2-(poly-substituted aryl)-6-amino-5-halo-4-pyrimidinecarboxylic acids and their use as herbicides

Abstract

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 Formula I: 
       
         
           
           
               
               
           
         
       
       wherein
 Q represents Cl; 
 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 
 
       
         
           
           
               
               
           
         
       
       wherein
 W 2  represents F; 
 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 Cl; and 
 R 3  and R 4  independently represent H or C 1 -C 4  alkyl; and 
 R A  represents H or C 1 -C 4 -alkyl. 
 
     
     
         2 . The compound of  claim 1 , wherein the compound is 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         3 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         7 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         8 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         11 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         12 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         13 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         14 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         15 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         16 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         17 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         18 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         19 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         20 . A herbicidal composition comprising a herbicidally effective amount of a compound of  claim 1  and an agriculturally acceptable adjuvant or carrier. 
     
     
         21 . A method of controlling undesirable vegetation comprising (a) post-emergently contacting the vegetation or locus thereof or (b) pre-emergently contacting the area where the undesirable vegation is to be controlled a herbicidally effective amount of the compound of  claim 1 . 
     
     
         22 . The method of  claim 21 , wherein the undesirable vegetation is controlled by post-emergently contacting the vegetation of locus thereof. 
     
     
         23 . The method of  claim 21 , wherein the undesirable vegetation is controlled by pre-emergently contacting the area where the undesirable vegation is to be controlled. 
     
     
         24 . The method of  claim 21 , wherein (a) or (b) is performed in the presence of rice, wherein the rice is not injured. 
     
     
         25 . The method of  claim 24 , wherein the rice is not injured one to twenty days after performing (a) or (b). 
     
     
         26 . The method of  claim 21 , wherein (a) or (b) is performed in the presence of rice, wherein the rice is injured to a lesser extent than the undesirable vegetation. 
     
     
         27 . The method of  claim 21 , wherein (a) or (b) is performed in the presence of wheat or barley, wherein the wheat or barley is not injured. 
     
     
         28 . The method of  claim 27 , wherein the wheat or barley is not injured one to twenty days after performing (a) or (b). 
     
     
         29 . The method of  claim 21 , wherein (a) or (b) is performed in the presence of wheat or barley, wherein the wheat or barley is injured to a lesser extent than the undesirable vegetation. 
     
     
         30 . The method of  claim 21 , wherein the undesirable vegetation is CHEAL, ABUTH, HELAN, LAMPU, PAPRH, VERPE, SCPJU, CYPDI, or MOOVA.