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3-(4-クロロフェニル)-1,1-ジメチル尿素
3-(4-クロロフェニル)-1,1-ジメチル尿素 · 3-(p-クロロフェニル)-1,1-ジメチル尿素 · モニュロン · 1,1-ジメチル-3-(4-クロロフェニル)尿素 · CMU剤 · 1,1-ジメチル-3-(p-クロロフェニル)尿素 · N'-(4-クロロフェニル)-N,N-ジメチル尿素 · 1,1-ジメチル-3-[4-クロロフェニル]尿素
識別子と物理属性
| CAS No. | 150-68-5 |
|---|---|
| 分子式 | C9H11ClN2O |
| 平均分子量 | 198.65 g/mol |
| 単同位体質量 | 198.05599065 g/mol |
| SMILES | CN(C)C(=O)Nc1ccc(Cl)cc1 |
| InChIKey | BMLIZLVNXIYGCK-UHFFFAOYSA-N |
| PubChem CID | 8800 |
| ChEMBL | CHEMBL467623 |
| ChEBI | CHEBI:38214 |
| EC No. | 205-766-1 |
| DTXSID | DTXSID0020311 |
| 現地名 | 3-(4-クロロフェニル)-1,1-ジメチル尿素 |
化学・物理的性質
| XLogP | 1.9 |
|---|---|
| 極性表面積 | 32.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 1 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 176 |
| pH | 6.26 SATURATED AQ SOLUTION |
| SpringerMaterials Properties | Boiling point |
| 農薬 | HerbicidesActive substance -> EU Pesticides database: Not approvedPesticides -> Herbicides, Urea DerivativePesticide (Monuron) -> USDA PDB |
| LogP（分配係数） | 2.01 |
| 臭い | SLIGHT ODOROdorless solid |
| 密度 | 1.27 at 68 °F (NTP, 1992) - Denser than waterwill sink1.27 @ 20 °C/20 °C1,27 g/cm3 |
| Color/Form | WHITE PLATES FROM METHANOLTHIN RECTANGULAR PRISMS FROM METHANOLPlatelets |
| 溶解度 | less than 1 mg/mL at 70.7 °F (NTP, 1992)Monuron-TCA is a crystalline solidmp 78-81 °C. Solubility (room temperature): 918 mg/l water400 g/kg 1,2-dichloroethane177 g/kg methanol91 g/kg xylene. It is acidic in reaction and incompatible with alkaline materials. /Monuron Trichloroacetate/VERY SLIGHTLY SOL IN NUMBER 3 DIESEL OILMODERATELY SOL IN METHANOL, ETHANOL, PRACTICALLY INSOL IN HYDROCARBON SOLVENTSSLIGHTLY SOL IN OIL & POLAR SOLVENTSSolubility (ppm): water 230 (@ 25 °C), acetone 52,000 (@ 27 °C), benzene 2900 (@ 27 °C)Sol in benzene: 3 g/kg at 27 °C262mg/L(25℃) |
| Corrosivity | NON-CORROSIVE |
| 沸点 | 365 to 392 °F at 760 mmHg (decomposes) (NTP, 1992)301.31°C (rough estimate) |
| Decomposition | When heated to decomposition it emits very toxic fumes of oxides of nitrogen and /hydrogen/ chloride ions. |
| 融点 | 338.9 to 340.7 °F (NTP, 1992)170.5-171.5 °C173-174 °C (lit.) |
| 蒸気圧 | 0Pa at 20℃ |
| 屈折率 | 1.5330 (estimate) |
| 貯蔵条件 | 0-6°C |
| pKa（酸解離定数） | 14.22±0.70(Predicted) |
| 外観・状態 | 結晶性固体 |
| 色 | 白い |
| Merck | 14,6261 |
| BRN | 2097922 |
| ヘンリー定数 | 1.7×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C9H11ClN2O/c1-12(2)9(13)11-8-5-3-7(10)4-6-8/h3-6H,1-2H3,(H,11,13) |
| InChIKey | BMLIZLVNXIYGCK-UHFFFAOYSA-N |
| SMILES | CN(C)C(=O)Nc1ccc(Cl)cc1 |
| LogP（分配係数） | 1.94 at 20℃ |
| EPAの化学物質情報 | Monuron (150-68-5) |
化学的特性
White, crystalline solid; odorless. Very low solubility in water and hydrocarbonsolvents; slightly soluble in oils; partially soluble inalcohols; stable toward oxidation and moisture.
