Herbicidally Active Composition

• US 20100190794A1
• Filed: 06/11/2008
• Published: 07/29/2010
• Est. Priority Date: 06/12/2007
• Status: Abandoned Application

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Sievernich, Bernd, Moberg, William Karl, Reinhard, Robert, Hupe, Eike, Kibler, Elmar
• Application Number:
  US12/663,795
• Publication Number:
  US 20100190794A1
• Time in Patent Office: Days
• US Class Current: 514/245
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 33/18 Nitro compounds
• CPC Class Codes: A01N 37/46 N-acyl derivatives
• CPC Class Codes: A01N 43/10 with sulfur as the ring hetero atom
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/42 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/70 Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 47/12 containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
• CPC Class Codes: A01N 47/30 Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Abstract

The present invention relates to herbicidally active compositions comprising at least one piperazinedione compound of the formula I

• • in which:
  • R^x, R^y are each hydrogen or together are a chemical bond;
  • R¹ is cyano or nitro;
  • R² is hydrogen, fluorine, chlorine, C₁-C₂-alkyl, ethenyl or C₁-C₂-alkoxy;
  • R³ is fluorine or hydrogen;
  • R⁴ is methyl;
  • R⁵ is hydrogen, methyl or ethyl;
  • R⁶ is hydrogen, methyl or ethyl; and
  • R⁷ is hydrogen or halogen;
  • and at least one further active compound selected from the group consisting of
  • b1) lipid biosynthesis inhibitors;
  • b2) acetolactate synthase inhibitors (ALS inhibitors);
  • b3) photosynthesis inhibitors;
  • b4) protoporphyrinogen-IX oxidase inhibitors,
  • b5) bleacher herbicides;
  • b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
  • b7) glutamine synthetase inhibitors;
  • b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
  • b9) mitose inhibitors;
  • b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);
  • b11) cellulose biosynthesis inhibitors;
  • b12) decoupler herbicides;
  • b13) auxin herbicides;
  • b14) auxin transport inhibitors;
  • b15) other herbicides, and
  • C) safeners.

Claims

1. A herbicidally active composition, comprising

A) at least one piperazinedione compound of the formula I

in which:

R^x, R^y are each hydrogen or together are a chemical bond;

R¹ is cyano or nitro;

R² is hydrogen, fluorine, chlorine, C₁-C₂-alkyl, ethenyl or C₁-C₂-alkoxy;

R³ is fluorine or hydrogen;

R⁴ is methyl;

R⁵ is hydrogen, methyl or ethyl;

R⁶ is hydrogen, methyl or ethyl; and

R⁷ is hydrogen or halogen;

and at least one further active compound selected from

B) herbicides of class b1) to b15);

b1) lipid biosynthesis inhibitors;

b2) acetolactate synthase inhibitors (ALS inhibitors);

b3) photosynthesis inhibitors;

b4) protoporphyrinogen-IX oxidase inhibitors,

b5) bleacher herbicides;

b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

b7) glutamine synthetase inhibitors;

b8) 7,8-dihydropteroate synthase inhibitors (DI-IP inhibitors);

b9) mitose inhibitors;

b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);

b11) cellulose biosynthesis inhibitors;

b12) decoupler herbicides;

b13) auxin herbicides;

b14) auxin transport inhibitors; and

b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;

and

C) safeners, and also

the agriculturally acceptable salts of the active compounds B and C and the agriculturally acceptable derivatives of the active compounds B and C, provided they have a carboxyl group.

2. The composition according to claim 1, where R^x and R^y in formula I together are a covalent bond.

3. The composition according to claim 2, comprising the compound of the formula I in the form of the (Z) isomer or in the form of a mixture of Z and E isomers which comprises predominantly the Z isomer.

4. The composition according to any of the preceding claims where R⁵ is methyl.

5. The composition according to any of the preceding claims where R⁶ is methyl.

6. The composition according to any of the preceding claims, comprising as piperazinedione compound a compound of the formula I.aa

in which R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the meanings mentioned above and R⁷ is located in the meta- or para-position to the point of attachment of the phenyl ring.

7. The composition according to claim 6, comprising the piperazinedione compound of the formula I.aa in the form of the enantiomer I.aa-S

in which R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the meanings mentioned above, and

R⁷ is located in the meta- or para-position to the point of attachment of the phenyl ring, or in the form of a mixture of the enantiomers which contains predominantly the S enantiomer.

8. The composition according to any of the preceding claims, comprising as piperazinedione compound a compound of the formula I.bb

in which R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the meanings mentioned above and R⁷ is located in the meta- or para-position to the point of attachment of the phenyl ring.

9. The composition according to claim 8 in which the benzylic groups of the 3- and the 6-position of the piperazine ring have a cis arrangement.

10. The composition according to claim 8, comprising the compound I.bb in the form of the (S,S) enantiomer, where the carbon atoms in the 3- and the 6-position of the piperazine ring have in each case the S configuration, or in the form of a mixture of enantiomers or a mixture of diastereomers having an enantiomeric excess and a diastereomeric excess, respectively, of the (S,S) enantiomer.

11. The composition according to claim 1, where the piperazinedione compound of the formula I is selected from the group consisting of:

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]benzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-ethenylbenzonitrile,

2-[5-(4-fluorobenzyl)I-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]benzo-nitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-ethenylbenzonitrile,

3-benzyl-6-[1-(2-nitrophenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-ethenyl-6-nitrophenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-nitrophenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-1,4-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methyl-6-nitrophenyl)methylidene]-1,4-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-1,4-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]benzonitrile,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methylbenzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]benzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methylbenzonitrile,

2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]benzonitrile,

2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methylbenzonitrile,

2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]benzonitrile,

2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methylbenzonitrile,

3-benzyl-6-[1-(2-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-methyl-6-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-ethenyl-6-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-nitrophenyl)methylidene]-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-methyl-6-nitrophenyl)methylidene]-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-nitrophenyl)-methylidene]-3-ethyl-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethyl-piperazine-2,5-dione,

3-benzyl-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethyl-piperazine-2,5-dione,

3-benzyl-6-[1-(2-methyl-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethyl-piperazine-2,5-dione,

3-benzyl-6-[1-(2-ethenyl-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethyl-piperazine-2,5-dione,

3-benzyl-6-[1-(2-nitrophenyl)methylidene]-3-ethyl-1-methylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-fluoro-6-nitrophenyl)-methylidene]-3-ethyl-1-methylpiperazine-2,5-dione,

3-benzyl-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-3-ethyl-1-methylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-3-ethyl-1-methylpiperazine-2,5-dione,

3-benzyl-6-[1-(2-methyl-6-nitrophenyl)methylidene]-3-ethyl-1-methylpiperazine-2,5-dione, and

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-benzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methylbenzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-benzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluoro-benzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methyl-benzonitrile,

2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-benzonitrile

2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile

2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile

2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methylbenzonitrile,

2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-benzonitrile,

2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-fluorobenzonitrile,

2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methoxybenzonitrile,

2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3,4-difluorobenzonitrile,

2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylidenemethyl]-3-methylbenzonitrile,

3-(4-fluorobenzyl)-6-[1-(2-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-1,3,4-trimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-1,3,4-trimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-1,3,4-trimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methyl-6-nitrophenyl)methylidene]-1,3,4-trimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-nitrophenyl)methylidene]-1,3-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-1,3-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-1,3-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-1,3-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methyl-6-nitrophenyl)methylidene]-1,3-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-nitrophenyl)methylidene]-3-ethyl-1,4-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methyl-6-nitrophenyl)methylidene]-3-ethyl-1,4-dimethyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-nitrophenyl)methylidene]-3-ethyl-1-methylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-fluoro-6-nitrophenyl)methylidene]-3-ethyl-1-methyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2,3-difluoro-6-nitrophenyl)methylidene]-3-ethyl-1-methyl-piperazine-2,5-dione,

3-(4-fluorobenzyl)-6-[1-(2-methoxy-6-nitrophenyl)methylidene]-3-ethyl-1-methyl-piperazine-2,5-dione and

3-(4-fluorobenzyl)-6-[1-(2-methyl-6-nitrophenyl)methylidene]-3-ethyl-1-methyl-piperazine-2,5-dione.

