Trichlorfon (ISO)

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H317：Kann allergische Hautreaktionen verursachen.

  H334：Kann bei Einatmen Allergie, asthmaartige Symptome oder Atembeschwerden verursachen.

  H410：Sehr giftig für Wasserorganismen mit langfristiger Wirkung.

• Sicherheit

  P273：Freisetzung in die Umwelt vermeiden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

Trichlorfon Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  WEISSE KRISTALLE.

• CHEMISCHE GEFAHREN

  Zersetzung beim Erhitzen und bei Kontakt mit Säuren und Basen unter Bildung giftiger Rauche. Greift viele Metalle an.

• ARBEITSPLATZGRENZWERTE

  TLV: (Einatembare Fraktion) 1 mg/m?(als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); BEI vorhanden; (ACGIH 2005).
  MAK nicht festgelegt (DFG 2005).
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation des Aerosols, über die Haut und durch Verschlucken.

• INHALATIONSGEFAHREN

  Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch bei Staubbildung schnell erreicht werden.

• WIRKUNGEN BEI KURZZEITEXPOSITION

  WIRKUNGEN BEI KURZZEITEXPOSITION:
  Möglich sind Auswirkungen auf das Nervensystem (durch cholinesterasehemmende Wirkung) mit nachfolgenden Krämpfen, Atemversagen und Tod. Cholinesterasehemmer. Exposition gegenüber hohen Konzentrationen kann zum Tod führen. Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.

• WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

  Wiederholter oder andauernder Kontakt kann zu Hautsensibilisierung führen. Möglich sind Auswirkungen auf das Nervensystem. Cholinesterasehemmer. Kumulative Wirkung möglich (s. AKUTE GEFAHREN/SYMPTOME).

• LECKAGE

  NICHT in die Kanalisation spülen. Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. An sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Atemschutzgerät, A/P2-Filter für organische Dämpfe und schädlichen Staub.

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R43:Sensibilisierung durch Hautkontakt möglich.
  R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.

• S-Sätze Betriebsanweisung:

  S24:Berührung mit der Haut vermeiden.
  S37:Geeignete Schutzhandschuhe tragen.
  S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
  S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
  S2:Darf nicht in die Hände von Kindern gelangen.

• Beschreibung

  Trichlorfon 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 <30 min, respectively.

• Chemische Eigenschaften

  Trichlorfon is a white to pale yellow crystalline solid.

• Chemische Eigenschaften

  White or almost white, crystalline powder.

• Verwenden

  Insecticide used to control ?ies and roaches.

• Verwenden

  anticholinergic, urinary incontenance therapy

• Verwenden

  One of the biologically active forms of nicotinic acid. Differs from NAD by an additional phosphate group at the 2?position of the adenosine moiety. Serves as a coenzyme of hydrogenases and dehydrogenases. Present in living cells primarily in the r

• Verwenden

  Trichlorfon is used to control a wide range of insects in many crops and to control household pests, flies in animal houses and ectoparasites in domestic animals.

• Verwenden

  Trichlorfon 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.

• Definition

  ChEBI: 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.

• Indications

  Metrifonate is an organophosphorous compound that is effective only in the treatment of S. haematobium. The active metabolite, dichlorvos, inactivates acetylcholinesterase and potentiates inhibitory cholinergic effects. The schistosomes are swept away from the bladder to the lungs and are trapped. Therapeutic doses produce no untoward side effects except for mild cholinergic symptoms. It is contraindicated in pregnancy, previous insecticide exposure, or with depolarizing neuromuscular blockers. Metrifonate is not available in the United States.

• Antimicrobial activity

  Useful activity is restricted to Schistosoma haematobium. It has little activity against other schistosomes. Although it exhibits activity against several other helminths, it is not used for their treatment.

