# US 10,368,545 B2 · Substituted 2-thioimidazolylcarboxamides as pesticides

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- Number: US 10,368,545 B2
- Document ID: US10368545B2
- Status: Granted
- Kind: B2
- Application number: 15/546,234
- Filed: 2016-02-05
- Published: 2018-01-11
- Granted: 2019-08-06
- Earliest claimed: 2015-02-09
- Assignees: Bayer CropScience AG
- Applicants: Bayer Cropscience Aktiengesellschaft
- Inventors: Reiner Fischer; Markus Heil; Johannes-Rudolf Jansen; Susanne Kuebbeler; David Wilcke; Adeline Koehler; Matthieu Willot; Sascha Eilmus; Kerstin Ilg; Olga Malsam; Peter Loesel; Daniela Portz; Wolfram Andersch
- Web page: https://patentgrep.com/patent/US10368545B2

## CPC

- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N 43/52: condensed with carbocyclic rings, e.g. benzimidazoles
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 43/88: six-membered rings with three ring hetero atoms
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to compounds of the general formula (I) in which Q, V, T, W, X, Y, n and A have the meanings given in the description—and to a process for their preparation and to their use for controlling animal pests.

## Claims

### Claim 1

A compound of formula (I)
wherein
Q represents oxygen or sulphur,
V represents a radical selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
W represents a radical selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
X represents a radical selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl which is saturated or unsaturated and optionally interrupted by heteroatoms, optionally substituted cycloalkylalkyl which is saturated or unsaturated and optionally interrupted by heteroatoms, optionally substituted aryl, hetaryl, optionally substituted arylalkyl, hetarylalkyl and cyano,
Y represents a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl which is optionally interrupted by heteroatoms, optionally substituted cycloalkylalkyl which is optionally interrupted by heteroatoms, arylalkyl, hetarylalkyl and cyano,
n represents a number 0, 1 or 2,
A represents a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl and optionally substituted cycloalkyl and cycloalkylalkyl which are optionally interrupted by heteroatoms,
T represents oxygen or an electron pair,
and/or a salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein
Q represents oxygen or sulphur,
V represents a radical selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and cyano,
W represents a radical selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and cyano,
X represents a radical selected from the group consisting of C1-C8-alkyl, C3-C8-alkenyl or C3-C8-alkynyl, optionally mono- or polysubstituted independently of one another by halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, cyano, C(O)OR2, CONR2R3, and/or C(G)R2; C3-C8-cycloalkyl or C5-C8-cycloalkenyl, optionally interrupted once or twice independently of one another by O, S(O)m, C(G)R2, NR4 and optionally mono- to tetrasubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano; straight-chain or branched C3-C8-cycloalkyl-C1-C4-alkyl or C5-C8-cycloalkenyl-C1-C4-alkyl, optionally interrupted once or twice independently of one another by O, S(O)m, C(G)R2, NR4 and optionally mono- to tetrasubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano; aryl, optionally mono- to trisubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, C1-C4-haloalkoxy, C1-C4-haloalkyl-S(O)m—, nitro and/or cyano; hetaryl, which can be optionally mono- to trisubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, C1-C4-haloalkoxy, C1-C4-haloalkyl-S(O)m—, nitro and/or cyano; and straight-chain or branched aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, optionally mono- to trisubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, C1-C4-haloalkoxy, C1-C4-haloalkyl-S(O)m—, nitro and/or cyano,
G represents O, N—CN, or N—OR2,
Y represents a radical selected from the group consisting of hydrogen; C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- or polysubstituted independently of one another by halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, and/or cyano; C3-C8-cycloalkyl, optionally mono- or disubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano; straight-chain or branched C3-C8-cycloalkyl-C1-C4-alkyl, optionally interrupted once or twice independently of one another by 0, S(O)m, CO, NR4 and optionally mono- to tetrasubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano; arylalkyl or hetarylalkyl, optionally mono- to trisubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, C1-C4-haloalkoxy, C1-C4-haloalkyl-S(O)m—, nitro and/or cyano; and cyano,
m represents a number 0, 1 or 2,
n represents a number 0, 1 or 2,
A represents a radical selected from the group consisting of hydrogen; C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- or polysubstituted independently of one another by halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, and/or cyano; C3-C6-cycloalkyl, optionally mono- or disubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano; and straight-chain or branched C3-C8-cycloalkyl-C1-C4-alkyl, optionally mono- or disubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano,
