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Diphenamid (ISO)
Diphenamide · N,N-DIMETHYL-2,2-DIPHENYLACETAMIDE · 12V · 80w · dif4 · ENIDE · Dimid · Dymid
Identifikatoren & physikalische Daten
| CAS No. | 957-51-7 |
|---|---|
| Summenformel | C16H17NO |
| Durchschnittliche Molmasse | 239,31 g/mol |
| Monoisotopische Masse | 239,13101416 g/mol |
| SMILES | CN(C)C(=O)C(c1ccccc1)c1ccccc1 |
| InChIKey | QAHFOPIILNICLA-UHFFFAOYSA-N |
| PubChem CID | 13728 |
| ChEMBL | CHEMBL2252192 |
| ChEBI | CHEBI:81915 |
| EC No. | 213-482-4 |
| DTXSID | DTXSID8024072 |
| Lokaler Name | Diphenamid (ISO) |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 244 |
| SpringerMaterials Properties | Fusion temperature |
| Pestizide | Pesticide -> EPA IRISHerbicidesActive substance -> EU Pesticides database: Not approvedPesticides -> Herbicides, OtherPesticide (Diphenamid) -> USDA PDB |
| LogP (Verteilungskoeffizient) | Log P: 2.17 |
| Geruch | NO APPRECIABLE ODOR |
| Dichte | 1.17 @ 23.3 °C1.2 g/cm³1.1700 |
| Color/Form | WHITECRYSTALS FROM ETHYL ACETATEWHITE PRISMSColorless |
| Löslichkeit | SOLUBILITY (G/100 ML SOLVENT @ 27 °C): 18.9 IN ACETONE, 16.5 IN N,N-DIMETHYLFORMAMIDE, 32.0 IN PHENYL CELLOSOLVE, 0.026 IN WATER, 5.01 IN XYLENEwater solubility = 260 mg/l @ 27 °CSolubility in water, g/100ml at 27 °C: 0.03239.9mg/L(25 ºC) |
| Corrosivity | Non-corrosive |
| Decomposition | When heated to decomposition it emits toxic fumes of oxides of nitrogen. |
| Schmelzpunkt | 134.5 TO 135.5 °CMP: 128-135 °C (TECHNICAL PRODUCT 95% PURE)132-136 °C(lit.) |
| Dampfdruck | 0.00000003 [mmHg]3.00X10-8 mm Hg @ 25 °C |
| Physical Description | Diphenamid appears as colorless to off-white crystals. Used as an herbicide.White solid[Hawley] Colorless or white solidTechnical product: Off-white solid[HSDB]WHITE SOLID IN VARIOUS FORMS. |
| Siedepunkt | 381.97°C (rough estimate) |
| Brechungsindex | 1.5500 (estimate) |
| Lagerbedingungen | 0-6°C |
| Aggregatzustand | Huff Powder |
| pKa (Säurekonstante) | -0.68±0.70(Predicted) |
| Farbe | White |
| Merck | 13,3339 |
| BRN | 2052009 |
| Henry-Konstante | 2.7×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong bases. |
| CAS Datenbank | 957-51-7 |
| NIST chemische Informationen | Fenam(957-51-7) |
| EPA chemische Informationen | Diphenamid (957-51-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | 2002/2076 |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzeneacetamide, N,N-dimethyl-.alpha.-phenyl-: Environment tier I assessment |
| Brandgefahren | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Brandpotenzial | Nonflammable |
| Gefahrenübersicht | No listed effects of short-term or long-term exposure[ICSC] Causes convulsions in high-dose animal experimentsNo effects in rats fed 10 mg/kg for 90 daysNon-irritant and non-sensitizer of skin in animal tests[HSDB] An irritant[MSDSonline] |
| Reaktive Gruppe | Amides and Imides |
| EG-Einstufung | Symbol: XnR: 22-52/53S: (2)-61 |
| FIFRA-Anforderungen | 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. Diphenamid 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: 0269Pesticide type: HerbicideRegistration Standard Date: 06/30/87Case 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): DiphenamidAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."Tolerances are established for residues of the herbicide diphenamid (N,N-dimethyl-2,2-diphenylacetamide) including its desmethyl metabolite (N-methyl-2,2-diphenylacetamide) in or on raw agricultural commodities as follows: peanut hay and foragepotatoes and strawberriespeanut hulls and soybean hay and foragecotton forageapples, cottonseed, fruiting vegetables, okra, peaches, peanuts, soybeans, and sweet potatoesmeat, fat, and meat byproducts of cattle, goats, hogs, horses, and sheepmilkand rasberries. |
| Reactivity Profile | DIPHENAMID is an amide. 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). This compound is decomposed by strong base or acid. |
| Chemical Dangers | Decomposes on heating at 210 °C and on burning. This produces toxic and corrosive gases including nitrogen oxides. Reacts with bases, strong acids and strong oxidants. |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity - category 4Acute Tox. 4 * |
| Brandbekämpfung | Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . |
| Sichere Lagerung | Separated from strong acids, bases and strong oxidants. |
| Entsorgungsverfahren | Recommendable method: Incineration. Peer-review: Large amt of diphenamid should be burned in incinerator with effluent gas scrubbing when well diluted with other wastes. Solid material can be dissolved in acetone or xylene to ease feeding into incinerator. (Peer-review conclusions of an IRPTC expert consultation (May 1985))Hydrolysis: Alkali hydrolysis: Slow reaction. Phenylacetic acid and dimethylamine are less phytotoxic. |
| Verschüttetes entsorgen | Do NOT let this chemical enter the environment. Then store and dispose of according to local regulations. If appropriate, moisten first to prevent dusting. |
| Preventive Measures | Prevent drifting. Keep away from the eyes. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea nuisance-causing concentration of airborne particles can, however, be reached quickly. |
