HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Chloramben
Naptol · AMBEN · AMIBEN · Amibin · Amoben · Ambiben · Vegaben · Vegiben
Identifikatoren & physikalische Daten
| CAS No. | 133-90-4 |
|---|---|
| Summenformel | C7H5Cl2NO2 |
| Durchschnittliche Molmasse | 206,02 g/mol |
| Monoisotopische Masse | 204,96973376 g/mol |
| SMILES | Nc1cc(Cl)cc(C(=O)O)c1Cl |
| InChIKey | HSSBORCLYSCBJR-UHFFFAOYSA-N |
| PubChem CID | 8630 |
| ChEMBL | CHEMBL446021 |
| ChEBI | CHEBI:82183 |
| EC No. | 205-123-5 |
| DTXSID | DTXSID2020262 |
| Lokaler Name | Chloramben |
Chemische & physikalische Eigenschaften
| XLogP | 2 |
|---|---|
| Polarare Oberfläche (TPSA) | 63,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 188 |
| Stoffklassen | Hazardous Air Pollutants (HAPs) |
| SpringerMaterials Properties | Fusion temperature |
| Pestizide | Pesticide -> EPA IRISHerbicidesActive substance -> EU Pesticides database: Not approvedPesticides -> Herbicides, Other |
| LogP (Verteilungskoeffizient) | log Kow = 1.111.46 |
| Geruch | ODORLESS |
| Color/Form | COLORLESS CRYSTALLINE SOLID |
| Löslichkeit | less than 0.1 mg/mL at 72 °F (NTP, 1992)water solubility = 700 mg/l @ 25 °CSOLUBILITY IN ETHANOL: 172 G/L @ 25 °CSOL IN ALKALISOLUBILITY IN ACETONE: 23.27 G/100 G @ 29 °CFor more Solubility (Complete) data for AMIBEN (9 total), please visit the HSDB record page.Acetonitrile (Slightly), DMSO (Sparingly), Metahnol (Slightly)700 mg/L (25 ºC) |
| Decomposition | DISASTER HAZARD: WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES SUCH AS /HYDROGEN/ CHLORIDE AND NITROUS OXIDES.... DANGEROUSWHEN ... /IN/ CONTACT WITH ACIDS OR ACID FUMES THEY EVOLVE HIGHLY TOXIC /HYDROGEN/ CHLORIDE FUMES. SOME ORG CHLORIDES DECOMP TO YIELD PHOSGENE. /CHLORIDES/ |
| Schmelzpunkt | 381 to 387 °F (NTP, 1992)200-201 °CMP: ABOVE 195 °C /TECHNICAL PRODUCT/200 °C |
| Dampfdruck | 0.007 mmHg at 212 °F (NTP, 1992)0.0000001 [mmHg]930 mPa @ 100 °C0.007 [mm Hg] @100 °C |
| Physical Description | Purplish white powder or light purple solid. (NTP, 1992)Colorless odorless solidTechnical product is purplish white solid[HSDB] |
| Stability/Shelf Life | RAPIDLY DECOMPOSED BY LIGHT |
| Siedepunkt | 312 °C |
| Dichte | 1.4062 (rough estimate) |
| Brechungsindex | 1.6100 (estimate) |
| Lagerbedingungen | 0-6°C |
| pKa (Säurekonstante) | 2.75±0.25(Predicted) |
| Aggregatzustand | Powder |
| Farbe | Pale Beige |
| Merck | 13,2082 |
| BRN | 2365906 |
| Henry-Konstante | 2.6×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Hauptanwendungen | peptide synthesis |
| InChI | 1S/C7H5Cl2NO2/c8-3-1-4(7(11)12)6(9)5(10)2-3/h1-2H,10H2,(H,11,12) |
| InChIKey | HSSBORCLYSCBJR-UHFFFAOYSA-N |
| SMILES | Nc1cc(Cl)cc(C(O)=O)c1Cl |
| CAS Datenbank | 133-90-4(CAS DataBase Reference) |
| NIST chemische Informationen | 3-Amino-2,5-dichlorobenzoic acid(133-90-4) |
| EPA chemische Informationen | Chloramben (133-90-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 7.1% (3 of 42) of reports.DangerH315 (92.9%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Dermatotoxicity2002/2076The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Flash point data for this compound is not available, but it is probably combustible. (NTP, 1992) |
| Brandpotenzial | Nonflammable |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: This compound emits toxic fumes when heated to decomposition. (NTP, 1992) |
