Insecticides used to control fruit fly pests have been implicated in negative effects on natural enemies, human health and the environment. As potential ‘softer’ insecticides, natural compounds such as essential oils and their constituents have received increased attention as insecticide candidates. Queensland fruit fly (Q-fly), Bactrocera tryoni (Froggatt), is the most economically damaging fruit fly species in Australia. Cuelure and melolure are plant-based attractants of males in Q-fly and many other dacine fruit flies and are structurally similar to benzyl acetone. We hypothesized that fluorination of benzyl acetone would introduce toxicity that could be exploited for insecticidal applications. Toxicity to Q-fly of nine fluorinated analogs of benzyl acetone as well as the known attractants cuelure and melolure was investigated. LC₅₀ and LC₉₀ values of the compounds were obtained using a surface-film assay method. Fluorination at the meta and/or para-position of benzene ring was found to increase toxicity to both Q-fly sexes. We further examined toxicity and short-range attraction to Q-fly using traps in outdoor cages. The nine fluorinated analogs of benzyl acetone were all highly toxic to male Q-flies, whereas cuelure and melolure were not. Some analogs were attractive to male Q-flies. None of the nine analogs, cuelure or melolure had an inhibitory effect on the proliferation of BEAS-2B human bronchial epithelial cells, suggesting very low or negligible mammalian toxicity. Fluorinated analogs of benzyl acetone have potential as new toxicants for Q-fly, and likely other insects, and some may also have attractive properties for cuelure-responding fruit flies.

中文翻译：

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环氟苄丙酮类似物在昆士兰果蝇（一种较柔软的杀虫剂）中的杀虫活性

用于控制果蝇害虫的杀虫剂已对天敌，人类健康和环境产生负面影响。作为潜在的“柔软”杀虫剂，天然化合物（例如精油）及其成分作为杀虫剂候选物受到越来越多的关注。昆士兰果蝇（Q-fly），Bactrocera tryoni（Froggatt），是澳大利亚最具经济破坏力的果蝇种类。Cuelure和melolure是Q-fly和许多其他dacine实蝇中雄性的植物性引诱剂，在结构上与苄基丙酮相似。我们假设苄基丙酮的氟化会引入可用于杀虫应用的毒性。研究了九种苄基丙酮的氟化类似物以及已知的引诱剂cuelure和melolure对Q-fly的毒性。使用表面膜测定法获得化合物的LC ₅₀和LC ₉₀值。间和/或对位氟化发现苯环的-位增加了对两个Q-蝇性别的毒性。我们使用室外网箱中的诱捕器进一步检查了对Q-fly的毒性和短程吸引。九种苄基丙酮的氟化类似物对雄性Q蝇均具有高毒性，而cuelure和melolure则无毒。一些类似物对雄性Q蝇具有吸引力。九种类似物cuelure或melolure均未对BEAS-2B人支气管上皮细胞的增殖产生抑制作用，表明哺乳动物毒性非常低或可忽略不计。苄基丙酮的氟化类似物具有潜在的Q-fly和其他昆虫的新毒剂的作用，并且对于响应cuelure的果蝇也具有吸引人的特性。