1,4-Dichloro-2,5-dimethoxybenzene

207.05

207.05

220-222-3

1U6950BY9X

151546

3077

DTXSID2024793

Colorless crystals

2909309013

18.5

3.44 /Estimated/

Chloroneb appears as white to tan solid or beige powder. Musty odor. (NTP, 1992)

1.66 g/cm³

133-135 °C

268 °C

>100 °C

1.524

H2O: <0.01 g/100 mL at 23 ºC

0-6°C

3X10-3 mm Hg @ 25 deg C

Oral-Rat LD50: 11000 mg/kg

Flammable; burning produces toxic chloride gas

Musty odor

Henry's Law constant = 1.02X10-4 atm-cu m/mole @ 25 °C /Estimated/

Hydroxyl radical reaction rate constant = 5.48X10-12 cu cm/molecule-sec @ 25 °C /Estimated/

Insoluble in water.

Ethers

CHLORONEB is stable at temperatures up to 514° F, in water in the presence of dilute acids or alkalis, and in the common organic solvents. It is subject to microbial decomposition in soil under moist conditions.

9

UN30779/PG3

2

51/53

61

CZ4750000

N

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

Stable.

P273

H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

PEASE HL, REISER RW; CHLORONEB; ANAL METHODS PESTIC PLANT GROWTH REGUL 7: 657-64 (1973). A REVIEW WITH 3 REFERENCES ON THE RECOMMENDED METHODS OF CHLORONEB DETERMINATION IN FORMULATIONS & RESIDUES.|California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Chloroneb as of July 13, 2003.

This chemical is combustible. (NTP, 1992)

|H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501|Aggregated GHS information provided by 131 companies from 2 notifications to the ECHA C&L Inventory.|H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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 store this material under ambient temperatures. (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)|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/

Chloroneb and its formulated products will catch fire /when exposed to flames/.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/

Avoid contact with skin or clothing. Wash hands and face thoroughly with soap and water after use and before eating or smoking.|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...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 chemical protective clothing. /Organochlorine pesticides, solid, toxic/|Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/|If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources 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. /Organochlorine pesticide, liquid/

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

SEDIMENT: Bed sediment samples collected from 23 sites within the South Platte River basin during August-November 1992 and August 1993 did not contain concentrations of chloroneb above the detection limit(1). Bed sediment samples from 18 sites on or near the floor of the San Joaquin Valley, CA, collected in October 1992, did not contain detectable concentrations of chloroneb (minimum reporting limit=5 ug/kg dry weight)(2).

URBAN/SUBURBAN: Chloroneb was not detected (detection limit=0.2 ng/cu m) in 24-hour ambient air samples collected in Kitakyushu City, Japan, on either 21 to 22 July 1991 or 23 to 24 April 1992; the sampling location was approximately 10 km from an agricultural area(1).

practically nontoxic

LD50 Rat oral >11,000 mg/kg|LD50 Rabbit percutaneous >5000 mg/kg

Chloroneb's production may result in its release to the environment through various waste streams; it's use as a systemic soil- and seed-fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 714(2) to 1,653(3), indicate that chloroneb is expected to have low mobility in soil(SRC). Volatilization of chloroneb from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 0.003 mm Hg at 25 °C(4) and its water solubility, 8 mg/L at 25 °C(5). Chloroneb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure value(5). In a field study, half-lives ranging from 3 to 6 months were measured for chloroneb in soil(6). More rapid biodegradation was reported in a laboratory study where half-lives of 4.3 and 2.7 days were reported in a silty clay loam soil(7).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 714(2) to 1,653(3), indicate that chloroneb is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.0X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 0.003 mm Hg at 25 °C(5) and its water solubility, 8 mg/L at 25 °C(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 17 hours and 9 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 190(SRC), calculated from its water solubility value(6) and a regression-derived equation(4), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data for chloroneb in aquatic environments were not located. While half-lives in a laboratory soil study indicate that chloroneb can be readily biodegraded (several days)(8), half-lives up to 180 days have been reported in a soil field study(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroneb, which has a vapor pressure of 0.003 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroneb 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 3 days(SRC), calculated from its rate constant of 5.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of chloroneb with photochemically-produced hydroxyl radicals has been estimated as 5.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chloroneb is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). The direct photolysis of chloroneb is not likely to be a major fate process(SRC) as most haloaromatics do not absorb strongly above 300 nm and their direct photolysis often proceeds with very low quantum efficiency(3).

