2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoic acid

(±)-Haloxyfop is a herbicide.

ChEBI: 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid is a monocarboxylic acid that is 2-phenoxypropanoic acid in which the hydrogen at the para position of the phenyl ring has been replaced by a [3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy group. It is a member of pyridines, an aromatic ether, a monocarboxylic acid, an organofluorine compound and an organochlorine compound.

Haloxyfop is synthesised as haloxyfop-R-methyl through a multi-step process that constructs its pyridyl ether structure. The synthesis typically begins with 2,3-dichloro-5-trifluoromethylpyridine, which is dissolved in a polar aprotic solvent like dimethylacetamide. This is reacted with (R)-(+)-2-(4-hydroxyphenoxy)propionic acid methyl ester in the presence of a base such as potassium carbonate under nitrogen atmosphere and heat, forming the key ether linkage via nucleophilic substitution. After the reaction, the mixture is cooled and subjected to vacuum distillation to remove solvents, followed by aqueous workup and acid washing to eliminate residual bases and impurities. The organic phase is then washed repeatedly with deionized water and dried, and the final product is obtained by desolventising under heat.

Selective, absorbed by roots and foliage. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

Herbicide; Metabolite