12. The composition according to claim 11, where the piperazinedione compound of the formula 1 is selected from 2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl]benzonitrile and 2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl]benzonitrile.

13. The composition according to claim 1 where the piperazinedione compound of the formula I is selected from the group consisting of:

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,

2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,

2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,

2-[5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxy-benzonitrile,

2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluoro-benzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,

2-[5-(4-fluoro benzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluoro-benzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxy-benzonitrile,

2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluoro-benzonitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzo-nitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxy-benzonitrile,

2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluoro-benzonitrile,

3-benzyl-6-(2-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-(2-fluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-(2-methoxy-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-benzyl-6-(2-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-(2-fluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-(2-methoxy-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,

3-benzyl-6-(2-nitrobenzyl)-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-(2-fluoro-6-nitrobenzyl)-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-1,4-dimethylpiperazine-2,5-dione,

3-benzyl-6-(2-methoxy-6-nitrobenzyl)-1,4-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,

3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione

and 3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione.

14. The composition according to claim 13, where the piperazinedione compound of the formula I is 2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile.

15. The composition according to any of the preceding claims, comprising at least one herbicide B, selected from the compounds listed below:

b1) from the group of the lipid biosynthesis inhibitors;

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

b2) from the group of the ALS inhibitors;

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;

b3) from the group of the photosynthesis inhibitors;

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors;

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, sulfentrazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)methylsulfamoyl]-benzamide (CAS 372137-35-4), ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7) and N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 45100-03-7);

b5) from the group of the bleacher herbicides;

aclonifen, amitrole, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, fluridone, fluorochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo-[3.2.1]oct-3-en-2-one (CAS 352010-68-5) and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors;

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors;

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors;

asulam;

b9) from the group of the mitose inhibitors;

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchioralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors;

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, thenylchlor and also isoxazoline compounds, different from pyroxasulfone, of the formula II

in which R₁, R₂, R₃, R₄, X, Y and n have the meanings below;

R₁, R₂, R₃, R₄ are each independently of one another hydrogen, halogen or C₁-C₄-alkyl;

Y is phenyl or monocyclic 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclyl which, in addition to carbon ring members, contains one, two or three identical or different heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members, where phenyl and heterocyclyl are unsubstituted or carry 1, 2 or 3 substituents R^yy selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl and C₁-C₄-haloalkoxy, preferably phenyl or 5- or 6-membered aromatic heterocyclyl (hetaryl) which, in addition to carbon ring members, contains one, two or three nitrogen atoms as ring members, where phenyl and hetaryl are unsubstituted or carry 1, 2 or 3 substituents R^yy;

X is oxygen or NH; and

n is zero or one;

b11) from the group of the cellulose biosynthesis inhibitors;

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides;

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides;

2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluoroxypyr, fluoroxypyr-butomethyl, fluoroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (CAS 858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors;

diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides;

bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters.

16. The composition according to claim 15, where the herbicides B are selected from the group consisting of:

b1) clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate;

b2) amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazon-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron;

b3) amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxynil and its salts and esters, chloridazone, chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, methabenzthiazuron, metribuzin, paraquat, paraquat-dichloride, phenmedipham, propanil, pyridate, simazine, terbuthylazine and thidiazuron;

b4) acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon-ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen-ethyl, sulfentrazone, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)methylsulfamoyl]benzamide (CAS 372137-35-4), ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7) and N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 45100-03-7);

b5) aclonifen, beflubutamid, benzobicyclon, clomazone, diflufenican, fluorochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfotole, pyrazolynate, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-hydroxy-3[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (CAS 352010-68-5) and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine (CAS 180608-33-7);

b6) glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

b7) glufosinate, glufosinate-ammonium;

b8) asulam;