R2 represents a radical selected from the group consisting of hydrogen; C1-C8-alkyl, C3-C8-alkenyl or C3-C8-alkynyl, optionally mono- or polysubstituted independently of one another by halogen, C1-C4-alkoxy, and/or C1-C4-alkyl-S(O)m—; C3-C8-cycloalkyl, optionally interrupted once by O, S(O)m and optionally mono- or disubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano; straight-chain or branched C3-C8-cycloalkyl-C1-C4-alkyl, optionally interrupted once by O, S(O)n and optionally mono- or disubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or cyano; aryl or hetaryl, optionally mono- to trisubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, C1-C4-haloalkoxy, C1-C4-haloalkyl-S(O)m—, nitro and/or cyano; and straight-chain or branched aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, optionally mono- to trisubstituted independently of one another by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, C1-C4-haloalkoxy, C1-C4-haloalkyl-S(O)m—, nitro and/or cyano,
R3 represents a radical selected from the group consisting of hydrogen; C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- or polysubstituted independently of one another by halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, and/or cyano,
R4 represents a radical selected from the group consisting of hydrogen; and C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- or polysubstituted independently of one another by halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O)m—, and/or cyano, or represents the radical CONR2R3 COR2, wherein R2 and R3 are as defined above,
T represents oxygen or an electron pair,
and/or a salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein
Q represents oxygen,
Y represents a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano,
W represents a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano,
X represents a radical selected from the group consisting of C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- to heptasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, cyano, C(O)OR2, CONR2R3, and/or C(G)R2; C3-C6-cycloalkyl, optionally interrupted once or twice independently of one another by O, S(O)m, CO, NR4 and optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano; straight-chain or branched C3-C6-cycloalkyl-C1-C2-alkyl, optionally interrupted once or twice independently of one another by O, S(O)m, CO, NR4 and optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano; phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl or imidazopyridinyl, which may optionally be substituted by phenyl which is mono- to trisubstituted independently of one another by fluorine, chlorine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m-, ethyl-S(O)m-, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m-, difluoroethyl-S(O)m-, trifluoromethyl-S(O)m-, nitro and/or cyano, or which may optionally be mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)n—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m—, difluoroethyl-S(O)m—, trifluoroethyl-S(O)m—, nitro and/or cyano; straight-chain or branched phenyl-C1-C2-alkyl, pyridyl-C1-C2-alkyl, pyrimidyl-C1-C2-alkyl, thiazolyl-C1-C2-alkyl or pyrazolyl-C1-C2-alkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, Me-S(O)m—, Et-S(O)m—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m—, difluoroethyl-S(O)m—, trifluoroethyl-S(O)m—, nitro and/or cyano; and cyano,
G represents O or N—OR2,
Y represents a radical selected from the group consisting of hydrogen; C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl, optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, and/or cyano; C3-C6-cycloalkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano; straight-chain or branched C3-C6-cycloalkyl-C1-C2-alkyl, optionally interrupted once or twice independently of one another by O, S(O)m, CO, NR4 and optionally mono- to tetrasubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano; aryl-C1-C2-alkyl or hetaryl-C1-C2-alkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, C1-C4-haloalkyl, trifluoromethyl, methoxy, ethoxy, cyano, nitro and/or cyano; and cyano,
m represents a number 0, 1 or 2,
n represents a number 0, 1 or 2,
A represents a radical selected from the group consisting of hydrogen; C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, and/or cyano; C3-C6-cycloalkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano; and straight-chain or branched C3-C6-cycloalkyl-C1-C2-alkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano,
R2 represents a radical selected from the group consisting of hydrogen; C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, and/or ethyl-S(O)m—; C3-C6-cycloalkyl, optionally interrupted once by O, S(O)m, and optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano; straight-chain or branched C3-C6-cycloalkyl-C1-C2-alkyl, optionally interrupted once by O, S(O)m and optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and/or cyano; phenyl or pyridyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m—, difluoroethyl-S(O)m—, trifluoroethyl-S(O)m—, nitro and/or cyano; and straight-chain or branched phenyl-C1-C2-alkyl, pyridyl-C1-C2-alkyl, pyrimidyl-C1-C2-alkyl or thiazolyl-C1-C2-alkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)n—, difluoroethyl-S(O)n—, trifluoroethyl-S(O)n—, nitro and/or cyano,
R3 represents a radical selected from the group consisting of hydrogen; and C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl, optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, and/or cyano,
R4 represents a radical selected from the group consisting of hydrogen; and C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl, optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, cyano, and/or represents the radical CONR2R3 or COR2, wherein R2 and R3 are as defined above,
T represents oxygen or an electron pair,
and/or a salt thereof.

