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Aggregation Pheromone of the Bearded Weevil, Rhinostomus barbirostris (Coleoptera: Curculionidae): Identification, Synthesis, Absolute Configuration and Bioactivity

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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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Acknowledgements

We thank the Coordination for Improvement of Higher Education Personnel (CAPES), the State of Bahia Research Foundation (FAPESB) and the National Institute of Science and Technology (INCT) Semiochemicals in Agriculture (CNPq Process 465511/2014-7 and FAPESP Process 2014/50871-0) for supporting research. We also thank Dr. Jeffrey R. Aldrich for his help in improving the English language corrections, and the Professors of the State University of Santa Cruz (UESC), Ivon Lobo and Rosenira Serpa, for assisting the GC-FID analyses, and Rosilene de Oliveira for preliminary GC-MS analyses.

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Authors and Affiliations

  1. Department of Exact and Technological Sciences, State University of Santa Cruz, Ilhéus, BA, 45662-900, Brazil

    Analú C. Reis & Carla F. Fávaro

  2. Department of Agrarian and Environmental Sciences, State University of Santa Cruz, Ilhéus, BA, 45662-900, Brazil

    Palmira L. S. Neta & Jéssica P. Jordão

  3. Lemos Maia Experimental Station, CEPLAC, Una, BA, 45690-000, Brazil

    José Inácio L. Moura

  4. Department of Chemistry, Federal University of Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil

    Diogo M. Vidal

  5. Department of Chemistry, Federal University of Paraná, Curitiba, PR, 81531-980, Brazil

    Paulo H. G. Zarbin

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  1. Analú C. Reis
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  2. Palmira L. S. Neta
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  3. Jéssica P. Jordão
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  7. Carla F. Fávaro
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Correspondence to Carla F. Fávaro.

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Reis, A.C., Neta, P.L.S., Jordão, J.P. et al. Aggregation Pheromone of the Bearded Weevil, Rhinostomus barbirostris (Coleoptera: Curculionidae): Identification, Synthesis, Absolute Configuration and Bioactivity. J Chem Ecol 44, 463–470 (2018). https://doi.org/10.1007/s10886-018-0957-x

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  • DOI: https://doi.org/10.1007/s10886-018-0957-x

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