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Vamidothion

PubChem CID
560193
Structure
Vamidothion_small.png
Vamidothion_3D_Structure.png
Molecular Formula
Synonyms
  • VAMIDOTHION
  • 2275-23-2
  • Vamidoate
  • Kilval
  • Trucidor
Molecular Weight
287.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-11
Description
Vamidothion is an organic thiophosphate that is N-methyl-2-[(2-sulfanylethyl)sulfanyl]propanamide in which the thiol group has been converted into the corresponding O,O-dimethyl thiophoshate. Formerly used as an insecticide and acaricide, it is no longer approved for use within the European Union. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide, an agrochemical, an antibacterial agent and an antifungal agent. It is an organic thiophosphate and an organothiophosphate insecticide. It is functionally related to a 2-((2-hydroxyethyl)sulfanyl)-N-methylpropionamide.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Vamidothion.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(2-dimethoxyphosphorylsulfanylethylsulfanyl)-N-methylpropanamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H18NO4PS2/c1-7(8(10)9-2)15-5-6-16-14(11,12-3)13-4/h7H,5-6H2,1-4H3,(H,9,10)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

LESVOLZBIFDZGS-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(C(=O)NC)SCCSP(=O)(OC)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H18NO4PS2
C8H18NO4PS2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2275-23-2

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 UN Number

2.3.5 ChEBI ID

2.3.6 DSSTox Substance ID

2.3.7 ICSC Number

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Kilval
  • O,O-dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl)phosphorothioate
  • vamidothion

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
287.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
287.04148740 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
287.04148740 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
115 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
16
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
256
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Colorless or white solid; [HSDB] Colorless solid; [MSDSonline]
COLOURLESS CRYSTALS.

3.2.2 Color / Form

Colorless needles
Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
White crystalline
Meister, R.T., Sine, C. (eds) Crop Protection Handbook Volume 92, Willoughby, OH, 2006., p. D 435

3.2.3 Melting Point

43 °C
Muller, F et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (2005). NY, NY: John Wiley & Sons; Acaricides. Online Posting Date: June 15, 2000.
White waxy solid. Melting point ca 40 °C. /technical vamidothion/
Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
46-48 °C

3.2.4 Solubility

Readily soluble in ... benzene, toluene, methyl ethyl ketone, ethyl acetate, acetonitrile, dichloromethane, cyclohexanone, chloroform (all at 1 kg/L). Almost insol in cyclohexane and petroleum ether.
Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
In water, 4 kg/L at 20 °C /miscible/
Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
Solubility in water: very good

3.2.5 Vapor Pressure

0.00000137 [mmHg]
Undergoes slight decomp at room temperature, but solutions in organic solvents (methyl ethyl ketone, cyclohexane) are stable. Decomposes in strong acid or alkaline media. VP: negligible at 20 °C.
Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
negligible at room temperature

3.2.6 Stability / Shelf Life

Undergoes slight decomposition at room temperature, but solutions in organic solvents (methyl ethyl ketone, cyclohexanone) are stable. Decomposed in strong acidic or alkaline media.
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A415 (1987)

3.2.7 Decomposition

When heated to decomposition it emits very toxic fumes of /phosphorous, sulfur and nitrogen oxides/.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2428

3.2.8 Corrosivity

Non-corrosive
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A415 (1987)

3.2.9 Ionization Efficiency

Ionization mode
Positive
logIE
3.33
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)
Reference

3.2.10 Kovats Retention Index

Standard non-polar
2036 , 2076.5 , 2075 , 2080 , 2083.8
Semi-standard non-polar
2104.4 , 2103.2 , 2114.3 , 2116.4

3.3 Chemical Classes

3.3.1 Pesticides

Acaricides, Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Organophosphate Insecticides
Pesticide (Vamidothion) -> USDA PDB

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 4
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NIST Number
53768
Library
Main library
Total Peaks
42
m/z Top Peak
87
m/z 2nd Highest
109
m/z 3rd Highest
145
Thumbnail
Thumbnail
2 of 4
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NIST Number
290123
Library
Replicate library
Total Peaks
95
m/z Top Peak
87
m/z 2nd Highest
145
m/z 3rd Highest
109
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 10
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Authors
B. Beck [dtc,com], J. Hollender [dtc]
Instrument
Exploris 240 Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
3.999 min
Precursor m/z
288.0488
Precursor Adduct
[M+H]+
Top 5 Peaks

