Synthesis, antifungal and insecticidal activity of novel [1,2,4]triazolo[4,3-a]pyridine derivatives containing a sulfide substructure

被引:10
作者
Xu, Fang-Zhou [1 ]
Shao, Jia-Hui [2 ]
Zhu, Yun-Ying [3 ]
Liu, Li-Wei [1 ]
Zhao, Yong-Hui [4 ]
Shan, Wei-Li [4 ]
Wang, Yan-Yan [1 ]
Wu, Jian [1 ]
Yang, Song [1 ]
Xue, Wei [1 ]
机构
[1] Guizhou Univ, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn, Minist Educ,Res & Dev Ctr Fine Chem, Guiyang 550025, Peoples R China
[2] Zaozhuang Univ, Coll Life Sci, Zaozhuang 277100, Peoples R China
[3] Guizhou Inst Technol, Sch Chem Engn, Guiyang 550001, Peoples R China
[4] Minist Agr, Inst Control Agrochem, Beijing 100125, Peoples R China
基金
中国国家自然科学基金;
关键词
1,2,4]Triazolo[4,3-a]pyridine; Sulfide; Synthesis; Antifungal activity; Insecticidal activity; MICROWAVE-ASSISTED SYNTHESIS; ONE-POT SYNTHESIS; CRYSTAL-STRUCTURE; ANTHRANILIC DIAMIDES; DESIGN; INHIBITORS; MOIETY; DFT; SAR;
D O I
10.1007/s11696-016-0006-6
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of [1,2,4]triazolo[4,3-a]pyridine derivatives bearing a sulfide substructure was designed, synthesized and characterized via H-1 center dot NMR, C-13 center dot NMR, IR and elemental analyses. Bioassay Results indicated some of the derivatives displayed good fungicidal activity on Rhizoctonia cerealis, moderated insecticidal activity against Plutella xylostella and good insecticidal activity on Helicoverpa armigera. The inhibitory effects of compounds 4g and 4u against Rhizotonia cerealis were 70.9% at 50 mu g mL(-1); the IC50 values of compounds 4d and 4s against Plutella xylostella were 43.87 and 50.75 mu g mL(-1), respectively. And the IC50 values of compounds 4d, 4q, and 4s on Helicoverpa armigera were 58.3, 77.14 and 65.31 mu g mL(-1), respectively, which were better than that of commercial chlorpyrifos (103.77 mu g mL(-1)).
引用
收藏
页码:729 / 739
页数:11
相关论文
共 30 条
[1]   SAR studies around a series of triazolopyridines as potent and selective PI3Kγ inhibitors [J].
Bell, Kathryn ;
Sunose, Mihiro ;
Ellard, Katie ;
Cansfield, Andrew ;
Taylor, Jess ;
Miller, Warren ;
Ramsden, Nigel ;
Bergamini, Giovanna ;
Neubauer, Gitte .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (16) :5257-5263
[2]   Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold [J].
Chen, Yin-Bo ;
Li, Ji-Ling ;
Shao, Xu-Sheng ;
Xu, Xiao-Yong ;
Li, Zhong .
CHINESE CHEMICAL LETTERS, 2013, 24 (08) :673-676
[3]   A Novel Triazolopyridine-Based Spleen Tyrosine Kinase Inhibitor That Arrests Joint Inflammation [J].
Ferguson, Gregory D. ;
Delgado, Mercedes ;
Plantevin-Krenitsky, Veronique ;
Jensen-Pergakes, Kristen ;
Bates, R. J. ;
Torres, Sanaa ;
Celeridad, Maria ;
Brown, Heather ;
Burnett, Kelven ;
Nadolny, Lisa ;
Tehrani, Lida ;
Packard, Garrick ;
Pagarigan, Barbra ;
Haelewyn, Jason ;
Nguyen, Trish ;
Xu, Li ;
Tang, Yang ;
Hickman, Matthew ;
Baculi, Frans ;
Pierce, Steven ;
Miyazawa, Keiji ;
Jackson, Pilgrim ;
Chamberlain, Philip ;
LeBrun, Laurie ;
Xie, Weilin ;
Bennett, Brydon ;
Blease, Kate .
PLOS ONE, 2016, 11 (01)
[4]  
Ghorab MM, 1996, PESTIC SCI, V48, P31, DOI 10.1002/(SICI)1096-9063(199609)48:1<31::AID-PS430>3.0.CO
[5]  
2-#
[6]  
Guan L.P., 2012, ARZNEIMITTELFORSCH, V62, P1, DOI DOI 10.1055/S-0032-1314821
[7]   Design, Synthesis, and Biological Screening of Novel Anthranilic Diamides [J].
Hua, Xuewen ;
Mao, Wutao ;
Fan, Zhijin ;
Ji, Xiaotian ;
Li, Fengyun ;
Zong, Guangning ;
Song, Haibin ;
Tatiana, Kalinina ;
Morzherin, Yury Yu. ;
Belskaya, Nataliya P. ;
Bakulev, Vasiliy A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (03) :865-875
[8]   Novel Anthranilic Diamide Insecticides: Design, Synthesis, and Insecticidal Evaluation [J].
Hua, Xuewen ;
Mao, Wutao ;
Fan, Zhijin ;
Ji, Xiaotian ;
Li, Fengyun ;
Zong, Guangning ;
Song, Haibin ;
Li, Juanjuan ;
Zhou, Like ;
Zhou, Lifeng ;
Liang, Xiaowen ;
Wang, Genhao ;
Chen, Xiaoyan .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2014, 67 (10) :1491-1503
[9]   Continued exploration of the triazolopyridine scaffold as a platform for p38 MAP kinase inhibition [J].
Jerome, Kevin D. ;
Rucker, Paul V. ;
Xing, Li ;
Shieh, Huey S. ;
Baldus, John E. ;
Selness, Shaun R. ;
Letavic, Michael A. ;
Braganza, John F. ;
McClure, Kim F. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (02) :469-473
[10]   Synthesis, crystal structure, herbicidal activities and 3D-QSAR study of some novel 1,2,4-triazolo[4,3-a]pyridine derivatives [J].
Liu, Xing-Hai ;
Xu, Xiao-Yan ;
Tan, Cheng-Xia ;
Weng, Jian-Quan ;
Xin, Jia-Hua ;
Chen, Jie .
PEST MANAGEMENT SCIENCE, 2015, 71 (02) :292-301