U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H9Cl4O4P
Molecular Weight 365.962
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of STIROFOS

SMILES

COP(=O)(OC)O\C(=C/Cl)C1=C(Cl)C=C(Cl)C(Cl)=C1

InChI

InChIKey=UBCKGWBNUIFUST-YHYXMXQVSA-N
InChI=1S/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-

HIDE SMILES / InChI
(E)-Tetrachlorovinphos is an (E)- isomer of Tetrachlorovinphos. Tetrachlorovinphos is an organophosphate cholinesterase inhibitor that is used as an insecticide. Tetrachlorvinphos was introduced and first used commercially in 1966 in the USA. Tetrachlorvinphos was originally registered for use on various food crops, livestock, pet animals. Tetrachlorvinphos is applied dermally to livestock to control flies and mites. It is used as an oral larvicide in cattle, hog, goats and horses; in cattle ear tags to control flies; in cattle feedlots; in poultry dust boxes to control poultry mites; and in poultry houses. Tetrachlorvinphos also is used in pet sleeping areas and pet flea collars and to control flies around refuse sites, recreational areas, and for general outdoor treatment. Tetrachlorvinphos can cause cholinesterase inhibition in humans; that is, it can overstimulate the nervous system causing nausea, dizziness, confusion, and at very high exposures (e.g., accidents or major spills), respiratory paralysis and death. In 2014, the Natural Resources Defense Council (NRDC) filed a lawsuit against the United States Environmental Protection Agency (EPA) seeking EPA to respond to NRDC’s 2009 petition to ban tetrachlorvinphos in common pet flea treatment products. Tetrachlorvinphos is reportedly registered for use in Canada, South Africa, and Australia.

Approval Year

PubMed

PubMed

TitleDatePubMed
Residue content of beef feedlot manure after feeding diethylstilbestrol, chlortetracycline and Ronnel and the use of stirofos to reduce population of fly larvae in feedlot manure.
1977
Residues of stirofos (rabon) in eggs of laying hens treated for northern fowl mite control by dipping.
1982 Mar
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.
2011 Feb 27
Peripheral nervous system function and organophosphate pesticide use among licensed pesticide applicators in the Agricultural Health Study.
2012 Apr
Patents

Sample Use Guides

Repeated daily doses of up to 15 mg tetrachlorvinphos fed to human volunteers were reported in an abstract to have no effect on plasma or red-cell cholinesterase activities.
Route of Administration: Oral
Name Type Language
STIROFOS
USAN  
USAN  
Official Name English
TETRACHLORVINPHOS [HSDB]
Common Name English
TETRACHLORVINPHOS [IARC]
Common Name English
TETRACHLORVINPHOS, Z-ISOMER
Common Name English
PHOSPHORIC ACID, 2-CHLORO-1-(2,4,5-TRICHLOROPHENYL)ETHENYL DIMETHYL ESTER, (Z)-
Common Name English
((Z)-2-CHLORO-1-(2,4,5-TRICHLOROPHENYL)VINYL), DIMETHOXY PHOSPHATE
Systematic Name English
GARDONA (CIS-ISOMER)
Common Name English
Z-TETRACHLORVINPHOS
Common Name English
TETRACHLORVINPHOS
HSDB   ISO   MI  
Common Name English
TETRACHLORVINPHOS [ISO]
Common Name English
STIROFOS [USAN]
Common Name English
2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate
Systematic Name English
TETRACHLORVINPHOS [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QP53BB04
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C152434
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
PRIMARY
PUBCHEM
5284462
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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CHEBI
35005
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
PRIMARY
CAS
22248-79-9
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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WIKIPEDIA
TETRACHLORVINPHOS
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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ECHA (EC/EINECS)
244-865-4
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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EPA CompTox
DTXSID1021320
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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ChEMBL
CHEMBL1452359
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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CAS
961-11-5
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
HSDB
4066
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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ALANWOOD
tetrachlorvinphos
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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ECHA (EC/EINECS)
213-506-3
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
ALTERNATIVE
SMS_ID
300000031275
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
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MERCK INDEX
m10607
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
PRIMARY Merck Index
FDA UNII
DM33MW89QU
Created by admin on Fri Dec 15 18:54:34 GMT 2023 , Edited by admin on Fri Dec 15 18:54:34 GMT 2023
PRIMARY