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Fosthietan

HCID 30684
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
21548-32-3
Standard SMILES
CCOP(=O)(N=C1SCS1)OCC
InChIKey
RHJOIOVESMTJEK-UHFFFAOYSA-N
Molecular formula
C6H12NO3PS2
Average molar mass
241.3 g/mol
Monoisotopic mass
240.99962259

Overview

Fosthietan is a pale yellow liquid with a mercaptan-like odor. Used as a nematocide and insecticide. Not registered as a pesticide in the U.S. (EPA, 1998)

Names & identifiers

Preferred name
Fosthietan
IUPAC
N-diethoxyphosphoryl-1,3-dithietan-2-imine
English name
FOSTHIETAN
Molecular formula
C6H12NO3PS2
Molecular weight
241.27

Names & synonyms

FOSTHIETAN21548-32-3Fosthietan [ANSI]NEMATAK4LD157TUHJHSDB 6449FOSTHIETAN [MI]FOSTHIETAN [ISO]Fosthietan [ANSI:ISO]EINECS 244-437-7FOSTHIETAN [HSDB]UNII-4LD157TUHJ
Show more names
geofoscl64475ac64475acconemnem-a-takent27,873geofos[qr]ac64475[qr]cl64475[qr]
EPA Pesticide Chemical Code 113301AC-64475CL-64475AI3-27873DTXSID4041993Fosthietan (ANSI)Phosphoramidic acid, N-1,3-dithietan-2-ylidene-, diethyl esterFosthietan (ANSI:ISO)

Database identifiers

CAS
21548-32-3
PubChem CID
30684
DTXSID
DTXSID4041993
ChEBI
CHEBI:82133
UNII
4LD157TUHJ
EC Number
244-437-7
Nikkaji
J10.915K

Properties

Computed structural properties

XLogP
0.7
Topological polar surface area
98.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
13
Formal charge
0
Complexity
230

Experimental & physicochemical properties

Pesticides · 3 items

Nematicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

LogPlog Kow = 0.68 /Estimated/
OdorMercaptan-like odor
Density · 3 items

1.3 at 77 °F (EPA, 1998) - Denser than water; will sink

1.3 g/cu cm at 25 °C

1.3 @25 °C

Color/FormPale yellow oil
Solubility · 2 items

In water, 5.00X10+4 mg/L at 25 °C

Sol in acetone, chloroform, methanol, toluene

Boiling Point250 °C @760 [mm Hg]
DecompositionWhen heated to decomp it emits very toxic fumes of /nitrogen, phosphorus, and sulfur oxides/.
Vapor Pressure · 4 items

6.5e-06 mmHg at 77 °F (EPA, 1998)

0.00000645 [mmHg]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

Danger

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

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 2 items

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits very toxic fumes of nitrogen oxides, phosphorus oxides and sulfur oxides. This compound is a liquid organophosphorus insecticide. Container may explode in heat of fire. (EPA, 1998)
Health HazardsThis compound is a liquid organophosphorus insecticide. Organic phosphorus insecticides are absorbed by the skin, as well as by the respiratory and gastrointestinal tracts. (EPA, 1998)
Hazards Summary · 1 item

A cholinesterase inhibitor; Can be absorbed through skin; [CAMEO] 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]

Chemistry & industry

Uses & manufacturing

Uses · 5 items

Used as soil insecticide and nematicide; [HSDB]

Not currently registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For fosthietan (USEPA/OPP Pesticide Code: 113301) 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./

Soil insecticide and nematicide /SRP 2005: Former use/

Methods of Manufacturing · 2 items

Reaction of diethyl phosphorochloridate with sodium thiocyanate, sodium hydrosulfide & dibromoethane.

Preparation: R.W. Addor, ZA 68 01064: idem, US 3470207 (1968, 1969 to American Cyanamid).

Formulations/PreparationsGranules (30 to 150 g ai/kg); water sol concentrate 250 g/l.
General Manufacturing Information · 4 items

Phosphoramidic acid, N-1,3-dithietan-2-ylidene-, diethyl ester: ACTIVE

Introduced by American Cyanamid in 1972 under code number AC 64475. US patent 3,476,837.

Nem-A-Tak discontinued by American Cyanamid Co.

...Effective in soil at 1 to 5 kg ai/ha. Care in application required to avoid phytotoxicity.

Applications · 3 items

DescriptionFosthietan is a pale yellow oil with a mercaptan-like odor. Molecular weight=241.28; Specific gravity(water=1)=1.3 g/cm3 at 25℃. Hazard Identification(based on NFPA-704 M Rating System): Health 3,Flammability 1, Reactivity 1. Moderately soluble in water.

UsesNematocide; insecticide.

