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Terbufos
CONTRAVE · Plydax · st-100 · HUNTER · TERTIN · ac92100 · Aragran · Counter
Identifikatoren & physikalische Daten
| CAS No. | 13071-79-9 |
|---|---|
| Summenformel | C9H21O2PS3 |
| Durchschnittliche Molmasse | 288,4 g/mol |
| Monoisotopische Masse | 288,04412954 g/mol |
| SMILES | CCOP(=S)(OCC)SCSC(C)(C)C |
| InChIKey | XLNZEKHULJKQBA-UHFFFAOYSA-N |
| PubChem CID | 25670 |
| ChEMBL | CHEMBL1406292 |
| ChEBI | CHEBI:38960 |
| EC No. | 235-963-8 |
| DTXSID | DTXSID2022254 |
| Lokaler Name | Terbufos |
Chemische & physikalische Eigenschaften
| XLogP | 4,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 101 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 206 |
| Stoffklassen | Flammable agents - 2nd degree |
| Pestizide | InsecticidesActive substance -> EU Pesticides database: Not approvedPesticides -> Organophosphate InsecticidesInsecticides, NematicidesPesticide (Terbufos) -> USDA PDB |
| LogP (Verteilungskoeffizient) | log Kow = 4.483.98 |
| Geruch | Mercaptan-like odor |
| Dichte | 1.105 at 75.2 °F (EPA, 1998) - Denser than waterwill sink1.105 g/cu cm @ 24 °CRelative density (water = 1): 1.11.105 @ 24°C |
| Color/Form | Slightly yellowish liquidSlightly reddish liquidClear, slightly brown liquid |
| Löslichkeit | Insoluble (<1 mg/ml) (NTP, 1992)Readily soluble in most organic solvents: aromatic hydrocarbons, chlorinated hydrocarbons, alcohols, acetoneIn water, 5.07 mg/l @ 25 °CSolubility in water, mg/l at 25 °C: 5.07 (very poor)Chloroform (Slightly), Methanol (Slightly) |
| Corrosivity | Non-corrosive to metals. |
| Flammpunkt | 190 °F (EPA, 1998)88 °C (Tag Open Cup) /Technical terbufos/87.8 °C88°C |
| Siedepunkt | 156 °F at 0.01 mmHg (EPA, 1998)69 °C @ 0.01 mm Hg68.9 °C156 °F at 0.01 mmHg315 °C @760 [mm Hg]69°C (0.01 mmHg) |
| Decomposition | This compound decomposes in the presence of acids or bases /and/... at temperatures over 120 °C.When heated to decomp, it emits very toxic fumes of /sulfur oxides and phosphorus oxides/.Decomposes on prolonged heating above 120 °C. Hydrolysis DT50 for tech. 2-3 days (pH 4-9). |
| Schmelzpunkt | -20.6 °F (EPA, 1998)-29 °C-29.2 °C-29°C |
| Dampfdruck | 3.46×10-2 Pa (25 °C) |
| Lagerbedingungen | APPROX 4°C |
| Aggregatzustand | Liquid |
| Farbe | Colorless, pale |
| Merck | 13,9233 |
| BRN | 1710115 |
| Henry-Konstante | 4.1×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C9H21O2PS3/c1-6-10-12(13,11-7-2)15-8-14-9(3,4)5/h6-8H2,1-5H3 |
| InChIKey | XLNZEKHULJKQBA-UHFFFAOYSA-N |
| SMILES | CCOP(=S)(OCC)SCSC(C)(C)C |
| CAS Datenbank | 13071-79-9(CAS DataBase Reference) |
| NIST chemische Informationen | Phosphorodithioic acid, s-[(tert-butylthio)methyl] o,o-diethyl ester(13071-79-9) |
| EPA chemische Informationen | Terbufos (13071-79-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)H300+H310+H330 (38.2%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Hazard Traits - Developmental ToxicityNeurotoxicityRegulation (EC) No 1107/2009 (amended)2002/2076Terbufos: 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Phosphorodithioic acid, S-[[(1,1-dimethylethyl)thio]methyl]O,O-diethyl ester: Environment tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This is a liquid organophosphorus pesticide. Fire may produce irritating or poisonous gases. Hydrolyzes under alkaline conditions. (EPA, 1998)Combustible. |
| Brandpotenzial | Moderate fire risk. |
| Gesundheitsgefahren | This material may be fatal if swallowed, inhaled, or absorbed through the skin. Repeated inhalation or skin contact may progressively increase susceptibility to poisoning. (EPA, 1998) |
| Gefahrenübersicht | Products containing >15% terbufos are Restricted Use Pesticides to be handled only by certified applicators. [EXTOXNET] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs] |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: I |
| Special Reports | USEPA/Office of Pesticide ProgramsInterim Reregistration Eligibility Decision (IRED) for Terbufos. EPA issues an IRED for a pesticide that is undergoing reregistration, requires a reregistration eligibility decision, and also needs a cumulative assessment under FQPA. The IRED, issued after EPA completes the individual pesticide\'s aggregate risk assessment, may include taking risk reduction measures -- for example, reducing risks to workers or eliminating uses that the registrant no longer wishes to maintain -- to gain the benefits of these changes before the final RED can be issued following the Agency\'s consideration of cumulative risks.[Available from, as of July 24, 2003: http://www.epa.gov/pesticides/reregistration/status.htm] |
