Prallethrin

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Prallethrin
Prallethrin skeletal.svg
Prallethrin 3D BS.png
Names
IUPAC name
2-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.041.246 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C19H24O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h1,9,14,16-17H,8,10H2,2-6H3 Yes check.svgY
    Key: SMKRKQBMYOFFMU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C19H24O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h1,9,14,16-17H,8,10H2,2-6H3
    Key: SMKRKQBMYOFFMU-UHFFFAOYAR
  • O=C2\C(=C(\C)C(OC(=O)C1C(/C=C(/C)C)C1(C)C)C2)CC#C
Properties
C19H24O3
Molar mass 300.40 g/mol
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 ?)

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.

Contents

Products

A mosquito repellent vaporizer Mosquito repellent 1.jpg
A mosquito repellent vaporizer

It is marketed as a mosquito repellent by Godrej as "GoodKnight Silver Power", SC Johnson as "All Out" and Southern Labs as "Quit Mozz" in India. It is also the primary insecticide in certain products for killing wasps and hornets, including their nests. It is the main ingredient in the consumer product "Hot Shot Ant & Roach Plus Germ Killer" spray. [1]

The vaporizer contains Prallethrin in isoparaffin solvents. The liquid is drawn up through a porous clay carbon wick by capillary action then vaporized with a heater.

Environmental effects

The World Health Organization published in 2004 that "Prallethrin is of low mammalian toxicity, with no evidence of carcinogenicity" and "is very toxic to bees and fish but of low toxicity to birds." [2]

Prallethrin is a member of the pyrethroid class of insecticides. Pyrethroids have historically been classified into two groups, Type I and Type II, based upon chemical structure and neurotoxicological effect. Type I pyrethroids lack an alpha-cyano moiety and induce a syndrome in rats consisting of aggressive sparring, altered sensitivity to external stimuli, and fine tremor progressing to whole-body tremor and prostration. These Type I pyrethroid-specific behaviors are collectively described as the T-syndrome. Type II pyrethroids contain an alpha-cyano moiety and produce a syndrome in rats that includes pawing, burrowing, salivation, and coarse tremors leading to choreoathetosis. These Type II pyrethroid-specific behaviors are collectively described as the CS-syndrome (Verschoyle and Aldridge 1980; Lawrence and Casida 1982). Prallethrin is structurally similar to Type I pyrethroids. The adverse outcome pathway (AOP) shared by pyrethroids involves the ability to interact with voltage-gated sodium channels (VGSCs) in the central and peripheral nervous system, leading to changes in neuron firing, and ultimately neurotoxicity. [3]

Neurotoxicity in animal models

Prallethrin has been evaluated for a variety of toxic effects in experimental toxicity studies. Neurotoxicity was observed throughout the database and is the most sensitive endpoint. Effects were seen across species, sexes, and routes of administration. In the acute rat neurotoxicity study, decreased exploratory behavior was seen at the time of peak effect. Reduced motor activity and transient tremors were also observed in the study. In the subchronic rat neurotoxicity study, a higher arousal rate was observed in animals at the highest dose tested. Clinical signs of neurotoxicity were also observed in other toxicity studies (subchronic and chronic oral studies in dogs, developmental toxicity studies in the rat and rabbit, 21-day dermal and 28-day inhalation studies in rats). No neurotoxic effects were observed in rats in the chronic toxicity study. [3]

Effects were also observed in the liver (rats, mice, and dogs), heart (dogs), and thyroid gland (rats). Some effects were also seen in the kidney (mice and rats). However, neurotoxicity was the most sensitive endpoint in the toxicology database, and other effects were generally seen in the presence of neurotoxicity and/or at higher doses. Liver effects observed included increased weight, elevated serum cholesterol and alkaline phosphatase activity, centrilobular hepatocyte vacuolation, histiocytic infiltration, enlarged liver, and perilobular hepatocellular hypertrophy. In dogs, myocardial fiber degeneration was seen in females in the subchronic study at the highest dose tested. Heart effects were also seen in one mid-dose female in the chronic study (hemorrhage and red discoloration). However, there was no dose response for the observed heart lesions in the study. Thyroid effects were observed in rats and consisted of increases in the number of small follicles and follicular cell hypertrophy and hyperplasia. The thyroid effects were seen in short-term studies in the presence of liver effects. Kidney effects observed were increased weights and histopathology. [3]

Developmental and reproduction studies are available for prallethrin. There was no evidence of increased quantitative or qualitative susceptibility in any of the studies. In the developmental studies, no toxic effects were noted in fetuses up to the highest doses tested. Maternal effects in the studies included tremors, salivation, exaggerated reflexes, and chromorhinorrhea (the discharge of a pigmented secretion from the nose). [4] In the reproduction study, decreased pup body weights were seen during the lactation period. Effects seen in parental animals were decreased body weights and body weight gains, increased liver weights and microscopic findings in the liver, kidney, thyroid, and pituitary. [3]

Toxicity in humans

Prallethrin is classified as “Not Likely to be Carcinogenic to Humans.” No tumors were observed in rat and mouse carcinogenicity studies up to the highest doses tested. In both the rat and mouse studies, the animals could have tolerated higher dose levels; however, EPA determined that dose levels were adequate to assess potential carcinogenicity. [3]

