Chlorfenapyr is a broad spectrum pesticide which is not approved for use in the EU, and only approved for limited applications in the US (applications for ornamental plants in greenhouses). It was originally rejected for FDA approval due to avian and aquatic toxicity. Data on human toxicity is still scarce, but it has moderate mammalian toxicity when taken orally, causing vacuolation of the nervous system in mice and rats. It is not persistent in ecosystems, and has low aqueous solubility.
Chlorfenapyr can also be used as an insect-proofing agent in wool, and has been investigated for applications in malaria control.
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3039634/
https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-129093_01-Jan-01.pdf
https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/136.htm
https://en.wikipedia.org/wiki/Chlorfenapyr
https://www.pwrc.usgs.gov/resshow/Albers/albers1.htm
Chlorfenapyr is a pyrrole pro-insecticide that is metabolized in vivo into CL 303268 by mixed function oxidases. Chlorfenapyr increases respiratory activity in German cockroaches when used at concentrations ranging from 1 to 10 μg per insect but has no effect on respiration in Sf9 cells when used at concentrations ranging from 1 to 100 μM and does not affect respiration in isolated rat liver mitochondria up to a concentration of 10 μM. Chlorfenapyr is active against a variety of insects including those susceptible and resistant to pyrethroid and organophosphate insecticides, including horn flies (H. irritans) as well as A. culicifacies and A. stephensi mosquitos that carry malaria (LC50s = 2-2.39% suspension impregnated on paper). Chlorfenapyr is lethal to rats with LD50 values of 441 and 1,152 mg/kg for male and female rats, respectively. Formulations containing chlorfenapyr have been used to control termites and in agriculture to control various insects.
Chlorfenapyr is a halogenated pyrrole based pro-insecticide. Chlorfenapyr functions by metabolizing into an active insecticide after entering the host. Chlorfenapyr is used primarily as a means of pes
t control on cotton.
ChEBI: Chlorfenapyr is a member of the class of pyrroles that is 4-bromo-1H-pyrrole-3-carbonitrile which is substituted at positions 1, 2 and 5 by ethoxymethyl, p-chlorophenyl and trifluoromethyl groups, respectively. A proinsecticide used for termite control and crop protection against several insects and mite pests. It has a role as a proinsecticide and a proacaricide. It is an organofluorine acaricide, an organochlorine acaricide, an organochlorine insecticide, an organofluorine insecticide, a member of monochlorobenzenes, a nitrile, a member of pyrroles and a hemiaminal ether. It is functionally related to a tralopyril.
Chlorfenapyr is produced commercially through a multi-step synthesis that centres on the creation of its key intermediate: 2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile. This compound is synthesised via a series of reactions involving halogenated aromatic precursors and pyrrole derivatives. Once the intermediate is obtained, it undergoes etherification with ethyl chloroacetate to form the final active ingredient, 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile.
A poison by ingestion. Moderately toxic by
inhalation.
Acaracide, Insecticide, Miticide: Severely Restricted for use in EU. Active in U.S. as a foliar spray in greenhouses for ornamental crops and target pests including mites, caterpillar pests, thrips, and fungus gnats. No food use in U.S. Used on ornamental crops in commercial greenhouses to control mites, caterpillar pests, thrips and fungus gnats. Not for food use. Not an approved substance in EU countries. Registered for use in the U.S.
AC 303630®; CL 303630®; PHANTOM®; PIRATE® 3 F; PYLON®; SUMILARV® chlorfenapyr Chemical class: Pyrrole (Pyrazole); Organofluorine
Limited systemic activity, mainly stomach but some contact action. Uncoupler of oxidative phosphorylation.
[1] BLACK B.C. Insecticidal Action and Mitochondrial Uncoupling Activity of AC-303,630 and Related Halogenated Pyrroles[J]. Pesticide Biochemistry and Physiology, 1994, 50 2: Pages 115-128. DOI:
10.1006/pest.1994.1064[2] C. SHEPPARD J A J. Increased Susceptibility of Pyrethroid-Resistant Horn Flies (Diptera: Muscidae) to Chlorfenapyr[J]. Journal of Economic Entomology, 1998, 91 1: 398-400. DOI:
10.1093/jee/91.2.398[3] KAMARAJU RAGHAVENDRA. Chlorfenapyr: a new insecticide with novel mode of action can control pyrethroid resistant malaria vectors.[J]. ACS Applied Bio Materials, 2011: 16. DOI:
10.1186/1475-2875-10-16
Insecticide; Acaricide; Miticide