### Claim 4 (depends on 1)

The compound of formula (I-A)
according to claim 1, and/or salt thereof.

### Claim 5 (depends on 1)

The compound of formula (I-B)
according to claim 1, and/or salt thereof.

### Claim 6 (depends on 4)

The compound according to claim 4 wherein
V represents a radical selected from the group consisting of hydrogen, fluorine, chlorine, methyl and cyano,
W represents a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl and cyano,
X represents a radical selected from the group consisting of C1-C6-alkyl, C3-C4-alkenyl or C3-C4-alkynyl, which are optionally mono-, di-, tri-, tetra-, pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, and/or cyano and may optionally be monosubstituted by the groups C(O)OR2, CONR2R3, C(G)R2; C3-C6-cycloalkyl, optionally interrupted once or twice independently of one another by O, S(O)m, CO, NR4 and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; C3-C6-cycloalkyl-methyl, optionally interrupted once or twice independently of one another by O, S(O)m, CO, NR4 and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; phenyl, pyridyl, pyrimidyl, thienyl, thiazolyl, oxazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl or imidazopyridinyl, which may optionally be substituted by phenyl which is mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m-, ethyl-S(O)n-, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m-, difluoroethyl-S(O)m-, trifluoroethyl-S(O)m-, nitro and/or cyano, or which may optionally be mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m—, difluoroethyl-S(O)m—, trifluoroethyl-S(O)m—, nitro and/or cyano; benzyl, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl or pyrazolyl-C1-C2-alkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, Me-S(O)m—, Et-S(O)m—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)n—, difluoroethyl-S(O)m—, trifluoroethyl-S(O)m—, nitro and/or cyano; and cyano,
G represents O or N—OR2,
Y represents a radical selected from the group consisting of hydrogen; and methyl, ethyl, propyl, allyl, propargyl or benzyl, optionally mono- to trisubstituted independently of one another by fluorine, methoxy, ethoxy, and/or cyano,
m represents a number 0, 1 or 2,
n represents a number 0, 1 or 2,
A represents a radical selected from the group consisting of hydrogen; and
methyl, ethyl, propyl, allyl, propargyl, cyclopropyl or cyclopropylmethyl, optionally mono- to trisubstituted independently of one another by fluorine, methoxy, ethoxy, and/or cyano,
R2 represents a radical selected from the group consisting of hydrogen; C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, optionally mono- to trisubstituted independently of one another by fluorine, chlorine, methoxy, ethoxy, methyl-S(O)m—, and/or ethyl-S(O)m—; C3-C6-cycloalkyl, optionally interrupted once by O, S(O)m and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; C3-C6-cycloalkylmethyl, optionally interrupted once by O, S(O)m and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; phenyl or pyridyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m—, difluoroethyl-S(O)m—, trifluoroethyl-S(O)m—, nitro and/or cyano; and benzyl, pyridylmethyl, pyrimidylmethyl or thiazolylmethyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)m—, difluoroethyl-S(O)m—, trifluoroethyl-S(O)m—, nitro and/or cyano,
R3 represents a radical selected from the group consisting of hydrogen; and C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl, optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, and/or cyano,
R4 represents a radical selected from the group consisting of hydrogen; and C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl, optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S(O)m—, ethyl-S(O)m—, and/or cyano; or represents the radical CONR2R3 or COR2, wherein R2 and R3 are as defined above,
T represents oxygen or an electron pair,
and/or a salt thereof.

