摘要/Abstract

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，¹³C 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500 μg/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100 μg/mL下对东方粘虫的杀灭活性均达100%，2个化合物在20 μg/mL下对东方粘虫仍具有40%的杀虫效果.此外，3个化合物在500 μg/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.
关键词: N-吡啶基吡唑, 吡唑肟, 合成, 生物活性
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 ¹H NMR, ¹³C NMR and elemental analysis. The preliminary bioassay showed that all the title compounds had 100% insecticidal activities against Mythimna separata Walker at 500 μg/mL. Five compounds displayed 100% mortality rate towards Mythimna separata Walker at 100 μg/mL. Two compounds both exhibited 40% mortality rate against Mythimna separata Walker at 20 μg/mL. In addition, three compounds had 40~60% insecticidal activities to Aphis medicaginis at 500 μg/mL. It is worthy of noting that 5-(2-bromophenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde-O-{1-(3-chloropyridin-2-yl)-3-[(6-chloropyridin-3-yl)methoxy]-1H-pyrazole-5-formyl}oxime (10b) and 5-(4-t-butylphen-oxy)-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.
Key words: N-pyridylpyrazole, pyrazole oxime, synthesis, bioactivity


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