Synthesis, Crystal Structure and Antifungal Activity of 1-(3,3-Dimethyl-2-oxobutyl)-N-phenyl-1H-1,2,4-triazole-3-carboxamide H-1,2,4-triazole-3-carboxamide

Fungicides play a vital role in protecting crops from fungal damage. However, fungicide resistance is one of the most important issues in modern agriculture. Hence, it is very necessary to develop new fungicides constinuously. Triazole compounds have received consider-able interest in agricultural chemistry due to a novel action mode, extremely high activity against phytopathogenic fungi, low acute toxicity to mammals, and environmentally benign characteristics. The title compound 1-(3,3-dimethyl -2-oxobutyl)-N-phenyl-1H-1,2,4-triazole-3-carboxamide 5, synthesized using methyl 1H-1,2,4 -triazole-3-carboxylate 1 as the start material, was successfully obtained via multiple synthesis route and finally characterized by 1H NMR,13C NMR, HRMS and single-crystal X-ray diffraction. Compound 5 (C15H18N4O2, Mr = 287.1500) belongs to the orthorhombic system, space group Pn21a, with a = 14.49451(11)& Aring;, b = 20.34686(18)& Aring;, c = 10.17021(9)& Aring;, V =2999.38(4) & Aring;(3), Z = 8, Dc= 1.268 g/cm(3), T = 293.55(14) K, mu (CuK alpha) = 0.710 mm(-1), F (000) =1216.0, the final R=0.0448, and wR = 0.1260 with I>=2 sigma (I). Furthermore, the results from biological assays indicated that the title compound exihibited a similar antifungal activity(EC50 =8.98 mg. L-1)compared to triadimefon (EC50=5.6 mg.L-1)against G. cingulatal. And had different degrees of weak activity against other phy-topathogenic fungi, including A. solani, S. sclerotiorum, G. saubinetii and T. cucumeris. Po-tentially, the result lay the foundation for the development of novel fungicides