EP2493844A2 - Halogenalkyl-substituierte amide als insektizide und akarizide - Google Patents

Halogenalkyl-substituierte amide als insektizide und akarizide

Info

Publication number
EP2493844A2
EP2493844A2 EP10768415A EP10768415A EP2493844A2 EP 2493844 A2 EP2493844 A2 EP 2493844A2 EP 10768415 A EP10768415 A EP 10768415A EP 10768415 A EP10768415 A EP 10768415A EP 2493844 A2 EP2493844 A2 EP 2493844A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
substituents
cyano
halogen
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Withdrawn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
EP10768415A
Other languages
German (de)
English (en)
French (fr)
Inventor
Markus Heil
Eike Kevin Heilmann
Alexander Sudau
Tobias Kapferer
Friedrich August MÜHLTHAU
Peter Jeschke
Arnd Voerste
Ulrich Görgens
Klaus Raming
Ulrich Ebbinghaus-Kintscher
Mark Drewes
Martin Adamczewski
Angela Becker
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 Intellectual Property GmbH
Original Assignee
Bayer CropScience AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP10768415A priority Critical patent/EP2493844A2/de
Publication of EP2493844A2 publication Critical patent/EP2493844A2/de
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
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    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
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    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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    • 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
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    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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Definitions

  • the present invention relates to novel pesticides, a process for their preparation and their use as active ingredients, in particular their use as insecticides and acaricides.
  • Certain cinnamic acid amides and their use as pharmaceuticals are described in the literature, see for example WO-A-2002/096858. It has now surprisingly been found that certain, in particular haloalkyl-substituted amides have strong insecticidal and acaricidal properties with good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility. However, the new compounds according to the invention are not disclosed in WO-A-2002/096858.
  • the present invention therefore relates to compounds of the general formula (I)
  • R is hydrogen, halogen, nitro, cyano, optionally substituted once or more than once, identically or differently, Q-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, CC 6 -alkoxy, C 1 -C -alkylthio, Ci-C 6 alkylsulfinyl, CC 6 alkylsulfonyl, C 3 -C 6 cycloalkyl, dC 6 - alkylcarbonyl, Ci-C 6 alkoxyimino-Ci-C6 alkyl, Ci-C 6 alkoxycarbonyl, Ci-C 6 alkoxycarbonyl, Ci-C 6 - alkylaminocarbonyl, Q-Ce-alkylaminocarbonyl, Ci-C 6 alkylaminosulfonyl, CC 6 - alkylsulfonylamino, tri (CC 6 alkyl) sily
  • substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C r C 6 alkyl, CC 6 alkoxy, C3-C 6 cycloalkyl, C r C 6 - haloalkoxy, Ci-Ce- Alkylthio, amino, C r C 6 alkylamino, Ci-C ö dial
  • R 4 is hydrogen, halogen or optionally mono- or polysubstituted by identical or different substituents, CC 6 alkyl, where the substituents are independently selected from halogen, QC ö alkyl or QC ö alkoxy,
  • R 8 represents hydrogen, cyano, hydroxy, optionally mono- or polysubstituted by identical or different substituents, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, CC 6 -alkoxy, QQ-alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, C 1 -C 6 -alkoxycarbonyl, arylalkyl or C 1 -C 4 -alkylsulphonyl, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, C 1 -C 6 - alkyl or Ci-C 6 alkoxy, Ci-C 4 alkoxycarbonyl, amino, Ci-C 6 - alkylamino, Ci-C 6 dialkylamino, aminocarbonyl, C r C 6 alkylaminocarbonyl, Ci-C 6 - alky
  • R 9 and R 10 are independently hydrogen, halogen, optionally mono- or polysubstituted by identical or different substituents, Ci-C ö alkyl or C3-C6-cycloalkyl, where the substituents are independently selected from halogen or C 6 - alkyl,
  • R 5 is hydrogen, halogen or optionally mono- or polysubstituted by identical or different substituents C r C 6 alkyl or Ci-C 6 alkoxy, wherein the substituents are independently selected from halogen, or C r Ce-alkyl
  • R 6 is hydrogen, halogen, nitro, cyano, amino, hydroxy, optionally mono- or polysubstituted by identical or different substituents
  • R 6 represents an optionally 1-2 heteroatoms from the series N, S, 0-containing CC 4 - carbon chain group which is attached to two adjacent ring positions Q 4 bound to Q 8 to form an aliphatic, aromatic or heteroaromatic ring which is optionally mono- or is substituted several times by CpCe-alkyl or halogen, where m is then equal to 2, m is 0, 1, 2, 3
  • X is C 1 -C 6 -haloalkyl or C 3 -C 6 -halocycloalkyl, which may optionally additionally be monosubstituted to trisubstituted, where the substituents are selected independently of one another from hydroxy, cyano, C 1 -C 4 -alkoxy, C r C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylaminocarbonyl or C 1 -C 4 -dialkylaminocarbonyl,
  • W stands for O or S
  • AY is in common cyano, or optionally mono- or polysubstituted hetaryl, heterocyclyl or oxoheterocyclyl, where the substituents are selected from halogen, nitro, cyano, amino, hydroxy, optionally monosubstituted or polysubstituted by identical or different substituents, C r C 6 alkyl, Ci-Qj-alkoxy, C, -C 6 alkoxy-C 6 alkyl, C, -C 6 alkylcarbonyl, C 2 -C 6 - alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, aryl, hetaryl, C r C 6 arylalkyl, C r C 6 - hetarylalkyl, aryloxy, hetaryloxy, sulfonyl, Ci-C6 alkylthio, Cj-C ö -Alky
  • R 11 and R 12 together are C 2 -C 5 -alkyl or C 3 -Cs-alkenyl, forming a 3-6 membered ring which may optionally contain 1 to 2 double bonds, or R 11 and R 13 , together represents C 2 -C 5 -alkyl or C 3 -C 5 -alkenyl, forming a 3-7 membered ring which may optionally contain 1 to 2 double bonds, and wherein
  • R 13 and R 14 are independently hydrogen, optionally mono- or polysubstituted by identical or different substituents, Ci-C6 alkyl or C 3 -C 6 cycloalkyl, C r C 6 - alkylcarbonyl, alkoxycarbonyl or aryloxycarbonyl CC are 6, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, Ci-C 6 alkyl or Ci-C ö alkoxy, or
  • R 13 and R 14 together represent C 2 -C 5 -alkyl or C 3 -C 5 -alkenyl, forming a 3-7 membered ring which may optionally contain 1 to 2 double bonds,
  • Y is hydrogen, mono- or polysubstituted by identical or different optionally substituted C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkenyl, aryl, hetaryl, heterocyclyl or oxoheterocyclyl, where the substituents are selected from halogen, nitro, cyano, hydroxy, from optionally mono- or polysubstituted by identical or different substituents, amino,
  • Q 1 to Q 3 independently of one another represent a carbon atom which is substituted by hydrogen or by R 1 , or stand for N, where the number of N atoms in Q 1 to Q 3 is a maximum of 2,
  • Q 4 represents a carbon atom which is substituted by hydrogen or R 6 or which is bonded to V, where then V does not equal R 4 , or is N,
  • Q 5 to Q 8 independently of one another represent a carbon atom which is substituted by hydrogen, R 6 or AY, or represents N, where the number of N atoms in Q 4 to Q 8 is a maximum of 2, where exactly one of Q 5 , Q 6 , Q 7 , Q 8 is substituted by AY, as well as salts and N-oxides of compounds of the formula (I) and their use for controlling animal pests
  • the compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
  • the compounds of formula (I) include optionally present diastereomers or enantiomers as well as E / Z isomers.
  • the substituted acrylamides are generally defined by the formula (I).
  • Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
  • Preferred, particularly preferred and very particularly preferred are compounds of the formula (I), as well as a process for combating pests using the compounds of the formula (I), where
  • R 1 is preferably hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted, identically or differently substituted C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C -alkynyl, C 1 -C 4 -alkoxy , Ci-C 4 alkylthio, C, -C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C 3 -C 4 - cycloalkyl, Ci-C4-alkylcarbonyl, CC 4 alkoxycarbonyl, Ci-C 4 alkylaminocarbonyl, Cp C4 dialkylaminocarbonyl or C is 4 alkylaminosulfonyl, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, Ci-C alkyl, Ci-C 4 alkoxy, C 3 -C 4 cycloal
  • R 2 preferably represents hydrogen, cyano, hydroxy, amino, or three times by identical or different optionally mono- substituted Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkynyl, Ci-C 4 - Alkoxy or C 3 -C 6 -cycloalkyl, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C 1 -C 4 -alkyl or CC 4 -alkoxy,
  • R 3 is preferably hydrogen, optionally mono- or polysubstituted by identical or different substituents C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C -cycloalkyl, aryl-C C 4 alkyl, Ci-C alkylcarbonyl, C r C 4 alkylsulfonyl, arylcarbonyl, hetarylcarbonyl, CC 4 alkoxycarbonyl or aryloxycarbonyl group, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, CC 6 alkyl, C r C 6 alkoxy, C 3 -C 6 cycloalkyl, CC 6 haloalkoxy, Ci-C alkylthio, C] -C 4 alkoxycarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl or C
  • Attachment point on the ring at one of the positions Q 4 to Q 8 and the respectively second-mentioned (right) attachment site to Y preferably wherein the values 0, 1 or 2 can assume, and being preferably an optionally substituted C 2 -C 4 alkyl which together with a carbon atom of positions Q 4 to Q 8 adjacent to the point of attachment of A forms a 5-6 membered ring, the substituents being independently selected from halogen, C 1 -C 3 -alkyl and C 1 -C 3 -alkyl. Alkoxy, and where
  • R 11 and R 12 independently of one another preferably represent hydrogen, cyano or optionally mono- to trisubstituted by identical or different substituents Ci-d-alkyl or C3-C6-cycloalkyl, wherein the substituents are independently selected from halogen, cyano, nitro , Hydroxy, CC 6 alkyl or C r C 6 alkoxy or
  • R 11 and R 12 together are C 2 -C 5 -alkyl or C 3 -C 5 -alkenyl, forming a 3-6 membered ring which may optionally contain 1 to 2 double bonds, or
  • R 11 and R 13 together are C 2 -C 5 -alkyl or C 3 -C 5 -alkenyl, forming a 3-7 membered ring which may optionally contain 1 to 2 double bonds, and wherein
  • R 13 and R 14 are each independently preferably hydrogen, optionally mono- or polysubstituted by identical or different substituents CC 4 alkyl or C3-C6-cycloalkyl, Q-C4 alkylcarbonyl, Ci-C 4 alkoxycarbonyl or aryloxycarbonyl, stand, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, Ci-C 4 alkyl or Ci-C alkoxy, or
  • R 13 and R 14 together represent C 2 -C 5 -alkyl or C 3 -C 5 -alkenyl, forming a 3-7 membered ring which may optionally contain 1 to 2 double bonds,
  • Y preferably represents hydrogen or optionally mono- or polysubstituted by identical or different substituents Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 -cycloalkyl, C3-C6 -Cycloalkenyl, an optionally mono- or polysubstituted, identically or differently substituted phenyl or an optionally mono- or polysubstituted heterocycle of the series thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,2,3 Triazolyl, 1, 2,4-triazolyl, 1,2,3-oxadiazolyl,
  • Q 1 to Q 3 independently of one another, preferably represent a carbon atom which is substituted by hydrogen or by R 1 , or is N, where the number of N atoms in Q 1 to Q 3 is a maximum of 2,
  • Q 4 preferably represents a carbon atom which is substituted by hydrogen or R 6 or which is bonded to V, where V is then not equal to R 4 , or is N,
  • Q 5 to Q 8 independently of one another preferably represent a carbon atom which is substituted by hydrogen, R 6 or AY, or represents N, where the number of N atoms in Q 4 to Q 8 is a maximum of 2, with exactly one out Q 5 , Q 6 , Q 7 , Q 8 is substituted by AY,
  • R 1 particularly preferably represents hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl which is optionally monosubstituted or polysubstituted by identical or different substituents, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, Ci-C 4 alkylsulfonyl, C, -C 4 alkylcarbonyl, CC 4 - alkoxycarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-dialkylaminocarbonyl or C 4 - alkylaminosulfonyl, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, C r C alkyl, C alkoxy, C 3 -C 4 cycloalkyl, Ci-C -haloalkoxy or C, -C 4 alkylthio,
  • R 3 is particularly preferably hydrogen, optionally mono- or polysubstituted by identical or different substituents QC 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, CC - alkylcarbonyl, Ci-C 4 alkylsulfonyl, C r C 4 alkoxycarbonyl or aryloxycarbonyl group, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, C] -C6 alkyl, CC 6 alkoxy or C r C alkoxycarbonyl,
  • V is particularly preferably R 4 , or is a bivalent chemical moiety which is selected from -O-, S, and -N (R 8 ) - and which is connected via a single bond with Q 4 , wherein
  • R 4 is particularly preferably hydrogen or optionally monosubstituted to trisubstituted by identical or different substituents, C r C 4 alkyl, where the substituents are independently selected from halogen, Ci-C alkyl or CC 4 alkoxy,
  • R 8 particularly preferably represents hydrogen, cyano, hydroxy, optionally mono- or polysubstituted by identical or different substituents, C] -C4 alkyl, C2-C 4 alkenyl, C 3 -C 4 - alkynyl, aryl-Ci-C - alkyl, Ci-C 4 alkoxy, CC 6 alkoxycarbonyl or C r C 4 - alkylcarbonyl, where the substituents are independently selected from halo, cyano, nitro, hydroxy, CC 6 alkyl, Ci-C 6 alkoxy, C 1 -C 4 alkoxycarbonyl, aminocarbonyl, C 1 -C 4 alkylaminocarbonyl, CC 4 -dialkylaminocarbonyl or arylCCC 4 -alkoxy
  • R 5 particularly preferably represents hydrogen, or represents optionally mono- to trisubstituted by identical or different substituents Q-Gi-alkyl, wherein the substituents are independently selected from halogen, C r C alkyl or C r C 4 alkoxy,
  • R 6 particularly preferably represents hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted by identical or different substituents C 4 -alkyl, C 2 -C 4 -alkynyl, C 4 -alkoxy, (C 4 -alkyl) -carbonyl, ( Ci-C4 alkylamino) carbonyl, (CC 4 dialkylamino) carbonyl, QC 4 - alkylthio, Ci-C4-alkylsulfinyl, Ci-C alkylsulfonyl, CC 4 alkylaminosulfonyl or QC 4 - alkylsulfonylamino, wherein the substituents are independently selected from halogen, cyano, nitro, C, -C 6 -alkyl, Ci-C 6 alkoxy, CC 6 haloalkoxy and C r C 6 alkylthio, or particularly preferably -OCH 2 0-
  • U is particularly preferably an optionally substituted C 2 -C 4 -alkyl which, together with a carbon atom of positions Q 4 to Q 8 adjacent to the point of attachment of A to the ring, forms a 5-6 membered ring, the substituents being selected independently of one another from C 1 -C 3 -alkyl and halogen, and wherein
  • R u and R 12 independently of one another particularly preferably represent hydrogen, represent Ci-C 4 alkyl or are C r C 4 haloalkyl, or
  • R 11 and R 12 together are C 2 -C 5 -alkyl or C 3 -C 5 -alkenyl, forming a 3-6 membered ring which may optionally contain 1 to 2 double bonds, or
  • R 11 and R 13 together are C 2 -C 5 alkyl or C 3 -C 5 alkenyl, forming a 3-7 membered ring which may optionally contain from 1 to 2 double bonds, and wherein R 13 and R 14 independently of one another particularly preferably represent hydrogen, represent optionally mono- or polysubstituted by identical or different substituents, Ci-C 4 alkyl or C3-C6 cycloalkyl, Ci-C4-alkylcarbonyl, aryloxycarbonyl, or C r C 4 -alkoxycarbonyl, wherein the substituents are independently selected from halo, cyano, Ci- C 4 alkyl or C r C 4 alkoxy, or
  • R 13 and R together are C 2 -C 5 -alkyl or C 3 -C 5 -alkenyl, forming a 3-7 membered ring which may optionally contain 1 to 2 double bonds,
  • Y particularly preferably represents hydrogen or represents optionally mono- or polysubstituted by identical or different substituents CrQ-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -
  • Alkylthio CC 6 alkylsulfinyl, C r C 6 alkylsulfonyl, (C 1 -C 6 alkoxy) carbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C] -C 6 alkylamino, C 3 -C 6 cycloalkylamino, (C r C 6 alkyl) C 3 -C 6 - cycloalkylamino, di (CC 4) alkylamino or C 6 alkylaminocarbonyl,
  • Q 1 to Q 3 independently of one another particularly preferably represent a carbon atom which is substituted by hydrogen or by R 1 , or is N, where the number of N
  • Q 4 particularly preferably represents a carbon atom which is substituted by hydrogen or R 6 or which is bonded to V, where V is then not equal to R 4 , or is N,
  • Q 5 to Q 8 independently of one another are particularly preferably a carbon atom which is substituted by hydrogen, R 6 or AY, or N, where the number of N atoms in Q 4 to Q 8 is at most 1, exactly one from Q 5 , Q 6 , Q 7 , Q 8 is substituted by AY,
  • R 1 very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, fluoromethyl, chloromethyl, trichloromethyl, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl , Dichloroethyl, trifluoroethyl, chlorofluoroethyl, chlorodifluoroethyl, dichlorofluoroethyl, tetrafluoroethyl, pentafluoroethyl, chlorotetrafluoroethyl, trichloroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, methoxy, ethoxy, n
  • n most preferably represents 1, 2 or 3 stands
  • R 2 very particularly preferably represents hydrogen, methyl or ethyl
  • R 3 very particularly preferably represents hydrogen, methyl, ethyl, 2-ethynyl, 2-propenyl, methoxymethyl, ethoxymethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, t-butoxycarbonyl or phenoxycarbonyl .
