [2- (2,2-Difluoro-7-methyl- [1,3] dioxolo [4,5-f] benzimidazol-6-yl) -3-ethylsulfonyl-pyrazolo [1,5-a] pyridine- 6-yl] cyclopropanecarbonitrile (1-3)
117,7 mg (0,10 mmol) l-[3-Brom-2-(2,2-difluor-7-methyl-[l,3]dioxolo[4,5-f]benzimidazol-6- yl)pyrazolo[l,5-a]pyridin-6-yl]cyclopropancarbonitril, 119,5 mg (1,02 mmol) Natriumethansulfinat und 2,9 mg (0,01 mmol) Kupfer(I)iodid wurden in 6 ml N,N-Dimethylformamid in einem Mikrowellen Synthesegerät (Anton Paar, Monowave 400) 4 h bei l40°C gerührt. Das Reaktionsgemisch wurde über Kieselgel abfiltriert, mit Acetonitril nachgewaschen und der Rückstand durch säulenchromatographische Aufreinigung über präparative HPLC mit einem Wasser / Acetonitril Gradienten als Lauftnittel gereinigt. logP (sauer): 3,18; MH+: 486; 1H-NMR(400 MHz, D6-DMSO) d ppm: 9.07 (s, 1H), 8.17 (d, 1H), 7,89 (s, 1 H), 7,81-7,84 (m, 2H), 3,95 (s, 3H), 3.80 (q, 2H), 1.81-1.85 (m, 2H), 1.71-1.75 (m, 2H), 1.21 (t, 3H). 117.7 mg (0.10 mmol) l- [3-bromo-2- (2,2-difluoro-7-methyl- [1,3] dioxolo [4,5-f] benzimidazol-6-yl) pyrazolo [1,5-a] pyridin-6-yl] cyclopropanecarbonitrile, 119.5 mg (1.02 mmol) sodium ethanesulfinate and 2.9 mg (0.01 mmol) copper (I) iodide were dissolved in 6 ml N, N- Dimethylformamide in a microwave synthesizer (Anton Paar, Monowave 400) stirred at 140 ° C for 4 h. The reaction mixture was filtered through silica gel, washed with acetonitrile and the residue was purified by column chromatography purification using preparative HPLC with a water / acetonitrile gradient as the running medium. logP (acidic): 3.18; MH + : 486; 1 H-NMR (400 MHz, D 6 -DMSO) d ppm: 9.07 (s, 1H), 8.17 (d, 1H), 7.89 (s, 1 H), 7.81-7.84 (m, 2H), 3.95 (s, 3H), 3.80 (q, 2H), 1.81-1.85 (m, 2H), 1.71-1.75 (m, 2H), 1.21 (t, 3H).
1- [3-Brom-2-(2,2-difluor-7-methyl- [1 ,3] dioxolo [4,5-f] benzimidazol-6-yl)pyrazolo [1 ,5-a] pyridin-6- yl] cyclopropancarbonitril 1- [3-bromo-2- (2,2-difluoro-7-methyl- [1,3] dioxolo [4,5-f] benzimidazol-6-yl) pyrazolo [1,5-a] pyridin-6 - yl] cyclopropanecarbonitrile
35,0 mg (0,02 mmol) l-[3-Brom-2-(2,2-difluoro-5H-[l,3]dioxolo[4,5-f]benzimidazol-6-yl)pyrazolo[l,5- a]pyridin-6-yl]cyclopropancarbonitril, 3,3 mg (0,02 mmol) Iodmethan und 5,7 mg (0,04 mmol) Kaliumcarbonat wurden in 5 ml Aceton 6 h bei Rückfluß gerührt. Das Lösungsmittel wurde abdestilliert, der Rückstand in Dichlormethan aufgenommen und mit einer gesättigten Natriumchlorid Lösung gewaschen. Die organische Phase wurde abgetrennt, über Natriumsulfat getrocknet und das organsiche Lösungsmittel im Vakuum abdestilliert. Der Rückstand wurde ohne weitere Reinigung in die nächste Stufe eingesetzt. 35.0 mg (0.02 mmol) l- [3-bromo-2- (2,2-difluoro-5H- [1,3] dioxolo [4,5-f] benzimidazol-6-yl) pyrazolo [l , 5- a] pyridin-6-yl] cyclopropanecarbonitrile, 3.3 mg (0.02 mmol) iodomethane and 5.7 mg (0.04 mmol) potassium carbonate were stirred in 5 ml acetone for 6 hours at reflux. The solvent was distilled off, the residue was taken up in dichloromethane and washed with a saturated sodium chloride solution. The organic phase was separated off, dried over sodium sulfate and the organic Distilled off solvent in vacuo. The residue was used in the next step without further purification.
