Piperazine Compounds With Herbicidal Action

A piperazine compound of the formula I

• in which
• A1 is phenyl or pyridinyl where Ra is attached in the ortho-position to the point of attachment of A1;
• A2 is phenyl or thienyl;
• Y1, Y2 are oxygen,
• Ra is selected from the group consisting of halogen, cyano, nitro, SF5, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C5-C8-cycloalkenyl, C5-C8-cycloalkynyl, C3-C6-cycloalkyl-(C1-C6)-alkyl, C5-C8-cycloalkenyl-(C1-C6)-alkyl, C5-C8-cycloalkynyl-(C1-C6)-alkyl, C3-C6-cycloalkyl-(C2-C6)-alkenyl, C5-C8-cycloalkenyl-(C2-C6)-alkenyl, C5-C8-cycloalkynyl-(C2-C6)-alkenyl, C3-C6-cycloalkyl-(C2-C6)-alkynyl, C5-C8-cycloalkenyl-(C2-C6)-alkynyl, C5-C8-cycloalkynyl-(C2-C6)-alkynyl, C4-C10-alkadienyl, C2-C6-alkynyl, [tri-(C1-C6)-alkylsilyl]-(C2-C6)-alkynyl, C7-C8-cycloalkynyl, aryl, phenyl-(C1-C6)-alkyl, phenyl-(C2-C6)-alkenyl, phenyl-(C2-C6)-alkynyl, phenylsulfonyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, heterocyclyl-(C2-C6)-alkenyl, heterocyclyl-(C2-C6)-alkynyl, phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl, Z1P(O)(OR9)2, Z1P(O)(OR9)(R9a), Z2B(OR10)2, Z3COR11, Z4NR12R13, Z5CH═N—O—R14, Z6OR15, Z7SR16, Z7S(O)R16 and Z7SO2R16;
• where the abovementioned aliphatic, cyclic or aromatic moieties of the substituent Ra are unsubstituted or may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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;
• Rb, Rc, Rd, Re and Rf are each independently of one another hydrogen or have one of the meanings given for Ra;
• where two radicals Ra, Rb or Rc attached to adjacent ring atoms of A1 or two radicals Rd, Re or Rf attached to adjacent ring atoms of A2 may also be straight-chain C3-C6-alkylene which may be partially or fully halogenated and may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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, in which a CH2 group in C3-C6-alkylene may be replaced by a carbonyl group, thiocarbonyl group or sulfonyl group and in which one or two non-adjacent CH2 groups in C3-C6-alkylene may in each case be replaced by oxygen, sulfur or a group NR34, where R34 has one of the meanings given for R12;
• R1 and R2 independently of one another are selected from the group consisting of:
• cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C5-C8-cycloalkenyl, C3-C6-alkynyl, C7-C8-cycloalkynyl, C3-C6-cycloalkyl-(C1-C6)-alkyl, C5-C8-cyclo-alkenyl-(C1-C6)-alkyl, C5-C8-cycloalkynyl-(C1-C6)-alkyl, C3-C6-cycloalkyl-(C2-C6)-alkenyl, C5-C8-cycloalkenyl-(C2-C6)-alkenyl, C5-C8-cycloalkynyl-(C2-C6)-alkenyl, C3-C6-cycloalkyl-(C2-C6)-alkynyl, C5-C8-cycloalkenyl-(C2-C6)-alkynyl, C5-C8-cycloalkynyl-(C2-C6)-alkynyl, phenyl, phenyl-(C1-C6)-alkyl, phenyl-(C2-C6)-alkenyl, phenyl-(C2-C6)-alkynyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, heterocyclyl-(C2-C6)-alkenyl, heterocyclyl-(C2-C6)-alkynyl, phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl, C(O)R21, NR22R23, OR24, SR24, S(O)R25, SO2R25 and Si(R25a)3;
• where R1 may additionally be hydrogen and
• where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents R1 and R2 independently of one another are unsubstituted or may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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;
• R3 is halogen, cyano, nitro or a radical R26, OR27, SR28, S(O)R28, SO2R28, NR29R30 or N(OR31)R32;
