Hydrazine-substituted anthranilic acid derivatives

An anthranilic acid derivative of general formula (I)

• in which
• R1 is hydrogen, amino, or hydroxyl or is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-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, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, (C1-C4-alkoxy)carbonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, or (C1-C4-alkyl)C3-C6-cycloalkylamino,
• R2, R3 independently of one another are hydrogen, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C2-C6-alkylaminocarbonyl, or C2-C6-dialkylaminocarbonyl or are C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-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, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylsulphimino, C1-C4-alkylsulphimino-C1-C4-alkyl, C1-C4-alkylsulphimino-C2-C5-alkylcarbonyl, C1-C4-alkylsulphoximino, C1-C4-alkylsulphoximino-C1-C4-alkyl, C1-C4-alkylsulphoximino-C2-C5-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, or C3-C6-trialkylsilyl, or
• R2 and R3 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, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, (C═O)OH, (C═O)NH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkyl sulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, tri(C1-C2)alkylsilyl, or (C1-C4-alkyl)(C1-C4-alkoxy)imino, or
• R2 and R3 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 C1-C2-alkyl, C1-C2-haloalkyl, halogen, cyano, amino, C1-C2-alkoxy, or C1-C2-haloalkoxy,
• R4 is a group selected from —C(═S)—R8, —C(═O)—R8, —C(═O)—OR9, —C(—S)—OR9, —C(═O)—SR10, —C(═S)—SR10, —(═O)—NR11R12, —C(═S)—NR11R12, —S(O)2—R13, or —S(O)2—NR14R15,
• or R3 and R4 together are ═CR16 if R2 and R3 are not joined to one another via two to six carbon atoms and do not form a ring,
• R5 is hydrogen, halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, SF5, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C4-alkoxy)imino, (C1-C4-alkyl)(C1-C4-alkoxy)imino, (C1-C4-haloalkyl)(C1-C4-alkoxy)imino, or C3-C6-trialkylsilyl, or
• two radicals R5 form, via adjacent carbon atoms, a ring which is —(CH2)3—, —(CH2)4—, —(CH2)5—, —(CH—CH—)2—, —OCH2O—, —O(CH2)2O—, —OCF2O—, —(CF2)2O—, —O(CF2)2O—, —(CH═CH—CH═N)—, or —(CH═CH—N═CH)—, or
• two radicals R5, 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, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, C1-C6-alkoxy, C1-C4-alkylthio(C1-C6-alkyl), C1-C4-alkylsulphinyl(C1-C6-alkyl), C1-C4-alkylsulphonyl(C1-C6-alkyl), C1-C4-alkylamino, di(C1-C4-alkyl)amino, or C3-C6-cycloalkylamino, or
• n is 0 to 3,
• X is O or S,
• R6 is C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-4-sulphinyl, C1-C4-alkylsulphony, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, halogen, cyano, nitro, or C3-C6-trialkylsilyl,
• QX is a heteroaromatic 5- or 6-membered ring which is substituted one or more times by identical or different substituents R7 and which may contain 1-3 heteroatoms from N, S, or O,
• A is optionally singly or multiply substituted —(C1-C6-alkylene)-, —(C1-C6-alkenylene)-, —(C1-C6-alkynylene)-, —R17—(C3-C6-cycloalkyl)-R17—, —R17—O—R17—, —R17—S—R17—, —R17—S(═O)—R17, —R17—S(═O)2—R17—, —R17—NH—(C1-C6-alkyl)-, —R17—N(C1-C6-alkyl)-R17—, —R17—C═NO(C1-C6-alkyl)-, —CHCO2(C1-C6-alkyl)-, —R17—C(═O)—R17—, —R17—C(O)NH—R17—, —R17—C(═O)N(C1-C6-alkyl)-R17, —R17—C(═O)NHNH—R17—, —R17—C(═O)N(C1-C6-alkyl)-NH—R17—, —R17—C(═O)NHN(C1-C6-alkyl)-R17—, —R17—O(C═O)—R17—, —R17—O(C═O)NH—R17—, —R17—O(C═O)N(C1-C6-alkyl)-R17—, —R17—S(═O)2NH—R17, —R17—S(═O)2N(C1-C6-alkyl)-R17—, —R17—S(C═O)—R17—, —R17—S(C═O)NH—R17—, —R17—S(═O)N(C1-C6-alkyl)-R17—, —R17—NHNH—R17—, —R17—NHN(C1-C6-alkyl)-R17—, —R17—N(C1-C6-alkyl)-NH—R17—, —R17—N(C1-C6-alkyl)-N(C1-C6-alkyl)-R17—, —R17—N═CH—O—R17—, —R17—NH(C═O)O—R17—, —R17—N(C1-C6-alkyl)-(C═O)O—R17—, —R17—NH(C═O)NH—R17—, —R17—NH(C═S)NH—R17—, —R17—NHS(═O)2—R17—, or —R17—N(C1-C6-alkyl)S(═O)2—R17—,
