Herbicidal compounds
View Patent ↗The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein A 1a , A 1b , R 1 , R 2 , R 3 and R 4 and R 5 are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), and to their use for controlling weeds, in particular in crops of useful plants.
1. A compound of Formula (I):
or an agronomically acceptable salt thereof,
wherein:
A 1a and A 1b are independently selected from CH and N, wherein A 1a and A 1b are not both CH;
R 1 is selected from the group consisting of C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxyC 1 -C 3 -alkyl-, C 1 -C 6 haloalkoxyC 1 -C 3 alkyl-, C 1 -C 6 haloalkyl-, C 2 -C 6 alkenyl-, C 2 -C 6 -haloalkenyl-, C 2 -C 6 alkynyl-, C 2 -C 6 haloalkynyl-, heteroaryl-, (C 3 -C 7 )-cycloalkyl-, heterocyclyl- and phenyl-, wherein the heteroaryl-, (C 3 -C 7 )-cycloalkyl-, heterocyclyl- and phenyl- are optionally substituted by one or more substituents selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl-, C 1 -C 6 haloalkyl-, C 3 -C 6 cycloalkyl-, C 1 -C 6 alkyl-S(O)p-, C 1 -C 3 alkoxy- and C 1 -C 6 alkoxyC 1 -C 4 alkyl-;
R 2 is selected form the group consisting of C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl-, C 1 -C 6 haloalkoxy-, C 1 -C 6 alkoxyC 1 -C 6 alkyl-, C 1 -C 3 alkoxyC 2 -C 3 alkoxyC 1 -C 3 alkyl-, C 1 -C 3 alkoxyC 1 -C 3 -haloalkyl-, C 1 -C 3 -alkoxyC 1 -C 3 -alkoxyC 2 -C 3 haloalkyl-, halogen, cyano, nitro, C 1 -C 6 alkyl-S(O)p-, C 1 -C 6 haloalkyl-S(O)p-, C 4 -C 6 oxasubstituted-cycloalkoxyC 1 -C 3 alkyl-, C 4 -C 6 -oxasubstituted-cycloalkoxy-C 1 -C 3 haloalkyl-, (C 1 -C 3 alkanesulfonyl-C 1 -C 3 alkylamino)-C 1 -C 3 alkyl- and (C 1 -C 3 alkanesulfonyl-C 3 -C 4 cycloalkylamino)-C 1 -C 3 alkyl-;
R 3 is aryl or a 5 or 6-membered heteroaryl, the heteroaryl containing one to three heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein the aryl or heteroaryl component may be optionally substituted by one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl-, C 2 -C 6 alkenyl-, C 2 -C 6 alkynyl-, C 1 -C 6 haloalkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 1 -C 6 alkoxyC 1 -C 3 alkoxy-, C 1 -C 6 haloalkoxy-, C 1 -C 6 alkyl-S(O)p-, —NR 6a R 6b , cyano and nitro;
R 4 is selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl-, C 3 -C 6 cycloalkyl-, C 1 -C 6 alkoxy-C 1 -C 3 alkyl-, C 1 -C 6 -haloalkoxyC 1 -C 3 -alkyl-, C 1 -C 6 haloalkyl-, C 2 -C 6 alkenyl-, C 2 -C 6 haloalkenyl-, C 2 -C 6 alkynyl-, C 2 -C 6 haloalkynyl-, C 1 -C 6 alkoxy-, C 1 -C 6 alkyl-S(O)p- and NR 6a R 6b ;
R 5 is selected from the group consisting of hydrogen, halogen and C 1 -C 6 alkyl-;
R 6a and R 6b are independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl or together form a C 4 -C 6 alkylene chain; and
p=0, 1 or 2.
2. The compound according to claim 1 , wherein A 1a and A 1b are N.
3. The compound of claim 1 , wherein R 1 is selected from the group consisting of methyl, ethyl and n-propyl.
4. The compound according to claim 1 , wherein R 2 is selected form the group consisting of C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl-, halogen and C 1 -C 6 alkyl-S(O) p —.
5. The compound according to claim 1 , wherein R 3 is an aryl or heteroaryl selected from the group consisting of phenyl, furanyl, thiophenyl, thiazolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, isothiazolyl, pyridyl, pyridazinyl, pyrazinyl, pyrimidinyl and triazolyl.
6. The compound according to claim 5 , wherein R 3 is selected from the group consisting of phenyl, isoxazolyl and pyrimidinyl.
7. The compound according to claim 1 , wherein R 4 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl- and C 1 -C 6 haloalkyl-.
8. The compound according to claim 7 , wherein R 4 is selected from the group consisting of hydrogen, methyl and trifluoromethyl.
9. The compound according to claim 1 , wherein R 5 is hydrogen.
10. A herbicidal composition comprising the compound of formula 1 according to claim 1 and an agriculturally acceptable formulation adjuvant.
11. The herbicidal composition according to claim 10 , further comprising at least one additional pesticide.
12. The herbicidal composition according to claim 11 , wherein the additional pesticide is a herbicide or herbicide safener.
13. A method of controlling weeds at a locus comprising applying to the locus of a weed, a weed controlling amount of the compound according to claim 1 .