title: Synthesis and fungicidal activity of N-thiazol-4-yl-salicylamides, a new family of anti-oomycete compounds.
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.
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors: Sarah
authors: S
authors: Sulzer-Mosse
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors: Fredrik
authors: F
authors: Cederbaum
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland. Electronic address: clemens.lamberth@syngenta.com.
authors: Clemens
authors: C
authors: Lamberth
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors: Guillaume
authors: G
authors: Berthon
authors: Syngenta Biosciences Pvt. Ltd, Research & Technology Centre, Santa Monica Works, Corlim, Ilhas, Goa 403 110, India.
authors: Jayant
authors: J
authors: Umarye
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors: Valeria
authors: V
authors: Grasso
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors: Alexandra
authors: A
authors: Schlereth
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors: Mathias
authors: M
authors: Blum
authors: Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors: Rita
authors: R
authors: Waldmeier
mesh_terms: D004305:Dose-Response Relationship, Drug; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009868:Oomycetes / Q000187:drug effects*; D012457:Salicylamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D005659:Fungicides, Industrial; D012457:Salicylamides; D013844:Thiazoles
keywords: Crop protection; Fungicide; Heterocycle; Salicylamide; Thiazole