2-(Poly-substituted aryl)-6-amino-5-halo-4-pyrimidinecarboxylic acids and their use as herbicides
View Patent ↗6-Amino-5-halo-4-pyrimidinecarboxylic acids having poly-substituted aryl substituents in the 2-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 represents a halogen;
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
a)
wherein
W 1 represents F or Cl;
X 1 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio or —NR 3 R 4 ;
Y 1 represents halogen or C 1 -C 4 haloalkyl 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 R4 independently represent H or C 1 -C 4 alkyl;
b)
wherein
W 2 represents F or Cl;
X 2 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio or —NR 3 R 4 ;
Y 2 represents halogen or C 1 -C 4 haloalkyl or, when X 2 and Y 2 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; and
c)
wherein
Y 3 represents halogen or C 1 -C 4 haloalkyl or, when Y 3 and Z 3 are taken together, represents —O(CH 2 ) n O— wherein n=1 or 2;
Z 3 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio or —NR 3 R 4 ; and
R 3 and R 4 independently represent H or C 1 -C 4 alkyl; and agriculturally acceptable derivatives of the carboxylic acid group.
2. A compound of claim 1 in which R 1 and R 2 independently represent H or C 1 -C 6 alkyl.
3. A compound of claim 1 in which Q represents Cl or Br.
4. A compound of claim 1 in which Ar represents
wherein
W 1 represents F or Cl;
X 1 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio or —NR 3 R 4 ;
Y 1 represents halogen or C 1 -C 4 haloalkyl 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.
5. A compound of claim 4 in which X 1 represents C 1 -C 4 alkoxy or —NR 3 R 4 .
6. A compound of claim 4 in which Y 1 represents Cl.
7. A compound of claim 1 in which Ar represents
wherein
W 2 represents F or Cl;
X 2 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio or —NR 3 R 4 ;
Y 2 represents halogen or C 1 -C 4 haloalkyl or, when X 2 and Y 2 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.
8. A compound of claim 7 in which X 2 represents C 1 -C 4 alkoxy or —NR 3 R 4 .
9. A compound of claim 7 in which Y 2 represents Cl.
10. A compound of claim 1 in which Ar represents
wherein
Y 3 represents halogen, C 1 -C 4 haloalkyl or, when Y 3 and Z 3 are taken together, represents —O(CH 2 ) n O— wherein n=1 or 2;
Z 3 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio or —NR 3 R 4 .
11. A compound of claim 10 in which Z 3 represents C 1 -C 4 alkoxy.
12. A compound of claim 10 in which Y 3 represents Cl.
13. A herbicidal composition comprising a herbicidally effective amount of a compound of Formula I, according to claim 1 , in a mixture with an agriculturally acceptable adjuvant or carrier.
14. 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 .