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3,5-Dichlor-N-(1,1-dimethylprop-2-inyl)benzamid
PRONAMIDE · PROPYZAMID · 3,5-DICHLORO-N-(1,1-DIMETHYL-2-PROPYNYL)BENZAMIDE · KERB · JUDO · PIZA · RAPIER · RH 315
Identifikatoren & physikalische Daten
| CAS No. | 23950-58-5 |
|---|---|
| Summenformel | C12H11Cl2NO |
| Durchschnittliche Molmasse | 256,12 g/mol |
| Monoisotopische Masse | 255,02176933 g/mol |
| SMILES | C#CC(C)(C)NC(=O)c1cc(Cl)cc(Cl)c1 |
| InChIKey | PHNUZKMIPFFYSO-UHFFFAOYSA-N |
| PubChem CID | 32154 |
| ChEMBL | CHEMBL283487 |
| ChEBI | CHEBI:34935 |
| EC No. | 245-951-4 |
| DTXSID | DTXSID2020420 |
| Lokaler Name | 3,5-Dichlor-N-(1,1-dimethylprop-2-inyl)benzamid |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 29,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 308 |
| SpringerMaterials Properties | Fusion temperature |
| Pestizide | Pesticide -> EPA IRISAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: ApprovedPesticides -> Herbicides, OtherEnvironmental transformation -> Pesticides (parent, predecessor) |
| LogP (Verteilungskoeffizient) | Log Kow = 3.43 |
| Geruch | ODORLESS |
| Color/Form | OFF-WHITE SOLIDWHITE CRYSTALSNEEDLESWhite powder |
| Löslichkeit | In water - 15 mg/l (25 °C). In methanol, isopropanol 150, cyclohexanone, methyl ethyl ketone 200, dimethyl sulfoxide 330 (all in g/l). Moderately soluble in benzene, xylene, carbon tetrachloride. Sightly soluble in petroleum ether.SOL IN MANY ALIPHATIC & AROMATIC SOLVENTS.Chloroform (Slightly), Methanol (Slightly)15mg/L(25 ºC) |
| Corrosivity | NONCORROSIVE UNDER NORMAL USE CONDITIONS. |
| Human Drugs | Pharmaceuticals |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 155-156 °CDecomposes above melting pointin solution for 28 days (pH 5-9, 20 °C) < 10% loss.153-155°C |
| Dampfdruck | 0.000085 [mmHg]8.5X10-5 MM HG @ 25 °C |
| Physical Description | 3,5-dichloro-n-(1,1-dimethyl-2-propynyl)benzamide is a white solid. Used as a selective herbicide.Off-white or white odorless solid[HSDB] Colorless or white crystalline solid[MSDSonline] |
| Siedepunkt | 340.9±42.0 °C(Predicted) |
| Dichte | 1.2742 (rough estimate) |
| Brechungsindex | 1.5490 (estimate) |
| Flammpunkt | 2 °C |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | 12.30±0.46(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Almost white |
| Merck | 14,7872 |
| BRN | 882391 |
| Henry-Konstante | 1.0×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Hauptanwendungen | agriculturecleaning productscosmeticsenvironmentalfood and beveragespersonal care |
| InChI | 1S/C12H11Cl2NO/c1-4-12(2,3)15-11(16)8-5-9(13)7-10(14)6-8/h1,5-7H,2-3H3,(H,15,16) |
| InChIKey | PHNUZKMIPFFYSO-UHFFFAOYSA-N |
| SMILES | CC(C)(NC(=O)c1cc(Cl)cc(Cl)c1)C#C |
| LogP (Verteilungskoeffizient) | 3.430 |
| CAS Datenbank | 23950-58-5(CAS DataBase Reference) |
| NIST chemische Informationen | Propyzamide(23950-58-5) |
| EPA chemische Informationen | Pronamide (23950-58-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH351: Suspected of causing cancer [Warning Carcinogenicity]P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)H351 (100%): Suspected of causing cancer [Warning Carcinogenicity] |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityRegulation (EC) No 1107/2009 (amended)Pronamide (Propyzamide) is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)03/39/EC, Reg. (EU) 2016/2016, Reg. (EU) 2018/755, Reg. (EU) 2018/84, Reg. (EU) 2020/1093, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012Propyzamide: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzamide, 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)-: Environment tier I assessment |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Gesundheitsgefahren | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Gefahrenübersicht | A mild skin and eye irritant (wettable powder formulation)Toxic to liver in animal studies[HSDB] May cause irritation[MSDSonline] |
