IP Library Granted Patent US 8,980,886
Granted Patent B2
US 8,980,886 · App. 13/160,281 · Granted Mar 17, 2015

Anthranilic acid derivatives

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Quick Facts
Patent No.
US 8,980,886
App. No.
13/160,281
Granted
Mar 17, 2015
Kind
B2
Abstract

The present invention relates to novel anthranilic acid derivatives of the general formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , Qx, A, Qy and n have the meanings given in the description, to their use as insecticides and acaricides for controlling animal pests, also in combination with other agents for activity boosting, and to a plurality of processes for their preparation.

Claims (49)

1. An anthranilic acid derivative of formula (I)

in which

R 1 represents hydrogen,

R 2 represents hydrogen,

R 3 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyano-n-propyl, 2-cyano-n-propyl, 3-cyano-n-propyl, 1-cyanoisopropyl,2-cyanoisopropyl, phenyl or pyridyl,

R 4 represents hydrogen, methyl, trifluoromethyl, cyano, fluorine, chlorine, bromine, iodine or trifluoromethoxy or two adjacent radicals R 4 represent —(CH 2 ) 4 —or —(CH═CH—) 2 —

n represents 0 to 3,

R 5 represents methyl, fluorine, chlorine, bromine or iodine,

Q X represents thiazole, oxazole, pyrrole, imidazole, triazole, pyrimidine, or phenyl, which is monosubstituted by the group R 7

A represents —CH 2 —, —CH(CH 3 ), C(CH 3 ) 2 , —CH 2 CH 2 —, —CH(CN)—, —CH 2 O —or —C(═O)—CH 2 —,

Q Y represents an optionally mono- or polysubstituted 5- or 6-membered heteroaromatic ring selected from the group consisting of Q-36 to Q-40, Q43, Q-58 to Q-59,Q62, Q63, an aromatic 9-membered fused heterobicyclic ring system Q-54 to Q-56 or a 5-membered heterocyclic ring Q-60 to Q-61 where the substituents independently of one another may be selected from the group consisting of C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 2 -alkoxy, halogen, cyano, hydroxyl, nitro and C 1 -C 2 -haloalkoxy

or where the substituents independently of one another may be selected from the group consisting of phenyl and a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy,

R 9 independently represents fluorine, chlorine or bromine

P represents 1,

Z represents N, CH, or CCl,

and wherein the compound of formula (I) can furthermore comprise an N-oxide and/or salt thereof,

wherein

2. A mixture of compounds according to claim 1 , in which Qy is Q62 and Q63, the ratio of a compound of the formula (I) in which Qy is Q62 to a compound of the formula (I) in which Qy is Q63 being 60:40 to 99:1.

3. A mixture of compounds according to claim 1 , in which Qy is Q58 and Q59, the ratio of a compound of the formula (I) in which Qy is Q58 to a compound of the formula (I) in which Qy is Q59 being 60:40 to 99:1.

4. A process for preparing a compound according to claim 1 , comprising

(A) reacting an aniline of formula (II)

in which X represents O,

optionally, with a carbonyl chloride of formula (III)

in the presence of an acid-binding agent; or

(B) reacting an aniline of formula (II)

in which X represents O,

optionally, with a carboxylic acid of the formula (IV)

in the presence of a condensing agent; or

(C) for the synthesis of an anthranilamide of formula (I) in which R 1 represents hydrogen,

optionally reacting a benzoxazinone of formula (V)

with an amine of the formula (VI)

in the presence of a diluent.

5. A composition comprising at least one compound according to claim 1 and at least one salt of formula (XXIV)

in which

D represents nitrogen or phosphorus,

R 10 , R 11 , R 12 , 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 -alkylen where the substituents may be selected from the group consisting of halogen, nitro and, cyano,

m represents 1, 2, 3 or 4,

R 14 represents an inorganic or organic anion.

6. A composition comprising at least one compound according to claim 1 and at least one penetrant of formula (XXV)

R-O—(-AO) V -R′  (XXV)

in which

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

R 1 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 a mixture of ethylene oxide and propylene oxide radicals or butylene oxide radicals and

V represents a number from 2 to 30.

7. An agrochemical composition comprising at least one compound according to claim 1 and at least one extender and/or surfactant.

8. A process for producing an agrochemical composition comprising mixing at least one compound according to claim 1 with at least one extender and/or surfactant.

9. Method for controlling animal pests comprising applying at least one compound according to of claim 1 to animal pests and/or phytopathogenic fungi and/or their habitat and/or seed.

10. A compound according to claim 1 , in which the compound has the following structure:

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 034892 FRAME: 0286. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 19, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035071/0680 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 034892/0286 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2011
From: FISCHER, RUEDIGER, DR.; GRONDAL, CHRISTOPH, DR.; HEIL, MARKUS, DR.; WROBLOWSKY, HEINZ-JUERGEN, DR.; GESING, DR. ERNEST RUDOLF, PROF; VOERSTE, ARND, DR.; GOERGENS, ULRICH
To: BAYER CROPSCIENCE AG
Reel/Frame 026830/0172 →