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Mephosfolan

HCID 9568069
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Basic information

CAS
950-10-7
Standard SMILES
CCOP(=O)(/N=C1\SCC(C)S1)OCC
InChIKey
LTQSAUHRSCMPLD-CMDGGOBGSA-N
Molecular formula
C8H16NO3PS2
Average molar mass
269.3 g/mol
Monoisotopic mass
269.03092272

Overview

Mephosfolan is a yellow to amber liquid. Works as an insecticide and acaricide. Not registered as a pesticide in the U.S. (EPA, 1998)

Names & identifiers

Preferred name
Mephosfolan
IUPAC
(E)-N-diethoxyphosphoryl-4-methyl-1,3-dithiolan-2-imine

Names & synonyms

MephospholanENT-25,991AC 47470Cytrolane insecticideCL 47470Diethyl (4-methyl-1,3-dithiolan-2-ylidene)phosphoroamidateEI 47470cyclic propylene-P,P-diethyl phosphonodithioimidocarbonate2-(Diethoxyphosphinylimino)-4-methyl-1,3-dithiolaneCyclic propylene (diethoxyphosphinyl)dithioimidocarbonateEI-47470O,O-Diethyl(4-methyl-1,3-dithiolan-2-ylidene)phosphoramidate
Show more names
AI3-25991(Diethoxyphosphinyl)dithioimidocarbonic acid cyclic propylene esterPhosphonodithioimidocarbonic acid cyclic propylene P,P-diethyl esterImidocarbonic acid, phosphonodithio-, cyclic propylene P,P-diethyl esterP,P-Diethyl cyclic propylene ester of phosphonodithioimidocarbonic acidPhosphoramidic acid, (4-methyl-1,3-dithiolan-2-ylidene)-, diethyl ester1,2-Propanedithiol, cyclic ester with P,P-diethyl phosphonodithioimidocarbonateDTXSID0058221

Database identifiers

CAS
950-10-7
PubChem CID
9568069
ChEMBL
CHEMBL2272786
ChEBI
CHEBI:82141
EC Number
213-447-3

Properties

Computed structural properties

XLogP
1
Topological polar surface area
98.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
15
Formal charge
0
Complexity
275

Experimental & physicochemical properties

Pesticides · 4 items

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Mephosfolan) -> USDA PDB

Density · 2 items

1.539 @ 26 °C

1.539 @ 26°C

Color/Form · 2 items

Colorless liquid

Yellow to amber liquid.

Solubility · 2 items

Soluble in acetone, xylene, benzene, ethanol and toluene, moderately soluble in water.

Solubility in water at 25 °C: 57 g/kg.

Boiling Point · 3 items

248 °F at 0.001 mmHg (EPA, 1998)

120 °C at 1X10-3 mmHg

410 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits very toxic fumes of /nitrogen oxides, phosphorous oxides and sulfur oxides/.
Vapor Pressure · 2 items

0.0000318 [mmHg]

0.0000000001 [mm Hg] @25 °C

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 (100%): 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 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, this material emits very toxic fumes of nitrogen oxides, phosphorus oxides and sulfur oxides. Stable at neutral pH. Hydrolyzed by acid or alkali. (EPA, 1998)
Health HazardsThis material is highly toxic if swallowed or absorbed through the skin. (EPA, 1998)
Hazards Summary · 1 item

A highly toxic cholinesterase inhibitor; [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

Pharmacology

Metabolism/Metabolites · 4 items

Undergoes oxidation at the methyl group to form primary alcohol in addition to the formation of the thiocyanate ion in plants.

In the urine of rats dosed with cytrolane, TLC and MS indicated that the methyl moiety was attacked to produce carboxylic ions. Hydrolysis of the P-N bond was followed by ring opening and release of thiocyanate. The latter was the main tissue metabolite.

(14)C Cytrolane ..., labeled at the imino carbon, was applied to leaves of cotton plants. After 42 days, about 60% of the label was recovered as unchanged cytrolane. A minor metabolite ... and a major metabolite ... were isolated as glucosides. Identification of the aglycones was made after hydrolysis of the glucosidic moiety with beta-glucosidase. Another minor metabolite was identified as thiocyanate. Other observed metabolites were not identified. The hydroxymethyl and its glucoside were also observed in other studies with cotton.

When (14)C labeled cytrolane was applied to rice, about 91% of the residue was unchanged material. The remainder of the radioactivity was composed of about 17 metabolites. Unextractable radioactivity was believed to be in the form of (14)C-labeled cellulose, lignin and starch. Fish kept in the rice paddy metabolized cytrolane to thiocyanate and many other metabolites.

Absorption, Distribution and ExcretionAbsorbed by the roots and leaves.

Uses & manufacturing

Uses · 6 items

Used as contact and stomach insecticide and acaricide for cotton, fruits, vegetables, maize, and other crops; [HSDB]

Not registered in the US for use as pesticide; [CAMEO]

Farming (Pesticides) [Category: Industry]

Has shown significant activity against certain of the more important borer insects such as European corn borer, sugar cane borer and fall armyworm.