146.0633 999

118.0322 5

Thumbnail
Thumbnail
License
CC BY-SA
2 of 10
View All
Authors
B. Beck [dtc,com], J. Hollender [dtc]
Instrument
Exploris 240 Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
3.999 min
Precursor m/z
288.0488
Precursor Adduct
[M+H]+
Top 5 Peaks

146.0633 999

118.0321 136

58.0651 36

86.0599 30

58.0289 8

Thumbnail
Thumbnail
License
CC BY-SA

4.2 IR Spectra

4.2.1 FTIR Spectra

Technique
FILM (CAST FROM CHLOROFORM)
Source of Sample
Riedel-De Haen AG
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Pesticide active substances -> Acaricides, Insecticides

7.2 EU Pesticides Data

Active Substance
vamidothion
Status
Not approved [Reg. (EC) No 1107/2009]
Legislation
2002/2076
ADI
0.008 mg/kg bw/day [JMPR 1988]

7.3 USDA Pesticide Data Program

8 Pharmacology and Biochemistry

8.1 Absorption, Distribution and Excretion

Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/
Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 1071
The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/
Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 147
... The organophosphorus insecticides are, in contrast to the chlorinated insecticides, rapidly metabolized & excreted and are not appreciably stored in body tissues. /Organophosphorus insecticides/
Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 832
Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/
Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 148
For more Absorption, Distribution and Excretion (Complete) data for VAMIDOTHION (7 total), please visit the HSDB record page.

8.2 Metabolism / Metabolites

Plasma and tissue enzymes are responsible for hydrolysis /of organophosphorus cmpd/ to the corresponding phosphoric and phosphonic acids ... The cytochrome P450s are responsible for converting the inactive phosphorothioates containing a phosphorus sulfur (thiono) bond to phosphorates with a phosphorus-oxygen bond, resulting in their activation. These mixed-function oxidases also play a role in deactivation of certain organophosphorus agents. /Anticholinesterase agents/
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 183
These chemicals are detoxified by cytochrome p450-mediated monooxygenases in the liver, but some metabolites are more toxic than parent cmpd ... Metabolites usually are detected from 12 to 48 hr postexposure. /Organophosphate cmpd/
Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 1071
... Metabolized in plants to the corresponding sulfoxide which is of similar activity to vamidothion but of greater persistence.
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 837
In mammals and insects, demethylation and hydrolysis to phosphoric acid.
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A415 (1987)
For more Metabolism/Metabolites (Complete) data for VAMIDOTHION (6 total), please visit the HSDB record page.

8.3 Mechanism of Action

Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation followed by depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/
Dreisbach, R.H. Handbook of Poisoning. 12th ed. Norwalk, CT: Appleton and Lange, 1987., p. 113
The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/
International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1638

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Used as systemic acaricide and insecticide for fruit trees, vines, ornamentals, beets, potatoes, cotton, rice, and other crops; Registered for use in many other countries; [HSDB]
Restricted Notes
No longer registered as a pesticide for use in the US; [HSDB] Banned in the EU for use as a biocide and agricultural insecticide; [eChemPortal: ESIS]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
Aphicide; miticide
Meister, R.T., Sine, C. (eds) Crop Protection Handbook Volume 92, Willoughby, OH, 2006., p. D-435
It is a systemic acaricide and insecticide.
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 837
Used on fruit trees, vines, ornamentals, beet, potatoes, cotton, rice, etc for persistent control of all species of aphids (especially woolly aphids), thrips, sawfly larvae, psyllids, spider mites, etc.
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A415 (1987)
Long-lasting systemic aphicide and miticide.
Farm Chemicals Handbook 1992. Willoughby, OH: Meister Publishing Co., 1992., p. C356
For Vamidothion there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
National Pesticide Information Retrieval System's USEPA/OPP Chemical Ingredients Database on Vamidothion (2275-23-2). Available from, as of April 16, 2007: https://npirspublic.ceris.purdue.edu/ppis/

9.2 Methods of Manufacturing

Vamidothion is produced by reaction of O,O-dimethylphosphoric acid chloride with the sodium salt of N-methylcarbamylethylmercaptoethanethiol.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V1 99 (2003)
... 2-Chloroethanol (ethylene chlorohydrin) is reacted with ethyl 2-mercapto propionate giving ethyl-2-(2-hydroxyethylthio)propionate. That intermediate is, in turn treated successively with methylamine and thionyl chloride to give 2-(2-chloroethylthio)-N-methylpropionamide. Condensation with O,O-dimethylphosphorothioate gives vamidothion.
Sittig, M. (ed.) Pesticide Manufacturing and Toxic Materials Control Encyclopedia. Park Ridge, NJ: Noyes Data Corporation. 1980., p. 762

