Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 58, Issue 9, Pages 5515-5522Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf100300a
Keywords
1,2,4-Triazole; pyrimidinylpiperazine; Mannich base; fungicidal activity; herbicidal activity
Funding
- National Basic Research Key Program of China [2003CB114406]
- Tianjin Natural Science Foundation [08JCYBJC00800, 07JCYBC00200]
- Specialized Research Fund for the Doctoral Program of Higher Education [20070055044]
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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), H-1 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, lprodione, 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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