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

1. A compound of Formula (I):

wherein

X is 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 alkylthio, or C 1 -C 3 haloalkylthio;

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 selected from F, Cl, or Br, 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 2 -C 4 haloalkynyl, 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 alkyl)carbonyl, (C 1 -C 3 haloalkyl)carbonyl, or cyano, with the proviso that R 2 is not SCH 3 ;

R 3 and R 4 are each 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, 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 alkylsulfonyl, tri(C 1 -C 6 alkyl)silyl, or di(C 1 -C 6 alkyl)phosphonyl, or R 3 and R 4 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 each 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′ together with the carbon atom to which they are attached form a 5- or 6-membered saturated ring;

Ar is Ar2, Ar3, Ar4, Ar5, or Ar6:

wherein

X 2 is H, F, Cl, Br, I, ethynyl, CH 3 , CFH 2 , CF 2 H, CF 3 , OCF 2 H, OCF 3 , CN, CONH 2 , CO 2 H, or NO 2 ;

X 3 is H, F, Br, I, ethynyl, CH 3 , CFH 2 , CF 2 H, CF 3 , OCF 2 H, OCF 3 , CN, CONH 2 , CO 2 H, or NO 2 ;

wherein

a) when Ar is

then X is CH, CF, CCl, or CCH 3

with the provisos that:

i) X 2 is not Cl, when R 2 is Cl and X is CH;

ii) X 2 is not Cl, Br, I, or CF 3 , when R 2 is OCH 3 and X is CF; and

b) when Ar is

then X is CH or CF

with the provisos that:

i) X 3 is not H, F, or CH 3 , when R 2 is Cl and X is CH;

ii) X 3 is not Br or I, when R 2 is OCH 3 and X is CF; and

c) when Ar is

then X is CH or CF

with the provisos that:

i) X 2 is not F, when R 2 is Cl and X is CH;

ii) X 2 is not Cl, Br, I, or CF 3 , when R 2 is OCH 3 and X is CF; and

d) when Ar is

then X is CH or CF

with the provisos that:

i) X 3 is not Br or I, when X is CF and R 2 is OCH 3 , and

e) when Ar is

then X is CH, or CF;

or an N-oxide or agriculturally acceptable salt thereof.

2. The compound of claim 1 , wherein Ar is Ar2.

3. The compound of claim 1 , wherein Ar is Ar3.

4. The compound of claim 1 , wherein Ar is Ar4.

5. The compound of claim 1 , wherein Ar is Ar5.

6. The compound of claim 1 , wherein Ar is Ar6.

7. The compound of claim 1 , wherein R 1′ is H or C 1 -C 8 alkyl.

8. The compound of claim 7 , wherein R 1′ is H or methyl.

9. The compound of claim 1 , wherein Y is hydrogen, halogen, or C 1 -C 3 alkyl.

10. The compound of claim 9 , wherein Y is H, F, Cl, or CH 3 .

11. The compound of claim 1 , wherein R 2 is halogen, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, or C 1 -C 4 haloalkylthio, with the proviso that R 2 is not SCH 3 .

12. The compound of claim 11 , wherein R 2 is halogen, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, or C 1 -C 4 alkoxy.

13. The compound of claim 12 , wherein R 2 is Cl, OCH 3 , or vinyl.

14. The compound of claim 1 , wherein R 3 and R 4 are each 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 alkyl)carbonyl, (C 1 -C 3 haloalkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl, (C 1 -C 6 alkyl)carbamyl, or tri(C 1 -C 6 alkyl)silyl, or R 3 and R 4 taken together represent ═CR 3′ R 4′ , wherein R 3′ and R 4′ are each 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.

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

16. The compound of claim 1 , wherein X 2 is H, Cl, Br, I, ethynyl, CH 3 , CF 2 H, CF 3 , OCF 2 H, or CN.

17. The compound of claim 2 , wherein X 2 is H, Cl, Br, I, ethynyl, CH 3 , CF 2 H, CF 3 , OCF 2 H, or CN.

18. The compound of claim 1 , wherein X 3 is H, Br, I, ethynyl, OCF 2 H, CN, or NO 2 .

19. The compound of claim 4 , wherein X 3 is H, Br, I, ethynyl, OCF 2 H, CN, or NO 2 .

20. The compound of claim 1 , wherein X 2 is H, F, Br, I, ethynyl, CH 3 , CF 3 , OCF 2 H, or CN.

21. The compound of claim 4 , wherein X 2 is H, F, Br, I, ethynyl, CH 3 , CF 3 , OCF 2 H, or CN.

22. The compound of claim 1 , wherein X 3 is H, F, Br, I, CH 3 , CF 2 H, CF 3 , OCF 2 H, or CN.

23. The compound of claim 5 , wherein X 3 is H, F, Br, I, CH 3 , CF 2 H, CF 3 , OCF 2 H, or CN.

24. The compound of claim 1 , wherein X 2 is Br or I.

25. The compound of claim 6 , wherein X 2 is Br or I.

26. A compound having the formula:

or an N-oxide or agriculturally acceptable salt thereof.

27. A herbicidal composition comprising the compound of claim 1 or an N-oxide or agriculturally acceptable salt thereof, and an agriculturally acceptable adjuvant or carrier.

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

29. The composition of claim 27 or 28 , further comprising a safener.

30. A method for controlling undesirable vegetation, which comprises applying the compound of claim 1 , or the composition of claim 27 .