Chlorthion

HCID 10372

Basic information

CAS
500-28-7
Standard SMILES
COP(=S)(OC)Oc1ccc([N+](=O)[O-])c(Cl)c1
InChIKey
NZNRRXXETLSZRO-UHFFFAOYSA-N
Molecular formula
C8H9ClNO5PS
Average molar mass
297.65 g/mol
Monoisotopic mass
296.9627583

Names & identifiers

Preferred name
Chlorthion
IUPAC
(3-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-lambda5-phosphane
English name
CHLORTHION
Molecular formula
C8H9ClNO5PS
Molecular weight
297.65

Names & synonyms

Chlorthion500-28-7Chlorthion methylChlortionCHLOROTHIONMethyl chlorothionChloorthionMethylchlorothionCompound 22/190Bayer 22/190BAY 22190OMS 217
Show more names
oms217B-22190bay22190ent18,861Chlothionoms217[qr]
p-Nitro-m-chlorophenyl dimethyl thionophosphateO-(3-Chloro-4-nitrophenyl) O,O-dimethyl phosphorothioateO,O-Dimethyl p-nitro-m-chlorophenyl thiophosphateENT 18,861O,O-Dimethyl O-(3-chloro-4-nitrophenyl) thiophosphateDimethyl 3-chloro-4-nitrophenyl thionophosphateO,O-Dimethyl O-(3-chloro-4-nitrophenyl) phosphorothioateNSC 8927

Database identifiers

CAS
500-28-7
PubChem CID
10372
DTXSID
DTXSID9041784
ChEMBL
CHEMBL160606
ChEBI
CHEBI:167184
UNII
3NTK55T19G
EC Number
207-902-5
Nikkaji
J152.065B

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
106 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
4
Heavy atoms
17

Experimental & physicochemical properties

LogPlog Kow= 3.45
Density1.437 @ 20 °C/4 °C
Color/FormPure compound is yellow crystals. ... Commercial product is a yellow oil.
Solubility · 5 items

Miscible in benzene, alcohol, ether

MISCIBLE IN AROMATIC SOLVENTS

SOL 1:25,000 IN WATER; READILY MISCIBLE IN TOLUENE & OIL

In water @ 20 °C, 40 mg/l; readily sol in common organic solvents with the exception of mineral oils

In water, 40 mg/l at 20 °C

CorrosivityNoncorrosive
Boiling Point · 3 items

136 °C @ 0.23 mm Hg

YELLOW OIL; BP: 125 °C @ 0.1 MM HG /COMMERCIAL PRODUCT/

BP: 136 °C @ 0.3 mbar; 112 °C @ 0.05 mbar

Physicochemical properties

Melting point
21 ° · 21°
Boiling point
0.1 · bp0.1 125°
Density
420 · d420 1.437
refractive index
20 · nD20 1.5661
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral];H312: Harmful in contact with skin [Warning Acute toxicity, dermal];H332: Harmful if inhaled [Warning Acute toxicity, inhalation];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]

P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

Hazard information

Fire PotentialNOT FLAMMABLE @ NORMAL TEMP; THERMAL DECOMPOSITION POINT ABOUT 150 °C
Hazards Summary · 1 item

A cholinesterase inhibitor; [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]

Special ReportsToxicology Review- Residue Reviews 63, 1, 1976
Hazard Classes and Categories · 3 items

Acute Tox. 4 (97.6%);Acute Tox. 4 (100%);Acute Tox. 4 (100%);Aquatic Acute 1 (100%);Aquatic Chronic 1 (100%)

Acute toxicity - category 4;Acute toxicity - category 4;Acute toxicity - category 4;Hazardous to the aquatic environment (acute) - category 1;Hazardous to the aquatic environment (chronic) - category 1

Acute Tox. 4 *;Acute Tox. 4 *;Acute Tox. 4 *;Aquatic Acute 1;Aquatic Chronic 1

Explosive Limits and PotentialCHLOROTHION (SELF-REACTIVE): WHEN SAMPLE WAS HEATED IN SMALL TEST TUBE IT DECOMPOSED & IN A FEW MIN RESIDUE EXPLODED.