9.3 Formulations / Preparations

Emulsifiable solution.
Meister, R.T., Sine, C. (eds) Crop Protection Handbook Volume 92, Willoughby, OH, 2006., p. D-435
Emulsifiable concentrate
Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
Soluble concentrate (400 g ai/l)
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 837

9.4 General Manufacturing Information

The WHO Recommended Classification of Pesticides by Hazard identifies Vamidothion (technical grade) as Class IB: highly hazardous; Main Use: insecticide.
WHO (2005) The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2004, International Programme on Chemical Safety, p.19
Not registered for use /in the United States/; Registered in many countries for cotton, hop, orchards, rice, sugarcane, vegetables, ornamentals; leafhoppers on rice.
Meister, R.T., Sine, C. (eds) Crop Protection Handbook Volume 92, Willoughby, OH, 2006., p. D-435

10 Identification

10.1 Analytic Laboratory Methods

Product analysis by hplc or glc ... Residues determined by glc
Tomlin CDS, ed. Vamidothion (2275-23-2) In: The e-Pesticide Manual, 13th Edition Version 3.2 (2005-06). Surrey UK, British Crop Protection Council.

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 5
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Pictogram(s)
Acute Toxic
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Precautionary Statement Codes

P264, P270, P273, P280, P301+P316, P302+P352, P317, P321, P330, P362+P364, P391, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Acute Tox. 4 (100%)

Aquatic Acute 1 (100%)

Acute toxicity (ingestion) - category 3

Acute toxicity (dermal) - category 4

Hazardous to the aquatic environment (acute) - category 1

11.1.3 Fire Hazards

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

11.1.4 Hazards Summary

A cholinesterase inhibitor that may have nervous system effects causing convulsions and respiratory failure; Can be absorbed through skin; [ICSC] No adverse histopathological findings, increased tumors, or signs of developmental, delayed neurological, or teratogenic toxicity; [HSDB] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
TLVs and BEIs - _Threshold Limit Values for Chemical Substances and Physical Agents & Biological Exposure Indices. _Cincinnati: ACGIH, 2020.

11.2 First Aid Measures

Inhalation First Aid
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

11.3 Fire Fighting

Use water spray, powder, foam, carbon dioxide.

11.3.1 Fire Fighting Procedures

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 677
If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use foam, dry chemical. or carbon dioxide. /Organophosphorus pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 679

11.4 Accidental Release Measures

11.4.1 Spillage Disposal

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Do NOT wash away into sewer. Then store and dispose of according to local regulations.

11.4.2 Cleanup Methods

Environmental considerations: Land spill: Dig a pit, pong, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 679
Environmental considerations: Water spill: use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 679
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 679
Environmental considerations: Land spill: Dig a pit, pong, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. /Organophosphorus pesticides, liquid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 677
For more Cleanup Methods (Complete) data for VAMIDOTHION (6 total), please visit the HSDB record page.

11.4.3 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

11.4.4 Preventive Measures

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 677
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, liquid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 677
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 679
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 679

11.5 Handling and Storage

11.5.1 Safe Storage

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed.

11.6 Exposure Control and Personal Protection

Exposure Summary
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
TLVs and BEIs - _Threshold Limit Values for Chemical Substances and Physical Agents & Biological Exposure Indices. _Cincinnati: ACGIH, 2020.

11.6.1 Inhalation Risk

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

11.6.2 Effects of Short Term Exposure

The substance may cause effects on the nervous system. This may result in convulsions and respiratory failure. Exposure at high levels could cause death. Cholinesterase inhibition. The effects may be delayed. Medical observation is indicated.

11.6.3 Effects of Long Term Exposure

Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.

11.6.4 Acceptable Daily Intakes

WHO RfD= 0.008 mg/kg
USEPA/OPP; Health Effects Div RfD/ADI Tracking Report p.59 (8/26/91)

11.6.5 Preventions

Fire Prevention
NO open flames.
Exposure Prevention
PREVENT DISPERSION OF DUST! IN ALL CASES CONSULT A DOCTOR!
Inhalation Prevention
Use ventilation (not if powder), local exhaust or breathing protection.
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear face shield or eye protection in combination with breathing protection.
Ingestion Prevention
Do not eat, drink, or smoke during work. Wash hands before eating.

