IP Library Granted Patent US 8,410,106
Granted Patent B2
US 8,410,106 · App. 13/022,957 · Granted Apr 2, 2013

Hydrazine-substituted anthranilic acid derivatives

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Quick Facts
Patent No.
US 8,410,106
App. No.
13/022,957
Granted
Apr 2, 2013
Kind
B2
Abstract

The present invention constitutes new hydrazine-substituted anthranilic acid derivatives of the general formula (I), in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Qx, A, Qy and n have the definitions indicated in the description, application thereof as insecticides and acaricides for controlling animal pests, alone and in combination with further agents for activity boosting, and a number of processes for their preparation.

Claims (93)

1. An anthranilic acid derivative of general formula (I)

in which

R 1 is hydrogen, amino, or hydroxyl or is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, each of which is optionally substituted one or more times by identical or different substituents, the substituents being selectable independently of one another from halogen, cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, (C 1 -C 4 -alkoxy)carbonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, or (C 1 -C 4 -alkyl)C 3 -C 6 -cycloalkylamino,

R 2 , R 3 independently of one another are hydrogen, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 2 -C 6 -alkylaminocarbonyl, or C 2 -C 6 -dialkylaminocarbonyl or are C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, each of which is optionally substituted one or more times by identical or different substituents, the substituents being selectable independently of one another from halogen, 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 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkylsulphimino, C 1 -C 4 -alkylsulphimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulphoximino, C 1 -C 4 -alkylsulphoximino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphoximino-C 2 -C 5 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, or C 3 -C 6 -trialkylsilyl, or

R 2 and R 3 independently of one another are a phenyl ring or a 5- or 6-membered unsaturated, partially saturated or saturated heterocycle, the phenyl ring or the heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, 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, (C═O)OH, (C═O)NH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkyl sulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, tri(C 1 -C 2 )alkylsilyl, or (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, or

R 2 and R 3 are joined to one another via two to six carbon atoms and form a ring which optionally additionally contains a nitrogen, sulphur or oxygen atom and may optionally be substituted one to four times by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, halogen, cyano, amino, C 1 -C 2 -alkoxy, or C 1 -C 2 -haloalkoxy,

R 4 is a group selected from —C(═S)—R 8 , —C(═O)—R 8 , —C(═O)—OR 9 , —C(—S)—OR 9 , —C(═O)—SR 10 , —C(═S)—SR 10 , —(═O)—NR 11 R 12 , —C(═S)—NR 11 R 12 , —S(O) 2 —R 13 , or —S(O) 2 —NR 14 R 15 ,

or R 3 and R 4 together are ═CR 16 if R 2 and R 3 are not joined to one another via two to six carbon atoms and do not form a ring,

R 5 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, SF 5 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -haloalkyl)(C 1 -C 4 -alkoxy)imino, or C 3 -C 6 -trialkylsilyl, or

two radicals R 5 form, via adjacent carbon atoms, a ring which is —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH—CH—) 2 —, —OCH 2 O—, —O(CH 2 ) 2 O—, —OCF 2 O—, —(CF 2 ) 2 O—, —O(CF 2 ) 2 O—, —(CH═CH—CH═N)—, or —(CH═CH—N═CH)—, or

two radicals R 5 , form via adjacent carbon atoms the fused rings below, which are optionally substituted one or more times by identical or different substituents, the substituents being selectable independently of one another from hydrogen, cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -halocycloalkyl, halogen, C 1 -C 6 -alkoxy, C 1 -C 4 -alkylthio(C 1 -C 6 -alkyl), C 1 -C 4 -alkylsulphinyl(C 1 -C 6 -alkyl), C 1 -C 4 -alkylsulphonyl(C 1 -C 6 -alkyl), C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, or C 3 -C 6 -cycloalkylamino, or

n is 0 to 3,

X is O or S,

R 6 is C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1-4 -sulphinyl, C 1 -C 4 -alkylsulphony, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halogen, cyano, nitro, or C 3 -C 6 -trialkylsilyl,

Q X is a heteroaromatic 5- or 6-membered ring which is substituted one or more times by identical or different substituents R 7 and which may contain 1-3 heteroatoms from N, S, or O,

