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Fentin acetate

Fentin acetate structure

Fentin acetate 

structure
  • CAS No:

    900-95-8

  • Formula:

    C20H18O2Sn

  • Chemical Name:

    Fentin acetate

  • Synonyms:

    Acetic acid,triphenylstannyl ester;Triphenyltin acetate;Stannane,(acetyloxy)triphenyl-;Stannane,acetoxytriphenyl-;GC 6936;ENT 25208;Fentin acetate;Lirostanol;Tin triphenyl acetate;TPTA;Triphenylaceto stannane;VP 19-40;Brestan 60;Liromatin;Brestan;Acetoxytriphenylstannane;Batasan;Phentin acetate;Suzu;Acetatotriphenylstannane;(Acetyloxy)triphenylstannane;Tinestan;Sunitron A;Brestanid;Betafen;NSC 76068

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

ChEBI: An organotin compound that is the O-acetyl derivative of triphenyltin hydroxide. A fungicide used to control blights on potatoes, leaf spot diseases on sugar beet and anthracnose on beans.


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.|Solid


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.|Fentin acetate is an organotin compound that is the O-acetyl derivative of triphenyltin hydroxide. A fungicide used to control blights on potatoes, leaf spot diseases on sugar beet and anthracnose on beans. It has a role as an antifungal agrochemical. It is an organotin compound and an acetate ester. It derives from a fentin hydroxide.

Fentin acetate Basic Attributes

409.07

409.07

212-984-0

76068

3146|3020

DTXSID6021408

Colorless crystals|Small needles

Characteristics

26.30000

2.21660

white Powder

1.55 g/cm3 @ Temp: 20 °C

122-123 °C

60 °C

H2O: 28 mg/L (20 ºC)

APPROX 4°C

1.9 x 10 -3 Pa (60 °C)

Oral-rat LD50: 125 mg/kg; Oral-Mouse LD50: 81 mg/kg

Thermal decomposition of toxic tin-containing gas

Converted to fentin hydroxide (triphenyltin hydroxide) in presence of water. Unstable in acids and alkalis at 22 °C. Decomposed by sunlight and atmospheric oxygen.

Slowly oxidized, hydrolyzed when exposed to air and moisture.

Organometallics

ACETOXYTRIPHENYLSTANNANE is subject to decomposition when exposed to air, light and moisture [EPA, 1998].

IT IS NEITHER FLAMMABLE NOR AUTOIGNITIBLE.

Safety Information

III

6.1

3146

24/25-26-37/38-40-41-48/23-50/53-63

26-28-36/37/39-45-60-61

WH6650000

T+;N,N,T+

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable when dry. Converted to fentin hydroxide in the presence of water. Unstable in acids & alkalis (22 deg C). Decomposed by sunlight & by atmospheric oxygen.

P201-P260-P273-P280-P304 + P340 + P310

H301 + H311-H315-H318-H330-H335-H351-H361d-H371-H372-H410

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Fentin acetate should be buried. It is stable when dry, but relatively easily decomposed when exposed to air and light finally forming inorganic tin compounds. Recommendable method: Landfill.

Incompatible with emulsifiable preparations and pastes.|RAPIDLY HYDROLYZED BY WATER TO HYDROXIDE|... Incompatible with oil emulsions and EC formulations.

Avoid air, light and moisture. (EPA, 1998)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P391, P403+P233, P405, and P501|H301+H311 (19.19%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P309+P311, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 198 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P333+P313, P361, P363, P403+P233, P405, and P501

(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. (Non-Specific -- Organotin pesticide, n.o.s.) Small fires: dry chemical, carbon dioxide, water spray, or foam. Large fires: water spray, fog, or foam. (EPA, 1998)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(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. Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal. Small dry spills: with clean shovel place material into clean, dry container and cover; move containers from spill area. Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

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)|WHEN HANDLING THIS MATERIAL, WEAR GOGGLES, A RESPIRATOR, RUBBER GLOVES, & PROTECTIVE CLOTHES.

IT IS NEITHER FLAMMABLE NOR AUTOIGNITIBLE.

The compounds should not be allowed to enter drains or watercourses. /Triphenyltin compounds/

Keep out of reach of children. Keep away from food, drink & animal feeding stuffs. If you feel unwell, seek medical advice (show the label where possible).|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. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. All contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

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 ... .

SEDIMENT: The concns of triphenyltin in harbor sediment in Lake Lucerne, Switzerland was high, up to 380 ug/g(1). High concns were restricted to the upper 4 cm and decreased significantly below. The dating of cores suggest that triphenyltin may persist for more than a decade in sediment. Small amounts of the mono- and di- phenyltin were also found in the upper layers of sediment.

Toxicity

highly toxic

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/

LD50 Rat female oral 140-298 mg/kg (Technical AI, in starch mucilage)|LD50 Rat oral 125 mg/kg|LD50 Rat intraperitoneal 8.5 mg/kg|LD50 Mouse male ip 7.9 mg/kg|For more Non-Human Toxicity Values (Complete) data for TRIPHENYLTIN ACETATE (21 total), please visit the HSDB record page.

Triphenyltin acetate's production and former use(1) as an agricultural fungicide(2), and as a biocide in marine antifouling paints(3) resulted in its release to the environment through various waste streams(SRC).

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).

Triphenyltin acetate on sugar beet leaves was rapidly broken down during the silage process. Within 5 weeks, triphenyltin acetate, originally present at a concentration of 2470 mg/kg of fresh leaves, had degraded completely.|The rate constant for the vapor-phase reaction of triphenyltin acetate with photochemically-produced hydroxyl radicals has been estimated as 5.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.7 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Triphenyltin compounds in environmental waters either exist as, or will rapidly be converted to triphenyltin oxides, carbonates, or hydrated cations(2). Triphenyltin cation may react with water and behave like a simple protic acid with the formation of triphenyltin hydroxide(3). In seawater, the chloride ion may compete effectively with hydroxide ions resulting in the presence of triphenyltin chloride in the mixture of triphenyltin species(3). Triphenyltin compounds may react with sulfides present in sediment, leading to the formation of bis(triphenyltin sulfide(2). Triphenyltin acetate on a watch glass is degraded to diphenyl-, monophenyl-, and inorganic tin species when irradiated at wavelengths >350 nm(2). It 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(4).

A BCF of 800 was measured in rainbow trout for triphenyltin acetate(1). According to a classification scheme(2), this BCF suggests that bioconcentration in aquatic organisms is high(SRC). The uptake and elimination rates of structurally-related radiolabeled triphenyltin hydroxide in guppies were 41 l/kg-day and 0.014/day, giving a BCF (uptake: elimination ratio) of 2900 l/kg (wet weight) during 30 days of exposure(1). For rainbow trout larvae the uptake and elimination rates were 22 l/kg-day and 0.031/day, respectively giving a BCF of 650 ml/g after 4 days; the lower BCF in the trout than the guppies being a result of the higher elimination rate. Since equilibrium was not reached, the bioconcentration factor was underestimated(1). The log BCFs of triphenyltin in crucian carp obtained in a 7-day experiment were 1.70 (muscle), 1.70 (vertebra); 2.05 (liver); and 1.49 (kidney)(3). In studies in which the bioaccumulation and elimination of triphentyltin in Red Sea bream (Pagrus major) was by direct uptake from water, from diet, and from both simultaneously, about a quarter of the bioaccumulation was due to dietary uptake(4). The bioaccumulation factor was 0.257. The elimination rate was 0.020/day and was independent of the source of uptake, water or diet. Bioaccumulation was also independent of the form of triphenyltin in the diet(4). Minnow (Phoxinus phoxinus) embryos/larvae and freshly hatched larvae were exposed to triphenyltin chloride in Lake Lucerne, Switzerland water at 16 °C(5). The BCF for embryo larvae was 530 at the end of a 192 hr uptake period. Newly hatched larvae had BCFs of 457 and 930 after 96 and 144 hours. At this time the BCF had not reached a plateau so the actual BCF was higher. While uptake of triphenyltin from water was rapid, elimination was absent during a 96-hr depuration period. The concn of the metabolites monophenyltin and diphenyltin were very low(5).

