Chloroneb

Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fungicides

Pesticide (Chloroneb) -> USDA PDB

log Kow = 3.44 /Estimated/

3.46

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

1.66

less than 0.1 mg/mL at 73 °F (NTP, 1992)

At 25 °C: 115 g/kg acetone, 89 g/kg xylene, 118 g/kg dimethylformamide, 133 g/kg dichloromethane

In water, 8.0 mg/L @ 25 °C

514 °F at 760 mmHg (NTP, 1992)

268 °C

271 to 275 °F (NTP, 1992)

133-135 °C

0.003 mmHg at 77 °F ; 7 mmHg at 284 °F (NTP, 1992)

0.01 [mmHg]

3X10-3 mm Hg @ 25 °C

This chemical does not meet GHS hazard criteria for 7% (3 of 43) of reports.

H411 (93%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 2 notifications to the ECHA C&L Inventory.

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

A skin irritant; No human cases of systemic poisoning have been reported; [EPA Pesticides] Low acute toxicity; A skin sensitizer; Unlikely to pose a dietary cancer risk; [EPA REDs] May cause irritation; May cause CNS depression; [MSDSonline]

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.

Tolerances are established for residues of the fungicide chloroneb (1,4-dichloro-2,5-dimethoxybenzene) and its metabolite 2,5-dichloro-4-methoxyphenol (calculated as chloroneb) in or on the following food commodities: bean; bean, forage; beet, sugar, roots; beet, sugar, tops; cattle, fat; cattle, meat; cattle, meat byproducts; cotton, forage; cotton, undelinted seed; goat, fat; goat, meat; goat, meat byproducts; hot, fat; hog, meat; hog, meat byproducts; horse, fat; horse, meat; horse, meat by products; milk; sheep, fat; sheep, meat; sheep, meat byproducts; soybean; and soybean, forage.

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. Chloroneb is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0007; Pesticide type: fungicide; Registration Standard Date: 09/01/1980 PB81-123804; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): chloroneb; Data Call-in (DCI) Date(s): 01/09/1992, 03/03/1995, 10/13/1995; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Aquatic Chronic 2 (93%)

Hazardous to the aquatic environment (Acute) - Category 2

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.

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/

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: 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.

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/

Tolerances are established for residues of the fungicide chloroneb (1,4-dichloro-2,5-dimethoxybenzene) and its metabolite 2,5-dichloro-4-methoxyphenol (calculated as chloroneb) in or on the following food commodities: bean 0.1 ppm (N); bean, forage 2 ppm; beet, sugar, roots 0.1 ppm (N); beet, sugar, tops 0.1 ppm (N); cattle, fat 0.2 ppm; cattle, meat 0.2 ppm; cattle, meat byproducts 0.2 ppm; cotton, forage 2 ppm; cotton, undelinted seed 0.1 ppm (N); goat, fat 0.2 ppm; goat, meat 0.2 ppm; goat, meat byproducts 0.2 ppm; hot, fat 0.2 ppm; hog, meat 0.2 ppm; hog, meat byproducts 0.2 ppm; horse, fat 0.2 ppm; horse, meat 0.2 ppm; horse, meat by products 0.2 ppm; milk 0.05 ppm (N); sheep, fat 0.2 ppm; sheep, meat 0.2 ppm; sheep, meat byproducts 0.2 ppm; soybean 0.1 ppm (N); and soybean, forage 2 ppm.

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/

LC50 Mallard duck oral >5000 mg/kg

LC50 Japanese quail oral >5000 mg/kg

LC50 Bluegill sunfish >4200 mg/L/46 hr /Conditions of bioassay not specified in source examined/

EC50 Daphnia magna (Water flea; intoxication, immobilization) 6.19 ppm/48 hr (95% confidence interval: 5.8-6.64 ppm); static

For more Ecotoxicity Values (Complete) data for CHLORONEB (6 total), please visit the HSDB record page.

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).

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).

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).

AEROBIC: In a soil field study conducted in Deleware, US, chloroneb was reported to have a half-life of 3 to 6 months following its incorporation 2 to 3 inches from the surface of a Keyport silt loam at a concentration of 2 lb active ingredient per acre(1). About 90% of the residual activity recovered from the soil after this period was the parent chloroneb(1). Half-lives of 10 to 180 days have been reported in soil(2). Chloroneb was added to samples of Chalmers silty clay loam soil (at 5.7 ug/g), Kentucky blue grass thatch(at 8.0 ug/g), and Kentucky blue grass clippings(at 8.0 ug/g) and incubated at 25 °C at a constant moisture (26, 76, and 75%, respectively)(3). Half-lives of 2.7, 8.7, and 69.3 days were reported for the soil, thatch, and grass clipping samples, respectively, when chloroneb was added as a single compound(3). Half-lives of 4.3, 8.7, and 69.3 days were reported for the soil, thatch, and grass clipping samples, respectively, when chloroneb was added as a mixture with triadimefon and vinclozolin(3).

Chloroneb ... is metabolized to its corresponding p-quinone in ... soil.

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).

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.

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).

Tolerances are established for residues of the fungicide chloroneb (1,4-dichloro-2,5-dimethoxybenzene) and its metabolite 2,5-dichloro-4-methoxyphenol (calculated as chloroneb) in or on the following food commodities: bean; bean, forage; beet, sugar, roots; beet, sugar, tops; cattle, fat; cattle, meat; cattle, meat byproducts; cotton, forage; cotton, undelinted seed; goat, fat; goat, meat; goat, meat byproducts; hot, fat; hog, meat; hog, meat byproducts; horse, fat; horse, meat; horse, meat by products; milk; sheep, fat; sheep, meat; sheep, meat byproducts; soybean; and soybean, forage.

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. Chloroneb is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0007; Pesticide type: fungicide; Registration Standard Date: 09/01/1980 PB81-123804; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): chloroneb; Data Call-in (DCI) Date(s): 01/09/1992, 03/03/1995, 10/13/1995; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

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.

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.

Used as systemic soil and seed fungicide in treatment of cotton, bean seeds, and turf; [HSDB] Used on seed treatment for sugar beets, soybeans, cotton, and beans; Turf use on lawns and golf courses; [EPA REDs]

Farming (Pesticides) [Category: Industry]

For chloroneb (USEPA/OPP Pesticide Code: 027301) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Systemic fungicides used in treatment of cotton and bean seeds and of turf.

It is highly fungistatic to rhizoctonia spp, moderately so to pythium spp, poorly to fusarium spp. It is used as a supplemental seed treatment for beans and soyabeans (1.63 g ai/kg), for cotton (2.44 g/kg); or as an in-furrow treatment for beans and soyabeans (68 g/ha), for cotton (90-135 g/ha). It is also used on turf grass to control snow mold (Typhula spp) (1.3-2.0 kg/ha) or pythium blight (880 g/ha).

Soil- and seed-fungicide /for/ control of seedling diseases (particularly Rhizoctonia species, but also Pythium and Sclerotium species) of cotton, beans, and soya beans. Applies to the soil or used as a seed treatment. Used as a seed treatment for control of seedling diseases of sugar beet. Also used for control of snow mold (Typhula species) and Pythium blight on turf grass.

(1975) 4.54X10+7 G (CONSUMPTION)

(1976) PROBABLY GREATER THAN 2.27X10+6 G

Chloroneb may be made by (a) chlorination of p-dimethoxybenzene or (b) the reaction of quinone with HCl to give monochlorohydroquinone. Oxidation of the hydroquinone gives monochloroquinone. Addition of HCl again gives dichlorohydroquinone. Diazomethane reacts with the dichlorohydroquinone to give 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/