Pyriofenone is a fungicide.
IKF 309 is a fungicidal imidazole derivative use for controlling plant diseases caused by fungal plant pathogens.
ChEBI: An aromatic ketone that is metrafenone in which the 3-bromo-6-methoxy-2-methylphenyl group is replaced by a 5-chloro-2-methoxy-4-methylpyridin-3-yl group. It is a fungicide developed for the control of powdery mildew in cereals and grape vines.
Production of IKF 309 (Pyriofenone) begins with methyl 2-chloro-4-methyl nicotinate. An SNAr
(nucleophilic aromatic substitution) reaction introduces a methoxy group
to the pyridine ring. The pyridine ring is selectively chlorinated to
yield an intermediate compound which is subsequently hydrolysed to the
corresponding acid, then converted to an acid chloride. The acid
chloride reacts with 3,4,5-trimethoxy-toluene under Lewis acid catalysis
to form the final ketone structure of pyriofenone. The final stage is
purification and crystallisation.
