Nematocidal sulfonamides

1. A compound selected from Formula 1, an N-oxide, or a salt thereof,

wherein

Z is O or S;

A 1 , A 3 and A 4 are independently N or CR 1 , provided that only one of A 1 , A 3 and A 4 must be N in each compound;

A 2 is C-CF 3 ;

each R 1 is independently H, halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 7 cycloalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O) 2 NR 11 R 12 ; or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , 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(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ;

R 2 is H, halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 7 cycloalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O) 2 NR 11 R 12 ; or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , 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(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ;

R 3 is H, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O) 2 NR 11 R 12 ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or C 1 -C 6 alkyl substituted with 1 or 2 substituents independently selected from the group consisting of phenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , 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 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ;

Q is phenyl, naphthalenyl, a 5- or 6-membered heteroaromatic ring or an 8- to 10-membered aromatic bicyclic ring system, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O) 2 R 9 , OS(O) 2 NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O) 2 R 9 , N(R 10 )S(O) 2 NR 11 R 12 and R 14 ;

each X is independently O or S;

each R 4 is independently H, NR 5a R 6a , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 or S(O) m R 9 ; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl 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(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 4a is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 5 is independently H, NR 5a R 6a , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O) 2 NR 11 R 12 ; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl 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(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 5a is independently H or C 1 -C 6 alkyl;

each R 6 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 7 cycloalkyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , S(O) m R 9a or S(O) 2 NR 11 R 12 ;

each R 6a is independently H, C 1 -C 6 alkyl, C(O)R 13 or C(O)OR 13 ;

each R 7 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl 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(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 7a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 8 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl 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(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 8a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 9 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl 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(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 9a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 10 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 7 cycloalkyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , S(O) m R 9a or S(O) 2 NR 11 R 12 ;

each R 11 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl 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(X)R 7a , C(O)OR 8a , C(O)NR 11a R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11a R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 11a is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;

each R 12 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl or C 3 -C 7 cycloalkyl;

each R 13 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ;

each R 14 is independently C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, each substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , 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 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a ; and

each m is independently 0, 1 or 2.

2. A compound of claim 1 wherein:

Z is O; and

Q is phenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7 and N(R 10 )C(O)R 7 .

3. A compound of claim 2 wherein:

Q is phenyl, pyridinyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, furanyl or thienyl, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7 and N(R 10 )C(O)R 7 .

4. A compound of claim 2 or 3 wherein:

each R 1 is independently halogen, cyano, nitro, OR 4 , C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 2 is H, halogen or C 1 -C 6 alkyl; and

R 3 is H, C(X)R 7 , C(O)OR 8 or S(O) m R 9 ; or C 1 -C 6 alkyl optionally substituted with 1 to 4 substituents independently selected from halogen.

5. A compound of claim 1 that is selected from the group consisting of:

N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxamide;

and

N-[[2-chloro-5-(trifluoromethyl)phenyl]sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyrimidine-2-carboxamide.

6. 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.

7. The composition of claim 6 wherein said composition further comprises 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, buprofezin, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin, clothianidin, cyantraniliprole, 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, all strains of Bacillus thuringiensis , entomopathogenic bacteria, all strains of Nucleo polyhydrosis viruses, 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, buprofezin, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-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, 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, all strains of Bacillus thuringiensis and all strains of Nucleo polyhydrosis viruses.

10. A method for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound of claim 1 .

11. The method of claim 10 wherein the environment is a plant.

12. The method of claim 10 wherein the environment is a seed.

13. The method of claim 12 wherein the seed is coated with the compound of Formula 1, an N-oxide or salt thereof, formulated as a composition comprising a film former or adhesive agent.

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