Synthesis and fungicidal activity of novel imidazole-based ketene dithioacetals. Issue 8 (1st May 2018)

• Record Type: Journal Article
• Authors: Jeanmart, Stephane; Gagnepain, Julien; Maity, Pulakesh; Lamberth, Clemens; Cederbaum, Fredrik; Rajan, Ramya; Jacob, Olivier; Blum, Mathias; Bieri, Stephane
• Is Part Of: Bioorganic & medicinal chemistry. Volume 26:Issue 8(2018)
• Page Start: 2009
• Page End: 2016
• Publication Date: 2018-05-01
• Subjects: Dithiolane -- Imidazole -- C14-demethylase inhibitor -- Fungicide -- Crop protection; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2018.02.051
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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.