TH87950B - Naphthalene and isosazoline are pest control agents used to control invertebrate pests. - Google Patents

Abstract

The disclosed DC60 (14/07/52) is a compound of formula 1, (chemical formula) 1, where R1 is a halogen, C1-C2 haloalkyl or C1-C2 haloalkoxy; R2 is H, halogen or cyano; R3 is H, halogen or CF3; R4 is H, C2-C7 alkyl carbonyl or C2-C7 alkoxycarbonyl; and R5 is C1-C6 alkyl or C1-C6 haloalkyl, all substituted by one. Independent and selective replacements of hydroxya, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl, C2-C7 alkylaminocarboxyl, C3-C9 dialkylaminocarbonyl, C2-C7 haloalkylaminocarbonyl and C3-C9 halodialkylaminocarbonyl were also revealed, which are compounds of formula 1. The method for controlling invertebrate pests consists of exposing the invertebrate pest or its environment to a biologically effective dose of the compound or element of the invention. The revealed element is a compound of formula 1, (chemical formula) where R1 is a halogen, C1-C2 haloalkyl or C1-C2 haloalkoxy; R2 is H, a halogen or cyano; R3 is H, halogen, or CF3; R4 is H, C2-C7 alkylcarbonyl or C2-C7 alkoxycarbonyl; and R5 is C1-C6 alkyl or C1-C6 haloalkyyl, each replaced by one independent and selective substituent from hydroxyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C7 alkylaminocarboxyl, C3-C9 dialkylaminocarbonyl, C2-C7 haloalkyylaminocarbonyl, and C3-C9 halodialkyaminocarbonyl. Also disclosed are the elements containing the compounds of formula 1, and the method for controlling invertebrate pests consists of exposing the invertebrate pest or its environment to a biologically effective dose of the compound or element of the invention.

Claims (30)

1. Compounds of formula 1, (chemical formula) 1, where R1 is a halogen, C1-C2 haloalkyl or C1-C2 haloalkoxy; R2 is H, halogen or cyano; R3 is H, halogen or CF3; R4 is H, C2-C7 alkyl carbonyl or C2-C7 alkoxycarbonyl; and R5 is C1-C6 alkyl or C1-C6 haloalkyl, are all replaced by one independent substitute which They are mutually exclusive and selected from hydroxya, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C7 alkylaminocarbonyl, C3-C9 dialkylaminocarbonyl, C2-C7 haloalkylaminocarbonyl and C3-C9 halodialkylaminocarbonyl; with the condition that when R1 and R3 are Cl, and R2 and R4 are H, then R5 is apart from CH2C(O)NHCH2CF3,CH2CH2OH or CH2CH2OCH3. 2. Compounds of claim 1, where R4 is H; and R5 is a C1-C6 alkyl substituted by one independent substitute from C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C7 alkylaminocarbonyl and C2-C7 haloalkylaminocarbonyl. 3. Compounds of claim 2, where R1 is Cl, Br, or CF3; R2 is H; and R3 is H, F, Cl, Br, or CF3. 4. The compound of claim 3, where R1 is CF3. 5. The compound of claim number 4, where R3 is Cl, Br, or CF3. 6. Compounds of claim 5, where R5 is a C1-C6 alkyl substituted by one C2-C7 alkylaminocarbonyl or C3-C7 haloalkylaminocarbonyl. 7. The compound of claim 1 selected from the group containing 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosasolis]-N-[2-(methylsulfonyl)ethyl]-1-naphthalenecarboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosasolis]-N-[2-(methylsulfonyl)ethyl]-1-naphthalenecarboxamide, 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(methylamino)-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(methylamino)-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-2-oxoethyl]-1-naphthalene Carboxamide, 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-[(1-methylethyl)amino]-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]A 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(methylamino)-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-2-oxoethyl]-1-naphthalene Carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(1-methylethyl)amino]-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]A 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(methylamino)-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl [4-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide, 4-[5-[3-chloro-5- ... [4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-1-methyl-2-methyl-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-1-methyl-2-methyl-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-1-methyl-2-methyl-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl [4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-1-methyl-2-methyl-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-1-methyl-2-methyl-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl [1-methyl-2-[(methylethyl)amino]-2-oxoate methyl]-1-naphthalene carboxamide, 4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide, 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl]-3-isosazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide, 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl]-3-isosazolyl 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-1-methyl-2-methyl-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[2-(ethylamino)-1-methyl-2-methyl-2-oxoethyl]-1-naphthalene carboxamide, 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl [1-methyl)-3-isosazolyl]-N-[1-methyl-2-[(methylethyl)amino]-2-oxoate methyl]-1-naphthalene carboxamide, and 4-[5-[3,5bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isosazolyl]-N-[1-methyl-2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide, 8. The composition for the control of invertebrate pests shall consist of the compounds of claim 1 and at least one additional component selected from a group of surfactants, solid diluents and liquid diluents, such composition shall be further supplemented with at least one additional biological compound or active substance. 9. Elements of claim number 8 where at least one compound or substance Additional biologically active compounds were selected from groups comprising abamectin, acephate, acevinosil, acetamiprid, acrinathrin, amidoflumate, amitraz, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistrifluron, borate, 3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide, buprofezin, kadukaphos, carbaryl, carbofuran, cartap, carzol, chlorantraniliprol, chlorfenapyr, chlorfluazuron, and chlorpyrifos. Chlorpyrifos-methyl, Chromafenoside, Chlorphenthesin, Clothianidin, Cyflumethofen, Cyfluthrin, Beta-cyfluthrin, Cyhalothrin, Gamma-cyhalothrin, Lambda-cyhalothrin, Cypermethrin, Alpha-cypermethrin, Zeta-cypermethrin, Cyromazine, Deltamethrin, Diafenthiuron, Diazinon, Dialdrin, Diflubenzuron, Dimethfluthrin, Dimehypo, Dimethoate, Dinote Furan, Diophenolan, Emamectin, Endosulfan, Esfenvalerate, Ethiprole, Ethofen Prox, Ethoxazole. Fenbutanin oxide, phenothiocarb, phenoxycarb, fenpropathrin, fenvalerate, fipronil, phonicamid, flubendiamide, flucythrinate, fluphenirim, flufenosuron, fluvalinate, tu-fluvalinate, phonofos, formetanate, phosthiazate, halofenoside, hexaflumuron, hexythiazox, hydratethilnon, imidacloprid, indozacarb, insecticidal soap, isofenphos, lufenurol, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb, methomyl. Methoprene, Methoxychlor, Methofluthrin, Monocrotophos, Methoxyfenozide, Nitenpyram, Nithiazine, Novaluron, Noviflumuron, Oxamyl, Parathion, Parathion-methyl, Permethrin, Phorate, Phosalone, Phosphate, Phosphamidon, Pyrimicarb, Profenofos, Profluthrin, Propargite, Protrifen-but, Pimethrocine, Pyrafluprol, Pyrethrin, Pyridaben, Pyridalyl, Pyrifluquinazone, Pyriprol, Pyriproxifen, Rotenone, Rianodine, Sphentoram, Spinosad, Spirodichlorfen. Spiromesifen, Spirotetramet, Sulprophos, Tebufenozide, Tebufenpyrad, Teflubenzuron, Tefluthrin, Terbuphos, Tetrachlorvinphos, Tetramethrin, Thiacloprid, Thiamethosaml, Thiodicarb, Thiosultab-sodium, Tolfenpyrad, Tralomethrin, Triazame, Trichlorfon, Triflumuron, Delta-endotoxin of Bacillus thuringiensis, Entomological pathogenic bacteria, Entomological pathogenic viruses, and Entomological pathogenic fungi. 10. Components of claim number 9 where at least one compound or substance Additional biologically active compounds were selected from groups comprising 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, kadukaphos, carbaryl, cartap, chlorantraniliprol, chlorfenapir, chlorpyrifos, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, and cypermethrin. Alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dialedrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, phenothiocarb, phenoxycarb, fenvalerate, fipronil, phonicamid, flubendiamide, flufenosuron, fluvalinete, formetanate, phosthiazate, hexaflumuron, hydramethylnon, imidacloprid, indozacarb, lufenurol, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide. Nitenpyram, Nithiazine, Novaluron, Oxamyl, Pimethrocine, Pyrethrin, Pyridaben, Pyridalyl, Pyriproxifen, Rhianodine, Sphentoram, Spinosad, Spirodichlorfen, Spiromesifen, Spirotetramet, Tebufenozide, Tetramethrin, Thiacloprid, Thiamethoxam, Thiodicarb, Thiosultab-sodium, Tralomethrin, Triazame, Triflumuron, Delta-endotoxin of Bacillus thuringiensis, all strains of Bacillus thuringiensis and all strains of nucleopolyhydrosis viruses. 11. The composition shall include the compounds of claim 1 and at least one carrier acceptable to a veterinarian, and such composition shall be further composed of at least one active compound for additional parasite control. 12. Components of claim 11 where at least one of the active compounds in further parasite elimination is anthelmintic (deworming). 13. Components of claim 11 where at least one active compound for further parasite elimination is selected from the group comprising abamectin, doramectin, emamectin, epinomectin, ivermectin, selamatein, milbemycin, mosidectin and pyrantel. 14. Elements of claim No. 11 in the form for execution by consumption. 15. Elements of claim No. 11 in the form for specific execution. 16. Elements of claim 11 in the form for extraintestinal action. 17. The method for controlling invertebrate pests consists of exposing the invertebrate pest or its environment to a biologically effective dose of the compound of claim 1. 18. The method for protection against parasitic infestations of invertebrates consists of administering effective doses of a compound of the formula 1, (chemical formula) 1, where R1 is a halogen, C1-C2 haloalkyl or C1-C2 haloalkoxy; R2 is H, halogen or cyano; R3 is H, halogen or CF3; R4 is H, C2-C7 alkyl carbonyl or C2-C7 alkoxycarbonyl; and R5 is C1-C6 alkyl or C1-C6 haloalkyl, each replaced by one independent agent. They are mutually exclusive and selected from hydroxya, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C7 alkylaminocarbonyl, C3-C9 dialkylaminocarbonyl, C2-C7 haloalkylaminocarbonyl and C3-C9 halodialkylaminocarbonyl; with the condition that when the animal is a rodent, the invertebrate parasite is a flea, and the effective dose for parasite control of the compounds of formula 1 is administered orally, subsequently the compounds of formula 1 are in addition to 4-[5-[3,5-(dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isozazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalene carboxamide 19. According to the method of claim 18, the effective dosage for parasite elimination of the compound of formula 1 is administered orally. 20. According to the method of claim number 18, the effective dosage for parasite elimination of the compounds in formula 1 is administered extraintestinally. 21. Method of claim 18: The effective dosage for parasite elimination of the compound of formula 1 is administered by injection. 22. According to the method of claim 18, the effective dosage of the compound of formula 1 for parasite elimination is administered locally. 23. The method of claim 18 is that the protected animals are mammals, birds or fish. 24. The method of claim 23 is that the animals protected are livestock. 25. The method of claim 23 is that the protected animal is of the canine family. 26. The method of claim 23 is that the protected animals are those of the feline family. 27. The method of claim number 18, by which the infestation is a parasite of invertebrates, is an ectoparasite. 28. The method of claim 18 is by parasitic infestation of invertebrates, i.e., arthropods. 29. The method of claim 18 by parasitic infestations of invertebrates, namely flies, mosquitoes, mites, ticks, lice, fleas, legless insect larvae, bed bugs or kissing insects. 30. Method of claim 29 where the animal is a cat or dog and the infestation is a parasite of the invertebrate, i.e., a flea, flea-like beetle, or tick.