Cypermethrin

HCID 2912CAS 52315-07-8

Basic information

Standard SMILES
CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
InChIKey
KAATUXNTWXVJKI-UHFFFAOYSA-N
Molecular formula
C22H19Cl2NO3
Average molar mass
416.3 g/mol
Monoisotopic mass
415.0741989

Names & identifiers

Preferred name
Cypermethrin
IUPAC
[cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
English name
[cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethyl-c yclopropane-1-carboxylate
Molecular formula
C22H19Cl2NO3
Molecular weight
0

Names & synonyms

cypermethrin52315-07-8SupercypermethrinBarricadeRipcordAmmoCypermethrineAgrothrinBasathrinCyperkillCymbushSherpa
Show more names
Zeta-Cypermethrin 95%3-(2,2-dichloroethenyl)-2,2-dimethyl[cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethyl-c yclopropane-1-carboxylate
UstaadArdapCymperatorCypercopalHilcyperinNeramethrinCreokhinCyperco

Database identifiers

CAS
52315-07-8、97955-44-7
PubChem CID
2912
DTXSID
DTXSID1023998
ChEBI
CHEBI:4042
UNII
1TR49121NP
EC Number
257-842-9、619-306-6
Nikkaji
J9.674A

Properties

Computed structural properties

XLogP
6
Topological polar surface area
59.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
7
Heavy atoms
28

Experimental & physicochemical properties

LogP · 2 items

log Kow = 6.60

6.3

OdorOdorless
Density · 2 items

1.25 g/cu cm at 20 °C

Relative density (water = 1): 1.1

Color/Form · 2 items

Viscous semi-solid

Colorless crystals - pure isomers

Solubility · 5 items

Soluble in methanol, acetone, xylene, dichloromethane

In acetone, chloroform, cyclohexanone, xylene greater than 450, ethanol 337, hexane 103 (all in g/L at 20 °C).

Soluble in methanol and methylene dichloride

In water, 4X10-3 mg/L at 20 °C

Solubility in water: none

CorrosivityNon-corrosive to metals

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral];H332: Harmful if inhaled [Warning Acute toxicity, inhalation];H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H373: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P319, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Warning

Hazard information

Regulatory Information · 5 items

Hazard Traits - Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Neurotoxicity; Other Toxicological Hazard Traits; Reproductive Toxicity;Authoritative List - CECBP - Priority Chemicals; CWA 303(c); CWA 303(d);Report - if used as a fragrance or flavor ingredient

Commission Regulation No 844/2012

Cypermethrin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

05/53/EC, Reg (EU) 2020/1511, Reg. (EU) 2017/1511, Reg. (EU) 2018/1262, Reg. (EU) 2019/1589, Reg. (EU) 2021/1449, Reg. (EU) 2021/2049, Reg. (EU) No 533/2013, Reg. (EU) No 540/2011

Cypermethrin: HSNO Approval: HSR002833 Approved with controls

Other Safety Information · 1 item

IMAP assessments - Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester: Environment tier I assessment;IMAP assessments - Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester: Human health tier I assessment

Fire HazardsCombustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary · 1 item

Classified as a Restricted Use Pesticide because its toxicity to fish; Moderately toxic by dermal absorption or ingestion with an oral LD50 in mice that varies from 82-779 mg/kg depending on the mixture of isomers; Causes liver changes in animals fed high doses; [EXTOXNET] Pyrethroids have low toxicity to humans after dermal exposure. Of 573 dermal or ingestion poisoning cases in China, 51 patients had disturbed consciousness and 34 had seizures. Of those, only five were occupationally exposed. Seizures are more commonly related to exposures to fenvalerate, flucythrinate, cypermethrin, deltapermethrin, and fluvalinate. Seizures have not been reported after exposure to permethrin. Pyrethroids may also cause paresthesias after skin contact. Paresthesias (stinging and numbness) usually begin 1-2 hours after contact and resolve within 24 hours. [EPA Pesticides, p. 87-8] Pyrethrins cause liver injury when fed to animals at high doses. [EXTOXNET]

EC ClassificationSymbol: Xn, N; R: 22-37/38-43-50/53; S: (2)-36/37/39-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II

Safety & protection

Fire FightingUse powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.
Fire Fighting Procedures · 2 items

Use dry powder, carbon dioxide, alcohol-resistant foam, sand, or earth for dealing with fires. Do not use water. Cool nearby drums with water spray. If pyrethroid products are involved in a major fire or in a fire involving other products, advise the fire service that protective clothing and breathing apparatus should be worn. Also, warn the authorities that pyrethroids are highly toxic for fish, and that the use of water should be confined to the cooling of unaffected stock, thus avoiding the accumulation of polluted run-off from the site.

