Synergistic weed control from applications of pyridine carboxylic acid herbicides and photosystem ii 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 photosystem II inhibitor, or an agriculturally acceptable salt or ester 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 photosystem II inhibitor, or an agriculturally acceptable salt or ester 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 photosystem II inhibitor, or an agriculturally acceptable salt or ester thereof, wherein the weight ratio of (a) in grams acid equivalent (g ae) to (b) in grams active ingredient (g ai) is from 1:300 to 4.3:1,
 wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (I)   
       
         
           
           
               
               
           
         
       
       wherein
 X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio or C 1 -C 3  haloalkylthio; 
 R 1  is OR 1′  or NR 1′ R 1′″ , wherein R 1′  is hydrogen, C 1 -C 8  alkyl, or C 7 -C 10  arylalkyl, and R 1″  and R 1′″  are independently hydrogen, C 1 -C 12  alkyl, C 3 -C 12  alkenyl, or C 3 -C 12  alkynyl; R 2  is halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  haloalkylthio, amino, C 1 -C 4  alkylamino, C 2 -C 4  haloalkylamino, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17  is hydrogen, F, or Cl; R 18  is hydrogen, F, Cl, C 1 -C 4  alkyl, or C 1 -C 4  haloalkyl; and R 19 , R 20 , and R 21  are independently C 1 -C 10  alkyl, C 3 -C 6  cycloalkyl, phenyl, substituted phenyl, C 1 -C 10  alkoxy, or OH; 
 R 3  and R 4  are independently hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkylcarbamyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  trialkylsilyl, C 1 -C 6  dialkylphosphonyl, or R 3  and R 4  taken together with N is a 5- or 6-membered saturated ring, or R 3  and R 4  taken together represent ═CR 3′ (R 4′ ), wherein R 3′  and R 4′  are independently hydrogen, C 1 -C 6  alkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, C 1 -C 6  alkoxy or C 1 -C 6  alkylamino, or, R 3′  and R 4′  taken together with ═C represent a 5- or 6-membered saturated ring; 
 A is one of groups A1 to A36 
 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         R 5 , if applicable to the A group, is hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino, C 2 -C 4  haloalkylamino, OH, or CN; 
         R 6 , R 6′ , and R 6″ , if applicable to the A group, are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino or C 2 -C 4  haloalkylamino, OH, CN, or NO 2 ; 
         R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino, C 1 -C 4  haloalkylamino, or phenyl; 
         R 8  is hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkylcarbamyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  trialkylsilyl, 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′  or NR 1′ R 1′″ , wherein R 1′  is hydrogen, C 1 -C 8  alkyl, or C 7 -C 10  arylalkyl, and R 1″  and R 1′″  are independently hydrogen, C 1 -C 12  alkyl, C 3 -C 12  alkenyl, or C 3 -C 12  alkynyl; 
 R 2  is halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  haloalkylthio, amino, C 1 -C 4  alkylamino, C 2 -C 4  haloalkylamino, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17  is hydrogen, F, or Cl; R 18  is hydrogen, F, Cl, C 1 -C 4  alkyl, or C 1 -C 4  haloalkyl; and R 19 , R 20 , and R 21  are independently C 1 -C 10  alkyl, C 3 -C 6  cycloalkyl, phenyl, substituted phenyl, C 1 -C 10  alkoxy, or OH; 
 R 3  and R 4  are independently hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkylcarbamyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  trialkylsilyl, C 1 -C 6  dialkylphosphonyl, or R 3  and R 4  taken together with N is a 5- or 6-membered saturated ring, or R 3  and R 4  taken together represent ═CR 3′ (R 4′ ), wherein R 3′  and R 4′  are independently hydrogen, C 1 -C 6  alkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, C 1 -C 6  alkoxy or C 1 -C 6  alkylamino, or, R 3′  and R 4′  taken together with ═C represent a 5- or 6-membered saturated ring; 
 A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36; 
 R 5  is hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino, C 2 -C 4  haloalkylamino, OH, or CN; 
 R 6 , R 6′ , and R 6″  are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino or C 2 -C 4  haloalkylamino, OH, CN, or NO 2 ; 
 R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino, C 2 -C 4  haloalkylamino, or phenyl; and 
 R 8  is hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkylcarbamyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  trialkylsilyl, 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, C 1 -C 8  alkyl, or C 7 -C 10  arylalkyl;   R 2  is halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, or C 1 -C 4  haloalkylthio;   R 3  and R 4  are hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, or R 3  and R 4  taken together represent ═CR 3′ (R 4′ ), wherein R 3′  and R 4′  are independently hydrogen, C 1 -C 6  alkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, C 1 -C 6  alkoxy or C 1 -C 6  alkylamino;   A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15, A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32;   R 5  is hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino, or C 2 -C 4  haloalkylamino;   R 6 , R 6′ , and R 6″  are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, CN, or NO 2 ;   R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, cyclopropyl, amino or C 1 -C 4  alkylamino; and   R 8  is hydrogen, C 1 -C 6  alkyl, C 1 -C 4  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, C 1 -C 6  alkoxycarbonyl, or C 1 -C 6  alkylcarbamyl.   
     
