Synthesis and Biological Activities of Substituted 2-Alkoxy-1, 3, 2-thiazaphospholidine 2-Sulfides

DOI NDL Digital Collections JASI Web Site Web Site Open Access
  • HIRASHIMA Akinori
    Department of Agricultural Chemistry, Kyushu University
  • YOSHII Yutaka
    Department of Agricultural Chemistry, Kyushu University
  • HARADA Yukiko
    Department of Agricultural Chemistry, Kyushu University Institute of Genetic Resources, Kyushu University
  • HE Hong-Wu
    Department of Agricultural Chemistry, Kyushu University Permanent address: Pesticidal Chemistry, Central China Normal University
  • ETO Morifusa
    Department of Agricultural Chemistry, Kyushu University

Bibliographic Information

Other Title
  • 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
  • 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

Search this article

Description

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.

Journal

Details 詳細情報について

Report a problem

Back to top