N-alkoxyamides of 6-(trisubstituted phenyl)-4-aminopicolinates and their use as selective herbicides for crops
View Patent ↗N-Alkoxyamides of 4-aminopicolinic acids and 6-amino-4-pyrimidinecarboxylates are selective herbicides for corn, canola and sugar beet.
1. A compound of Formula I:
wherein
X represents CH, CF, or N;
Y represents phenyl substituted with 1-4 substituents independently selected from halogen, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, cyano, nitro, N(R 4 ) 2 , or where two adjacent substituents are taken together as —OCH 2 O—;
Z represents halogen, C 1 -C 3 alkoxy, or C 2 -C 4 alkenyl;
R 1 represents H, C 1 -C 3 alkyl, C 2 -C 4 acyl, or benzyl;
R 2 represents H, C 1 -C 3 alkyl, or C 2 -C 4 acyl;
R 3 represents H, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylcarbonyl, alkylthio, alkylsulfonyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkenyl, haloalkenyl, C 2 -C 8 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl, alkylcycloalkyl, alkylcycloalkenyl, unsubstituted or substituted arylalkyl, or R 2 and R 3 together with the O and N atoms to which they are joined form an unsubstituted or substituted 5- to 7-membered ring optionally containing one further heteroatom selected from O, N, and S; and
R 4 represents H or C 1 -C 3 alkyl; or a salt thereof.
2. The compound of claim 1 in which X represents CH or N.
3. The compound of claim 1 in which Z represents halogen or methoxy.
4. The compound of claim 1 in which R 1 and R 2 represent hydrogen.
5. The compound of claim 1 in which R 3 represents C 1 -C 4 alkyl, C 2 -C 6 alkenyl or unsubstituted or para-substituted benzyl.
6. The compound of claim 1 , which is not a salt.
7. The compound of claim 1 , wherein X is CH.
8. The compound of claim 1 , wherein Y is phenyl substituted with 3 substituents.
9. The compound of claim 1 , wherein Y is phenyl substituted with 1-4 substituents independently selected from halogen or C 1 -C 3 alkoxy.
10. The compound of claim 1 , wherein X represents CH or N; Y represents substituted phenyl; Z represents halogen or methoxy; R 1 and R 2 represent hydrogen; and R 3 represents C 1 -C 4 alkyl, C 2 -C 6 alkenyl or unsubstituted or para-substituted benzyl.
11. The compound of claim 1 , wherein the compound is
12. A compound of the following formula:
or a salt thereof.