Extinguish fire using agent suitable for type of surrounding fire. /Pyrethrins/

Storage Conditions · 2 items

Store technical material and formulations away from heat, under lock and key, and out of the reach of children, animals, and unauthorized personnel. Store in an area designated for insecticide storage, preferably without drains. Store away from other chemicals, foodstuffs, and animal feed.

Pyrethrins with piperonyl butoxide topical preparations should be stored in well-closed containers at a temperature less than 40 °C, preferably between 15-30 °C. /Pyrethrins/

Cleanup Methods · 3 items

Avoid exposure, if possible by the use of appropriate protective clothing and masks. Empty any product remaining in damaged or leaking containers into a clean empty drum and label. Absorb spillage with lime, damp sawdust, sand, or earth and dispose of safely (see below). If spillage is large, contain it by building a barrier of earth or sandbags. Decontaminate empty, damaged, or leaking containers with a 10% sodium carbonate solution added at the rate of at least 1 litre per 20 L drum. Puncture containers to prevent reuse.

/Transportation/ accident procedures: Avoid exposure - if possible by the use of appropriate protective clothing and masks. Keep spectators away from leaking or spilled product and prevent smoking or the use of naked flames in the immediate vicinity. Extinguish fires with dry powder, carbon dioxide, alcohol-resistant foam, sand, or earth. Prevent liquid from spreading to other cargo, vegetation, or waterways by containing it with the most readily available barrier material, e.g., earth or sand. Absorb spilled liquid and cover contaminated areas with earth, lime, sand, or other absorbent material. Sweep up and place in a secure container for subsequent safe disposal.

Spillages of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: these should be removed by vacuum cleaning, or by dissolving them in water, or other solvent in the factory environment. /Pesticides/

Toxicology

Treatment · 1 item

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (L363)

Interactions · 5 items

The effects of dissolved organic carbon in the form of Aldrich humic acid on the accumulation and acute toxicities of three synthetic pyrethroids - fenvalerate, deltamethrin, and cyhalothrin - to Daphnia magna in laboratory experiments were investigated. Concn of dissolved organic carbon as low as 2.6 mg/L, 3.2 mg/L, and 3.1 mg/L for deltamethrin fenvalerate, and cyhalothrin, respectively, resulted in a significant decrease in bioaccumulation. Acute toxicities of all three pyrethroids were found to decrease as dissolved organic carbon concn increased; eg, at a dissolved organic carbon concn of 15.5 mg/L, the acute toxicity of fenvalerate was reduced by a factor of 17. The percentages of deltamethrin and fenvalerate bound to dissolved organic carbon increased as dissolved organic carbon concn increased after 2 hr and 24 hr contact times. At low concn of dissolved organic carbon (eg, 1.7 mg/L), as much as 40% of fenvalerate and 20% of deltamethrin were found sorbed to the dissolved material. After 24 hr contact times, 76.4 and 80.8% of fenvalerate and deltamethrin, respectively, were bound to dissolved organic carbon. Reverse-phase partition coefficients for both fenvalerate and deltamethrin were found to vary with dissolved organic carbon concn and were in the range 1.0 to 4.8 to 5.6.

The acute administration of 1R,cis, alpha S-cypermethrin, deltamethrin fenvalerate and permethrin produced a dose-dependent lowering of the dose of pentylenetetrazol required to elicit a seizure in rats. The proconvulsant action of cypermethrin displayed stereospecificity in that the 1R, cis, alpha S isomer of cypermethrin was the most potent compound tested, while the non-insecticidal isomer, 1S,cis, alpha R-cypermethrin, was devoid of proconvulsant activity. Pretreatment of rats with PK 11195, an antagonist of the peripheral-type benzodiazepine binding site, elicited a complete reversal of the proconvulsant actions of both deltamethrin and permethrin. In contrast, pretreatment with phenytoin did not alter the pyrethroid-induced proconvulsant activity. These results suggest that the effects of pyrethroids on pentylenetetrazol seizure threshold are mediated via an interaction with peripheral-type benzodiazepine binding sites.

