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Thiometon

HCID 12541
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Basic information

CAS
640-15-3
Standard SMILES
CCSCCSP(=S)(OC)OC
InChIKey
OPASCBHCTNRLRM-UHFFFAOYSA-N
Molecular formula
C6H15O2PS3
Average molar mass
246.4 g/mol
Monoisotopic mass
245.99718024

Overview

Thiometon is an organothiophosphate insecticide, an organosulfur compound and an organic thiophosphate. It has a role as an acaricide, an agrochemical and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is functionally related to a 2-(ethylsulfanyl)ethanethiol.

Names & identifiers

Preferred name
Thiometon
IUPAC
2-ethylsulfanylethylsulfanyl-dimethoxy-sulfanylidene-λ5-phosphane
English name
Thiometon
Molecular formula
C6H15O2PS3
Molecular weight
246.35

Names & synonyms

THIOMETONEkatin640-15-3IntrathionIntrationEkatin aerosolDithiomethonDithiometonLuxistelmDithiometasystoxEkatin ULVEbicid
Show more names
m81M 81Medrinsan230VeltinNimeton
EkatimEkatin WFEkatin WF ULVBayer 23129SAN 230BAY 23129O,O-Dimethyl-S-(2-ethylmercaptoethyl) dithiophosphateYDI0MXQ7IR

Database identifiers

CAS
640-15-3
PubChem CID
12541
DTXSID
DTXSID9042469
ChEBI
CHEBI:38962
UNII
YDI0MXQ7IR
EC Number
211-362-6
Nikkaji
J4.414H

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
101 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
7
Heavy atoms
12
Formal charge
0
Complexity
146

Experimental & physicochemical properties

SpringerMaterials PropertiesBoiling point
Pesticides · 3 items

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

LogP · 2 items

0.51

3.46

OdorCharacteristic odor
Density · 2 items

1.209 @ 20 °C

Relative density (water = 1): 1.2

Color/FormColorless oil
Solubility · 4 items

It is slightly soluble in light petroleum; soluble in most organic solvents.

200 mg/l in water @ 25 °C

Readily soluble in common organic solvents. Slightly soluble in petroleum ether and mineral oils.

Solubility in water, g/100ml at 25 °C: 0.02

CorrosivityNon-corrosive
Boiling Point · 2 items

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

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P280, P301+P316, P302+P352, P317, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Danger

H301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P280, P301+P316, P302+P352, P317, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information2002/2076
Other Safety InformationIMAP assessments - Phosphorodithioic acid, S-[2-(ethylthio)ethyl] O,O-dimethylester: Human health tier I assessment
Fire HazardsCombustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.
Hazards Summary · 1 item

A cholinesterase inhibitor that may cause nervous system effects; Can be absorbed through skin; [ICSC] A weak mutagen; [HSDB] Cholinesterase inhibition observed in short term animal studies, but no adverse histopathological or other changes; No evidence of delayed neurotoxicity, significant reproductive toxicity, or teratogenicity in animal studies; [INCHEM PDS: Thiometon - 1988] 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

Mechanism of Action · 5 items

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/

The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/

... The serum cholinesterase activity of 14 men and 16 women at seven approximately equal intervals throughout one 24 hr day was measured. The lowest average value, ... was 92% of the mean of all values at other sampling times. The next lowest value was 98.7% of the same mean. /It was/ concluded that the small variation observed did not take the form of a regular curve but was entirely individual without correspondence to hour. /Organic phosphorus pesticides/

For more Mechanism of Action (Complete) data for THIOMETON (6 total), please visit the HSDB record page.

