title: Synthesis of N-substituted phthalimides and their antifungal activity against Alternaria solani and Botrytis cinerea.
abstract: 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.
authors.affiliation: University of Chinese Academy of Sciences, People's Republic of China; Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China.
authors.forename: Le
authors.initials: L
authors.lastname: Pan
authors.affiliation: Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China.
authors.forename: Xiuzhuang
authors.initials: X
authors.lastname: Li
authors.affiliation: Institute of Chinese Medicinal Herbs, Gansu Academy of Agricultural Sciences, Lanzhou 730070, People's Republic of China.
authors.forename: Chengwen
authors.initials: C
authors.lastname: Gong
authors.affiliation: Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China.
authors.forename: Hui
authors.initials: H
authors.lastname: Jin
authors.affiliation: Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China. Electronic address: bqin@licp.cas.cn.
authors.forename: Bo
authors.initials: B
authors.lastname: Qin
mesh_terms: D000528:Alternaria / Q000187:drug effects*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D020171:Botrytis / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D010797:Phthalimides / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000935:Antifungal Agents; D010797:Phthalimides
keywords: Antifungal activity; IC(50) values; N-substituted phthalimides; Synthesis