• the substituents being selectable independently of one another from halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, or halo-C1-C6-alkyl,
• where —(C3-C6-cycloalkyl)- in the ring may optionally contain 1 to 2 heteroatoms selected from N, S, or O,
• R17 is linear or branched —(C1-C6-alkylene)- or is a direct bond, or
• two or more radicals R17 independently of one another are linear or branched —(C1-C6-alkylene)-, or are a direct bond,
• QY 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, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, CO2H, CO2NH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, tri(C1-C2)alkylsilyl, or (C1-C4-alkyl)(C1-C4-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 C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, NO2, OH, C1-C4-alkoxy, or C1-C4-haloalkoxy substituents,
• R7 is C3-C6-cycloalkyl or
• R independently at each occurrence is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-haloalkylsulphonyl, or (C1-C4-alkyl)C1-C4-alkoxyimino,
• m is 0 to 4,
• Z is N, CH, CF, CCl, CBr or CI,
• R8 is hydrogen or is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C6-alkyl or C4-C12-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, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylsulphimino, C1-C4-alkylsulphimino-C1-C4-alkyl, C1-C4-alkylsulphimino-C2-C5-alkylcarbonyl, C1-C4-alkylsulphoximino, C1-C4-alkylsulphoximino-C1-C4-alkyl, C1-C4-alkylsulphoximino-C2-C5-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl, amino, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-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, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, (C═O)OH, CONH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkylamino, C3-C6-cycloalkylamino, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, tri(C1-C2)alkylsilyl, or (C1-C4-alkyl)(C1-C4-alkoxy)imino, or
• R8 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, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, (C═O)OH, CONH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphony C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, tri(C1-C2)alkylsilyl, or (C1-C4-alkyl)(C1-C4-alkoxy)imino,
• R9, R10, R13, R14 and R15 independently of one another are C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C6-alkyl or C4-C12-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, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylsulphimino, C1-C4-alkylsulphimino-C1-C4-alkyl, C1-C4-alkylsulphimino-C2-C5-alkylcarbonyl, C1-C4-alkylsulphoximino, C1-C4-alkylsulphoximino-C1-C4-alkyl, C1-C4-alkylsulphoximino-C2-C5-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl, amino, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-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, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, (C═O)OH, CONH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, tri(C1-C2)alkylsilyl or (C1-C4-alkyl)(C1-C4-alkoxy)imino, or
• R9, R10, R13, R14 and R15 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, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, (C═O)OH, CONH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, tri(C1-C2)alkylsilyl, or (C1-C4-alkyl)(C1-C4-alkoxy)imino,
• R11 and R12 independently of one another are hydrogen or are R9,
• R16 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, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, (C═O)OH, CONH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, tri(C1-C2)alkyl or (C1-C4-alkyl)(C1-C4-alkoxy)imino,
• and N-oxides and salts thereof.