NAPHTHALENE ISOXAZOLINE INVERTEBRATE PEST CONTROL AGENTS

• US 20100254959A1
• Filed: 06/20/2008
• Published: 10/07/2010
• Est. Priority Date: 06/26/2007
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Xu, Ming, Long, Jeffrey Keith, Lahm, George Philip
• Granted Patent: US 8,410,153 B2
• Time in Patent Office: Days
• US Class Current: 424/93.461
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: A61P 33/14 Ectoparasiticides, e.g. scabicides
• CPC Class Codes: C07D 261/04 having one double bond between ring members or between a ring member and a non-ring member

Abstract

Disclosed are compounds of Formula 1,

wherein

• • R¹ is 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 alkylcarbonyl or C₂-C₇ alkoxycarbonyl; and
  • R⁵ is C₁-C₆ alkyl or C₁-C₆ haloalkyl, each substituted with one substituent independently selected from hydroxy, 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.
    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.

Claims

1. A compound of Formula 1,

2. A compound of claim 1 wherein

R⁴ is H;

and

R⁵ is C₁-C₆ alkyl substituted with one substituent independently selected from C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₂-C₇ alkylaminocarbonyl and C₂-C₇ haloalkylaminocarbonyl.

3. A compound of claim 2 wherein

R¹ is Cl, Br or CF₃;

R² is H; and

R³ is H, F, Cl, Br or CF₃.

4. A compound of claim 3 wherein

R¹ is CF₃.

5. A compound of claim 4 wherein

R³ is Cl, Br or CF₃.

6. A compound of claim 5 wherein

R⁵ is C₁-C₆ alkyl substituted with one C₂-C₇ alkylaminocarbonyl or C₃-C₇ 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, bistrifluron, 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,

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.