| 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. Terbufos 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: 0109Pesticide type: Insecticide and fungicide (nematicide)Registration Standard Date: 09/01/88Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.Active ingredient (AI): TerbufosData Call-in (DCI) Date(s): 09/15/92, 10/13/95AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.Tolerances are established for combined residues of the insecticide terbufos (S-((1,1-dimethyl)thio)methyl) O,O-diethyl phosphorodithioate) and its cholinesterase-inhibiting metabolites in or on the following raw commodities: bananasbeet, sugar, rootsbeet, sugar, topscorn, field, foddercorn, field, foragecorn, pop, foddercorn, pop, foragecorn, graincorn, sweet, kernel plus cob with husks removedcorn, sweet, foragecorn, sweet, foddersorghum, foddersorghum, forageand sorghum, grain.A time-limited tolerance to expire December 15, 1997 is established for combined residues of the insecticide/nematicide terbufos (S-((1,1-dimethyl)thio)methyl) O,O-diethyl phosphorodithioate) and its cholinesterase-inhibiting metabolites in or on the following raw agricultural commodity: coffee bean, green.Based on its review, EPA has identified risk management measures that it believes are necessary to address the human health and environmental risks associated with the current use of terbufos. The EPA is now publishing its interim decision on the reregistration eligibility of and risk management decision for the current uses of terbufos and its associated human health and environmental risks. The reregistration eligibility and tolerance reassessment decisions for terbufos will be finalized once the cumulative risks for all of the organophosphate pesticides are considered. The ...Interim Reregistration Eligibility Decision for Terbufos, which was approved on September 28, 2001, contains the Agencys decision on the individual chemical terbufos. |
| Reactivity Profile | Organothiophosphates, such as TERBUFOS, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. This compound decomposes in the presence of acids or bases (NTP, 1992). |
| Brandbekämpfung | This is a liquid organophosphorus pesticide. Wear positive pressure breathing apparatus and special protective clothing. Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposaldo not scatter the material.In case of fire in the surroundings: all extinguishing agents allowed. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer immediately for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.Rinse mouth. Refer immediately for medical attention. Give a slurry of activated charcoal in water to drink. |
| Erste Hilfe | Note: Terbufos is a cholinesterase inhibitor. |
| Sichere Lagerung | Separated from food and feedstuffs and oxidizing materials. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. |
| Expositionsschutz und Persönliche Schutzausrüstung | Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baselineButylcholinesterase activity in serum or plasma = 60% of individual's baselineSample at end of shift[TLVs and BEIs] |
| 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. /Organophosphorus pesticides, liquid, flammable, toxicOrganophosphorus pesticides, liquid, toxic/If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) /Organophosphorus pesticides, solid, toxic/ |
| Lagerbedingungen | You should store this chemical in a freezer and away from all mineral acids and bases. |
| Reinigungsverfahren | Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid, flammable, toxicOrganophosphorus pesticides, liquid, toxicOrganophosphorus pesticides, solid, toxic/Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid, flammable, toxicEnvironmental 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 soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, liquid, flammable, toxic |
| Freisetung ohne Brand | This is a liquid organophosphorus pesticide. Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. Do not touch spilled materialstop leak if you can do so without risk. Use water spray to reduce vapors. |
| 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 | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in covered containers. Then store and dispose of according to local regulations. |
| Preventive Measures | /Use/ freshly laundered, long-sleeved work clothing daily. Clean cap, gloves (rubber, cotton) while transferring from package to equipment. Launder or discard cotton gloves after each days's usewash rubber gloves with soap and water after each use. Do not wear the same gloves for other work. Destroy and replace gloves frequently. Launder clothing before reuse. Wash thoroughly with soap and water before eating or smoking. Bathe at the end of the work day, change outer clothing.Not for use or storage in or around the house.Keep out of reach of domestic animals.Do not breathe dust, do not contaminate food or feed products.For more Preventive Measures (Complete) data for TERBUFOS (13 total), please visit the HSDB record page. |
