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Synthesis of H3-Ethyl Parathion

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Tritium is a very valuable radioisotope for labeling compounds used in metabolic studies, for it combines good stability (half-life 12.5 years) with the potential for obtaining specific activities very much larger than with C14. Tritium purchased as H32O is cheap, and a method is available for using H32O for labeling some aromatic pesticides. This method, however, is unsuitable for labeling most organophosphates (Hilton and O'Brien 1964). We have therefore frequently synthesized organophosphates from H3-alcohols. Unfortunately, these H3 alcohols are expensive, and the isotopic yields in the usual syntheses are relatively low on a micro scale. Thus Potter and O'Brien (1964) had a 2.5% isotopic yield in synthesizing parathion by reacting H3 ethanol with P2S5, chlorinating and reacting with p-nitrophenate. The drawbacks to the usual procedures are, 1st, the H3-alcohol is introduced in the 1st step, and losses of H3 inevitably occur in each of the later steps, 2nd, one customarily “drives” the ethylating step by using a large excess of ethanol, and of course this is impossible when labeled ethanol is employed.

Document Type: Research Article

Publication date: October 1, 1965

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  • Journal of Economic Entomology is published bimonthly in February, April, June, August, October, and December. The journal publishes articles on the economic significance of insects and is divided into the following sections: apiculture & social insects; arthropods in relation to plant disease; forum; insecticide resistance and resistance management; ecotoxicology; biological and microbial control; ecology and behavior; sampling and biostatistics; household and structural insects; medical entomology; molecular entomology; veterinary entomology; forest entomology; horticultural entomology; field and forage crops, and small grains; stored-product; commodity treatment and quarantine entomology; and plant resistance. In addition to research papers, Journal of Economic Entomology publishes Letters to the Editor, interpretive articles in a Forum section, Short Communications, Rapid Communications, and Book Reviews.
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