Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-triazole) Mannich bases containing piperazine rings.

J Agric Food Chem

State Key Laboratory of Elemento-organic Chemistry, Tianjin Key Laboratory of Pesticide Science, Elemento-Organic Chemistry Institute, Nankai University, Tianjin, China.

Published: May 2010

AI Article Synopsis

  • Researchers developed new triazole compounds (Mannich bases 6 and 7) containing pyrimidinylpiperazine rings and analyzed them using IR, NMR, and elemental analysis.
  • Fungicidal tests showed that many of these compounds exhibited strong activity, outperforming some commercial fungicides like Dimethomorph and Thiophanate-methyl.
  • Based on further analysis, five new compounds were created, and two of them (6-A1 and 7-A2) demonstrated effective fungicidal activity against a specific fungus, Pseudoperonospora cubensis, achieving 96.9% and 84.9% effectiveness, respectively.

Article Abstract

A series of trifluoromethyl-substituted 1,2,4-triazole Mannich base 6 and bis(1,2,4-triazole) Mannich base 7 containing pyrimidinylpiperazine rings via the Mannich reaction were synthesized and characterized by infrared (IR), (1)H nuclear magnetic resonance (NMR), and elemental analysis. The fungicidal tests indicated that most of compounds 6 and 7 possessed excellent fungicidal activity. Among 19 novel compounds, some showed superiority over commercial fungicides Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin. Some compounds also exhibited favorable herbicidal activity in the preliminary studies. On the basis of the comparative molecular field analysis (CoMFA), five novel compounds were subsequently synthesized, their activities were estimated fairly accurately, and compounds 6-A1 and 7-A2 displayed good fungicidal activity against Pseudoperonospora cubensis (96.9 and 84.9%) as 6h and 7c, respectively.

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http://dx.doi.org/10.1021/jf100300aDOI Listing

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