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Deuterated analogues of 4,8-dimethyldecanal, the aggregation pheromone of Tribolium castaneum: synthesis and pheromonal activity

✍ Scribed by Junheon Kim; Shigeru Matsuyama; Takahisa Suzuki

Publisher: John Wiley and Sons
Year: 2004
Tongue: French
Weight: 149 KB
Volume: 47
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.881

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✦ Synopsis

Abstract

To elucidate the deuterium isotope effect (DIE) in pheromonal activity and to investigate the biosynthetic pathway of 4,8‐dimethyldecanal (4,8‐DMD; 1), the aggregation pheromone of the red flour beetle (Tribolium castaneum), deuterated analogues of 4,8‐DMDs (2, 3, 4, and 5), were synthesized and their pheromonal activities were tested using a two‐hole pitfall olfactometer. Although no apparent DIE was observed in their pheromonal activities, 4,8‐DMD‐1‐d~1~ (2) was less attractive than other analogues, which suggested that the bond distance between the formyl group of 1 and its receptor was critical in pheromone recognition by T. castaneum. Copyright © 2004 John Wiley & Sons, Ltd.

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