Fluazuron

Chemical Properties

White Powder

Uses

A pesticide, like other BPUs it interferes with chitin synthesis.

Uses

Fluazuron is used for the strategic control of the cattle tick Boaphilus microplus on beef cattle.

Definition

ChEBI: Fluazuron is an N-acylurea that is urea in which one of the hydrogens has been replaced by a 3,6-difluorobenzoyl group, while a hydrogen attached to the other nitrogen has been replaced by a 4-chloro-3-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenyl group. It is used to control ticks in cattle. It has a role as a mite growth regulator and an acaricide. It is an organofluorine acaricide, an organochlorine acaricide, a member of monochlorobenzenes, a N-acylurea, a chloropyridine, an aromatic ether and a member of phenylureas.

Synthesis

A method for chemically synthesizing fluazuron comprises the following steps of: subjecting 2-chloro-5-nitrophenol and 2,3-dichloro-5-methyl triflouro pyridine to an etherifying reaction to prepare etherate; reducing to generate 4-chloro-3-(3-chloro-5-methyl triflouro2-pyridyloxy) aniline by taking ethanol or methanol as solvents and sodium bisulfide as a reducing agent; subjecting 2,6-difluorobenzamide and triphosgene to an N-acylation reaction to obtain 2,6-difluorobenzoyl isocyanate; and subjecting 4-chloro-3-(3-chloro-5methyl triflouro2-pyridyloxy) aniline and the 2,6-difluorobenzoyl isocyanate to an addition reaction to prepare the fluazuron.1

Metabolic pathway

Only limited information is available in the open literature on the metabolism of fluazuron in animals. Based on its use, information on metabolism in soils and plants is not relevant.

Degradation

Fluazuron is less stable at alkaline pH than under acidic conditions. The hydrolysis DT₅₀ at 25 °C was reported to be 14 days at pH 3, 7 days at pH 5,20 hours at pH 7 and 0.5 hours at pH 9 (PM).

References

[1]CN101906070A