4-amino-6-(1,3-benzodioxole)picolinates and their use as herbicides
Described herein are 4-amino-6-(1,3-benzodioxole)picolinic acids, compositions comprising 4-amino-6-(1,3-benzodioxole)picolinic acids, and the use of these compounds and compositions to control undesirable vegetation.
1. A compound defined by Formula I:
wherein
R 2 is halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, or C 1 -C 4 alkoxy; and
R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, or formyl;
or an agriculturally acceptable salt, ester, or N-oxide thereof
wherein the compound defined by Formula I has improved herbicidal activity as compared to the following compound:
2. The compound of claim 1 , wherein the compound is defined by Formula IA:
wherein
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, phenyl, substituted phenyl, or C 7 -C 12 arylalkyl;
R 2 is halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, or C 1 -C 4 alkoxy; and
R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, or formyl:
or an agriculturally acceptable salt or N-oxide thereof.
3. The compound of claim 1 , wherein R 2 is halogen, C 2 -C 4 -alkenyl, or C 1 -C 4 -alkoxy.
4. The compound of claim 1 , wherein R 2 is Cl, methoxy, vinyl, or 1-propenyl.
5. The compound of claim 1 , wherein R 2 is Cl.
6. The compound of claim 1 , wherein R 3 and R 4 are both hydrogen.
7. The compound of claim 1 , wherein the compound is defined by the structure below
8. The compound of claim 1 , wherein the compound is defined by the structure below
9. The compound of claim 1 , wherein the compound is defined by the structure below
10. The compound of claim 1 , wherein the compound is defined by the structure below
11. A herbicidal composition comprising the compound of claim 1 and an agriculturally acceptable adjuvant or carrier, wherein the compound of claim 1 is a herbicide.
12. The composition of claim 11 , further comprising at least one additional herbicidal compound.
13. The composition of claim 11 , further comprising a safener.
14. A herbicidal composition comprising the compound of claim 7 and an agriculturally acceptable adjuvant or carrier.
15. A herbicidal composition comprising the compound of claim 8 and an agriculturally acceptable adjuvant or carrier.
16. A herbicidal composition comprising the compound of claim 9 and an agriculturally acceptable adjuvant or carrier.
17. A herbicidal composition comprising the compound of claim 10 and an agriculturally acceptable adjuvant or carrier.
18. A method for controlling undesirable vegetation comprising applying a herbicidally effective amount of a compound of claim 1 directed to the undesirable vegetation, or to an area adjacent to the undesirable vegetation, or to an area where control of undesirable vegetation is desired, or to soil or water.
19. A method for controlling undesirable vegetation comprising applying a herbicidally effective amount of the composition of claim 11 directed to the undesirable vegetation, or to an area adjacent to the undesirable vegetation, or to an area where control of undesirable vegetation is desired, or to soil or water.
20. A method for controlling undesirable vegetation comprising applying a herbicidally effective amount of the composition of claim 13 directed to the undesirable vegetation, or to an area adjacent to the undesirable vegetation, or to an area where control of undesirable vegetation is desired, or to soil or water.