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J Chem Ecol. 2019 Apr;45(4):356-365. doi: 10.1007/s10886-019-01056-6. Epub 2019 Feb 23.

Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae).

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Eco-Chemistry, Department of Chemical Engineering, Mid Sweden University, SE-851 70, Sundsvall, Sweden.
Department of Ecology, Swedish University of Agricultural Sciences, Box 7044, SE-750 07, Uppsala, Sweden.
Eco-Chemistry, Department of Chemical Engineering, Mid Sweden University, SE-851 70, Sundsvall, Sweden.


The bark beetle Polygraphus punctifrons (Coleoptera: Curculionidae) is a species that feeds on Norway spruce (Picea abies) and is found in the Northern parts of Europe and Russia. The release of volatile organic compounds (VOCs) produced by males and females of P. punctifrons when the beetles bore into spruce stem sections in a laboratory environment was studied using solid phase microextraction (SPME). The sampled VOCs emitted by boring beetles were analysed by gas chromatography and mass spectrometry (GCMS). (+)-2-[(1R,2S)-1-Methyl-2-(prop-1-en-2-yl)cyclobutyl]ethanol [(+)-(1R,2S)-grandisol] and (-)-(R)-1-isopropyl-4-methyl-3-cyclohexen-1-ol [(-)-(R)-terpinen-4-ol] were identified to be male specific volatiles. The identity of the compounds was confirmed by comparison with synthetic samples. Field trials with synthetic compounds in Sweden showed that racemic grandisol per se was strongly attractive for both males and females, while (-)-(R)-terpinen-4-ol was not. Further, when adding (-)-(R)-terpinen-4-ol to rac-grandisol, a synergistic effect was observed as the trap catch of P. punctifrons was fourfold. (-)-(R)-Terpinen-4-ol by its own did not attract P. punctifrons but Polygraphus poligraphus, and the latter was also attracted to traps baited with a 10:90 mixture of the two compounds. Thus, we have identified (+)-(1R,2S)-grandisol as a main component and (-)-(R)-terpinen-4-ol as a minor component of the aggregation pheromone of P. punctifrons. This opens future possibilities to monitor and, if necessary, manage populations of P. punctifrons.


(+)-(1R,2S)-Grandisol; (−)-(R)-Terpinen-4-ol; Enantiomeric separation; Picea abies; Preparative fraction collection; SPME

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