Chemical and Photochemical Transformation of the Insecticide Cartap Hydrochloride into Nereistoxin

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  • TSAO Rong
    Laboratory of Pesticide Chemistry, Department of Agricultural Chemistry, Kyushu University
  • ETO Morifusa
    Laboratory of Pesticide Chemistry, Department of Agricultural Chemistry, Kyushu University

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Other Title
  • 殺虫剤カルタップ塩酸塩からネライストキシンへの化学的・光化学的変化
  • 殺虫剤カルタップ塩酸塩からネライストキシンへの化学的・光化学的変化〔英文〕
  • サッチュウザイ カルタップ エンサンエン カラ ネライストキシン エ ノ カガ

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Description

The insecticide cartap hydrochloride, S, S′-[2-(dimethylamino)trimethylene]bis (thiocarbamate), was oxidized with N-bromosuccinimide to give nereistoxin, 4-N, N-dimethyl-amino-1, 2-dithiolane. Nereistoxin was also produced as a main product through photoreaction under UV irradiation by a high pressure mercury lamp (λ>300nm) and UV lamps (λ=254 and 373nm) in aqueous and methanolic solutions, and on glass and silica gel surfaces, respectively. It is assumed that both the chemical and photo-induced oxidations led to the direct formation of nereistoxin. Decomposition was faster on the silica gel surface than on the glass surface, probably owing to the larger surface area of the former. Effects of some photosensitizers were also investigated, among which rose bengal and chlorophyllin showed a great accelerating effect on cartap photodecomposition.

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