Chlorfenapyr

4-bromo- 2-(4 -chlorophenyl )-1- ethoxymethyl -5-trifluoromethyl -pyrrole- 3-carbonitrile

White solid

Fixed

0.543 g · cm -3 ( bulk density )

100-101 ° C

Practically insoluble in water

Risk

• 441 mg · kg -1 ( LD50, rat, oral)
• 1152 mg · kg -1 ( LD50, rat, oral)
• > 2000 mg · kg -1 ( LD50, Rabbit, transdermal)

Template: Infobox chemical / molecular formula search available

Chlorfenapyr is a chemical compound selected from the group of the pyrroles.

History

On 12 December 1994, the American Cyanamid Company introduced (now part of BASF ) its application for approval of Chlorfenapyr in cotton.

Production and representation

Chlorfenapyr can be obtained through a series of reaction of p- chlorobenzaldehyde ( Strecker synthesis, then bipolar addition of acrylonitrile to further pyrroline, via hydrogen abstraction on the pyrrole followed by bromination ).

Properties

Chlorfenapyr is a white solid that is practically insoluble in water.

Use

Chlorfenapyr is used as an insecticide and acaricide on ornamentals in commercial greenhouse cultivation against mites, caterpillar pests, thrips and fungus gnats, but not for food crops. It is a pro- insecticide is, the biological activity depends on the activation by a different chemical connection. The oxidative removal of the N - ethoxymethyl group of mixed-function oxidases produced by Chlorfenapyr the link CL 303,268th This decouples the oxidative phosphorylation in the mitochondria, which, thus cell death and eventually the death of the organism resulted in an interruption of ATP production.

In the U.S., the approval of the agent for cotton against the " armyworm " (Spodoptera frugiperda ) by the EPO was withdrawn, as turned out to serious effects on reproduction of birds by the means and alternatives for Chlorfenapyr are available.

On the basis of Chlorfenapyr BASF aims to develop a new generation of malaria prevention products from 2010.

In Germany, Switzerland and Austria no pesticide is approved, containing the active substance, but it is offered in remedies for bed bugs.