新型芳基吡唑脲类化合物的合成及活性评价  

Synthesis and bioactivity evaluation of novel urea derivatives of arylpyrazoles

作　　者：盛情情 赵晨 燕颍 徐汉虹[1] 

机构地区：[1]天然农药与化学生物学教育部重点实验室/华南农业大学农学院,广东广州510642

出　　处：《华南农业大学学报》2018年第2期75-81,共7页Journal of South China Agricultural University

基　　金：广东省自然科学基金(2017A030310490;2014A030311044);广州市科技计划项目(201510010299)

摘　　要：【目的】对氟虫腈结构进行衍生改造,寻找作用于昆虫中枢神经系统的新型活性化合物,为新杀虫剂的开发提供实践经验和理论指导。【方法】运用中间体衍生化策略,以氟虫腈为原料,经2步反应合成6个新型芳基吡唑脲类化合物(2a^2f),MS、~1H NMR和^(13)C NMR分析确认化合物2a^2f的结构;采用浸叶法测定目标化合物对3龄小菜蛾幼虫的生物活性;利用膜片钳技术检测目标化合物对昆虫中枢嗅觉神经元的毒性作用方式。【结果】生测结果表明化合物2a毒力最大,12 h LC_(50)值为6.17μg·mL^(–1);电生理数据显示,化合物2b、2d、2e、2f对神经元的作用方式不同于母体化合物,呈现出神经元膜电位短暂去极化,继而膜电位逐渐超级化,并伴随自发电活动被抑制。【结论】在具有生物活性的分子上引入酰胺脲键,是改变农药对昆虫中枢神经系统毒性作用方式的潜在策略,对新农药创制具有一定指导意义。【 Objective】 To explore new active compounds targeting the central nervous system of insects via structural modification of flpronil, and provide practical experience and theoretical guidance for development of new insecticides.【 Method】 Using fipronil as the primary material, six new urea derivatives of arylpyrazoles （2a-2f） were synthesized through two step reactions according to intermediate derivatization strategy. The structures were identified by MS, !H NMR and 13C NMR. The bioactivities of the target compounds on third instar larvae of Plutella xylostella were evaluated by the leaf immersion method. The toxic effects of these target compounds on central olfactory neurons in 只 were detected by patch clamp technique. [Result】 Thepreliminary bioassay showed that compound 2a had the most toxicity with 6.17 ^ig＊mL_1 LC50 after 12 hours. Electrophysiological data showed that compounds 2b, 2d, 2e and 2f acted on the neurons in a different manner compared to the parent compounds. The membrane potential of the neurons displayed a transient depolarization, and gradually hyperpolarized accompanying with the inhibition of self-generation activities.【 Conclusion】 Introducing urea structure to bioactive molecules is a potential strategy to change the way pesticides act on the central nervous system of insects, and provides a guidance for the development of new pesticides.

关 键 词：芳基吡唑 脲类衍生物 生物活性 中枢嗅觉神经元 杀虫剂 浸叶法 膜片钳技术 

分 类 号：S482.3[农业科学—农药学]