4-(4-haloalkyl-3-thiobenzoyl)pyrazoles and use thereof as herbicides
View Patent ↗A description is given of 4-(4-haloalkyl-3-thiobenzoyl)pyrazoles of the formula (I) and of their use as herbicides. In this formula (I), X, Y, R 1 , R 2 , R 3 , and R 4 are radicals such as hydrogen and organic radicals such as alkyl.
1. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole of formula (I) and/or salt thereof
in which
X is (C 1 -C 4 )-alkyl,
Y is (C 1 -C 4 )-haloalkyl,
R 1 is (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl,
R 3 is hydrogen or (C 1 -C 4 )-alkyl,
R 4 is hydrogen, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl, and (C 1 -C 4 )-alkoxy,
m is 0, 1, 2 or 3, and
n is 0, 1 or 2, with the proviso that Y is not trifluoromethyl.
2. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or salt as claimed in claim 1 , in which
X is (C 1 -C 4 )-alkyl,
Y is (C 1 -C 4 )-haloalkyl,
R l is (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl,
R 3 is hydrogen or (C 1 -C 4 )-alkyl,
R 4 is hydrogen, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl, and (C 1 -C 4 )-alkoxy,
m is 0, 1, 2 or 3, and
n is 0, 1 or 2, with the proviso that Y is not trifluoromethyl.
3. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or salt as claimed in claim 1 , in which
X is (C 1 -C 4 )-alkyl,
Y is trichloromethyl, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, pentafluoroethyl or heptafluoroisopropyl,
R 1 is (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl,
R 3 is hydrogen or (C 1 -C 4 )-alkyl,
R 4 is hydrogen, n-propylsulfonyl, methoxyethylsulfonyl, phenylsulfonyl, 4-methyl -phenylsulfonyl, or thiophenyl-2-sulfonyl, and
n is 0, 1 or 2.
4. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or salt as claimed in claim 1 , in which
X is methyl,
Y is difluoromethyl or pentafluoroethyl,
R 1 is methyl,
R 2 is methyl,
R 3 is hydrogen or methyl,
R 4 is hydrogen, and
n is 1 or 2.
5. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or salt as claimed in claim 1 , in which
X is methyl,
Y is pentafluoroethyl,
R 1 is methyl,
R 2 is methyl,
R 3 is hydrogen or methyl,
R 4 is hydrogen, and
n is 1 or 2.
6. A herbicidal composition which comprises a herbicidally effective amount of at least one compound as claimed in claim 1 .
7. The herbicidal composition as claimed in claim 6 in a mixture with at least one formulation auxiliary.
8. The herbicidal composition as claimed in claim 6 , comprising at least one further pesticidally active compound from the group of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.
9. The herbicidal composition as claimed in claim 6 , comprising a safener.
10. The herbicidal composition as claimed in claim 6 , comprising a further herbicide.
11. A method for controlling unwanted plants, which comprises applying an effective amount of at least one compound as claimed in claim 1 to plants and/or to a location of unwanted plant growth.
12. A herbicidal composition as claimed in claim 6 which is capable of controlling unwanted plants.
13. The composition as claimed in claim 12 , wherein the compound of formula (I) and/or salt is capable of controlling unwanted plants in crops of useful plants.
14. The composition as claimed in claim 13 , wherein the useful plants are transgenic useful plants.
15. A method for controlling unwanted plants, which comprises applying an effective amount of at least one compound as claimed in claim 2 to plants and/or to a location of unwanted plant growth.
16. A method for controlling unwanted plants, which comprises applying an effective amount of at least one compound as claimed in claim 3 to plants and/or to a location of unwanted plant growth.
17. A method for controlling unwanted plants, which comprises applying an effective amount of at least one compound as claimed in claim 4 to plants and/or to a location of unwanted plant growth.
18. A method for controlling unwanted plants, which comprises applying an effective amount of at least one compound as claimed in claim 5 to plants and/or to a location of unwanted plant growth.