HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Ioxynil (ISO)
Loxynil · 4-HYDROXY-3,5-DIIODOBENZONITRILE · Iotox · ACTRIL · IOTRIL · Mylone · TOTRIL · Certol
Identifikatoren & physikalische Daten
| CAS No. | 1689-83-4 |
|---|---|
| Summenformel | C7H3I2NO |
| Durchschnittliche Molmasse | 370,91 g/mol |
| Monoisotopische Masse | 370,83041 g/mol |
| SMILES | N#Cc1cc(I)c(O)c(I)c1 |
| InChIKey | NRXQIUSYPAHGNM-UHFFFAOYSA-N |
| PubChem CID | 15530 |
| ChEMBL | CHEMBL509523 |
| ChEBI | CHEBI:81821 |
| EC No. | 216-881-1 |
| DTXSID | DTXSID8022161 |
| Lokaler Name | Ioxynil (ISO) |
Chemische & physikalische Eigenschaften
| XLogP | 2 |
|---|---|
| Polarare Oberfläche (TPSA) | 44 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 176 |
| LogP (Verteilungskoeffizient) | Log Kow = 0.90 at pH 6.53.51 |
| Geruch | Faint phenolic /tech grade/Odorless when pure |
| Color/Form | Colorless crystalline solid |
| Löslichkeit | SOLUBILITY IN WATER @ 20-25 °C: 22% /LITHIUM SALT/14% /SODIUM SALT/10.7% /POTASSIUM SALT/SOLUBILITY IN WATER: 0.005% @ 20 °CIN CYCLOHEXANONE: 14%IN DIMETHYLFORMAMIDE: 74%SLIGHTLY SOL IN CHLOROFORMSOL IN ETHERAT 25 °C: IN ACETONE MORE THAN 10 G/100 MLIN BENZENE 1.1 G/100 MLIN CARBON TETRACHLORIDE 0.14 G/100 MLIN METHANOL 3.3 G/100 MLIN WATER 130 PPMIn water 50 mg/l (25 °C). In acetone 70, ethanol, methanol 20, cyclohexanone 140, tetrahydrofuran 340, dimethylformamide 740, chloroform 10, carbon tetrachloride <1 (all in g/l, 25 °C)Solubility in water: noneInsoluble |
| Corrosivity | Non-corrosive |
| Siedepunkt | Sublimes at circa 140 °C/0.1 mm Hg282.6±40.0 °C(Predicted) |
| Decomposition | When heated to decomposition ... emits toxic fumes of /hydrogen iodide and hydrogen chloride/. |
| Schmelzpunkt | 212-213 °CCREAM POWDERFAINT PHENOLIC ODORMELTING POINT: 200 °C /TECHNICAL PRODUCT/ |
| Dampfdruck | 0.00000014 [mmHg]Vapor pressure: 2.77X10-5 mm Hg at 105 °C /Octanoate/Less than 1 mPa at 20 °CVapor pressure, Pa at 20 °C: |
| Physical Description | Colorless odorless solid[ICSC] Technical product is cream solidDecomposed by sunlight and ultraviolet light[HSDB] Powder[MSDSonline]ODOURLESS COLOURLESS CRYSTALS. |
| Stability/Shelf Life | PRACTICALLY NON-VOLATILENO DETERIORATION IN LESS THAN 2 YEARS OF STORAGEVery stable to acids and bases. Decomposed by sunlight and UV light. |
| Dissociation Constants | PK: 3.96 |
| Dichte | 2.4947 (estimate) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | 4.95±0.23(Predicted) |
| BRN | 2364041 |
| Henry-Konstante | 1.3×102 mol/(m3Pa) at 25℃, Mackay et al. (2006) |
| CAS Datenbank | 1689-83-4(CAS DataBase Reference) |
| NIST chemische Informationen | Benzonitrile, 4-hydroxy-3,5-diiodo-(1689-83-4) |
| EPA chemische Informationen | Ioxynil (1689-83-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]H312: Harmful in contact with skin [Warning Acute toxicity, dermal]H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]H331: Toxic if inhaled [Danger Acute toxicity, inhalation]H361d ***: Suspected of damaging the unborn child [Warning Reproductive toxicity]H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P321, P330, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | 04/58/EC, Reg. (EU) 2022/801, Reg. (EU) No 540/2011Ioxynil: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Gefahrenübersicht | A mild skin and eye irritantCan be absorbed through skinMay be a developmental toxin, based on animal studies[ICSC] In acute poisoning, workers had vomiting, increase in body temperature, excessive perspiration, elevated thiocyanate in urine, and abnormal liver enzymesNo adverse effects were observed in 90-day 111 ppm oral study with ratsInhibited oxidative phosphorylation in rat liver mitochondria[HSDB] See Benzonitrile. |
| EG-Einstufung | Symbol: T, NR: 21-23/25-36-48/22-63-50/53S: (1/2)-36/37-45-60-61-63 |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: III |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including nitrogen oxides, iodine and cyanide compounds. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Packaging and Labelling | Do not transport with food and feedstuffs. Marine pollutant. |
| DOT Hazard Classification | IoxynilMarine pollutant |
