Synthesis and antifungal activities of novel nicotinamide derivatives containing 1,3,4-oxadiazole

Chemistry Central Journal

Volumn 7, Issue 1, 2013, Pages

  Wu, Jian ^a   Kang, Shenghong ^a   Luo, Lijun ^a   Shi, Qingcai ^a   Ma, Juan ^a   Yin, Juan ^a   Song, Baoan ^a   Hu, Deyu ^a   Yang, Song ^a  

^a GUIZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875834037     PISSN: None     EISSN: 1752153X     Source Type: Journal    
DOI: 10.1186/1752-153X-7-64     Document Type: Article

References (32)

1. Bai GH, Gregory S. Management and resistance in wheat and barley to fusarium head blight. Annu Rev Phytopathol 2004, 42:135-161. 10.1146/annurev.phyto.42.040803.140340, 15283663.
2. De Wolf ED, Madden LV, Lipps PE. Risk assessment models for wheat Fusarium head blight epidemics based on within-season weather data. Phytopathol 2003, 93:428-435.
3. Komori T, Ujita S, Inoue T. Preparation of N-(3-phenoxybenzyl)nicotinamide derivatives as plant fungicides. Chem Abstr 2010, 154:64642.
4. Kozlevcar B, Leban I, Turel I, Segedin P, Petric M, Pohleven F, White Andrew JP, Williams DJ, Sieler J. Complexes of copper(II) acetate with nicotinamide: preparation, characterization and fungicidal activity; crystal structures of [Cu2(O2CCH3)4(nia)] and [Cu2(O2CCH3)4(nia)2]. Polyhedron 1999, 18:755-762.
5. Komori T, Ujita S, Inoue T. Preparation of N-(4-phenoxybenzyl)pyridine-3-carboxamide derivatives as plant fungicides. Chem Abstr 2010, 154:64641.
6. Frackenpohl J, Hense A, Arnold C, Franken EM, Malsam O, Sanwald E, Goergens U. Preparation of Nicotinamides as Agrochemical Insecticides. Chem Abstr 2008, 152:287405.
7. Yokoi S, Obayashi T, Sato K, Nagai J, Kawagishi A, Mtsuo S. Pest control compositions containing N-heteroaryl-nicotinamides and insecticides, acaricides, or nematocides. Chem Abstr 2005, 142:256292.
8. Zhu YC, Yuan LP, Cao J, Shen XX, Lu DH, Ni CC, Shen Z, Chen L, Zhang YB. Synthesis and bioactivity of 2-benzylsulfanyl nicotinamide derivatives. Agrichemicals 2008, 10:287-291.
9. Gesing ERF, Mueller KH, Kysela E, Drewes MW, Dahmen P, Feucht D, Pontzen R. Preparation of N-phenylnicotinamides for use as herbicides. Chem Abstr 2001, 134:266207.
10. Jeschke P, Lindner W, Bonse G, Santel HJ, Luerssen K, Schmidt RR, Hartwig J. Herbicidal and plant-mematocidal compositions based on mercaptonicotinic acid derivatives. Chem Abstr 1993, 119:160137.
11. Chung IM, Kim JJ, Chun SC, Ahmad A. Potential herbicidals and growth regulators constituents in rice hulls of oryza sativa. J Chem 2008, 20:820-822.
12. Thomas AB, Nanda RK, Kothapalli LP, Deshpande AD. Synthesis and antimicrobial activity of N-[2-(aryl/substituted aryl)-4-oxo-1,3-thiazolidin- 3-yl]pyridine-4-carboxamide. J Kor Chem Soc 2011, 55:960-968.
13. Vijay V, Soni N, Khanna V. Synthesis and antimicrobial activity of 5-arylidine derivatives of N-(2-(4-chlorophenyl)-4-oxo-3-thiazolidinyl)isonicotinamide. Inter J Res Pharm Sci 2011, 1:34-43.
14. Wu J, Kang SH, Song BA, Hu DY, He M, Jin LH, Song Y. Synthesis and antibacterial activity against ralstonia solanacearum for novel hydrazone derivatives containing a pyridine moiety. Chem Cent J 2012, 6:28. 10.1186/1752-153X-6-28, 3359257, 22483270.
15. Dhore JW, Pethe GB, Wagh SP, Thorat GD. Synthesis, characterization and biological studies of some triazolyl isonicotinamide. Arch Appl Sci Res 2011, 3:407-414.
16. Liu CL. World Pesticides: Fungicide 2006, Beijing: Chemical Industry Press.
17. Queron PY, Grosjean-Cournoyer MC, Desbordes P, Genix P, Hartmann B, Mattes A, Kunz K, Fischer R, Gaertzen O, Ort O, Mansfield D, Villier A. N-[4-(pyridin-2-yl)butyl]-carboxamide derivatives as fungicides, their preparation, fungicidal compositions, and use for the control of phytopathogenic fungi. Chem Abstr 2008, 148:121597.
18. Wen F, Zhang H, Yu ZY, Jin H, Yang Q, Hou TP. Design, synthesis and antifungal/insecticidal evaluation of novel nicotinamide derivatives. Pestic Biochem Phy 2010, 98:248-253.
19. Xu WM, Yang S, Bhadury P, He J, He M, Gao LL, Hu DY, Song BA. Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors. Pestic Biochem Phy 2011, 101:6-15.
20. Jin LH, He J, He M, Xu WM, Yang S. The preliminary study of inhibitory mechanism of sulfone compounds xa202 and xt208 against Gibberella zeae. Afr J Micr Res 2011, 5:4889-4895.
21. Xu WM, He J, He M, Han FF, Chen XH, Pan ZX, Wang J, Tong MG. Synthesis and antifungal activity of novel sulfone derivatives containing 1,3,4-oxadiazole moieties. Molecules 2011, 16:9129-9141. 10.3390/molecules16119129, 22045041.
22. Xu WM, Han FF, He M, Hu DY, He J, Yang S, Song BA. Inhibition of tobacco bacterial wilt with sulfone derivatives containing an 1,3,4-oxadiazole moiety. J Agric Food Chem 2012, 60:1036-1041. 10.1021/jf203772d, 22208183.
23. Chen CJ, Song BA, Yang S, Xu GF, Bhadury PS, Jin LH, Hu DY, Li QZ, Liu F, Xue W, Chen Z. Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimeth -oxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives. Bioorg Med Chem 2007, 15:3981-3989. 10.1016/j.bmc.2007.04.014, 17452108.
24. Liu F, Luo XQ, Song BA, Bhadury PS, Yang S, Jin LH, Xue W, Hu DY. Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety. Bioorg Med Chem 2008, 16:3632-3640. 10.1016/j.bmc.2008.02.006, 18329885.
25. Wu J, Song BA, Hu DY, Yue M, Yang S. Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures. Pest Manag Sci 2012, 68:801-810. 10.1002/ps.2329, 22190278.
26. Wright SW, Petraitis JJ, Abelman MM, Batt DG, Bostrom LL, Corbett RL, Decicco CP, Di Meo SV, Freimark B, Giannaras JV, Green AM, Jetter JW, Nelson DJ, Orwat MJ, Pinto DJ, Pratta MA, Sherk SR, Williams JM, Magolda RL, Aner EC. Heteroaryl-fused 2-phenylisothiazolone inhibitors of cartilage breakdown. J Med Chem 1994, 37:3071-3078. 10.1021/jm00045a012, 7932530.
27. Pommer EH, Zeeh B, Goetz N, Girgensohn B. Fungicidal compositions containing pyridine carboxylic acid derivatives. Chem Abstr 1976, 84:39707.
28. Clark DA, Lahm GP, Smith BK, Barry JD, Clagg DG. Synthesis of insecticidal fluorinated anthranilic diamides. Bioorg Med Chem 2008, 16:3163-3170. 10.1016/j.bmc.2007.12.017, 18207749.
29. Rose U. 2-Aryl-substituted 4H-3,1-benzoxazin-4-ones as novel active substances for the cardiovascular system. J Heterocyclic Chem 1991, 28:2005-2012.
30. Fallon GD, Francis CL, Johansson K, Liepa AJ, Woodgate RCJ. N, N-Dialkyl-N′-Chlorosulfonylchloroformamidines in Heterocyclic Synthesis. II. Thiazolo-, Thiadiazolo-, and Oxadiazolo- Fused [1,2,4,6] Thiatriazine Dioxides. Austr J Chem 2005, 58:891-900.
31. Wu J, Wang J, Hu DY, He M, Jin LH, Song BA. Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety. Chem Cent J 2012, 6:51. 10.1186/1752-153X-6-51, 3539435, 22647315.
32. Song SQ, Zhou LG, Li D, Tang D, Li JQ, Jiang WB. Antifungal activity of five plants from Xinjiang. Nat Prod Res Dev 2004, 16:157-159.