Dicapthon
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Dicapthon
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CAS No:
2463-84-5
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Formula:
C8H9ClNO5PS
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Chemical Name:
Dicapthon
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Synonyms:
Phosphorothioic acid,O-(2-chloro-4-nitrophenyl) O,O-dimethyl ester;OMS 214;ENT 17,035;American Cyanamid 4124;O-(2-Chloro-4-nitrophenyl) O,O-dimethyl phosphorothioate;Di-Captan;Dicapthon;O,O-Dimethyl O-2-chloro-4-nitrophenyl phosphorothioate;Experimental Insecticide 4124;Isochlorthion;p-Nitro-o-chlorophenyl dimethyl thionophosphate;BAY 14981;ENT 17035;Dicapthion;Insecticide ACC 4124
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CAS No:
Dicapthon Basic Attributes
297.65
297.65
6RQZ0Q90M7
DTXSID0041850
CRYSTALS FROM METHANOL|WHITE SOLID FROM METHANOL
29201900
Characteristics
106
3.58 at 20 deg C
Solid
1.499g/cm3
53 °C
355.8ºC at 760mmHg
169ºC
1.586
Water solubility= 14.7 mg/l at 20 deg C
3.6X10-6 mm Hg
Oral-rat LD50: 284 mg/kg; Oral-Mouse LD50: 331 mg/kg
Decomposes toxic phosphorus oxide, sulfur oxide, nitrogen oxide, chloride gas by heating
Henry's Law constant= 9.59X10-8 atm-cu m/mole (est).
Safety Information
III
6.1(b)
2783
3
21/22
36
TE7875000
Xn
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
P264, P270, P280, P301+P310, P302+P352, P312, P321, P322, P330, P361, P363, P405, P501
H301
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P280, P301+P310, P302+P352, P312, P321, P322, P330, P361, P363, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
USE OF RUBBER GLOVES, GOGGLES, RESPIRATOR, & OTHER PROTECTIVE CLOTHING IS ADVISABLE. /ORGANOPHOSPHATE INSECTICIDES/
... GREAT CARE SHOULD BE EXERCISED IN HANDLING ... WHEN SPRAYING & DUSTING ... CONTAMINATED CLOTHING SHOULD BE CHANGED FREQUENTLY. /ORGANOPHOSPHATE INSECTICIDES/|If material not on fire and not involved in fire: Keep sparks, flames, and othersources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, NOS/|Personnel protection: Keep upwind. Wear appropriate chemical protective gloves, boots and goggles. Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organophosphorus pesticides, liquid, NOS/|If material not on fire and not involved in fire: Keep sparks, flames, and othersources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, NOS/|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. Avoid bodily contact with the material. Wear appropriate chemical protective gloves, boots and goggles. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate protective clothing. /Organophosphorus pesticides, solid, NOS/
Toxicity
highly toxic
LD50 Rat oral 500-1000 mg/kg|LD50 Mouse oral 475 mg/kg|LD50 Rat female oral 330 mg/kg|LD50 Rat male dermal 790 mg/kg|LD50 Rat female dermal 1250 mg/kg
Dicapthon's former use as an insecticide(1) releases the compound directly to the environment through applications in sprays, powders and other routes of application(SRC).
TERRESTRIAL FATE: Since dicapthon hydrolyzes in water(1), it will likely hydrolyze in moist soil(SRC); at 20 °C, aqueous hydrolysis half-lives of 49 days (pH 6.1) and 29 days (pH 7.4) have been determined(1); hydrolysis increases with alkalinity, so the degradation rate of dicapthon in soil will probably increase with alkalinity(SRC). In one soil persistence study (soil pH 6.2), dicapthon had a soil half-life of 43 days in sealed vials(1). Insufficient data are available to access the relative importance of biodegradation in soil. Based upon Koc estimates ranging from 865 to 2100(2-3,SRC), dicapthon is expected to have low mobility in soil(4,SRC).|AQUATIC FATE: Dicapthon can degrade in water through aqueous hydrolysis; at 20 °C, hydrolysis half-lives of 49 days (pH 6.1) and 29 days (pH 7.4) have been determined(1); the hydrolysis rate increases as the pH increases. Insufficient data are available to access the relative importance of biodegradation or photodegradation in water. Based upon Koc estimates ranging from 865 to 2100(2-3,SRC), some partitioning from the water column to sediment and suspended material may occur(SRC). Aquatic volatilization is not expected to be an important fate process(SRC).|ATMOSPHERIC FATE: Based upon a reported vapor pressure of 3.6X10-6 mm Hg at 20 °C(1), dicapthon can exist in both the vapor and particulate phases in the ambient atmosphere(2,SRC). It will degrade rapidly in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 6 hr(3,SRC). Particulate phase dicapthon and aerosols released to air during applications of dicapthon insecticides will be removed from air physically by dry and wet deposition(SRC).
