Herbicidal thiazole compounds
The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein Q, R 1 , R 3 , R 4 and n are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.
1 . A compound of Formula (I):
or an agronomically acceptable salt thereof,
wherein
Q is a 5-membered aromatic heterocyclic ring selected from the group consisting of:
wherein R 2 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, cyclopropyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy-, C 1 -C 2 haloalkoxy-, halogen, —C(O)C 1 -C 4 alkyl, NO 2 , —CH 2 CN, —CN and —S(O) p C 1 -C 4 alkyl;
X is O or S(O) p ;
each R 1 is independently selected from the group consisting of halogen, —CN, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy-, C 1 -C 4 haloalkoxy- and —S(O) p C 1 -C 4 alkyl;
R 3 is selected from the group consisting of hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl and C 2 -C 3 alkenyl;
R 4 is selected from the group consisting of hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl and C 2 -C 3 alkenyl;
n=0, 1 or 2; and
p=0, 1 or 2.
2 . The compound of Formula (I) according to claim 1 , wherein Q is selected from the group consisting of Q1, Q2 and Q5.
3 . The compound of Formula (I) according to claim 1 , wherein Q is Q2.
4 . The compound according to claim 1 , wherein n is 1 and R 1 is fluoro.
5 . The compound according to claim 4 , wherein R 1 is 3-fluoro.
6 . The compound according to claim 1 , wherein R 3 is selected from the group consisting of hydrogen, chloro, bromo and difluoromethyl.
7 . The compound according to claim 1 , wherein R 4 is selected from the group consisting of hydrogen, chloro, bromo, methyl, vinyl and difluoromethyl.
8 . A herbicidal composition comprising a compound according to claim 1 and an agriculturally acceptable formulation adjuvant.
9 . A herbicidal composition according to claim 8 , further comprising at least one additional pesticide.
10 . A herbicidal composition according to claim 9 , wherein the additional pesticide is a herbicide.
11 . A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to claim 8 .
12 . A compound selected from Compound 1.001-1.035 according to Formula (I):
CMP
n
R 1
Q
x
R 3
R 4
1.001
1
3-F
5-(3
O
H
CF 2 H
difluoromethyl)-
isoxazole
1.002
1
3-F
5-(3-
O
H
vinyl
difluoromethyl)-
isoxazole
1.003
1
3-F
5-(3-
O
H
H
difluoromethyl)-
isoxazole
1.004
1
3-F
5-(3.
O
H
Br
difluoromethyl)-
isoxazole
1.005
1
3-F
5-(3-
O
H
CH 3
difluoromethyl)-
isoxazole
1.006
1
3-F
5-(3-
O
H
Cl
difluoromethyl)-
isoxazole
1.007
1
3-F
5-(3-
O
Br
H
difluoromethyl)-
isoxazole
1.008
1
3-F
5-(3-
O
Cl
H
difluoromethyl)-
isoxazole
1.009
3-F
5-(3-
O
CF 2 H
H
difluoromethyl)-
isoxazole
1.010
3
6-F
5-(3-
O
H
Cl
difluoromethyl)-
isoxazole
1.011
3
6-CH 3
5-(3-
O
H
Cl
difluoromethyl)-
isoxazole
1.012
3
3-CN
5-(3-
O
H
CI
difluoromethyl)-
isoxazole
1.013
3
3-CN
5-(3-
O
H
Br
difluoromethyl)-
isoxazole
1.014
1
3-CN
5-(3-
O
H
CF 2 H
difluoromethyl)-
isoxazole
1.015
1
3-CN
4-
O
H
Br
(vifluoromethyl)
pyrazol-1-yl
1.016
1
3-CN
4-
O
H
CH 3
(trifluoromethyl)
pyrazol-1-yl
1.017
1
3-CN
4-
O
H
CF 2 H
(trifluoromethyl)
pyrazol-1-yl
1.018
1
3-CN
4-
O
H
Cl
(trifluoromethyl)
pyrazol-1-yl
1.019
1
3-Cl
5-(3-
O
H
CF 2 H
difluoromethyl)
isoxazole
1.020
1
3-Br
5-(3-
O
H
CF 2 H
difluoromethyl)
isoxazole
1.021
0
—
5-(3-
O
H
CF 2 H
difluoromethyl)
isoxazole
1.022
1
3-Cl
5-(3-
O
H
Cl
difluoromethyl)
isoxazole
1.023
1
3-Br
5-(3-
O
H
Cl
difluoromethyl)
isoxazole
1.024
1
3-Br
5-(3-
O
H
Br
difluoromethyl)
isoxazole
1.025
1
3-Cl
5-(3-
O
H
Br
difluoromethyl)
isoxazole
1.026
0
H
5-(3-
O
H
Cl
difluoromethyl)
isoxazole
1.027
0
H
5-(3-
O
H
Br
difluoromethyl)
isoxazole
1.028
1
3-Br
5-(3-
O
Cl
Cl
difluoromethyl)
isoxazole
1.029
1
3-F
5-(3-
O
Cl
Cl
difluoromethyl)
isoxazole
1.030
1
3-Br
5-(3-
O
CF 2 H
Cl
difluoromethyl)
isoxazole
1.031
1
3-F
5-(3-
O
Cl
H
difluoromethyl)
isoxazole
1.032
1
3-Cl
5-(3-
O
Cl
Cl
difluoromethyl)
isoxazole
1.033
1
3-F
5-(3-
O
CF 3
H
difluoromethyl)
isoxazole
1.034
1
3-Br
5-(3-
O
CF 3
H
difluoromethyl)
isoxazole
1.035
1
3-F
5-(3-
O
CF 3 H
Cl.
difluoromethyl)
isoxazole
13 . The compound according to claim 12 , selected from:
3-(DIFLUOROMETHYL)-5-[2-[5-(DIFLUOROMETHYL) THIAZOL-2-YL]OXY-6-FLUORO-PHENYL]ISOXAZOLE (1.001);
5-[2-(5-BROMOTHIAZOL-2-YL)OXY-6-FLUORO-PHENYL]-3-(DIFLUOROMETHYL)ISOXAZOLE (1.004);
3-(DIFLUOROMETHYL)-5-[2-FLUORO-6-(5-VINYLTHIAZOL-2-YL)OXY-PHENYL]ISOXAZOLE (1.002);
3-(DIFLUOROMETHYL)-5-[2-FLUORO-6-(5-METHYLTHIAZOL-2-YL)OXY-PHENYL]ISOXAZOLE (1.005); and
5-[2-(5-CHLOROTHIAZOL-2-YL) SULFANYL-6-FLUORO-PHENYL]-3-(DIFLUOROMETHYL)ISOXAZOLE (1.031).
14 . A herbicidal composition comprising a compound according to claim 12 and an agriculturally acceptable formulation adjuvant.
15 . The herbicidal composition according to claim 14 , further comprising at least one additional pesticide.
16 . The herbicidal composition according to claim 14 , further comprising at least one additional pesticide or a herbicide safener.
17 . A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of the composition according to claim 14 .