• Allgemeine Beschreibung

  Metrifonate is an organophosphate thatwas originally developed to treat schistosomiasis under thetrade name Bilarcil. It is an irreversible cholinesteraseinhibitor with some selectivity for BuChE over AChE. Itachieves sustained cholinesterase inhibition by its nonenzymaticmetabolite dichlorvos (DDVP), a long-actingorganophosphate. Its use in mild-to-moderate Alzheimerdisease was suspended recently because of adverse effectsexperienced by several patients during the clinical evaluationof this product. Toxicity at the neuromuscular junctionis probably attributable to the inhibition by the drug of neurotoxicesterase, a common feature of organophosphates.

• Allgemeine Beschreibung

  Chlorophos is a white crystalline solid. Soluble in water, benzene, chloroform, ether; insoluble in oils. Chlorophos is a wettable powder. Chlorophos can cause illness by inhalation, skin absorption and/or ingestion. Chlorophos is used as a pesticide.

• Air & Water Reaktionen

  Chlorophos decomposes at higher temperatures in water and at pH <5.5. Chlorophos is sensitive to prolonged exposure to moisture. Chlorophos is unstable in alkaline solutions.

• Reaktivität anzeigen

  Chlorophos is incompatible with alkalis. Chlorophos is corrosive to black iron and mild steel. Chlorophos is corrosive to metals. Chlorophos is subject to hydrolysis.

• Health Hazard

  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.

• Brandgefahr

  Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

• Landwirtschaftliche Anwendung

  Insecticide, Anthelmintic: Not approved for use in EU countries . Registered for use in the U.S. except California. Trichlorfon has non-agriculture uses on golf course turf, home lawns and similar venues, and in non-food contact areas of food and meat processing plants. Also on ornamental shrubs and plants, and ornamental and bait fish ponds. Overseas, trichlorfon is used as cattle pour-on, which is classified as a food-use. It is used against insects such as lepidopteran larvae (caterpillars), white grubs, mole crickets, cattle lice, sod webworms, leaf miners, stink bugs, flies, ants, cockroaches, earwigs, crickets, diving beetles, water scavenger beetles, water boatman, backswimmers, water scorpions, giant water bugs and pillbugs. All food and feed uses in the U.S. were voluntarily canceled November 21, 1995. It was used on Brussels sprouts, barley, beets, blueberries, beans (dryand snap), corn, field corn, popcorn, sweet corn, cotton, cow peas, lima beans, tomatoes, cabbage, carrots (including tops), cauliflower, collards, cowpeas, southern peas, blackeyed peas, crowder peas, pumpkins, collards, lettuce and alfalfa, cotton, peanuts, peppers, pumpkins, tobacco, soybeans and treatment to manure. U.S. Maximum Allowable Residue Levels for the residues of Trichlorfon [40 CFR 180.198]: in or on the following raw agricultural commodities: cattle, fat 0.1ppm (negligible residue); cattle, meat byproducts 0.1ppm (negligible residue); and cattle, meat 0.1ppm (negligible residue)

• Pharmazeutische Anwendungen

  An organophosphorus compound. It is soluble in water and stable at room temperature. At higher temperatures it decomposes to the insecticide dichlorvos.

• Handelsname

  AEROL 1 (PESTICIDE)®; AGROFOROTOX®; ANTHON®; BAY 15922®; BAYER 15922®; BAYER L 13/59®; BILARCIL®; BOVINOX®[C]; BRITON®; BRITTEN®; CEKUFON®; CHLORAK®; CHLOROFTALM®; CICLO-SOM®; COMBOT®; COMBOT EQUINE®; DANEX®[C]; DEP®; DEPTHON®; DIMETOX®; DIPTEREX®; DIPTEREX® 50; DIPTEVU®; DITRIFON®; DYLOX®; DYLOX-METASYSTOX-R®; DYREX®; DYVON®; EQUINO-ACID®; EQUINO-AID®; FLIBOL E®; FLIEGENTELLE®; FOROTOX®; FOSCHLOR®; FOSCHLOR R®; FOSCHLOR R-50®; LEIVASOM®; LOISOL®; MASOTEN®[C]; MAZOTEN®; NEGUVON®; NEGUVON A®; PHOSCHLOR R50®; PROXOL®; RICIFON®; RITSIFON®; SATOX 20WSC®; SOLDEP®; SOTIPOX®; TRICHLORPHON FN®; TRINEX®; TUGON®; TUGON FLY BAIT®; TUGON STABLE SPRAY®; VERMICIDE BAYER 2349®; VOLFARTOL®; VOTEXIT®; WEC 50®; WOTEXIT®

