Trichlorfon (ISO)

Trichlorfon

HCID 5853CAS 52-68-6

Grundinformationen

Standard-SMILES
COP(=O)(OC)C(O)C(Cl)(Cl)Cl
InChIKey
NFACJZMKEDPNKN-UHFFFAOYSA-N
Summenformel
C4H8Cl3O4P
Durchschnittliche Molmasse
257,43 g/mol
Monoisotopische Masse
255,92257841

Überblick

Trichlorfon is a white crystalline solid. It is a wettable powder. It can cause illness by inhalation, skin absorption and/or ingestion. It is used as a pesticide.

Namen und Bezeichner

Bevorzugter Name
Trichlorfon
IUPAC
2,2,2-trichloro-1-dimethoxyphosphorylethanol
Lokaler Name
Trichlorfon (ISO)
Englischer Name
Trichlorfon
Summenformel
C4H8Cl3O4P
Molmasse
257.44

Namen und Synonyme

TRICHLORFONMetrifonate52-68-6ChlorophosMetriphonateTrichlorphonChlorofosMethyl chlorophosTrichlorofonDyloxChloroxyphosTrichlorophon
Weitere Namen anzeigen
DEPdimethyl esterTRICHLOFONNeguvon
BilarcilChloroftalmDipterexFoschlorAnthonCombotProxolDanex

Datenbank-Bezeichner

CAS
52-68-6、56042-26-3、56042-27-4
PubChem CID
5853
DTXSID
DTXSID0021389
ChEMBL
CHEMBL167150
ChEBI
CHEBI:6908
UNII
1MVY4KU98F、37VCQ9C0OG、DBF2DG4G2K
EC Number
200-149-3
Nikkaji
J2.309D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,5
Polarare Oberfläche (TPSA)
55,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
3
Schwere Atome
12

Experimentelle und physikochemische Eigenschaften

Chemical ClassesMutagens
SpringerMaterials PropertiesCrystal structure
Pesticides · 6 Einträge

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

Insecticides

Pesticide (Trichlorfon) -> USDA PDB

LogP · 3 Einträge

log Kow = 0.51

0.48

1.7

Odor · 2 Einträge

Ethyl ether-like

Weak, characteristic odor

Density · 5 Einträge

1.73 at 68 °F (USCG, 1999) - Denser than water; will sink

1.73 g/cu cm at 20 °C

Relative density (water = 1): 1.73

1.73

1.73 @ 20°C

Physikochemische Eigenschaften

Schmelzpunkt
77 · 77-81 °C
Siedepunkt
100 °C · 100°C
Dichte
1.73 · 1.73
Dampfdruck
2.1 · 2.1×10-4Pa (20 °C)
Brechungsindex
1.3439 · 1.3439
storage temp.
2 · 2-8°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Danger

H301 (29.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P342+P316, P362+P364, P391, P403, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Phosphonic acid, P-(2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester

Commission Regulation (EC) No 451/2000

Trichlorfon is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2007/356

Trichlorfon: Does not have an individual approval but may be used under an appropriate group standard

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 - Phosphonic acid, (2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

Combustible.

Fire PotentialThis material may burn, but does not ignite readily.
Health Hazards · 1 Eintrag

INHALATION, INGESTION, AND SKIN ABSORPTION. Inhibits cholinesterase. Headache, depressed appetite, nausea, miosis are symptoms of light exposures. Moderate effects are peritoneal paralysis, diarrhea, salivation, lacrimation, sweating, dyspnea, substernal tightness, slow pulse, tremors, muscular cramps and ataxia. Severe symptoms are: pyrexia, cyanosis, pulmonary edema, areflexia, loss of sphincter control, paralysis, coma, heart block, shock and respiratory failure. EYES: Increases permeability of blood vessels in anterior eye. Reduces corneal sensitivity with glaucoma, abnormalities in intraocular tension or decreased visual acuity. (USCG, 1999)

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Rest. Refer for medical attention .

