Polymorphs and amorphous forms of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1h-pyrazole-3-carbonitrile
AssigneeMakhteshim Chemical Works Ltd.
InventorSharona ZAMIR
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Abstract
The present invention relates to novel crystalline polymorphs, solvate pseudomorphs and amorphous form of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoroethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (fipronil). The present invention also provides methods for preparing the novel polymorphs, pseudomorphs and amorphous form, as well as insecticidal or pesticidal compositions comprising same, and methods of use thereof as pesticidal agents.
Claims27
A compound selected from the group consisting of a toluene hemi solvate (FS-T) pseudomorph of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile;
- a methyl isobutyl ketone (MIBK) hemi solvate (FS-M) pseudomorph of 5-amino-1-[2,6-dichloro-4(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile;
- an amorphous. 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile;
- and a crystalline polymorph Form III of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile, exhibiting an X-ray powder diffraction pattern having characteristic peaks expressed in degrees 2θ (+/−0.20° θ) at about 15.6, 16.7, 27.2, and 31.9.
A process for the preparation of a toluene hemi solvate (FS-T) pseudomorph of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile, the process comprising the steps of crystallizing said compound from toluene;
- and isolating the resulting crystals.
A process for the preparation of a methyl isobutyl ketone (MIBK) hemi solvate (FS-M) pseudomorph of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile, the process comprising the steps of preparing a solution of said compound in MIBK and n-hexane;
- slowly evaporating the solvent;
- and isolating the resulting crystals.
A process for the preparation of amorphous 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile, the process comprising the steps of heating said compound to a temperature greater than its melting point;
- cooling;
- and isolating the resulting product.
Dependencies are inferred from the claim text.