     
         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, halogen, C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio or C 1 -C 3  haloalkylthio; 
 R 1  is OR 1′  or NR 1′ R 1′″ , wherein R 1′  is hydrogen, C 1 -C 8  alkyl, or C 7 -C 10  arylalkyl, and R 1″  and R 1′″  are independently hydrogen, C 1 -C 12  alkyl, C 3 -C 12  alkenyl, or C 3 -C 12  alkynyl; 
 R 2  is halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  haloalkylthio, amino, C 1 -C 4  alkylamino, C 2 -C 4  haloalkylamino, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17  is hydrogen, F, or Cl; R 18  is hydrogen, F, Cl, C 1 -C 4  alkyl, or C 1 -C 4  haloalkyl; and R 19 , R 20 , and R 21  are independently C 1 -C 10  alkyl, C 3 -C 6  cycloalkyl, phenyl, substituted phenyl, C 1 -C 10  alkoxy, or OH; 
 R 3  and R 4  are independently hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkylcarbamyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  trialkylsilyl, C 1 -C 6  dialkylphosphonyl, or R 3  and R 4  taken together with N is a 5- or 6-membered saturated ring, or R 3  and R 4  taken together represent ═CR 3′ (R 4′ ), wherein R 3′  and R 4′  are independently hydrogen, C 1 -C 6  alkyl, C 3 -C 6  alkenyl, C 3 -C 6  alkynyl, C 1 -C 6  alkoxy or C 1 -C 6  alkylamino, or, R 3′  and R 4′  taken together with ═C represent a 5- or 6-membered saturated ring; 
 R 6  and R 6′  are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino or C 2 -C 4  haloalkylamino, OH, CN, or NO 2 ; 
 R 7  and R 7′  are independently hydrogen, halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4  alkenyl, C 2 -C 4  haloalkenyl, C 2 -C 4  alkynyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, amino, C 1 -C 4  alkylamino, C 2 -C 4  haloalkylamino, or phenyl; and 
 R 8  is hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl, formyl, C 1 -C 3  alkylcarbonyl, C 1 -C 3  haloalkylcarbonyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkylcarbamyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  trialkylsilyl, 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 . The composition of  claim 1 , wherein (b) comprises a nitrile herbicide. 
     
     
         8 . The composition of  claim 7 , wherein (b) comprises bromoxynil or an agriculturally acceptable salt or ester thereof. 
     
     
         9 . The composition of  claim 1 , wherein (b) comprises a benzothiadiazinone herbicide. 
     
     
         10 . The composition of  claim 9 , wherein (b) comprises bentazon or an agriculturally acceptable salt thereof. 
     
     
         11 . The composition of  claim 1 , wherein (b) comprises a urea herbicide. 
     
     
         12 . The composition of  claim 11 , wherein (b) comprises isoproturon. 
     
     
         13 . The composition of  claim 1 , wherein (b) comprises a triazinone herbicide. 
     
     
         14 . The composition of  claim 13 , wherein (b) comprises metribuzin or an agriculturally acceptable salt. 
     
     
         15 . The composition of  claim 1 , wherein (b) comprises a triazine herbicide. 
     
     
         16 . The composition of  claim 15 , wherein (b) comprises atrazine or an agriculturally acceptable salt. 
     
     
         17 . The composition of  claim 1 , wherein the weight ratio of (a) to (b) is from 1:90 to 5:1. 
     
     
         18 . (canceled) 
     
     
         19 . (canceled) 
     
     
         20 . The composition of  claim 1 , further comprising an agriculturally acceptable adjuvant or carrier. 
     
     
         21 . The composition of  claim 1 , further comprising an additional pesticide. 
     
     
         22 . The composition of  claim 1 , wherein the active ingredients in the composition consist of (a) and (b). 
     
     
         23 . (canceled) 
     
     
         24 . The composition of  claim 1 , which wherein the composition is provided as a herbicidal concentrate. 
     
     
         25 . 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 herbicidally effective amount of the composition of  claim 1 . 
     
     
         26 - 41 . (canceled) 
     
     
         42 . The method of  claim 25 , wherein (a) and (b) are applied post-emergence to the undesirable vegetation. 
     
     
         43 - 45 . (canceled) 
     
     
         46 . The method of  claim 25 , wherein (a) is applied in amount of from 0.1 g ae/ha to 300 g ae/ha. 
     
     
         47 . (canceled) 
     
     
         48 . The method of  claim 25 , wherein (b) is applied in amount of from 5 g ai/ha to 4000 g ai/ha. 
     
     
         49 - 51 . (canceled) 
     
     
         52 . The method of  claim 25 , further comprising applying an additional pesticide. 
     
     
         53 . (canceled) 
     
     
         54 . (canceled) 
     
     
         55 . The method of  claim 25 , wherein the undesirable vegetation includes a broadleaf weed. 
     
     
         56 . The method of  claim 25 , wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed. 
     
     
         57 . (canceled) 
     
     
         58 . (canceled) 
     
     
         59 . The method of  claim 25 , wherein the undesirable vegetation includes velvetleaf, pigweed, rape, thistle, nutsedge, large crabgrass, barnyardgrass, poinsettia, common sunflower, ivyleaf morningglory, wild pansy, ivy-leaved speedwell, or a combination thereof. 
     
     
         60 . The method of  claim 25 , wherein the active ingredients applied to the vegetation or an area adjacent the vegetation or applied to soil or water to control the emergence or growth of vegetation consist of (a) and (b).