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: Urea, N'-(4-chlorophenyl)-N,N-dimethyl-Commission Regulation (EC) No 1490/20022002/2076Status: Active Update: 27-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/24776Urea, N'-(4-chlorophenyl)-N,N-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.The 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.) |
| 輸送ラベル（DOT） | Class 9 |
| 火災危険 | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| 火災の可能性 | ... NON-FLAMMABLE. |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include fall in blood pressure, convulsions or coma. Other symptoms may include ataxia, drowsiness, hyporeflexia, pallor, tachypnea, dacryorrhea, aciduria, diarrhea, epistaxis, hyperreflexia and irritability. |
| 有害性の概要 | Urea-derived herbicides have low toxicity in animal feeding studiesMay induce methemoglobinemia[HSDB] Systemic toxicity unlikely unless large amounts ingested[EPA Pesticides, p. 122] Causes anemia and methemoglobinemia in animal experiments[Merck Index] |
| 反応性グループ | Amides and Imides |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of Monuron in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 266 (1988) NIH Publication No. 88-2522 |
| FIFRA 要件 | 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. Monuron 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, as amended in 1988. Case No: 0045Pesticide type: HerbicideRegistration Standard Date: 06/30/83,07/01/83Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.Active ingredient (AI): MonuronAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled." |
| Reactivity Profile | MONURON is a chlorinated urea derivative. May react with azo and diazo compounds to generate toxic gases. May react with strong reducing agents to generate flammable gases. Reacts as a weak base. Combustion generates mixed oxides of nitrogen (NOx). |
| Air and Water Reactions | Insoluble in water. Is hydrolyzed slowly by acids and alkalis, and more rapidly on heating (NTP, 1992). |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Carcinogenicity - category 2Acute toxicity (Oral) - Category 4Carc. 2 |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 応急処置 | 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. |
| 消火手順 | Self-contained breathing apparatus, rubber gloves, hats, suits, and boots must be worn. |
| 保管条件 | Keep in well ventilated area. |
| 非火災時の漏出対応 | 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 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% 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 60-70% 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. |
| 処分方法 | Treatment at elevated temp by acid or base yields dimethylamine and 3,4-dichloroaniline. Hydrolysis is not recommended as a disposal procedure because of the generation of the toxic product, 3,4-dichloraniline and dimethylamine. Recommendable method: Incineration. Not recommendable method: Hydrolysis. Peer review: Incineration in a unit with effluent gas scrubbing is recommendable. (Peer-review conclusions of an IRPTC expert consultation May 1985)) |
| Preventive Measures | AVOID INHALING ANY DUST, SPRAY MIST & STRONG VAPOR. /HERBICIDES/ |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| 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)PROTECT SKIN & HAIR ... USE ONLY APPROVED RESPIRATORY PROTECTIVE EQUIPMENT, WHEN LABEL DIRECTIONS ADVISE NEED. /HERBICIDES/Wear rubber gloves for all handling. |
| 相互作用 | IN PRESENCE OF MODERATE AMT OF CARBARYL, DEGRADATION /OF MONURON IN COTTON PLANTS/ BEYOND MONO-DEMETHYLATION WAS INHIBITED. ... 4-BENZOTHIOPHENE-N-METHYLCARBAMATE WAS AS EFFECTIVE AS CARBARYL.FLAVINS (FLAVINMONONUCLEOTIDE) HAVE BEEN SHOWN TO CAUSE PHOTOINACTIVATION OF PHENYLUREAS, SUCH AS MONURON, IN VITRO. |
| 生態毒性値 | LC50 BOBWHITE QUAIL GREATER THAN 5000 PPM/5 DAYS (AGE 17 DAYS, NO MORTALITY TO 5000 PPM)LC50 JAPANESE QUAIL GREATER THAN 5000 PPM/5 DAYS (AGE 12 DAYS, NO MORTALITY AT 1250 PPM, 7% AT 2500 PPM, 21% AT 5000 PPM)LC50 RING-NECKED PHEASANT 4682 PPM/5 DAYS (AGE 15 DAYS, 95% CONFIDENCE LIMIT 3902-5746 PPM)LC50 MALLARD DUCK GREATER THAN 5000 PPM/5 DAYS (AGE 10 DAYS, NO MORTALITY AT 1250 PPM, 10% AT 2500 PPM, 10% AT 5000 PPM)LC50 Japanese quail (Coturnix japonica), 14 days old, oral (5 day ad libitum in diet) >5,000 ppm |
| 環境中動態 | TERRESTRIAL FATE: Biodegradation appears to be the major process by which monuron may be lost from most soils(1-2). The loss of monuron from soil surface by photolysis may account for a small fraction of loss of monuron as most of the monuron would move deeper into soil with rain(1). Volatilization loss of monuron from dry soil or wet soils should not be important(1). Monuron may moderately leach in most soils(3-4). Depending on the nature of soil and climatic conditions, the field half-life of monuron in soil range from less than 30 days to 166 days(5-7).AQUATIC FATE: At low concns (on the order of ug/l), the major process for the loss of monuron from water appears to be biodegradation(1-2). Neither hydrolysis nor any other chemical reaction is important for the loss of monuron in water(1,3). Monuron may photolyze in surface layers of water where sunlight penterates(1). The photolysis half-life of monuron in aqueous solution by natural sunlight is estimated to be 15 days(4). Photolysis is accelerated by the presence of surfactants(5). Based upon the low vapor pressure(6) and high water solubility(7), monuron should not volatilize from water. Monuron is not expected to bioconcentrate in aquatic organisms(7).ATMOSPHERIC FATE: Based upon on its vapor pressure, 5.03X10-7 mm Hg at 25 °C(1), monuron is expected to be present partially in the vapor phase and partially in the particulate form in air(2,SRC). Vapor phase monuron will react with photochemically produced hydroxyl radicals with a half-life of 6.7 hr(3-4). Monuron may also be removed from the atmosphere by dry and wet deposition(SRC). |
| 有害作用 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Milk Concentrations | IN RATS GIVEN 875 MG/KG BODY WT ORALLY, ... MONURON RELATED MATERIAL WAS ... SECRETED INTO MILK OF LACTATING ANIMALS. |
| 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=150-68-5] |
| Soil Adsorption/Mobility | The Koc values for monuron determined from experimental adsorption isotherms or estimated using recommended regression equations range from 83 to 225(1-6). According to a suggested classification scheme(9), Koc values of this magnitude indicate that monuron is moderately to highly mobile in soil. Soil thin layer chromatographic studies also indicate that monuron is moderately mobile in soil(5,7). The adsorption of monuron in soil is virtually independent of pH and clay content of soil, but the adsorption increases with increase in organic carbon content(6,8). However, other investigators concluded that the adsorption of monuron increases with an increase in the clay content of soil(10). |
| Natural Pollution Sources | Monuron is not known to occur naturally(1). |
| Artificial Pollution Sources | Since monuron is commercially produced and used as a herbicide(1), it will be released to the environment during the manufacture and particularly during the use of the herbicide(SRC). Accidental spills during loading/unloading and shipment will also release monuron in the environment(SRC). |
| Environmental Biodegradation | /INVESTIGATORS/ ... WERE ABLE TO ISOLATE FROM BROOKSTON SILTY CLAY LOAM A BACTERIUM OF GENUS PSEUDOMONAS WHICH UTILIZED MONURON AS SOLE SOURCE OF CARBON.Several pure cultures of bacteria including Pseudomonas, Xanthomonas, Sarcina, and Bacillus and fungi including Penicillium and Aspergillus are capable of degrading monuron(1-3). The major process for the loss of monuron from water is biodegradation(3). At a concentration of 6-7 mg/l, no loss of monuron by mixed microorganisms from river water and sewage was observed in 16 wk(5). However, in a soil-water system, appreciable biodegradation occurred after 16 weeks and 15% of monuron was recovered after 128 wk(4). At an initial concn of 10 ug/l in sewage water, monuron started to mineralize on day 45 and about 20% of monuron mineralized by day 84(6). No mineralization of monuron was observed in 84 days at a concn of 10 mg/l(6). Besides carbon dioxide, products with chromatographic characteristics of 4-(chlorophenyl)urea and 4-chloroaniline were also identified(6).Monuron is lost from soil primarily through biodegradation(1,3). Monuron loss from two soils was about 40% in 22 wk at a concn of 4 ppm(1). In a clay loam soil, approx. 10% of monuron mineralized to carbon dioxide in 90 days(1). Hydroxylation products of monuron have been identified in soil(5). Except for most heavily treated soils (above 16 lbs/acre), approx. 90% of monuron disappeared in 1 yr. During the second year, loss averaged about 62%(3). Monuron's degradation is a function of application rate(2). Biodegradation is favored by high temperature adequate moisture and high soil organic matter content(2). When monuron was incubated with sediments from a pond under anaerobic conditions, no ring-substituted products were detected in 73 days(4). Therefore, monuron may persist in soil and sediments under anaerobic conditions(SRC). |
| Carcinogen Classification | MonuronGroup 3: Not classifiable as to its carcinogenicity to humansVolume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987440 pagesISBN 92-832-1411-0 (out of print)19911990 |
| Environmental Bioconcentration | From its water solubility and a regression equation, the bioconcentration factor (BCF) for monuron in aquatic organisms has been estimated to be 29(1). Based on a log Kow value of 1.94(2) and a regression equation(3), the BCF value can be estimated to be 17(SRC). Both these values indicate that bioconcentration of monuron in aquatic organisms should not be important(1,SRC). The low rate of uptake and fast depuration (depuration half-life of 0.45 days) of monuron from catfish (Ictalurus melas)(4) also indicates that bioconcentration will not be important(SRC). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | YS6300000 |
| 輸送番号（UN） | UN 3077 9/PG 3 |
| 毒性 | LD50 orally in rats: 3700 mg/kg (Bailey, White) |
| 税関コード | 29242990 |
| 危険文句（R） | 22-40-50/53 |
| 化審法 | (3)-2194 |
| 危険表示 | Xn,N |
| 安全措置（S） | 36/37-60-61 |
| 危険等級 | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 2 |
| 包装等級 | III |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 150-68-5(Hazardous Substances Data) |
用途
用途
尿素系除草剤
使用
Monuron may be used as a reference standard in the determination of monuron in rice and corn using high performance liquid chromatography coupled with fluorescence detection combined with ultraviolet decomposition and post-column derivatization.
一般的な説明
White crystalline solid or white powder with a slight odor. Melting point 175°C. Moderately toxic by ingestion. Used as an herbicide.
製法・合成法
純化方法
Crystallise monuron from MeOH. [Beilstein 12 IV 1191.]