Metabolism/Metabolites · 3 items

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 paroxonase, and by the cytochrome p-450 systems. Considerable variability exists in the human population for organophosphate metabolism by these routes. The A-esterases are found in plasma and in the hepatic endoplasmic reticulum and can hydrolyze a large number of organophosphorus compounds ... by splitting the anhydride, P-F, P-CN, or ester bond. /Anticholinesterase agents/

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Compound notes

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110 °C at 0.1 mm Hg

at O.013kPa: 110 °C

Vapor DensityRelative vapor density (air = 1): 8.5
Vapor Pressure · 3 items

0.000017 [mmHg]

1.7X10-5 mm Hg at 20 °C

Vapor pressure, Pa at 20 °C: 0.02

Refractive IndexRefractive index: 1.5515

Physicochemical properties

Melting point
25 ℃ · <25℃
Boiling point
110 °C · 110°C
Density
1.209 g/cm3 · 1.209 g/cm3 (20℃)
vapor pressure
3.99 · 3.99×10-2 Pa (20 °C)
refractive index
1.568 · 1.568 (589.3 nm 20℃)
Flash point
70 °C · 70 °C
storage temp.
2 · 2-8°C
solubility
soluble in No data available
Water Solubility
200 mg · 200 mg l-1(25 °C)
form
liquid
color
Clear blue
Henry's Law Constant
3.5 · 3.5×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
CAS DataBase Reference
640 · 640-15-3
EWG's Food Scores
1 · 1
FDA UNII
0 MXQ7IR · YDI0MXQ7IR
EPA Substance Registry System
Thiometon (640-15-3)
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301-H312
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501-P280-P302+P352-P312-P322-P363-P501
Hazard Codes
T,N
Risk Statements
21 · 21-25-20/21-66-65-51/53-40
Safety Statements
36 · 36/37-45-62-61
RIDADR
3018 · 3018
HazardClass
6.1 · 6.1(a)
PackingGroup
II
Hazardous Substances Data
640 · 640-15-3(Hazardous Substances Data)
EC ClassificationSymbol: T; R: 21-25; S: (1/2)-36/37-45
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
Chemical DangersDecomposes on heating and on burning. This produces toxic fumes including phosphorus oxides and sulfur oxides.
Packaging and LabellingDo not transport with food and feedstuffs.
History and Incidents · 1 item

Major industrial accidents pose a serious threat to surrounding habitats. Each accident is unique in terms of pollutants released, pollutant concentrations and pollutant dispersal. The habitats receiving the pollutants are also unique. These factors mean that assessing the environmental and ecological impact of any given pollution event will be complex. Case histories of the biological impact of chemicals released from industrial accidents are reviewed to determine how to assess ecotoxicity of pollutants involved.

DOT Emergency Guidelines · 5 items

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/

For more DOT Emergency Guidelines (Complete) data for THIOMETON (16 total), please visit the HSDB record page.

Other Hazardous Reactions · 1 item

A portion of even the most flammable materials is likely to be lost by vaporization. ... The smoke from an open fire used to destroy pesticides will contain some of the poison. Burning should be attempted only in an isolated place. Inhalation of smoke must be avoided. /Pesticides/

Hazard Classes and Categories · 5 items

Acute Tox. 3 (97.6%)

Acute toxicity (ingestion) - category 3

Acute toxicity (Oral) - Category 2

Hazardous to the aquatic environment (Acute) - Category 2

Acute Tox. 3 *

Safety & protection

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

Fresh air, rest. Refer for medical attention.

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.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Rest. Refer for medical attention .

Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.
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

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. 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/

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/

Storage Conditions · 4 items

Formulations are said to be stable for at least 2 yr when stored below 40 °C.

Rooms used for storage only should be soundly constructed & fitted with secure locks. Floors should be kept clear & pesticides clearly identified. If repacking is carried out in storage rooms, adequate light should be available; floors should be impervious & sound ... . /Pesticides/

Pesticides containers must be provided with labels indicating the degree of toxicity of the product they contain. The labels must not only give a short description of how to use the prepn, but also state basic precautions to be taken when applying it. /Organophosphorus pesticides/

Pesticides of any degree of toxicity should be transported in containers which are clearly labelled, leak-proof, and not easily damaged. They should never be transported /or stored/ beside, or above any type of food, and all spillages should be immediately reported. /Pesticides/

