Ethyl 4-[2-(substituted benzyl)hexyloxy]benzoates: Anti-juvenile hormone agents with juvenile hormone activity

Shuhei Yoshtoa, Kenjiro Furuta, Kiyo Ashibe, Norihiro Fujita, Seiji Nishhcawa, Naotaka Yamada, Eiichi Kuwano

Research output: Contribution to journalArticle

Abstract

A large number of ethyl [2-(substituted benzyl)hexyloxy]benzoates and related compounds were prepared and their activity to induce precocious metamorphosis was evaluated in larvae of Bombyx mori, which was obviously recognized as a juvenile hormone (JH)-deficiency symptom. Introduction of a methyl, chloro or fluoro substituent at the 2-position on the benzene ring increased the activity in comparison with that of ethyl (2-benzylhexyloxy) benzoate (KF-13) in a dose range of 1-40 μg, however, no consistent dose-response relationship was obtained in these compounds as well as KF-13. The 4-methoxybenzyl analog showed strong precocious metamorphosis-inducing activity at both low and high doses, while introduction of other substituents such as a methyl, chloro, fluoro or ethyl group at the 3- and 4-position on the benzene ring decreased the activity at low doses. The JH activity of synthesized compounds was examined by bioassay using allatectomized 4th instar larvae. In the ethyl [2-(substituted benzyl)hexyloxy]benzoate series, a correlation was observed between JH activity and anti-JH activity; Compounds which induced high percentages of precocious metamorphosis at lower doses had obvious JH activity. Compounds possessing weak precocious metamorphosis-inducing activity showed little JH activity.

Original languageEnglish
Pages (from-to)185-190
Number of pages6
JournalJournal of the Faculty of Agriculture, Kyushu University
Volume54
Issue number1
Publication statusPublished - Feb 1 2009

Fingerprint

benzyl benzoate
Juvenile Hormones
juvenile hormones
precocious metamorphosis
benzene
dosage
Benzene
Larva
Bombyx
larvae
Benzoates
benzoates
Bombyx mori
Biological Assay
signs and symptoms (animals and humans)
dose response
instars
bioassays

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Agronomy and Crop Science

Cite this

Ethyl 4-[2-(substituted benzyl)hexyloxy]benzoates : Anti-juvenile hormone agents with juvenile hormone activity. / Yoshtoa, Shuhei; Furuta, Kenjiro; Ashibe, Kiyo; Fujita, Norihiro; Nishhcawa, Seiji; Yamada, Naotaka; Kuwano, Eiichi.

In: Journal of the Faculty of Agriculture, Kyushu University, Vol. 54, No. 1, 01.02.2009, p. 185-190.

Research output: Contribution to journalArticle

Yoshtoa, Shuhei ; Furuta, Kenjiro ; Ashibe, Kiyo ; Fujita, Norihiro ; Nishhcawa, Seiji ; Yamada, Naotaka ; Kuwano, Eiichi. / Ethyl 4-[2-(substituted benzyl)hexyloxy]benzoates : Anti-juvenile hormone agents with juvenile hormone activity. In: Journal of the Faculty of Agriculture, Kyushu University. 2009 ; Vol. 54, No. 1. pp. 185-190.
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