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Dicapthon

PubChem CID
17168
Structure
Dicapthon_small.png
Dicapthon_3D_Structure.png
Dicapthon__Crystal_Structure.png
Molecular Formula
Synonyms
  • DICAPTHON
  • 2463-84-5
  • Isochlorthion
  • Dicapthion
  • Captec
Molecular Weight
297.65 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dicapthon.png

1.2 3D Conformer

1.3 Crystal Structures

COD Number
Associated Article
Baughman, Russell G.; Hall, Gabriel B.. Two organophosphorus pesticides: methyl parathion and dicapthon. Acta Crystallographica Section C 2014;70(10):975-977. DOI: 10.1107/S2053229614020233
Crystal Structure Depiction
Crystal Structure Depiction
Hermann-Mauguin space group symbol
P 1 21/c 1
Hall space group symbol
-P 2ybc
Space group number
14
a
10.9108 Å
b
17.0968 Å
c
6.8940 Å
α
90.00 °
β
101.65 °
γ
90.00 °
Z
4
Z'
1
Residual factor
0.0441

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-λ5-phosphane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H9ClNO5PS/c1-13-16(17,14-2)15-8-4-3-6(10(11)12)5-7(8)9/h3-5H,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

OTKXWJHPGBRXCR-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COP(=S)(OC)OC1=C(C=C(C=C1)[N+](=O)[O-])Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H9ClNO5PS
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
297.65 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
296.9627583 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
296.9627583 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
106 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
17
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
318
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

White solid; [Hawley]

3.2.2 Color / Form

CRYSTALS FROM METHANOL
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 479
WHITE SOLID FROM METHANOL
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 184

3.2.3 Melting Point

53 °C
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 479

3.2.4 Solubility

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 479
SOL IN CYCLOHEXANE
Sax, N.I. Dangerous Properties of Industrial Materials. 6th ed. New York, NY: Van Nostrand Reinhold, 1984., p. 2015
Water solubility= 14.7 mg/l at 20 °C
Bowman BT, Sans WW; J Environ Sci Health B18: 221-7 (1983)

3.2.5 Vapor Pressure

0.0000036 [mmHg]
3.6X10-6 mm Hg
Freed VH et al; Pestic Biochem Physiol 10: 203-11 (1979)

3.2.6 LogP

log Kow= 3.58 at 20 °C
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 471

3.2.7 Decomposition

When heated to decomposition it emits very toxic fumes of /phosphorus oxides, sulfur oxides, nitrogen oxides and hydrogen chloride/.
Sax, N.I. Dangerous Properties of Industrial Materials. 6th ed. New York, NY: Van Nostrand Reinhold, 1984., p. 2015

3.2.8 Kovats Retention Index

Standard non-polar
1959 , 1963.9

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.4.2 Pesticides

Pesticides -> Organophosphate Insecticides

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 5
View All
NIST Number
118997
Library
Main library
Total Peaks
182
m/z Top Peak
262
m/z 2nd Highest
125
m/z 3rd Highest
79
Thumbnail
Thumbnail
2 of 5
View All
NIST Number
28949
Library
Replicate library
Total Peaks
41
m/z Top Peak
262
m/z 2nd Highest
125
m/z 3rd Highest
79
Thumbnail
Thumbnail

4.2 IR Spectra

4.2.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
American Cyanamid Company
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3 Other Spectra

Intense mass spectral peaks: 262 m/z (100%), 125 m/z (64%), 79 m/z (35%), 47 m/z (23%)
Hites, R.A. Handbook of Mass Spectra of Environmental Contaminants. Boca Raton, FL: CRC Press Inc., 1985., p. 300

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Absorption, Distribution and Excretion

/ORGANOPHOSPHORUS INSECTICIDES/ ... ARE ABSORBED INTO BODY BY RESPIRATORY, GASTROINTESTINAL, & CUTANEOUS PATHWAYS. /ORGANOPHOSPHORUS INSECTICIDES/
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 109
IN GENERAL, BECAUSE OF RAPID HYDROLYSIS & EXCRETION IN URINE, ORGANOPHOSPHORUS COMPD ARE NOT ACCUMULATED & STORED IN ANIMAL BODY. /ORGANOPHOSPHORUS COMPD/
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 110

7.2 Metabolism / Metabolites

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 ... .
Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 149
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/
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-34
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.
Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1012

7.3 Mechanism of Action

CHOLINESTERASE INHIBITOR.
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 479

