Synthesis and biological activity of novel anti-juvenile hormone agents

Eiichi Kuwano, Norihiro Fujita, Kenjiro Furuta, Naotaka Yamada

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Ethyl 4-[2-(tert-butylcarbonyloxy)butoxy]benzoate (ETB) is a partial juvenile hormone (JH) antagonist which targets larval epidermis. We converted ETB to ethyl 4-(2-substituted alkyloxy)benzoates. These compounds induced precocious metamorphosis in the silkworm, Bombyx mori, which is a clear sign of JH deficiency, and their activity was completely counteracted by the simultaneous application of a JH agonist, methoprene. Among these novel compounds, ethyl 4-(2-benzylhexyloxy)benzoate (KF-13) showed high precocious metamorphosis-inducing activity at low doses, but its activity decreased with increasing dose, probably due to their JH-like activity. KF-13 is an enantiomeric compound. The (S)-enatiomer of KF-13 was more active than the (R)-enantiomer at low doses, but at high doses the activity was reversed (R>S). Hemolymph JH esterase activity, which is indispensable for the initiation of pupation in normal last-instar larvae, was induced in 4th-instar larvae by treatment with KF-13. 2-(6-Methyl-3-pyridyloxy)hexyl and 2-phenoxyhexyl analogs showed JH activity when topically applied to allatechtomized 4th-instar larvae.

Original languageEnglish
Pages (from-to)14-16
Number of pages3
JournalJournal of Pesticide Science
Volume33
Issue number1
DOIs
Publication statusPublished - Mar 7 2008

Fingerprint

Juvenile Hormones
juvenile hormones
bioactive properties
benzoates
precocious metamorphosis
synthesis
instars
Larva
dosage
juvenile hormone antagonists
Bombyx
Benzoates
larvae
juvenile hormone esterase
hormone agonists
methoprene
juvenile hormone analogs
Methoprene
epidermis (animal)
enantiomers

All Science Journal Classification (ASJC) codes

  • Insect Science
  • Health, Toxicology and Mutagenesis

Cite this

Synthesis and biological activity of novel anti-juvenile hormone agents. / Kuwano, Eiichi; Fujita, Norihiro; Furuta, Kenjiro; Yamada, Naotaka.

In: Journal of Pesticide Science, Vol. 33, No. 1, 07.03.2008, p. 14-16.

Research output: Contribution to journalArticle

Kuwano, Eiichi ; Fujita, Norihiro ; Furuta, Kenjiro ; Yamada, Naotaka. / Synthesis and biological activity of novel anti-juvenile hormone agents. In: Journal of Pesticide Science. 2008 ; Vol. 33, No. 1. pp. 14-16.
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