摘要/Abstract

利用活性亚结构拼接原理，设计制备了18个未见文献报道的新型含1，2，4-三唑环结构单元的吡唑肟醚衍生物.通过¹H NMR、¹³C NMR和元素分析等手段确认了其结构.初步的生物活性测试结果表明，部分目标化合物对粘虫、蚜虫和朱砂叶螨表现出良好的杀灭效果.在测试浓度为500 μg/mL时，目标化合物对粘虫的致死率在90%～100%，与对照药阿维菌素的杀虫效果相近，其中有4个化合物对蚜虫的致死率均为100%，与对照药吡虫啉的防效相当；1-甲基-3-甲基-5-（3，5-二氟苯氧基）-1H-吡唑-4-甲醛-O-[4-（1H-1，2，4-三唑-1-基）苯甲基]肟（8p）对朱砂叶螨的致死率为100%，与对照药唑螨酯的防效相当.当测试浓度降为100 μg/mL时，5个化合物对粘虫的致死率在90%～100%，3个化合物对蚜虫的致死率在80%～100%；化合物8p对朱砂叶螨的致死率为80%.当测试浓度降至20 μg/mL时，2个化合物对粘虫的致死率分别为75%和70%.另外，部分化合物对人肝癌（SMMC-7721）细胞显示出一定的抗肿瘤活性.
关键词: 1,2,4-三唑, 吡唑肟醚, 合成, 生物活性
Eighteen novel pyrazole oxime ethers containing 1,2,4-triazole moiety were designed and synthesized according to the method of active substructure combination. Their structures were characterized by ¹H NMR, ^{13C NMR, and elemental analyses. Preliminary bioassay showed that some target compounds showed good insecticidal activities against} Oriental armyworm, Aphis medicaginis and Tetranychus cinnabarinus. At the concentration of 500 μg/mL, target compounds had insecticidal activity against Oriental armyworm with 90%~100%, which were similar to the control of avermectin, four compounds showed 100% insecticidal activity against Aphis medicaginis, which were similar to imidacloprid. The lethal rate of 1- methyl-3-methyl-5-(3,5-difluorophenoxy)-1H-pyrazole-4-carbaldehyde-O-[4-(1H-1,2,4-triazol-1-yl)phenylmethyl]oxime (8p) against Tetranychus cinnabarinus was 100%, which was similar to that of fenpyroximate. When the concentration was reduced to 100 μg/mL, six compounds exhibited insecticidal activity against Oriental armyworm with 90%~100%, three compounds showed insecticidal activity against Aphis medicaginis with 80%~100%, and compound 8p had acaricidal activity against Tetranychus cinnabarinus with 80%. At the concentration of 20 μg/mL, the lethal rates of two compounds against Oriental armyworm were 75% and 70%, respectively. Additionally, some compounds exhibited certain anti-tumor activity against human hepatocellular carcinoma SMMC-7721 cells.
Key words: 1,2,4-triazole, pyrazole oxime ether, synthesis, bioactivity


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