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used as insecticide and acaricide for agricultural, household, and public health pest control; Also used for tick control in domestic animals; [HSDB]
Restricted Notes
Cancelled--no longer registered as a pesticide for use in the US; [HSDB]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.172 (Spring, 1998) EPA 738-R-98-002
INSECTICIDE
Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993., p. C-112
Aphicide
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 360
Acaracide
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 471

8.2 Methods of Manufacturing

BY REACTION OF DIMETHYL PHOSPHOROCHLORIDOTHIONATE WITH ALKALI METAL 2-CHLORO-4-NITROPHENATE OR WITH 2-CHLORO-4-NITROPHENOL IN PRESENCE OF SUITABLE BASE.
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 184

8.3 General Manufacturing Information

PRODUCTION DISCONTINUED BY AMERICAN CYANAMID CO.
Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993., p. C-112
... DICAPTHON ... /IS USED/ IN HOUSEHOLD, PUBLIC HEALTH, & AGRICULTURAL PEST CONTROL.
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 104
OF PROMISING INSECTICIDAL ACTIVITY GIVING OVER 90% KILL OF APHID @ CONCN OF 1:28000 IN WATER; EFFECTIVE AGAINST BOLL WEEVIL WITH GOOD RESIDUAL ACTIVITY.
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 184
EMPLOYED TO CONTROL TICKS ON DOGS & OTHER DOMESTIC ANIMALS.
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 2. New York: Marcel Dekker, Inc., 1976., p. 354

9 Identification

9.1 Analytic Laboratory Methods

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.
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 184
GENERAL METHOD FOR ORGANOCHLORINE & ORGANOPHOSPHORUS PESTICIDES, USING THIN LAYER OR GAS CHROMATOGRAPHIC DETERMINATIONS ON RESIDUES.
Association of Official Analytical Chemists. Official Methods of Analysis. 10th ed. and supplements. Washington, DC: Association of Official Analytical Chemists, 1965. New editions through 13th ed. plus supplements, 1982., p. 13/466 29.001
MACRO & MICRO METHOD /FOR DETERMINATION OF PHOSPHORUS IN PLANTS/ SPECTROPHOTOMETRIC OR COLORIMETRIC METHODS. /PHOSPHORUS/
Association of Official Analytic Chemists. Official Methods of Analysis of the AOAC. 14th ed. Arlington, VA: Association of Official Analytic Chemists, Inc., 1984., p. 53/3.096-100
Phosphorus was determined by a continuous flow method using fluorescence quenching of Rhodamine 6G with molybdophosphate. /Phosphorus/
Motomizu S et al; Bunseki Kagaku 33 (2): 116-9 (1984)
For more Analytic Laboratory Methods (Complete) data for DICAPTHON (9 total), please visit the HSDB record page.

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]

Precautionary Statement Codes

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Acute Tox. 3 (100%)

10.1.3 Hazards Summary

A cholinesterase inhibitor; [Hawley] The only adverse effect noted in one year feeding study with rats (250 ppm highest dose group) was retarded growth; [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]
Hawley - Lewis RJ. _Hawley's Condensed Chemical Dictionary, _15th Ed. New York: John Wiley & Sons, 2007.
TLVs and BEIs - _Threshold Limit Values for Chemical Substances and Physical Agents & Biological Exposure Indices. _Cincinnati: ACGIH, 2020.

10.2 Accidental Release Measures

10.2.1 Preventive Measures

... GREAT CARE SHOULD BE EXERCISED IN HANDLING ... WHEN SPRAYING & DUSTING ... CONTAMINATED CLOTHING SHOULD BE CHANGED FREQUENTLY. /ORGANOPHOSPHATE INSECTICIDES/
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 110
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/
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1992., p. 713
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/
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1992., p. 713
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/
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1992., p. 713
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/
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1992., p. 713

10.3 Exposure Control and Personal Protection

Exposure Summary
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]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
TLVs and BEIs - _Threshold Limit Values for Chemical Substances and Physical Agents & Biological Exposure Indices. _Cincinnati: ACGIH, 2020.

