Citation: Xun Xiao, Ni Yadan, Li Jinfeng, Ding Ying, Zhang Min, Wang Yang, Hu Lanping, Zhou Huanyu, Yang Bing, Shi Jian, Gao Lei, Dai Hong. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a N-Pyridylpyrazole Moiety[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1638-1646. doi: 10.6023/cjoc202002024 shu

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

Xun Xiao ^a,† ,
Ni Yadan ^a,† ,
Li Jinfeng ^a ,
Ding Ying ^a ,
Zhang Min ^a ,
Wang Yang ^a ,
Hu Lanping ^a,, ,
Zhou Huanyu ^a ,
Yang Bing ^a,, ,
Shi Jian ^b ,
Gao Lei ^a ,
Dai Hong ^a,,

a.
College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
b.
Analysis and Testing Center, Nantong University, Nantong, Jiangsu 226019

Corresponding author: Hu Lanping, hlp@ntu.edu.cn Yang Bing, yangbing111@ntu.edu.cn Dai Hong, daihong_2015@aliyun.com

^†

Received Date: 18 February 2020
Revised Date: 6 March 2020
Available Online: 11 March 2020
Fund Project: the National Natural Science Foundation of China 21372135the Science and Technology Project Fund of Nantong City MS12019060Project supported by the National Natural Science Foundation of China (No. 21372135) and the Science and Technology Project Fund of Nantong City (No. MS12019060)

Figures(3)

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.
- N-pyridylpyrazole,
- pyrazole oxime,
- synthesis,
- bioactivity
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