4-(3-aminobenzoyl)-1,3-dimethylpyrazoles and their use as herbicides
View Patent ↗What is described are 4-(3-aminobenzoyl)-1,3-dimethylpyrazoles of the general formula (I) and their use as herbicides. In this general formula (I), R 1 and R 2 are radicals such as hydrogen and organic radicals, such as alkyl, alkenyl and alkynyl. Y is hydrogen or a protective group, such as tosyl.
1. A 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof
in which
R 1 is hydrogen or (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl; and
Y is hydrogen.
2. A herbicidal composition which comprises a herbicidally effective amount of at least one compound of formula (I), or a salt thereof, as claimed in claim 1 .
3. The herbicidal composition as claimed in claim 2 as a mixture with formulation auxiliaries.
4. A method for controlling unwanted plants which comprises applying an effective amount of at least one compound of formula (I), or a salt thereof, as claimed in claim 1 to the plants or a site of unwanted plant growth.
5. The method as claimed in claim 4 wherein the compounds of formula (I), or a salt thereof, are used for controlling unwanted plants in crops of useful plants.
6. The method as claimed in claim 5 wherein the useful plants are transgenic useful plants.
7. A method for controlling unwanted plants which comprises applying an effective amount of a herbicidal composition as claimed in claim 2 to the plants or a site of unwanted plant growth.
8. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof, as claimed in claim 1 , wherein:
R 1 is (C 1 -C 4 )-alkyl.
9. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof
wherein:
R 1 is hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl;
R 2 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl; and
Y is (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, or (C 1 -C 4 )-alkylbenzoyl-(C 1 -C 6 )-alkyl, 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.
10. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof, as claimed in claim 1 , wherein R 1 is Me.
11. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof, as claimed in claim 1 , wherein R 2 is Me, Et, n-Pr, or i-Pr, c-Pr, or CH 2 -c-Pr.
12. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof, as claimed in claim 9 , wherein Y is Ph-SO 2 or PhC(O).
13. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof, as claimed in claim 1 , wherein:
R 1 is H; and
R 2 is Me, Et, n-Pr, i-Pr, c-Pr, n-Bu, s-Bu, i-Bu, t-Bu, or CH 2 -c-Pr.
14. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof, as claimed in claim 1 , wherein:
R 1 is CH 3 ; and
R 2 is Me, Et, n-Pr, i-Pr, c-Pr, n-Bu, s-Bu, i-Bu, t-Bu, or CH 2 -c-Pr.
15. The 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (I), or a salt thereof, as claimed in claim 9 , wherein:
R 1 is H;
R 2 is Et; and
Y is Ph-SO 2 or PhC(O).
16. A 4-(3-aminobenzoyl)-1,3-dimethylpyrazole of formula (II), or a salt thereof
17. A 4-(3-aminobenzoyl)-1,3-dimethylpyrazole as claimed in claim 1 , which is a compound of formula (I-4), or a salt thereof
18. A 4-(3-aminobenzoyl)-1,3-dimethylpyrazole as claimed in claim 1 , which is a compound of formula (I-5), or a salt thereof
19. A 4-(3-aminobenzoyl)-1,3-dimethylpyrazole as claimed in claim 1 , which is a compound of formula (I-2), or a salt thereof; or a compound of formula (I-43), or salt thereof