Tetrachlor-p-benzochinon

3-4.9

2.19

1.97 (NTP, 1992) - Denser than water; will sink

1.97

Relative density (water = 1): 2.0

GOLDEN-YELLOW PLATELETS FROM ACETIC ACID OR ACETONE; MONOCLINIC PRISMS FROM BENZENE OR TOLUENE OR BY SUBLIMATION IN VACUO

YELLOW LEAFLETS OR PRISMS

less than 1 mg/mL at 70 °F (NTP, 1992)

ALMOST INSOL IN COLD PETROLEUM ETHER, COLD ALCOHOL; SPARINGLY SOL IN CHLOROFORM, CARBON DISULFIDE, CARBON TETRACHLORIDE; SOLUBLE IN ETHER. INSOLUBLE IN WATER.

g/100 g: in acetone 33, ether 16, dimethylformamide 5.4, solvent naphtha 5.4, benzene 1.3, methanol about 0.1, carbon tetrachloride about 0.1, dibutyl phthalate about 0.1

ALMOST INSOL IN WATER (1:4000)

In water, 250 mg/l at room temperature

Solubility in water: none

Sublimes (NTP, 1992)

Sublimes

SUBLIMES AT BOILING POINT

552 °F (decomposes) (NTP, 1992)

292 °C (SEALED TUBE)

290 °C

0 mmHg at 68 °F approximately (NTP, 1992)

0.0000051 [mmHg]

5.1X10-6 MM HG @ 25 °C

Vapor pressure, Pa at 25 °C:

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Chemical: 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrachloro-

2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrachloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrachloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

Status: Active Update: 05-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2069

Chloranil: Does not have an individual approval but may be used under an appropriate group standard

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Not combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

A skin, eye, and respiratory tract irritant; May cause CNS effects with heavy exposures resulting in unconsciousness; [ICSC] A skin, mucous membrane, and respiratory tract irritant; May cause CNS depression and liver damage; [CAMEO] Symptoms of poisoning include watery diarrhea, CNS depression, coma, and death; Has caused corneal necrosis in rabbit eyes; Emergency medical treatment: see Dichlone-chloranil; [HSDB] Effects in high-dose animal studies include liver tumors, increase in cellular immune response, fatty liver degeneration, and changes in clotting factors and leukocyte count; [RTECS] See Dichlone.

Skin Irrit. 2 (100%)

Eye irritation - category 2

Acute toxicity (Inhalation: Dusts and mists) - Category 4

Skin Irrit. 2

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rest. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

TERRESTRIAL FATE: An average Rf value of 0.00, obtained in a soil TLC bioassay, indicates that chloranil is immobile in this soil system(1). Chloranil adsorbed strongly to two soil samples; amending the two soil samples with humic material resulted in the increased adsorption of the pesticide(2). Based on limited data, chloranil is expected to biodegrade in soil(SRC). Chloranil at 50 ug/ml had half-lives of 6, 4, and 5 days in non-sterile samples of soil, sewage, and fresh water, respectively(3). The rates of disappearance of chloranil were slightly lower in the sterilized samples. Different degradation products were reported for the non-sterile samples(3). Volatilization of chloranil is not expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.6X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(5). Volatilization from dry soil surfaces(SRC) should not occur based on a measured vapor pressure of 5.1X10-6 mm Hg(4). Chloranil should photodegrade on soil surfaces; chloranil, exposed to sunlight, forms the tetrachlorohydroquinone and the trichlorohydroxyquinone in 68% and 28% yields, respectively(6).

