Cypermethrin

Last updated
Cypermethrin
Alpha-cypermethrin.svg
Cypermethrin 3d model.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH Cypermethrin
PubChem CID
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 Yes check.svgY
    Key: KAATUXNTWXVJKI-UHFFFAOYSA-N Yes check.svgY
  • 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
P03BA02 ( WHO ) QP53AC08 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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 Pesticide Information Center (NPIC) (previously National Pesticides Telecommunication Network) in the USA [1] . It is found in many household ant and cockroach killers, including Raid, Ortho, Combat, ant chalk, and some products of Baygon in Southeast Asia.

Contents

Uses

Cypermethrin is used in agriculture to control ectoparasites which infest cattle, sheep, and poultry. [2]

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. [3] 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. [4] 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. [5]

Study in animals

Cypermethrin is very toxic to cats which cannot tolerate the therapeutic doses for dogs. [6] 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 reproductive system by Elbetieha et al. 2001. [7] In another result, after 15 days of continual dosing, both androgen receptor levels and serum testosterone levels were significantly reduced. These data suggested that cypermethrin can induce impairments of the structure of seminiferous tubules and spermatogenesis in male rats at high doses. [8]

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. [9]

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. [10] Cypermethrin is classified as a possible human carcinogen, because it causes an increase in the frequency of lung tumors in female mice. Cypermethrin has been linked to an increase in bone marrow micronuclei in both mice and humans. [11]

One study showed that cypermethrin inhibits “gap junctional intercellular communication”, which plays an important role in cell growth and is inhibited by carcinogenic agents. [12] Studies have shown that residue from cypermethrin can last for 84 days in the air, on walls, the floor and on furniture. [13]

Environmental effects

Cypermethrin is a broad-spectrum insecticide, which means it kills beneficial insects as well as the targeted insects. [14] Fish are particularly susceptible to cypermethrin, [15] [16] but when used as directed, application around residential sites poses little risk to aquatic life. [17] Resistance to cypermethrin has developed quickly in insects exposed frequently and can render it ineffective. [18]

Related Research Articles

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, industrial buildings, for vector control, and control of insect parasites of animals and humans.

<span class="mw-page-title-main">Piperonyl butoxide</span> Chemical compound

Piperonyl butoxide (PBO) is a pale yellow to light brown liquid organic compound used as an adjuvant component of pesticide formulations for synergy. That is, despite having no pesticidal activity of its own, it enhances the potency of certain pesticides such as carbamates, pyrethrins, pyrethroids, and rotenone. It is a semisynthetic derivative of safrole and is produced from the condensation of the sodium salt of 2-(2-butoxyethoxy) ethanol and the chloromethyl derivative of hydrogenated safrole (dihydrosafrole); or through 1,2-Methylenedioxybenzene.

<span class="mw-page-title-main">Pyrethrin</span> Class of organic chemical compounds with insecticidal properties

The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.

<span class="mw-page-title-main">Bifenthrin</span> Chemical compound

Bifenthrin is a pyrethroid insecticide. It is widely used against ant infestations.

<span class="mw-page-title-main">Pyrethroid</span> Class of insecticides

A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums. Pyrethroids are used as commercial and household insecticides.

<span class="mw-page-title-main">Fenvalerate</span> Chemical compound

Fenvalerate is a synthetic pyrethroid insecticide. It is a mixture of four optical isomers which have different insecticidal activities. The 2-S alpha configuration, known as esfenvalerate, is the most insecticidally active isomer. Fenvalerate consists of about 23% of this isomer.

<span class="mw-page-title-main">Permethrin</span> Medication and insecticide

Permethrin is a medication and an insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As an insecticide, it can be sprayed onto outer clothing or mosquito nets to kill the insects that touch them.

<span class="mw-page-title-main">Imidacloprid</span> Chemical compound

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

<span class="mw-page-title-main">Allethrins</span> Class of synthetic chemicals used as insecticides

The allethrins are a group of related synthetic compounds used in insecticides. They are classified as pyrethroids, i.e. synthetic versions of pyrethrin, a chemical with insecticidal properties found naturally in Chrysanthemum flowers. They were first synthesized in the United States by Milton S. Schechter in 1949. Allethrin was the first pyrethroid.

<span class="mw-page-title-main">Deltamethrin</span> Chemical compound

Deltamethrin is a pyrethroid ester insecticide. Deltamethrin plays a key role in controlling malaria vectors, and is used in the manufacture of long-lasting insecticidal mosquito nets; however, resistance of mosquitos and bed bugs to deltamethrin has seen a widespread increase.

