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Aggregation Pheromone of the Bearded Weevil, Rhinostomus barbirostris (Coleoptera: Curculionidae): Identification, Synthesis, Absolute Configuration and Bioactivity.
Reis, Analú C; Neta, Palmira L S; Jordão, Jéssica P; Moura, José Inácio L; Vidal, Diogo M; Zarbin, Paulo H G; Fávaro, Carla F.
Afiliação
  • Reis AC; Department of Exact and Technological Sciences, State University of Santa Cruz, Ilhéus, BA, 45662-900, Brazil.
  • Neta PLS; Department of Agrarian and Environmental Sciences, State University of Santa Cruz, Ilhéus, BA, 45662-900, Brazil.
  • Jordão JP; Department of Agrarian and Environmental Sciences, State University of Santa Cruz, Ilhéus, BA, 45662-900, Brazil.
  • Moura JIL; Lemos Maia Experimental Station, CEPLAC, Una, BA, 45690-000, Brazil.
  • Vidal DM; Department of Chemistry, Federal University of Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil.
  • Zarbin PHG; Department of Chemistry, Federal University of Paraná, Curitiba, PR, 81531-980, Brazil.
  • Fávaro CF; Department of Exact and Technological Sciences, State University of Santa Cruz, Ilhéus, BA, 45662-900, Brazil. carlaffavaro@gmail.com.
J Chem Ecol ; 44(5): 463-470, 2018 May.
Article em En | MEDLINE | ID: mdl-29658050
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.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Atrativos Sexuais / Gorgulhos Tipo de estudo: Diagnostic_studies Limite: Animals Idioma: En Ano de publicação: 2018 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Atrativos Sexuais / Gorgulhos Tipo de estudo: Diagnostic_studies Limite: Animals Idioma: En Ano de publicação: 2018 Tipo de documento: Article