4-amino-6-(pyridyl and 2-substitutedphenyl)-picolinates and 6-amino-2-(pyridyl and 2-substitutedphenyl)-pyrimidine-4-carboxylates and their use as herbicides
4-amino-6-(pyridyl and 2-substitutedphenyl)-picolinic acids and their derivatives; 6-amino-2-(pyridyl and 2-substitutedphenyl)-pyrimidine-4-carboxylates and their derivatives; and methods of using the same as herbicides.
1. A compound of Formula (I):
wherein
X is CY, wherein Y is hydrogen or halogen;
R 1 is OR 1′ , wherein R 1′ is H, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl;
R 2 is halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, or C 1 -C 4 alkoxy;
R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, formyl, (C 1 -C 3 alkyl)carbonyl, (C 1 -C 3 haloalkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl, (C 1 -C 6 alkyl)carbamyl, (C 1 -C 6 alkyl)sulfonyl, tri(C 1 -C 6 alkyl)silyl, di(C 1 -C 6 alkyl)phosphonyl, or R 3 and R 4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ R 4′ , wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with the carbon atom to which they are attached form a 5- or 6-membered saturated ring;
Ar is:
X 2 is F, Cl, Br, I, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, CN, or NO 2 ;
W 2 is hydrogen or F; and
Z 3 is C 1 -C 4 haloalkyl, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, or C 1 -C 4 alkoxy;
or an N-oxide or agriculturally acceptable salt thereof.
2. The compound according to claim 1 , wherein W 2 is hydrogen.
3. The compound of claim 1 , wherein R 2 is Cl.
4. The compound of claim 1 , wherein Z 3 is C 1 haloalkyl, C 1 alkyl, C 2 alkenyl, C 2 alkynyl, or C 1 alkoxy.
5. The compound of claim 1 , wherein Y is F.
6. The compound of claim 5 , wherein Z 3 is C 1 haloalkyl, C 1 alkyl, C 2 alkenyl, C 2 alkynyl, or C 1 alkoxy.
7. The compound of claim 6 , wherein X 2 is Cl.
8. The compound of claim 1 , wherein R 3 and R 4 are each hydrogen.
9. The compound of claim 8 , wherein X 2 and R 2 are each Cl.
10. The compound of claim 8 , wherein Z 3 is C 1 haloalkyl, C 1 alkyl, C 2 alkenyl, C 2 alkynyl, or C 1 alkoxy.
11. A compound having the formula:
or an N-oxide or agriculturally acceptable salt thereof.
12. A herbicidal composition comprising the compound of claim 1 and an agriculturally acceptable adjuvant or carrier.
13. The composition of claim 12 , further comprising at least one additional herbicidal compound.
14. The composition of claim 12 , further comprising a safener.