4-(3-alkylthiobenzoyl)pyrazoles and their use as herbicides
View Patent ↗4-(3-Alkylthiobenzoyl)pyrazoles of the formula (I) are described as herbicides. In this formula (I), X, Y, R 1 , R 2 , R 3 and R 4 represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.
1. A 4-(3-alkylthiobenzoyl)pyrazole of formula (I) and/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 6 )-alkyl,
R 4 is hydrogen, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl, benzyl, where the five last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy;
X is OR 5 , OCOR 5 or OSO 2 R 6 ,
R 5 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 ) -cycloalkyl-(C 1 -C 6 )-alkyl or phenyl-(C 1 -C 6 )-alkyl, where the six last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen, OR 7 and S(O) m R 8 ,
R 6 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl -(C 1 -C 6 )-alkyl or phenyl-(C 1 -C 6 )-alkyl, each of which is substituted by s radicals selected from the group consisting of halogen, OR 7 and S(O) m R 8 ,
R 7 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 8 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
Y is (C 1 -C 6 )-haloalkyl,
m is 0, 1 or 2,
n is 0, 1 or 2,
s is 0, 1, 2 or 3.
2. The 4-(3-alkylthiobenzoyl)pyrazole as claimed in claim 1 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 6 )-alkyl,
R 4 is hydrogen, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl, benzyl, where the five last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy;
X is OR 5 ,
R 5 is (C 1 -C 6 )-alkyl substituted by s methoxy or ethoxy groups,
Y is (C 1 -C 6 )-haloalkyl,
s is 0, 1, 2 or 3.
3. The 4-(3-alkylthiobenzoyl)pyrazole as claimed in claim 1 in which
R 1 is methyl, ethyl, n-propyl or isopropyl,
R 2 is hydrogen, methyl, ethyl, n-propyl or isopropyl,
R 3 is methyl, ethyl, n-propyl or isopropyl,
R 4 is hydrogen, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl, benzyl, where the five last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy;
X is OR 5 ,
R 5 is (C 1 -C 6 )-alkyl,
Y is (C 1 -C 6 )-haloalkyl,
s is 0, 1, 2 or 3.
4. The 4-(3-alkylthiobenzoyl)pyrazole as claimed in claim 1 in which
R 1 is methyl, ethyl, n-propyl or isopropyl,
R 2 is hydrogen, methyl, ethyl, n-propyl or isopropyl,
R 3 is methyl, ethyl, n-propyl or isopropyl,
R 4 is hydrogen, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl, benzyl, where the five last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy;
X is OR 5 ,
R 5 is (C 1 -C 6 )-alkyl,
s is 0, 1, 2 or 3.
5. A herbicidal composition comprising a herbicidally effective amount of at least one compound as claimed in claim 1 .
6. The herbicidal composition as claimed in claim 5 in a mixture with at least one formulation auxiliary.
7. A method for controlling unwanted plants which comprises applying an effective amount of at least one compound as claimed in claim 1 to the plants and/or to a site of unwanted vegetation.
8. A herbicidal composition as claimed in claim 5 for controlling unwanted plants.
9. A composition as claimed in claim 8 wherein the compound of the formula (I) and/or salt thereof is capable of being used for controlling unwanted plants in crops of useful plants.
10. A composition as claimed in claim 9 wherein the useful plants are transgenic useful plants.