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Esfenvalerate

Esfenvalerate structure

CAS No:
66230-04-4
Formula:
C25H22ClNO3
Chemical Name:
Esfenvalerate
Synonyms:
Benzeneacetic acid,4-chloro-α-(1-methylethyl)-,(S)-cyano(3-phenoxyphenyl)methyl ester,(αS)-;Benzeneacetic acid,4-chloro-α-(1-methylethyl)-,cyano(3-phenoxyphenyl)methyl ester,[S-(R*,R*)]-;Fenvalerate α;(S)-α-Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)isovalerate;S 5602Aα;Esfenvalerate;Fenvalerate Aα;Aα;OMS 3023;Sumicidin Aα;Sumi-alpha;S 1844;Sumi-alfa;Asana;(S,S)-Fenvalerate;Asana XL;Sumidan;α-Sum;1S,1′S-Fenvalerate;Sumi-Gold;Soumi Gold;72650-28-3
Categories:
Agrochemicals > Insecticides

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Description

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

Esfenvalerate Basic Attributes

Molecular Weight：

419.9

Exact Mass：

419.90

EC Number：

613-911-9

HScode：

2926909090

Characteristics

PSA：

59.3

XLogP3：

6.2

Appearance：

COLOURLESS-TO-WHITE CRYSTALS.

Density：

1.175 g/cm³ @ Temp: 25 °C

Melting Point：

59-60.2 °C

Boiling Point：

151-167 °C

Flash Point：

256°C

Refractive Index：

1.586

Water Solubility：

Solubility in water: none

Storage Conditions：

0-6°C

Vapor Pressure：

Vapour pressure at 20°C: negligible

Toxicity：

Oral-Rat LD50: 70.2 mg/kg; Oral-Mouse LD50: 185 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and chloride gases

Specific rotation：

D25 -15.0° (c = 2.0 in CH3OH)

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811

wgk germany：

hazard class code：

23/25-43-50/53

safety instructions：

24-36/37/39-45-60-61

RTECS Number：

CY1576367

Marks：

T;N,N,T

Storage features：

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stability/Shelf Life：

Pyrethrins /are/ stable for long periods in water-based aerosols where emulsifiers give neutral water systems. /Pyrethrins/

Precautionary statement(s)：

P261-P273-P280-P301 + P310 + P330-P304 + P340 + P312-P403 + P233

Hazard Statements：

H301 + H331-H317-H410

Toxicity

Toxicity class：

highly toxic

Esfenvalerate Use and Manufacturing

Methods of Manufacturing

Fenvalerate has two asymmetric carbon atoms in its molecule, so there are four optical isomers of S, S, S, R, R, S, R, and R. Among them, S and S have the highest drug efficacy, and R and R have the lowest drug efficacy. The main methods of increasing S and S body are as follows. The chiral phase transfer catalyst was used to synthesize (S)-(-)-α-methylbenzylamine as the resolving agent, and the racemic α-isopropyl-p-chlorophenylacetic acid was resolved to obtain the S-acid. Synthesize the corresponding S-acid chloride. Then it reacts with m-phenoxybenzaldehyde and sodium cyanide, using chiral N-benzyl cinconidine ammonium chloride (BCDC) as a phase transfer catalyst to obtain diastereomers S, S and S, R body, of which S, S body excess 5%. This method is simple in operation, mild in reaction conditions and high in yield, and is a promising method for asymmetric synthesis. The choice of the chiral phase transfer catalyst and the reaction conditions of this method need to be explored. Chemical Resolution-The epimer is first chemically resolved from α-isopropyl-p-chlorophenylacetic acid to form S-acid. After acid chlorination, it is then reacted with m-phenoxybenzaldehyde and sodium cyanide to produce Fenvalerate S, S body and S, R body. Then use their physical and chemical properties to separate them. Finally, the S, R body epimer is made into S, S body. S, S body is cis-valeric acid. This method has been industrialized in Japan. The advantages are S, S body with high purity, good quality, and high yield. The disadvantage is that R acid needs to be developed, and the cost is relatively high. The epimerization method uses the physical and chemical properties of the isomers (S, R and R, S enantiomers) and the β isomers (S, S and R, R enantiomers) to separate them. Then the body epimer is β-body. This method has low investment, simple operation, and mild reaction conditions. It is a promising process and has been industrialized.

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.

Material

Phosphorus oxychloride

Sodium benzoate

Thionyl chloride

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