11.7 Transport Information

11.7.1 DOT Emergency Guidelines

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
For more DOT Emergency Guidelines (Complete) data for VAMIDOTHION (16 total), please visit the HSDB record page.

11.7.2 Shipping Name / Number DOT/UN/NA/IMO

UN 3018; Organophosphorus pesticides, liquid, toxic, not otherwise specified
UN 3017; Organophosphorus pesticides, liquid, toxic, flammable, not otherwise specified, flashpoint between 23 °C and 61 °C
UN 2783; Organophosphorus pesticides, solid, toxic, not otherwise specified
UN 2784; Organophosphorus pesticides, liquid, flammable, toxic, not otherwise specified, flashpoint less than 23 °C
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for VAMIDOTHION (6 total), please visit the HSDB record page.

11.7.3 Standard Transportation Number

49 216 74; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 216 75; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, liquid)
49 105 44; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 105 45; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, liquid)
49 216 76; Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 216 77; Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, other than liquid)

11.7.4 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 15, 2006: https://www.ecfr.gov
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
International Air Transport Association. Dangerous Goods Regulations. 47th Edition. Montreal, Quebec Canada. 2006., p. 231
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
International Maritime Organization. International Maritime Dangerous Goods Code. London, UK. 2004., p. 149, 134

11.7.5 Packaging and Labelling

Do not transport with food and feedstuffs.

11.7.6 EC Classification

Symbol: T, N; R: 21-25-50; S: (1/2)-36/37-45-61

11.7.7 UN Classification

UN Hazard Class: 6.1; UN Pack Group: III

11.8 Regulatory Information

Status Regulation (EC)
2002/2076

11.9 Other Safety Information

Chemical Assessment

IMAP assessments - Phosphorothioic acid, O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-oxoethyl]thio]ethyl] ester: Environment tier I assessment

IMAP assessments - Phosphorothioic acid, O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-oxoethyl]thio]ethyl] ester: Human health tier I assessment

12 Toxicity

12.1 Toxicological Information

12.1.1 Exposure Routes

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

12.1.2 Symptoms

Inhalation Exposure
Pupillary constriction, muscle cramp, excessive salivation. Sweating. Nausea. Dizziness. Laboured breathing. Convulsions. Unconsciousness.
Skin Exposure
MAY BE ABSORBED! See Inhalation.
Ingestion Exposure
Abdominal cramps. Vomiting. Diarrhoea. Further see Inhalation.

12.1.3 Adverse Effects

Other Poison - Organophosphate

12.1.4 Acute Effects

12.1.5 Toxicity Data

LC50 (rat) = 1,730 mg/m3/4h

12.1.6 Interactions

ANTICHOLINESTERASE (ORGANOPHOSPHORUS) INSECTICIDES ANTAGONIZE POLARIZING MUSCLE RELAXANTS. PHENOTHIAZINES /AND THIOXANTHENES/: ... MAY ENHANCE TOXIC EFFECTS OF ORGANOPHOSPHORUS INSECTICIDES. /INSECTICIDES, ORGANOPHOSPHORUS/
Martin E. Hazards of Medication: A Manual on Drug Interactions, Incompatibilities, Contraindications and Adverse Effects. Philadelphia: J.B. Lippincott Co., 1971., p. 637

