Citation: 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 shu

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

Zhu Yue ^a,† ,
Zheng Dandan ^a,† ,
Ni Yadan ^a ,
Li Jinfeng ^a ,
Zhou Huanyu ^a ,
Hu Lanping ^a,, ,
Li Ling ^a ,
Ju Jianfeng ^a,, ,
Chen Jiazheng ^a ,
Li Hong ^b ,
Shi Yujun ^a ,
Dai Hong ^a,b,,

a.
College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
b.
Nantong Fengtian Chemical Industry Co. Ltd, Nantong, Jiangsu 226005

Corresponding author: Hu Lanping, hlp@ntu.edu.cn Ju Jianfeng, ju.jf@ntu.edu.cn Dai Hong, daihong_2015@aliyun.com

^†

Received Date: 11 October 2019
Revised Date: 29 October 2019
Available Online: 13 November 2019
Fund Project: the Natural Science Foundation of Jiangsu Province No.BK20160413Project supported by the National Natural Science Foundation of China Nos. 21372135the Science and Technology Project Fund of Nantong City Nos. MS12017022-4Project supported by the National Natural Science Foundation of China 21802075Project 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)the Science and Technology Project Fund of Nantong City JC2018118the Science and Technology Project Fund of Nantong City MS12019060

Figures(3)

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.
- oxazole,
- pyrazole oxime,
- synthesis,
- biological activity
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