Synthesis and Antifungal Activity of Substituted 2‐Aryl Benzimidazoles Derivatives

Abstract

Benzimidazole fungicides were among the early systemic fungicides developed and used for controlling a wide variety of plant diseases. During the course of our screening process for active compounds, two 2‐aryl benzimidazoles derivatives bearing sulfoxide group (6b and 6c) have been demonstrated to exhibit good inhibition activity against high‐resistant isolate of Botrytis cinerea compared with carbendazim, and the inhibition rates are up to 46.67% and 51.11% at the concentration of 10 μg/mL, which might be considered as the active framework for the discovery of novel fungicide to high‐resistant isolate of B. cinerea.

Design, synthesis, biological assessment and in silico ADME prediction of new 2-(4-(methylsulfonyl) phenyl) benzimidazoles as selective cyclooxygenase-2 inhibitors

“…The product was extracted with EtOAc, and anhydrous Na 2 SO 4 was used to dry the organic layer to obtain the crude product, which was recrystallized from ethyl alcohol to obtain the targeted compounds 8a–c. 48 …”

“…Oxone (3.2 mmol, 1 g) dissolved in water then added and stirred under reux at 60-70 C. Oxidation was monitored by TLC then the reaction mixture was poured into cold water (50 ml). The product was extracted with EtOAc, and anhydrous Na 2 SO 4 was used to dry the organic layer to obtain the crude product, which was recrystallized from ethyl alcohol to obtain the targeted compounds 8a-c. 48 4.1. and anhydrous K 2 CO 3 (10 mmol, 1 g) was stirred cold for 2 h then ethyl chloroacetate (1.83 mmol, 0.256 ml) was added portion-wise. The reaction mixture was reuxed for 10 h then poured into ice and the product was obtained upon ltration.…”

SAR Analysis of Heterocyclic Compounds with Monocyclic and Bicyclic Structures as Antifungal Agents

“…Huang et al [104] have synthesized 2-aryl benzimidazoles derivatives (49 a-c and 50 b-c) and evaluated the antifungal activity against benzimidazoles-sensitive and high-resistant isolates of B. cinerea (Figure 36). Compounds 50 b and 50 c with a sulfoxide group showed moderate inhibitory activity (inhibitory rates: 41.33 %-53.33 %), while compounds 49 a-c containing a methylthio group showed no inhibitory activity at a concentration of 10 μg/mL, suggesting that the sulfoxide group played an important role in the antifungal activity.…”

“…Huang et al [104] . have synthesized 2‐aryl benzimidazoles derivatives ( 49 a – c and 50 b – c ) and evaluated the antifungal activity against benzimidazoles‐sensitive and high‐resistant isolates of B. cinerea (Figure 36).…”

Structure and Microbiological Activity of 1H-benzo[d]imidazole Derivatives

“…Our interests include benzimidazoles, which exhibit multidirectional biological activity [ 11 ]. It was found, among others, that antibacterial and antifungal agents can be found in this group [ 12 , 13 ]. We focused in particular on benzimidazoles substituted at the C-2 position with cyclohexylethyl, cyclohexylpropyl and phenylpropyl moieties ( Figure 1 ).…”