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Phosphamidon

PubChem CID
3032604
Structure
Phosphamidon_small.png
Phosphamidon_3D_Structure.png
Molecular Formula
Synonyms
  • PHOSPHAMIDON
  • Dimecron
  • 13171-21-6
  • (Z)-Phosphamidon
  • Fosfamidone
Molecular Weight
299.69 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-11
Description
Phosphamidon is a pale yellow oily liquid with a faint odor. Used as an insecticide for citrus, cotton, and deciduous fruit and nuts. and as an acaricide. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Phosphamidon is a trialkyl phosphate, an organophosphate insecticide, an organochlorine insecticide and an organophosphate nematicide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an acaricide and an agrochemical. It is functionally related to a N,N-diethyl-3-hydroxybut-2-enamide.
Phosphamidon is a synthetic trialkyl phosphate compound and organophosphate acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as a colorless or yellow oily liquid with a faint odor, and exposure occurs by inhalation, ingestion, or contact.
See also: (E)-Phosphamidon (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Phosphamidon.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(Z)-3-chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3/b9-8-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RGCLLPNLLBQHPF-HJWRWDBZSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCN(CC)C(=O)/C(=C(\C)/OP(=O)(OC)OC)/Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H19ClNO5P
Computed by PubChem 2.2 (PubChem release 2021.10.14)
C10H19ClNO5P

2.3 Other Identifiers

2.3.1 CAS

13171-21-6

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 UN Number

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 ICSC Number

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Dimecron
  • Phosphamidon

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
299.69 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
299.0689374 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
299.0689374 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
65.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
18
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
359
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
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
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

Phosphamidon is a pale yellow oily liquid with a faint odor. Used as an insecticide for citrus, cotton, and deciduous fruit and nuts. and as an acaricide. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Colorless to yellow liquid; [ICSC]
COLOURLESS-TO-YELLOW OILY LIQUID.

3.2.2 Color / Form

Pale-yellow liquid
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. 1754
COLORLESS LIQUID
NIOSH/CDC. NIOSH Recommendations for Occupational Safety and Health Standards Sept. 1986. (Supplement to Morbidity and Mortality Weekly Report 35 No. 15, Sept. 26, 1986), p. 906
Oil
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 424

3.2.3 Odor

FAINT ODOR
Worthing, C. R. (ed.). Pesticide Manual. 6th ed. Worcestershire, England: British Crop Protection Council, l979., p. 424

3.2.4 Boiling Point

324 °F at 1.5 mmHg (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
120 °C @ 0.001 mm Hg; 162 °C 1.5 mm Hg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315
at 0.2kPa: 162 °C

3.2.5 Melting Point

-49 °F (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
-45 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315

3.2.6 Flash Point

greater than 200 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.7 Solubility

greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Miscible with most org solvents except saturated hydrocarbons; 1 g dissolves in about 30 g hexane
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315
In water, miscible @ 25 °C
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 966
Solubility in water: miscible

3.2.8 Density

1.2132 at 77 °F (EPA, 1998) - Denser than water; will sink
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
1.2132 @ 25 °C/4 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315
Relative density (water = 1): 1.2

3.2.9 Vapor Pressure

2.5e-05 mmHg at 68 °F (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
0.0000165 [mmHg]
1.65X10-5 mm Hg @ 25 °C
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 966
Vapor pressure, Pa at 20 °C: 0.0033

3.2.10 LogP

0.8

3.2.11 Stability / Shelf Life

ISOMERIC MIXT STABLE IN NEUTRAL & ACID MEDIA; HALF-LIFE @ 23 °C= 13.8 DAYS @ PH 7, 2.2 DAYS @ PH 10
Martin, H. and C.R. Worthing (eds.). Pesticide Manual. 4th ed. Worcestershire, England: British Crop Protection Council, 1974., p. 409
DECOMP ABOVE 160 °C /E-ISOMER/
Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 529
Stable in neutral or acidic media; hydrolyzed by alkali.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315
Solutions of this chemical in water, DMSO, 95% ethanol and acetone should be stable for 24 hr under normal lab conditions (RAD).
DHHS/National Toxicology Program; Chemical Health & Safety Data File. Available from: https://ntp-db.niehs.nih.gov/cgi/iH_Indexes/Chem_H&S/iH_Chem_H&S_Frames.html on Phosphamidon (13171-21-6) as of June 27, 2003.

3.2.12 Decomposition

When heated to decomposition it emits toxic fumes of /phosphorous and nitric oxides/.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 1626
Hydrolyzed by alkali with t1/2 of 14 day at pH 7 and 23 °C; 2.2 day at pH 10.
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 1801
Produces highly toxic phosphorus oxides and chlorides fumes above 160 °C.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20tr

3.2.13 Viscosity

DENSITY: 1.22 @ 20 °C/4 °C; VISCOSITY: 70 CENTIPOISES @ 25 °C /TECHNICAL PRODUCT/
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 457

3.2.14 Corrosivity

Corrosive to iron, tin, aluminum; non-corrosive to polyethylene
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. Old Woking, Surrey, United Kingdom: Royal Society of Chemistry/Unwin Brothers Ltd., 1983., p. A326/Oct 83

3.2.15 Refractive Index

Index of refraction: 1.4718 @ 25 °C/D
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315

3.2.16 Collision Cross Section

162.25 Ų [M+Na]+

155.99 Ų [M+H]+

S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.2.17 Kovats Retention Index

1 of 2
Standard non-polar
1787 , 1825 , 1833 , 1849 , 1837 , 1850 , 1826 , 1808 , 1835.2 , 1855.2 , 1790.1 , 1852.3
Semi-standard non-polar
1860 , 1866 , 1811 , 1870 , 1793.3 , 1861.5 , 1791.8 , 1868 , 1861.3 , 1868.8 , 1853.8 , 1846.5
Standard polar
2831
2 of 2
Standard non-polar
1851.7

3.2.18 Other Experimental Properties

Stable in neutral or acid media; hydrolyzed by alkali.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315
Commercial product consists of 73/27 mixture of cis (Z)/ trans (E) isomers.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1315
Oil-water partition coefficient: 0.79
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20tr

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Pesticides

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

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 7
View All
NIST Number
125533
Library
Main library
Total Peaks
172
m/z Top Peak
127
m/z 2nd Highest
264
m/z 3rd Highest
72
Thumbnail
Thumbnail
2 of 7
View All
NIST Number
290351
Library
Main library
Total Peaks
157
m/z Top Peak
127
m/z 2nd Highest
264
m/z 3rd Highest
72
Thumbnail
Thumbnail

4.2 Other Spectra

Intense mass spectral peaks: 127 m/z (100%), 72 m/z (61%), 264 m/z (46%), 138 m/z (35%)
Hites, R.A. Handbook of Mass Spectra of Environmental Contaminants. Boca Raton, FL: CRC Press Inc., 1985., p. 283

6 Chemical Vendors

7 Drug and Medication Information

7.1 Reported Fatal Dose

5. 5= Extremely toxic: Probable oral lethal dose (human) 5-50 mg/kg, between 7 drops and 1 teaspoonful for 70 kg person (150 lb).
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-292

8 Agrochemical Information

8.1 Agrochemical Category

Insecticide
Pesticide active substances -> Acaricides, Insecticides

8.2 EU Pesticides Data

Active Substance
phosphamidon
Status
Not approved [Reg. (EC) No 1107/2009]
Legislation
2002/2076
ADI
0.0005 mg/kg bw/day [JMPR 1986]

8.3 USDA Pesticide Data Program

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors
Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)
Insecticides
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

9.2 Absorption, Distribution and Excretion

The main eliminative route for phosphamidon...in rats and lactating goats was via kidneys, but small amount of several metabolites were secreted into milk of lactating goats. Only traces of unchanged /phosphamidon/ were present amongst excretory products. Desethylphosphamidon was present in urine of treated animals, whereas both phosphamidon amide and dechlorophosphamidon amide occurred in urine and milk of lactating goats. ...alpha-Chloro-nn-diethylacetoacetamide was detected in urine and in milk.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 287
After ip injection of cis or trans phosphamidon-(32)P in male white rats, excreta was collected... About 60% of dose--either isomer--was recovered within 24 hr...most from urine... .
Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 276
Phosphamidon is a systemic insecticide rapidly absorbed by the plant... In plants 50% loss occurs in about 2 days.
Worthing, C. R. (ed.). Pesticide Manual. 6th ed. Worcestershire, England: British Crop Protection Council, l979., p. 424
Early appearance of symptoms and steepness of acute dose-response curves (increased dosage levels produced disproportionately large increase in response) indicate that phosphamidon is rapidly and thoroughly taken up from GI tracts of birds.
U.S. Department of the Interior, Fish and Wildlife Service. Handbook of Toxicity of Pesticides to Wildlife. Resource Publication 153. Washington, DC: U.S. Government Printing Office, 1984., p. 64
Phosphamidon is absorbed by the respiratory and gastrointestinal tracts as well as by the skin. ...Experimental animal studies have shown that most of a radiolabelled doses of organophosphorus pesticides is rapidly excreted in expired air, urine, and feces.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20tr