/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/

Piperonyl butoxide potentiates /insecticidal activity/ of pyrethrins by inhibiting the hydrolytic enzymes responsible for pyrethrins' metabolism in arthropods. When piperonyl butoxide is combined with pyrethrins, the insecticidal activity of the latter drug is increased 2-12 times /Pyrethrins/

For more Interactions (Complete) data for CYPERMETHRIN (9 total), please visit the HSDB record page.

Target OrgansGastrointestinal
Health Effects · 1 item

At high doses, signs of poisoning attributable to cypermethrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema (L863).

Ecotoxicity Values · 5 items

LD50; Species: Anas platyrhynchos (Mallard duck, male) oral >9520 mg a.i./kg bw /92.9% a.i. technical/ /from table/

LD50; Species: Anas platyrhynchos (Mallard duck, female) oral >11227 mg a.i./kg bw /92.9% a.i. technical/ /from table/

LC50; Species: Anas platyrhynchos (Mallard duck, juvenile) diet >2634 ppm for 8 days

LD50; Species: Colinus virginianus (bobwhite quail) oral >2000 mg a.i./kg /97.1% a.i. Beta cypermethrin/ /from table/

For more Ecotoxicity Values (Complete) data for CYPERMETHRIN (67 total), please visit the HSDB record page.

Environmental Fate · 4 items

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 20,800 to 503,000(2-4), indicate that cypermethrin is expected be immobile in soil(SRC). Volatilization of cypermethrin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), based upon its vapor pressure, 1.7X10-9 mm Hg(2), and water solubility, 4X10-3 mg/L(2). Cypermethrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). The photodegradation of the cis- and trans-isomers of cypermethrin were studied by exposing various soil surface applications to sunlight for 7-10 days(5); half-lives on soil surfaces exposed to sunlight ranged from 0.6-1.9 days while half-lives on dark soil were >7 days(5). The half-lives were 4.1 to 17.6 days for trans-cypermethrin and 12.5 to 56.4 days for the cis-cypermethrin under aerobic conditions in an incubated soil(5), indicating rapid biodegradation. After spray applications in an orchard, the half-life of cypermethrin on vegetation under pear and apricot trees ranged from 14-17 days(6); soil contained no detectable cypermethrin after 100-120 days(6). After spraying wheat herbage, cypermethrin residues fell to 50% after 1 day and to 5% after 27 days(7).

TERRESTRIAL FATE: Cypermethrin degradation in soil was rapid, the trans-isomer degraded more rapidly than the cis-isomer. Thirty to 60% of cypermethrin applied was converted to (14)CO2. Hydrolysis of the ester was the primary pathway and produced the carboxylic acid plus 3-phenoxybenzyl alcohol or 3-phenoxybenzaldehyde cyanohydrin. Both of the latter compounds were converted to 3-phenoxybenzoic acid. Another pathway produced the 3-(4-hydroxyphenoxy)benzyl ester which was in turn hydrolyzed. The degradation rate of trans-cypermethrin and cis-cypermethrin was most rapid on sandy clay and sandy loam. About 50% of trans-cypermethrin and cis-cypermethrin applied to the soils decomposed in 2 weeks and 4 weeks, respectively. Six degradation products were observed in soil: the 3-(4-hydroxyphenoxy)benzyl ester; 3-(4-hydroxyphenoxy)benzoic acid; 3-phenoxybenzoic acid; and (+ or -)-cis- and (+ or -)-trans-3-(2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarboxylic acid. Carbon dioxide was also observed.