General DescriptionPale yellow liquid with a mercaptan-like odor. Used as a nematocide and insecticide. Not registered as a pesticide in the U.S.

Upstream & downstream products

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

6.45X10-6 mm Hg at 25 °C

0.0000065 [mm Hg] @25 °C

Refractive IndexIndex of refraction: 1.5348 at 25 °C/D
Henry's Law ConstantHenry's Law constant = 4.11X10-11 atm-cu m/mol at 25 °C /Estimated/
Physical Description · 2 items

Fosthietan is a pale yellow liquid with a mercaptan-like odor. Used as a nematocide and insecticide. Not registered as a pesticide in the U.S. (EPA, 1998)

Pale yellow liquid; [HSDB]

Physicochemical properties

Boiling point
57.25 °C · 57.25°C
Density
25 · d25 1.3
refractive index
25 · nD25 1.5348
solubility
Chloroform (Slightly), Ethyl Acetate (Slightly)
form
Oil
pka
-4.95 · -4.95±0.20(Predicted)
color
Pale Yellow to Light Yellow
Water Solubility
50 g/L · 50g/L(25 ºC)
Henry's Law Constant
2.4 · 2.4×105 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Moisture Sensitive
FDA UNII
4 LD157TUHJ · 4LD157TUHJ
EPA Substance Registry System
Fosthietan (21548-32-3)
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
300 · H300-H310
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501
Hazard Codes
T+
Risk Statements
27 · 27/28
Safety Statements
36 · 36/37-45
RIDADR
3018 · 3018
TSCA
TSCA listed
HazardClass
6.1 · 6.1(a)
PackingGroup
I
Hazardous Substances Data
21548 · 21548-32-3(Hazardous Substances Data)
Toxicity
50 in · LD50 in rats, mice (mg/kg): 5, 18 orally (Whitney, Aston)
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity Profile · 1 item

Organophosphates, such as FOSTHIETAN, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
CERCLA Reportable Quantities · 1 item

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. Fosthietan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Hazard Classes and Categories · 3 items

Acute Tox. 2 (100%)

Acute toxicity (dermal) - category 1

Acute Tox. 1

Safety & protection

Fire Fighting · 1 item

This compound is a liquid organophosphorus insecticide. Stay upwind; keep out of low areas. Move containers from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. Wear positive pressure breathing apparatus and special protective clothing.

First AidWarning: Effects may be delayed up to 12 hours. Caution is advised.
Exposure Control and Personal Protection · 1 item

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]

Nonfire Spill Response · 1 item

This compound is a liquid organophosphorus insecticide. 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.

Disposal Methods · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Protective Action Criteria (PAC) · 3 items

0.43 [mg/m3]

4.7 [mg/m3]

28 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

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)

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a water solubility of 5.00X10+4 mg/L(2) and a regression-derived equation(3), indicates that fosthietan is expected to have very high mobility in soil(SRC). Volatilization of fosthietan from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.11X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 6.45X10-6 mm Hg(4), and water solubility(2). Fosthietan is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data for fosthietan were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a water solubility of 5.00X10+4 mg/L(2) and a regression-derived equation(3), indicates that fosthietan is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.11X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 6.45X10-6 mm Hg(4), and water solubility(2). According to a classification scheme(5), an estimated BCF of 1(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data for fosthietan were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fosthietan, which has a vapor pressure of 6.45X10-6 mm Hg at 25 deg(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fosthietan 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 40 minutes(SRC), calculated from its rate constant of 5.79X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase fosthietan may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsOther Poison - Organophosphate
Soil Adsorption/Mobility · 1 item

The Koc of fosthietan is estimated as 11(SRC), using a water solubility of 5.00X10+4 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that fosthietan is expected to have very high mobility in soil.

Artificial Pollution SourcesFosthietan's former production and use as an insecticide(1) may have resulted in its direct release to the environment(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 1 was calculated for fosthietan(SRC), using a water solubility of 5.00X10+4 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for fosthietan is estimated as 4.11X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 6.45X10-6 mm Hg(1), and water solubility, 5.00X10+4 mg/L(2). This Henry's Law constant indicates that fosthietan is not expected to volatilize from moist soil or water surfaces(3). Fosthietan is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of fosthietan with photochemically-produced hydroxyl radicals has been estimated as 5.79X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 40 minutes at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Measured hydrolysis data for this substance were not available. Phosphate esters such as phosthietan do hydrolyze. However, half-lives for compounds that contain this functional group are typically less than 10 years at pH 7(2).

