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J Chem Ecol

Title:		"Aggregation Pheromone of the Bearded Weevil, Rhinostomus barbirostris (Coleoptera: Curculionidae): Identification, Synthesis, Absolute Configuration and Bioactivity"
Author(s):		Reis AC; Neta PLS; Jordao JP; Moura JIL; Vidal DM; Zarbin PHG; Favaro CF;
Address:		"Department of Exact and Technological Sciences, State University of Santa Cruz, Ilheus, BA, 45662-900, Brazil. Department of Agrarian and Environmental Sciences, State University of Santa Cruz, Ilheus, BA, 45662-900, Brazil. Lemos Maia Experimental Station, CEPLAC, Una, BA, 45690-000, Brazil. Department of Chemistry, Federal University of Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil. Department of Chemistry, Federal University of Parana, Curitiba, PR, 81531-980, Brazil. Department of Exact and Technological Sciences, State University of Santa Cruz, Ilheus, BA, 45662-900, Brazil. carlaffavaro@gmail.com"
Journal Title:		J Chem Ecol
Year:		2018
Volume:		20180416
Issue:		5
Page Number:		463 - 470
DOI:		10.1007/s10886-018-0957-x
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"The bearded weevil, Rhinostomus barbirostris (Coleoptera: Curculionidae: Dryophthorinae), attacks coconut trees, oil palms and other species of Arecaceae. Besides direct damage, R. barbirostris may be a vector of diseases in coconut and oil palms, such as stem bleeding (resinosis) and red ring disease. Currently, the only method to control this weevil is by visual observation of damage and removal of infected plants. Semiochemical-based trapping could improve the effectiveness of monitoring and management of R. barbirostris. In comparisons of volatiles released by R. barbirostris males and females by gas chromatography (GC) two male-specific compounds were observed. GC-mass spectrometry (MS) and GC-Fourier transform-infrared (FTIR) analyses of the natural compounds suggested these were diastereoisomers of 5-hydroxy-4-methylheptan-3-one, also known as sitophilure, a pheromone component of other dryophthorine species. Synthesis of the mixture of all four stereoisomers of sitophilure was performed in two steps, and the chemical structures were confirmed by comparing GC retention times and MS and FTIR spectra of natural and synthetic compounds. The absolute configurations of the two male-specific compounds were elucidated by enantioselective GC; the major component was the (4S,5R)-isomer, and the minor component (4S,5S)-sitophilure. In analyses by GC-electroantennography (EAG) the antennae of male and female R. barbirostris only responded to the (4S,5R)-isomer of the synthetic sitophilure. The stereoisomeric mixture of sitophilure was attractive to both sexes of R. barbirostris in laboratory experiments in the presence of sugar cane volatiles, and a similar result was obtained in a preliminary field trapping test"
Keywords:		"Animals Female Gas Chromatography-Mass Spectrometry Male Molecular Conformation Sex Attractants/*analysis/chemical synthesis/*metabolism Sexual Behavior, Animal Weevils/chemistry/*physiology 5-hydroxy-4-methylheptan-3-one Palm weevil Semiochemicals Sitoph;"
Notes:		"MedlineReis, Analu C Neta, Palmira L S Jordao, Jessica P Moura, Jose Inacio L Vidal, Diogo M Zarbin, Paulo H G Favaro, Carla F eng 2018/04/17 J Chem Ecol. 2018 May; 44(5):463-470. doi: 10.1007/s10886-018-0957-x. Epub 2018 Apr 16"