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

Akinori Hirashima, Yutaka Yoshii, Yukiko Harada, Hong wu He, Morifusa Eto

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


4-Isobutyl-2-methoxy-l,3,2-thiazaphospholidine 2-sulfide (iBMTS) and the related thiazaphospholidines were prepared by reacting phosphorodichloridothionate and /?-aminothiols, which were obtained from the corresponding /?-aminoalcohols via /?-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.

Original languageEnglish
Pages (from-to)499-507
Number of pages9
JournalJournal of Pesticide Science
Issue number3
Publication statusPublished - 1991

All Science Journal Classification (ASJC) codes

  • Insect Science
  • Health, Toxicology and Mutagenesis


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