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O,O-Diethyl-O-1-phenyl-1,2,4-triazol-3-ylthio-phosphat

Triazophos

HCID 32184
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Grundinformationen

CAS
24017-47-8
Standard-SMILES
CCOP(=S)(OCC)Oc1ncn(-c2ccccc2)n1
InChIKey
AMFGTOFWMRQMEM-UHFFFAOYSA-N
Summenformel
C12H16N3O3PS
Durchschnittliche Molmasse
313,31 g/mol
Monoisotopische Masse
313,06499955

Überblick

Yellowish oil. Used to control insects, mites, and nematodes. Not registered as a pesticide in the U.S. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
Triazophos
IUPAC
diethoxy-[(1-phenyl-1,2,4-triazol-3-yl)oxy]-sulfanylidene-λ5-phosphane
Lokaler Name
O,O-Diethyl-O-1-phenyl-1,2,4-triazol-3-ylthio-phosphat
Englischer Name
Triazophos
Summenformel
C12H16N3O3PS
Molmasse
313.31

Namen und Synonyme

Triazophos24017-47-8HostathionTRIAZOFOSHOE 2960O,O-diethyl O-(1-phenyl-1H-1,2,4-triazol-3-yl) phosphorothioateDTXSID9037612HOE 2960 OJPhosphorothioic acid, O,O-diethyl O-(1-phenyl-1H-1,2,4-triazol-3-yl) esterTriazofosz1-Phenyl-1,2,4-triazolyl-3-(O,O-diethylthionophosphate)O,O-Diethyl O-(1-phenyl-1H-1,2,4-triazol-3-yl)phosphorothioate
Weitere Namen anzeigen
TRY1-Phenyl-3-(O,O-diethyl-thionophosphoryl)-1,2,4-triazoleO,O-diethyl-O-(1-phenyl-1,2,4-triazol-3-yl)phosphorothioateABLESPARKTRELKAhoe2960FULSTOPTRIUMPH
AI3-277646099J8L0EEHOE-2960DTXCID7017612CHEBI:38963Phosphorothioic acid, O,O-diethyl O-(1-phenyl-1,2,4-triazolyl) esterRefChem:1908741-phenyl-3-(O,O-diethylthiophosphoryl)-1,2,4-triazole

Datenbank-Bezeichner

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,5
Polarare Oberfläche (TPSA)
90,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
7
Schwere Atome
20
Formalladung
0
Komplexität
332

Experimentelle und physikochemische Eigenschaften

Pesticides · 5 Einträge

Pesticides

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Triazophos) -> USDA PDB

LogP · 2 Einträge

log Kow = 3.34

3.55

Density · 3 Einträge

1.247 at 68 °F (EPA, 1998) - Denser than water; will sink

1.2514 g/cu cm at 20 °C

1.25 @ 20°C

Color/FormYellowish-brown oil
Solubility · 5 Einträge

Soluble in organic solvents

In water, 39 mg/L at 20 °C

In water, 24.7 mg/L at 20 °C

In acetone, dichloromethane, methanol, isopropanol, ethyl acetate and plyethyleneglycols >500; n-hexane 11.1 (all in g/L at 20 °C)

0.7 g/100 mL in n-hexane at 20 °C

Boiling Point · 3 Einträge

Decomposes before boiling (EPA, 1998)

Decomposes on distillation

350 °C @760 [mm Hg]

Melting Point · 3 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P317, P321, P330, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P317, P321, P330, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 2 Einträge

Regulation (EC) No 1107/2009 (amended)

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.)

DOT LabelPoison
Fire HazardsThis is an organophosphate pesticide. Some of these materials may burn but none of them ignite readily. Container may explode in heat of fire. Fire may produce irritating or poisonous gases. Degraded by acids and alkalis. (EPA, 1998)
Health Hazards · 1 Eintrag

This is an organophosphate pesticide. This material is a cholinesterase inhibitor and acts on the central nervous system. Organic phosphorus insecticides are absorbed by the skin as well as by the respiratory and gastrointestinal tracts. (EPA, 1998)

Hazards Summary · 1 Eintrag

A cholinesterase inhibitor; Can be absorbed through skin; [CAMEO] 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]

Chemie und Industrie

Pharmakologische Informationen

Biological Half-Life · 2 Einträge

The metabolic fate of triazophos was examined in beagle dogs, ... the mean half-life in blood was 3.6 hr.

The metabolic fate of triazophos was studied in 23 female Wistar (WISKf (SPF 71)) rats given triazophos labeled at the 3 position (radiochemical purity, 98%) as a single oral dose of about 5 mg/kg bw in sesame oil by gastric intubation. ... The mean half-life of radioactivity in the blood was 3.8 hr.

Metabolism/Metabolites · 3 Einträge

... In male and female rats intubated with the radioactive compound in olive oil at a dose of 0.56 mg/rat (equivalent to 3.1-4.3 mg/kg bw per day) for 12 consecutive days. ... The main urinary metabolite was urea-14C, representing 85% of the radioactivity excreted by this route. Other metabolites detected in the urine were (3-14C)1-phenyl-1,2,4-triazol-3-ol, (3-14C)1-phenylsemicarbazide and (14C)semicarbazide, all conjugated with glucuronic acid. Each of these three metabolites accounted for 3-5% of the 14C eliminated in urine. Low concentrations of two unidentified metabolites were also found. In the feces, unchanged (14C)triazophos (40% of the total activity in feces) and (3-14C)1-phenyl-1,2,4-triazol-3-ol (60% of the activity) were identified. ...

The metabolic fate of triazophos was examined in beagle dogs ... two female dogs were treated by gastric intubation with (14C)triazophos at a dose of 4.4-4.8 mg/kg bw in sesame oil. Urinary excretion predominated, representing an average of 85% of the administered dose after 24 hr and 92% after 48 hr. Fecal elimination accounted for 0.3% of the administered dose after 24 hr and and 7.2% after 48 hr. Maximal blood concentrations were attained after 2 hr. After 48 hr, no radioactivity was detectable in blood. ... Residual concentrations in tissues were not determined because the animals were not killed at termination. Qualitatively, the metabolic fate of triazophos in dogs was similar to that in rats. The urine contained the same three metabolites as in rats, namely 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole (18% of the administered dose) and its glucuronide (60%) and sulfate (5%) conjugates. One metabolite was found only in dog urine (representing 11% of the administered dose), which was thought to be another sulfate ester conjugate of the 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole metabolite. Quantitatively, less of this metabolite was present in dog urine (18% of the administered dose) at the time of analysis than in rats (43%). The instability of the glucuronide conjugate and its potential conversion to the free metabolite were also observed in dogs, and the somewhat higher concentration of the glucuronide metabolite in the urine of dogs (60% of the administered dose) than of rats (36%) was considered not to be significant. Unchanged triazophos was not detected in urine. The feces contained low concentrations of triazophos and the free 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole metabolite as well as five unidentified metabolites at about 0.7, 0.3 and 7.3% of the administered dose, respectively. ...

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
CAS
24017-47-8
PubChem CID
32184
DTXSID
DTXSID9037612
ChEMBL
CHEMBL1553726
ChEBI
CHEBI:38963
UNII
6099J8L0EE
EC Number
245-986-5
Nikkaji
J16.809B

32 to 41 °F for technical grade (EPA, 1998)

5 °C

5 °C

Vapor Pressure · 5 Einträge

1e-05 mmHg (EPA, 1998)

0.0000029 [mmHg]

Vapor pressure = 13 mPa @ 55 °C

2.9X10-6 mm Hg at 30 °C

0.00001 [mm Hg] @25 °C

Physical Description · 2 Einträge

Yellowish oil. Used to control insects, mites, and nematodes. Not registered as a pesticide in the U.S. (EPA, 1998)

Light brown liquid; mp = 0-5 deg C; [Merck Index] Yellowish liquid; [HSDB]

Stability/Shelf LifeStable to sunlight
Ionization Efficiency · 6 Einträge

Positive

3.03

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section180.2 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9037612]

Physikochemische Eigenschaften

Schmelzpunkt
0 · 0-5°C
Siedepunkt
260 °C · 260°C
Dichte
1.247 · 1.247
Dampfdruck
3.9 · 3.9×10-4 Pa (30 °C)
Flammpunkt
25 °C · 25 °C
storage temp.
4 °C · APPROX 4°C
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
pka
-0.15 · -0.15±0.50(Predicted)
Aggregatzustand
liquid
Farbe
Light yellow to brown
Wasserlöslichkeit
30 · 30-40 mg/L at 20 ºC
BRN
682554 · 682554
Henry's Law Constant
3.2 · 3.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Hygroscopic
Major Application
agricultureenvironmental
InChI
1S/C12H16N3O3PS/c1-3-16-19(20,17-4-2)18-12-13-10-15(14-12)11-8-6-5-7-9-11/h5-10H,3-4H2,1-2H3
InChIKey
AMFGTOFWMRQMEM-UHFFFAOYSA-N
SMILES
CCOP(=S)(OCC)Oc1ncn(n1)-c2ccccc2
NIST chemische Informationen
Triazophos(24017-47-8)
EPA chemische Informationen
Triazophos (24017-47-8)
Reactive GroupAmines, Phosphines, and Pyridines
Special ReportsWHO/IPCS; Pesticide Residues in Food - 1991. Part II - Toxicology (1992)
Reactivity Profile · 1 Eintrag

Organophosphates, such as TRIAZOFOS, 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.

DOT Hazard Classification · 2 Einträge

Triazophos

Marine pollutant

Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
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. Triazofos is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Hazard Classes and Categories · 3 Einträge

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute Tox. 3 *

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

This is an organophosphate pesticide. Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

First AidWarning: Effects may be delayed. Caution is advised. Vital signs should be monitored closely.
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]

Storage Conditions · 1 Eintrag

Pesticides of any degree of toxicity should be transported in containers which are clearly labelled, leak-proof and not easily damaged. They should never be transported beside or above any type of food, and all spillages should be immediately reported. Any foodstuffs transported in the same compartment as a pesticide may thus be held, pending examination to ensure that it has not been in any way contaminated. ... Pesticides of moderate or higher hazard should be so stored that only authorized persons can have access to them. It is particularly important that children should be excluded from any contact with pesticide concentrates or residues. Spillages often occur in storage and repacking rooms and must be cleaned up with care. Rooms used for storage only should be soundly constructed and fitted with secure locks. Floors should be kept clear and the pesticides clearly identified. If repacking is carried out in storage rooms, adequate light should be available; floors should be impervious and sound; washing facilities should be available ... /Pesticides/

Nonfire Spill ResponseAvoid inhalation and skin contact. This is an organophosphate pesticide. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors.
Disposal Methods · 2 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Preventive Measures · 5 Einträge

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

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. /Organophosphorus pesticides, liquid, NOS/

Personnel protection: Keep upwind. Wear appropriate chemical protective gloves, boots and goggles. Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organophosphorus pesticides, liquid, NOS/

If material not on fire and not involved in fire: Keep sparks, flames, and othersources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, NOS/

For more Preventive Measures (Complete) data for TRIAZOPHOS (11 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Protective Action Criteria (PAC) · 3 Einträge

0.25 [mg/m3]

2.8 [mg/m3]

12 [mg/m3]

Personal Protective Equipment (PPE) · 2 Einträge

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Workers ... must be given personal protective equipment comprising overalls made of a tight fabric or polyvinyl chloride, gloves & rubber boots. They must wear a respirator with an activated-carbon gas filter cartridge affording protection for a determined number of hours. The eyes should be protected by goggles. /Organophosphorus pesticides/

Toxikologische Informationen

Ecotoxicity ValuesLD50; Species: /Coturnix japonica/ (Japanese quail) oral 4.2-27.1 mg/kg
Environmental Fate · 4 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 355(2), indicates that triazophos is expected to have moderate mobility in soil(SRC). Volatilization of triazophos from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 2.9X10-6 mm Hg(3), and water solubility, 39 mg/L(3). Triazophos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Triazophos, incubated at 22 °C for 64 or 84 days, had half-lives of 17-23 days in five soils, in three soils half-lives were 39-46 days, and in one soil an extrapolated half-life of 87 days(4). Triazophos, incubated at 27 °C in a clay loam soil and in a loam soil, had half-lives of 2 and 5 days, respectively(4).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 355(2), indicates that triazophos 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 3.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.9X10-6 mm Hg(4), and water solubility, 39 mg/L(4). According to a classification scheme(5), an estimated BCF of 74(SRC), from a log Kow of 3.34(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis half-lives of 30-250 days were measured for triazophos in water at 25 °C(7). Half-lives of <35 days were measured for triazophos both in water and in a water:sediment slurry(7). Triazophos had a measured half-life of 41 days in river water (pH 7.3 and 22 °C); a half-life of 47 days was measured in filtered river water at the same pH and temperature(8). A half-life of 27 days was measured in sea water (pH 8.1 and 22 °C) for triazophos(8). No distinction was made between losses due to biodegradation, hydrolysis, adsorption, or photolysis(8). Photodegradation half-lives of 21 days and 67 days were measured for river water and sea water, respectively(8); however, as this experiment was conducted in an open system, other factors may have had an effect(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triazophos, which has a vapor pressure of 2.9X10-6 mm Hg at 30 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase triazophos 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 4 hours(SRC), calculated from its rate constant of 9.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase triazophos may be removed from the air by wet or dry deposition(SRC). Triazophos does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Triazophos degradation was studied in nine soils. In two different standard German soils, the half-life was calculated to be about 18 days and about 87 days. In nearly all soils, three unidentified cmpds and traces of the hydroxytriazole occurred rapidly and in amounts of 1-6% of the initial radioactivity. 14-CO2 was also recovered.

Food Survey Values · 2 Einträge

Triazophos was detected, at unreported concentrations, during a 1978-1982(1) and a 1983-1986(2) survey of US domestic and import commodities. Triazophos was detected in six of 10 unprocessed eggplant samples and in one of 10 processed eggplant samples at 8.8 to 27.5 and 6.2 ppb, respectively, in samples taken from Alexandria City, Egypt from June 1997 to August 1998(3). Triazophos was undetected (detection limit 0.2 ppb) in 30 tomato, 20 cucumber, 18 potato, 12 apple, 20 grape and 12 orange processed and unprocessed samples taken in the same survey(3). Triazophos was analyzed in 397 samples collected in eight local markets from six Egyptian governorates (Cairo, Giza, Qualubiya, Beni Suef, Minufiya and Ismailia) in 1995 and was not detected in tomato, cabbage, cauliflower, carrot, courgette, cucumber, eggplant, green beans, green peas, lettuce, onion, pepper, apple, cantaloupe, grape, guava, mango, orange, peach or strawberry(4). Triazophos was also analyzed in 1579 samples collected in the same Egyptian governorates in 1996 and was not detected in cabbage, grape leaf, lettuce, melokhia, spinach, watercress, artichoke, broad bean, cauliflower, cantaloupe, cucumber, eggplant, green beans, green peas, okra, onion, pepper, squash, carrot, sweet potato, taro, banana, fig, lemon, lime, mango, peach, pear, plum, or pomegranate(5).

Triazophos was not detected in grapefruit, lemon, mandarin/clementine, orange, apple, pear, quince, apricot, cherries, peach, nectarine, plum, grape, strawberry, blackberry, hip, boysenberry, elderberry, raspberry, rowanberry, bilberry, red and black current, gooseberry, banana, fig, kiwi, pomegranate, beetroot, carrot, celeriac, horseradish, parsnip, parsley root, radish, garlic, onion, spring onion, tomato, pepper, eggplant, cucumber, melon, watermelon, squash, sweet corn, broccoli, cauliflower, Brussel sprout, white, red, spring, Oxheart or Chinese cabbage, kale, lettuce, spinach, chive, dill, marjoram, oregano, parsley, rosemary, thyme, bean, pea, celery, leek, rhubarb, mushroom, sunflower seed or potato in the 1995-1996 Danish national pesticide monitoring program(1). A market basket survey of produce conducted in Trinidad, West Indies from Oct 1996 to May 1997 reported that triazophos was detected in celery at 1.74 to 40.20 mg/kg, in lettuce at 4.88 mg/kg and in pak-choi at 0.16 to 4.74 mg/kg(2). Triazophos was not detected in sweet pepper, cabbage, cauliflower, cucumber, spinach, chive tomato, hot pepper, cilantro, okra, watercress, eggplant, sorrel fruit or green beans(2). Triazophos was not detected (detection limit 1 ug/kg) in 298 raw milk samples obtained directly from tank trucks during delivery at nine Italian dairy plants, sampling took place Oct 2004, Jan and May 2005(3).

Adverse EffectsOther Poison - Organophosphate
Milk ConcentrationsTriazophos was not detected (detection limit 1 ug/kg) in 298 raw milk samples obtained directly from tank trucks during delivery at nine Italian dairy plants, sampling took place Oct 2004, Jan and May 2005(1).
Average Daily IntakeCalculated daily ingestion of triazophos was 1.4 ng/person from citrus fruits, 17.8 ng/person from pitted and seedy fruits, and 86 ng/person from vegetables in the Region of Murcia in Spain(1).
Ecotoxicity Excerpts/OTHER TERRESTRIAL SPECIES/ Toxic to bees.
Plant Concentrations · 2 Einträge

In plants to which triazphos had been applied, the residues at harvest consisted mainly of unchanged triazophos plus 1-phenyl-3-hydroxy-1,2,4-triazole (1/5 of the total residue), and traces of the P=O analog of triazophos. Fifteen wk after application of triazophos to cotton, residues consisted of triazophos (0.02 ppm), 1-phenyl-3-hydroxy-1,2,4-triazole (0.01 ppm) and an unidentified cmpd (0.01 ppm). The latter was probably a desethyl analog. Similar results were obtained with beans and rice.

Triazophos levels in wheat grain, and in leaf and stem material were 0.187-1.865, and 3.168-44.506 mg/kg, respectively, in 2003 and 0.023-1.396, and 2.040-12.909, respectively, in 2004(1).

Animal ConcentrationsTriazophos was detected in 2% of honeybee samples at concentrations of 0.005 to 0.009 mg/kg, dead bee samples were collected in bags suspended under beehives (only worker bees were analyzed) in the district of Bologna, Italy(1).
Medical Surveillance · 1 Eintrag

Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications for work with OPP /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to OPP until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/

Soil Adsorption/Mobility · 1 Eintrag

The Koc of triazophos has been reported to be 355(1). According to a classification scheme(2), this Koc value suggests that triazophos is expected to have moderate mobility in soil(SRC). S-type adsorption isotherms were determined for triazophos in two types of soil, a black soil(66.3 meq/100 g soil; 1.65% organic matter; 109.3 sq m/g soil; 29.7 me/100 g soil) and a red soil (1.35 meq/100 g soil; 1.24% organic matter; 23.9 sq m/g soil; 10.4 me/100 g soil)(3). The black soil had higher adsorptive capacity than the red soil; adsorptive strength was greatest for both soils at pH 6-7. Rate constants for the reaction of triazophos with both soils varied from 0.0227-0.0246/min(3). The addition of a 0.2 m water layer over two days to soil columns containing triazophos resulted in no leaching of this compound from the columns(4).

Human Toxicity Excerpts · 4 Einträge

/HUMAN EXPOSURE STUDIES/ In ... a preliminary study, triazophos (purity, 90%) initially prepared in ethanol and then diluted with tap water to provide single nominal doses of 0.012 and 0.062 mg/kg bw per day in a dose volume of approximately 100 mL was administered sequentially to one 41-year-old man orally. The lower dose was administered on day 1 and the higher dose on days 2, 3 and 4, followed by a 7-day recovery period. Blood samples for determination of plasma and erythrocyte cholinesterase activities by a modification of the Ellman technique, were taken from the finger tip before dosing on all treatment days, 0.5, 1 and 2 hr after dosing on days 1 and 2, and 2 and 5 hr after dosing on days 3 and 4. Samples were also taken on recovery days 3 and 7. No apparent change in plasma cholinesterase activity was found on days 1 and 2, but decreases estimated (because of an uncertain baseline) at 20% and up to 34% were observed on days 3 and 4, respectively. Some residual depression by 21% and 14% was found on days 3 and 7 of the recovery period, respectively. Treatment had no apparent effect on erythrocyte cholinesterase activity. The man experienced headache for 3 days from day 2 of dosing to day 1 after dosing was stopped, which might have been related to treatment. ...

/HUMAN EXPOSURE STUDIES/ In a larger study, triazophos (purity, 88%), initially prepared in and stored as a dilution in 30% ethanol before dosing, was administered over 3 weeks at a nominal dose of 0.0125 mg/kg bw per day in 150 mL of lime juice to volunteers from the staff of the laboratory at which the study was performed. Lime juice without the test material was given to participants for about 1 week before dosing. The volunteers, described as healthy, were 13 men aged 17-59 years (average, 26 years) and 12 women aged 16-51 years (average, 28 years). They were given the test material only during the five days of the work week, with a break on weekends. They were observed for overt signs of toxicity. After dosing, they were observed for an additional 4 weeks. A medical history was taken before study initiation, and a physical examination and blood and urine analyses were conducted before treatment and after the end of the treatment-free recovery period. Subjects were requested to inform the investigators if they felt unwell. Plasma and erythrocyte cholinesterase activities were measured. Blood samples for measurement of cholinesterase activity were taken three times before dosing, three times during weeks 1 and 2 of dosing, four times during week 3 of dosing and three times during each week of the treatment-free period. A 20% depression in individual plasma or erythrocyte cholinesterase activity relative to the mean value for the individual before dosing was considered grounds for discontinuing dosing. All 25 subjects completed the study. A slight but statistically significant decrease in group mean blood pressure from that before dosing in women and minor alterations in group mean values in either sex for some hematological and clinical chemical parameters were within normal limits for the laboratory and considered not to be related to treatment. About 50% of the women reported urinating more often, with some feeling of urgency during the first week of dosing, which was attributed to psychosocial causes. One man reported feeling tired and listless during the second week of dosing. Although this individual's plasma cholinesterase activity fell to a limit of concern at the end of the week, the attending physician opted to continue dosing. The plasma cholinesterase activity of this individual did not decrease further during the rest of the study. Another man reporting feeling tired and listless during the second and third weeks of dosing and also had headache, sore throat and soreness in the nose and ear. Two women had diarrhea or diarrhea and vomiting during the second week of dosing, causing absence from work. Another man was absent due to gastrointestinal upset during week 4 after dosing. The authors mentioned that gastrointestinal viral-type infections that had affected workers who were not participating in the study might have been a factor in some of the symptoms noted. The plasma cholinesterase activity of two men and one woman dropped rapidly during the first week of treatment, such that dosing was stopped for 6 days. It was re-commenced during treatment week 3, when the enzyme activity rose to levels considered sufficient. Decreased plasma cholinesterase activity at the end of dosing relative to the mean before dosing, by about 20%, was noted in some individuals, whereas little change in plasma cholinesterase activity was seen in others. The activity of some individuals never completely returned to the values before treatment. Erythrocyte cholinesterase activity was not affected, and no statistically significant changes were observed in cholinesterase activity with the methods used. Evaluation of the symptoms reported suggested that they could generally be explained by non-treatment-related factors. ... The NOAEL was 0.0125 mg/kg bw per day.

Regulatorische Informationen

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. Triazofos is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Sicherheitsdaten

wgk
3
ridadr
3018
hs_code
29339900
RTECS-Nr.
TF5635000
risk_code
21-23/25-50/53-38-10
Toxizität
LD50 in rats (mg/kg): 82 orally, 1100 dermally (Thier); LD50 in rats (mg/kg): 107 i.p.; in rabbits (mg/kg): 280 dermally (Hay)
hazard_code
T;N,N,T
safety_code
1/2-36/37-45-60-61
hazard_class
6.1(a)
packing_group
II
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
24017-47-8(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 1 InhalationAcute Tox. 3 OralAcute Tox. 4 DermalAquatic Acute 1Aquatic Chronic 1

The metabolic fate of triazophos was studied in 23 female Wistar (WISKf (SPF 71)) rats given triazophos labeled at the 3 position (radiochemical purity, 98%) as a single oral dose of about 5 mg/kg bw in sesame oil by gastric intubation...The glucuronide was unstable and was apparently converted to the parent compound at room temperature. Unchanged triazophos was not detected in urine. ...

Absorption, Distribution and Excretion · 4 Einträge

The metabolic fate of triazophos was examined in beagle dogs ... two female dogs were treated by gastric intubation with (14C)triazophos at a dose of 4.4-4.8 mg/kg bw in sesame oil. Urinary excretion predominated, representing an average of 85% of the administered dose after 24 hr and 92% after 48 hr. Fecal elimination accounted for 0.3% of the administered dose after 24 hr and 7.2% after 48 hr. Maximal blood concentrations were attained after 2 hr. After 48 hr, no radioactivity was detectable in blood. ... Residual concentrations in tissues were not determined because the animals were not killed at termination. Qualitatively, the metabolic fate of triazophos in dogs was similar to that in rats. The urine contained the same three metabolites as in rats, namely 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole (18% of the administered dose) and its glucuronide (60%) and sulfate (5%) conjugates. One metabolite was found only in dog urine (representing 11% of the administered dose), which was thought to be another sulfate ester conjugate of the 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole metabolite. Quantitatively, less of this metabolite was present in dog urine (18% of the administered dose) at the time of analysis than in rats (43%). The instability of the glucuronide conjugate and its potential conversion to the free metabolite were also observed in dogs, and the somewhat higher concentration of the glucuronide metabolite in the urine of dogs (60% of the administered dose) than of rats (36%) was considered not to be significant. Unchanged triazophos was not detected in urine. The feces contained low concentrations of triazophos and the free 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole metabolite as well as five unidentified metabolites at about 0.7, 0.3 and 7.3% of the administered dose, respectively. ...

The metabolic fate of triazophos was studied in 23 female Wistar (WISKf (SPF 71)) rats given triazophos labeled at the 3 position (radiochemical purity, 98%) as a single oral dose of about 5 mg/kg bw in sesame oil by gastric intubation. Twenty animals were used to investigate excretion and metabolism and the three others for blood assays. Pooled urine and fecal samples were collected after 24, 48, and 96 hr, and blood samples were taken 0, 0.5, 2, 4, 6, 8, 24 and 48 hr after administration. The maximal concentrations in blood were attained after about 4 hr. ... The recovery rate of 98% after 96 hr indicates that excretion was relatively complete. The predominant route of excretion was urinary, with > 90% of the administered radioactivity excreted within 48 hr. Fecal elimination accounted for 4.5% of the administered dose after 48 hr. The residual concentrations of radioactivity in the tissues analyzed (liver, kidney, lung, heart, brain, spinal cord and retroperitoneal and subcutaneous fat) were highest in kidney and liver but were still relatively low: <0.004 ppm. Pooled urine contained three identifiable metabolites, 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole (43% of the administered dose) and its glucuronide (36%) and sulfate conjugates (13%). The glucuronide was unstable and was apparently converted to the parent compound at room temperature. Unchanged triazophos was not detected in urine. ...

