Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer

It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3-5 day intervals), respectively, with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic 1 is presented. The absolute configuration of natural 1 from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed.