Contact
insecticides often involve the interaction of whole organisms
and toxicant crystal surfaces. The crystalline phase of these compounds
has not, however, been considered for the optimization of insecticide
performance. Lindane (1R,2r,3S,4R,5r,6S-hexachlorocyclohexane) has been one of the most widely used
insecticides, but other (inactive) stereoisomers accompanying its
manufacture have led to massive chemical waste remediation problems.
Crystalline polymorphs are also isomers in the broadest sense, yet
only one crystal structure of lindane has been reported. Herein, we
report the discovery and characterization of two new polymorphs, Forms
II and III. The efficacy of Forms I, II, and III against Drosophila
melanogaster revealed an inverse correlation between lethality
and thermodynamic stability; the least stable kills fastest. This
understanding provides a crystal engineering opportunity wherein formulations
containing the most active contact insecticide polymorph can achieve
infectious disease prophylaxis while reducing environmental exposure
and associated chemical waste.
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