Fentin acetate

HCID 16682804CAS 900-45-8

Grundinformationen

Standard-SMILES
CC(=O)[O][Sn]([c]1ccccc1)([c]1ccccc1)[c]1ccccc1
InChIKey
WDQNIWFZKXZFAY-UHFFFAOYSA-M
Summenformel
C20H18O2Sn
Durchschnittliche Molmasse
409,1 g/mol
Monoisotopische Masse
410,03287452

Überblick

Stannane, acetoxytriphenyl- appears as a white crystalline solid. Melting point 123-131 °C (253-268 °F). Used as a fungicide, algaecide and molluscicide. Controls early and late blight on potatoes.

Namen und Bezeichner

Bevorzugter Name
Fentin acetate
IUPAC
triphenylstannyl acetate

Namen und Synonyme

Fentin acetateTRIPHENYLTIN ACETATE900-95-8Phentin acetatePhentinoacetateFentinacetatLiromatinLirostanolBatasanSuzuAcetoxytriphenylstannaneFenolovo acetate
Weitere Namen anzeigen
Tin triphenyl acetateTriphenylaceto stannaneAcetatotriphenylstannaneFentin acetaatFentine acetateFintin acetatoFentin azetatBrestan 60

Datenbank-Bezeichner

CAS
900-45-8、900-95-8
PubChem CID
16682804
DTXSID
DTXSID6021408
ChEBI
CHEBI:81918
EC Number
212-984-0

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
5
Schwere Atome
23

Experimentelle und physikochemische Eigenschaften

Chemical ClassesMetals -> Tin Compounds, Organic
Pesticides · 2 Einträge

Fungicides, Herbicides

Active substance -> EU Pesticides database: Not approved

LogPlog Kow = 3.43
Density · 2 Einträge

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

1.55 g/cu cm @ 20 °C

Color/Form · 2 Einträge

Colorless crystals

Small needles

Solubility · 3 Einträge

In water, about 9 mg/l at pH 5 and 20 °C.

In ethanol 22, ethyl acetate 82, dichloromethane 460, hexane 5, toluene 89 (all in g/l at 20 °C).

0.009 mg/mL at 20 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

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

P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P320, P321, P330, P332+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301+H311 (94.4%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P354+P338, P308+P316, P316, P317, P318, P319, P320, P321, P330, P332+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 3 Einträge

Regulation (EC) No 1107/2009 (amended)

2002/478/EC

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 - Stannane, (acetyloxy)triphenyl-: Human health tier I assessment
DOT LabelPoison
Fire HazardsAvoid air, light and moisture. (EPA, 1998)
Fire PotentialIT IS NEITHER FLAMMABLE NOR AUTOIGNITIBLE.
Health HazardsVery toxic, irritant to skin. (EPA, 1998)

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

(Non-Specific -- Organotin pesticide, n.o.s.) Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

First Aid · 1 Eintrag

Signs and Symptoms of Stannane, Acetoxytriphenyl- Exposure: Acute exposure to stannane, acetoxytriphenyl- may result in severe headache, nausea, vomiting, cramping, abdominal pain, skin burns or dermatitis, visual defects including photophobia (sensitivity to light), convulsions, and loss of consciousness. Occasionally bronchitis may also be noted.

Exposure Control and Personal Protection0.002 [mg/m3], inhalable fraction, as Sn[German Research Foundation (DFG)]
Storage ConditionsSTORE UNDER DARK & DRY CONDITION.
Cleanup MethodsThe compounds should not be allowed to enter drains or watercourses. /Triphenyltin compounds/
Nonfire Spill Response · 1 Eintrag

(Non-Specific -- Organotin pesticide, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. Do not touch spilled material; stop leak if you can do it without risk. Use water spray to reduce vapors.

Toxikologische Informationen

Health EffectsBreathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (L307, L308)
Environmental Fate · 4 Einträge

TERRESTRIAL FATE: AROMATIC LABELED (14)C-TRIPHENYLTIN ACETATE ... ADDED TO SOIL AT LEVELS OF 5.0 & 10.0 PPM & SHIELDED FROM LIGHT ... /HAD HALF-LIFE OF/ APPROX 140 DAYS. CONSTANT LINEAR RATE OF CARBON DIOXIDE EVOLUTION OCCURRED UP TO 80TH DAY, AT WHICH TIME 1/3 OF PHENYL CARBON HAD BEEN RELEASED. RATE THEN FELL TO LESS THAN HALF INITIAL RATE.

