rac-3α*-[(Z)-2-クロロ-3,3,3-トリフルオロ-1-プロペニル]シクロプロパン-1α*-カルボン酸[(S*)-シアノ(3-フェノキシフェニル)メチル]

lambda-Cyhalothrin

HCID 6440557

基本情報

CAS
76703-65-6
標準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
分子式
C23H19ClF3NO3
平均分子量
449.8 g/mol

概要

(1S)-cis-(alphaR)-cyhalothrin is a cyclopropanecarboxylate ester.

名称と識別子

優先名称
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
現地名
rac-3α*-[(Z)-2-クロロ-3,3,3-トリフルオロ-1-プロペニル]シクロプロパン-1α*-カルボン酸[(S*)-シアノ(3-フェノキシフェニル)メチル]
英語名
λ-Cyhalothrin
分子式
C23H19ClF3NO3
分子量
449.85

名称と別名

lambda-CyhalothrinKarate91465-08-6IconWarriorOXYFLYZ44TGV333KLambda cyhalothrinDTXSID7032559Cyclopropanecarboxylic acid, 3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (R)-cyano(3-phenoxyphenyl)methyl ester, (1S,3S)-rel-DTXCID00196593lambdacyhalothrin
名称をさらに表示
カラトrac-3α*-[(Z)-2-クロロ-3,3,3-トリフルオロ-1-プロペニル]シクロプロパン-1α*-カルボン酸[(S*)-シアノ(3-フェノキシフェニル)メチル]Λ-シハロトリン標準品ラムダシハロトリンΛ‐シハロトリン標準品Λ-シハロトリン STANDARDλ-シハロトリン Standard, 100 µg/mL in MeOHrel-(1R*,3R*)-3-[(Z)-2-クロロ-3,3,3-トリフルオロ-1-プロペニル]-2,2-ジメチルシクロプロパンカルボン酸(αS*)-α-シアノ-3-フェノキシベンジルカラテラムダ-シハロスリン(S)-シアノ(3-フェノキシフェニル)メチル (1R,3R)-3-(2-クロロ-3,3,3-トリフルオロプロパ-1-エン-1-イル)-2,2-ジメチルシクロプロパン-1-カルボキシラート(1R,2R)-2-(2-クロロ-3,3,3-トリフルオロ-1-プロペニル)-3,3-ジメチルシクロプロパン-1-カルボン酸(S)-シアノ(3-フェノキシフェニル)メチルランブダ-シハロトリン(1R,Z)-3-(2-クロロ-3,3,3-トリフルオロ-1-プロペニル)-2,2-ジメチルシクロプロパンカルボ ン酸=α-シアノ-3-フェノキシベンジルλ-CyhalothrinLambda CyhalothrineL-CYHALOTHRINL-Cyhalothrin,100 μL/mL in MeOHcyano-3-phenoxybenzyl-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethyl cyclopropanecarboxylatePP321Matado
RefChem:5935CHEBI:39325415-130-776703-65-6lambda-Cyhalothrin [ISO]Cyhalothrin K(1S)-cis-(alphaR)-cyhalothrinlambda-Cyhalothrin, (-)-

データベース識別子

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

物性

構造計算による物性

XLogP
6.1
極性表面積
59.3 Ų
水素結合供与体数
0
水素結合受容体数
7
回転可能結合数
7
重原子数
31

実験および物理化学的性質

Pesticides · 3 件

Insecticides

Active substance -> EU Pesticides database: Approved

Pesticide

LogP7.0
DensityRelative density (water = 1): 1.3
SolubilitySolubility in water: none
Endocrine DisruptorsPotential endocrine disrupting compound
Decomposition275 °C

物理化学的性質

融点
49.2 °C · 49.2°C
沸点
187 · 187-190°C
比重(密度)
1.3225 · 1.3225 (estimate)
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
外見
Solid

化学的性質

化学的特性olorless to beige powder; or viscous yellowish-brown liquid. Mild odor. Liquid formulations containing organic solvents may be flammable.

安全と法規制

GHS分類

GHS Classification · 6 件

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)

危険有害性情報

Regulatory Information · 5 件

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

Other Safety InformationIMAP assessments - Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester,[1.alpha.(S*),3.alpha.(Z)]-(.+-.)-: Human health tier I assessment
Fire HazardsLiquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.
EC ClassificationSymbol: T+, N; R: 21-25-26-50/53; S: (1/2)-28-36/37/39-38-45-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
Chemical DangersDecomposes on burning. This produces toxic fumes including nitrogen oxides, hydrogen chloride and hydrogen fluoride.

安全と保護具

Fire FightingUse alcohol-resistant foam, dry sand, powder, carbon dioxide.
First Aid Measures · 4 件

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 .

Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Cool. Keep in a well-ventilated room.
Spillage Disposal · 1 件

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.

Eye PreventionWear safety spectacles.
Skin PreventionProtective clothing.

毒性情報

Treatment · 1 件

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 · 1 件

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 · 2 件

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 · 1 件

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 · 5 件

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 · 1 件

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.

安全データ

wgk
3
rtecs
GZ1227780
ridadr
UN 2810 6.1/PG 3
毒性
LD50 (technical grade) in male, female rats (mg/kg): 79, 56 orally; 632, 696 dermally (Jutsum)
risk_code
21-25-26-50/53-20/21/22
hazard_code
T+;N,N,T+,Xn

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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 · 2 件

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.

用途と製造

UsesPyrethroids are used as insecticides. (L857)
Household ProductsInformation on 73 consumer products that contain lambda-Cyhalothrin in the following categories is provided:

応用分野

使用Insecticide; pyrethrin analog

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