Metabolism of O, O-Dipropyl S-[2-(2-Methyl- 1-piperidinyl)- 2-oxo-ethyl] Phosphorodithioate (C 19 490) in the Rat

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The fate of O, O-dipropyl S-[2-(2-methyl-1-piperidinyl)-2-oxo-ethyl] phosphorodithioate (C 19 490, piperophos), an active ingradient of herbicides Rilof® and Avirosan®, was investigated in rats using 2-methyl [14C]-labelled material. After single oral doses (0.5 to 30 mg/kg body weight) the radioactivity was rapidly excreted, mainly through urine. Nine days after receiving a dose of 5.4 mg/kg the residues in liver, fat, kidney, muscle, blood and brain were below 0.03 ppm C 19 490 equivalents. Thirteen urine metabolites, representing 55% of the dose applied, were isolated and their structures elucidated by spectroscopic methods. The degradation of C 19 490 in the rat proceeds via hydrolysis of the thiolo phosphate followed by methylation of the sulfhydryl group. The methylthio derivative is either oxidized at the sulfur or hydroxylated at the piperidme moiety. Hydroxylation at the α-C leads via ring opening to carboxylic acids. The hydroxypiperidine derivatives are conjugated with glucuronic acid. No unchanged C 19 490 was excreted with the urine and the amount of 14CO2 expired was below 0.5% of the dose.
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