2-アルコキシ-1,3,2-チアザホスホリジン2-スルフィドの合成と生物活性

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  • 平島 明法
    Department of Agricultural Chemistry, Kyushu University
  • 吉井 豊
    Department of Agricultural Chemistry, Kyushu University
  • 原田 夕紀子
    Department of Agricultural Chemistry, Kyushu University Institute of Genetic Resources, Kyushu University
  • 賀 紅武
    Department of Agricultural Chemistry, Kyushu University Permanent address: Pesticidal Chemistry, Central China Normal University
  • 江藤 守総
    Department of Agricultural Chemistry, Kyushu University

書誌事項

タイトル別名
  • Synthesis and Biological Activities of Substituted 2-Alkoxy-1, 3, 2-thiazaphospholidine 2-Sulfides
  • 2-アルコキシンー1,3,2-チアザホスホリジン2-スルフィドの合成と生物活性〔英文〕
  • 2 アルコキシン 1 3 2 チアザホスホリジン 2 スルフィド ノ ゴウセイ

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説明

4-Isobutyl-2-methoxy-1, 3, 2-thiazaphospholidine 2-sulfide (iBMTS) and the related thiazaphospholidines were prepared by reacting phosphorodichloridothionate and β-aminothiols, which were obtained from the corresponding β-aminoalcohols via β-aminoalkyl hydrogen sulfate and 2-mercaptothiazoline followed by hydrochloric acid-catalyzed hydrolysis. Thiazaphospholidines had a higher insecticidal activity than the corresponding oxazaphospholidines against female Musca domestica houseflies by topical application. Methoxy derivatives were more potent insecticides than ethoxy derivatives. Oxazaphospholidines with a more bulky hydrophobic branched-alkyl substituent at C4 or phenyl at C5 were more potent than those with a less bulky hydrophobic substituent. In thiazaphospholidines, however, the effect of introduction of a bulky hydrophobic substituent at C4 was not as significant as in oxazaphospholidines in increasing the insecticidal activity. Neither oxazaphospholidines nor thiazaphospholidines activated adenylate cyclase of Periplaneta americana ventral-nervecord homogenates, but both reduced octopamine-stimulated adenylate-cyclase activity.

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