1- [3-Brom-2-(2,2-difhioro-5H- [1 ,3] dioxolo [4,5-f] benzimidazol-6-yl)pyrazolo [1 ,5-a] pyridin-6- yl]cyclopropancarbonitril 1- [3-bromo-2- (2,2-difhioro-5H- [1,3] dioxolo [4,5-f] benzimidazol-6-yl) pyrazolo [1,5-a] pyridin-6-yl ] cyclopropanecarbonitrile
200 mg (1,06 mmol) 2,2-Difluor-l,3-benzodioxol-5,6-diamin und 384 mg (1,19 mmol) 3-Brom-6-(l- cyanocyclopropyl)pyrazolo[l,5-a]pyridin-2-carbonsäure wurden in Pyridin (25 mL) vorgelegt. 315 mg200 mg (1.06 mmol) of 2,2-difluoro-l, 3-benzodioxol-5,6-diamine and 384 mg (1.19 mmol) of 3-bromo-6- (l-cyanocyclopropyl) pyrazolo [1,5 -a] pyridine-2-carboxylic acid were placed in pyridine (25 mL). 315 mg
(1,59 mmol) EDCI wurden zugegeben und das Gemisch für 8 h bei l20°C gerührt. Das Lösungsmittel wurde abdestilliert, der Rückstand in Dichlormethan aufgenommen und mit einer gesättigten Natriumchlorid Lösung gewaschen. Die organische Phase wurde über Natriumsulfat getrocknet, das Lösungsmittel im Vakuum abdestilliert und der Rückstand über präparative HPLC mit einem Wasser / Acetonitril Gradienten als Laufimittel gereinigt. Das Produkt wurde ohne weitere Reinigung in die nächste Stufe eingesetzt. (1.59 mmol) EDCI were added and the mixture was stirred at 120 ° C. for 8 h. The solvent was distilled off, the residue was taken up in dichloromethane and washed with a saturated sodium chloride solution. The organic phase was dried over sodium sulfate, the solvent was distilled off in vacuo and the residue was purified by preparative HPLC using a water / acetonitrile gradient as the eluent. The product was used in the next step without further purification.
In Analogie zu Beispiel (1-3) und gemäß den oben beschriebenen Herstellverfahren läßt sich die folgende Verbindung der Formel (I) hersteilen: The following compound of the formula (I) can be prepared analogously to Example (1-3) and according to the preparation processes described above:
1- [3-Ethylsulfonyl-2- [2,2-difluor-7-methyl- [1,3] dioxolo-imidazo [4,5-b] pyridin-6-yl] pyrazolo [1,5- a]pyridin-6-yl] cyclopropancarbonitril (1-4) 1- [3-ethylsulfonyl-2- [2,2-difluoro-7-methyl- [1,3] dioxolo-imidazo [4,5-b] pyridin-6-yl] pyrazolo [1,5-a] pyridine -6-yl] cyclopropanecarbonitrile (1-4)
logP (sauer): 3,22; MH+: 487; ^-NMR^OO MHz, D6-DMSO) d ppm: 9.09 (s, 1H), 8.41 (s, 1H), 8,18 (d, 1 H), 7,84 (d, 1H), 3,95 (s, 3H), 3.81 (q, 2H), 1.81-1.85 (m, 2H), 1.71-1.75 (m, 2H), 1.22 (t, 3H). Anwendungsbeispiele logP (acidic): 3.22; MH + : 487; ^ -NMR ^ OO MHz, D 6 -DMSO) d ppm: 9.09 (s, 1H), 8.41 (s, 1H), 8.18 (d, 1H), 7.84 (d, 1H), 3, 95 (s, 3H), 3.81 (q, 2H), 1.81-1.85 (m, 2H), 1.71-1.75 (m, 2H), 1.22 (t, 3H). Examples of use
Boophilus microplus -Iniektionstest  Boophilus microplus initiation test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Lösungsmittel und verdünnt das Konzentrat mit Lösungsmittel auf die gewünschte Konzentration. To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.
Imΐ der Wirkstofflösung wird in das Abdomen von 5 vollgesogenen, adulten, weiblichen Rinderzecken (Boophilus microplus) injiziert. Die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. In the active ingredient solution, 5 fully soaked, adult female ticks (Boophilus microplus) are injected into the abdomen. The animals are transferred into trays and kept in an air-conditioned room.
Die Wirkungskontrolle erfolgt nach 7 Tagen auf Ablage fertiler Eier. Eier, deren Fertilität nicht äußerlich sichtbar ist, werden bis zum Larvenschlupf nach etwa 42 Tagen im Klimaschrank aufbewahrt. Eine Wirkung von 100 % bedeutet, dass keine der Zecken fertile Eier gelegt hat, 0% bedeutet, dass alle Eier fertil sind. The effects are checked after 7 days on the laying of fertile eggs. Eggs, whose fertility is not visible from the outside, are kept in the climate chamber until the larvae hatch after about 42 days. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 20pg/Tier: 1-4 Ctenocephalides felis - Oraltest In this test, e.g. the following compounds of the preparation examples have an effect of 80% at a rate of 20pg / animal: 1-4 Ctenocephalides felis - oral test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zwecks Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid. Durch Verdünnen mit titriertem Rinderblut erhält man die gewünschte To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. The desired one is obtained by dilution with titrated beef blood
Konzentration. Ca. 20 nüchterne adulte Katzenflöhe ( Ctenocephalides felis ) werden in eine Kammer eingesetzt, die oben und unten mit Gaze verschlossen ist. Auf die Kammer wird ein Metallzylinder gestellt, dessen Unterseite mit Parafilm verschlossen ist. Der Zylinder enthält die Blut-Wirkstoffzubereitung, die von den Flöhen durch die Parafilmmembran aufgenommen werden kann. Concentration. Approx. 20 fasting adult cat fleas (Ctenocephalides felis) are placed in a chamber which is closed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood drug preparation that the fleas can absorb through the parafilm membrane.
