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80844-07-1

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80844-07-1 Usage

Description

Etofenprox belongs to a pyrethroid derivative that is commonly used as an insecticide in agriculture, horticulture, viticulture, forestry, animal health and public health against various insect pests. It can be found as an active ingredient in a variety of pest control products, which is effective to control broad spectrum of pests, such as crawling and flying insects. In the field of agriculture, etofenprox can be applied on a broad range of crops, including rice, fruits, vegetables, corn, soybeans and tea, which is poorly absorbed by roots and little translocation occurs within plants. It is also used for the public health by controlling adult mosquitoes, non biting midges, biting and non-biting flies, which may carry the pathogen. Besides, etofenprox can be found as an component in flea and tick medications for dogs and cats. Etofenprox is a new type of insecticide with low mammalian toxicity, which can be decomposed in soil by anaerobic and aerobic microorganisms. It functions by strongly disrupting the transmission of nervous impulses and causes paralysis and death to the target insect.

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 80844-07-1 differently. You can refer to the following data:
1. Insecticide.
2. Etofenprox is used to control a wide variety of insects on fruit, tea, soyabeans and many vegetables. It is also used in public health and animal health.

Definition

ChEBI: An aromatic ether that is the 3-phenoxybenzyl ether of 2-(4-ethoxyphenyl)-2-methylpropan-1-ol.

Agricultural Uses

Insecticide: Approved for use in the U.S. and more than a dozen EU countries.

Trade name

MTI 500?; PUNKASO?; TREBON?; ZOECON? RF-316

Metabolic pathway

Etofenprox is one of the few members of a new class, the non-ester pyrethroids. It lacks the ester bond and therefore is not subject to facile chemical or biochemical hydrolysis. Metabolic options will be limited to oxidative processes. Little has been published in the scientific literature. Its photochemistry has been described and metabolic oxidation products have been noted.

Degradation

Etofenprox is stable in acid and alkaline media for more than 100 days at 80 °C. It is reasonably stable to light under normal conditions of use but it is photodegradable. Under conditions where allethrin was degraded with a half-life of 0.5 hours, etofenprox had a half-life of 3 hours (Tsao and Eto, 1990). The major product was the ester formed by oxidation at the benzylic carbon atom to form 2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzoate (2), clearly the result of hydroxylation and dehydrogenation. This ester was found to be non-toxic to houseflies. It was cleaved to form 3PBA (5) and the alcohol (6). 6 was degraded via decarboxylation to 7 and 8. A concurrent reaction of etofenprox was O-de-ethylation to the phenol (3). A similar array of products was seen in both aqueous suspension and as a thin film on glass. It should be noted that this study did not utilise radiolabelled compound.

Check Digit Verification of cas no

The CAS Registry Mumber 80844-07-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,0,8,4 and 4 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 80844-07:
(7*8)+(6*0)+(5*8)+(4*4)+(3*4)+(2*0)+(1*7)=131
131 % 10 = 1
So 80844-07-1 is a valid CAS Registry Number.
InChI:InChI=1/C25H28O3/c1-4-27-22-15-13-21(14-16-22)25(2,3)19-26-18-20-9-8-12-24(17-20)28-23-10-6-5-7-11-23/h5-17H,4,18-19H2,1-3H3

80844-07-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name etofenprox

1.2 Other means of identification

Product number -
Other names ETOFENPROX

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:80844-07-1 SDS

80844-07-1Synthetic route

3-phenoxybenzyl bromide
51632-16-7

3-phenoxybenzyl bromide

2-(4-ethoxyphenyl)-2,2-dimethylethanol
83493-63-4

2-(4-ethoxyphenyl)-2,2-dimethylethanol

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
With potassium hydroxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 0.583333h; Irradiation;95%
(m-phenoxyphenyl)methyl chlorosulfite

(m-phenoxyphenyl)methyl chlorosulfite

2-(4-ethoxyphenyl)-2,2-dimethylethanol
83493-63-4

2-(4-ethoxyphenyl)-2,2-dimethylethanol

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
at 50℃; for 2h;93%
ethyl iodide
75-03-6

ethyl iodide

3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether
80854-21-3

3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 25℃; for 14h; Inert atmosphere;86%
3-Phenoxybenzyl alcohol
13826-35-2

3-Phenoxybenzyl alcohol

4-(2'-chloro-1',1'-dimethylethyl)ethoxybenzene
83493-80-5

4-(2'-chloro-1',1'-dimethylethyl)ethoxybenzene

A

etofenprox
80844-07-1

etofenprox

B

3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether
80854-21-3

3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 110 - 120℃; for 15h;A 42.5%
B 8.5%
3-phenoxybenzyl bromide
51632-16-7

3-phenoxybenzyl bromide

2-methyl-2-(m-/p-ethoxyphenyl)-1-propanol

2-methyl-2-(m-/p-ethoxyphenyl)-1-propanol

A

etofenprox
80844-07-1

etofenprox

B

2-Methyl-2-(m-ethoxyphenyl)propyl m-(phenoxy)benzyl ether

2-Methyl-2-(m-ethoxyphenyl)propyl m-(phenoxy)benzyl ether

Conditions
ConditionsYield
With potassium hydroxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 8h;
neophyl chloride
515-40-2

neophyl chloride

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / HNO3; H2SO4
2: 67 percent / K2CO3 / acetone / 15 h / 40 °C
3: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
1-chloro-2-methyl-2-(4-nitrophenyl)propane
99359-77-0

