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Tetradifon
Sulfone · Diphenylsulfon · TCDS · V-18 · Duphar · Mition · TEDION · TEDONE
Identifikatoren & physikalische Daten
| CAS No. | 116-29-0 |
|---|---|
| Summenformel | C12H6Cl4O2S |
| Durchschnittliche Molmasse | 356 g/mol |
| Monoisotopische Masse | 353,88426115 g/mol |
| SMILES | O=S(=O)(c1ccc(Cl)cc1)c1cc(Cl)c(Cl)cc1Cl |
| InChIKey | MLGCXEBRWGEOQX-UHFFFAOYSA-N |
| PubChem CID | 8305 |
| ChEMBL | CHEMBL437926 |
| ChEBI | CHEBI:39330 |
| EC No. | 204-134-2 |
| DTXSID | DTXSID7021316 |
| Lokaler Name | Tetradifon |
Chemische & physikalische Eigenschaften
| XLogP | 5,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 42,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 400 |
| SpringerMaterials Properties | Fusion temperature |
| Pestizide | Acaricides, InsecticidesActive substance -> EU Pesticides database: Not approvedPesticides -> Organochlorine PesticidesPesticide (Tetradifon) -> USDA PDB |
| LogP (Verteilungskoeffizient) | log Kow= 4.61 |
| Geruch | ODORLESS |
| Dichte | 1.151 @ 20 °CRelative density (water = 1): 1.51.5630 (estimate) |
| Color/Form | Crystals from benzeneWhite, crystalline powder |
| Löslichkeit | Solubility in acetone 67.3, methanol 3.46, ethyl acetate 67.3, hexane 1.52, dichloromethane 297, xylene 105 (all in g/L, 20 °C)Soluble in aromatic hydrocarbon solvents, dioxanAT 18 °C: 0.4 G/100 G PETROLEUM ETHER7.1 G/100 G ETHYL ACETATE10.5 G/100 G METHYL ETHYL KETONEAND 1.6 G/100 G CARBON TETRACHLORIDE.In water, 7.80X10-2 mg/L @ 20 °CSol in water ... at 20 °C, 0.08 mg/l.Solubility in water at 20 °C: none50ug/L(10 ºC) |
| Corrosivity | NON-CORROSIVE |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen chloride and sulfur oxides/. |
| Schmelzpunkt | 146.5 - 147.5 °CMELTING POINT: 144 °C /Technical product/148-149 °C146.5-147.5° |
| Dampfdruck | 2.40X10-10 mm Hg at 20 °CVapor pressure, Pa at 20 °C: |
| Siedepunkt | 484.0±45.0 °C(Predicted) |
| Lagerbedingungen | 0-6°C |
| Aggregatzustand | Solid |
| Farbe | White to off-white |
| Merck | 13,9273 |
| BRN | 2292528 |
| Henry-Konstante | 6.9×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C12H6Cl4O2S/c13-7-1-3-8(4-2-7)19(17,18)12-6-10(15)9(14)5-11(12)16/h1-6H |
| InChIKey | MLGCXEBRWGEOQX-UHFFFAOYSA-N |
| SMILES | Clc1ccc(cc1)S(=O)(=O)c2cc(Cl)c(Cl)cc2Cl |
| CAS Datenbank | 116-29-0(CAS DataBase Reference) |
| NIST chemische Informationen | P-chlorophenyl, 2,4,5-trichlorophenyl sulfone(116-29-0) |
| EPA chemische Informationen | Tetradifon (116-29-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 71 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P273, P391, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Benzene, 1,2,4-trichloro-5-(4-chlorophenyl)sulfonyl-: 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. |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzene, 1,2,4-trichloro-5-[(4-chlorophenyl)sulfonyl]-: Environment tier I assessment |
| Brandgefahren | Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents. |
| Gefahrenübersicht | Decomposed by heat and flames forming toxic vapors including hydrogen chloride and sulfur oxidesThe substance may have effects on the kidneys and liver. [ICSC] May cause irritation[MSDSonline] |
| Special Reports | WHOEnviron Health Criteria 67: Tetradifon p.9 (1986) |
| FIFRA-Anforderungen | Tolerances are established for residues of the insecticide tetradifon (2,4,5,4'-tetrachlorodiphenyl sulfone) in or on raw agricultural commodities as follows: appleapricotcherrycitron, citruscrabapplescucumberfigfig, dried fruitgrapefruithop, driedhop, vinelemonlimemeatmelonmilknectarineorange, sweetpeachpearpeppermintplum, prune, freshpumpkinquincespearmint, topsstrawberryand tangerine.Pesticide chemicals that cause related pharmacological effects will be regarded as having an additive deleterious action. Where residues from two or more chemicals in the same class are present in or on a raw agricultural commodity the tolerance for the total of such residues shall be the same as that having the lowest numerical tolerance in this class. Tetradifon is a member of the class of chlorinated organic pesticides.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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Tetradifon is found on List B. Case No: 2655Case 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): 4-Chlorophenyl 2,4,5-trichlorophenyl sulfoneAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled." |
