Benzoyl-substituted phenylalanineamides

A herbicidal composition comprising a herbicidally effective amount of at least one benzoyl-substituted phenylalanineamide of the formula I

• in which the variables are as defined below:
• R1 is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, nitro, hydroxycarbonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkylthio, or phenyl;
• R2, R3, R4, R5 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, nitro, amino, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylthio or C1-C6-alkoxycarbonyl;
• R6, R7 are hydrogen, hydroxyl or C1-C6-alkoxy;
• R8 is C1-C6-alkyl, C1-C4-cyanoalkyl or C1-C6-haloalkyl;
• R9 is OR6, SR17 or NR18R19;
• R10 is hydrogen or C1-C6-alkyl;
• R11, R12 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, hydroxyl, nitro, hydroxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkyl, tri(C1-C6-alkyl)silyloxy-C1-C4-alkyl, C1-C4-alkylthio, (hydroxycarbonyl)-C1-C6-alkyl, (C1-C6-alkoxycarbonyl)-C1-C6-alkyl, (hydroxycarbonyl)-C2-C6-alkenyl, (C1-C6-alkoxycarbonyl)-C2-C6-alkenyl, (hydroxycarbonyl)-C1-C4-alkoxy, (C1-C4-alkoxycarbonyl)-C1-C4-alkoxy, (C1-C4-alkylcarbonyl)oxy-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkoxy-C1-C4-alkyl, (C1-C4-alkylsulfonyl)oxy-C1-C4-alkyl, C1-C4-alkyl-O—C(O)-[C1-C4-alkyl-O]3—C1-C4-alkyl, carbamoyloxy-C1-C4-alkyl, (C1-C4-alkylaminocarbonyl)oxy-C1-C4-alkyl, [di(C1-C4-alkyl)aminocarbonyl]oxy-C1-C4-alkyl, [(C1-C4-haloalkylsulfonyl)aminocarbonyl]oxy-C1-C4-alkyl, benzyloxy, where the phenyl ring may be substituted by 1 to 3 radicals from the group consisting of halogen and C1-C4-alkyl, amino, C1-C4-alkylamino, di(C1-C4-alkyl)amino, (C1-C4-alkylsulfonyl)amino, C1-C4-(haloalkylsulfonyl)amino, (C1-C4-alkylcarbonyl)amino, carbamoylamino, (C1-C4-alkylamino)carbonylamino, [di(C1-C4-alkyl)amino]carbonylamino, [(C1-C4-haloalkylsulfonyl)aminocarbonyl]-amino, phenyl or heterocyclyl, where the phenyl and the heterocyclyl radical of the two last-mentioned substituents may carry one to three radicals from the following group:
• halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, hydroxycarbonyl and C1-C6-alkoxycarbonyl;
• R13, R14, R15 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, nitro, hydroxyl, C1-C4-alkylthio or benzyloxy;
• R16, R17, R18 are hydrogen, C1-C6-alkyl, tri(C1-C6-alkyl)silyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl, formyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, N—(C3-C6-alkenyl)-N—(C1-C6-alkyl)aminocarbonyl, N—(C3-C6-alkynyl)-N—(C1-C6-alkyl)aminocarbonyl, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)aminocarbonyl, N—(C3-C6-alkenyl)-N—(C1-C6-alkoxy)aminocarbonyl, N—(C3-C6-alkynyl)-N—(C1-C6-alkoxy)aminocarbonyl, di(C1-C6-alkyl)aminothiocarbonyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxyimino-C1-C6-alkyl, N—(C1-C6-alkylamino)imino-C1-C6-alkyl or N-(di-C1-C6-alkylamino)imino-C1-C6-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)-aminocarbonyl or C1-C4-alkylcarbonyloxy;
• phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl, phenylcarbonyl-C1-C6-alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N—(C1-C6-alkyl)-N-(phenyl)aminocarbonyl, phenyl-C1-C6-alkylcarbonyl, heterocyclyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl, heterocyclylsulfonylaminocarbonyl, N—(C1-C6-alkyl)-N-(heterocyclyl)aminocarbonyl or heterocyclyl-C1-C6-alkylcarbonyl,
• where the phenyl and the heterocyclyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy
• SO2R20;
• —C(O)—[C1-C4-alkyl-O]3—C1-C4-alkyl;
• or
• —C(O)—O—C1-C4-alkyl-O-phenyl, where the phenyl radical may optionally be substituted by one to three radicals from the group consisting of halogen and C1-C4-alkyl;
• R19 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl,
• where the alkyl and cycloalkyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C3-C6-cycloalkyl, C1-C9 alkoxy, C1-C4-alkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)amino-carbonyl or C1-C4-alkylcarbonyloxy;
• or
• phenyl, phenyl-C1-C6-alkyl, heterocyclyl or heterocyclyl-C1-C6-alkyl, where the phenyl and the heterocyclyl radicals of the 4 last-mentioned substituents may be partially or fully halogenated, and/or may carry one to three of the following groups:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• R20 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups:
• C1-C6-alkyl, C1-C6-haloalkyl or C1-C4-alkoxy;
• or an agriculturally useful salt thereof and auxiliaries customary for formulating crop protection agents.