TERRESTRIAL FATE: If triphenyltin acetate is released to soil, it either exists as or is rapidly converted to triphenyltin oxides, hydroxides, carbonates, or hydrated cations(1). In a laboratory soil leaching study, triphenyltins were strongly attached to soil(2). This also suggests that triphenyltins (such as triphenyltin acetate) may be expected to have low mobility in soil(SRC). The Freundlich parameters, log k and 1/n, for triphenyltin to sediment were 1.81 and 0.793, respectively(3). Volatilization from moist soil surfaces is not expected to be an important fate process because the cation, oxides, hydroxides, or carbonates are not expected to volatilize(SRC). Triphenyltin acteate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-7 mm Hg(4). Triphenyltin acetate undergoes biodegradation in the environment(SRC). Bacteria have been reported to cleave aryl-tin bonds in triphenyltin acetate(5). Triphenyltin acetate degrades in normal, fertile, agricultural field at 11-16 °C in <6 wks under aerobic conditions and 6-18 weeks under anaerobic conditions(6).

AQUATIC FATE: If triphenyltin acetate is released to soil, it either exists as or is rapidly converted to triphenyltin oxides, carbonates, or hydrated cations(1). Triphenyltin cation may react with water and behave like a simple protic acid with the formation of triphenyltin hydroxide(2). In seawater, the chloride ion may compete effectively with hydroxide ions resulting in the presence of triphenyltin chloride(2). Triphenyltin compounds may react with sulfides present in sediment, leading to the formation of bis(triphenyltin) sulfide(1). Cations, such as triphenyltin cation, generally adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC). Triphenyltin cation may be susceptible to photolysis in water since triphenyltin hydroxide dissolved in pure water was approx 72% photodegraded by sunlight in 36 days apparently by a radical process; diphenyltin species were the only products observed(3). Triphenyltin acetate on a watch glass is degraded to diphenyl-, monophenyl-, and inorganic tin species when irradiated at wavelengths >350 nm(1). According to a classification scheme(4), a BCF of 800 for rainbow trout(5), suggests the potential for bioconcentration of triphenyltin cation in aquatic organisms is high(SRC). Triphenyltin may biodegrade in aquatic environments(SRC). Bacteria have been reported to cleave aryl-tin bonds in triphenyltin acetate(6). Triphenyltin acetate degrades in normal, fertile, agricultural field at 11-16 °C in <6 wks under aerobic conditions and 6-18 weeks under anaerobic conditions(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triphenyltin acetate, which has an estimated vapor pressure of 4.8X10-7 mm Hg at 25 °C(2) will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase triphenyltin acetate 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 2.7 days(SRC), calculated from its rate constant of 5.9X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase triphenyltin acetate may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesOral (L308) ; inhalation (L308) ; dermal (L308)
Milk Concentrations · 2 Einträge

During oral dosing of sheep for 20 days with fentin acetate at the rate of 10 mg/day, (113)tin was found in the milk at an average concentration of 0.0017 ppm.

Cows fed sugar beets leaves containing triphenyltin acetate at 1 mg/kg had concn of 0.004 mg/kg in their milk(1).

