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- Title
Synthesis and Biological Evaluation of Isosteric Analogs of Mandipropamid for the Control of Oomycete pathogens.
- Authors
Na Su; Zhen-Jun Wang; Li-Zhong Wang; Xiao Zhang; Wei-Li Dong; Hong-Xue Wang; Zheng-Ming Li; Wei-Guang Zhao
- 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. A series of isosteric analogues of mandipropamid were designed and synthesized via 'click chemistry'. The bioassay results have indicated that some of the title compounds exhibited moderate fungicidal activitiy against Pseudoperonospora cubensis, and the activity has been systematically studied as a function of molecular structure
- Subjects
OOMYCETES; BIOLOGICAL assay; MOLECULAR structure; HYDROGEN bonding; ASCOMYCETES; PLANT parasites
- Publication
Chemical Biology & Drug Design, 2011, Vol 78, Issue 1, p101
- ISSN
1747-0277
- Publication type
Article
- DOI
10.1111/j.1747-0285.2011.01093.x