A is optionally singly or multiply substituted —(C 1 -C 6 -alkylene)-, —(C 1 -C 6 -alkenylene)-, —(C 1 -C 6 -alkynylene)-, —R 17 —(C 3 -C 6 -cycloalkyl)-R 17 —, —R 17 —O—R 17 —, —R 17 —S—R 17 —, —R 17 —S(═O)—R 17 , —R 17 —S(═O) 2 —R 17 —, —R 17 —NH—(C 1 -C 6 -alkyl)-, —R 17 —N(C 1 -C 6 -alkyl)-R 17 —, —R 17 —C═NO(C 1 -C 6 -alkyl)-, —CHCO 2 (C 1 -C 6 -alkyl)-, —R 17 —C(═O)—R 17 —, —R 17 —C(O)NH—R 17 —, —R 17 —C(═O)N(C 1 -C 6 -alkyl)-R 17 , —R 17 —C(═O)NHNH—R 17 —, —R 17 —C(═O)N(C 1 -C 6 -alkyl)-NH—R 17 —, —R 17 —C(═O)NHN(C 1 -C 6 -alkyl)-R 17 —, —R 17 —O(C═O)—R 17 —, —R 17 —O(C═O)NH—R 17 —, —R 17 —O(C═O)N(C 1 -C 6 -alkyl)-R 17 —, —R 17 —S(═O) 2 NH—R 17 , —R 17 —S(═O) 2 N(C 1 -C 6 -alkyl)-R 17 —, —R 17 —S(C═O)—R 17 —, —R 17 —S(C═O)NH—R 17 —, —R 17 —S(═O)N(C 1 -C 6 -alkyl)-R 17 —, —R 17 —NHNH—R 17 —, —R 17 —NHN(C 1 -C 6 -alkyl)-R 17 —, —R 17 —N(C 1 -C 6 -alkyl)-NH—R 17 —, —R 17 —N(C 1 -C 6 -alkyl)-N(C 1 -C 6 -alkyl)-R 17 —, —R 17 —N═CH—O—R 17 —, —R 17 —NH(C═O)O—R 17 —, —R 17 —N(C 1 -C 6 -alkyl)-(C═O)O—R 17 —, —R 17 —NH(C═O)NH—R 17 —, —R 17 —NH(C═S)NH—R 17 —, —R 17 —NHS(═O) 2 —R 17 —, or —R 17 —N(C 1 -C 6 -alkyl)S(═O) 2 —R 17 —,

the substituents being selectable independently of one another from halogen, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or halo-C 1 -C 6 -alkyl,

where —(C 3 -C 6 -cycloalkyl)- in the ring may optionally contain 1 to 2 heteroatoms selected from N, S, or O,

R 17 is linear or branched —(C 1 -C 6 -alkylene)- or is a direct bond, or

two or more radicals R 17 independently of one another are linear or branched —(C 1 -C 6 -alkylene)-, or are a direct bond,

Q Y is a 5- or 6-membered, partially saturated or saturated heterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system or is phenyl, the ring or ring system being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, 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, CO 2 H, CO 2 NH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, tri(C 1 -C 2 )alkylsilyl, or (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino,

or the substituents being selectable independently of one another from phenyl or a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be substituted one or more times by identical or different 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, or C 1 -C 4 -haloalkoxy substituents,

R 7 is C 3 -C 6 -cycloalkyl or

R independently at each occurrence is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphonyl, or (C 1 -C 4 -alkyl)C 1 -C 4 -alkoxyimino,

m is 0 to 4,

Z is N, CH, CF, CCl, CBr or CI,

R 8 is hydrogen or is C 1 -C 6 -alkyl, 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 or C 4 -C 12 -bicycloalkyl, each of which is optionally substituted one or more times by identical or different substituents, the substituents being selectable independently of one

another from halogen, 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 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkylsulphimino, C 1 -C 4 -alkylsulphimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulphoximino, C 1 -C 4 -alkylsulphoximino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphoximino-C 2 -C 5 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 3 -C 6 -trialkylsilyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, a phenyl ring or a 3- to 6-membered unsaturated, partially saturated or saturated heterocycle, the phenyl ring or heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, 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, (C═O)OH, CONH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkylamino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, tri(C 1 -C 2 )alkylsilyl, or (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, or

R 8 is a phenyl ring or a 3- to 6-membered unsaturated, partially saturated or saturated heterocycle, the heteroatoms being selected from N, S, or O, where the phenyl ring or heterocycle is optionally substituted one or more times by identical or different substituents, and where the substituents are selectable independently of one another from hydrogen, 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, (C═O)OH, CONH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphony C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, tri(C 1 -C 2 )alkylsilyl, or (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino,

