title: Benzofurazan derivatives as antifungal agents against phytopathogenic fungi.
abstract: A series of benzofurazan derivatives were prepared and evaluated for their biological activities against four important phytopathogenic fungi, namely, Rhizoctonia solani, Sclerotinia sclerotiorum, Fusarium graminearum and Phytophthora capsici, using the mycelium growth inhibition method. The structures of these compounds were characterized by (1)H NMR, (13)C NMR, and HRMS. N-(3-chloro-4-fluorophenyl)-7-nitrobenzo[c][1,2,5]oxadiazol-4-amine (A3) displayed the maximum antifungal activity against R. solani (IC50 = 1.91 μg/mL), which is close to that of the positive control Carbendazim (IC50 = 1.42 μg/mL). For other benzofurazan derivatives with nitro group at R(4) position (A series), 9 out of 30 compounds exhibited high antifungal effect against strain R. solani, with IC50 values less than 5 μg/mL. Most of the derivatives with substituents at R(2) and R(3) positions (B series) displayed moderate growth inhibition against S. sclerotiorum (IC50 < 25 μg/mL). Also, several benzofuran derivatives with nitro group at R(4) position and another conjugated aromatic ring at the R(1) position of the phenyl ring displayed high antifungal capability against strain R. solani. Compounds with substituents at R(2) and R(3) position had moderate efficacy against strain S. sclerotiorum.
authors.affiliation: College of Pharmaceutical Science, Soochow University, Suzhou 215123, Jiangsu, PR China.
authors.forename: Lili
authors.initials: L
authors.lastname: Wang
authors.affiliation: College of Plant Protection, Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, PR China.
authors.forename: Ying-Ying
authors.initials: YY
authors.lastname: Zhang
authors.affiliation: School of Biology & Basic Medical Sciences, Soochow University, Suzhou 215123, Jiangsu, PR China.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.affiliation: College of Pharmaceutical Science, Soochow University, Suzhou 215123, Jiangsu, PR China.
authors.forename: Feng-you
authors.initials: FY
authors.lastname: Liu
authors.affiliation: College of Plant Protection, Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, PR China.
authors.forename: Ling-Ling
authors.initials: LL
authors.lastname: Cao
authors.affiliation: College of Pharmaceutical Science, Soochow University, Suzhou 215123, Jiangsu, PR China.
authors.forename: Jing
authors.initials: J
authors.lastname: Yang
authors.affiliation: College of Pharmaceutical Science, Soochow University, Suzhou 215123, Jiangsu, PR China. Electronic address: qiaochunhua@suda.edu.cn.
authors.forename: Chunhua
authors.initials: C
authors.lastname: Qiao
authors.affiliation: College of Plant Protection, Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, PR China. Electronic address: yeyh@njau.edu.cn.
authors.forename: Yonghao
authors.initials: Y
authors.lastname: Ye
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry* / Q000494:pharmacology*; D001583:Benzoxazoles / Q000737:chemistry*; D005658:Fungi / Q000187:drug effects* / Q000254:growth & development / Q000502:physiology; D020128:Inhibitory Concentration 50; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development; D010944:Plants / Q000382:microbiology*
chemical_list: D000935:Antifungal Agents; D001583:Benzoxazoles; C020160:benzofurazan
keywords: Antifungal activity; Benzofurazan derivatives; Phytopathogenic fungi