3-halo-(arly)-4-iminotetrahydropicolinates and their use as herbicides
View Patent ↗3-Halo-6-(aryl)-4-iminotetrahydropicolinic acids having mono-, di- tri- and tetra-substituted aryl substituents in the 6-position, and their acid derivatives, are herbicides demonstrating a broad spectrum of weed control.
1. A compound of the Formula I
wherein
R represents —OS(O) 2 R 1 , —OC(O)R 1 , —OC(O)OR 1 ;
R 1 represents C 1 -C 4 alkyl or unsubstituted or substituted phenyl;
Q represents Cl or Br; and
W represents H, F or Cl;
X represents H, F, Cl or C 1 -C 4 alkoxy;
Y represents halogen; and
Z represents H or F; and
R A represents H, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl.
2. The compound of claim 1 , wherein W represents H or F, X represents H, F or C 1 -C 4 alkoxy, Y represents Cl and Z represents H.
3. An herbicidal composition comprising an herbicidally effective amount of a compound as claimed in claim 1 , in admixture with an agriculturally acceptable adjuvant or carrier.
4. A method of controlling undesirable vegetation which comprises contacting the vegetation or locus thereof with or applying to soil to prevent the emergence of vegetation an herbicidally effective amount of a compound of claim 1 .
5. The compound of claim 1 , wherein R is —OS(O) 2 CH 3 .
6. The compound of claim 1 , wherein R is —OC(O)CH 3 .
7. The compound of claim 1 , wherein Z is H.
8. The compound of claim 1 , wherein W is F, X is methoxy, Y is Cl, and Z is H.
9. The compound of claim 1 , which R A is methyl or ethyl.
10. The compound of claim 1 , wherein the compound is:
11. The compound of claim 1 , wherein the compound is:
12. The compound of claim 1 , wherein the compound is:
13. The compound of claim 1 , wherein the compound is:
14. The composition of claim 3 , wherein W represents H or F, X represents H, F or C 1 -C 4 alkoxy, Y represents Cl and Z represents H.
15. The composition of claim 3 , wherein the compound is:
16. The method of claim 4 , wherein W represents H or F, X represents H, F or C 1 -C 4 alkoxy, Y represents Cl and Z represents H.
17. The method of claim 4 , wherein the compound is:
18. The method of claim 4 , wherein the undesirable vegetation is pigweed, sunflower, ivyleaf morningglory, wild oat, giant foxtail, lambsquarters, bindweed, velvetleaf, or barnyardgrass.
19. The method of claim 4 , wherein the contacting is performed pre-emergently.
20. The method of claim 4 , wherein the contacting is performed post-emergently.