  • V is very particularly preferably R 4 , or is -O- or -N (R 8 ) -, and is connected via a single bond with Q 4 , wherein
  • R 4 very particularly preferably represents hydrogen or methyl
  • R 8 very particularly preferably represents hydrogen, methyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoeth-2-yl, propyl, phenylmethyl, prop-2-en-1-yl, prop-2-yn-1-one yl, benzyloxy, methoxycarbonyl, ethoxycarbonyl, Methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonyleth-2-yl,
  • R very particularly preferably represents hydrogen
  • R 6 very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethynyl, propynyl, fluoromethyl, Chloromethyl, trichloromethyl, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, trifluoroethyl, chlorofluoroethyl, chlorodifluoroethyl, fluorodichloroethyl, tetrafluoroethyl, pentafluoroethyl, chlorotetrafluoroethyl, trichloroethyl, hepta
  • X is very particularly preferred for trifluoromethyl, difluoromethyl, fluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1, 2 , 2,2-tetrafluoroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl or nonafluoro-n-butyl,
  • W is very particularly preferably O
  • AY together very particularly preferably cyano or optionally mono- or polysubstituted heterocyclyl of the series l, 2,4-oxadiazol-3-yl, lH-imidazol-1-yl, lH-pyrazol-1-yl, lH-l, 2nd , 4-triazol-1-yl, 1H-l, 2,3-triazol-1-yl, 1H-l, 3,4-triazol-1-yl, 1H-1,2,3,4-tetrazole-1 -yl or 2H-l, 2,3,4-tetrazol-1-yl, wherein the substituents are selected from fluoro, chloro, cyano, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, n- or i Propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, fluorometh
  • U very particularly preferably represents ethyl or n-propyl which, together with a carbon atom of positions Q 4 to Q 8 adjacent to the point of attachment of A to the ring, forms a 5 or 6 membered ring,
  • p is very particularly preferably 0, 1, 2, and wherein
  • R 11 and R 12 very particularly preferably represent hydrogen or methyl
  • R 13 and R 14 very particularly preferably represent hydrogen, methyl, ethyl, cyclopropyl, cyanoethyl, 2-ethynyl, 2-propenyl, methoxymethyl, ethoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i-propylcarbonyl, n-butylcarbonyl, t-butylcarbonyl , Methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, t-butoxycarbonyl or phenoxycarbonyl,
  • Y very particularly preferably represents hydrogen or represents optionally mono- or polysubstituted, identically or differently substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- or neo-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, with up to 5 substituents selected from fluoro or chloro, and up to 2 substituents may be selected from bromine, cyano, nitro, hydroxy, amino, methylamino, dimethylamino, cyclopropyl, trifluoromethyl, methoxy, ethoxy, n- or i-
  • Q 1 to Q 3 independently of one another very particularly preferably represent a carbon atom which is substituted by hydrogen or by R 1 or is N, where the number of N atoms in Q 1 to Q 3 is at most 1, very particularly preferably Is a carbon atom which is substituted by hydrogen or R 6 or which is bonded to V, where V is then not equal to R 4 , Q to Q independently of one another very particularly preferably represent a carbon atom which is substituted by hydrogen, R 6 or AY, or N, where the number of N atoms in Q 5 to Q 8 is at most 1 and exactly one of Q 5 , Q 6 , Q 7 , Q 8 is substituted by A-Y.
  • Preferred compounds according to the invention are novel compounds of the formulas (IA) to (ED)
  • R 3 , R 8 , (R 6 ) m , X, A and Y (ie A, Y and AY) represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
  • preferred compounds according to the invention are the compounds of the general formulas (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) shown in Tables 1 to 7 and in particular those in the tables 1 to 7 listed specific compounds.
  • the present compounds of the general formula ( ⁇ ) may optionally have a chiral carbon atom.
  • these substituents may have both an (R) and an (S) configuration.
  • the present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms are independently
  • one chiral center may have the (S) configuration and the other chiral center may have the (S) configuration.
  • the compounds of formula (I) also include optionally present diastereomers or enantiomers as well as E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
  • the invention also relates to the use of the compounds of the general formula (I) according to the invention for the preparation of pesticides.
  • the invention also relates to pesticides containing compounds of the general formula (I) according to the invention and / or salts thereof in biologically active contents of> 0.00000001 wt .-%, preferably> 0.001 wt .-% to 95 wt .-%, based on the Weight of pesticide.
  • the invention also relates to methods for controlling animal pests, in which compounds of the general formula (I) according to the invention are allowed to act on animal pests and / or their habitat.
  • the active compounds according to the invention are suitable for plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are against normal sensitive and resistant species as well as effective against all or individual stages of development.
  • the above mentioned pests include:
  • Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp .. From the class of the arachnids e.g.
  • Acarus spp. Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri , Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phylloc
  • Chilopoda e.g. Geophilus spp., Scutigera spp.
  • Coleoptera e.g. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Attagenus spp.
  • Migdolus Spp. Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp., Popillia japonica, Premnotrypes spp., Psylliodes spp.
  • Ptinus spp. Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Starchus spp., Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp. Zabrus spp ..
  • Hyppobosca spp. Hypoderma spp., Liriomyza spp. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia spp., Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp , Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp ..
  • helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum , Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Ne
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Eurygaster spp. Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Monaionion atratum, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp.
  • Hymenoptera e.g. Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Lepidoptera From the order of Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius , Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., Conopomorph
  • Copitarsia spp. Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella Spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homoeosoma spp , Homona s, Ho
  • Tuta absoluta eg Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla e.g. Scutigerella spp.
  • Thysanoptera e.g. Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura e.g. Lepisma saccharina.
  • the plant parasitic nematodes include e.g. Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • the compounds of formula (I) may optionally also in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as Agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) are used. They leave optionally also be used as intermediates or precursors for the synthesis of other active ingredients.
  • the present invention further relates to formulations and application forms prepared therefrom as crop protection agents and / or pesticides such.
  • B. drench, drip and spray comprising at least one of the active compounds according to the invention.
  • the use forms contain other crop protection agents and / or pesticides and / or the effect of improving adjuvants such as penetration enhancers, eg.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more active compounds according to the invention, further agrochemical active substances.
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or other auxiliaries, such as adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance impregnated natural products, active ingredient-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance impregnated natural products, active ingredient-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Excipients which can be used are those which are suitable for imparting special properties to the formulation of the active ingredient or to the forms of use prepared from these formulations (such as, for example, pest control or crop protection agents such as spray liquors or seed dressings), such as certain technical properties and / or special biological properties Properties.
  • Typical adjuvants include: extenders, solvents and carriers.
  • polar and non-polar organic chemical liquids e.g. 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), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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 dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • Suitable solid carriers are, in particular: ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules in question: eg broken and fractionated natural rocks such Calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks.
  • ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates
  • synthetic minerals such as finely divided silica, alumina and silicates
  • liquefied gaseous diluents or solvents can be used.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylarylpolyglycolether, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydroly
  • Suitable emulsifiers and / or foam-formers are, in particular: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are nonionic and / or ionic substances, for example from the classes of alcohol POE and / or POP ethers, acid and / or POPPOE esters, alkylaryl and / or POP POE ethers, fatty and / or POP-POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitan or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO-ether adduct
  • POP polyoxypropylene
  • POE polyoxyethylene
  • PO propylene oxide
  • EO ethylene oxide
  • Further suitable oligo- or polymers for example starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with, for example, (poly) alcohols or (poly) amines.
  • lignin and its sulfonic acid derivatives simple and modified Celluloses, aromatic and / or aliphatic sulfonic acids and their adducts with formaldehyde.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • additives may be included in the formulations and the applications derived therefrom.
  • Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Further additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or Isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil methyl ester, 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 oil ethoxylate (10) or Isotridecyl ethoxylate (12)
  • fatty acid esters such as rapeseed oil or soybean oil methyl ester
  • fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammoni
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of active ingredient, more preferably between 0.01 and 95 wt .-% active ingredient, most preferably between 0.5 and 90 wt .-% of active ingredient, based on the weight of Formulation.
  • the active ingredient can be used in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other agrochemical active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers, semiochemicals or even with agents to improve plant properties.
  • agrochemical active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers, semiochemicals or even with agents to improve plant properties.
  • the active compounds according to the invention can furthermore be present in the form of insecticides in their commercial formulations and in the formulations prepared from these formulations in admixture with synergists.
  • Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention may furthermore, when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations, be present in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
  • the active substance content of the application forms (pest control agents) prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active ingredient, preferably between 0.00001 and 1% by weight, based on the weight of the application form.
  • the application is done in a custom forms adapted to the application.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, (spraying) spraying, spraying, sprinkling, evaporation, atomization, misting , (Ver) spreading, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer wrapping, etc. It is also possible , the active ingredients after the ultra-low Apply volume method or to inject the active ingredient preparation or the active ingredient itself in the soil.
  • a preferred direct treatment of the plants is foliar application, i. Active ingredients according to the invention are applied to the foliage, wherein the treatment frequency and the application rate can be adjusted to the infestation pressure of the respective pest.
  • the active compounds according to the invention enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the active compounds according to the invention on the habitat of the plant.
  • This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the active compounds of the invention, or by the soil application, i. the active compounds according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants.
  • this may also be by metering the compounds of the invention in a solid form (e.g., as granules) into a flooded paddy field.
  • the active compounds according to the invention can also be used in mixtures with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance.
  • synergistic effects i. E. the effectiveness of the mixtures is greater than the sum of the effectiveness of the individual compounds.
  • Suitable mixing partners are, for example, the following compounds:
  • Acetylcholinesterase (AChE) inhibitors such as
  • Carbamates for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate , Trimethacarb, XMC and xylylcarb; or organophosphates, eg acephates, azamethiphos, azinphos (-methyl, -ethyl), cadusafos, chloroethoxyfos, chlorfenvinphos, chloroforms, chlorpyrifos (-methyl), coumaphos, cyanophos, Demeton S-methyl, di
  • GABA-controlled chloride channel antagonists such as organochlorines, e.g. Chlordane and endosulfan (alpha); or
  • Fiproles phenylpyrazoles
  • Ethiprole e.g. Ethiprole
  • Fipronil e.g. Fipronil
  • Pyrafluprole e.g. Pyrafluprole
  • Pyrethroids e.g. Acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin (beta), cyhalothrin (gamma, lambda), cypermethrin (alpha, beta , theta, ceta-), cyphenothrin [(IR) - / r ⁇ ms isomers], deltamethrin, dimefluthrin, empenthrin [(isZ) - (IR) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, Flumethrin, fluvalinate (tau-), halfenprox, imiprothrin, metofi
  • nicotinergic acetylcholine receptor agonists such as nicotinergic acetylcholine receptor agonists
  • Neonicotinoids e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or
  • Allosteric acetylcholine receptor modulators such as
  • chloride channel activators such as Avermectins milbemycins, eg abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone analogs e.g. Hydroprene, kinoprene, methoprene; or fenoxycarb; Pyritexyfen.
  • agents with unknown or nonspecific modes of action such as fumigants, e.g. Methyl bromide and other alkyl halides; or
  • chloropicrin sulfuryl fluoride
  • Borax Tartar emetic.
  • mite growth inhibitors e.g. Clofentezine, diflovidazine, hexythiazox, etoxazole.
  • Microbial disruptors of insect intestinal membrane such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins, e.g. CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • insect intestinal membrane such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins, e.g. CrylAb, CrylAc, C
  • inhibitors of oxidative phosphorylation, ATP disruptors such as diafenthiuron; or organotin compounds, e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetradifon.
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap (hydrochloride), thiocylam, and thiosultap (-sodium).
  • inhibitors of chitin biosynthesis type 0, such as benzoylureas, e.g. Bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • benzoylureas e.g. Bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Moulting agents such as Cyromazine.
  • ecdysone agonist disruptors such as Diacylhydrazines, eg chromafenozide, Halofenozide, Methoxyfenozide and Tebufenozide.
  • Octopaminergic agonists such as amitraz.
  • Acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or
  • tetronic acid derivatives e.g. Spirodiclofen and spiromesifen
  • tetramic acid derivatives e.g. Spirotetramat.
  • ryanodine receptor effectors such as diamides, e.g. flubendiamide,
  • Chlorantraniliprole (Rynaxypyr), Cyantraniliprole (Cyazypyr) and 3-Bromo-N- ⁇ 2-bromo-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl ⁇ -1- (3-chloropyridin-2-yl) - 1 H-pyrazole-5-carboxamide (known from WO2005 / 077934) or methyl 2- [3,5-dibromo-2 - ( ⁇ [3-bromo-1- (3-chloro-2-yl) -lH -pyrazol-5-yl] carbonyl ⁇ amino) benzoyl] -1,2-dimethylhydrazinecarboxylate (known from
  • drugs with unknown mechanism of action such as azadirachtin, amidoflumet, benzoximate, bifenazate, quinomethionate, cryolites, cyflumetofen, dicofol, fluensulfone (5-chloro-2 - [(3,4,4-trifluorobut-3-en-l-yl) sulfonyl] -l, 3-thiazoles), flufenerim, pyridalyl and pyrifluquinazone; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo) and the following known active compounds
  • inhibitors of ergosterol biosynthesis such as aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamide, fenpropidin, fenpropimorph, Fluquinconazole, flu rimidol, flusilazole, flutriafol, furconazole, furconazole cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazole,
  • inhibitors of respiration such as bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture of syn-epimeric racemate 1RS, 4SR, 9RS and anti- more highly enriched racemates 1RS, 4SR, 9SR, isopyrazam (anti-epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), isopyrazam (syn-epimeric racemate 1RS , 4SR, 9RS), isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), is
  • inhibitors of respiration at the complex III of the respiratory chain, such as ametoctradine, amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestroburin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin , Pyraoxystrobin, pyribencarb, trifloxystrobin, (2E) -2- (2 - ⁇ [6- (3-chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yl] oxy ⁇ phenyl) -2- (methoxyimino) - N-methylethaneamide, (2E) -2- (methoxyimino) -N-methyl-2- (2- ⁇ [( ⁇ (1 ⁇ )
  • Mitosis and cell division inhibitors such as benomyl, carbendazim, chlfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7- (4-methylpiperidine-1) yl) -6- (2,4,6-trifluoro-henyl) [l, 2,4] triazolo [l, 5-a] pyrimidine and 3-chloro-5- (6-chloro-pyridin-3-yl) -6- methyl-4- (2,4,6-trifluorohexyl) pyridazine.
  • Compounds with multisite activity such as Bordeaux mixture, captafol, captan, chlorothalonil, copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichlofluanid, dithianone, dodine, dodine free base, Ferbam, Fluorofolpet, Folpet, guazatine, guazatin acetate , Iminoctadine, iminoctadinal besylate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, zinc metiram, copper oxine, propamidine, propineb, sulfur and sulfur preparations such as calcium polysulfide, thiram, tolylfluanid, zineb and ziram.
  • copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichlofluanid
  • resistance inducers such as acibenzolar-S-methyl, isotianil, probenazole and tiadinil.
  • inhibitors of amino acid and protein biosynthesis such as andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim and
  • inhibitors of ATP production such as fentin acetate, fentin chloride, fentin hydroxide and silthiofam.
  • inhibitors of cell wall synthesis such as Benthiavalicarb, ⁇ , ⁇ ⁇ , iprovalicarb, mandipropamide, polyoxins, polyoxorim, validamycin A and valproate.
  • inhibitors of lipid and membrane synthesis such as biphenyl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb, Iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl.
  • inhibitors of melanin biosynthesis such as carpropamide, diclocymet, fenoxanil, fthalide, p rquilon and tricyclazole.
  • Inhibitors of nucleic acid synthesis such as benalaxyl, benalaxyl-M (iralaxyl), bupirimate, clozylacone, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxolic acid.
  • signal transduction inhibitors such as chlozolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen and vinclozolin.
  • Decouplers such as binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap.
  • Other compounds such as benthiazole, bethoxazine, capsimycin, carvone, quinomethionate, chlorazafenone, cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophene, diclomethine, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomat, fenpyrazine, flumetover, fluoromide , Flusulfamide, flutianil, fosetyl-aluminum, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methylisothiocyanate, metrafenone, mild
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, nebulizing, spreading, brushing, injecting, casting and in propagating material, in particular in seeds, further by single or multi-layer wrapping.
  • plants and their parts can be treated.
  • wild species or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant varieties and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the terms "parts” or “parts of plants” or “plant parts” have been explained above. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques.
  • plants can be varieties, biotypes and genotypes. Preference is given to plants from the group of crops. Ornamentals, lawns, commonly used trees that are used as ornamental plants in public and private areas, and forest stands.
  • the forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees.
  • crops as used herein refers to crops used as plants for the production of food, feed, fuel or for technical purposes.
  • crops that can be treated with the active compounds of the invention include, for.
  • the following plant species turf, vines, cereals, for example wheat, barley, rye, oats, rice, maize and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg.
  • Particularly suitable target cultures for the treatment with the active compounds according to the invention are the following plants: bamboo wool, eggplant, turf, pome fruit, stone fruit, berry fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soybeans, Rapeseed, tomato, paprika, melons, cabbage, potato and apple.
  • Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.
  • trees which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P jeffregi, P. Baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus.
  • trees which can be improved according to the method of the invention, may be mentioned: From the species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis.
  • the present invention may also be practiced on any turfgrass, including "cool season turfgrasses” and “warm season turfgrasses”.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents usable in the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering power facilitated harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products, which exceed the actual expected effects.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
  • transgenic plants mentions important crops, such as cereals (wheat, rice), maize, soya, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), Corn, soya, potato, cotton, tobacco and oilseed rape are particularly emphasized.
  • Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a) , CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants”). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • the genes which confer the desired properties (“traits") can also occur in combinations with one another in the transgenic plants.
  • Examples of “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rapeseed
  • IMI® tolerance against imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Clearfield® varieties eg corn
  • the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • the compounds of the present invention can be used to control a variety of pests including, for example, noxious sucking insects, biting insects and other plant parasitic pests, storage pests, pests that destroy industrial materials, and use and control pests, including animal health parasites, such as their extinction and eradication.
  • the present invention thus also includes a method of controlling pests.
  • the active substances according to the present invention act against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasites includes in particular helminths such as cestodes, nematodes or trematodes, and protozoa such as kozzidia.
  • Ectoparasites are typically and preferably arthropods, especially insects such as flies (stinging and licking), parasitic fly larvae, lice, hair-pieces, feathers, fleas and the like; or acarids such as ticks, for example ticks or leather ticks, or mites such as mange mites, mites, feather mites and the like.
  • These parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; specific examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus;
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi;
  • Nematocerina and Brachycerina eg Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp , Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp.
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Ornithonyssus spp. Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; specific examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp .; special examples are: Cheyletiella yasguri, Cheyletiella yasguri,
  • the active compounds according to the invention are also suitable for controlling arthropods, helminths and protozoa which infect animals.
  • the animals include farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
  • farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
  • the animals also include domestic animals - also referred to as pets - such as pets. Dogs, cats, parlots, aquarium fish and so-called experimental animals such. Hamsters, guinea pigs, rats and mice.
  • control of the parasites can also help to prevent the transmission of infectious substances.
  • control means that the active ingredients act by determining the presence of the parasite in question reduce an animal affected by such parasites to harmless levels. More specifically, as used herein, “control” means that the agent kills the subject parasite, inhibits its growth, or inhibits its proliferation.
  • the active compounds of the invention when used for the treatment of animals, can be used directly.
  • they are used as pharmaceutical compositions which may contain pharmaceutically acceptable excipients and / or adjuvants known in the art.
  • the active ingredients may be shampoo or suitable, in aerosols or non-pressurized sprays, eg Pump sprays and atomizer sprays, applicable, formulated formulations.
  • the active compounds according to the invention can be used as formulations (for example powders, wettable powders, WP), emulsions, emulsifiable concentrates (EC), flowable agents, homogeneous solutions and Suspension concentrates [suspension concentrates, "SC"]) containing the active ingredients in an amount of 1 to 80% by weight, apply directly or after dilution (eg 100 to 10 000 times dilution) or use them as a chemical bath.
  • the active compounds according to the invention can be used in combination with suitable synergists or other active substances such as, for example, acaricides, insecticides, anthelmintics, antiprotozoal agents.
  • the compounds according to the invention exhibit a high insecticidal activity against insects which destroy industrial materials. Accordingly, the present invention also relates to the use of the compounds of the invention for the protection of industrial materials against attack or destruction by insects.
  • insects By way of example and preferably without limiting however, the following insects are mentioned: Beetles such as Hylotrupes b Camillus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Bristle tails like Lepisma saccharina.
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the ready-to-use agents may optionally contain further insecticides and, if appropriate, one or more fungicides.
  • the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • the active substances are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in enclosed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Acarina for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Saltatoria e.g. Acheta domesticus.
  • Dermaptera e.g. Forficula auricularia.
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • the invention also relates to a process for the preparation of compounds of general formula (I),
  • the invention also relates to a preferred alternative process for preparing the compounds of the general formula (1-3) according to the invention, which is shown in formula scheme 3, in which a) amines of the general formula (III)
  • the invention further relates to the compounds of the general formula (VI) which are obtained as intermediates in the process according to the invention for the preparation of compounds of the general formula (1-3).
  • a preferred compound of general formula (VI) is N- ⁇ 2,2,2-trifluoro-1- [3- (trifluoromethyl) phenyl] ethyl ⁇ acrylamide, their preparation in the
  • a sulfurizing reagent such as e.g. Lawesson's reagent, ammonium sulfide or diphosphorus pentasulfide.
  • Formula Schemes 7 to 10 show how the compounds of formula II can be obtained.
  • L is halogen or hydroxy, be represented by the reaction of amines of general structure (III) with activated carboxylic acid derivatives of the general structure (II).
  • a base such as triethylamine or sodium hydroxide
  • coupling reagents such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1, 1'-carbonyl-1H-imidazole, and similar compounds.
  • Suitable coupling reagents for carrying out the dartylation process are all those which are suitable for producing an ester or amide bond (cf., for example, Bodansky et al., Peptide Synthesis, 2nd ed., Wiley & Sons, New York, 1976, Gross, Meienhofer , The Peptides: Analysis, Synthesis, Biology (Academic Press, New York, 1979), and mixed anhydrides can also be used to prepare (I). [J. Am. Chem.
  • chloroformates such as isobutyl chloroformate, isopropyl chloroformate, etc. Diethyl acetyl chloride, trimethyl acetyl chloride and the like may also be used.
  • Compounds (1-2) according to the invention can also be prepared by reacting compounds of the general structure (1-1) according to the invention with an alkylating or acylating agent of general structure (IV), as shown in equation 2, for example.
  • Methyl iodide in the presence of a suitable base, e.g. Sodium hydride, wherein in the formulas (1-1), (rV) and (1-2)
  • L 1 represents chlorine, bromine, iodine, tosylate or mesylate
  • R 3a is C r C 4 alkyl or CC 4 alkylcarbonyl.
