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Phosacetim

HCID 20056
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
4104-14-7
Standard SMILES
CC(N)=NP(=S)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1
InChIKey
XIBXUAZIZXDFTG-UHFFFAOYSA-N
Molecular formula
C14H13Cl2N2O2PS
Average molar mass
375.2 g/mol
Monoisotopic mass
373.9812412

Overview

Phosacetim is a solid. (EPA, 1998)

Names & identifiers

Preferred name
Phosacetim
IUPAC
N'-bis(4-chlorophenoxy)phosphinothioylethanimidamide

Names & synonyms

4104-14-7PHOSACETIMPhosazetimDRC-714AI3-27854O,O-Bis(p-chlorophenyl) acetimidoylamidothiophosphatDTXSID5040330DRC 714O,O-Bis(4-chlorophenyl) N-acetimidoylphosphoramidothioateO,O-Di-(p-chlorophenyl) N-acetamidino phosphoramidothioateO,O-Bis(p-chlorophenyl)acetimidophosphoroamidothioateRefChem:173484
Show more names
DTXCID3020330223-874-77B08Z34L7OBAY 38819Bayer 38819GophacideO,O-Bis(4-chlorophenyl) (1-iminoethyl)phosphoramidothioateO,O-Bis(p-chlorophenyl) acetimidoylamidothiophosphate

Database identifiers

CAS
4104-14-7
PubChem CID
20056
EC Number
223-874-7

Properties

Computed structural properties

XLogP
5.5
Topological polar surface area
88.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
22
Formal charge
0
Complexity
409

Experimental & physicochemical properties

PesticidesPesticides -> Rodenticides
Color/FormWhite crystalline powder
SolubilitySol in chlorinated hydrocarbons (methylene chloride); slightly sol in alcohol, benzene, and ether
Boiling Point400 °C @760 [mm Hg]
DecompositionWhen heated to decomposition it emits very toxic fumes of /hydrogen chloride and nitrogen, phosphorus, and sulfur oxides/.
Melting Point104-106 °C
Vapor Pressure · 2 items

0.00000007 [mmHg]

0.0001 [mm Hg] @25 °C

Physical Description · 2 items

Phosacetim is a solid. (EPA, 1998)

White solid; [HSDB]

Stability/Shelf LifeBelieved to be stable under normal use conditions

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, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

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

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationThe 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.)
Fire HazardsWhen heated to decomposition, emits toxic fumes, primarily chlorides and oxides of nitrogen, sulfur and phosphorus. Avoid extreme heat. (EPA, 1998)
Health HazardsHighly toxic by mouth and skin exposure. (EPA, 1998)
Hazards SummaryInhibits cholinesterase; [HSDB] Extremely toxic cholinesterase inhibitor; [CAMEO] Highly toxic by ingestion and skin contact; [eChemPortal: ESIS]
Reactive GroupAmines, Phosphines, and Pyridines
FIFRA Requirements · 1 item

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Phosacetim is found on List B. Case No: 2520; Pesticide type: rodenticide; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): O,O-Bis(p-chlorophenyl) acetimidoylphosphoramidothioate; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled.".

Chemistry & industry

Pharmacology

Mechanism of ActionThe main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase ... /Organophosphorus pesticides/
Absorption, Distribution and ExcretionOrganophosphorus pesticides are rapidly absorbed into the body through the mucous membrane of the digestive tract, the respiratory system, & the skin, and are conveyed by the blood to various body tissues. /Organophosphorus pesticides/

Uses & manufacturing

Uses · 6 items

Used as rodenticide for gophers, rats, and mice (bait concentrate); [HSDB]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered products ... "cancelled.".

For phosacetim (USEPA/OPP Pesticide Code: 018501) 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./

Rodenticide

Formulations/PreparationsIt is marketed as a 2% bait concentrate ... /SRP 2005: Former use/
Use ClassificationRODENTICIDES
General Manufacturing InformationDiscontinued by Bayer AG.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Reactivity Profile · 1 item

Organothiophosphates, such as PHOSACETIM, 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. Phosacetim is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Hazard Classes and Categories · 2 items

Acute toxicity (dermal) - category 1

Acute Tox. 1

Safety & protection

First AidWarning: Extremely toxic by all routes of exposure. Effects may be delayed up to 12 hours. Caution is advised.
Nonfire Spill ResponseAvoid skin contact. (EPA, 1998)
Disposal Methods · 2 items

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.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Protective Action Criteria (PAC) · 3 items

0.34 [mg/m3]

3.7 [mg/m3]

9.5 [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

Ecotoxicity Values · 2 items

LD50 Gopher oral 1.0 mg/kg

LD50 Peromyscus maniculatus (Deer mouse) oral 18 mg/kg

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.6X10+4(SRC), determined from a structure estimation method(2), indicates that phosacetim is expected to be immobile in soil(SRC). Volatilization of phosacetim from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-9 atm-cu m/mole(3)(SRC), using a fragment constant estimation method(3). Phosacetim is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.4X10-8 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.6X10+4(SRC), determined from a structure estimation method(2), indicates that phosacetim is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.8X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 140(SRC), from an estimated log Kow of 3.69(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phosacetim, which has an estimated vapor pressure of 7.4X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase phosacetim may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsOther Poison - Organophosphate
Acute Toxicity LinkChemical: PHORAZETIM
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for phosacetim can be estimated to be 5.6X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that phosacetim is expected to be immobile in soil.

Human Toxicity Excerpts · 1 item

/SIGNS AND SYMPTOMS/ Exposure to the vapor or to particulate material may cause miosis, sometimes unequal, hyperanemia of the conjunctiva, dimness of vision, rhinorrhoea, frontal headache, bronchoconstriction, incr bronchial secretion, cough, nausea, vomiting, and fasciculation and sweating at the site of contact. Toxic effects may incl anorexia, abdominal cramps, nausea, vomiting, diarrhea, incontinence, eye changes, weakness, dyspnoea, bronchospasm, lachrymation, incr salivation and sweating, bradycardia, hypotension or hypertension due to asphyxia, cyanosis, and muscular twitching of the eyelids, tongue, face, and neck, possibly progressing to convulsions. CNS symptoms incl restlessness, anxiety, dizziness, drowsiness, tremor, ataxia, depression, confusion, and coma. Death may occur from depression of the resp or cardiovascular system. /Organophosphorus insecticides/

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

An estimated BCF of 140 was calculated for phosacetim(SRC), using an estimated log Kow of 3.69(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for phosacetim is estimated as 4.8X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phosacetim is expected to be essentially nonvolatile from water surfaces(2). Phosacetim is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.4X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of phosacetim with photochemically-produced hydroxyl radicals has been estimated as 2.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Phosacetim may undergo hydrolysis under basic conditions in the environment(2), however this is not expected to be an important fate process. Phosacetim is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

Probable Routes of Human Exposure · 1 item

Occupational exposure and general population exposure should be low or non-existent since phosacetim is no longer produced or used. In the past, phosacetim was released directly to the environment as a pesticide and exposure to this compound was primarily in the workplace where phosacetim was produced or used. (SRC)

Environmental Fate/Exposure Summary · 1 item

Phosacetim's former production and use as a rodenticide may have resulted in its direct release to the environment. If released to air, an estimated vapor pressure of 7.4X10-8 mm Hg at 25 °C indicates phosacetim will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase phosacetim will be removed from the atmosphere by wet and dry deposition. If released to soil, phosacetim is expected to have no mobility based upon an estimated Koc of 5.6X10+4. Biodegradation data were not available. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4.8X10-9 atm-cu m/mole. If released into water, phosacetim is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 140 suggests the potential for bioconcentration in aquatic organisms is high. Phosacetim may undergo hydrolysis under basic conditions in the environment, however this is not expected to be an important fate process. Occupational exposure and general population exposure should be low or non-existent since phosacetim is no longer produced or used. In the past, phosacetim was released directly to the environment as a pesticide and exposure to this compound was primarily in the workplace where phosacetim was produced or used. (SRC)

Regulatory information

FIFRA Requirements · 1 item

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Phosacetim is found on List B. Case No: 2520; Pesticide type: rodenticide; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): O,O-Bis(p-chlorophenyl) acetimidoylphosphoramidothioate; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled.".

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. Phosacetim is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .