52645-53-1 Usage
Uses
Used in Pest Control:
Permethrin is used as an insecticide for controlling lice, ticks, mites, and fleas. It is effective due to its action on neural cell membranes, causing paralysis in the targeted arthropods.
Used in Medical Treatments:
Permethrin is used as a treatment for infestation with Sarcoptes scabiei (scabies). It is also utilized as an antihyperlipidemic and cholesterol sequestrant.
Used in Military Applications:
Permethrin-treated military uniforms are effective against human body lice, providing protection for soldiers in the field.
Used in Personal Care:
A 1% permethrin cream rinse (Nix) preparation is used for treating head lice with a single application, proving more effective than other treatments like RID.
Used in Fabric and Clothing Treatment:
Permethrin is used to treat clothing, sleeping bags, tents, and fabric used for insect screening. It is particularly helpful in preventing tick and chigger bites, as these crawling arthropods must travel across the treated fabric. The spray formulation is stable through several wash cycles, and a liquid concentrate can be used to impregnate fabric for an extended period.
Used in Combination with DEET-containing Repellents:
The combination of a DEET-containing repellent and permethrin-treated clothing is highly effective against a wide range of biting arthropods, providing additional protection against insect bites.
Indications
Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It
acts on neural cellmembranes, delaying repolarization and causing paralysis. The
compound has no reported adverse properties, is heat and light stable, has 70%
to 80% ovicidal activity, and leaves an active residue on the scalp.
Permethrin 0.5% spray kills ticks and repels mosquitoes and stable flies. It is broken
down when applied to skin and, hence, should be applied to clothing, shoes, tents,
and so on. Spray only enough to moisten the material. Spray on clothing at least 2
hours before wearing. One treatment should last through a few washings.
Air & Water Reactions
Insoluble in water.
Contact allergens
Pyrethroids, also called pyrethrinoids, are neurotoxic
synthetic compounds used as insecticides, with irritant
properties. Cypermethrin and fenvalerate have been
reported as causing positive allergic patch tests, but
only fenvalerate was relevant in an agricultural worker.
Pharmacology
Permethrin is a synthetic pyrethroid that interferes with the influx of sodium
through cell membranes, leading to neurologic paralysis and death of the mite.
There is minimal percutaneous absorption (<2%), which is rapidly hydrolyzed
and excreted in the urine. Permethrin 5% dermal cream (Elimite) is applied for
8 to 12 hours to the entire body from the chin down and is then washed off.
Clinical Use
Permethrin is 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid (3-phenoxyphenyl)methylester or 3-(phenoxyphenyl)methyl (±)-cis, trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate(Nix). This synthetic pyrethrinoid compound is more stablechemically than most natural pyrethrins and is at least as activeas an insecticide. Of the four isomers present, the1(R),trans and 1(R),cis-isomers are primarily responsiblefor the insecticidal activity. The commercial product is amixture consisting of 60% trans and 40% cis racemic isomers.It occurs as colorless to pale yellow low-melting crystalsor as a pale yellow liquid and is insoluble in water butsoluble in most organic solvents.Permethrin exerts a lethal action against lice, ticks, mites,and fleas. It acts on the nerve cell membranes of the parasitesto disrupt sodium channel conductance. It is used as apediculicide for the treatment of head lice. A single applicationof a 1% solution effects cures in more than 99% ofcases. The most frequent side effect is pruritus, which occurredin about 6% of the patients tested.
Safety Profile
Poison by inhalation, intravenous, and intracerebral routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of Cl-. See also ESTERS
Veterinary Drugs and Treatments
Permethrin is synthetic pyrethroid that acts as an adulticide insecticide/miticide. It has knockdown activity against fleas, lice, ticks, and
certain mites (e.g., Cheyletiella, Sarcoptes scabiei) and also has repellant activity. In small animal medicine, it is used primarily for fleas
and ticks on dogs. In large animal and food animal medicine, there are many products (not listed below) available for pour-on, dusting,
and spray use for flies, lice, mites, mosquitoes, ticks and keds.
Permethrin acts by disrupting the sodium channel current in arthropod nerve cell membranes, resulting in paralysis and death.
