title: Male-produced sex pheromone of the cerambycid beetle Hedypathes betulinus: chemical identification and biological activity.
abstract: We identified, synthesized, determined the diel periodicity of release, and tested the bioactivity of components of the male-produced sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae: Lamiinae). Gas chromatographic-mass spectrometric analysis of headspace volatiles from adult beetles showed three male-specific compounds, which were identified as (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (major component), (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), and (E)-6,10-dimethyl-5,9-undecadien-2-ol. Release of these chemicals was dependent on time of the photoperiod and presence of the host plant. Pheromone release took place primarily during the photophase, with maximum release occurring between 4 and 6 hr after the onset of photophase. The amount of pheromone released by males was much greater when they were in the presence of their host plant than when they were not. In Y-tube olfactometer tests, a ternary mixture of the compounds was attractive to female beetles, although the individual compounds were not attractive by themselves. Addition of volatiles from the host plant greatly increased the attractiveness of the ternary pheromone mixture and of the major pheromone component alone.
authors.affiliation: Laboratório de Semioquímicos, Departamento de Química, Universidade Federal do Paraná, CP 19081, CEP 81531-990, Curitiba, PR, Brazil.
authors.forename: Marcy G
authors.initials: MG
authors.lastname: Fonseca
authors.forename: Diogo M
authors.initials: DM
authors.lastname: Vidal
authors.forename: Paulo H G
authors.initials: PH
authors.lastname: Zarbin
mesh_terms: D000818:Animals; D001938:Brazil; D001517:Coleoptera / Q000145:classification / Q000187:drug effects* / Q000502:physiology; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D010675:Pheromones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D017440:Photoperiod; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D012726:Sexual Behavior, Animal / Q000187:drug effects* / Q000502:physiology; D013997:Time Factors; D055549:Volatile Organic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D010675:Pheromones; D012724:Sex Attractants; D055549:Volatile Organic Compounds
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