Synthesis and fungicidal activity of methyl (E)-1-(2-((E)-2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)-2-(1-arylidene)hydrazine-1-carboxylates †‡
- 6 February 2021
- journal article
- research article
- Published by Springer Science and Business Media LLC in Molecular Diversity
- Vol. 26 (2), 801-813
- https://doi.org/10.1007/s11030-021-10187-6
Abstract
To discover novel strobilurin fungicides, a series of methyl (E)-1-(2-((E)-2-methoxy-1-(methoxy-imino)-2-oxoethyl)benzyl)-2-(1-arylidene)hydrazine-1-carboxylates were designed based on the principle of biologically active splicing and the receptor target structure. The fungicidal activity results show that this class of compounds has excellent fungicidal activity, especially against S. sclerotiorum (Lib.) deBary, wheat white powder and puccinia polysora. The result of structure–activity relationship implied that the introduction of t-butyl in the side chain facilitates the hydrophobic interaction between the compound and the active site. The electrostatic effect of the substituents on the benzene ring is also a key factor affecting such activities. Among them, the compound I-1 not only showed a fungicidal effect comparable to that of kresoxim-methyl in vivo, but also had an excellent inhibitory effect on spore germination of P. oryzae Cav in vitro, which indicated that it could be used as a potential commercial fungicide for plant disease control. Graphic abstractKeywords
Funding Information
- the National Key Research and Development Plan (2018YFD0200103)
This publication has 20 references indexed in Scilit:
- Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine MoietiesChinese Journal of Organic Chemistry, 2015
- Synthesis and Evaluation O-Benzyl Oxime-ether Derivatives Containing β-Methoxyacrylate Moiety for Insecticidal and Fungicidal ActivitiesBulletin of the Korean Chemical Society, 2014
- Structural Basis of Resistance to Anti-Cytochrome bc1 Complex Inhibitors: Implication for Drug ImprovementCurrent Pharmaceutical Design, 2014
- Synthesis of novel strobilurin–pyrimidine derivatives and their antiproliferative activity against human cancer cell linesBioorganic & Medicinal Chemistry Letters, 2013
- Regioselective synthesis of fraxinellone-based hydrazone derivatives as insecticidal agentsBioorganic & Medicinal Chemistry Letters, 2012
- Fluacrypyrim, a novel STAT3 activation inhibitor, induces cell cycle arrest and apoptosis in cancer cells harboring constitutively‐active STAT3International Journal of Cancer, 2010
- Synthesis, Fungicidal, and Insecticidal Activities of β-Methoxyacrylate-Containing N-Acetyl Pyrazoline DerivativesJournal of Agricultural and Food Chemistry, 2008
- Molecular complexes at a glance: automated generation of two-dimensional complex diagramsBioinformatics, 2006
- Crystallographic Studies of Quinol Oxidation Site Inhibitors: A Modified Classification of Inhibitors for the Cytochrome bc1 ComplexJournal of Molecular Biology, 2004
- Crystal Structure of the Cytochrome bc 1 Complex from Bovine Heart MitochondriaScience, 1997