StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project:[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HCID 11442Erstellt: 27. Oktober 2026

Allethrins

D-ALLETHRIN · ESBIOL(R) · D-alletrin · PYRESYN(TM) · BIOALLETHRIN · ESDEPALLETHRINE · Caswell no. 025a · trans-allethrine

https://huagongshe.com/de/chemical/11442

Molekülstruktur von Allethrins

Identifikatoren & physikalische Daten

CAS No.28057-48-9
SummenformelC19H26O3
Durchschnittliche Molmasse302,4 g/mol
Monoisotopische Masse302,18819469 g/mol
SMILESC=CCC1=C(C)C(OC(=O)C2C(C=C(C)C)C2(C)C)CC1=O
InChIKeyZCVAOQKBXKSDMS-UHFFFAOYSA-N
PubChem CID11442
ChEMBLCHEMBL1872535
ChEBICHEBI:34572
EC No.209-542-4
DTXSIDDTXSID8035180

Chemische & physikalische Eigenschaften

XLogP4,8
Polarare Oberfläche (TPSA)43,4
H-Brücken-Donoren0
H-Brücken-Akzeptoren3
Frei drehbare Bindungen6
Schwere Atome22
Formalladung0
Komplexität573
ArzneimittelPharmaceuticals
PestizideAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedPesticides -> Pyrethrins/PyrethroidsPesticide (Allethrin) -> USDA PDB
LogP (Verteilungskoeffizient)4.78
DichteRelative density (water = 1): 1.01
LöslichkeitSolubility in water: none
FlammpunktGREATER THAN 140 °F130 °C66 °C
Siedepunkt165-170BP: 140 °C at 0.1 mm Hg. Vaporizes without decomposition when heated at 150 °C.at 0.013kPa: 140 °C
DecompositionWhen heated to decomposition it emits acrid fumes.
Schmelzpunkt~4 °C
DampfdruckPale, yellow, oily liquid. Specific gravity, d 20/4: 1.005-1.015. Vapor pressure: 1.2X10-4 mm Hg at 30 °C. Miscible with most organic solvents at 20-25 °C. /Pynamin forte/Vapor pressure, Pa at 20 °C:
BrechungsindexOily pale yellow liquid. Index of refraction: 1.5156 at 20.6 °C/D. UV max (ethanol): 232 nm (epsilon 23000). Practically insoluble in water. /Allethrin II/
Physical DescriptionAllethrin appears as a clear amber-colored viscous liquid. Insoluble and denser than water. Toxic by ingestion, inhalation, and skin absorption. A synthetic household insecticide that kills flies, mosquitoes, garden insects, etc.D-trans-allethrin is a clear to amber viscous liquid. A synthetic insecticide structurally similar to pyrethrin.Yellow liquid with a mild aromatic odor[EXTOXNET]PALE YELLOW VISCOUS LIQUID.
Lagerbedingungen0-6°C
EPA chemische InformationenCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1- propenyl)-, (1S)-2-methyl-4-oxo-3-(2-propenyl)- 2-cyclopenten-1-yl ester, (1R,3R)-(28057-48-9)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302+H332 (20.4%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation]P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 142 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302 (48.5%): Harmful if swallowed [Warning Acute toxicity, oral]
Regulatorische InformationenHazard Traits - Developmental ToxicityEndocrine ToxicityReproductive ToxicityAllethrins is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2002/2076Allethrin: HSNO Approval: HSR003289 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Weitere SicherheitsinformationenIMAP assessments - Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, [1R-[1.alpha.(S*),3.beta.]]-: Environment tier I assessmentIMAP assessments - Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester: Environment tier I assessment
DOT-KennzeichnungPoisonClass 9
BrandgefahrenExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:Combustible. Liquid formulations containing organic solvents may be flammable.
BrandpotenzialSlight fire hazard.Combustible
GesundheitsgefahrenExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
GefahrenübersichtSlightly toxic after skin absorption or ingestion with an oral LD50 of 1100 mg/kg in male ratsLiver injury is detected in animal experiments with high oral doses. [EXTOXNET] See Bioallethrin, RN: 584-79-2, with LCLo (rats) = 13,800 mg/m3/4H and a vapor pressure = 0.0000012 mm Hg. [ChemIDplus] 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]
Reaktive GruppeEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
EG-EinstufungSymbol: Xn, NR: 20/22-50/53S: (2)-36-60-61Note: C
UN-EinstufungUN Hazard Class: 6.1UN Pack Group: III
