Synthesis and antibacterial activity against ralstonia solanacearum for novel hydrazone derivatives containing a pyridine moiety

Chemistry Central Journal

Volumn 6, Issue 1, 2012, Pages

  Wu, Jian ^a,b   Kang, Shenghong ^a,b   Song, Baoan ^a,b   Hu, Deyu ^a,b   He, Ming ^a,b   Jin, Linhong ^a,b   Yang, Song ^a,b  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b GUIZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84859378892     PISSN: None     EISSN: 1752153X     Source Type: Journal    
DOI: 10.1186/1752-153X-6-28     Document Type: Article

References (30)

1. Salanoubat M, Genin S, Artiguenave F, Gouzy J, Mangenot S, Arlat M, Billaultk A, Brottier P, Camus JC, Cattolico L, Chandler M, Choisne N, Claudel-Renard C, Cunnac S, Demange N, Gaspin C, Lavie M, Moisan A, Robert C, Saurin W, Schiex T, Siguier P, Thébault P, Whalen M, Wincker P, Levy M, Weissenbach J, Boucher CA. Genome sequence of the plant pathogen Ralstonia solanacearum. Nature 2002, 415:497-502. 10.1038/415497a, 11823852.
2. Álvarezi B, Biosca EG, López MM. On the life of Ralstonia solanacearum, a destructive bacterial plant pathogen. Current research, technology and education topics in applied microbiology and microbial biotechnology 2010, 1:267-279. Spain: Formatex, Bada-joz, Mendez-Vilas A.
3. Li ZF, Wu SL, Bai XF, Liu Y, Lu JF, Liu Y, Xiao BG, Lu XP, Fan LJ. Genome Sequence of the Tobacco Bacterial Wilt Pathogen Ralstonia solanacearum. J Bacteriol 2011, 193:6088-6089. 10.1128/JB.06009-11, 21994922.
4. Turner M, Jauneau A, Genin S, Tavella MJ, Vailleau F, Gentzbittel L, Jardinaud MF. Dissection of Bacterial Wilt on Medicago truncatula Revealed Two Type III Secretion System Effectors Acting on Root Infection Process and Disease Development. Plant Physiol 2009, 150:1713-1722. 10.1104/pp.109.141523, 2719136, 19493968.
5. Mukaihara T, Tamura N. Identification of novel Ralstonia solanacearum type III effector proteins through translocation analysis of hr B-regulated gene products. Microbiology 2009, 155:2235-2244. 10.1099/mic.0.027763-0, 19406897.
6. Minakata S, Hamada T, Komatsu M, Tsubo H, Kikuta H, Ohshiro Y. Synthesis and Biological Activity of 1H-Pyrrolo [2, 3-b] pyridine Derivatives: Correlation between Inhibitory Activity against the Fungus Causing Rice Blast and Ionization Potential. J Agric Food Chem 1997, 45:2345-2348.
7. Bis SJ, Canada EJ, Cooper DH, Galka CS, Kirby N, Ouimette DG, Podhorez DE, Pieczko M, Rezac R, Rieder B, Swayze JK, Hegde VB, Sampson GL. 2-Methoxyimino-2-(pyridinyl oxymethyl)phenyl acetamides with carboxylic acid derivatives on the pyridine ring as fungicides. WO 9833772, 1998[Chem Abstr 1998, 129:161497].
8. Foor SR, Walker MP. Synergistic fungicide compositions containing at least one N'- (2-pyridinyl) methyl-3-pyridinecarboxamide derivative and one or more further fungicides useful for controlling fungal plant diseases. WO 2003079787. 2003[Chem Absr 2003, 140:141086].
9. Wakita T, Kinoshita K, Yasui N, Yamada E, Kawahara N, Kodaka K. Synthesis and Structure-activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part. J Pestic Sci 2004, 29:348-355.
10. Shao XS, Xu ZP, Zhao XF, Xu XY, Tao LM, Li Z, Qian XH. Synthesis, Crystal Structure, and Insecticidal Activities of Highly Congested Hexahydroimidazo[1,2-a] pyridine Derivatives: Effect of Conformation on Activities. J Agric Food Chem 2010, 58:2690-2695. 10.1021/jf902513t, 20000414.
11. Hegde SG, Mahoney MD. Synthesis and Herbicidal Activity of 5-(Haloalkyl)-Substituted Thiazole [4,5-b] pyridine-3(2H)-acetic Acid Derivatives. J Agric Food Chem 1993, 41:2131-2134.
12. Hanagan MA, Selby TP, Sharpe PL, Sheth RB, Stevenson TM. Herbicidal Amides. WO 2005070889[Chem Abstr 2005, 143:193910].
13. Mansfield DJ, Rieck H, Greul JN, Coqueron PY, Genix P, Grosjean-Cournoyer MC, Perez J, Villier A. Preparation of heteroarylcarboxamides as fungicides. EP 1449841, 2004 [Chem Abstr 2004, 141:207064].
14. Watanabe T, Araki N. Pyridylmethyl Derivatives of 2,6-Dichloroisonicotinic Acid, Process for Production of the Same, and Disease Controllers for Agricultural and Horticultural Use. WO 2005068430, 2005[Chem Abstr 2005, 143:172764].
15. Lee SF, Gliedt M. Substituted Isoxazoles as Fungicides. WO, 2006031631[P]. 2006..
16. Mansfield DJ, Cooke T, Thomas PS, Coqueron PY, Vors JP, Briggs GG, Lachaise H, Rieck H, Desbordes P, Grosjean-Cournoyer MC. Novel 2-Pyridylethylbenzamide Derivative. WO, 2004016088[P]. 2004. [Chem Abstr 2004, 140:176744].
17. Elcken K, Goetz N, Harreus A, Eberhard A, Gisela L, Harald R. Anilide Derivatives and Their Use to Combat Botrytis. EP 0545099, 1993[Chem Abstr 1993, 119:160132].
18. Clough JM, Godfrey CRA, Hutchings MG, Aathony VM. Methyl 3-methoxy-2-phenylpropenoate derivatives useful as plant fungicides and plant growth regulators, their fungicidal compositions, and processes and intermediates for their preparation. EP 278595, 1988[Chem Abstr 1988, 109:270725].
19. Küçükgüz T, Oruç EE, Rollas S, Sahin F, Ozbek A. Synthesis, Characterization and biological activity of novel 4- thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002, 37:197-206. 10.1016/S0223-5234(01)01326-5, 11900864.
20. Rollas S, Gülerman N, Erdeniz H. Synthesis and antimicrobial activity of some new hydrazones of 4-fluorobenzoic acid hydrazide and 3-acetyl-2,5-disubstituted-1,3,4-oxadiazo- lines. Farmaco 2002, 57:171-174. 10.1016/S0014-827X(01)01192-2, 11902660.
21. Savini L, Chiasserini L, Travagli V, Pellerano C, Novellino E, Cosentino S, Pisano MB. New α-heterocyclichydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. Eur J Med Chem 2004, 39:113-122. 10.1016/j.ejmech.2003.09.012, 14987820.
22. Young D, Shaber S, Avila-adame C, Breaux N, Ruiz J, Siddall T, Webster J. Fungicidal compositions including hydrazone derivatives and copper useful for controlling growth of fungi and their preparation. WO 2010083319, 2010[Chem Abstr 2010, 153:204054].
23. Yang XD. Synthesis and biological activity of hydrazone derivatives containing pyrazole. J Chem Res 2008, 9:489-491.
24. Okuno T, Furusawa I, Matsuura K, Shishiyama J. Mode of action of ferimzone, a novel systemic fungicide for rice disease: Biological properties against Pyricularia oryzae in vitro. Phytopathology 1989, 79:827-832.
25. Hayward A. C: Biology and epidemiology of bacterial wilt caused by Pseudomonas solanacearum. Annu Rev Phytopathol 1991, 29:65-87. 10.1146/annurev.py.29.090191.000433, 18479193.
26. Lahm GP. Preparation of novel anthranilamides useful for controlling invertebrate pests. WO 2006023783, 2006[Chem Abstr 2010, 144:274265].
27. 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 2011, DOI 10.1002/ps.2329.
28. Wu J, Yang S, Song BA, Bhadury PS, Hu DY, Zeng S, Xie HP. Synthesis and insecticidal activities of novel neonicotinoid analogs bearing an amide moiety. J Heterocyclic Chem 2011, 48:901-906.
29. Kandile NG, Mohamed MI, Zaky H, Mohamed HM. Novel pyridazine derivatives: Synthesis and antimicrobial activity evaluation. Eur J Med Chem 2009, 44:1989-1996. 10.1016/j.ejmech.2008.09.047, 19013692.
30. Lee JY, Moon SS, Hwang BK. Isolation and in vitro and in vivo activity against Phytophthora capsici and Colletotrichum orbiculare of phenazine-1-carboxylic acid from Pseudomonas aeruginosa strain GC-B26. Pest Manag Sci 2003, 59:872-882. 10.1002/ps.688, 12916768.