Synthetic Studies on Semiochemicals Related to the Pest Control

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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.