alpha-Cypermethrin

alpha-Cypermethrin Basic information
Product Name:alpha-Cypermethrin
Synonyms:ALPHAMETHRIN;ALPHAMETHRIN(R);ALPHA-CYPERMETHRIN;AMMO(R);ALFOXYLATE;3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID CYANO(3-PHENOXYPHENYL)METHYL ESTER;[1A(S(R)),3A]-(+/-)-CYANO-(3-PHENOXYPHENYL)METHYL-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANE CARBOXYLATE;AGROTRINA
CAS:67375-30-8
MF:C22H19Cl2NO3
MW:416.3
EINECS:614-054-3
Product Categories:Pesticide intermediates;Pesticides;AcaricidesPesticides&Metabolites;Pesticides&Metabolites;PesticidesPesticides;PyrethroidsMore...Close...;Alpha sort;C;CAlphabetic;CO - CZMethod Specific;Endocrine Disruptors (Draft)Method Specific;EPA;Insecticides;Oeko-Tex Standard 100
Mol File:67375-30-8.mol
alpha-Cypermethrin Structure
alpha-Cypermethrin Chemical Properties
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. Sealed in dry,2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form neat
Water Solubility  0.01 mg l-1 (25 °C)
BRN 8444118
Stability:Stable. Incompatible with strong oxidizing agents.
EPA Substance Registry System.alpha.-Cypermethrin (67375-30-8)
Safety Information
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
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data67375-30-8(Hazardous Substances Data)
MSDS Information
ProviderLanguage
alpha-Cypermethrin English
SigmaAldrich English
alpha-Cypermethrin Usage And Synthesis
Chemical Propertiesalpha-cypermethrin is a colorless crystalline solid or viscous yellowish-brown semisolid mass. mild aromatic odor. easily soluble in alcohols, ketones and aromatic hydrocarbon organic solvents, such as cyclohexanone 515g/l, xylene 315g/l, solubility in water 5 ~ 10mg/l (0.01 ~ 0.2mg/l). it is relatively stable under acidic and neutral conditions, easy to hydrolyze under strong alkaline conditions, and has good thermal stability.
Usesalpha-Cypermethrin is a synthetic pyrethroid pesticide used in large-scale commercial agricultural applications as well as in consumer products for domestic purposes.
Usesinsecticide
UsesAlpha-cypermethrin is used to control a wide range of insects, especially Lepidoptera, in fruit, vines, vegetables, cereals, beans, beets, cotton, ornamentals and forestry and other crops. It is also used for insect control in public health and for ectoparasite control on animals.
DefinitionChEBI: 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.
Agricultural UsesInsecticide: 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 nameBESTOX®; CONCORD®; DOMINEX®; FASTAC®; FENDONA®; FMC 45497®[C]; NRDC 160®; RENEGADE®; WL-85871® Cypermethrin-s: FURY® (s-isomer); FMC 56701® (s-isomer)
Potential Exposurealpha-Cypermethrin useds 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. alpha-Cypermethrin only is a United States Environmental Protection Agency Restricted Use Pesticide (RUP).
Metabolic pathwayAlpha-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.
ShippingUN3349 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.
DegradationAlpha-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.
IncompatibilitiesMay 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.
Waste DisposalDo 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.
alpha-Cypermethrin Preparation Products And Raw materials
Raw materialsEthanol-->Hydrochloric acid-->Xylene-->Sodium cyanide-->3-Phenoxybenzaldehyde-->Permethric acid
Cyclopropane rich-d-t-Prallethrin BETA-CYPERMETHRIN alpha-Cypermethrin 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE Vinyl ester resin VINYL PROPIONATE CHLORODIMETHYLVINYLSILANE D-AMPHETAMINE HYDROCHLORIDE Phenothrin rich_d_transallethrin Permethrin Cyclopropanecarboxylic acid Cyano Vinyl resin Cyphenothrin D-Phenothrin Diethylstilbestrol

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