1. Synthesis and fungicidal activity of novel imidazole-based ketene dithioacetals
- Author
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Clemens Lamberth, Fredrik Cederbaum, Julien Daniel Henri Gagnepain, Stephane Bieri, Stephane Jeanmart, Mathias Blum, Pulakesh Maity, Olivier Jacob, and Ramya Rajan
- Subjects
Antifungal Agents ,Stereochemistry ,Clinical Biochemistry ,Alternaria solani ,Pharmaceutical Science ,Ketene ,Microbial Sensitivity Tests ,Botryotinia fuckeliana ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Dithiolane ,Fungal Proteins ,Sterol 14-Demethylase ,Structure-Activity Relationship ,chemistry.chemical_compound ,Acetals ,Ascomycota ,Drug Discovery ,Imidazole ,Molecular Biology ,Binding Sites ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Imidazoles ,Alternaria ,food and beverages ,Erysiphe necator ,Ethylenes ,Ketones ,biology.organism_classification ,Protein Structure, Tertiary ,0104 chemical sciences ,Molecular Docking Simulation ,Fungicide ,14-alpha Demethylase Inhibitors ,Cytochrome P450 Family 51 ,biology.protein ,Molecular Medicine ,Demethylase - Abstract
Novel imidazole-based ketene dithioacetals show impressive in planta activity against the economically important plant pathogens Alternaria solani, Botryotinia fuckeliana, Erysiphe necator and Zymoseptoria tritici. Especially derivatives of the topical antifungal lanoconazole, which bear an alkynyloxy or a heteroaryl group in the para-position of the phenyl ring, exhibit excellent control of the mentioned phytopathogens. These compounds inhibit 14α -demethylase in the sterol biosynthesis pathway of the fungi. Synthesis routes starting from either benzaldehydes or acetophenones as well as structure-activity relationships are discussed in detail.
- Published
- 2018