Grundinformationen
- Standard-SMILES
CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1- InChIKey
KAATUXNTWXVJKI-UHFFFAOYSA-N- Summenformel
- C22H19Cl2NO3
- Durchschnittliche Molmasse
- 416,3 g/mol
- Monoisotopische Masse
- 415,0741989
Namen und Bezeichner
- Bevorzugter Name
- Cypermethrin
- IUPAC
- [cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
- Englischer Name
- [cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethyl-c yclopropane-1-carboxylate
- Summenformel
- C22H19Cl2NO3
- Molmasse
- 0
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6
- Polarare Oberfläche (TPSA)
- 59,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 643
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 6.60
6.3
Density
1.25 g/cu cm at 20 °C
Relative density (water = 1): 1.1
Color/Form
Viscous semi-solid
Colorless crystals - pure isomers
Solubility
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
Decomposition
When heated to decomp it emits toxic fumes of /cyanide, nitrogen oxides, chloride/.
220 °C
Melting Point
70 °C
MP: 60-80 °C (technical)
60-80 °C
158 °F
Vapor Pressure
1.7X10-9 mm Hg at 20 °C
Vapor pressure, Pa at 20 °C:
1.7x10-9 mmHg
Physical Description
An emulsifiable concentrate or wettable powder composed of a mixture of eight different isomers; [EXTOXNET]
YELLOW VISCOUS LIQUID-TO-PASTE WITH CHARACTERISTIC ODOUR.
Yellow viscous liquid or semi-solid. Pure isomers are colorless crystals.
Stability/Shelf Life
Relatively stable in neutral & weakly acidic media, with optimum stability at pH 4. Hydrolyzed in alkaline media. Relatively stable to light in field situations. Thermally stable up to 220 °C.
Pyrethrins ... /are/ stable for long periods in water-based aerosols where ... emulsifiers give neutral water systems. /Pyrethrins/
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
Gefahrenhinweise
Regulatory Information
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
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
Hazards Summary
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]
Special Reports
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Cypermethrin (revised 01/14/08), EPA OPP-2005-0293 (June 14/ 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of January 6, 2011: http://www.epa.gov/pesticides/reregistration/status.htm]
WHO; Environ Health Criteria 82: Cypermethrin (1991). EHC are designed for scientists and administrators responsible for the establishment of safety standards and regulations and provide basic scientific risk evaluations of a wide range of chemicals and groups of chemicals.
WHO; Health and Safety Guide for Cypermethrin. Companion document to the Environmental Health Criteria 82[Available from, as of February 16, 2011: http://www.inchem.org/documents/hsg/hsg/hsg022.htm]
IPCS; Poisons Information Monograph 163, Cypermethrin. Poisons Information Monographs (PIM) are a global database with evaluated information on substances commonly involved in cases of poisoning.[Available at, as of February 16, 2011: http://www.inchem.org/documents/pims/chemical/pim163.htm]
FIFRA Requirements
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.
History and Incidents
Cypermethrin poisoning was reported in five office workers at an accounting office of approximately 1000 sq ft in size that was treated for insect control. Treatment inside the building was accomplished by vertical drilling and injecting the chemical under the slab. Exterior walls were drilled from outside the foundation; cypermethrin was then injected in these holes. The employees entered the building 2 days after treatment and experienced dizziness, headaches, nausea, and vertigo immediately. Turning on the air conditioning system worsened their symptoms After 5 min they left the building; however, they repeatedly reentered the building for short periods. Six days later fans were used to draw off the vapors. Airborne concn were below the limit of analysis by 13 days after treatment whereupon the employees reentered the building, only to suffer a return of their symptoms which again worsened when the air conditioning unit was turned on. Six weeks later air sampling indicated concn less than the detection limit. Wipe samples showed the greatest concn, 4240.0 ug/sq foot to be on the hallway carpet between two applicator holes. Several of the holes drilled by the applicator were drilled into the transverse ducts running underground and connecting with the main duct. Cypermethrin had been directly injected into the ventilation ducts. The exact exposure levels to which the workers had been subjected when they turned on the air conditioning unit was not known.
DOT Hazard Classification
Cypermethrin
Severe marine pollutant
Sicherheit und Schutzausrüstung
First Aid Measures
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 .