| Hazard Classes and Categories | Acute Tox. 3 (100%)Acute Tox. 4 (100%)Eye Irrit. 2 (100%)Repr. 2 (61.3%)Repr. 2 (38.7%)STOT RE 2 (100%)Aquatic Acute 1 (100%)Aquatic Chronic 1 (100%)Reproductive toxicity - category 2Acute toxicity - category 3Acute toxicity - category 4Eye irritation - category 2Hazardous to the aquatic environment (acute) - category 1Hazardous to the aquatic environment (chronic) - category 1Specific target organ toxicity (repeated exposure) - category 2Acute Tox. 3 *Acute Tox. 4 *STOT RE 2 *Aquatic Chronic 1 |
| Skin, Eye, and Respiratory Irritations | Avoid skin and eye contact and inhalation of spray fumes. Prevent drifting. |
| Brandbekämpfung | Use water spray, powder, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .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 | Provision to contain effluent from fire extinguishing. Separated from strong oxidants and food and feedstuffs. |
| Expositionsschutz und Persönliche Schutzausrüstung | 2.0 [mg/m3], inhalable fraction, as CN[German Research Foundation (DFG)] |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Eye Prevention | Wear safety goggles or face shield. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C. |
| Skin Prevention | Protective gloves. Protective clothing. |
| Exposure Prevention | STRICT HYGIENE! AVOID ALL CONTACT! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN! IN ALL CASES CONSULT A DOCTOR! |
| Ingestion Prevention | Do not eat, drink, or smoke during work. Wash hands before eating. |
| Wechselwirkungen | DIFFERENTIAL FOLIAR...UPTAKE MAY...BE AFFECTED BY THE PRESENCE OR ABSENCE OF A SURFACTANT IN THE HERBICIDE FORMULATION. |
| Ökotoxizitätswerte | LD50 MALLARD ORAL 1200 MG/KG /TECHNICAL IOXYNIL OCTANOATE/LD50 PHEASANT ORAL 1000 MG/KG /TECHNICAL IOXYNIL OCTANOATE/LC50 HARLEQUIN FISH 3.3 PPM/48 HR /SODIUM SALT/ |
| Umweltverhalten | TERRERSTRIAL FATE: IOXYNIL IS LOOSELY BOUND, PROBABLY TO THE COLLOIDAL FRACTION OF SOILS. DISAPPEARANCE IS LESS RAPID IN STERILE SOILS INDICATING THAT SOIL MICROBES AID BREAKDOWN. ... RESULTANT AVG PERSISTENCE: VIRTUALLY NO PREEMERGENCE EFFECT FROM NORMAL APPLICATION RATES @ ANY PERIOD AFTER SPRAYING.TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 75(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that Bantrol will have high mobility in soil(SRC). Bantrol is expected to rapidly biodegrade in soil under aerobic conditions with a measured half-life of 9-10 days(4). Some degradation in anaerobic environments is possiblecyano-labelled Bantrol under anaerobic conditions released a small amount of 14CO2(5). Metabolites from the aerobic biodegradation of Bantrol were 3,5-diiodo-4-hydroxybenzamide and 3,5-diiodo-4-hydroxybenzoic acid(5). Volatilization of Bantrol should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 5.5X10-10 atm-cu m/mole(SRC), using a recommended regression equation(6). Volatilization from dry soil surfaces is not expected(SRC) based on an estimated vapor pressure of 1.4X10-7 mm Hg(SRC), from a fragment constant method(7).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 75(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), suggests that Bantrol will not adsorb to suspended solids and sediment in water(SRC). Based on soil studies, Bantrol is expected to biodegrade under aerobic conditionssome biodegradation may be seen in anaerobic environments(SRC). An aerobic biodegradation half-life of 9-10 days was measured in a clay loam soil with high organic matter content(3). Metabolites from the aerobic biodegradation of Bantrol were 3,5-diiodo-4-hydroxybenzamide and 3,5-diiodo-4-hydroxybenzoic acid(4). Bantrol should not volatilize from water surfaces based on an estimated Henry's Law constant of 5.5X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF value of 3(1,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Bantrol was stable for several weeks in natural water exposed to UV light10% degradation required greater than 1 month(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Bantrol, which has an estimated vapor pressure of 1.4X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase Bantrol 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 about 75 days(3,SRC). Particulate-phase Bantrol may be physically removed from the air by wet and dry deposition(SRC). |
