Polygraphus poligraphus

In Polygraphus poligraphus the (4k)-enantiomer of terpinen-4-ol 234, acts as an aggregation pheromone [467]. The compound is accompanied by the thujanols 251 and 252 which may be biogenetically close to terpinen-4-ol and keep the same configuration at C4 [440]. 

Kohnle U., Francke W. and Bakke A. (1985) Polygraphus poligraphus (L.) response to enantiomers of beetle specific terpene alcohols and a bicyclic ketal. Z. ang. Ent. 100, 5-8. 

Monoterpenic hydrocarbons play an important role in the chemical communication between coniferous trees and forest insects. Complicated relationships between the activity of a pheromone and its enantiomeric composition have been revealed. Some forest insects respond only to one enantiomer or to specific proportions of two enantiomers. Sometimes an inactive enantiomer blocks its active antipode. For example monoterpenic alcohol (-)-terpinen-4-ol of enantiomeric purity >99% is aggregating pheromone of the beetle Polygraphus poligraphus while a racemic composition of this monoterpenoid failed to attract the beetles [19]. 

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