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Phosfolan

HCID 13689
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Basic information

CAS
947-02-4
Standard SMILES
CCOP(=O)(N=C1SCCS1)OCC
InChIKey
ILBONRFSLATCRE-UHFFFAOYSA-N
Molecular formula
C7H14NO3PS2
Average molar mass
255.3 g/mol
Monoisotopic mass
255.01527265

Overview

Phosfolan is a colorless to yellow solid. Used as an insecticide. (EPA, 1998)

Names & identifiers

Preferred name
Phosfolan
IUPAC
N-diethoxyphosphoryl-1,3-dithiolan-2-imine
English name
PHOSFOLAN
Molecular formula
C7H14NO3PS2
Molecular weight
255.29

Names & synonyms

Phosfolan947-02-4PhospholanCYOLANECyolane insecticideAmerican cyanamid 47031American cyanamide 47031American cyanamid CL-47031American cyanamid AC 47,031OMS 646CyalaneCyolan
Show more names
oms646ac47031Cayolancl47031ei47031
ENT 25,830DTXSID1042285AC 47031CL 47031EI 470312-(Diethoxyphosphinylimino)-1,3-dithiolaneCHJ98J84AYDiethyl 1,3-dithiolan-2-ylidenephosphoramidate

Database identifiers

CAS
947-02-4
PubChem CID
13689
DTXSID
DTXSID1042285
ChEBI
CHEBI:82145
UNII
CHJ98J84AY
EC Number
213-423-2
Nikkaji
J9.472B

Properties

Computed structural properties

XLogP
0.6
Topological polar surface area
98.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
14
Formal charge
0
Complexity
241

Experimental & physicochemical properties

PesticidesPesticides -> Organophosphate Insecticides
Color/FormSOLID
Solubility · 3 items

SOL IN CYCLOHEXANONE

SOL IN WATER, ACETONE, BENZENE, ETHANOL, CYCLOHEXANE, TOLUENE; SLIGHTLY SOL IN ETHER; SPARINGLY SOL IN HEXANE

Water solubility 650,000 mg/L at 25 deg

Boiling Point · 2 items

239 to 244.4 °F at 0.001 mmHg (EPA, 1998)

410 °C @760 [mm Hg]

Melting Point · 3 items

98.6 to 113 °F (EPA, 1998)

36.5 °C

39.5 °C

Vapor Pressure · 2 items

0.000053 [mmHg]

0.0001 [mm Hg] @25 °C

Physical Description · 2 items

Phosfolan is a colorless to yellow solid. Used as an insecticide. (EPA, 1998)

Colorless to yellow solid; [CAMEO] Yellow crystalline solid; [MSDSonline]

Stability/Shelf LifeStable in aq soln under neutral or slightly acidic conditions but hydrolyzed at pH greater than 9 or less than 2.

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 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.)
DOT LabelPoison
Fire Hazards · 1 item

(Non-Specific -- Organophosphorus Pesticide, n.o.s.) This material may burn but does not ignite readily. Container may explode in heat of fire. When heated to decomposition, it emits very toxic fumes of oxides of phosphorus, sulfur, and nitrogen. Hydrolyzed by alkalies. (EPA, 1998)

Health HazardsSimilar to parathion. Death may result due to respiratory arrest as a result of paralysis of respiratory muscles and intense bronchoconstriction. Also considered a cholinesterase inhibitor. (EPA, 1998)
Hazards Summary · 1 item

Decreased erythrocyte cholinesterase activity in heavy occupational exposure by 31-43% by the end of the first hour; Nearly half of the cholinesterase activity had recovered by 48 hours, with full recovery taking 3-4 weeks; No adverse clinical observations in 90 day feeding with dogs at 1 mg/kg; Cholinesterase inhibition noted in animal studies, but no chronic neurotoxicity seen in chickens surviving high doses; [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]

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

... IN PLANTS & ANIMALS, /PHOSFOLAN/ IS METABOLIZED AT THE N-P BOND TO LESS TOXIC, WATER-SOLUBLE COMPOUNDS.

