Four crystalline polymorphs of the proinsecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile] have been identified and characterized by polarized light optical microscopy, differential scanning calorimetry, Raman spectroscopy, X-ray diffraction, and electron diffraction. Three of the four structures were considered polytypic. Chlorfenapyr polymorphs show similar lethality against fruit flies (Drosophila melanogaster) and mosquitoes (Anopheles quadrimaculatus) with the least stable polymorph showing slightly higher lethality. Similar activities may be expected to be consistent with structural similarities. Knockdown kinetics, however, depend on an internal metabolic activating step, which further complicates polymorph-dependent bioavailability.

Department of Chemistry and Molecular Design Institute New York University 29 Washington Place New York City New York 10003 United States

Department of Chemistry University at Buffalo Buffalo New York 14260 3000 United States

Department of Molecular Chemistry and Materials Science Weizmann Institute of Science Rehovot 76100 Israel

Department of Structure Analysis Institute of Physics Czech Academy of Sciences Na Slovance 2 1999 Prague 8 Prague 18221 Czech Republic

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