First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong bases and food and feedstuffs. Keep in a well-ventilated room.
Firefighting HazardsSpecial hazards arising from the substance or mixture: Carbon oxides, oxides of phosphorus, hydrogen chloride gas.
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]

Toxikologische Informationen

Treatment · 1 Eintrag

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 5 Einträge

The aim of this study is to determine the effect of levamisole and levamisole-trichlorfon combination on isolated sheep trachea. Contraction was achieved with levamisole concentrations (10(-8)-10(-3) M) on tracheal strips of adult sheep (> 1 year of age). Pretreatment with trichlorfon (10(-7) M)-levamisole (10(-7) M) decreased the pD2 and E(max) of Ach when compared to levamisole pretreatment (p < or = 0.01). Pretreatment with levamisole (10(-7) M), decreased the E(max) (p < or = 0.01) and pD2 (p < 0.05) of bethanechol concentrations (10(-8)-10(-3) M) significantly. Pretreatment with atropine (10(-6) M) decreased the E(max) of levamisole (10(-4) M) significantly (p < 0.05). To conclude, levamisole acted mainly on the muscarinic receptors of the sheep trachea and this effect was partly inhibited by atropine. Adverse interaction was present between levamisole and trichlorfon.

In the forward mutation test system ade6 of the yeast Saccharomyces pombe, trichlorfon in combination with azinphos-methyl produced clearly synergistic effects for toxicity and mutagenicity. The addition of S9 microsomal liver fraction decreased the efficiency of single and combined treatments.

12 organophosphorus insecticides were tested for toxicity and mutagenicity in the forward mutation test system ade6 of the yeast Schizosaccharomyces pombe. EMS and MMS were selected as positive controls. 3 compounds, dichlorvos, trichlorfon and paraoxon, showed a linear dose-response relationship. Among the other compounds investigated, methyl derivatives, though in general more toxic than ethyl derivatives, did not significantly increase the mutation frequency. Trichlorfon, tested in combination with malathion, methylparathion or methylazinphos (guthion), produced clearly synergistic effects for both toxicity and mutagenicity. The addition of S9 microsomal liver fraction decreased the efficiency of both single and combined treatments only where a dose-response relationship or a synergistic effect was obtained.

Two randomized crossover studies were conducted to examine the effects of a combination of aluminum hydroxide (aluminium hydroxide) and magnesium hydroxide (Maalox TC), cimetidine, and ranitidine on the pharmacokinetics of trichlorfon (metrifonate) and its metabolite in a total of 34 healthy subjects (ages 45-75 yr) who received a single oral tablet of 50 mg trichlorfon alone, with or 90 min before a suspension of Maalox TC, or with or after pretreatment with oral tablets of 400 mg cimetidine or 150 mg ranitidine. The ratios and 90% confidence intervals (trichlorfon with comedication/trichlorfon alone) of AUC and Cmax of the drug and its metabolites fulfilled the criteria defined for showing lack of relevant interaction for all treatment comparisons in both studies. Trichlorfon was well tolerated.

For more Interactions (Complete) data for Trichlorfon (6 total), please visit the HSDB record page.

Health Effects · 1 Eintrag

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Ecotoxicity Values · 5 Einträge

LC50; Species: Gammarus fasciatus (/Scud/) mature; Conditions: static bioassay without aeration, 21 °C, pH 7.2-7.5, water hardness 40-50 mg/L as calcium carbonate and alkalinity of 30-35 mg/L; Concentration: 40 ug/L for 96 hr (95% confidence limit: 26-60 ug/L) /Technical material 98%/

LC50; Species: Procambarus (Crayfish) mature; Conditions: static bioassay without aeration, 12 °C, pH 7.2-7.5, water hardness 40-50 mg/L as calcium carbonate and alkalinity of 30-35 mg/L; Concentration: 7800 ug/L for 96 hr (95% confidence limit: 6520-9330 ug/L) /Technical material 98%/

LC50; Species: Pteronarcella badia (/Stonefly/) naiads; Conditions: static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/L as calcium carbonate and alkalinty of 30-35 mg/L; Concentration: 11 ug/L for 96 hr (95% confidence limit: 7.6-16 ug/L) /Technical material 98%/

LC50; Species: Pteronarcys california (/Stonefly/) second year class; Conditions: static bioassay without aeration, 16 °C, pH 7.2-7.5, water hardness 40-50 mg/L as calcium carbonate and alkalinity of 30-35 mg/L; Concentration: 35 ug/L/96 hr (95% confidence limit: 22-55 ug/L) /Technical material 98%/

For more Ecotoxicity Values (Complete) data for Trichlorfon (85 total), please visit the HSDB record page.

