Cypermethrin

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Cypermethrin
Names
IUPAC name
[Cyano-(3-phenoxyphenyl)methyl]3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.052.567 Edit this at Wikidata
KEGG
MeSH Cypermethrin
UNII
  • InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3 checkY
    Key: KAATUXNTWXVJKI-UHFFFAOYSA-N checkY
  • InChI=1/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3
    Key: KAATUXNTWXVJKI-UHFFFAOYAW
  • Cl/C(Cl)=C/C3C(C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C
Properties
C22H19Cl2NO3
Molar mass 416.30 g/mol
Pharmacology
QP53AC08 (WHO
)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cypermethrin (CP) is a synthetic pyrethroid used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. It behaves as a fast-acting neurotoxin in insects. It is easily degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. It is a non-systemic and non-volatile insecticide that acts by contact and ingestion, used in agriculture and in pest control products. Exposure to sunlight, water and oxygen will accelerate its decomposition. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticides Telecommunications Network (NPTN). It is found in many household ant and cockroach killers, including Raid, Ortho, Combat, ant chalk, and some products of Baygon in Southeast Asia.

Uses

Cypermethrin is used in agriculture to control

ectoparasites which infest cattle, sheep, and poultry.[1]

Human exposure

Cypermethrin is moderately toxic through skin contact or ingestion. It may cause irritation to the skin and eyes. Symptoms of dermal exposure include numbness, tingling, itching, burning sensation, loss of bladder control, incoordination, seizures and possible death.

Pyrethroids may adversely affect the central nervous system. Human volunteers given dermal doses of 130 μg/cm2 on the earlobe experienced local tingling and burning sensations. One man died after eating a meal cooked in a 10% cypermethrin/oil mix that was mistakenly used for cooking oil.[2] Shortly after the meal, the victim experienced nausea, prolonged vomiting, stomach pains, and diarrhea which progressed to convulsions, unconsciousness and coma. Other family members exhibited milder symptoms and survived after hospital treatment.

It may cause allergic skin reactions in humans.[3] Excessive exposure can cause nausea, headache, muscle weakness, salivation, shortness of breath and seizures.

In humans, cypermethrin is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, which are eliminated in the urine. Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdosage may be confirmed by quantitation of cypermethrin in blood or plasma.[4]

Study in animals

Cypermethrin is very toxic to cats which cannot tolerate the therapeutic doses for dogs.[5] This is associated with UGT1A6 deficiency in cats, the enzyme responsible for metabolizing cypermethrin. As a consequence, cypermethrin remains much longer in the cat's organs than in dogs or other mammals and can be fatal in large doses.

In male rats cypermethrin has been shown to exhibit a toxic effect on the

seminiferous tubules and spermatogenesis in male rats at high doses.[7]

Long-term exposure to cypermethrin during adulthood is found to induce dopaminergic neurodegeneration in rats, and postnatal exposure enhances the susceptibility of animals to dopaminergic neurodegeneration if rechallenged during adulthood.[8]

If exposed to cypermethrin during pregnancy, rats give birth to offspring with developmental delays. In male rats exposed to cypermethrin, the proportion of abnormal sperm increases. It causes genetic damage: chromosomal abnormalities increased in bone marrow and spleen cells when mice were exposed to cypermethrin.

micronuclei in both mice and humans.[10]

One study showed that cypermethrin inhibits “gap junctional intercellular communication”, which plays an important role in cell growth and is inhibited by carcinogenic agents.[11] Studies have shown that residue from cypermethrin can last for 84 days in the air, on walls, the floor and on furniture.[12]

Environmental effects

Cypermethrin is a broad-spectrum insecticide, which means it kills beneficial insects as well as the targeted insects.[13] Fish are particularly susceptible to cypermethrin,[14][15] but when used as directed, application around residential sites poses little risk to aquatic life.[16] Resistance to cypermethrin has developed quickly in insects exposed frequently and can render it ineffective.[17]

References

  1. ^ "Cypermethrin". FAO.
  2. ISBN 978-0-8493-4361-2
    .
  3. ^ "Cypermethrin". Extension Toxicology Network.
  4. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 389-391.
  5. PMID 18271821
    .
  6. PMID 22020228
    .
  7. S2CID 22178796
    .
  8. S2CID 207158692
    .
  9. S2CID 41816737
    .
  10. PMID 3974628
    .
  11. S2CID 10055706
    .
  12. S2CID 37107396
    .
  13. doi:10.1002/etc.5620110907
    .
  14. doi:10.1016/0166-445X(82)90014-5
    .
  15. S2CID 211134591
    .
  16. ^ "Cypermethrin" (PDF). National Pesticide Information Center.
  17. doi:10.1093/jee/84.2.363
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Cypermethrin&oldid=1212407389"