4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyramidine-4-carboxylates and their use as herbicides

1. A compound of Formula (I):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio;

R 1 is C 3 -C 12 alkynyl or C 1 -C 3 alkyl substituted with CN;

R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl;

R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH;

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, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is 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 ═C represent a 5- or 6-membered saturated ring;

R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN;

R 6 and R 6′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ;

R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl;

R 8 is 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, formyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, arylcarbonyl, heteroarylcarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, arylsulfonyl, C 1 -C 6 trialkylsilyl, amino, C 1 -C 4 alkylamino, cyano, or phenyl;

or an N-oxide or agriculturally acceptable salt thereof.

2. The compound of claim 1 , wherein

X is N, CH, CF, CCl, or CBr;

R 1 is C 3 -C 12 alkynyl or C 1 -C 3 alkyl substituted with CN;

R 2 is chlorine;

R 3 and R 4 are hydrogen;

R 5 is hydrogen, halogen, OH, amino, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamino, or cyclopropyl;

R 6 and R 6′ are independently hydrogen, halogen, OH, NH 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyclopropyl, or vinyl;

R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, cyclopropyl, C 1 -C 3 alkylamino, or phenyl; and

R 8 is hydrogen, C 1 -C 3 alkyl, phenyl, or C 1 -C 3 alkylcarbonyl;

or an N-oxide or agriculturally acceptable salt thereof.

3. The compound of claim 1 , wherein

X is CH, CF, or N;

R 1 is C 3 -C 12 alkynyl or C 1 -C 3 alkyl substituted with CN;

R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, or C 1 -C 4 haloalkylthio;

R 3 and R 4 are 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, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, 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;

R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, or C 2 -C 4 haloalkylamino;

R 6 and R 6′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, CN, or NO 2 ;

R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, cyclopropyl, amino or C 1 -C 4 alkylamino;

R 8 is 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, formyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, arylcarbonyl, heteroarylcarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, arylsulfonyl, C 1 -C 6 trialkylsilyl, amino, C 1 -C 4 alkylamino, cyano, or phenyl.

4. The compound of claim 3 , wherein: R 2 is halogen, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, or C 1 -C 4 alkoxy.

5. The compound of claim 4 , wherein R 2 is Cl, methoxy, vinyl, or 1-propenyl.

6. The compound of claim 3 , wherein R 3 and R 4 are hydrogen.

7. The compound of claim 3 , wherein R 5 is hydrogen or F.

8. The compound of claim 7 , wherein R 5 is F.

9. The compound of claim 3 , wherein R 6 is hydrogen or F.

10. The compound of claim 3 , wherein R 6 and R 6′ are hydrogen.

11. The compound of claim 3 , wherein R 6′ is hydrogen.

12. The compound of claim 3 , wherein:

R 2 is halogen, C 2 -C 4 -alkenyl, C 2 -C 4 haloalkenyl, or C 1 -C 4 alkoxy;

R 5 is hydrogen or F;

R 6 is hydrogen or F;

R 6′ is hydrogen; and

R 7 and R 7′ are independently hydrogen or halogen.

13. The compound of claim 12 , wherein R 2 is chlorine, methoxy, vinyl, or 1-propenyl.

14. The compound of claim 12 , wherein R 3 and R 4 are hydrogen.

15. The compound of claim 13 , wherein R 3 and R 4 are hydrogen.

16. The compound of claim 12 , wherein X is CF.

17. The compound of claim 13 , wherein X is CF.

18. The compound of claim 14 , wherein X is CF.

19. The compound of claim 15 , wherein X is CF.

20. The compound of claim 3 , wherein:

R 2 is chlorine, methoxy, vinyl, or 1-propenyl; and

R 3 and R 4 are hydrogen.

21. The compound of claim 3 , wherein:

R 2 is chlorine, methoxy, vinyl, or 1-propenyl;

R 3 and R 4 are hydrogen; and

X is CF.

22. The compound of claim 21 , wherein the compound is prop-2-yn-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinate.

23. The compound of claim 21 , wherein the compound is cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinate.

24. A herbicidal composition comprising the compound of claim 1 and an agriculturally acceptable adjuvant or carrier.

25. The composition of claim 24 , further comprising at least one additional herbicidal compound.

26. The composition of claim 24 , further comprising a safener.

27. A method for controlling undesirable vegetation comprising:

providing the compound of claim 1 ; and

applying the compound to an undesirable vegetation or a locus thereof.

28. A method for controlling undesirable vegetation comprising:

providing the composition of claim 25 ; and

applying the composition to an undesirable vegetation or a locus thereof.