Department of Chemistry, Technion-Israel Institute of Technology, 32000, Technion City, Haifa, Israel.
J Chem Ecol. 1992 Feb;18(2):165-81. doi: 10.1007/BF00993751.
(Z,Z)-6,9-cis-(3S,4R)-Epoxynonadecadiene9a and (Z,Z,Z)-3,6,9-nonadecatriene have been identified as sex pheromone components in female ovipositor extracts and effluvia of the geometridBoarmia selenaria. The identification was based on relative retention times on gas chromatographic columns, GC-MS, chemical enantioselective syntheses, EAG, wind-tunnel behavioral experiments, and field tests. A single female ovipositor extract contained an average of 42 ng of (Z,Z)-6,9-cis-3,4-epoxynonadecadiene and 2 ng of (Z,Z,Z)-3,6,9-nonadecatriene.EAG, wind-tunnel behavioral studies, and field tests demonstrated that maleB. selenaria exhibit preferential attraction for the (3S,4R)-enantiomer of (Z,Z)-6,9-cis-3,4-epoxynonadecadiene. Only in effluvia and ovipositor extracts of calling females was (Z,Z)-6,9-cis- 3,4-epoxynonadecadiene detected, whereas relatively high amounts of (Z,Z,Z)-3,6,9-nonadecatriene were found in noncalling females. Wind-tunnel behavioral studies showed that (Z,Z,Z)-3,6,9-nonadecatriene did not elicit any response in the males, and when tested in combination with a mixture of monoepoxynonadecadienes, (Z,Z,Z)-3,6,9-nonadecatriene decreased the observed behavioral responses. A possible precursor role for (Z,Z,Z)-3,6,9-nonadecatriene in the pheromonal system is discussed.
(Z,Z)-6,9-顺式-(3S,4R)-环氧壬烯-9a 和 (Z,Z,Z)-3,6,9-壬三烯已被鉴定为斜纹夜蛾 Boarmia selenaria 雌虫产卵器提取物和挥发出的性信息素成分。鉴定是基于在气相色谱柱上的相对保留时间、GC-MS、化学对映选择性合成、EAG、风洞行为实验和田间测试。单个雌虫产卵器提取物平均含有 42ng 的 (Z,Z)-6,9-顺式-3,4-环氧壬烯和 2ng 的 (Z,Z,Z)-3,6,9-壬三烯。EAG、风洞行为研究和田间测试表明，雄性 B. selenaria 对 (Z,Z)-6,9-顺式-3,4-环氧壬烯的 (3S,4R)-对映体表现出优先吸引力。只有在鸣叫雌虫的挥发出和产卵器提取物中检测到 (Z,Z)-6,9-顺式-3,4-环氧壬烯，而在不鸣叫的雌虫中发现相对较高量的 (Z,Z,Z)-3,6,9-壬三烯。风洞行为研究表明，(Z,Z,Z)-3,6,9-壬三烯在雄性中没有引起任何反应，当与单环氧壬烯混合物一起测试时，(Z,Z,Z)-3,6,9-壬三烯降低了观察到的行为反应。讨论了 (Z,Z,Z)-3,6,9-壬三烯在信息素系统中可能作为前体的作用。
