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Demeton-S

HCID 24723
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Basic information

CAS
126-75-0
Standard SMILES
CCOP(=O)(OCC)SCCSCC
InChIKey
GRPRVIYRYGLIJU-UHFFFAOYSA-N
Molecular formula
C8H19O3PS2
Average molar mass
258.3 g/mol
Monoisotopic mass
258.05132381

Overview

Demeton-S is an organothiophosphorus compound.

Names & identifiers

Preferred name
Demeton-S
IUPAC
1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane
English name
DEMETON S
Molecular formula
C8H19O3PS2
Molecular weight
258.34

Names & synonyms

Demeton-S126-75-0ThioldemetonDemetonthiolISOSYSTOXIsodemetonIzosystoxThiol systoxPO-SystoxDemeton-S [ISO]Izosystox [Czech]Mercaptofos teolovy
Show more names
isSDeMetoDEMETON SDemeton-S 0thiolsystoxSystox-thiol
IS [Pesticide]Mercaptofos teolovy [Russian]Diethyl S-(2-ethioethyl)thiophosphateDTXSID9037535HSDB 6201IS (pesticide)EINECS 204-801-8O,O-Diethyl S-(2-eththioethyl)phosphorothioate

Database identifiers

CAS
126-75-0
PubChem CID
24723
DTXSID
DTXSID9037535
ChEMBL
CHEMBL1900921
ChEBI
CHEBI:82117
UNII
3UQ7N6O63K
EC Number
204-801-8
Nikkaji
J5.387B

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
86.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
9
Heavy atoms
14
Formal charge
0
Complexity
168

Experimental & physicochemical properties

SpringerMaterials PropertiesBoiling point
Pesticides · 3 items

Pesticides -> Organophosphate Insecticides

Pesticide (Demeton-S) -> USDA PDB

Pesticide degradation product

OdorTechnical grade demeton has a pronounced mercaptan-like odor.
Density · 2 items

Specific gravity: 1.132 at 21 °C

Relative density (water = 1): 1.13

Color/FormColorless oil
Solubility · 3 items

Soluble in most organic solvents.

In water, 2,000 mg/L at 20 °C

Solubility in water, g/100ml at 20 °C: 0.2

Boiling Point · 2 items

128 °C at 1 mm Hg

at 0.1kPa: 128 °C

DecompositionWhen heated to decomposition it emits toxic fumes of /phosphorous and sulfur oxides/.
Vapor Density

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

Fire HazardsCombustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary · 1 item

A cholinesterase inhibitor that may cause CNS effects resulting in convulsions and respiratory depression; Can be absorbed through skin; [ICSC] Effects in high-dose animal studies include inhibition of cholinesterase activity and decreased growth rate, but no histological changes; [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]

EC ClassificationSymbol: T+; R: 27/28; S: (1/2)-28-36/37-45
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: I
Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes including phosphorus oxides and sulfur oxides.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

THE THIOETHER SULFUR OF BOTH.../DEMETON-O AND DEMETON-S/ IS OXIDIZED, METABOLICALLY, TO THE SULFOXIDE AND SULFONE.

FOLLOWING APPLICATION TO PLANTS, DEMETON-S RAPIDLY GAVE RISE TO THREE METABOLITES, TWO OF WHICH PERSISTED FOR AS LONG AS 15 WK.

Absorption, Distribution and Excretion · 3 items

DEMETON-S RAPIDLY PENETRATES INTO PLANTS.

UP TO 14 DAYS AFTER THE TOPICAL APPLICATION OF DEMETON S TO COTTON, THIS ISOMER ACCUMULATED RAPIDLY IN THE LEAVES.

THE PRINCIPAL ROUTE OF ELIMINATION IN THE MOUSE WAS THROUGH THE URINE, 50 TO 70% OF AN ORALLY ADMIN DOSE BEING ELIMINATED IN 24 HR, 90% OF WHICH WAS IN THE FORM OF HYDROLYZED NONTOXIC PRODUCTS.

Uses & manufacturing

Uses · 4 items

Formerly used as an insecticide; [HSDB]

Farming (Pesticides) [Category: Industry]

Insecticide /Former/

Isosystox is an ingedient in the insecticide demeton which is composed of demeton-S (isosystox) and demeton-O in an isomeric ratio of 35:65. /Former/

Methods of Manufacturing · 1 item

PREPN /OF DEMETON/ BY THE REACTION OF 2-HYDROXYETHYL ETHYL SULFIDE ON DIETHYL PHOSPHOROCHLORIDOTHIOATE IN TOLUENE IN THE PRESENCE OF ANHYDROUS SODIUM CARBONATE AND METALLIC COPPER. ISOMERIZATION OCCURS AND THE RESULTANT PRODUCED IS AN APPROXIMATELY 65-35 MIXT OF COMPOUNDS DEMETON AND DEMETON-S.

