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Esfenvalerate

Basic information Description Sources Safety Supplier Related

Esfenvalerate Basic information

Product Name:
Esfenvalerate
Synonyms:
  • ASANA
  • ASANA (TM)
  • HALLMARK
  • FERTIALPHA
  • FORALPHA
  • ESFENVALERATE
  • Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
  • AMICIDIN SUPER
CAS:
66230-04-4
MF:
C25H22ClNO3
MW:
419.91
EINECS:
613-911-9
Product Categories:
  • Insecticide
  • EQ - EZMethod Specific
  • PesticidesPesticides
  • Alpha sort
  • E
  • E-GMethod Specific
  • Endocrine Disruptors (Draft)Alphabetic
  • EPA
  • Insecticides
  • Oeko-Tex Standard 100
  • Pesticides&Metabolites
  • Pyrethroids
Mol File:
66230-04-4.mol
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Esfenvalerate Chemical Properties

Melting point:
59°C
Boiling point:
151-167°C
alpha 
D25 -15.0° (c = 2.0 in CH3OH)
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)
Water Solubility 
0.002 mg l-1 (25 °C)
BRN 
4275674
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
Esfenvalerate (66230-04-4)
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Safety Information

Hazard Codes 
T;N,N,T
Risk Statements 
23/25-43-50/53
Safety Statements 
24-36/37/39-45-60-61
RIDADR 
UN 2811
WGK Germany 
3
RTECS 
CY1576367
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29269090
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).

MSDS

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Esfenvalerate Usage And Synthesis

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

Chemical Properties

Viscous yellow or amber liquid or white or amber crystalline solid.

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

Insecticide.

Uses

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

Definition

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

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®

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.

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.

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

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.

Incompatibilities

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

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

EsfenvalerateSupplier

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