| Gefahrenübersicht | Chloramben is used as a herbicide on a number of crops. Limited information is available on the health effects of chloramben. Acute (short-term) exposure to high levels of chloramben in humans results in mild to moderate dermal irritation. No information is available on the chronic (long-term) effects of chloramben in humans. Animal studies have reported effects on the liver from chronic oral exposure to chloramben. A National Toxicology Program Study reported that oral exposure to chloramben caused liver tumors in mice, but not in rats. EPA has not classified chloramben for potential carcinogenicity.Rapidly excreted after ingestion[EXTOXNET PIP - Chloramben] Little or no sensitization reactions observed in male guinea pigsHistopathological liver changes observed in 18-month dietary study of mice (LOAEL of 15 mg/kg/day for hepatic effects)[ToxPlanet: EPA - Health Effects Assessments] A mild to moderate skin irritant[HSDB] A skin and strong eye irritantTargets the liver[Sigma-Aldrich MSDS] |
| Reaktive Gruppe | Acids, Carboxylic |
| Special Reports | USEPA/ODWHealth Advisories for 50 Pesticides (8/88) NTIS No. PB88-245931DHEW/NCIBioassay of Chloramben for Possible Carcinogenicity (1977) Technical Rpt Series No. 25 DHEW Pub No. (NIH) 77-825 |
| FIFRA-Anforderungen | Tolerances are established for residues of the herbicide chloramben in or on the following raw agricultural commodities: beans driedbeans, limabeans, snapbeans, vinescantaloupescorn, field, foddercorn, field, foragecorn, field, graincucumberspeanutspeanuts, foragepeas, pigeonpeas, pigeon, foragepepperspumpkinssoybeanssoybeans, foragesquash, summersquash, wintersunflower seedsweet potatoesand tomatoes. |
| Reactivity Profile | CHLORAMBEN reacts with sodium hypochlorite solutions (NTP, 1992). |
| Luftstandards | Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Amiben is included on this list. |
| Air and Water Reactions | Insoluble in water. |
| Brandbekämpfung | Fires involving this material can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (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. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol 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 | Reuse: The use of chemical reagents as a means of disposal is not recommended at the present time. Amiben's shelf life is of sufficient duration to allow for total use of the product in accordance with label directions. On this basis, there should be few instances of small quantities of excess amiben requiring disposal. For the decontamination of amiben containers, the National Agricultural Chemical Association (USA) recommends triple rinse. "Triple rinse" means the flushing of containers three times, each time using a volume of the normal diluent equal to approx ten percent of the container's capacity and adding the rinse liquid to the spray mixture or disposing it by the method prescribed for disposing of the pesticide.Incinerate in a unit equipped with an effluent gas scrubber at a temperature above 1000 C about 1-2 seconds. Recommendable method: Incineration.Wet Oxidation: Studies of wet oxidation process applied to amiben herbicide process wastes indicate 88 to 99.5% destruction of the active ingredient. |
| Preventive Measures | Avoid skin and eye contact, inhalation of spray mists and drifting. |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Allowable Tolerances | Tolerances are established for residues of the herbicide chloramben in or on the following raw agricultural commodities: beans dried: 0.1 ppmbeans, lima: 0.1 ppmbeans, snap: 0.1 ppmbeans, vines: 0.1 ppmcantaloupes: 0.1 ppmcorn, field, fodder: 0.1 ppmcorn, field, forage: 0.1 ppmcorn, field, grain: 0.1 ppmcucumbers: 0.1 ppmpeanuts: 0.1 ppmpeanuts, forage: 0.1 ppmpeas, pigeon: 0.1 ppmpeas, pigeon, forage: 0.1 ppmpeppers: 0.1 ppmpumpkins: 0.1 ppmsoybeans: 0.1 ppmsoybeans, forage: 0.1 ppmsquash, summer: 0.1 ppmsquash, winter: 0.1 ppmsunflower seed: 0.1 ppmSweet potatoes: 0.1 ppmand tomatoes: 0.1 ppm. |
