Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Carrying 1,3,4-Oxadiazole Unit

被引:7
作者
Wang, Yang [1 ]
Ye, Hao [1 ]
Qian, Cheng [1 ]
Yao, Wei [1 ]
Li, Hong [2 ]
Wang, Kai [1 ]
Hu, Lanping [1 ]
Li, Ling [1 ]
Wu, Jinming [1 ]
Dai, Hong [1 ]
机构
[1] Nantong Univ, Coll Chem & Chem Engn, Nantong 226019, Peoples R China
[2] Nantong Fengtian Chem Ind Co Ltd, Nantong 226005, Peoples R China
基金
中国国家自然科学基金;
关键词
1,3,4-oxadiazole; pyrazole oxime ether; synthesis; insecticidal activity; BIOLOGICAL-ACTIVITIES; NEMATOCIDAL ACTIVITY; DERIVATIVES; IDENTIFICATION; BIOACTIVITIES;
D O I
10.6023/cjoc201908006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In search of novel pyrazole oxime ether derivatives with potent bioactivities, fifteen new pyrazole oxime ethers were designed and synthesized by introducing 1,3,4-oxadiazole moiety into the C-4 position of pyrazole based on the structure of fenpyroximate. Their structures were confirmed by H-1 NMR, C-13 NMR and elemental analysis. Preliminary bioassay data showed that some title compounds possessed good insecticidal activities against Oriental armyworm or Aphis medicaginis at the concentration of 500 and 100 mu g/mL. At 100 mu g/mL, compounds 10a, 10e, 10f and 10j displayed 100% mortality rate against Oriental armyworm, and compounds 10g, 10j and 10l showed insecticidal activity against Aphis medicaginis with 100%. In addition, compound 10l had 100% mortality rate against Tetranychus cinnabarinus at 500 mu g/mL.
引用
收藏
页码:232 / 238
页数:7
相关论文
共 27 条
[1]   Synthesis and Biological Activities of Novel Pyrazole Oxime Esters Containing Substituted Pyrazolyl Group [J].
Dai, Hong ;
Huang, Meiling ;
Ge, Shushan ;
Sun, Siyu ;
Shen, Aibao ;
Cheng, Xiaoyan ;
Li, Chunjian ;
Shi, Jian .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (12) :3289-3295
[2]   Synthesis and Bioactivities of Novel Pyrazole Oxime Ethers Containing Substituted Pyrazolyl Group [J].
Dai, Hong ;
Yao, Wei ;
Sun, Siyu ;
Li, Ling ;
Shi, Lei ;
Qian, Hongwei ;
Li, Chunjian ;
Shi, Jian ;
Shi, Yujun .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (12) :3155-3162
[3]   Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Containing Substituted Tetrazolyl Group [J].
Dai, Hong ;
Yao, Wei ;
Du, Xianchao ;
Wang, Xianglong ;
Wu, Jinming ;
Chen, Qingwen ;
Li, Chunjian ;
Shi, Jian ;
Zhang, Haijun .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (12) :3267-3273
[4]   Development of novel bis-pyrazole derivatives as antitumor agents with potent apoptosis induction effects and DNA damage [J].
Dai, Hong ;
Ge, Shushan ;
Guo, Jing ;
Chen, Shi ;
Huang, Meiling ;
Yang, Jiaying ;
Sun, Siyu ;
Ling, Yong ;
Shi, Yujun .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 :1066-1076
[5]   Synthesis and Biological Activities of Novel Pyrazole Amide Derivatives Containing Substituted Isoxazole Group [J].
Dai, Hong ;
Yao, Wei ;
Ye, Linyu ;
Fang, Yuan ;
Shi, Yujun ;
Song, Chan ;
Li, Chunjian ;
Shi, Jian .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (08) :2165-2171
[6]   Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Pyrimidine Group [J].
Dai, Hong ;
Ye, Linyua ;
Li, Yang ;
Fang, Yuan ;
Shi, Yujun ;
Liang, Zhipeng ;
Shi, Jian .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (04) :1020-1026
[7]   Synthesis and bioactivities of novel pyrazole oxime derivatives containing a 1,2,3-thiadiazole moiety [J].
Dai, Hong ;
Ge, Shushan ;
Li, Gang ;
Chen, Jia ;
Shi, Yujun ;
Ye, Linyu ;
Ling, Yong .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (18) :4504-4507
[8]   Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety [J].
Dai, Hong ;
Chen, Jia ;
Li, Hong ;
Dai, Baojiang ;
He, Haibing ;
Fang, Yuan ;
Shi, Yujun .
MOLECULES, 2016, 21 (03)
[9]   Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl-5-subsituent-1H-pyrazole-4-carbaldehyde-O-(4-trifluoromethylbenzoyl)oximes [J].
Dai, Hong ;
Li, Hong ;
Jin, Zhichao ;
Liu, Wenyong ;
Xiao, Yao ;
He, Haibing ;
Wang, Qingmin ;
Shi, Yujun .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (01) :185-190
[10]   Synthesis and insecticidal activities of novel pyrazole oxime ether derivatives with different substituted pyridyl rings [J].
Fu, Cuirong ;
Pei, Jiang ;
Ning, Yu ;
Liu, Min ;
Shan, Pengcheng ;
Liu, Jun ;
Li, Yongqiang ;
Hu, Fangzhong ;
Zhu, Youquan ;
Yang, Huazheng ;
Zou, Xiaomao .
PEST MANAGEMENT SCIENCE, 2014, 70 (08) :1207-1214