Triphenyltin acetate

Ascher and Nemny 495) found that residues of triphenyltin acetate on glass, resulting from the evaporation of acetone solutions thereof, were, on contact to houseflies, less toxic with rising concentration. As triphenyltin acetate is likely to be a self-associated polymer in the solid state [similar to trimethyltin acetate (355)] and in concentrated solutions, it was suggested 495) that the monomer, which exists in dilute solutions, is toxic to insects, and the polymer, nontoxic. Interestingly, in this connection, a triphenyltin methacrylate copolymer has 470) a very low mammalian toxicity (acute, oral LDso for mice >2000 mg/kg). 

It has been well established that triphenyltin compounds are broken down photochemically to inorganic tin via the di- and monophenyltin derivatives both under laboratory (505, 506) and natural (507) conditions. In soil, triphenyltin acetate is converted microbiologically (505) into inorganic tin, as is tricyclohexyltin hydroxide (502). The latter compound is also photochemically broken down to inorganic tin (502, 508). 

Strmac, M. and Braunbeck, T. (1999). Effects of triphenyltin acetate on survival, hatching success, and liver ultrastructure of early life stages of zebrafish (Danio rerio). Ecotoxicology and Environmental 44, 25-39. 

With stannous octoate-promoted polymerization, the metal species is believed to function as the catalyst and water (added or endogenous), or alcohol, serves as the initiator (Fig. 2). This mechanism is supported by recent kinetic studies of PCL polymerization in the presence of triphenyltin acetate (46). After an induction period, polymerization is zero order with respect to monomer and near first... 

TBPA f-Butylperoxy acetate TPhT-Ac Triphenyltin acetate... 

Analysis by cathodic reduction of triphenyltin acetate in pesticide preparations131 and in samples from marine sources132 can reach detection limits of 1CT8 M to 2.5 x 10 9 M,... 

Bis(tributyltin)oxide in antifouling paint was found to change to tributyltin chloride and an unknown organotin species by Allen and coworkers106. The organotin species appear to be held strongly within the paint film. In the case of triphenyltin chloride and triphenyltin acetate, evidence of dephenylation to form diphenyltin and monophenyltin compounds has been obtained. 

Lepus triphenyltin acetate/kg ration for growth in all groups. Tissue concentrations ... 

A recent area of interest has been the mass spectra of organotin pesticides (160,161), for example, triphenyltin acetate that fragments as follows ... 

Synonyms Triethyltin iodide dibutyltin chloride tributyltin chloride triphenyltin acetate bis(tributyltin) oxide triphenyltin chloride... 

Triphenyltin Acetate Liver damage has occurred from occupational exposure to triphenyltin acetate. In two cases, both developed hepatomegaly one had slightly elevated SGPT and SCOT activity. Occupational exposure to a 20% solution produced skin irritation 2-3 days after prolonged contact with contaminated clothing. Other nonspecific effects of exposure have included headache, nausea, vomiting, diarrhea, and blurred vision. ... 

Fed diets with 25, 50, or 100 mg triphenyltin acetate/kg ration for 15 days, then 5 days on clean feed, 15 days on test diet,... 

Nangniot and Martens [3] determined triphenyltin acetate fungicide in vegetable matter by a method based on the hanging drop mercury electrode. 

Animal studies tend to confirm the dermal/ocular effects reported for humans. Bis(tributyltin)oxide is a severe irritant to the skin and an extreme eye irritant in rabbits (Sheldon 1975). By contrast, tributyltin fluoride and triphenyltin fluoride produced only minimal skin irritation but were also extreme eye irritants (Sheldon 1975). Other acute studies have likewise demonstrated the skin irritating potential of bis(tributyltin)oxide and triphenyltin acetate in rats (Klimmer 1969 Pelikan and Cerny 1968). 

Manzo L, Richelmi P, Sabbioni E, et al. 1981. Poisoning by triphenyltin acetate. Report of two cases and determination of tin in blood and urine by neutron activation analysis. Clin Toxicol 18 1343-1353. 

On the other hand, triphenyltin acetate and triphenyltin hydroxide were the first commercial products introduced during the early 1960s followed by triphenyltin chloride, tricyclohexyltin hydroxide, bis(trineophenyltin) oxide, and tricyclohexatin-1,2,4-triazole, respectively. Triphenyltin hydroxide was one of the recommended pesticides for rice and necessary for countries like Thailand where rice is a major component of both domestic and export markets (Visoottiviseth, 2001). 

Triaryltin compounds such as triphenyltin hydroxide (TPTH, Fentin hydroxide, Du-Ter, I), or triphenyltin acetate (TPTOAC, Brestan, II) have been shown to be effective as protectant fungicides. These compounds have demonstrated other activity such as antifoulants, bactericides and algi-cides. Due to their low phytotoxicity they have been developed for plant protection. In several cases they have been reported to exhibit the unusual property of deterring insects from feeding. (2 )... 

The trimethyltin and in particular the tri-n-hexyl- and tri-n-octyltin compounds were notably inactive. Triphenyltin acetate exhibited moderate to high activity. 

Since the early finding in 1972 that triphenyltin acetate (but not the corresponding chloride) retards tumour growth in mice [161], a number of organotin derivatives have been prepared and tested in vitro and in vivo [162-166]. 

The production of triphenyltin hydroxide [76-87-9] and triphenyltin acetate [900-95-8] start with triphenyltin chloride, which is prepared by the Kocheshkov redistribution reaction from tetraphenyltin and tin tetrachloride. The hydroxide is prepared from the chloride by hydrolysis with aqueous sodium hydroxide. The acetate can be made directly from the chloride using sodium acetate or from the hydroxide by neutralization with a stoichiometric quantity of acetic acid. 

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