| Protective Action Criteria (PAC) | 11 [mg/m3]120 [mg/m3]690 [mg/m3] |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992) |
| Wechselwirkungen | ... CAFFEINE & CHLORAMBEN REACTED TO FORM AN INSOL COMPLEX IN STOMACH OF RATS. DECREASED GI ABSORPTION OF (14)C CAFFEINE WAS ASSOCIATED WITH AN INCOMPLETE DISSOCIATION OF THE CHLORAMBEN-CAFFEINE COMPLEX IN THE INTESTINAL TRACT. |
| Zielorgane | Hepatic |
| Umweltverhalten | LOSS /OF CHLORAMBEN/ BY LEACHING WAS MOST PRONOUNCED FROM A SANDY SOIL & WAS PROGRESSIVELY LESS AS CLAY & ORGANIC COMPONENTS INCREASED.VOLATILITY & SOIL MOVEMENT ARE MORE DEPENDENT ON FORM OF CHLORAMBEN APPLIED THAN ON SOIL TYPE. ...ALUMINUM & AMMONIUM SALTS... WERE EASILY LEACHED FROM SEVERAL ARKANSAS SOILS. METHYL & BUTOXYETHYL ESTERS RESISTED LEACHING, WHILE AMIDE WAS INTERMEDIATE WITH RESPECT TO LEACHING./FROM INVESTIGATIVE STUDIES/ ... ONE MIGHT EXPECT THAT CHLORAMBEN PERSISTENCE ... /MAY/ BE GREATEST AS THE BUTOXYETHYL ESTER IN DRY SOIL OF HIGH ORG CONTENT & LEAST FOR ... SALT IN A MOIST SANDY SOIL WHERE HIGH RAINFALL WOULD ACCELERATE LEACHING.ABSORPTION OF CHLORAMBEN TO SOIL PARTICLES SIGNIFICANTLY REDUCED HERBICIDAL ACTIVITY. ... IN ONE INSTANCE, UNDER CONTROLLED LAB CONDITIONS, A MUCK SOIL ABSORBED 29% OF APPLIED CHLORAMBEN, WHEREAS A SILTY CLAY LOAM ABSORBED ONLY 9%. ... DESORPTION OF CHLORAMBEN FROM MUCK SOILS IS SLOW.For more Environmental Fate (Complete) data for AMIBEN (9 total), please visit the HSDB record page. |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Acute Toxicity Link | Chemical: CHLORAMBEN |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=133-90-4] |
| EPA IRIS Information | ChlorambenHepatic1.5 x 10 ^-2 mg/kg-day |
| Soil Adsorption/Mobility | Amiben is expected to have anionic properties in most soil systems under environmental conditions (pH 5-9). When a column of Ella island soil type (pH 3.8, 1.6% organic matter, 82.7% sand, 12.2% silt, and 5.2% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 1.4 ppm (24.6%) and 5.0 ppm (18.5%) Amiben adsorbed to the soil, respectively. When a column of Kewaunee clay soil type (pH 6.4, 3.8% organic matter, 14% sand, 35.1% silt, and 48.7% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm 14COOH-labelled Amiben, 0.6 ppm (11.1%) and 2.6 ppm (9.8%) Amiben adsorbed to the soil, respectively. When a column of Poygan silty clay soil type (pH 7.2, 10% organic matter, 6% sand, 58.9% silt, and 33.6% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm 14COOH-labelled Amiben, 1.4 ppm (24.6%) and 5.4 ppm (20.1%) Amiben adsorbed to the soil, respectively. Therefore, soil pH and organic matter content are the primary factors controlling Amiben adsorption with higher adsorption to soil occurring either at a low pH with a low organic matter content or at a neutral pH with a high organic matter content(1).In a study of the adsorption of organic herbicides by montmorillonite, Amiben at an initial concentration of 500 umol/L exhibited no adsorption or negative adsorption to Na-montmorillonite soil (pH 6.8 and 87.0 cation exchange capacity) and H-montmorillonite soil (pH 3.35 and 73.5 cation exchange capacity)(3). Amiben was more strongly adsorbed to soil with high organic matter contentfurthermore, adsorption of Amiben to soil particles significantly reduced herbicidal activity(5). Based on adsorption studies of 12 soils, a mean Koc value of 190 was determined for amiben(1). In another adsorption study, an experimental Koc value of 21 was determined for Amiben(2). These Koc values indicate that Amiben will have high to very high mobility in soil and will leach(4). However, protonated Amiben may exhibit higher adsorption at lower pHs than its Koc values indicate(SRC). |
