# US 2010/0167933 A1 · Piperazine Compounds With Herbicidal Action

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- Number: US 2010/0167933 A1
- Document ID: US20100167933A1
- Status: Published application
- Kind: A1
- Application number: 12/663,756
- Filed: 2008-06-20
- Published: 2010-07-01
- Earliest claimed: 2007-06-22
- Inventors: Eike Hupe; Thomas Seitz; Matthias Witschel; Dschun Song; William Karl Moberg; Liliana Parra Rapado; Frank Stelzer; Andrea Vescovi; Trevor William Newton; Robert Reinhard; Bernd Sievernich; Klaus Grossmann; Thomas Ehrhardt; Michael Rack; Elmar Kibler
- Web page: https://patentgrep.com/patent/US20100167933A1

## CPC

- C07D 239/54: as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 239/22: with hetero atoms directly attached to ring carbon atoms
- C07D 239/49: with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
- C07D 239/58: Two sulfur atoms
- C07D 239/70: condensed with carbocyclic rings or ring systems
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 401/10: linked by a carbon chain containing aromatic rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D 417/10: linked by a carbon chain containing aromatic rings
- C07D 471/14: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 491/10: Spiro-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The present invention relates to piperazine compounds of the general formula I defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation. In formula I, A1, A2 independently of one another are aryl or heteroaryl, where Ra is attached in the ortho-position to the point of attachment of A1 to a carbon atom or a nitrogen atom of A1, Y1, Y2 are oxygen, sulfur or a group NRy1, and the variables Ra, Rb, Rc, Rd, Re, Rf, R1, R2, R3, R4, R5, R6, R7, and R8 have the meanings mentioned in the claims and the description.

## Claims

### Claim at position 1

1-53. (canceled)

### Claim 54

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.

### Claim 55 (depends on 54)

The compound according to claim 54 in which A1 and A2 are each phenyl.

### Claim 56 (depends on 54)

The compound according to claim 54 in which:
Ra is selected from the group consisting of halogen, cyano, nitro, C(═O)—R11, phenyl and a 5- or 6-membered heterocyclic radical which has 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S as ring atoms, where phenyl and the heterocyclic radical are unsubstituted or may have 1, 2, 3 or 4 substituents independently of one another selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, where
R11 is hydrogen, C1-C6-alkyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, [di-(C1-C6)-alkyl]amino, C1-C6-alkoxy-amino, N—C1-C6-alkoxy-N—C1-C6-alkylamino, C1-C6-alkylsulfonylamino, C1-C6-alkylaminosulfonylamino, [di-(C1-C6)-alkylamino]sulfonylamino, phenyl, phenoxy, phenylamino, naphthyl or heterocyclyl, and the abovementioned aliphatic, cyclic or aromatic moieties of the substituent R11 may be partially or fully halogenated.

### Claim 57 (depends on 54)

The compound of claim 54 in which
Rb is hydrogen, halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C1-C4-alkoxy, C1-C4-haloalkoxy, benzyl or a group S(O)nR16a in which R16a is C1-C4-alkyl or C1-C4-haloalkyl and n is 0, 1 or 2; and
Rc is hydrogen or halogen.

### Claim 58 (depends on 54)

The compound of claim 54 in which
Rd, Re independently of one another are selected from the group consisting of hydrogen, halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C1-C4-alkoxy and C1-C4-haloalkoxy; and
Rf is hydrogen.

### Claim 59 (depends on 54)

The compound of claim 54 in which
R1 is hydrogen, C1-C6-alkyl or C1-C6-alkylcarbonyl.

### Claim 60 (depends on 54)

The compound of claim 54 in which
R2 is C1-C6-alkyl or C1-C6-alkylcarbonyl.

### Claim 61 (depends on 54)

The compound of claim 54 in which
R3 is R26 or OR27, where
R26 and R27 independently of one another are selected from the group consisting of hydrogen, C1-C6-alkyl C1-C6-alkylcarbonyl, phenyl-C1-C6-alkyl, phenylcarbonyl, where the abovementioned aliphatic or aromatic moieties of the substituents may be partially or fully halogenated, and a group SO2R33, where
R33 is C1-C6-alkyl or phenyl, and where the phenyl substituent may be partially or fully halogenated and/or may carry one to three C1-C6-alkyl groups.

### Claim 62 (depends on 61)

The compound according to claim 61 in which R3 is hydrogen.

### Claim 63 (depends on 54)

The compound of claim 54 in which R4 is hydrogen.

### Claim 64 (depends on 54)

The compound of claim 54 in which R5 is hydrogen, methyl or hydroxyl.

### Claim 65 (depends on 54)

The compound of claim 54 in which R3 together with R5 is a chemical bond.

### Claim 66 (depends on 54)

The compound of claim 54 in which
R6 is halogen, cyano, nitro, C2-C8-alkenyl, C2-C8-alkynyl or C(O)R61.

### Claim 67 (depends on 54)

The compound of claim 54 in which R7 and R8 are hydrogen.

### Claim 68 (depends on 54)

The compound of claim 54 in which R1 together with a radical R6 is a 3-, 4- or 5-membered carbon chain in which one carbon atom may be replaced by O, S or a group NRD, 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.

### Claim 69 (depends on 68)

The compound of claim 68 in which R1 together with the radical R6 is CH2CH2CH2 or CH2CH2CH2CH2 in which 1, 2, 3 or 4 of the hydrogen atoms may be replaced by radicals selected from the group consisting of halogen, cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.

### Claim 70 (depends on 54)

The compound of claim 54 in which 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.

### Claim 71 (depends on 70)

The compound of claim 70 in which R3 together with the radical R5 is CH2, O or a group NRI in which RI is hydrogen or C1-C4-alkyl.

### Claim 72 (depends on 54)

A composition comprising a herbicidally effective amount of the piperazine compound of claim 54 or an agriculturally useful salt thereof and auxiliaries customary for formulating crop protection agents.

### Claim 73 (depends on 54)

A method for controlling unwanted vegetation wherein a herbicidally effective amount of the piperazine compound of claim 54 or an agriculturally useful salt thereof is applied to on plants, their seed and/or their habitat.