An estimated BCF of 190 was calculated for chloroneb(SRC), using a measured water solubility of 8 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered physically or chemically once released into the environment.

1.26e+03 L/kg|Koc values of 1,653(1), 1,260(2), 1,200(3), and 714(4) were measured for chloroneb in soil(SRC). According to a classification scheme(5), these estimated Koc values suggest that chloroneb is expected to have low mobility in soil. In a soil TLC plate study using Hagerstown silty clay loam soil (pH 6.8, 2.5% organic matter, 39.5% clay), chloroneb was immobile(6). In a field study, chloroneb was incorporated into a Keystone silt loam to a depth of 2 to 3 inches. After 6 months, nearly all of the chloroneb remained in the treated layer of soil(7).

The Henry's Law constant for chloroneb is estimated as 1.0X10-4 atm-cu m/mole(SRC) from its vapor pressure,0.003 mm Hg(1), and water solubility, 8 mg/l(2). This Henry's Law constant indicates that chloroneb is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 17 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 9 days(SRC). Chloroneb's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Chloroneb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Chloroneb was not detected (detection limit not reported) in groundwater sampled from 14 wells in California from 1984 to 1989(1). Chloroneb was not detected (detection limit not reported) in groundwater sampled from 5 wells in two California counties during July 1994 to June 1995(2). Chloroneb was not detected (minimum reporting limit=0.70 ug/L) during the 5-year National Survey of Pesticides in drinking water wells (783 rural domestic wells and 566 community water system wells)(3).|SURFACE WATER: Chloroneb was not detected (detection limit=0.01 ng/mL) in 10 water samples collected from 9 golf courses around Singapore during April and May 1994; 6 samples from artificial ponds or lakes in the golf course and 4 samples were from fresh rain water accumulated beside the fairways(1). Water samples from the mouth of the Shinano River, Japan, were collected once a month from May to September 1996; chloroneb was not detected in any samples (limit of detection=0.01 ug/mL)(2).

Chloroneb was not detected (detection limit of 0.025 ppm) during a pesticide residue screening program on 6,970 produce samples representing 81 varieties of vegetables and fruits (80% domestic, 20% foreign)(1).

Occupational exposure to chloroneb may occur through inhalation of dust and dermal contact with this compound at workplaces where chloroneb is produced or used. (SRC)

In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Solid Organochlorines/|Chloroneb was fed to rats, cows and dogs. In urine, metabolite found was 2,5-dichloro-4-methoxyphenol in free and conjugated form probably as glucuronides and sulfates. This was not detected in hydrolyzed feces. No metabolites were found in milk.|It is a systemic fungicide which is taken up by roots, concentrated in the roots and in lower stem portions, rendering them fungistatic.