Prallethrin tested negative in the majority of the genotoxicity studies. It also tested negative in an in vitro chromosomal aberration study in Chinese Hamster Ovary (CHO K1) cells without metabolic activation, but tested positive at all doses with metabolic activation. However, clastogenicity was not clearly dose-related, was seen at nontoxic and slightly toxic doses, and was not expressed in in vivo studies and structure-activity comparisons with the other pyrethroids revealed no correlations with clastogenicity. Other gene mutation, chromosomal aberration, and unscheduled DNA synthesis (UDS) studies were negative; therefore, there is no concern for genotoxicity. [3]

Acute lethality studies conducted with prallethrin indicate moderate acute toxicity via the oral and inhalation routes of administration (Category II) and low acute toxicity via the dermal route (Categories IV). It is not irritating to the skin (Category IV) but is minimally irritating to the eye (Category IV). It is not a dermal sensitizer. The weight of evidence from the available guideline, non-guideline, mechanism of action, and pharmacokinetics studies supports characterizing the toxicological profile of pyrethroids, including prallethrin, as being rapid in onset and associated with acute, peak exposures. Also, there is no apparent increase in hazard from repeated/chronic exposures to prallethrin. [3]

Related Research Articles

<span class="mw-page-title-main">Toxicity</span> Degree of harmfulness of substances

Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a substructure of the organism, such as a cell (cytotoxicity) or an organ such as the liver (hepatotoxicity). By extension, the word may be metaphorically used to describe toxic effects on larger and more complex groups, such as the family unit or society at large. Sometimes the word is more or less synonymous with poisoning in everyday usage.

<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.

<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">Bifenthrin</span> Chemical compound

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

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

Ethion (C9H22O4P2S4) is an organophosphate insecticide. Ethion is known to affect a neural enzyme called acetylcholinesterase and prevent it from working.

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

Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity to the GABAA receptors of insects, than to those of mammals, and to its action on GluCl channels, which do not exist in mammals. As of 2017, there did not appear to be significant resistance among fleas to fipronil.

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

Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after The Second World War. Other noteworthy examples of COCs include DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. It is a colourless solid. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.

<span class="mw-page-title-main">Phosmet</span> Organophosphate non-systemic insecticide

Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.

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

Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinated hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents.

<span class="mw-page-title-main">1,1,2,2-Tetrachloroethane</span> Chemical compound

1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.

<span class="mw-page-title-main">Organophosphate poisoning</span> Medical condition

Organophosphate poisoning is poisoning due to organophosphates (OPs). Organophosphates are used as insecticides, medications, and nerve agents. Symptoms include increased saliva and tear production, diarrhea, vomiting, small pupils, sweating, muscle tremors, and confusion. While onset of symptoms is often within minutes to hours, some symptoms can take weeks to appear. Symptoms can last for days to weeks.

<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">Hexachlorocyclopentadiene</span> Chemical compound

Hexachlorocyclopentadiene (HCCPD), also known as C-56, Graphlox, and HRS 1655, is an organochlorine compound with the formula C5Cl6. It is a precursor to pesticides, flame retardants, and dyes. It is a colourless liquid, although commercial samples appear lemon-yellow liquid sometimes with a bluish vapour. Many of its derivatives proved to be highly controversial, as studies showed them to be persistent organic pollutants. An estimated 270,000 tons were produced until 1976, and smaller amounts continue to be produced today. Two prominent manufacturers are Velsicol Chemical Corporation in the US and by Jiangsu Anpon Electrochemicals Co. in China.

<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">Microcystin-LR</span> Chemical compound

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<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">Triazofos</span> Chemical compound

Triazofos is a chemical compound used in acaricides, insecticides, and nematicides.

<span class="mw-page-title-main">EPN (insecticide)</span> Chemical compound

EPN is an insecticide of the phosphonothioate class. It is used against pests such as European corn borer, rice stem borer, bollworm, tobacco budworm, and boll weevil.

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

Novaluron, or (±)-1-[3-chloro-4-(1,1,2-trifluoro-2-trifluoro- methoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea, is a chemical with pesticide properties, belonging to the class of insecticides called insect growth regulators. It is a benzoylphenyl urea developed by Makhteshim-Agan Industries Ltd.. In the United States, the compound has been used on food crops, including apples, potatoes, brassicas, ornamentals, and cotton. Patents and registrations have been approved or are ongoing in several other countries throughout Europe, Asia, Africa, South America, and Australia. The US Environmental Protection Agency and the Canadian Pest Management Regulatory Agency consider novaluron to pose low risk to the environment and non-target organisms and value it as an important option for integrated pest management that should decrease reliance on organophosphorus, carbamate and pyrethroid insecticides.

<span class="mw-page-title-main">Lithium toxicity</span> Medical condition

Lithium toxicity, also known as lithium overdose, is the condition of having too much lithium. Symptoms may include a tremor, increased reflexes, trouble walking, kidney problems, and an altered level of consciousness. Some symptoms may last for a year after levels return to normal. Complications may include serotonin syndrome.

References

  1. "Over-the-Counter Insecticides for Home, Yard and Garden Use 2012 Survey, Fort Collins, Colorado" (PDF). colostat.edu. Colorado State University. 2012. Retrieved May 1, 2015.
  2. "WHO specifications and evaluations for public health pesticides - Prallethrin" (PDF). who.int. World Health Organization. November 2004. Archived from the original (PDF) on 2016-07-05. Retrieved April 30, 2015.
  3. 1 2 3 4 5 6 7 "Prallethrin; Pesticide Tolerances". National Archives and Records Administration. 2014.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  4. Danner, Horace G. (2013). A Thesaurus of Medical Word Roots. p. 92.