Heteroaroyl-substituted serine amides

A heteroaroyl-substituted serineamide of the formula (I)

• in which the variables are as defined below:
• A is 5- or 6-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or one oxygen, or sulfur atom, which heteroaryl may be partially or fully halogenated and/or may carry 1 to 3 radicals selected from the group consisting of cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy and C1-C6-alkoxy-C1-C4-alkyl;
• R1, R2 are hydrogen, hydroxyl or C1-C6-alkoxy;
• R3 is C1-C6-alkyl, C1-C4-cyanoalkyl or C1-C6-haloalkyl;
• R4 is hydrogen, C1-C6-alkyl, 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, aminocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, 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, (C1-C6)alkylaminothiocarbonyl, di-(C1-C6-alkyl)aminothiocarbonyl, (C1-C6-alkyl)cyanoimino, (amino)cyanoimino, [(C1-C6-alkyl)amino]cyanoimino, [di(C1-C6-alkyl) -amino]cyanoimino, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxyimino-C1-C6-alkyl, N—(C1-C6-alkylamino)imino-C 1-C6-alkyl, N-(di-C1-C6-alkylamino)imino -C1-C6-alkyl or tri-C1-C4-alkylsilyl,
• 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-C6-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkyl-C1-C4-alkoxycarbonylamino, 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, or phenyl-C1-C6-alkylcarbonyl,
• where the phenyl radical 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;
• or
• SO2R7;
• R5 and R6 together with the carbon atom to which they are attached form a first 3- to 12-membered saturated or partially unsaturated ring which is carbocyclic or contains 1 to 3 nitrogen atoms, 0 to 3 nitrogen atoms and 1 oxygen or sulfur atom, 0 to 2 nitrogen atoms and 2 oxygen or sulfur atoms, 0 or 1 nitrogen atom and 1 oxygen and 1 sulfur atom, 3 oxygen or sulfur atoms, 2 oxygen atoms and 1 sulfur atom, or 1 oxygen atom and 2 sulfur atoms,
• where the first ring is unsubstituted or substituted by 1 to 3 substituents, in the case of halogen also up to the maximum possible number, selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, trialkylsilyloxy, formyl, C1-C6-alkyl -carbonyl, C3-C6-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylamino-carbonyl, C3-C6-alkynylaminocarbonyl, 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) -amino-carbonyl, 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-alkoxyimino-C1-C6-alkyl, N—(C1-C6-alkylamino)-imino-C1-C6-alkyl or N-(di-C1-C6-alkylamino)-imino-C1-C6-alkyl, amino, formylamino, C1-C6-alkylcarbonylamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylamino, formyl -C1-C6-alkylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, di-(C1-C6-alkyl)amino, amino-carbonylamino, C1-C6-alkylamino-carbonylamino, di(C1-C6-)alkylamino-carbonylamino, C1-C6-alkylthio, C1-C6alkylsulfonyl, alkylsulfonyloxy, alkylsulfonylamino, C1-C6-alkylsulfinyl, C1-C6-alkylsulfimino, C1-C6-alkyl-C1-C6-alkylsulfimino, carbonyl, thiocarbonyl, imino, alkylimino, hydroxyimino, alkoxyimino, aminoimino, alkylaminoimino, di-(alkyl)aminoimino, alkylcarbonylaminoimino, alkylsulfonylaminoimino, C1-C6-vinylidenyl, C1-C6-alkoxyvinylidene, di-C1-C6-alkylaminovinylidene,
• 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, heterocyclyl -sulfonylaminocarbonyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclyloxy -carbonyl, heterocyclylaminocarbonyl, N—(C1-C6-alkyl)-N-(heterocyclyl) -aminocarbonyl and heterocyclyl-C1-C6-alkylcarbonyl,
• wherein the phenyl and the heterocyclyl radical of the 17 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of nitro, cyano, C1-C4alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
• and where the first ring is monocyclic or fused to a second 3- to 7-membered saturated, partially unsaturated or fully unsaturated ring which is carbocyclic or contains 1 to 3 nitrogen atoms, 0 to 2 nitrogen atoms and 1 oxygen atom or sulfur atom, 0 to 1 nitrogen atom and 2 oxygen atoms or sulfur atoms, 0 to 1 nitrogen atom and 1 oxygen atom and 1 sulfur atom, 2 oxygen atoms and 1 sulfur atom, or 1 oxygen atom and 2 sulfur atoms,
• where the fused ring is unsubstituted or substituted by 1 to 3 substituents, in the case of halogen also up to the maximum possible number, selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C3-C6-alkenyl, C1-C6-haloalkyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy and C1-C6-alkylsulfonyl,
• and where the first ring is not bridged or bridged by a 1- to 4-membered saturated or unsaturated chain which contains no heteroatoms or contains 1 to 2 nitrogen atoms, 0 or 1 nitrogen atom and 1 oxygen atom or 1 sulfur atom, 0 or 1 nitrogen atom and 2 oxygen atoms or 2 sulfur atoms, or 0 or 1 nitrogen atom and 1 oxygen atom and 1 sulfur atom,
• where the bridge is unsubstituted or substituted by 1 to 3 substituents, in the case of halogen also up to the maximum possible number, selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C3-C6-alkenyl, C1-C6-haloalkyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy and C1-C6-alkylsulfonyl;
• R7 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.