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Labelled organophosphorus pesticides. I. Synthesis of carbon-14 labelled O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate (sumithion®)

✍ Scribed by Akira Yoshitake; Kazuo Kawahara; Takeshi Kamada; Michio Endo

Publisher
John Wiley and Sons
Year
1977
Tongue
French
Weight
366 KB
Volume
13
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

O,O‐Dimethyl O‐(3‐methyl‐4‐nitrophenyl) phosphorothioate (I) (Sumithion®), an organophosphorus insecticide, was labelled with carbon‐14 individually at the aryl methyl and the phenyl ring. The synthetic procedures are shown in Fig. 1 and 2. Coupling reaction of 3‐methoxyphenylmagnesium bromide with methyl‐^14^C iodide followed by O‐demethylation gave 3‐methyl‐^14^C‐phenol, which was nitrosated with sodium nitrite and subsequently oxidized with 30% nitric acid to give 3‐methyl‐^14^C‐4‐nitrophenol in the overall yield of 48% from methanol‐^14^C. Condensation of 3‐methyl‐^14^C‐4‐nitrophenol with O,O‐dimethyl phosphorochloridothioate gave Sumithion‐(aryl methyl‐^14^C) in 89% yield.

Grignard reaction of 1‐bromo‐3‐methoxybenzene‐^14^C~6~ with methyl iodide afforded 1‐methoxy‐3‐methylbenzene‐^14^C~6~ in good yield and the latter was converted to Sumithion‐(phenyl‐^14^C) by the similar procedures used for the aryl methyl labelling. The overall yield of sumithion‐(phenyl‐^14^C) was 43% from 3‐bromophenol‐^14^C~6~.

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