| 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.Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.Other Poison - Uncoupler |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion. |
| Signs and Symptoms | Dizziness. Headache. Sweating. Vomiting. Weakness. Fever.MAY BE ABSORBED! Pain. Redness.See Inhalation. |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. Avoid release to the environment in circumstances different to normal use. |
| Soil Adsorption/Mobility | The Koc of Bantrol is estimated as approximately 75(SRC), using a measured log Kow of 0.90(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that Bantrol has high mobility in soil(SRC). Alkaline soils adsorbed small amounts of Bantrol on soil particles(4). |
| Atmospheric Concentrations | URBAN AIR: Bantrol was not detected in air collected from Kitakyushu, Japan, in either July 1991 or April 1992 (detection limit=0.4 ng/cu m)(1). |
| Human Toxicity Excerpts | SYMPTOMS OF POISONING: INCREASED BODY TEMPERATURE, SWEATING & INCR RESPIRATION.FOUR WORKERS INVOLVED IN PRODUCTION OF IOXYNIL SUDDENLY DEVELOPED SUBACUTE POISONING. SYMPTOMS: WT LOSS DUE TO EXCESSIVE PERSPIRATION, FEVER, EMESIS. ELEVATED THIOCYANATE LEVELS IN URINE AND ENZYMES SGOT, CREATINE PHOSPHOKINASE, LACTATE DEHYDROGENASE & ALDOLASE WERE ELEVATED. THE URINARY THIOCYANATE LEVELS WERE ELEVATED IN THREE CASES (15-40 MG/L), WHILE NO AROMATIC AMINES WERE FOUND.A 54 yr old man who had undergone gastrectomy swallowed a small amount of an unknown fluid, which he had stored with his homemade wine. He died 45 min later en route to the hospital. Chemical analysis ... established that the remaining material was ioxynil at a concn of 11.3%. It was estimated that the victim had swallowed 2000-3000 mg. Alcohol was also present at a concn of 0.135%. Autopsy revealed hyperemia of all organs, edema of the lungs, and edema of the brain with an occipital cone.Signs and symptoms: Gastroenteritis, fever/hyperthermia (increased metabolic rate). /From table/ |
| Artificial Pollution Sources | Bantrol's use as a selective contact herbicide outside of the United States(1,2), will result in its direct release to the environment(SRC). |
| Environmental Biodegradation | ...IOXYNIL.../HAS/ HALF-LIFE OF LESS THAN 2 WK IN SOILS. WHEN STERILE SOILS WERE TREATED WITH IOXYNIL...LITTLE OR NO DEGRADATION WAS /DETECTED/... IN NONSTERILE SOILS...DEGRADATION WAS RAPID. DEGRADATION PRODUCTS FROM NONSTERILE SOILS TREATED WITH ...IOXYNIL WERE...IDENTIFIED AS THE BENZOIC ACID DERIVATIVES WITH TRACES OF INORGANIC IODIDE FROM IOXYNIL./Researchers/ attributed the reduced effectiveness of ... herbicide during adaptation studies to microbial degradation. Recent studies ... have also provided indirect evidence for the adaptation of Erwinia carotovora, Pseudomonas fluorescens, and Bacillus species to ioxynil.In nonsterile soil, Bantrol was biodegraded to 3,5-diiodo-4-hydroxybenzoic acid through its intermediate amidefree iodine was also liberated(1). Degradation of both ring and cyano-labelled Bantrol to CO2 in a clay loam soil with high organic matter content was measured14CO2 was released more quickly initially from the cyano-labelled Bantrol(2). No 14CO2 was released from autoclaved soil or from ring-labelled Bantrol under anaerobic conditions(2). Cyano-labelled Bantrol under anaerobic conditions released a small amount of 14CO2. Metabolites from the aerobic biodegradation of Bantrol were 3,5-diiodo-4-hydroxybenzamide and 3,5-diiodo-4-hydroxybenzoic acid(2). The aerobic half-life of Bantrol degradation in a clay loam soil with high organic matter content was 9-10 days(3). |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 3276 |
| Zollcode | 29269095 |
| RTECS-Nr. | DI4025000 |
| R-Sätze (R) | 63-50/53-48/22-36-23/25-21 |
| Gefahrensymbole | N-T,N,T |
| Sicherheitshinweise (S) | 61-60-45-36/37-63 |
| Gefahrenklasse | 6.1 |
| Verpackungsgruppe | III |
| Gefahrstoffdaten | 1689-83-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
3,5-Diiodo-4-hydroxybenzonitrile is used in the preparation of herbicides Bromoxynil and Ioxynil.