A SINGLE ORAL DOSE (2 MG/KG) TO RAT OF [(14)C-(C=N)]PHOSFOLAN WAS RAPIDLY METABOLIZED TO GIVE AS MAJOR METABOLITES THIOCYANATE AND CARBON DIOXIDE (20%). ... FOURTEEN MINOR URINARY METABOLITES WERE IDENTIFIED ... THE LIKELY INITIAL STEPS IN BIOTRANSFORMATION OF PHOSFOLAN ARE P-N CLEAVAGE &/OR S-OXIDATION.

Results are presented of studies on the metabolism of two (14)C-dithiolane insecticides (phosfolan and mephosfolan) labeled in the imido carbon position. Rats, cotton plants, and a simulated rice paddy environment were used in the studies. In rats, both insecticides showed their major degradation route to be hydrolysis to iminodithiolane, then to thiocyanate, then CO2. In cotton plants treated with mephosfolan, hydroxylation of the methyl moiety of the iminodithiolane ring and conjugation as glucoside was a significant pathway. When a rice paddy environment was treated with mephosfolan, mephosfolan was found in the rice plants, but did not accumulate in the rice grain. The rice plants assimilated mephosfolan rapidly, degraded it, and incorporated the (14)C-carbon into the natural plant products. Mephosfolan was readily metabolized by fish in the paddy environment into the thiocyanate and many polar metabolites.

Absorption, Distribution and Excretion · 2 items

A SINGLE ORAL DOSE (2 MG/KG) TO THE RAT OF (14)C-(C=N)PHOSFOLAN (CYOLANE) WAS RAPIDLY METABOLIZED ... THIOCYANATE WAS PRESENT IN LIVER, KIDNEY, & FAT, & WAS ALSO EXCRETED IN THE URINE (24%).

CYOLANE IS ... ACTIVE ... IN PLANTS THROUGH ROOT & FOLIAR ABSORPTION.

Uses & manufacturing

Uses · 3 items

Used as systemic insecticide; [HSDB]

Farming (Pesticides) [Category: Industry]

SYSTEMIC INSECTICIDE; LEAF-PENETRATING, FOR LEAF-FEEDING LARVAE AND OTHER COTTON INSECTS. /DISCONTINUED/

Methods of ManufacturingBY THE REACTION OF 2-IMINO-1,3-DITHIOLAN WITH DIETHYL PHOSPHOROCHLORIDATE.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Collision Cross Section165.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1042285]
Other Experimental PropertiesBP: 115-118 °C @ 1X10-3 MM HG; COLORLESS TO YELLOW SOLID; SOLUBILITY: 650 G/L WATER; SOL IN ACETONE, BENZENE, CYCLOHEXANE, ETHANOL, TOLUENE; SLIGHTLY SOL IN ETHER; SPARINGLY SOL IN HEXANE /TECHNICAL/

Physicochemical properties

Melting point
40.75 °C · 40.75°C
Boiling point
116.5 °C · 116.5°C
Density
1.42 · 1.42±0.1 g/cm3(Predicted)
refractive index
25 D · n25D 1.5463
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly)
pka
-4.95 · -4.95±0.20(Predicted)
form
solid
color
White to Off-White
Henry's Law Constant
5.1 · 5.1×104 mol/(m3Pa) at 25℃, Ebert et al. (2023)
EWG's Food Scores
1 · 1-2
FDA UNII
98 J84AY · CHJ98J84AY
EPA Substance Registry System
Phosfolan (947-02-4)
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
300 · H300+H310
Precautionary statements
264 · P264-P280-P301+P310-P302+P350-P310
Hazard Codes
T+
Risk Statements
27 · 27/28
Safety Statements
28 · 28-36/37-45
RIDADR
2783 · 2783
RTECS
6475000 · NJ6475000
TSCA
TSCA listed
HazardClass
6.1 · 6.1(a)
PackingGroup
I
Hazardous Substances Data
947 · 947-02-4(Hazardous Substances Data)
Reactive GroupAmines, Phosphines, and Pyridines
Special ReportsUSEPA; Chemical Profile: Phosfolan (1985). Chemical identity; exposure limits; physicochemical data; fire and explosion data; reactivity data; health hazrads; uses (insecticide); precautions for safe handling and use.
Reactivity Profile · 1 item

