Synthesis and Bioassay Determination of Two Enantiomers of Schwarz's Compound, A Juvenile Hormone Analog

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John Klassen


Schwarz's Compound is a juvenile hormone (JH) analog similar to methoprene, a bioregulator with known JH activity on Orthoptera, Hymenoptera and Diptera. A novel organic synthesis of the two enantiomers of Schwarz's Compound (2-ethoxy-9-(p-isopropylphenyl)-2,6-dimethylnonane) was completed. The step in the synthesis which resulted in stereospecificity of the products was the addition of (R and S) citronellal through the Wittig reaction. Characterization and structure verification was completed using NMR, IR, GC-MS, and GC. Bioassays of the synthesized enantiomers were done on crickets, paper wasps, flesh flies, and mealworms to determine the level of activity and which enantiomer displays the most biological activity. Each target organism was treated with two different concentrations of each of the enantiomers. Effects were evaluated through morphological examination, timing of development, and dissection and measurement of the gonadal tissues to determine activity of the two enantiomers of Schwarz's Compound.