Herbicides comprising benzoylcyclohexanediones and safeners

1. A herbicidal composition comprising:

A) a herbicidally effective amount of one or more compounds of the formula (I)

in which the symbols and indices have the following definitions:

R 1 is nitro, amino, halogen, cyano, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-haloalkynyl, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkoxycarbonyl, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylcarbonyl, (C 1 -C 4 )-alkylaminosulfonyl, (C 1 -C 4 )-dialkylaminosulfonyl, (C 1 -C 4 )-alkylcarbamoyl, (C 1 -C 4 )-dialkylcarbamoyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylamino or (C 1 -C 4 )-dialkylamino;

R 2 is (C 1 -C 4 )-haloalkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkoxy-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkoxy, tetrahydrofuran-2-yl-methoxy-(C 1 -C 4 )-alkyl, tetrahydrofuran-3-yl-methoxy-(C 1 -C 4 )-alkyl or a heterocyclic radical from the group consisting of isoxazol-3-yl and 4,5-dihydroisoxazol-3-yl which is substituted by a radical from the group consisting of cyanomethyl, ethoxymethyl and methoxymethyl;

R 3 is OR 5 , cyano, halogen, cyanato, thiocyanato, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl, (C 2 -C 4 )-alkenylthio, (C 2 -C 4 )-alkenylsulfinyl, (C 2 -C 4 )-alkenylsulfonyl, (C 2 -C 4 )-alkynylthio, (C 2 -C 4 )-alkynylsulfinyl, (C 2 -C 4 )-alkynylsulfonyl, (C 1 -C 4 )-haloalkylthio, (C 2 -C 4 )-haloalkenylthio, (C 2 -C 4 )-haloalkynylthio, (C 1 -C 4 )-haloalkylsulfinyl, (C 2 -C 4 )-haloalkenylsulfinyl, (C 2 -C 4 )-haloalkynylsulfinyl, (C 1 -C 4 )-haloalkylsulfonyl, (C 2 -C 4 )-haloalkenylsulfonyl or (C 2 -C 4 )-haloalkynylsulfonyl;

R 4 is (C 1 -C 4 )-alkyl;

R 5 is hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl;

a is 0, 1, 2 or 3;

b is 0, 1 or 2; and

B) an antidote-active amount of one or more compounds of the formula

in which the symbols and indices have the following definitions:

n′ is a natural number from 1 to 5,

W is a radical

m′ is 0 or 1;

R 17 is are identical or different and are hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl;

R 18 is are identical or different and are OR 24 , SR 24 or NR 24 R 25 or a saturated or unsaturated 3- to 7-membered heterocycle containing at least one nitrogen atom and up to 3 heteroatoms which is bonded by the nitrogen atom to the carbonyl group in (II) or (III) and is unsubstituted or substituted by radicals from the group consisting of (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and unsubstituted or substituted phenyl;

R 24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical;

R 25 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or substituted or unsubstituted phenyl; and

R 29 is identical or different and are hydrogen, (C 1 -C 8 )-alkyl, (C 1 C 6 )-haloalkyl, (C 3 -C 12 )-cycloalkyl or substituted or unsubstituted phenyl;

inclusive of the stereoisomers and the agriculturally customary salts.

2. The herbicidal composition as claimed in claim 1 , comprising compounds of the formula (I) wherein the symbols and indices have the following definitions:

R 1 is nitro, cyano, chlorine, fluorine, methyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl;

R 2 is pentafluoroethoxymethyl, 2,2-difluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2,2,3,3-tetrafluoropropoxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, cyclopropyloxy, tetrahydrofuran-2-ylmethoxymethyl, methoxyethoxyethoxymethyl, or 4,5-dihydroisoxazol-3-yl which is substituted by a radical from the group consisting of cyanomethyl, ethoxymethyl and methoxymethyl;

R 3 is OR 5 ;

R 5 is hydrogen;

a is 2;

b is 0, and the two radicals R 1 are in positions 2 and 4 of the phenyl ring.

