Diphenyltin Chloride Research Articles

Toxicity of Diphenyltin Chloride on viable count of aerobic bacteria from River Benue.

This research was carried out to determine the toxicity of diphenyltin chloride on viable count of freshwater aerobic bacteria. Water samples obtained from a depth of 15 cm at five sampling points along river Benue were spiked with 3 mM of DPTCl to have a duplicate setup of three (3) treatments. Organotin degradation was determined by measuring the decrease in the concentration of DPTCl using an X-ray fluorescence spectrophotometer on days 0, 14, 28, 42, and 56 and the viable count of bacteria was also determined using spread plate technique on MSA. DPTCl concentration was further varied (5 mM, 7 mM and 10 mM) to test levels of toxicity to viable count of bacteria as well as bacterial resistance. patio sequencing technique was used to determine the metagenomics of bacteria species capable of DPTCl degradation from the water samples. Percentage of chemically degraded (40.29%) during the initial two weeks of experiment when the bacterial population was high, was more than the percentage degraded (11.49%) during the last two weeks of the experiment when the biocidal effect of DPTCl had drastically reduced the bacterial population. Of the initial bacterial viable count of 47.2 x 102 that survived the 56 days degradation exercise, only 1.8x101 (0.38%) grew on 7 mM concentration of DPTCl, and none on 10 mM DPTCl. The impact of DPTCl on the viable count of bacteria was statistically significant. Stenotrophomonas spp (29.6%) was the dominant bacterium in DPT degradation, others include; Comamonas spp (9.31%), Microbacterium spp (8.41%) Pseudomonas viridiflava (4.18%), and Stenotrophomonas geniculata (3.46%). Organotins. Diphenyltin though a di-alkyl organotin, is equally a toxic and persistent pollutant that cannot be easily degraded without the use of nutrient amendment. The toxic effect of DPT as demonstrated in this study shows that TPT and other tri-alkyl organotin should not be considered detoxified especially against microorganisms simply because they have been de-alkylated.Sites contaminated by organotins should not be considered remediated until all di and mono alkyl derivatives are completely degraded. Since our natural environments usually have no sufficient nutrient amendments for elimination of pollutants, there is need to engage abiotic processes that can assist the activities of microorganisms in order to speed up remediation process.

Acute Toxicity of Organotin on Fresh Water Shrimps and its Resistance by Marine Bacteria

Abstract: This present study was aimed at investigating the acute toxicity of organotin on fresh water shrimps and its resistance to marine bacteria. 200 water shrimps were exposed to varying concentrations of Tributyltin Chloride (TBTCL) and Diphenyltin Chloride (DPTCL) for 96 hours and a probit was used to determine the lethal dose (LD50). 200g of sediment from Onne sea port Rivers State was manually polluted by TBTCL and DPTCL for 56 days. Organotin resistant bacteria were screened on mineral salt medium at different concentration of the organotin using the spread plate technique. Results from this study showed a lethal doze (LD50) of 4.24mg/l after 24 hours and 1.97mg/l after 48 hours for TBTCl on fresh water shrimps and a lethal doze of 21.05mg/l after 24 hours, 0.83mg/l after 48 hours and 0.006mg/l after 72 hours for DPTCl. The total viable count of bacteria obtained from varying concentrations of TBTCl indicates that approximately 65% of bacterial populations were resistant to 3.0mM of TBTCl and DPTCI since these isolates could grow on MSA supplemented with TBTCI and DPTCI. Statistically, there was no significant difference between the bacterial loads between the different concentrations of TBTCL. Acute toxicity effect of TBTCl and DPTCl on fresh water shrimps reveals TBTCl and DPTCl as one of the toxic substances in the marine ecosystem however; marine bacteria can be harnessed for their resistant abilities.

