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Chloroneb
CHLORONEB · 1,4-DICHLORO-2,5-DIMETHOXYBENZENE · nuflod · Teremec · Demosan · Demasan · CHLORNEB · terraneb
Identifikatoren & physikalische Daten
| CAS No. | 2675-77-6 |
|---|---|
| Summenformel | C8H8Cl2O2 |
| Durchschnittliche Molmasse | 207,05 g/mol |
| Monoisotopische Masse | 205,99013486 g/mol |
| SMILES | COc1cc(Cl)c(OC)cc1Cl |
| InChIKey | PFIADAMVCJPXSF-UHFFFAOYSA-N |
| PubChem CID | 17581 |
| ChEMBL | CHEMBL3183369 |
| ChEBI | CHEBI:3628 |
| EC No. | 220-222-3 |
| DTXSID | DTXSID2024793 |
| Lokaler Name | Chloroneb |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 18,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 127 |
| SpringerMaterials Properties | Chemical shift |
| Pestizide | FungicidesActive substance -> EU Pesticides database: Not approvedPesticides -> FungicidesPesticide (Chloroneb) -> USDA PDB |
| LogP (Verteilungskoeffizient) | log Kow = 3.44 /Estimated/3.46 |
| Geruch | Musty odor |
| Dichte | 1.66 (NTP, 1992) - Denser than waterwill sink1.3354 (rough estimate) |
| Color/Form | Colorless crystals |
| Löslichkeit | 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 dichloromethaneIn water, 8.0 mg/L @ 25 °C<0.01 g/100 mL at 23 ºC |
| Flammpunkt | 322 °F (NTP, 1992)>100 °C |
| Siedepunkt | 514 °F at 760 mmHg (NTP, 1992)268 °C268°C |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen chloride/ |
| Schmelzpunkt | 271 to 275 °F (NTP, 1992)133-135 °C133-135°C |
| Dampfdruck | 0.003 mmHg at 77 °F7 mmHg at 284 °F (NTP, 1992)0.01 [mmHg]3X10-3 mm Hg @ 25 °C |
| Brechungsindex | 1.5537 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Solid |
| Farbe | White to off-white |
| BRN | 1952749 |
| Henry-Konstante | 9.7×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C8H8Cl2O2/c1-11-7-3-6(10)8(12-2)4-5(7)9/h3-4H,1-2H3 |
| InChIKey | PFIADAMVCJPXSF-UHFFFAOYSA-N |
| SMILES | COc1cc(Cl)c(OC)cc1Cl |
| CAS Datenbank | 2675-77-6(CAS DataBase Reference) |
| NIST chemische Informationen | 1,4-Dichloro-2,5-dimethoxybenzene(2675-77-6) |
| EPA chemische Informationen | Chloroneb (2675-77-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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] |
|---|---|
| Regulatorische Informationen | Chloroneb is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141) |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Brandpotenzial | Chloroneb and its formulated products will catch fire /when exposed to flames/. |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include vomiting, tremors and convulsions. |
| Gefahrenübersicht | A skin irritantNo human cases of systemic poisoning have been reported[EPA Pesticides] Low acute toxicityA skin sensitizerUnlikely to pose a dietary cancer risk[EPA REDs] May cause irritationMay cause CNS depression[MSDSonline] |
| Reaktive Gruppe | Ethers |
| Special Reports | PEASE HL, REISER RWCHLORONEBANAL 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 RegulationToxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Chloroneb as of July 13, 2003. |
| FIFRA-Anforderungen | 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: beanbean, foragebeet, sugar, rootsbeet, sugar, topscattle, fatcattle, meatcattle, meat byproductscotton, foragecotton, undelinted seedgoat, fatgoat, meatgoat, meat byproductshot, fathog, meathog, meat byproductshorse, fathorse, meathorse, meat by productsmilksheep, fatsheep, meatsheep, meat byproductssoybeanand 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: 0007Pesticide type: fungicideRegistration Standard Date: 09/01/1980 PB81-123804Case 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): chloronebData Call-in (DCI) Date(s): 01/09/1992, 03/03/1995, 10/13/1995AI 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. |
| Reactivity Profile | 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. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Aquatic Chronic 2 (93%)Hazardous to the aquatic environment (Acute) - Category 2 |
| Brandbekämpfung | 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) |
| Erste Hilfe | 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. |
| Brandbekämpfungsverfahren | 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/ |
| Lagerbedingungen | Store in a cool, dry place. |
| Reinigungsverfahren | 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/ |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Preventive Measures | 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/ |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Allowable Tolerances | 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 ppmbeet, sugar, roots 0.1 ppm (N)beet, sugar, tops 0.1 ppm (N)cattle, fat 0.2 ppmcattle, meat 0.2 ppmcattle, meat byproducts 0.2 ppmcotton, forage 2 ppmcotton, undelinted seed 0.1 ppm (N)goat, fat 0.2 ppmgoat, meat 0.2 ppmgoat, meat byproducts 0.2 ppmhot, fat 0.2 ppmhog, meat 0.2 ppmhog, meat byproducts 0.2 ppmhorse, fat 0.2 ppmhorse, meat 0.2 ppmhorse, meat by products 0.2 ppmmilk 0.05 ppm (N)sheep, fat 0.2 ppmsheep, meat 0.2 ppmsheep, meat byproducts 0.2 ppmsoybean 0.1 ppm (N)and soybean, forage 2 ppm. |
| Personal Protective Equipment (PPE) | 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, liquidOrganochlorine pesticide, solid, toxic/ |
| Ökotoxizitätswerte | LC50 Mallard duck oral >5000 mg/kgLC50 Japanese quail oral >5000 mg/kgLC50 Bluegill sunfish >4200 mg/L/46 hr /Conditions of bioassay not specified in source examined/EC50 Daphnia magna (Water fleaintoxication, immobilization) 6.19 ppm/48 hr (95% confidence interval: 5.8-6.64 ppm)staticFor more Ecotoxicity Values (Complete) data for CHLORONEB (6 total), please visit the HSDB record page. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 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). |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Soil Adsorption/Mobility | 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). |
| Atmospheric Concentrations | 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 1992the sampling location was approximately 10 km from an agricultural area(1). |
| Artificial Pollution Sources | Chloroneb's production may result in its release to the environment through various waste streamsit's use as a systemic soil- and seed-fungicide(1) will result in its direct release to the environment(SRC). |
| Environmental Biodegradation | 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/Soil Concentrations | 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). |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Environmental Bioconcentration | 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. |
| Volatilization from Water/Soil | 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). |
| Landesrichtlinien für Trinkwasser | (FL) FLORIDA 91 ug/l |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN3077 9/PG 3 |
| RTECS-Nr. | CZ4750000 |
| R-Sätze (R) | 51/53 |
| Gefahrensymbole | N |
| Sicherheitshinweise (S) | 61 |
| Gefahrenklasse | 9Aquatic Chronic 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 2675-77-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Chloroneb was developed by Du Pont de Nemours Co. in 1967. It differs from the compounds described above in that it does not contain nitro-groups. In common with other chlorobenzene fungicides, chloroneb has a low mammalian toxicity and a significant vapor pressure so that it was used as a soil fungicide in the culture of beans, cucumber, and cotton (20). In contrast with the nitrobenzene compounds, Phytophthora spp. are rather sensitive to chloroneb. Pythium spp. vary in sensitivity to chloroneb. Because of its low water solubility, chloroneb is only very weakly systemic (21,22).