4-(3-Aminobenzoyl)-1 methylpyrazoles and their use as herbicides
View Patent ↗What is described are 4-(3-aminobenzoyl)pyrazoles of the general formula (I) and their use as herbicides. In this 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-methylpyrazole of the formula (I), or a salt thereof
in which
R 1 is hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl,
R 2 is (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;
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, (C 1 -C 4 )-alkylbenzoyl-(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.
2. The 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 in which
R 1 is hydrogen or (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, di-(C 1 -C 2 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 2 )-alkyl;
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, (C 1 -C 4 )-alkylbenzoyl-(C 1 -C 6 )-alkyl or benzyl, each of which is substituted by m methyl groups,
m is 0 or 1.
3. The 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 in which
R 1 is hydrogen or (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, di-(C 1 -C 2 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 2 )-alkyl;
Y is hydrogen.
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 a plant or a site of unwanted plant growth.
7. A method for controlling unwanted plants comprising applying an effective amount of a herbicidal composition as claimed in claim 4 to a plant or to a site of unwanted plant growth.
8. A 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. A method as claimed in claim 8 wherein the useful plants are transgenic useful plants.
10. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I) as claimed in claim 1 wherein, when Y is hydrogen, said 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 may occur in one of the following tautomeric structures:
11. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I) or a salt thereof, as claimed in claim 1 comprising an acidic proton which may be removed by reaction with a base.
12. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 11 wherein an acidic proton is removed by a base selected from the group consisting of hydrides, hydroxides and carbonates of lithium, sodium, potassium, magnesium and calcium, and also ammonia and organic amines.
13. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 which is present in the form of a salt.
14. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 13 wherein said salt is formed by forming an adduct with an organic acids and/or an inorganic acids.
15. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 which exists as stereoisomer and/or mixtures thereof.
16. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 , wherein Y comprises hydrogen.
17. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 , wherein R 1 comprises hydrogen or methyl.
18. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 , wherein R 1 comprises hydrogen, methyl, ethyl, propyl, cyclopropyl, or —(CH 2 ) 3 —O—CH 3 .
19. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 , wherein R 1 and R 2 comprise methyl.
20. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a salt thereof, as claimed in claim 1 , wherein
Y is hydrogen;
R 1 and R 2 are methyl.