  • amines of the formula (III) are first reacted with acrylic acid derivatives of the formula (V) to give acrylic acid amides of the formula (VI).
  • Suitable reaction conditions for this reaction correspond to the reaction conditions given for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in formula scheme 1.
  • Compounds of formula (I) may also be obtained by conversion of functional groups from other compounds of formula (I), as illustrated in formula scheme 4.
  • carboxylic ester derivatives of the formula (1-4), which can be synthesized by the methods given in formula schemes 1 or 3, are prepared first analogously to processes generally known from the literature, in the presence of a base, such as e.g. Hydrolyzed to a carboxylic acid of formula (1-5) (see, for example, J. Am. Chem. Soc., 1986, 108, 4603).
  • Carboxylic acids of the formula (1-5) can then be reacted with amines of the formula (XIII) to give carboxylic acid amide derivatives of the formula (1-6).
  • the possible reaction conditions for this reaction have already been indicated for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in formula scheme 1.
  • nitriles of the formula (1-7) which can be synthesized by the methods given in formula schemes 1 or 3, are initially reduced in analogy to processes generally known from the literature to amines of the formula (1-8).
  • suitable reducing agents are hydrogen in the presence of a catalyst, for example palladium on carbon (cf., for example, J. Am. Chem. Soc. 1928, 50, 3370) or lithium aluminum hydride (cf., for example, Org. Reac., 1951, 6, 469).
  • Amines of formula (1-8) can then be reacted with carboxylic acid derivatives of formula (XIV) to give carboxylic acid amide derivatives of formula (1-9).
  • the possible reaction conditions for this reaction have already been indicated for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in equation 1.
  • Nitro compounds of the formula (1-10) which can be synthesized by the methods given in formula schemes 1 or 3 are first reduced in analogy to processes generally known from the literature to amines of the formula (I-II). Suitable methods for such reductions are, in particular, metal-mediated reactions, such as e.g. Tin (II) chloride, iron powder, zinc powder and similar compounds.
  • metal-mediated reductions, e.g. with tin (II) chloride can be made according to an OrganicSyntheses Coli. Vol. (III), 453 described methods.
  • Z-cinnamic acid amide derivatives of formula (1-15) can be obtained as shown in formula scheme 6b.
  • compounds of the formula (VII) are first reacted with propiolic acid of the formula (XXV) in the presence of a palladium catalyst, such as bis (triphenylphosphine) palladium dichloride, and copper salts, such as copper (I) iodide, to give alkyne acids of the formula (XXVI) ( Lit .: WO2006 / 002981).
  • a palladium catalyst such as bis (triphenylphosphine) palladium dichloride
  • copper salts such as copper (I) iodide
  • Suitable reaction conditions for this reaction correspond to the reaction conditions given for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in formula scheme 1.
  • the compounds of the formula (XXVII) can then be reacted with hydrogen in the presence of a suitable catalyst, for example the Lindlar catalyst, selectively to Z-cinnamic acid amides of the formula (1-15) (cf., for example, Journal of Organic Chemistry 2003, 68, 2913-2920).
  • N-substituted indole derivatives of general formula (1-17) can be obtained as shown in formula scheme 6c, wherein
  • R 8a is R 8 except hydrogen.
  • indoles of the general formula (1-16) which can be synthesized by the process indicated in formula scheme 1, are reacted with compounds of the general formula (IVa) in the presence of a base, such as, for example, potassium carbonate.
  • Carboxylic acids of the general formula (II) where L is OH are commercially available, known from the literature or can be synthesized by methods known from the literature. Thus cinnamic acid derivatives of the formula (IIa) are obtained
  • L 2 is chlorine, bromine, iodine or triflate
  • L 3 is H or C 1 -C 4 -alkyl, where two substituents L 3 can also form a 5- or 6-membered ring.
  • first compounds of the formula (VII) are reacted with boronic acids or boronic esters of the formula (XV) in the presence of a palladium catalyst to give cinnamic esters of the formula (XVI).
  • a palladium (II) compound such as bis (tricyclohexylphosphine) palladium (II) dichloride can be used.
  • the carboxylic acid esters of the formula (XVI) are converted into the corresponding cinnamic acids of the formula (II-2) by generally known processes, for example by alkaline hydrolysis with sodium hydroxide, or alternatively by varying the reaction conditions (eg the temperature or the reaction time) during the CC coupling already be obtained as free acids.
  • Scheme 8 (preparation of compounds of general formula II-2)
  • L 4 is fluorine, chlorine or bromine
  • Y'-A'-H is an optionally substituted triazole, pyrazole, tetrazole or imidazole, which carries a free NH function, where as substituents which are in the general definition of A or Y. radicals mentioned come into question.
  • aldehydes of the formula (XVII) are first reacted with heterocycles of the formula (XVIII), if appropriate in the presence of a base, to give partially known aldehydes of the formula (IXX) (cf., WO 2008019760, Tetrahedron (2001), 57 (22 ), 4781-4785.).
  • Aldehydes of the formula (LXX) can then be converted into cinnamic acids of the formula (II-2) analogously to processes known in the literature using malonic acid in the presence of a nitrogen base, for example piperidine with decarboxylation (for example Bioorganic & Medicinal Chemistry Letters (2008), 18 (5 ), 1663-1667, Journal of the Indian Chemical Society (2007), 84 (6), 612-614, Journal of Chemical Research (2005), (6), 364-365.).
  • a nitrogen base for example piperidine with decarboxylation
  • L 5 is chlorine or bromine
  • ALK is a Ci-C 4 alkyl group.
  • hydroxyaldehydes of the formula (XX) are initially reacted with alkyl halocarboxylates, such as haloacetic acid ethyl esters of the formula (XXI) in the presence of a base, such as e.g. Potassium carbonate to Benzofurancarbonklareestem the formula (XXII) implemented.
  • alkyl halocarboxylates such as haloacetic acid ethyl esters of the formula (XXI)
  • a base such as e.g. Potassium carbonate to Benzofurancarbonklam the formula (XXII) implemented.
  • the carboxylic esters of formula (XXII) are then prepared by well-known methods, e.g. by alkaline hydrolysis with sodium hydroxide as the base, converted into the corresponding Benzofurancarbonklaren of formula (II-3).
  • New indole carboxylic acids of formula (II-4) can be obtained as shown in formula scheme 10.
  • anilines of the formula (XXIII) are first converted into iodoanilines of the formula (XXIV) and then with pyruvic acid in the presence of palladium acetate and a base, such as l, 4-diazabicyclo [2.2.2] octane DABCO converted to benzofurancarboxylic esters of the formula ( ⁇ -4).
  • halogenating reagents such as thionyl chloride, thionyl bromide, phosphoryl chloride, oxalyl chloride, phosphorus trichloride, etc. getting produced.
  • Haloalkyl-substituted amines of the general formula (III) are commercially available, known from the literature or can be synthesized by methods known from the literature. For example, aryl halides can be reacted in the presence of magnesium in a Grignard reaction with haloalkyl carboxylic acid esters. The resulting ketones can then be converted by a reductive amination into the corresponding amines (DE-A-2723464). 2,2,2-trifluoro-1- (pyridin-4-yl) ethanamine is commercially available and can be prepared analogously to the procedure in Angew. Chem. 1998, 1 10, 6, 880-881 and J. Mol. Cat. B: Enzymatic 30 (2004) 61-68.
  • Novel compounds of formula (III-1) can be obtained as shown in formula scheme 10a.
  • a metallating reagent such as e.g. Magnesium, a Grignard compound, n-butyl lithium or tert.
  • Butyllithium reacted to an organometallic intermediate, which is then reacted with a compound of formula ( ⁇ ), whereby ketones of formula (XXX) are obtained.
  • ketones (XXX) e.g.
  • aryl halides of the formula (VII) are known or can be prepared by methods known in principle (see, for example, WO-A-2009055077, EP-A-1445253, EP-A-661258, US-A-6252090, Chemical & Pharmaceutical Bulletin (1992), 40 (7), 1789-92, Chemical & Pharmaceutical Bulletin (1994), 42 (4), 913-16, Compt. (1954), 237,357.).
  • New (het) aryl halides of general formula (VII) may be e.g. obtained by the following methods.