AQUATIC FATE: Adsorption to organic matter in the water is expected(SRC); chloranil was shown to bind to dissolved humic acids in water either through a charge-transfer or electron donor-acceptor mechanism(1). Based on limited data, chloranil should biodegrade in water(SRC). Chloranil at 50 ug/ml had measured half-lives of 6, 4, and 5 days in non-sterile samples of soil, sewage, and fresh water, respectively(2). The rates of disappearance of chloranil were slightly lower in the sterilized samples. Different degradation products were reported for the non-sterile samples(2). Chloranil is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 6.6X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(3) and water solubility(4). An estimated BCF value of 30(1,SRC), from a measured water solubility(4), suggests that chloranil may moderately bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloranil, which has a measured vapor pressure of 5.1X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chloranil 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 14 days(3,SRC). Particulate-phase chloranil may be physically removed from the air by wet and dry deposition(SRC).

Cough. Sore throat.

Redness.

Redness. Pain.

Diarrhoea.

An average Rf value of 0.00, obtained in a soil TLC bioassay (Hagerstown silty clay loam with 2.5% organic matter, 39.5% clay, pH of 6.8), indicates that chloranil is immobile in this soil system(1). Chloranil adsorbed strongly onto two soil samples (A= pH 7.4, organic carbon of 0.5%; B= pH 8.2, organic carbon 1.0%); adsorption was increased when the two soil samples were amended with humic material. Retention of chloranil was believed due to the chemical reactivity characteristic of its quinonic structure(2). Chloranil was shown to bind to dissolved humic acids in water through either a charge-transfer or electron donor-acceptor mechanism(3).

TOXIC DOSES PRODUCE WATERY DIARRHEA, CENTRAL NERVOUS DEPRESSION, COMA, & DEATH. SKIN IRRITANT IN HIGH CONCN...

The quinones tetrachloro-1,4-benzoquinone (1,4-TCBQ) and its glutathione conjugate (GS-1,4-TCBQ) are potent irreversible inhibitors of most human glutathione S-transferase (GST) isoenzymes. Human pi, psi, and mu are almost completely inhibited at a molar ratio 1,4-TCBQ/GST = 2/1. The isoenzyme B1B1 was inhibited up to 75%, and higher concn (1,4-TCBQ/GST = 6/1) were needed to reach this maximum effect. For these isoenzyme 75-85% of the maximal amount of inhibition was already reached on incubation of equimolar ratios of 1,4-TCBQ and subunit GST, while approx 1 nmol (0.82-0.95) 1,4-(U-(14)C-TCBQ per nmol subunit GST could be covalently bound. ... GST isoenzymes possess only one cysteine in or near the active site of GST, which is completely responsible for the inhibition. ... Human isoenzyme B2B2 which has no cysteine, was not inhibited and no 1,4TCBQ was inhibited to it. The rate of inhibition was studied at 0 deg: 1,4-TCBQ, trichloro-1,4-benzoquinone and GS-1,4-TCBQ all inhibit GST very fast. Especially for B1B1, the inhibition of glutathione conjugate is significantly faster than inhibition by 1,4-TCBQ: the glutathione moiety seems to target the quinone to the enzyme. ...

EXPOSURE OF AQ PENTACHLOROPHENOL SOLN TO EITHER SUNLIGHT OR LAB ULTRAVIOLET LIGHT RESULTED IN DEGRADATION. DISPLACEMENT OF CHLORIDE BY HYDROXIDE PRODUCED TETRACHLOROHYDROQUINONE WHICH WAS SUBSEQUENTLY AIR-OXIDIZED TO CHLORANIL.

PENTACHLORONITROBENZENE WAS DECOMPOSED IN AIR & NITROGEN AT 400 °C. MAJOR DECOMPOSITION PRODUCT WAS HEXACHLOROBENZENE. TETRACHLOROBENZOQUINONE WAS ALSO PRODUCED.

Chloranil's use as a fungicide and seed protectant with secondary insect repellent and bactericidal effects(1) may result in its direct release to the environment(SRC). Chloranil's production and use as a dye intermediate, in the manufacture of electrodes for pH measurements, or as a reagent(2) will result in its release to the environment through various waste streams(SRC).

