CHLORFENAPYR: MODE OF ACTION AND METABOLISM

CHLORFENAPYR:

Chlorfenapyr is a pyrrole group of insecticide that is 4-bromo-1H-pyrrole-3-

carbonitrile which is substituted by ethoxymethyl, p-chlorophenyl and trifluoromethyl groups at
1, 2 and 5 positions respectively. This are proinsecticide mainly used for control of termite and
mite pests. It has a role as a proinsecticide and a proacaricide. It derives from a compound named
as tralopyril.

STRUCTURE:

CHLORFENAPYR

PROPERTIES:

 It shows Contact & Stomach action and it also have some systemic actions.
 It shows good translaminar action.
 Affected insects immediately stop feeding and reduce the yield loss.
 Relatively safe for beneficial insects.
 Best fit for IPM programs.
 It is highly compatible with all other pesticides.
 It is a Broad-spectrum insecticide used against Thrips, Mites and Termites.
 This insecticide mainly used for vector management.

MODE OF ACTION OF CHLORFENAPYR:

Chlorfenapyr is a pro-insecticide because due to oxidative removal of the N-

ethoxymethyl group of chlorfenapyr by Mixed Function Oxidases (MFO) inside insect body
leads to a formation of toxic compound which is identified as CL 303268 which uncouples
oxidative phosphorylation in the mitochondria, resulting in disruption of ATP production and
loss of energy leading to cell dysfunction and subsequent death of the organism. This molecule
has low mammalian toxicity and is classified as slightly hazardous insecticide as per WHO
criterion.
 Oxidative phosphorylation Uncoupler

METABOLISM OF CHLORFENAPYR:

Four common chlorfenapyr animal metabolites found are

1. AC 312,094,
2. AC 303,268,
3. AC 322,250 and
4. AC 325,195.

Among the four AC 303,268 shows high acute oral toxicity (LD50 = 27 mg/kg) and It is present
at significant levels in livestock when they fed on insecticide sprayed crop materials.

METABOLIC PROCESS:

1. N-dealkylation
2. Dehalogenation
3. Hydroxylation
4. Oxidation
5. Conjugation

ANIMAL METABOLISM

Chlorfenapyr undergoes extensive metabolism for vertebrates as well as insects involving

modification of the phenyl ring and the substituents of the pyrrole ring. The metabolic pathways
of chlorfenapyr include N-dealkylation, dehalogenation and hydroxylation of both the phenyl
and the pyrrole ring, hydroxylation and oxidation of the N-alkyl group and conjugation to
endogenous components.

ENVIRONMENT METABOLISM

Metabolism of chlorfenapyr take places by aerobic degradation in soil, photo-degradation

on soil, aqueous hydrolysis and photolysis.
RECOMMENDATION:

CROP PEST DOSE

Thrips, Mites 200 ml / Acre
COTTON
Army worm, American bollworm 320 ml / Acre

REFERENCE:

 Krieger, R. 2001. “Handbook of Pesticide Toxicology”. Volume 2, 2nd ed. Academic

Press, p. 1242-1243.
 Raghavendra, K., T. K. Barik, P. Sharma, R. M. Bhatt, H. C. Srivastava, U. Sreehari and
A. P. Dash.2011. “Chlorfenapyr: a new insecticide with novel mode of action can control
pyrethroid resistant malaria vectors”. Malaria Journal.10:16.
 Lovell, J.B., D.E. Wright, I.E. Gard, T.E. Miller, M.E. Treacy, R.W. Addor and V.M.
Kamhi. 1990. “An insecticide/acaricide from a novel class of chemistry”. Brighton Crop
Protection Conference. Pests and Diseases, British Crop Protection Council, Croyden,
UK, 37-42.
 Oliver, S.V., M.L. Kaiser, O.R. Wood, M. Coetzee, M. Rowland and B.D. Brooke. 2010.
“Evaluation of the pyrrole insecticide chlorfenapyr against pyrethroid resistant and
susceptible Anopheles funestus (Diptera: Culicidae)”. Trop Med Int Health, 15:127-131.

QUESTIONS:
1. Chlorfenapyr belongs to _____________group of insecticide. (Ans. Pyrrole)
2. Chemical name of chlorfenapyr_____________________. (Ans. 4-bromo-1H-pyrrole-3-
carbonitrile which is substituted by ethoxymethyl, p-chlorophenyl and trifluoromethyl
groups at 1, 2 and 5 positions)
3. Chlorfenapyr is example of __________________ (Ans. Proinsecticide)
4. Mode of action of chlorfenapyr________________ (Ans. Uncoupler of oxidative
phosphorylation)
5. Chlorfenapyr is mainly used in the control of _________________ (Ans. Mites and
termite)
6. For vector control ____________insecticide. (Ans. Chlorfenapyr)
7. Chlorfenapyr is converted into toxic form after the removal of _________________
(Ans. N-ethoxymethyl group)
8. The toxic form of chlorfenapyr produced in insect body________________ (Ans. CL
303268)
9. As per WHO criterion chlorfenapyr is classified as ___________________ (Ans. slightly
hazardous insecticide)
10. The enzyme that converts chlorfenapyr into toxic form inside insect body is___________
(Ans. Mixed Function Oxidase)
2marks
 1. What is the mode of action of chlorfenapyr?
2. Write about the metabolism of chlorfenapyr?
5marks
1. Write the mode of action and metabolism of chlorfenapyr?