Chlormephos

HCID 32739CAS 24934-91-6

Basic information

Standard SMILES
CCOP(=S)(OCC)SCCl
InChIKey
QGTYWWGEWOBMAK-UHFFFAOYSA-N
Molecular formula
C5H12ClO2PS2
Average molar mass
234.7 g/mol
Monoisotopic mass
233.9704867

Names & identifiers

Preferred name
Chlormephos
IUPAC
chloromethylsulfanyl-diethoxy-sulfanylidene-lambda5-phosphane
English name
CHLORMEPHOS
Molecular formula
C5H12ClO2PS2
Molecular weight
234.7

Names & synonyms

CHLORMEPHOSChlormefosChlormethylfos24934-91-6DotanCaswell No. 195BChlormephos [BSI:ISO]S-Chloromethyl O,O-diethyl phosphorodithioateChlormephos [ISO]Phosphorodithioic acid, S-(chloromethyl) O,O-diethyl esterCCRIS 1623DTXSID1037511
Show more names
MC2188P 2188ai3-25533caswellno195bchlormephos(bsi,iso)CHLORMEPHOS STANDARD
MC 2188HSDB 6456S-(chloromethyl) O,O-diethyl phosphorodithioateEINECS 246-538-1UNII-1N10F47JUSS-(Chloromethyl) O,O-diethylphosphorodithioateEPA Pesticide Chemical Code 295300BRN 1680996

Database identifiers

CAS
24934-91-6
PubChem CID
32739
DTXSID
DTXSID1037511
ChEMBL
CHEMBL1882960
ChEBI
CHEBI:38603
UNII
1N10F47JUS
EC Number
246-538-1
Nikkaji
J53.800K

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
75.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
6
Heavy atoms
11

Experimental & physicochemical properties

LogP3.0 (estimated)
Density · 4 items

1.26 (EPA, 1998) - Denser than water; will sink

1.260 at 20 °C

Relative density (water = 1): 1.26

1.26 @25 °C

Color/Form · 2 items

Colorless liquid

Pale-colored liquid.

Solubility · 3 items

60 mg/l water at 20 °C

Miscible with most organic solvents

Solubility in water, g/100ml at 20 °C: 0.006 (very poor)

CorrosivityCorrosive to some metals.
Flash Point>100 °C

Physicochemical properties

Melting point
25 °C · 25°C
Boiling point
1 mm · bp1mm 93-95°; bp0.1 Torr 81-85°
Density
20 · d20 1.260
vapor pressure
7.6 Pa · 7.6 Pa (30 °C)
refractive index
220 · nD220 1.5244
Flash point
100 °C · 100 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral];H310: Fatal in contact with skin [Danger Acute toxicity, dermal];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

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

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 Hazards · 2 items

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Container may explode in heat of fire. Fire and runoff from control water may produce irritating or poisonous gases. (EPA, 1998)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) This material is poisonous; it may be fatal if inhaled, swallowed, or absorbed through the skin. (EPA, 1998)
Hazards Summary · 1 item

A non-systemic cholinesterase inhibitor; [Merck Index] May be absorbed through skin; A cholinesterase inhibitor; [ICSC] 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]

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters;Halogenated Organic Compounds

Safety & protection

Fire Fighting · 2 items

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Stay upwind; keep out of low areas. Move container 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. Wear positive pressure breathing apparatus and special protective clothing.;(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)

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention. Wear protective gloves when administering first aid.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

First Aid · 1 item

Warning: Effects may be delayed up to 12 hours. Caution is advised.;Note: Chlormephos is a cholinesterase inhibitor.;Signs and Symptoms of Chlormephos Exposure: Acute exposure to chlormephos may produce the following signs and symptoms: sweating, pinpoint pupils, blurred vision, headache, dizziness, profound weakness, muscle spasms, seizures and coma. Mental confusion and psychosis may occur. Excessive salivation, nausea, vomiting, anorexia, diarrhea, and abdominal pain may also occur. The heart rate may decrease following oral exposure or increase following dermal exposure. Chest pain may be noted. Hypotension (low blood pressure) may be observed, although hypertension (high blood pressure) is not uncommon. Respiratory symptoms include dyspnea (shortness of breath), pulmonary edema, respiratory depression, and respiratory paralysis.;Emergency Life-Support Procedures: Acute exposure to chlormephos exposure 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 chlormephos.;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 100% humidified 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. Rush to a health care facility.;Dermal/Eye Exposure:;1. Remove victims from exposure. Emergency personnel should avoid self-exposure to chlormephos.;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 100% humidified 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. Rush 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.

Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
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]

Fire Fighting Procedures · 2 items

For small fires, use dry chemical, carbon dioxide, water spray, or foam. For large fires, use water spray, fog, or foam.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. 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, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/

Toxicology

Interactions · 4 items

Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/

In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/

BARBITURATES ARE POTENTIATED BY ANTICHOLINESTERASES. ALTHOUGH BARBITURATES MAY BE USED CAUTIOUSLY IN TREATING CONVULSIONS, EXTREME CARE IS ESSENTIAL IN HANDLING POISONINGS DUE TO ANTICHOLINESTERASES, PARTICULARLY ORGANOPHOSPHORUS PESTICIDES. ECHOTHIOPHATE, A CHOLINESTERASE INHIBITOR USED AS MIOTIC, POTENTIATES OTHER SUCH INHIBITORS ... USED FOR OTHER PURPOSES (ADDITIVE EFFECTS) OR POSSIBLY SYNERGISTIC. THOSE EXPOSED TO ORGANOPHOSPHATE INSECTICIDES MUST TAKE STRICT PRECAUTIONS. ... ORGANOPHOSPHORUS INSECTICIDES: ADDITIVE ANTICHOLINESTERASE EFFECTS. HAZARDOUS. PATIENTS ON ANTICHOLINESTERASES (EVEN TOPICAL, SUCH AS EYE DROPS) SHOULD AVOID AREAS WHERE ORGANOPHOSPHORUS INSECTICIDES ... RECENTLY ... USED. /ANTICHOLINESTERASE/

ANTICHOLINESTERASE (ORGANOPHOSPHORUS) INSECTICIDES ANTAGONIZE POLARIZING MUSCLE RELAXANTS. PHENOTHIAZINES /AND THIOXANTHENES/: ... MAY ENHANCE TOXIC EFFECTS OF ORGANOPHOSPHORUS INSECTICIDES. /INSECTICIDES, ORGANOPHOSPHORUS/

Ecotoxicity Values · 5 items

LC50 Harlequin fish (Rasbora heteromorpha) 4.8 mg/L/24 hr, Flow-through

LC50 Harlequin fish (Rasbora heteromorpha) 3.5 mg/L/48 hr, Flow-through

LC50 Harlequin fish (Rasbora heteromorpha) 2.5 mg/L/96 hr, Flow-through

LD50 Quail oral 260 mg/kg

LC50 harlequin fish = 1.5 mg/L /Conditions of bioassay not specified/

Environmental Fate · 4 items

In soil, chlormephos is converted to ethion.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1100(SRC), determined from an estimated log Kow of 3.0(2,SRC) and a recommended regression-derived equation(3), indicates that chlormephos is expected to have low mobility in soil(SRC). Volatilization of chlormephos from moist soil surfaces may be important(SRC) given an estimated Henry's Law constant of 2.9X10-4 atm-cu m/mole(SRC), from its experimental values for vapor pressure, 0.057 mm Hg(4), and water solubility, 60 mg/l(4). Volatilization may be inhibited by adsorption to soil(SRC). In soil, chlormephos is converted to ethion(4). The half-life of chlormephos in a sandy loam soil was 28 days(5).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1100(SRC), determined from an estimated log Kow of 3.0(2,SRC) and a recommended regression-derived equation(3), indicates that chlormephos is expected to adsorb to suspended solids and sediment in water(SRC). Chlormephos may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.9X10-4 atm-cu m/mole(SRC), from its experimental values for vapor pressure, 0.057 mm Hg(4), and water solubility, 60 mg/l(4). Estimated volatilization half-lives for a model river and model lake are 9.1 hours and 7.5 days, respectively(3,SRC). Volatilization may be inhibited by adsorption to sediment in the water column(SRC). According to a classification scheme(5), an estimated BCF of 120(3,SRC), from an estimated log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is high(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlormephos, which has a measured vapor pressure of 0.057 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chlormephos 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 about 3.9 hours(3,SRC).

Adverse EffectsOther Poison - Organophosphate
Exposure RoutesThe substance can be absorbed into the body in hazardous amounts by inhalation, through the skin and by ingestion.
Signs and Symptoms · 4 items

Dizziness. Nausea. Sweating. Muscle twitching. Pupillary constriction, muscle cramp, excessive salivation. Laboured breathing. Convulsions. Unconsciousness.

MAY BE ABSORBED! See Inhalation.

Blurred vision.

Abdominal cramps. Diarrhoea. Vomiting. Further see Inhalation.

Regulatory 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.)

