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Reduction of Carpophilus freemani Dobson (Coleoptera: Nitidulidae) aggregation pheromone response by synthetic analogues

Analogues of (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene, the major component of the aggregation pheromone of Carpophilus freemani Dobson (Coleoptera: Nitidulidae), were synthesized and the potency of these compounds in suppressing the response of C. freemani to its pheromone in a wind tunnel bioas...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1999-03, Vol.47 (3), p.1189-1195
Main Authors: Petroski, R.J, Weisleder, D
Format: Article
Language:English
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Summary:Analogues of (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene, the major component of the aggregation pheromone of Carpophilus freemani Dobson (Coleoptera: Nitidulidae), were synthesized and the potency of these compounds in suppressing the response of C. freemani to its pheromone in a wind tunnel bioassay was determined. The most potent compounds reduced behavioral response to pheromone 83-96% when the inhibitors were present in 10-fold excess. These compounds are (1Z,3E,5E)-1-methoxy-3-ethyl-5-methyl-1,3,5-heptatriene, (1E,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1, 3,5-heptatriene, and (1Z,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1, 3,5-heptatriene. In the presence of fermenting bread dough (a pheromone synergist), the most potent inhibitory compound, (1Z,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1, 3,5-heptatriene, was less effective in reducing mean landings (69% vs 99%) than when dough was absent. This inhibitory compound causes a reduction of response to pheromone but does not cause a reduction of response to fermenting food-type volatiles such as fermenting bread dough. Analogues of pheromones that strongly reduce response to pheromones by insects might be useful as biochemical probes to study the pharmacophoric (three-dimensional structure) requirements for pheromone perception.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf9809378