ChemicalBook--->CAS DataBase List--->67375-30-8

67375-30-8

67375-30-8 Structure

67375-30-8 Structure
IdentificationBack Directory
[Name]

alpha-Cypermethrin
[CAS]

67375-30-8
[Synonyms]

FURY
CCN52
AUZAR
ARRIVO
bestox
Bcstox
Fendana
wl85871
concord
dominex
AMMO(R)
OMS 3004
Renegade
AGROTRINA
FASTAC(R)
BASATHRIN
BESTOX(R)
DOMINEX(R)
fastac10ec
FLOCORD(R)
FENDONA(R)
ALFOXYLATE
Alphaguard
alphametrin
RENEGADE(R)
alfamethrin
BARRICIDE(R)
ALPHAMETHRIN
a-Cypermethrin
alpha-Cypermet
ALPHAMETHRIN(R)
ZETA-CYPERMETHRIN
alpha-cypermetrin
ALPHA-CYPERMETHRIN
Alpha-cypermrthrin
TRANS-CYPERMETHRIN
cypermethrin,alpha
α-Cypermethrin E.C.
cypermethrin(alpha)
alpha-cypermethrin (bsi,iso)
ALPHA-CYPERMETHRIN, 250MG,NEAT
(1S)-cis-(alphaR)-cypermethrin
Alphacypermethrin - Mixed isomers
ALPHA-CYPERMETHRIN PESTANAL, 100 MG
alpha-Cypermethrin 250mg [67375-30-8]
(1-alpha(s*),3-alpha)-(+-)-noxyphenyl)methyleste
zyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CYANO (3-PHENOXYPHENYL)METHYL-3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL
(1rciss)and(1scisr)enantiomericisomerpairofalpha-cyano-3-phenoxyben
Phenoxybenzyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate
3alpha]-(+-)-cyano(3-phenoxyphenyl)methyl3-(2,2-dichloroethenyl)-[1alpha(s*
2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate-α-cyano-(3-phenoxy)-benzylester
(R,S)-ALPHA-CYANO-3-PHENOXYBENZYL-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
(R,S)-α-cyano-3-phenoxybenzyl(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(R)-Cyano-3-phenoxybenzyl (1S,3S)-rel-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate
Cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, (+-)-cis isomer
(1S,3S)-(R)-Cyano(3-phenoxyphenyl)Methyl 3-(2,2-dichlorovinyl)-2,2-diMethylcyclopropanecarboxylate
3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID CYANO(3-PHENOXYPHENYL)METHYL ESTER
(R,S)-alpha-Cyano-(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, (+-)-cis isomer
(+/-)(A)-CYANO-3-PHENOXYBENZYL (+) CIS-TRANS-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-CYCLOPROPANE CARBOXYLATE
[1A(S(R)),3A]-(+/-)-CYANO-(3-PHENOXYPHENYL)METHYL-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANE CARBOXYLATE
cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate, (1A(S*), 3A)-(+-)-
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (S)-
3-(2,2-dichloroethenyl)-2,2-dimethyl-,(R)-cyano(3-phenoxyphenyl)methylester,(1S,3S)-rel-Cyclopropanecarboxylicacid
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (R)-cyano(3-phenoxyphenyl)methyl ester, (1S,3S)-rel-
3-(2,2-dichloroethenyl)-2,2-dimethyl-,cyano(3-phenoxyphenyl)methylester,(1-alpha(s*),3-alpha)-(+-cyclopropanecarboxylicaci
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (1alpha(s*),3alpha)-(+/-)-
[EINECS(EC#)]

257-842-9
[Molecular Formula]

C22H19Cl2NO3
[MDL Number]

MFCD00055328
[MOL File]

67375-30-8.mol
[Molecular Weight]

416.3
Chemical PropertiesBack Directory
[Appearance]

Colorless crystalline solid or viscous yellowish-brown semisolid mass. Mild aromatic odor.
[Melting point ]

78-81°C
[Boiling point ]

200°C (rough estimate)
[density ]

1.12
[vapor pressure ]

2.3×10-7Pa (20 °C)
[refractive index ]

1.6200 (estimate)
[Fp ]

100 °C
[storage temp. ]

−20°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

neat
[Water Solubility ]

0.01 mg l-1 (25 °C)
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[BRN ]

8444118
[Henry's Law Constant]

1.0×100 mol/(m3Pa) at 25℃, HSDB (2015)
[Major Application]

agriculture
environmental
[InChI]

1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3
[InChIKey]

KAATUXNTWXVJKI-UHFFFAOYSA-N
[SMILES]

CC1(C)C(\C=C(\Cl)Cl)C1C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2
[EPA Substance Registry System]

Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2, 2-dimethyl-, (R)-cyano(3-phenoxyphenyl) methyl ester, (1S,3S)-rel-(67375-30-8)
Hazard InformationBack Directory
[Chemical Properties]

colourless crystals or white powder
[Uses]

insecticide
[Uses]

α-Cypermethrin is a synthetic pyrethroid pesticide used in large-scale commercial agricultural applications as well as in consumer products for domestic purposes.
[Potential Exposure]

Pyrethroid Insecticide used for the control of a wide range of chewing and sucking insects (particularly lepidotera, coleoptera, and hemiptera) in fruit (including citrus), vegetables, vines, cereals, maize, beet, oilseed rape, potatoes, cotton, rice, soya beans, forestry, and other crops. Control of cockroaches, mosquitoes, flies, and other insect pests in public health; and flies in animal houses. Also used as an animal ectoparasiticide. zeta- Cypermethrin only is a United States Environmental Protection Agency Restricted Use Pesticide (RUP).
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions) if breathing has stopped, and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Do not induce vomiting when formulations containing petroleum solvents are ingested. Otherwise, give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN3349 Pyrethroid pesticide, solid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material. UN3352 Pyrethroid pesticide, liquid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
[Incompatibilities]

