Grundinformationen
- Standard-SMILES
CC1(C)[C@H](/C=C(\Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)c1cccc(Oc2ccccc2)c1- InChIKey
ZXQYGBMAQZUVMI-GCMPRSNUSA-N- Summenformel
- C23H19ClF3NO3
- Durchschnittliche Molmasse
- 449,8 g/mol
Überblick
(1S)-cis-(alphaR)-cyhalothrin is a cyclopropanecarboxylate ester.
Namen und Bezeichner
- Bevorzugter Name
- lambda-Cyhalothrin
- IUPAC
- trans-[(R)-cyano-(3-phenoxyphenyl)methyl] (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
- Lokaler Name
- alpha-Cyan-3-phenoxybenzyl-3-(2-chlor-3,3,3-trifluorprop-1-enyl)-2,2-dimethylcyclopropan-carboxylat, 1:1 Gemisch der(Z)-(1R,3R), S-ester und(Z)-(1S,3S), R-ester
- Englischer Name
- λ-Cyhalothrin
- Summenformel
- C23H19ClF3NO3
- Molmasse
- 449.85
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
76703-65-6、91465-08-6- PubChem CID
- 6440557
- DTXSID
DTXSID7032559- ChEMBL
CHEMBL2251732- ChEBI
CHEBI:39327- UNII
- 375WQ7596S、Z44TGV333K
- EC Number
- 415-130-7
- Nikkaji
- J3.235.957D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,1
- Polarare Oberfläche (TPSA)
- 59,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 31
- Formalladung
- 0
- Komplexität
- 736
Experimentelle und physikochemische Eigenschaften
Pesticides
Insecticides
Active substance -> EU Pesticides database: Approved
Pesticide
Collision Cross Section
190.4 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7032559]
199.44 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+; Note: drift peak 1 (of 2)]
Physikochemische Eigenschaften
- Schmelzpunkt
- 49.2 °C · 49.2°C
- Siedepunkt
- 187 · 187-190°C
- Dichte
- 1.3225 · 1.3225 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- Farbe
- White to off-white
- Merck
- 13 · 13,2787
- Henry's Law Constant
- 5 · 5.0×101 mol/(m3Pa) at 25℃, Maniere et al. (2011)
- Stabilität
- Light Sensitive
- InChI
- 1S/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/b19-12-/t17-,18+,20-/m0/s1
- InChIKey
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N
- SMILES
- CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)c2cccc(Oc3ccccc3)c2
- LogP
- 7 · 7.000
- CAS Datenbank
- 91465 · 91465-08-6(CAS DataBase Reference)
- NIST chemische Informationen
- «LAMBDA»-cyhalothrin(91465-08-6)
- EPA chemische Informationen
- .lambda.-Cyhalothrin (91465-08-6)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P317, P320, P321, P330, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Danger
H301+H311 (10.8%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]
P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P308+P316, P316, P317, P320, P321, P330, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Regulation (EC) No 178/2002 (amended)
Lambda cyhalothrin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
00/80/EC, 2010/77/EU, Reg. (EU) 2015/1885, Reg. (EU) 2016/146, Reg. (EU) 2018/155, Reg. (EU) 2023/114, Reg. (EU) 2024/324, Reg. (EU) 2026/1421, Reg. (EU) No 2019/724, Reg. (EU) No 540/2011
REACH registered substance: A mixture of: α-cyano-3-phenoxybenzyl (Z)-(1R,3R)-[(S)-3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)]-2,2-dimethylcyclopropanecarboxylate; α-cyano-3-phenoxybenzyl (Z)-(1S,3S)-[(R)-3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)]-2,2-dimethylcyclopropanecarboxylate (EC: 415-130-7)
Lambda-cyhalothrin: HSNO Approval: HSR003295 Approved with controls
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute toxicity - category 2
Acute toxicity (Oral) - Category 3
Acute toxicity (Inhalation: Dusts and mists) - Category 2
Acute Tox. 2 *
Sicherheit und Schutzausrüstung
First Aid Measures
Fresh 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.
Do NOT induce vomiting. Refer for medical attention .
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
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)
Health Effects
At high doses, signs of poisoning attributable to cyhalothrin 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)
Exposure Routes
The substance can be absorbed into the body by inhalation of dust or mist and by ingestion.
Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).
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)
Signs and Symptoms
Burning sensation. Convulsions. Cough. Laboured breathing. Shortness of breath. Sore throat.
Redness. Pain.
Redness. Pain.
Abdominal pain. Cough.
Following dermal exposure to cyhalothrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of cyhalothrin. Paralysis can occur after exposure. (L857)
ICSC Environmental Data
The substance is very toxic to aquatic organisms. This substance may be hazardous to the environment. Special attention should be given to mammals and bees. The substance may cause long-term effects in the aquatic environment. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.
RAIS Toxicity Values
0.00093
OPP
USGS Health-Based Screening Levels for Evaluating Water-Quality
lambda-Cyhalothrin
Pesticide
6.2
Acute HHBP for children; The acute dietary exposure assessment is protective of chronic dietary exposures.
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
EPA Human Health Benchmarks for Pesticides
Lambda cyhalothrin
0.00093
6.2
Children
Human Health Benchmarks for Pesticides - 2021 Update
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2810 6.1/PG 3
- RTECS-Nr.
- GZ1227780
- risk_code
- 21-25-26-50/53-20/21/22
- Toxizität
- LD50 (technical grade) in male, female rats (mg/kg): 79, 56 orally; 632, 696 dermally (Jutsum)
- hazard_code
- T+;N,N,T+,Xn
- safety_code
- 1/2-28-36/37/39-38-45-60-61-13
- hazard_class
- 6.1
- packing_group
- III
- Speicherklasse
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 3 DermalAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Cyhalothrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. The main route of metabolism is, as anticipated, via hydrolysis of the ester linkage. The cyclopropane-carboxylic acid moiety is subsequently excreted via the urine as the glucuronide conjugate. The 3-phenoxybenzyl moiety is further metabolized by loss of the nitrile group, oxidation of the aldehyde form to a carboxylic acid, aromatic hydroxylation at the 4' position, and formation of the 4- O-sulfate conjugate of 3-(4-hydroxyphenoxy)benzoic acid. (L871)
MeSH Pharmacological Classification
Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Pesticides 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.
Verwendung und Herstellung
Anwendungen
VerwendenInsecticide; pyrethrin analog
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