Chinese Journal of Organic Chemistry >
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).
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
Zhou Qian , Zheng Dandan , Shi Yujun , Yao Wei , Qian Hongwei , Ding Ying , Wei Zhonghao , Shen Aibao , Feng Xia , Shi Jian , Dai Hong . Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Containing an Oxazole Moiety[J]. Chinese Journal of Organic Chemistry, 2018 , 38(12) : 3318 -3325 . DOI: 10.6023/cjoc201807048
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