title: Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide.
abstract: To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by (1)H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52mg/L.
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Peng
authors.initials: P
authors.lastname: Lei
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Xu
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Juan
authors.initials: J
authors.lastname: Du
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Xin-Ling
authors.initials: XL
authors.lastname: Yang
authors.affiliation: Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China.
authors.forename: Hui-Zhu
authors.initials: HZ
authors.lastname: Yuan
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Gao-Fei
authors.initials: GF
authors.lastname: Xu
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. Electronic address: lyun@cau.edu.cn.
authors.forename: Yun
authors.initials: Y
authors.lastname: Ling
mesh_terms: D001203:Ascomycota / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
chemical_list: D005659:Fungicides, Industrial
keywords: 1,2,3,4-Tetrahydroquinoline; Carboxamide; Fungicidal activities; Synthesis