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3-Hydroxyhexan-2-one and 3-Methylthiopropan-1-ol as Pheromone Candidates for the South American Cerambycid Beetles Stizocera phtisica and Chydarteres dimidiatus dimidiatus, and Six Related Species

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Abstract

Here, we study the pheromone chemistry of two South American cerambycid beetle species, and their behavioral responses to candidate pheromone components. Adult males of Stizocera phtisica Gounelle (subfamily Cerambycinae: tribe Elaphidiini) produced a sex-specific blend of (R)-3-hydroxyhexan-2-one with lesser amounts of 3-methylthiopropan-1-ol. In field bioassays, traps baited with racemic 3-hydroxyhexan-2-one and 3-methylthiopropan-1-ol did not catch conspecific beetles, but did catch both sexes of a sympatric species, Chydarteres dimidiatus dimidiatus (F.) (Cerambycinae: Trachyderini). We found that males of this species also produce (R)-3-hydroxyhexan-2-one and 3-methylthiopropan-1-ol, and small amounts of 2-phenylethanol. Subsequent bioassays with these compounds showed that a blend of 3-hydroxyhexan-2-one and 3-methylthiopropan-1-ol constitutes the aggregation-sex pheromone of C. d. dimidiatus, with 2-phenylethanol not influencing the attraction of conspecifics. During the field bioassays, six other species in the Cerambycinae also were caught in significant numbers, including Aglaoschema ventrale (Germar) (tribe Compsocerini), congeners Chrysoprasis aurigena (Germar), Chrysoprasis linearis Bates, and an unidentified Chrysoprasis species (Dichophyiini), and Cotyclytus curvatus (Germar) and Itaclytus olivaceus (Laporte & Gory) (both Clytini), suggesting that one or more of the compounds tested are also pheromone components for these species.

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Acknowledgements

We thank Antonio Santos-Silva (Museum of Zoology of USP) for identifying the cerambycid species. We also thank Araci and Cassio Silva, Fernando Madalon and Jean Carlos Alvarez for assisting with the field experiments. We gratefully acknowledge financial support from INCT-Semiochemicals in Agriculture (Fundação de Amparo à Pesquisa do Estado de São Paulo and Conselho Nacional de Desenvolvimento Científico e Tecnológico, grants: #2014/50871-0 and #465511/2014-7) to JMSB and United States Department of Agriculture—Animal and Plant Health Inspection Service (grant #s 15, 16, 17, 18, 19, and 20-8130-1422-CA to JGM and LMH, and grant # 20-8130-0909-CA to WDS). Field collections of the study species in Brazil were conducted under SISBIO permit #46395 from the Brazilian Ministry of the Environment. This work was registered with the National System for the Management of Genetic Heritage and Associated Traditional Knowledge (SisGen, Brazil) under #AE3897B.

Funding

This work was supported by INCT-Semioquímicos na Agricultura (Fundação de Amparo à Pesquisa do Estado de São Paulo and Conselho Nacional de Desenvolvimento Científico e Tecnológico, grants: #2014/50871–0 and #465511/2014–7) and United States Department of Agriculture—Animal and Plant Health Inspection Service (grant #s 15, 16, 17, 18, 19, 20–8130-1422-CA and 20–8130-0909-CA).

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Authors and Affiliations

  1. Department of Entomology and Acarology, University of São Paulo, Piracicaba, SP, 13418900, Brazil

    Weliton D. Silva & José Mauricio S. Bento

  2. Department of Entomology, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA

    Lawrence M. Hanks

  3. Departments of Entomology and Chemistry, University of California, Riverside, CA, 92521, USA

    Jocelyn G. Millar

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  1. Weliton D. Silva
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  2. Lawrence M. Hanks
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  3. José Mauricio S. Bento
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  4. Jocelyn G. Millar
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by Weliton Silva, Lawrence Hanks and Jocelyn Millar. The first draft of the manuscript was written by Weliton Silva. Lawrence Hanks and Jocelyn Millar reviewed and edited previous versions of the manuscript. All authors read and approved the final manuscript. Grants in support of the work were written by Lawrence Hanks, José Maurício Bento, and Jocelyn Millar.

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Correspondence to Weliton D. Silva.

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We dedicate this manuscript to the memory of our friend and colleague Professor Dr. Dr. h.c. mult. Wittko Francke, a superb chemical ecologist whose laboratory carried out pioneering studies on the semiochemistry of cerambycid beetles.

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Silva, W.D., Hanks, L.M., Bento, J.M.S. et al. 3-Hydroxyhexan-2-one and 3-Methylthiopropan-1-ol as Pheromone Candidates for the South American Cerambycid Beetles Stizocera phtisica and Chydarteres dimidiatus dimidiatus, and Six Related Species. J Chem Ecol 47, 941–949 (2021). https://doi.org/10.1007/s10886-021-01313-7

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