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The beetle  Homalinotus depressus  (Coleoptera: Curculionidae) is a major pest of coconuts in the Northern region of Brazil, for which environmentally friendly methods of control are desired. Behavioral responses of  H .  depressus  to airborne volatile extracts from conspecifics suggested the presence of a male-produced aggregation pheromone. GC analyses of these extracts showed the presence of four male-specific compounds. Analytical data in combination with the synthesis of standards led to the identification of the male-released semiochemicals as epoxyisophorone ( 1 ), isophorone ( 2 ), homalinol ( 3 ), and 2-hydroxyisophorone ( 4 ), of which ( 3 ) was the major constituent. The configuration of homalinol was determined to be  cis  on the basis of retention times of synthetic  cis  and  trans  synthetic standards. Enantiomers of  cis -homalinol were obtained in high enantiomeric excess by using biocatalysis. Their separation on a GC enantioselective column (β-Dex325®), allowed us to unambiguously determine that the absolute configuration of natural homalinol was (1 R ,2 R ,6 S ). Field bioassays demonstrated that both the synthetic major compound per se and mixtures of all four male-specific compounds were attractive to  H .  depressus .

Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae