title: Synthesis and biological evaluation of isosteric analogs of mandipropamid for the control of oomycete pathogens.
abstract: A series of isosteric analogs of mandipropamid were designed and synthesized via 'click chemistry'. The amide bond of mandipropamid was substituted by a 1,2,3-triazole functional group. The bioassay results have indicated that some of the title compounds exhibited moderate fungicidal activity against Pseudoperonospora cubensis, and the activity has been systematically studied as a function of molecular structure. The low activity of the mandipropamid analog that contains a lipid chain is likely due to the presence of a weak hydrogen bond donor in the 1,2,3-triazole. Furthermore, we have performed the molecular modeling and found that N-methylamide could be more effective than amide as the surrogates to 1,2,3-triazole, which ultimately leads to a longer distance (1.1 Å longer) between the two substitutes in the 1,4-disubstituted 1,2,3-triazole compound.
authors: National Pesticide Engineering Research Center (Tianjin), State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China.
authors: Na
authors: N
authors: Su
authors: Zhen-Jun
authors: ZJ
authors: Wang
authors: Li-Zhong
authors: LZ
authors: Wang
authors: Xiao
authors: X
authors: Zhang
authors: Wei-Li
authors: WL
authors: Dong
authors: Hong-Xue
authors: HX
authors: Wang
authors: Zheng-Ming
authors: ZM
authors: Li
authors: Wei-Guang
authors: WG
authors: Zhao
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D009868:Oomycetes / Q000187:drug effects*; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000935:Antifungal Agents; D002264:Carboxylic Acids; C550943:mandipropamid