  • Novel compounds of formula (VII-1) can be obtained as shown in formula scheme 10b.
  • carboxylic acids of formula (XXXI) are reacted with amines of the formula (XIII).
  • the possible reaction conditions for this reaction have already been indicated for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in equation 1.
  • nitrile derivatives of the formula (XXXV) are first reduced with a reducing agent, such as, for example, lithium aluminum hydride, to give amines of the formula (XXXVI).
  • Amines of the formula (XXXVI) can then be reacted with carboxylic acid derivatives of the formula (XIV) to give carboxylic acid amide derivatives of the formula (VII-3).
  • the possible reaction conditions for this reaction have already been indicated for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in equation 1.
  • halogen derivatives of formula (XXXVII) are reacted with a Boc-protected amine of formula (XXXVIII) in the presence of a base, e.g. Sodium hydride reacted. Subsequently, the protecting group is cleaved to give secondary amines of the formula (VII-4).
  • Carboxylic acids of the general formula (II) where L is OH are commercially available, known from the literature or can be synthesized by methods known from the literature (formula schemes 7 to 10). The preparation of the carboxylic acid halides of the general formula (II) in which L is halogen is explained in connection with formula scheme 10.
  • the process according to the invention for the preparation of the novel compounds of the formula (I) is preferably carried out using a diluent.
  • Suitable diluents for carrying out the process according to the invention, besides water, are all inert solvents. As examples are :.
  • Halogenated hydrocarbons for example chlorohydrocarbons, such as tetrachlorethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (for example methanol, Ethanol, isopropanol, butanol), ethers (for example ethyl propyl ether, methyl tert-butyl ether, n-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dipropyl ether, diis
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally at absolute pressures between 0.1 and 15 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, if appropriate also under a protective gas atmosphere (for example under nitrogen, argon or helium) and the reaction mixture is generally stirred for several hours at the required temperature.
  • a reaction auxiliary for example under nitrogen, argon or helium
  • the workup is carried out by customary methods (see the preparation examples).
  • As basic reaction auxiliaries for carrying out the process according to the invention it is possible to use all suitable acid binders.
  • alkaline earth or alkali metal compounds eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium
  • amidine bases or guanidine bases eg 7-methyl-l, 5,7-triaza- bicyclo (4.4.0) dec-5-ene (MTBD), diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1,8-diazabicyclo (5.4.0) undecene (DBU )
  • Cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), ⁇ , ⁇ , ⁇ , ⁇ -tetramethyl-l, 8-naphthalenediamine, pentamethylpiperidine) and amines, especially tertiary amines, (eg triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine , Triamylamine, trihexylamine, ⁇ , ⁇ -dimethylaniline, N, N-dimethyl-toluidine, N, N-dimethyl-p-aminopyridine, N-methyl-pyrrolidine, N-methyl-piperidine, N-methyl-imidazole, N-methyl pyrazole, N-methyl-moholin, N-methyl-hexamethylenediamine, pyridine, 4-pyrroli
  • acidic reaction auxiliaries for carrying out the process according to the invention it is possible to use all mineral acids (for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid), Lewis acids (for example aluminum (III) chloride, boron trifluoride or etherate) , Titanium (V) chloride, tin (V) chloride, and organic acids (eg, formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or para-toluenesulfonic acid
  • the formula schemes 1 1 - 21 show, by way of example, the preparation of specific preferred compounds of the general formula I according to the invention. -
  • RT room temperature, i. 20 ° C
  • 1 eq means 1 equivalent.
  • Step 1
  • reaction solution was stirred at room temperature for 18 hours, then diluted with dichloromethane, washed three times with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residue was stirred with diisopropyl ether.
  • the resulting mixture was treated with saturated NaCl solution, the phases were separated and the aqueous phase was washed with 200-300 ml of diethyl ether.
  • the combined ethereal phases were dried over magnesium sulfate and the solvent was then removed on a rotary evaporator.
  • step 2 the following compounds of the general formula II-1 were also obtained: (2E) -3- [4- (pyridin-2-yl) carbamoyl] -3-trifluoromethylphenyl] acrylic acid starting from 4 bromo-N- (pyridin-2-yl) -2- (trifluoromethyl) benzamide.
  • HPLC-MS: log P 1.69; Mass (mz): 337.04 (M + H)
  • Washed sodium bicarbonate solution and saturated sodium chloride solution dried over sodium sulfate, filtered and concentrated to dryness in vacuo. There remains 453 mg as a mixture of the tert-butyl ester and the free acid, which was used without further purification for the next step.
  • Step 5 2 - ( ⁇ 2 ⁇ - Trifluoro-1- [3- (trifluoromethyl) phenyl] ethyl ⁇ carbamoyl) -1-benzofuran-6-carboxylic acid
  • the solution was treated with saturated sodium bicarbonate solution and extracted several times with ethyl acetate.
  • the combined organic phases were washed successively with sodium thiosulfate solution and with water, dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel.
  • Cyclopropylamine (862 mg, 15.1 mmol) was dissolved in 4 mL dichloromethane and treated dropwise under argon with a solution of trimethylaluminum in toluene (2M, 7.55 mL, 15.1 mmol). It was stirred for 30 min and then methyl 6-iodo-4- (trifluoromethyl) nicotinate (500 mg, 1.51 mmol) (synthesis analogous to J. Med. Chem., 2008, 51, 3133-3144 by esterification of Nicotinic acid) dissolved in 3 mL dichloromethane. It was heated to reflux overnight and, after cooling to room temperature, water was added cautiously.
  • the mixture was extracted with ethyl acetate and the organic phase washed with potassium sodium tartrate solution, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo.
  • the purification is carried out by means of silica gel chromatography with the eluent cyclohexane ethyl acetate (EA) (0% EA to 30% EA).
  • N-cyclopropyl-6-iodo-4- (trifluoromethyl) nicotinamide (125mg, 0.34mmol) and ethyl (2E) -3- (4,4,5,5-tetramethyl-1,2,2-dioxaborolane -2-yl) acrylate (93 mg, 0.41 mmol) were dissolved in 2 mL of 1,4-dioxane and dissolved under argon with sodium carbonate (180 mg, 1.72 mmol) and bis (tricyclohexylphosphine) palladium (II) dichloride added.
  • the reaction mixture was heated for 10 min at 120 ° C (80 W) in the microwave microwave (CEM Discover).
  • reaction mixture was filtered through kieselguhr and the filtrate was taken up in ethyl acetate, washed with hydrochloric acid (1 M), dried over magnesium sulfate, filtered and concentrated in vacuo.
  • the residue was taken up in 1.5 ml of ethanol, combined with sodium hydroxide solution (III) and stirred at room temperature overnight.
  • reaction mixture was added to ice cold dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated to dryness in vacuo.
  • Step 1 EthyI-6-chloro-1-methyl-2 - ( ⁇ 2Si-trifluoro-1- [3- (trifluoromethyl) phenyl] ethyl ⁇ carbamoyl) -H-indole-5-carboxylate
  • Step 2 N 5 -Allyl-6-chloro-1-methyl-N 2 - ⁇ 2, 5 -trifluoro-1- [3- (trifluoromethyl) phenyl] ethyl ⁇ -H-indole-2,5-dicarboxamide (Compound No. Ic-32 in Table 3)
  • the mixture was extracted with ethyl acetate and the organic phase washed with potassium sodium tartrate solution, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo.
  • the purification is carried out by means of silica gel chromatography with the eluent cyclohexane / ethyl acetate (EE) (0% EA to 30% EA).
  • reaction mixture was diluted with ethyl acetate, washed successively with hydrochloric acid (2 M) and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness in vacuo.
  • the residue was dissolved in N, N-dimethylformamide (1 ml) and treated with 4- (4,6-dimethoxy [1,3,5] triazin-2-yl) -4-methylmorpholinium chloride hydrate (973 mg, 3.52 mmol) and 2 , 2,2-Trifluoro-l- [3-trifluoromethylphenyl] ethanamine (780 mg, 3.20 mmol) and stirred at room temperature overnight.
  • reaction solution was added with hydrochloric acid (1 M) and extracted with ethyl acetate.
  • organic phase was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated to dryness in vacuo.
  • the residue was purified by silica gel chromatography using the eluent cyclohexane / ethyl acetate (EA) (0% EA to 40% EA).
