Raspberry ketone analogs: Vapour pressure measurements and attractiveness to Queensland fruit fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae)

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The Queensland fruit fly, Bactrocera tryoni (Froggatt) (Q-fly), is a major horticultural pest in Eastern Australia. Effective monitoring, male annihilation technique (MAT) and mass trapping (MT) are all important for control and require strong lures to attract flies to traps or toxicants. Lure strength is thought to be related in part to volatility, but little vapour pressure data are available for most Q-fly lures. Raspberry ketone (4-(4-hydroxyphenyl)-2-butanone) and analogs that had esters (acetyl, difluoroacetyl, trifluoroacetyl, formyl, propionyl) and ethers (methyl ether, trimethylsilyl ether) in replacement of the phenolic group, and in one case also had modification of the 2-butanone side chain, were measured for their vapour pressures by differential scanning calorimetry (DSC), and their attractiveness to Q-fly was assessed in small cage environmentally controlled laboratory bioassays. Maximum response of one category of compounds, containing both 2-butanone side chain and ester group was found to be higher than that of the other group of compounds, of which either of 2-butanone or ester functionality was modified. However, linear relationship between vapour pressure and maximum response was not significant. The results of this study indicate that, while volatility may be a factor in lure effectiveness, molecular structure is the dominating factor for the series of molecules investigated.

LanguageEnglish
Article numbere0155827
Pages1-16
Number of pages16
JournalPLoS ONE
Volume11
Issue number5
DOIs
Publication statusPublished - 19 May 2016

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Tephritidae
Bactrocera tryoni
Vapor Pressure
raspberries
Pressure measurement
Fruits
vapor pressure
ketones
Vapor pressure
Diptera
ethers
Esters
Volatilization
esters
Methyl Ethers
Ethers
Bioassay
Differential Scanning Calorimetry
Molecular Structure
differential scanning calorimetry

Bibliographical note

Copyright the Author(s) 2016. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Cite this

@article{0046978c55454bc99bb5bb32d57ff69a,
title = "Raspberry ketone analogs: Vapour pressure measurements and attractiveness to Queensland fruit fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae)",
abstract = "The Queensland fruit fly, Bactrocera tryoni (Froggatt) (Q-fly), is a major horticultural pest in Eastern Australia. Effective monitoring, male annihilation technique (MAT) and mass trapping (MT) are all important for control and require strong lures to attract flies to traps or toxicants. Lure strength is thought to be related in part to volatility, but little vapour pressure data are available for most Q-fly lures. Raspberry ketone (4-(4-hydroxyphenyl)-2-butanone) and analogs that had esters (acetyl, difluoroacetyl, trifluoroacetyl, formyl, propionyl) and ethers (methyl ether, trimethylsilyl ether) in replacement of the phenolic group, and in one case also had modification of the 2-butanone side chain, were measured for their vapour pressures by differential scanning calorimetry (DSC), and their attractiveness to Q-fly was assessed in small cage environmentally controlled laboratory bioassays. Maximum response of one category of compounds, containing both 2-butanone side chain and ester group was found to be higher than that of the other group of compounds, of which either of 2-butanone or ester functionality was modified. However, linear relationship between vapour pressure and maximum response was not significant. The results of this study indicate that, while volatility may be a factor in lure effectiveness, molecular structure is the dominating factor for the series of molecules investigated.",
author = "Park, {Soo J.} and Renata Morelli and Hanssen, {Benjamin L.} and Jamie, {Joanne F.} and Jamie, {Ian M.} and Siderhurst, {Matthew S.} and Taylor, {Phillip W.}",
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Raspberry ketone analogs : Vapour pressure measurements and attractiveness to Queensland fruit fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae). / Park, Soo J.; Morelli, Renata; Hanssen, Benjamin L.; Jamie, Joanne F.; Jamie, Ian M.; Siderhurst, Matthew S.; Taylor, Phillip W.

In: PLoS ONE, Vol. 11, No. 5, e0155827, 19.05.2016, p. 1-16.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Morelli, Renata

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AU - Jamie, Joanne F.

AU - Jamie, Ian M.

AU - Siderhurst, Matthew S.

AU - Taylor, Phillip W.

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