Terbufos

HCID 25670CAS 13071-79-9

Grundinformationen

Standard-SMILES
CCOP(=S)(OCC)SCSC(C)(C)C
InChIKey
XLNZEKHULJKQBA-UHFFFAOYSA-N
Summenformel
C9H21O2PS3
Durchschnittliche Molmasse
288,4 g/mol
Monoisotopische Masse
288,04412954

Überblick

Technical product is a clear, colorless to pale yellow liquid. Used as a soil insecticide. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
Terbufos
IUPAC
tert-butylsulfanylmethylsulfanyl-diethoxy-sulfanylidene-λ5-phosphane
Lokaler Name
Terbufos
Englischer Name
Terbufos
Summenformel
C9H21O2PS3
Molmasse
288.43

Namen und Synonyme

TERBUFOSCounter13071-79-9ContravenCounter 15G soil insecticideDTXSID2022254AC 92100St-100AI3-27920Counter 15GM83BN0F8R9Phosphorodithioic acid S-((tert-butylthio)methyl) O,O-diethyl ester
Weitere Namen anzeigen
CONTRAVEPlydaxHUNTERTERTINac92100Aragranac92,100
S-tert-Butylthiomethyl O,O-diethyl phosphorodithioateS-(((1,1-Dimethylethyl)thio)methyl) O,O-diethyl phosphorodithioateS-(((1,1-Dimethylethyl)thio)methyl)-O,O-diethyl phosphorodithioateAC-92100Phosphorodithioic acid, S-[[(1,1-dimethylethyl)thio]methyl] O,O-diethyl esterS-((tert-Butylthio)methyl)O,O-diethylphosphorodithioateDTXCID702254CHEBI:38960

Datenbank-Bezeichner

CAS
13071-79-9
PubChem CID
25670
DTXSID
DTXSID2022254
ChEMBL
CHEMBL1406292
ChEBI
CHEBI:38960
UNII
M83BN0F8R9
EC Number
235-963-8
Nikkaji
J8.081K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,5
Polarare Oberfläche (TPSA)
101 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
8
Schwere Atome
15

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
Pesticides · 6 Einträge

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Insecticides, Nematicides

Pesticide (Terbufos) -> USDA PDB

Pesticide

LogP · 3 Einträge

log Kow = 4.48

4.48

3.98

OdorMercaptan-like odor
Density · 5 Einträge

1.105 at 75.2 °F (EPA, 1998) - Denser than water; will sink

1.105 g/cu cm @ 24 °C

Relative density (water = 1): 1.1

1.105 at 75.2 °F

1.105 @ 24°C

Color/Form · 3 Einträge

Slightly yellowish liquid

Slightly reddish liquid

Clear, slightly brown liquid

Physikochemische Eigenschaften

Schmelzpunkt
-29 °C · -29°C
Siedepunkt
69 °C · 69°C (0.01 mmHg)
Dichte
1.105 · 1.105
Dampfdruck
3.46 · 3.46×10-2 Pa (25 °C)
Flammpunkt
88 °C · 88°C
storage temp.
4 °C · APPROX 4°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H300: 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)

Danger

H300+H310+H330 (38.2%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute 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)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Hazard Traits - Developmental Toxicity; Neurotoxicity

Regulation (EC) No 1107/2009 (amended)

2002/2076

Terbufos: 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.)

Other Safety InformationIMAP assessments - Phosphorodithioic acid, S-[[(1,1-dimethylethyl)thio]methyl]O,O-diethyl ester: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

This is a liquid organophosphorus pesticide. Fire may produce irritating or poisonous gases. Hydrolyzes under alkaline conditions. (EPA, 1998)

Combustible.

Fire PotentialModerate fire risk.
Health HazardsThis 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)

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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 disposal; do not scatter the material.

In case of fire in the surroundings: all extinguishing agents allowed.

First Aid Measures · 4 Einträge

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.

First AidNote: Terbufos is a cholinesterase inhibitor.
Safe StorageSeparated from food and feedstuffs and oxidizing materials. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection · 1 Eintrag

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

Fire Fighting Procedures · 2 Einträge

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, toxic; Organophosphorus 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/

Toxikologische Informationen

Interactions · 1 Eintrag

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/

Ecotoxicity Values · 5 Einträge

LC50 Phasianus colchicus (ring necked pheasant) dietary 145 mg/kg/8 day

LC50 Anas platyrhynchos (mallard duck) dietary 185 mg/kg/8 day

LC50 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.

Environmental Fate · 3 Einträge

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 °C; it 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.

Food Survey Values · 1 Eintrag

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.

Adverse EffectsOther Poison - Organophosphate
Exposure RoutesThe substance can be absorbed into the body in hazardous amounts by ingestion, by inhalation and through the skin.

Regulatorische Informationen

FIFRA Requirements · 4 Einträge

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: 0109; Pesticide type: Insecticide and fungicide (nematicide); Registration Standard Date: 09/01/88; Case 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): Terbufos; Data Call-in (DCI) Date(s): 09/15/92, 10/13/95; AI 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: bananas; beet, sugar, roots; beet, sugar, tops; corn, field, fodder; corn, field, forage; corn, pop, fodder; corn, pop, forage; corn, grain ; corn, sweet, kernel plus cob with husks removed; corn, sweet, forage; corn, sweet, fodder; sorghum, fodder; sorghum, forage; and 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.

