ChemicalBook--->CAS DataBase List--->80844-07-1

80844-07-1

80844-07-1 Structure

80844-07-1 Structure
IdentificationMore
[Name]

Ethofenprox
[CAS]

80844-07-1
[Synonyms]

1-((2-(4-ethoxyphenyl)-2-methylpropoxy)methyl)-3-phenoxybenzene
ETHOFENPROX
ETOFENPROX
NUKIL
PUNKASO
TREBON
VECTRON
1-((2-(4-ethoxyphenyl)-2-methylpropoxy)methyl)-3-phenoxy-benzen
3-phenoxybenzyl2-(4-ethoxyphenyl)-2-methylpropylether
ethophenprox
mti500
2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether
Zoecon RF-316
2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl)-2-methylpropoxy)methyl)-3-phenoxybenzene
Benzene, 1-2-(4-ethoxyphenyl)-2-methylpropoxymethyl-3-phenoxy-
etofenprox (bsi,iso)
ETOPHENPROX
ethoporoxyfen
Lenatop
PEPE
[EINECS(EC#)]

407-980-2
[Molecular Formula]

C25H28O3
[MDL Number]

MFCD00210287
[Molecular Weight]

376.49
[MOL File]

80844-07-1.mol
Chemical PropertiesBack Directory
[Appearance]

solid
[Melting point ]

36.4-38.0°
[Boiling point ]

445.03°C (rough estimate)
[density ]

1.1386 (rough estimate)
[vapor pressure ]

32×10-3 Pa (100 °C)
[refractive index ]

nD20.2 1.5732
[storage temp. ]

0-6°C
[solubility ]

DMSO: 100 mg/mL (265.61 mM)
[form ]

neat
[Water Solubility ]

<0.001 mg l-1(25 °C)
[color ]

Off-white to light yellow
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Henry's Law Constant]

7.4×101 mol/(m3Pa) at 25℃, Maniere et al. (2011)
[Major Application]

agriculture
environmental
[InChI]

1S/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
[InChIKey]

YREQHYQNNWYQCJ-UHFFFAOYSA-N
[SMILES]

CCOc1ccc(cc1)C(C)(C)COCc2cccc(Oc3ccccc3)c2
[CAS DataBase Reference]

80844-07-1(CAS DataBase Reference)
[NIST Chemistry Reference]

Etofenprox(80844-07-1)
[EPA Substance Registry System]

80844-07-1(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Environment (GHS09)
GHS09
[Signal word ]

Warning
[Hazard statements ]

H362-H410
[Precautionary statements ]

P201-P260-P263-P273-P308+P313-P391
[RIDADR ]

UN 3077 9 / PGIII
[WGK Germany ]

2
[RTECS ]

DA0670000
[REACH Registrations]

Inactive
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
Lact.
[Toxicity]

LD50 in rats, mice (mg/kg): >2880, >107200 orally; >2140, >2140 dermally
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Diethyl ether-->Thionyl chloride-->Aluminum chloride-->Carbon disulfide-->Isobutyric acid-->Methanesulfonic acid-->Isobutyryl chloride-->Phenetole
Questions And AnswerBack Directory
[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.
Hazard InformationBack Directory
[Chemical Properties]

solid
[Uses]

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.
[Uses]

Insecticide.
[Definition]

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

The commercial production of eofenprox involves a multi-step organic synthesis starting with a benzyl alcohol derivative. This intermediate undergoes etherification with a phenoxybenzyl halide, followed by esterification with a carboxylic acid or acid chloride to form the final ether-ester structure characteristic of eofenprox. The process is carefully controlled to maintain the stereochemistry and purity required for biological activity.
[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
[Mechanism of action]

Broad-spectrum with contact and stomach action. Sodium channel modulator.
[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.
[Pesticide Type]

Insecticide
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

80844-07-1(sigmaaldrich)
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