Special ReportsUSEPA/Office of Pesticide ProgramsReregistration Eligibility Decision for Allethrins 167pp. EPA 738-R-07-001 (June 2007). This document provides a thorough review of the scientific data underlying allethrin isomers' registration and fulfills the EPA's requirement to determine whether pesticides containing the active ingredients are eligible for reregistration before calling in data on products.Papadopoulou-Mourkidou EResidue Rev 89: 179-208 (1983). A review with many references on analysis of allethrin & other pyrethroid insecticides.WHOEnvironmental Health Criteria 87: Allethrins - Allethrin, d-Allethrin, Bioallethrin, S-Bioallethrin (1989). EHC publications are monographs designed for scientists and administrators responsible for the establishment of safety standards and regulations. This series issued by the International Programme on Chemical Safety (IPCS), provides basic scientific risk evaluation of a wide range of chemicals and groups of chemicals.
FIFRA-AnforderungenThe Agency has completed its assessment of the human health and ecological risks associated with the use of pesticide products containing the allethrins. The Agency has determined that allethrin-containing products are eligible for reregistration provided that label amendments are made as outlined in Chapter V. ... Based on its evaluation of the allethrins, the Agency has determined that products containing allethrins, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this document, the Agency may take regulatory action to address the risk concerns from the use of the allethrins. If all changes outlined in this document are incorporated into the product labels, then all current risks for the allethrins will be adequately mitigated for the purposes of this determination under FIFRA.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 future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Allethrin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0437Pesticide type: insecticideRegistration Standard Date: 03/24/88Case 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): AllethrinAI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."
BrandbekämpfungExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
Erste-Hilfe-MaßnahmenFresh air, rest.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.Fresh air, rest. Refer for medical attention.
Erste HilfeExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Sichere LagerungProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.
BrandbekämpfungsverfahrenUse carbon dioxide, foam, or dry chemical /on fires involving pyrethroids/. /Pyrethrum/Fire-fighting: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive-pressure mode. /Pyrethrum/
LagerbedingungenPyrethrins 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/Store in a closed drum in a cool, dry place.
Freisetung ohne BrandExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.This pesticide is toxic to fish and aquatic invertebrates. Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollutant Discharge Eliminations System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance, contact your State Water Board or Regional Office of the Environmental Protection AgencyDo not apply directly to water, or to areas where surface water is present, or to inter-tidal areas below the mean high water mark. Do not contaminate water when cleaning equipment or disposing of equipment washwater or rinsate.It could be ... buried in noncrop land away from water. In each of these cases it would be better to mix the product with lime. Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amt of combustible material. Recommendable methods: Incineration & landfill.
Verschüttetes entsorgenPersonal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Do NOT wash away into sewer. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive MeasuresFollow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry.Discard clothing or other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them.Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet.Users should remove clothing/ PPE immediately if pesticide gets inside, then wash thoroughly and put on clean clothing.For more Preventive Measures (Complete) data for ALLETHRINS (11 total), please visit the HSDB record page.
Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Eye PreventionWear safety goggles.
TreatmentFollowing 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)