Disposal Methods · 5 items

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

The pure thiometon is unstable. It is hydrolyzed in aqueous soln. Recommendable method: Incineration. Peer-review: Large amt should be incinerated in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

All organic pesticides, whether of botanical or synthetic origin, can be destroyed by incineration. /Organic pesticides/

Manufacturers or formulators of very large amounts of pesticides may find it advantageous to build incinerators adequate to destroy all organic pesticides and equipped with scrubbers to remove acid wastes. /Organic pesticides/

Spillage Disposal · 1 item

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT wash away into sewer. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 5 items

In some situations where personnel may become accidently contaminated ... it is necessary to provide shower bath in addition to the usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... /Pesticides/

Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/

Small packages of pesticides are preferable for individual application in order to limit the quantities to be weighed & metered. A special vessel with long stirring rod for dilution & suspension of the poison must be available in order to reduce manual handling to a minimum. The strict observance of hygiene rules--no smoking & no food intake during work. Thorough washing with soap after work, changing protective clothing before going home--is of utmost importance. /Organophosphorus pesticides/

Containers ... should be cleaned with a suspension of bleaching powder in water or with other alkaline soln after soaking for 24 hr and then be rinsed with hot water. /Organophosphorus pesticides/

For more Preventive Measures (Complete) data for THIOMETON (8 total), please visit the HSDB record page.

Eye PreventionWear safety spectacles or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.

Toxicology

Interactions · 5 items

Testosterone reduces the hemolytic action of Ekatin on the morphotic blood elements by accelerating maturation of erythroblastic cells. Testosterone, by accelerating the metabolism of the pesticide causes a defective defence process of the organism by decreasing the number of macrophages. Intoxication of androgenized /Coturnix coturnix (pharaoh quail)/ with Ekatin leads to a breakdown of the systemic adaptive mechanism by rapid and early switching on the adrenal cortex in response to stress caused by poisoning.

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 Carp 13.2 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Rasbora heteromorpha (harlequin fish) 4.7 mg/l/24 hr in a flow-through bioassay

LC50 Rasbora heteromorpha (harlequin fish) 3.7 mg/l/48 hr in a flow-through bioassay

LC50 Rasbora heteromorpha (harlequin fish) 3.2 mg/l/96 hr in a flow-through bioassay

LC50 Saccobranchus fossilis 11.0 mg/l/96 hr in a static bioassay

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 240(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(3), indicates that thiometon will have moderate mobility in soil(SRC). Based on limited data, this compound is expected to biodegrade in soil(SRC). Thiometon added to Rhine River water at 50 ug/l was nearly completely degraded within 40-50 days at 10 °C; sterile water samples did not degrade this compound(4). From soil studies, the biodegradation of thiometon will primarily result in the oxidation of the aliphatic dialkyl sulfur atom to sulfoxides and sulfones(5). Thiometon may also hydrolyze, particularly in alkaline soils, based on studies in water(4) giving rate constants for neutral and base-catalyzed hydrolysis of 1.1X10-7 /sec and 6.6X10-3 /sec, respectively(4) for this compound. Volatilization of thiometon is not expected to be significant from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.8X10-8 atm-cu m/mole(SRC), determined from experimental values for water solubility(2) and vapor pressure(6). Volatilization from dry soil surfaces is not expected(SRC) based on a measured vapor pressure of 1.7X10-5 mm Hg(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 240(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(1), indicates that thiometon is not expected to adsorb to suspended solids and sediment in water(SRC). Based on limited data, this compound is expected to biodegrade in water(SRC). Thiometon added to Rhine River water at 50 ug/l was nearly completely degraded within 40-50 days at 10 °C; sterile water samples did not degrade this compound(4). From soil studies, the biodegradation of thiometon will primarily result in the oxidation of the aliphatic dialkyl sulfur atom to sulfoxides and sulfones(5). Thiometon is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 2.8X10-8 atm-cu m/mole(SRC), from experimental values of water solubility(2) and vapor pressure(5). This compound is expected to hydrolyze; rate constants for the neutral hydrolysis and base-catalyzed hydrolysis of thiometon were 1.1X10-7 /sec and 6.6X10-3 /M-sec at 20 °C, respectively(3). Thiometon is not expected to directly photodegrade; however, it may react with singlet oxygen in water with an estimated half-life of 1000 days for a winter day and 100 days for a summer day(4). An estimated BCF value of 30(1,SRC), from a measured water solubility(2), suggests that thiometon will not bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiometon, which has a measured vapor pressure of 1.7X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thiometon 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 4 hours(3,SRC). Particulate-phase thiometon may be physically removed from the air by wet and dry deposition(SRC).

