Nematocidal heterocyclic amides

1. A compound selected from Formula 1 when used as a nematocide,

wherein

R 1 is H or methyl;

R 2 is H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl, each unsubstituted or substituted with at least one R 5 ;

R 3 is C 2 -C 16 alkyl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl or C 3 -C 6 cycloalkyl, each unsubstituted or substituted with at least one R 6 ;

R 4 is Cl or Br;

each R 5 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 alkylsulfonyl;

each R 6 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl or SiR a R b R c ; and

each R a , R b and R c is independently C 1 -C 6 alkyl;

provided that (i) when R 1 and R 2 are H, then R 3 is other than C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, cyclopropyl, —CH 2 OCH 3 , —CH 2 SCH 3 , unsubstituted C 2 -C 3 alkyl, or C 2 -C 3 alkyl substituted with Cl or Br (ii) when R 1 is methyl, then R 3 is other than ethyl; and (iii) when R 1 is H and R 2 is methyl, then R 3 is other than ethyl.

2. A compound selected from Formula 1a when used as a nematocide,

wherein

R 2 is H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl, each unsubstituted or substituted with at least one R 5 ;

R 3 is C 2 -C 16 alkyl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl or C 3 -C 6 cycloalkyl, each unsubstituted or substituted with at least one R 6 ;

R 4 is Cl, Br, I, CF 3 or cyano;

each R 5 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 alkylsulfonyl;

each R 6 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl or SiR a R b R c ; and

each R a , R b and R c is independently C 1 -C 6 alkyl.

3. A compound selected from Formula 1b when used as a nematocide,

wherein

R 2 is H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl, each unsubstituted or substituted with at least one R 5 ;

R 3 is C 2 -C 16 alkyl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl or C 3 -C 6 cycloalkyl, each unsubstituted or substituted with at least one R 6 ;

R 4 is Cl, Br, I, CF 3 or cyano;

each R 5 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 alkylsulfonyl;

each R 6 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl or SiR a R b R c ; and

each R a , R b and R c is independently C 1 -C 6 alkyl.

4. 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.

5. The composition of claim 4 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopyropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, buprofezin, cadusafos, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cycloxaprid, 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, fenitrothion, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin, fluensulfone, fluopyram, flupyradifurone, fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin, nicotine, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbute, pyflubumide, pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon, pyriminostrobin, pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tioxazafen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumezopyrim, triflumuron, Bacillus thuringiensis delta-endotoxins, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

6. The composition of claim 5 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acetamiprid, acrinathrin, afidopyropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flufenoxuron, flufenoxystrobin, fluensulfone, flupiprole, flupyradifurone, fluvalinate, formetanate, fosthiazate, heptafluthrin, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, meperfluthrin, metaflumizone, methiocarb, methomyl, methoprene, methoxyfenozide, metofluthrin, monofluorothrin, nitenpyram, nithiazine, novaluron, oxamyl, pyflubumide, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron, Bacillus thuringiensis delta-endotoxins, all strains of Bacillus thuringiensis and all strains of nucleo polyhedrosis viruses.

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

8. A composition comprising (i) a compound of Formula 1a and a compound of Formula 1b,

wherein the ratio of 1b to 1a is at least 55:45; and

wherein

R 2 is H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl, each unsubstituted or substituted with at least one R 5 ;

R 3 is C 2 -C 16 alkyl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl or C 3 -C 6 cycloalkyl, each unsubstituted or substituted with at least one R 6 ;

R 4 is Cl, Br, I, CF 3 or cyano;

each R 5 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 alkylsulfonyl;

each R 6 is independently halogen, cyano, C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl or SiR a R b R c ; and

each R a , R b and R c is independently C 1 -C 6 alkyl; and

(ii) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

9. The composition of claim 8 wherein the compound of Formula 1b is present in a nematocidally effective amount.

10. A method for controlling a soil-dwelling nematode comprising contacting the nematode or its environment with a biologically effective amount of the composition of claim 8 .