4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides

Abstract

4-Amino-6-(heterocyclic)picolinic acids and their derivatives; 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their derivatives; and methods of using the same as herbicides.

1 - 32 . (canceled) 
     
     
         33 . A compound of the 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  alkoxy, 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 A3 or A15 
 
       
         
           
           
               
               
           
         
         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; 
         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 N-oxide or agriculturally acceptable salt thereof. 
       
     
     
         34 . The compound of  claim 33 , wherein
 X is N or CY, wherein Y is hydrogen or halogen;   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;   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;   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.   
     
     
         35 . The compound of  claim 34 , wherein X is CF, CCl, or CBr. 
     
     
         36 . The compound of  claim 35 , wherein X is CY, wherein Y is CF. 
     
     
         37 . The compound of  claim 35 , wherein X is CY, wherein Y is CCl. 
     
     
         38 . The compound of  claim 35 , wherein X is CY, wherein Y is CBr. 
     
     
         39 . The compound of  claim 34 , wherein R 2  is Cl, methoxy, vinyl, or 1-propenyl. 
     
     
         40 . The compound of  claim 34 , wherein R 3  and R 4  are hydrogen. 
     
     
         41 . The compound of  claim 34 , wherein A is A3. 
     
     
         42 . The compound of  claim 34 , wherein A is A15. 
     
     
         43 . The compound of  claim 34 , wherein R 5  is hydrogen or F. 
     
     
         44 . The compound of  claim 43 , wherein R 5  is F. 
     
     
         45 . The compound of  claim 34 , wherein R 6  is hydrogen or F. 
     
     
         46 . The compound of  claim 34 , wherein R 6 , R 6′ , R 6″ , R 7 , and R 7′  are all hydrogen. 
     
     
         47 . A herbicidal composition comprising a compound of  claim 33  and an agriculturally acceptable adjuvant or carrier. 
     
     
         48 . The composition of  claim 47 , further comprising an additional component selected from the group consisting of an insecticide, a herbicide, a fungicide, a safener, a growth regulator, or a combination thereof. 
     
     
         49 . The composition of  claim 47 , further comprising a herbicide selected from 2.4-D, 2,4-DB, MCPA, dichlorprop, mecoprop, dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, aminopyralid, or quinclorac. 
     
     
         50 . The composition of  claim 47 , further comprising a herbicide selected from ametridione, ametryn, amibuzin, anisuron, atraton, atrazine, bentazon-sodium, benzthiazuron, bromobonil, bromofenoxim, bromoxynil, buturon, chlorazine, chlorbromuron, chloreturon, chlorotoluron, chloroxuron, chloroxynil, cumyluron, cyanatryn, cyanazine, cycluron, cyprazine, daimuron, desmetryn, dichloralurea, difenoxuron, dimefuron, dimethametryn, dipropetryn, diuron, eglinazine, ethidimuron, fenuron, fluothiuron, hexazinone, ioxynil, ipazine, isoproturon, isouron, linuron, mesoprazine, metamitron, methabenzthiazuron, methiuron, methometon, methoprotryne, methyldymron, metobenzuron, metobromuron, metoxuron, metribuzin, monisouron, monolinuron, monuron, neburon, noruron, phenobenzuron, procyazine, proglinazine, prometon, prometryn, propazine, pyraclonil, sebuthylazine, secbumeton, simazine, simeton, simetryn, tebuthiuron, terbumeton, terbuthylazine, terbutryn, tetrafluoron, thiazafluoron, thidiazuron, triaziflam, or trietazine 
     
     
         51 . The composition of  claim 47 , further comprising a herbicide selected from amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucetosulfuron, flumetsulam, flupyrsulfuron, foramsulfuron, halosulfuron-methyl, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metosulam, metsulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-methyl, pyroxsulam, rimsulfuron, sulfometuron, sulfosulfuron, thiencarbazone-methyl, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, or tritosulfuron. 
     
     
         52 . The composition of  claim 47 , further comprising a safener selected from mefenpyrdiethyl, isoxadifen-ethyl, cloquintocet-mexyl, or dichlormid 
     
     
         53 . 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 a compound of  claim 33 .