Chloranil at 50 ug/ml had half-lives of 6, 4, and 5 days in non-sterile samples of soil, sewage, and fresh water, respectively. The rates of disappearance of chloranil were slightly lower in the sterilized samples. In sea water, complete disappearance required 28 weeks in both sterile and non-sterile samples; degradation was faster initially, through the first 15 weeks, in non-sterile samples suggesting some biodegradation was occurring(1). Non-sterile samples in all cases gave an increased number of degradation products(1).

An estimated BCF value of 30 was calculated for chloranil(SRC), using a measured water solubility of 250 mg/l(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that moderate, not high bioconcentration in aquatic organisms may occur(SRC).

The Henry's Law constant for chloranil is estimated as 6.6X10-9 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 5.1X10-6 mm Hg(1), and water solubility, 250 mg/l(2). This value indicates that chloranil will be essentially nonvolatile from water surfaces(3,SRC). Chloranil's values for vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC).

...DRY DUST APPLIED TO RABBIT EYES IS SAID TO HAVE CAUSED CORNEAL NECROSIS.

INGESTION MAY CAUSE DIARRHEA &/OR CNS DEPRESSION.

CHLORANIL ORALLY ADMIN TO MICE AT CONCN OF 80-215 MG/KG/DAY WAS QUESTIONABLY TUMORIGENIC. /FROM TABLE/

GROUPS OF 30 XENOPUS LAEVIS EMBRYOS @ TAIL-BUD STAGE EXPOSED TO 1.25-1.75 PPM FOR 1-10 DAYS SHOWED ABNORMALITIES OF OTOLITH, OPTIC CUP, & GENERAL PIGMENTATION. THEY HAD SPORADIC CONVULSIVE MOVEMENT & WERE UNABLE TO MAINTAIN PROPER BALANCE.

For more Non-Human Toxicity Excerpts (Complete) data for CHLORANIL (7 total), please visit the HSDB record page.

FUNGICIDAL PROPERTIES... ACTIVITY ATTRIBUTED TO ROLE IN OXIDATION-REDUCTION PROCESSES AND TO INHIBITION OF CARBOXYLASES.

... Tetrachloro-1,4-benzoquinone, a cmpd previously shown to inactivate glutathione S-transferases very efficiently by covalent binding in or close to the active site, completely prevented the alkylation of the enzyme by iodoacetamide, indicating that the reaction had taken place with the cysteine residues. ... Evidence was obtained for the covalent binding of three benzoquinone molecules per subunit, ie equivalent to the number of cysteine residues present. This threefold binding /resulted/ with a fourfold molar excess of the benzoquinone, illustrating high reactivity of this cmpd. Comparison of the number of amino acid residues modified by tetrachloro-1,4-benzoquinone with the decr of catalytic activity revealed an almost complete inhibition after modification of one cysteine residue.

MICROBIAL DEGRADATION OF SODIUM PENTACHLOROPHENATE WAS STUDIED IN MIXED MICROBIAL COMMUNTIES & IN AXENIC BACTERIAL CULTURE. EVIDENCE WAS OBTAINED FOR THE PROBABLE PARTICIPATION OF 2,6-DICHLOROHYDROQUINONE & TETRACHLOROHYDROQUINONE OR TETRACHLOROBENZOQUINONE AS INTERMEDIATES IN CATABOLISM OF SODIUM PENTACHLORPHENATE.

A SMALL AMT OF CHLORANIL WAS FOUND IN THE URINE OF ANIMALS ADMIN SODIUM PENTACHLOROPHENOL. CHLORANIL WAS ALSO DETECTED IN INTESTINAL TISSUES & LIVERS OF MICE.

WHEN CHLORANIL WAS ADDED TO CULTURES OF ASPERGILLUS NIGER, NEUROSPORA CRASSA, OR MUCOR SP, RAPID BUILDUP OF FREE RADICALS...OBSERVED BY ELECTRON SPIN RESONANCE SPECTROSCOPY. YEAST SUSPENSIONS & EXTRACTS ALSO EXHIBIT RAPID BUILDUP & DECAY OF FREE RADICAL. THIS CORRESPONDS TO SEMIQUINONE.