| Reaktive Gruppe | Amides and Imides |
| Special Reports | USEPAPronamide Position Document 2/3 (1979) EPA/SPRD-80/68. Report contains information on the uses, environmental residues and health hazards of pronamide.GOLD LS, ET ALENVIRON HEALTH PERSPECT 79 (0): 259-72 (1989). SUMMARY OF CARCINOGENIC POTENCY AND POSITIVITY FOR 492 RODENT CARCINOGENS IN THE CARCINOGENIC POTENCY DATABASE. |
| RCRA-Anforderungen | U192As stipulated in 40 CFR 261.33, when pronamide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| FIFRA-Anforderungen | Tolerances are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: alfalfa (fresh, storage, and hay)applesartichokesblackberriesblueberriesboysenberriescattle (fat, mbyp, meat, kidney, and liver)cherriesclovercrown vetcheggsendive (escarole)goats (fat, mbyp, meat, kidney, and liver)grapeshogs (fat, mbyp, meat, kidney, and liver)horses (fat, mbyp, meat, kidney, and liver)lettucemilknectarinespeachespearsplumspoultry (fat, mbyp, meat, kidney, and liver), radicchio greens (tops)raspberiessainfoinsheep (fat, mbyp, meat, kidney, and liver)trefoil.Tolerances with regional registration are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: peas (dried, winter)rhubarb.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. Propyzamide 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: 0082Pesticide type: herbicideRegistration Standard Date: 04/15/86Case Status: RED Approved 03/94OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.Active ingredient (AI): PropyzamideData Call-in (DCI) Date(s): 09/28/90, 06/10/94, 03/03/95AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI. |
| Reactivity Profile | 3,5-DICHLORO-N-(1,1-DIMETHYL-2-PROPYNYL)BENZAMIDE is a chlorinated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| Brandbekämpfung | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Erste Hilfe | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Lagerbedingungen | THERE ARE NO SPECIAL STORAGE PROBLEMS UNDER NORMAL AMBIENT CONDITIONS. STORAGE AT HIGH TEMP (GREATER THAN 50 °C) SHOULD BE AVOIDED. |
| Freisetung ohne Brand | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U192, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. |
| Preventive Measures | SAFETY PRECAUTIONS FOR HANDLING & APPLICATION: AVOID SKIN CONTACT. DO NOT BREATHE DUST OR SPRAY MIST. IN CASE OF EYE CONTACT, WASH WITH COPIOUS QUANTITIES OF WATER. DO NOT CONTAMINATE FOOD OR FEEDSTUFFS. DO NOT PERMIT DRIFT TO NONTARGET AREAS. |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Allowable Tolerances | Tolerances are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: alfalfa (fresh, storage, and hay), 10 ppmapples, 0.1 ppmartichokes, 0.1 ppmblackberries, 0.5 ppmblueberries, 0.5 ppmboysenberries, 0.5 ppmcattle (fat, mbyp (except kidney and liver) and meat), 0.02 ppmcattle (kidney and liver), 0.2 ppmcherries, 0.1 ppmclover, 5.0 ppmcrown vetch, 5.0 ppmeggs, 0.02 ppmendive (escarole), 2.0 ppmgoats (fat, mbyp (except kidney and liver) and meat), 0.02 ppmgoats (kidney and liver), 0.2 ppmgrapes, 0.1 ppmhogs (fat, mbyp (except kidney and liver) and meat), 0.02 ppmhogs (kidney and liver), 0.2 ppmhorses (fat, mbyp (except kidney and liver) and meat), 0.02 ppmhorses (kidney and liver), 0.2 ppmlettuce, 1.0 ppmmilk, 0.02 ppmnectarines, 0.1 ppmpeaches, 0.1 ppmpears, 0.1 ppmplums, 0.1 ppmpoultry (fat, mbyp (except kidney and liver) and meat), 0.02 ppmpoultry (kidney and liver), 0.2 ppmradicchio greens (tops) 2.0 ppmraspberies, 0.05 ppmsainfoin, 5.0 ppmsheep (fat, mbyp (except kidney and liver) and meat), 0.02 ppmsheep (kidney and liver), 0.2 ppmtrefoil, 5.0 ppm.Tolerances with regional registration are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: peas (dried, winter), 0.05 ppmrhubarb, 0.1 ppm. |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:...GENERAL PERCAUTIONS: Take special care to avoid contact with the eyes, skin, or clothing. Wash clothing and gloves after use. PROTECTIVE CLOTHING: The following items of clothing are required when mixing or applying pronamide: a) Long-sleeved shirts and long pants, preferably one piece (overalls). b) Hat with brim. c) Heavy duty fabric or rubber work gloves. |
| Wechselwirkungen | ACTIVATED CARBON PROTECTED NEW PLANTINGS OF RYEGRASS, TALL FESCUE, ORCHARD GRASS, KENTUCKY BLUEGRASS AND COLONIAL BENTGRASS AGAINST PRONAMIDE. |
| Gesundheitliche Auswirkungen | Propyzamide is pratically non-toxic to mammals on an acute oral exposure basis., however a 2-generation reproduction study in rats found that propyzamide caused effects on both adult and offspring body size. |
| Umweltverhalten | TERRESTRIAL FATE: MOVEMENT OF PRONAMIDE IS GREATEST IN COARSE TEXTURED SOILS. LEACHING OF MOST SOIL RESIDUALS OCCURS IN LOAMY SANDS AND IN SILT LOAMS.TERRESTRIAL FATE: Spring spraying of 3 kg kerb/ha controlled weeds and left 0.15 mg propyzamide/kg in harvested flower heads of Anthemis nobilis and the top 5 cm of soil. At 5-10 cm, the residue was 0.056 mg/kg. The rate of herbicide decay depended more on the temp than on the soil moisture.TERRESTRIAL FATE: Based on a recommended classification scheme(1), experimental Koc values from 200-800(2-4), indicate that pronamide will have low to moderate mobility in soil(SRC). Very little leaching of pronamide occurs in most soil types as it is readily adsorbed on organic matter and other colloidal exchange sites(5,6). Pronamide is degraded via both biotic and abiotic pathways to a number of transformation products in soils(7,SRC). Initial transformation reactions in soil include cyclization to form 2-(3,5-dichlorophenyl)-4,4-dimethyl-5-methyleneoxazoline followed by hydrolysis to N-(1,1-dimethylacetonyl)-3,5-dichlorobenzamide(7). These two transformation products and small amounts of unchanged pronamide represented over 96% of the herbicide recovered 90 days after soil treatment(7). Other degradation products were present in trace amounts and were the result of alterations in the terminal carbons of the propynyl side chain(7). Transformation to the cyclized and subsequent hydrolysis products occurred about three times more rapidly in a non-sterilized soil as compared to the sterilized soil over a 33 day period(8)formation of carbon dioxide in the non-sterilized, but not in the sterilized soil indicated biological mediation(8).TERRESTRIAL FATE: Loss of pronamide from soil surfaces due to photodecomposition may occur(1,2). The average persistence of pronamide when applied at recommended herbicidal rates is variable (2-9 months) and depends on soil types and climatic conditions with residual activity greater in sandy soils with low organic carbon content(2). The degradation half-life of pronamide in 18 different soil types at 25 °C ranged from 9.5 to 32.4 days(3). The degradation half-life in 5 different soils varied from 23-42 days at 25 °C and from 63-112 days at 15 °C(4). Observed half-life under field conditions in a sandy loam soil varied from 40-80 days(5). Observed half-lives under field