摘要/Abstract

为了探索与发现具有优异活性的内酯类新烟碱杀虫剂，利用骨架跃迁引入二硫环戊烯酮新药效团，设计合成了一系列结构新颖的1，2-二硫环戊烯酮类新烟碱化合物.所合成化合物结构均经核磁共振（NMR）和高分辨质谱（HRMS）等方法确证.初步生物活性测试表明，目标化合物对苜蓿蚜虫和褐飞虱都具有一定的杀虫活性，其中4-氯-5-（（（6-氯吡啶-3-基）甲基）（甲基）氨基）-3H-1，2-二硫醇-3-酮（3a），4-氯-5-（（（6-氯吡啶-3-基）甲基）（乙基）氨基）-3H-1，2-二硫醇-3-酮（3b），4-氯-5-（（（6-氯吡啶-3-基）甲基）（丙基）氨基）-3H-1，2-二硫醇-3-酮（3c）和4-氯-5-（（（6-氯吡啶-3-基）甲基）（2，2-二氟乙基）氨基）-3H-1，2-二硫醇-3-酮（3g）在100 μg/mL浓度下对苜蓿蚜虫的致死率均超过90%，3g在4 μg/mL对苜蓿蚜具有40%的致死率.此外3g在100 μg/mL浓度下对稻飞虱的致死率超过70%，可做深入的结构优化与杀虫活性探究.
关键词: 新烟碱杀虫剂, 二硫环戊烯酮, 合成, 杀虫活性
In search of novel neonicotinoid insecticides with potent bioactivities, a series of 1,2-dithiocyclopentenone derivatives were designed and synthesized by introducing dithiocyclopentenone into neonicotinoids skeleton. The structures of all compounds were confirmed by nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HRMS). Biological activities of all the title compounds were evaluated systematically. Preliminary bioassays indicated that all synthesized compounds exhibited moderate insecticidal activities. 4-Chloro-5-(((6-chloropyridin-3-yl)methyl)(methyl)amino)-3H-1,2-di-thiol-3-one (3a), 4-chloro-5-(((6-chloropyridin-3-yl)methyl)(ethyl)amino)-3H-1,2-dithiol-3-one (3b), 4-chloro-5-(((6-chloro-pyridin-3-yl)methyl)(propyl)amino)-3H-1,2-dithiol-3-one (3c) and 4-chloro-5-(((6-chloropyridin-3-yl)methyl)(2,2-difluoro-ethyl)amino)-3H-1,2-dithiol-3-one (3g) exhibited >90% mortality rate against Aphis craccivora at 100 μg/mL. Compound 3g exhibited 40% insecticidal activity to aphids at 4 μg/mL and >70% mortality rate against Nilaparvata Lugens at 100 μg/mL, and could be utilized in insecticide research with further optimization.
Key words: neonicotinoid insecticide, dithiocyclopentenone, synthesis, insecticidal activity


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