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Design, Synthesis, and Antifungal Activities of 3-Acyl Thiotetronic Acid Derivatives: New Fatty Acid Synthase Inhibitors.

Emerging fungal phytodiseases are increasingly becoming a food security threat. Twenty-six new 3-acylthiotetronic acid derivatives were designed, synthesized, characterized, and evaluated for activities against Valsa mali, Curvularia lunata, Fusarium graminearum, and Fusarium oxysporum f. sp. lycopersici. Among the 26 compounds, 6f was the most effective against V. mali, C. lunata, F. graminearum, and F. oxysporum f. sp. lycopersici with median effective concentrations (EC50 ) of 4.1, 3.1, 3.6, and 4.1 μg/mL, respectively, while the corresponding EC50 were 0.14, 6.7, 22.4, and 4.3 μg/mL of the fungicide azoxystrobin; 4.2, 41.7, 0.42, and 0.12 μg/mL of the fungicide carbendazim; and >50, 0.19, 0.43, and BS > 50 μg/mL of the fungicide fluopyram. The inhibitory potency against V. mali fatty acid synthase agreed well with the in vitro antifungal activity. The molecular docking suggested that the 3-acylthiotetronic acid derivatives targeted the C171Q KasA complex. The findings help understanding the mode of action and design and synthesis of novel potent fungicides.

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