Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer reviewed journal
Publication Acceptance Date: 1/26/2005
Publication Date: 1/1/2005
Citation: Zhang, A., Nie, J. 2005. Enantioselective synthesis of the female sex pheromone of the pink hibiscus mealybug, maconellicoccus hirsutus.. Journal of Agricultural and Food Chemistry. 53(7):2451-2455. Interpretive Summary: The hibiscus or pink mealybug (PHM), is a serious agricultural pest that attacks more than 200 plants, shrubs, and trees. Its wide host range favors rapid spread and complicates effective control. Potential losses of $750 million per year have been estimated if the insect cannot be controlled in the United States. To date, detection of PHM infestations relies on visual inspection, although live virgin females can be used as an attractant source; however, limited availability and low survivorship of live virgin females made this application impractical. A synthetic pheromone would provide a much more economical, convenient, and useful survey tool. The present research was launched to help manage the PHM infestation in the continental U. S. The female PHM releases a novel four-member ring alcohol ester that together with lavandulyl ester constitutes the sex pheromone to attract males from a distance. The skeleton of this four-member ring alcohol has not been reported previously. In order to unambiguously confirm the identified structure, determine the active form of the pheromone, and provide material for field biological testing, each individual pheromone component has been synthesized. Field test results indicated that a synthetic blend of the two esters is a potent attractant of males. The pheromone trap will not impede biological control eradication programs currently underway in the Caribbean region, California, and Florida by APHIS, however, it will enable the future development of mass trapping, attract-and-kill, and mating disruption technologies for growers to manage this pest.
Technical Abstract: The pink hibiscus mealybug, Maconellicoccus hirsutus (Green), is an exotic insect pest and recently invaded Southern California and Florida. The female M. hirsutus releases a novel cyclobutanoid monoterpene alcoholic ester that together with lavandulyl ester constitutes the sex pheromone to attract males from a distance. The enantioselective synthesis of the major sex pheromone component, maconelliyl 2-methylbutanoate 1, from '-pinene is reported. Absolute configurations of both natural occurring maconelliyl 2-methylbutanoate 1 and minor component, lavandulyl 2-methylbutanoate 2, have been established as RS by comparison of the naturally occurring compounds with the optically active isomers derived from the enantioselective synthesis.