May react violently with strong oxidi- zers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders, or dust. Incompatible with silver compounds. Mixture with some silver compounds forms explosive salts of silver oxalate.
[Description]

Alpha-cypermethrin is a widely used pyrethroid insecticide. It has a low aqueous solubility, in relatively volatile and, based on its chemical properties, is not expected to leach to groundwater. However, it is considered to be a serious water pollutant. It is moderately persistent in soil and has been known to persist in water. It is highly toxic to mammals and a recognised irritant. It is relatively non-toxic to birds but is highly toxic to most aquatic organisms and honeybees. Alpha-cypermethrin is moderately toxic to earthworms.
[Waste Disposal]

Do not discharge into drains or sewers. Burn in incinerator specifically designed for pes- ticide disposal or dispose as a Hazardous waste in a landfill approved and licensed for the disposal of pesticides. Consult with environmental regulatory agencies for guid- ance on acceptable disposal practices. Ultimate disposal of the chemical must consider: the material’s impact on air quality; potential migration in soil or water; effects on ani- mal, aquatic, and plant life; and conformance with environ- mental and public health regulations.
[Definition]

ChEBI: Cypermethrin is a carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile. It has a role as a pyrethroid ester insecticide, a pyrethroid ester acaricide, an agrochemical and a molluscicide. It is an organochlorine compound, a nitrile, an aromatic ether and a cyclopropanecarboxylate ester. It is functionally related to a 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid.
[Production Methods]

Alpha-cypermethrin is produced commercially through a multi-step chemical synthesis that isolates the most biologically active isomers of cypermethrin. The process begins with the synthesis of the isomeric-mixture of cypermethrin and involves reacting 3-phenoxybenzyl alcohol with cyanoacetic acid derivatives and dichlorovinyl cyclopropane carboxylic acid. The alpha isomer is isolated using chiral resolution or selective crystallization.
[Agricultural Uses]

Insecticide: A U.S. EPA restricted Use Pesticide (RUP) (zeta-Cypermethrin only). Used for the control of a wide range of chewing and sucking insects (particularly Lepidotera, Coleoptera, and Hemiptera) in fruit (including citrus), vegetables, vines, cereals, maize, beet, oilseed rape, potatoes, cotton, rice, soya beans, forestry, and other crops. Control of cockroaches, mosquitoes, flies, and other insect pests in public health; and flies in animal houses. Also used as an animal ectoparasiticide.
[Trade name]

BESTOX®; CONCORD®; DOMINEX®; FASTAC®; FENDONA®; FMC 45497®[C]; NRDC 160®; RENEGADE®; WL-85871® Cypermethrin-s: FURY® (s-isomer); FMC 56701® (s-isomer)
[Mechanism of action]

Non-systemic with contact and stomach action. Sodium channel modulator.
[Metabolic pathway]

Alpha-cypermethrin is composed of two of the four cis-cypermethrin isomers (i.e. two of the eight cypermethrin isomers). These are the lRcisaS and 1ScisaR isomers. The fate of alpha-cypermethrin specifically has been reported for soils, rat and human. Metabolite analysis was conducted in enough detail to indicate that the fate of this mixture is very similar to its fate when presented to biological systems as part of cis-cypermethrin. Thus reference can be made to the cypermethrin entry for details. The structure and Scheme numbering used below refers to the cypermethrin entry.
[Degradation]

Alpha-cypermethrin is stable as a solid but it is readily hydrolysed in solution under alkaline conditions. By analogy with cypermethrin, the rate-determining step in dilute solution is nucleophilic attack by OH-. Half-lives of cis-cypermethrin in river water and sea water at 25 °C were 21 and 24 days, respectively. Major products were 3-(2,2-dichlorovinyl)- 2,2-dimethylcyclopropanecarboxylic acid (2, DCVA), 3-phenoxybenzaldehyde (9, 3PBAl) and a-carbamoyl-3-phenoxybenzyl 3-(2,2- dichlorovinyl)-2,2-dimethylcyclopropanecarboxyltae (the amide 3); minor products were the a-carboxy analogue of 3 (4) and 3-phenoxybenzoic acid (10,3PBA) (see cypermethrin, Schemes la and lb).
Photodecomposition would be expected to be similar to that of cis-cy permethrin.
[Pesticide Type]

Insecticide; Veterinary substance
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)Health Hazard (GHS08)Environment (GHS09)
GHS06,GHS08,GHS09
[Signal word ]

Danger
[Hazard statements ]

H301-H335-H373-H410
[Precautionary statements ]

P260-P264-P270-P273-P301+P310-P314
[Hazard Codes ]

Xn,N,T
[Risk Statements ]

20/22-37-50/53-48/22-25
[Safety Statements ]

24-36/37/39-60-61-45
[RIDADR ]

UN 2810 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

GZ1250000
[REACH Registrations]

Active
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[Storage Class]

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
[Hazard Classifications]

Acute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 1
STOT RE 2
STOT SE 3
[Hazardous Substances Data]

67375-30-8(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Hydrochloric acid-->Xylene-->Sodium cyanide-->3-Phenoxybenzaldehyde-->Permethric acid
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

alpha-Cypermethrin (67375-30-8).msds
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