| Chemical Dangers | Decomposes on heating and on burning. This produces toxic fumes including sulfur oxides and hydrogen chloride. |
| Packaging and Labelling | Do not transport with food and feedstuffs. |
| Other Hazardous Reactions | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered. |
| Toxic Combustion Products | The substance decomposes on heating and on burning producing toxic fumes including sulfur oxides, hydrogen chloride. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Specific target organ toxicity - Single exposure - Category 2 (respiratory organs) |
| Standard Transportation Number | 49 216 72Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, nec, other, than agricultural).49 216 73Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, agricultural, nec, other than liquid). |
| Brandbekämpfung | Use alcohol-resistant foam, powder, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Refer for medical attention . |
| Sichere Lagerung | Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/ |
| Reinigungsverfahren | Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/ |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/ |
| Eye Prevention | Wear safety spectacles. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered. |
| Skin Prevention | Protective gloves. |
| Exposure Prevention | PREVENT DISPERSION OF DUST! |
| Ökotoxizitätswerte | LD50 Mallard oral > 2,000 mg/kg, male, 4 mo oldLC50 Colinus virginianus (Bobwhite quail) dietary >5000 mg/kg/8 dayLC50 Coturnix japonica (Japanese quail) dietary >5000 mg/kg/8 dayLC50 Anas platyrhyncus (Mallard duck) dietary >5000 mg/kg/8 dayFor more Ecotoxicity Values (Complete) data for TETRADIFON (12 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7700(SRC), determined from a log Kow of 4.61(2) and a regression-derived equation(3), indicates that tetradifon is expected to be immobile in soil(SRC). Volatilization of tetradifon from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant estimated as 1.44X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.40X10-10 mm Hg(2), and water solubility, 7.80X10-2 mg/L(2). Tetradifon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). One persistence study indicated that 81% of tetradifon applied to an orchard with loamy soil (3.1% organic content, pH 7.4 and 26% clay) persisted for a minimum of 6 monthspost application time was not given and samples were collected in the summer of 1967 and tested in 1968(4). Tetradifon did not persist in silty clay (4.9% organic content, pH 7.4 and 42% clay) approximately 2 yrs postapplication(4). Incubation of tetradifon with inocula of rumina bacteria or ciliated protozoa under anaerobic conditions suggests that tetradifon is not nutritionally used for growth of the organism and that this compound does not stimulate endogenous gas production(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7700(SRC), determined from a log Kow of 4.61(2) and a regression-derived equation(3), indicates that tetradifon is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.44X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.40X10-10 mm Hg(2), and water solubility, 7.80X10-2 mg/L(2). According to a classification scheme(4), an estimated BCF of 1900(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Based on a persistence study in soil(6), biodegradation of tetradifon in water may not be an imporatant fate process.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetradifon, which has a vapor pressure of 2.40X10-10 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tetradifon may be removed from the air by wet and dry deposition(SRC). Particulate-phase tetradifon is stable in sunlight(3). |
