Solid forms of nematocidal sulfonamides

1. A polymorph of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide designated Form A characterized by a room-temperature powder Cu(Kα1) X-ray diffraction pattern having at least the 2θ reflection positions

2θ

30.367

29.131

27.995

27.611

26.49

25.973

25.604

24.285

23.582

19.789.

2. A polymorph of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide as a 1 to 1 solvate with toluene designated Form TS characterized by a room-temperature powder Cu(Kα1) X-ray diffraction pattern having at least the 2θ reflection positions

2θ

28.913

26.942

25.672

24.451

23.316

22.429

20.325

19.053

18.603

12.871.

3. A method for preparing the polymorph Form A of claim 1 comprising forming a slurry with a solvent of one or more solid forms of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide selected from the group of forms B, C, D, having a powder Cu(Kα1) X-ray diffraction pattern in accordance with that shown in FIG. 1 , solvates, amorphous forms and mixtures of any of the foregoing with Form A and maintaining the slurry while the solid forms of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide convert to polymorph Form A.

4. The method of claim 3 wherein the solid forms of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide comprises a mixture of polymorphs Form A and Form B.

5. The method of claim 3 wherein the slurry is heated to a temperature between 30° C. and the boiling point of the solvent and agitated.

6. The method of claim 3 wherein the slurry is agitated.

7. The method of claim 3 wherein the solvent comprises water, a C 5 -C 8 alkane, a C 1 -C 4 alkanol or a C 3 -C 4 ketone.

8. The method of claim 7 wherein the solvent comprises water or methanol.

9. A method for preparing the polymorph Form A of claim 1 comprising,

(A) contacting 8-chloro-6-trifluoromethyl-imidazo[1,2-a]pyridine-2-carbonyl chloride or a salt thereof and 2-chloro-5-methoxybenzene sulfonamide in the presence of a first solvent to form a reaction mixture containing an intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

(B) separating the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)-sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide, and

(C) contacting the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide with a second solvent, optionally heated to a temperature between 30° C. and the boiling point of the second solvent, to convert the intermediate solid form to the polymorph Form A of claim 1 .

10. The method of claim 9 wherein the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide is a solvate.

11. The method of claim 10 wherein the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide is a solvate with toluene.

12. The method of claim 9 wherein the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide is an unsolvated polymorph or mixture of polymorphs.

13. The method of claim 9 wherein the first solvent comprises a mixture of toluene with ethyl acetate and the second solvent comprises water, methanol, acetone or n-heptane.

14. A nematocidal composition comprising (a) the polymorph Form A of claim 1 and (b) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid carriers.

15. A nematocidal composition comprising (a) the polymorph Form A of claim 1 and (b) at least one other nematocide, insecticide or fungicide.

16. A method for protecting a plant from nematodes comprising applying to the plant, or portion, or seed thereof, or to the growing medium of the plant, a nematocidally effective amount of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide comprising the polymorph Form A of claim 1 .

17. The nematicidal composition of claim 15 wherein component (b) is selected from: 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, triflumezopyrim, triflumuron, all strains of Bacillus thuringiensis and all strains of Nucleo polyhedrosis viruses.