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Allethrins

From Wikipedia, the free encyclopedia
Class of synthetic chemicals used as insecticides
Allethrin I (R = −CH3)
Allethrin II (R = −COOCH3)

Theallethrins are a group of related synthetic compounds used ininsecticides. They are classified aspyrethroids, i.e. synthetic versions ofpyrethrin, a chemical with insecticidal properties found naturally inChrysanthemum flowers. They were first synthesized in the United States by Milton S. Schechter in 1949. Allethrin was the firstpyrethroid.[1]

They are commonly used inultra-low volume sprays for outdoormosquito control, and in many household insecticides such asRAID, as well asmosquito coils.

Chemical structure

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

Toxicity

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Chronic exposure to allethrins alters the plasma biochemical profile of humans and may have adverse health effects.[2]Bioallethrin has been shown to cause oxidative damage, cellular toxicity and necrosis of human lymphocytes studied in vitro.[3] It is highly toxic to fish and aquatic invertebrates. At normal application rates, allethrin is slightly toxic to bees.[4] Insects subject to exposure become paralyzed (nervous system effect) before dying. Allethrins are toxic to cats[5] because they either do not produce, or produce less of certainisoforms ofglucuronosyltransferase, which serve in hepatic detoxifying metabolism pathways.[6]

Notes

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  1. ^Ujihara, Kazuya (25 July 2019)."The history of extensive structural modifications of pyrethroids".Journal of Pesticide Science.44 (4):215–224.doi:10.1584/jpestics.D19-102.PMC 6861428.PMID 31777441.
  2. ^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.
  3. ^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.
  4. ^"Pesticide Information Profile - Allethrin". pmep.cce.cornell.edu.
  5. ^"Pyrethrin and Permethrin Toxicity in Dogs and Cats". peteducation.com. Archived fromthe original on 2024-05-26. Retrieved2013-05-12.
  6. ^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.

References

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External links

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Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
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