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Replacement of carcinogenic alkylating agent ethylene oxide in the synthesis of (Z)-3-dodecen-1-YL (E)-2-butenoate, sex pheromone of sweet-potato weevil,Cylas formicarius elegantulus (summers) andCylas formicarius formicarius (F.)

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Abstract

An alternative synthesis of (Z)-3-dodecen-1-y1 (E)-2-butenoate without use of carcinogenic ethylene oxide and HMPA is described. By coupling of the tetrahydropyranyl (THP) ether of 3-butyn-1-ol with 1-bromooctane with sodamide in liquid ammonia, 12-(2-tetrahydropyranyloxy)-9-dodecyne was obtained; subsequent hydrolysis and semihydrogenation afforded (Z)-3-dodecen-1-ol. The alcohol was then reacted with crotonyl chloride to give the desired crotonate with a total yield of 29.8%. Males of sweet-potato weevil,Cylas formicarius were strongly attracted to the synthetic sex pheromone. The attraction from the dispenser of polyethylene tube was better than the attraction from the dispenser of rubber septum in the field.

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Authors and Affiliations

  1. Pesticide Chemistry Department, Taiwan Agricultural Chemical and Toxic Substances Research Institute (TACTRI), Taiwan R.O.C.

    Chi-Chu Lo & Ming-Der Hung

  2. Tao Yuan District Agricultural Improvement Station, Taiwan, R.O.C.

    Cheng-Jiung Liu

Authors
  1. Chi-Chu Lo
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  2. Ming-Der Hung
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  3. Cheng-Jiung Liu
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Lo, CC., Hung, MD. & Liu, CJ. Replacement of carcinogenic alkylating agent ethylene oxide in the synthesis of (Z)-3-dodecen-1-YL (E)-2-butenoate, sex pheromone of sweet-potato weevil,Cylas formicarius elegantulus (summers) andCylas formicarius formicarius (F.). J Chem Ecol 18, 95–103 (1992). https://doi.org/10.1007/BF00993745

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  • DOI: https://doi.org/10.1007/BF00993745

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