Environmental Fate · 4 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 6-79(2-3) indicate that trichlorfon is expected to have high to very high mobility in soil(SRC). Volatilization of trichlorfon from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-11 atm-cu m/mole(SRC), based upon its vapor pressure, 7.8X10-6 mm Hg(4), and water solubility, 1.2X10+5 mg/L(5). Trichlorfon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Trichlorfon, at an initial concentration of 2 ppm in soil, degraded 100% in 1.5 months at pH values of 3-4.6 and in 0.5 months at pH values of 8.7-9.05(6). Half-lives in clay (pH 7.9) and calcerous (pH 8.1) soils have been determined to be 1.15 and 1.05 days, respectively(7). Persistence of trichlorfon in soils has been reported as 2 weeks or less and is degraded by ammonifying microorganisms(8). Trichlorfon degrades rapidly in aerobic soils with reported half-lives of approximately 1-27 days under non-sterile conditions(9). The dissipation half-life of trichlorfon from plants has been estimated to be 2.36-3.10 days(10).

TERRESTRIAL FATE: The reported half-life for trichlorfon in aerobic soils was reported as 3-27 days. Using standard practices for application of pesticides to golf greens, trichlorfon dissipation half-lives were found to be 1.1 and 6 days in 1996 and 1997, respectively(1). Loss of trichlorfon due to volatilization, clipping removal and leaching from the greens was minimal(1). Dissipation of trichlorfon in individual components of the greens were as follows(1):[Table#2326]

AQUATIC FATE: Based on a classification scheme(1), Koc values of 6-79(2-3) indicate that trichlorfon may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 2.2X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 7.8X10-6 mm Hg(5), and water solubility, 1.2X10+5 mg/L(6). Trichlorfon is subject to hydrolysis and decomposition proceeds more rapidly with heating, and above pH 6(7). Hydrolysis half-lives (22 °C) of trichlorfon were reported as 510 days (pH 4), 46 hours (pH 7), and <30 minutes (pH 9)(7). According to a classification scheme(8), an estimated BCF of 3(SRC), from its log Kow of 0.51(9) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low. Complete biodegradation of trichlorfon in river water occurred within 5 days at 10 mg/L, 13 days at 20 mg/L, and 20 days at 30 mg/L(11). In screening studies carried out at 20 °C using activated sludge inoculum, the aerobic biodegradation rate of trichlorfon was determined to be 0.28/day with a half-life of 2.5 days(12). Trichlorfon underwent photochemical conversion to dichlorvos when irradiated under UV light in an aqueous solution(13).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlorvos, which has a vapor pressure of 0.0158 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dichlorvos is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone and nitrate radicals; the half-life for these reactions in air is estimated to be 11-19 hours, 70 days and 3.2 hours(SRC), calculated from respective rate constants of 2.0X10-11 to 3.5X10-11(3-5), 1.7X10-19(5) and 2.5X10-13(5) cu cm/molecule-sec. Dichlorvos absorbs light in the UV range with a maximum absorbance of 295-305 nm and was found to have a photodegradation rate constant of 2.652X10-9 L/sec, giving it a photodegradation half-life of about 7.25 hours(6).

Food Survey Values · 2 Einträge

Trichlorfon was detected in 1 of 13,980 food samples collected by state food laboratories in 10 states (California, Florida, Indiana, Massachusetts, Michigan, New York, North Carolina, Oregon, Virginia, Wisconsin) during fiscal year 1988; it was not detected in 13,085 food samples collected during a similar study conducted in fiscal year 1989(1). In a study of grapes, 60% of trichlorfon residues were found in the skin; levels were higher in grape juice concentrate, raisins, and wine than in grapes, and trichlorfon accumulated in wine(2). Trichlorfon applied as a veterinary medicine can produce residues in meat(3). Trichlorfon was not detected (detection limit 9.35 ng/g) in 278 honey samples collected in 2003-2004 from 33 locations throughout Turkey(4).