<span class="mw-page-title-main">Mirex</span> Chemical compound

Mirex is an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants but by virtue of its chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. The spread of the red imported fire ant was encouraged by the use of mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976. It is prohibited by the Stockholm Convention on Persistent Organic Pollutants.

<span class="mw-page-title-main">Phenothrin</span> Chemical compound

Phenothrin, also called sumithrin and d-phenothrin, is a synthetic pyrethroid that kills adult fleas and ticks. It has also been used to kill head lice in humans. d-Phenothrin is used as a component of aerosol insecticides for domestic use. It is often used with methoprene, an insect growth regulator that interrupts the insect's biological lifecycle by killing the eggs.

<span class="mw-page-title-main">Cyhalothrin</span> Synthetic pyrethroid used as insecticide

Cyhalothrin is an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids, such as cyhalothrin, are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.

<span class="mw-page-title-main">Dinoseb</span> Chemical compound used as a herbicide

Dinoseb is a common industry name for 6-sec-butyl-2,4-dinitrophenol, a herbicide in the dinitrophenol family. It is a crystalline orange solid which does not readily dissolve in water. Dinoseb is banned as an herbicide in the European Union (EU) and the United States because of its toxicity.

<span class="mw-page-title-main">Methiocarb</span> Chemical compound

Methiocarb is a carbamate pesticide which is used as an insecticide, bird repellent, acaricide and molluscicide since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol and mercaptodimethur.

<span class="mw-page-title-main">Acetamiprid</span> Chemical compound

Acetamiprid is an organic compound with the chemical formula C10H11ClN4. It is an odorless neonicotinoid insecticide produced under the trade names Assail, and Chipco by Aventis CropSciences. It is systemic and intended to control sucking insects (Thysanoptera, Hemiptera, mainly aphids) on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, cotton, cole crops, and ornamental plants. It is also a key pesticide in commercial cherry farming due to its effectiveness against the larvae of the cherry fruit fly.

<span class="mw-page-title-main">Empenthrin</span> Chemical compound

Empenthrin (also called vaporthrin) is a synthetic pyrethroid used in insecticides. It is active against broad spectrum of flying insects including moths and other pests damaging textile. It has low acute mammalian toxicity (its oral LD50 is above 5000 mg/kg in male rats, above 3500 mg/kg in female rats and greater than 3500 mg/kg in mice). It is however very toxic to fish and other aquatic organisms (96-hour LC50 in Oncorhynchus mykiss is 1.7 μg/L, 48-hour EC50 in Daphnia magna is 20 μg/L).

<span class="mw-page-title-main">Tefluthrin</span> Synthetic pyrethroid used as insecticide

Tefluthrin is the ISO common name for an organic compound that is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.

<span class="mw-page-title-main">Ethoprophos</span> Chemical compound

Ethoprophos (or ethoprop) is an organophosphate ester with the formula C8H19O2PS2. It is a clear yellow to colourless liquid that has a characteristic mercaptan-like odour. It is used as an insecticide and nematicide and it is an acetylcholinesterase inhibitor.

<span class="mw-page-title-main">Fenpropathrin</span> Chemical compound

Fenpropathrin, or fenopropathrin, is a widely used pyrethroid insecticide in agriculture and household. Fenpropathrin is an ingestion and contact synthetic pyrethroid. Its mode of action is similar to other natural (pyrethrum) and synthetic pyrethroids where in they interfere with the kinetics of voltage gated sodium channels causing paralysis and death of the pest. Fenpropathrin was the first of the light-stable synthetic pyrethroids to be synthesized in 1971, but it was not commercialized until 1980. Like other pyrethroids with an α-cyano group, fenpropathrin also belongs to the termed type II pyrethroids. Type II pyrethroids are a more potent toxicant than type I in depolarizing insect nerves. Application rates of fenpropathrin in agriculture according to US environmental protection agency (EPA) varies by crop but is not to exceed 0.4 lb ai/acre.

