The Asian eulophid wasp Tetrastichus planipennisi is being released in North America as a biocontrol agent for the emerald ash borer (Agrilus planipennis), a very destructive invasive buprestid beetle that is devastating ash trees (Fraxinus spp.). We identified, synthesized, and tested a female-produced sex pheromone for the wasp. The key component eliciting behavioral responses from male wasps in flight tunnel bioassays was identified as (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene. Female specificity was demonstrated by gas chromatographic (GC) comparison of male and female volatile emissions and whole body extracts. The identification was aided by coupled gas chromatography/mass spectrometry analysis, microchemical reactions, NMR, GC analyses with a chiral stationary phase column, and matching GC retention times and mass spectra with those of synthetic standards. The tetramethyl-triene hydrocarbon was synthesized as a mixture of two enantiomeric pairs of diastereomers, and as the pure insect-produced stereoisomer. In flight-tunnel bioassays, males responded to both the natural pheromone and the chiral synthetic material by upwind flight and landing on the source. In contrast, the mixture of four stereoisomers was not attractive, indicating that one or more of the “unnatural” stereoisomers antagonized attraction. Field trials, using yellow pan traps baited with natural pheromone, captured significantly more male wasps than control traps over a four week trial. The identified pheromone could increase the efficiency and specificity of the current detection methods for Tetrastichus planipennisi and aid in the determination of parasitoid establishment at release sites.

中文翻译：

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女性生产的四齿拟雌性性信息素，是一种为防治外来翡翠灰钻erAgrilus planipennis而进行生物防治的拟寄生物。

亚洲灵长类黄蜂Tetrastichus planipennisi在北美被释放出来，作为一种对绿灰bore（Agrilus planipennis）的生物防治剂，Agrilus planipennis是一种破坏性极强的入侵性甲壳虫，具有毁灭性，它毁坏了灰树（Fraxinus spp。）。我们鉴定，合成并测试了黄蜂的雌性性信息素。在飞行隧道生物测定中引起雄性黄蜂行为反应的关键成分被确定为（6 S，10 S）-（2 E，4 E，8 E）-4,6,8,10-四甲基三苯甲基-2,4,8-三烯。通过气相色谱（GC）比较男性和女性挥发物排放物和全身提取物，证明了女性的特异性。结合气相色谱/质谱分析，微化学反应，NMR，使用手性固定相色谱柱进行GC分析以及将GC保留时间和质谱与合成标准品相匹配，可以帮助进行鉴定。合成了四甲基三烯碳氢化合物，是两个非对映异构体的对映异构体对的混合物，并且是由昆虫产生的纯立体异构体。在飞行隧道生物测定中，雄性通过逆风飞行并着陆在源头上，对天然信息素和手性合成材料做出了反应。相反，四种立体异构体的混合物没有吸引力，表明一种或多种“非天然”立体异构体拮抗了吸引力。在为期四周的试验中，使用使用天然信息素诱饵的黄色泛陷阱进行的田间试验比对照陷阱捕获的雄性黄蜂数量要多得多。鉴定出的信息素可以提高当前检测方法的效率和特异性Tetrastichus planipennisi并帮助确定释放部位的寄生物。