Probable Routes of Human ExposureOccupational exposure and general population exposure should be low or non-existent since fosthietan is no longer produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 item

Fosthietan's former production and use as an insecticide may have resulted in its direct release to the environment. If released to air, a vapor pressure of 6.45X10-6 mm Hg at 25 °C indicates fosthietan will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fosthietan 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 40 minutes. Particulate-phase fosthietan will be removed from the atmosphere by wet and dry deposition. If released to soil, fosthietan is expected to have very high mobility based upon an estimated Koc of 11. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4.11X10-11 atm-cu m/mole. Fosthietan is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data for fostheitan were not available. If released into water, fosthietan is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 1 suggests the potential for bioconcentration in aquatic organisms is low. Measured hydrolysis data for this substance were not available. Phosphate esters such as fosthietan do hydrolyze .However, half-lives for compounds that contain this functional group are typically less than 10 years at pH 7. Occupational exposure and general population exposure should be low or non-existent since fosthietan is no longer produced or used. (SRC)

Antidote and Emergency Treatment · 4 items

Emergency and supportive measures. Caution: rescuers and health care providers must take measures to prevent direct contact with the skin or clothing of contaminated victims, because secondary contamination and serious illness may result, especially with potent pesticides and nerve agents. Maintain an open airway and assist ventilation if necessary. Pay careful attention to respiratory muscle weakness; sudden respiratory arrest may occur. If intubation is required, note potential interactions between neuromuscular blockers and cholinesterase inhibitors. Administer supplemental oxygen. Treat hydrocarbon pneumonitis, seizures, and coma if they occur. Observe asymptomatic patients for at least 8-12 hours to rule out delayed-onset symptoms, especially after extensive skin exposureor ingestion of a highly fat-soluble agent. /Organophosphates and carbamates/

Specific drugs and antidotes. Specific treatment includes the antimuscarinic agent atropine and the enzyme reactivator pralidoxime. Give atropine ... repeated frequently as needed. Large cumulative doses of atropine ... may occasionally be required in severe cases. The most clinically important indication for continued atropine administration is persistent wheezing or bronchorrhea. Note: Atropine will reverse muscarinic but not nicotinic effects. Pralidoxime is a specific antidote for organophosphate toxicity, that acts to regenerate the enzyme activity at all affected sites (muscarinic, nicotinic, and probably CNS; however, it does not reactivate plasma cholinesterase). Pralidoxime should be given immediately to reverse muscular weakness and fasciculations... . It is most effective if started within the first 24 hours of the exposure before irreversible phosphorylation of the enzyme, but may still be effective if given late, particularly after exposure to highly lipid soluble compounds. Pralidoxime is not generally recommended for carbamate intoxication, because in such cases the cholinesterase inhibition is spontaneously reversible and short-lived. However, if the exact agent is not identified and the patient has significant toxicity, pralidoxime should be given empirically. /Organophosphates and carbamates/

Decontamination. Note: Rescuers must wear chemical-protective clothing and gloves when handling a grossly contaminated victim. If there is heavy liquid contamination with a solvent such as xylene or toluene, clothing removal and victim decontamination should be carried out outdoors or in a room with high-flow ventilation. 1. Skin. Remove all contaminated clothing and wash exposed areas with soap and water, including the hair and under the nails. Irrigate exposed eyes with copious tepid water or saline. 2. Ingestion. a. Prehospital. Administer activated charcoal, if available. Do not induce vomiting because of the risk of abrupt onset of toxicity. b.Hospital. Administer activated charcoal (cathartics are not necessary if the patient already has diarrhea). Perform gastric lavage for large recent ingestions. /Organophosphates and carbamates/

Non-Human Toxicity Values · 5 items

LD50 Rat oral 5 mg/kg

LD50 Mouse oral 18 mg/kg

LD50 Rat male oral 4.7 to 7.7 mg/kg /Technical Nem-A-Tak/

LD50 Rat female oral 6.9 mg/kg /Technical Nem-A-Tak/

For more Non-Human Toxicity Values (Complete) data for FOSTHIETAN (11 total), please visit the HSDB record page.

Regulatory information

CERCLA Reportable Quantities · 1 item

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. Fosthietan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Safety data

tsca
TSCA listed
ridadr
3018
Toxicity
LD50 in rats, mice (mg/kg): 5, 18 orally (Whitney, Aston)
risk_code
27/28
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T+
safety_code
36/37-45
hazard_class
6.1(a)
packing_group
I
Hazard statements
H300-H310
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501
Hazardous Substances Data
21548-32-3(Hazardous Substances Data)

Upstream raw materials

Petroleum crude oilIsothiocyanate, polymer-bound, 200-400Diethyl chlorophosphatePhosphorus oxitrichlorideAmmonium thiocyanateDibromomethane

Additional notes

DefinitionChEBI: Fosthietan is a phosphoric ester.

Enhanced elimination. Dialysis and hemoperfusion are not generally indicated because of the large volume of distribution... /Organophosphates and carbamates/