Synthesis, Crystal Structure and Antifungal Activity of 1-(3,3 -Dimethyl-2-oxobutyl)-N-phenyl-1H-1,2,4-triazole-3-carboxamide | [Journal of Chemical Society of Pakistan • 2024]

Author(s):

1. Guang Rong Cai: Sichuan Provincial Key Laboratory for Characteristic Plant Development and Research, Sichuan University of Arts and Science, Dazhou, 163000, China.

2. Zhi Fang Li: Dazhou Vocational College of Chinese Medicine , Dazhou, 163000, China.

3. Yan Chuan Gong: Sichuan Provincial Key Laboratory for Characteristic Plant Development and Research, Sichuan University of Arts and Science, Dazhou, 163000, China.

4. Xue Dong: Sichuan Provincial Key Laboratory for Characteristic Plant Development and Research, Sichuan University of Arts and Science, Dazhou, 163000, China.

5. Wen Su Cai: Sichuan Provincial Key Laboratory for Characteristic Plant Development and Research, Sichuan University of Arts and Science, Dazhou, 163000, China.

Abstract:

Summary: 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 considerable interest in ag-ricultural chemistry due to a novel action mode, extremely high activity against phytopatho-genic fungi, low acute toxicity to mammals, and environmentally benign characteristics. The title com-pound 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 dif-fraction. Compound 5 (C15H18N4O2, Mr = 287.1500) belongs to the orthorhombic system, space group Pn21a, with a = 14.49451(11)Å, b = 20.34686(18)Å, c = 10.17021(9)Å, V =2999.38(4) Å3, Z = 8, Dc= 1.268 g/cm3, T = 293.55(14) K, µ (CuKa) = 0.710 mm-1, F (000) =1216.0, the final R=0.0448, and wR = 0.1260 with I>=2s (I). Furthermore, the results from biological assays indicated that the title com-pound exihibited a similar antifungal activity(EC 50 =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 phytopatho-genic fungi, including A. solani, S. sclerotiorum, G. saubinetii and T. cucumeris. Potentially, the result lay the foundation for the development of novel fungicides.

Page(s): 485-490

DOI: 10.52568/001556/JCSP

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 46, Issue: 5, Year: 2024

Keywords:

Antifungal activity , Crystal structure , synthesis , Amide , Triazole

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