Chlorfenapyr is a

pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...

, and specifically a pro-insecticide (meaning it is metabolized into an active insecticide after entering the host), derived from a class of microbially produced compounds known as

halogen The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is ...

ated

pyrrole Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-meth ...

History and Applications

Chlorfenapyr was developed by

Cyanamid American Cyanamid Company was a leading American conglomerate which became one of the nation's top 100 manufacturing companies during the 1970s and 1980s, according to the Fortune 500 listings at the time. It started in fertilizer, but added ...

from the natural product dioxapyrrolomycin, which was isolated from ''

Streptomyces ''Streptomyces'' is the largest genus of Actinomycetota and the type genus of the family Streptomycetaceae. Over 500 species of ''Streptomyces'' bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, ...

fumanus''. The

United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...

initially denied registration in 2000 for use on cotton primarily because of concerns that the insecticide was toxic to birds and because effective alternatives were available. However, it was registered by the EPA in January, 2001 for use on non-food crops in greenhouses. In 2005, the EPA established a tolerance for residues of chlorfenapyr in or on all food commodities. Chlorfenapyr is also used as a wool insect-proofing agent, and was introduced as an alternative to synthetic pyrethroids due to a lower toxicity to mammalian and aquatic life. In April 2016, in Pakistan, 31 people died when their food was spiked with chlorfenapyr.

Mode of Action

Chlorfenapyr works by disrupting the production of

adenosine triphosphate Adenosine triphosphate (ATP) is an organic compound that provides energy to drive many processes in living cells, such as muscle contraction, nerve impulse propagation, condensate dissolution, and chemical synthesis. Found in all known forms of ...

, specifically, "Oxidative removal of the N-ethoxymethyl group of chlorfenapyr by

mixed function oxidase Mixed-function oxidase is the name of a family of oxidase enzymes that catalyze a reaction in which each of the two atoms of oxygen in O2 is used for a different function in the reaction. Oxidase is a general name for enzymes that catalyze oxidat ...

s forms the compound

CL 303268 CL or cl may refer to: Arts and entertainment * CL (rapper) or Lee Chae-rin (born 1991), singer and rapper, former leader of the K-pop girl group 2NE1 * Creative Loafing, a newspaper publisher Brands and enterprises * Colgate-Palmolive's NYS ...

. CL 303268 uncouples oxidative phosphorylation at the mitochondria, resulting in disruption of production of ATP, cellular death, and ultimately organism mortality."

Safety

According to its Safe Data Sheet, chlorfenapyr is "very toxic to aquatic life with long lasting effects".

Notes

External links

31 Die in Pakistan from Chlorfenapyr poisoning

Australian Pesticides and Veterinary Medicines Authority
{{insecticides Insecticides Nitriles Pyrroles Organobromides Chloroarenes Trifluoromethyl compounds Ethers