4-amino-6-(halo-substituted-alkyl)-picolinates and their use as herbicides
View Patent ↗Provided herein are 4-amino-6-(halo-substituted-alkyl)-picolinic acids and their derivatives, compositions comprising the acids and their derivatives, and methods of use thereof as herbicides.
1. A compound of Formula (I):
wherein
R 1 is a fluoro substituted C 1 -C 4 alkyl or fluoro substituted C 2 -C 4 alkenyl, with the proviso that R 1 is not 1,1-difluoroethyl or trifluoromethyl;
R 2 is H, Cl or F;
R 3 is halogen;
R 4 is H, C 1 -C 4 alkyl or alkylaryl;
W is —N 3 , —NR 5 R 6 , —NHOH, —NHCOR 6 or —N═CR 7 R 8 ;
wherein
R 5 represents H or C 1 -C 4 alkyl;
R 6 represents H, C 1 -C 4 alkyl or C 1 -C 4 alkoxy;
R 5 and R 6 taken together with N represent a 5- or 6-membered saturated or unstaurated ring which may contain additional O, S or N heteroatoms;
R 7 represents H or C 1 -C 4 alkyl;
R 8 represents C 1 -C 4 alkoxy or C 1 -C 4 alkylamine;
or a N-oxide or agriculturally acceptable salt thereof.
2. The compound of claim 1 , wherein R 1 is difluoromethyl.
3. The compound of claim 1 , wherein R 1 is 1-fluoroethyl.
4. The compound of claim 1 , wherein R 3 is Cl.
5. The compound of claims 1 , wherein R 4 is H and W is NH 2 .
6. The compound of claim 1 , wherein R 4 is CH 3 and W is NH 2 .
7. The compound of claim 1 , wherein R 1 is 1-fluoroethyl, R 2 is H, and R 3 is Cl.
8. The compound of claim 1 , wherein R 1 is difluoromethyl, R 2 is H, and R 3 is Cl.
9. A herbicidal composition comprising the compound of claim 1 and one or more agriculturally acceptable adjuvants or carriers.
10. The composition of claim 9 , further comprising a herbicide safener.
11. A method of controlling undesirable vegetation which comprises contacting undesirable vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation the compound of claim 1 .
12. The method of claim 11 , wherein the undesirable vegetation is controlled in glyphosate tolerant crops, glufosinate tolerant crops, dicamba tolerant crops, 2,4-D tolerant crops, ALS tolerant crops, or ACCase tolerant crops.
13. The method of claim 11 , wherein the undesirable vegetation is controlled in wheat.
14. The method of claim 11 , wherein the undesirable vegetation is controlled in rice.
15. The method of claim 11 , wherein the undesirable vegetation is controlled in corn.
16. The method of claim 11 , wherein the undesirable vegetation is controlled in pasture grass.