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Tetrachlorvinphos

CAS No.
22248-79-9
Chemical Name:
Tetrachlorvinphos
Synonyms
ROL;CVMP;ipo8;Rabon;Ravap;Appex;Rabond;Vinfos;Gardon;Dust M
CBNumber:
CB1673649
Molecular Formula:
C10H9Cl4O4P
Molecular Weight:
365.96
MDL Number:
MFCD00078729
MOL File:
22248-79-9.mol
Last updated:2023-05-15 10:43:03

Tetrachlorvinphos 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 Reference 22248-79-9(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII DM33MW89QU
Proposition 65 List Tetrachlorvinphos
IARC 2B (Vol. 30, Sup 7, 112) 2017
NIST Chemistry Reference Tetrachlorvinphos(22248-79-9)
EPA Substance Registry System Tetrachlorvinphos (22248-79-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS09
Signal word  Warning
Hazard statements  H302-H410
Precautionary statements  P264-P270-P273-P301+P312-P391-P501
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
Toxicity LD50 in male, female rats (mg/kg): 1100, 1125 orally (Gaines)

Tetrachlorvinphos price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Usbiological 483637 IPO8 22248-79-9 100ul $499 2021-12-16 Buy
AHH MT-59100 Tetrachlorvinphos 98% 22248-79-9 5g $280 2021-12-16 Buy
Product number Packaging Price Buy
483637 100ul $499 Buy
MT-59100 5g $280 Buy

Tetrachlorvinphos Chemical Properties,Uses,Production

Description

Tetrachlorvinphos 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 Properties

Technical 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 Properties

Powder.Partially soluble in chloroform; slightly soluble in water.

Uses

Tetrachlorvinphos 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.

Uses

Insecticide.

Uses

Tetrachlorvinphos 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.

Definition

ChEBI: 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.

Hazard

Cholinesterase inhibitor. Questionable carcinogen.

Carcinogenicity

When 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 Fate

Tetrachlorvinphos 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 pathway

The 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).

Degradation

Tetrachlorvinphos 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 evaluation

Acute oral LD50 for rats: 4,000-5,000 mg/kg

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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 SD 8447 Stirofo Tetrachlorvinphos, (Z) Vinfos RABON(R) STIRIFOS STIROFOS STIROPHOS Ravap REVAP(R) TETRACHLORVINPHOS, 1GM, NEAT TETRACHLORVINPHOS PESTANAL, 250 MG Phosphoric acid, (1Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl ester stirofos (esa) stirofox tetrachlorvinphos (bsi,iso) TETRACHLOVINPOS TETRACHLOROVINPHOS SHELLSD-8447 (Z)-O,O-dimethyl-O-[1-(2,4,5-trichlorophenyl)-2 -chlorovinyl] phosphate Gardon O,O-dimethyl-O-[1-(2,4,5-trichlorophenyl)-2-chloro]vinylphosphate GARDONA GARDONA(R) DIMETHYL-1-[2,4,5-TRICHLOROPHENYL]-2-CHLOROVINYL PHOSPHATE DEBANTIC CVMP (z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenylphosphoric acid dimethyl ester (Z)-2-Chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl phosphate (Z)-2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate 2,4,5-trichloro-alpha-(chloromethylene)-benzylalcohodimethylphosphate 2,4,5-trichloro-alpha-(chloromethylene)benzylphosphate Appex cis-Gardona Dietreen Dust M ENT 25,841 Gardcide Gordona ipo8 Rabona Dimethyl 2,4,5-trichloro-alpha-(chloromethylene)benzyl phosphate Phosphoric acid, 2-chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl ester, (Z) 2,4,5-Trichloro-alpha-(chloromethylene)benzyl phosphate ester 2-Chloro-1-(2,4,5-trichlorophenyl)vinyl Dimethylphosphate, (Z)- C14513 Tetrachlorvinphos Tetrachlorvinphos Solution, 100ppm Tetrachlorvinphos Standard Tetrachlorvinphos