R 9 , R 10 , R 13 , R 14 and R 15 independently of one another are C 1 -C 6 -alkyl, 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 or C 4 -C 12 -bicycloalkyl, each of which is optionally substituted one or more times by identical or different substituents, the substituents being selectable independently of one another from halogen, 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 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkylsulphimino, C 1 -C 4 -alkylsulphimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulphoximino, C 1 -C 4 -alkylsulphoximino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphoximino-C 2 -C 5 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, C 3 -C 6 -trialkylsilyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, a phenyl ring or a 3- or 6-membered unsaturated, partially saturated or saturated heterocycle, the phenyl ring or heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, 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, (C═O)OH, CONH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, tri(C 1 -C 2 )alkylsilyl or (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, or

R 9 , R 10 , R 13 , R 14 and R 15 independently of one another are a phenyl ring or are a 3- to 6-membered unsaturated, partially saturated or saturated heterocycle, the heteroatoms being selected from N, S, or O, the phenyl ring or heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, 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, (C═O)OH, CONH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, tri(C 1 -C 2 )alkylsilyl, or (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino,

R 11 and R 12 independently of one another are hydrogen or are R 9 ,

R 16 is a phenyl ring or is a 5- or 6-membered heteroaromatic ring, the heteroatoms being selected from the series N, S, or O, the ring being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, 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, (C═O)OH, CONH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, tri(C 1 -C 2 )alkyl or (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino,

and N-oxides and salts thereof.

2. The anthranilic acid derivative of general formula (I) according to claim 1 ,

in which

R 1 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, cyano(C 1 -C 6 -alkyl), C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphinyl-C 1 -C 4 -alkyl, or C 1 -C 4 -alkylsulphonyl-C 1 -C 4 -alkyl,

R 2 and R 3 independently of one another are hydrogen or are C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl optionally substituted one or more times by identical or different substituents, the substituents being selectable independently of one another from halogen, cyano, C 2 -C 6 -alkoxycarbonyl, or C 2 -C 6 -alkylcarbonyl,

R 4 is —C(═O)—R 8 , —C(═O)—OR 9 , —C(═O)—SR 10 , —C(═O)—NR 11 R 12 , —S(O) 2 —R 13 , or —S(O) 2 —NR 14 R 15 ,

R 5 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, or C 1 -C 4 -haloalkylthio, or

two adjacent radicals R 5 are —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH═CH—) 2 —, —OCH 2 O—, —O(CH 2 ) 2 O—, —OCF 2 O—, —(CF 2 ) 2 O—, —O(CF 2 ) 2 O—, —(CH═CH—CH═N)—, or —(CH═CH—N═CH)—,

n is 0 to 2,

X is O or S,

R 6 is C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halogen, cyano, nitro, or C 3 -C 6 -trialkylsilyl,

Q X is a heteroaromatic 5-membered ring which is substituted one or more times by identical or different substituents R 7 and which may contain 1-3 heteroatoms from N, O, or S, or is a heteroaromatic 6-membered ring which is substituted one or more times by identical or different substituents R 7 and which may contain 1-3 nitrogen atoms,

A is optionally singly or multiply substituted —(C 1 -C 4 -alkylene)-, —(C 1 -C 4 -alkenylene)-, —(C 1 -C 4 -alkynylene)-, —R 17 —(C 3 -C 6 -cycloalkyl)-R 17 —, —R 17 —, —R 17 —S—R 17 —, —R 17 —S(—O)—R 17 —, —R 17 —S(═O) 2 —R 17 —, —R 17 —NH—(C 1 -C 4 -alkyl)-, —R 17 —N(C 1 -C 4 -alkyl)-R 17 —, —R 17 —C═NO(C 1 -C 4 -alkyl)-, —R 17 —C(═O)—R 17 —, —R 17 —C(═S)—R 17 , —R 17 —C(═O)NH—R 17 —, —R 17 —C(═O)N(C 1 -C 4 -alkyl)-R 17 —, —R 17 —S(═O) 2 NH—R 17 —, —R 17 —S(═O) 2 N(C 1 -C 4 -alkyl)-R 17 —, —R 17 —NH(C═O)O—R 17 —, —R 17 —N(C 1 -C 4 -alkyl)-(C═O)O—R 17 —, —R 17 —NH(C═O)NH—R 17 —, —R 17 —NHS(═O) 2 —R 17 —, or —R 17 —N(C 1 -C 4 -alkyl)S(═O) 2 —R 17 —, the substituents being selectable independently of one another from halogen, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or halo-C 1 -C 6 -alkyl,