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. Chlormephos 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

rtecs
TD5170000
ridadr
3018
Toxicity
LD50 in rats (mg/kg): 7 orally; 27 dermally; LC50 in fish: 1.5 mg/l (Lynch)
risk_code
27/28-50/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS09

Chemistry & industry

Pharmacology

Mechanism of Action · 5 items

The signs of poisoning due to organophosphorus cmpd are those due to accumulation of acetylcholine & hence overstimulation of parasympathetic nervous system. It is usual to divide them under 3 headings: muscarinic, nicotinic & central. Muscarinic signs ... consist of hypersalivation, lacrimation, sweating & nasal discharge. Miosis, dyspnea, vomiting, diarrhea & frequency of urination ... Nicotinic effects consist of fasciculation of muscles, weakness & paralysis. Central nervous system effects include nervousness, apprehension, ataxia, convulsions & coma. Death is due to resp failure, or sometimes cardiac arrest. There is little difference between signs produced by different organophosphorus compounds, but route of absorption may influence one system more than another. /Organophosphorus cmpd/

The characteristic pharmacological effects of the anti-ChE agents are due primarily to the prevention of hydrolysis of ACh by AChE at sites of cholinergic transmission. Transmitter thus accumulates, and the response to ACh that is liberated by cholinergic impulses or that is spontaneously released from the nerve ending is enhanced. With most of the organophosphorus agents ... virtually all the acute effects of moderate doses are attributable to this action. /Anticholinesterase agents/

The cardiovascular actions of anticholinesterase agents are complex, since they reflect both ganglionic and postganglionic effects of accumulated ACh on the heart and blood vessels. The predominant effect on the heart from the peripheral action of accumulated ACh is bradycardia, resulting in a fall in cardiac output. Higher doses usually cause a fall in blood pressure, often as a consequence of effects of anticholinesterase agents on the medullary vasomotor centers of the CNS. /Anticholinesterase agents/

Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase. ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/

For more Mechanism of Action (Complete) data for CHLORMEPHOS (7 total), please visit the HSDB record page.

Metabolism/Metabolites · 3 items

In rats, following oral admin, there is almost complete elimination within 24 hr in the urine as diethyl phosphate and diethyl phosphorothioate.

Plasma and tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric and phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/

The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paraoxonases. These enzymes are found in the plasma and liver and hydrolyze a large number of organophosphorus compounds ... by cleaving the phosphoester, anhydride, P-F, or P-CN bonds. /Anticholinesterase agents/

Absorption, Distribution and Excretion · 5 items

In rats, following oral admin, there is almost complete elimination within 24 hr in the urine as diethyl phosphate and diethyl phosphorothioate.

Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/

The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/

Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/

For more Absorption, Distribution and Excretion (Complete) data for CHLORMEPHOS (8 total), please visit the HSDB record page.

Uses & manufacturing

Uses · 5 items

Used as insecticide applied to soil; [Merck Index]

Not registered as a pesticide for use in the US; [CAMEO] Banned in the EU for use as a biocide and agricultural insecticide; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

Non-systemic insecticide with contact and some stomach action.

Soil insecticide

Impurities... major impurity ethion. /Technical material circa 85%/
Methods of ManufacturingProduced by reaction of an alkali salt of diethyl dithiophosphoric acid and bromochlormethane.
Formulations/Preparations · 3 items

The technical grade is 90-93% pure. /Technical grade/

GR

Granules containing 5 or 10% ai

General Manufacturing Information · 2 items

Dotan, a microgranular formulation containing 5-10% chlormephos.

Combination: Can be combined with various systemic organophosphorus insecticides.

Applications · 5 items

DescriptionChlormephos is an organophosphate, colorlessliquid. Molecular weight=234.70; Boiling point =81-85℃ at 0.1 mmHg. Hazard Identification (based onNFPA 704 M Rating System): Health 3, Flammability 2,Reactivity 0. Soluble in water; solubility=60 mg/L at20℃.

UsesInsecticide primarily for soil applications.

UsesChlormephos is used to control soil insects such as wireworms in a number of crops.

UsesChlormefos has agricultural applications. Useful for preparing compositions for controlling plant diseases.

General DescriptionColorless liquid. Used as a soil insecticide. Not registered as a pesticide in the U.S.

Additional notes

DefinitionChEBI: Chlormephos is an organic thiophosphate, an organothiophosphate insecticide and an organochlorine insecticide. It has a role as an agrochemical and an EC 3.1.1.7 (acetylcholinesterase) inhibitor.

Related reactions

1 records

Linked notes

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