Mesoionic pesticides

Abstract

Disclosed are compounds of Formula 1, wherein R 1 is phenyl or pyridinyl, each optionally substituted with Q and up to 3 substituents independently selected from R 2 ; each R 2 is independently halogen, cyano, SF 5 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C 4 haloalkylthio; and Q is phenyl or pyridinyl, each optionally substituted with up to 5 substituents independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention. Further disclosed are methods for increasing vigor of a crop plant comprising contacting the crop plant, the seed from which the crop plant is grown or the locus of the crop plant with a biologically effective amount of a compound or composition of the invention.

What is claimed is: 
     
         1 . A compound of Formula 1, 
       
         
           
           
               
               
           
         
         wherein
 R 1  is phenyl or pyridinyl, each optionally substituted with Q and up to 3 substituents independently selected from R 2 ; 
 each R 2  is independently halogen, cyano, SF 5 , C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio or C 1 -C 4  haloalkylthio; and 
 Q is phenyl or pyridinyl, each optionally substituted with up to 5 substituents independently selected from the group consisting of halogen, cyano, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 4  alkoxy and C 1 -C 4  haloalkoxy. 
 
       
     
     
         2 . A compound of  claim 1  wherein
 R 1  is phenyl optionally substituted with Q and up to 3 substituents independently selected from R 2 ; and 
 Q is phenyl or pyridinyl, each optionally substituted with up to 3 substituents independently selected from the group consisting of halogen, cyano, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 4  alkoxy and C 1 -C 4  haloalkoxy. 
 
     
     
         3 . A compound of  claim 2  wherein
 R 1  is phenyl optionally substituted with up to 3 substituents independently selected from the group consisting of halogen, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 4  alkoxy and C 1 -C 4  haloalkoxy. 
 
     
     
         4 . A compound of  claim 3  that is selected from the group consisting of:
 2-hydroxy-4-oxo-3-phenyl-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(4-fluorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 2-hydroxy-3-(2-methoxyphenyl)-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 2-hydroxy-3-(3-methoxyphenyl)-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(2,4-difluorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(2-bromophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(2-fluorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-[2-fluoro-5-(trifluoromethyl)phenyl]-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 2-hydroxy-3-(3-methylphenyl)-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-[4-fluoro-3-(trifluoromethyl)phenyl]-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt (i.e. compound 12 of Index Table A); 
 3-(4-chloro-2-fluorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(2-chlorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-[3-chloro-5-(trifluoromethyl)phenyl]-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(3,5-dichlorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(3,5-dichloro-4-fluorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; 
 3-(4′-cyano-5,2′-dimethyl[1,1′-biphenyl]-3-yl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; and 
 3-(3-chlorophenyl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt. 
 
     
     
         5 . A composition comprising a compound of  claim 1  and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. 
     
     
         6 . The composition of  claim 5  further comprising at least one additional biologically active compound or agent. 
     
     
         7 . The composition of  claim 6  wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, bensultap, bifenthrin, bifenazate, bistrifluron, borate, buprofezin, cadusafos, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin, clothianidin, cyantraniliprole, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate, halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumuron,  Bacillus thuringiensis  delta-endotoxins, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi. 
     
     
         8 . A composition for protecting an animal from an invertebrate parasitic pest comprising a parasiticidally effective amount of a compound of  claim 1  and at least one carrier. 
     
     
         9 . A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of  claim 1 . 
     
     
         10 . A method for increasing vigor of a crop plant comprising contacting the crop plant, the seed from which the crop plant is grown or the locus of the crop plant with a biologically effective amount of a compound of  claim 1 . 
     
     
         11 . A treated seed comprising a compound of  claim 1  in an amount of from about 0.0001 to 1% by weight of the seed before treatment.