新型含噁唑环结构的吡唑肟醚类化合物的合成与杀虫活性研究
收稿日期: 2018-07-26
修回日期: 2018-08-29
网络出版日期: 2018-09-05
基金资助
国家自然科学基金（No.21372135）、江苏省"六大人才高峰"（No.2013-SWYY-013）、南通市科技计划（No.MS22015020）和江苏省大学生创新训练计划（No.201810304016Z）资助项目
Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Containing an Oxazole Moiety
Received date: 2018-07-26
Revised date: 2018-08-29
Online published: 2018-09-05
Supported by
Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013), and the Science and Technology Project Fund of Nantong City (No. MS22015020) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201810304016Z).
为了从吡唑肟醚类化合物中寻找新的活性物质，利用活性亚结构拼接原理，设计并合成了一系列新型含噁唑环结构的吡唑肟醚类衍生物共计15个.通过1H NMR、13C NMR和元素分析等手段确证了目标化合物的结构.初步的生物活性测试结果表明，大多数目标化合物对朱砂叶螨、蚜虫和粘虫显示出良好的防治效果.在测试浓度为500 μg/mL时，10个化合物对朱砂叶螨均具有80%以上杀死率，其中4个化合物对朱砂叶螨表现出与对照药唑螨酯相当的防治效果，9个化合物对蚜虫的杀死率均达100%，与对照药吡虫啉的杀虫效果相近，14个化合对粘虫的杀死率均为100%，与对照药啶虫丙醚的防效相当.当测试浓度为100 μg/mL时，3个化合物对朱砂叶螨的杀死率均为60%，2个化合物对蚜虫的杀死率分别为90%和100%.当测试浓度降至20 μg/mL时，1，3-二甲基-5-（4-甲基苯氧基）-1H-吡唑-4-甲醛-O-[4-（噁唑-5-基）苯甲基]肟（7i）对蚜虫仍呈现出一定的杀虫效果，其杀死率为60%.
周钱 , 郑丹丹 , 石玉军 , 姚炜 , 钱宏炜 , 丁颖 , 魏中昊 , 沈爱宝 , 冯霞 , 石健 , 戴红 . 新型含噁唑环结构的吡唑肟醚类化合物的合成与杀虫活性研究[J]. 有机化学, 2018 , 38(12) : 3318 -3325 . DOI: 10.6023/cjoc201807048
In order to find new pyrazole oxime ether derivatives with potent bioactivities, fifteen novel pyrazole oxime ethers containing an oxazole moiety were designed and prepared according to the method of active substructure combination. Their structures were confirmed through 1H NMR, 13C NMR, and elemental analysis. Preliminary bioassay showed that most of the title compounds displayed wonderful insecticidal activities against Oriental armyworm, Aphis medicaginis and Tetranychus cinnabarinus. At the concentration of 500 μg/mL, ten compounds exhibited acaricidal activity against Tetranychus cinnabarinus with over 80%, especially four compounds indicated comparable insecticidal activity against Tetranychus cinnabarinus to that of the control of fenpyroximate, the lethal rates of nine compounds against Aphis medicaginis were all 100%, which were near to that of imidacloprid, and the lethal rates of fourteen compounds against Oriental armyworm were all 100%, which were similar to that of pyridalyl. At the concentration of 100 μg/mL, the lethal rates of three compounds against Tetranychus cinnabarinus were all 60%, and the lethal rates of two compounds against Aphis medicaginis were 90% and 100%. When the concentration was reduced to 20 μg/mL, compound 1,3-dimethyl-5-(4-methylphenoxy)-1H-pyrazole-4-carbaldehyde-O-[4-(oxazol-5-yl)phenylmethyl]oxime (7i) still had insecticidal activity against Aphis medicaginis with 60%.
Key words： oxazole; pyrazole oxime ether; synthesis; insecticidal activity
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