Chloroneb was fed to rats, cows and dogs. In urine, metabolite found was 2,5-dichloro-4-methoxyphenol in free and conjugated form probably as glucuronides and sulfates. This was not detected in hydrolyzed feces. No metabolites were found in milk. After incubation of chloroneb with 10,000g supernate fraction of beef liver, the same metabolite was observed. Snapbeans, grown in a greenhouse, were treated with (14)C-ring-labeled chloroneb. Analysis of plant tissues showed presence of 2,5-dichloro-4-methoxyphenol, 2,5-dichlorohydroquinone and 2,5-dichloroquinone.|2,5-Dichloro-4-methoxyphenol was isolated as the only metabolite of chloroneb in urine of dogs, rats, and cows maintained on chloroneb-containing diets. 2,5-Dichloro-4-methoxyphenol was found in both free form and as conjugates, presumably glucuronides and sulfonates.|Chloroneb ... is metabolized to its corresponding p-quinone in plants.|/Young bean plants metabolized chloroneb/ ...to 2,5-dichloro-4-methoxyphenol (DCMP) and then converted to the beta-d-glucoside. ...Eight organisms demethylated chloroneb and methylated 2,5-dichloro-4-methoxyphenol (DCMP) /during incubation/: Fusarium solani (F pisi), Fusarium solani (F phaseoli), Mucor ramannianus, Cephalosporium gramineum, Aspergillus fumigatus, Verticillium albo-otrum, Cephalosporium gregatum, and Chaetomium globosum. Six organisms were capable only of demethylating chloroneb: Sclerotinia sclerotiorum, Helminthosporium victoriae, Corynebacterium fascians, Stemphyllium sarcinaeforme, Cladosporium cucumerinum, and Helminthosporium sativum. Three organisms were capable of methylating 2,5-dichloro-4-methoxyphenol (DCMP) but did not degrade chloroneb to decomposition: Trichoderma viride, Penicillium frequentans, and Rhizoctonia solani. In other studies, mycelium of Rhizooctonia solani degraded chloroneb to 2,5-dichloro-4-methoxyphenol (DCMP) ...Neurospora crassa metabolized chloroneb slowly to a compound thought to be an aglycoside.|... Chloroneb was stable when incubated with rumen fluid up to 6 hr. A metabolite was produced with the fungicide was incubated with the 10,000-G superntant beef liver fraction. Its gas chromatographic retention time was identical to that of the 2,5- dichloro-4-methoxyphenol metabolite mentioned above. In hydrolyzed urine, a peak having the identical retention time of this phenol metabolite was also observed.

Fungitoxicity is due to specific inhibition of DNA polymerization.

SYMPTOMS: Symptoms of exposure to this compound include vomiting, tremors and convulsions. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of chlorine. (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)

Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. /Organochlorine insecticides/|Persons exceptionally exposed to organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. If convulsions occur, place the victim in the left lateral decubitus position with the head down. Move away furniture or other solid objects that may be a source of injury. If jaw movements are violent, place padded tongue blades between the teeth to protect the tongue. Whenever possible, remove dentures and other removable dental work. Aspirate oral and pharyngeal secretions, and, when possible, insert an oropharyngeal airway to maintain an open passage unobstructed by the tongue. Minimize noise and any manipulation of the patient that may trigger seizure activity. Administer oxygen by mask. Maintain pulmonary gas exchange by mechanically assisted ventilation whenever respiration is depressed. /Solid organochlorine insecticides/

chloroneb

Technical material 90% purity. ... Demosan 65w: wettable powder, 65% active ingredient; demosan 10d: dust, 10% active ingredient; tersan sp: turf fungicide, 65% active ingredient.|Wettable powders and flowable concentrate|Nuflo D|Soil fungicide 1823|For more Formulations/Preparations (Complete) data for CHLORONEB (10 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Chloroneb (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|Suggested soil control of seedling diseases of cotton: demosan 65w: method: in-furrow spray; rate/acre: 1.3-2.0 lb active ingredient (ai); demosan 10d: method: in-furrow dust; rate/acre: 1-2 lb (ai); demosan 65w: method: planter-box or hopper box; rate/acre: 6.5 ounces/100 lb (ai) (seed overcoat). /From table/

DETERMINATION OF CHLORONEB RESIDUES BY MICROCOULOMETRIC GC.|Product and residue analysis may be determined by GLC.|Method: EPA-TSC/NERL 508, Determination of Chlorinated Pesticides in Water by Gas Chromatography with an Electron Capture Detector; Analyte: chloroneb; Matrix: ground water and finished drinking water; Method Detection Limit: 0.5 ug/L.|Method: EPA-NERL 525.2, Determination of Organic Compounds in Drinking Water by Liquid-Solid Extraction and Capillary Column Gas Chromatography/Mass Spectrometry; Analyte: chloroneb; Matrix: finished drinking water, source water, drinking water in any treatment stage; Method Detection Limit: 0.088 ug/L.|For more Analytic Laboratory Methods (Complete) data for CHLORONEB (8 total), please visit the HSDB record page.

Agrochemicals -> Fungicides