9.3 Metabolism / Metabolites

Desethylphosphamidon was present in the urine of treated.../lactating goats/ both phosphamidon amide and dechlorophosphamidon amide occurred in the urine and milk...alpha-chloro-nn-diethylacetoacetamide was detected in urine and in milk.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 287
After ip injection of cis or trans (32)P-phosphamidon in male white rats... about 60% of dose...was recovered within 24 hr after injection, most from urine. Hydrolytic products were almost entirely dimethyl phosphate, with small amount of phosphoric acid and o-demethyl phosphamidon. After foliar treatment of cotton, phosphamidon, o-demethyl phosphamidon, n-desethyl phosphamidon, hydroxyethyl phosphamidon, and dimethyl phosphate were detected externally. Internally, orthophosphate and an unknown were observed in addition to the foregoing compound. In fifth-instar tobacco budworms and bollworms, metabolism of the two isomers was similar. After injection of labeled phosphamidon.../phosphamidon, O-demethyl phosphamidon, hydroxyethyl phosphamidon, n-desethyl phosphamidon, phosphoric acid/ were observed in internal extracts /and excreta/.
Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 276
Desethyl phosphamidon...alpha-chloroacetoacetic acid diethylamide, alpha-chloroacetoacetic acid ethylamide, dimethyl phosphoric acid, and unchanged phosphamidon were isolated from bean plants treated with (14)C-labeled phosphamidon. ...Metabolism of phosphamidon is unusual in that facile deethylation of the diethylamide moiety occurs with no demethylation at one of the methoxy groups. Environmental factors such as temperature and, to a lesser extent, light influence plant metabolism of phosphamidon to desethyl phosphamidon with increased rates at higher temperatures.
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 180
Rats received (32)P- and/or (14)C-labeled phosphamidon by stomach tube. .../Among metabolites found were/ vinyl hydroxyphosphamidon amide...and two compound containing only the carbon label but not further identified. Rat and rabbit liver homogenates metabolized phosphamidon... /des-n-ethyl phosphamidon and phosphamidon amide/ were found in small quantities but the hydroxy compound were not detected... .
Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 292
For more Metabolism/Metabolites (Complete) data for PHOSPHAMIDON (6 total), please visit the HSDB record page.

9.4 Mechanism of Action

Organophosphorus pesticides exert their acute effects by inhibiting acetylcholinesterase in the nervous system with subsequent accumulation of toxic levels of acetylcholine. They may also inhibit butylcholinesterases as well as other esterase. The function of butylcholinesterases is unknown, but its inhibition can provide an indication of exposure to an organophosphate. In many cases, the organophosphorylated enzyme is fairly stable, so that recovery from intoxication may be slow. Reactivation of inhibited enzyme may occur spontaneously, the rates of reactivation depending on the tissue as well as on the chemical group attached to the enzyme. Higher doses of oximes failed to alter the reactivation of in vitro human AchE inhibited by organophosphorus compunds.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20trade%2
Cholinesterase inhibitor.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 872

9.5 Transformations

10 Use and Manufacturing

10.1 Uses

Sources/Uses
Used as systemic insecticide for deciduous fruits and nuts, cotton, rice, cereals, potatoes, soy beans, and other crops; [HSDB] Used as acaricide; [CAMEO]
Restricted Notes
Cancelled--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]
The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.142 (Spring, 1998) EPA 738-R-98-002
For phosphamidon (USEPA/OPP Pesticide Code: 018201) 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./
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Phosphamidon (13171-21-6). Available from, as of July 1, 2003: https://npirspublic.ceris.purdue.edu/ppis/
INSECTICIDE FOR CITRUS AND COTTON CROPS, DECIDUOUS FRUIT & NUT CROPS
SRI
Systemic insecticide with strong stomach action. Used for sucking insects, stemborers in rice, aphids in various crops.
Farm Chemicals Handbook 2002. Meister Publishing Co., 2002., p. C-316
For more Uses (Complete) data for PHOSPHAMIDON (6 total), please visit the HSDB record page.

10.1.1 Use Classification

Hazard Classes and Categories ->
INSECTICIDES

10.2 Methods of Manufacturing

Phosphamidon is produced by reaction of trimethylphosphite with alpha,alpha-dichloroacetic acid diethylamide.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V1 98 (2003)
Worthing, C. R. (ed.). Pesticide Manual. 6th ed. Worcestershire, England: British Crop Protection Council, l979., p. 424

10.3 Impurities

In technical preparations of phosphamidon, gamma-chlorophosphamidon is present at a level of one to two percent of the total product.
Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 292

10.4 Formulations / Preparations

LIQUID, SOLUBLE CONCENTRATES, ULV FOR WATERLESS SPRAYING.
Farm Chemicals Handbook 2002. Meister Publishing Co., 2002., p. C-316
TECHNICAL PRODUCT IS OF 92% PURITY; DIMERCRON 20 (200 G/L), DIMERCRON 50, DIMERCROM 100 AND DIMERCRON ULVAIR 250
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 457
Main brand names/Trade names: Apamidon, Ciba 570, C-570, D-Cron, Dimecron, Dixon, ENT 25,515, Famfos, Merkon, ML-97, Or-1,911, Phosphamidone, Phosron, Pillarcron, Sundaram 1975 , Swat, Umecron.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20trade%20names

10.5 Consumption Patterns

INSECTICIDE FOR CITRUS, 33%; INSECTICIDE FOR COTTON, 33%; INSECTICIDE FOR DECIDUOUS FRUITS AND NUTS, 33% (1978)
SRI

10.6 U.S. Production

(1976) NOT PRODUCED COMMERCIALLY IN US
SRI
(1978) 1.36X10+8 GRAMS (CONSUMPTION, ESTIMATE)
SRI

10.7 U.S. Imports

(1976) No Data
SRI
(1978) No Data
SRI

10.8 U.S. Exports

(1976) No Data
SRI
(1978) No Data
SRI

10.9 General Manufacturing Information

The WHO Recommended Classification of Pesticides by Hazard identifies Phosphamidon (technical grade) as Class IA: extremely hazardous; Main Use: insecticide. According to the PIC /Prior Informed Consent/ Convention, export of /Phosphamidon/ can only take place with the prior informed consent of the importing Party. ...(further information can be found at: http://www.pic.int/).
WHO (2005) The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2004, International Programme on Chemical Safety, p.16,39
Phosphamidon is compatible with all except highly alkaline pesticides, though for an unknown reason, its biological activity is reduced by copper oxychloride.
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 373
Patents: ...British patent 829576; Belgian patent 552284; US patent 2908605; Phosphamidon exists as a mixture of 70% (z)-isomer (beta-isomer) and 30% (e)-isomer (alpha-isomer)... the (z)-isomer has the greater insecticidal activity.
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. 668
NOT PRODUCED COMMERCIALLY IN US
SRI
Status: Cancelled ... RED/ Voluntary cancellation 9/96
United States Environmental Protection Agency/ Prevention, Pesticides and Toxic Substances; Status of Pesticides in Registration, Reregistration, and Special Review. (1998) EPA 738-R-98-002, p. 458

11 Identification

11.1 Analytic Laboratory Methods

Method: AOAC 993.01, Phosphamidon in Technical and Formulated Products, Liquid Chromatographic Method; Analyte: Phosphamidon; Matrix: Technical, suspension concentrates, and liquid formulations.[
Horwitz W, ed.; Official Methods of Analysis of AOAC International 17th ed. (2000). CD-ROM, AOAC International, Gaithersburg, MD]
Two-dimensional gas chromatography with capillary columns and parallel detection with flame-photometric and electron-capture detection were used to analyze pesticide residues in food.
Stan HJ, Mrowetz D; Residue analysis of pesticides in food by two-dimensional gas chromatography with capillary columns and parallel detection with flame-photometric and electron-capture detection; J Chromatogr 279: 173-87 (1983)
The negative-ion mass spectra of phosphamidon obtained by chemical-ionization with methane, under electron-capture conditions, is reported. The influence of different ionization parameters on the total ion current and the relative intensities of the various fragment ions were studied. Few fragment ions were observed, although they were characteristic for the class of cmpd. The occurrence of the molecular anion is strongly dependent on the molecular structure and its ability to stabilize the radical formed in the primary electron capture region by charge delocalization. Negative-ion mass spectrometry with multiple ion detection may be a valuable tool for residue analysis in food and environmental samples.
Stan HJ, Kellner G; Negative chemical ionization mass spectrometry of organophosphorus pesticides; Biomed Mass Spectrom 9 (11): 483-92 (1982)
Phosphamidon was determined by 2-dimensional TLC on silica gel, using petroleum ether-Et20 (5:1 and 1:2, respectively). Rf values were tabulated.
Korsos IM, Lantos J; Thin-layer chromatographic identification of pesticides; Novenyvedelem (Budapest) 20 (1): 30-4 (1984)
For more Analytic Laboratory Methods (Complete) data for PHOSPHAMIDON (8 total), please visit the HSDB record page.