General Manufacturing Information/DEMETON IS/ ISOMERIC MIXTURE CONSISTING OF DEMETON-O & DEMETON-S (O,O-DIETHYL O(AND S)-ETHYLMERCAPTOETHYL THIOPHOSPHATES). ANOTHER NAME FOR DEMETON-S IS ISOSYSTOX.

Applications

UsesColinesterase inhibitor. Insecticide

Upstream & downstream products

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Relative vapor density (air = 1): 8.92
Vapor Pressure · 3 items

0.000262 [mmHg]

2.6X10-4 mm Hg at 20 °C

Vapor pressure, Pa at 20 °C: 0.035

Refractive IndexINDEX OF REFRACTION: 1.5 @ 18 °C/D
Physical Description · 2 items

Colorless liquid; [ICSC] Liquid with an unpleasant odor; May be decomposed by light and air; [MSDSonline]

COLOURLESS OILY LIQUID.

Physicochemical properties

Melting point
95 · 95-97℃
Boiling point
1340 C · 1340C
Density
1.228 g/cm3 · 1.228 g/cm3 (20 ºC)
refractive index
1.5207 · 1.5207 (589.3 nm 20℃)
Flash point
45 °C · 45 °C
storage temp.
0 · 0-6°C
solubility
Chloroform (Slightly), Methanol (Slightly), Hexane, Ethyl Acetate, Dichloromethane
form
Oil
color
Clear Colourless
Water Solubility
2 g/L · 2g/L(20 ºC)
Henry's Law Constant
2 · 2.0×102 mol/(m3Pa) at 25℃, HSDB (2015)
FDA UNII
3 UQ7N6O63K · 3UQ7N6O63K
EPA Substance Registry System
Demeton-S (126-75-0)
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
3018 · 3018
RTECS
3130000 · TF3130000
HazardClass
6.1 · 6.1(a)
PackingGroup
I
Hazardous Substances Data
126 · 126-75-0(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 1500ug/kg
Packaging and LabellingDo not transport with food and feedstuffs.
Hazard Classes and Categories · 3 items

Acute Tox. 1 (100%)

Acute toxicity (dermal) - category 1

Acute Tox. 1

Safety & protection

Fire FightingUse foam, powder, carbon dioxide.
First Aid Measures · 4 items

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

Remove contaminated clothes. Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

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

Give a slurry of activated charcoal in water to drink. Rest. Refer for medical attention .

Safe StorageSeparated from food and feedstuffs. Dry. Keep in a well-ventilated room. 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]

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.

Spillage Disposal · 1 item

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Eye PreventionWear face shield.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT GENERATION OF MISTS! AVOID ALL CONTACT! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN! IN ALL CASES CONSULT A DOCTOR!
Ingestion PreventionDo not eat, drink, or smoke during work. Wash hands before eating.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 70 measured in an unspecified soil(2), indicates that demeton-S is expected to have high mobility in soil(SRC). Volatilization of demeton-S from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-8 atm-cu m/mole (SRC) derived from its vapor pressure, 2.6X10-4 mm Hg(4), and water solubility, 2,000 mg/L(3). Volatilization from dry soil is not expected(SRC) based on the vapor pressure(3). Demeton-S was photolyzed 69, 74, and 24% when incorporated into 3 different soils and irradiated in natural sunlight for 8 days(4), suggesting direct or indirect photolysis may be an important fate process for this compound on soil surfaces(SRC). The half-life of demeton-S-methyl in soil was reported as 26 days(5), suggesting that demeton-S may be susceptible to biodegradation in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 70 measured in soil(2), indicates that demeton-S 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 4.9X10-8 atm-cu m/mole (SRC) derived from its vapor pressure, 2.6X10-4 mm Hg(4), and water solubility, 2,000 mg/L(4). According to a classification scheme(5), an estimated BCF of 11(SRC), from its water solubility(4) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The chemical hydrolysis half-life of demeton-S was reported as 53 days at pH 5.7 and 27 °C, with 1,2-bis(ethylthio)ethane identified as its major hydrolysis byproduct(6). Demeton-S was photodegraded when applied to soil surfaces and exposed to natural sunlight(7), suggesting that pholysis may be an important environmental fate process(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), demeton-S, which has a vapor pressure of 2.6X10-4 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phase. Vapor-phase demeton-S is degraded in the atmosphere by reaction with photochemically generated hydroxyl radicals. The half-life for this reaction in air is estimated as 5 hours from its rate constant of 8X10-11 cm/molec-sec(SRC), derived using a structure estimation method(3). Particulate-phase demeton-S may be removed from the air by wet or dry deposition(SRC). Demeton-S was photodegraded when applied to soil surfaces and exposed to natural sunlight(4), suggesting photolysis in the atmosphere is possible(SRC).