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Flöhe abgetötet wurden; 0 % bedeutet, dass keiner der Flöhe abgetötet wurde. After 2 days, the death rate is determined in%. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 100 ppm: 1- 1 , 1-4 Diabrotica balteata - Sprühtest In this test, for example, the following compounds of the preparation examples show an action of 100% at an application rate of 100 ppm: 1- 1, 1-4 Diabrotica balteata - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1 ,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether  Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
Vorgequollene Weizenkömer ( Triticum aestivum ) werden in einer mit Agar und etwas Wasser gefüllten Multiwell-Platte für einen Tag inkubiert (5 Saatkörner pro Kavität). Die gekeimten Weizenkömer werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Anschließend wird jede Kavität mit 10-20 Käferlarven von Diabrotica balteata infiziert. Pre-swollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and a little water (5 seeds per cavity). The germinated wheat grains are sprayed with an active ingredient preparation of the desired concentration. Then each cavity is infected with 10-20 beetle larvae from Diabrotica balteata.
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Weizenpflanzen wie in der unbehandelten, nicht infizierten Kontrolle gewachsen sind; 0 % bedeutet, dass keine Weizenpflanze gewachsen ist. After 7 days, the effect is determined in%. 100% means that all wheat plants have grown as in the untreated, uninfected control; 0% means that no wheat plant has grown.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 500g/ha (= 160pg/Kavität): 1-2, 1-3, 1-5. In this test, e.g. B. the following compounds of the preparation examples effect of 100% at a rate of 500g / ha (= 160pg / cavity): 1-2, 1-3, 1-5.
Spodoptera frugiperda - Sprühtest Spodoptera frugiperda - spray test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether  Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
Maisblattscheiben (Zea mays ) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms ( Spodoptera frugiperda ) besetzt.  Corn leaf disks (Zea mays) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are covered with caterpillars of the army worm (Spodoptera frugiperda).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: I- 1 , 1-2, 1-3, 1-4, 1-5. 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, e.g. B. the following compounds of the preparation examples effect of 100% at a rate of 100g / ha: I-1, 1-2, 1-3, 1-4, 1-5.
Phaedon cochleariae - Sprühtest Phaedon cochleariae - spray test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether  Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
Chinakohlblattscheiben (Brassica pekinensis ) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt.  Chinese cabbage leaf slices (Brassica pekinensis) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Käferlarven abgetötet wurden; 0 % bedeutet, dass keine Käferlarven abgetötet wurden. 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.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: 1-1, 1-4. In this test, e.g. B. the following compounds of the preparation examples effect of 100% at a rate of 100g / ha: 1-1, 1-4.
Myzus persicae - Oraltest Myzus persicae - oral test
Lösungsmittel: 100 Gewichtsteile Aceton Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser bis zum Erreichen der gewünschten Konzentration auf. Solvent: 100 parts by weight of acetone. To produce a suitable preparation of active compound, dissolve 1 part by weight of active compound with the specified parts by weight of solvent and make up to the desired concentration with water.
50 mΐ der Wirkstoffzubereitung werden in Mikrotiterplatten überführt und mit 150m1 50 mΐ of the active ingredient preparation are transferred to microtiter plates and with 150m1
IPL41 Insektenmedium (33% + 15% Zucker) auf eine Endvolumen von 200 mΐ aufgefüllt. Anschließend werden die Platten mit Parafilm verschlossen, durch den eine gemischte Population der GrünenIPL41 insect medium (33% + 15% sugar) to a final volume of 200 mΐ. Then the plates are sealed with parafilm, through which a mixed population of greens
Pfirsichblattlaus (Myzus persicae ), die sich in einer zweiten Mikrotiterplatte befindet, hindurchstechen und die Lösung aufiiehmen kann. Peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce through and absorb the solution.
Nach 5 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 4ppm: I- 1 , 1-2, 1-3, 1-4. After 5 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, e.g. B. the following compounds of the preparation examples effect of 100% at an application rate of 4ppm: I-1, 1-2, 1-3, 1-4.
Mvzus persicae - Sprühtest Mvzus persicae - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1 ,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether  Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weitererTo produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To make more
Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Test concentrations are diluted with water containing emulsifier.
Chinakohlblattscheiben ( Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus ( Myzus persicae ) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Nach 5 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.  Chinese cabbage leaf slices (Brassica pekinensis), which are affected by all stages of the green peach aphid (Myzus persicae), are sprayed with an active ingredient preparation of the desired concentration. After 5 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 100g/ha: 1-4. In this test, e.g. B. the following compounds of the preparation examples effect of 90% at a rate of 100g / ha: 1-4.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: 1-1. In this test, e.g. B. the following compounds of the preparation examples effect of 100% at a rate of 100g / ha: 1-1.