R 7 is the radical

or

R 7 is C 3 -C 6 -cycloalkoxy,

R independently at each occurrence is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylsulphonyl, or (C 1 -C 4 -alkyl)C 1 -C 4 -alkoxyimino,

m is 1, 2 or 3,

R 8 is hydrogen or singly or multiply identically or differently substituted C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, the substituents being selectable independently of one another from halogen, cyano, a phenyl ring or a 3- or 6-membered unsaturated, partially saturated or saturated heterocycle, the phenyl ring or heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen, cyano, NO 2 , C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy, or

R 8 is a phenyl ring or is a 3- to 6-membered unsaturated, partially saturated or saturated heterocycle, the heteroatoms being selected from N, S, or O, and the phenyl ring or heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, C 1 -C 6 -haloalkyl, halogen, or cyano,

Z is N, CH, CF, CCl, CBr, or CI,

R 9 , R 10 , RR 13 , R 14 and R 15 independently of one another are singly or multiply identically or differently substituted C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, the substituents being selectable independently of one another from halogen, cyano, a phenyl ring or a 3- to 6-membered unsaturated, partially saturated or saturated heterocycle, the phenyl ring or heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen, cyano, NO 2 , C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy, or

R 9 , R 10 , R 13 , R 14 , and R 15 independently of one another are a phenyl ring or are a 3- to 6-membered unsaturated, partially saturated or saturated heterocycle, the heteroatoms being selected from N, S and O, the phenyl ring or the heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen, or cyano,

R 11 and R 12 independently of one another are hydrogen or are R 9 ,

R 16 is a phenyl ring or is a 5- or 6-membered heteroaromatic frig where the heteroatoms are selected from N, S, or O, the ring being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen, cyano, NO 2 , C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy,

R 17 is linear or branched —(C 1 -C 4 -alkylene)- or is a direct bond,

Q Y is a 5- or 6-membered, partially saturated or a saturated heterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, the heteroatoms being selectable from N, S, or O, the ring or the ring system being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, 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, CO 2 H, CO 2 NH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, or C 1 -C 4 -haloalkylsulphonyl,

or the substituents being selectable independently of one another from phenyl or a 5- or 6-membered heteroaromatic ring, where the phenyl or the ring may optionally be substituted one or more times by identical or different 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, or C 1 -C 4 -haloalkoxy substituents.

3. The anthranilic acid derivative of general formula (I) according to either of claim 1 or 2 ,

in which

R 1 is hydrogen, methyl, ethyl, cyclopropyl, cyanomethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, or methylsulphonylmethyl,

R 2 and R 3 independently of one another are hydrogen, methyl ethyl, isopropyl, or tert-butyl,

R 4 is —C(═O)—R 8 or —C(═O)—OR 9 ,

R 5 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, halogen, cyano, or C 1 -C 2 -haloalkoxy, or

two adjacent radicals R 5 are —(CH 2 ) 4 —, —(CH═CH—) 2 —, —O(C 1-12 ) 2 O—, —O(CF 2 ) 2 O—, —(CH═CH—CH═N)— or —(CH═CH—N═CH)—,

n is 1 or 2,

X is O,

R 6 is C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, fluoro, chloro, bromo, iodo, cyano, nitro, or C 3 -C 6 -trialkylsilyl,

Q X is a heteroaromatic 5- or 6-membered ring which is substituted one or more times by identical or different substituents R 7 and is selected from the group consisting of furan, thiophene, pyrazole, triazole, imidazole, thiazole, oxazole, isoxazole, isothiazole, thiadiazole, oxadiazole, pyrrole, pyridine, pyrimidine, pyridazine and pyrazine,

A is —CH 2 —, —CH 2 O—, —CH 2 OCH 2 —, —CH 2 S—, —CH 2 SCH 2 —, —CH 2 N(C 1 -C 4 -alkyl)-, —CH 2 N(C 1 -C 4 -alkyl)CH 2 —, —CH(Hal)-, —C(halo) 2 -, —CH(CN)—, —CH 2 (CO)—, —CH 2 (CS)—, —CH 2 CH(OH)—, -cyclopropyl-, —CH 2 (CO)CH 2 —, —CH(C 1 -C 4 -alkyl)-, —C(Di—C 1 -C 6 -alkyl)-, —CH 2 CH 2 —, —CH═CH—, or —C═NO(C 1 -C 6 -alkyl)-,

