Synthesis and Biological Activity Test of the Pheromone of the Asiatic Leafroller Moth

사과나무잎말이나방의 성 페로몬 합성과 생물활성시험

  • Suk-Ku Kang (Department of Chemistry, Sung Kyun Kwan University) ;
  • Min-Suk Ku (Department of Chemistry, Sung Kyun Kwan University) ;
  • Kwanghyun No (Department of Chemistry, Sookmyung Women's University) ;
  • Jeong-Oon Lee (Department of Entomology, Institute of Agricultural Sciences)
  • 강석구 (성균관대학교 이과대학 화학과) ;
  • 구민숙 (성균관대학교 이과대학 화학과) ;
  • 노광현 (숙명여자대학교 이과대학 화학과) ;
  • 이정운 (농촌진흥청 농업기술연구소 곤충과)
  • Published : 1987.12.20


Synthesis and Biological activity test are described for the (E)-11-tetradecen-1-yl acetate and (Z)-11-tetradecen-1-yl acetate, the sex pheromone of the Asiatic leafroller moth (Archippus breviplicanus Walsingham). 10-Bromodecan-1-ol THP ether was prepared from 10-bromodecan-1-ol. In liquid ammonia with THF and HMPA as cosolvents, sodium acetylide could be alkylated with 10-bromodecan-1-al THP ether to give 11-dodecyn-1-ol THP ether. 11-Dodecyn-1-ol THP ether was then treated with n-Buli in THF to give the lithium acetylide, which was alkylated with bromoethane to afford 11-tetradecyn-1-ol THP ether. 11-Tetradecyn-1-ol THP ether was then reduced over $Pd/BaSO_4$ and with Na in liquid $NH_3$ to give (Z)-11-tetradecen-1-ol THP ether and (E)-11-tetradecen-1-ol THP ether, respectively. (Z)-and (E)-11-Tetradecen-1-ol THP ether thus obtained were deprotected by refluxing in the presence of PPTS and ethanol. (Z)-and (E)-11-tetradecen-1-ol were acetylated with acetic anhydride to afford the final products, (Z)-11-tetradecen-1-yl acetate (1) and (E)-11-tetradecen-1-yl acetate (2), respectively. The synthetic pheromone thus obtained was attractive to the males of the Asiatic leafroller moth in the field.



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