Food Survey ValuesThiometon was detected in fresh citrus fruits, pitted and seedy fruits, and vegetables from the Region of Murcia, Spain in 1989(1). The calculated daily ingestion of thiometon was 65.3, 11.1, and 0 ng/person, respectively(1).
Adverse EffectsOther Poison - Organophosphate
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Signs and Symptoms · 3 items

Dizziness. Sweating. Laboured breathing. Nausea. Pupillary constriction, muscle cramp, excessive salivation.

MAY BE ABSORBED! Further see Inhalation.

Abdominal cramps. Vomiting. Diarrhoea. Weakness. Muscle twitching. Convulsions. Unconsciousness. Further see Inhalation.

ICSC Environmental DataThe substance is toxic to aquatic organisms. This substance may be hazardous to the environment. Special attention should be given to bees. Avoid release to the environment in circumstances different to normal use.
Medical Surveillance · 3 items

Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications for work with /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/

A final diagnosis of mild to moderate acute organophosphate pesticide poisoning is rarely justified unless all of the following five conditions are present: 1. A definite history of exposure to an organophosphate pesticide. 2. A latent interval of not more than a few hours between that last exposure and the onset of illness. 3. A clinical picture in which most or all of the following signs or symptoms are present: headache, blurred vision, weakness, tightness in chest, and constricted pupils. 4. Reduction of plasma and RBC cholinesterase activity to a level substantially below 50% of baseline values. Because of the wide normal range of RBC cholinesterase in the population, symptoms may be present with reported "normal" levels. 5. An acute illness that is not substantially longer than 48 hours. The classic presentation for acute organophosphate toxicity includes history, evidence of exposure to organophosphate (garlic odor), signs/symptoms of cholinergic excess, improvement with atropine or pralidoxime, and inhibition of cholinesterase in blood. /Organophosphate pesticide poisoning/

... Surveillance of workers could be carried out through measurement of blood or urinary levels of the cmpd to which they are exposed, or through measurement of a metabolite. /Organic phosphorus pesticides/

Soil Adsorption/Mobility · 1 item

The Koc of thiometon is estimated as approximately 240(SRC), using a measured water solubility of 200 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that thiometon has moderate mobility in soil(SRC). Rf values for thiometon in a silt loam soil at pH 4, pH 7, and pH 10 were 0.89, 0.87, and 0.23, respectively; Rf values in a sandy loam soil under the same pH conditions were 0.92, 0.88, and 0.86, respectively(4). A silt loam soil with organic matter added and one without added organic matter had Rf values of 0.87 and 0.77, respectively; a sandy loam soil with organic matter added and one without had Rf values of 0.88 and 0.91, respectively(5).

Human Toxicity Excerpts · 5 items

Twelve female agricultural workers exposed to thiometon were followed for at least 6 months. Changes were reported in catalase, cytochrome oxidase and ceruloplasmin and the changes persisted in some of the workers for the entire period.