• Mechanism of action

  In vivo, metrifonate rapidly rearranges to O,O-dimethyl O-(2,2-dichlorovinyl) phosphate, which is a potent inhibitor of schistosome acetylcholinesterase. This paralyzes the parasites because of the accumulation of acetylcholine, which functions as inhibitory transmitter . Trade name: Bilarcil (Bayer).

• Pharmakokinetik

  Metrifonate is rapidly absorbed after oral administration, achieving a peak concentration in plasma within 1–2 h. It undergoes chemical transformation to dichlorvos, which is the active molecule. Dichlorvos is rapidly and extensively metabolized and excreted mainly in the urine.

• Clinical Use

  Urinary schistosomiasis (especially mass chemotherapy control programs)

• Nebenwirkungen

  Various side effects such as abdominal pain, gastrointestinal upsets and vertigo occur in many patients. As the worms release their hold of the veins in the bladder they pass through the blood system to the lungs, where they disintegrate; this may cause some of the side effects. Cholinesterase levels in the blood and on erythrocytes are depressed, but the significance of this is unknown.

• Sicherheitsprofil

  Poison by ingestion, inhalation, inti-aperitoneal, subcutaneous, intravenous, and intramuscular routes. Moderately toxic by skin contact. Human systemic effects: true cholinesterase. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. An eye irritant. When heated to decomposition it emits very toxic fumes of Cland POx.

• mögliche Exposition

  Trichlorfon is used as an agricultural and forest insecticide.

• Carcinogenicity

  When rats were fed diets that contained 0, 50, 100, 200, 250, 400, 500, or 1000 ppm (equivalent to about 0.5, 12.5, 25, or 50 mg/kg/day) for 17 or 24 months, no treatment-related effects occurred in those fed 50–250 ppm . Histopathological results suggested the occurrence of mammary tumors in rats fed 400, 500, and 1000 ppm. In another study, when rats were fed diets containing 0, 50, 250, 500, or 1000 ppm (equivalent to about 2.5, 12.5, 25, or 50 mg/kg/day) trichlorfon for 24 months, no treatment-related effects other than whole-blood cholinesterase depression at 1000 ppm occurred . There was no increase in the incidence of either benign or malignant tumors, including mammary tumors.

• Environmental Fate

  Soil. Trichlorfon degraded in soil to dichlorvos (alkaline conditions) and desmethyl dichlorvos (Mattson et al., 1955).
  Plant. In cotton leaves, the metabolites identified included dichlorvos, phosphoric acid, O-demethyl dichlorvos, O-demethyl trichlorfon, methyl phosphate and dimethyl phosphate (Bull and Ridgway, 1969). Chloral hydrate and trichloroethanol were r
  Pieper and Richmond (1976) studied the persistence of trichlorfon in various foliage following an application rate of 1.13 kg/ha. Concentrations of the insecticide found at day 0 and 14 were 81.7 ppm and 7 ppb for willow foliage, 12.6 ppm and 670 ppb for
  Chemical/Physical. At 100°C, trichlorfon decomposes to chloral. Decomposed by hot water at pH <5 forming dichlorvos (Worthing and Hance, 1991).

