Synthesis and Biological Activities of Novel N-Pyridylpyrazole Amide Compounds Carrying Isoxazole Unit

被引:1
作者
Zheng, Dandan [1 ]
Ni, Yadan [1 ]
Qian, Cheng [1 ]
Zhang, Min [1 ]
Zhang, Zichan [1 ]
Dai, Hong [1 ]
Zhou, Beibei [1 ]
Zhang, Lifang [1 ]
机构
[1] Nantong Univ, Coll Chem & Chem Engn, Nantong 226019, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
isoxazole; N-pyridylpyrazole; synthesis; biological activity; INSECTICIDAL ACTIVITIES; ACID-DERIVATIVES; DESIGN; BIOACTIVITIES; INHIBITORS;
D O I
10.6023/cjoc202008014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of new N-pyridylpyrazole amides bearing substituted isoxazole moiety were designed and prepared based on chlorantraniliprole. These compounds were structurally determined through H-1 NMR, C-13 NMR and elemental analyses. Bioassay results displayed that all designed compounds showed a mortality rate of 100% towards Oriental armyworm at the dosage of 500 mu g/mL. At the dosage of 100 mu g/mL, the mortality rates of four compounds towards Oriental armyworm were 80%similar to 100%. Two compounds had 40%similar to 50% insecticidal activities towards Oriental armyworm at the concentration of 20 mu g/mL. At the concentration of 500 mu g/mL, five compounds demonstrated 90%similar to 100% insecticidal activities against Aphis medicaginis. Moreover, at the dosage of 500 mu g/mL, two compounds exhibited 70%similar to 80% insecticidal activities against Tetranychus cinnabarinus.
引用
收藏
页码:4249 / 4257
页数:9
相关论文
共 28 条
  • [1] Synthesis of Spiro[indole-3,5′-isoxazoles] with Anticancer Activity via a Formal [4+1]-Spirocyclization of Nitroalkenes to Indoles
    Aksenov, Alexander V.
    Aksenov, Dmitrii A.
    Arutiunov, Nikolai A.
    Aksenov, Nicolai A.
    Aleksandrova, Elena V.
    Zhao, Zhenze
    Du, Liqin
    Kornienko, Alexander
    Rubin, Michael
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) : 7123 - 7137
  • [2] Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators
    Bi, Fangchao
    Song, Di
    Zhang, Nan
    Liu, Zhiyang
    Gu, Xinjie
    Hu, Chaoyu
    Cai, Xiaokang
    Venter, Henrietta
    Ma, Shutao
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 159 : 90 - 103
  • [3] Chai B., 2009, CHIN J PESTIC, V48, P13
  • [4] Synthesis of heterocycle-modified betulinic acid derivatives as antitumor agents
    Cui, Hai-Wei
    He, Yuan
    Wang, Jinhua
    Gao, Wei
    Liu, Ting
    Qin, Min
    Wang, Xue
    Gao, Cheng
    Wang, Yan
    Liu, Ming-Yao
    Yi, Zhengfang
    Qiu, Wen-Wei
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 95 : 240 - 248
  • [5] Design, synthesis, and bioactivities of novel oxadiazole-substituted pyrazole oximes
    Dai, Hong
    Chen, Jia
    Li, Gang
    Ge, Shushan
    Shi, Yujun
    Fang, Yuan
    Ling, Yong
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (04) : 950 - 953
  • [6] Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives
    Dai, Hong
    Ye, Linyu
    Zhuang, Huiyang
    Dai, Baojiang
    Fang, Yuan
    Shi, Yujun
    [J]. MOLECULES, 2015, 20 (12): : 21870 - 21880
  • [7] Synthesis, Structure and Insecticidal Activities of Some Novel Amides Containing N-Pyridylpyrazole Moeities
    Dong, Wei-Li
    Xu, Jing-Ying
    Xiong, Li-Xia
    Li, Zheng-Ming
    [J]. MOLECULES, 2012, 17 (09) : 10414 - 10428
  • [8] Anticancer platinum(II) complexes bearing N-heterocycle rings
    Facchetti, Giorgio
    Rimoldi, Isabella
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2019, 29 (11) : 1257 - 1263
  • [9] Pyrazole-Isoindoline-1,3-dione Hybrid: A Promising Scaffold for 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
    He, Bo
    Dong, Jin
    Lin, Hong-Yan
    Wang, Meng-Yao
    Li, Xian-Kai
    Zheng, Bai-Feng
    Chen, Qiong
    Hao, Ge-Fei
    Yang, Wen-Chao
    Yang, Guang-Fu
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2019, 67 (39) : 10844 - 10852
  • [10] Design, synthesis and insecticidal activities of novel acetamido derivatives containing N-pyridylpyrazole carboxamides
    Kang, Shenghong
    Song, Baoan
    Wu, Jian
    He, Ming
    Hu, Deyu
    Jin, Linhong
    Zeng, Song
    Xue, Wei
    Yang, Song
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 67 : 14 - 18