Metabolic O-dealkylation of 1-(4′-ethylphenoxy)-3,7-dimethyl-7-methoxy or ethoxy-trans-2-octene, potent juvenoids

Bruce D. Hammock, Sarjeet S. Gill, Lassie Hammock, John E. Casida

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

1-(4′-Ethylphenoxy)-3,7-dimethyl-7-methoxy or ethoxy-trans-2-octene (the ethyl-methoxide and ethyl-ethoxide) are more stable in some biological systems and less stable in others than 1-(4′-ethylphenoxy)-3,7-dimethyl-6,7-epoxy-trans-2-octene (the ethyl-epoxide). In housefly adults and mealworm pupae the persistence increases in the order of the ethyl-epoxide, -methoxide and -ethoxide but with adult stable flies the epoxide is of intermediate stability. The alkoxides are metabolized in living insects and microsomal oxidase systems of houseflies and mouse liver mainly by O-dealkylation, at a higher rate for the methoxide than the ethoxide, but benzylic oxidation of the ethyl group also occurs and is more important in the degradation of the ethyl-epoxide than the ethyl-alkoxides. The photostability on silica gel is slightly better for the ethyl-ethoxide than the -methoxide or -epoxide.

Original languageEnglish (US)
Pages (from-to)12-18
Number of pages7
JournalPesticide Biochemistry and Physiology
Volume5
Issue number1
DOIs
StatePublished - 1975

Fingerprint

Dealkylation
juvenile hormone analogs
Epoxy Compounds
epoxides
Houseflies
Muscidae
Tenebrio
Pupa
Silica Gel
Stomoxys calcitrans
Biological systems
photostability
Liver
Insects
silica gel
Oxidoreductases
pupae
Degradation
Oxidation
oxidation

ASJC Scopus subject areas

  • Agronomy and Crop Science
  • Biochemistry
  • Physiology

Cite this

Metabolic O-dealkylation of 1-(4′-ethylphenoxy)-3,7-dimethyl-7-methoxy or ethoxy-trans-2-octene, potent juvenoids. / Hammock, Bruce D.; Gill, Sarjeet S.; Hammock, Lassie; Casida, John E.

In: Pesticide Biochemistry and Physiology, Vol. 5, No. 1, 1975, p. 12-18.

Research output: Contribution to journalArticle

Hammock, Bruce D. ; Gill, Sarjeet S. ; Hammock, Lassie ; Casida, John E. / Metabolic O-dealkylation of 1-(4′-ethylphenoxy)-3,7-dimethyl-7-methoxy or ethoxy-trans-2-octene, potent juvenoids. In: Pesticide Biochemistry and Physiology. 1975 ; Vol. 5, No. 1. pp. 12-18.
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