WechselwirkungenINSECTICIDAL ACTIVITIES OF ALLETHRIN ARE ENHANCED BY PYRETHRIN SYNERGISTS SUCH AS PIPERONYL BUTOXIDE OR BIS(2,3,3,3-TETRACHLOROPROPYL) ETHER, OR N-(2-ETHYLHEXYL)-8,9,10-TRINORBORN-5-ENE-2,3-DICARBOXIMIDE.Diazepam delayed the onset of action of deltamethrin, but not of allethrin, in both the mouse and cockroach.... The ability of agents which alter neurotransmission to prevent or potentiate the effect of convulsive doses of technical grade (15.5% cis, 84.5% trans) allethrin was examined. Intraperitoneal pretreatment with drugs which block noradrenergic receptors or norepinephrine synthesis such as pentobarbital, chlorpromazine, phentolamine, and reserpine depressed the tremor induced by allethrin. The inhibitory effect of reserpine was reversed by phenylephrine. Both the serotonergic blocker, methysergide and the serotonin depletor, p-chlorophenylalanine potentiated the effect of allethrin. Thus, allethrin produces its neurotoxic responses in mice by acting on the brain and spinal levels. Furthermore, adrenergic excitatory and serotonergic inhibitory mechanisms may be involved in the neural pathway through which the allethrin-induced tremor is evoked.Synergists for pyrethroid /insecticidal activity/ may include the following: sesamin, sesamolin, piperonyl-butoxide, Tropital, Sesamex, propyl-isomer, satroxan, sulfoxide, piperonylcyclonene, MGK 264, Synepirin 500, and SKF 5254. /Pyrethroids, data derived from table/For more Interactions (Complete) data for ALLETHRINS (8 total), please visit the HSDB record page.
Gesundheitliche AuswirkungenAs for every type I pyrethroid, allethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia can also occur after dermal exposure to allethrin. It is likely to be a human carcinogen by the oral route. (L857)
ÖkotoxizitätswerteLD50 /Anas platyrhynchos/ (Mallard duck, male, 3-4 months old) oral <2000 mg/kgLC50Species: Gammarus lacustris (Scud, age 2 months)Conditions: freshwater, static, 21.1 °C, pH 7.1, alkalinity 30 mg/L CaCO3Concentration: 38 ug/L for 24 hr (95% confidence interval: 30-49 ug/L) /formulated product/Concentration: 20 ug/L for 48 hr (95% confidence interval: 14-28 ug/L) /formulated product/Concentration: 11 ug/L for 96 hr (95% confidence interval: 8-15 ug/L) /formulated product/For more Ecotoxicity Values (Complete) data for ALLETHRINS (136 total), please visit the HSDB record page.
Umweltverhalten... allethrin is among the least persistent of all pyrethroids and is less persistent than cyallethrins, cyfluthrin, cyhalothrin, deltamethrin, fenvalerate, tefluthrin, and tralomethrin. /Allethrin/
LebensmitteluntersuchungswerteThere are no food uses for the allethrins currently registered ...
Unerwünschte WirkungenNeurotoxin - Other CNS neurotoxin
ExpositionspfadeThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.Inhalation (L858)oral (L858)dermal (L858)eye contact (L858).
ToxizitätsübersichtIDENTIFICATION AND USE: Allethrins is a clear to amber colored viscous liquid which is miscible with most organic solvents. It is completely soluble with chloroform, ethyl acetate, toluene and dichloromethane and it is stable under normal conditions and use. Allethrins are a mixture of isomers and the product is used as an insecticide. HUMAN EXPOSURE and TOXICITY: Despite their extensive world wide use, there are relatively few reports of human pyrethroid poisoning. In individuals exposed to pyrethroids, dermalapplication to the skin has resulted in paresthesia and may be stimulated by increases in heat, sunlight, scratching, humidity, or the application of water. Pyrethroid ingestion can cause sore throat, nausea, vomiting and abdominal pain. Dizziness and fatigue are common, and palpitations, chest tightness and blurred vision have also occurred. Contact allergy to pyrethroids has also been noted. Upper respiratory tract symptoms can include rhinitis, sneezing, scratchy throat, oral mucosa and laryngeal edemalower respiratory symptoms can include cough, shortness of breath, wheezing and chest pain and an asthma like condition. S-bioallethrin caused an inhibition of human lymphocyte proliferation in 72 hr culture in a concentration dependent manner. Pyrethroids are not cholinesterase inhibitors. Pyrethrins are irritating to the eye. Skin rash on moist areas of the body have been observed. Employees with chronic respiratory and skin diseases may be at increated risk to pyrethrum exposure. Persons sensitive to rag weed may show sensitiziation to pyrethroids. Individuals may be exposed to allethrins during pesticide applications and inhalation exposures may result when consumers use space spray products, patio foggers, mosquito coils and fly mats. ANIMAL STUDIES: When undiluted and diluted technical allethrin in olive oil were applied to the dorsal skin of rabbits. No differences were noted between treated and control animals. Solutions of different concentrations of allethrin applied to the eyes of rabbits produced eyelid closure, slight