| Atmospheric Concentrations | Amiben was reported in ambient air between 1970 and 1971(1). |
| Human Toxicity Excerpts | MILD TO MODERATE DERMAL IRRITATION, NO EVIDENCE OF SYSTEMIC TOXICITY. |
| Artificial Pollution Sources | Amiben is used as an herbicide and it is released to the environment by ground spray or granular application(1). |
| Environmental Biodegradation | STUDIES WITH SOIL MICROFLORA INDICATED THAT BREAKDOWN OF AMIBEN OCCURRED...& THAT THE CARBOXYL WAS CLEAVED SLOWLY BUT STEADILY.MOVES READILY IN SANDY SOILS OR FOLLOWING HEAVY RAINS. ... BROKEN DOWN BY MICROORGANISMS. ... SOME PHOTOCHEMICAL LOSS IN AQUEOUS SOLN. ON MOIST SOIL LOSS REPORTED BUT SOIL MUST REMAIN MOIST FOR LOSS TO OCCUR ... AVG PERSISTENCE @ RECOMMENDED RATES: APPROXIMATELY 6 TO 8 WEEKS.When a column of Ella island soil type (pH 3.8, 1.6% organic matter, 82.7% sand, 12.2% silt, and 5.2% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 56.2 and 39.1% biodegradation was observed for Amiben, respectively. When a column of Kewaunee clay soil type (pH 6.4, 3.8% organic matter, 14% sand, 35.1% silt, and 48.7% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 42.7 and 27.7% biodegradation was observed for Amiben, respectively. When a column of Poygan silty clay soil type (pH 7.2, 10% organic matter, 6% sand, 58.9% silt, and 33.6% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 40.3 and 22.6 % biodegradation was observed for Amiben, respectively(1).In an aerobic biodegradation study in a Honeoye silt loam at 25 °C and pH 6.5, amiben biodegraded slowly at rate of 4,500, 6,500, 11,500, and 74,000 cpm (cumulative (14)-CO2 evolution) after 7, 14, 28, and 112 days, respectively(1). According to a bioassay using the soybean plant and 50 ppm Amiben in soil, there was no breakdown of Amiben over an 11-month incubation period in moist soil at 15 °Cat incubation temperatures of 25 and 35 °C, Amiben breakdown over an 11-month period was 42 and 46 percent, respectively(2). Amiben showed the greatest loss of activity in Staten Island peaty muck (42% dissolved organic carbon and pH 5.8) which suggests that the rate of degradation depends on the organic content(3). |
| Landesrichtlinien für Trinkwasser | (FL) FLORIDA 110 ug/L(MN) MINNESOTA 100 ug/l(WI) WISCONSIN 150 ug/l |
| Bundesrichtlinien für Trinkwasser | EPA 100 ug/l |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3077 9/PG 3 |
| Zollcode | 29224999 |
| RTECS-Nr. | DG1925000 |
| R-Sätze (R) | 45-36/37/38-40 |
| Toxizität | Nontoxic to fish (Hartley and Kidd, 1987)acute oral LD50 for rats 5,620 mg/kg (Hartley and Kidd, 1987), 3,500 mg/kg (RTECS, 1985). |
| Gefahrensymbole | T,Xn |
| Sicherheitshinweise (S) | 53-22-26-36/37/39-45-36 |
| Gefahrenklasse | 9Carc. 1BEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 133-90-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Chloramben may be used as an analytical reference standard for the determination of the analyte in water samples using liquid chromatography with electrochemical detection (LC-EC).