1. Synthesis and fungicidal activity of N-thiazol-4-yl-salicylamides, a new family of anti-oomycete compounds
- Author
-
Fredrik Cederbaum, Guillaume Berthon, Alexandra Schlereth, Rita Waldmeier, Valeria Grasso, Sarah Sulzer-Mosse, Mathias Blum, Jayant Umarye, and Clemens Lamberth
- Subjects
medicine.drug_class ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Carboxamide ,Microbial Sensitivity Tests ,Biochemistry ,Structure-Activity Relationship ,chemistry.chemical_compound ,Salicylamides ,Drug Discovery ,medicine ,Thiazole ,Molecular Biology ,Oomycete ,Dose-Response Relationship, Drug ,Molecular Structure ,biology ,Chemistry ,Organic Chemistry ,biology.organism_classification ,Fungicides, Industrial ,Pythium ultimum ,Thiazoles ,Oomycetes ,Plasmopara viticola ,Phytophthora infestans ,Molecular Medicine ,Downy mildew - Abstract
A novel class of experimental fungicides has been discovered, which consists of special N-thiazol-4-yl-salicylamides. They originated from amide reversion of lead structures from the patent literature and are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Plasmopara viticola (grapevine downy mildew) and Pythium ultimum (damping-off disease). Structure–activity relationship studies revealed the importance of a phenolic or enolic hydroxy function in the β-position of a carboxamide. An efficient synthesis route has been worked out, which for the first time employs the carbonyldiimidazole-mediated Lossen rearrangement in the field of thiazole carboxylic acids. more...
- Published
- 2015
- Full Text
- View/download PDF