Fire Fighting Procedures
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
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
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/
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Incinerate cypermethrin in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert (May 1985)).
Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. /Pyrethrin products/
Spillage Disposal
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Do NOT wash away into sewer. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive Measures
Avoid contact with skin. Keep out of any body of water. Do not contaminate water by cleaning of equipment or disposal of waste. Do not reuse empty container. Destroy it by perforating or crushing. /Pyrethrum/
If /pyrethrins/ are not involved in a fire: keep /pyrethrins/ out of water sources and sewers. Build dikes to contain flow as necessary. /Pyrethrins/
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Toxikologische Informationen
Treatment
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
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.
Health Effects
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
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
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).
Food Survey Values
According to compiled results of the US Food and Drug Administration's pesticide residue monitoring programs (including the Total Diet Study) for fiscal years 1978-1990, cypermethrin has been detected as a pesticide residue in American foods(1-4). As part of the FDA Total Diet Study, the concentrations of cypermethrin detected in boiled collards, raw iceberg lettuce, and boiled broccoli were 0.442 ppm (range, 0.052-1.247 ppm), 0.0185 ppm (range, 0.013-0.024 ppm), and 0.013 ppm, respectively(5). During a 5-yr period from 1982-1986, FDA's Los Angeles District Laboratory analyzed 19,581 samples of domestic and imported food and feed commodities for pesticide residues(2); cypermethrin was detected in only 2 samples at concentrations of 0.1-0.5 ppm(2). For fiscal years 1988 and 1989, 27,065 food samples were collected and analyzed for pesticide residues by 10 state laboratories (CA, NY, FL, IN, MA, MI, NC, OR, VA and WI)(6); cypermethrin was detected in only 1 sample (concentration not reported)(7). Fruits (802) and vegetables (1536) collected by the food inspection branch from farms, food terminals, warehouses and points of consumer purchase in Ontario, Canada 1991 to 1995 had 221 reported detections of cypermethrin at <5 ug/g(8).
Between July 1988 and June 1990 in Pakistan, foods were tested for cypermethrin residues(1). Cypermethrin was not detected in fenugreek, aubergine(brinjal), sweet potato, potato, green pepper, capsicum, radish, garlic, peas, french beans, mustard, ginger, arum, gourd, cow pea, radish seeds, parsley, long cucumber, cluster bean, lemon, peach, apple, persimmon (amlok), banana, pomegranate, grapes, musk melon, orange, grapefruit, papaya, sapota, Ziziphus, cherry, plum, apricot, pear, watermelon, sugar cane, or cheeko in the same study(1).;Table: Positive cypermethrin detections. [Table#6096]
Cypermethrin was analyzed in 397 samples collected in 8 local markets from 6 Egyptian governorates (Cairo, Giza, Qualubiya, Beni Suef, Minufiya and Ismailia) in 1995 and was reported not detected in cabbage, cauliflower, carrot, courgette, cucumber, eggplant, green beans, green peas, lettuce, onion, pepper, apple, cantaloupe, grape, guava, mango, orange, peach or strawberry, but was detected in 1 of 62 tomato samples at a concentration of 1.1 mg/kg(1). Cypermethrin was also analyzed in 1579 samples collected in the same Egyptian governorates in 1996 and was not detected in cabbage, grape leaf, lettuce, melokhia, spinach, watercress, artichoke, broad bean, cauliflower, cantaloupe, cucumber, eggplant, green beans, green peas, okra, onion, pepper, squash, carrot, sweet potato, taro, banana, fig, lemon, lime, mango, peach, pear, plum, or pomegranate(2). Cypermethrin was detected in 8 of 86 tomato at 0.28 mg/kg, 1 of 49 apple at 0.14 mg/kg, 1 of 5 apricot at 0.57 mg/kg, 4 of 54 date at 0.37 mg/kg, 3 of 47 grape at 0.46 mg/kg, 1 of 72 guava at 0.12 mg/kg, 1 of 64 orange at 0.05 mg/kg and 2 of 38 strawberry at 0.35 mg/kg(2). Cypermethrin was detected in 20% of 30 tomato samples and 30% of 20 grape samples at 2.4 to 19.1 and 4.1 to 30.1 ppb, respectively, in samples taken from Alexandria City, Egypt from June 1997 to August 1998(4). Cypermethrin was undetected (detection limit 1.0 ppb) in 10 eggplant, 20 cucumber, 18 potato, 12 apple and 12 orange samples taken in the same survey(3).
