Naphthalene Isoxazoline Invertebrate Pest Control Agents

Abstract

Disclosed are compounds of Formula 1, wherein R 1 is halogen, C 1 -C 2 haloalkyl or C 1 -C 2 haloalkoxy; R 2 is H, halogen or cyano; R 3 is H, halogen or CF 3 ; R 4 is H, C 2 -C 7 alkylcarbonyl or C 2 -C 7 alkoxycarbonyl; and R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, each substituted with one substituent independently selected from hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 2 -C 7 alkylaminocarbonyl, C 3 -C 9 dialkylaminocarbonyl, C 2 -C 7 haloalkylaminocarbonyl and C 3 -C 9 halodialkylaminocarbonyl. 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.

What is claimed is: 
     
         1 . A compound of Formula 1, 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is halogen, C 1 -C 2  haloalkyl or C 1 -C 2  haloalkoxy; 
 R 2  is H, halogen or cyano; 
 R 3  is H, halogen or CF 3 ; 
 R 4  is H, C 2 -C 7  alkylcarbonyl or C 2 -C 7  alkoxycarbonyl; and 
 R 5  is C 1 -C 6  alkyl or C 1 -C 6  haloalkyl, each substituted with one substituent independently selected from hydroxy, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 2 -C 7  alkylaminocarbonyl, C 3 -C 9  dialkylaminocarbonyl, C 2 -C 7  haloalkylaminocarbonyl and C 3 -C 9  halodialkylaminocarbonyl; 
 provided that when R 1  and R 3  are Cl, and R 2  and R 4  are H, then R 5  is other than CH 2 C(O)NHCH 2 CF 3 , CH 2 CH 2 OH or CH 2 CH 2 OCH 3 . 
 
     
     
         2 . A compound of  claim 1  wherein
 R 4  is H; and 
 R 5  is C 1 -C 6  alkyl substituted with one substituent independently selected from C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 2 -C 7  alkylaminocarbonyl and C 2 -C 7  haloalkylaminocarbonyl. 
 
     
     
         3 . A compound of  claim 2  wherein
 R 1  is Cl, Br or CF 3 ; 
 R 2  is H; and 
 R 3  is H, F, Cl, Br or CF 3 . 
 
     
     
         4 . A compound of  claim 3  wherein
 R 1  is CF 3 . 
 
     
     
         5 . A compound of  claim 4  wherein
 R 3  is Cl, Br or CF 3 . 
 
     
     
         6 . A compound of  claim 5  wherein
 R 5  is C 1 -C 6  alkyl substituted with one C 2 -C 7  alkylaminocarbonyl or C 3 -C 7  haloalkylaminocarbonyl. 
 
     
     
         7 . A compound of  claim 1  that is selected from the group consisting of
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfonyl)ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfonyl)ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfonyl)ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(ethylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-[(1-methylethyl)amino]-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(ethylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-[(1-methylethyl)amino]-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(ethylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-[(1-methylethyl)amino]-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-(methylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(ethylamino)-1-methyl-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-[(1-methylethyl)amino]-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-(methylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(ethylamino)-1-methyl-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-[(1-methylethyl)amino]-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-(methylamino)-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(ethylamino)-1-methyl-2-oxoethyl]-1-naphthalenecarboxamide, 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-[(1-methylethyl)amino]-2-oxoethyl]-1-naphthalenecarboxamide, and 
 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide. 
 
     
     
         8 . A composition for controlling an invertebrate pest comprising a compound of  claim 1  and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, said composition optionally further comprising at least one additional biologically active compound or agent. 
     
     
         9 . The composition of  claim 8  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, bifenthrin, bifenazate, bistrifluoron, borate, 3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide, buprofezin, cadusafos, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin, clothianidin, 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, methiodicarb, 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, 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. 
     
     
         10 . The composition of  claim 9  wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acetamiprid, acrinathrin, amitraz, avermectin, azadirachtin, bifenthrin, 3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide, buprofezin, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, fluvalinate, formetanate, fosthiazate, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, tebufenozide, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumuron.  Bacillus thuringiensis  delta-endotoxins, all strains of  Bacillus thuringiensis  and all strains of  Nucleo polyhydrosis  viruses. 
     
     
         11 . A composition comprising a compound of  claim 1  and at least one veterinarily acceptable carrier, said composition optionally further comprising at least one additional parasiticidally active compound. 
     
     
         12 . The composition of  claim 11  wherein the at least one additional parasiticidally active compound is an anthelmintic. 
     
     
         13 . The composition of  claim 11  wherein the at least one additional parasiticidally active compound is selected from the group consisting of abamectin, doramectin, emamectin, eprinomectin, ivermectin, selamectin, milbemycin, moxidectin and pyrantel. 
     
     
         14 . The composition of  claim 11  in a form for oral administration. 
     
     
         15 . The composition of  claim 11  in a form for topical administration. 
     
     
         16 . The composition of  claim 11  in a form for parenteral administration. 
     
     
         17 . 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 . 
     
     
         18 . A method for protecting an animal from an invertebrate parasitic pest comprising administering to the animal a parasiticidally effective amount of a compound of Formula 1, 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is halogen, C 1 -C 2  haloalkyl or C 1 -C 2  haloalkoxy; 
 R 2  is H, halogen or cyano; 
 R 3  is H, halogen or CF 3 ; 
 R 4  is H, C 2 -C 7  alkylcarbonyl or C 2 -C 7  alkoxycarbonyl; and 
 R 5  is C 1 -C 6  alkyl or C 1 -C 6  haloalkyl, each substituted with one substituent independently selected from hydroxy, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 2 -C 7  alkylaminocarbonyl, C 3 -C 9  dialkylaminocarbonyl, C 2 -C 7  haloalkylaminocarbonyl and C 3 -C 9  halodialkylaminocarbonyl; 
 provided that when the animal is a mouse, the invertebrate parasitic pest is a flea, and the parasiticidally effective amount of the compound of Formula 1 is administered orally, then the compound of Formula 1 is other than 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide. 
 
     
     
         19 . The method of  claim 18  wherein the parasiticidally effective amount of a compound of Formula 1 is administered orally. 
     
     
         20 . The method of  claim 18  wherein the parasiticidally effective amount of a compound of Formula 1 is administered parenterally. 
     
     
         21 . The method of  claim 20  wherein the parasiticidally effective amount of a compound of Formula 1 is administered by injection. 
     
     
         22 . The method of  claim 18  wherein the parasiticidally effective amount of a compound of Formula 1 is administered topically. 
     
     
         23 . The method of  claim 18  wherein the animal to be protected is a mammal, avian or fish. 
     
     
         24 . The method of  claim 23  wherein the animal to be protected is livestock. 
     
     
         25 . The method of  claim 23  wherein the animal to be protected is a canine. 
     
     
         26 . The method of  claim 23  wherein the animal to be protected is a feline. 
     
     
         27 . The method of  claim 18  wherein the invertebrate parasitic pest is an ectoparasite. 
     
     
         28 . The method of  claim 18  wherein the invertebrate parasitic pest is an arthropod. 
     
     
         29 . The method of  claim 18  wherein the invertebrate parasitic pest is a fly, mosquito, mite, tick, louse, flea, maggot, bed bug or kissing bug. 
     
     
         30 . The method of  claim 29  wherein the animal is a cat or dog and the invertebrate parasitic pest is a flea, tick or mite.