title: Synthesis and fungicidal activity of quinolin-6-yloxyacetamides, a novel class of tubulin polymerization inhibitors.
abstract: A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula necator (grape powdery mildew). Their fungicidal activity is due to their ability to inhibit fungal tubulin polymerization, leading to microtubule destabilization. An efficient synthesis route has been worked out, which allows the diverse substitution of four identified key positions across the molecular scaffold.
authors.affiliation: Syngenta Crop Protection AG, Research Chemistry, Schaffhauserstr. 101, CH-4332 Stein, Switzerland. Electronic address: clemens.lamberth@syngenta.com.
authors.forename: Clemens
authors.initials: C
authors.lastname: Lamberth
authors.affiliation: Syngenta Crop Protection AG, Research Chemistry, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Fiona Murphy
authors.initials: FM
authors.lastname: Kessabi
authors.affiliation: Syngenta Crop Protection AG, Research Chemistry, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Renaud
authors.initials: R
authors.lastname: Beaudegnies
authors.affiliation: Syngenta Crop Protection AG, Research Chemistry, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Laura
authors.initials: L
authors.lastname: Quaranta
authors.affiliation: Syngenta Crop Protection AG, Research Chemistry, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Stephan
authors.initials: S
authors.lastname: Trah
authors.affiliation: Syngenta Crop Protection AG, Research Chemistry, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Berthon
authors.affiliation: Syngenta Crop Protection AG, Research Chemistry, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Fredrik
authors.initials: F
authors.lastname: Cederbaum
authors.affiliation: Syngenta Crop Protection AG, Research Biology, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Gertrud
authors.initials: G
authors.lastname: Knauf-Beiter
authors.affiliation: Syngenta Crop Protection AG, Research Biology, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Valeria
authors.initials: V
authors.lastname: Grasso
authors.affiliation: Syngenta Crop Protection AG, Research Biology, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
authors.forename: Stephane
authors.initials: S
authors.lastname: Bieri
authors.affiliation: Syngenta Ltd, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
authors.forename: Andy
authors.initials: A
authors.lastname: Corran
authors.affiliation: Syngenta Ltd, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
authors.forename: Urvashi
authors.initials: U
authors.lastname: Thacker
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D055750:Phytophthora infestans / Q000187:drug effects; D011804:Quinolines / Q000737:chemistry; D004718:Saccharomycetales / Q000187:drug effects; D013329:Structure-Activity Relationship; D050257:Tubulin Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000081:Acetamides; D000935:Antifungal Agents; D011804:Quinolines; D050257:Tubulin Modulators; C037219:quinoline
keywords: Crop protection; Fungicide; Heterocycle; Quinoline; Tubulin