Cypermethrin was detected in cabbage at a concentration of 23 ug/kg in Greece between March and April 1998(1). Agricultural products monitored in Prefecture, Japan from April 1995 to March 2000, found cypermethrin in 10 of 291 domestic tomato/spinach samples at concentrations of <0.5 ug/g, and in 3 of 106 Japanese persimmon samples at concentrations of <0.05 ug/g, but was not detected in any of the other 368 products sampled(2). Of 173 agricultural products analyzed in 2006 in Japan, six were reported to contain cypermethrin at 3.8-290 ng/g(3). Cypermethrin was not detected (detection limit 0.015 mg/kg) in 130 commercial egg samples taken from Sao Paulo City, Brazil from Oct 2003 to July 2005(4). In a market basket survey conducted Oct 1996 to May 1997 in Trinidad, West Indies, cypermethrin was not detected in sweet pepper, cabbage, celery, lettuce, cauliflower, pak-choi, cucumber, spinach, chive, tomato, hot pepper, cilantro, okra, watercress, eggplant, sorrel fruit or green beans(5). Cotton seeds, used as an edible oil, tested for cypermethrin from 5 locations in Punjab, India were reported as <0.01 mg/kg from the first pick but had concentrations of <0.01 to 0.247 mg/kg from the second pick(6). Cypermethrin was detected in 3 of 7 tomato samples at 0.04 to 0.16 mg/kg and in 1 of 2 potato samples at 0.50 mg/kg, cypermethrin was not detected in cabbage, peppers, onions or cucumbers, samples were taken July thru Aug 2006 from open field and plastic shed conditions in Belgrade, Serbia(7). Cypermethrin was not detected (detection limit 0.04 mg/kg) in mangoes treated with multi-class pesticides in Lucknow, Ultar Pradesh(8). Of 270 samples taken cypermethrin was detected in 11 apple and one citrus fruit sample taken 1999 to 2001 in Karachi, Pakistan at levels of a trace to 5.56 ppm(9). Cypermethrin was detected in garlic, onion, radish, sugar beet, turnip, mint, salad, spinach, brinjal, chilies, cucumber, Lady's fingers, luffa, pumpkin, peas, tomato, cabbage and cauliflo
Results of cypermethrin application to jute sacks containing cowpea or lentils (seeds obtained from New Delhi) at 15 or 25 mg/sq m to test seed contamination(1).;Table: Units mg/kg; detection limit not reported [Table#6097]
Exposure Routes
The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).
Milk Concentrations
ENVIRONMENTAL: Pyrethroids (permethrin, cyfluthrin, cypermethrin and deltamethrin) were found in the breastmilk of nursing mothers in 3 South African towns. Average levels in breastmilk ranged from 8.3 to 48.4 mcg/L in the 3 towns. The source was thought to be from a dusting powder widely available and used in gardening. The dosage and route of exposure (i.e., topical, inhalation, oral) could not be determined. All milk levels were below the allowable daily limit for permethrin.
A study was undertaken to determine residues of cypermethrin in the milk of cows wearing ear tags impregnated with cypermethrin (to control horn flies and other insects)(1); 60 milk samples were collected from 10 cows over a 21-day period(1); 49 samples were below detection limits of 4 ug/kg(1); concentrations in the butterfat of the other samples ranged from 4.0 to 9.6 ug/kg(1).
Toxicity Summary
Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)
Ecotoxicity Excerpts
/BIRDS and MAMMALS/ Results of reproductive studies in mallard ducks and bobwhite quail show no treatment-related effects on adult birds, reproductive parameters, or offspring at the highest dietary concentrations tested in these studies (50 mg a.i/kg diet).
/AQUATIC SPECIES/ ... A freshwater fish Channa punctatus was exposed to subacute concentrations of ... cypermethrin ... for 96 hr ... Significant enhancement in the level of DNA was recorded in all tissues of the fish at high concentration of cypermethrin, whereas RNA and protein contents increased in tissues at all concentrations of cypermethrin tested. ... Cypermethrin treatment induced RNA/DNA ratio in all fish organs tested ... . Protein/DNA ratios were found to be tissue specific in treatments ...
