The Synthesis of C14-Labeled Piperonyl Butoxide and Its Fate in the Madeira Roach1

Abstract

Radioactive piperonyl butoxide, [alpha]-[2-(n-butoxy-ethoxy)-ethoxy]-4,5-methylenedioxy-2-propyltoluene-[alpha]C14, having a calculated activity of 0.157 [mu]c/mg, was prepared by reacting C14-labeled paraformaldehyde with dihydrosafrole then condensing the product with the sodium salt of diethylene glycol n-butyl ether. UV and infra-red spectra of the compound are presented. Three procedures for locating piperonyl butoxide on paper chro- matograms developed with acetonitrile-methanol-water as the solvent system are described. The effect of several organic solvents on 2 colorimetric tests for piperonyl butoxide was investigated. About 88% of the radioactive piperonyl butoxide, applied topically to male and female Madeira roaches (Leuco-phaea maderae) was absorbed in 3 days while about 50% of the radioactivity was recovered in 7 days. Paper chromatographic analysis of fecal extracts showed that less than 50% of the radio-activity was from piperonyl butoxide, the remainder consisted of unidentified, water-soluble metabolites. The internal distribution of radioactivity in female Madeira roaches showed that the brain and thoracic ganglia, fore-gut, and hind-gut and Malpi-ghian tubules contained the greatest amounts of radioactivity per unit weight.