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

1 of 4
View All
Pictogram(s)
Acute Toxic
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

H311 (87.2%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H330 (12.8%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H341 (87.2%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

H400 (87.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (87.2%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P391, P403+P233, 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 47 reports by companies from 3 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.

12.1.2 Hazard Classes and Categories

Acute Tox. 2 (100%)

Acute Tox. 3 (87.2%)

Acute Tox. 1 (12.8%)

Muta. 2 (87.2%)

Aquatic Acute 1 (87.2%)

Aquatic Chronic 1 (87.2%)

Germ cell mutagenicity - category 2

Hazardous to the aquatic environment (acute) - category 1

Hazardous to the aquatic environment (chronic) - category 1

Acute toxicity (dermal) - category 3

Acute toxicity (ingestion) - category 2

12.1.3 Health Hazards

This material is extremely toxic; the probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful for a 150-lb person. It is a cholinesterase inhibitor. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

12.1.4 Fire Hazards

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Container may explode in heat of fire. Heat above 320F may cause decomposition and evolution of highly toxic fumes of phosphorus oxides and chlorides. Hydrolyzes in alkali. Stable in neutral and acid media. Hydrolyzes in alkali. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

12.1.5 Hazards Summary

An eye irritant; Can be absorbed through skin; A cholinesterase inhibitor that may cause CNS effects resulting in convulsions and respiratory depression; [ICSC] Gamma-Chlorophosphamidon, present as an impurity at a level of 1-2% in the technical product, is approximately 20 times more potent as a human cholinesterase inhibitor; In a human test involving unprotected exposure from aircraft spraying in a paddy field, volunteers experienced immediate eye irritation and depression of plasma cholinesterase by as much as 50%; No evidence of delayed neurotoxicity in hens; [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.

12.1.6 Skin, Eye, and Respiratory Irritations

In a test of the effect of direct exposure during agricultural spraying, 32 volunteers varying in age from 10 to 70 years stayed in paddy fields while phosphamidon was applied by aircraft and for 1 hour afterward. ... The ultra low-volume application was at a rate of 550 g/ha, that is, at almost twice the recommended rate. The volunteers wore their usual light clothing and no other protection. Most of the 32 people experienced irritation of their conjunctivae immediately after the application ...
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 374

12.2 Safety and Hazard Properties

12.2.1 Acute Exposure Guideline Levels (AEGLs)

12.2.1.1 AEGLs Table
AEGLs
AEGL 1: Notable discomfort, irritation, or certain asymptomatic non-sensory effects. However, the effects are not disabling and are transient and reversible upon cessation of exposure (Unit: mg/m3)
10 min
NR
30 min
NR
60 min
NR
4 hr
NR
8 hr
NR
AEGLs
AEGL 2: Irreversible or other serious, long-lasting adverse health effects or an impaired ability to escape (Unit: mg/m3)
10 min
0.37 mg/m3
30 min
0.37 mg/m3
60 min
0.30 mg/m3
4 hr
0.19 mg/m3
8 hr
0.093 mg/m3
AEGLs
AEGL 3: Life-threatening health effects or death (Unit: mg/m3)
10 min
1.1 mg/m3
30 min
1.1 mg/m3
60 min
0.90 mg/m3
4 hr
0.57 mg/m3
8 hr
0.28 mg/m3
12.2.1.2 AEGLs Notes

NR=Not recommended due to insufficient data

AEGLs Status: Proposed

12.3 First Aid Measures

Inhalation First Aid
Fresh air, rest. 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!). Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

12.3.1 First Aid

Note: Phosphamidon is a cholinesterase inhibitor.

Signs and Symptoms of Acute Phosphamidon Exposure: Acute exposure to phosphamidon may produce pinpoint pupils, blurred vision, headache, dizziness, muscle spasms, and profound weakness. Vomiting, diarrhea, abdominal pain, seizures, and coma may also occur. The heart rate may decrease following oral exposure or increase following dermal exposure. Hypotension (low blood pressure) may occur, although hypertension (high blood pressure) is not uncommon. Chest pain may be noted. Respiratory effects include dyspnea (shortness of breath), respiratory depression, and respiratory paralysis. Psychosis may occur.

Emergency Life-Support Procedures: Acute exposure to phosphamidon may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.

Inhalation Exposure:

1. Move victims to fresh air. Emergency personnel should avoid self-exposure to phosphamidon.

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.

3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

4. Transport to a health care facility.

Dermal/Eye Exposure:

1. Remove victims from exposure. Emergency personnel should avoid self- exposure to phosphamidon.

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.

3. Remove contaminated clothing as soon as possible.

4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.

5. Wash exposed skin areas three times with soap and water.

6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

7. Transport to a health care facility.

Ingestion Exposure:

1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.

2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of phosphamidon is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step

4.Ipecac should not be administered to children under 6 months of age.Warning: Ingestion of phosphamidon may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step

4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal.

4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water.

5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults.

6. Transport to a health care facility. (EPA, 1998)

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

12.4 Fire Fighting

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Stay upwind; keep out of low areas. Move containers from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) This material may burn, but does not ignite readily. For small fires, use dry chemical, carbon dioxide, water spray, or foam. For large fires, use water spray, fog, or foam. (EPA, 1998)

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
In case of fire in the surroundings, use appropriate extinguishing media.

12.4.1 Fire Fighting Procedures

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. 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, dry chemical or carbon dioxide. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic/
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 698
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.) /Organophosphorus pesticides, solid, toxic/
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 699
Fire Service personnel should extinguish fires with alcohol-resistant foam, water spray, or dry powder.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20trade%20names

12.5 Accidental Release Measures

12.5.1 Isolation and Evacuation

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

12.5.2 Spillage Disposal

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable non-metallic containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

12.5.3 Cleanup Methods

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 698
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 698
Environmental considerations: Land spill: Dig a pit, pond, 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, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 698
Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer. (Extra personal protection: complete protective clothing including self-contained breathing apparatus).
IPCS, CEC; International Chemical Safety Card on Phosphamidon (March 1995). Available from, as of June 30, 2003: https://www.inchem.org/pages/icsc.html

12.5.4 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.
Hydrolysis...: Treat phosphamidon by alkali, then mix the product with a portion of soil rich in organic matter. ...Recommendable method: Incineration. Peer-review: Incineration in a unit with effluent gas scrubbing is recommendable for large amounts. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
United Nations. Treatment and Disposal Methods for Waste Chemicals (IRPTC File). Data Profile Series No. 5. Geneva, Switzerland: United Nations Environmental Programme, Dec. 1985., p. 236
Hydrolysis: Hydrolysis products are pH dependent. Acidic hydrolysis yields alpha-chloroacetoacetic acid diethylamide. The amide can subsequently degrade to diethyl amine, carbon dioxide and chloroacetone in strong acid or with heating. A different series of products have been identified for the alkaline hydrolysis. Although the diethyl amide of alpha-chloroacetoacetic acid appears to initially form, it very rapidly hydrolyzes, even in weak alkaline soln, and yields chloride and the diethylamide of alpha-hydroxyacetoacetic acid. In strong alkali this amide can slowly hydrolyze to yield acetic acid and glycolic acid diethylamide. The product, glycolic acid diethylamide, is stable in base. The hydrolysis products are non-toxic and rapidly assimilated into natural constituents. Empty containers should be rinsed by an alkaline soln.
United Nations. Treatment and Disposal Methods for Waste Chemicals (IRPTC File). Data Profile Series No. 5. Geneva, Switzerland: United Nations Environmental Programme, Dec. 1985., p. 236

12.5.5 Preventive Measures

Poisonous if swallowed, inhaled, or absorbed through skin. ... Do not get in eyes, on skin or clothing. Do not breathe mist. ... Wash thoroughly after handling. Do not drink any alcoholic beverage before or during spraying since alcohol promotes absorption of organic phosphates.
Farm Chemicals Handbook 2002. Meister Publishing Co., 2002., p. C-316
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, toxic
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 699
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, toxic/
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 698
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. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, flammable, toxic/
Association of American Railroads/Bureau of Explosives; Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads. Pueblo, CO. 2002., p. 698
For more Preventive Measures (Complete) data for PHOSPHAMIDON (10 total), please visit the HSDB record page.

