The Common Natural Products ( S)-α-Terpineol and ( E)-2-Hexenol are Important Pheromone Components of Megacyllene antennata (Coleoptera: Cerambycidae)

Abstract

We report here the pheromone of Megacyllene antennata (White) (Coleoptera: Cerambycidae), a species native to southwestern North America whose larvae feed in woody tissues of mesquite ( Prosopis species; Fabaceae). Adult males sex-specifically produced a blend of eight common natural products, including the monoterpene alcohol ( S)-α-terpineol; the monoterpenes ( S)-limonene and terpinolene; the aromatic alcohols ( R)-1-phenylethanol and 2-phenylethanol; and ( E)-2-hexenol, ( E)-2-hexenal, and 1-hexanol. Individual males produced the components in varying amounts, but ( S)-α-terpineol and ( E)-2-hexenal were always present and together constituted the majority of the blend. A synthetic reconstruction of the complete blend attracted both males and females of M. antennata during field bioassays, as did all subsets of the blend that included ( S)-α-terpineol and ( E)-2-hexenol. Adults were most strongly attracted to blends of the latter two compounds when in ratios approaching parity. Neither of the compounds were present in the bouquet of volatiles emitted by host plants of the larvae.