Premium
Synthesis and bioactivity of ( 13 Z , 15 E )‐octadecadienal: A sex pheromone component from Micromelalopha siversi Staudinger (Lepidoptera: Notodontidae)
Author(s) -
Liu Fu,
Guo Li,
Zhang Sufang,
Kong Xiangbo,
Zhang Zhen
Publication year - 2021
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.6015
Subject(s) - pheromone , lepidoptera genitalia , stereochemistry , sex pheromone , electroantennography , chemistry , wittig reaction , biology , botany
BACKGROUND 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. RESULTS Four unsaturated aliphatic aldehydes, Z 13, E 15‐18:Ald, Z 13, Z 15‐18:Ald, E 13, E 15‐18:Ald, and E 13, Z 15‐18: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, Z 13, E 15‐18:Ald was the main component, and a small amount of Z 13, Z 15‐18:Ald was also detected, with a ratio of approximately 7:3. However, the results of GC‐electroantennographic detection (GC‐EAD) showed that Z 13, E 15‐18:Ald was the only compound with electrophysiological activity, whereas Z 13, Z 15‐18:Ald elicited no activity. In the field, traps baited with only Z 13, E 15‐18:Ald resulted in much superior results to those with Z 13, Z 15‐18:Ald as well as the Z 13, E 15‐18:Ald and Z 13, Z 15‐18:Ald binary mixture. CONCLUSIONS Based on geometrically selective synthesis and bioactivity tests, the active sex pheromone component of M. siversi has been identified as Z 13, E 15‐18:Ald, the pheromone component that has not been identified in Lepidoptera before. The synthetic component was attractive to male moths in preliminary field traps, which provides novel technologies to monitor and control this pest.