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 journalArticle

10 Citations (Scopus)

Abstract

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
Volume16
Issue number3
DOIs
Publication statusPublished - Jan 1 1991

Fingerprint

Houseflies
adenylate cyclase
Sulfides
sulfides
Adenylyl Cyclases
bioactive properties
chemical derivatives
Octopamine
Periplaneta
octopamine
synthesis
Hydrochloric Acid
Periplaneta americana
hydrochloric acid
topical application
Musca domestica
acid hydrolysis
Insecticides
Sulfates
hydrogen

All Science Journal Classification (ASJC) codes

  • Insect Science
  • Health, Toxicology and Mutagenesis

Cite this

Synthesis and Biological Activities of Substituted 2-Alkoxy-1,3,2-thiazaphospholidine 2-Sulfides. / Hirashima, Akinori; Yoshii, Yutaka; Harada, Yukiko; He, Hong wu; Eto, Morifusa.

In: Journal of Pesticide Science, Vol. 16, No. 3, 01.01.1991, p. 499-507.

Research output: Contribution to journalArticle

Hirashima, Akinori ; Yoshii, Yutaka ; Harada, Yukiko ; He, Hong wu ; Eto, Morifusa. / Synthesis and Biological Activities of Substituted 2-Alkoxy-1,3,2-thiazaphospholidine 2-Sulfides. In: Journal of Pesticide Science. 1991 ; Vol. 16, No. 3. pp. 499-507.
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