6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
View Patent ↗4-Aminopicolinic acids having tri- and tetra-substituted aryl substituents in the 6-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.
1. A compound of the formula I
wherein
Q 1 represents H or F;
Q 2 represents a halogen with the proviso that when Q 1 is H then Q 2 is Cl or Br;
R 1 and R 2 independently represent H, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, hydroxy, C 1 -C 6 alkoxy, amino, C 1 -C 6 acyl, C 1 -C 6 carboalkoxy, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl or C 1 -C 6 dialkyl phosphonyl or R 1 and R 2 taken together with N represent a 5- or 6-membered saturated ring; and
Ar represents a polysubstituted aryl group selected from the group consisting of
wherein
W 1 represents halogen;
X 1 represents F, Cl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —CN, —NR 3 R 4 or fluorinated acetyl or propionyl;
Y 1 represents C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or —CN, or, when X 1 and Y 1 are taken together, represents —O(CH 2 ) n O— wherein n=1 or 2; and
R 3 and R 4 independently represent H or C 1 -C 4 alkyl;
wherein
W 2 represents F or Cl;
X 2 represents F, Cl, —CN, —NO 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —NR 3 R 4 or fluorinated acetyl or propionyl;
Y 2 represents halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or —CN, or, when W 2 represents F, X 2 and Y 2 taken together represent —O(CH 2 ) n O— wherein n=1 or 2; and
R 3 and R 4 independently represent H or C 1 -C 6 alkyl; and
wherein
Y 3 represents halogen, —CN or —CF 3 ;
Z 3 represents F, Cl, —CN, —NO 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —NR 3 R 4 or fluorinated acetyl or propionyl; and
R 3 and R 4 independently represent H, or C 1 -C 6 alkyl;
and agriculturally acceptable derivatives of the carboxylic acid group.
2. A compound of claim 1 in which R 1 and R 2 represent H.
3. A compound of claim 1 in which Q 1 represents H.
4. A compound of claim 1 in which Q 2 represents Cl.
5. A compound of claim 1 in which Q 1 represents H and Q 2 represents Cl.
6. A compound of claim 1 in which Ar represents
wherein
W 1 represents halogen;
X 1 represents F, Cl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —CN, —NR 3 R 4 or fluorinated acetyl or propionyl;
Y 1 represents C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or —CN, or, when X 1 and Y 1 are taken together, represents —O(CH 2 ) n O— wherein n=1 or 2; and
R 3 and R 4 independently represent H or C 1 -C 4 alkyl.
7. A compound of claim 6 in which W 1 represents Cl or F.
8. A compound of claim 6 in which X 1 represents C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl or —NR 3 R 4 .
9. A compound of claim 6 in which Y 1 represents Cl, Br or —CF 3 .
10. A compound of claim 1 in which Ar represents
wherein
W 2 represents F or Cl;
X 2 represents F, Cl, —CN, —NO 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —NR 3 R 4 or fluorinated acetyl or propionyl;
Y 2 represents halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or —CN, or, when W 2 represents F, X 2 and Y 2 taken together represent —O(CH 2 ) n O— wherein n=1 or 2; and
R 3 and R 4 independently represent H or C 1 -C 6 alkyl.
11. A compound of claim 10 in which X 2 represents C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl or —NR 3 R 4 .
12. A compound of claim 10 in which Y 2 represents Cl, Br or —CF 3 .
13. A compound of claim 1 in which Ar represents
wherein
Y 3 represents halogen, —CN or —CF 3 ;
Z 3 represents F, Cl, —CN, —NO 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —NR 3 R 4 or fluorinated acetyl or propionyl; and
R 3 and R 4 independently represent H, or C 1 -C 6 alkyl.
14. A compound of claim 13 in which Y 3 represents Cl, Br or —CF 3 .
15. A compound of claim 13 in which Z 3 represents C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl or —NR 3 R 4 .
16. A herbicidal composition comprising an herbicidally effective amount of a compound of Formula I, according to claim 1 , in admixture with an agriculturally acceptable adjuvant or carrier.
17. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil to prevent the emergence of vegetation an herbicidally effective amount of a compound of Formula I, according to claim 1 .