Discovery of Methyl (5Z)-[2-(2,4,5-Trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetates as Antifungal Agents against Potato Diseases
Konstantin L. Obydennova✉, Л. А. Хамидуллинаa b, Alexey Galushchinskiya, Svetlana Shatunovaa, Marya F. Kosterinaa, Tatiana A. Kalininaa, Zhijin Fanc d, Tatiana Vladimirovna Glukharevaa, Yu. Yu. Morzherina
- aUral Federal University, 19 Mira Street, Ekaterinburg 620002, Russia
- bPostovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences (UB RAS), 22 Sofia Kovalevskaya Street, Ekaterinburg 620990, Russia
- cState Key Laboratory of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People’s Republic of China
- dState Key Laboratory of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China
- ✉Corresponding author
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Abstract
Synthesis, isomerism, and fungicidal activity against potato diseases of new (5 Z )-[2-(2,4,5-trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetate derivatives with 1,3-thiazolidine-4-one and pyrrolidine-2,3,5-trione moieties linked by an exocyclic C═C bond were described. Their structures were clearly confirmed by spectroscopic and spectrometric data (Fourier transform infrared spectroscopy, 1 H and 13 C nuclear magnetic resonance, and mass spectrometry), elemental analysis, and X-ray diffraction crystallography. A bioassay for antifungal activity in vitro against Phytophthora infestans, Fusariun solani, Alternaria solani, Rhizoctonia solani, and Colletotrichum coccodes demonstrated that 2,4,5-trioxopyrrolidin-1,3-thiazolidine derivatives exhibited a relatively broad spectrum of antifungal activity. One of the compounds showed considerable activity against all of the strains; in the case of F. solani, P. infestans, and A. solani, it possesses comparable or better fungicidal efficacy than the positive control Consento. Consequently, this compound is a promising fungicidal candidate for plant protection.