Environmental Fate
Soil. Permethrin biodegraded rapidly via hydrolysis yielding 3-(2,2-dichloroethenyl)-
2,2-dimethylcyclopropanecarboxylic acid and 3-phenoxybenzyl alcohol (Kaufman et al.,
1981). The reported half-life in soil containing 1.3–51.3% organic matter and pH 4.2–7.7
is <38 days (Worthing and Hance, 1991)In lake water, permethrin degraded more rapidly than in flooded sediment to transand cis-(dichlorovinyl)dimethylcyclopropanecarboxylic acid. The cis isomer was more
stable toward biological and chemical degradation than the trans isomer (Sharom and
SolomPlant. Metabolites identified in cotton leaves included trans-hydroxypermethrin, 2′-
hydroxypermethrin, 4′-hydroxypermethrin, dichlorovinyl acid, dichlorovinyl acid conjugates, hydroxydichlorovinyl acid, hydroxydichlorovinyl acid conjugates, pheDislodgable residues of permethrin on cotton leaves 0, 24, 48, 72 and 96 hours after
application (1.1 kg/ha) were (cis:trans): 0.26:0.38, 0.24:0.34, 0.22:0.32, 0.16:0.24 and
0.15:0.21 μg/m2, respectively (Buck et al., 1980).Photolytic. Photolysis of permethrin in aqueous solutions containing various solvents
(acetone, hexane and methanol) under UV light (λ >290 nm) or on soil in sunlight initially
resulted in the isomerization of the cyclopropane moiety and ester cl
Metabolic pathway
Permethrin was one of the first photostable pyrethroids suitable for field
use.It served as a precursor for others such as its α-cyano analogue,
cypermethrin. As it lacks the cyano group it has no chirality at the acarbon
atom and therefore consists of a mixture of only four isomers. It is
hydrolysed more readily than cypermethrin because it is an ester of a
primary alcohol.
Much of the early research on the metabolism of the synthetic, photostable
pyrethroids was conducted by Casida and co-workers on permethrin.
The published results greatly assisted subsequent work on the
analogues. This is stressed because some of the information reported
below will draw on the metabolic schemes given in the cypermethrin
entry.
The environmental fate of permethrin and its metabolism in plants,
insects, animals and fish have been reported. The insecticide is metabolised
by ester cleavage to its constituent acid and alcohol and subsequent
conjugation of these. The primary metabolites are also subject to oxidation
prior to conjugation. Permethrin itself is also subject to oxidation, the cisisomers
more so than the trans-isomers because the former is more slowly
hy droly sed.
Degradation
Permethrin is stable as a solid but it is readily hydrolysed in solution
under alkaline conditions; it is most stable at pH 4. It is relatively resistant
to photodegradation in the context of field use but it undergoes facile
photoisomerism (Holmstead et al., 1978). It can be degraded under
laboratory conditions affording DCVA (2) and 3-phenoxybenzyl alcohol
(3PBAlc, 3). Under appropriate conditions, trans-permethrin affords 29%
trans-DCVA and 13% cis-DCVA. The mechanisms of these reactions
have been reviewed in detail by Ruzo (1982). Permethrin is resistant to
photo-oxidation; other reactions, such as dechlorination, are of minor
importance. The degradation products are shown in Scheme 1.
Toxicity evaluation
Acute oral LD50 for rats: 430-4,000 mg/kg (cis:trans ca.
40:60); ca. 6,000 mg/kg (cis:trans ca. 20:80)
Check Digit Verification of cas no
The CAS Registry Mumber 52645-53-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,6,4 and 5 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 52645-53:
(7*5)+(6*2)+(5*6)+(4*4)+(3*5)+(2*5)+(1*3)=121
121 % 10 = 1
So 52645-53-1 is a valid CAS Registry Number.
InChI:InChI=1/C21H20Cl2O3/c1-20(2)17(12-18(22)23)21(20,19(24)25)13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17H,13H2,1-2H3,(H,24,25)/p-1
52645-53-1Relevant articles and documents
Use of prochloraz for wood protection
-
, (2009/06/27)
The active compound prochloraz and fungicidal compositions based on prochloraz are highly suitable for protecting wood and timber products against attack and/or destruction by soft-rot fungi.
Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively
Nakatsuji, Hidefumi,Morimoto, Mami,Misaki, Tomonori,Tanabe, Yoo
, p. 12071 - 12080 (2008/03/13)
We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.