b9) benfluralin, dithiopyr, ethalfluralin, oryzalin, pendimethalin, thiazopyr and trifluralin;

b10) acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, pretilachlor, pyroxasulfone, thenylchlor as well as isoxazoline compounds of the formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

b11) dichlobenil, isoxaben, flupoxam;

b13) 2,4-D and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, fluoroxypyr-meptyl, MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (CAS 858956-08-8) and its salts and esters;

b14) diflufenzopyr and diflufenzopyr-sodium;

b15) bromobutide, cinmethylin, cumyluron, dalapon, difenzoquat, difenzoquat-metilsulfate, DSMA, dymron (=daimuron), flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, indanofan, metam, methylbromide, MSMA, oxaziclomefone, pyributicarb, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters.

17. The composition according to claim 15, where the herbicides B are selected from the group consisting of:

b1) clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, esprocarb, prosulfocarb, thiobencarb, triallate;

b2) bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-sodium, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, tritosulfuron;

b3) atrazine, diuron, fluometuron, hexazinone, isoproturon, metribuzin, paraquat, paraquat-dichloride, propanil and terbuthylazine;

b4) flumioxazin, oxyfluorfen, sulfentrazone, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)-methylsulfamoyl]benzamide (CAS 372137-35-4) and ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6);

b5) clomazone, diflufenican, fluorochloridone, isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione, topramezone and 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]-carbonyl]bicyclo[3.2.1]oct-3-en-2-one (CAS 352010-68-5);

b6) glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

b7) glufosinate, glufosinate-ammonium;

b9) pendimethalin and trifluralin;

b10) acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, S-metolachlor, pyroxasulfone as well as isoxazoline compounds of the formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined in claim 16;

b11) isoxaben;

b13) 2,4-D and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, fluoroxypyr-meptyl, quinclorac, quinmerac and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (CAS 858956-08-8) and its salts and esters;

b14) diflufenzopyr and diflufenzopyr-sodium,

b15) dymron (=daimuron), indanofan, oxaziclomefone and triaziflam.

18. The composition according to any of the preceding claims, comprising at least one active compound selected from the herbicides of classes b1), b2), b3), b4), b5), b9), b11) and b13).

19. The composition according to any of claims 1 to 17, comprising at least one active compound selected from the herbicides of class b10).

20. The composition according to any of the preceding claims, comprising at least one safener C selected from the group consisting of benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, MON4660 [CAS RN 71526-07-3], naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4).

21. The composition according to any of the preceding claims in which the weight ratio of component A to component B is in the range of from 500:

1 to 1;

500.

22. The composition according to claim 21 in which the weight ratio of component A to component C is in the range of from 100:

1 to 1;

100.

23. The composition according to claim 21 in which the weight ratio of component B to component C is in the range of from 500:

1 to 1;

500.

24. The composition according to any of the preceding claims in the form of a crop protection composition formulated as a 1-component composition comprising an active compound combination comprising at least one piperazinedione compound of the formula I and at least one further active compound selected from the herbicides B and the safeners C, and at least one solid or liquid carrier and/or one or more surfactants.

25. The composition according to any of claims 1 to 23 in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one piperazinedione compound of the formula I, a solid or liquid carrier and/or one or more surfactants, and a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and/or one or more surfactants.

26. A method for controlling unwanted vegetation wherein a herbicidally effective amount of a composition according to any of claims 1 to 25 is allowed to act on plants, their habitat or seed.

27. The method according to claim 26 wherein a composition according to any of claims 1 to 25 is applied before, during and/or after emergence of the unwanted plants, where the herbicidally active components A) and B) and/or C) are applied simultaneously or in succession.

28. The method according to claim 26 wherein the leaves of the crop plants and the unwanted plants are treated.

29. The use of compositions according to any of claims 1 to 25 for controlling unwanted vegetation.

30. The use of compositions according to any of claims 1 to 25 for controlling unwanted vegetation in crops of the following plant species:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica raps var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus armeniaca, Prunus avium, Prunus cerasus, Prunus dulcis, Prunus domestica, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.