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Prallethrin

Prallethrin structure

CAS No:
23031-36-9
Formula:
C19H24O3
Chemical Name:
Prallethrin
Synonyms:
Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-,2-methyl-4-oxo-3-(2-propyn-1-yl)-2-cyclopenten-1-yl ester;Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methylpropenyl)-,ester with 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one,trans-(±)-;Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propenyl)-,2-methyl-4-oxo-3-(2-propynyl)-2-cyclopenten-1-yl ester;Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methylpropenyl)-,ester with 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one;2-Cyclopenten-1-one,4-hydroxy-3-methyl-2-(2-propynyl)-,2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate,trans-(±)-;S 4068;Prallethrin;S 4068SF;Rethrinpropargyl;Etoc;Acetylene C permethrin;Prallethrine;23031-13-2;24909-64-6;24909-53-3
Categories:
Agrochemicals > Insecticides

Description

The original medicine is an oil like liquid. At b.p.>313.5℃ , the relative density is 1.03. It is easy to dissolve in methanol and hexane. The solubility is >50% at normal temperature, The solubility in the water at 25 C is 8.03mg/L, The distribution coefficient is 30800.

Prallethrin Basic Attributes

Molecular Weight：

300.39

Exact Mass：

300.39

EC Number：

245-387-9

HScode：

2916209027

Characteristics

PSA：

43.4

XLogP3：

4.49 at 25 deg C

Appearance：

solid

Density：

1.03 at 20 deg C/4 deg C

Melting Point：

<25 °C

Boiling Point：

>313.5 °C

Flash Point：

139 °C

Water Solubility：

In hexane, methanol, xylene, >500 g/kg at 20-25 deg C

Storage Conditions：

2-8°C

Vapor Pressure：

﹤4.3×10 -5 Pa (23.1 °C)

Safety Information

Transport codes：

UN28116.1/PG2

wgk germany：

hazard class code：

22-23-50/53

safety instructions：

45-60-61

Marks：

T,N

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P261-P273-P311-P501

Hazard Statements：

H302-H331-H410

GHS Classification：

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P284, P301+P312, P304+P340, P310, P311, P320, P321, P330, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 86 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl chrysanthemate

Prallethrin Use and Manufacturing

Methods of Manufacturing

Preparation of cyproterenol in the presence of sodium ethoxide and absolute ethanol, ethyl acetoacetate and propargyl benzene sulfonate were stirred and reacted for 8 hours, and then refluxed for 1 hour to prepare 2-propargyl-3-oxobutanoic acid Ethyl acetate, yield 85.3%. The product from the previous step was added dropwise to a 10% Na2CO3 solution, and the azeotrope of the product and water was distilled off at the same time to produce 5-oxo-1-hexyne, with a yield of 63.8%. Heat MgCH3OH and iodine to reflux, distill methanol, add dimethylformamide (DMF), pass CO2 to saturation, heat and distill the remaining methanol to the distillation temperature of 140 ℃, still pass CO2 during distillation, and finally pass 1h CO2 An MMC (methyl magnesium carbonate)-DMF solution was prepared. Add 5-oxo-1-hexyne to the MMC-DMF solution, stir and heat to above 110°C to react for 2h, distill out DMF, add hydrochloric acid and water until the solid is dissolved, extract with ether, add KOH solution to get 25% 3 -Potassium oxo-6-heptanoate solution. Adjust the above solution to pH 8, raise the temperature to 35°C, add pyruvaldehyde dropwise, maintain the pH at 8 to react for 16h, cool, and saturate the reaction solution with common salt and extract with ether to obtain 3-hydroxy-8-nonyne-2, 5- The yield of dione is 41.6%～46.8%. Add 10% NaOH to the solution of 3-hydroxy-8-nonyne-2, 5-dione in diethyl ether dropwise after 2.5h, keep at -8～10℃, then continue the reaction at -8～-5℃ for 3h, use The concentrated hydrochloric acid was adjusted to neutrality, saturated with common salt, and extracted with ether to obtain a yellow liquid cyproterone with a yield of 59.9%. The above route is an improvement of the Schechter route. The literature reports that the Schechter synthesis route is as follows: cyproterone can also be prepared by furan derivatives. In view of the fact that the reaction of propargyl halides with magnesium can produce Grignard reagents, it is usually necessary to add mercury salts. To avoid environmental pollution, zinc salts can be used instead of mercury salts. In the continuous Grignard reaction, the combination of propargyl chloride and propargyl bromide can make the reaction very stable. Then the furfural transposition reaction and isomerization reaction are carried out. The transposition reaction is performed under acidic conditions, and the isomerization reaction is performed under basic conditions. Synthesis of cyproterenol 4-hydroxy-3-methyl-2-propargylcyclopentenone reacts with chrysanthemum chloride to synthesize cyhalothrin (the synthesis of chrysanthemum chloride is the same as that of pyrethroid chloride).

Uses

Insecticide.

Computed Properties

Molecular Weight:300.4
XLogP3:4.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:300.17254462
Monoisotopic Mass:300.17254462
Topological Polar Surface Area:43.4
Heavy Atom Count:22
Complexity:620
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Acetylacetone

Ethyl acetate

Ethanol

Dimethylformamide

Price Analysis

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