Water solvent method for esterification and amide formation between acid chlorides and alcohols promoted by combined catalytic amines: Synergy between N-methylimidazole and N,N,N′,N′-tetramethylethylenediamine (TMEDA)
Nakatsuji, Hidefumi,Morita, Jun-Ichi,Misaki, Tomonori,Tanabe, Yoo
, p. 2057 - 2062 (2007/10/03)
An efficient method for esterification between acid chlorides and alcohols in water as solvent has been developed by combining the catalytic amines, N-methylimidazole and N,N,N′,N′-tetramethylethylenediamine (TMEDA). The present Schotten-Baumann-type reaction was performed by maintaining the pH at around 11.5 using a pH controller to prevent the decomposition of acid chlorides and/or esters and to facilitate the condensation. The choice of catalysts (0.1 equiv.) was crucial: the combined use of N-methylimidazole and TMEDA exhibited a dramatic synergistic effect. The catalytic amines have two different roles: (i) N-methylimidazole forms highly reactive ammonium intermediates with acid chlorides and (ii) TMEDA acts as an effective HCl binder. The production of these intermediates was rationally supported by a careful 1H NMR monitoring study. Related amide formation was also achieved between acid chlorides and primary or secondary amines, including less nucleophilic or water-soluble amines such as 2-(or 4-)chloroaniline, the Weinreb N-methoxyamine, and 2,2-dimethoxyethanamine.
Method for producing cyclopropanecarboxylates
-
, (2008/06/13)
There is disclosed a method for producing cyclopropanecarboxylates of the formula (3): by transesterification in the presence of a lanthanoid metal alkoxide
Methods for producing cyclopropane carboxylates
-
, (2008/06/13)
There is provided a method for producing a cyclopropanecarboxylate of formula (3): wherein R1, R2, R3, R4 and R5 each independently represent:a hydrogen atom, halogen atom,an optionally substituted alkyl group and the like; andR7 represents:an optionally substituted alkyl group, and the like,which is characterized byreacting a cyclopropanecarboxylate of the formula (1) wherein R1, R2, R3, R4 and R5 are as defined above, andR6 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group,with a monohydroxy compound of the formula (2):R7OH ??(2) wherein R7 is the same as defined above,in the presence of an alkali metal hydroxide.
Method for producing cyclopropanecarboxylates
-
Example 1, (2008/06/13)
There is provided a method for producing a cyclopropanecarboxylate of formula (1):???which comprises contacting???a cyclopropanecarboxylate of formula (2):???with a monohydroxy compound of formula (3):R7OH???in the presence of a lithium compound of formula (4):R8OLiwherein R1, R2, R3, R4and R5each independently representa hydrogen atom, a halogen atom,a substituted or unsubstituted alkyl group,a substituted or unsubstituted alkenyl group, ora substituted or unsubstituted aryl group;R6represents an alkyl group having 1 to 10 carbon atoms ora substituted or unsubstituted phenyl group;R7and R8do not simultaneously represent the same and each independently representa substituted or unsubstituted alkyl group, ora substituted or unsubstituted aryl group.
Fungicidal active compound combinations
-
, (2008/06/13)
The present application relates to new active compound combinations composed, on the one hand, of prior art compounds metaconazole, 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl-methyl)cyclopentanol and imidacloprid, 1-[(6-chloro-3-pyridinyl)-methyl]-4,5-dihydro-N-nitro-1H-imidazole-2-amine, and, on the other hand, of other prior-art active compounds, the combinations being extremely suitable for the protection of wood products.
Anti-fouling compositions
-
, (2008/06/13)
An anti-fouling composition comprising a carrier, and a binder, the improvement which comprises an effective amount of at least one insecticide. The composition is applied to the surfaces of articles which come into contact with seawater or brackish water, especially wood. Other conventional anti-fouling agents may also be present.
Para-hydroxyphenylacetic acid for reducing the repellency of insecticides
-
, (2008/06/13)
The present invention relates to the new use of p-hydroxyphenylacetic acid, by itself or in a mixture with other chemical compounds, for reducing the repellency of insecticides in the control of cockroaches, and to cockroach control compositions which comprise these mixtures, details being found in the description.
Search for Routes of Synthesis of Permethrin and Chloropermethrin Starting from Halogen-containing Alkenoic Acids
Badanyan,Stepanyan,Mikaelyan,Ovivyan,Panosyan
, p. 34 - 41 (2007/10/03)
Promising procedures were developed for the synthesis of permethrin and I-chloropermethrin starting from acid chloride, nitrile, and esters of 3,3-dimethyl-2,2,4,6,6-pentachloro-5-alkenoic acid and 3,3-dimethyl-2,2,6,6-tetrachloro-5-alken-4-olide, which were prepared by adding derivatives of trichloroacetic acid to 1,1-dichloro-4-methyl-1,3-pentadiene in the presence of catalytic amounts of monovalent copper ions and amine.
