Synthesis and fungicidal activity of a series of novel aryloxylepidines.
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.
Kirby
N V
NV
Dow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, IN 46268-1054, USA. nkirby@dowagro.com
Daeuble
J F
JF
Davis
L N
LN
Hannum
A C
AC
Hellwig
K
K
Lawler
L K
LK
Parker
M H
MH
Pieczko
M E
ME
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*
D005659:Fungicides, Industrial; D011799:Quinazolines; C087876:fenazaquin