Brownbanded cockroach

FIGURE 2 Pheromone structures of the American cockroach (periplanone B), the brownbanded cockroach (supellapyrone), bark beetles (ipsdienol enantiomers), and the cabbage looper moth (six acetates). 

The EAG technique as a bioassay tool for active fractions has been used in the identification of sex pheromones of many insect species in several orders and remains as a key factor in the identification of pheromones. In the recent identification of the brownbanded cockroach pheromone supellapyrone (7) (Figure 2), the EAG technique was used throughout the entire process of isolating and purifying active material from 12,000... 

Liang, D., Zhang, A., Kopanic, R. J., Jr, Roelofs, W. L. and Schal, C. S. (1998). Field and laboratory evaluation of female sex pheromone for the detection, monitoring, and management of brownbanded cockroaches (Dictyoptera Blattellidae). Journal of Economic Entomology 91 48CM85. 

Mori, K. and Takeuchi, Y. (1994). Synthesis of (2ft,4ft)-supcl I apyrone, the sex pheromone of the brownbanded cockroach. Proceedings of the Japan Academy, Series B, Physical and Biological Sciences 70 143-145. 

In 1993 Roelofs and coworkers in the USA isolated and identified supellapyrone (115, Figure 4.73) as the female-produced sex pheromone of the brownbanded cockroach (Supella longipalpa). Meinwald proposed its stereochemistry as 27 ,47 . After preparing (27 , 47 )-115128 and (27 ,47 )-115,129 we synthesized all of the four stereoisomers of 115 as shown in Figure 4.73.130... 

Behavioral responses of the brownbanded cockroach to the four stereoisomers of supellapyrone (115) were studied carefully by Schal and coworkers.131 In field tests, males are attracted to the natural (25,45)-115, but also to the high concentrations of (25,45)-isomer. In an olfactometer in the laboratory, (25,45)-U5 was the most active isomer with just 0.3 pg being sufficient to elicit 50% male response. Males are also attracted to (25,4/ )- and (25,45)-isomers in the olfactometer, but at much higher dosage (lOOx) than the natural isomers. At any of the doses tested, (25,45 )-l 15 did not elicit behavioral responses. In this case of 5. longipalpa, the stereochemistry-pheromone activity relationships are not simple but complicated. 

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