2-(poly-substituted aryl)-6-amino-5-halo-4-pyrimidinecarboxylic acids and their use as herbicides
View Patent ↗6-Amino-5-halo-4-pyrimidinecarboxylic acids having poly-substituted aryl substituents in the 2-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.
1. A compound of Formula I:
wherein
Q represents Cl;
R 1 and R 2 independently represent H, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, hydroxy, C 1 -C 6 alkoxy, amino, C 1 -C 6 acyl, C 1 -C 6 carboalkoxy, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl or C 1 -C 6 dialkyl phosphonyl or R 1 and R 2 taken together with N represent a 5- or 6-membered saturated ring; and
Ar represents
wherein
W 2 represents F or Cl;
X 2 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio or —NR 3 R 4 ;
Y 2 represents Cl; and
R 3 and R 4 independently represent H or C 1 -C 4 alkyl; and
R A represents H or C1-C4-alkyl.
2. The compound of claim 1 , wherein the compound is
3. The compound of claim 1 , wherein the compound is:
4. The compound of claim 1 , wherein the compound is:
5. The compound of claim 1 , wherein the compound is:
6. The compound of claim 1 , wherein the compound is:
7. The compound of claim 1 , wherein the compound is:
8. The compound of claim 1 , wherein the compound is:
9. The compound of claim 1 , wherein the compound is:
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 compound of claim 1 , wherein the compound is:
15. The compound of claim 1 , wherein the compound is:
16. The compound of claim 1 , wherein the compound is:
17. The compound of claim 1 , wherein the compound is:
18. The compound of claim 1 , wherein the compound is:
19. The compound of claim 1 , wherein the compound is:
20. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1 and an agriculturally acceptable adjuvant or carrier.
21. A method of controlling undesirable vegetation comprising (a) post-emergently contacting the vegetation or locus thereof or (b) pre-emergently contacting the area where the undesirable vegation is to be controlled a herbicidally effective amount of the compound of claim 1 .
22. The method of claim 21 , wherein the undesirable vegetation is controlled by post-emergently contacting the vegetation of locus thereof.
23. The method of claim 21 , wherein the undesirable vegetation is controlled by pre-emergently contacting the area where the undesirable vegation is to be controlled.
24. The method of claim 21 , wherein (a) or (b) is performed in the presence of rice, wherein the rice is not injured.
25. The method of claim 24 , wherein the rice is not injured one to twenty days after performing (a) or (b).
26. The method of claim 21 , wherein (a) or (b) is performed in the presence of rice, wherein the rice is injured to a lesser extent than the undesirable vegetation.
27. The method of claim 21 , wherein (a) or (b) is performed in the presence of wheat or barley, wherein the wheat or barley is not injured.
28. The method of claim 27 , wherein the wheat or barley is not injured one to twenty days after performing (a) or (b).
29. The method of claim 21 , wherein (a) or (b) is performed in the presence of wheat or barley, wherein the wheat or barley is injured to a lesser extent than the undesirable vegetation.
30. The method of claim 21 , wherein the undesirable vegetation is CHEAL, ABUTH, HELAN, LAMPU, PAPRH, VERPE, SCPJU, CYPDI, or MOOVA.