Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/4/2008
Publication Date: 4/1/2008
Citation: Khrimian, A., Lance, D.R., Schwarz, M., Leonhardt, B., Mastro, V. 2008. Sex pheromone of browntail moth, Euproctis chrysorrhoea (L.). Synthesis and field deployment. Journal of Agricultural and Food Chemistry. 56(7):2452-2456. Interpretive Summary: Insect pests cause a significant damage to crops and forests, and monitoring their populations aids greatly to reducing pesticide use and biological control. Pheromones, or chemicals that trigger a natural behavioral response in another member of the same species, are commonly used as baits for sampling insect populations. The browntail moth is a pest of forest and orchard trees but it also possesses stinging hairs causing severe dermatitis that often necessitates the control of this insect species. Pheromone of the browntail moth was previously identified but the synthesis has not been reported. Herein we report on the synthesis and successful field application of the browntail moth pheromone in Cape Cod, Massachusetts. The results of this study are of interest to other chemists and entomologists involved in the research of potential pest control compounds, and to State and Federal agencies involved in monitoring and controlling insect pests of agriculture and forests.
Technical Abstract: The browntail moth, Euproctis chrysorrhoea (L.), in native to Eurasia, where periodic outbreaks result in defoliation of forest, shade and ornamental trees. At present, known U.S. populations are limited to coastal islands and dunes in Maine and Massachusetts. In addition to the damage caused by defoliation, human contact with larval urticating hairs often results in severe dermatitis. Hence, tools for monitoring and controlling the moth populations are desirable. The female-produced sex pheromone of the browntail moth was identified but the synthesis had not been published. Now we report on the synthesis of the pheromone of the browntail moth, (7Z,13Z,16Z,19Z)-docosatetraenyl isobutyrate, using in a key step a Wittig olefination of (6Z)-13-(tetrahydopyranyloxy)tridecenal with (3Z,6Z)-nonadienyltriphenylphosphonium salts. Field trappings of male E. chrysorrhoea, conducted with rubber septa and string formulations of the pheromone, including dose-response, pheromone purity, and dispenser-aging trials, revealed that traps baited with 250 µg of pheromone of 88-94% geometric purity (main impurity being 13E isomer) on rubber septa are suitable for monitoring the moth populations during the entire flight season.