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

1. A compound of the 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 OR 1′ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl;

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 alknyl, 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 alknyl, 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;

A is one of groups A3 to A12, A15 to A20, or A25 to A36

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 , 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 alknyl, 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, or phenyl;

or an N-oxide or agriculturally acceptable salt thereof.

2. A compound of the Formula (I):

wherein

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

R 1 is O R1′ , wherein R 1′ is hydrogen or C 1 -C 4 alkyl;

R 2 is chlorine;

R 3 and R 4 are hydrogen;

A is one of groups A3 to A12 or A15 to A20

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 , 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, or 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 OR 1′ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl;

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 alknyl, 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 alknyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino;

A is A3, A7, A8, A9, A10, A11, A12, A15, A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32;

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 , 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 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, or C 1 -C 6 alkylcarbamyl.

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 A is one of groups A3, A7, A8, A9, A10, and A15.

8. The compound of claim 7 wherein A is one of groups A3 and A15.

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

10. The compound of claim 9 wherein R 5 is F.

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

12. The compound of claim 3 wherein R 6″ is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, C 2 -C 4 alkynyl, CN, or NO 2 .

13. The compound of claim 3 wherein R 6 , R 6′ , and R 6″ are all hydrogen.

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

15. 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;

R 6″ , if applicable to the relevant A group, is hydrogen, halogen, C 1 -C 4 haloalkyl, cyclopropyl, CN, or NO 2 ; and

R 7 and R 7 ′, if applicable to the relevant A group, are independently hydrogen or halogen.

16. The compound of claim 15 wherein R 2 is chlorine, methoxy, vinyl, or 1-propenyl.

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

18. The compound of claim 16 wherein R 3 and R 4 are hydrogen.

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

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

21. The compound of claim 17 wherein X is CF.

22. The compound of claim 18 wherein X is CF.

23. The compound of claim 3 wherein:

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

R 3 and R 4 are hydrogen; and

A is A15.

24. The compound of claim 3 wherein:

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

R 3 and R 4 are hydrogen;

X is CF; and

A is A15.

25. The compound of claim 24 which is methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinate.

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

27. The composition of claim 26 , further comprising at one additional herbicidal compound.

28. The composition of claim 26 further comprising a safener.

29. The composition of claim 27 further comprising a safener.

30. A method for controlling undesirable vegetation which comprises applying the compound of claim 1 to the undesirable vegetation or locus thereof.

31. A method for controlling undesirable vegetation which comprises applying the compound of claim 26 to the undesirable vegetation or locus thereof.