• Stoffwechselwegen

  The metabolism of trichlorfon has been reviewed by Zayed et al. (1967), Sawicki (1973) and Zayed (1974). Trichlorfon is a non-systemic insecticide with favourable mammalian toxicity. There is considerable evidence that trichlorfon requires in vivu activation via dehydrochlorinatation to yield dichlorvos which is the active acetylcholinesterase inhibitor. This reaction is quite facile in slightly basic solution and the subsequent routes for the metabolism of trichlorfon are apparently the same as those of dichlorvos. However, there has been considerable controversy on the role played by this reaction in vivu since many workers have failed to identify dichlorvos as a metabolite in plants, mammals or insects treated with trichlorfon. It was realised that trichlorfon was a very much poorer inhibitor of acetylcholinesterase than dichlorvos and most considered that its insecticidal activity must be due to metabolism to dichlorvos as an activating step in an analogous way that phosphorothioates are metabolised to phosphates. Metcalf et al. (1959) and Miyamoto (1959) proposed that trichlorfon was totally inactive as an inhibitor of acetylcholinesterase and that any inhibition seen in vitru was due to some conversion to dichlorvos during the course of the assay for anticholinesterase activity. Metcalf et al. (1959) also reported the identification of dichlorvos in trichlorfon-treated houseflies. This conclusion was by no means universal and Arthur and Casida (1957) argued that trichlorfon was the active acetylcholinesterase inhibitor and the identification of a glucuronide conjugate of trichloroethanol was evidence that the primary route of stage I metabolism was hydrolysis of the P< bond. Other work, however, has provided evidence for the in vivu production of dichlorvos and it seems probable that the failure of some experiments to detect it is due to its rapid metabolism, resulting in a very low steadystate concentration. The metabolism of trichlorfon can be envisaged as being either through a deactivation route via demethylation and/or conjugation followed by breakdown of the demethylated products or an activation reaction to yield dichlorvos which is then degraded via a hydrolytic mechanism to yield dimethyl phosphate and dichloroacetaldehyde or demethylated by glutathione-S-methyl transferase. These competing reactions have been investigated in mammals and insects and it is the balance of activation and degradative metabolism which confers the favourable mammalian toxicity of trichlorfon in comparison with that of dichlorvos.

• Stoffwechsel

  Trichlorfon administered to mammals is rapidly metabolized and excreted almost completely in the urine within 6 h. Majormetabolites are dimethyl hydrogen phosphate, methyl dihydrogen phosphate, and conjugates of dichloroacetic acid and trichloroethanol. Trichlorfon is rapidly broken down in soil.

• Versand/Shipping

  UN2783 Organophosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

• Degradation

  Trichlorfon is subject to hydrolysis and dehydrochlorination. Decomposition proceeds more rapidly with heating and above pH 6. It is rapidly converted by alkalis to dichlorvos (2) which is then hydrolysed. DT₅₀ s at pH 4,7 and 9 were 510 days, 46 hours and <30 min respectively at 20 °C. Photolysis is slow (PM).
  Trichlorfon undergoes a facile rearrangement in the presence of mild base or heat to yield dichlorvos (2) and one mole of HCI (Barthel et al., 1955; Lorenz et al., 1955; Mattson et al., 1955). This reaction was shown to be first order in both trichlorfon concentration and [OH^-] with a calculated t_1/2 of 5 hours at pH 7.0 (37 °C) (Miyamoto, 1959). A mechanism for this reaction is shown in Scheme 1.

• Toxicity evaluation

  The acute oral LD₅₀ for rats is about 450 mg/kg. Inhalation LC50 (1 h) for rats is >0.5 mg/L air. NOEL (2 yr) for rats is 100 mg/kg diet (5 mg/kg/d). ADI is 0.01 mg/kg b.w.

• Inkompatibilitäten

  This chemical may be characterized as an organo-phosphate or-chlorine compound. Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducin g agents such as hydrideds and active metals. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.Alkaline materials: lime, lime sulfur, etc. Corrosive to iron, steel and possibly to other metals.

• Waste disposal

  Add a combustible solvent and burn in a furnace equipped with an afterburner and an alkali scrubber.In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

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