Definition
ChEBI: An ethyl ester resulting from the formal condesnation of the carboxy group of flufenpyr with ethanol. It is used as a contact herbicide for the control of broad-leaved weeds. It acts as a protoporphyrinogen oxidase inhibitor, causing protoporphyrins to acc
mulate, damaging the membrane structure and cellular function. No longer approved for use in the European Union.
Production Methods
Flufenpyr-ethyl is commercially produced through a multi-step synthesis involving the condensation of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinone with ethyl bromoacetate. This reaction forms the ethyl ester of a phenoxyacetic acid derivative, incorporating a pyridazinone ring with multiple halogen substitutions for enhanced herbicidal activity. The synthesis is typically carried out under reflux in polar aprotic solvents, followed by purification steps such as crystallisation or chromatography.
Mechanism of action
Protoporphyrinogen oxidase inhibitor