A process for preparing herbicidal compositions comprising mixing a herbicidally effective amount of at least one benzoyl-substituted phenylalanineamide of the formula I

• in which the variables are as defined below:
• R1 is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, nitro, hydroxycarbonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkylthio, or phenyl;
• R2, R3, R4, R5 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, nitro, amino, C1-C6-alkylamino, di(C1-C6-amino C1-C6-alkylthio or C1-C6-alkoxycarbonyl;
• R6, R7 are hydrogen, hydroxyl or C1-C6-alkoxy;
• R8 is C1-C6-alkyl, C1-C4-cyanoalkyl or C1-C6-haloalkyl;
• R9 is OR16, SR17 or NR18R19;
• R10 is hydrogen or C1-C6-alkyl;
• R11, R12 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, hydroxyl, nitro, hydroxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkyl, tri(C1-C6-alkyl)silyloxy-C1-C4-alkyl, C1-C4-alkylthio, (hydroxycarbonyl)-C1-C6-alkyl, (C1-C6-alkoxycarbonyl)-C1-C6-alkyl, (hydroxycarbonyl)-C2-C6-alkenyl, (C1-C6-alkoxycarbonyl)-C2-C6-alkenyl, (hydroxycarbonyl)-C1-C4-alkoxycarbonyl-C1-C4-alkoxy, (C1-C4-alkylcarbonyl)oxy-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkoxy-C1-C4-alkyl, (C1-C4-alkylsulfonyl)oxy-C1-C4-alkyl, C1-C4-alkyl-O—C(O)-[C1-C4-alkyl-O]3—C1-C4-alkyl, carbamoyloxy-C1-C4-alkyl, (C1-C4-alkylaminocarbonyl)oxy-C1-C4-alkyl, [di(C1-C4-alkyl)aminocarbonyl]oxy-C1-C4-alkyl, [(C1-C4-haloalkylsulfonyl)aminocarbonyl]oxy-C1-C4-alkyl, benzyloxy, where the phenyl ring may be substituted by 1 to 3 radicals from the group consisting of halogen and C1-C4-alkyl, amino, C1-C4-alkylamino, di(C1-C4-alkyl)amino, (C1-C4-alkylsulfonyl)amino, C1-C4-(haloalkylsulfonyl)amino, (C1-C4-alkylcarbonyl)amino, carbamoylamino, (C1-C4-alkylamino)carbonylamino, [di(C1-C4-alkyl)amino]carbonylamino, [(C1-C4-haloalkylsulfonyl)aminocarbonyl]-amino, phenyl or heterocyclyl, where the phenyl and the heterocyclyl radical of the two last-mentioned substituents may carry one to three radicals from the following group:
• halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, hydroxycarbonyl and C1-C6-alkoxycarbonyl;
• R13, R14, R15 are hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, nitro, hydroxyl, C1-C4-alkylthio or benzyloxy;
• R16, R17, R18 are hydrogen, C1-C6-alkyl, tri(C1-C6-alkyl)silyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl, formyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, N—(C3-C6-alkenyl)-N—(C1-C6-alkyl)aminocarbonyl, N—(C3-C6-alkynyl)-N—(C1-C6-alkyl)aminocarbonyl, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)aminocarbonyl, N—(C3-C6-alkenyl)-N—(C1-C6-alkoxy)aminocarbonyl, N—(C3-C6-alkynyl)-N—(C1-C6-alkoxy)aminocarbonyl, di(C1-C6-alkyl)aminothiocarbonyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxyimino-C1-C6-alkyl, N—(C1-C6-alkylamino)imino-C1-C6-alkyl or N-(di-C1-C6-alkylamino)imino-C1-C6-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)-aminocarbonyl or C1-C4-alkylcarbonyloxy;
• phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl, phenylcarbonyl-C1-C6-alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N—(C1-C6-alkyl)-N-(phenyl)aminocarbonyl, phenyl-C1-C6-alkylcarbonyl, heterocyclyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl, heterocyclylsulfonylaminocarbonyl, N—(C1-C6-alkyl)-N-(heterocyclyl)aminocarbonyl or heterocyclyl-C1-C6-alkylcarbonyl,
• where the phenyl and the heterocyclyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy
• SO2R20;
• —C(O)—[C1-C4-alkyl-O]3—C1-C4-alkyl;
• or
• —C(O)—O—C1-C4-alkyl-O-phenyl, where the phenyl radical may optionally be substituted by one to three radicals from the group consisting of halogen and C1-C4-alkyl;
• R19 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl,
• where the alkyl and cycloalkyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)amino-carbonyl or C1-C4-alkylcarbonyloxy;
• or
• phenyl, phenyl-C1-C6-alkyl, heterocyclyl or heterocyclyl-C1-C6-alkyl, where the phenyl and the heterocyclyl radicals of the 4 last-mentioned substituents may be partially or fully halogenated, and/or may carry one to three of the following groups:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• R20 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl,
• where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups:
• C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
• or an agriculturally useful salt thereof with auxiliaries customary for formulating crop protection agents.