Trichlorfon was not detected in the following food products(1-4):[Table#2328]

Regulatorische Informationen

FDA Requirements · 5 Einträge

Oral dosage form new animal drugs. Mebendazole and trichlorfon powder. ... Indications for use: It is used in horses for the treatment of infections of bots (Gastrophilus intestinalis and G. nasalis), large roundworms (Parascaris equorum), large strongyles (Strongylus edentatus, S. equinus, S. vulgaris), small strongyles, and pinworms (Oxyuris equi.)

Oral dosage form new animal drugs. Mebendazole and trichlorfon paste. ... Indications for use: It is used in horses for the treatment of infections of bots (Gastrophilus intestinalis and G. nasalis), large roundworms (Parascaris equorum), large strongyles (Strongylus edentatus, S. equinus, S. vulgaris), small strongyles, and pinworms (Oxyuris equi.)

Oral dosage form new animal drugs. Oxfendazole and trichlorfon paste. ... Indications for use: The drug is used in horses for removal of bots (Gasterophilus intestinalis, 2nd and 3rd instars; G. nasalis, 3rd instar) and the following gastrointestinal worms: Large roundworms (Parascaris equorum), pinworms (Oxyuris equi), adult and 4th stage larvae; large strongyles (Strongylus edentatus, S. vulgaris, and S. equinus); and small strongyles.

Oral dosage form new animal drugs. Thiabendazole with trichlorfon. ... Indications for use /in horses/. For the treatment and control of bots (Gasterophilus spp.), large strongyles (Strongylus spp.), small strongyles (genera Cyathostomum, Cylicobrachytus, Craterostomum, Oesophagodontus, Poteriostomum), pinworms (Oxyuris spp., Strongyloides spp.), and ascarids (Parascaris spp.).

For more FDA Requirements (Complete) data for Trichlorfon (7 total), please visit the HSDB record page.

FIFRA Requirements · 5 Einträge

Tolerances are established for residues of the insecticide trichlorfon (dimethyl (2,2,2-trichloro-1-hydroxyethyl) phosphonate) in or on the following food commodities:[Table#2327]

EPA has concluded, after completing its assessment of the cumulative risks associated with exposures to all of the OPs /including trichlorfon/, that: (1) the pesticides covered by the IREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) are indeed eligible for reregistration; and (2) the pesticide tolerances covered by the IREDs and TREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) meet the safety standard under Section 408(b)(2) of the FFDCA. Thus, with regard to the OPs, EPA has fulfilled its obligations as to FFDCA tolerance reassessment and FIFRA reregistration, other than product-specific reregistration.

Based on a review of generic data and public comments on the Agency's revised risk assessments for the active ingredient trichlorfon, the Agency has sufficient information on the human health effects of trichlorfon to make an interim decision as part of the tolerance reassessment process under FQPA. Because the Agency has not yet completed its cumulative risk assessment for the OPs, this interim decision does not fully address tolerance reassessment as required by Section 408(q) of the FQPA; however, the Agency has completed its assessment of risk from dietary exposure to trichlorfon alone. When the cumulative assessment is considered, the FQPA tolerance reassessment requirement will be completed. Nothing in this report precludes the Agency from making further FQPA determinations and tolerance-related rulemaking that may be required on this pesticide or any other in the future. The Agency has also not considered risks associated with exposure to DDVP resulting from trichlorfon use. DDVP, although a trichlorfon degradate, is a registered OP pesticide that is currently undergoing reregistration. Once the DDVP IRED is complete, the Agency will determine whether the DDVP exposure resulting from trichlorfon use poses risk concerns. The Agency may determine that further action is necessary after assessing the cumulative risk of the organophosphate class. At that time, the Agency may also address any other risk concerns that may arise including risks associated with DDVP exposure. ... The Agency has determined that aggregate dietary risk from exposure to trichlorfon may exceed the Agency's level of concern for children 1-6 years when the source of drinking water is surface water. Therefore, mitigation measures are needed at this time to address this concern.

Based on the reviews of the generic data for the active ingredient Trichlorfon, the Agency has sufficient information on the health effects of Trichlorfon and on its potential for causing adverse effects in fish and wildlife and the environment. Where the potential for adverse effects was identified, the Agency and the registrant agreed upon risk mitigation measures. The Agency has determined that all Trichlorfon products, labeled for non-food uses as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing Trichlorfon are eligible for reregistration if labeing and other changes specified in this document are implemented.

