Chlorthion
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Chlorthion
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CAS No:
500-28-7
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Formula:
C8H9ClNO5PS
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Chemical Name:
Chlorthion
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Synonyms:
Phosphorothioic acid,O-(3-chloro-4-nitrophenyl) O,O-dimethyl ester;Phosphorothioic acid,O-(3-chloro-4-nitrophenyl) O,O-di-Me ester;OMS 217;O-(3-Chloro-4-nitrophenyl) O,O-dimethyl phosphorothioate;Chlorothion;Chlorthion;Compound 22/190;O,O-Dimethyl O-3-chloro-4-nitrophenyl phosphorothioate;O,O-Dimethyl O-(3-chloro-4-nitrophenyl) thiophosphate;Methylchlorothion;Chlorthion methyl;O,O-Dimethyl O-(3-chloro-4-nitrophenyl)thionophosphate;BAY 22190;NSC 8927
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CAS No:
Description
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.
Chlorthion Basic Attributes
297.65
297.65
207-902-5
3NTK55T19G
8927
DTXSID9041784
Pure compound is yellow crystals. ... Commercial product is a yellow oil.
2920190090
Characteristics
106
3.45
1.437 g/cm3 @ Temp: 20 °C
21 °C
136 °C @ Press: 0.23 Torr
175.5±30.7 °C
1.586
In water, 40 mg/l at 20 deg C
2-8°C
4X10-6 mm Hg @ 20 deg C
Oral-rat LD50: 625 mg/kg; Oral-Mouse LD50: 794 mg/kg
Open flame is flammable; heat releases toxic nitrogen oxide, sulfur oxide, phosphorus oxide, chloride gas
CHLOROTHION (SELF-REACTIVE): WHEN SAMPLE WAS HEATED IN SMALL TEST TUBE IT DECOMPOSED & IN A FEW MIN RESIDUE EXPLODED.
VAPOR PRESSURE: 7X10-6 MM HG @ 30 °C /TECHNICAL/
Noncorrosive
Safety Information
UN28116.1/PG3
3
20/21/22-50/53
13-60-61
TE8050000
Xn,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Hydrolyzed by alkali
P261-P273-P280-P302 + P352 + P312-P304 + P340 + P312-P501
H302 + H312 + H332-H410
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.
Toxicology Review- Residue Reviews 63, 1, 1976
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, and P501
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/
NOT FLAMMABLE @ NORMAL TEMP; THERMAL DECOMPOSITION POINT ABOUT 150 °C
CHLOROTHION (SELF-REACTIVE): WHEN SAMPLE WAS HEATED IN SMALL TEST TUBE IT DECOMPOSED & IN A FEW MIN RESIDUE EXPLODED.
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/
Toxicity
moderately toxic
Chlorthion'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).
.../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).
The rate constant for the vapor-phase reaction of chlorthion with photochemically-produced hydroxyl radicals has been estimated as 5.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours (SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chlorthion was found to undergo hydrolysis at 20, 30, 40, 50, and 60 °C with a half-life of 138, 36, 10, 3, and 1 days, respectively(2). Stability also decreases with extremes of pH(2).
35.48|A BCF of 29(1) was measured in pond snails. According to a classification scheme(2), this BCF suggests the potential for bioconcentration of chlorthion in aquatic organisms is low.
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.
The Henry's Law constant for chlorthion is estimated as 4.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4X10-6 mm Hg(1), and water solubility, 40 mg/l(2). This Henry's Law constant indicates that chlorthion is expected to be essentially nonvolatile from water surfaces(3). Chlorthion's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces will not occur(SRC). Chlorthion is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4X10-6 mm Hg(1).
Occupational exposure to chlorthion may have occurred through dermal contact with this compound at workplaces where chlorthion was produced or used. (SRC)
Drug Information
3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG OR BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).|ESTIMATED HUMAN FATAL DOSE 60.0 G. /FROM TABLE/
...absorbed by intact skin.
/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.
0.34 Days
Basic Treatment: Establish a patent airway. 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 normal saline 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/|Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. 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. Rarely is diazepam necessary ... . For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors for hypotension with a normal fluid volume. 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. Depending on the severity of poisoning, doses of atropine ranging from very low to as high as 300 mg/day may be required, or even continuous infusion. The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. 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. Favorable response to a test dose of atropine (1 mg in adults, 0.01 mg/kg in children under 12 years) can help differentiate poisoning by anticholinesterase agents from other conditions. However, lack of response, with no evidence of atropinization (atropine refractoriness) is typical of more severe 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 CHLOROTHION (17 total), please visit the HSDB record page.
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.
Chlorthion Use and Manufacturing
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).
Insecticide.
(1972) LESS THAN 4.54X10+5 GRAMS|(1975) LESS THAN 4.54X10+5 GRAMS
USEPA/OPP PC Code 034501; Trade Names: Chlorothion, Bay 22/190.
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.
Analysis of products: Extraction with ether or petroleum ether, followed by washing with 1% sodium carbonate soln, redn of the nitro group with zinc duct in glacial acetic acid/hydrochloric acid (9:1), & titration of the amine with sodium nitrite & iodine-starch (WHO Specifications for pesticides, 2nd edition, Geneva, 1961). Analysis of residues: Dependent on the moisture content of the sample, extraction with either acetone or chloroform, clean-up by liquid-liquid extraction or column chromatography, & gas chromatographic determination with electron-capture detection (Methodensammlung Rueckstandsanalytik, 22). For colorimetric determination see Zweig G, Analytical Methods for Pesticides, Growth Regulators & Food Additives, Vol II, 78, & for gas chromatographic determination with electron capture detection see Zweig G, Analytical Methods for Pesticides, Growth Regulators & Food Additives, Vol VI, 322-24 (1972).
MANY OF /THE ORGANOPHOSPHATE/...PESTICIDES...ARE SUCH POWERFUL INHIBITORS OF CHOLINESTERASE THAT VERY SENSITIVE ENZYMATIC METHODS FOR THEIR MICRO-DETERMINATION HAVE BEEN DEVELOPED.../SEE PA GIANG & SA HALL, ANAL CHEM 23: 1830 (1951)./
Computed Properties
Molecular Weight:297.65
XLogP3:3.5
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:296.9627583
Monoisotopic Mass:296.9627583
Topological Polar Surface Area:106
Heavy Atom Count:17
Complexity:318
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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