Abstract
Based on benzoxazole and benzothiazole scaffold as an important pharmacophore, two series of 2-(aryloxymethyl) benzoxazole and benzothiazole derivatives were synthesized and their antifungal effects against eight phytopathogenic fungi were evaluated. Compounds 5a, 5b, 5h, and 5i exhibited significant antifungal activities against most of the pathogens tested. Especially 5a, 5b, 5h, 5i, 5j, and 6h inhibited the growth of F. solani with IC50 of 4.34–17.61 μg/mL, which were stronger than that of the positive control, hymexazol (IC50 of 38.92 μg/mL). 5h was the most potent inhibitor (IC50 of 4.34 μg/mL) against F. Solani, which was about nine times more potent than hymexazol. Most of the test compounds displayed significant antifungal effects against B. cinerea (IC50 of 19.92–77.41 μg/mL), among them, 5a was the best one (IC50 of 19.92 μg/mL). The structure-activity relationships (SARs) were compared and analyzed. The result indicates that the electron-drawing ability and position of the substituents have a significant impact on biological activities. Furthermore, docking studies were carried out on the lipid transfer protein sec14p from S. cerevisiae, and preliminarily verified the antifungal activities. Taken together, these results provide 2-(phenoxymethyl)benzo[d]oxazole as an encouraging framework that could lead to the development of potent novel antifungal agents.
Highlights
Plant diseases lead to serious losses to agriculture worldwide and pose an emerging threat to the global food security [1]
In order to overcome these disadvantages, we reacted unfriendly to the environment [18,19]
Compared minutes to provide the required intermediate 4, to our delight, the yield was up to 87%
Summary
Plant diseases lead to serious losses to agriculture worldwide and pose an emerging threat to the global food security [1]. Phytopathogenic fungi, which are extremely difficult to manage in agricultural production, have caused the most serious problems, accounting for 70–80% of plant diseases. Several important fungal plant pathogens, such as the genera Colletotrichum, Botrytis, Alternaria, and Fusarium have attracted great attention due to their typical infected disease symptoms (e.g., anthracnose caused by Colletotrichum species characterized by sunken necrotic lesions usually surrounded by a red margin) [2]. Chemical treatments have shown promising prospect in the control of the disease [3]. There is an increasing need for more safe and environment friendly antifungal agents to effectively control these plant diseases
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