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
80844-07-1Relevant 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.