Demeton-S
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Demeton-S
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CAS No:
126-75-0
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Formula:
C8H19O3PS2
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Chemical Name:
Demeton-S
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Synonyms:
Phosphorothioic acid,O,O-diethyl S-[2-(ethylthio)ethyl] ester;Demeton-S;Isosystox;Thioldemeton;O,O-Diethyl S-[2-(ethylthio)ethyl] phosphorothioate;Ethylthionodemeton;Systox-thiol;Demetonthiol;Demeton thiolo;O,O-Diethyl S-[2-(ethylthio)ethyl] thiophosphate;1-Diethoxyphosphorylsulfanyl-2-ethylsulfanylethane;Mercaptophos thiol
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CAS No:
Description
COLOURLESS OILY LIQUID.
COLOURLESS OILY LIQUID.
Demeton-S is an organothiophosphorus compound.
Characteristics
95.94000
2.38
COLOURLESS OILY LIQUID.
1.132 g/cm3 @ Temp: 21 °C
95-97 °C
128 °C @ Press: 1 Torr
45 °C
1.493
Solubility in water, g/100ml at 20°C: 0.2
0-6°C
2.6X10-4 mm Hg at 20 deg C
Relative vapour density (air = 1): 8.92
Technical grade demeton has a pronounced mercaptan-like odor.
Henry's Law constant = 4.9X10-8 atm-cu m/mol at 25 °C (est)
Hydroxyl radical reaction rate constant = 8.0X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
I
6.1(a)
3018
27/28
28-36/37-45
TF3130000
T+
Separated from food and feedstuffs. Dry. Keep in a well-ventilated room. Store in an area without drain or sewer access.
Thin films undergo conversion to more hydrophilic compounds when exposed to air and light.
P264-P280-P301 + P310-P302 + P350-P310
H300 + H310
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.
Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P262, P264, P270, P280, P301+P310, P302+P350, P310, P321, P322, P330, P361, P363, P405, and P501|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 41 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Use foam, powder, carbon dioxide.
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.
Separated from food and feedstuffs. Dry. Keep in a well-ventilated room. Store in an area without drain or sewer access.
No 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.
The substance may cause effects on the central nervous system. This may result in convulsions and respiratory depression. Cholinesterase inhibition. Exposure could cause death. The effects may be delayed. Medical observation is indicated.
NO open flames.
PREVENT GENERATION OF MISTS! AVOID ALL CONTACT! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN! IN ALL CASES CONSULT A DOCTOR!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield.
Toxicity
LD50 Rat oral 1.5 mg/kg|LD50 Rat ip 1.5 mg/kg|LD50 Mouse ip 1.85 mg/kg|LD50 Mouse sc 6 mg/kg|LD50 Guinea pig ip 5.5 mg/kg
Demeton-S's former production and use as a component of the insecticide demeton(1) resulted in its direct release to the environment(SRC).
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).
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).
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).
70.79 L/kg|The 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).
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).
Since demeton is no longer registered for use in the United States, current occupational exposure and exposure to the general population is expected to be low or non existent. (SRC)
Drug Information
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.
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.
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.
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Organophosphates and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2 PAM). USE UNDER DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. In rare cases diazepam or lorazepam may be necessary ... . Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and related compounds/|Airway protection. Insure that a clear airway exists. Intubate the patients and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/|Atropine sulfate. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access if difficult to obtain. ... Atropine does not reactivate the cholinesterase enzyme or accelerate disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. ... The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for ISOSYSTOX (21 total), please visit the HSDB record page.
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Dizziness. Nausea. Vomiting. Pupillary constriction, muscle cramp, excessive salivation. Laboured breathing. Convulsions. Unconsciousness.
MAY BE ABSORBED! Muscle twitching. Further see Inhalation.
Redness. Redness. Pain.
Demeton-S Use and Manufacturing
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.
Colinesterase inhibitor. Insecticide
/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.
ANALYTE: DEMETON-O & DEMETON-S. MATRIX: AIR. PROCEDURE: COLLECTION ON MIXED CELLULOSE ESTER FILTER FOLLOWED BY XAD-2, DESORPTION WITH TOLUENE, GAS CHROMATOGRAPHY/FLAME PHOTOMETRIC DETECTION. RANGE: 0.06-0.33 MG/CU M.|Method: EPA-OSW 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: isosystox; Matrix: solid waste matrices, soils, air sampling media and water samples; Detection Limit: 10 ug/L.|Method: EPA-OSW 8141B; Procedure: gas chromatography with either a flame photometric detector (FPD) or a nitrogen-phosphorus detector (NPD); Analyte: isosystox; Matrix: water, soil, and waste samples; Detection Limit: not provided.|Method: NIOSH 5514, Issue 2; Procedure: gas chromatography, phosphorus flame photometric detector; Analyte: systox; Matrix: air; Detection Limit: 0.1 ug per sample. /Systox/|Product analysis by glc ... or by alkaline hydrolysis and titration of the excess of alkali ... or of the thiol with iodine. Residues determined by glc ... or by oxidation to phosphoric acid which is measured by standard colorimetric procedures.
Computed Properties
Molecular Weight:258.3
XLogP3:2.3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:9
Exact Mass:258.05132381
Monoisotopic Mass:258.05132381
Topological Polar Surface Area:86.1
Heavy Atom Count:14
Complexity:168
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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