conjunctival hyperemia and lacrimation. Allethrin solution applied topically to the backs of male guinea pigs and then rechallenged showed a sporadic pink color on the site of application. Histological examination revealed slight lymphocytic and monocytic infiltration of the dermis in allethrin treated animals. Bioallethrin did not produce any irritation, but produced slight sensitization in guinea pigs. It was also a slight irritant to the skin of rabbits. Rats exposed to allethrin mosquito repellant had significant increases in weights livers and adrenal gland in males, brain and thyroid in females. Changes in liver enzymes were also noted. Allethrin administered in the diets to male Wistar rats a decrease in body weight gain, and increases in liver and kidney weights were observed. Bile ductile proliferation was also noted. ICR mice exposed to a mist of d-allethrin or S-bioallethrin. No significant effects were noted in pregnant ICR mice exposed to d-allethrin or S-Bioallethrin on gestation days 7-12. Allethrin given allethrin by intubation to pregnant albino rabbits there was no evidence of compound related effects. Allethrin was strongly positive at low doses. The mutagenic potential of allethrin was examined in a wide range of tests including in vitro/in vivo gene mutation, DNA damage and repair, and in vitro/in vivo structural aberration the results of the tests were negative. Allethrin was found to be mutagenic in Salmonella typhimurium reversion assay systems in TA 100, TA 104 and TA 97 strains and required metabolic activation. Allethrin did not show evidence of treatment related effects on micronuclei frequency in mouse bone marrow smears. Fish are sensitive to allethrin toxicity when they are exposed to this insecticide in elevated water temperatures/ In plants allethrin is not phototoxic.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)
Ökotoxizitätsauszüge/AQUATIC SPECIES/ The biological activity in fish is affected by temperature. The toxicity of 1R or (+)- trans-allethrin for the bluegill was about 1.5 times higher at 22 °C than at 12 °C ... . Water hardness and pH did not have any significant effects on the toxicity for fish ... . Allethrin is generally less toxic in arthropods than in fish, with the exception of the stonefly, which is the most susceptible insect ... ./AQUATIC SPECIES/ A search of the EIIS (Environmental Incident Information System) database for ecological incidents (run on Dec. 2, 2005) identified a total of one ecological incident involving an allethrin (allethrinPC Code: 004001). The allethrin involved in the incident is no longer registered (i.e., all of its uses have been cancelled). The incident occurred on a fish farm in Ventura County, CA, in Dec. 2000, and it involved the death of 13,000 rainbow trout. The reported cause of the incident was an act of sabotage (i.e., it was the result of intentional misuse). The certainty index was reported as highly probable and it was reported that, there seemed to be no doubt about the cause of the fish kill, although no tissue or water samples were reported./AQUATIC SPECIES/ The toxicity of natural pyrethrins and five pyrethroids was determined with coho salmon (Oncorhynchus kisutch), steelhead trout (Salmo gairdneri), fathead minnow (Pimephales promelas), channel catfish (Icatlurus punctatus), bluegill (Lepomis macrochirus), and yellow perch (Perca flavescens). The 96-hour LC50s in static tests at 12 degrees C ranged from 24.6 to 114 ug/L of natural pyrethrins and from 0.110 to 1,140 ug/L of pyrethroids. Two pyrethroids, RU-11679 and SBP-1382 (R), were over 10 times more toxic than pyrethrum extract in the flow-through tests. Coldwater species of fish were more sensitive than warmwater species to all the compunds. Temperature (12-22 degrees C) influences the toxicity of natural pyrethrin and the pyrethroids. The natural pyrethrin was more toxic to fish in pH 6.5 than in pH 9.5 water, but the toxicity of pyrethroids was not influenced in the pH range. The two most toxic pyrethroids, RU-11679 and SBP-1382, were deactivated more rapidly in water solutions than natural pyrethrins, S-bioallethrin, dimethrin, and d-trans allethrin. /S-bioallethrin, d-trans allethrin, other pyrethrins and pyrethroids//PLANTS/ Non-phytotoxic
Signs and SymptomsCough.Redness.
Acute Toxicity LinkChemical: ALLETHRINChemical: DOWICIL 75Chemical: D-TRANS ALLETHRIN
UN-TransportnummerUN3082 9/PG 3
Zollcode29183000
R-Sätze (R)20/22-50/53
GefahrensymboleXn,N
Sicherheitshinweise (S)36-60-61