IKF 309 Chemical Properties

Melting point:

91-94°C

Boiling point:

519.8±50.0 °C(Predicted)

Density 

1.214±0.06 g/cm3(Predicted)

storage temp. 

Amber Vial, -20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

pka

-0.80±0.28(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Light Sensitive

LogP

4.469 (est)

EPA Substance Registry System

Methanone, (5-chloro-2-methoxy-4-methyl-3-pyridinyl)(2,3,4-trimethoxy-6-methylphenyl)- (688046-61-9)

IKF 309 Usage And Synthesis

Uses

Pyriofenone is a fungicide.

Uses

IKF 309 is a fungicidal imidazole derivative use for controlling plant diseases caused by fungal plant pathogens.

Definition

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.

Synthesis

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.