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Published on: March 27, 2014
Discovery of Ternary Aromatic (Heterocyclic) Thione/Thioether Derivatives as Phloem-Mobile Fungicidal Candidates
Jinchao Shi1, Panpan Yin1, Xuyang Zhang1
1Key Laboratory of Sustainable Crop Production in the Middle Reaches of the Yangtze River (Co-Construction by Ministry and Province), College of Agriculture, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
Abstract:
Plant fungal diseases severely threaten global crop production. To develop novel antifungal agents, we designed and synthesized a series of novel ternary aromatic (heterocyclic) thione/thioether derivatives and evaluated their antifungal activity. Most of these compounds exhibited excellent antifungal activity in vitro against Sclerotinia sclerotiorum and Rhizoctonia cerealis. In particular, compounds C3, C7, C8, and C11 exhibited remarkable antifungal activity against S. sclerotiorum, with median effective concentration (EC50) values of 0.479, 0.476, 0.240, and 0.390 μg/mL, respectively, which were more potent than that of the positive control carbendazim (0.586 μg/mL). A further in vivo test confirmed that compound C8 possessed better protective efficacy (78.3%) than carbendazim (58.8%) at 200 μg/mL. The 3D-QSAR model highlighted the dominant role of steric effects on the antifungal activity. Further studies revealed that compound C8 is phloem-mobile, rapidly translocates to roots, and strongly inhibits sclerotial formation. In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha. This study demonstrates that compound C8 has potential as an efficient phloem-mobile fungicide.
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