Vergleichsbeispiele Comparative examples
Mvzus persicae - Sprühtest fMYZUPEl  Mvzus persicae - spray test fMYZUPEl
Lösungsmittel: 14 Gewichtsteile Dimethylformamid Solvent: 14 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bei erforderlicher Zugabe von Ammoniumsalzen oder/und Penetrationsförderem werden diese jeweils in einer Konzentration von 1000 ppm der Präparatelösung zugefügt. To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and the mixture is filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier. If it is necessary to add Ammonium salts and / or penetration promoters are each added to the preparation solution in a concentration of 1000 ppm.
Paprikapflanzen ( Capsicum annuum), die stark von der Grünen Pfirsichblattlaus ( Myzus persicae ) befallen sind, werden durch Sprühen mit der Wirkstoffzubereitung in der gewünschten Konzentration behandelt.  Paprika plants (Capsicum annuum), which are heavily infested with the green peach aphid (Myzus persicae), are treated by spraying with the active ingredient preparation in the desired concentration.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Tiere abgetötet wurden; 0 % bedeutet, dass keine Tiere abgetötet wurden.  After the desired time, the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle  In this test, e.g. B. the following compounds of the preparation examples superior activity over the prior art: see table
Diabrotica balteata - Drenchtest fDIABBA) Diabrotica balteata - Drentest fDIABBA)
Lösungsmittel: 7 Gewichtsteile Dimethylformamid  Solvent: 7 parts by weight of dimethylformamide
Emulgator: 2 Gewichtsteile Alkylarylpolyglykolether  Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration, wobei das Erdvolumen in das gedrencht wird, mitberücksichtigt werden muss. Es ist darauf zu achten, dass in der Erde eine Konzentration von 40 ppm Emulgator nicht überschritten wird. Zur Herstellung weiterer Testkonzentrationen wird mit Wasser verdünnt.  To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, taking into account the volume of soil into which it is threshed. It is important to ensure that a concentration of 40 ppm emulsifier in the soil is not exceeded. To prepare further test concentrations, dilute with water.
Jeweils 5 Maiskörner werden in mit Erde gefüllte Töpfe ausgesät (Zea mays ) und am darauffolgenden Tag mit der Wirkstoffzubereitung der gewünschten Konzentration angegossen. Nach einem Tag werden ca. 25 L2-Larven des Maiswurzelbohrers ( Diabrotica balteata ) hinzugegeben.  In each case 5 corn kernels are sown in pots filled with soil (Zea mays) and poured on the following day with the preparation of active compound of the desired concentration. After a day, approximately 25 L2 larvae of the corn rootworm (Diabrotica balteata) are added.
Nach 8 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle 5 Pflanzen gekeimt und gewachsen sind; 0 % bedeutet, dass keine Pflanze aufgelaufen ist.  After 8 days, the effect is determined in%. 100% means that all 5 plants have germinated and grown; 0% means that no plants have emerged.
Bei diesem Test zeigt z. B. die folgende Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle  In this test, e.g. B. the following compounds of the preparation examples superior activity over the prior art: see table
*dat = days after treatment  * dat = days after treatment

Claims

Patentansprüche : Claims:
1. Verbindungen der Formel (I) 1. Compounds of formula (I)
in welcher in which
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2- C6)Alkinyl, (C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl, Halogen(C3-Cs)cycloalkyl, (C3-R 1 for (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 - C6) alkynyl, (C 2 -C 6 ) Haloalkynyl, (C 3 -Cs) cycloalkyl, halo (C 3 -Cs) cycloalkyl, (C 3 -
C6)Cycloalkyl-(Ci-C6)alkyl, (C3-C6)Cycloalkyl-(Ci-C6)halogenalkyl, (Ci-C6)Alkyl-(C3- Cs)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, (C3-C8)Cycloalkyl-(C3-Cs)cycloalkyl, Spiro-(C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C4-Ci2)Bicycloalkyl, (Ci-C6)Cyanoalkyl, (Ci- C6)Alkoxy-(Ci-C6)alkyl, (C2-C6)Cyanoalkenyl, (C3-C6)Cycloalkyl-(C2-C6)alkenyl, (C2-C6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6 ) cycloalkyl- (Ci-C 6 ) haloalkyl, (Ci-C6) alkyl- (C3- Cs) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) cycloalkyl, (C 3 -C 8 ) cycloalkyl- (C 3 -Cs) cycloalkyl, spiro- (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, (C 4 -Ci 2 ) bicycloalkyl, (Ci-C6) cyanoalkyl, (Ci-C6) alkoxy- (Ci-C6) alkyl, (C 2 -C 6 ) cyanoalkenyl, (C 3 -C 6 ) cycloalkyl- (C 2 -C 6 ) alkenyl, (C 2 -
C6)Cyanoalkinyl, (C3-C6)Cycloalkyl-(C2-C6)alkinyl, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (C2- C6)Alkenyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkenyloxy-(Ci-C6)alkyl, (C2-C6)Alkinyloxy-(Ci- C4)alkyl, (C2-C6)Halogenalkinyloxy-(Ci-C6)alkyl, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci-C6) cyanoalkynyl, (C 3 -C 6 ) cycloalkyl- (C 2 -C 6 ) alkynyl, (Ci-C6) haloalkoxy- (Ci-C6) alkyl, (C 2 - C6) alkenyloxy- (Ci-C6) alkyl , (C 2 -C 6 ) haloalkenyloxy- (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkynyloxy- (Ci-C 4 ) alkyl, (C 2 -C 6 ) haloalkynyloxy- (Ci-C 6 ) alkyl, (Ci-C6) alkylthio- (Ci-C6) alkyl, (Ci