10.3.1 Personal Protective Equipment (PPE)

USE OF RUBBER GLOVES, GOGGLES, RESPIRATOR, & OTHER PROTECTIVE CLOTHING IS ADVISABLE. /ORGANOPHOSPHATE INSECTICIDES/
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 110

10.4 Regulatory Information

10.4.1 FIFRA Requirements

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. O-(2-Chloro-4-nitrophenyl) O,O-dimethyl phosphorothioate is found on List B. Case No: 2785; Pesticide type: insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): O-(2-Chloro-4-nitrophenyl) O,O-dimethyl phosphorothioate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.172 (Spring, 1998) EPA 738-R-98-002

11 Toxicity

11.1 Toxicological Information

11.1.1 Adverse Effects

Other Poison - Organophosphate

11.1.2 Acute Effects

11.1.3 Antidote and Emergency Treatment

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/
MORGAN DP; RECOGNITION AND MANAGEMENT OF PESTICIDE POISONINGS. 4TH ED, P. 6_ EPA 540/9-88-001. WASHINGTON, DC, U.S. GOVERNMENT PRINTING OFFICE, MARCH 1989
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/
MORGAN DP; RECOGNITION AND MANAGEMENT OF PESTICIDE POISONINGS. 4TH ED, P.7 EPA 540/9-88-001. WASHINGTON, DC: U.S. GOVERNMENT PRINTING OFFICE, MARCH 1989
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/
MORGAN DP; RECOGNITION AND MANAGEMENT OF PESTICIDE POISONINGS. 4TH ED, P.7 EPA 540/9-88-001. WASHINGTON, DC: U.S. GOVERNMENT PRINTING OFFICE, MARCH 1989
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/
MORGAN DP; RECOGNITION AND MANAGEMENT OF PESTICIDE POISONINGS. 4TH ED, P.8 EPA 540/9-88-001. WASHINGTON, DC: U.S. GOVERNMENT PRINTING OFFICE, MARCH 1989
For more Antidote and Emergency Treatment (Complete) data for DICAPTHON (8 total), please visit the HSDB record page.

11.1.4 Medical Surveillance

... /ESTIMATION/ OF BLOOD CHOLINESTERASE LEVELS IS OF VALUE IN ... DETECTION OF OVER-EXPOSURE. /ORGANOPHOSPHATE INSECTICIDES/
White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 110

11.1.5 Human Toxicity Excerpts

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/
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-340
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/
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-340
... 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 ... .
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 360
Cholinesterase inhibitor
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 376

11.1.6 Non-Human Toxicity Excerpts

OF COMPARATIVELY LOW MAMMALIAN TOXICITY ... RATS MAINTAINED FOR 1 YR ON DIETS CONTAINING 25, 100 & 250 PPM SHOWED RETARDED GROWTH ONLY @ TWO HIGHER LEVELS. SKIN ABSORPTION APPARENTLY SLIGHT SINCE GUINEA PIGS WERE UNAFFECTED BY SINGLE APPLICATION OF 18 HR DURATION OF 2 G/KG.
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 184
LETHAL AMT OF ORGANOPHOSPHATES CAUSE DEATH BY COMBINATION OF EFFECTS OF MUSCARINIC, NICOTINIC & CENTRAL CHOLINERGIC OVERSTIMULATION &/OR RECEPTOR PARALYSIS. THUS HYPOTENSION, BRADYCARDIA, BRONCHOCONSTRICTION & BRONCHIAL FLUID ACCUMULATION, INABILITY OF TONICALLY RIGID ... RESP MUSCLES TO WORK PROPERLY, CYANOSIS, & CENTRAL RESPIRATORY DEPRESSION ARE MANIFESTED. THE ANIMAL DIES OF ASPHYXIA. /ORGANOPHOSPHATES/
Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 988
ANTICHOLINESTERASES MAY EXERT DEPRESSANT ACTION ON CONDITIONED BEHAVIOR. LOWER DOSES MAY PRODUCE STIMULATION, HIGHER DOSES DEPRESSION. CHLORTHION RECORDED TO HAVE DEPRESSANT EFFECT ON CONDITIONED BEHAVIOR.
BIGNAMI GATTI GL G; EXCERPTA MED INT CONG SER 8 (118): 93-106 (1967)

11.1.7 Non-Human Toxicity Values

LD50 Rat oral 500-1000 mg/kg
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V13 440 (1981)
LD50 Mouse oral 475 mg/kg
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 471
LD50 Rat female oral 330 mg/kg
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 360
LD50 Rat male dermal 790 mg/kg
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 360
LD50 Rat female dermal 1250 mg/kg
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 360

11.2 Ecological Information

11.2.1 Ecotoxicity Values

TLm Mercenaria mercenaria (hard clam) 3.34 mg/l/48 hr, eggs /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 471

