3-Aminocarbonyl substituted benzoylpyrazolones
View Patent ↗A description is given of derivatives of benzoylpyrazoles of the formula (I) and of their use as herbicides. In this formula (I) R 1a , R 1b , R 1c , R 2 , R 3 , R 4 and R 5 stand for various radicals, X for a bridging atom, L for a carbon chain and Y for a chalcogen atom.
1. A compound of the formula (I) or salt thereof
in which the radical and the indices have the following definitions:
X is O;
L is CH;
Y is oxygen;
R 1a , R 1b , R 1c independently are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato,
(C 1 -C 6 )-alkyl-CO—O, (C 1 -C 6 )-alkyl-S(O) n —O, (C 1 -C 6 )-alkyl-S(O) m , (C 1 -C 6 )-haloalkyl-S(O) m , (C 3 -C 7 )-cycloalkyl-S(O) m , di-(C 1 -C 6 )-alkyl-N—SO 2 , (C 1 -C 6 )-alkyl-SO 2 —NH, (C 1 -C 6 )-alkyl-NH—CO, di-(C 1 -C 6 )-alkyl-N—CO, (C 1 -C 6 )-alkyl-SO 2 —[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-CO—[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-O—CH 2 , (C 1 -C 6 )-alkyl-S(O) n —CH 2 , (C 1 -C 6 )-alkyl-NH—CH 2 ,
or are each (C 1 -C 6 )-alkyl-(Y) p , (C 2 -C 6 )-alkenyl-(Y) p , (C 2 -C 6 )-alkynyl-(Y) p , (C 3 -C 9 )-cycloalkyl-(Y) p , (C 3 -C 9 )-cycloalkenyl-(Y) p , (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkyl-(Y) p or (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkenyl-(Y) p each of which is substituted by v radicals from the group consisting of cyano, nitro and halogen;
R 2 and R 3 together with the nitrogen atom linking them form a pyyrole ring;
R 4 is hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl, (C 3 -C 9 )-cycloalkyl or (C 3 -C 9 )-halocycloalkyl;
R 5 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 9 )-cycloalkyl, (C 3 -C 9 )-halo-cycloalkyl, or is phenyl substituted by v radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and halo-(C 1 -C 4 )-alkoxy;
R 6 is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, halo-(C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkoxycarbonyl, halo-(C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, halo-(C 1 -C 6 )-alkylaminocarbonyl,(C 1 -C 6 )-dialkylaminocarbonyl, halo-(C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-alkylsulfonyl, halo-(C 1 -C 6 )-alkylsulfonyl, or is benzyl, benzoyl, benzoylmethyl, phenoxycarbonyl or phenylsulfonyl each of which is substituted by v radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and halo-(C 1 -C 4 )-alkoxy;
m
is 1 or 2;
n
is 0, 1 or 2;
p
is 0 or 1;
v
is 0, 1, 2 or 3;
w and x
independently are each 0, 1, 2, 3 or 4;
w and x should not both be zero at the same time.
2. A compound as claimed in claim 1 , wherein R 1c is hydrogen.
3. A compound as claimed in claim 1 , wherein
R 1a , R 1b independently are each F, Cl, Br, CH 3 , CH 3 S, CH 3 O, CH 3 SO 2 , C 2 H 5 SO 2 , CF 3 CH 2 SO 2 , cyclopropyl-SO 2 , CF 3 or NO 2 .
4. A compound as claimed in claim 1 , wherein
R 4 is hydrogen, methyl or cyclopropyl.
5. A compound as claimed in claim 1 , wherein
R 6 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkylsulfonyl, or is benzoyl or phenylsulfonyl each of which is substituted by v radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and halo-(C 1 -C 4 )-alkoxy.
6. A compound as claimed in claim 1 , wherein
R 1a , R 1b independently are each Cl, Br, NO 2 , CH 3 , CH 3 SO 2 or C 2 H 5 SO 2 ; and
R 5 is methyl or ethyl.
7. A herbicidal composition comprising a herbicidally effective amount of at least one compound of the general formula (I) as claimed in claim 1 .
8. A herbicidal composition as claimed in claim 7 in a mixture with formulating auxiliaries.
9. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the general formula (I) as claimed in claim 1 to the plants or to the site of the unwanted plant growth.
10. The use as claimed in claim 9 , wherein the unwanted plants in crops of useful plants.
11. The use as claimed in claim 10 , wherein the useful plants are transgenic.
12. A method of controlling unwanted plants, which comprises applying the herbicidal composition as claimed in claim 7 to the plants or to the site of the unwanted plant growth.
13. A method of controlling unwanted plants, which comprises applying the herbicidal composition as claimed in claim 8 to the plants or to the site of the unwanted plant growth.