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Psyche
Volume 2012, Article ID 536149, 8 pages
http://dx.doi.org/10.1155/2012/536149
Research Article

Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay

1Beltsville Agricultural Research Center, Agricultural Research Service, USDA, Building 007, Room 326, BARC-West, 10300 Baltimore Avenue, Beltsville, MD 20705, USA
2Department of Employment, Economic Development and Innovation, Horticulture and Forestry Science, 28 Peters Street, P.O. Box 1054, Mareeba, QLD 4880, Australia
3School of Biological Sciences, The University of Queensland, Brisbane, QLD 4072, Australia

Received 14 February 2012; Accepted 21 April 2012

Academic Editor: Jocelyn G. Millar

Copyright © 2012 Ashot Khrimian et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The banana-spotting bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae), is one of the principal pests of tree fruits and nuts across northern and eastern Australia. Apart from visual damage assessment, there are currently no reliable methods for monitoring bug activity to aid management decisions. An attractant pheromone for this species that could be used as a trap lure could potentially fill this void. Earlier, two male-specific compounds were identified in airborne extracts from A. lutescens lutescens, (E,E)-α-farnesene and (R,E)-nerolidol; an unknown compound with a molecular weight 220 was also detected. We now report the identification of this hitherto unknown compound as (R,E,E)-α-farnesene-10,11-oxide. Synthesis of this epoxide was conducted using a regioselective asymmetric dihydroxylation of a sulfolene. A blend mimicking the natural proportions of (E,E)-α-farnesene, (R,E)-nerolidol, and (R,E,E)-α-farnesene-10,11-oxide attracted male and female A. lutescens lutescens as well as nymphs in the field, verifying that the aggregation pheromone comprises or is contained within this group of compounds.