### Claim 7 (depends on 4)

The compound according to claim 4 wherein
V represents hydrogen or fluorine,
W represents a radical selected from the group consisting of hydrogen, chlorine, bromine and methyl,
X represents a radical selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, 2,2-dimethylpropyl, hexyl, neohexyl, allyl, methallyl, 2-butenyl, propargyl, and 2-butynyl, which are optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methylsulphanyl, ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl, and/or ethylsulphonyl and may optionally be monosubstituted by the groups C(O)OR2, CONR2R3, and/or C(G)R2; cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally interrupted once or twice independently of one another by O, S(O)m, CO, NR4 and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, optionally interrupted once or twice independently of one another by O, S(O)m, CO, NR4 and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; phenyl, pyridyl, pyrimidyl, thienyl, thiazolyl, oxazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl or imidazopyridinyl, which may optionally be substituted by phenyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methylsulphanyl, ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, difluoromethoxy, trifluoromethoxy, trifluoromethylsulphanyl, trifluoromethylsulphinyl, trifluoromethylsulphonyl, difluoromethylsulphanyl, difluoromethylsulphinyl, difluoromethylsulphonyl, trifluoroethylsulphanyl, trifluoroethylsulphinyl trifluoroethylsulphonyl, nitro and/or cyano; benzyl, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl or pyrazolyl-C1-C2-alkyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methylsulphanyl, ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, difluoromethoxy, trifluoromethoxy, trifluoromethylsulphanyl, trifluoromethylsulphinyl, trifluoromethylsulphonyl, difluoromethylsulphanyl, difluoromethylsulphinyl, difluoromethylsulphonyl, trifluoroethylsulphanyl, trifluoroethylsulphinyl trifluoroethylsulphonyl, nitro and/or cyano; and cyano,
G represents O or N—OR2,
Y represents a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl and benzyl,
m represents a number 0, 1 or 2,
n represents a number 0, 1 or 2,
A represents a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl, propargyl, cylopropyl and cyclopropylmethyl,
R2 represents a radical selected from the group consisting of hydrogen; methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, methallyl, 2-butenyl, propargyl or 2-butynyl, optionally mono- to trisubstituted independently of one another by fluorine, chlorine, methoxy, and/or ethoxy; cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally interrupted once by O or S(O)m and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, optionally interrupted once by O or S(O)m and optionally mono- or disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, and/or cyano; phenyl or pyridyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methylsulphanyl, ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, difluoromethoxy, trifluoromethoxy, trifluoromethylsulfanyl, trifluoromethylsulphinyl, trifluoromethylsulphonyl, difluoromethylsulphanyl, difluoromethylsulphinyl, difluoromethylsulphonyl, trifluoroethylsulphanyl, trifluoroethylsulphinyl, trifluoroethylsulphonyl, nitro and/or cyano; and benzyl, pyridylmethyl, pyrimidylmethyl or thiazolylmethyl, optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, nitro and/or cyano,
R3 represents a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and allyl,
R4 represents a radical selected from the group consisting of hydrogen; and methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or allyl, which may optionally be substituted once to three times independently of one another by fluorine, methoxy, ethoxy, or cyano; or
represents the radical CONR2R3 or COR2, wherein R2 and R3 are as defined above,
T represents oxygen or an electron pair,
and/or a salt thereof.

