4-(4-trifluoromethyl-3-thiobenzoyl)pyrazoles and their use as herbicides
View Patent ↗What is described are 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazoles of the general formula (I) and their use as herbicides. In this formula (I), R 1 , R 2 , R 3 and R 4 are radicals such as hydrogen and organic radicals, such as alkyl. Y is hydrogen or a protective group, such as tosyl.
1. A 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of the formula (I), or a salt thereof
in which
R 1 is (C 1 -C 4 )-alkyl,
R 2 is hydrogen or (C 1 -C 4 )-alkyl,
R 3 is (C 1 -C 4 )-alkyl,
R 4 is (C 1 -C 4 )-alkyl,
Y 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 selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy,
m is 0, 1, 2 or 3,
n is 0, 1 or 2.
2. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of the formula (I) or a salt thereof as claimed in claim 1 in which
R 1 is methyl or ethyl,
R 2 is hydrogen, methyl or ethyl,
R 3 is methyl or ethyl,
R 4 is methyl or ethyl,
Y is hydrogen, (C 1 -C 3 )-alkylsulfonyl, (C 1 -C 2 )-alkoxy-(C 1 -C 4 )-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl or benzyl, each of which is substituted by m methyl groups,
m is 0 or 1,
n is 0, 1 or 2.
3. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of the formula (I) or a salt thereof as claimed in claim 1 in which
R 1 is methyl or ethyl,
R 2 is hydrogen, methyl or ethyl,
R 3 is methyl or ethyl,
R 4 is methyl or ethyl,
Y is hydrogen,
n is 0, 1 or 2.
4. A herbicidal composition which comprises a herbicidally effective amount of at least one compound of the formula (I) or a salt thereof as claimed in claim 1 .
5. The herbicidal composition as claimed in claim 4 as a mixture with formulation auxiliaries.
6. A method for controlling unwanted plants which comprises applying an effective amount of at least one compound of the formula (I) or a salt thereof as claimed in claim 1 to the plants or a site of unwanted plant growth.
7. A method for controlling unwanted plants comprising using a compound of formula (I) or a salt thereof of claim 1 .
8. The method as claimed in claim 7 wherein the compounds of the formula (I) or a salt thereof are used for controlling unwanted plants in crops of useful plants.
9. The method as claimed in claim 8 wherein the useful plants are transgenic useful plants.
10. A method for controlling unwanted plants which comprises applying an effective amount of a herbicidal composition as claimed in claim 4 to the plants or a site of unwanted plant growth.
11. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein R 1 is methyl.
12. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein R 2 is hydrogen.
13. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein R 3 is methyl.
14. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein R 4 is methyl.
15. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein Y is hydrogen.
16. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein n is 2.
17. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein
R 1 is methyl;
R 2 is hydrogen;
R 3 is methyl;
R 4 is methyl;
Y is hydrogen; and
n is 2.
18. A method for controlling unwanted plants comprising using a compound of formula (I) or a salt thereof of claim 17 .
19. A herbicidal composition comprising a herbicidally effective amount of a compound of the formula (I) or a salt thereof as claimed in claim 17 .
20. The 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazole of formula (I) or a salt thereof according to claim 1 , wherein
R 1 is ethyl;
R 2 is hydrogen;
R 3 is methyl;
R 4 is methyl;
Y is hydrogen; and
n is 2.