80844-07-1 Usage
Description
Etofenprox is a pyrethroid derivative commonly used as an insecticide in various sectors, including agriculture, horticulture, viticulture, forestry, animal health, and public health. It is an effective active ingredient in pest control products, targeting a broad spectrum of pests such as crawling and flying insects. With low mammalian toxicity and the ability to decompose in soil, etofenprox strongly disrupts the transmission of nervous impulses in insects, leading to paralysis and death.
Uses
Used in Agriculture:
Etofenprox is used as an insecticide for a wide variety of crops, including rice, fruits, vegetables, corn, soybeans, and tea. It is poorly absorbed by roots and has minimal translocation within plants.
Used in Public Health:
Etofenprox is used to control adult mosquitoes, non-biting midges, and biting and non-biting flies, which may carry pathogens.
Used in Animal Health:
Etofenprox can be found as a component in flea and tick medications for dogs and cats, helping to control these parasites and protect the health of pets.
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.