Gas chromatographic and polarographic determination of nereistoxin and nereistoxin monoxide

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  • NISHI Kiyoshi
    Chemical Research Laboratories, Central Research Division Takeda Chemical Industries Ltd.
  • ASHIDA Yasuko
    Chemical Research Laboratories, Central Research Division Takeda Chemical Industries Ltd.
  • TAN Nobutsura
    ResearchLaboratories, Agricultural Chemicals Division, Takeda Chemical Industries Ltd.
  • SUGITA Norio
    ResearchLaboratories, Agricultural Chemicals Division, Takeda Chemical Industries Ltd.

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Other Title
  • ガスクロマトグラフィー及びポーラログラフィーによるネライストキシンとネライストキシンモノオキシドとの分別定量法
  • ガス クロマトグラフィー オヨビ ポーラログラフィー ニヨル ネライストキシン

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Abstract

Nereistoxin monoxide (4-dimethylamino-1, 2-dithiolane 1-oxide) and nereistoxin (4-dimethylamino-1, 2-dithiolane) which were considered to be metabolites of cartap hydrochloride {2-dimethylaminotrimethylene S, S'-bis (thiocarbamate) hydrochloride} in soil and plant tissue, were determined by gas chromatography (GC) and polarography. On GC analysis, nereistoxin monoxide and nereistoxin dissolved in acetic acid-methanol were directly injected since nereistoxin monoxide is stable in acidic solution. The minimum detection amount of nereistoxin monoxide and nereistoxin with a FPD was as low as 1 ng. Nereistoxin monoxide in acidic solution showed a fourelectron reduction wave due to the formation of thiosulfinate accompanied with an adsorption wave on polarography. Nereistoxin monoxide was easily hydrolyzed in alkaline solution to give 2-dimethylamino-3-mercaptopropanesulfinic acid (DMSA) and the reduction wave disappeared. DMSA showed an anodic wave due to the formation of mercaptide accompanied with an adsorption wave and the wave height is proportional to the concentration. Nereistoxin monoxide and nereistoxin were determined separately by the anodic wave (E1/2=-0.30 V vs. SCE) from DMSA and the reduction wave (E1/2=-0.52 V vs. SCE) after the hydrolysis of the mixture since nereistoxin was stable in alkaline solution. The hydrolysis of nereistoxin monoxide in aqueous solution was base-catalyzed pseudo-first reaction within pH 812. The half-life (t1/2) of this compound at pH 10.5 was 10 min at 25°C.

Journal

  • BUNSEKI KAGAKU

    BUNSEKI KAGAKU 28 (3), 137-142, 1979

    The Japan Society for Analytical Chemistry

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