Synthesis and bioactivity of (13Z,15E)-octadecadienal: A sex pheromone component from Micromelalopha siversi Staudinger (Lepidoptera: Notodontidae)

Pest Management Science
Fu LiuZhen Zhang

Abstract

Micromelalopha siversi (Staudinger) (Lepidoptera: Notodontidae) is a defoliator of poplar trees, Populus spp. (Salicaceae). In our previous study, 13,15-octadecadienal has been conformed as a female-produced candidate sex pheromone component of M. siversi, but the Z/E stereochemistry of the 1,3-diene system has not been identified so far. Four unsaturated aliphatic aldehydes, Z13,E15-18:Ald, Z13,Z15-18:Ald, E13,E15-18:Ald, and E13,Z15-18:Ald, were synthesized from the commercially available 12-bromo-1-decanol mainly by alkylation of lithium alkyne, normal Wittig or Wittig-Schlosser olefination, and hydroboration-protonolysis. According to gas chromatography (GC) analysis of pheromone gland extracts, Z13,E15-18:Ald was the main component, and a small amount of Z13,Z15-18:Ald was also detected, with a ratio of approximately 7:3. However, the results of GC-electroantennographic detection (GC-EAD) showed that Z13,E15-18:Ald was the only compound with electrophysiological activity, whereas Z13,Z15-18:Ald elicited no activity. In the field, traps baited with only Z13,E15-18:Ald resulted in much superior results to those with Z13,Z15-18:Ald as well as the Z13,E15-18:Ald and Z13,Z15-18:Ald binary mixture. Based on geometrically selecti...Continue Reading

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

SPSS

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