22248-79-9 Usage
Description
Tetrachlorvinphos, also known as Rabon and Gardona, is an organophosphate insecticide that was initially registered for use in the United States in 1966. It is a tan-to-brown crystalline solid with an aromatic odor and is stable at temperatures below 100°C. Tetrachlorvinphos is partially soluble in chloroform, slightly soluble in water, and has limited solubility in most aromatic hydrocarbons.
Uses
Used in Agriculture:
Tetrachlorvinphos is used as an insecticide for controlling lepidopterous and dipterous larvae in various crops, including fruit, cotton, maize, rice, tobacco, and vegetables. It helps protect these crops from damage caused by these pests.
Used in Livestock and Poultry:
Tetrachlorvinphos is commonly used as a feed additive to control flies in livestock and poultry. It is also used in the form of dusts, sprays, dips, and collar ingredients to control ticks and fleas on domestic pets, particularly in the poultry industry.
Used in Equine Industry:
In horses, tetrachlorvinphos is used in the form of feed additives, specifically as a feed-through larvicide, to control pests.
Used in Public Health:
Tetrachlorvinphos is also utilized in the control of public health pests, manure flies associated with livestock, and poultry as a feed additive, contributing to a healthier environment for both animals and humans.
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
Check Digit Verification of cas no
The CAS Registry Mumber 22248-79-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,2,4 and 8 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 22248-79:
(7*2)+(6*2)+(5*2)+(4*4)+(3*8)+(2*7)+(1*9)=99
99 % 10 = 9
So 22248-79-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H9Cl4O4P/c1-16-19(15,17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5+
22248-79-9Relevant articles and documents
Macrocyclic plant acaricides
-
, (2008/06/13)
Compounds of the formula I STR1 in which either R is methyl and there is a double bond in the 9,10-position, or in which R is hydrogen and there is a single bond in the 9,10-position, are highly active against Acarina which damage plants.