Identification of (1R, 2S)-grandisal and (1R, 2S)-grandisol in Pissodes castaneus male-produced volatiles: evidence of a sex pheromone

Abstract

O gorgulho-da-casca-do-pinus, Pissodes castaneus (De Geer, 1775) (Coleoptera, Curculionidae) é uma praga florestal que foi detectada no Brasil em 2001 e atualmente se encontra distribuída nos três estados da Região Sul, causando grande preocupação para o setor florestal. Os objetivos deste estudo foram isolar, identificar e avaliar a atividade comportamental dos voláteis produzidos pelos machos de P. castaneus. Nossos resultados indicam que a comunicação entre indivíduos desta espécie é mediada por feromônios, o que foi evidenciado pela atração significativa de fêmeas pelos voláteis produzidos pelos machos. Testes comportamentais realizados com os insetos e sua planta hospedeira, Pinus taeda, indicam que os compostos produzidos pelos machos atuam como feromônios sexuais e que os compostos liberados pela planta hospedeira não aumentam a atividade destes compostos. Os compostos produzidos pelos machos de P. castaneus foram identificados como (1R, 2S)-grandisal e (1R, 2S)-grandisol, em excesso enantiomérico superior a 95%.The banded pine weevil, Pissodes castaneus (De Geer, 1775) (Coleoptera, Curculionidae) is a forest pest recorded in Brazil since 2001, which is already distributed in the three states of the Southern Region, causing great concern to the forestry sector. Objectives of our study were to isolate, identify, and assess the behavioral activity of male-produced volatiles of P. castaneus. Our results indicate that communication between conspecifics of P. castaneus is mediated by pheromones, as verified by the significant attraction of females to male-produced volatiles. Behavioral tests performed with the insects and the host plant, Pinus taeda, showed that male-produced compounds may act as sex pheromones and that the compounds released by the host plant did not enhance the activity of the male-produced volatiles. The chemical structures of the male specific volatile compounds produced by P. castaneus were determined to be (1R, 2S)-grandisal and (1R, 2S)-grandisol in an enantiomeric excess exceeding 95%.

(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevil Conotrachelus psidii (Coleoptera: Curculionidae)

“…19,20) Thus, despite the analysis of DHS extract of male C. psidii was not performed in the chiral column, the presence of enantiomeric pure papayanal is reinforced by biogenetic reasons. In two other Curculionidae species, papaya weevil (Pseudopiazurus obesus), 21) and banded pine weevil (Pissodes castaneus), 22) the mixture of (1R,2S)-(+)-grandisal and (1R,2S)-(+)-grandisol, aldehyde and alcohol, were identified as aggregation pheromones.…”

Pest survey card on Pissodes cibriani, P. fasciatus, P. nemorensis, P. nitidus, P. punctatus, P. strobi, P. terminalis, P. yunnanensis and P. zitacuarense

“…There is evidence that, at least in some species (P. nemorensis, P. strobi, the European P. castaneus) the males produce aggregation pheromones that attract unmated females and other males (Booth et al, 1983;Phillips et al, 1984;Hibbard and Webster, 1993;Marques et al, 2011). The role played by pheromones suggests they are potentially useful in trapping for detection.…”

Identification and genetic diversity of two invasive Pissodes spp. Germar (Coleoptera: Curculionidae) in their introduced range in the southern hemisphere

“…in South America remained unconfirmed for many years (Abgrall et al, 1999;Anon, 1970;O'Brien, 1989). Zaleski et al (2013) and Marques et al (2011) mentioned that the Pissodes sp. in Brazil is P. castaneus.…”