Definition
ChEBI: Teflubenzuron is a N-acylurea that is N-carbamoyl-2,6-difluorobenzamide substituted by a 3,5-dichloro-2,4-difluorophenyl group at the terminal nitrogen atom. It has a role as a xenobiotic, an environmental contaminant and an insecticide. It is a dichlorobenzene, a N-acylurea and a difluorobenzene. It is functionally related to a N-benzoylurea.
Production Methods
Teflubenzuron is synthesised through a multi-step organic process designed to construct its complex difluorinated and dichlorinated aromatic structure. The production typically begins with the preparation of two key intermediates: a substituted benzoyl chloride and a substituted phenylurea. One route involves reacting 2,6-difluorobenzoyl chloride with 3,5-dichloro-2,4-difluoroaniline to form the urea linkage central to teflubenzuron’s structure. This condensation reaction is carried out under controlled conditions, often using solvents like toluene and a base such as triethylamine to facilitate the coupling. The final compound is then purified.
Mechanism of action
Systemic. Inhibitor of chitin biosynthesis affecting CHS1.
Metabolic pathway
There is limited published information on the metabolism of teflubenzuron
but an IPCS review is in preparation. Metabolic processes reported
are cleavage of the urea bond and hydroxylation of both phenyl rings,
including replacement of a fluorine in the 3,5-dichloro-2,4-difluorophenyl
ring (see Scheme 1).
Degradation
Teflubenzuron is more readily hydrolysed at alkaline pH than in acid
media. The DT50 at 50 °C was 5 days at pH 7 and 4 hours at pH 9 (PM).
Toxicity evaluation
Acute oral LD50 for rats: >5,000 mg/kg
Pesticide Type
Insecticide; Veterinary substance
