Etofenprox

Chemical properties

solid

The Uses of Etofenprox

Etofenprox is used to control a wide variety of insects on fruit, tea, soyabeans and many vegetables. It is also used in public health and animal health.

The Uses of Etofenprox

Insecticide.

Definition

ChEBI: An aromatic ether that is the 3-phenoxybenzyl ether of 2-(4-ethoxyphenyl)-2-methylpropan-1-ol.

Agricultural Uses

Insecticide: Approved for use in the U.S. and more than a dozen EU countries.

Trade name

MTI 500®; PUNKASO®; TREBON®; ZOECON® RF-316

Metabolic pathway

Etofenprox is one of the few members of a new class, the non-ester pyrethroids. It lacks the ester bond and therefore is not subject to facile chemical or biochemical hydrolysis. Metabolic options will be limited to oxidative processes. Little has been published in the scientific literature. Its photochemistry has been described and metabolic oxidation products have been noted.

Degradation

Etofenprox is stable in acid and alkaline media for more than 100 days at 80 °C. It is reasonably stable to light under normal conditions of use but it is photodegradable. Under conditions where allethrin was degraded with a half-life of 0.5 hours, etofenprox had a half-life of 3 hours (Tsao and Eto, 1990).
The major product was the ester formed by oxidation at the benzylic carbon atom to form 2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzoate (2), clearly the result of hydroxylation and dehydrogenation. This ester was found to be non-toxic to houseflies. It was cleaved to form 3PBA (5) and the alcohol (6). 6 was degraded via decarboxylation to 7 and 8. A concurrent reaction of etofenprox was O-de-ethylation to the phenol (3). A similar array of products was seen in both aqueous suspension and as a thin film on glass. It should be noted that this study did not utilise radiolabelled compound.