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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 3: 774 - 781

DOI: https://doi.org/10.6023/cjoc201910013

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety

  • Zhu Yue ,
  • Zheng Dandan ,
  • Ni Yadan ,
  • Li Jinfeng ,
  • Zhou Huanyu ,
  • Hu Lanping ,
  • Li Ling ,
  • Ju Jianfeng ,
  • Chen Jiazheng ,
  • Li Hong ,
  • Shi Yujun ,
  • Dai Hong
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019;
    b Nantong Fengtian Chemical Industry Co. Ltd, Nantong, Jiangsu 226005

Received date: 2019-10-11

  Revised date: 2019-10-29

  Online published: 2020-04-02

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21372135, 21802075), the Natural Science Foundation of Jiangsu Province (No. BK20160413), and the Science and Technology Project Fund of Nantong City (Nos. MS12017022-4, JC2018118, MS12019060).

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Abstract

In search of novel pyrazole oximes with good biological activities, twenty pyrazole oxime compounds were prepared by introducing an oxazole unit into pyrazole oxime based on the structure of fenpyroximate. The structures of the target compounds were confirmed by 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay displayed that some target compounds had wonderful insecticidal activities against Oriental armyworm or Aphis medicaginis at the concentrations of 500 and 100 μg/mL. At the concentration of 100 μg/mL, 5-(3-fluorophenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlo-rophenyl)oxazol-2-yl)methyl)oxime (9j), 5-(4-fluorophenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlorophenyl)-oxazol-2-yl)methyl)oxime (9k), 5-(4-t-butylphenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlorophenyl)oxazol-2-yl)methyl)oxime (9r) and 5-(4-methoxyphenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlorophenyl)oxazol-2-yl)me-thyl)oxime (9s) showed 100% mortality rate against Oriental armyworm, and 5-(4-bromophenoxy)-1,3-dimethyl-1H-pyra-zole-4-formyl-O-((5-(4-fluorophenyl)oxazol-2-yl)methyl)oxime (9g) and 9s exhibited 100% insecticidal property against Aphis medicaginis. Additionally, compound 9s possessed 70% insecticidal activity against Tetranychus cinnabarinus at 500 μg/mL.

Key words： oxazole; pyrazole oxime; synthesis; biological activity

Cite this article

Zhu Yue , Zheng Dandan , Ni Yadan , Li Jinfeng , Zhou Huanyu , Hu Lanping , Li Ling , Ju Jianfeng , Chen Jiazheng , Li Hong , Shi Yujun , Dai Hong . Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety[J]. Chinese Journal of Organic Chemistry, 2020 , 40(3) : 774 -781 . DOI: 10.6023/cjoc201910013

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