Journal of Chemical Ecology (2004) 30, 631-641

A. Zada, S. Ben-Yehuda, E. Dunkelblum, M. Harel, F. Assael and Z. Mendel (2004)
Synthesis and biological activity of the four stereoisomers of 4-methyl-3-heptanol: main component of the aggregation pheromone of Scolytus amygdali
Journal of Chemical Ecology 30 (3), 631-641
Abstract: Stereoisomers of 4-methyl-3-heptanol are major components of aggregation pheromones of bark beetles and trail pheromones of ants. Recently, (3S,4S)-4-methyl-3-heptanol (I) has been tentatively identified as the main component of the aggregation pheromone of the almond bark beetle, Scolytus amygdali (Coleoptera: Scolytidae). The four stereoisomers of 4-methyl-3-heptanol were prepared and bioassayed. Key steps included preparation of chiral 4-methyl-3-heptanones using SAMP and RAMP reagents, reduction to the corresponding alcohols, and stereospecific transesterification with vinyl acetate with lipase AK catalysis. In field tests, only (3S,4S)-4-methyl-3-heptanol attracted beetles in combination with the synergist (3S,4S)-4-methyl-3-hexanol, whereas (3R,4S)- and (3R,4R)-4-methyl-3-heptanols were inhibitory.
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Link to article at publishers website
Database assignments for author(s): A. Zada, Zvi Mendel

Research topic(s) for pests/diseases/weeds:
pheromones/attractants/traps

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Pest and/or beneficial records:

Beneficial	Pest/Disease/Weed	Crop/Product	Country	Quarant.
	Scolytus amygdali