12.1.7 Antidote and Emergency Treatment

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Organophosphates and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 294
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2 PAM). USE UNDER DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. In rare cases diazepam or lorazepam may be necessary ... . Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 294-5
Emergency and supportive measures. Caution: Rescuers and health-care providers must take measures to prevent direct contact with the skin or clothing of contaminated victims, because secondary contamination and serious illness may result, especially with potent pesticides or nerve agents. 1. Maintain an open airway and assist ventilation if necessary. Pay careful attention to respiratory muscle weakness because sudden respiratory arrest may occur. This is often preceded by increasing weakness of neck flexion muscles. In intubation is required, a nondepolarizing agent should be used because the effect of succinylcholine will be extended secondary to the inhibition of PChE. Administer supplemental oxygen. 2. Treat hydrocarbon pneumonitis, seizures, and coma if they occur. Seizures should be treated with benzodiazepines such as diazepam. 3. Observe asymptomatic patient for at least 8-12 hours to rule out delayed-onset symptoms, especially after extensive skin exposure of ingestion of a highly fat-soluble agent. /Organophosphorus and carbamate compounds/
Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 295
Specific drugs and antidotes. Specific treatment includes the antimuscarinic agent atropine and the enzyme reactivator pralidoxime. 1. Give atropine... until signs of atropinization are present (decreased secretion and wheezing, increased hear rate). The most clinically important indication for continued atropine administration is persistent wheezing or bronchorrhea. Tachycardia is not a contraindication to more atropine. Note: Atropine will reverse muscarinic but not nicotinic effects. 2. Pralidoxime (2-PAM, Protopam) is a specific antidote that acts to regenerate the enzyme activity at all affected sites prior to aging. Other oximes include obidoxime and HI-6. Oximes may be less effective against dimethyl compounds compared with diethyl agents. a. Pralidoxime should be given immediately to reverse muscular weakness and fasciculations: ... . It is most effective if started early, before irreversible phosphorylation of the enzyme, but may still be effective if given later, particularly after exposure to highly lipid-soluble compounds. It is unclear how long oxime therapy should be continued, but it seems reasonable to continue it for 24 hr after the patient becomes asymptomatic. b. Pralidoxime generally is not recommended for carbamate intoxication, because in such cases the cholinesterase inhibition is spontaneously reversible and short-lived. However, if the exact agent is not identified and the patient has significant toxicity, pralidoxime should be given empirically. /Organophosphorus and carbamate compounds/
Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 295
For more Antidote and Emergency Treatment (Complete) data for VAMIDOTHION (6 total), please visit the HSDB record page.

12.1.8 Medical Surveillance

Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications for work with /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/
International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1646
A final diagnosis of mild to moderate acute organophosphate pesticide poisoning is rarely justified unless all of the following five conditions are present: 1. A definite history of exposure to an organophosphate pesticide. 2. A latent interval of not more than a few hours between that last exposure and the onset of illness. 3. A clinical picture in which most or all of the following signs or symptoms are present: headache, blurred vision, weakness, tightness in chest, and constricted pupils. 4. Reduction of plasma and RBC cholinesterase activity to a level substantially below 50% of baseline values. Because of the wide normal range of RBC cholinesterase in the population, symptoms may be present with reported "normal" levels. 5. An acute illness that is not substantially longer than 48 hours. The classic presentation for acute organophosphate toxicity includes history, evidence of exposure to organophosphate (garlic odor), signs/symptoms of cholinergic excess, improvement with atropine or pralidoxime, and inhibition of cholinesterase in blood. /Organophosphate pesticide poisoning/
Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 1074

12.1.9 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ Eighteen people using vamidothion on crops were examined. The concentration of the product in air was 0.024 mg/cu m 50 meters away from the point of application. Symptoms recorded were a very slight drop in pulse rate and arterial blood pressure in 8 subjects. For 10 minutes, a reduction of 4-11% in blood cholinesterase was observed.
FAO/WHO; JMPR Pesticide Residues in Food, Part II Toxicology - Vamidothion (1985). Available from, as of November 8, 2006: https://www.inchem.org/documents/jmpr/jmpmono/v85pr19.htm
/SIGNS AND SYMPTOMS/ Organophosphate insecticides ... are potent cholinesterase enzyme inhibitors that act by interfering with the metabolism of acetylcholine, which results in accumulation of acetylcholine at neuroreceptor transmission sites. Exposure produces a broad spectrum of clinical effects indicative of massive overstimulation of the chlorinergic system, including muscarinic effects (parasympathetic), nicotinic effects (sympathetic and motor), and CNS effects. These effects present clinically as feeling of headache, weakness, dizziness, blurred vision, psychosis, respiratory difficulty, paralysis, convulsions, and coma. Typical findings are given by the mnemonic "SLUD." which stands for salivation, lacrimation, urination, and defecation. A small percentage of patients may fail to demonstrate miosis, a classic diagnostic hallmark. Onset of clinical manifestation of organophosphate poisoning usually occurs within 12 hours of exposure. /Organophosphate insecticides/
Amdur, M.O., J. Doull, C.D. Klaasen (eds). Casarett and Doull's Toxicology. 4th ed. New York, NY: Pergamon Press, 1991., p. 936
/SIGNS AND SYMPTOMS/ A follow up study of 232 people three years after a history of organophosphorus pesticide poisoning disclosed only one person with slight residual blurring of vision that might have been related to the earlier poisoning, though at the time of poisoning over one third of the people had blurring, which lasted only a day or two after exposure was discontinued. The possible exceptional case had findings suggestive of basilar artery insufficiency, rather than effects of poisoning. /Organophosphorus pesticide poisoning/
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 679
/SIGNS AND SYMPTOMS/ The duration of illness depends on the severity of poisoning, since several months may be required for cholinesterase activity to return to normal levels. Symptoms of mild to moderate organophosphate poisoning usually resolve by 1 month. A follow up study of pesticide workers who developed acute organophosphate poisoning revealed that episodes of headache, visual disturbances, nausea, and vomiting persisted 10 weeks after the acute episode, but the effect of reexposure to organophosphates could not be evaluated. /Organophosphate pesticide/
Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 1073
For more Human Toxicity Excerpts (Complete) data for VAMIDOTHION (11 total), please visit the HSDB record page.