Safety & protection

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]

Storage Conditions · 1 item

...MUST BE STORED IN ITS SEALED ORIGINAL CONTAINERS, IN WELL-AIRED, FRESH & DRY STOREHOUSES OR IN SHADED & POSSIBLY WELL-AIRED PLACES. IT IS RECOMMENDED THAT THE PRODUCT'S TEMP...NOT EXCEED 25-30 °C, & KEEP...AWAY FROM SOURCES OF HEAT, FREE FLAMES OR SPARK-GENERATING EQUIPMENT. CONTAINERS MUST BE STACKED IN SUCH A WAY AS TO PERMIT FREE CIRCULATION OF AIR...AT BOTTOM & INSIDE OF PILES. STORAGE AREAS MUST BE LOCATED AT SUITABLE DISTANCE FROM INHABITED BUILDINGS, ANIMAL SHELTERS, & FOOD STORES; MOREOVER, THEY MUST BE INACCESSIBLE TO UNAUTHORIZED PERSONS, CHILDREN, & DOMESTIC ANIMALS. /PROTHOATE/

Disposal Methods · 1 item

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.

Preventive Measures · 4 items

ANY MATERIAL SPILLED ON SKIN SHOULD BE IMMEDIATELY REMOVED WITH SOAP & WATER. WHEN SPRAYING & DUSTING...CONTAMINATED CLOTHING SHOULD BE CHANGED FREQUENTLY. /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/

THE STRICT OBSERVANCE OF HYGIENE RULES- NO SMOKING AND NO FOOD INTAKE DURING WORK, THOROUGH WASHING WITH SOAP AFTER WORK, CHANGING PROTECTIVE CLOTHING BEFORE GOING HOME- IS OF THE UTMOST IMPORTANCE. /ORGANOPHOSPHORUS PESTICIDES/

THE PROTECTIVE CLOTHING SHOULD BE KEPT IN SEPARATE PLACES WHERE IT CANNOT BE CONTAMINATED WITH TOXIC CHEMICALS. IT SHOULD BE FORBIDDEN TO KEEP THIS CLOTHING IN LIVING QUARTERS. PROTECTIVE CLOTHING MUST BE WASHED AT LEAST ONCE A WEEK AND EACH TIME IT IS CONTAMINATED WITH PESTICIDES. BEFORE WASHING THE CLOTHING SHOULD BE SOAKED FOR SEVERAL HOURS IN A CALCIUM CARBONATE SOLUTION. /PESTICIDES/

Personal Protective Equipment (PPE) · 2 items

USE OF RUBBER GLOVES, GOGGLES, RESPIRATOR &...PROTECTIVE CLOTHING. /ORGANOPHOSPHORUS PESTICIDES/

WORKERS HANDLING AND APPLYING ORGANOPHOSPHORUS PESTICIDES ... MUST BE GIVEN PERSONAL PROTECTIVE EQUIPMENT COMPRISING OVERALLS MADE OF A TIGHT FABRIC OR POLYVINYL CHLORIDE, GLOVES AND RUBBER BOOTS. THEY MUST WEAR A RESPIRATOR WITH AN ACTIVATED-CARBON GAS FILTER CARTRIDGE AFFORDING PROTECTION FOR A DETERMINED NUMBER OF WORKING HOURS. THE EYES SHOULD BE PROTECTED BY GOGGLES. ... /ORGANOPHOSPHORUS PESTICIDES/