| Wechselwirkungen | Because different classes of enzymes may be inhibited, the effects of organophosphorus pesticide poisoning may be complex and potentially at least could involve interactions with drugs as well as with other pesticides or chemicals. Potentiation may also involve solvents or other components of formulated pesticides. Certain drugs such a phenothiazines, antihistamines, CNS depressants, barbiturates, xanthines (theophylline), aminoglycosides and parasympathomimetic agents are to be avoided because of increased toxicity. /Organophosphorus pesticides/ |
| Ökotoxizitätswerte | LC50 Phasianus colchicus (ring necked pheasant) dietary 145 mg/kg/8 dayLC50 Anas platyrhynchos (mallard duck) dietary 185 mg/kg/8 dayLC50 Salmo gairdneri (rainbow trout) 0.01 mg/l/96 hr /Conditions of bioassay not specified/LC50 Lepomis macrochirus (bluegill sunfish) 0.004 mg/l/96 hr /Conditions of bioassay not specified/For more Ecotoxicity Values (Complete) data for TERBUFOS (10 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 500-5000(2-5), indicate that terbufos is expected to have low to slight mobility in soil(SRC). Volatilization of terbufos from moist soil surfaces is expected(SRC) given a Henry's Law constant of 0.000024 atm-cu m/mole(SRC), derived from a vapor pressure of 0.00032 mm Hg(6) and a water solubility of 5.07 mg/l(7). However, adsorption to soil is expected to attenuate volatilization(SRC). Terbufos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). Half-lives in soil ranged from 11-17 days(8,9). Hydrolysis and microbial degradation are the primary dissipation processes for terbufos in the environment when it is applied to soil as required by the current label(10).AQUATIC FATE: Based on a classification scheme(1), Koc values in the range of 500-5000(2-5), indicate that terbufos is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(6) based upon a Henry's Law constant of 0.000024 atm-cu m/mole(SRC), derived from a vapor pressure of 0.00032 mm Hg(7) and water solubility of 5.07 mg/l(8). Using this Henry's Law constant and an estimation method(9), volatilization half-lives for a model river and model lake are 2.8 and 26 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 43 days if adsorption is considered(10). According to a classification scheme(11), an estimated BCF of 560(SRC), from a log Kow of 4.48(12), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Terbufos was incubated in natural, sterilized and distilled water, with an initial pH of 8.8 at 20 °Cit disappeared rapidly (half-life = 3 days) in all systems(13). The half-lives of terbufos in distilled, deionized unbuffered water, and in buffered solution at pH 5, 7, and 9 under natural sunlight (Clemson, SC) were 0.940, 1.35, 1.12, and 1.05 hours(14).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terbufos, which has a vapor pressure of 0.00032 mm Hg at 20-25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase terbufos 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 1.6 hours(SRC), calculated from its rate constant of 2.4X10-10 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). While terbufos was found to degrade in solution upon exposure to sunlight(4), no data were found regarding direct photolysis in air by sunlight. |
| Lebensmitteluntersuchungswerte | Terbufos was qualitatively found as residue in samples tested during the Food and Drug Administration pesticide residue monitoring of various food samples for the test period of 1978-1982(1) and 1983-1986(2). Terbufos was detected in the ethyl acetate and dichloromethane extracts of brown rice, potato, cabbage, lettuce, carrot, cucumber, shiitake mushroom, apple, strawberry, and banana obtained from a local retail store in Japan(3). Of the 16,198 imported commodities sampled from Jan 1992-Mar 1994 in the US, terbufos was found in one sample of imported fresh pears (n=775), at a concn in the range of 0.05-0.1 ppm(4). Terbufos was not detected as residues during the 1992(5) and 1994(6) US regulatory monitoring studies. |
| Unerwünschte Wirkungen | Other Poison - Organophosphate |
| Expositionspfade | The substance can be absorbed into the body in hazardous amounts by ingestion, by inhalation and through the skin. |
| Milk Concentrations | Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/ |