Groups of five male and five female Wistar SPF rats given a single oral dose of (14C)triazophos (labeled at the 3 position of the triazole ring) in olive oil by intubation at a dose of 2.8 mg/rat (equivalent to 15-21 mg/kg bw), excreted 76% of the administered dose in urine and 21% in feces within 48 hr. No significant difference in the rate or route of elimination was found between the sexes. Analysis of tissues from animals killed 4 days after treatment showed that 14C residues represented < 0.04% of the administered dose in kidneys, gonads, brain, muscle and skin, 0.089% in liver and 0.31% in the gastrointestinal tract. Rapid elimination of (14C)triazophos was also observed in male and female rats intubated with the radioactive compound in olive oil at a dose of 0.56 mg/rat (equivalent to 3.1-4.3 mg/kg bw per day) for 12 consecutive days, with 70-83% of the administered dose recovered in urine and 18-31% in feces during the dosing period. Four days after the end of the 12-day treatment, the concentration of 14C residues in most of the tissues analyzed (subcutaneous fat, kidney, gonads, liver, brain, muscle and skin) did not exceed 0.0008% of the administered dose. The exception was the gastrointestinal tract, which still contained 0.5% of the dose. It is not clear whether urine and feces from the study with single and multiple doses were analyzed for metabolites separately and whether the metabolic profiles were qualitatively or quantitatively similar.

(14)C-Triazophos, dissolved in oil, was administered to white rats in single and repeated doses. When given as a single dose, 76% of the applied label was excreted within 4 days in urine and 21% in feces. When given repeatedly on 12 consecutive days, 69-83% of the daily applied label was excreted in urine and 18-30% in feces. The feces contained unchanged triazophos and the hydrolysis product 1-phenyl-glucuronide, phenylsemicarbazide glucuronide and semicarvazide glucuronide. Identification of metabolites was made with TLV, IR and MS. Two other metabolites were observed but not identified. Neither triazophos nor the oxon analog were observed in urine.

Verwendung und Herstellung

Uses · 5 Einträge

Used as broad spectrum insecticide and acaricide for fruit and cereals; [HSDB]

Not registered with the EPA for use as pesticide in the US; [CAMEO] Banned in the EU for use as a biocide and agricultural insecticide; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

Acaricide/miticide, insecticide, nematacide.

For aphids, beetles, borers, bugs, foliar-feeding larvae, fruit flies, leafhoppers, leafminers, nematodes, scales, soil insects, thrips, mites and whiteflies in fruits, vegetables, and ornamentals.

Methods of Manufacturing · 2 Einträge

Triazophos is produced by reaction of 1-phenyl-3-hydroxy-1H-1,2,4-triazole, suspended in acetone, with diethoxythiophosphoryl chloride in the presence of triethylamine.

Phenylhydrazine + sodium cyanate + formamide + O,O-diethyl phosphorochlorothioate (cyanate addition/condensation/dehydrochlorination)

Formulations/Preparations · 5 Einträge

Emulsifiable concentrate

Premix Partners: Chlorfluazuron; Chlorpyrifos; Deltamethrin.

HOE 2960

Formulation: Emulsifiable concentrates, wettable powders, ultralow-volume liquids, granules.

For more Formulations/Preparations (Complete) data for TRIAZOPHOS (10 total), please visit the HSDB record page.

General Manufacturing InformationThe WHO Recommended Classification of Pesticides by Hazard identifies triazophos (technical grade) as Class IB: highly hazardous; Main Use: insecticide.

Anwendungen

VerwendenTriazophos is used to control chewing and sucking insects and mites in a wide range of crops. It is also used to control some nematodes in ornamentals and strawberries.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

PhenylhydraziniumchloridConcentrated hydrochloric acidXylol, IsomerengemischTriethylammoniumchloridapolipoprotein H (beta-2-glycoprotein I)4-ChlorbenzaldehydToluolKaliumcarbonatAmeisensureHarnstoff15%)">Trimethylamin, in wässriger Lösung(C > 15%)NatriumhydrogencarbonatDichlormethanChlorthiophosphorsäure-0,0-diethylesterEMULSIFIERNatriumhydroxidPhenicarbazidPhenylhydrazin

Nachgelagerte Produkte

Trichlorfon+Triazophos,E.C.Abametin+Triazophos,E.C.

Anbieter100 Anbieter

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/SIGNS AND SYMPTOMS/ The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, & loss of orientation. Psychic disorders, nystagmus, trembling of the hands & other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis & paralysis develop. /Organophosphorus pesticides/

/OTHER TOXICITY INFORMATION/ The clinical signs associated with organophosphorus compound poisoning are due to accumulation of acetylcholine and hence over-stimulation of the parasympathetic nervous system. /Organophosphorus insecticides/