References

  1. "Cypermethrin" (PDF). 5 Nov 2024.
  2. "Cypermethrin". FAO.
  3. Ecobichon, Donald J. (1993). Pesticides and Neurological Diseases. CRC Press. p. 306. ISBN   978-0-8493-4361-2.
  4. "Cypermethrin". Extension Toxicology Network.
  5. R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 389-391.
  6. Linnett, P-J (2008-01-01). "Permethrin toxicosis in cats". Australian Veterinary Journal. 86 (1–2): 32–35. doi:10.1111/j.1751-0813.2007.00198.x. ISSN   1751-0813. PMID   18271821.
  7. Koureas, Michalis; Tsakalof, Andreas; Tsatsakis, Aristidis; Hadjichristodoulou, Christos (2012). "Systematic review of biomonitoring studies to determine the association". Toxicology Letters. 210 (2). Elsevier: 155–168. doi:10.1016/j.toxlet.2011.10.007. ISSN   0378-4274. PMID   22020228.
  8. Hu, JX; Li, YF; Li, J; Pan, C; He, Z; Dong, HY; Xu, LC (2011). "Toxic effects of cypermethrin on the male reproductive system: With emphasis on the androgen receptor". Journal of Applied Toxicology. 33 (7): 576–585. doi:10.1002/jat.1769. PMID   22147539. S2CID   22178796.
  9. Singh, AK; Tiwari, MN; Upadhyay, G; Patel, DK; Singh, D; Prakash, O; Singh, MP (2012). "Long term exposure to cypermethrin induces nigrostriatal dopaminergic neurodegeneration in adult rats: Postnatal exposure enhances the susceptibility during adulthood". Neurobiology of Aging. 33 (2): 404–15. doi:10.1016/j.neurobiolaging.2010.02.018. PMID   20371137. S2CID   207158692.
  10. Amer, S.M.; et al. (1993). "Induction of chromosomal aberrations and sister chromatid exchange in vivo and in vitro by the insecticide cypermethrin". Journal of Applied Toxicology. 13 (5): 341–345. doi:10.1002/jat.2550130508. PMID   8258631. S2CID   41816737.
  11. Amer, S.M.; E.I. Aboulela (1985). "Cytogenetic effects of pesticides. III. Induction of micronuclei in mouse bone marrow by the insecticides cypermethrin and rotenone". Journal of Mutation Research. 155 (3): 135–142. doi:10.1016/0165-1218(85)90132-6. PMID   3974628.
  12. Tateno, C.; Ito, Seiichi; Tanaka, Mina; Yoshitake, Akira; et al. (1993). "Effects of pyrethroid insecticides on gap junctional intecellular communications in Balb/c3T3 cells by dye-transfer assay". Cell Biology and Toxicology. 9 (3): 215–222. doi:10.1007/BF00755600. PMID   8299001. S2CID   10055706.
  13. Wright, C.G.; R.B. Leidy & H.E. Dupree Jr. (1993). "Cypermethrin in the ambient air and on surfaces of rooms treated for cockroaches". Bulletin of Environmental Contamination and Toxicology. 51 (3): 356–360. doi:10.1007/BF00201752. PMID   8219589. S2CID   37107396.
  14. Pascual, J.A.; S.J. Peris (1992). "Effects of forest spraying with two application rates of cypermethrin on food supply and on breeding success of the blue tit (Parus caeruleus)". Environmental Toxicology and Chemistry. 11 (9): 1271–1280. doi:10.1002/etc.5620110907.
  15. Stephenson, R.R. (1982). "Aquatic toxicology of cypermethrin. I. Acute toxicity to some freshwater fish and invertebrates in laboratory tests". Aquatic Toxicology. 2 (3): 175–185. doi:10.1016/0166-445X(82)90014-5.
  16. Ranjani, T. Sri; Pitchika, Gopi Krishna; Yedukondalu, K.; Gunavathi, Y.; Daveedu, T.; Sainath, S. B.; Philip, G. H.; Pradeepkiran, Jangampalli Adi (2020-02-07). "Phenotypic and transcriptomic changes in zebrafish (Danio rerio) embryos/larvae following cypermethrin exposure". Chemosphere. 249: 126148. Bibcode:2020Chmsp.249l6148R. doi:10.1016/j.chemosphere.2020.126148. ISSN   1879-1298. PMID   32062212. S2CID   211134591.
  17. "Cypermethrin" (PDF). National Pesticide Information Center.
  18. Martinez-Cabrillo, J.L.; et al. (1991). "Responses of populations of the tobacco budworm (Lepidopterea: Noctuidae) from northwest Mexico to pyrethroids". Journal of Economic Entomology. 84 (2): 363–366. doi:10.1093/jee/84.2.363.