YIELDS TETRACHLOROBENZOSEMIQUINONE IN ESCHERICHIA). /FROM TABLE/

Cultures of the basidiomycete Mycena avenacea TA8480 were shown to metabolize pentachlorophenol, tetrachloro-p-hydroquinone and 2,3,5,6-tetrachloro-p-benzoquinone. The first metabolite of the pentachlorophenol degradation pathway was identified as 2,3,5,6-tetrachloro-p-hydroquinone. ... Dechlorination of 2,3,5,6-tetrachloro-p-hydroquinone yielded 3,5,6-trichloro-2-hydroxy-p-benzoquinone. ...

Used as a dye intermediate, oxidizing agent, vulcanizing agent, dehydrogenation reagent, and veterinary topical medication; Also used as a fungicide in seed treatment and foliar application and to make chloranil electrodes for pH measurements; [HSDB]

Farming (Pesticides) [Category: Industry]

IN MFR OF CHLORANIL ELECTRODES FOR PH MEASUREMENTS; TO MFR CMPD USED IN DYE INDUSTRY; AS REAGENT FOR PAMAQUINE (PLASMOCHIN) IN URINE (BLUE COLOR). FUNGICIDE

AS OXIDIZING AGENT

ON MOIST ECZEMAS OF DOGS & IN FLEA POWDERS

FUNGICIDE IN SEED TREATMENT; FOLIAR APPLICATION

2023: <50,000 lb

(1975) 9.08X10+7 GRAMS (CONSUMPTION)

REACTION OF CYCLOHEXANE AND HYDROGEN CHLORIDE MIXED WITH OXYGEN, PASSED OVER AN OXIDATION CATALYST

...FROM PARA-PHENYLENEDIAMINE OR PHENOL BY TREATING WITH POTASSIUM CHLORATE & HCL. BECAUSE OF ITS GREAT RESISTANCE TO FURTHER OXIDN, CHLORANIL IS FORMED AS FINAL PRODUCT OF CHLORATE-HCL OXIDN OF MANY AROMATIC CMPD. FOR COMPREHENSIVE LIST SEE HUNTRESS, ORGANIC CHLORINE CMPD. LAB PROCEDURE STARTING WITH PHENOL OR PARA-CHLOROPHENOL.

(A) BY OXIDN OF TRICHLOROPHENOL WITH CHROMIC ACID. (B) BY TREATING PHENOL WITH HYDROCHLORIC ACID & POTASSIUM CHLORATE. TETRACHLOROQUINONE IS SEPARATED FROM TRICHLOROQUINONE SIMULTANEOUSLY PRODUCED BY WATER SOLUBILITY OF LATTER.

From phenol, p-chlorophenol, or p-phenylenediamine by treatment with potassium chlorate and hydrochloric acid.

For more Methods of Manufacturing (Complete) data for CHLORANIL (7 total), please visit the HSDB record page.

Pharmaceutical and Medicine Manufacturing

2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrachloro-: ACTIVE

COMPATIBLE WITH OTHER COMMON SEED PROTECTION PREPARATIONS.

CHLORANIL IS...USED AS SEED TREATMENT FOR VARIETY OF FIELD & VEGETABLE CROPS @ FROM 3-12 OZ/100 LB OF SEED APPLIED DRY OR AS SLURRY. IT IS ALSO USED AS SPRAY FOR TURF, FOR MILDEWS OF CABBAGE & CANTALOUPE, & FOR CELERY & TOBACCO SEEDLINGS.

TWO OF CHLORINE ATOMS IN PARA POSITION ARE EASILY SUBSTITUTED, & COMPD SUCH AS 2,5-DIANILINO-3,6-DICHLORO-QUINONE ARE MUCH USED IN DYE INDUSTRY.

Not sold in many countries