Box-Wilson Optimization of N-(5-nitro-1H-benzimidazol-2-yl)propanamide Synthesis and Its Agrochemical Activity
Abstract
Benzimidazole derivatives are considered to be compounds with potential biological activity. It is important to synthesize their derivatives with high yields, select biologically active compounds from the synthesized compounds, and optimize the synthesis process of the selected compounds. The aim of this study was to obtain a new benzimidazole derivative, N-(5-nitro-1H-benzo[d]imidazol-2-yl)propionamide, as a promising biologically active compound, by nitration of N-(1H-benzo[d]imidazol-2-yl)propionamide and to optimize the synthesis conditions. To increase the yield of the target product, the reaction conditions were optimized using a mathematical design of experiments approach (Box-Wilson method). The main technological parameters such as optimal temperature (0°C), reaction time (5 hours), molar ratio of reagents (1:6:9), and yield (85.3%) were determined; a regression model was constructed and optimal synthesis conditions were created. The structure of the synthesized compound was characterized by 1H, 13C NMR, IR spectral data. In addition, N-(5-nitro-1H-benzo[d]imidazol-2-yl) propionamide showed significant activity against the phytopathogenic fungi Fusarium oxysporum (33.3%) and Aspergillus niger (26.6%). It showed 100% inhibition of herbicidal activity in wheat and cucumber seedlings. In this study, for the first time, optimized conditions were identified for the synthesis of N-(5-nitro-1H-benzo[d]imidazol-2-yl)propionamide in high yield. The obtained data demonstrate significant biological activity of the compound and highlight its potential as a promising lead for the development of new agrochemicals.