Electroantennogram responses of synthetic periplanone-A and periplanone-B in the american cockroach
The electroantennogram responses of synthetic (−)-periplanone-B (PB) and (−)-periplanone-A (PA) were evaluated by using the antennae of the unmated male American cockroachPeriplaneta americana L. The threshold concentrations of the pheromone activities for the two chemicals were similar. Neither a synergistic nor an inhibitory response was noted, and only an additive effect was detected when PA and PB were applied as a mixture.
Electroantennogram Responses and Field Trapping of Asian Cockroach (Dictyoptera: Blattellidae) with Blattellaquinone, Sex Pheromone of the German Cockroach (Dictyoptera: Blattellidae)
ABSTRACT 
 The Asian cockroach, Blattella asahinai Mizukubo, first introduced to Florida in 1986, has been spreading throughout the southeastern United States. Populations can reach extremely high densities and cause damage to crops as well as become a nuisance in residential settings. Because the German cockroach, Blattella germanica L., is its closest extant relative, we characterized the B. asahinai male response to blattellaquinone, the sex pheromone of the German cockroach, in an effort to develop monitoring tools for B. asahinai. Electroantennogram (EAG) analysis was conducted on B. asahinai and B. germanica males and females, and revealed that the antennae of males of both species responded significantly more to blattellaquinone than females, and in both males and females absolute EAG responses of B. asahinai were greater than in B. germanica males and females, respectively. However, normalized male EAG response curves and ED50 values (effective dose to elicit 50% of maximal response) did not differ significantly between the two species. Results of field trapping experiments demonstrated that male B. asahinai were more attracted to blattellaquinone than any other life stage, and 10 µg of blattellaquinone attracted the most males. These results suggest that blattellaquinone or a similar compound might be a component of the sex pheromone of B. asahinai females.
Studies on sex pheromone of American cockroach, with emphasis on structure elucidation of periplanone-A
Two independently biologically active compounds, periplanone A and periplanone B can be isolated from fecal material of the American cockroach,Periplaneta americana. In fecal material these occur in a ratio of 1 ∶ 10 while, in intestinal tracts only periplanone B has been found. The latter has been identified as (1Z,5E)-1,10(14)-diepoxy-4(15),5-germacradien-9-one; the identification was confirmed by synthesis. Only the CD (−) enantiomer (1R,2R,5E,7S,10R) exhibited activity. The lower threshold of activity of both natural and synthetic CD (−) pheromone, is 10−6–10−7 μg. Periplanone A has been identified (apart from its stereochemical configuration) as 7-methylene-4-isopropyl-12-oxa-tricyclo[4.4.2.01,5]-9-dodecen-2-one). The structure of this rather unstable compound could be deduced by comparing its NMR, UV, IR, and mass spectra with the NMR and mass spectra of its rearrangement product. Both structures still require confirmation by synthesis, but their spectral data are in complete agreement with the proposed structures. The presence of only periplanone B in the gut and the presence of both periplanone A and periplanone B in the feces suggests that periplanone B is a genuine sex pheromone, whereas peri-planone A might be a biologically active transformation product, which in turn can isomerize into a more stable, but inactive compound.