Design,synthesis and fungicidal activity of isothiazole–thiazole derivatives |
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| Authors: | Qi-Fan Wu Bin Zhao Zhi-Jin Fan Jia-Bao Zhao Xiao-Feng Guo Dong-Yan Yang Nai-Lou Zhang Bin Yu Tatiana Kalinina Tatiana Glukhareva |
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| Affiliation: | State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071 P. R. China, Fax: +86-22-23503620, +86-23499464 ; The Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira Str., Ekaterinburg 620002 Russia, |
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| Abstract: | 3,4-Dichloroisothiazoles can induce systemic acquired resistance (SAR) to enhance plant resistance against a subsequent pathogen attack, and oxathiapiprolin exhibits excellent anti-fungal activity against oomycetes targeting at the oxysterol-binding protein. To discover novel chemicals with systemic acquired resistance and fungicidal activity, 21 novel isothiazole–thiazole derivatives were designed, synthesized and characterized according to the active compound derivatization method. Compound 6u, with EC50 values of 0.046 mg L−1 and 0.20 mg L−1 against Pseudoperonospora cubensis (Berk. et Curt.) Rostov and Phytophthora infestans in vivo, might act at the same target as oxysterol binding protein (PcORP1) of oxathiapiprolin; this result was validated by cross-resistance and molecular docking studies. The expression of the systemic acquired resistance gene pr1 was significantly up-regulated after treating with compound 6u for 24 h (43-fold) and 48 h (122-fold). These results can help the development of isothiazole–thiazole-based novel fungicides.Compound 6u exhibits ultrahigh fungicidal activity by acting at its potent target PcORP1 and induces systemic acquired resistance by activating the salicylic acid pathway. |
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