12.1.10 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of 10 male rats were administered 3 or 6 mg vamidothion/kg/day orally for one month. It was reported that body weight was unaffected, no animals died and no clinical signs of toxicity occurred. Haematological examination including examination of bone marrow and chemical analysis of urine and blood showed no abnormalities except for blood cholinesterase activity which was depressed by 50% (3 mg/kg/day) or /60%/ (6 mg/kg/day). Brain cholinesterase levels were not depressed. The weights and histological appearance of organs were unaffected by treatment.
FAO/WHO; JMPR Pesticide Residues in Food, Series 3 - Vamidothion (1973). Available from, as of November 8, 2006: https://www.inchem.org/documents/jmpr/jmpmono/v073pr24.htm
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of five male and five female rats were fed on diets containing 0, 0.2, 1 and 5 ppm vamidothion for six weeks after which the test substance was withdrawn from the diet. Regular observation of plasma and erythrocyte cholinesterase activity showed that only in the plasma of female rats on the 5 ppm diet was enzyme activity consistently depressed to a significant extent. The enzyme level returned to normal within five weeks. Cholinesterase activity was not depressed significantly at lower dosage levels.
FAO/WHO; JMPR Pesticide Residues in Food, Series 3 - Vamidothion (1973). Available from, as of November 8, 2006: https://www.inchem.org/documents/jmpr/jmpmono/v073pr24.htm
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of rats were administered, by gavage, doses of approximately 2, 5 or 10 mg vamidothion/kg daily for three months. At the end of the test serum acetylcholinesterase activity was decreased to 35%, 12% and 8%, respectively, of the normal value.
FAO/WHO; JMPR Pesticide Residues in Food, Series 3 - Vamidothion (1973). Available from, as of November 8, 2006: https://www.inchem.org/documents/jmpr/jmpmono/v073pr24.htm
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of three dogs were administered orally 0, 1 and 2 mg/vamidothion/kg/day for one month. Two dogs received 8 mg/kg/day for one month. No effect was seen on growth except for one animal on the highest dose level which developed diarrhea (cause unknown). Hematological indices and blood coagulation were normal. Slight differences between groups in urine urobilinogen, glucose and bile salts, serum protein, PSP clearance and behaviour could not be attributed to treatment. In particular no neurological abnormalities were seen although erythrocyte cholinesterase was severely depressed (100% inhibition at sixteenth day with 8 mg/kg dosage regime).
FAO/WHO; JMPR Pesticide Residues in Food, Series 3 - Vamidothion (1973). Available from, as of November 8, 2006: https://www.inchem.org/documents/jmpr/jmpmono/v073pr24.htm
For more Non-Human Toxicity Excerpts (Complete) data for VAMIDOTHION (22 total), please visit the HSDB record page.

12.1.11 Non-Human Toxicity Values

LD50 Rat oral 64 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2428
LD50 Mice oral 40 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2428
LD50 Mice dermal 1500 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2428
LD50 Guinea pig oral 85 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2428
For more Non-Human Toxicity Values (Complete) data for VAMIDOTHION (10 total), please visit the HSDB record page.

12.2 Ecological Information

12.2.1 Ecotoxicity Values

LD50 Pheasant oral 35 mg/kg
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A415 (1987)

12.2.2 ICSC Environmental Data

The substance is harmful to aquatic organisms. This substance may be hazardous to the environment. Special attention should be given to birds and bees. Avoid release to the environment in circumstances different to normal use.