3. The herbicidal composition as claimed in claim 1 , wherein the ratio of herbicide to safener is from 1:10 to 10:1.

4. The herbicidal composition as claimed in claim 1 , comprising a further herbicide.

5. The herbicidal composition as claimed in claim 1 wherein component B is ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.

6. The herbicidal composition as claimed in claim 1 wherein component B is of formula (II) and W is W4, and wherein component A is

7. The herbicidal composition as claimed in claim 1 wherein component B is ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate, and wherein component A is

8. The herbicidal composition as claimed in claim 1 , wherein

R 24 is hydrogen, (C 1 -C 8 )-alkyl, (C 3 -C 12 )-cycloalkyl, (C 2 -C 8 )-alkenyl and (C 2 -C 18 )-alkynyl, where the carbon-containing groups can be substituted by one or more radicals R 50 ;

R 50 is identical or different and is halogen, hydroxyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkylthio, (C 2 -C 8 )-alkenylthio, (C 2 -C 8 )-alkynylthio, (C 2 -C 48 )-alkenyloxy, (C 2 -C 8 )-alkynyloxy, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkoxy, cyano, mono- and di-(C 1 -C 4 )-alkyl)amino, carboxyl, (C 1 -C 8 )-alkoxycarbonyl, (C 2 -C 8 )-alkenyloxycarbonyl, (C 1 -C 8 )-alkylthiocarbonyl, (C 2 -C 8 )-alkynyloxycarbonyl, (C 1 -C 8 )-alkylcarbonyl, (C 2 -C 8 )-alkenylcarbonyl, (C 2 -C 8 )-alkynylcarbonyl, 1-(hydroxyimino)-(C 1 -C 6 )alkyl, 1-[(C 1 -C 4 )-alkylimino]-(C 1 -C 4 )-alkyl, 1-[(C 1 -C 4 )-alkoxyimino]-(C 1 -C 6 )-alkyl, (C 1 -C 8 )-alkylcarbonylamino, (C 2 -C 8 )-alkenylcarbonylanuno, (C 2 -C 8 )-alkynylcarbonylamino, aminocarbonyl, (C 1 -C 8 )-alkylaminocarbonyl, di-(C 1 -C 6 )-alkylaminocarbonyl; (C 2 -C 6 )-alkenylaninocarbonyl, (C 2 -C 6 )-alkynylaminocarbonyl, (C 1 -C 8 )-alkoxycarbonylamino, (C 1 -C 8 )-alkylaminocarbonylamino, (C 1 -C 6 )-alkylcarbonyloxy which is unsubstituted or substituted by R 51 , or is (C 2 -C 6 )-alkenylcarbonyloxy, (C 2 -C 6 )-alkynylcarbonyloxy, (C 1 -C 8 )-alkylsulfonyl, phenyl, phenyl-(C 1 -C 6 )-alkoxy, phenyl-(C 1 -C 6 )alkoxycarbonyl, phenoxy, phenoxy-(C 1 -C 6 )-alkoxy, phenoxy-(C 1 -C 6 )alkoxycarbonyl, phenylcarbonyloxy, phenylcarbonylamino, phenyl-(C 1 -C 6 )alkylcarbonylamino, for the phenyl ring being the last-mentioned 9 radicals unsubstituted or mono- or polysubstituted by radicals R 52 ; SiR′ 3 , OSiR′ 3 , R′ 3 Si-((C 1 -C 8 )-alkoxy, —CO—O—NR′ 2 , —O—N═CR′ 2 , —N═CR′ 2 , —O—NR′ 2 , —NR′ 2 , —CH(OR′) 2 , —O—(CH 2 ) m —CH(OR′) 2 , —CR′″(OR′) 2 , —O—(CH 2 ) m CR′″(OR″) 2 or by R″O—CHR′″CHCOR″—(C 1 -C 6 )-alkoxy,

