4-trifluoromethylpyrazolyl-substituted pyridines and pyrimidines
View Patent ↗A description is given of 4-trifluoromethylpyrazolyl-substituted pyridines and pyrimidines of the formula (I) and of their use as herbicides. In this formula (I), R 1 , R 2 , R 3 and R 4 stand for various radicals, A for an aromatic or heteroaromatic radical, and Z denotes a nitrogen or carbon atom.
1. A compound of the formula (I) or N-oxide or salt thereof,
in which the radicals and indices have the following definitions:
Z is N or CR 8 ;
Y is a radical from the group Y1 to Y7:
R 1 and R 2 independently are each hydrogen, halogen, cyano, isocyano, OH, COOR 10 , COR 10 , CH 2 OH, CH 2 SH, CH 2 NH 2 , NO 2 , CSNH 2 , CONH 2 , (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 -alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkoxy, (C 1 -C 2 )-alkoxy-(C 1 -C 2 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 -alkynyl, (C 3 -C 4 )-alkenyloxy, (C 3 -C 4 )-alkynyloxy, (C 1 -C 2 )-alkylthio-(C 1 -C 2 )-alkyl, S(O) n R 9 , (C 1 -C 2 )-alkylsulfonyl-(C 1 -C 2 )-alkyl, amino, (C 1 -C 4 )-alkylamino, (C 1 -C 3 )-alkylcarbonylamino, (C 1 -C 4 )-alkylsulfonylamino or di-(C 1 -C 4 )-alkylamino;
R 3 and R 4 independently are each hydrogen, halogen, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy or halo-(C 1 -C 4 )-alkoxy;
R 5 is halogen, cyano, (C 1 -C 4 -alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 )-C 4 )-alkoxy, halo-(C 1 -C 4 )-alkylthio, (C 3 -C 5 )-cycloalkyl, halo-(C 3 -C 5 )-cycloalkyl, SF 5 , S(O) n R 9 , (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkynyl;
R 6 is hydrogen, halogen, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkoxy or S(O) n R 9 ;
R 7 is (C 1 -C 4 )-alkyl;
R 8 is hydrogen, halogen, cyano, NO 2 , (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, hydroxy, amino, (C 1 -C 4 )-alkylamino, (C 1 -C 3 )-alkylcarbonylamino, (C 1 -C 4 )-alkylsulfonylamino, di-(C 1 -C 4 )-alkylamino or S(O) n R 9 ;
R 9 is hydrogen, (C 1 -C 4 )-alkyl or halo-(C 1 -C 4 )-alkyl;
R 10 is hydrogen or (C 1 -C 4 )-alkyl;
n is 0, 1 or 2.
2. A compound as claimed in claim 1 , wherein Y is a radical from the group Y1 to Y6.
3. A compound as claimed in claim 1 , wherein R 1 and
R 2 independently are each hydrogen, halogen, cyano, OH, CHO, vinyl, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, vinyl or (C 1 -C 4 )-alkoxy.
4. A compound as claimed in claim 1 , wherein R 3 and R 4 independently are each hydrogen, halogen, methyl or methoxy.
5. A compound as claimed in claim 1 , wherein
R 1 is hydrogen, halogen, cyano, CHO, methoxy, methyl or ethyl, and
R 2 is hydrogen, OH, methyl, ethyl, methoxy or ethoxy.
6. A compound as claimed in claim 1 , wherein R 3 and R 4 are each hydrogen or methyl.
7. A compound as claimed in claim 1 , wherein R 8 is hydrogen, halogen or (C 1 -C 4 )-alkyl.
8. A compound as claimed in claim 1 , wherein R 5 is halogen, cyano, halo-(C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkoxy or halo-(C 1 -C 4 )-alkylthio.
9. A compound as claimed in claim 1 , wherein R 6 is hydrogen.
10. A herbicidal composition comprising a herbicidally effective amount of at least one compound of the formula (I) as claimed in claim 1 .
11. A herbicidal composition as claimed in claim 10 in a mixture with formulation auxiliaries.
12. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the formula (I) as claimed in claim 1 to the plants or to the site of the unwanted plant growth.
13. The method as claimed in claim 12 , wherein the compound of the formula (I) is used to control unwanted plants in crops of useful plants.
14. The method as claimed in claim 13 , wherein the useful plants are transgenic.