The rate constant for the vapor phase reaction of dicapthon with photochemically produced hydroxyl radicals has been estimated to be 6.1X10-11 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 6 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). At 20 °C, the aqueous hydrolysis half-life of dicapthon in phosphate buffered solution was experimentally determined to be 29 days at pH 7.4 and 49 days at pH 6.1(2).
77.62|Using a flow-through system and a 3-11 day exposure period,a dicapthon BCF (extractable lipid basis) of 891 was measured in guppy fish (Poecilia reticulata)(1). Based upon a measured log Kow of 3.58(2) and a water solubility of 14.7 mg/l at 20 °C(3), the BCF of dicapthon can be estimated to be 310 and 136, respectively, from regression derived equations(4,SRC). These BCF values suggest that some bioconcentration may occur in aquatic organisms(SRC).
Based upon a measured log Kow of 3.58(1) and a water solubility of 14.7 mg/l at 20 °C(2), the Koc of dicapthon can be estimated to be 2100 and 995, respectively, from regression derived equations(3,SRC). Using a structure estimation method(4), the Koc can be estimated to be 865(4,SRC). According to a suggested classification scheme(5), these estimated Koc values suggest that dicapthon has low mobility in soil(SRC).
Based upon a vapor pressure of 3.6X10-6 mm Hg(1) and a water solubility of 14.7 mg/L at 20 °C(2), the Henry's Law constant for dicapthon can be estimated to be 9.59X10-8 atm-cu m/mole (SRC). This value of Henry's Law constant indicates that dicapthon is essentially nonvolatile from water(3).
Occupational exposure to dicapthon may occur through dermal contact and inhalation of sprays, especially to workers applying the compound as an insecticide. (SRC)
Drug Information
/ORGANOPHOSPHORUS INSECTICIDES/ ... ARE ABSORBED INTO BODY BY RESPIRATORY, GASTROINTESTINAL, & CUTANEOUS PATHWAYS. /ORGANOPHOSPHORUS INSECTICIDES/|IN GENERAL, BECAUSE OF RAPID HYDROLYSIS & EXCRETION IN URINE, ORGANOPHOSPHORUS COMPD ARE NOT ACCUMULATED & STORED IN ANIMAL BODY. /ORGANOPHOSPHORUS COMPD/
RABBIT & RAT LIVER MICROSOMES & HOUSEFLY MICROSOMES PLUS NADPH2 & O2 WERE INCUBATED WITH DICAPTHON. IN EACH CASE, CORRESPONDING PHENOL WAS FOUND. ACTIVATION OF DICAPTHON TO CORRESPONDING OXON ANALOG WAS OBSERVED. SOME CONVERSION OF OXON ANALOG TO CORRESPONDING PHENOL WAS ALSO OBSERVED ... .|YIELDS 2-CHLORO-4-NITROPHENOL IN RAT, IN RABBIT, IN FLY. YIELDS 2-CHLORO-4-NITROPHENYL DIMETHYL PHOSPHATE IN RAT, IN RABBIT, IN FLY. /FROM TABLE/|A relatively high proportion of the total metabolism in the rat involves alkyl phosphate hydrolysis, as is true of other dialkyl compounds, in contrast to diethyl compounds.
1.02 Days
CHOLINESTERASE INHIBITOR.
