title: Design, synthesis, and fungicidal activities of imino diacid analogs of valine amide fungicides.
abstract: The novel imino diacid analogs of valine amides were synthesized via several steps, including the protection, amidation, deprotection, and amino alkylation of valine, with the resulting structures confirmed by (1)H and (13)C NMR and HRMS. Bioassays showed that some of these compounds exhibited good fungicidal activity. Notably, isopropyl 2-((1-((1-(3-fluorophenyl)ethyl)amino)-3-methyl-1-oxobutan-2-yl)amino)propanoate 5i displayed significant levels of control, at 50%, against Erysiphe graminis at 3.9μM as well as a level of potency very similar to the reference azoxystrobin, which gave 60% activity at this concentration. The present work demonstrates that imino diacid analogs of valine amides could be potentially useful key compounds for the development of novel fungicides against wheat powdery mildew.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
authors.forename: Man
authors.initials: M
authors.lastname: Sun
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
authors.forename: Hui-Hui
authors.initials: HH
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Tian
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
authors.forename: Jian-Qiang
authors.initials: JQ
authors.lastname: Li
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China. Electronic address: zwg@nankai.edu.cn.
authors.forename: Wei-Guang
authors.initials: WG
authors.lastname: Zhao
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001203:Ascomycota / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D014633:Valine / Q000737:chemistry
chemical_list: D000577:Amides; D005659:Fungicides, Industrial; D014633:Valine
keywords: Fungicidal activity; Imino diacid; Synthesis; Valine amide