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 language | English |
|---|---|
| Pages (from-to) | 185-190 |
| Number of pages | 6 |
| Journal | Journal of the Faculty of Agriculture, Kyushu University |
| Volume | 54 |
| Issue number | 1 |
| Publication status | Published - Feb 1 2009 |
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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 journal › Article
}
TY - JOUR
T1 - Ethyl 4-[2-(substituted benzyl)hexyloxy]benzoates
T2 - Anti-juvenile hormone agents with juvenile hormone activity
AU - Yoshtoa, Shuhei
AU - Furuta, Kenjiro
AU - Ashibe, Kiyo
AU - Fujita, Norihiro
AU - Nishhcawa, Seiji
AU - Yamada, Naotaka
AU - Kuwano, Eiichi
PY - 2009/2/1
Y1 - 2009/2/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=63649149375&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=63649149375&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:63649149375
VL - 54
SP - 185
EP - 190
JO - Journal of the Faculty of Agriculture, Kyushu University
JF - Journal of the Faculty of Agriculture, Kyushu University
SN - 0023-6152
IS - 1
ER -