Toxicity Summary · 2 Einträge

IDENTIFICATION: Triphenyltin compounds are triphenyl derivatives of tetravalent tin. They are colorless solids with low vapor pressures. They are lipophilic and have low solubility in water. Triphenyltin compounds have been used extensively as algicides and molluscicides in antifouling paints since the 1960s. Use of triorganotins in antifouling paints has been restricted in many countries because of their catastrophic effects on the oyster industry and more general effects on the aquatic ecosystem. HUMAN EXPOSURE: There are no data concerning the occupational exposure to triphenyltin compounds. A few poisoning case reports does describe neurotoxic effecys, which appeared to persist. Exposure of the general public to triphenyltin compounds occurs mostly from ingestion of contaminated seafood. ANIMAL/PLANT STUDIES: Triphenyltin compounds given orally to rats are not readily absorbed and are excreted primarily in the feces and partly in the urine. They are metabolized to diphenyltin, and monophenyltin, and non-extractable bound residues. Absorbed triphenyltin compounds accumulate in the kidney and liver to the greatest extent, with smaller amounts in other organs. Triphenyltin compounds, applied dermally can penetrate through the skin in a time and dose dependent manner. Triphenyltin exerts a variety of health effects in various animal species, including effects on the immune system, reproductive/developmental effects at levels near those that are maternially toxic, hyperplasia/adenomas in endocrine organs, apoptosis in thymus cells, calcium release in sarcoplasmic reticulum cells, and eye irritation. Triphenyltin compounds are moderately acutely toxic to rats. They are not carcinogenic, but some data show that they are co-clastogenic. Reproductive and developmental effects include a decrease in the number of inplantations and live fetuses (at 1.0 mg triphenyltin acetate/kg body weight per day in a rabbit gavage study), reduction in litter size/pup weight and in relative thymus or spleen weightin the weanlings (at 1.5 mg triphenyltin acetate/kg body weight per day in the diet of a two generation reproduction study in rats). Triphenyltin compounds affect the immune system. Triphenyltin compounds exert deleterous effects on aquatic organisms at low concentrations. Triphenyltin is considered an endocrine disruptor, because of imposex, a phenomenon in which female gastropods develop male sex organs. /Triphenyltin cmpd & Triphenyltin acetate/

Organotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (L308, A182, A184)

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. Stannane, acetoxytriphenyl- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered for and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

State Drinking Water Guidelines(MN) MINNESOTA 4000 ug/l /Tin/

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

The phasic distribution of spermatogenesis tubules after treatment with triphenyltin acetate and triphenyltin chloride was investigated in rats. Male albino Holtzman rats were divided into groups and administered triphenyltin acetate and triphenyltin chloride in the diet at 20 mg/kg/day for 20 days. Four animals from each group were killed on day 21 of treatment. Testes were removed and studied histologically for the presence or absence of sperm in tubules. Remaining animals were placed on regular food from day 25 of treatment for an additional 70 days and then treated as other animals. Although all eight phases of spermatogenesis were evident in triphenyltin acetate treated animals, as in controls, a general paucity of mature sperms and a relative predominance of earlier phases was evident. Sperm deficiencies were noted in phases 3 through 5 and the number of tubules was 33 percent of controls in phase 8. The latter indicated a possible effect of triphenyltin acetate on sertoli cells. In triphenyltin chloride treated animals, the tubules contained few sperm, especially in phases 2 to 5, and showed no normal phase distribution characteristics. No tubules advanced beyond phase 5. Triphenyltin chloride treated animals differed significantly in phase 4, indicating and interruption in the meiotic process. After normal diet for 70 days, triphenyltin acetate treated animals showed spermatogenesis similar to that of controls in all phases and in maturity of sperm. In the triphenyltin chloride treated group, spermatogenesis was similar to controls in all respects. The phasic distribution and tubule appearance were indicative of complete recovery of spermatogenic epithelium. /It was/ concluded that the difference in effects of the two triphenyltin compounds on the phasic distribution of cell association in tubules may be due to the actual concentration of the triphenyltin moiety reaching the active site.

Biological Half-Life · 2 Einträge

... /ANIMALS/ HAVE A BIOLOGICAL HALF-LIFE OF 20 HR WHILE /THEIR/ METABOLIC PRODUCTS ... HAVE BIOLOGICAL HALF-LIFE OF 8-70 DAYS.

BIOLOGICAL HALF TIME WAS EST AT 9.4 DAYS FROM SC INJECTION OF (113)TIN-TRIPHENYLTIN IN GUINEA PIGS. /TRIPHENYL TIN/

Metabolism/Metabolites · 3 Einträge

INTACT (113)TIN-DIPHENYLTIN & (113)TIN-MONOPHENYLTIN WERE ONLY CMPD IDENTIFIED IN FECES OF GUINEA PIGS ADMIN (113)TIN-TRIPHENYLTIN ACETATE SUBCUTANEOUSLY.

Triphenyltin acetate, which is resistant to the in-vitro dealkylation system, /the microsome-soluble reduced nicotinamide adenine dinucleotide system containing cytochrome p450 dependent mono-oxygenase/ is metabolized, probably by some other mechanism to diphenyl- & monophenyltin, & inorganic tin.

Though tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (L308)

MeSH Pharmacological Classification · 2 Einträge

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.