12.2.3 Environmental Fate / Exposure Summary

Vamidothion's former production and use in the US as an acaricide and insecticide resulted in its direct release to the environment. If released to air, an estimated vapor pressure of 1.4X10-6 mm Hg at 25 °C indicates vamidothion will exist solely in the particulate phase in the atmosphere. Particulate-phase vamidothion will be removed from the atmosphere by wet or dry deposition. During an aqueous photolysis test vamidothion degraded at a high rate in the presence of a photosensitizer, but it degraded only 2% after 6 hours in a 100 mg/L sample containing vamidothion, distilled water, and 2-4% methanol. Therefore, aqueous photolysis of vamidothion is not expected to be an important fate process. If released to soil, vamidothion is expected to have low mobility based upon an estimated Koc of 810. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 8.6X10-16 atm-cu m/mole. Vamidothion is expected to undergo biodegradation in the environment based on an observed half-life of 1-1.5 days in soil. If released into water, vamidothion is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. The rate of hydrolysis of phosphate esters has been observed to increase with increasing pH; the half-life of vamidothion in water is 36.5 days at 30 °C at a pH of 4.5 and 25.4 hours at 70 °C and pH 6.9. Based on these data, vamidothion is expected to undergo hydrolysis at least to some degree in most waters, and will do so much more quickly in warm, alkaline waters. Occupational exposure and general population exposure should be low or non-existent since vamidothion is no longer produced or used in the US. In the past, vamidothion was applied directly to the trees, vines, ornamentals and crops as an acaricide and insecticide. (SRC)

12.2.4 Artificial Pollution Sources

Vamidothion's former production and use in the US as an acaricide and insecticide(1) may have resulted in its direct release to the environment through various waste streams(SRC).
(1) Muller F et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (2005). NY, NY: John Wiley & Sons; Acaricides. Online Posting Date: June 15, 2000.

12.2.5 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 810(SRC), determined from a structure estimation method(2), indicates that vamidothion is expected to have low mobility in soil(SRC). Volatilization of vamidothion from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.6X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Vamidothion is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-6 mm Hg(SRC), determined from a fragment constant method(4). Vamidothion is expected to biodegrade in the environment based on an observed half-life of 1-1.5 days in soil at 22 °C(5).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(5) Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 810(SRC), determined from a structure estimation method(2), indicates that vamidothon is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.6X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.16(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Vamidothion is expected to biodegrade in the environment based on an observed half-life of 1-1.5 days in soil at 22 °C(8).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(7) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(8) Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vamidothion, which has an estimated vapor pressure of 1.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Vapor-phase vamidothion is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.8 days(SRC), calculated from its rate constant of 5.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase vamidothion may be removed from the air by wet or dry deposition(SRC). Vamidothion, present at a concn of 100 mg/L in distilled water with 2-4% methanol, degraded only 2% after 6 hours during an aqueous photolysis test which used a suntest apparatus consisting of a xenon arc lamp emitting 300-800 nm of light(4), suggesting that vamidothion is not susceptible to direct photolysis(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Barcelo D et al; Toxicol Environ Chem 38: 183-99 (1993)

12.2.6 Environmental Biodegradation

AEROBIC: A biodegradation half-life for vamidothion in the soil has been reported as 1.0-1.5 days at 22 °C(1). Details concerning test methods were not found. Based on this information, biodegradation of vamidothion in the soil is expected to be an important fate process(SRC).
(1) Tomlin CDS, ed; Vamidothion (2275-23-2). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.

12.2.7 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of vamidothion with photochemically-produced hydroxyl radicals has been estimated as 5.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Vamidothion is expected to undergo aqueous hydrolysis under environmental conditions(2). A hydrolysis half-life of 36.5 days at 30 °C and at a pH of 4.5 was observed(2), which corresponds to a half-life of about 91 days at 20 °C(SRC), using a factor change of 2.5 based on the 10 deg temperature difference(3). The aqueous hydrolysis half-life of vamidothion in a pH 6.9 buffered ethanol-water solution (20:80) was determined to be 25.4 hours at 70 °C(4). Over the pH range of 3.0 to 7.0, the hydrolysis rate of phosphate esters is relatively constant although the rate generally increases at pH 7.0 and increases significantly (several fold to an order of magnitude) at pH 9.0(5). Based on these data, vamidothion is expected to undergo hydrolysis at least to some degree in most waters, and will do so much more quickly in warm, alkaline waters(SRC). Vamidothion, present at a concn of 100 mg/L in distilled water with 2-4% methanol, degraded only 2% after 6 hours during an aqueous photolysis test which used a suntest apparatus consisting of a xenon arc lamp emitting 300-800 nm of light(6). However, after 5% of acetone was added as a photosensitizer, the remainder of the vamidothion degraded 80, 70, 62, 56, 34, 17, and 5% after 30, 60, 90, 120, 180, 240, and 300 minutes, respectively(6). Based on these data, aqueous photolysis is not expected to be an important environmental fate process(SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Singh NC et al; in Amer Chem Soc Agrochemicals 191st Natl Meg #84 (1986)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)
(4) Faust SD et al; Environ Letters 3: 171-201 (1972)
(5) Ruzicka JH et al; J Chromat 31: 37-47 (1967)
(6) Barcelo D et al; Toxicol Environ Chem 38: 183-99 (1993)