| Ökotoxizitätsauszüge | /BIRDS and MAMMALS/ "Severe" signs of toxicity (tremors, shallow breathing, motionless crouching, and loss of righting reflex) occurred among deer mice given single oral doses of 1.69 or 2.48 mg/kg terbufos by gavagemortality was 33% among mice given 1.69 mg/kg and 63% among mice given 2.48 mg/kg. Deaths occurred between 0.4 and 70 hr after dosing, and 90% of mice died between 2 and 9 hr after treatment./BIRDS and MAMMALS/ ...Deer mice receiving graded single oral doses of terbufos exhibited dose-dependent inhibition of brain /acetylcholinesterase/ activity, ...recovery was not detected over a 96 hr period, suggesting that brain /acetylcholinesterase/ activity response to the highly toxic terbufos was atypical of /organophosphate/ pesticides. ...Brain /acetylcholinesterase/ activity was only inhibited by 12-40% in the majority of mice that died./BIRDS and MAMMALS/ Red-winged blackbirds are more sensitive to terbufos and diazinon intoxication than are European starlings, and the young of both species are more sensitive than the adults. When mortality is used as the endpoint, adult starlings are approximately 103 times less sensitive to terbufos intoxication than are 2-day old starling chicks and 137 times less sensitive than adult red-wings. Adult red-wings were only 4.1 times less sensitive than 0 to 3-day old red-wing chicks. Adult starlings were approximately 47 times less sensitive to diazinon toxicity than 2-day old starling nestlings and 65 times less sensitive than adult red-wings. Adult red-wings were 3.8 times less sensitive to diazinon than 0- to 3-day old red-wing nestlings. Plasma and brain ChE activity was depressed in starling and red-wing adults in a dose-dependent fashion, but the relationship between dose, and plasma and brain ChE depression was more evident in some nestling age groups than in others. Baseline ChE activity cannot be invoked to explain the sensitivity difference between species. Baseline ChE activities in both brain and plasma increase with age in both species. These changes may account in part for the greater sensitivity of the young as compared to the adult./AQUATIC SPECIES/ A 96-hr aqueous exposure and a 12-hr dietary exposure of juvenile red swamp crayfish, Procambarus clarkii, to terbufos produced median lethal concentrations (LC50s) of 5.9 g/L (95% CI: 4.4, 8.1) and 4.4 g/g pellet (95% CI: 2.9, 6.7), respectively. Aberrant behavior, such as loss of motor control and equilibrium, was noted at concentrations almost 50% of the aqueous LC50 and 80% of the dietary LC50. As concentration increased, AChE activity decreased and mortality and aberrant behavior increased. I50s, the percentage of AChE inhibition at which 50% of the crayfish died, for aqueous and dietary exposures were 76.5% (95% CI: 67.4, 85.6) and 86.1% (95% CI: 78.1, 94.1) of control activity, respectively.For more Ecotoxicity Excerpts (Complete) data for TERBUFOS (10 total), please visit the HSDB record page. |
| Signs and Symptoms | See Ingestion.EASILY ABSORBED! See Ingestion.Blurred vision. Headache. Dizziness. Muscle spasms. Weakness. Vomiting. Diarrhoea. Abdominal pain. |
| Acute Toxicity Link | Chemical: TERBUFOS |
| Effluent Concentrations | Sediment from nine sampling sites located in the Suerte River basin in Costa Rica were analyzed for pesticides(1). Terbufos was detected in one of the nine samples from an open canal flowing from a banana packing facility at a concn of 154 ug/kg dry weight, and was not detected at the other sampling sites(1). Terbufos was detected in 2 of 32 samples in effluent from two banana packing plants in the Suerte River basin, Costa Rica(1). |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. Bioaccumulation of this chemical may occur in 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. |
| CERCLA-Meldepflichtmengen | Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Terbufos is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs. |
| Landesrichtlinien für Trinkwasser | (FL) FLORIDA 0.18 ug/l(ME) MAINE 0.35 ug/l |
| Bundesrichtlinien für Trinkwasser | EPA 0.4 ug/L |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2810 |
| Zollcode | 29309090 |
| RTECS-Nr. | TD7200000 |
| R-Sätze (R) | 27/28-50/53 |
| Toxizität | LD50 orally in quail: 15 mg/kg (Hill, Camardese) |
| Gefahrensymbole | T+N,N,T+ |
| Sicherheitshinweise (S) | 36/37-45-60-61 |
| Gefahrenklasse | 6.1(a)Acute Tox. 1 DermalAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1 |
| Verpackungsgruppe | I |
| Lagerklasse | 6.1A - Combustible, acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 13071-79-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Terbufos is used to control soil pests in maize, sugar beet and vegetables and also nematodes in sugar beet and bananas.