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66230-04-4

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66230-04-4 Usage

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

Different sources of media describe the Uses of 66230-04-4 differently. You can refer to the following data:
1. 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.
2. Insecticide.
3. Esfenvalerate possesses a broad range of insecticidal activity and it is used on cotton, fruit, vegetables and other crops.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 66230-04-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,2,3 and 0 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 66230-04:
(7*6)+(6*6)+(5*2)+(4*3)+(3*0)+(2*0)+(1*4)=104
104 % 10 = 4
So 66230-04-4 is a valid CAS Registry Number.
InChI:InChI=1/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

66230-04-4 Well-known Company Product Price

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  • Sigma-Aldrich

  • (46277)  Esfenvalerate  PESTANAL®, analytical standard

  • 66230-04-4

  • 46277-100MG

  • 747.63CNY

  • Detail

66230-04-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Esfenvalerate

1.2 Other means of identification

Product number -
Other names (S)-cyano(3-phenoxyphenyl)methyl (2S)-2-(4-chlorophenyl)-3-methylbutanoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:66230-04-4 SDS

66230-04-4Synthetic route

sodium cyanide
143-33-9

sodium cyanide

S-(+)-2-(4-chlorophenyl)isovaleryl chloride
66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

3-Phenoxybenzaldehyde
39515-51-0

3-Phenoxybenzaldehyde

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
With N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide In water; 1,2-dichloro-ethane at 0 - 5℃; for 2.25h;36%
α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate
956498-38-7

α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate

A

(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
67614-32-8

(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate

B

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
With ammonia In methanol at -19 - 17℃; for 17 - 260h; Purification / work up; Resolution of racemate;A n/a
B 23%
Stage #1: α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate In n-heptane; toluene for 2h; Heating / reflux; Resolution of racemate;
Stage #2: In methanol at -16 - 0℃; for 65 - 240h; Purification / work up;
iron rust In methanol at -5 - 12℃; for 30h; Purification / work up; Resolution of racemate;
S-(+)-2-(4-chlorophenyl)isovaleryl chloride
66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

(S)-m-phenoxybenzaldehyde cyanohydrin
39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8

(S)-m-phenoxybenzaldehyde cyanohydrin

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
With pyridine
S-(+)-2-(4-chlorophenyl)isovaleryl chloride
66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

(S)-m-phenoxybenzaldehyde cyanohydrin
39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8

(S)-m-phenoxybenzaldehyde cyanohydrin

A

esfenvalerate
66230-04-4

esfenvalerate

B

[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate
66267-77-4

[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate

Conditions
ConditionsYield
With pyridine In dichloromethane a) 0 deg C 1 h, b) r.t., overnight; Yield given. Title compound not separated from byproducts;
2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
39515-47-4

2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

S-(+)-2-(4-chlorophenyl)isovaleryl chloride
66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

A

esfenvalerate
66230-04-4

esfenvalerate

B

[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate
66267-77-4

[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate

Conditions
ConditionsYield
With pyridine In dichloromethane for 0.5h; Acylation;A 495 mg
B 645 mg
2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride
51631-50-6

2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride

(S)-m-phenoxybenzaldehyde cyanohydrin
39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8

(S)-m-phenoxybenzaldehyde cyanohydrin

A

(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
67614-32-8

(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate

B

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
With pyridine In hexane; acetate buffer at 0℃; pH=4.5; Title compound not separated from byproducts;
(S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate
298702-31-5

(S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pseudomonas cepacia lipase gelozyme; AcOH; 1-butanol / hexane / 3 h / 20 °C / Enzymatic reaction
2: pyridine / acetate buffer; hexane / 0 °C / pH 4.5
View Scheme
2-(4-chlorophenyl)-3-methylbutyric acid
2012-74-0, 55291-27-5, 55332-38-2, 63640-09-5

2-(4-chlorophenyl)-3-methylbutyric acid

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: via (S)-(-)-α-methylbenzylamine salt
2: SOCl2; DMF / CHCl3 / 1 h / 60 °C
3: 495 mg / pyridine / CH2Cl2 / 0.5 h
View Scheme
S-isopropyl-4-chlorophenylacetic acid
55332-38-2

S-isopropyl-4-chlorophenylacetic acid

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2; DMF / CHCl3 / 1 h / 60 °C
2: 495 mg / pyridine / CH2Cl2 / 0.5 h
View Scheme
3-Phenoxybenzaldehyde
39515-51-0

3-Phenoxybenzaldehyde

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / tetrahydrofuran; H2O / 0.5 h / 20 °C
2: 495 mg / pyridine / CH2Cl2 / 0.5 h
View Scheme
Multi-step reaction with 3 steps
2: Candida cylindracea lipase / H2O / 23 h / 30 °C / pH 5
3: pyridine
View Scheme
Multi-step reaction with 3 steps
2: 49 percent / Arthrobacter lipase / H2O / 23 h / 40 °C / further lipases and immobilized Arthrobacter lipase; effect of pH, temperature and (S)/(R) mixture of the acetate
3: pyridine
View Scheme
O-acetyl-(S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
113301-28-3