| Lebensmitteluntersuchungswerte | Tetradifon was detected at concns of 0.006 and 0.044 ppm in 2 of 216 total-diet samples from 18 markets consisting of 82 foods collected from 3 different geographical areas(1). Tetradifon was detected in 1 of 6 fruit composites from Boston, MA at a concn of 0.044 ppm, 2 of 6 fruit composites from Los Angeles, CA at concns of 0.006 and 0.011 ppm, and 1 of 6 meat, fish and poultry composites from Los Angeles, CA at a concn of 0.076 ppm from June 1965 to April 1966(2). During October 1, 1981 to September 30, 1986, tetradifon was found in 6 of 19,851 agricultural commodities at a concn range of >0-0.1 ppm(3). Tetradifon residues were qualitatively detected in 2 of 13,085 food samples during FY89(4) and it was found in raw agricultural commodities during FY78-82(5). |
| 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. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of dust. |
| Ökotoxizitätsauszüge | /BIRDS and MAMMALS/ Tetradifon is relatively non-toxic for birds. ...Its toxicity /was studied/ for 4 species: bobwhite quail, ring-necked pheasant, mallard (all at 10 days of age), and 12-day-old Japanese quail. Tetradifon was included in food at concentrations of up to 5000 mg/kg and fed to the birds for 5 days. The mortality rate was estimated at 8 days. Bobwhite quail showed a 10% mortality rate at 5000 mg tetradifon/kg diet, but no deaths occurred in any other species./BIRDS and MAMMALS/ Signs of intoxication of mallards after oral administration of LD50 (more than 2000 mg/kg): ataxia, wing twitching, imbalance, and slowness. Signs appeared as soon as 1 hr after treatment. Remission had occurred by the day following treatment./AQUATIC SPECIES/ Waterfleas (Daphnia magna) were exposed to water suspensions of tetradifon of 0.2 or 2.0 mg/L for 48 hr (both concentrations exceed the water solubility of tetradifon). No toxic effects were observed./AQUATIC SPECIES/ The guppy (Lebistes reticulatus) showed signs of intoxication when exposed to tetradifon at 1 mg/L for 5 hr but recovered completely after being transferred to untreated water. Guppies, 3-4 weeks old, did not show any signs of intoxication when exposed to suspensions containing 2 mg technical tetradifon/L for 96 hr.For more Ecotoxicity Excerpts (Complete) data for TETRADIFON (8 total), please visit the HSDB record page. |
| Signs and Symptoms | Redness. |
| Acute Toxicity Link | Chemical: TETRADIFON |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. Avoid release to the environment in circumstances different to normal use. |
| Soil Adsorption/Mobility | The Koc of tetradifon is estimated as 7,700(SRC), using a log Kow of 4.61(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that tetradifon is expected to be immobile in soil. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ In photo-patch tests on 51 patients, ...tetradifon /was found/ to be one of the least active compounds of 29 pesticides tested./OTHER TOXICITY INFORMATION/ No reports of human poisonings have followed its extensive use in Europe. |
| Fish/Seafood Concentrations | Tetradifon concns averaged 1190 and 194 ng/g fresh weight in dead and live Mugil spp. viscera, respectivelytetradifon respective concns averaged 467 and 456 ng/g in dead and live Mugil spp. muscle taken from natural waters beside the Mediterranean sea(1). |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN3077 9/PG 3 |
| RTECS-Nr. | WR5850000 |
| R-Sätze (R) | 22-50/53 |
| Toxizität | LD50 orally in rats: 556 mg/kg (Ben-dyke) |
| Gefahrensymbole | Xn,N |
| Sicherheitshinweise (S) | 60-61 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 116-29-0(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1 |
Anwendungen & Verwendung
Verwenden
Acaricide. Ovicide on deciduous fruits, citrus, cotton and other crops.