If triphenyltin acetate is released to soil, it either exists as, or rapidly converted to oxides, hydroxides, carbonates, or hydrated cations(1). Oxides, hydroxides, carbonates or cations are not expected to leach through soil into groundwater(SRC). 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).

In water, triphenyltin compounds are expected to exist as triphenyltin oxides, carbonates, or hydrated cations(1). Volatilization from water surfaces is not expected to be an important fate process because the cation, oxides, hydroxides, or carbonates are not expected to volatilize(SRC). For example, no volatilization loss of triphenyltin was observed over a period of 6 days from a one ppm distilled water solution of triphenyltin hydroxide at pH 8.2 (unbuffered) and 32 °C with a solution surface area of 54 sq cm(2). Triphenyltin acetate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-8 mm Hg(3).

Triphenyltin acetate is one of the many pesticides present in surface water in The Netherlands, primarily in the Rhine River(1). It is one of the most widely used pesticides in the Rhine and Meuse basins(1).

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).

Inhalation, skin contact, swallowing.|Occupational exposure to triphenyltin acetate may occur through inhalation and dermal contact with this compound at workplaces where triphenyltin acetate is produced or used. (SRC)

Drug Information

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)|An agent that causes the production of physical defects in the developing embryo. (See all compounds classified as Teratogens.)

... /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.

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.

... /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/

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.

Very toxic, irritant to skin. (EPA, 1998)

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. Emergency Life-Support Procedures: Acute exposure to stannane, acetoxytriphenyl- may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victim to fresh air. Emergency personnel should avoid self-exposure to stannane, acetoxytriphenyl-. 2. Evaluate vital signs including pulse and respiratory rate and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to stannane, acetoxytriphenyl-. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of stannane, acetoxytriphenyl- is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age.Warning: Ingestion of stannane, acetoxytriphenyl- may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)

Several human poisonings from occupational exposures have been described but no deaths. Severe headache is a common symptom, as are nausea, vomiting, and epigastric pain, even in respiratory exposures. Glycosuria and hyperglycemia were encountered in several victims, as was dizziness, ... loss of consciousness occurred in 2 farmers after spraying.|Liver damage, in one case irreversible, has been reported in people spraying triphenyltin acetate, although exposure to other toxic compounds cannot be excluded. General malaise, headache, dizziness, & enlarged liver were the main symptoms in a patient who had 48 ug tin/l in his blood & 113 ug tin/l in his urine at the time of admission to hospital, after spraying a 60% triphenyltin acetate solution. Nine days after admission he developed diffuse erythema, but completely recovered 3 days later.|The majority of accidental poisonings involving systemic effects have been due to occupational exposure to triphenyltin acetate. Systemic effects reported to have followed both dermal & inhalation exposure include general malaise, gastric pain, dryness of the mouth, visual disturbances & shortness of breath. An enlarged liver & elevated levels of liver aminotransferase activity have been found in some cases. Recovery has generally been complete but in one case, where a man spilled an agricultural cmpd on his hands & chest, the liver damage persisted for 2 yr.|A case of triphenyltin acetate poisoning is described. The patient, who had been exposed mainly to cutaneous absorption, showed acute stages of an urticarial eruption, signs of hepatic injury, slight glucose intolerance, & EEG abnormalities. Concomitant with the highest concns of tin in plasma & the peak of tin excretion in urine, neutrophils did not show the normal incr in actin polymerization after stimulation with a chemotactic peptide (100 nM fMLP). The peak of urinary excretion of tin occurred between the fifth & the sixth day after poisoning; subsequently, the rate of excretion became slow, suggesting biphasic kinetics with the possibility of a cumulative trend.|For more Human Toxicity Excerpts (Complete) data for TRIPHENYLTIN ACETATE (6 total), please visit the HSDB record page.

