2-(4-((3-Chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)-propanoic acid methyl ester

Chemical Properties

Flupyrifos is colorless crystal, melting point 55~57℃, vapor pressure 0.80mPa(25℃), KowlgP=4.07.Henry's constant 3.23×10-2Pa-m3 /mol(calculated value), solubility in water 9.3mg/L(25℃); solubility in other solvents(kg/kg, 20℃): acetonitrile 4.0, acetone 3.5, dichloromethane 3.0, xylene 1.27. Dichloromethane 3.0, Xylene 1.27.

Uses

Haloxyfop-R-methyl-d3 is a labeled analogue of (R)-Haloxyfop Methyl Ester (H104020), which is a herbicide. It is used in the study of reduced rates of the acetyl-co enzyme A carboxylase (ACCase)-inhibiting herbicide.

Definition

ChEBI: Haloxyfop-P-methyl is a methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate that has R configuration. It is a proherbicide (by hydrolysis of the methyl ester) for the herbicide haloxyfop-P, the most active enantiomer of the racemic herbicide haloxyfop. It has a role as a proherbicide, an EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor and an agrochemical. It is functionally related to a haloxyfop-P. It is an enantiomer of a (S)-haloxyfop-methyl.

Production Methods

Haloxyfop R-methyl is synthesised 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.

Mechanism of action

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

Pesticide Type

Herbicide