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Tetrachlorvinphos

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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
Mol File:
22248-79-9.mol
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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
Water Solubility 
11mg l-1(20°C)
form 
solid
Merck 
13,9267
CAS DataBase Reference
22248-79-9(CAS DataBase Reference)
NIST Chemistry Reference
Tetrachlorvinphos(22248-79-9)
IARC
2B (Vol. 30, Sup 7, 112) 2017
EPA Substance Registry System
Tetrachlorvinphos (22248-79-9)
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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 Data
22248-79-9(Hazardous Substances Data)
Toxicity
LD50 in male, female rats (mg/kg): 1100, 1125 orally (Gaines)

MSDS

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Tetrachlorvinphos Usage And Synthesis

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

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

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.

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.

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.

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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