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.
作者
荀校
倪亚丹
李金峰
丁颖
张敏
王杨
胡兰萍
周环宇
杨冰
石健
高磊
戴红
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)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
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。
