title: Reduction of Carpophilus freemani dobson (Coleoptera: nitidulidae) aggregation pheromone response by synthetic analogues.
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.
authors.affiliation: 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
authors.forename: R J
authors.initials: RJ
authors.lastname: Petroski
authors.forename: D
authors.initials: D
authors.lastname: Weisleder
mesh_terms: D000818:Animals; D001681:Biological Assay; D001939:Bread; D001517:Coleoptera; D005285:Fermentation; D008958:Models, Molecular; D008968:Molecular Conformation; D010675:Pheromones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C411254:4,8-dimethyl-1,3,7-nonatriene; D010675:Pheromones; D013729:Terpenes