12.6 Handling and Storage

12.6.1 Nonfire Spill Response

Caution : Explosion potential is high. Containers may explode in heat of fire. Highly toxic phosphorus oxides and chlorides may be emitted when phosphamidon is heated to decomposition. Avoid sources of extreme heat.

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors.

Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal.

Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

12.6.2 Safe Storage

Store in an area without drain or sewer access. Well closed. Keep in a well-ventilated room. Separated from bases and food and feedstuffs.

12.6.3 Storage Conditions

You should store this material under ambient temperatures.
DHHS/National Toxicology Program; Chemical Health & Safety Data File. Available from: https://ntp-db.niehs.nih.gov/cgi/iH_Indexes/Chem_H&S/iH_Chem_H&S_Frames.html on Phosphamidon (13171-21-6) as of June 27, 2003.
It... is packed in polyethylene containers.
Martin, H. and C.R. Worthing (eds.). Pesticide Manual. 4th ed. Worcestershire, England: British Crop Protection Council, 1974., p. 409

12.7 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.

12.7.1 Inhalation Risk

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

12.7.2 Effects of Short Term Exposure

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

12.7.3 Effects of Long Term Exposure

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

12.7.4 Allowable Tolerances

Tolerances (expressed as phosphamidon) for residues of the insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate) including all of its related cholinesterase-inhibiting compounds in or on raw agricultural commodities are established as follows: apples, 1.0 ppm (Expiration/Revocation Date 12/31/02)
40 CFR 180.239; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 1, 2003: https://www.ecfr.gov

12.7.5 Personal Protective Equipment (PPE)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Firefighters should wear full protective clothing including self-contained breathing apparatus.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20trade%20names
Wear a pesticide respirator jointly /certified/ by the Mining Enforcement and Safety Administration and by the National Institute for Occupational Safety and Health. Wear natural rubber gloves, protective clothing, and goggles.
Farm Chemicals Handbook 2002. Meister Publishing Co., 2002., p. C-316

12.7.6 Preventions

Exposure Prevention
STRICT HYGIENE! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN! IN ALL CASES CONSULT A DOCTOR!
Inhalation Prevention
Use ventilation, 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.

12.8 Stability and Reactivity

12.8.1 Air and Water Reactions

Water soluble. Hydrolyzed by alkali with a half-life at 73 °F of 13.8 days at pH 7 and 2.2 days at pH 10 (NTP, 1992).
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.8.2 Reactive Group

Amides and Imides

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Halogenated Organic Compounds

Hydrocarbons, Aliphatic Unsaturated

12.8.3 Reactivity Profile

PHOSPHAMIDON is corrosive to iron, tin and aluminum. Incompatible with alkaline preparations and should not be mixed with copper oxychloride, captan, folpet or sulfur. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.8.4 Hazardous Reactivities and Incompatibilities

Reacts with bases (hydrolysis). Attacks metals such as iron, tin and aluminium.
IPCS, CEC; International Chemical Safety Card on Phosphamidon (March 1995). Available from, as of June 30, 2003: https://www.inchem.org/pages/icsc.html
It is also incompatible with alkaline preparations and should not be mixed with copper oxychloride, captan, folpet or sulphur.
DHHS/National Toxicology Program; Chemical Health & Safety Data File. Available from: https://ntp-db.niehs.nih.gov/cgi/iH_Indexes/Chem_H&S/iH_Chem_H&S_Frames.html on Phosphamidon (13171-21-6) as of June 27, 2003.

12.9 Transport Information

12.9.1 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. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. 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 PHOSPHAMIDON (16 total), please visit the HSDB record page.

12.9.2 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 PHOSPHAMIDON (6 total), please visit the HSDB record page.

12.9.3 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)

12.9.4 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 October 22, 2002: 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 44th ed. 2003. International Air Transport Association, Montreal, Canada., p. 224
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.
IMDG; International Maritime Dangerous Goods Code; International Maritime Organization p.6213-2,3270,6219,6220,6221 (1998)
Severe marine pollutant
49 CFR 172.101, Appendix B; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 1, 2003: https://www.ecfr.gov

12.9.5 DOT Label

Poison

12.9.6 Packaging and Labelling

Do not transport with food and feedstuffs. Severe marine pollutant.

12.9.7 EC Classification

Symbol: T+, N; R: 24-28-68-50/53; S: (1/2)-23-36/37-45-60-61

12.9.8 UN Classification

UN Hazard Class: 6.1; UN Pack Group: II

12.10 Regulatory Information

Status Regulation (EC)
2002/2076

12.10.1 CERCLA Reportable Quantities

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Phosphamidon is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.
40 CFR 355; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 1, 2003: https://www.ecfr.gov

12.10.2 FIFRA Requirements

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Phosphamiidon is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0157; Pesticide type: Insecticide; Registration Standard Date: 12/87; Case Status: The last registered pesticide products containing this pesticide were voluntarily cancelled by their registrants while EPA was developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Phosphamiidon; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.142 (Spring, 1998) EPA 738-R-98-002
Tolerances (expressed as phosphamidon) for residues of the insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl diemthyl phosphate) including all of its related cholinesterase-inhibiting compounds in or on raw agricultural commodities are established as follows: apples (Expiration/Revocation Date 12/31/02)
40 CFR 180.239; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 1, 2003: https://www.ecfr.gov
Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. Formulation: Liquid formulations 75% and greater; Use Pattern: Rice; Classification: Resticted; Criteria Influencing Restriction: Acute dermal toxicity. Residue effects on mammalian species. Residue effects on avian species.
40 CFR 152.175; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 1, 2003: https://www.ecfr.gov
Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. Formulation: Dust formulations 1.5% and greater; Use Pattern: All uses; C Classification: Restricted; Criteria Influencing Restriction: Acute dermal toxicity. Residue effects on mammalian species. Residue effects on avian species.
40 CFR 152.175; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 1, 2003: https://www.ecfr.gov

12.11 Other Safety Information

Chemical Assessment

IMAP assessments - Phosphoric acid, 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester: Human health tier I assessment

IMAP assessments - Phosphoric acid, 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester: Environment tier I assessment

12.11.1 Special Reports

DHEW/NCI; Bioassay of Phosphamidon for Possible Carcinogenicity (1979) Technical Rpt Series No. 16 DHEW Pub No. (NIH) 79-816

13 Toxicity

13.1 Toxicological Information

13.1.1 Evidence for Carcinogenicity

Cancer Classification: Group C Possible Human Carcinogen
USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch: "Chemicals Evaluated for Carcinogenic Potential" (April 2006)

13.1.2 Carcinogen Classification

Substance
NTP Technical Report
TR-016: Bioassay of Phosphamidon for Possible Carcinogenicity (CASRN 13171-21-6) (1979 )
Peer Review Date
Conclusion for Male Rat
Equivocal Evidence Equivocal Evidence
Conclusion for Female Rat
Equivocal Evidence Equivocal Evidence
Conclusion for Male Mice
No Evidence No Evidence
Conclusion for Female Mice
No Evidence No Evidence
Summary
It is concluded that under the conditions of this bioassay, technical-grade phosphamidon was not carcinogenic for B6C3F1 mice. The data obtained in this bioassay with Osborne-Mendel rats are insufficient to allow the interpretation that technical-grade phosphamidon is carcinogenic in this species.

13.1.3 Exposure Routes

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

13.1.4 Symptoms

Inhalation Exposure
Sweating. Muscle twitching. Pupillary constriction, muscle cramp, excessive salivation. Diarrhoea. Dizziness. Laboured breathing. Vomiting. Convulsions. Unconsciousness. Symptoms may be delayed.
Skin Exposure
MAY BE ABSORBED! Further see Inhalation.
Eye Exposure
Redness. Pain.
Ingestion Exposure
Abdominal cramps. Further see Inhalation.