An agent that causes the production of physical defects in the developing embryo.

Absorption, Distribution and Excretion · 5 Einträge

... /Based on oral & ip admin to rats, mice & guinea pigs/ absorption from the GI tract is poor compared with that from the peritoneum.

Absorption from the skin is poor. During oral dosing of sheep for 20 days with fentin acetate at the rate of 10 mg/day, tin was found in milk at an avg concn of 0.0017 ppm. (113)Tin was present as fentin acetate & in 2 unidentified forms. Seventeen days after dosing was stopped, the concn had fallen to the limits of detectability. During treatment, the concn of (113)tin was 0.0029 ppm in the blood & 0.0075 ppm in the urine. Eight days after dosing was stopped, the liver, kidney, lung, pancreas, gall bladder, & brain contained higher concn of (113)tin than did other organs, & the level was still incr in the liver after 218 days. In cows & sheep, triphenyltin is excreted chiefly in the feces. Triphenyltin is rapidly distributed to all tissues, including the brain of rats. It can still be detected in the brain of rats & guinea pigs more than 30 days after a single dose.

WHEN TAKEN IN BY ANIMALS, PROBABLY AS RESIDUE ON GREEN FODDER ... /IT/ WAS RAPIDLY EXCRETED WITH /FECES/. ... SMALL AMT ABSORBED WAS PARTLY EXCRETED IN URINE & PARTLY DISTRIBUTED THROUGHOUT WHOLE BODY.

CUTANEOUS APPLICATION OF (113)TIN-TRIPHENYLTIN ACETATE IN GUINEA PIGS RESULTED IN 3.04% & 7.97% OF DOSE BEING ABSORBED THROUGH SKIN, WHILE 16.3% & 12.4% WERE FOUND IN APPLICATION AREA 1 & 2 DAYS AFTER TREATMENT. RADIOACTIVITY WAS FOUND IN LIVER, KIDNEY & BRAIN IN LARGE AMT FOLLOWING SC INJECTION OF (113)TIN-TRIPHENYLTIN ACETATE, ALTHOUGH ABSORPTION PROCEEDED SLOWLY FROM INJECTION SITE. ABOUT 83% OF DOSE WAS ELIMINATED THROUGH FECES WITHIN 20 DAYS & BIOLOGICAL HALF TIME WAS EST AT 9.4 DAYS FROM SC INJECTION OF (113)TIN-TRIPHENYLTIN IN GUINEA PIGS. INTACT (113)TIN-DIPHENYLTIN & (113)TIN-MONOPHENYLTIN WERE ONLY CMPD IDENTIFIED IN FECES AFTER SC ADMIN.

For more Absorption, Distribution and Excretion (Complete) data for TRIPHENYLTIN ACETATE (8 total), please visit the HSDB record page.

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 6 Einträge

Used as an acaricide (miticide) and algaecide in rice and potato rot; [Ullmann] Used as fungicide on potatoes, sugar beets, and nuts; Not currently registered with the EPA for use in the US; [HSDB] Used as molluscicide; [CAMEO]

Banned for use as a pesticide for plant protection and biocide in the EU; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

For Triphenyltin acetate (USEPA/OPP Pesticide Code: 496700) there are 0 labels match. /SRP: Not registered for current 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./

Fungicide. Controls early and late blight on potatoes. Cercospora on sugar beets, peanuts, scab on pecans. /Former use/

Triphenyl tin compounds are ... also used as a biocide in antifouling paints. /Triphenyltin compounds/ /Former/

Methods of Manufacturing/Triphenyltin acetate/ can be made directly from triphenyltin chloride using sodium acetate or from the hydroxide by neutralization with a stoichiometric quantity of acetic acid.
Formulations/Preparations · 5 Einträge

USEPA/OPP Pesticide Code 496700; Trade Names: Brestan. /Former/

WETTABLE POWDER (190 & 540 G AI/KG). 'BRESTAN', WETTABLE POWDER (540 G FENTIN ACETATE + 160 G MANEB/KG)

Tech grade is >94% pure

Tinestan WP 20 (Fentin acetate 20%); Tinestan WP 60 (Fentin acetate 60%).

Flowable suspension, wettable powder.

General Manufacturing InformationAcetic acid, triphenylstannyl ester: ACTIVE

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