Toxicology

Environmental Fate · 4 items

.../SOME ORGANOPHOSPHORUS INSECTICIDES/...BREAK DOWN INTO TOXIC COMPONENTS & ACCUM, PROBABLY AS RESULT OF AGING, WEATHERING, PLANT ALTERATION OR OTHER DEGRADATION. /ORGANOPHOSPHORUS INSECTICIDES/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1800(SRC), determined from a log Kow of 3.45(2) and a regression-derived equation(3), indicates that chlorthion is expected to have low mobility in soil(SRC). Volatilization of chlorthion from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4X10-6 mm Hg(4), and water solubility, 40 mg/l(5). Chlorthion is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4X10-6 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1800(SRC), determined from a log Kow of 3.45(2) and a regression-derived equation(3), indicates that chlorthion is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4X10-6 mm Hg(7), and water solubility, 40 mg/l(4). According to a classification scheme(5), a measured BCF of 29(6), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorthion, which has a vapor pressure of 4X10-6 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorthion 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 7 hrs(SRC), calculated from its rate constant of 5.9X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase chlorthion may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsOther Poison - Organophosphate
Medical Surveillance · 1 item

Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. /SRP: Protect from exposure those individuals with/ 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/

Soil Adsorption/Mobility · 1 item

The Koc of chlorthion is estimated as 1800(SRC), using a log Kow of 3.45(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chlorthion is expected to have low mobility in soil.

Human Toxicity Excerpts · 5 items

A CHOLINESTERASE INHIBITOR. SYMPTOMS SIMILAR TO PARATHION.

SYMPTOMATOLOGY: 1. NAUSEA...VOMITING, ABDOMINAL CRAMPS, DIARRHEA, EXCESSIVE SALIVATION... 2. HEADACHE, GIDDINESS, VERTIGO & WEAKNESS. 3. RHINORRHEA & SENSATION OF TIGHTNESS IN CHEST ARE COMMON IN INHALATION EXPOSURE. 4. BLURRING OR DIMNESS OF VISION, MIOSIS... TEARING, CILIARY MUSCLE SPASM, LOSS OF ACCOMMODATION & OCULAR PAIN... MYDRIASIS...SOMETIMES SEEN...PROBABLY DUE TO SYMPATHO-ADRENAL DISCHARGE. 5. LOSS OF MUSCLE COORDINATION, SLURRING OF SPEECH, FASCICULATIONS & TWITCHING OF MUSCLES (PARTICULARLY OF TONGUE & EYELIDS), & GENERALIZED PROFOUND WEAKNESS. 6. MENTAL CONFUSION, DISORIENTATION & DROWSINESS. /PARATHION/

SYMPTOMATOLOGY: 7. DIFFICULTY IN BREATHING, EXCESSIVE SECRETION OF SALIVA & OF RESP TRACT MUCUS, ORONASAL FROTHING, CYANOSIS, PULMONARY RALES & RHONCHI & HYPERTENSION, (PRESUMABLY DUE TO ASPHYXIA). 8. RANDOM JERKY MOVEMENTS, INCONTINENCE, CONVULSIONS, & COMA. 9. DEATH PRIMARILY DUE TO RESP ARREST ARISING FROM FAILURE OF RESP CENTER, PARALYSIS OF RESP MUSCLES, INTENSE BRONCHOCONSTRICTION OR ALL THREE. /PARATHION/

TOXICITY IS LOW, IN SPITE OF HIGH ANTICHOLINESTERASE POTENCY (A DISTINCTION ASCRIBED TO SLOW TISSUE ABSORPTION).

Toxic by inhalation & ingestion.

Artificial Pollution SourcesChlorthion's production and former use as an insecticide(1) may have resulted in its direct release to the environment(SRC). Chlorthion is not a registered pesticide product in the US(2).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
rtecs
TE8050000
ridadr
UN2811 6.1/PG 3
Toxicity
LD50 in male, female rats (mg/kg): 880, 980 orally (Gaines)
risk_code
20/21/22-50/53

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

/It is/ rapidly hydrolyzed to dimethyl thiophosphate & 3-chloro-4-nitrophenol. To a limited extent, there is oxidation to the phosphate & hydrolysis to phosphoric acid & 3-chloronitrophenol.

