80854-21-3

Basic information

• Product Name: etofenprox-desethyl
• Synonyms: etofenprox desethyl;etofenprox-desethyl;Etofenprox-desethyl, 10 μg /μL in cyclohexane
• CAS NO: 80854-21-3
• Molecular Formula: C₂₃H₂₄O₃
• Molecular Weight: 348.44
• Mol File: 80854-21-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 481.7°C at 760 mmHg
• Flash Point: 245.1°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 6.67E-10mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: etofenprox-desethyl(CAS DataBase Reference)
• NIST Chemistry Reference: etofenprox-desethyl(80854-21-3)
• EPA Substance Registry System: etofenprox-desethyl(80854-21-3)

Safety Data

• Hazardous Substances Data: 80854-21-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H24O3/c1-23(2,19-11-13-20(24)14-12-19)17-25-16-18-7-6-10-22(15-18)26-21-8-4-3-5-9-21/h3-15,24H,16-17H2,1-2H3

Upstream product

• 80854-14-4 2-(4-chlorophenyl)-2-methylpropyl alcohol 
• 57225-86-2 methyl 2-(4-chlorophenyl)-2-methylpropanoate 
• 71-43-2 benzene 
• 103-73-1 Phenetole 
• 99359-77-0 1-chloro-2-methyl-2-(4-nitrophenyl)propane 
• 515-40-2 neophyl chloride 
• 13826-35-2 3-Phenoxybenzyl alcohol 
• 83493-80-5 4-(2'-chloro-1',1'-dimethylethyl)ethoxybenzene 

Downstream Products

• 162965-61-9 3-phenoxybenzyl 2-{4-(methoxycarbonylmethyloxy)phenyl}-2-methylpropyl ether 
• 80844-07-1 etofenprox 
• 111856-48-5 3-phenoxybenzyl 2-(4-difluorochloromethoxyphenyl)-2-methylpropyl ether 
• 111872-58-3 halfenprox 
• 132931-15-8 potassium salt of 3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether 

Relevant articles and documents

Synthesis and stereostructure-activity relationship of novel pyrethroids possessing two asymmetric centers on a cyclopropane ring

2-Methylcyclopropane pyrethroid insecticides bearing chiral cyanohydrin esters or chiral ethers and two asymmetric centers on the cyclopropane ring, were synthesized. These compounds were designed using a “reverse connection approach” between the isopropyl group in Fenvalerate, and between two dimethyl groups in an Etofenprox analogue (the methyl, ethyl form), respectively. These syntheses were achieved by accessible ring opening reactions of commercially available (±)-, (R)-, and (S)-propylene oxides using 4-chlorobenzyl cyanide anion as the crucial step, giving good overall yield of the product with >98% ee. The insecticidal activity against the common mosquito (Culex pipiens pallens) was assessed for pairs of achiral diastereomeric (1R*,2S*)-, (1R*,2R*)-cyanohydrin esters, and (1R*,2S*)-, (1R*,2R*)-ethers; only the (1R*,2R*)-ether was significantly effective. For the enantiomeric (1S,2S)-ether and (1R,2R)-ether, the activity was clearly centered on the (1R,2R)-ether. The present stereostructure?activity relationship revealed that (i) cyanohydrin esters derived from fenvalerate were unexpectedly inactive, whereas ethers derived from etofenprox were active, and (ii) apparent chiral discrimination between the (1S,2S)-ether and the (1R,2R)-ether was observed. During the present synthetic study, we performed alternative convergent syntheses of Etofenprox and novel 4-EtO-type (1S,2S)- and (1R,2R)-pyrethroids from the corresponding parent 4-Cl-type pyrethroids, by utilizing a recently-developed hydroxylation cross-coupling reaction.

Synthesis of ethophenprox

An ethophenprox synthesis from easily available p-nitroneophyl chloride was developed. The reduction of the latter to aniline derivative followed by Sandmayer's and Claisen's reactions furnished p-ethoxyneophyl chloride that by condensation with 3-phenoxybenzyl alcohol in the presence KOH in DMSO yielded ethophenprox.

Insecticidal resin coating film

An insecticidal resin coating film comprising a combination of an acrylonitrile and/or methacrylonitrile copolymer resin and an insecticidal component selected from the group consisting of specified compounds exhibits an insecticidal effect, since the compound is kept on the surface of the coating film in a state capable of exhibiting its insecticidal effect for a long period of time.

2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives

The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: STR1 wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: STR2 or the following general formula [III]: STR3 wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.