  • tert-Butyl [4-bromo-2- (trifluoromethyl) benzyl] carbamate was prepared by reacting 1- [4-bromo-2- (trifluoromethyl) phenyl] methanamine hydrochloride with di-terti-butyl dicarbonate in analogy to tert-butyl - (5-bromo-2,3-dihydro-1H-indene-1-yl) carbamate from Synthesis Example 15, Step 1.
  • the crude product was purified by preparative HPLC (Phenomenex Gemini C18 5 ⁇ ; 125A; Aqua 50x21.2mm; Gradient: 0-1.5 min. 78% water, 20% acetonitrile, 1.5-10.0 min. Linear gradient to 18% water, 80% acetonitrile, 10.0-14.00 min. 18% water, 20% acetonitrile; Modifier: 10% NH4HC03 admixed with 2mL / min).
  • reaction mixture was then stirred for 45 minutes at -78 ° C and then added dropwise with the aid of a syringe in portions at -78 ° C to a solution of 3.71 g (26.17 mmol) of ethyl trifluoroacetate in 40 ml of dry ether. Thereafter, the entire reaction mixture was first stirred for 10 minutes at -78 ° C and then for one hour at room temperature. For workup, the entire reaction mixture was added to water and extracted with ether. The organic phase was separated and dried at 40 ° C in vacuo (due to the high volatility of the compound a maximum of 10 mbar). This gave 4.06 g (75.9% of theory) of 2,2,2-trifluoro-l- [3-fluoro-5- (trifluoromethyl) phenyl] -ethanone, which was isolated as a hydrate.
  • Stage 1 (4-bromo-2-fluorophenyl) ethanamine
  • THF 120mL
  • 75mL 150mM
  • 2M solution of methylmagnesium bromide in diethyl ether 200mL
  • 200mL methanol
  • 5.7 g (150 mM) of sodium borohydride were added in portions and the mixture was stirred at room temperature for 16 h. Thereafter, the reaction mixture was concentrated under vacuum and 200mL of water was added.
  • R 2 , R 4 and R 5 are H
  • X is CF 3 and (R ' ) n , R 3 , (R 6 ) m , A and Y have the meaning given in Table 1.
  • the numbers 2 to 6 represent the positions on the aromatic rings.
  • R 2 , R 3 , R 4 and R 5 are H, X is CF 3 and Q 1 , Q 2 , Q 3 , (R l ) n,, (R 6 ) m , A and Y are as shown in Table 2 have meaning indicated.
  • the numbers 2 to 6 represent the positions on the 5 aromatic rings.
  • R 2 and R 5 are H
  • X is CF 3 and (R ') n , R 3 , V, (R 6 ) m , A and Y have the meaning given in Table 3.
  • the numbers 2 to 6 or 2 to 5 represent the positions on the 5 aromatic rings.
  • R 2 , R 3 , R 4 are H and X, (R ' ) n , R 5 , (R 6 ) m , A and Y have the meaning given in Table 4.
  • the numbers 2 to 6 represent the positions on the aromatic rings.
  • R 2 , R 3 , R 4 and R 5 are H, X is CF 3 and Q 4 , Q 5 , (R ! ) n,, (R 6 ) m , A and Y are as shown in Table 5 Have meaning.
  • the numbers 2 to 6 represent the positions on the aromatic rings.
  • R 2 , R 3 , R 4 and R 5 are H, X is CF 3 and (R ' ) n , (R 6 ) m , A and Y have the meaning given in Table 7 5.
  • the numbers 2 to 6 represent the positions on the aromatic rings.
  • Boophilus microplus test (BOOPMI injection)
  • CTECFE Ctenocephalides felis oral
  • fasting adult fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom.
  • a metal cylinder is placed on the chamber, the underside of which is sealed with parafilm.
  • the cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
  • the compounds according to the invention exhibit the listed effect: 95% action at an application rate of 20 ppm: Ia-73; Ia-31
  • dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • a 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 emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
  • dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • a 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 emulsifier-containing water to the desired concentration.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm ⁇ Spodoptera frugiperdd).
  • the compounds according to the invention exhibit the listed effect: 83% action at an application rate of 20 g / ha: Ia-23; Ia-72; Ia-82
  • dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • a 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 emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • the abovementioned compounds according to the invention exhibit the activity listed: 100% action at an application rate of 20 g / ha: Ia-21, Ia-22, Ia-23, Ia-37, Ia-41, Ia-43, Ia 47, Ia-48, Ia-51, Ia-54, Ia-56, Ia-57, Ia-58, Ia-59, Ia-60, Ia-61, Ia-62, Ia-63, Ia-64, Ia-65, Ia-66, Ia-67, Ia-68, Ia-69, Ia-70, Ia-71, Ia-72, Ia-73, Ia-74, Ia-75, Ia-76, Ia 78, Ia-79, Ia-80, Ia-82, Ia-83, Ia-84, Ia-86, Ia-87, Ia-88, Ia-89, Ia-90, Ia-91, Ia-92, la-93, la
  • dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • Bean leaf disks Phaseol s vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • Tick nymphs ⁇ Amblyomma hebraeum are placed in perforated plastic cups and dipped for one minute at the desired concentration.
  • the ticks are transferred to filter paper in a Petri dish and stored in a climate cabinet.
  • Test animals adult sucked females of Boophilus microplus strain Parkhurst - SP resistant
  • Dimethylsulfoxide 10 mg of active ingredient are dissolved in 0.5 ml of dimethyl sulfoxide. In order to prepare a suitable formulation, the active compound solution is diluted with water to the particular desired concentration.
  • This preparation of active compound is pipetted into tubes. 8-10 ticks are transferred to another tube with holes. The tube is dipped into the preparation of the active ingredient with all ticks being completely wetted. After draining the liquid, the ticks are transferred to filter discs in plastic trays and stored in an air conditioned room. The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not externally visible are stored in glass tubes until larval hatching in the climatic chamber. An effect of 100% means that no tick has laid fertile eggs. In this test, e.g. the following compounds of the preparation examples an effect of 100% at an application rate of lOOppm: Ia-1 12, Ia-162
  • Boophilus microplus test (BOOPMI injection)
  • 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.
  • the drug solution is injected into the abdomen (Boophilus microplus), the animals are transferred to trays and stored in an air-conditioned room. The effect control takes place on storage of fertile eggs.
  • the following compounds of the preparation examples have an effect of 100% at an application rate of 20 ⁇ g / animal: Ia-5, Ia-8, Ia-18, Ia-19, Ia-21, Ia-22, Ia-23, Ia-24, I-29, Ia-30, Ia-31, Ia-32, Ia-36, Ia-40, Ia-41, Ia-42, Ia-43, Ia-44, Ia-45,
  • CTECFE Ctenocephalides felis oral
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. A portion of the concentrate is diluted with citrated bovine blood and the desired concentration produced.
  • Approximately 20 fasting adult fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom.
  • a metal cylinder is placed on the chamber, the underside of which is sealed with parafilm.
  • the cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane. After 2 days the kill is determined in%. 100% means that all fleas have been killed; 0% means that no flea has been killed.

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EP10768415A 2009-10-27 2010-10-14 Halogenalkyl-substituierte amide als insektizide und akarizide Withdrawn EP2493844A2 (de)

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PCT/EP2010/006285 WO2011054436A2 (de) 2009-10-27 2010-10-14 Halogenalkyl-substituierte amide als insektizide und akarizide
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US20110105532A1 (en) 2011-05-05
WO2011054436A3 (de) 2011-07-07
MX336183B (es) 2016-01-11
US8889878B2 (en) 2014-11-18
IL231407A (en) 2014-11-30
IL218986A0 (en) 2012-06-28
CN102741222B (zh) 2015-12-02
CO6531496A2 (es) 2012-09-28
BR112012010042A2 (pt) 2015-09-29
IL218986A (en) 2016-12-29
CN102741222A (zh) 2012-10-17
AR078641A1 (es) 2011-11-23
IL231407A0 (en) 2014-04-30
TW201136518A (en) 2011-11-01
US20130172390A1 (en) 2013-07-04
WO2011054436A2 (de) 2011-05-12
US8710242B2 (en) 2014-04-29
WO2011054436A8 (de) 2012-02-16
KR20120102617A (ko) 2012-09-18
MX2012004886A (es) 2012-05-23
UY32940A (es) 2011-05-31

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