Brestan

Fentin acetate Use and Manufacturing

Methods of Manufacturing

Phenylmagnesium bromide reacts with tin tetrachloride to produce triphenyltin chloride, and then reacts with sodium hydroxide to produce triphenyltin hydroxytin, and finally reacts with acetyl chloride to produce potato plague tin.

Uses

Triphenyltin Acetate is an organotin compound. Triphenyltin Acetate much like its hydroxide analogue is used as a fungicide and antifeeding compound for insect control. Recent studies show that Triphenyltin Acetate may have adverse effects on the reproductive and immune systems and may disrupt the endocrine system.

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.

Acetic acid, triphenylstannyl ester: ACTIVE

Product analysis is by hydrolysis to fentin hydroxide which is measured by potentiometric titration; or by gas liquid chromatography of a derivative. Residues may be determined by atomic-adsorption spectrophotometry of total tin.|FIVE LABORATORIES COLLABORATIVELY STUDIED 2 PROCEDURES FOR THE QUANTITATIVE DETERMINATION OF TRIPHENYLTIN COMPOUNDS IN TECHNICAL MATERIAL & IN PESTICIDE FORMULATIONS. BOTH PROCEDURES INCLUDED AN EXTRACTION STEP & A POTENTIOMETRIC TITRATION, BUT DIFFERED IN HOW THE BY PRODUCTS WERE REMOVED. THE 1ST WAS BASED ON CLEANUP WITH SODIUM TARTRATE & IN THE 2ND, ALKALINE ALUMINA WAS USED FOR PURIFICATION. THE REPRODUCIBILITY & THE REPEATABILITY WERE BETTER WITH THE ALUMINA METHOD THAN WITH THE TARTRATE METHOD. THE AVERAGE SYSTEMATIC DIFFERENCE BETWEEN THE 2 METHODS WAS -2.3%. THE METHOD BASED ON ALKALINE ALUMINA CLEANUP WAS ADOPTED AS AN INTERIM CIPAC METHOD.|DETERMINATION OF TRIPHENYLTIN COMPOUNDS & TRICYCLOHEXYLTIN HYDROXIDE BY GAS CHROMATOGRAPHY OF THEIR DERIVATIVES. A GAS-LIQUID CHROMATOGRAPHIC METHOD IS REPORTED FOR THE DETERMINATION OF TRIPHENYLTIN DERIVATIVES & TRICYCLOHEXYLTIN HYDROXIDE AFTER THEIR CONVERSION (BY WAY OF GRIGNARD REACTION CATALYZED BY COPPER CHLORIDE) TO TETRAPHENYLTIN & TRICYCLOHEXYLPHENYLTIN. THE RECOVERY OF TETRAPHENYLTIN & TRICYCLOHEXYLPHENYLTIN WAS SATISFACTORY IN THE RANGE OF 50 TO 3000 UG. DIFFERENT COLUMNS WERE TESTED USING FLAME-IONIZATION DETECTION. FOR BOTH DERIVATIVES, THE RESPONSE WAS LINEAR FROM 0.05 TO 3.00 UG. RESULTS OF THERMAL ANALYSIS, IR SPECTROSCOPY, & MASS SPECTROMETRY ARE REPORTED.

Agrochemicals -> Fungicides, Herbicides

Computed Properties

Molecular Weight:409.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:410.032882
Monoisotopic Mass:410.032882
Topological Polar Surface Area:26.3
Heavy Atom Count:23
Complexity:332
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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