Herbicidal 3-amino-2-thiomethylbenzoylpyrazoles

1. A compound of the formula (I) or salt thereof

in which

R 1 is C 1 –C 6 alkyl;

R 2 and R 3 independently of one another are hydrogen, C 3 –C 6 cycloalkyl, C 2 –C 6 alkenyl, C 2 –C 6 alkynyl or C 1 –C 6 alkyl substituted s times by radicals from the group consisting of halogen, C 1 –C 4 alkoxy and C 1 –C 4 alkylthio,

or

NR 2 R 3 forms a 5- or 6-membered heterocyclic radical from the group consisting of 1-pyrrolyl, 1-pyrrolidinyl, 1-piperidinyl, 1-pyrazolyl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, 1-tetrazolyl, 1-pyrazolidinyl, 1-imidazolyl, 2-isoxazoldinyl, 3-oxazolidinyl, 1,2,3-oxadiazolidin-2-yl, 1,2,3-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-2-yl, 1,2,3-oxadiazolidin-4-yl, 1,3,4-oxadiazolidin-3-yl, 1,3,4-oxadiazolidin-4-yl, 3-thiazolidinyl, 2,3-thiadiazolidin-2-yl, 1,2,3-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-2-yl, 1,2,3-thiadiazolidin-4-yl, 1,3,4-thiadiazolidin-3-yl, 1,3,4-thiadiazolidin-4-yl, 1-morpholinyl, 2,3-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-1-yl, 1,2-dihydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 3,4,5,6-tetrahydropyridin-1-yl, 1-piperazinyl and 1-tetrahydropyrimidinyl, the aforementioned heterocyclic radicals being substituted s times by substituents from the group consisting of halogen, cyano, C 1 –C 4 alkoxy, trifluoromethyl, trifluoroethyl, fluoro-C 1 –C 3 alkyl, fluoro-C 1 –C 3 alkoxy, cyano-C 1 –C 4 alkyl, C 3 –C 6 cycloalkyl, C 3 –C 6 cycloalkyl-C 1 –C 4 -alkyl, C 1 –C 3 alkoxymethyl;

R 4 is hydrogen, halogen, C 1 –C 4 alkyl, halo-C 1 –C 4 alkyl, C 1 –C 4 alkoxy, C 1 –C 4 alkylthio, C 1 –C 4 alkylsulfinyl or C 1 –C 4 alkylsulfonyl;

R 5 is hydrogen, C 1 –C 6 alkylcarbonylmethyl, phenylsulfonyl, C 1 –C 4 alkylsulfonyl substituted s times by halogen, phenylsulfonyl substituted once by methyl or halogen, benzyl substituted s times by halogen, nitro or methoxy, or benzoylmethyl substituted s times by halogen, nitro, methyl or methoxy;

R 6 is C 1 –C 4 alkyl;

R 7 is hydrogen, (C 1 –C 4 )alkyl or C 3 –C 6 cycloalkyl;

n is 0, 1 or 2;

s is 0, 1, 2 or 3;

t is 1, 2 or 3.

2. A compound as claimed in claim 1 , wherein

R 1 is methyl;

R 2 and R 3 independently of one another are hydrogen, cyclopropyl, C 1 –C 6 alkyl, C 2 –C 6 alkenyl, C 2 –C 6 alkynyl or C 1 –C 6 alkyl substituted by a C 1 –C 4 alkoxy radical,

or

NR 2 R 3 forms a 5- or 6-membered heterocyclic radical from the group consisting of 1-pyrrolyl, 1-pyrrolidinyl, 1-piperidinyl, 1-pyrazolyl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, 1-tetrazolyl, 1-pyrazolidinyl, 1-imidazolyl, 2-isoxazoldinyl, 3-oxazolidinyl, 1,2,3-oxadiazolidin-2-yl, 1,2,3-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-2-yl, 1,2,3-oxadiazolidin-4-yl, 1,3,4-oxadiazolidin-3-yl, 1,3,4-oxadiazolidin-4-yl, 3-thiazolidinyl, 2,3-thiadiazolidin-2-yl, 1,2,3-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-2-yl, 1,2,3-thiadiazolidin-4-yl, 1,3,4-thiadiazolidin-3-yl, 1,3,4-thiadiazolidin-4-yl, 1-morpholinyl, 2,3-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-1-yl, 1,2-dihydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 3,4,5,6-tetrahydropyridin-1-yl, 1-piperazinyl and 1-tetrahydropyrimidinyl, the abovementioned heterocyclic radicals being substituted s times by substituents from the group consisting of halogen, methoxy and trifluoromethyl,

and

n is 0 or 2.

3. A compound as claimed in claim 1 , wherein

R 4 is bromine, chlorine, fluorine, trifluoromethyl, methylsulfonyl or ethylsulfonyl, and

R 5 is hydrogen, n-propylsulfonyl or benzoylmethyl.

4. A compound as claimed in 1, wherein

R 6 is methyl or ethyl, and

R 7 is hydrogen, methyl or cyclopropyl.

5. A compound as claimed in claim 1 , wherein

R 2 and R 3 independently of one another are hydrogen, methyl, ethyl, cyclopropyl or methoxyethyl,

or

NR 2 R 3 forms a radical from the group consisting of 1-pyrrolyl, 1-pyrazolyl, 1-morpholinyl and 1-piperazinyl.

6. A herbicidal composition comprising a herbicidally effective amount of at least one compound of the formula (I) as claimed in claim 1 .

7. A herbicidal composition as claimed in claim 6 in a mixture with formulating auxiliaries.

8. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the formula (I) as claimed in claim 1 to the plants or to the site of the unwanted plant growth.

9. A compound as claimed in claim 2 , wherein

R 4 is bromine, chlorine, fluorine, trifluoromethyl, methylsulfonyl or ethylsulfonyl, and

R 5 is hydrogen, n-propylsulfonyl or benzoylmethyl.

10. A method of controlling unwanted plants, which comprises applying an effective amount of a herbicidal composition as claimed in claim 6 to the plants or to the site of the unwanted plant growth.

11. A method of controlling unwanted plants, which comprises applying an effective amount of a herbicidal composition as claimed in claim 7 to the plants or to the site of the unwanted plant growth.

12. The method of claim 8 , wherein the unwanted plants are in crops of useful plants.

13. The method of claim 12 , wherein the useful plants are transgenic.

14. The method of claim 10 , wherein the unwanted plants are in crops of useful plants.

15. The method of claim 14 , wherein the useful plants are transgenic.

16. The method of claim 11 , wherein the unwanted plants are in crops of useful plants.

17. The method of claim 16 , wherein the useful plants are transgenic.