O-acetyl-(S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / ethanol / diisopropyl ether / 6 h / 25 °C / lipase from Pseudomonas cepacia (Amano)
2: pyridine / CH2Cl2 / a) 0 deg C 1 h, b) r.t., overnight
View Scheme
alpha-cyano-3-phenoxybenzyl acetate
61066-87-3

alpha-cyano-3-phenoxybenzyl acetate

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida cylindracea lipase / H2O / 23 h / 30 °C / pH 5
2: pyridine
View Scheme
Multi-step reaction with 2 steps
1: 49 percent / Arthrobacter lipase / H2O / 23 h / 40 °C / further lipases and immobilized Arthrobacter lipase; effect of pH, temperature and (S)/(R) mixture of the acetate
2: pyridine
View Scheme
cyclo(D-phenylalanyl-D-histidine)

cyclo(D-phenylalanyl-D-histidine)

2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
39515-47-4

2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

(p-chlorophenyl)isopropylketene
92742-11-5

(p-chlorophenyl)isopropylketene

esfenvalerate
66230-04-4

esfenvalerate

racemic alpha-isopropyl-p-chlorophenylacetyl chloride

racemic alpha-isopropyl-p-chlorophenylacetyl chloride

(S)-m-phenoxybenzaldehyde cyanohydrin
39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8

(S)-m-phenoxybenzaldehyde cyanohydrin

esfenvalerate
66230-04-4

esfenvalerate

Conditions
ConditionsYield
With pyridine In methanol; hexane; toluene
esfenvalerate
66230-04-4

esfenvalerate

A

1-allyl-4-chlorobenzene
1745-18-2

1-allyl-4-chlorobenzene

B

4-chloro(ethylbenzene)
622-98-0

4-chloro(ethylbenzene)

C

2-(4-Chlorophenyl)ethanol
1875-88-3

2-(4-Chlorophenyl)ethanol

D

2-(4-chlorophenyl)-3-methylbutyric acid
2012-74-0, 55291-27-5, 55332-38-2, 63640-09-5

2-(4-chlorophenyl)-3-methylbutyric acid

E

1-chloro-4-(1-methylprop-2-en-1-yl)benzene
23853-78-3

1-chloro-4-(1-methylprop-2-en-1-yl)benzene

F

3-phenoxybenzoic acid
3739-38-6

3-phenoxybenzoic acid

G

2-(4-Chloro-phenyl)-propionic acid
938-95-4

2-(4-Chloro-phenyl)-propionic acid

H

3-Phenoxybenzaldehyde
39515-51-0

3-Phenoxybenzaldehyde

I

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

J

methyl N-hydroxybenzene carboximidoate

methyl N-hydroxybenzene carboximidoate

Conditions
ConditionsYield
With dihydrogen peroxide In methanol; water at 25℃; for 4h; pH=10.95;

66230-04-4Relevant articles and documents

Process for preparing (S)- alpha-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl)-isovalerate

-

Page/Page column 16; 17; 19-21; 24; 25, (2008/06/13)

The present invention relates to an environmentally benign process for the preparation of (S)-α-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl)isovalerate from its diastereomeric mixture (RS)-α-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl) isovalerate.

'Gelozymes' in organic synthesis. Part 2: Candida rugosa lipase mediated synthesis of enantiomerically pure (S)-cyano(3-phenoxyphenyl)methyl butyrate

Fadnavis, Nitin W.,Babu, Ravi Luke,Sheelu, Gurrala,Deshpande, Ashlesha

, p. 1695 - 1699 (2007/10/03)

Significant changes in enantioselectivity (E) have been observed when the butanoate ester of (±)-1-hydroxy-1-(3-phenoxyphenyl)acetonitrile was subjected to hydrolysis in acetate buffer (pH 4.5, E = 6.4) and alcoholysis with 1-butanol in hexane catalysed by Candida rugosa lipase (E = 45). Enantiomerically pure (S)-butanoate ester so obtained (e.e. 98.4%) was converted to the corresponding (S)-cyanohydrin using Pseudomonas cepacia (Amano Ps) gelozyme. This strategy overcomes the problem of separation of the unwanted (R)-ester from the (S)-cyanohydrin.

Halogen alkenyl azolyl microbicides

-

, (2008/06/13)

Novel halogenoalkenyl-azolyl derivatives of the formula STR1 in which R1 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heteroaryl, R2 represents alkyl, halogenoalkyl, 1-hydroxyalkyl, 2-hydroxyalkyl, 1-hydroxyhalogenalkyl, 1-alkenyl or 2-alkenyl, X1 represents fluorine, chlorine, bromine or iodine, X2 represents fluorine, chlorine, bromine or iodine, and Y represents nitrogen or a CH group, and addition products thereof with acids or metal salts are very active as microbicides in plant protection and in the protection of materials.

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