Wood cockroaches in the genus Parcoblatta, comprising 12 species endemic to North America, are highly abundant in southeastern pine forests and represent an important prey of the endangered red-cockaded woodpecker, Picoides borealis. The broad wood cockroach, Parcoblatta lata, is among the largest and most abundant of the wood cockroaches, constituting >50% of the biomass of the woodpecker's diet. Because reproduction in red-cockaded woodpeckers is affected dramatically by seasonal and spatial changes in arthropod availability, monitoring P. lata populations could serve as a useful index of habitat suitability for woodpecker conservation and forest management efforts. Female P. lata emit a volatile, longdistance sex pheromone, which, once identified and synthesized, could be deployed for monitoring cockroach populations. We describe here the identification, synthesis, and confirmation of the chemical structure of this pheromone as (4Z,11Z)-oxacyclotrideca-4,11-dien-2-one [= (3Z,10Z)-dodecadienolide; herein referred to as "parcoblattalactone"]. This macrocyclic lactone is a previously unidentified natural product and a previously unknown pheromonal structure for cockroaches, highlighting the great chemical diversity that characterizes olfactory communication in cockroaches: Each long-range sex pheromone identified to date from different genera belongs to a different chemical class. Parcoblattalactone was biologically active in electrophysiological assays and attracted not only P. lata but also several other Parcoblatta species in pine forests, underscoring its utility in monitoring several endemic wood cockroach species in red-cockaded woodpecker habitats.pheromone monitoring | surveillance | wildlife conservation M any animals-especially nocturnal insects-have evolved sexually dimorphic sex pheromones as an efficient and relatively private communication channel for mate attraction and mate choice (1). Sex pheromones also function in species discrimination, and therefore pheromone blends also play prominent roles in premating reproductive isolation of closely related species and in speciation (1, 2).Most cockroach species are nocturnal, and they profoundly rely on pheromones for intraspecific communication. For example, females of the broad wood cockroach, Parcoblatta lata, a species endemic to pine forests of the southeastern United States, have short wings, are incapable of flight, and therefore have limited dispersal capability. However, by emitting a volatile sex pheromone sexually receptive females are able to recruit males, which are excellent flyers, efficiently (3). Females and nymphs thus are able to remain in the relatively protected habitat beneath the sloughing bark of decaying logs, whereas males incur the greater energetic cost of mate-finding and predation that is associated with greater movement. Our earlier behavioral observations suggested the presence of a female sex pheromone, emitted during a "calling" display, and anatomical and electrophysiological studies confirmed that female-specific ter...