Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1638-1646.DOI: 10.6023/cjoc202002024 Previous Articles     Next Articles


荀校a, 倪亚丹a, 李金峰a, 丁颖a, 张敏a, 王杨a, 胡兰萍a, 周环宇a, 杨冰a, 石健b, 高磊a, 戴红a   

  1. a 南通大学化学化工学院 江苏南通 226019;
    b 南通大学分析测试中心 江苏南通 226019
  • 收稿日期:2020-02-18 修回日期:2020-03-06 发布日期:2020-03-11
  • 通讯作者: 胡兰萍, 杨冰, 戴红;;
  • 基金资助:

Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a N-Pyridylpyrazole Moiety

Xun Xiaoa, Ni Yadana, Li Jinfenga, Ding Yinga, Zhang Mina, Wang Yanga, Hu Lanpinga, Zhou Huanyua, Yang Binga, Shi Jianb, Gao Leia, Dai Honga   

  1. a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019;
    b Analysis and Testing Center, Nantong University, Nantong, Jiangsu 226019
  • Received:2020-02-18 Revised:2020-03-06 Published:2020-03-11
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21372135) and the Science and Technology Project Fund of Nantong City (No. MS12019060).

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