Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Oxadiazole Moiety

被引:6
作者
Dai, Hong [1 ]
Ding, Ying [1 ]
Du, Xianchao [1 ]
Yao, Wei [1 ]
Chen, Qingwen [1 ]
Wang, Xianglong [1 ]
Zhong, Sulin [2 ]
Cao, Xiongfei [2 ]
Shi, Yujun [1 ]
机构
[1] Nantong Univ, Coll Chem & Chem Engn, Nantong 226019, Peoples R China
[2] United Nations Nantong Pesticide Forulat Dev Ctr, Nantong 226006, Peoples R China
关键词
oxadiazole; pyrazole oxime; synthesis; biological activity; ACTIVITY-RELATIONSHIP SAR; INSECTICIDAL ACTIVITY; DERIVATIVES; DESIGN; 1,2,4-OXADIAZOLE; BIOACTIVITIES; OXAZOLE; ANALOGS;
D O I
10.6023/cjoc201802015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In order to find novel pyrazole oximes with good bioactivities, a series of novel pyrazole oxime derivatives containing substituted oxadiazole moiety were designed and synthesized according to the method of active substructure combination. Their structures were confirmed by H-1 NMR, C-13 NMR and elemental analysis. Preliminary bioassay data indicated that some title compounds showed good insecticidal activities. At the concentration of 500 mu g/mL, 9 compounds possessed insecticidal activity against Oriental army worm with 80%similar to 100%. When the concentration was lowered to 100 mu g/mL, 3 compounds still displayed significant insecticidal activity against Oriental army worm with 70%, 60% and 70%. Additionally, one compound had 60% insecticidal activity against Aphis medicaginis at 500 mu g/mL.
引用
收藏
页码:1755 / 1762
页数:8
相关论文
共 24 条
[1]   Synthesis and bioassay evaluation of 1-(4-substitutedideneaminooxymethyl)-phenyl-3-(2,6-difluorobenzoyl)ureas [J].
Chen, Li ;
Ou, Xiao-Ming ;
Mao, Chun-Hui ;
Shang, Jian ;
Huang, Run-Qiu ;
Bi, Fu-Chun ;
Wang, Qing-Min .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (11) :3678-3683
[2]   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
[3]   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)
[4]   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
[5]   Synthesis and Biological Activities of Novel Substituted Pyrazole Oximes Containing Substituted Pyridine Group [J].
Dai, Hong ;
Zhuang, Huiyang ;
Shi, Lei ;
Li, Gang ;
Zhang, Haijun ;
Fang, Yuan ;
Dai, Baojiang .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (11) :2399-2404
[6]   Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives [J].
Dai, Hong ;
Ye, Linyu ;
Zhuang, Huiyang ;
Dai, Baojiang ;
Fang, Yuan ;
Shi, Yujun .
MOLECULES, 2015, 20 (12) :21870-21880
[7]   The thiazoylmethoxy modification on pyrazole oximes: Synthesis and insecticidal biological evaluation beyond acaricidal activity [J].
Dai, Hong ;
Xiao, Yan-Shuang ;
Li, Zhong ;
Xu, Xiao-Yong ;
Qian, Xu-Hong .
CHINESE CHEMICAL LETTERS, 2014, 25 (07) :1014-1016
[8]   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
[9]  
HAMAGUCHI H, 1995, J PESTIC SCI, V20, P173
[10]   The toxic and anti-feedant activity of 2H-pyridazin-3-one-substituted 1,3,4-oxadiazoles against the armyworm Pseudaletia separata (Walker) and other insects and mites [J].
Huang, QC ;
Qian, XH ;
Song, GH ;
Cao, S .
PEST MANAGEMENT SCIENCE, 2003, 59 (08) :933-939