Search

2-Ethyl-3,6-dimethylpyrazine (EDMP) was an alarm pheromone component isolated from the mandibular gland of the red imported fire ant, Solenopsis invicta Buren. Several pyrazine analogues have been previously found to elicit significant alarm responses in S. invicta workers. This study aimed to separate the commercially available 2-ethyl-5(6)-methylpyrazine (EMP), i.e., a mixture of 2-ethyl-6-methylpyrazine (2E6MP) and 2-ethyl-5-methylpyrazine (2E5MP), and to examine both electroantennogram (EAG) and behavioral responses of S. invicta workers to EMP and the purified isomers. HPLC separations were achieved using a polysaccharide chiral stationary phase (Chiralpak AD-H) column with both mobile phases: Cyclohexane/isopropanol, and hexane/isopropanol. A ratio of 99:1 was selected for the separation of EMP at semipreparative level. The structures of the isomers obtained through the cyclohexane/isopropanol mobile phase were confirmed by detailed analyses of 2D-HSQC- and -HMBC-NMR data. The two isomers showed differential methine C⁻H correlations evidenced by 2D-HMBC-NMR spectra. The two concentrated fractions obtained through hexane/isopropanol mobile phase were subjected to EAG test and behavioral bioassay on S. invicta workers. The two HPLC−purified isomers, 2E6MP and 2E5MP, and their mixture (1:1) at same dose elicited similar EAG and alarm responses, indicating that these two isomers are equally active. The 2D-NMR−spectroscopic characterization, and electrophysiological and alarm activities of 2E6MP and 2E5MP were reported here for the first time.

The rice stem borer, Chilo suppressalis (Walker), and the rice leaf folder, Cnaphalocrocis medinalis Guenée, are two of the most destructive lepidopteran pests in rice. Since these two pyralid insects overlap in their occurrence in rice paddy fields, farmers prefer to set their pheromone-baited traps together in the rice fields for their monitoring. However, our field observation demonstrated that no male adult of C. suppressalis was captured in traps baited with commercial sex pheromone of C. suppressalis (CCS) combined with commercial sex pheromone of C. medinalis (CCM). To confirm that the C. medinalis sex pheromone component(s) interfere with the attraction of males of the rice stem borers to their conspecific females, single components of C. medinalis sex pheromone combined with CCS in traps were tested in the laboratory and rice paddy field. The results revealed that the two alcohol components in CCM, i.e. (Z)-11-octadecen-1-ol (Z11-18: OH) and (Z)-13-octadecen-1-ol (Z13-18: OH) may cause a significant reduction in capturing C. suppressalis males caused by CCS. We recommend against using these sex pheromones together in the field and suggest that Z11-18: OH and Z13-18: OH could be potential inhibitors or antagonists of C. suppressalis sex pheromone to control the rice stem borer. [ABSTRACT FROM AUTHOR]

The first, third, and fifth instar larvae of Asian corn borer, Ostrinia furnacalis (Guenée) (Lepidoptera: Pyralidae), were treated with a lethal dose 30% of deltamethrin to determine its sublethal effects on chemical communication of the adult survivors. The capability of all males surviving deltamethrin to contact the pheromone source in a wind tunnel was significantly reduced, but those treated as the first and third instars also exhibited lower percentages of `orientation,'' `up-wind flight,'' and `approaching'' behaviors than the control males. Female moths from the deltamethrin treatment exhibited similar calling periodicity and percentages to the control moths during 10-h scotophase. However, approximately 20% of the females that survived the pyrethroid in the first and third instars contained significantly higher amounts of sex pheromone and wider coefficients of variation of the ratio of E12-tetradecenyl acetate to its Z isomer in those female survivors. There was no significant difference in the pheromone titers and coefficients of variation in control females and the females treated in the fifth instars. The present study indicates that the Asian corn borer may possess a compensation system by which the males that survived treatment at larval stage present a lower response to the pheromone, while the female survivors produce and release more pheromone. [Copyright &y& Elsevier]