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

Dizziness. Nausea. Vomiting. Pupillary constriction, muscle cramp, excessive salivation. Laboured breathing. Convulsions. Unconsciousness.

MAY BE ABSORBED! Muscle twitching. Further see Inhalation.

Redness. Redness. Pain.

Abdominal cramps. Diarrhoea. Further see Inhalation.

ICSC Environmental Data · 1 item

This substance may be hazardous to the environment. Special attention should be given to fish and bees. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.

Soil Adsorption/MobilityThe Koc value for demeton-S was reported as 70 in an unspecified soil(1). According to a classification scheme(2), this Koc value suggests that demeton-S is expected to have high mobility in soil(SRC).
Artificial Pollution SourcesDemeton-S's former production and use as a component of the insecticide demeton(1) resulted in its direct release to the environment(SRC).
Environmental BiodegradationAEROBIC: The half-life of demeton-S-methyl in soil was reported as 26 days(1), suggesting that demeton-S may be susceptible to biodegradation in soil(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 8 was calculated in fish for demeton-S(SRC), using a water solubility of 2,000 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 isosystox is estimated as 4.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 2.6X10-4 mm Hg(1), and water solubility, 2,000 mg/L(1). This Henry's Law constant indicates that isosystox is expected to be essentially nonvolatile from moist soil and water surfaces(2). Isosystox is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Non-Human Toxicity Excerpts · 4 items

/LABORATORY ANIMALS: Acute Exposure/ The daily administration of 0.75 mg/kg of Demeton-S for 3 days caused a progressive decrease in the cholinesterase activity of the brain, serum and submaxillary glands

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of 12 to 18 female rats fed 50 ppm (48% Demeton-S) for 16 weeks showed signs of poisoning and the growth-rate was affected. No histological changes were observed. Groups receiving 10 and 20 ppm showed severe inhibition of the brain and blood cholinesterase activity, while 3 ppm still gave 30% inhibition of blood cholinesterase activity. One ppm did not cause significant inhibition.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ With daily doses of 2.5 mg of demeton (30% Demeton-S per kg body-weight) for 48 days, no toxic changes were observed (10 animals), but there was an inhibition of blood cholinesterase activity.

/OTHER TOXICITY INFORMATION/ The IC50s for inhibition of cortical AChE activity were: parathion, 390 uM; paraoxon, 0.005 uM; malathion, 210 uM; malaoxon, 0.036 uM; demeton-S, 2.9 uM; DFP, 0.52 uM; and echothiophate, 0.006 uM. The IC50s for inhibition of hippocampal AChE activity were: parathion, 180 uM; paraoxon, 0.003 uM; malathion, 160 uM; malaoxon, 0.035 uM; demeton-S, 1.9 uM; DFP, 0.55 uM; and echothiophate, 0.004 uM. Disulfoton did not inhibit AChE activity over the tested concentration range. Only echothiophate competed with QNB /(quinuclidinyl benzilate, a muscarinic antagonist)/ binding and only at concentrations >100 uM. All organophosphates competed with CD /(cis-methyldioxolane, an agonist that binds to a subtype of muscarinic receptors)/ binding. The inhibition constants (Kis) for inhibition of CD binding in rat cortical membranes ranged from 0.004 to 51 uM, echothiophate being the most potent and parathion the least potent. The Kis in the hippocampal membranes varied from 0.004 to 25 uM, echothiophate being the most potent inhibitor and parathion the least potent. The IC50s for inhibition of AChE activity and Kis for competing with CD binding were significantly correlated in both tissues.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of demeton-S with photochemically-produced hydroxyl radicals has been estimated as 8X10-11 cu cm/molec-sec(SRC), using a structure estimation method(1). This corresponds to an atmospheric half-life of 5 hours at a hydroxyl radical concentration of 5X10+5 hydroxyl radicals per cu cm(1). The chemical hydrolysis half-life of demeton-S was reported as 53 days at pH 5.7 and 27 °C, with 1,2-bis(ethylthio)ethane identified as its major hydrolysis byproduct(2). The half-life increased to 347 days at 15 °C(2). Demeton-S was photolyzed 69, 74, and 24% when incorporated into 3 different soils and irradiated in natural sunlight for 8 days(3), suggesting direct or indirect photolysis may be an important fate process for this compound(SRC).

Safety data

rtecs
TF3130000
ridadr
3018
Toxicity
LD50 oral in rat: 1500ug/kg
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
126-75-0(Hazardous Substances Data)

Upstream raw materials

Ethyl 2-hydroxyethyl sulfideThiophosphoryl chloride

Additional notes

DefinitionChEBI: Demeton-S is an organothiophosphorus compound.