• R4 is hydrogen, halogen, cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C5-C8-cycloalkenyl, C2-C6-alkynyl, C5-C8-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-[C1-C6-alkoxycarbonyl]-C1-C6)-alkyl or a radical COR21, OR27, SR28, S(O)R28, SO2R28, NR29R30 or N(OR31)R32,
• where the abovementioned aliphatic, cyclic or aromatic moieties of the substituent R4 independently of one another are unsubstituted or may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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;
• R5 is hydrogen, halogen, cyano, nitro, hydroxyl, C1-C8-alkyl, C2-C8-alkenyl, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C2-C8-alkynyl, C4-C8-alkadienyl, C7-C8-cycloalkynyl, C5-C8-cycloalkenyl-(C1-C6)-alkyl, C5-C8-cycloalkynyl-(C1-C6)-alkyl, C3-C6-cycloalkyl-(C2-C6)-alkenyl, C5-C8-cycloalkenyl-(C2-C6)-alkenyl, C5-C8-cycloalkynyl-(C2-C6)-alkenyl, C3-C6-cycloalkyl-(C2-C6)-alkynyl, C5-C8-cycloalkenyl-(C2-C6)-alkynyl, C5-C8-cycloalkynyl-(C2-C6)-alkynyl, tri-(C1-C6)-alkylsilyl, [tri-(C1-C6)-alkylsilyl]-(C2-C6)-alkynyl, phenyl, phenyl-(C1-C6)-alkyl, phenyl-(C2-C6)-alkenyl, phenyl-(C2-C6)-alkynyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, heterocyclyl-(C2-C6)-alkenyl, heterocyclyl-(C2-C6)-alkynyl, phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl, C(O)R61, Z8NR62R63, Z11CH═N—O—R64, OR65, Z9SR65a, Z9S(O)R66, Z9S(O)2R66 or Z10P(O)(OR67)2;
• or
• R3 together with R5 is a chemical bond;
• R6 is halogen, cyano, nitro, C2-C8-alkenyl, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C2-C8-alkynyl, C4-C8-alkadienyl, C7-C8-cycloalkynyl, C5-C8-cycloalkenyl-(C1-C6)-alkyl, C5-C8-cycloalkynyl-(C1-C6)-alkyl, C3-C6-cycloalkyl-(C2-C6)-alkenyl, C5-C8-cycloalkenyl-(C2-C6)-alkenyl, C5-C8-cycloalkynyl-(C2-C6)-alkenyl, C3-C6-cycloalkyl-(C2-C6)-alkynyl, C5-C8-cycloalkenyl-(C2-C6)-alkynyl, C5-C8-cycloalkynyl-(C2-C6)-alkynyl, tri-(C1-C6)-alkylsilyl, [tri-(C1-C6)-alkylsilyl]-(C2-C6)-alkynyl, phenyl, phenyl-(C1-C6)-alkyl, phenyl-(C2-C6)-alkenyl, phenyl-(C2-C6)-alkynyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, heterocyclyl-(C2-C6)-alkenyl, heterocyclyl-(C2-C6)-alkynyl, phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl, C(O)R61, Z8NR62R63, Z11CH═N—O—R64, OR65, Z9SR65a, Z9S(O)R66, Z9S(O)2R66 or Z10P(O)(OR67)2;
• where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents R4, R5 and R6 independently of one another may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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;
• R7 is halogen, cyano, nitro or a radical R26, OR27, SR28, S(O)R28, SO2R28, NR29R30 or N(OR31)R32;
• R8 has one of the meanings given for R4;
• R9, R10 and R67 are each independently of one another hydrogen or C1-C6-alkyl and the radicals R10 in Z2B(OR10)2 may together form a C2-C4-alkylene chain;
• or
• R9a is C1-C6-alkyl;
• R11, R61 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C5-C8-cycloalkenyl, C2-C6-alkynyl, C7-C8-cycloalkynyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, C1-C6-alkoxyamino, di-(C1-C6-alkoxy)amino, C1-C6-alkylsulfonylamino, C1-C6-alkylaminosulfonylamino, [di-(C1-C6-alkyl)-amino]sulfonylamino, C3-C6-alkenylamino, C3-C6-alkynylamino, N-(C2-C6-alkenyl)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkyl)-amino, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)-amino, N—(C2-C6-alkenyl)-N—(C1-C6-alkoxy)-amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkoxy)-amino, phenyl, phenoxy, phenylamino, naphthyl or heterocyclyl;