12.2.8 Environmental Bioconcentration

An estimated BCF of 3.2 was calculated for vamidothion(SRC), using an estimated log Kow of 0.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.9 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of vamidothion can be estimated to be 810(SRC). According to a classification scheme(2), this estimated Koc value suggests that vamidothion is expected to have low mobility in soil.
Using a structure estimation method based on molecular connectivity indices(1), the Koc of vamidothion can be estimated to be 810(SRC). According to a classification scheme(2), this estimated Koc value suggests that vamidothion is expected to have low mobility in soil.

12.2.10 Volatilization from Water / Soil

The Henry's Law constant for vamidothion is estimated as 8.6X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that vamidothion is expected to be essentially nonvolatile from water surfaces(2). Vamidothion is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-6 mm Hg(SRC), determined from a fragment constant method(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)

12.2.11 Environmental Water Concentrations

SURFACE WATER: Vamidothion has been detected in surface water resources in The Netherlands(1).
(1) Oskam G et al; Water Supply 11: 1-17 (1993)

12.2.12 Food Survey Values

A Danish study conducted by the Danish Pesticide Monitoring Program from 1995-1996 analyzed for, but did not detect, vamidothion in food commodities such as cereal, fruits, vegetables, bran, fish, and animal products(1).
(1) Juhler RK et al; J AOAC International 82: 337-58 (1999)

12.2.13 Milk Concentrations

Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/
Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 148

12.2.14 Probable Routes of Human Exposure

Occupational exposure to vamidothion may occur through dermal contact with this compound at workplaces where vamidothion is produced or used. (SRC)

13 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Chemical Co-Occurrences in Literature

14.5 Chemical-Gene Co-Occurrences in Literature

14.6 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 KEGG: Pesticides

17.4 ChemIDplus

17.5 UN GHS Classification

17.6 NORMAN Suspect List Exchange Classification

17.7 EPA DSSTox Classification

17.8 EPA Substance Registry Services Tree

17.9 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Phosphorothioic acid, O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-oxoethyl]thio]ethyl] ester
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. ILO-WHO International Chemical Safety Cards (ICSCs)
  9. ChEBI
  10. EU Pesticides Database
  11. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  12. USDA Pesticide Data Program
  13. Hazardous Chemical Information System (HCIS), Safe Work Australia
  14. NITE-CMC
    O,O-Dimethyl S-2-[1-(N-methylcarbamoyl)ethylthio]ethyl phosphorothioate; Vamidothion - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-0290e.html
    O,O-Dimethyl S-2-[1-(N-methylcarbamoyl)ethylthio]ethyl phosphorothioate; Vamidothion - FY2020 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/20-mhlw-2051e.html
  15. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
    vamidothion (ISO); O,O-dimethyl S-2-(1-methylcarbamoylethylthio) ethyl...
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  16. Japan Chemical Substance Dictionary (Nikkaji)
  17. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  18. Kruve Lab, Ionization & Mass Spectrometry, Stockholm University
    vamidothion
  19. MassBank Europe
  20. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
    Pesticide1_Vamidothion_C8H18NO4PS2_Phosphorothioic acid, O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-oxoethyl]thio]ethyl] ester
    https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27LESVOLZBIFDZGS-UHFFFAOYSA-N%27)
  21. Metabolomics Workbench
  22. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  23. SpectraBase
  24. Springer Nature
  25. Wikidata
  26. PubChem
  27. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  28. GHS Classification (UNECE)
  29. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  30. EPA Substance Registry Services
  31. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  32. PATENTSCOPE (WIPO)
CONTENTS