Synthesis and anti-juvenile hormone activity of ethyl 4-(2-benzylalkyloxy) benzoates and their enantiomers

Kenjiro Furuta, Kiyo Ashibe, Hiromitsu Shirahashi, Norihiro Fujita, Haruna Yamashita, Naotaka Yamada, Eiichi Kuwano

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A number of ethyl 4-(2-benzylalkyloxy)benzoates were prepared and their activity to induce precocious metamorphosis was evaluated in larvae of the silkworm, Bombyx mori, which was clearly recognized as a juvenile hormone (JH)-deficiency symptom. Ethyl 4-(2-benzylhexyloxy)benzoate (6) and its 2-benzylheptyloxy analog (7) were found to induce precocious metamorphosis at relatively low doses. Both enantiomers of 6 and 7 were prepared using a chiral auxiliary oxazolidinone. (S)-Enatiomers were more active than (R)-isomers at low doses of 0.1 and 1 μg, but at higher doses their activity was reversed. The activity of compound 6 could be fully counteracted by methoprene, a JH agonist, but not by the dietary administration of 20-hydroxyecdysone. The ester group was important in the ability to induce precocious metamorphosis. The (S)-enatiomer of 6 prolonged the duration of the instar and delayed the onset of cocoon spinning when applied to 5th instar larvae, suggesting that this compound might have JH-like activity as well as anti-JH activity.

Original languageEnglish
Pages (from-to)99-105
Number of pages7
JournalJournal of Pesticide Science
Volume32
Issue number2
DOIs
Publication statusPublished - May 31 2007

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Juvenile Hormones
precocious metamorphosis
Benzoates
enantiomers
benzoates
juvenile hormones
synthesis
Bombyx
Larva
instars
Methoprene
dosage
Ecdysterone
hormone agonists
Oxazolidinones
methoprene
ecdysterone
cocoons
Bombyx mori
spinning

All Science Journal Classification (ASJC) codes

  • Insect Science
  • Health, Toxicology and Mutagenesis

Cite this

Synthesis and anti-juvenile hormone activity of ethyl 4-(2-benzylalkyloxy) benzoates and their enantiomers. / Furuta, Kenjiro; Ashibe, Kiyo; Shirahashi, Hiromitsu; Fujita, Norihiro; Yamashita, Haruna; Yamada, Naotaka; Kuwano, Eiichi.

In: Journal of Pesticide Science, Vol. 32, No. 2, 31.05.2007, p. 99-105.

Research output: Contribution to journalArticle

Furuta, Kenjiro ; Ashibe, Kiyo ; Shirahashi, Hiromitsu ; Fujita, Norihiro ; Yamashita, Haruna ; Yamada, Naotaka ; Kuwano, Eiichi. / Synthesis and anti-juvenile hormone activity of ethyl 4-(2-benzylalkyloxy) benzoates and their enantiomers. In: Journal of Pesticide Science. 2007 ; Vol. 32, No. 2. pp. 99-105.
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