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Cycloprothrin

HCID 91686
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
63935-38-6
Standard-SMILES
CCOc1ccc(C2(C(=O)OC(C#N)c3cccc(Oc4ccccc4)c3)CC2(Cl)Cl)cc1
InChIKey
CGTWCAVZZBLHQH-UHFFFAOYSA-N
Summenformel
C26H21Cl2NO4
Durchschnittliche Molmasse
482,4 g/mol
Monoisotopische Masse
481,0847635

Überblick

A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. (L811)

Namen und Bezeichner

Bevorzugter Name
Cycloprothrin
IUPAC
[cyano-(3-phenoxyphenyl)methyl] 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylate
Englischer Name
CYCLOPROTHRIN
Summenformel
C26H21Cl2NO4
Molmasse
482.36

Namen und Synonyme

Cycloprothrin63935-38-6CyclosalPhencyclateGJD87S7ZH6Cyclopropanecarboxylic acid, 2,2-dichloro-1-(4-ethoxyphenyl)-, cyano(3-phenoxyphenyl)methyl esterGH-414NK-8116[cyano-(3-phenoxyphenyl)methyl] 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylateDTXSID0058148(cyano-(3-phenoxyphenyl)methyl) 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylateRefChem:129957
Weitere Namen anzeigen
gh414CH-414nk8116CyclopaslFencylatefencyclatenyl)methylester
DTXCID6031916cyano(3-phenoxyphenyl)methyl 2,2-dichloro-1-phenylcyclopropane-1-carboxylate(RS)-alpha-Cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylateCHEBI:39283Cycloprothrin [ISO]Cyclosal (insecticide)GH 414UNII-GJD87S7ZH6

Datenbank-Bezeichner

CAS
63935-38-6

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,2
Polarare Oberfläche (TPSA)
68,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
9
Schwere Atome
33
Formalladung
0
Komplexität
723

Experimentelle und physikochemische Eigenschaften

LogP4.19
Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt
25 ℃ · <25℃
Siedepunkt
142.5 °C · 142.5 °C
Dichte
1.36 · 1.36±0.1 g/cm3(Predicted)
Dampfdruck
2.13 · 2.13×10-6 Pa (20 °C)
storage temp.
2 · 2-8°C
Wasserlöslichkeit
0.09 mg · 0.09 mg l-1(25 °C)
BRN
14340823 · 14340823
InChI
1S/C26H21Cl2NO4/c1-2-31-20-13-11-19(12-14-20)25(17-26(25,27)28)24(30)33-23(16-29)18-7-6-10-22(15-18)32-21-8-4-3-5-9-21/h3-15,23H,2,17H2,1H3
InChIKey
CGTWCAVZZBLHQH-UHFFFAOYSA-N
SMILES
CCOc1ccc(cc1)C2(CC2(Cl)Cl)C(=O)OC(C#N)c3cccc(Oc4ccccc4)c3

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Gefahrenhinweise

Regulatory InformationChemical: Cyclopropanecarboxylic acid, 2,2-dichloro-1-(4-ethoxyphenyl)-, cyano(3-phenoxyphenyl)methyl ester
Hazard Classes and Categories · 3 Einträge

Skin Sens. 1 (100%)

Skin sensitization - Category 1

Skin sensitization - Category 1B

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Following ingestion, pyrethriods are hydrolysed by various digestive enzymes in the gastro-intestinal tract. However, a small portion of the insecticidally active compounds or its derivatives are absorbed, as shown by their toxicity and their effect on the liver. Pyrethriods may also be absorbed following inhalation or dermal contact. They are rapidly distributed to most tissues, particularly to those with a high lipid content, and are concentrated in central and peripheral nervous tissues. Pyrethriods or their metabolites are not known to be stored in the body or to be excreted in the milk, but no study of the matter has employed modern methods. The major metabolic pathways for pyrethriods are hydrolysis of the central ester bond, oxidative attacks at several sites, and conjugation reactions, to produce a complex array of primary and secondary water-soluble metabolites that undergo urinary excretion. Metabolism is believed to involve nonspecific microsomal carboxyesterases and microsomal mixed function oxidases, which are located in nearly all tissue types, with particularly high activities in the liver. Metabolites are excreted in the urine and faeces. (L857, L889)

Verwendung und Herstellung

UsesPyrethroids are used as insecticides. (L857)

Anwendungen

VerwendenCycloprothrin is used to control rice water weevils and other insects in paddy rice, fruit, vegetables, tea, cotton, soyabeans and in forestry.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

m-Phenoxybenzaldehyd1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester

Zugehörige Reaktionen

0
Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
91686
DTXSID
DTXSID0058148
UNII
GJD87S7ZH6
EC Number
613-404-2
Nikkaji
J106.045G
Health Effects · 1 Eintrag

Pyrethroid 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, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis, can also occur following pyrethriod poisoning. (L857)

Toxicity Summary · 1 Eintrag

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 · 1 Eintrag

Spilling on the head, face and eyes can result in pain, lacrimation, photophobia, congestion, and edema of the conjunctiva and eyelids. Ingestion cases epigastric pain, nausea, vomiting, headache, dizziness, anorexia, fatigue, tightness in chest, blurred vision, paresthesia, palpitations, coarse muscular fasciculations, and disturbances of conciousness. In servere poisonings, convulsive attacks with opisthotonos and loss of conciousness have occurred. (T10)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
3
ridadr
UN 3077 9 / PGIII
hs_code
29269090
risk_code
43-50/53
hazard_code
Xi,N
safety_code
36/37-60-61
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Skin Sens. 1
Benzylalkohol
Natriumcyanid
α-Bromtoluol
Alkohol 3-phenoxybenzyl
Cyhalothrin
Benzonitril
CYCLOPROPANOYL CHLORIDE
2 sodium salt
Cyclopropancarbonsure

Anbieter37 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: A carboxylic ester having 2,2-dichloro-1-phenylcyclopropanecarboxylic acid as the acid component and hydroxy(3-phenoxyphenyl)acetonitrile as the alcohol component.