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

Abstract

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.

사과무늬잎말이나방의 성 유인물질인 (Z)-11-테트라데센-1-일 아세테이트(1)와 (E)-11-테트라데센-1-일 아세테이트(2)를 합성하여 생물활성시험을 수행하였다. 10-브로모데칸-1-올과 DHP에서 얻어지는 10-브로모데칸-1-올 THP에테르를 아세틸렌소디움음이온과 알킬화시켜 11-도데신-1-올 THP에테르를 합성하였다. 이것을 부틸리튬으로 처리하여 얻어지는 리튬음이온을 브로모에탄과 반응시켜 11-테트라데센-1-올 THP에테르를 얻었다. 이것을 $Pd/BaSO_4$하에서 수소환원시켜 (Z)-11-테트라데센-1-올 THP에테르를 얻었고, $Na/NH_3$와 금속환원시켜 (E)-11-테트라데센-1-올 THP에테르를 얻었다. (Z)-와 (E)-형의 화합물을 보호기를 제거한 후 아세트산무수물로 아세틸화하여 (Z)-11-테트라데센-1-일 아세테이트와 (E)-11-테트라데센-1-일 아세테이트를 각각 얻었다. 합성된 성 페로몬에 대한 사과무늬잎말이나방 숫컷의 성 유인력을 시험해 본 결과 활성이 있음이 밝혀졌다.

Keywords

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