Discovery of Novel Pyrazol-5-yl-benzamide Derivatives Containing a Thiocyanato Group as Broad-Spectrum Fungicidal Candidates

Abstract

In an effort to promote the development of new fungicides, a series of 48 novel N-(1-methyl-4-thiocyanato-1Hpyrazol-5-yl)-benzamide derivatives A1−A36 and B1−B12 were designed and synthesized by incorporating a thiocyanato group into the pyrazole ring, and their fungicidal activities were evaluated against Sclerotinia sclerotiorum, Valsa mali, Botrytis cinerea, Rhizoctonia solani, and Phytophthora capsici. In the in vitro antifungal/antioomycete assay, many of the target compounds exhibited good broadspectrum fungicidal activities. Among them, compound A36 displayed the best antifungal activity against V. mali with an EC 50 value of 0.37 mg/L, which was significantly higher than that of the positive controls fluxapyroxad (13.3 mg/L) and dimethomorph (10.3 mg/L). Meanwhile, compound B6 exhibited the best antioomycete activity against P. capsici with an EC 50 value of 0.41 mg/L, which was higher than that of azoxystrobin (29.2 mg/L) but lower than that of dimethomorph (0.13 mg/L). Notably, compound A27 displayed broad-spectrum inhibitory activities against V.

Active Discovery of the Allosteric Inhibitor Targeting Botrytis cinerea Chitinase Based on Neural Relational Inference for Food Preservation

“…However, the escalating resistance of B. cinerea poses a substantial impediment to the development of innovative fungicides. A growing body of research suggests the continuous discovery of competitive inhibitors. − Nevertheless, the selective pressure exerted on the pathogen by competitive inhibitors is anticipated to further fortify the resistance of B. cinerea . − Consequently, this sets in motion a detrimental cycle, hindering the advancement of efficacious inhibitors against B. cinerea . In contrast, allosteric inhibitors, distinguished by their unique biological conformational characteristics, emerge as a novel strategy to alleviate the development of resistance in pathogenic microorganism inhibitors .…”

Design, Synthesis, and Fungicidal Activities of Novel N-(Pyrazol-5-yl)benzamide Derivatives Containing a Diphenylamine Moiety

“…Analysis of the ultrastructure of S. sclerotiorum hyphae was conducted using TEM, following the protocol that had been previously reported …”

Fungicidal Activity of New Pyrrolo[2,3-d]thiazoles and Their Potential Action on the Tryptophan Metabolic Pathway and Wax Biosynthesis

“…The organelles of B. cinerea were observed and photographed by TEM (Hitachi, Tokyo, Japan). 39,40 ■ RESULTS AND DISCUSSION Chemistry Synthesis. The pharmacophore pyrrolo [2,3d]thiazole has been widely used in pharmaceuticals but has seldom been reported in the field of agrochemicals.…”