Synthetic Studies on Semiochemicals Related to the Pest Control

害虫防治相关化学信息素的综合研究

• 批准号: 11660101
• 负责人: KUWAHARA Shigefumi
• 金额: $ 1.86万
• 依托单位: Tohoku University (2000)Ibaraki University (1999)
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1999
• 资助国家: 日本
• 起止时间: 1999 至 2000
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-11660101/
• 关键词: stink bug; sesquiterpene; pheromone; cockroach; periplanone; spodoptera exigua; volicitin; leaf miner moth; Tynacantha marginata; sesquiterpene; Diels-Alder reaction; periplanone-D; periplanone-C; volicitin; 5,9-dimethylpentadecane; Perileu

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.

从巴西掠食性臭虫Tynacantha marginata Dallas的信息素腺中分离得到一种新型倍半萜（9-异丙基- 4,6 -二甲基三环[4.4.0.0^< 5,9 >]dec3 -en-2-one）的外消旋体和光学活性形式，分别通过分子内双Michael环加成和分子内Diels-Alder反应合成。这项合成工作使我们能够确定假设的信息素的绝对构型，以及所提出的结构的确认。此外，还合成了其他半化学物质，如黄斑大蠊和咖啡夜蛾的性信息素，以及黑斑夜蛾反刍物中含有的一种激发子（名为volicitin）。通过对大蠊性信息素的合成，对先前报道的大蠊性信息素d的物理和光谱数据进行了修正。

项目成果

S.Kuwahara: "Synthesis of some insect semiochemicals."Journal of Pesticide Science. 25. 451-455 (2000)

S.Kuwahara：“一些昆虫化学信息素的合成。”农药科学杂志。

S.Kuwahara,T.Liang,W.S.Leal,J.Ishikawa,O.Kodama: "Synthesis of all four possible stereoisomers of 5,9-dimethyl-pentadecane, the sex pheromone component of the coffee leaf miner moth"Bioscience,Biotechnology,and Biochemistry. 64・12. 2723-2726 (2000)

S. Kuwahara、T. Liang、W. S. Leal、J. Ishikawa、O. Kodama：“咖啡潜叶蛾的性信息素成分 5,9-二甲基十五烷的所有四种可能的立体异构体的合成”生物科学，生物技术，和生物化学 64・12。

Shigefumi Kuwahara et.al.: "Preparation of (-)-periplanone D and its physical and spectroscopic properties"Bioscience,Biotechnology,and Biochemistry. 64(3). 600-602 (2000)

Shigefumi Kuwahara 等人：“(-)-periplanone D 的制备及其物理和光谱特性”生物科学、生物技术和生物化学。

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)

Shigefumi Kuwahara：“5,9-二甲基十五烷（咖啡斑蛾的主要性信息素成分）的所有四种可能立体异构体的合成”生物科学、生物技术和生物化学。

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)

S.Kuwahara、S.Hamade、W.S.Leal、J.Ishikawa 和 O.Kodama：“从椿象 Tynacantha marginata 的信息素腺中分离出一种新型倍半萜烯的合成”四面体。