Tabanca Nurhayat, Cloonan Kevin R, Nesterkina Mariia, Gill Micah A, Montgomery Wayne S, Kravchenko Iryna, Kendra Paul E
USDA-ARS, Subtropical Horticulture Research Station, Miami, FL, USA.
Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) - Helmholtz Centre for Infection Research (HZI), Saarbrücken, Germany.
Pest Manag Sci. 2024 Aug 3. doi: 10.1002/ps.8324.
The Mediterranean fruit fly, Ceratitis capitata, is one of the most economically important insect pests attacking fruits and vegetables in tropical and subtropical areas of the world. Semiochemical-based pest management programs are being used to provide environmentally friendly control methods for medflies. The goals of the current study were to discover potential new, attractive, kairomones by designing, synthesizing, and testing simplified ethers of thymol and carvacrol along with their ether derivatives in short-range attraction assays and electroantennogram (EAG) assays with male C. capitata. To the best of our knowledge, this study represents the first investigation of thymol and carvacrol, and their respective ethers for attractancy to C. capitata, a major agricultural pest worldwide.
In short-range attraction bioassays, parent compounds, thymol and carvacrol, along with their propyl, butyl, benzyl, and octyl ethers captured the most male C. capitata. The attraction patterns changed over time and captures were only significant if they were greater than the positive control tea tree oil (TTO) at 90 min. In EAG assays, thymol benzyl, octyl ethers, and carvacrol benzyl ether evoked significantly greater antennal responses than their parent compounds. The EAG responses did not correlate with short-range male attraction. The aliphatic side chains of thymol and carvacrol had a small effect on the activity. Future studies will investigate the long-range attraction of the ethers that elicited large EAG responses.
This report provides new information for discovering potential kairomones through synthesis and structure-activity studies for sterile male medflies. Thymol, carvacrol, and several of their ether derivatives displayed improved longevity of attraction compared with TTO (a strong medfly attractant), with significantly higher captures than TTO observed at 90 min in laboratory bioassays. Further chemical synthesis of thymol and carvacrol ethers within this series may lead to the development of ethers that are more attractive or persistent than their parent compounds, thymol and carvacrol. © 2024 Society of Chemical Industry. This article has been contributed to by U.S. Government employees and their work is in the public domain in the USA.
地中海实蝇（Ceratitis capitata）是世界热带和亚热带地区危害水果和蔬菜的最具经济重要性的害虫之一。基于信息素的害虫管理计划正被用于为地中海实蝇提供环境友好型防治方法。本研究的目标是通过设计、合成并测试百里香酚和香芹酚的简化醚及其醚衍生物，在雄性地中海实蝇的近距离引诱试验和触角电位（EAG）试验中，发现潜在的新型、有吸引力的利它素。据我们所知，本研究是对百里香酚和香芹酚及其各自的醚对地中海实蝇（一种全球主要农业害虫）引诱性的首次研究。
在近距离引诱生物测定中，母体化合物百里香酚和香芹酚及其丙基、丁基、苄基和辛基醚捕获了最多的雄性地中海实蝇。引诱模式随时间变化，只有在90分钟时捕获量大于阳性对照茶树油（TTO）时，捕获量才具有显著性。在EAG试验中，百里香酚苄基醚、辛基醚和香芹酚苄基醚引起的触角反应明显大于它们的母体化合物。EAG反应与雄性近距离引诱不相关。百里香酚和香芹酚的脂肪族侧链对活性影响较小。未来的研究将调查引起大EAG反应的醚的远距离引诱性。
本报告通过对不育雄性地中海实蝇的合成和构效关系研究，为发现潜在的利它素提供了新信息。与TTO（一种强力的地中海实蝇引诱剂）相比，百里香酚、香芹酚及其几种醚衍生物显示出更长的引诱持续时间，在实验室生物测定中，90分钟时的捕获量显著高于TTO。该系列中百里香酚和香芹酚醚的进一步化学合成可能会导致开发出比其母体化合物百里香酚和香芹酚更具吸引力或更持久的醚。©2024化学工业协会。本文由美国政府雇员贡献，在美国其作品属于公共领域。