• R12 and R62 independently of one another are hydrogen, C1-C6-alkyl, C1-C8-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-alkenyl, C3-C6-alkenyloxy, C5-C8-cycloalkenyl, C3-C6-alkynyl, C3-C6-alkynyloxy, C7-C8-cycloalkynyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, di-(C1-C6-alkyl)aminocarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonyl-(C1-C6)-alkyl, C1-C6-alkylsulfonyl, C1-C6-alkylaminosulfonyl, di-(C1-C6-alkyl)aminosulfonyl, phenylcarbonyl, phenylaminocarbonyl, phenylsulfonyl, phenylsulfonylaminocarbonyl or heterocyclylcarbonyl;
• R13 and R63 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C5-C8-cycloalkenyl, C3-C6-alkynyl, C3-C6-alkynyloxy, C7-C8-cycloalkynyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, di-(C1-C6-alkyl)aminocarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonyl-(C1-C6)-alkyl, C1-C6-alkylsulfonyl, C1-C6-alkylaminosulfonyl, di-(C1-C6-alkyl)aminosulfonyl, phenylcarbonyl, phenylaminocarbonyl, phenylsulfonyl, phenylsulfonylaminocarbonyl or heterocyclylcarbonyl;
• R14, R64 independently of one another are hydrogen, C1-C6-alkyl, C2-C6-alkenyl or phenyl;
• R15, R65a independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C5-C8-cycloalkenyl, C3-C6-alkynyl, C7-C8-cycloalkynyl, C3-C6-cycloalkyl-(C1-C6)-alkyl, C5-C8-cycloalkenyl-(C1-C6)-alkyl, C5-C8-cycloalkynyl-(C1-C6)-alkyl, C3-C6-cycloalkyl-(C2-C6)-alkenyl, C5-C8-cycloalkenyl-(C2-C6)-alkenyl, C5-C8-cycloalkynyl-(C2-C6)-alkenyl, C3-C6-cycloalkyl-(C2-C6)-alkynyl, C5-C8-cycloalkenyl-(C2-C6)-alkynyl, C5-C8-cycloalkynyl-(C2-C6)-alkynyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl-(C1-C6)-alkyl, [di-(C1-C6)-alkoxycarbonyl]-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, hetaryl or hetaryl-(C1-C6)-alkyl;
• R65 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C5-C8-cycloalkenyl, C3-C6-alkynyl, C7-C8-cycloalkynyl, C3-C6-cycloalkyl-(C1-C6)-alkyl, C5-C8-cycloalkenyl-(C1-C6)-alkyl, C5-C8-cycloalkynyl-(C1-C6)-alkyl, C3-C6-cycloalkyl-(C2-C6)-alkenyl, C5-C8-cycloalkenyl-(C2-C6)-alkenyl, C5-C8-cycloalkynyl-(C2-C6)-alkenyl, C3-C6-cycloalkyl-(C2-C6)-alkynyl, C5-C8-cycloalkenyl-(C2-C6)-alkynyl, C5-C8-cycloalkynyl-(C2-C6)-alkynyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl-(C1-C6)-alkyl, [di-(C1-C6)-alkoxycarbonyl]-(C1-C6)-alkyl, phenyl or phenyl-(C1-C6)-alkyl;
• R16, R66 independently of one another are C1-C6-alkyl, C1-C6-alkoxy, phenyl or phenoxy;
• Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10 and Z11 independently of one another are a bond, —CH2—, —CH2—CH2—, —O—CH(R17)—, —S—CH(R18)—, —S(O)—CH(R19)— or —SO2CH(R20—, in which R17, R18, R19 and R20 independently of one another are hydrogen or C1-C6-alkyl;
• R21 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C5-C8-cycloalkenyl, C2-C6-alkynyl, C7-C8-cycloalkynyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, C3-C6-alkenylamino, C3-C6-alkynylamino, C1-C6-alkylsulfonylamino, N—(C2-C6-alkenyl)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkyl)-amino, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)-amino, phenyl, phenylamino, phenoxy, naphthyl or heterocyclyl;
• R22 and R23 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C5-C8-cycloalkenyl, C3-C6-alkynyl, C7-C8-cycloalkynyl or C1-C6-alkylcarbonyl;
