Synergistic weed control from applications of pyridine carboxylic acid herbicides and synthetic auxin herbicides and/or auxin transport inhibitors

Abstract

Disclosed herein are herbicidal compositions comprising a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. Also disclosed herein are methods of controlling undesirable vegetation which comprise applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof, wherein (a) and (b) are each added in an amount sufficient to provide a herbicidal effect.

1 . A herbicidal composition comprising a synergistic herbicidally effective amount of
 (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof, and   (b) a synthetic auxin herbicide selected from the group consisting of 2,4-D, 2,4-DB, MCPA, dichlorprop, mecoprop, dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, aminopyralid, quinclorac, agriculturally acceptable salts and esters thereof, and combinations thereof,   wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (I)   
       
         
           
           
               
               
           
         
       
       wherein
 X is N or CY, wherein Y is hydrogen or halogen 
 R 1  is OR 1′ , wherein R 1′  is hydrogen or C 1 -C 4  alkyl, 
 R 2  is chlorine; 
 R 3  and R 4  are hydrogen; 
 A is A3 or A15 
 
       
         
           
           
               
               
           
         
         R 5  is hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 1 -C 3  alkoxy, amino, C 1 -C 4  alkylamino, OH, or CN; 
         R 6  and R 6′  are independently hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 2 -C 4  alkenyl, C 1 -C 3  alkoxy, amino, OH, or CN; 
         R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 1 -C 3  alkoxy, C 1 -C 3  alkylthio, amino, C 1 -C 4  alkylamino, or phenyl; 
         R 8  is hydrogen, C 1 -C 3  alkyl, C 1 -C 3  alkylcarbonyl, or phenyl; 
         or an agriculturally acceptable N-oxide or salt thereof. 
       
     
     
         2 . The composition of  claim 1 , wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (II) 
       
         
           
           
               
               
           
         
         wherein
 R 1  is OR 1′ , wherein R 1′  is hydrogen or C 1 -C 4  alkyl; 
 R 2  is chlorine; 
 R 3  and R 4  are hydrogen; 
 A is A3 or A15; 
 R 5  is hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 1 -C 3  alkoxy, amino, C 1 -C 4  alkylamino, OH, or CN; 
 R 6  and R 6′  are independently hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 2 -C 4  alkenyl, C 1 -C 3  alkoxy, amino, OH, or CN; 
 R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 1 -C 3  alkoxy, C 1 -C 3  alkylthio, amino, C 1 -C 4  alkylamino, or phenyl; and 
 R 8  is hydrogen, C 1 -C 3  alkyl, C 1 -C 3  alkylcarbonyl, or phenyl; 
 or an agriculturally acceptable N-oxide or salt thereof. 
 
       
     
     
         3 . The composition of  claim 2 , wherein
 R 1  is OR 1′ , wherein R 1′  is hydrogen, or C 1 -C 4  alkyl;   R 2  is chlorine;   R 3  and R 4  are hydrogen;   A is A3 or A15;   R 5  is hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 3  alkoxy, amino, or C 1 -C 4  alkylamino;   R 6  or R 6′  are independently hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 2 -C 4  alkenyl, C 1 -C 3  alkoxy, or CN;   R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, alkoxy, C 1 -C 3  alkylthio, cyclopropyl, amino, or C 1 -C 4  alkylamino; and   R 8  is hydrogen, C 1 -C 3  alkyl, or C 1 -C 3  alkylcarbonyl.   
     
     
         4 . The composition of  claim 1 , wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (III): 
       
         
           
           
               
               
           
         
         wherein
 X is N or CY, wherein Y is hydrogen or halogen; 
 R 1  is OR 1′ , wherein R 1′  is hydrogen or C 1 -C 4  alkyl; 
 R 2  is chlorine; 
 R 3  and R 4  are hydrogen; 
 R 6  and R 6′  are independently hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 2 -C 4  alkenyl, C 1 -C 3  alkoxy, OH, or CN; 
 
         R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, cyclopropyl, C 1 -C 3  alkoxy, C 1 -C 3  alkylthio, amino, C 1 -C 4  alkylamino, or phenyl; and 
         R 8  is hydrogen, C 1 -C 3  alkyl, C 1 -C 3  alkylcarbonyl, or phenyl; 
         or an agriculturally acceptable N-oxide or salt thereof. 
       
     
     
         5 . The composition of  claim 1 , wherein the pyridine carboxylic acid herbicide comprises one of the following: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         6 . The composition of  claim 1 , wherein the pyridine carboxylic acid herbicide comprises 
       
         
           
           
               
               
           
         
       
     
     
         7 . (canceled) 
     
     
         8 . (canceled) 
     
     
         9 . The composition of  claim 1 , wherein the weight ratio of (a) to (b) is from 1:8000 to 300:1. 
     
     
         10 . (canceled) 
     
     
         11 . (canceled) 
     
     
         12 . (canceled) 
     
     
         13 . (canceled) 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . (canceled) 
     
     
         17 . The composition of  claim 1 , further comprising a herbicidal safener. 
     
     
         18 . The composition of  claim 1 , further comprising an agriculturally acceptable adjuvant or carrier. 
     
     
         19 . The composition of  claim 1 , further comprising an additional pesticide. 
     
     
         20 . The composition of  claim 1 , wherein the active ingredients in the composition consist of (a) and (b). 
     
     
         21 . The composition of  claim 1 , which wherein the composition is provided as a herbicidal concentrate. 
     
     
         22 . A method of controlling undesirable vegetation comprising applying to vegetation or an area adjacent the vegetation or applying to soil or water to control the emergence or growth of vegetation a synergistic herbicidally effective amount of the composition of  claim 1 . 
     
     
         23 - 50 . (canceled) 
     
     
         51 . The method of  claim 22 , wherein the undesirable vegetation is controlled in spring barley ( Hordeum vulgare , HORVS), winter wheat ( Triticum aestivum , TRZAW), spring wheat ( Triticum aestivum , TRZAS), common rice ( Oryza sativa , ORYSA), maize ( Zea mays , ZEAMX), or combinations thereof. 
     
     
         52 - 53 . (canceled) 
     
     
         54 . The method of  claim 22 , wherein the undesirable vegetation includes a broadleaf weed. 
     
     
         55 - 59 . (canceled)