All the organophosphorus insecticides have a cumulative effect by progressive inhibition of cholinesterase ... /Organophosphorus insecticides/

The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, & loss of orientation. Psychic disorders, nystagmus, trembling of the hands & other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis & paralysis develop. /Organophosphorus pesticides/

Organophosphorus cmpd can produce dermal irritation but most are weak sensitizers. /Organophosphate cmpd/

For more Human Toxicity Excerpts (Complete) data for THIOMETON (16 total), please visit the HSDB record page.

Artificial Pollution SourcesThiometon is released directly to the environment during its use as a systemic insecticide for the control of aphids, woolly aphids, suckers, sawfly larvae, thrips, and mites(1).

Safety data

ridadr
3018
risk_code
21-25-20/21-66-65-51/53-40
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T,N
safety_code
36/37-45-62-61
hazard_class
6.1(a)
packing_group
II
Hazard statements
H301-H312
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501-P280-P302+P352-P312-P322-P363-P501
Hazardous Substances Data
640-15-3(Hazardous Substances Data)

These chemicals are detoxified by cytochrome p450-mediated monooxygenases in the liver, but some metabolites are more toxic than parent cmpd ... Metabolites usually are detected from 12 to 48 hr postexposure. /Organophosphate cmpd/

MeSH Pharmacological Classification · 2 items

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

A pesticide or chemical agent that kills mites and ticks. This is a large class that includes carbamates, formamides, organochlorines, organophosphates, etc, that act as antibiotics or growth regulators.

Absorption, Distribution and Excretion · 5 items

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/

Following their absorption, most organophosphorus cmpd are excreted almost entirely as hydrolysis products in the urine. /Anticholinesterase agents/

For more Absorption, Distribution and Excretion (Complete) data for THIOMETON (6 total), please visit the HSDB record page.

Uses & manufacturing

Uses · 4 items

Used as systemic insecticide to protect ornamentals, fruits, vegetables, and other crops; [HSDB]

Farming (Pesticides) [Category: Industry]

Systemic insecticide against aphids, phyllids, woolly aphids, sawflies, jassids, thrips and mites.

Control of sucking insects (aphids, woolly aphids, suckers, sawfly larvae, thrips, etc.), bryobia mites, tetranychid mites, and fruit-tree red spider mites (non-OP resistant) on a wide range of crops, including ornamentals, strawberries, citrus and other fruit, swedes, turnips, brassicas, other vegetables, olives, some ornamentals.

Methods of Manufacturing · 1 item

It can be prepared by the reaction of 2-ethylthioethyl chloride with sodium O,O-dimethyl phosphorodithioate or by the reaction of 2-ethylthioethanol with O,O,-dimethyl hydrogen phosphorodithioate and p-toluenesulfonyl chloride in the presence of an acid binding agent.

Formulations/Preparations · 5 items

Thiometon is available as 20 and 25% emulsifiable concentrates and 2% dust.

Ekatin (emulsifible concentrate 250 g/acre/kg)

Ekatin (ULV 150 g acre/kg)

Ultra-low volume liquid and emulsifiable concentrate

For more Formulations/Preparations (Complete) data for THIOMETON (6 total), please visit the HSDB record page.

General Manufacturing InformationPatents DE 917668 to Bayer; CH 319579 to Sandoz
Applications · 2 items

DescriptionThiometon is the thion (P=S) analog of demeton-Smethyl. It is a colorless oil, bp 104 C/0.3 mm Hg, vp 39.9 mPa (20 C). The water solubility is 200 mg/L (27 C). It is highly soluble inmost organic solvents except alkanes. Log Kow = 3.15. It is hydrolyzed in alkaline and acidic media; DT50 (25 C) values at pH 3, 6, and 9 are 25, 27, and 17 d, respectively.

UsesThiometon is used to control sucking insects and mites on a wide range of crops.

Upstream & downstream products

Downstream products

0,0-Dimethyl Thiophosphate
Additional notes · 1 item

DefinitionChEBI: Thiometon is an organic thiophosphate, an organothiophosphate insecticide and an organosulfur compound. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. It is functionally related to a 2-(ethylsulfanyl)ethanethiol.