11.2.2 Environmental Fate / Exposure Summary

Dicapthon's use as an insecticide releases the compound directly to the environment through applications in sprays, powders and other routes of application. If released to the atmosphere, dicapthon will degrade rapidly in the vapor phase by reaction with photochemically produced hydroxyl radicals (half-life of about 6 hr). Particulate phase dicapthon and aerosols released to air during spray applications of dicapthon insecticides will be removed from air physically by dry and wet deposition. If released to moist soil or water, dicapthon will degrade through aqueous hydrolysis. At 20 °C, aqueous hydrolysis half-lives of 49 days (pH 6.1) and 29 days (pH 7.4) have been determined; hydrolysis increases with alkalinity, so the degradation rate in soil and water should increase with increasing pH. Insufficient data are available to access the relative importance of biodegradation in soil or water. Based upon Koc estimates ranging from 865 to 2100, dicapthon is expected to have low mobility in soil. Occupational exposure may occur through dermal contact and inhalation of sprays, especially to workers applying the compound as an insecticide. (SRC)

11.2.3 Artificial Pollution Sources

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).
(1) Meister RT; Farm Chemicals Handbook 1987. Willoughby,OH: Meister PublishingCo p. C86 (1987)

11.2.4 Environmental Fate

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).
(1) Freed VH et al; J Agric Food Chem 27: 706-8 (1979)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods Washington,DC: Amer Chem Soc p. 4-9 (1990)
(3) Meylan W et al; Environ Sci Technol 26: 1560-6 (1992)
(4) Swann RL et al; Res Rev 85: 23 (1983)
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).
(1) Freed VH et al; J Agric Food Chem 27: 706-8 (1979)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods Washington,DC: Amer Chem Soc p. 4-9 (1990)
(3) Meylan W et al; Environ Sci Technol 26: 1560-6 (1992)
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).
(1) Freed VH et al; Pestic Biochem Physiol 10: 203-11 (1979)
(2) Bidleman TF; Environ Sci Technol 22: 361-7 (1988)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-9 (1993)
(4) Nations BK, Hallberg GR; J Environ Qual 21: 486-92 (1992)

11.2.5 Environmental Abiotic Degradation

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).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-9 (1993)
(2) Freed VH et al; J Agric Food Chem 27: 706-8 (1979)

11.2.6 Environmental Bioconcentration

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).
(1) De Bruijn J, Hermens J; Environ Toxicol Chem 10: 791-804 (1991)
(2) Hansch C, Leo AJ; Medchem Project Issue No.26 Claremont,CA: Pomona College (1985)
(3) Bowman BT, Sans WW; J Environ Sci Health B18: 221-7 (1983)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods Washington,DC: Amer Chem Soc pp. 5-4,5-10 (1990)

11.2.7 Soil Adsorption / Mobility

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).
(1) Hansch C, Leo AJ; Medchem Project Issue No.26 Claremont,CA: Pomona College (1985)
(2) Bowman BT, Sans WW; J Environ Sci Health B18: 221-7 (1983)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods Washington,DC: Amer Chem Soc p. 4-9 (1990)
(4) Meylan W et al; Environ Sci Technol 26: 1560-6 (1992)
(5) Swann RL et al; Res Rev 85: 23 (1983)

11.2.8 Volatilization from Water / Soil

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).
(1) Freed VH et al; Pestic Biochem Physiol 10: 203-11 (1979)
(2) Bowman BT, Sans WW; J Environ Sci Health B18: 221-7 (1983)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods Washington,DC: Amer Chem Soc pp. 15-15 to 15-29 (1990)

11.2.9 Probable Routes of Human Exposure

Occupational exposure to dicapthon may occur through dermal contact and inhalation of sprays, especially to workers applying the compound as an insecticide. (SRC)

12 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound

13 Literature

13.1 Consolidated References

13.2 Springer Nature References

13.3 Chemical Co-Occurrences in Literature

13.4 Chemical-Gene Co-Occurrences in Literature

13.5 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 ChemIDplus

16.2 ChEMBL Target Tree

16.3 UN GHS Classification

16.4 NORMAN Suspect List Exchange Classification

16.5 EPA DSSTox Classification

16.6 EPA Substance Registry Services Tree

16.7 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (2-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-λ⁵-phosphane
    https://echa.europa.eu/substance-information/-/substanceinfo/100.152.403
    (2-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-λ⁵-phosphane (EC: 623-752-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/157002
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Hazardous Substances Data Bank (HSDB)
  7. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  8. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  9. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  12. SpectraBase
  13. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. Springer Nature
  15. SpringerMaterials
    O,O-dimethyl O-(2-chloro-4-nitrophenyl)phosphorothioate
    https://materials.springer.com/substanceprofile/docs/smsid_ofysybzztygbviph
  16. Wikidata
  17. PubChem
  18. GHS Classification (UNECE)
  19. EPA Substance Registry Services
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS