Mesoionic pesticides

1. A compound of Formula 1,

wherein

X is O;

Y is O;

R 1 is phenyl or a 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkylaminocarbonyl, C 3 -C 7 dialkylaminocarbonyl, C(O)N CH 2 Z 2 CH 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkoxyalkyl, S(O) n R 12 , S(O) 2 R 13 , C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, SF 5 , Si(CH 3 ) 3 , CHO, hydroxy, OC(O)R 19 and N(R 20 )C(O)R 19 ;

R 2 is C 2 -C 6 alkyl, C 1 -C 6 haloalkyl or CR 5 R 6 CH 2 OR 21 ; or

R 2 is C 4 -C 7 cycloalkylalkyl optionally substituted with 1 to 4 substituents selected from the group consisting of halogen, C 1 -C 2 alkyl, 1 cyclopropyl and 1CF 3 ;

R 3 and R 4 are taken together with the contiguous linking nitrogen and carbon atoms to form an optionally substituted ring R-2

Z is C(R 8a )═C(R 8b ), provided that the C(R 8a )═C(R 8b ) moiety is oriented so the carbon atom bonded to R 8b is connected as R 3 in Formula 1;

each R 5 is independently H, F, Cl, cyano or C 1 -C 4 alkyl;

each R 6 is independently H, F, Cl or CH 3 ;

R 8a is H;

R 8b is H or F;

each R 12 is independently C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

each R 13 is independently C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino or —N CH 2 Z 2 CH 2 ;

each R 19 is independently C 1 -C 4 alkyl;

each R 20 is independently H or C 1 -C 4 alkyl;

each R 21 is independently H or C 1 -C 4 alkyl;

each n is independently 0, 1 or 2; and

each Z 2 is independently CH 2 CH 2 , CH 2 CH 2 CH 2 or CH 2 OCH 2 .

2. The compound of claim 1 wherein

R 1 is phenyl or pyridinyl, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkylaminocarbonyl, C 3 -C 7 dialkylaminocarbonyl, C(O)N CH 2 Z 2 CH 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkoxyalkyl, S(O) n R 12 , S(O) 2 R 13 , C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, SF 5 , Si(CH 3 ) 3 , CHO, hydroxy, OC(O)R 19 and N(R 20 )C(O)R 19 .

3. The compound of claim 2 wherein

each R 5 is independently H or C 1 -C 4 alkyl.

4. The compound of claim 3 wherein

each R 5 is independently H or methyl.

5. The compound of claim 4 wherein

R 6 is H.

6. The compound of claim 1 that is selected from the group consisting of

3-(2,4-difluorophenyl)-2-hydroxy-4-oxo-1-(2,2,2-trifluoroethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt;

3-(4-fluorophenyl)-2-hydroxy-4-oxo-1-(2,2,2-trifluoroethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt; and

2-hydroxy-4-oxo-3-phenyl-1-(2,2,2-trifluoroethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt.

7. 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, said composition optionally further comprising at least one additional biologically active compound or agent.

8. The composition of claim 7 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 (cyantraniliprole), 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, 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.

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, 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 (cyantraniliprole), 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.

10. 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.

11. 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 .

12. A treated seed comprising a compound of claim 1 in an amount of from 0.0001 to 1% by weight of the seed before treatment.