13.1.6 Adverse Effects

Other Poison - Organophosphate

13.1.7 Acute Effects

13.1.8 Toxicity Data

LC50 (rat) = 135 mg/m3/4h

13.1.9 Interactions

...Phosphamidon and dimethylvinphos, have their acute toxicities reduced by phenobarbital pre-treatment.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 307
Vitamin C, when admin concurrently with a pesticide ... phosphamidon ... could significantly decr the frequency of pesticide induced clastogenic and mitosis disruptive changes in the bone marrow cells of young Swiss Albino mice. Of these three doses (10, 20 or 40 mg/kg/bw) of the vitamin, the one which is double the human therapeutic dose (20 mg/kg/bw/day) was the most effective as an antimutagen to be followed by 40 mg and 10 mg. None of these doses of vitamin C showed any genotoxicity of their own for the parameters studied here.
Kahn PK, Sinha SP; Mutat Res 298 (3): 157-61 (1993)
Because different classes of enzymes may be inhibited, the effects of organophosphorus pesticide poisoning may be complex and potentially at least could involve interactions with drugs as well as with other pesticides or chemicals. Potentiation may also involve solvents or other components of formulated pesticides. Certain drugs such as phenothiazines, antihistamines, CNS depressants, barbiturates, xanthines (theophylline), aminoglycosides and parasympathomimetic agents are to be avoided because of increased toxicity.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20tr
/When citiolone was administered with phosphamidon/... significant depletion was observed in the glutathione-S-transferase activity as well as in the level of total and non-protein bound sulfhydryl groups in various CNS regions of phosphamidon intoxicated rats. When citiolone was administered alone, there was a remarkable elevation in glutathione-S-transferase activity. However, significant protection against glutathione-S-transferase inhibition was observed when phosphamidon and citiolone were administered simultaneously.
Naqvi SMZ, Hasan M; Neuroreport 2 (1): 61-3 (1991)

13.1.10 Antidote and Emergency Treatment

Airway protection. Insure that a clear airway exists. Intubate the patients and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 40
Atropine sulfate. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access if difficult to obtain. Depending on the severity of poisoning, doses of atropine ranging from very low to as high as 300 mg/day may be required, or even continuous infusion. The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate the cholinesterase enzyme or accelerate disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. Favorable response to a test dose of atropine (1 mg in adults, 0.01 mg/kg in children under 12 years) can help differentiate poisoning by anticholinesterase agents from other conditions. However, lack of response, with no evidence of atropinization (atropine refractoriness) is typical of more severe poisonings. The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. ...Do not administer atropine or pralidoxime prophylactically to workers exposed to organophosphate pesticides. Prophylactic dosage with either atropine or pralidoxime may mask early signs and symptoms of organophosphate poisoning and thus allow the worker to continue exposure and possibly progress to more severe poisoning. Atropine itself may enhance the health hazards of the agricultural work setting: impaired heat loss due to reduced sweating and impaired ability to operate mechanical equipment due to blurred vision. This can be caused by mydriasis, one of the effects of atropine. /Organophosphate pesticides/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 41
Glycopyrolate has been studied as an alternative to atropine and found to have similar outcomes using continuous infusion. Ampules of 7.5 mg of glycopyrolate were added to 200 ml of saline and this infusion was titrated to the desired effects of dry mucous membranes and heart rate above 60 beats/min. During this study, atropine was used as a bolus for a heart rate less than 60 beats/min. The other apparent advantage to this regimen was a decreased number of respiratory infections. This may represent an alternative when there is a concern for respiratory infection due to excessive and difficult to control secretions, and in the presence of altered level of consciousness where the distinction between atropine toxicity or relapse of organophosphate poisoning is unclear. /Organophosphate pesticides/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 41
Pralidoxime. Before administration of pralidoxime, draw a blood sample (heparinized) for cholinesterase analysis (since pralidoxime tends to reverse the cholinesterase depression). Administration pralidoxime (Protopam, 2-PAM), a cholinesterase reactivator, in cases of severe poisoning by organophosphate pesticides in which respiratory depression, muscle weakness, and/or twitching are severe. When administered early (usually less than 48 hours after poisoning) pralidoxime relieves the nicotinic as well as the muscarinic effects of poisoning. Pralidoxime works by reactivating the cholinesterase and also by slowing the "aging" process of phosphorylated cholinesterase to a non-reactivatable form. ... Dosage of pralidoxime may be repeated in 1-2 hours, then at 10-12 hour intervals if needed. In very severe poisonings, dosage rates may be doubled. Repeated doses of pralidoxime are usually required. In cases that involve continuing absorption of organophosphate (as after ingestion of large amounts), or continuing transfer of highly lipophilic organophosphate from fat into blood, it may be necessary to continue administration of pralidoxime for several days beyond the 48 hour post-exposure interval usually cited as the limit of its effectiveness. ... Blood pressure should be monitored during administration because of the occasional occurrence of hypertensive crisis. Administration should be slowed or stopped if blood pressure rises to hazardous levels. Be prepared to assist pulmonary ventilation mechanically if respiration is depressed during or after pralidoxime administration. If intravenous injection is not possible, pralidoxime may be given by deep intramuscular injection. /Organophosphate pesticides/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 41
For more Antidote and Emergency Treatment (Complete) data for PHOSPHAMIDON (18 total), please visit the HSDB record page.

13.1.11 Medical Surveillance

In humans occupationally exposed to phosphamidon, urinary excretion of dimethylphosphate is detectable at an exposure level insufficient to depress plasma or erythrocyte cholinesterase. Also, it has been reported that trace amounts of these alkylphosphate metabolites may occur in urine of unexposed subjects. Therefore, a comparison with reference groups or individuals pre-exposure values is recommended when exposed workers are tested.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20tr
Measurement of whole blood-AChE is the most widely adopted method for monitoring the effects of occupational exposure to organophosphorus insecticides. Physiological variations in blood ChE levels occur in a healthy person and are seen among a population. It has been estimated that the coefficient of variation for AChE activity in samples from an individual is 8-11%, and that a decrease of 23% below pre-exposure level may, therefore, be considered significant. If the average of several pre-exposure values were available, then a decrease of 17% would be significant. It has been recommended that, if measured activity is reduced by 30% or more of the pre-exposure value, AChE measurements should be repeated at appropriate intervals to confirm the results. Depressions of AChE or ChE in excess of 20-25% are considered diagnostic of exposure but not, necessarily, indicative of hazard. Depressions of 30-50% or more are considered indicators for removal of an exposed individual from further contact with pesticides until levels return to normal. /Organophosphorus Pesticides/
WHO; Environ Health Criteria 63: Organophosphorus pesticides (1986). Available from, as of July 22,2003: https://www.inchem.org/pages/ehc.html
...Organophosphorus pesticides may undergo hydrolysis in vivo to yield substituted phosphoric acids that are subsequently excreted in urine. Advances in gas chromatography and combined gas chromatography/mass spectrometry (GC/MS) have made it possible to analyse the urine of exposed persons for the presence of appropriate metabolites. It is usually necessary to preserve the sample by the addition of chloroform, to concentrate or extract the metabolite(s), and to convert them to suitably-volatile derivatives that can be detected by GC. Obviously, access to a well-equipped analytical laboratory, capable of the quick processing of samples, is a necessary factor if monitoring by urine analysis is proposed. However, in some cases, simpler and sensitive colorimetric tests are available for screening the urine of exposed persons. Thus, 4-nitrophenol can be measured directly in the urine of workers exposed to parathion. Consideration of the concentration of metabolite(s) in the urine can be helpful in determining patterns of exposure, and these concentrations can be calibrated against the effects on AChE for a particular pesticide. However, the time-course and peak of excretion of metabolites appears to vary according to dose, so that serial sampling and analyses of urine are desirable. Levels of metabolite alone cannot be considered a guide to hazard. This is obvious when it is realized that pesticides that have very different toxicities may yield identical acidic metabolites. Thus, the level of metabolites in urine, after exposure to sufficient amounts of the very toxic parathion-methyl to depress blood-AChE to 50%, will be much lower than that of the identical metabolites, following exposure to the related fenitrothion, which is about 40 times less toxic. /Organophosphorus Pesticides/
WHO; Environ Health Criteria 63: Organophosphorus pesticides (1986). Available from, as of July 22,2003: https://www.inchem.org/pages/ehc.html
SRP: Workers should undergo an annual medical exam. Contraindications for work with organophosporous pesticides are organic diseases of the CNS, mental disorders and epilepsy, and pronounced endocrine disorders. Blood cholinesterase, both plasma and RBC, 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 until cholinesterase activity is restored. /Organophosphorous pesticides/