C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkylthio-(Ci- Cö)alkyl, (Ci-C6)Halogenalkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkylsulfonyl-(Ci-C6)alkyl, oder Tri-(Ci-C6)alkylsilyl steht, C6) alkylsulfinyl- (Ci-C6) alkyl, (Ci-C6) alkylsulfonyl- (Ci-C6) alkyl, (Ci-C6) haloalkylthio- (Ci-C ö ) alkyl, (Ci-C6) haloalkylsulfinyl- (Ci C6) alkyl, (Ci-C6) haloalkylsulfonyl- (Ci-C6) alkyl, or tri- (Ci-C6) alkylsilyl,
R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci- Ce)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C6)Halogenalkylthio, (Ci-C6)Halogenalkylsulfinyl, (Ci- C6)Halogenalkylsulfonyl oder für (Ci-C6)Halogenalkyl-(C3-C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-C8)cycloalkyl, (Ci-R 2 , R 3 independently of one another for hydrogen, halogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (Ci-Ce) alkoxy, (Ci-C 6 ) haloalkoxy, (Ci-C 6 ) haloalkylthio , (Ci-C 6 ) haloalkylsulfinyl, (Ci-C 6 ) haloalkylsulfonyl or for (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -C 8 ) cycloalkyl, (Ci
C6)Halogenalkyl-(C3-C8)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-C8)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-Cö)Alkyl oder Halogen substituiertes Cyano(C3- C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes Spiro-(C3-C8)cycloalkyl-(C3-C8)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes (C4-Ci2)Bicycloalkyl stehen, wobei einer der Reste R2 oder R3 ausgewählt sein muss aus Ci-C6)Halogenalkyl-(C3- C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-C8)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-C 6 ) haloalkyl- (C 3 -C 8 ) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) halogenocycloalkyl, optionally singly or multiply substituted by (Ci-C ö ) alkyl or halogen cyano (C3- C6) cycloalkyl, spiro (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, optionally mono- or polysubstituted with cyano or halogen, or optionally mono- or polysubstituted with cyano or halogen (C 4 -Ci 2 ) bicycloalkyl stand, where one of the radicals R 2 or R 3 must be selected from Ci-C6) haloalkyl- (C3-C8) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -C8) cycloalkyl, (Ci-C6) haloalkyl - (C3-
C8)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-C8)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-C6)Alkyl oder Halogen substituiertem Cyano(C3-C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem Spiro-(C3- C8)cycloalkyl-(C3-Cs)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem (C4-Ci2)Bicycloalkyl, n für 0, 1 oder 2 steht, C8) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) halocycloalkyl, optionally simple or polysubstituted by (Ci-C 6) alkyl or halogen, cyano (C 3 -C 6) cycloalkyl, optionally mono- or polysubstituted with halogen or cyano spiro (C 3 - C 8) cycloalkyl- (C 3 -Cs) cycloalkyl or optionally mono- or polysubstituted (C 4 -Ci 2 ) bicycloalkyl, n is 0, 1 or 2, cyano or halogen,
Q für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 bis Q5 steht , Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1 to Q5,
wobei in which
R4 für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Hydroxyalkyl, (Ci-R 4 for (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci-C 4 ) hydroxyalkyl, (Ci
C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl,C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C alkyl 4), (C 2 -C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, ( C 2 -C 4 ) alkynyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl,
Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci-C4)Alkylcarbonyl-(Ci-C4)alkyl steht, Halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkylthio- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfinyl- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfonyl- (Ci-C 4 ) alkyl or (Ci-C 4 ) alkylcarbonyl- (Ci-C 4 ) alkyl,
R5 für (Ci-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (Ci-C6)Halogenalkyl, (C2-C6)Halogenalkenyl,R 5 for (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) haloalkenyl,
(C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl oder Halogen(C3-Cs)cycloalkyl steht, R6 für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-(C 2 -C 6 ) haloalkynyl, (C 3 -Cs) cycloalkyl or halogen (C 3 -Cs) cycloalkyl, R 6 represents hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) Haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -
C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3- C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkoxyimino, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci- C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci- C4)Halogenalkylsulfonyl, (Ci-C Alkylsulfonyloxy, (Ci-C4)Alkylcarbonyl, (Ci- C^Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl- aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci-C4)Alkylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl oder Di-(Ci-C4)alkylaminosulfonyl steht und C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 - C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C4) alkoxyimino, (Ci-C 4) alkylthio, ( Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci C 4 ) haloalkylsulfonyl, (Ci-C alkylsulfonyloxy, (Ci-C 4 ) alkylcarbonyl, (Ci-C ^ haloalkylcarbonyl, aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkylaminocarbonyl, (Ci -C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylamino, di- (Ci-C 4 ) alkylamino, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl or di- (Ci-C 4 ) alkylaminosulfonyl and
A für N (Stickstoff) oder C(H) steht. A stands for N (nitrogen) or C (H).
2. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher 2. Compounds of formula (I) according to claim 1, in which
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2- C6)Alkinyl, (C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl, Halogen(C3-Cs)cycloalkyl, (C3- C6)Cycloalkyl-(Ci-C6)alkyl, (C3-C6)Cycloalkyl-(Ci-C6)halogenalkyl, (Ci-C6)Alkyl-(C3- Cg)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, (Ci-C6)Cyanoalkyl, (Ci- C6)Hydroxyalkyl, (Ci-C6)Alkoxy-(Ci-Cö)alkyl, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (Ci- C6)Alkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfinyl-(Ci-C6)alkyl oder (Ci-C6)Alkylsulfonyl-(Ci- C6)alkyl steht, R 1 for (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 - C6) alkynyl, (C 2 -C 6 ) Haloalkynyl, (C 3 -Cs) cycloalkyl, halogen (C 3 -Cs) cycloalkyl, (C 3 - C6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6 ) cycloalkyl- (Ci-C 6 ) haloalkyl , (Ci-C 6 ) alkyl- (C 3 - Cg) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) cycloalkyl, (Ci-C6) cyanoalkyl, (Ci-C6) hydroxyalkyl, (Ci C6) alkoxy- (Ci-C ö ) alkyl, (Ci-C6) haloalkoxy- (Ci-C6) alkyl, (Ci- C6) alkylthio- (Ci-C6) alkyl, (Ci-C6) alkylsulfinyl- (Ci C6) alkyl or (Ci-C6) alkylsulfonyl- (Ci-C6) alkyl,
R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci- Ce)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C6)Halogenalkylthio, (Ci-C6)Halogenalkylsulfinyl, (Ci- C6)Halogenalkylsulfonyl oder für (Ci-C6)Halogenalkyl-(C3-C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-Cs)cycloalkyl, (Ci- C6)Halogenalkyl-(C3-C8)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-C4)Alkyl oder Halogen substituiertes Cyano(C3- C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes Spiro-(C3-Cs)cycloalkyl-(C3-C8)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertes (C4-Ci2)Bicycloalkyl stehen, wobei einer der Reste R2 oder R3 ausgewählt sein muss aus (Ci-C6)Halogenalkyl-(C3- C8)cycloalkyl, (Ci-C6)Cyanoalkyl-(C3-C8)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-R 2 , R 3 independently of one another for hydrogen, halogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-Ce) alkoxy, (Ci-C6) haloalkoxy, (Ci-C6) haloalkylthio, (Ci C6) haloalkylsulfinyl, (Ci-C6) haloalkylsulfonyl or for (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -Cs) cycloalkyl, (Ci-C 6 ) Haloalkyl- (C 3 -C 8 ) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) halocycloalkyl, optionally singly or multiply substituted by (Ci-C 4 ) alkyl or halogen cyano (C 3 - C 6 ) cycloalkyl optionally monosubstituted or polysubstituted by cyano or halogen spiro, (C 3 -Cs) cycloalkyl (C 3 -C 8) cycloalkyl or optionally mono- or multiply-substituted by cyano or halogen (C 4 -C stand 2) bicycloalkyl, where one of the radicals R 2 or R 3 must be selected from (Ci-C6) haloalkyl- (C3- C8) cycloalkyl, (Ci-C 6 ) cyanoalkyl- (C 3 -C8) cycloalkyl, (Ci-C6) haloalkyl- (C3-
C8)cyanocycloalkyl, (Ci-C6)Halogenalkyl-(C3-C8)halogencycloalkyl, gegebenfalls einfach oder mehrfach durch (Ci-C4)Alkyl oder Halogen substituiertem Cyano(C3-C6)cycloalkyl, gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem Spiro-(C3- C8)cycloalkyl-(C3-C8)cycloalkyl oder gegebenenfalls einfach oder mehrfach mit Cyano oder Halogen substituiertem (C4-Ci2)Bicycloalkyl, n für 0, 1 oder 2 steht, Q für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 bis Q5 steht, C8) cyanocycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -C 8 ) halogenocycloalkyl, optionally singly or multiply by (Ci-C 4 ) alkyl or halogen-substituted cyano (C 3 -C 6 ) cycloalkyl, optionally singly or multiply with cyano or halogen substituted spiro- (C3-C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl or optionally singly or multiply with cyano or halogen substituted (C 4 -Ci 2 ) bicycloalkyl, n is 0, 1 or 2 , Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1 to Q5,
wobei in which
R4 für (Ci-C4)Alkyl, (Ci-C Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Hydroxyalkyl, (Ci- C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci-C4)Alkylcarbonyl-(Ci-C4)alkyl steht, R 4 is (Ci-C 4) alkyl, (Ci-C haloalkyl, (Ci-C 4) cyanoalkyl, (Ci-C 4) hydroxyalkyl, (Ci C 4) alkoxy (Ci-C alkyl 4), ( Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 -C 4 ) haloalkenyloxy- (Ci-C 4) alkyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (Ci-C 4) alkyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl- (C 3 - C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkylthio- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfinyl- (Ci-C 4 ) alkyl, (Ci C 4 ) alkylsulfonyl- (Ci-C 4 ) alkyl or (Ci-C 4 ) alkylcarbonyl- (Ci-C 4 ) alkyl,
R5 für (Ci-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (Ci-C6)Halogenalkyl, (C2- C6)Halogenalkenyl, (C2-C6)Halogenalkinyl, (C3-Cs)Cycloalkyl oder Halogen(C3-Cs)cycloalkyl steht, R 5 is for (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C 6 ) haloalkyl, (C 2 - C6) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (C 3 -Cs) cycloalkyl or halogen (C 3 -Cs) cycloalkyl,
R6 für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2- C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3- C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkoxyimino, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci- C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-R 6 for hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4 ) Alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 - C 6 ) cycloalkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl- (C 3 - C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C4) alkoxyimino, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci- C4 ) Alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci
C4)Halogenalkylsulfonyl, (Ci-C4)Alkylsulfonyloxy, (Ci-C4)Alkylcarbonyl, (Ci- C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl- aminocarbonyl, (Ci-C4)Alkylsulfonylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl oder Di-(Ci-C4)alkylaminosulfonyl steht und A für N (Stickstoff) oder C(H) steht. C 4 ) haloalkylsulfonyl, (Ci-C 4 ) alkylsulfonyloxy, (Ci-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkylaminocarbonyl , (Ci-C 4 ) alkylsulfonylamino, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl or di- (Ci-C 4 ) alkylaminosulfonyl and A stands for N (nitrogen) or C (H).
3. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher 3. Compounds of formula (I) according to claim 1, in which
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl oder (C3-Cs)Cycloalkyl steht, R2 für Wasserstoff, Halogen, (Ci-C Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy, (Ci-C4)Halogenalkylthio, (Ci-C4)Halogenalkylsulfinyl oder (Ci- C4)Halogenalkylsulfonyl steht, R 1 represents (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C3-Cs) cycloalkyl, R 2 represents hydrogen, halogen, (Ci-C alkyl, (Ci-C4) haloalkyl, (Ci C4) alkoxy, (Ci-C4) haloalkoxy, (Ci-C4) haloalkylthio, (Ci-C4) haloalkylsulfinyl or (Ci-C4) haloalkylsulfonyl,
R3 für (Ci-C4)Halogenalkyl-(C3-C8)cycloalkyl, Spiro-(C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C4-R 3 for (Ci-C 4 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, spiro- (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, (C 4 -
Ci2)Bicycloalkyl oder gegebenfalls einfach oder zweifach durch (Ci-C4)Alkyl oder Halogen substituiertes Cyano(C3-C6)cycloalkyl steht, n für 0, 1 oder 2 steht, Ci 2 ) bicycloalkyl or optionally single or double cyano (C 3 -C 6 ) cycloalkyl substituted by (Ci-C 4 ) alkyl or halogen, n stands for 0, 1 or 2,
Q für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 bis Q5 steht, Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1 to Q5,
wobei in which
R4 für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci- C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2-C4)Alkenyloxy-(Ci-C4)alkyl, (C2- C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl oder (C3-C6)Cycloalkyl steht, für (Ci-C6)Halogenalkyl, (C2-C6)Halogenalkenyl, (C2-C6)Halogenalkinyl oder Halogen(C3- Cs)cycloalkyl steht, R6 für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3-C6)Cycloalkyl, (Ci- C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci- C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl oder (Ci- C4)Halogenalkylsulfonyl steht und A für N (Stickstoff) oder C(H) steht. R 4 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci C 4) -haloalkoxy - (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkenyloxy- (Ci-C 4 ) alkyl, (C 2 - C 4 ) alkynyl, (C 2 -C 4 ) Alkynyloxy- (Ci-C 4 ) alkyl or (C 3 -C 6 ) cycloalkyl represents (Ci-C6) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl or halogen (C 3 - Cs) cycloalkyl, R 6 for hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl or (Ci-C 4 ) haloalkylsulfonyl and A represents N (nitrogen) or C (H).
4. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher 4. Compounds of formula (I) according to claim 1, in which
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl oder (C3-Cs)Cycloalkyl steht, R 1 represents (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl or (C 3 -Cs) cycloalkyl,
R2 für Wasserstoff, (Ci-C4)Alkyl oder Halogen steht, R3 für (Ci-C4)Halogenalkyl-(C3-Cs)cycloalkyl, Spiro-(C3-C8)cycloalkyl-(C3-Cs)cycloalkyl oderR 2 represents hydrogen, (Ci-C 4 ) alkyl or halogen, R 3 represents (Ci-C 4 ) haloalkyl- (C 3 -Cs) cycloalkyl, spiro- (C 3 -C 8 ) cycloalkyl- (C 3 - Cs) cycloalkyl or
Cyano(C3-C6)cycloalkyl steht, n für 0, 1 oder 2 steht, Cyano (C 3 -C 6 ) cycloalkyl, n stands for 0, 1 or 2,
Q für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql, Q2, Q3 und Q5 steht, Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2, Q3 and Q5,
wobei in which
R4 für (Ci-CQAlkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl steht, R 4 represents (Ci-CQalkyl or (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl,
R5 für (Ci-C6)Halogenalkyl steht, R 5 represents (Ci-C6) haloalkyl,
R6 für Wasserstoff, Methyl, Ethyl, Methoxy, Cyano, Halogen oder (Ci-C2)Halogenalkyl steht und A für N (Stickstoff) oder C(H) steht. R 6 represents hydrogen, methyl, ethyl, methoxy, cyano, halogen or (Ci-C 2 ) haloalkyl and A stands for N (nitrogen) or C (H).
5. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher 5. Compounds of formula (I) according to claim 1, in which
R1 für (Ci-C4)Alkyl steht, R2 für Wasserstoff steht, R3 für Cyanocyclopropyl oder Cyanocylcobutyl steht, n für 2 steht, R 1 stands for (Ci-C4) alkyl, R 2 stands for hydrogen, R 3 stands for cyanocyclopropyl or cyanocylcobutyl, n stands for 2,
Q für ein heteroaromatisches 9-gliedriges oder l2-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 , Q2 und Q5 steht, Q stands for a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5,
wobei in which
R4 für (Ci-C Alkyl steht, R5 für (Ci-C Flalogenalkyl steht, R 4 stands for (Ci-C alkyl, R 5 stands for (Ci-C flalogenalkyl,
R6 für Wasserstoff steht und R 6 represents hydrogen and
A für N (Stickstoff) oder C(H) steht. A stands for N (nitrogen) or C (H).
6. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher 6. Compounds of formula (I) according to claim 1, in which
R1 für Ethyl steht, R 1 represents ethyl,
R2 für Wasserstoff steht, R 2 represents hydrogen,
R3 für 1 -Cyanocyclopropyl steht, n für 2 steht, R 3 represents 1-cyanocyclopropyl, n stands for 2,
Q für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Q 1 , Q2 und Q5 steht, Q represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q 1, Q2 and Q5,
wobei in which
R4 für Methyl steht, R 4 represents methyl,
R5 für Trifluormethyl oder Pentafluorethyl steht, R6 für Wasserstoff steht und R 5 represents trifluoromethyl or pentafluoroethyl, R 6 represents hydrogen and
A für N (Stickstoff) oder C(H) steht. A stands for N (nitrogen) or C (H).
7. Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass wenigstens einer der Reste R2 oder R3 für Cyano(C3-C6)cycloalkyl steht und der jeweils andere Rest ausgewählt ist aus Wasserstoff, (Ci-C4)Alkyl oder Halogen. 7. Compounds of formula (I) according to any one of claims 1 to 6, characterized in that at least one of the radicals R 2 or R 3 is cyano (C3-C6) cycloalkyl and the other radical is selected from hydrogen, (Ci -C4) alkyl or halogen.
8. Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass R3 für Cyano(C3-C6)cycloalkyl steht. 8. Compounds of formula (I) according to any one of claims 1 to 6, characterized in that R 3 is cyano (C3-C6) cycloalkyl.
9. Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass9. Compounds of formula (I) according to any one of claims 1 to 8, characterized in that
R5 für (Ci-C6)Halogenalkyl, (C2-C6)Halogenalkenyl, (C2-C6)Halogenalkinyl oder Halogen(C3- Cx)cycloalkyl steht. R 5 represents (Ci-C 6 ) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl or halogen (C3-Cx) cycloalkyl.
10. Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass R5 für (Ci-C6)Halogenalkyl steht. 10. Compounds of formula (I) according to any one of claims 1 to 8, characterized in that R 5 represents (Ci-C 6 ) haloalkyl.
1 1. Verbindungen der Formel (G) gemäß Anspruch 1 , 1 1. Compounds of formula (G) according to claim 1,
CO, wobei Q, R4, R5 und R6 die in Bedeutungen gemäß einem der Ansprüche 3 bis 6 haben. CO, where Q, R 4 , R 5 and R 6 have the meanings according to any one of claims 3 to 6.
12. Agrochemische Formulierung enthaltend Verbindungen der Formel (1) gemäß einem der Ansprüche 1 bis 1 1, sowie Streckmittel und/oder oberflächenaktive Substanzen. 12. Agrochemical formulation containing compounds of formula (1) according to any one of claims 1 to 1 1, and extenders and / or surface-active substances.
13. Agrochemische Formulierung gemäß Anspruch 12 zusätzlich enthaltend einen weiteren agrochemischen Wirkstoff. 13. Agrochemical formulation according to claim 12 additionally containing a further agrochemical active ingredient.
14. Verfahren zur Bekämpfung von tierischen Schädlingen dadurch gekennzeichnet, dass man eine Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 1 1 oder eine agrochemische Formulierung gemäß einem der Ansprüche 12 oder 13 auf die tierischen Schädlinge und/oder ihren Lebensraum einwirken lässt. 14. A method for controlling animal pests, characterized in that a compound of the formula (I) according to one of claims 1 to 11 or an agrochemical formulation according to one of claims 12 or 13 is allowed to act on the animal pests and / or their habitat .
15. Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 1 1 oder von agrochemischen Formulierungen gemäß einem der Ansprüche 12 oder 13 zur Bekämpfung von tierischen Schädlingen. 15. Use of compounds of formula (I) according to one of claims 1 to 1 1 or of agrochemical formulations according to one of claims 12 or 13 for controlling animal pests.
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