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

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, H andC 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.

Five-Membered Nitrogen Heterocycles as New Lead Compounds in Drug Discovery

“…In their work, they found that almost all synthesized compounds showed fungicidal activity and, specifically derivatives 151-153 exhibited a concentrationdependent activity on C. albicans biofilm (Figure 15). On the other hand, Obydennov et al 74 In the preparation of 2,4,5-pyrrolidinetrione core structures 154-159, Obydennov et al 74 followed a straightforward synthetic protocol using enamides and oxalyl chloride as starting materials. In their route, Obydennov et al 74 Malaria has killed hundreds of thousands people every year.…”

Bipolarithizole A, an antifungal phenylthiazole-sativene merosesquiterpenoid from the potato endophytic fungus Bipolaris eleusines

“…At present, the common antimicrobial agents against potato diseases are a variety of synthetic fungicides, which in addition to being beneficial, also have adverse effects on the host and the environment, resulting in pathogen resistance to the fungicides. [8][9][10] Therefore, new and effective natural fungicides are urgently required.…”

Synthesis and Antifungal and Insecticidal Activities of Novel N-Phenylbenzamide Derivatives Bearing a Trifluoromethylpyrimidine Moiety

“…e traditional commercial fungicides and insecticides used to prevent and control plant diseases could increase the yield, improve the quality of agricultural products, and also not reduced huge loss annually [5,6]. However, the misuse of traditional fungicides and insecticides had speeded up the resistance of plant diseases, which is rapidly becoming a huge challenge in agriculture [7,8]. erefore, it is still an urgent and meaningful task to develop the novel, highly efficient, and promising pesticides.…”