| Title: | Reduction of Carpophilus freemani dobson (Coleoptera: nitidulidae) aggregation pheromone response by synthetic analogues |
| Author(s): | Petroski RJ; Weisleder D; |
| Address: | "USDA, REE, Agricultural Research Service, National Center for Agricultural Utilization Research, Bioactive Agents Research and Analytical Support Units, 1815 North University Street, Peoria, Illinois 61604, USA. petrosrj@mail.ncaur.usda.gov" |
| ISSN/ISBN: | 0021-8561 (Print) 0021-8561 (Linking) |
| Abstract: | "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" |
| Keywords: | "Animals Biological Assay Bread *Coleoptera Fermentation Models, Molecular Molecular Conformation Pheromones/chemical synthesis/*chemistry/*pharmacology Structure-Activity Relationship Terpenes/chemical synthesis/*chemistry/pharmacology;" |
| Notes: | "MedlinePetroski, R J Weisleder, D eng 1999/12/20 J Agric Food Chem. 1999 Mar; 47(3):1189-95. doi: 10.1021/jf9809378" |
