Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/13/1996
Publication Date: N/A
Citation: Interpretive Summary: The plum curculio, Conotrachelus nenuphar, is an important pest of apples, peaches, plums and cherries east of the Rocky Mountains. Effective control of this pest is hindered by problems in detecting weevils before they seriously damage the crop. Scientists at the National Center for Agricultural Utilization Research, Peoria, IL, identified a pheromone (an attractant that insects use to locate other individuals of the same species) produced by male plum curculios. The pheromone was found to consist of a single component. This compound was synthesized in the laboratory and tested in the field. Insect traps baited with the synthetic compound captured both male and female plum curculios. This synthetic plum curculio pheromone may be useful in detecting plum curculios before they damage orchard crops and could reduce the use of pesticides on these crops.
Technical Abstract: (+)-(1R,2S)-1-methyl-2-(1-methylethenyl)-cyclobutaneacetic acid [1A] was isolated from male plum curculios, Conotrachelus nenuphar (Herbst) (Coleoptera: Curculionidae), feeding on plums and apples. Its structure was determined using achiral and chiral glc, eims, optical rotation, and 1H and 13C nmr, and was confirmed by synthesis. The racemic acid (a synthetic mixture of 1A and its enantiomer) attracted both female and male plum curculios when used to bait traps placed in several species of fruit trees. It is suggested that 1A is the major component of an aggregation pheromone of the plum curculio, and the trivial name, nenupharic acid, is proposed. Potential uses for nenupharic acid, as well as possible ways to increase its effectiveness, are discussed.