Insecticide, acaricide

It is a contact and stomach inseticide, and is used for the control of aphids, bollworms, mites, stem borers and whiteflies on such major crops as cotton, maize, field crops, fruit and vegetables.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Refractive Index
Index of refraction: 1.5354 at 26 °C/D
Physical Description · 2 items

Mephosfolan is a yellow to amber liquid. Works as an insecticide and acaricide. Not registered as a pesticide in the U.S. (EPA, 1998)

Colorless or yellow to amber liquid; [HSDB]

Stability/Shelf Life · 3 items

It is stable in water under neutral, slightly acid or basic conditions. Photodegradation in an aqueous environment.

Hydrolysed at pH < 2 and at pH > 9 /technical/

... Hydrolyzed by acid or alkali.

Reactive Group
Amines, Phosphines, and Pyridines
Reactivity Profile · 1 item

When heated to decomposition, MEPHOSFOLAN emits very toxic fumes of nitrogen oxides, phosphorus oxides and sulfur oxides. Stable at neutral pH. Hydrolyzed by acid or alkali. [EPA, 1998]. Organophosphates, such as MEPHOSFOLAN, 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.

DOT Hazard Classification · 2 items

Mephosfolan

Marine pollutant

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. Mephosfolan 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

Shipment Methods and Regulations · 3 items

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)./

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.

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.

Safety & protection

Fire Fighting(Non-Specific -- Organic Phosphate, Liquid) Use water spray to absorb vapors. Avoid breathing vapors. Keep upwind. Wear self-contained breathing apparatus. Avoid bodily contact with the material. Wear full 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

(Non-Specific -- Organic Phosphate, Liquid) Use water spray to knock down vapors. Build dikes to contain material as necessary. Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Downwind evacuation should be considered. (EPA, 1998)

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

0.82 [mg/m3]

9 [mg/m3]

54 [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 · 4 items

LC50 Salmo spp (Trout) 2.12 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Cyprinus carpio (Carp) 54.5 mg/l/96 hr /Conditions of bioassay not specified/

LD50 Coturnix coturnix japonica (Japanese quail) oral 12.8 mg/kg

TC50 Apis mellifera (Honeybee) topical application 0.0035 mg/bee

Environmental Fate · 1 item

The persistence of mephosfolan and phorate in soils treated previously with these insecticides and in previously untreated soils was studied in lab incubations. Accelerated loss of mephosfolan was induced by a single pretreatment. More than 95% of freshly applied mephosfolan degraded in previously treated hop yard soils after 8 wk at 15 °Compared with 23-35% in the corresponding previously untreated soils. In organic soils, total phorate residues declined more quickly in the previously treated soils than in similar untreated soils, largely because of more rapid degradation of phorate sulfoxide and, especially, of phorate sulfone. It is concluded that accelerated degradation of these insecticides probably limits their performance in some circumstances and that further studies are needed to determine the extent of the phenomenon.

Adverse EffectsOther Poison - Organophosphate
Non-Human Toxicity Excerpts · 3 items

In 90 day feeding trials with male albino rats receiving < or = 15 mg/kg diet, no significant effect was observed on wt gain but there was a reduction in erythrocyte and brain cholinesterase activity.

Cotton foliage may be injured in high-rainfall conditions.

A contact and stomach poison with systemic activity in plants through root and foliar absorption.

Antidote and Emergency Treatment · 5 items

1. INSURE THAT A CLEAR AIRWAY EXISTS BY ASPIRATION OF SECRETIONS IF NECESSARY. ADMIN OXYGEN BY MECHANICALLY ASSISTED PULMONARY VENTILATION IF RESPIRATION IS DEPRESSED. IMPROVE TISSUE OXYGENATION AS MUCH AS POSSIBLE BEFORE ADMIN ATROPINE TO MINIMIZE RISK OF VENTRICULAR FIBRILLATION. IN SEVERE POISONINGS, IT MAY BE NECESSARY TO SUPPORT PULMONARY VENTILATION MECHANICALLY FOR SEVERAL DAYS. 2. ADMIN ATROPINE SULFATE IV, OR IM IF IV INJECTION IS NOT POSSIBLE. ... IN MODERATELY SEVERE POISONING: ADULT DOSAGE AND CHILDREN OVER 12 YR: 0.4-2.0 MG REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED. MAINTAIN ATROPINIZATION WITH REPEATED DOSAGE OF 0.02-0.05 MG/KG BODY WEIGHT. /ORGANOPHOSPHATE PESTICIDES/

