新型含N-吡啶基吡唑结构的吡唑肟类衍生物的合成与生物活性  

Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a N-Pyridylpyrazole Moiety

作　　者：荀校 倪亚丹 李金峰 丁颖 张敏 王杨 胡兰萍[1] 周环宇 杨冰 石健[2] 高磊 戴红[1] Xun Xiao;Ni Yadan;Li Jinfeng;Ding Ying;Zhang Min;Wang Yang;Hu Lanping;Zhou Huanyu;Yang Bing;Shi Jian;Gao Lei;Dai Hong(College of Chemistry and Chemical Engineering,Nantong University,Nantong,Jiangsu 226019;Analysis and Testing Center,Nantong University,Nantong,Jiangsu 226019)

机构地区：[1]南通大学化学化工学院,江苏南通226019 [2]南通大学分析测试中心,江苏南通226019

出　　处：《有机化学》2020年第6期1638-1646,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21372135);南通市科技计划(No.MS12019060)资助项目。

摘　　要：为了探索与发现具有优良生物活性的吡唑肟类衍生物,利用活性基团拼接法,以杀螨剂唑螨酯为先导化合物,引入N-吡啶基吡唑结构单元,设计合成了20个未见文献报道的新型吡唑肟类化合物,化合物结构均经~1H NMR, ^(13)C NMR和元素分析确认.生物活性初步测试结果表明,所有目标化合物在500μg/mL浓度下对东方粘虫均呈现出100%的杀虫活性. 5个化合物在100μg/mL下对东方粘虫的杀灭活性均达100%, 2个化合物在20μg/mL下对东方粘虫仍具有40%的杀虫效果.此外,3个化合物在500μg/mL浓度下对苜蓿蚜的致死率为40%~60%.值得注意的是,5-(2-溴苯氧基)-1,3-二甲基-1H-吡唑-4-甲醛-O-{1-(3-氯吡啶-2-基)-3-[(6-氯吡啶-3-基)甲氧基]-1H-吡唑-5-甲酰基}肟(10b)和5-(4-叔丁基苯氧基)-1,3-二甲基-1H-吡唑-4-甲醛-O-{1-(3-氯吡啶-2-基)-3-[(6-氯吡啶-3-基)甲氧基]-1H-吡唑-5-甲酰基}肟(10k)对东方粘虫的杀虫活性较为突出,可作深入的结构优化与杀虫活性探究.In search of novel pyrazole oxime compounds with potent bioactivities,twenty pyrazole oxime derivatives were synthesized by introducing N-pyridylpyrazole unit into pyrazole oxime skeleton,based on the lead of fenpyroximate.The title compounds were structurually characterized by 1 H NMR,13C NMR and elemental analysis.The preliminary bioassay showed that all the title compounds had 100%insecticidal activities against Mythimna separata Walker at 500μg/mL.Five compounds displayed 100%mortality rate towards Mythimna separata Walker at 100μg/mL.Two compounds both exhibited 40%mortality rate against Mythimna separata Walker at 20μg/mL.In addition,three compounds had 40~60%insecticidal activities to Aphis medicaginis at 500μg/mL.It is worthy of noting that 5-(2-bromophenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehydeO-{1-(3-chloropyridin-2-yl)-3-[(6-chloropyridin-3-yl)methoxy]-1H-pyrazole-5-formyl}oxime(10b)and 5-(4-t-butylphenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde-O-{1-(3-chloropyridin-2-yl)-3-[(6-chloropyridin-3-yl)methoxy]-1H-pyrazole-5-formyl}oxime(10k)which have potent insecticidal activities against Mythimna separata Walker,can be utilized in insecticide research with further optimization.

关 键 词：N-吡啶基吡唑 吡唑肟 合成 生物活性 

分 类 号：O626[理学—有机化学] TQ450.1[理学—化学]