Synthesis and fungicidal activity of novel 3,5-diarylpyrazole derivatives

Abstract

(E)-3-(2-chlorophenyl)-1-(2,4-dichlorophenyl)prop-2-en-1-one was prepared from 2-chlorobenzaldehyde followed by cyclization with hydrazine monohydrate. Eight new 3-(2,4-Di-chlorophenyl)-5-(2-chlorophenyl)-4,5- dihydro-N-acylpyrazole derivatives were synthesized and characterized by elemental analysis, IR and ¹H NMR spectroscopy. The experimental results show that the inhibition ratio of compounds 3f towards H. Oryzae and P. oryzae at 50 mg·L^-1 is 55.2% and 57.1%, respectively. The inhibition ratio of compounds 3g towards H. Oryzae, P. oryza, S. Sclerotiorum at 50 mg·L^-1 is 53.3%, 60.0%, 50.4% respectively.

References

1. Tanitame A, Oyamada Y, Ofuji K, Kyoya Y, Suzuki K, Ito H, Kawasaki M, Nagai K, Wachid M, Yamagishi J I . Design, synthesis and structure–activityrelationship studies of novel indazole analogues as DNA gyrase inhibitorswith Gram-positive antibacterial activity. Bioorg Med Chem Lett, 2004, 14: 2857–2862. doi:10.1016/j.bmcl.2004.03.044
2. Bekhita A A, Abdel-Aziem T . Design, synthesis and biologicalevaluation of some pyrazole derivatives as anti-inflammatory-antimicrobialagentsBioorg Med Chem, 2004, 12: 1935–1945
3. Lee C S, Allwine D A, Barbachyn M R, Grega K C, Dolak L A, Ford C W, Jensen R M, Seest E P, Hamel J C, Schaadt R D, Stapert D, Yagi B H, Zurenkoc G E, Genina M J, Carbon–carbon-linked(pyrazolylphenyl) oxazolidinones with antibacterial activity againstmultiple drug resistant gram-positive and fastidious gram-negativebacteria. Bioorg Med Chem, 2001, 9: 3243–3252. doi:10.1016/S0968-0896(01)00233-4
4. Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Suzuki K, Ueda T, Terauchi H, Kawasaki M, Nagai K, Wachie M, Yamagishib J I . Synthesis and antibacterialactivity of novel and potent DNA gyrase inhibitors with azole ring. Bioorg Med Chem, 2004, 12: 5515–5524. doi:10.1016/j.bmc.2004.08.010
5. Boyer F E, Vara Prasad J V N, Choy A L, Chupak L, Dermyer M R, Synthesis and SAR of novel conformationally-restrictedoxazolidinones possessing Gram-positive and fastidious Gram-negativeantibacterial activity. Part 1: Substituted pyrazoles. Bioorg Med Chem Lett, 2007, 17: 4694–4701. doi:10.1016/j.bmcl.2007.05.056
6. Tanitame A, Oyamada Y, Ofuji K, Terauchi H, Kawasaki M, Wachic M Yamagishi J, Synthesis and antibacterial activity of a novel seriesof DNA gyrase inhibitors: 5-[(E)-2-arylvinyl]pyrazoles. Bioorg Med Chem Lett, 2005, 15: 4299–4306
7. Liu X H, Pin C, Song B A, Pinaki S B, Zhu H L, wang S F, Novel 1-(5-substituted-3-substituted-4,5-dihydropyrazol-1-yl)ethanoneoxime ester derivatives:synthesis, structure and antibacterial activity. Bioorg Med Chem Lett, 2008, 16: 4075–4082
8. Liu X H, Li B, ZhuH L, Song B A . Novel 5-arylpyrazole derivatives: synthesis, structure, and antibacterial activity. Austra J Chem, 2008, 61: 223–230. doi:10.1071/CH07253
9. Liu X H, Song B A, Zhu H L, Zuo R B, Synthesis,characterization andantibacterial activity of new 3, 5-diaryl pyrazoleoxime ester derivatives. Chin J Chem, 2008, 26: 505–509. doi:10.1002/cjoc.200890095
10. Liu X H, Zhi L P, Song B A . Novel 5-aryl pyrazole oxime ester derivatives: synthesis,structure and antibacterial activity. ChemRes Chinese U, 2008, 24(4): . doi: 1005-9040(2008)-03-001-07
11. Liu X H, Wang S F, Song B A . Synthesis and bactericidal activities of novel pyrazole-1-carbothioamidederivatives. Front Chem China, 2007, 2(3): 311–314. doi:10.1007/s11458-007-0057-x
12. Liu X H, Bai L S, Wang S F . Synthesis and antibacterial activity of 5-(2-hydroxyphenyl)-3-methylaminopyrazole. Chin J Synth Chem, 2006, 14(2): 147–149 (in Chinese)
13. Liu X H, Bau L S, Wang S F . Synthesis of 5-(2- hydroxy-6-methoxylphenyl)-3-methyl-4,5-dihydropyrazole-1-carbothioamide derivatives. Chin J Synth Chem, 2006, 14(3): 272–274 (in Chinese)
14. Liu X H . Synthesis and fungicide activity of novel arylpyrazole derivatives. Chin J Synth Chem, 2007, 15(2)212–215 (in Chinese)
15. Liu X H, Zhu J, Pan C X, Song B A . Synthesisand fungicide activity of novel 5-arylpyrazole derivatives. Chin J Appl Chem, 2007, 24(10): 1162–1166 (inChinese)
16. Liu X H . Synthesis and characterize of 5-(2-hydroxy-6-methoxylphenyl)-3-methylaminopyrazole. J Anhui Univ Technol, 2006, 23(3): 275–277 (in Chinese). doi: 10.1007/s11771-006-0123-4