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 C 1 ; 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 alkylcarbamoyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphoryl, 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;

A is one of groups Ar3 to Ar24:

R 5 is 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, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, or C 2 -C 4 haloalkylamino.

R 6 is 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, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, or C 2 -C 4 haloalkylamino;

R 6′ is hydrogen or halogen;

R 6″ 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, CN or NO 2 ;

R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or C 1 -C 3 alkoxy;

R 8 and R 8′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or C 1 -C 3 alkoxy;

R 9 , R 9′ , R 9″ and R 9′″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or C 1 -C 3 alkoxy;

R 10 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 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, or C 1 -C 6 trialkylsilyl;

or an N-oxide or an agriculturally acceptable salt thereof;

provided A is not

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

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

4. The compound of claim 1 wherein R 3 and R 4 are both hydrogen.

5. The compound of claim 1 wherein X is N, CH, or CF.

6. The compound of claim 1 wherein R 5 is hydrogen or halogen.

7. The compound of claim 6 wherein R 5 is hydrogen or F.

8. The compound of claim 1 wherein R 6 is hydrogen or F.

9. The compound of claim 1 wherein R 6′ is hydrogen.

10. The compound of claim 1 wherein:

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

R 3 and R 4 are both hydrogen; and

X is N, CH, or CF.

11. The compound of claim 1 wherein:

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

R 3 and R 4 are hydrogen; and

X is N, CH, or CF;

Ar is Ar7, Ar9, Ar10, Ar13, Ar15, Ar16, Ar19, Ar21, or Ar22;

R 5 is hydrogen or F;

R 6 is hydrogen or F;

R 6′ is hydrogen;

R 7 , R 7′ , R 8 , R 8′ , R 9 , R 9′ , R 9″ , and R 9′″ , if applicable to the relevant Ar group, are independently hydrogen or fluorine.

12. The compound of claim 1 wherein:

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

R 3 and R 4 are hydrogen; and

X is N, CH, or CF.

13. The compound of claim 1 wherein:

R 2 is chlorine;

R 3 and R 4 are hydrogen; and

X is N, CH, or CF.

14. The compound of claim 1 wherein:

R 2 is methoxy;

R 3 and R 4 are hydrogen; and

X is N, CH, or CF.

15. The compound of claim 1 wherein:

R 2 is vinyl or 1-propenyl;

R 3 and R 4 are hydrogen; and

X is N, CH, or CF.

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

17. The composition of claim 16 , further comprising an additional herbicidal compound.

18. The composition of claim 16 , further comprising a safener.

19. A method for controlling vegetation comprising applying a herbicidally effective amount of a compound of claim 1 .