1. INSURE THAT A CLEAR AIRWAY EXISTS BY ASPIRATION OF SECRETIONS IF NECESSARY. ADMIN OXYGEN BY MECHANICALLY ASSISTED PULMONARY VENTILATION IF RESPIRATION IS DEPRESSED. IMPROVE TISSUE OXYGENATION AS MUCH AS POSSIBLE BEFORE ADMIN ATROPINE TO MINIMIZE RISK OF VENTRICULAR FIBRILLATION. IN SEVERE POISONINGS, IT MAY BE NECESSARY TO SUPPORT PULMONARY VENTILATION MECHANICALLY FOR SEVERAL DAYS. 2. ADMIN ATROPINE SULFATE IV, OR IM IF IV INJECTION IS NOT POSSIBLE. ... IN MODERATELY SEVERE POISONING: ADULT DOSAGE AND CHILDREN OVER 12 YR: 0.4-2.0 MG REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED. MAINTAIN ATROPINIZATION WITH REPEATED DOSAGE OF 0.02-0.05 MG/KG BODY WEIGHT. /ORGANOPHOSPHATE PESTICIDES/|2. SEVERELY POISONED INDIVIDUALS MAY EXHIBIT REMARKABLE TOLERANCE TO ATROPINE; TWO OR MORE TIMES THE DOSAGES SUGGESTED ABOVE MAY BE NEEDED. THE DOSE OF ATROPINE MAY BE INCREASED AND THE DOSING INTERVAL DECREASED AS NEEDED TO CONTROL SYMPTOMS. CONTINUOUS IV INFUSION OF ATROPINE MAY BE NECESSARY WHEN ATROPINE REQUIREMENTS ARE MASSIVE. REVERSAL OF MUSCARINIC SYMPTOMS AND SIGNS, NOT AN ARBITRARY DOSE LIMIT, IS THE DESIRED END-POINT. PRESERVATIVE-FREE ATROPINE PRODUCTS SHOULD BE USED WHENEVER POSSIBLE. NOTE: PERSONS NOT POISONED OR ONLY SLIGHTLY POISONED BY ORGANOPHOSPHATES MAY DEVELOP SIGNS OF ATROPINE TOXICITY FROM SUCH LARGE DOSES. FEVER, MUSCLE FIBRILLATIONS, AND DELIRIUM ARE THE MAIN SIGNS OF ATROPINE TOXICITY. IF THESE APPEAR WHILE THE PATIENT IS FULLY ATROPINIZED, ATROPINE ADMINISTRATION SHOULD BE DISCONTINUED, AT LEAST TEMPORARILY, WHILE THE SEVERITY OF POISONING IS REEVALUATED. /ORGANOPHOSPHATE PESTICIDES/|3. DRAW BLOOD SAMPLE (HEPARINIZED) FOR CHOLINESTERASE ANALYSIS BEFORE ADMINISTRATION OF PRALIDOXIME, WHICH TENDS TO REVERSE THE CHOLINESTERASE DEPRESSION. 4. ADMIN PRALIDOXIME (PROTOPAM, 2-PAM) IN CASES OF SEVERE POISONING...IN WHICH RESP DEPRESSION, MUSCLE WEAKNESS & TWITCHINGS ARE SEVERE. ... ADULT DOSAGE AND CHILDREN OVER 12): GIVE 1.0-2.0 G IV @ NO MORE THAN 0.2 G/MIN. CHILD'S DOSE (UNDER 12 YR): GIVE 20-50 MG/KG (DEPENDING ON SEVERITY) IV, INJECTING NO MORE THAN HALF TOTAL DOSE/MIN. DOSAGE...MAY BE REPEATED IN 1-2 HR, THEN @ 10-12 HR INTERVAL IF NEEDED. IN VERY SEVERE POISONINGS, DOSAGE...MAY BE DOUBLED. /ORGANOPHOSPHATE PESTICIDES/|4. BE PREPD TO ASSIST PULMONARY VENTILATION MECHANICALLY IF RESP ... DEPRESSED ... . 5. IN PATIENTS WHO HAVE BEEN POISONED BY ORGANOPHOSPHATE CONTAMINATION OF SKIN, CLOTHING, HAIR, AND/OR EYES, DECONTAMINATION MUST PROCEED CONCURRENTLY WITH WHATEVER RESUSCITATIVE AND ANTIDOTAL MEASURES ARE NECESSARY TO PRESERVE LIFE. ... 