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Trichlorfon is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0104; Pesticide type: insecticide; Registration Standard Date: 06/30/84; Case Status: RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): trichlorfon; Data Call-in (DCI) Date(s): 09/10/91, 03/03/95, 02/14/97; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

CERCLA Reportable Quantities · 1 Eintrag

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1 Eintrag

Trichlorfon is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

Sicherheitsdaten

wgk
3
ridadr
UN 3077 9/PG 3
hs_code
29319090
RTECS-Nr.
TA0700000
risk_code
22-43-50/53
Toxizität
LD50 in male, female rats (mg/kg): 630, 560 orally (Gaines)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

P - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

Biological Half-Life · 4 Einträge

...The half-time of trichlorfon in human plasma is approximately 2 hours.

The biological half-life of trichlorfon was 80 min /in mice/.

... Following a 133 mg/kg oral dose, trichlorfon was not detected ... Calculated half-lives /of dichlorvos (a nonenzymatic breakdown product of trichlorfon)/ in /rat/ blood, adipose tissue, muscle, and liver were 7, 11, 10, and 12 days, respectively.

After acute oral treatment of healthy male volunteers with a 2, 5, 7.5, or 12 mg/kg dose of trichlorfon (metrifonate) ... the half-life of ... dichlorvos /in blood/ was about 3.8 hr ...

Metabolism/Metabolites · 6 Einträge

Trichlorfon and dichlorvos levels were followed in plasma and RBCs of 7 individuals given single oral doses of 7.5-10 mg/kg trichlorfon repeated after 2 wk for treating schistosomiases. The relationship of dichlorvos to trichlorfon in plasma and RBCs was about 1%. A biphasic curve for the elimination of trichlorfon in plasma developed; the first phase had a half-life of 0.4 to 0.6 hr, and the second phase had a half-life of about 3 hr. Clearance of trichlorfon was primarily due to formation of dichlorvos.

... Trichlorfon (and its /metabolic/ product dichlorvos) is very rapidly absorbed and cleared in humans. After acute oral treatment of healthy male volunteers with a 2, 5, 7.5, or 12 mg/kg dose of trichlorfon (metrifonate), the maximum blood concentration of trichlorfon was obtained between 12 min and 2 hr and the half-life in blood was about 2 hr. The concentrations of dichlorvos ... closely followed those of trichlorphon at a constant ratio of about 1 to 100. The concentrations of trichlorfon were detectable up to 8 hr, but those of dichlorvos had fallen bellow the level of detection by then. Both plasma and RBC cholinesterases were readily inhibited and were still low after 24 hr - none of the volunteers complained of side effects (and the half-life of ... dichlorvos was about 3.8 hr).

The predominant metabolic pathway that involves cleavage of the P-C phosphonate bond that generates trichloroethanol and dimethyl phosphate which are then excreted in urine. Quantitatively minor pathways of metabolism include demethylation ... and (nonenzymatic) dehydrochlorination of dichlorvos which is rapidly metabolized to dichloroethanol and dimethyl phosphate which are then excreted in urine.

Dichlorvos was detected in the brain of mice after ip injection of trichlorfon. Following dermal and intragastric application of trichlorfon to cows, the parent compound and dichlorvos were detected in the milk up to 22 days after application.

For more Metabolism/Metabolites (Complete) data for Trichlorfon (13 total), please visit the HSDB record page.

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

MeSH Pharmacological Classification · 3 Einträge

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

Absorption, Distribution and Excretion · 5 Einträge

Absorbed by skin.

Trichlorfon ... is not readily absorbed by cotton leaves.

In cow, (32)P-labeled trichlorfon administered orally ... /was/ eliminated in urine, about 65% of administered dose ... /was/ excreted in 12 hr. ... 75% ... of compound of unknown structure. ... Less than 0.2% of administered dose ... in milk ... Blood contained ... max of 15.1 ug equivalent 2 hr after administration, decreased ... to about 1 ug equivalent after 24 hr.

The absorption, distribution, and excretion of trichlorfon in mammals is rapid: about 70-80% of a dose administered orally to mice was excreted during the first 12 hr after treatment. The biological half-life of trichlorfon was 80 min. ...3 hr after an iv injection of (14)CH3O-trichlorfon to rats, trace amounts of radioactivity were found in the liver, lungs, kidney, heart, spleen and blood.

