Ultraviolet irradiation of fenitrothion and the synthesis of the photolytic oxidation products

Journal Article · Wed Dec 31 23:00:00 EST 1975 · J. Agric. Food Chem.; (United States)

DOI:https://doi.org/10.1021/jf60206a021· OSTI ID:7259231

Greenhalgh, R; Marshall, W D

The ultraviolet irradiation of fenitrothion in oxygenated solutions produced isomerization, oxidation, and solvolysis. In hexane, both the P=S and the aryl methyl group were oxidized to give fenitrooxon and formylfenitrothion. Small amounts of denitrofenitrothion were also formed. Irradiation in methanol gave carbomethoxyfenitrothion formed from oxidation followed by solvolysis. Isomerization of fenitrothion to its S-methyl isomer took place on a small scale in all solvents; however, no S-aryl isomer was detected. Irradiation of hydroxymethylfenitrothion in hexane readily gave formyl- and carboxyfenitrothion. This supports the suggestion that hydroxymethylfenitrothion is a reactive intermediate formed in the photolysis of fenitrothion. Several potential oxidation products, hydroxymethyl, formyl, carboxy, and carbomethoxy analogues of fenitrothion and fenitrooxon were prepared together with the S-aryl isomer. The mass spectral (MS) and nuclear magnetic resonance (NMR) data, gas chromatographic (GC), and thin-layer chromatographic (TLC) properties of these compounds and other fenitrothion derivatives are given.

• Research Organization: Chemistry and Biology Research Inst., Ottawa
• OSTI ID: 7259231
• Journal Information: J. Agric. Food Chem.; (United States), Journal Name: J. Agric. Food Chem.; (United States) Vol. 24:4; ISSN JAFCA
• Country of Publication: United States
• Language: English

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CHEMICAL REACTIONS
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RADIATION EFFECTS
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ULTRAVIOLET RADIATION