1-chloro-2-methyl-2-(4-nitrophenyl)propane

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 67 percent / K2CO3 / acetone / 15 h / 40 °C
2: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
Phenetole
103-73-1

Phenetole

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2SO4 / 5 h / 20 °C
2: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
benzene
71-43-2

benzene

1,x-dichloro-octane

1,x-dichloro-octane

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / H2SO4
2: 91 percent / HNO3; H2SO4
3: 67 percent / K2CO3 / acetone / 15 h / 40 °C
4: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
methyl 2-(4-chlorophenyl)-2-methylpropanoate
57225-86-2

methyl 2-(4-chlorophenyl)-2-methylpropanoate

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
3: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / water; 1,4-dioxane / 16 h / 100 - 115 °C / Inert atmosphere
4: potassium carbonate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C / Inert atmosphere
View Scheme
2-(4-chlorophenyl)-2-methylpropyl alcohol
80854-14-4

2-(4-chlorophenyl)-2-methylpropyl alcohol

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
2: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / water; 1,4-dioxane / 16 h / 100 - 115 °C / Inert atmosphere
3: potassium carbonate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C / Inert atmosphere
View Scheme
3-Phenoxybenzyl 2-(4-chlorophenyl)-2-methylpropyl ether

3-Phenoxybenzyl 2-(4-chlorophenyl)-2-methylpropyl ether

etofenprox
80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / water; 1,4-dioxane / 16 h / 100 - 115 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C / Inert atmosphere
View Scheme
thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

etofenprox
80844-07-1

etofenprox

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C37H35O3S2(1+)*C2F3O2(1-)

C37H35O3S2(1+)*C2F3O2(1-)

Conditions
ConditionsYield
With Thianthrene In acetonitrile at -78 - 25℃;84%
sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

etofenprox
80844-07-1

etofenprox

C37H35O3S2(1+)*BF4(1-)

C37H35O3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: thianthrene-5-oxide; etofenprox With trifluoroacetic anhydride In acetonitrile at -78 - 25℃; Sealed tube;
Stage #2: sodium tetrafluoroborate In dichloromethane; water
84%
1,1-bis(phenylsulfonyl)ethylene
39082-53-6

1,1-bis(phenylsulfonyl)ethylene

etofenprox
80844-07-1

etofenprox

(3-(2-(4-ethoxyphenyl)-2-methylpropoxy)-3-(3-phenoxyphenyl)propane-1,1-diyldisulfonyl)dibenzene

(3-(2-(4-ethoxyphenyl)-2-methylpropoxy)-3-(3-phenoxyphenyl)propane-1,1-diyldisulfonyl)dibenzene

Conditions
ConditionsYield
With [Ir(3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl)2(4,4'-bis(trifluoromethyl)bipyridine)]PF6 In dichloromethane for 48h; Sealed tube; Inert atmosphere; Irradiation;84%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

etofenprox
80844-07-1

etofenprox

C37H35O3S2(1+)*BF4(1-)

C37H35O3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; etofenprox With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 15h; Schlenk technique;
Stage #2: sodium tetrafluoroborate In dichloromethane; water
74%
4-fluoro-2-methylphenol
452-72-2

4-fluoro-2-methylphenol

etofenprox
80844-07-1

etofenprox

C32H32O5

C32H32O5

Conditions
ConditionsYield
With iodosodilactone at 90℃; for 18h; Sealed tube;42%
O-(p-toluenesulfonyl)-N-methylhydroxylamine
25370-97-2

O-(p-toluenesulfonyl)-N-methylhydroxylamine

etofenprox
80844-07-1

etofenprox

2-ethoxy-N-methyl-5-(2-methyl-1-((3-phenoxybenzyl)oxy)propan-2-yl)aniline

2-ethoxy-N-methyl-5-(2-methyl-1-((3-phenoxybenzyl)oxy)propan-2-yl)aniline

Conditions
ConditionsYield
With air at 20℃; for 36h; chemoselective reaction;37%
etofenprox
80844-07-1

etofenprox

C27H29N3O3

C27H29N3O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic anhydride / acetonitrile / 15 h / -40 - 25 °C / Schlenk technique
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrakis(acetonitrile)copper(I)tetrafluoroborate; tetramethyl ammoniumhydroxide / acetonitrile; dimethyl sulfoxide / 8 h / 15 °C / Inert atmosphere; Irradiation
View Scheme

80844-07-1Downstream Products

80844-07-1Relevant articles and documents

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

Taniguchi, Takashi,Taketomo, Yasuaki,Moriyama, Mizuki,Matsuo, Noritada,Tanabe, Yoo

supporting information, (2019/03/26)

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

Rakhimov,Galin,Tomilov,Le

, p. 1629 - 1634 (2007/10/03)

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.

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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