Identification and Synthesis of Leptotriene, a Unique Sesquiterpene Hydrocarbon from Males of the Leaffooted Bugs Leptoglossus zonatus and L. occidentalis

The leaffooted bugs Leptoglossus zonatus and L. occidentalis (Hemiptera: Coreidae) cause substantial damage in tree nut crops in North America and pine seed orchards in North America and Europe, respectively. Sexually mature males of both species produce a number of aldehydes, esters, and sesquiterpenes, which are hypothesized to constitute an aggregation pheromone attractive to both sexes. Among the volatiles produced by males of both species, we identified a unique sesquiterpene hydrocarbon, given the common name leptotriene (5), which elicited strong responses from antennae of both sexes in electroantennogram assays. Here, we report its structure and its synthesis from (-)-(E)-beta-caryophyllene (1).

Automated summary

The leaffooted bugs Leptoglossus zonatus and L. occidentalis cause significant damage to tree nut crops in North America and pine seed orchards in North America and Europe, respectively. Males of both species produce a unique sesquiterpene called leptotriene, which attracts both sexes.