AQUATIC FATE: Based on a classification scheme(1), Koc values of 20,800 to 503,000(2-4), indicate that cypermethrin is expected to adsorb to suspended solids and sediment(SRC). In a pond experiment, surface applications of cypermethrin gradually partitioned to sediment with sediment concentrations exceeding surface and subsurface water concentrations after 13 days(5); in another pond experiment, dispersion of surface applications to subsurface water and sediment was very slow(5); however, after 4 wks, the concentration in the sediment exceeded the water concentrations(5). Volatilization from water surfaces is not expected(6) based upon an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.7X10-9 mm Hg(2), and water solubility, 0.004 mg/L(2). According to a classification scheme(7), BCFs of 420 in golden ide fish (Leuciscus idus melanotus)(8), 430 in rainbow trout (Oncorhynchus mykiss)(9) and 468 in bluegill (Lepomis macrochirus)(10) suggest bioconcentration in aquatic organisms is high(SRC). Cypermethrin was found to be stable to hydrolysis at pH 5 and 7, and had a half-life of 1.8 to 2.5 days at pH 9(3). The photodegradation of the cis- and trans-isomers of cypermethrin was studied by exposing various aqueous solutions to sunlight for 7-10 days; the half-lives in distilled water solution were 2.6-3.6 days in sunlight and >10 days in dark controls(11); the half-lives in river and seawater were 0.6-1.0 days and >10 days in dark controls(11). Cypermethrin is expected to biodegrade based on biodegradation half-lives of 11.6 to 30.4 days in water at 15 to 19 °C, pH 7.7, and biological oxygen demand of 2.2 mg/L(12). Anaerobic and aerobic half-lives of cypermethrin in water of 9 to 17 days were also reported(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cypermethrin, which has a vapor pressure of 1.7X10-9 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase cypermethrin may be removed from the air by wet or dry deposition(SRC).

Regulatory information

Regulatory Information · 5 items

Hazard Traits - Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Neurotoxicity; Other Toxicological Hazard Traits; Reproductive Toxicity;Authoritative List - CECBP - Priority Chemicals; CWA 303(c); CWA 303(d);Report - if used as a fragrance or flavor ingredient

Commission Regulation No 844/2012

Cypermethrin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

05/53/EC, Reg (EU) 2020/1511, Reg. (EU) 2017/1511, Reg. (EU) 2018/1262, Reg. (EU) 2019/1589, Reg. (EU) 2021/1449, Reg. (EU) 2021/2049, Reg. (EU) No 533/2013, Reg. (EU) No 540/2011

Cypermethrin: HSNO Approval: HSR002833 Approved with controls

FIFRA Requirements · 4 items

Tolerances are established for residues of the insecticide cypermethrin (+/-)alpha cyano-(3-phenoxyphenyl)methyl(+/-)cis,trans-3(2,2-dichloroethenyl-2,2-dimethylcyclopropanecarboxylate in or on the following commodities: [Table#6094]

Tolerances are established for residues of the insecticide Z-cypermethrin (S-cyano(3-phenoxyphenyl) methyl (+/-))(cis-trans 3-(2,2-dichloroethenyl)-2,2 dimethylcyclopropanecarboxylate and its inactive R-isomers in or on the following raw agricultural commodities: /zeta-Cypermethrin/ [Table#6095]

The Agency has completed its assessment of the dietary, residential, occupational and ecological risk associated with the use of cypermethrin. Based on this assessment the Agency has sufficient information to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that cypermethrin containing products are eligible for reregistration provided that label amendments are made as outlined in this RED. ... Based on its evaluation of cypermethrin, the Agency has determined that cypermethrin products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA and FQPA. Accordingly, should a registrant fail to implement any of the reregistration requirements identified in this document, the Agency may take regulatory action to address the risk concerns from the use of cypermethrin. If all changes outlined in this document are incorporated into the product labels, then all current risks for cypermethrin will be adequately mitigated for the purposes of this determination.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Cypermethrin is found on List B. Case No: 2130; Pesticide type: Insecticide (Acaricide); Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): alpha-cyano(3-phenoxyphenyl)methyl(+-)cis,trans-3-(2,2-dichlorovinyl- 2,2-dimethylcyclopropanecarboxylate; Data Call-in (DCI) Date(s): 07/01/91, 03/03/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

State Drinking Water Guidelines(FL) FLORIDA 350 ug/L

Chemistry & industry

Pharmacology

ATC Code · 2 items

P - Antiparasitic products, insecticides and repellents;P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents;P03B - Insecticides and repellents;P03BA - Pyrethrines;P03BA02 - Cypermethrin

QP - Antiparasitic products, insecticides and repellents;QP53 - Ectoparasiticides, insecticides and repellents;QP53A - Ectoparasiticides for topical use, incl. insecticides;QP53AC - Pyrethrins and pyrethroids;QP53AC08 - Cypermethrin

Mechanism of Action · 5 items

Pyrethroid insecticides are synthetic neurotoxins patterned after the naturally occurring pyrethrins. Their mechanism of action is thought to involve effects primarily at the voltage-sensitive sodium channel of both insect & mammalian neurons, although recent studies have raised the possibility that these cmpds may also act at the gamma-aminobutyric acid receptor-chloride ionophore complex. Here we show that active pyrethroids of the alpha-cyano-3-phenoxybenzyl class allosterically enhance the binding of (3)H-batrachotoxinin-A 20-alpha-benzoate to voltage-sensitive sodium channels of rat brain in a dose-dependent & stereospecific manner. Comparison of the rank order of potency for enhancement of (3)H-batrachotoxinin-A 20-alpha-benzoate binding & insecticidal activity in a series of toxic steroisomers of cypermethrin, representative of the class, reveals a correlation between the two measures. These results support a sodium channel site model for pyrethroid action & suggest a useful & practical method to help evaluate the relationship between the sodium channel & insecticidal potency for members of this class of cmpds.

Following absorption through the chitinous exoskeleton of arthropods, pyrethrins stimulate the nervous system, apparently by competitively interfering with cationic conductances in the lipid layer of nerve cells, thereby blocking nerve impulse transmissions. Paralysis and death follow. /Pyrethrins/

The efforts of this study were directed at defining the importance of esterases, mixed function oxidases and mitochondrial respiratory chain enzymes in in vitro covalent binding of cismethrin and the two cyanopyrethroids, cypermethrin and deltamethrin to phenobarbital induced rat liver homogenate and microsomes. Each enzyme system was selectively inhibited to elucidate the activation mechanism involved. Piperonyl-butoxide and carbon-monoxide were used to inhibit mixed function oxidases. Tetraethylpyrophosphate inhibited esterase and trichloropropene-oxide inhibited epoxide-hydrolase. Potassium cyanide or rotenone was used to block the mitochondrial electron transport. The study demonstrated that covalent binding of cismethrin, cypermethrin, and deltamethrin was dependent on pyrethroid concentration. Inhibition of esterases and mitochondrial respiration only slightly altered the covalent binding level. Inhibition of cytochrome p450 and mixed function oxidases reduced the covalent binding, making it almost nonexistent. The covalent binding was decreased by 50% through an 80% inhibition of epoxide-hydrolase. In vitro, the comparison of data between alcohol and acid labeling of the same pyrethroid suggested that the whole molecule was bound to proteins in an activation process, perhaps epoxidation, and that hydrolysis could only occur afterwards. The role of cytochrome p450 dependent monooxygenases in the covalent binding process was stressed.

Interaction with sodium channels is not the only mechanism of action proposed for the pyrethroids. Their effects on the CNS have led various workers to suggest actions via antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, or actions on calcium ions. Since neurotransmitter specific pharmacological agents offer only poor or partial protection against poisoning, it is unlikely that one of these effects represents the primary mechanism of action of the pyrethroids, & most neurotransmitter release is secondary to incr sodium entry. /Pyrethroids/

For more Mechanism of Action (Complete) data for CYPERMETHRIN (12 total), please visit the HSDB record page.

Metabolism/Metabolites · 6 items

In the case of cypermethrin, the relative importance of an esterase attack as opposed to an oxidative one is more important than for permethrin; for trans-cypermethrin the ratio is 93.2% to 17.3% and for cis-cypermethrin 41.5% to 37.6% in the mouse system. In case of deltamethrin (which has only a cis-isomer) the ratio is 28.3% to 41%. Since the mouse system shows a high oxidative ratio, the above figures seem to indicate that esterase metabolism in these pyrethroids is at least as important as the oxidative ones.

The major degradation pathway of cypermethrin is hydrolysis of the ester linkage to /yield ultimately/ 3-phenoxybenzoic acid and 3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylic acid. (From the cis-isomer both cis- and trans- cyclopropanecarboxylic acids are found.) A minor degradative route is ring hydroxylation to give an alpha-cyano-3-(4-hydroxyphenyl)benzyl ester followed by hydrolysis to produce the corresponding hydroxycarboxylic acid.

When administered to rats and mice, a large part of trans-cypermethrin was eliminated in urine in 24 hr. Under similar conditions, 80% of administered 3-phenoxybenzoic acid was eliminated. When cis-cypermethrin was administered, more was excreted via feces. The major urinary metabolite in mice, from trans-cypermethrin and 3-phenoxybenzoic acid, was identified with the aid of MS and NMR as N-(3-phenoxybenzoyl)taurine. A minor metabolite was identified as the sulfate of 3-(4-hydroxyphenoxy)benzoic acid. The taurine conjugate was not found in the rat urine. In rats, the major metabolite was the sulfate conjugate of 3-(4-hydroxyphenoxy)-benzoic acid. Mouse liver microsomal + NADPH preparations hydroxylated trans- and cis-cypermethrin at the t- and c-methyl groups and the 4' and 5 positions. Hydroxylation at the 5 position of trans-cypermethrin was detected only with microsomes treated with tetraethyl pyrophosphate to inhibit esterase activity.

The major metabolic reactions of trans- and cis-cypermethrin were cleavage of ester linkage, oxidation at the trans- and cis-methyl cyclopropane ring and at 4'-position of the phenoxy group, and conversion of the CN group to SCN ion. The following minor species differences were observed: (1) oxidation at 5- and 6-positions of the alcohol moiety was observed in mice but not in rats; (2) ester metabolites such as 2'-OH, 5-OH, and trans-OH,4'-OH-cypermethrin were detected in feces of mice but not of rats. The remarkable species difference in metabolites was the PBacid-taurine conjugate, which was the predominant metabolite in mice, but it was not detected in rats.

For more Metabolism/Metabolites (Complete) data for CYPERMETHRIN (9 total), please visit the HSDB record page.

Cypermethrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. The main route of metabolism was, as anticipated, via hydrolysis of the ester linkage. The cyclopropane-carboxylic acid moiety is subsequently excreted via the urine as the glucuronide conjugate (L857).

MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion · 5 items

On single oral administration of each of (14)C-(1RS)-trans- and (1RS)-cis-cypermethrin labeled in the benzyl ring, the cyclopropane ring, or the CN group to male and female rats at 1-5 mg/kg, carbon-14 from the acid and alcohol moieties was rapidly and almost completely excreted into the urine and feces. The carbon-14 from the CN group was relatively slowly excreted in the urine and feces, the total recovery being 50-67%. The tissue residues of rats treated with the acid- or alcohol-labeled preparations were generally very low except for the fat (ca. 1 ppm). In contrast, the CN-labeled preparation showed relatively high residue levels, especially in the stomach (contents), intestines, and skin.

Dermal exposure to cypermethrin during spray application at up to 46 mg/hr led to an estimation that approximately 3% was absorbed.

Exposure to cypermethrin & its absorption during aerial spraying of an ultra low volume formulation were studied. A contract pilot & mixer/loader at each of two commercial cotton farms in Mississippi were monitored for dermal exposure to cypermethrin during 12 aerial spray applications. Each operation consisted of 1 mixing/loading operation & 1 application of 50 gal of dilute spray soln for about 30 min. Three volunteer mixer/loaders collected their total urine output for 24 hr periods from 1 or 2 days before to 6 days after exposure. Absorption of cypermethrin was evaluated by determining cypermethrin urinary metabolites. All mixer/loaders wore protective equipment. Total potential & actual dermal exposures were estimated. Avg potential exposures (protected & exposed skin) were 1.07 & 10.5 mg/8 hr day (mg/day) for pilots & mixer/loaders, respectively. Actual skin exposures averaged 0.67 mg/day for pilots & 2.43 mg/day for mixer/loaders. 67% of the total potential exposures to pilots occurred on the hands. For the mixer/loaders, exposure involved primarily the arms, trunk, & hands, amounting to 37, 24, & 17% of total exposure, respectively. Absorption by mixer/loaders determined from analyses of urinary metabolites amounted to 46 to 78 ug cypermethrin equivalents per 3 mixed loads & per 12 simulated mixed loads. /It was/ concluded that exposure of pilots & mixer/loaders during aerial application of ultra low volumes is minimal. Only a small proportion of the cypermethrin that contacts the skin is absorbed.

1. Dose excretion studies with cypermethrin (as a 1:1 cis/trans mixture) & alphacypermethrin (1 of the 2 disastereoisomer pairs which constitute cis cypermethrin) were carried out with, in each case, 2 volunteers/dose level. The studies included (a) single oral alphacypermethrin doses of 0.25 mg, 0.50 mg & 0.75 mg followed by repeated alphacypermethrin doses at the same levels, daily for 5 days, (b) repeated oral cypermethrin doses of 0.25 mg, 0.75 mg & 1.5 mg daily for 5 days, & (c) a single dermal application of 25 mg cypermethrin to the forearm. Urine was monitored for the free & conjugated 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid before & after dosing. 2. Metab & rate of excretion of a single oral dose of alphacypermethrin was similar to that of cis cypermethrin, on average, 43% of the dose was excreted as the cyclopropanecarboxylic acid in the first 24 hr urine. There was no incr in urinary metabolite excretion when alphacypermethrin was admin as a repeated oral dose. Subjects excreted, on average, 49% of the dose as the cyclopropanecarboxylic acid in the subsequent 24 hr periods after dosing. 3. There was no incr in the urinary cyclopropanecarboxylic acid excretion when cypermethrin was admin as a repeated oral dose. Subjects excreted, on average, 72% of the trans isomer dose & 45% of the cis isomer dose respectively in the subsequent 24 hr periods after dosing. 4. Approx 0.1% of the applied dermal dose of 25 mg cypermethrin was excreted within 72 hr as the urinary cyclopropanecarboxylic acid. No conclusions can be drawn from such urinary excretion data as to the concn of cypermethrin & its metabolites in the skin or other organs, or the possibility of other routes of metab or excretion.

For more Absorption, Distribution and Excretion (Complete) data for CYPERMETHRIN (9 total), please visit the HSDB record page.

Uses & manufacturing

Uses · 6 items

Pyrethrins are insecticides used mainly in households; Also used to kill insects on pets and in grain storage bins and poultry pens. Dusts containing 0.3% to 0.5% pyrethrins are used on crops. [EXTOXNET]

Farming (Pesticides) [Category: Industry]

For cypermethrin (USEPA/OPP Pesticide Code: 109702) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insecticides (pyrethroid ester insecticides) (Compend Pest Common Names available at

For zeta-cypermethrin (USEPA/OPP Pesticide Code: 129064) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./ /zeta-Cypermethrin/

Cypermethrin is registered for agricultural use as a foliar application on food and feed crops including cotton, pecans, peanuts, broccoli and other Brassicas, and sweet corn. Cypermethrin can be applied to livestock in eartags, and to horses. Cypermethrin is also registered for use on industrial, commercial, and residential sites. It is registered for outdoor use as a soil residual termiticide and to control insect pests such as ants in and on structures, impervious surfaces (in perimeter and crack and crevice treatments) and lawns. Cypermethrin can also be applied indoors to control ants, cockroaches, fleas, and other insects.

Consumption PatternsIn 1992, the estimated annual agricultural application of cypermethrin in the United States was 98 metric tons.
Methods of ManufacturingCypermethrin is produced by condensation of 3-phenoxybenzaldehyde with 3-(2,2-dichlorovinyl)- 2,2-dimethylcyclopropanecarboxylic acid.
Formulations/Preparations · 5 items

Emulsifiable concentrate, ULV, wettable powder.

PREMIX PARTNERS: Acetamiprid; Amitraz; Chlorpyrifos; Chlorpyrifos-methyl; Dichlorvos; Dimethoate; Endosulfan; Ethion; Fenitrothion; Malathion; Phenthoate; Piperonyl Butoxide; Profenofos; Quinalphos; Tetramethrin.

Emulsifiable concentrate. /zeta-Cypermethrin/

PREMIX PARTNERS: Bifenthrin. /zeta-Cypermethrin/

For more Formulations/Preparations (Complete) data for CYPERMETHRIN (111 total), please visit the HSDB record page.

Household ProductsInformation on 62 consumer products that contain Cypermethrin in the following categories is provided:;• Inside the Home;• Pesticides;• Pet Care
Use Classification · 3 items

Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes

Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

Suppliers50 total

湖北博杰生物科技有限公司0713-2060728 15629612610
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
Shaanxi LonierHerb Bio Technology Co Ltd+86-86-+86-86-029-87551862 15002946897 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Cypermethrin is a carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile. It has a role as a pyrethroid ester insecticide, a pyrethroid ester acaricide, an agrochemical and a molluscicide. It is an organochlorine compound, a nitrile, an aromatic ether and a cyclopropanecarboxylate ester. It is functionally related to a 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid.

Related reactions

26 records

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