Chloranil

245.88

245.88

393006

204-274-4

01W5X7N5XV

0780

8432

DTXSID2020266

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

29147090

34.1

3-4.9

Clear Liquid

1.97 g/cm³

290 °C

Sublimes

>100℃

1.595

H2O: insoluble

Store below +30°C.

Vapour pressure, Pa at 25°C:

Relative vapour density (air = 1): 8.5

Oral-Rat LD50: 4000 mg/kg

Combustion produces toxic chloride gas

148.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

REACTS WITH ALKALIES TO FORM SALTS OF CHLOROANILIC ACID|Stable in closed containers. Decomposed by alkalies. Slowly decomposed by sunlight. Stable in acidic media.

Insoluble in water.

Halogenated Organic Compounds

CHLORANIL is sensitive to excessive light and heat. This chemical is incompatible with strong oxidizing agents. It reacts with alkalis. (NTP, 1992)

Non-corrosive

III

9

UN 3077 9/PG 3

2

36/38-50/53-20

37-60-61-22

DK6825000

Xi,N,Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

GOOD STORAGE STABILITY

P273-P305 + P351 + P338-P501

H315-H319-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.

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.

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, and P501|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501|Aggregated GHS information provided by 238 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]|P260, P261, P271, P280, P304+P312, P304+P340, P305+P351+P338, P310, P312, P314, P403+P233, P405, and P501

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.

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. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

MAY BE IRRITATING TO SKIN, MUCOUS MEMBRANES.

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.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. Exposure at high levels could cause unconsciousness.

PREVENT DISPERSION OF DUST! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN!

Avoid inhalation of dust and mist.

Protective gloves.

Wear safety goggles.

moderately

ORAL LD50 OF TECHNICAL CHLORANIL FREE OF TETRACHLORODIBENZO-P-DIOXINS WAS 6951 MG/KG IN FEMALE RATS.

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).

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).

...QUINONE PHOTOLYSIS... REDN TO HYDROQUINONE & DIMERIZATION OF NAPHTHOQUINONES TO CYCLOBUTANE DERIV ARE KNOWN, & REPLACEMENT OF CHLORINE SUBSTITUENTS WITH HYDROXYLS, AS DEMONSTRATED IN CONVERSION OF CHLORANIL TO CHLORANILIC ACID...APPEARS TO OCCUR READILY.|The rate constant for the vapor-phase reaction of chloranil with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 14 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Chloranil was not degraded following exposure to UV light for 1 hour(2). When chloranil, in ethanol, is exposed to sunlight it forms the tetrachlorohydroquinone and the trichlorohydroxyquinone in 68% and 28% yields, respectively(3). Rates of disappearance in sterile soil were slightly lower than in non-sterile soil(4). In seawater, complete disappearance required 28 days in both sterile and non-sterile samples; some biodegradation occured in non-sterile samples(4).

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).

208.93 L/kg|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).

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).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2097 workers (762 of these are female) are potentially exposed to chloranil in the USA(1).

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG; BETWEEN 1 OZ & 1 PINT FOR 70 KG PERSON (150 LB).

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

POORLY ABSORBED /WHEN ADMIN ORALLY IN RATS/. ...NOT ABSORBED PERCUTANEOUSLY.

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. ...

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.

SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, respiratory system and digestive system. Other symptoms include watery diarrhea, central nervous system depression, liver damage, coma and death. ACUTE/CHRONIC HAZARDS: This compound is an irritant of the mucous membranes and skin. It may be harmful by eye or skin contact, inhalation or ingestion. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, chlorine and hydrogen chloride gas. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

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.

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. ...

2,3,5,6-Tetrachloro-1,4-benzoquinone

The substance can be absorbed into the body by inhalation of dust and by ingestion.

Cough. Sore throat.

Redness.

Redness. Pain.

FUNGICIDE, OF WHICH 50% IS USED IN SEED TREATMENT FOR FIELD CROPS, AND 50% IN SEED TREATMENT FOR VEGETABLES (1975)

Wettable powder; dust; seed dressing powder.

Synthetic dye and pigment manufacturing|2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrachloro-: ACTIVE|T - indicates a substance that is the subject of a final TSCA section 4 test rule.|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

FOR RESIDUE ANALYSIS, (A) STRIP TREATED SEED WITH ACETONE, ADD ANHYD DIETHYLAMINE & MEASURE YELLOW COLOR @ 450 NM; (B) TREAT BENZENE SOLN WITH ALKALI & MEASURE COLOR OF AQ LAYER @ 545 NM.|GC ANALYSIS OF PESTICIDES IS DISCUSSED WITH REFERENCE TO SAMPLE PREPARATION.|Analysis of products: Reduction of chloranil with potassium iodide and potentiometric titration of the liberated iodine with sodium thiosulphate or total chlorine determination by the Stpanov method or Parr bomb decomposition.|Analysis of residues: Extraction with benzene, clean-up of the extract, reaction with diphenyl-p-phenylenediamine to give a blue colour, transfer of the dye into the aqueous-acid phase, and determination by spectrophotometry at 700 nm.|EPA-B Method PMD-TLC. Thin-Layer Chromatography Systems for Identification of Pesticides-System 2.