/AQUATIC SPECIES/ ... This paper investigate/s/ the response of GST activity in the /shore crab, Carcinus maenas exposed to cypermethrin/, and also the time course of the induction process. GST activity is significantly increased in Carcinus exposed to nominal concentrations of 50 and 500 ng/L of water-borne cypermethrin. Carcinus demonstrate a significant elevation in GST activity following intra-cephalothoracic injection with 10 ng of cypermethrin. GST activity returns to basal levels after 36 hr. The potential application of GST activity in Carcinus as a biomarker of cypermethrin exposure is discussed. 206409
/AQUATIC SPECIES/ The effect of exposure to sub-lethal concentrations of cypermethrin ... on biochemical parameters of muscle, blood and enzyme activities in brain, liver and kidney of the Indian major carp, Labeo rohita was studied. The sub-lethal exposure studies were done for up to 45 days at 1/10 and 1/50 of 96 hr LC50 of cypermethrin. The 96 hr LC50 was found to be 0.139 ppm. RNA levels decreased while DNA levels were elevated. Acid phosphatase was unchanged while alkaline phosphatase was depleted. Brain acetylcholinesterase activity was decreased significantly (P<0.05) over a period of 45 days at both cypermethrin concentrations. Lactate dehydrogenase activity in brain and liver was elevated, but inhibited in kidney. Succinate dehydrogenase and ATPase activities were depleted in brain, kidney and liver. There was a decrease in serum protein level over control at both concentrations of the pyrethroid. Blood glucose level and total leucocytes were elevated compared with controls at either concentration from day 15 to day 45. Hemoglobin percentage and total erythrocytes decreased in both sub-lethal concentrations. ...
For more Ecotoxicity Excerpts (Complete) data for CYPERMETHRIN (44 total), please visit the HSDB record page.
Regulatorische Informationen
Regulatory Information
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
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.
Chemie und Industrie
Pharmakologische Informationen
ATC Code
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
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
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).
Absorption, Distribution and Excretion
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.
Verwendung und Herstellung
Uses
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.
Formulations/Preparations
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.
Use Classification
Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes
Insecticides
Environmental transformation -> Pesticides (parent, predecessor)
General Manufacturing Information
The WHO Recommended Classification of Pesticides by Hazard identifies cypermethrin (technical grade) as Class IB: highly hazardous; Main Use: insecticide.
Natural pyrethrins, the insecticidal ingredient occurring in the flowers of Tanacetum cinerariaefolium (also known as Chrysanthemum cinerariaefolium or Pyrethrum cineratiae-folium), have been used widely for human and animal health protection by controlling indoor pest insects such as cockroaches, houseflies, and mosquitoes. Natural pyrethrins consist of six compounds (pyrethrin I and II; jasmolin I and II; and cinerin I and II). ... Extensive efforts on modification of chemical structures have been made ... to improve chemical properties in terms of stability in the environment (air, light, and heat) as well as better biological performance (higher selective toxicology). From these investigations, many synthetic pyrethroids have been elaborated ... . They can be classified into the so-called first-generation pyrethroids, which are esters of chrysanthemic acid and alcohols having furan ring and terminal side chain moieties, is to be he highly sensitive to light, air, and temperature. Therefore, these pyrethroids have been used mainly for control of indoor pests. On the other hand, the second generation pyrethroids, which commonly have 3-phenoxybenzyl alcohol derivatives in the alcohol moiety, have excellent insecticidal activity as well as sufficient stability in outdoor conditions by replacement of photolabile moieties with dichlorovinyl, dibromovinyl substituent and aromatic rings. Thus, the second generation pyrethroids are used worldwide for agricultural pests.
The WHO Recommended Classification of Pesticides by Hazard identifies alpha-cypermethrin (technical grade) as Class II: moderately hazardous; Main Use: insecticide. /alpha-Cypermethrin/
alpha-Cypermethrin ... Insecticide ... US: Currently not registered. Outside US: in Jordan. /alpha-Cypermethrin/
For more General Manufacturing Information (Complete) data for CYPERMETHRIN (12 total), please visit the HSDB record page.
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