IP Library Granted Patent US 8,324,390
Granted Patent B2
US 8,324,390 · App. 12/654,384 · Granted Dec 4, 2012

Tetrazole-substituted anthranilamides as pesticides

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Quick Facts
Patent No.
US 8,324,390
App. No.
12/654,384
Granted
Dec 4, 2012
Kind
B2
Abstract

The present invention relates to tetrazole-substituted anthranilamides of the formula (I) in which R 1 , R 2 , R 3 R 4 , R 5 , n, X and Q have the meanings given in the description—and to their use as insecticides and/or acaricides, also in combination with other agents such as penetrants and/or ammonium salts or phosphonium salts.

Claims (49)

1. A tetrazole-substituted anthranilamide compound of formula (I)

in which

R 1 represents methyl or chlorine,

R 2 represents halogen, cyano, methyl or C 1 -C 4 -alkylsulphonyl,

R 3 represents hydrogen, or represents C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -cycloalkyl-C 1 -C 6 -alkyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another is selected from the group consisting of halogen, amino, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 3 -C 6 -cycloalkylamino and a 5- or 6-membered heteroaromatic ring,

n represents 1, 2, 3 or 4,

X represents N, CH, CF, CCl, or CBr,

R 4 independently of one another represents hydrogen, cyano, halo-C 1 -C 6 -alkyl, halogen or halo-C 1 -C 4 -alkoxy,

R 5 represents hydrogen or C 1 -C 6 -alkyl,

Q represents one of the tetrazole radicals from the group Q-1 to Q-11 below:

or a salt of a compound of formula (I).

2. A compound of formula (I-1) according to claim 1

in which

R 1 represents methyl or chlorine,

R 2 represents halogen, cyano or methyl,

R 3 represents hydrogen, or represents C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -cycloalkyl-C 1 -C 6 -alkyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another is selected from the group consisting of halogen, amino, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 3 -C 6 -cycloalkylamino and a 5- or 6-membered heteroaromatic ring,

Q represents one of the tetrazole radicals from the group Q-1 to Q-7 below:

or a salt of a compound of formula (I-1).

3. A compound of formula (I-1) according to claim 2 , where

R 1 represents methyl,

R 2 represents halogen, cyano or methyl,

R 3 represents hydrogen, or represents C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another is selected from the group consisting of halogen, cyano, amino, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 3 -C 6 -cycloalkyl and a 5- or 6-membered heteroaromatic ring which contains 1 or 2 heteroatoms selected from the group consisting of N, O and S, where two oxygen atoms are not adjacent to one another in the ring,

Q represents the radicals Q-1, Q-2, or Q-6,

Q also represents the radicals Q-3, Q-4, Q-5, or Q-7,

or a salt of a compound of formula (I-1).

4. A composition comprising at least one compound of formula (I) according to claim 1 and at least one salt of formula (XI)

in which

D represents nitrogen or phosphorus,

R 10 , R 11 , R 12 , and R 13 independently of one another represent hydrogen, or in each case optionally substituted C 1 -C 8 -alkyl or mono- or polyunsaturated, optionally substituted C 1 -C 8 -alkylene, where the substituents is selected from the group consisting of halogen, nitro and cyano,

m represents 1, 2, 3 or 4, and

R 14 represents an inorganic or organic anion.

5. A composition comprising at least one compound of formula (I) according to claim 1 and at least one penetrant of formula (XII)

R—O-(-AO) v —R′  (XII),

in which

R represents straight-chain or branched alkyl having 4 to 20 carbon atoms,

R′ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or n-hexyl,

AO represents an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical, or represents mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals, and

v represents a number from 2 to 30.

6. A method for controlling animal pests, comprising allowing a compound of formula (I) according to claim 1 to act on animal pests and/or their habitat.

7. A process for preparing an agrochemical composition, comprising mixing a compound of the formula (I) according to claim 1 with an extender and/or a surfactant.

8. A method for controlling animal pests, comprising allowing a compound of formula (I-1) according to claim 2 to act on animal pests and/or their habitat.

9. A method for controlling animal pests, comprising allowing a composition according to claim 4 to act on animal pests and/or their habitat.

10. A method for controlling animal pests, comprising allowing a composition according to claim 5 to act on animal pests and/or their habitat.

11. A process for preparing an agrochemical composition, comprising mixing a compound of formula (I-1) according to claim 2 with an extender and/or a surfactant.

12. A process for preparing an agrochemical composition, comprising mixing a composition according to claim 4 with an extender and/or a surfactant.

13. A process for preparing an agrochemical composition, comprising mixing a composition according to claim 5 with an extender and/or a surfactant.

14. A method for protecting plants, comprising allowing at least a compound of formula (I) according to claim 1 to act on said plants and/or seeds and/or plant propagation material and/or plant parts formed later from said plant propagation material.

15. A method for protecting plants, comprising allowing a composition according to claim 4 to act on said plants and/or seeds and/or plant propagation material and/or plant parts formed later from said plant propagation material.

16. A method for protecting plants, comprising allowing a composition according to claim 5 to act on said plants and/or seeds and/or plant propagation material and/or plant parts formed later from said plant propagation material.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2018
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 047578/0121 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035005/0420 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2010
From: FISCHER, RUDIGER, DR.; FUNKE, CHRISTIAN, DR.; GESING, ERNST RUDOLF, DR.; GRONDAL, CHRISTOPH, DR.; HENSE, ACHIM, DR.; BECKER, ANGELA, DR.; FRANKEN, EVA-MARIA, DR.; MALSAM, OLGA, DR.; VOERSTE, ARND, DR.; GORGENS, ULRICH; WROBLOWSKY, HEINZ-JUERGEN, DR.
To: BAYER CROPSCIENCE AG
Reel/Frame 024367/0273 →