Organophosphates, such as PHOSFOLAN, 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 ReactionsHydrolyzed by alkalis. [EPA, 1998].
Hazard Classes and Categories · 4 items

Acute Tox. 2 (100%)

Acute toxicity (dermal) - category 1

Acute toxicity (Oral) - Category 2

Acute Tox. 1

Safety & protection

Fire Fighting(Non-Specific -- Organophosphorus Pesticide, n.o.s.) 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 AidNote: Phosfolan is a cholinesterase inhibitor.
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(Non-Specific -- Organophosphorus Pesticide, n.o.s.) Keep unnecessary people away. Do not touch spilled material. Use water spray to reduce vapors. Take up spills with noncombustible absorbent materials.
Isolation and EvacuationExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Protective Action Criteria (PAC) · 3 items

0.027 [mg/m3]

0.29 [mg/m3]

1.8 [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 · 5 items

LD50 HOUSE SPARROW PERCUTANEOUS 18 MG/KG

LD50 HOUSE SPARROW ORAL 2.4 MG/KG

LD50 QUELEA PERCUTANEOUS 10 MG/KG

LD50 QUELEA ORAL 1.8 MG/KG

LD50 Mallard 3 mo old males oral 3.18 mg/kg (95% confidence limit 2.52-4.00 mg/kg) /Technical, 89.5%/

Environmental Fate · 5 items

TERRESTRIAL FATE: IT IS NON-PERSISTENT IN SOIL ... .

TERRESTRIAL FATE: THE BIOLOGICAL HALF LIFE OF CYOLANE IN SANDY LOAM SOIL COLUMN WAS 3.5 DAYS. TOTAL CYOLANE IN DRAINAGE WATER AFTER 14 DAYS WAS 60.6% OF THE ORIGINAL AMT PLACED ON THE COLUMN. ONE HR AFTER CYOLANE WAS PLACED ON THE COLUMN, 20.62% WAS FOUND IN THE FIRST INCH, 10.08% IN THE SECOND INCH, 4.46% IN THE THIRD INCH, 4.61% IN THE FOURTH INCH, 9.50% IN THE FIFTH INCH, AND 19.46% IN THE SIXTH INCH.

TERRESTRIAL FATE: If released to soil, an estimated soil adsorption coefficient of 2.8(1-2,SRC) indicates that cyolane will display very high mobility in soil(3). Cyolane may undergo slow hydrolysis in basic soils with a pH >9(2,SRC).

AQUATIC FATE: If released to water, cyolane is expected to undergo rapid sensitized photolysis(1-2). The half-life for the sunlight photolysis of cyolane is expected to range from 14-18 days in the upper layer of clear water(1). Cyclic S,S-dipropylene dithiocarbonate, 2-imino-5-methyl-1,3-dithilane, diethyl phosphate, ethyl phosphate and phosphoric acid are produced in this reaction(1). Cyolane may undergo slow hydrolysis in basic waters with a pH >9(3,SRC). An estimated bioconcentration factor of 0.32(3-4,SRC) and an estimated soil adsorption coefficient of 2.8(3-4,SRC) indicate that cyolane will not bioconcentrate in fish and aquatic organisms nor will it adsorb to sediment and suspended organic matter(SRC).

ATMOSPHERIC FATE: If released to the atmosphere, cyolane may undergo a rapid gas-phase reaction with photochemically produced hydroxyl radicals. An estimated half-life for this process is 7 hours(2,SRC). It may undergo atmospheric removal by direct photolytic degradation(1,2,SRC). The water solubility of cyolane, 650,000 mg/L at 25 °C(4) indicates that it may also undergo atmospheric removal by wet deposition processes(SRC).

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

A soil adsorption coefficient of 2.8 can be calculated for cyolane using an appropriate regression equation(1,SRC) and its water solubility, 650,000 mg/L at 25 °C(2). This value indicates that cyolane will display very high mobility in soil(3).

Natural Pollution SourcesCyolane is an anthropogenic compound and it is not known to be produced by natural sources. (SRC)
Human Toxicity Excerpts · 2 items

WORKERS EXPOSED TO PHOSFOLAN SHOWED A HIGH REDUCTION IN CHOLINESTERASE ACTIVITY OF THE ERYTHROCYTES. THIS DECR IN THE ACTIVITY AT THE END OF THE FIRST HR RANGED 13.6-43.8% AND 31.1-43.8% IN THE LESS EXPOSED AND HIGHLY EXPOSED WORKERS, RESPECTIVELY. ABOUT HALF OF THE INHIBITED ENZYME ACTIVITY WAS RECOVERED AFTER 48 HR. THE RATE OF RECOVERY WAS SLOW AFTER THAT & IT TOOK APPROX 3-4 WK TO RETURN TO PREEXPOSURE LEVEL.

Symptomatology: 1. Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... 2. Headache, giddiness, vertigo & weakness. 3. Rhinorrhea & sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis ... Tearing, ciliary muscle spasm, loss of accommodation & ocular pain ... Mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction or all three. /Parathion/

Artificial Pollution SourcesCyolane is an experimental systemic insecticide use for the control of several cotton, cabbage and tobacco insects(1-2) and it was released to the environment where it was experimentally used(SRC).
Environmental Bioconcentration · 1 item

A bioconcentration factor of 0.32 can be calculated for cyolane using an appropriate regression equation(1,SRC) and its water solubility, 650,000 mg/L at 25 °C(2). This value indicates that cyolane will not bioconcentrate in fish and aquatic organisms(SRC).

Non-Human Toxicity Excerpts · 5 items

IN 90-DAY FEEDING TRIALS DOGS RECEIVING 1 MG/KG DAILY SHOWED NO CLINICAL SYMPTOMS.

CYOLANE-TREATED ALFALFA HAY WAS FED TO COW 1 YR AFTER TREATMENT OF ALFALFA. CHOLINESTERASE WAS DEPRESSED & DID NOT RETURN TO NORMAL LEVELS UNTIL 3 MO AFTER FEEDING OF CYOLANE-CONTAMINATED HAY HAD BEEN DISCONTINUED.

Signs of intoxication /in mallards/: Polydipsia, ataxia, wings spread, wing-drop, falling, prostration, using wings for pedestrian locomotion, immobility, wing tremors, bradypnea, dyspnea, spasms, tonic convulsions, terminal wing-beat convulsions and opisthotonos. Signs appeared as soon as 8 min and mortalities usually occurred about 30 min after treatment. Prolonged signs included asthenia and myasthenia. Remission took up to 1 wk. /Technical, 85.9%; oral admin/

MUSCARINIC SIGNS OF /ORGANOPHOSPHORUS CMPD/ ... CONSIST OF HYPERSALIVATION, LACRIMATION, SWEATING & NASAL DISCHARGE. MIOSIS, DYSPNEA, VOMITING, DIARRHEA & FREQUENCY OF URINATION ... NICOTINIC EFFECTS CONSIST OF FASCICULATION OF MUSCLES, WEAKNESS & PARALYSIS. THE CENTRAL EFFECTS INCL NERVOUSNESS, APPREHENSION, ATAXIA, CONVULSIONS & COMA. DEATH IS DUE TO RESP FAILURE, OR SOMETIMES CARDIAC ARREST. THERE IS LITTLE DIFFERENCE BETWEEN SYMPTOMS PRODUCED BY DIFFERENT ... CMPD, BUT ROUTE OF ABSORPTION MAY INFLUENCE ONE SYSTEM MORE THAN ANOTHER. /ORGANOPHOSPHORUS CMPD/

For more Non-Human Toxicity Excerpts (Complete) data for CYOLANE (7 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 item

The half-lives for the sunlight photolysis of cyolane in distilled water and rice patty water were 18 days and 14 days(1). The products of this photosensitized reaction were cyclic S,S-dipropylene dithiocarbonate, 2-imino-5-methyl-1,3-dithilane, diethyl phosphate, ethyl phosphate and phosphoric acid(1). Aqueous solutions of cyolane initially at a concn of approx 1500 mg/g decreased to approx 100 mg/g after 300 hours of irradiation by Egyptian sunlight(2). Photolysis on leaf surfaces was slower than that observed in water(2). Cyolane is stable to hydrolysis under neutral and acidic pHs (> pH 2) but slowly decomposes at pHs >9(3). An estimated rate constant for the gas-phase reaction of cyolane with photochemically produced hydroxyl radicals of 5.4X10-11 cu cm/molec-sec(4,SRC) translates to an atmospheric half-life of 7 hours(SRC) using an average atmospheric hydroxyl radical concn of 5X10-5 molec/cu m(4).

Environmental Fate/Exposure Summary · 1 item

Cyolane is an anthropogenic compound which was considered as a systemic a systemic insecticide. It could be released to the enivornment if it were produced, formulated or used as an insecticide. If released to soil, it is expected to display very high mobility. Cyolane may undergo slow hydrolysis in basic soils with a pH >9. If released to water, cyolane is expected to undergo rapid sensitized photolysis. The half-life for the sunlight photolysis of cyolane in the upper layer of clear water is expected to range from 14-18 days. Cyolane may undergo slow hydrolysis in basic waters with a pH >9. Cyolane is not expected to bioconcentrate in fish and aquatic organisms nor will it adsorb to sediment and suspended organic matter. If released to the atmosphere, cyolane may undergo a rapid gas-phase reaction with photochemically produced hydroxyl radicals at an estimated half-life of 7 hours. It may also undergo atmospheric removal by direct photolytic degradation and by wet deposition processes. Occupational exposure to cyolane may occur by dermal contact during its production, formulation or use. (SRC).

Non-Human Toxicity Values · 3 items

LD50 CHICKEN ORAL 5.2 MG/KG

LD50 Rat oral 8.9 mg/kg

LD50 Rabbit dermal 23 mg/kg

Safety data

tsca
TSCA listed
rtecs
NJ6475000
ridadr
2783
risk_code
27/28
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T+
safety_code
28-36/37-45
hazard_class
6.1(a)
packing_group
I
Hazard statements
H300+H310
Precautionary statements
P264-P280-P301+P310-P302+P350-P310
Hazardous Substances Data
947-02-4(Hazardous Substances Data)
Formulations/PreparationsEMULSIFIABLE CONCENTRATE (250 G AI/LITER) AND GRANULES (20-50 G AI/KG).
General Manufacturing Information · 3 items

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

... IT IS A SYSTEMIC INSECTICIDE FOR USE AGAINST SUCKING INSECTS, MITES & LEPIDOPTEROUS LARVAE. IT CONTROLS PRODENIA SPECIES & SPODOPTERA LITTORALIS ON COTTON @ 0.75-1.0 KG/HA; JASSIDS & WHITEFLIES @ 0.5 KG/HA; TRICHOPLUSIA NI AT 1 KG/HA; ALSO THRIPS TABACI AT 30 G/100 L.

CYOLANE IS A CONTACT & STOMACH POISON WITH SYSTEMIC ACTIVITY IN PLANTS THROUGH ROOT & FOLIAR ABSORPTION. IN FIELD TRIALS IT HAS GIVEN EXCELLENT CONTROL OF...LYGUS BUGS (LYGUS HESPERUS), ALFALFA WEEVIL (HYPERA POSTICA), MITES, THRIPS, ALABAMA ARGILLACE JASSID AND WHITEFLIES OF COTTON; CYRTOPELTIS OF TOBACCO.

Applications · 3 items

UsesInsecticide.

UsesPhosfolan was identified and determined to be a residual pesticide in okra samples.

General DescriptionColorless to yellow solid. Used as an insecticide.

Upstream & downstream products

Upstream raw materials

Sodium acetateDiphenyl etherDithiolan-2-imine

Downstream products

Phosphorous acid chloride and phosphorus dichloride

Additional notes

DefinitionChEBI: Phosfolan is a phosphoric ester.