conditions averaged about 40 days in 14 different soil types(6). Pronamide had increasingly rapid initial biodegradation rates with increasing numbers of previous treatments(7). Half-lives for pronamide were approximately 45, 35, 22, and 18 days, respectively, in plots treated for the first, second, third, and fourth time(7). Volatilization of pronamide should not be an important fate process from moist or dry soil surfaces(SRC) given an estimated Henry's Law constant of 1.9X10-6 atm-cu m/mole(8,9,SRC) and an experimental vapor pressure of 8.5X10-5 mm Hg, respectively(8). However, under very hot and dry conditions, volatilization has been noted(2).For more Environmental Fate (Complete) data for PRONAMIDE (6 total), please visit the HSDB record page. |
| Lebensmitteluntersuchungswerte | Pronamide was detected during monitoring of imported and domestic pears at unreported concentrations (1992-1993)(1). Pronamide was detected during the FDA's program for monitoring pesticide residues in raw agricultural commodities from 1978-82(2) and 1983-86(3), 1989(4), and 1990(5) (unreported concentration). |
| 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. |
| Signs and Symptoms | Propyzamide causes local irritation when applied to the skin. |
| EPA IRIS Information | Pronamide7.5 x 10 ^-2 mg/kg-day |
| Soil Adsorption/Mobility | Very little leaching of pronamide occurs in most soil types as it is readily adsorbed on organic matter and other colloidal exchange sites(1). Adsorption distribution experiments with 18 different soil types has shown that, in general, pronamide adsorption increases proportionately with an increase in organic matter content(2). Soil partition coefficients were measured for pronamide in seven soils (organic carbon ranged from 0.01-16.9%pH from 5.2-7.2)Kd values ranged from 0.04-72.2 with higher values corresponding to soils with higher organic carbon content(Koc values of 400-427(SRC))(3). Koc values of 204(4) and 800(5) were measured in soil for this compound. Pronamide had a pesticide leaching potential index value of 36 out of 100 indicating that this pesticide is not likely to leach significantly(6). According to a recommended classification scheme(7), these estimated Koc values suggest that pronamide has low to moderate mobility in soil(SRC). |
| Natural Pollution Sources | Pronamide is not known to occur naturally. (SRC) |
| Atmospheric Concentrations | URBAN/SUBURBAN: Pronamide was detected in ambient air in Kitakyushu in 1991-1992 at concentrations from 0.17-0.28 ng/cu m(1). |
| Human Toxicity Excerpts | THE WETTABLE POWDER FORMULATION IS ONLY MILDLY IRRITATING TO EYES & SKIN. |
| Artificial Pollution Sources | Pronamide's production and use as a herbicide to control broadleaf and grass weeds(1) results in its direct release to the environment(SRC). This compound is used on alfalfa, apple, artichoke, grape, lettuce, raspberry, and seed crops(2). |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Landesrichtlinien für Trinkwasser | (AZ) ARIZONA 52 ug/l(FL) FLORIDA 53 ug/L(ME) MAINE 23 ug/l |
| Bundesrichtlinien für Trinkwasser | EPA 50 ug/l |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 3077 |
| Zollcode | 29242990 |
| RTECS-Nr. | CV3460000 |
| R-Sätze (R) | 40-50/53-36-20/21/22-11 |
| Toxizität | LD50 in male, female rats (mg/kg): 8350, 5620 orally (Viste) |
| Gefahrensymbole | XnN,N,Xn,F |
| Sicherheitshinweise (S) | 36/37-60-61-36-26 |
| Gefahrenklasse | 9Aquatic Acute 1Aquatic Chronic 1Carc. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 23950-58-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Selective pre-emergence herbicide.