| Exposure Prevention | PREVENT DISPERSION OF DUST! |
| Allowable Tolerances | Tolerances are established for residues of the herbicide diphenamid (N,N-dimethyl-2,2-diphenylacetamide) including its desmethyl metabolite (N-methyl-2,2-diphenylacetamide) in or on raw agricultural commodities as follows: 2 ppm in or on peanut hay and forage1 ppm in or on potatoes and strawberries0.5 ppm in or on peanut hulls and soybean, hay and forage0.2 ppm in or on cotton forage0.1 ppm (negligible residue) in or on apples, cottonseed, fruiting vegetables, okra, peaches, peanuts, soybeans, and sweet potatoes0.05 ppm (negligible residue) in meat, fat, and meat byproducts of cattle, goats, hogs, horses, and sheep0.01 ppm (negligible residues) in milkand 1.0 ppm in or on rasberries. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Zielorgane | Hepatic |
| Ökotoxizitätswerte | EC50 DAPHNIA MAGNA 58 MG/L/48 HR, IMMOBILIZATION (95% CONFIDENCE LIMIT 43-79 MG/L) AT 21 °C, 1ST INSTAR. STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.EC50 CYPRIDOPSIS VIDUA 51 MG/L/48 HR, IMMOBILIZATION (95% CONFIDENCE LIMIT 37-71 MG/L) AT 21 °C, MATURE. STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.LC50 ASELLUS MORE THAN 100 MG/L/96 HR AT 15 °C, MATURE. STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.LC50 GAMMARUS FASCIATUS MORE THAN 100 MG/L/96 HR AT 15 °C, MATURE. STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.For more Ecotoxicity Values (Complete) data for DIPHENAMID (7 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Diphenamid has an estimated Koc of 210(3) and therefore would be expected to leach moderately in soil. Biodegradation is the primary degradative pathway for loss of diphenamid from soils(1-2). The persistence of diphenamid in soil will depend on the soil type, moisture content and the temperature of soil(2). Under warm, moist conditions, the average persistence of diphenamid after application at recommended rates is 3-6 months(2). At higher application rates and under low rainfall or colder temperatures, diphenamid may persist in soil longer than 6 months(5-6). The rate of biodegradation increases moderately in soils that have been previously treated with diphenamid. Diphenamid is non volatile and appears to be stable in sunlight(2).AQUATIC FATE: Neither hydrolysis(1-2) nor photolysis by sunlight(3-4) should be important for the degradation of diphenamid in water. Based on its ability to undergo biodegradation in soil(5), biodegradation should be the most important process for diphenamid in water(SRC). A Koc value of 210(6) indicates that diphenamid may be moderately adsorbed to suspended solids and sediment in water(SRC). The estimated BCF value of 27(6) indicates that bioconcentration of diphenamid in aquatic organisms will not be important(SRC).ATMOSPHERIC FATE: Based on a vapor pressure of 3X10-8 mm Hg(1), diphenamid should be present mostly in the particulate form in air, but a small amount may be present in the vapor phase(2,SRC). Based on an estimation method(3), vapor phase diphenamid may be removed from the atmosphere with a half-life of 10.6 hrs due to reaction with photochemically produced hydroxyl radicals(SRC). Partial removal of particulate diphenamid from the air may occur by dry deposition(SRC). Both vapor and particle phase diphenamid may be partly removed from the atmosphere by wet deposition. |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Expositionspfade | The substance can be absorbed into the body by ingestion. |
| Signs and Symptoms | Vomiting. |
| Acute Toxicity Link | Chemical: DIPHENAMIDE |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal. |
| EPA IRIS Information | DiphenamidHepatic3 x 10 ^-2 mg/kg-day |
| Soil Adsorption/Mobility | DIPHENAMID IS NOT TIGHTLY ADSORBED ON SOIL COLLOIDS. IT LEACHES RAPIDLY IN SANDYSOILS BUT SLOWLY IN LOAM OR CLAY SOILS. IN SANDY SOILS, RETENTION OF AN EFFECTIVE CONCN IN THE WEED SEED GERMINATION ZONE WITH HEAVY RAINFALL CAN BE A PROBLEM.A Koc of 210 for diphenamid has estimated from its water solubility(1-2). According to a suggested classification scheme, this Koc value indicates that diphenamid would be moderately mobile in soil(5). Soil thin layer chromatography studies indicates that the average retention factor (Rf) of diphenamid in a silty loam soil is 0.49(3-4). This Rf value also indicates that diphenamid has moderate mobility in soil(3). |
| Natural Pollution Sources | Diphenamid is not known to occur naturally. (SRC) |
| Human Toxicity Excerpts | ASSUMED TO ... /HAVE EMETIC/ EFFECTS IN MAN. MAY INDUCE CONVULSIONS. |
| Landesrichtlinien für Trinkwasser | (CA) CALIFORNIA 200 ug/l(FL) FLORIDA 210 ug/L |
| Bundesrichtlinien für Trinkwasser | EPA 200 ug/l |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN3077(solid) |
| Zollcode | 29242990 |
| RTECS-Nr. | AB8050000 |
| R-Sätze (R) | 22-52/53 |
| Toxizität | LD50 orally in rats: 700 mg/kg (Bailey, White) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 61 |
| Gefahrstoffdaten | 957-51-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Diphenamid is a pesticide found in representative agricultural produce (brown rice, orange, spinach and potatoes).