Molnár Béla, Kárpáti Zsolt, Szocs Gábor, Hall David R
Plant Protection Institute, Hungarian Academy of Sciences, H-1525, Budapest, P.O. Box 102, Hungary.
J Chem Ecol. 2009 Jun;35(6):706-14. doi: 10.1007/s10886-009-9641-5. Epub 2009 May 21.
The honey locust gall midge, Dasineura gleditchiae Osten Sacken 1866 (Diptera: Cecidomyiidae) is the main pest of ornamental varieties of the honey locust tree, Gleditsia triacanthos L., in North America, and is now becoming a pest of concern in Europe. Female midges were observed to emerge in the early morning with their ovipositor extended until they mated. Volatiles were collected from virgin females in a closed-loop stripping apparatus and analyzed by gas chromatography (GC) coupled to electroantennographic (EAG) recording from the antenna of a male midge. A single EAG response was observed, which was assumed to be to the major component of the female sex pheromone. This was identified as (Z)-2-acetoxy-8-heptadecene by comparison of its mass spectrum and GC retention times on different columns with those of synthetic standards and by micro-analytical reactions. This compound was synthesized, and the individual enantiomers were produced by kinetic resolution with lipase from Candida antarctica. Analysis of the naturally-produced compound on a cyclodextrin GC column indicated it was the (R)-enantiomer. In EAG dose-response measurements, the (R)-enantiomer alone or in the racemic mixture evoked significant responses from the antennae of male D. gleditchiae, whereas the (S)-enantiomer did not. In field trapping tests, the (R)-enantiomer attracted male D. gleditchiae. The racemic compound was equally attractive, but the (S)-enantiomer was not attractive. Both the pure (R)-enantiomer or racemic (Z)-2-acetoxy-8-heptadecene, applied to red rubber septa in a dose range of 3-30 microg, constitute a strongly attractive bait in sticky traps for monitoring the flight of D. gleditchiae.
刺槐瘿蚊（Dasineura gleditchiae Osten Sacken，1866年）（双翅目：瘿蚊科）是北美刺槐（Gleditsia triacanthos L.）观赏品种的主要害虫，目前在欧洲也逐渐成为令人关注的害虫。观察到雌蚊在清晨出现，产卵器伸出，直至交配。在闭环脱附装置中收集未交配雌蚊的挥发物，并通过气相色谱（GC）结合雄性瘿蚊触角的电触角图（EAG）记录进行分析。观察到单一的EAG反应，假定其针对雌蚊性信息素的主要成分。通过将其质谱和在不同柱上的GC保留时间与合成标准品进行比较，并通过微量分析反应，将其鉴定为（Z）-2-乙酰氧基-8-十七碳烯。合成了该化合物，并通过南极假丝酵母脂肪酶的动力学拆分制备了各个对映体。在环糊精GC柱上对天然产生的化合物进行分析表明它是（R）-对映体。在EAG剂量反应测量中，单独的（R）-对映体或外消旋混合物均可引起雄性刺槐瘿蚊触角的显著反应，而（S）-对映体则无此反应。在田间诱捕试验中，（R）-对映体吸引了雄性刺槐瘿蚊。外消旋化合物同样具有吸引力，但（S）-对映体没有吸引力。以3-30微克的剂量范围施用于红色橡胶隔片的纯（R）-对映体或外消旋（Z）-2-乙酰氧基-8-十七碳烯，在粘性诱捕器中构成用于监测刺槐瘿蚊飞行的强吸引力诱饵。