• R24 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C5-C8-cycloalkenyl, C3-C6-alkynyl, C7-C8-cycloalkynyl, C3-C6-cycloalkyl-(C1-C6)-alkyl, C5-C8-cycloalkenyl-(C1-C6)-alkyl, C5-C8-cycloalkynyl-(C1-C6)-alkyl, C3-C6-cycloalkyl-(C2-C6)-alkenyl, C5-C8-cycloalkenyl-(C2-C6)-alkenyl, C5-C8-cycloalkynyl-(C2-C6)-alkenyl, C3-C6-cycloalkyl-(C2-C6)-alkynyl, C5-C8-cycloalkenyl-(C2-C6)-alkynyl, C5-C8-cycloalkynyl-(C2-C6)-alkynyl, phenyl or phenyl-(C1-C6)-alkyl;
• R25 is C1-C6-alkyl, C1-C6-alkoxy, phenyl or phenoxy;
• R25′ is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C5-C8-cycloalkenyl, C3-C6-alkynyl, C7-C8-cycloalkynyl, phenyl or phenyl-(C1-C6)-alkyl;
• where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents R9, R9a, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R25a, R61, R62, R62a, R63, R64, R65, R65a, R66 and R67 independently of one another are unsubstituted or may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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;
• R26, R27, R28, R29 and R32 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, formyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxy-(C1-C6)-alkyl, C1-C6-alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkylaminocarbonyl, 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, N-(di-C1-C6-alkylamino)-imino-C1-C6-alkyl or [tri-(C1-C4)-alkyl]silyl, where the abovementioned aliphatic or isocyclic moieties of the substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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, 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 or heterocyclyl moieties of the 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;
• or S(O)OR33, where n is 1 or 2;
• R30 and R31 independently of one another are hydrogen;
• C1-C6-alkyl;
• C3-C6-cycloalkyl;
• C2-C6-alkenyl;
• C2-C6-alkynyl, where aliphatic or isocyclic moieties of the substituents R30 and R31 independently of one another are unsubstituted or may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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;
• heterocyclyl;
• or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl moieties of the 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;
• and
• R33 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl, where the phenyl substituent 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;
• where one or more of the following provisions may also be met:
• a) R2 together with one of the radicals Ra or Rb is a covalent bond or a 1-, 2-, 3- or 4-membered carbon chain in which one carbon atom may be replaced by O, S or a group NRF, where one of the carbon atoms may carry a carbonyl oxygen atom and/or in which the carbon atoms, in addition to hydrogen, may carry 1, 2, 3 or 4 radicals selected from the group consisting of halogen, cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
• b) R3 together with the radical R5 is a 1-, 2-, 3- or 4-membered carbon chain in which one carbon atom may be replaced by O, S or a group NRI, where one of the carbon atoms may carry a carbonyl oxygen atom and/or in which the carbon atoms, in addition to hydrogen, may carry 1, 2, 3 or 4 radicals selected from the group consisting of halogen, cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
• where R6 is not C1-C6-alkoxy and may be partially or fully halogenated and/or may carry one to three of the following groups:
• cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, 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, if R3 together with R5 is a chemical bond;
• or a salt thereof.