Allethrins

Last updated
Allethrin I (R = -CH3)
Allethrin II (R = -COOCH3) Allethrin 2D.svg
Allethrin I (R = −CH3)
Allethrin II (R = −COOCH3)

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.

Contents

They are commonly used in ultra-low volume sprays for outdoor mosquito control, and in many household insecticides such as RAID, as well as mosquito coils.

Chemical structure

Allethrin I and allethrin II differ by having a methyl group and a methyl ester, respectively, on one terminus. Each of these allethrins consists of the eight possible stereoisomers. A partly enantiopure variant of allethrin I, consisting of only two stereoisomers in an approximate ratio of 1:1, is called bioallethrin. The same mixture of isomers, but in an approximate ratio of 3:1, is known as esbiothrin.

Toxicity

Chronic exposure to allethrins alters the plasma biochemical profile of humans and may have adverse health effects. [1] [ unreliable medical source? ] Bioallethrin has been shown to cause oxidative damage, cellular toxicity and necrosis of human lymphocytes studied in vitro. [2] It is highly toxic to fish and aquatic invertebrates. At normal application rates, allethrin is slightly toxic to bees. [3] Insects subject to exposure become paralyzed (nervous system effect) before dying. Allethrins are toxic to cats [4] because they either do not produce, or produce less of certain isoforms of glucuronosyltransferase, which serve in hepatic detoxifying metabolism pathways. [5]

Notes

  1. Narendra, M.; Kavitha, G.; Helah Kiranmai, A.; Raghava Rao, N.; Varadacharyulu, N.C. (September 2008). "Chronic exposure to pyrethroid-based allethrin and prallethrin mosquito repellents alters plasma biochemical profile". Chemosphere. 73 (3): 360–364. Bibcode:2008Chmsp..73..360N. doi:10.1016/j.chemosphere.2008.05.070. PMID   18657844.
  2. Arif, Amin; Quds, Ruhul; Mahmood, Riaz (December 2021). "Bioallethrin enhances generation of ROS, damages DNA, impairs the redox system and causes mitochondrial dysfunction in human lymphocytes". Scientific Reports. 11 (1): 8300. doi:10.1038/s41598-021-87799-3. PMC   8050322 . PMID   33859309.
  3. "Pesticide Information Profile - Allethrin". pmep.cce.cornell.edu.
  4. "Pyrethrin and Permethrin Toxicity in Dogs and Cats". peteducation.com. Archived from the original on 2013-05-25. Retrieved 2013-05-12.
  5. Court, M. H.; Greenblatt, D. J. (2000). "Molecular genetic basis for deficient acetaminophen glucuronidation by cats: UGT1A6 is a pseudogene, and evidence for reduced diversity of expressed hepatic UGT1A isoforms". Pharmacogenetics. 10 (4): 355–369. doi:10.1097/00008571-200006000-00009. PMID   10862526.

Related Research Articles

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

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. 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.

Pyrethrum was a genus of several Old World plants now classified as Chrysanthemum or Tanacetum which are cultivated as ornamentals for their showy flower heads. Pyrethrum continues to be used as a common name for plants formerly included in the genus Pyrethrum. Pyrethrum is also the name of a natural insecticide made from the dried flower heads of Chrysanthemum cinerariifolium and Chrysanthemum coccineum. The insecticidal compounds present in these species are pyrethrins.

<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 a synergist component of pesticide formulations. 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.

<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 chemicals

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 clothing or mosquito nets to kill the insects that touch them.

<span class="mw-page-title-main">Organophosphate</span> Organic compounds with the structure O=P(OR)3

In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid.

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

Tetramethrin is a potent synthetic insecticide in the pyrethroid family. It is a white crystalline solid with a melting point of 65-80 °C. The commercial product is a mixture of stereoisomers.

<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">Resmethrin</span> Chemical compound

Resmethrin is a pyrethroid insecticide with many uses, including control of the adult mosquito population.

<span class="mw-page-title-main">Mortein</span> Australian pesticide brand

Mortein is an Australian brand of household insecticide owned by the British company Reckitt. Together with its sister product Aerogard, a popular insect repellent, Mortein is widely used in Australia and is marketed internationally. It is also available in New Zealand, India, Pakistan, Fiji, and the Comoros. The brand has been represented in television commercials by cartoon antagonist Louie the Fly.

<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 the ISO common name for 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">Prallethrin</span> Chemical compound

Prallethrin is a pyrethroid insecticide. Prallethrin 1.6% w/w liquid vaporizer is a repellent insecticide which is generally used for the control of mosquitoes in the household.

A fogger is any device that creates a fog, typically containing an insecticide for killing insects and other arthropods. Foggers are often used by consumers as a low cost alternative to professional pest control services. The number of foggers needed for pest control depends on the size of the space to be treated, as stated for safety reasons on the instructions supplied with the devices. The fog may contain flammable gases, leading to a danger of explosion if a fogger is used in a building with a pilot light or other naked flame.

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

Cyfluthrin is a pyrethroid insecticide and common household pesticide. It is a complex organic compound and the commercial product is sold as a mixture of isomers. Like most pyrethroids, it is highly toxic to fish and invertebrates, but it is far less toxic to humans. It is generally supplied as a 10–25% liquid concentrate for commercial use and is diluted prior to spraying onto agricultural crops and outbuildings.

<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">Fenpropathrin</span>

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