R 51 is identical or different and is halogen, nitro, (C 1 -C 4 )-alkoxy and phenyl which is unsubstituted or substituted by one or more radicals R 51 ,

R 52 is identical or different and is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy or nitro;

R′ is identical or different and is hydrogen, (C 1 -C 4 )-alkyl, phenyl which is unsubstituted or substituted by one or more radicals R 52 , or two radicals R′ together form a (C 2 -C 6 )-alkanediyl chain;

R″ is identical or different and is (C 1 -C 4 )-alkyl, or two radicals R″ together form a (C 2 -C 6 )-alkanediyl chain;

R′″ is hydrogen or (C 1 -C 4 )-alkyl;

m is 0, 1, 2, 3, 4, 5 or 6.

9. The herbicidal composition as claimed in claim 8 , wherein

R 24 is hydrogen, (C 1 -C 8 )-alkyl or (C 3 -C 7 )-cycloalkyl, the above carbon-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono or disubstitutedby radicals R 50 ,

R 50 is identical or different and is hydroxyl, (C 1 -C 4 )-alkoxy, carboxyl, (C 1 -C 4 )-alkoxycarbonyl, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-alkynyloxycarbonyl, 1-(hydroxyimino)-(C 1 -C 4 )-alkyl, 1-[(C 1 -C 4 )-alkylimino]-(C 1 -C 4 )-alkyl and 1-[(C 1 -C 4 )-alkoxyimino]-(C 1 -C 4 -alkyl; —SiR′ 3 , —O—N═CR′ 2 , —N═CR′ 2 , —NR′ 2 and ONR′ 2 where R′ is identical or different and is hydrogen, (C 1 -C 4 )-alkyl or, as a pair, a (C 4 -C 5 )-alkanediyl chain,

R 29 is identical or different and are hydrogen, (C 1 -C 8 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, amino, mono- and di-[(C 1 -C 4 -alkyl]amino, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio and (C 1 -C 4 )alkylsulfonyl;

R 17 is identical or different and are hydrogen, halogen, methyl, ethyl, methoxy, ethoxy, or (C 1 or C 2 ).

10. The herbicidal composition as claimed in claim 1 , wherein

R 17 is halogen, nitro or (C 1 -C 4 )-haloalkyl;

R 18 is a radical of the formula OR 24 ;

R 24 is hydrogen, (C 1 -C 8 )-alkyl or (C 3 -C 7 )-cycloalkyl, where the above carbon-containing radicals are unsubstituted or mono- or polysubstiftutedby identical or different halogen radicals or up to disubstituted by identical or different radicals selected from the group consisting of hydroxyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxycarbonyl, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-alkynyloxycarbonyl, 1-(hydroxyimino)-(C 1 -C 4 )-alkyl, 1-[(C 1 -C 4 )-alkylimino]-(C 1 -C 4 )-alkyl, 1-[(C 1 -C 4 )-alkoxymino]-(C 1 -C 4 )-alkyl and radicals of the formulae —SiR′ 3 , —O—N═R′ 2 , —N═CR′ 2 , —NR′ 2 and —O—NR′ 2 , where the radicals R′ in the abovementioned formulae are identical or different and are hydrogen, (C 1 -C 4 )-alkyl or, as a pair, are (C 4 or C 5 )-alkanediyl;

R 29 is identical or different and are hydrogen, (C 1 -C 8 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or phenyl which is unsubstituted or substituted by one or more of the radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro, (C 1 -C 4 )-haloalkyl and (C 1 -C 4 )-haloalkoxy.

11. A method of controlling weed plants in crops which comprises applying a herbicidally active amount of a herbicidal composition as claimed in claim 1 to the weed plants, plants, seeds of plants, or the area on which the plants are growing.

12. The method as claimed in claim 11 , wherein the plants are from the group consisting of sugar cane, corn, wheat, rye, barley, oats, rice, sorghum, cotton, and soya.

13. The method as claimed in claim 11 , wherein the plants have been genetically modified.