### Claim 8 (depends on 1)

The compound of formula (I-A)
according to claim 1, wherein
V represents hydrogen,
W represents a radical selected from the group consisting of hydrogen, chlorine and bromine,
X represents a radical selected from the group consisting of methyl, ethyl, n-butyl, n-pentyl, n-propyl, isopropyl, allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydropyranyl, tetrahydrothiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]-bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl, methylthioethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 3-chloro-2,2,3,3-tetrafluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 2,2,2-trifluoroethylthioethyl, methylcarbonylmethyl, cyclopropylcarbonylmethyl, tert-butylcarbonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, hydroxycarbonylmethyl, carbamoylmethyl, N-methylcarbamoylmethyl, N-cyclopropylcarbamoylmethyl, N,N-dimethylcarbamoylmethyl, 2-methoximinopropyl, cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl, 3-methylthiophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-diemethylaminophenyl, 2-fluorophenyl, 2-methoxyphenyl, 2-dimethylaminosulphonylphenyl, 2-dimethylaminocarbamoylphenyl, 3-nitrophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl, 2,5-dichlorophenyl, 3,5-dichlorophenyl, 4-chloro-3-trifluoromethylphenyl, 2,4,5-trichlorophenyl, 2-pyridyl, 5-(2-chloro)pyridyl, 2-(5-methyl)pyridyl, 2-(6-methyl)pyridyl, 2-(3-trifluoromethyl)pyridyl, 2-pyrimidyl, 2-(4-methyl)pyrimidyl, 2-(5-methyl)pyrimidyl, 2-(4-methoxy)pyrimidyl, 2-(5-fluoro)pyrimidyl, 2-(4-trifluoromethyl)pyrimidyl, 2-(5-trifluoromethyl)pyrimidyl, 2-(4,6-dimethyl)pyrimidyl, 2-(4,5-dimethyl)pyrimidyl, 2-(4,6-dimethoxy)pyrimidyl, —CH2-2-pyrimidyl, —CH2-2-pyrazinyl, —CH2-5-(1-methyl)imidazolyl, —CH2-3-(1-methyl)pyrazolyl, —CH2-4-pyridyl, —CH2-2-pyridyl, —CH2-2-(1-methyl)imidazolyl, —CH2-3-pyridyl, —CH2-2-furanyl, —CH2-5-(2-chloro)pyridyl, benzyl, 3,4-dichlorobenzyl, 2,6-difluorobenzyl, 2-fluoro-6-methoxybenzyl, 2,6-dichlorobenzyl, 2-chloro-6-trifluoromethylbenzyl, 2-chloro-6-fluorobenzyl, —CH2-2-(4,6-dimethoxy)pyrimidyl, 2,6-dimethylbenzyl, —CH2-1-(3-nitro-5-methyl)pyrazolyl, 2-(1-methyl)benzimidazolyl, 2-(5-methyl)oxadiazolyl, 2-[3-methyl-6-(trifluoromethyl)imidazo[4.5]pyridinyl, 3-[4-ethyl-5-(trifluoromethyl)]-1,2,4-triazolyl, 3-[4-methyl-5-(trifluoromethyl)]-1,2,4-triazolyl, 3-[4-methyl-5-(difluoromethyl)]-1,2,4-triazolyl, 2-(5-phenyl)-1,3,4-thiadiazolyl, 2-(1-methyl-5-phenyl)imidazolyl, 2-(4,5-dimethyl)oxazolyl, 2-(1-methyl-5-methoxycarbonyl)imidazolyl, 2-(1-methyl)imidazolyl, and 1,2-ethanediyl,
Y represents methyl, ethyl or benzyl,
n represents a number 0 or 2,
A represents hydrogen or methyl,
T represents an electron pair,
and/or a salt thereof;
or
a compound of formula (I-B)
according to claim 1, where
V represents hydrogen,
W represents a radical selected from the group consisting of hydrogen, chlorine and bromine
X represents a radical selected from the group consisting of 4,6-dimethylpyrimidyl, n-butyl, n-pentyl, benzyl, methyl, 3-methylthiophenyl, 2,2,2-trifluoroethyl, phenyl, 4-methylphenyl, pyrimidyl, ethylthioethyl, 2-nitrophenyl, and cyclopropylmethyl,
Y represents methyl,
n represents a number 0 or 2,
A represents hydrogen or methyl,
T represents an electron pair,
and/or a salt thereof.

### Claim 9 (depends on 8)

The compound of formula (I-A) or (I-B) according to claim 8, wherein
W represents hydrogen and
A represents methyl.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein W is hydrogen, Y is C1-C6-alkyl, and A is C1-C6-alkyl.

### Claim 11 (depends on 1)

A composition, comprising at least one compound according to claim 1 and one or more customary extenders and/or surfactants optionally for controlling one or more animal pests.

### Claim 12 (depends on 1)

An agrochemical formulation comprising at least one compound according to claim 1 in a biologically effective amount of from 0.00000001 to 98% by weight based on the weight of the agrochemical formulation, and one or more extenders and/or surfactants.

### Claim 13 (depends on 12)

The agrochemical formulation according to claim 12, additionally comprising a further agrochemically active compound.

### Claim 14 (depends on 1)

A method for controlling one or more animal pests, comprising allowing at least one compound according to claim 1 or a composition thereof to act on the animal pests and/or a habitat thereof.

### Claim 15 (depends on 14)

A method according to claim 14, where surgical, therapeutic and diagnostic treatment of the human or animal body is excluded.

### Claim 16 (depends on 1)

A product comprising at least one compound according to claim 1 for controlling one or more animal pests.

### Claim 17 (depends on 1)

A product comprising at least one compound according to claim 1 for protecting propagation material of one or more plants.