3-CHLORO-4-NITROPHENYL DIMETHYL PHOSPHOROTHIOATE YIELDS 3-CHLORO-4-NITROPHENOL IN RAT, RABBIT, & IN FLY; IT YIELDS 3-CHLORO-4-NITROPHENYL DIMETHYL PHOSPHATE IN RAT, RABBIT, & FLY: NAKATSUGAWA T, TOLMAN NM, & DAHM PA; BIOCHEM PHARMAC 17: 1517 (1968). /FROM TABLE/

...INVESTIGATORS EXAMINED METABOLISM OF...CHLORTHION...IN RAT & COCKROACH. BY MEANS OF ION EXCHANGE CHROMATOGRAPHY, SUBSTANTIAL AMT OF DEALKYLATED ORGANOPHOSPHORUS COMPD WERE FOUND IN URINE OF RATS AFTER ORAL ADMIN.

Absorption, Distribution and Excretion...absorbed by intact skin.

Uses & manufacturing

Uses · 5 items

Used as insecticide to control various agricultural and household pests; Also used to protect livestock and as veterinary anthelmintic; [HSDB]

No longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For Chlorthion (USEPA/OPP PC code 034501) there are 0 labels match./SRP: Not registered for current use in the U.S./

Insecticide /SRP: Former use/

U.S. Production · 2 items

(1972) LESS THAN 4.54X10+5 GRAMS

(1975) LESS THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 2 items

REACTION OF 4-NITRO-3-CHLOROPHENOL WITH O,O-DIMETHYL CHLOROTHIONOPHOSPHATE IN THE PRESENCE OF POTASSIUM CARBONATE & COPPER POWDER

Prepn: Schrader, Angew Chem 66, 265 (1954); US patent 2,701,259 (1955 to Bayer).

Formulations/PreparationsUSEPA/OPP PC Code 034501; Trade Names: Chlorothion, Bay 22/190.
General Manufacturing Information · 4 items

CHLORTHION CONTROLS WIDE RANGE OF AGRICULTURAL & HOUSEHOLD INSECTS, INCL HOUSEFLIES, MOSQUITOES, & ROACHES. CHLORTHION IS NO LONGER IN COMMON USAGE.

SOME OF THE LESS DANGEROUS /ORGANOPHOSPHORUS COMPOUNDS/...HAVE FOUND FAVOR AS SYSTEMIC INSECTICIDES FOR USE IN ANIMALS, PARTICULARLY AGAINST WARBLE-FLY INFESTATION IN CATTLE, & AS ANTHELMINTICS: THESE INCLUDE CHLORTHION, TRICHLORPHON, DIAZINON, & FENCHLORPHOS.

Not listed

Material believed to be no longer manufactured, or marketed for crop protection use.

Applications · 2 items

DescriptionChlorthion is an organophosphate insecticide. It has a moderate aqueous solubility and not considered to be volatile. Chlorthion is not persistent in soil systems and, based on its physico-chemical properties, it is only slightly mobile and not expected to leach to groundwater. It is moderately toxic to most biodiversity but there may be a higher risk for bees. It has a moderate mammalian toxicity, is a cholinesterase inhibitor and a neurotoxin.

UsesInsecticide.

Upstream & downstream products

Suppliers14 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
杭州扬德医药科技有限公司0571-81953185 +86-15381198709 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Chlorthion is an organic thiophosphate that is O,O-dimethyl O-phenyl phosphorothioate substituted by a chloro group at position 3 and a nitro group at position 4. It is a potent cholinesterase inhibitor and used as an insecticide for the control of a wide range of insects. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor and an agrochemical. It is a C-nitro compound, an organic thiophosphate, a member of monochlorobenzenes and an organothiophosphate insecticide.

Related reactions

1 records

Compound notes

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