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2000 Fiscal Year Final Research Report Summary

Synthetic Studies on Semiochemicals Related to the Pest Control

Research Project

Project/Area Number 11660101
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTohoku University (2000)
Ibaraki University (1999)

Principal Investigator

KUWAHARA Shigefumi  Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Associate Professor, 大学院・農学研究科, 助教授 (30170145)

Project Period (FY) 1999 – 2000
Keywordsstink bug / sesquiterpene / pheromone / cockroach / periplanone / spodoptera exigua / volicitin / leaf miner moth
Research Abstract

Synthesis of both the racemate and optically active forms of a novel sesquiterpene (9-isopropyl-4, 6-dimethyltricyclo [4.4.0.0^<5, 9>] dec-3-en-2-one) isolated from the pheromone gland of a Brazilian predatory stink bug, Tynacantha marginata Dallas, was achieved via a intramolecular double Michael cycloaddition and intramolecular Diels-Alder reaction, respectively. This synthetic work enabled us to determine the absolute configuration of the putative pheromone in addition to the confirmation of the proposed structure. Other semiochemicals such as the sex pheromones of Periplaneta fuliginosa and Perileucoptera coffeella, and an elicitor (named volicitin) contained in the regurgitant of Spodoptera exigua were also synthesized in optically active forms. The synthesis of the sex pheromone of Periplaneta fuliginosa led to the correction of prviously reported physical and spectroscopic data of this pheromone called periplanone-D.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Shigefumi Kuwahara: "Preparation of (-)-periplanone D and its physical and spectroscopic properties"Bioscience, Biotechnology, and Biochemistry. 64. 600-602 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ting Liang: "Simple Synthesis of 5,9-dimethylated long-chain alkanes, the sex pheromones of leaf miner moths"Bioscience, Biotechnology, and Biochemistry. 64. 2474-2477 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shigefumi Kuwahara: "Synthesis of all four possible stereoisomers of 5,9-dimethylpentadecane, the major sex pheromone component of the coffee leafminer moth"Bioscience, Biotechnology, and Biochemistry. 64. 2723-2726 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shigefumi Kuwahara: "Synthesis of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas"Tetrahedron. 56. 8111-8117 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shigefumi Kuwahara: "Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata"Synthesis. 1930-1935 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 桑原重文: "昆虫の生産する生態相関物質の合成研究"日本農薬学会誌. 25. 451-455 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Kuwahara, I.Nagashima, W.S.Leal, J.Ishikawa, and O.Kodama: "Preparation of (-)-periplanone D and its physical and spectroscopic properties."Bioscience, Biotechnology, and Biochemistry. 64. 600-602 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Liang, S.Kuwahara, M.Hasegawa, and O.Kodama: "Facile synthesis of 5, 9-dimethylated long-chain alkanes, the sex pheromone of leaf miner moths"Bioscience, Biotechnology, and Biochemistry. 64. 2474-2477 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Kuwahara, T.Liang, W.S.Leal, J.Ishikawa, and O.Kodama: "Synthesis of all four possible stereoisomers of 5, 9-dimethylpentadecane, the major sex pheromone component of the coffee leaf miner moth, Perileucoptera coffeella"Bioscience, Biotechnology, and Biochemistry. 64. 2723-2726 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Kuwahara, S.Hamade, W.S.Leal, J.Ishikawa, and O.Kodama: "Synthesis of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata"Tetrahedron. 56. 8111-8117 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Kuwahara, J.Ishikawa, W.S.Leal, S.Hamade, and O.Kodama: "Synthesis of Both Enantiomers of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas."Synthesis. 1930-1935 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Kuwahara: "Synthesis of some insect semiochemicals."Journal of Pesticide Science. 25. 451-455 (2000)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2002-03-26  

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