2. SEVERELY POISONED INDIVIDUALS MAY EXHIBIT REMARKABLE TOLERANCE TO ATROPINE; TWO OR MORE TIMES THE DOSAGES SUGGESTED ABOVE MAY BE NEEDED. THE DOSE OF ATROPINE MAY BE INCREASED AND THE DOSING INTERVAL DECREASED AS NEEDED TO CONTROL SYMPTOMS. CONTINUOUS INTRAVENOUS INFUSION OF ATROPINE MAY BE NECESSARY WHEN ATROPINE REQUIREMENTS ARE MASSIVE. REVERSAL OF MUSCARINIC SYMPTOMS AND SIGNS, NOT AN ARBITRARY DOSE LIMIT, IS THE DESIRED END-POINT. PRESERVATIVE-FREE ATROPINE PRODUCTS SHOULD BE USED WHENEVER POSSIBLE. NOTE: PERSONS NOT POISONED OR ONLY SLIGHTLY POISONED BY ORGANOPHOSPHATES MAY DEVELOP SIGNS OF ATROPINE TOXICITY FROM SUCH LARGE DOSES. FEVER, MUSCLE FIBRILLATIONS, AND DELIRIUM ARE THE MAIN SIGNS OF ATROPINE TOXICITY. IF THESE APPEAR WHILE THE PATIENT IS FULLY ATROPINIZED, ATROPINE ADMINISTRATION SHOULD BE DISCONTINUED, AT LEAST TEMPORARILY, WHILE THE SEVERITY OF POISONING IS REEVALUATED. /ORGANOPHOSPHATE PESTICIDES/

3. DRAW BLOOD SAMPLE (HEPARINIZED) FOR CHOLINESTERASE ANALYSIS BEFORE ADMINISTRATION OF PRALIDOXIME, WHICH TENDS TO REVERSE THE CHOLINESTERASE DEPRESSION. 4. ADMIN PRALIDOXIME (PROTOPAM, 2-PAM) IN CASES OF SEVERE POISONING ... IN WHICH RESP DEPRESSION, MUSCLE WEAKNESS & TWITCHINGS ARE SEVERE. ... ADULT DOSAGE AND CHILDREN OVER 12): GIVE 1.0-2.0 G IV @ NO MORE THAN 0.2 G/MIN. CHILD'S DOSE (UNDER 12 YR): GIVE 20-50 MG/KG (DEPENDING ON SEVERITY) IV, INJECTING NO MORE THAN HALF TOTAL DOSE/MIN. DOSAGE ... MAY BE REPEATED IN 1-2 HR THEN @ 10-12 HR INTERVAL IF NEEDED. IN VERY SEVERE POISONINGS, DOSAGE ... MAY BE DOUBLED. /ORGANOPHOSPHATE PESTICIDES/

4. BE PREPD TO ASSIST PULMONARY VENTILATION MECHANICALLY IF RESP ... DEPRESSED ... . 5. IN PATIENTS WHO HAVE BEEN POISONED BY ORGANOPHOSPHATE CONTAMINATION OF SKIN, CLOTHING, HAIR, AND/OR EYES, DECONTAMINATION MUST PROCEED CONCURRENTLY WITH WHATEVER RESUSCITATIVE AND ANTIDOTAL MEASURES ARE NECESSARY TO PRESERVE LIFE. ... 6. IF ... INGESTED IN QUANTITY PROBABLY SUFFICIENT TO CAUSE POISONING, THE STOMACH AND INTESTINE MUST BE EMPTIED. A. EMPTY THE STOMACH BY INTUBATION, ASPIRATION, AND LAVAGE, USING SLURRY OF ACTIVATED CHARCOAL IN ISOTONIC SALINE. RIGOROUS PRECAUTIONS MUST BE TAKEN TO PROTECT THE AIRWAY FROM ASPIRATION OF REGURGITATED. IF VICTIM IS UNCONSCIOUS OR OBTUNDED, INSERT A CUFFED ENDOTRACHEAL TUBE PRIOR TO GASTRIC INTUBATION. KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING GASTRIC INTUBATION AND LAVAGE ... . KEEP VICTIM'S HEAD TURNED TO THE LEFT. /ORGANOPHOSPHATE PESTICIDES/

For more Antidote and Emergency Treatment (Complete) data for MEPHOSFOLAN (8 total), please visit the HSDB record page.

RAIS Toxicity Values · 4 items

9e-05

HEAST Current

0.0009

HEAST Current

Non-Human Toxicity Values · 4 items

LD50 Rat oral 8.9 mg/kg

LD50 Rabbit albino dermal 9.7 mg/kg

LD50 Mouse albino oral 11.3 mg/kg

LD50 (24 hr) Albino rabbit male percutaneous 28.7 mg technical/kg

Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 · 6 items

5.70e+00

7.40e+01

1.80e+00

1.00e+01

2.60e-03

9e-05

Hazard Quotient Level 3 or Cancer Risk Level 1E-04 · 6 items

1.70e+01

2.20e+02

5.40e+00

1.00e+01

9e-05

Volatile

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. Mephosfolan 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.

Methods of Manufacturing
Condensation of diethyl phosphoryl chloride and 2-imino-4-methyl dithiolane.
Formulations/Preparations · 3 items

25% W/V EC

2% granules

EC (250 or 750 g ai/l); GR (20-100 g/kg).

General Manufacturing Information · 3 items

Phosphoramidic acid, N-(4-methyl-1,3-dithiolan-2-ylidene)-, diethyl ester: ACTIVE

Introduced in 1963 by Cyanamid International under the code number EI 47470, trademark cytrolane ... .

Insecticidal contact and stomach poison with systemic activity.