13.1.12 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ In a test of the effect of direct exposure during agricultural spraying, 32 volunteers varying in age from 10-70 years stayed in paddy fields while phosphamidon was applied by aircraft and for 1 hr afterward. ...The ultra low-volume application was at a rate of 550 g/ha, that is, at almost twice the recommended rate. The volunteers wore their usual light clothing and no other protection. Most of the 32 people experienced irritation of their conjunctivae immediately after the application; that was the only clinical effect. ...Plasma cholinesterase of the people showed a depression of 0-25% in 19 subjects, 26-50% in 19 subjects, and over 50% in 2 subjects. Maximal depression occurred from 1 to 3 days after exposure; recovery was complete by the 9th day. There was no significant effect on red cell cholinesterase.
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 374
/HUMAN EXPOSURE STUDIES/ One pregnant woman who was involved in a serious acute exposure to mevinphos and phosphamidon delivered a normal child; another exposed woman who became pregnant shortly after the incident also had a normal child.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20tr
/HUMAN EXPOSURE STUDIES/ In technical preparations of phosphamidon, gamma-chlorophosphamidon is present at a level of 1-2% of the total product. This compound inhibits...human cholinesterase about 20 times more than pure phosphamidon. /gamma-Chlorophosphamidon/
Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 292
/HUMAN EXPOSURE STUDIES/ ...Cauliflower workers who experienced acute poisoning by OP insecticides mevinphos (Phosdrin) and phosphamidon (Dimecron) /were studied/. The workers had begun work tying leaves over the heads of the plants only 6 hr after the field had been sprayed. Sixteen such workers were followed in weekly clinics with interviews and plasma and red blood cell (RBC) cholinesterase levels. Comparatively non-persistent symptoms (i.e., they had typically resolved by 10 weeks) included nausea, dizziness, vomiting, abdominal pain, ataxia, and night sweats or insomnia. Symptoms that persisted in at least three of the 16 subjects at 10 weeks or more included blurred vision/vision disturbance (56%), headache (25%), anxiety (41%), weakness, and anorexia. Symptoms persisted for up to 10 weeks, varying by symptom and individual. Six of the subjects initially had RBC AChE values within the normal laboratory range, but follow-up testing showed activity to have been significantly inhibited.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20trade%2
For more Human Toxicity Excerpts (Complete) data for PHOSPHAMIDON (13 total), please visit the HSDB record page.

13.1.13 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Effects of exposure for 96 hr to 35.4 ppm (the median lethal concn) of phosphamidon on histopathological and biochemical alterations in the liver and kidney of Nemachelius denisonii were studied. Vacuolated hepatocytes, necrosis, and damage to connective tissue in the liver were found. In kidneys, shrinkage of the glomeruli and swelling on the renal tubules were detected. Inhibition of alkaline phosphatase, glucose 6-phosphatase, and lactic dehydrogenase activities in the liver and kidney were observed.
Rashatwar SS, Ilyas R; Effect of phosphamidon in a freshwater teleost fish Nemachelius denisonii (Day) - histopathological and biochemical studies; J Environ Biol 5 (1): 1-8 (1984)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposurey/ .../There was/ no effect on rats fed up to 10 mg/kg/day for 90 days except slower weight gain, weight gain /was/ normal at 2.5 mg/kg level.
Spencer, E.Y. Guide to the Chemicals Used in Crop Protection. 6th ed. Publication 1093, Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1973., p. 410
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In ... feeding studies in dogs, phosphamidon was tolerated at a dose of 5 mg/kg for 90 days without effect. In subacute inhalation studies, dogs, guinea pigs, and rats were exposed to an atmosphere containing 0.125 mg/L phosphamidon for 6 hr/day, 5 days/week for 90 days without any marked toxic effects.
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4832
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Phosphamidon technical (purity = 92.1%; LOT #: FL 851179; opaque, dark brown liquid; density 1.28 mg/ml) was administered dermally at 0 (no vehicle used), 10, 100, or 1,000 (reduced to 750 mg/kg after day 13) mg/kg/day to 5 New Zealand white rabbits/sex/dose (5x/wk for 3 weeks--15 days total). 130 days later, 0 (deionized water), 0.1, or 1.0 mg/kg/day of phosphamidon technical was administered to 5 rabbits/sex/dose on the same treatment schedule as the first experiment. ...Systemic NOEL = 100 mg/kg/day (subacute superficial dermatitis and erythema/edema were observed in both sexes). ChE NOEL >1.0 <10 mg/kg/day (significant inhibition of brain cholinesterase activity was observed in both sexes at >10 mg/kg/day).
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: https://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Phosphamidon as of June 23, 2003.
For more Non-Human Toxicity Excerpts (Complete) data for PHOSPHAMIDON (31 total), please visit the HSDB record page.

13.1.14 Human Toxicity Values

The probable fatal dose of phosphamidon for an adult by ingestion is 5-50 mg/kg bw. The estimated fatal dose in humans (~70 kg) is 490 mg by oral ingestion.
IPCS; Poisons Information Monograph 454 on Phosphamidon (August 2001). Available from, as of June 26, 2003: https://www.inchem.org/documents/pims/chemical/pim454.htm#1.5%20Main%20brand%20names/%20main%20tr

13.1.15 Non-Human Toxicity Values

LD50 Rat oral 17.4 mg/kg
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. 668
LD50 Mouse sc 26 mg/kg
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 373
LD50 Mouse ip 5.8 mg/kg
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 373
LD50 Mouse iv 6 mg/kg
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 373
For more Non-Human Toxicity Values (Complete) data for PHOSPHAMIDON (18 total), please visit the HSDB record page.

13.1.16 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=13171-21-6]

13.1.17 National Toxicology Program Studies

A bioassay of technical grade phosphamidon for possible carcinogenicity was conducted using Osborne-Mendel rats and B6C3F1 mice. The test material was admin in feed to 50 rats and 50 mice of each sex at one of two doses, either 80 or 160 ppm. The were fed the test chemical for 80 wk, then observed without cmpd admin for 30 or 31 wk; the low dose male mice were fed for 71 wk, then observed for 19 wk; the high dose male mice were fed for 62 wk, then observed for 28 wk; the low and high dose female mice were fed for 80 wk, then observed for 10 or 11 wk. Matched controls consisted of 10 untreated rats or 10 untreated mice of each sex; pooled controls consisted of the matched controls combined with 85 male and 85 female untreated rats or 80 male and 80 female untreated mice from similar bioassays of eight other test chemicals. ... In male rats, the combined incidence of hemangiomas and hemangiosarcomas in the spleen showed a statistically significant (p=0.012) dose related trend. However, the comparison with matched controls was not significant, and the historical records of this laboratory on untreated males of this strain show a tumor incidence of 6/240 (3%) with incidences in individual control groups as high as 3/9 (99%) and 2/9 (22%), compared with 5/49 (10%) seen in the high dose group in this study. No hemangiomas or hemangiosarcomas were found in females. In female rats, the Cochran-Armitage test for dose related trend was significant (p=0.003) for C cell adenomas and carcinomas of the thyroid when pooled controls were compared with the dosed groups. The incidences of these tumors were also significant when low dose females (p=0.003) and high dose females (p=0.004) were compared directly with pooled controls. However, the historical records of this laboratory show a tumor incidence of 16/235 (7%) in untreated female rats of this strain of female rats, with incidences in individual control groups as high as 3/9 (33%) and 3/10 (30%); these data are therefore considered marginal and insufficient to establish an association between the tumors and the admin of the chemicals. In males, the incidence of these tumors was not statistically significant. In mice, no tumor occurred at a higher incidence in dosed animals than in controls. It is concluded that under the conditions of this bioassay, technical grade phosphamidon was not carcinogenic for B6C3F1 mice. The data obtained in this bioassay with Osborne-Mendel rats are insufficient to allow the interpretation that technical grade phosphamidon is carcinogenic in this species. Levels of Evidence of Carcinogenicity: Male Rats: Equivocal; Female Rats: Equivocal; Male Mice: Negative; Female Mice: Negative.
Bioassay of Phosphamidon for Possible Carcinogenicity (1979) Technical Rpt Series No. 16 DHEW Pub No. (NIH) 79-816, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014

13.2 Ecological Information

13.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

13.2.2 Ecotoxicity Values

LD50 ANAS PLATYRHYNCHOS (MALLARD) ORAL 3.05 MG/KG, 3 MO OLD FEMALES (95% CONFIDENCE LIMIT 2.91-5.00) /SAMPLE PURITY 80%/
U.S. Department of the Interior, Fish and Wildlife Service. Handbook of Toxicity of Pesticides to Wildlife. Resource Publication 153. Washington, DC: U.S. Government Printing Office, 1984., p. 64
LD50 PERDIX PERDIX (PARTRIDGE) ORAL 9.7 MG/KG, 3 MO OLD FEMALES & MALES (95% CONFIDENCE LIMIT 8.3-11.3)
U. S. Department of the Interior, Fish & Wildlife Service, Bureau of Sport Fisheries & Wildlife. Handbook of Toxicity of Pesticides to Wildlife. Washington, D. C.: U. S. Government Printing Office, 1970., p. 94
LD50 ZENAIDA MACROURA (MOURNING DOVE) ORAL MALES AND FEMALES 2.0-4.0 MG/KG
U. S. Department of the Interior, Fish & Wildlife Service, Bureau of Sport Fisheries & Wildlife. Handbook of Toxicity of Pesticides to Wildlife. Washington, D. C.: U. S. Government Printing Office, 1970., p. 94
LD50 ZENAIDA ASIATICA (WHITE WINGED DOVE) ORAL, ADULT MALE AND FEMALE, 2.93 MG/KG (95% CONFIDENCE LIMIT 2.44-3.66 MG/KG) /SAMPLE PURITY 80%/
U.S. Department of the Interior, Fish and Wildlife Service. Handbook of Toxicity of Pesticides to Wildlife. Resource Publication 153. Washington, DC: U.S. Government Printing Office, 1984., p. 64
For more Ecotoxicity Values (Complete) data for PHOSPHAMIDON (15 total), please visit the HSDB record page.

13.2.3 Ecotoxicity Excerpts

/AQUATIC SPECIES/ /Phosphamidon/ may be hazardous to the environment; special attention should be given to aquatic organisms, birds and honey bees.
IPCS, CEC; International Chemical Safety Card on Phosphamidon (March 1995). Available from, as of June 30, 2003: https://www.inchem.org/pages/icsc.html
/AQUATIC SPECIES/ Glycogen levels were decreased and lactic acid levels increased in the tissues (hepatopancreas, foot, and mantle) of mussels exposed to phosphamidon (8 ppm for 48 hr). /Phosphamidon/ decreased oxidative metabolism in the tissues of the mussels. Consequently, the mussels switch over to anaerobiasis as an adaptive measure to combat the induced toxicity.
Moorthy KS et al; Bull Environ Contam Toxicol 30 (2): 219-22 (1983)
/AQUATIC SPECIES/ Dimecron (2.50-6.00 ppm), produced elevated activity of fructose 1,6-diphosphate aldolase of liver, brain and gill tissues in Clarias batrachus exposed for 24-96 hr. The toxic conditions produced by the pesticide ultimately caused the death of the fish due to the failure of the respiratory center of the brain. The breakdown of proteins and the diabetic condition caused by the pesticides possibly increased aldolase activity.
Tandon RS, Dubey A; Toxic effects of two organophosphorus pesticides on fructose 1,6-diphosphate aldolase activity of liver, brain and gills of the freshwater fish Clarias batrachus; Environ Pollut, Ser A 31 (1): 1-7 (1983)
/AQUATIC SPECIES /Phosphamidon is/... slightly toxic to fish.
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 457
For more Ecotoxicity Excerpts (Complete) data for PHOSPHAMIDON (12 total), please visit the HSDB record page.

13.2.4 ICSC Environmental Data

The substance is very toxic to aquatic organisms. This substance may be hazardous to the environment. Special attention should be given to birds and bees. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.

13.2.5 Environmental Fate / Exposure Summary

Phosphamidon's former production and use as an insecticide and acaricide may have resulted in its direct release to the environment. If released to air, a vapor pressure of 1.65X10-5 mm Hg at 25 °C indicates phosphamidon will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phosphamidon will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 10.5 hrs. Phosphamidon will react with ozone, exhibiting an atmospheric half-life of about 7 days. Particulate-phase phosphamidon will be removed from the atmosphere by wet and dry deposition. If released to soil, phosphamidon is expected to have very high mobility based upon retardation factors (Rf) of 0.91-0.92 in loam soils. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.5X10-12 atm-cu m/mole. Soil half-lives ranging from approximately <3 to 6 days have been reported. If released into water, phosphamidon is not expected to adsorb to suspended solids and sediment based upon the Rf values. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. A BCF of <1 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis half-lives at 23 °C of 74 days, 13.8 days, and 2.2 days at pH 4, 7, and 10, respectively, have been reported. Occupational exposure and general population exposure should be low or non-existent since phosphamidon is no longer produced or used in the US. In the past, phosphamidon was applied directly to fruit orchards as an spray and exposure to this compound was primarily by inhalation. (SRC)

13.2.6 Artificial Pollution Sources

Phosphamidon's former(1) production and use as an insecticide and acaricide(2) may have resulted in its direct release to the environment(SRC).
(1) USEPA/OPPTS; Status of Pesticides in Reregistration and Special Review. Washington, DC: Off Prevention Pest Toxic Sub/USEPA. 458 pages. USEPA-738/R-98-002. pp. 458 (1998)
(2) Metcalf RL; in Kirk-Othmer Encycl Chem Technol. 4th. NY, NY: John Wiley & Sons 14: 556 (1995)

13.2.7 Environmental Fate

TERRESTRIAL FATE: Based on a a soil thin layer chromatography study, retardation factors (Rf) of 0.91-0.92 in a silt loam, silt loam, and a fine sandy loam(1), indicate that phosphamidon has very high mobility in soil(SRC). Volatilization of phosphamidon from moist soil surfaces is not expected to be an important fate process(2) given an estimated Henry's Law constant of 1.5X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Phosphamidon is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.65X10-5 mm Hg(4). Half-lives in loam, loamy sand, and sand of approximately 6, 3, and <3 days, respectively(5), indicate that biodegradation of phosphamidon may be an important environmental fate process in soil.
(1) Khan S, Khan NN; Soil Sci 142: 214-22 (1986)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Tomlin C, ed; The Pesticide Manual World Compendium. 11th ed., Surrey, England: British Crop Protection Council p. 965 (1997)
(5) Benyon KI et al; Res Rev 47: 55-142 (1973)
AQUATIC FATE: Based on a a soil thin layer chromatography study, retardation factors (Rf) of 0.91-0.92 in a silt loam, silt loam, and a fine sandy loam(1) indicate that phosphamidon is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 1.5X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), a BCF of <1(5) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Phosphamidon's hydrolysis half-lives at 23 °C are 74 days, 13.8 days, and 2.2 days at pH 4, 7, and 10, respectively(6).
(1) Khan S, Khan NN; Soil Sci 142: 214-22 (1986)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)
(5) Min KJ, Cha CG; Bull Environ Contam Toxicol 65: 611-17 (2000)
(6) Anliker R, Beriger E; Res Rev 37: 1-14 (1971)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phosphamidon, which has a vapor pressure of 1.65X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phosphamidon 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 10.5 hrs(SRC), calculated from its rate constant of 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase phosphamidon may be removed from the air by wet and dry deposition(SRC). The rate constant for the vapor-phase reaction of phosphamidon with ozone has been estimated as 1.6X10-16 cu cm/molecule-sec at 25 °C(SRC), derived using a structure estimation method(1); this corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Tomlin C, ed; The Pesticide Manual World Compendium. 11th ed., Surrey, England: British Crop Protection Council p. 965 (1997)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Atkinson R, Carter WPL; Chem Rev 84: 437-70 (1984)

13.2.8 Environmental Biodegradation

AEROBIC: When applied at 5 ppm, the half-lives of phosphamidon in loam, loamy sand, and sand was approximately 6, 3, and <3 days, respectively(1,2). At an application rate of 1 ppm, the half-life in loam and silt was three to four weeks(1,2). No data on sterile controls were presented, and the pH of the soils studied were not reported.
(1) Voss G, Geissbuhler H; Res Rev 37: 133-52 (1971)
(2) Benyon KI et al; Res Rev 47: 55-142 (1973)

13.2.9 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of phosphamidon with photochemically-produced hydroxyl radicals has been estimated as 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of phosphamidon with ozone has been estimated as 1.6X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Atkinson R, Carter WPL; Chem Rev 84: 437-70 (1984)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
Phosphamidon is stable in neutral and weakly acid solutions but is rapidly hydrolyzed in alkaline solutions(2). The half-lives at 23 °C are 74 days, 13.8 days, and 2.2 days at pH 4, 7, and 10; at 45 °C the respective half-lives are 6.6 days, 2.1 days, and 3.3 hrs(3). The hydrolysis products are dimethyl phosphate and alpha-chloroacetoacetic acid diethylamide(3). Stability studies with seawater, freshwater, and in water-sediment systems in which the sediment was additionally washed to remove exchangeable ions indicate that exchangeable ions in the sediment facilitate hydrolysis and a higher ionic strength reduces this rate(1).
(1) Sarkar A, Sen Gupta R; Ind J Mar Sci 15: 72-4 (1986)
(2) Melnikov NN; Res Rev 36: 1-447 (1971)
(3) Anliker R, Beriger E; Res Rev 37: 1-14 (1971)

13.2.10 Environmental Bioconcentration

BCFs of <1 were measured for phosphamidon in zebrafish (Brachydanio rerio) using OECD test guideline 305 in a continuous flow-through system operated for 168 hrs with test concns of 995.4 and 198.3 ug/l(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). Bioconcentration of phosphamidon is unlikely due to its high water solubility(1), very low lipophilicity(1) and very rapid depuration(1,3).
(1) Min KJ, Cha CG; Bull Environ Contam Toxicol 65: 611-17 (2000)
(2) Franke C et al; Chemosphere 29: 1501-14 (1994)
(3) Geissbuhler H et al; Res Rev 37: 39-60 (1971)

13.2.11 Soil Adsorption / Mobility

The leaching behavior of phosphamidon in sand, loamy sand, loam, and silt soil in a 15 cm column was studied after 150 cm of rain applied(2). All the added phosphamidon leached through the sand and sandy loam soil, while most of the residue was in the lower third of the column(2). With the silt soil, residues were rather evenly distributed throughout the column and in the leachate, although the greatest fraction of residue was in the upper third of the column. In contrast with the good total recoveries in the other cases, recovery with the silt column was only 39%(2). According to a soil thin layer chromatography study with four soils, phosphamidon was very mobile (retardation factor (Rf) 0.91-0.92) in a silt loam (0.83% organic matter, pH 7.9), silt loam (0.72% organic matter, pH 6.6), and a fine sandy loam (0.52% organic matter, pH 8.8)(1). It was less mobile (Rf = 0.66) in a sandy loam (0.69% organic matter, pH 10.5)(1).
(1) Khan S, Khan NN; Soil Sci 142: 214-22 (1986)
(2) Voss G, Geissbuhler H; Res Rev 37: 133-52 (1971)

13.2.12 Volatilization from Water / Soil

The Henry's Law constant for phosphamidon is estimated as 1.5X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phosphamidon is expected to be essentially nonvolatile from water surfaces(2). Phosphamidon is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.65X10-5 mm Hg(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) Tomlin C, ed; The Pesticide Manual World Compendium. 11th ed., Surrey, England: British Crop Protection Council p. 965 (1997)

13.2.13 Atmospheric Concentrations

The concn of phosphamidon in air 18-24 hr after spraying in an apple orchard was <0.005 mg/cu m in calm weather and not detectable with a 1-2 m/sec wind(1). Temperatures were high in both cases. Similarly, 23 hr after phosphamidon was sprayed in a grapefruit orchard under clear, calm, and warm weather conditions, the phosphamidon concn 1.5 m above ground was <0.01 mg/cu m(1).
(1) Voss G, Geissbuhler H; Res Rev 37: 133-52 (1971)

13.2.14 Food Survey Values

In a pesticide screening study of 81 varieties of domestic and imported produce (6970 samples), no residues of phosphamidon were found above the detection limit of 0.50 ppm(1). According to FDAs Total Diet Study, April 1982-April 1984, the dietary intake of phosphamidon for each of seven population groups of different sex and age ranging from toddlers to seniors was <0.1 ng/kg body weight/day(2). According to FDA's Total Diet Study, phosphamidon residues are not present in food items consumed by infants(2). Phosphamidon is destroyed by heat >160 °C(3). After 1 hr of cooking, residue levels in apples and pears decreased by 80%(3). In a 1992-1993 FDA survey of domestic and imported pears and tomatoes, phosphamidon was not detected in any of the 710 domestic and 949 imported pear samples tested; neither was it detected in the 1219 domestic and 144 imported tomato samples tested(4).
(1) Schattenberg HJ III, Hsu JP; AOAC Inter 75 925-33 (1992)
(2) Gunderson EL; J Assoc Off Anal Chem 71: 1200-9 (1988)
(3) Benyon KI et al; Res Rev 47: 55-142 (1973)
(4) Roy RR et al; J AOAC Inter 78: 930-40 (1995)

13.2.15 Plant Concentrations

The concn of phosphamidon on treated foliage 18-24 hr after spraying in an apple orchard was 20 ppm(1). Foliage in a grapefruit orchard contained 150 ppm phosphamidon 23 hours after spraying(1). Phosphamidon is rapidly absorbed and metabolized in plants(3). Reported initial half-lives are of the order of 1-2 days(1,2,3). Degradation then proceeds more slowly with residues decreasing to the 0.5 ppm level or less in about 1 week in leafy plants and 2-3 weeks in fruit after normal application(1,2,3).
(1) Voss G, Geissbuhler H; Res Rev 37: 133-52 (1971)
(2) Geissbuhler H et al; Res Rev 37: 39-60 (1971)
(3) Worthing CR, Walker SB, eds; The Pesticide Manual 8th ed Suffolk, England: Lavenham Press Ltd (1987)

13.2.16 Animal Concentrations

Phosphamidon is rapidly metabolized in animals(1) and therefore residues should not be present in animals unless recently exposed.
(1) Geissbuhler H et al; Res Rev 37: 39-60 (1971)

13.2.17 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

13.2.18 Probable Routes of Human Exposure

Occupational exposure and general population exposure should be low or non-existent since phosphamidon is no longer produced or used in the US. In the past, phosphamidon was applied directly to fruit orchards as an spray and exposure to this compound was primarily by inhalation. (SRC)
Secondary exposure of children through contact with their parents' contaminated clothing can also occur. /Organophosphorus pesticides/
IPCS; Poisons Information Monograph G001: Organophosphorus pesticides. (Date of last update: March 1998). Available from: https://www.inchem.org/documents/pims/chemical/pimg001.htm as of July 23, 2003.

14 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Chemical Co-Occurrences in Literature

15.5 Chemical-Gene Co-Occurrences in Literature

15.6 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Chemical-Target Interactions

18 Biological Test Results

18.1 BioAssay Results

19 Classification

19.1 MeSH Tree

19.2 NCI Thesaurus Tree

19.3 ChEBI Ontology

19.4 KEGG: Pesticides

19.5 ChemIDplus

19.6 CAMEO Chemicals

19.7 UN GHS Classification

19.8 NORMAN Suspect List Exchange Classification

19.9 EPA DSSTox Classification

19.10 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Phosphoric acid, 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAMEO Chemicals
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    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA Acute Exposure Guideline Levels (AEGLs)
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
  8. FDA Global Substance Registration System (GSRS)
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    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
  9. Hazardous Substances Data Bank (HSDB)
  10. ILO-WHO International Chemical Safety Cards (ICSCs)
  11. NJDOH RTK Hazardous Substance List
  12. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  13. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
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    https://haz-map.com/About
  14. ChEBI
  15. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  16. ChEMBL
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    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  17. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  18. EPA Pesticide Ecotoxicity Database
  19. EU Pesticides Database
  20. USDA Pesticide Data Program
  21. Hazardous Chemical Information System (HCIS), Safe Work Australia
  22. NITE-CMC
    phosphamidon - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-1009e.html
  23. 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
    phosphamidon (ISO); 2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  24. Japan Chemical Substance Dictionary (Nikkaji)
  25. 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
  26. Metabolomics Workbench
  27. 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
  28. SpectraBase
  29. USGS Columbia Environmental Research Center
  30. 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/
    Phosphamidon
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  31. NTP Technical Reports
  32. Springer Nature
  33. SpringerMaterials
    dimethyl[2-chloro-1-m-2-(N,N-dimethylcarbamoyl)vinyl]phosphate
    https://materials.springer.com/substanceprofile/docs/smsid_xnpsbmtmflgtgsgj
  34. Wikidata
  35. Wikipedia
  36. 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
  37. PubChem
  38. GHS Classification (UNECE)
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
  41. NCBI
CONTENTS