ChemicalBook--->CAS DataBase List--->66230-04-4

66230-04-4

66230-04-4 Structure

66230-04-4 Structure
IdentificationMore
[Name]

Esfenvalerate
[CAS]

66230-04-4
[Synonyms]

AMICIDIN SUPER
ASANA
ASANA (TM)
Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
ESFENVALERATE
FERTIALPHA
FORALPHA
HALLMARK
(S)-A-CYANO-3-PHENOXY BENZYL-(S)-2-(4-CHLOROPHENYL)-3-METHYL-BUTYRATE
SUMI-ALFA
SUMI-ALPHA
(s-(r*,r*))-hyleste
(S)-.alpha.-Cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl)-3-methylbutyricester
(S)-alpha-Cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate
[s-(r*,r*]-cyano(3-phenoxyphenyl)methyl4-chloro-2-(1-methylethyl)benzeneacetat
4-chloro-alpha-(1-methylethyl)-benzeneaceticacicyano(3-phenoxyphenyl)met
aalpha
Asana xl
asanaxl
Benzeneaceticacid,4-chloro-.alpha.-(1-methylethyl)-,cyano(3-phenoxyphenyl)-methylester,(S-(R*,R*))
[EINECS(EC#)]

613-911-9
[Molecular Formula]

C25H22ClNO3
[MDL Number]

MFCD00203302
[Molecular Weight]

419.9
[MOL File]

66230-04-4.mol
Chemical PropertiesBack Directory
[Appearance]

Viscous yellow or amber liquid or white or amber crystalline solid.
[Melting point ]

59°C
[alpha ]

D25 -15.0° (c = 2.0 in CH3OH)
[Boiling point ]

151-167°C
[density ]

d2323 1.163
[vapor pressure ]

2×10-7 Pa (25 °C)
[refractive index ]

1.6500 (estimate)
[storage temp. ]

0-6°C
[solubility ]

DMSO : 100 mg/mL (238.15 mM; Need ultrasonic)
[form ]

neat
[Water Solubility ]

0.002 mg l-1 (25 °C)
[color ]

White to light yellow
[BRN ]

4275674
[Henry's Law Constant]

2.4×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
[Major Application]

agriculture
environmental
[InChI]

1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m1/s1
[InChIKey]

NYPJDWWKZLNGGM-RPWUZVMVSA-N
[SMILES]

CC(C)[C@H](C(=O)O[C@H](C#N)c1cccc(Oc2ccccc2)c1)c3ccc(Cl)cc3
[LogP]

6.220
[CAS DataBase Reference]

66230-04-4(CAS DataBase Reference)
[NIST Chemistry Reference]

Benzeneacetic acid, 4-chloro-«alpha»-(1-methylethyl)-, cyano (3-phenoxyphenyl)methyl ester,(s-(r*,r*))-(66230-04-4)
[EPA Substance Registry System]

66230-04-4(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

T;N,N,T
[Risk Statements ]

R23/25:Toxic by inhalation and if swallowed .
R43:May cause sensitization by skin contact.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
[Safety Statements ]

S24:Avoid contact with skin .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
[RIDADR ]

UN 2811
[WGK Germany ]

3
[RTECS ]

CY1576367
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29269090
[Storage Class]

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

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

66230-04-4(Hazardous Substances Data)
[Toxicity]

LC50 (96-hour) for fathead minnows 0.69 mg/L (Worthing and Hance, 1991); acute oral LD50 for rats 75 mg/kg (Hartley and Kidd, 1987).
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Thionyl chloride-->Phosphorus oxitrichloride-->Bromine-->Sodium cyanide-->Fenvalerate-->3-Phenoxybenzaldehyde-->Butyryl chloride-->Permethric acid-->L-1-Phenylethylamine-->Cinchonidine-->Disodium 2-naphthol-3,6-disulfonate-->4-Chlorophenylacetic acid-->1-Amino-8-naphthol-4-sulfonic acid-->S 5602A-Beta-->3-Phenoxybenzaldehyde cyanohydrin, 70 wt% solution in ether
[Preparation Products]

S-5602Bα
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Esfenvalerate(66230-04-4).msds
Hazard InformationBack Directory
[Potential Exposure]

Esfenvalerate is a synthetic pyrethroid Insecticide used to control wide range of pests such as moths, flies, beetles, and other insects. It is used on vegetable crops (soya beans, sugar cane), tree fruit, cotton, maize, sorghum and nut crops, and noncrop lands. It also isused on a wide variety of household pests. It is usually mixed with a wide variety of other types of pesticides such as carbamate compounds or organophosphates and has the naturally occurring compound fenvalerate for use in the United States Esfenvalerate is almost identical to fenvalerate. Much of the data for fenvalerate is applicable to the pesticide esfenvalerate (E:0207) because the two compounds contain the same components. The only differences in the two products are the relative proportions of the four separate constituents (isomers). Esfenvalerate has become the preferred compound because it requires lower applications rates than fenvalerate, is less chronically toxic, and is a more powerful insecticide. A United States Environmental Protection Agency Restricted Use Pesticide (RUP). Incompatibilities: Oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); strong acids. Moisture may cause hydrolysis/ decomposition.
[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]

Oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); strong acids. Moisture may cause hydrolysis/ decomposition.
[Chemical Properties]

Viscous yellow or amber liquid or white or amber crystalline solid.
[Waste Disposal]

Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers
[Uses]

Esfenvalerate is the most potent insecticidal isomer of Fenvalerate (F279450), a pyrethroid insecticide used to control insects from food crops, animal feed and cotton products.
[Uses]

Esfenvalerate possesses a broad range of insecticidal activity and it is used on cotton, fruit, vegetables and other crops.
[Uses]

Insecticide.
[Definition]

ChEBI:Esfenvalerate is a fenvalerate. It has a role as a pyrethroid ester insecticide and an agrochemical.
[Production Methods]

Esfenvalerate is commercially produced through stereoselective synthesis of the active (S)-isomer of fenvalerate, a synthetic pyrethroid insecticide. The process involves esterification of (S)-alpha-cyano-3-phenoxybenzyl alcohol with (2S)-2-(4-chlorophenyl)-3-methylbutyric acid. This reaction yields esfenvalerate, which is more biologically active than the racemic mixture found in fenvalerate.
[Agricultural Uses]

Insecticide: A U.S. EPA restricted Use Pesticide (RUP). Esfenvalerate is a synthetic insecticide used to control a wide range of pests such as moths, flies, beetles, and other insects. It is used on vegetable crops (soya beans, sugar cane), tree fruit, cotton, maize, sorghum and nut crops, and non-crop lands. It also is used on a wide variety of household pests. It is usually mixed with a wide variety of other types of pesticides such as carbamate compounds or organophosphates and has the naturally occurring compound fenvalerate for use in the U.S. Esfenvalerate is almost identical to fenvalerate. Much of the data for fenvalerate is applicable to the pesticide esfenvalerate because the two compounds contain the same components. The only differences in the two products are the relative proportions of the four separate constituents (isomers). Esfenvalerate has become the preferred compound because it requires lower application rates than fenvalerate, is less chronically toxic, and is a more powerful insecticide.
[Trade name]

AMERICARE®; ASANA®; ASANA-XL®; ASANA® DPX-YB656-84; ENFORCER®; EVERCIDE®; HALMARK®; OMS-3023®; S-1844®; S-5602 ALPHA®; SUMI-ALFA®; SUMI-ALPHA®; SS-PYDRIN®; SUMICIDIN A-ALPHA®
[Mechanism of action]

Contact and stomach action. Sodium channel modulator.
[Environmental Fate]

Chemical/Physical. May hydrolyze in aqueous solutions forming acetic acid and other compounds.
[Metabolic pathway]

Esfenvalerate is the 2SαS-isomer of fenvalerate (which is racemic). It possesses some small differences in physical properties when compared with the racemate. Overall, the degradation and metabolism of the two compounds are very similar. Reference should be made to the fenvalerate entry. An important exception, which is discussed fully in the latter entry, is that esfenvalerate does not form the cholesterol ester conjugate that has been shown to be responsible for granulomatous changes in several tissues on repeated dosing of fenvalerate.
[storage]

Store at -20°C
[Degradation]

Esfenvalerate is hydrolysed in aqueous alkali to its constituent acid and alcohol; the latter decomposes to 3-phenoxybenzaldehyde and cyanide ion as described for fenvalerate and cypermethrin. Photodecomposition occurs as for fenvalerate.
[Pesticide Type]

Insecticide
Questions And AnswerBack Directory
[Description]

Esfenvalerate is a synthetic pyrethoid insecticide – a class of pesticides originating from the chrysanthemum flower, which disrupt sodium channels. It has replaced fenvalerate, a less effective and more chronically toxic enantiomer. It can be used for general pest control, including spiders, fleas, scorpions, moths, beetles, etc. It is frequently applied on vegetable, nut, and non-crop products, often in combination with other active ingredients such as carbamate compounds and organophosphates. Product labels containing esfenvalerate include Sumi-Alpha, Hounddog, Sven, Asana, and Esfenvalerate 5EC, manufactured variously by BASF, Greencrop, and Standon.
[Sources]

http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/esfenvalerate-ext.html
https://en.wikipedia.org/wiki/Esfenvalerate
https://www.domyown.com/esfenvalerate-c-114_374.html
https://en.wikipedia.org/wiki/Pyrethroid
https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/esfenvalerate
https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/269.htm
Spectrum DetailBack Directory
[Spectrum Detail]

Esfenvalerate(66230-04-4)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

66230-04-4(sigmaaldrich)
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