title: Synthesis and fungicidal activity of tubulin polymerisation promoters. Part 3: imidazoles.
abstract: A novel class of experimental fungicides has been discovered, which consists of special tetrasubstituted imidazoles. They are highly active against important phytopathogens, such as Botrytis cinerea (grey mould), Uncinula necator (grape powdery mildew), Mycosphaerella graminicola (wheat leaf blotch) and Alternaria solani (potato and tomato early blight). Their fungicidal efficacy is due to their ability to promote fungal tubulin polymerization, which leads to a disruption of microtubule dynamics. These imidazoles are five-membered ring analogs of similar substituted triazolopyrimidines and pyridazines with the same mode of action. A concise four-step synthesis route has been used to prepare them from commercially available starting materials.
authors.affiliation: Syngenta Crop Protection AG, Crop Protection Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland. clemens.lamberth@syngenta.com
authors.forename: Clemens
authors.initials: C
authors.lastname: Lamberth
authors.forename: Raphael
authors.initials: R
authors.lastname: Dumeunier
authors.forename: Stephan
authors.initials: S
authors.lastname: Trah
authors.forename: Sebastian
authors.initials: S
authors.lastname: Wendeborn
authors.forename: Jeremy
authors.initials: J
authors.lastname: Godwin
authors.forename: Peter
authors.initials: P
authors.lastname: Schneiter
authors.forename: Andy
authors.initials: A
authors.lastname: Corran
mesh_terms: D000528:Alternaria / Q000187:drug effects; D001203:Ascomycota / Q000187:drug effects; D020171:Botrytis / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010935:Plant Diseases / Q000382:microbiology*; D010940:Plant Proteins / Q000378:metabolism; D010944:Plants / Q000378:metabolism / Q000382:microbiology; D014404:Tubulin / Q000378:metabolism; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D005659:Fungicides, Industrial; D007093:Imidazoles; D010940:Plant Proteins; D014404:Tubulin; D050257:Tubulin Modulators