Issue 3, 2011
From the journal:

RSC Advances

Synthesis of piperitone-derived halogenated lactones and their effect on aphid probing, feeding, and settling behavior†‡

Aleksandra Grudniewska,a   Katarzyna Dancewicz,b   Agata Białońska,c   Zbigniew Ciunik,c   Beata Gabryś*b  and  Czesław Wawrzeńczyk*a  

* Corresponding authors

a Department of Chemistry, Wrocław University of Environmental and Life Sciences, , Norwida 25, 50-375 Wrocław, Poland
E-mail: czeslaw.wawrzenczyk@up.wroc.pl
Fax: +48 71 3284124
Tel: +48 71 3205257

b Department of Biology and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland

c Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław, Poland

Abstract

Five racemic and five enantiomeric pairs of new halolactones with the p-menthane system were obtained in two or three step synthesis from racemic and optically active cis- and trans-piperitols. The key steps of the syntheses were the Claisen-Johnson rearrangement of piperitols to γ,δ-unsaturated esters and haloloctonization of γ,δ-unsaturated esters or acids. The structures of the compounds were confirmed by spectroscopic and crystallographic data. Antifeedant activity of all iodo-, bromo- and chlorolactones and racemic piperitone against Myzus persicae was examinated. The effect of these compounds on probing, feeding, and settling behavior of M. persicae in vivo was studied.

Graphical abstract: Synthesis of piperitone-derived halogenated lactones and their effect on aphid probing, feeding, and settling behavior

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Article information

DOI
https://doi.org/10.1039/C1RA00270H
Article type
Paper
Submitted
03 Jun 2011
Accepted
09 Jun 2011
First published
17 Aug 2011

RSC Adv., 2011,1, 498-510

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Synthesis of piperitone-derived halogenated lactones and their effect on aphid probing, feeding, and settling behavior

A. Grudniewska, K. Dancewicz, A. Białońska, Z. Ciunik, B. Gabryś and C. Wawrzeńczyk, RSC Adv., 2011, 1, 498 DOI: 10.1039/C1RA00270H

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