Multicomponent reactions in fungicide research: the discovery of mandipropamid.
Isocyanide-based multicomponent reactions of the Ugi- and Passerini-type have been valuable tools for the rapid exploration of the novel fungicidal compound classes of phenylglycinamides and mandelamides. Mandipropamid (6), which was discovered during this derivatisation, displays excellent activity against the economically important phytopathogens Phytophthora infestans (potato and tomato late blight) and Plasmopara viticola (grape downy mildew).
Lamberth
Clemens
C
Syngenta Crop Protection AG, Research Chemistry, Schwarzwaldallee 215, CH-4058 Basel, Switzerland. clemens.lamberth@syngenta.com
Jeanguenat
Andre
A
Cederbaum
Fredrik
F
De Mesmaeker
Alain
A
Zeller
Martin
M
Kempf
Hans-Joachim
HJ
Zeun
Ronald
R
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001550:Benzamidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010838:Phytophthora / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014633:Valine / Q000737:chemistry
D000577:Amides; D001550:Benzamidines; D002264:Carboxylic Acids; D005659:Fungicides, Industrial; C550943:mandipropamid; C005555:propamidine; D014633:Valine