Synthesis of N-substituted phthalimides and their antifungal activity against Alternaria solani and Botrytis cinerea

• Published in: Microbial pathogenesis 2016-06, Vol.95, p.186-192
• Main Authors: Pan, Le, Li, Xiuzhuang, Gong, Chengwen, Jin, Hui, Qin, Bo
• Format: Article
• Language: English
• Subjects: Alternaria - drug effects; Alternaria solani; Antifungal activity; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Botrytis - drug effects; Botrytis cinerea; IC50 values; Inhibitory Concentration 50; Microbial Sensitivity Tests; Models, Molecular; Molecular Structure; N-substituted phthalimides; Phthalimides - chemical synthesis; Phthalimides - pharmacology; Synthesis
• ISSN: 0882-4010; 1096-1208
• DOI: 10.1016/j.micpath.2016.04.012

As organosulfur and organophosphorus agents, phaltane and phosmet are facing great challenges for the environmental contamination, mammalian toxicity and increasing resistance with long term use. It is efficient and meaningful to develop phthalimide-based alternatives with non-sulfur and non-phosphorus groups. A series of N-substituted phthalimides were synthesized and their antifungal activity against two disastrous phytopathogenic fungi, Alternaria solani and Botrytis cinerea was evaluated in vitro. Most of them showed significant antifungal activity against both of fungi, or either of them selectively. N-vinylphthalimide (4) and 8-[4-(phthalimide-2-yl) butyloxy] quinoline (13) were identified as the most promising candidates against B. cinerea and A. solani with the IC50 values of 7.92 μg/mL and 10.85 μg/mL respectively. The brief structure-activity relationships have revealed that vinyl, quinolyl, bromide alkyl and benzyl substitutions were appropriate substituents and coupling functional moieties indirectly with optimum alkyl chain was efficient to prepare phthalimides related fungicides. [Display omitted] •Non-sulfur and non-phosphorus phthalimides were synthesized.•Their antifungal activity was evaluated.•The efficacious compounds were discovered.•The structure-activity relationships provided meaningful guidance for preparing phthalimides related fungicides.