6. IF ... INGESTED IN QUANTITY PROBABLY SUFFICIENT TO CAUSE POISONING, THE STOMACH AND INTESTINE MUST BE EMPTIED. A. EMPTY THE STOMACH BY INTUBATION, ASPIRATION, AND LAVAGE, USING SLURRY OF ACTIVATED CHARCOAL IN ISOTONIC SALINE. RIGOROUS PRECAUTIONS MUST BE TAKEN TO PROTECT THE AIRWAY FROM ASPIRATION OF REGURGITATED. IF VICTIM IS UNCONSCIOUS OR OBTUNDED, INSERT A CUFFED ENDOTRACHEAL TUBE PRIOR TO GASTRIC INTUBATION. KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING GASTRIC INTUBATION AND LAVAGE ... . KEEP VICTIM'S HEAD TURNED TO THE LEFT. /ORGANOPHOSPHATE PESTICIDES/|For more Antidote and Emergency Treatment (Complete) data for DICAPTHON (8 total), please visit the HSDB record page.
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. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. /Parathion/|Symptomatology: 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction or all three. /Parathion/|... Dicapthon was tested for safety and for its ability to control malaria mosquitoes. The 50% water-wettable powder was applied as a 5% suspension of active ingredient at a rate of 2 g/sq m to the inside of 219 homes and 262 other structures. The buildings had mud walls and thatch roofs. The workers wore waterproof hats, rubber gloves, shoes, and overalls that were washed daily. Workers who weighed out individual pump charges into bags wore respirators in addition to the other protective equipment. No complaints attributable to dicapthon were received from either the workers or from the inhibitants of sprayed houses. Whole blood cholinesterase activity was slightly depressed in the workers but not in the inhabitants ... .|Cholinesterase inhibitor
Dicapthon Use and Manufacturing
It is prepared with O, O-dimethylphosphorus sulfide chloride and 2-chloro-4-nitrophenol as raw materials.
Insecticide.
PRODUCTION DISCONTINUED BY AMERICAN CYANAMID CO.|... DICAPTHON ... /IS USED/ IN HOUSEHOLD, PUBLIC HEALTH, & AGRICULTURAL PEST CONTROL.|OF PROMISING INSECTICIDAL ACTIVITY GIVING OVER 90% KILL OF APHID @ CONCN OF 1:28000 IN WATER; EFFECTIVE AGAINST BOLL WEEVIL WITH GOOD RESIDUAL ACTIVITY.|EMPLOYED TO CONTROL TICKS ON DOGS & OTHER DOMESTIC ANIMALS.
MACRO: WASH ETHER SOLN WITH 1% SODIUM CARBONATE TO REMOVE PHENOL, REDUCE DICAPTHON BY TREATMENT OF ETHER SOLN WITH ZINC-ACID SOLN & TITRATE AMINO GROUP SO OBTAINED WITH STD SODIUM NITRITE SOLN (AMERICAN CYANAMID). QUANTITATIVE PHOSPHORIMETRIC PROCEDURE FOR ANALYSIS.|GENERAL METHOD FOR ORGANOCHLORINE & ORGANOPHOSPHORUS PESTICIDES, USING THIN LAYER OR GAS CHROMATOGRAPHIC DETERMINATIONS ON RESIDUES.|MACRO & MICRO METHOD /FOR DETERMINATION OF PHOSPHORUS IN PLANTS/ SPECTROPHOTOMETRIC OR COLORIMETRIC METHODS. /PHOSPHORUS/|Phosphorus was determined by a continuous flow method using fluorescence quenching of Rhodamine 6G with molybdophosphate. /Phosphorus/|For more Analytic Laboratory Methods (Complete) data for DICAPTHON (9 total), please visit the HSDB record page.
Computed Properties
Molecular Weight:297.65
XLogP3:3.6
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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