03125naa a2200265 a 450000100080000000500110000800800410001910000210006024501450008126000090022652023330023565300220256865300290259065300180261965300170263770000190265470000260267370000200269970000140271970000150273370000190274870000190276770000150278677300580280119511872023-03-07       2012    bl uuuu     u00u1 u    #d1 aMORAES, M. C. B.  aSex Pheromone Communication in Two Sympatric Neotropical Stink Bug Species Chinavia ubica and Chinavia impicticornis.h[electronic resource]  c2012  aChinavia and Nezara spp. stink bugs (Heteroptera: Pentatomidae) include over100 species, with highest diversity in Afrotropical and Neotropical regions. Species thus far studied in these genera utilize trans-(Z)-(4S)-bisabolene epoxide (BE) and cis-(Z)-(4S)-BE as major sex pheromone components, with species specificity ensured by different ratios of the two compounds. Gas chromatography (GC) and coupled GC-mass spectrometry (GC-MS) analyses of a volatiles fromC. ubicamales revealed the presence of two BE isomers in approximately a 90:10 ratio, which were shown by microprobe 1 HNMRtobe cis-(Z)-BE and trans-(Z)-BE isomers, respectively. Analyses of volatiles from C. impicticornis males suggested the presence of a single isomer, trans(Z)-BE, in high purity (&gt90%). The absolute configurations of the isomers produced by C. ubica and C. impicticornis were determined using chiral GC analysis (?-DEX column). Oxidative microchemistry of synthetic standards of cis-(Z)-(4S)-BE and trans-(Z)-(4R)-BE, and volatiles from male of C.ubica, revealed the absolute stereochemistry of the cis-(Z)-BE to be (1R,2S,4S)[cis-(Z)-(4S) for short]. Similarly, analyses of trans-(Z)-(4S)-BE and cis-(Z)-(4R)-BE standards, and volatiles from males of C. ubica and C. impicticornis,revealed the absolute stereochemistry of the trans-(Z)-BE to be(1S,2R,4S)[trans-(Z)-(4 S) for short]. Olfactometer bioassays with synthetic BEs confirmed attraction of female C. ubica and C. impicticornis to conspecific synthetic pheromone, but not to heterospecific synthetic pheromone. Chinavia impicticornis appeared not to discriminate behaviorally between the conspecific pheromone and its enantiomer. Coupled GC-electroantennography with antennae from females suggested that C. ubica and C. impicticornis possess olfactory receptors for both cis-(Z)-(4S)-BE and trans-(Z)-(4S)-BE. The results in this study confirm that C. ubica and C. impicticornis,as forother Chinavia and Nezara spp., utilize cis-(Z)-(4S)-BE and trans-(Z)-(4S)-BE as sex pheromone components, with different ratios guaranteeing species specificity. Furthermore, the results suggest that the absolute stereochemistry of BEs may be less important for conspecific recognition than the relative stereochemistry between the epoxide group and the alkyl substituent on the bisabolene ring.  aFeromônio sexual  aHeteroptera Pentatomidae  aPraga de soja  aSoybean pest1 aLAUMANN, R. A.1 aOLIVEIRA, M. W. M. de1 aWOODCOCK, C. M.1 aMAYON, P.1 aHOOPER, A.1 aPICKETT, J. A.1 aBIRKETT, M. A.1 aBORGES, M.  tJournal of Chemical Ecologygv. 38, p. 836-845, 2012.