R 7 is the radical

R independently at each occurrence is hydrogen, halogen, cyano, or C 1 -C 4 -haloalkyl,

m is 1 or 2,

Z is N, CH, CF, CCl, or CBr,

R 8 is hydrogen, or is methyl, ethyl, isopropyl or tert-butyl optionally singly or multiply identically or differently substituted, the substituents being selectable independently of one another from halogen, cyano, phenyl or pyridyl, where the phenyl or pyridyl is optionally substituted one or more times by identical or different hydrogen, trifluoromethyl, cyano, fluoro, chloro, bromo, or trifluoromethoxy substituents, or

R 8 is phenyl, or pyridyl or is a 3- to 6-membered saturated heterocycle, containing 1-2 heteroatoms from N, S, or O, the phenyl or pyridyl ring or heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen, or cyano,

R 9 , R 10 , R 13 , R 14 and R 15 independently of one another are optionally singly or multiply identically or differently substituted methyl, ethyl, isopropyl or tert-butyl, the substituents being selectable independently of one another from halogen, cyano, phenyl or pyridyl, where phenyl or pyridyl is optionally substituted by one or more identical or different trifluoromethyl, cyano, fluoro, chloro, or trifluoromethoxy substituents, or

R 9 , R 10 , R 13 , R 14 and R 15 independently of one another are phenyl, pyridyl or are a 3- to 6-membered saturated heterocycle containing 1-2 heteroatoms from N, S, or O, the phenyl or pyridinyl ring or the heterocycle being optionally substituted one or more times by identical or different substituents, and the substituents being selectable independently of one another from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen, or cyano,

R 11 and R 12 independently of one another are hydrogen or are R 9 ,

R 16 is phenyl, pyridyl, pyrimidinyl, furan, or thiophene which is optionally substituted by one or more identical or different substituents, the substituents being selectable independently of one another from hydrogen, trifluoromethyl, cyano, fluoro, chloro, or trifluoromethoxy,

R 17 is methylene, ethylene, propylene, isopropylene, n-butylene, sec-butylene, isobutylene, or a direct bond,

Q Y is an optionally singly or multiply identically or differently substituted 5- or 6-membered heteroaromatic ring from the series Q-1 to Q-53, Q-58 to Q-59, or Q-62 to Q-63, or an aromatic 9-membered fused heterobicyclic ring system Q-54 to Q-56, or a 5-membered heterocyclic ring Q-60 or Q-61, the substituents being selectable independently of one another from C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 2 -alkoxy, halogen, cyano, hydroxyl, nitro, or C 1 -C 2 -haloalkoxy,

or the substituents being selectable independently of one another from phenyl or a 5- or 6-membered heteroaromatic ring, where the phenyl or the ring may optionally be substituted one or more times by identical or different 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 -haloeycloalkyl, halogen, CN, NO 2 , OH, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy substituents

4. A mixture comprising at least two compounds of the general formula (I) according to claim 3 , in which Qy of at least a first compound is Q62, and Qy of at least a second compound is Q63, and wherein the ratio of said at least first compound to said at least second compound being 60:40 to 99:1.

5. A mixture comprising at least two compounds of the general formula (I) according to claim 3 , in which Qy of at least a first compound is Q58, and Qy of at least a second compounds is Q59, and wherein the ratio of said at least first compound to said at least second compound being 60:40 to 99:1.

6. A compound of general formula (VII),

in which R 1 , R 2 , R 3 , R 5 , R 6 , n, Qx, A and Qy are as defined in claim 1 .

7. An agrochemical composition comprising at least one compound of formula (I) according to claim 1 or the mixture of compounds of formula (I) according to claim 5 or claim 6 , and one or more extenders and/or one or more surface-active substances.

8. A process for producing an agrochemical composition comprising mixing at least one compound of the general formula (I) according to claim 1 or mixing the mixture of compounds of the general formula (I) according to claim 5 or claim 6 with one or more extenders and/or one or more surface-active substances.

9. An anthranilic acid derivative having the following structural formula:

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035051/0325 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2011
From: FISCHER, RUDIGER; WROBLOWSKY, HEINZ-JUERGEN; GESING, ERNST RUDOLF; GRONDAL, CHRISTOPH; HENSE, ACHIM; VOERSTE, ARND
To: BAYER CROPSCIENCE AG
Reel/Frame 026513/0737 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2011
From: FISCHER, RUDIGER; WROBLOWSKY, HENIZ-JUERGEN; GESING, ERNST RUDOLF; GRONDAL, CHRISTOPH; HENSE, ACHIM; VOERSTE, ARND
To: BAYER CROPSCIENCE AG
Reel/Frame 026284/0677 →