CERCLA Reportable Quantities · 1 Eintrag

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.

State Drinking Water Guidelines · 2 Einträge

(FL) FLORIDA 0.18 ug/l

(ME) MAINE 0.35 ug/l

Federal Drinking Water GuidelinesEPA 0.4 ug/L

Sicherheitsdaten

wgk
3
ridadr
UN 2810
hs_code
29309090
RTECS-Nr.
TD7200000
risk_code
27/28-50/53
Toxizität
LD50 orally in quail: 15 mg/kg (Hill, Camardese)

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

The organophosphorus compounds owe their biological activities to the capacity of the central P atom to phosphorylate the esteratic site of the enzyme, cholinesterase, which is an essential constituent of the nervous system not only of Insecta but also of all higher animals. /Organophosphorus compounds/

Organophosphates poison insects and mammals primarily by phosphorylation of the acetylcholinesterase enzyme at nerve endings. ... At sufficient dosage, loss of enzyme function allows accumulation of acetylcholine (the impulse- transmitter substance) at cholinergic neuroeffector junctions (muscarinic effects, and at skeletal myoneural junctions and in autonomic ganglia (nicotinic effects). Organophosphates also impair nerve impulse transmission in the brain ... . /Organophosphate pesticides/

Metabolism/Metabolites · 2 Einträge

Metabolism occurs principally by oxidation, hydrolysis by esterases, and by transfer of portions of the molecule to glutathione. Oxidation of organophosphorus insecticides may result in more or less toxic products. The glutathione transferase reactions produce products, that are, in most cases, of low toxicity. Hydrolytic and transferase reactions affect both thioates and their oxons. /Organophosphorus Pesticides/

Biotransformation of terbufos in rat liver revealed four metabolites in the effluent prepared with a C18 cartridge after the rat liver was perfused for one hour in situ. Analysing the spectrogram of GC-IR and GC-MS, metabolite IV appeared to be an oxidative desulfuration product of terbufos with the formula C9H21O3PS2, the recovery of which in the effluent was 2.13%; metabolite I appeared to be an hydrolysate of metabolite IV with the formula C5H13O3PS, the recovery of which was 0.13%; metabolite II appeared to be an hydrolysate of terbufos with the formula C5H13O2PS2, the recovery of which was 2.65%; metabolite III appeared to be a methylate of metabolite II, with the formula C6H15O2PS2, the recovery of which was 1.42%. Relatively the recovery of terbufos was 40.8%. These results were in accord with the regular metabolic pattern in vivo of phosphorothioates with a thioether group.

Absorption, Distribution and Excretion · 3 Einträge

A metabolism study of rats indicated that 83% of a single administration of 0.8 mg/kg terbufos was excreted in the urine in the form of metabolites and 3.5% in the feces during 168 hours. No terbufos accumulated in tissues.

Rapidly absorbed through skin.

Among 11 farmers who applied a formulated terbufos product while planting corn, ...no alkyl phosphates were detected in urine... /after an estimated respiratory dose of 0.009 mg/cu m terbufos/.

Verwendung und Herstellung

Uses · 6 Einträge

Used as a granular insecticide and nematicide applied to the soil for crops of corn, grain, sorghum, sugar beets, and bananas; [ACGIH]

Farming (Pesticides) [Category: Industry]

For terbufos (USEPA/OPP Pesticide Code: 105001) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Soil insecticide

Control of ... nematodes in beet, maize, cotton, sorghum, onions, cabbage, and bananas

... Effective initial and residual activity against soil dwelling arthropods. Soil application of granules controls Diabrotica species larvae on maize, Tetanops myopaeformis on sugar beet, Delia brassicae on cabbages, millipedes, onion maggots, symphylids, wireworms and other soil dwelling arthropods. Various above ground pests also are controlled on plants grown in terbufos treated soil. It has nematicidal activity.

Methods of ManufacturingTerbufos is prepared by treating O,O-diethyldithiophosphoric acid with formaldehyde and tert-butanethiol.
Formulations/Preparations · 5 Einträge

Technical product (85-88% purity)

Granular

Trade Names: Counter, Counter 15G, ENT 27920

...Applied as a granular formulation (15 and 20% active ingredient)... .

For more Formulations/Preparations (Complete) data for TERBUFOS (6 total), please visit the HSDB record page.

Use Classification · 2 Einträge

Insecticides, Nematicides

INSECTICIDES

General Manufacturing InformationThe WHO Recommended Classification of Pesticides by Hazard identifies Terbufos (technical grade) as Class IA: extremely hazardous; Main Use: insecticide-applied to soil: not used with herbicides or plant growth regulators.

Anwendungen

VerwendenTerbufos is used to control soil pests in maize, sugar beet and vegetables and also nematodes in sugar beet and bananas.

Vor- und nachgelagerte Produkte

Zugehörige Reaktionen

2

Verknüpfte Notizen

Wird geladen…