For more Absorption, Distribution and Excretion (Complete) data for Trichlorfon (15 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

Applied to crops, livestock, shrubs, and trees to kill cockroaches, crickets, silverfish, bedbugs, fleas, cattle grubs, flies, ticks, leafminers, and leaf-hoppers; also used to kill fish and domestic animal parasites; [EXTOXNET] Also used as therapeutic anthelmintic (schistosoma); [Merck Index] A general purpose non-agricultural systemic insecticide; Used mostly for home and golf course turf, but also used for ornamentals, food and meat processing facilities (non-food contact surfaces), and ornamental and bait fish ponds; Used in other countries as pour-on cattle treatment; [Reference #2] Used in the EU on fruit trees, vegetables, field crops, and greenhouse crops; [EFSA]

Farming (Pesticides) [Category: Industry]

Anthelmintics; Cholinesterase Inhibitors; Insecticides.

For trichlorfon (USEPA/OPP Pesticide Code: 057901) 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./

MEDICATION (VET)

Non-systemic insecticide with contact and stomach action. Insecticidal control in agriculture, horticulture, forestry, food storage, gardening, households, and animal husbandry. In particular, control of Diptera, Lepidoptera, Hymenoptera, Hemiptera and Coleoptera on many crops. ...Also used to control household pests, such as flies, cockroaches, fleas, bed bugs, silverfish, ants, etc.; as a fly bait in farm buildings and animal houses; and for control of ectoparasites on domestic animals.

Impurities · 1 Eintrag

... Impurities are 2,2-dichlorovonyl dimethyl phosphate: dichlorvos (0-0.2%), trichloroacetaldehyde (0-0.05%), dichloroacetaldehyde (0-0.03%), methyl hydrogen 2,2,2-trichloro-1-hydroxyethylphosphonate; demethyl trichlorfon (0-0.03%), and water (less than 0.3%). The technical product also contains phosphoric acid, 2,2,2-trichloro-1-hydroxyethylphosphoric acid, and dimethyl phosphite.

U.S. Production · 2 Einträge

(1977) NOT PRODUCED COMMERCIALLY IN US

(1982) NOT PRODUCED COMMERCIALLY IN US

Consumption Patterns · 2 Einträge

INSECTICIDE FOR NON-AGRICULTURAL USES EXCL FORESTS, 40%; FOREST, 30%; VEGETABLES, 20%; COTTON, 10% (1980)

Estimated US use of trichlorfon, 568,000 lb in 1989, 1,060,000 lbs in 1966.

Methods of Manufacturing · 2 Einträge

... Reaction of dimethyl hydrogen phosphite with trichloroacetaldehyde.

Prepn: W. Lorenz, United States of America patent 2701225 (1955 to Bayer).

Formulations/Preparations · 5 Einträge

Dipterex Technical Insecticide (Bayer Environmental Science): Active ingredient: trichlorfon 80%.

Dylox 80 Concentrate Insecticide (Bayer Environmental Science): Active ingredient: trichlorfon 80%.

Dylox 80 Turf and Ornamental Insecticide (Bayer Environmental Science): Active ingredient: trichlorfon 80%.

Dylox 6.2 Granular Insecticide (Bayer Environmental Science): Active ingredient: trichlorfon 6.2%.

For more Formulations/Preparations (Complete) data for Trichlorfon (14 total), please visit the HSDB record page.

Anwendungen · 2 Einträge

BeschreibungTrichlorfon is a colorless crystalline powder. It is soluble in water (120 g/L) and most organic solvents, except aliphatic hydrocarbons. Log Kow = 0.43. Trichlorfon is rapidly converted to dichlorvos by alkalis (2) and then hydrolyzed; DT50 (22 C) values at pH 4, 7, and 9 are 510 d, 46 h, and

VerwendenTrichlorfon is an irreversible organophosophate acetylcholinesterase inhibitor and the prodrug of Dichlorvos (D435950). Trichlorfon have also shown potential actions to be utilized as an effective org anophosphorus pesticide.

Anbieter50 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: A phosphonic ester that is dimethyl phosphonate in which the hydrogen atom attched to the phosphorous is substituted by a 2,2,2-trichloro-1-hydroxyethyl group.

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