title: Synthesis and fungicidal activity of a series of novel aryloxylepidines.
abstract: A series of novel (hetero) aryloxylepidine derivatives was devised as hybrid structures of the phenoxyquinoline and phenethoxyquin(az)oline fungicides. Synthesis of these targets required the development of several new routes to derivatised 4-hydroxymethylquinolines, and subsequent coupling with phenols or haloarenes. The aryloxylepidines generally showed moderate broad-spectrum fungicidal activity across several diseases of cereals. Substitution of the quinoline ring with chlorine at the 7- and/or 5-positions gave molecules with high levels of protectant activity against Erysiphe graminis f sp tritici (powdery mildew of wheat), but this did not improve the level of fungicidal activity against other diseases. In vitro activity against mitochondrial electron transport complex I (MET) derived from Ustilago maydis showed that 8-fluorolepidine analogues were moderately active at this target site, while the more fungicidally active 7- and 5,7-substituted compounds were inactive. This indicates that MET is not the primary target of these highly active powdery mildewicides.
authors.affiliation: Dow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, IN 46268-1054, USA. nkirby@dowagro.com
authors.forename: N V
authors.initials: NV
authors.lastname: Kirby
authors.forename: J F
authors.initials: JF
authors.lastname: Daeuble
authors.forename: L N
authors.initials: LN
authors.lastname: Davis
authors.forename: A C
authors.initials: AC
authors.lastname: Hannum
authors.forename: K
authors.initials: K
authors.lastname: Hellwig
authors.forename: L K
authors.initials: LK
authors.lastname: Lawler
authors.forename: M H
authors.initials: MH
authors.lastname: Parker
authors.forename: M E
authors.initials: ME
authors.lastname: Pieczko
mesh_terms: D001203:Ascomycota / Q000187:drug effects*; D004579:Electron Transport / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology; D008928:Mitochondria / Q000187:drug effects; D015394:Molecular Structure; D006109:Poaceae / Q000382:microbiology; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology; D014588:Ustilago / Q000187:drug effects*
chemical_list: D005659:Fungicides, Industrial; D011799:Quinazolines; C087876:fenazaquin