Famoxadone: the discovery and optimisation of a new agricultural fungicide

Famoxadone (3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dion e), is a new agricultural fungicide recently commercialized by DuPont under the trade name Famoxate(R) Famoxadone is a member of a new class of oxazol idinone fungicides that demonstrate excellent control of plant pathogens in the Ascomycete, Basidiomycete, and Oomycete classes that infect grapes, ce reals, tomatoes, potatoes and other crops. DuPont's entry into the oxazolid inone area resulted from the procurement of 5-methyl-5-phenyl-3-phenylamino -2-thioxo-4-oxazolidinone (1) from Professor Detlef Geffken, then at the Un iversity of Bonn, An extensive analog program was initiated immediately aft er the fungicidal activity of 1 was discovered through routine greenhouse t esting. The discovery program in the oxazolidinone area eventually culminat ed in the advancement of famoxadone to commercial development in the early 1990s. The synthesis of various oxazolidinone ring systems and the developm ent of the structure-activity relationships that led to the discovery of fa moxadone are described. (C) 2001 Society of Chemical Industry.