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Tetrachlorvinphos

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CAS:22248-79-9
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CAS:22248-79-9
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CAS:22248-79-9
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Tetrachlorvinphos Basic information
Product Name:Tetrachlorvinphos
Synonyms:ncic00168;o,o-dimethyl-o-2-chlor-1-(2,4,5-trichlorphenyl)-vinyl-phosphat;Phosphoric acid, 2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl ester, (Z)-;phosphoricacid,2-chloro-1-(2,4,5-trichlorophenyl)ethenyldimethylester;phosphoricacid,2-chloro-1-(2,4,5-trichlorophenyl)vinyldimethylester;Rabon;Rabond;ROL
CAS:22248-79-9
MF:C10H9Cl4O4P
MW:365.96
EINECS:244-865-4
Product Categories:
Mol File:22248-79-9.mol
Tetrachlorvinphos Structure
Tetrachlorvinphos Chemical Properties
Melting point 97-98 °C(lit.)
Boiling point 399.5±42.0 °C(Predicted)
density 1.520±0.06 g/cm3(Predicted)
vapor pressure 6.0×10-6 Pa (20 °C)
storage temp. 0-6°C
solubility Acetonitrile (Slightly), Methanol (Slightly)
Water Solubility 11mg l-1(20°C)
form solid
Merck 13,9267
CAS DataBase Reference22248-79-9(CAS DataBase Reference)
IARC2B (Vol. 30, Sup 7, 112) 2017
NIST Chemistry ReferenceTetrachlorvinphos(22248-79-9)
EPA Substance Registry SystemTetrachlorvinphos (22248-79-9)
Safety Information
Hazard Codes Xn,N,F
Risk Statements 21/22-50/53-36-20/21/22-11-22
Safety Statements 36-60-61-36/37-16
RIDADR UN 3077 9/PG 3
RTECS TB9100000
HS Code 29199000
Hazardous Substances Data22248-79-9(Hazardous Substances Data)
ToxicityLD50 in male, female rats (mg/kg): 1100, 1125 orally (Gaines)
MSDS Information
ProviderLanguage
Tetrachlorvinphos English
Tetrachlorvinphos Usage And Synthesis
DescriptionTetrachlorvinphos was initially registered for use in the United States in 1966 for use on various food crops, livestock, and pet animals, and in around buildings. Its use on food crops were voluntarily canceled in the United States in 1987; however, it is used on food crops in developing countries. Tetrachlorvinphos is sold under the trade names Rabon and Gardona.
Chemical PropertiesTechnical tetrachlorvinphos is a tan-to-brown crystalline solid. Tetrachlorvinphos is stable at ,100 C and slowly hydrolyzed at 50°C. Aromatic odor.
Soluble in water at 24°C 15 ppm; limited solubility in most aromatic hydrocarbons.
Chemical PropertiesPowder.Partially soluble in chloroform; slightly soluble in water.
UsesTetrachlorvinphos is commonly used as a feed additive to control flies in livestock and as dusts, sprays, dips, and collar ingredient to control ticks and fleas on domestic pets. It is extensively used in poultry. In horses, its formulations are commonly used as a feed additive (feed-through tetrachlorvinphos) larvicide. In addition, tetrachlorvinphos is also used in the control of public health pests, manure flies associated with livestock, and poultry as a feed additive.
UsesInsecticide.
UsesTetrachlorvinphos is used to control lepidopterous and dipterous larvae in fruit and lepidopterous larvae in cotton, maize, rice, tobacco and vegetables. It is also used against nuisance flies in animal houses, animal ectoparasites and stored product pests.
DefinitionChEBI: Tetrachlorvinphos is an alkenyl phosphate, a dialkyl phosphate, an organophosphate insecticide, an organochlorine insecticide and a trichlorobenzene. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an agrochemical, an EC 3.1.1.8 (cholinesterase) inhibitor and an acaricide. It is functionally related to a 1-phenylethenol.
HazardCholinesterase inhibitor. Questionable carcinogen.
CarcinogenicityWhen rats were given diets with 0, 4250, or 8500 ppm tetrachlorvinphos for 80 weeks, both males and females had a high incidence of thyroid C-cell hyperplasia, and females had increased incidences of adrenal cortical adenomas and thyroid C-cell adenomas .
Environmental FateTetrachlorvinphos is nonpersistent in the environment. The primary route of dissipation is through biotic degradation. Based on its use pattern, risks of contamination of groundwater or surface water by tetrachlorvinphos are minimal.
Metabolic pathwayThe chemical structure of tetrachlorvinphos is very close to that of chlorfenvinphos and the routes of metabolic breakdown have been shown to be very similar. Technical tetrachlorvinphos is usually >95% Z-isomer, unlike chlorfenvinphos which is an E/Z mixture. As with chlorfenvinphos, the major routes of detoxification are by dealkylation and hydrolysis to yield desmethyltetrachlorvinphos and 2,2’,4’,5’- tetrachloroacetophenone plus dimethyl phosphate, respectively. Further metabolism of the chloroacetophenone moiety then leads, via reduction or hydrolysis and glutathione-dependent displacement of the side chain chlorine substituent, to the formation of 1-(2,4,5-trichlophenyl) ethane-l,Z-diol and 1-(2,4,5-trichlorophenyl)ethan-l-owl hich are conjugated with glucose or glucuronic acid to afford the ultimate metabolites. Oxidation of the β carbon atom to give 2,4,5-trichloromandelic acid followed by decarboxylation leads to the formation of 2,4,5-trichlorobenzoic acid which is conjugated with glycine in some mammals as the final metabolite. The metabolic routes were summarised by Beynon et al. (1973).
DegradationTetrachlorvinphos is hydrolysed slowly in neutral, acidic and slightly alkaline aqueous solutions but hydrolysed rapidly in strongly alkaline solutions to metabolites 3 and 5 (PM). Dureja et al. (1987) reported the photochemical degradation of tetrachlorvinphos in water, ethanol, ether and hexane irradiated with a xenon lamp. In polar solvents, the main product was desmethyltetrachlorvinphos (2), whereas in non-polar solvents such as hexane the reaction yielded dimethyl phosphate (3), 2,4,5-trichloroacet ophenone (4) and 2,2’,4’,5’-tetrachloroacetophenone (5). Interconversion of the Z- and Ε-isomers has been observed on leaves (Beynon and Wright, 1969). These pathways are shown in Scheme 1.
Toxicity evaluationAcute oral LD50 for rats: 4,000-5,000 mg/kg
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