Aerobic Degradation of Tributyltin Chloride and Dip-Henyltin Chloride by Marine Bacteria from Onne Port Nigeria

Aerobic Degradation of Tributyltin Chloride and Dip-Henyltin Chloride by Marine Bacteria from Onne Port Nigeria

Synthesis and some spectral properties of diphenylsilicon salicylate and a comparision of the antifungal efficacy of diphenylsilicon chloride, acetate and salicylate and diphenyltin chloride, acetate and salicylate on Candida albicans

Synthesis and some spectral properties of diphenylsilicon salicylate and a comparision of the antifungal efficacy of diphenylsilicon chloride, acetate and salicylate and diphenyltin chloride, acetate and salicylate on <i>Candida albicans</i>

Synthesis and characterization of a linked, π-π stacked organotin compound of 2-mercapto-6-nitrobenzothiazolyl diphenyltin chloride with 2-ethoxyl-6-nitrobenzothiazole

The new organotin compound, Ph2Sn(Cl)[S(C7H3N2O2S)]·[(C7H3N2O2S)OEt], assembled by an intermolecular aromatic benzothiazole–benzothiazole π-π stacking interaction, has been synthesized by the reaction of diphenyltin dichloride with 2-mercapto-6-nitrobenzothiazole. The title compound was characterized by elemental, IR, 1H NMR, and X-ray crystallography analyses. Single-crystal X-ray diffraction data reveals that the title compound has two different molecular components. The component Ph2Sn(Cl)[S(C7H3N2O2S)] has a pentacoordinate tin, which further forms an infinite one-dimensional chain by intermolecular non-bonded Cl···S interactions, resulting in an intercalation lattice that holds (C7H3N2O2S)OEt molecules. The formation of the molecule (C7H3N2O2S)OEt as well as its intercalated mechanism has also been discussed.Key words: organotin, assemble, π-π stacking interaction, 2-mercapto-6-nitrobenzothiazole, non-bonded interaction, crystal structure.

Effect of phenyltin compounds on lipid bilayer organization

Phenyltin compounds are known to be biologically active. Their chemical structure suggests that they are likely to interact with the lipid fraction of cell membranes. Using fluorescence and NMR techniques, the effect of phenyltin compounds on selected regions of model lipid bilayers formed from phosphatidylcholine was studied. The polarization of N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl) dipalmitoyl-L-phosphatidylethanolamine and desorption of praseodymium ions was used to probe the polar region, whereas the polarization of 1 - (4 - trimethylammoniumphenyl) - 6 - phenyl -1,3,5-hexatriene p-toluenesulfonate measured the hydrophobic core of the membrane. In addition, changes in the N-(5-fluoresceinthiocarbanoly)dipalmitoyl - L - α - phosphatidyl -ethanolamine fluorescence intensity indicated the amount of charge introduced by organotin compounds to the membrane surface. There were no relevant changes of measured parameters when tetraphenyltin was introduced to the vesicle suspension. Diphenyltin chloride causes changes of the hydrophobic region, whereas the triphenyltin chloride seems to adsorb in the headgroup region of the lipid bilayer. When the hemolytic activity of phenyltin compounds was measured, triphenyltin chloride was the most effective whereas diphenyltin chloride was much less effective. Tetraphenyltin causes little damage. Based on the presented data, a correlation between activity of those compounds to hemolysis (and toxicity) and the location of the compound within the lipid bilayer could be proposed. In order to inflict damage on the plasma membrane, the compound has to penetrate the lipid bilayer. Tetraphenyltin does not partition into the lipid fraction; therefore its destructive effect is negligible. The partition of the compound into the lipid phase is not sufficient enough, by itself, to change the structure of the lipid bilayer to a biologically relevant degree. The hemolytic potency seems to be dependent on the location of the compound within the lipid bilayer. Triphenyltin chloride which adsorbs on the surface of the membrane, causes a high level of hemolysis, whereas diphenyltin chloride, which penetrates much deeper, seems to have only limited potency.

Determination of the Standard Potentials and Equilibrium Constants for Eleven Organotin Compounds

Eleven organotin compounds (OTC) were potentiometrically titrated in methanol to determine their standard potentials,E0, and ionization constants,Keq. The classical method for potentiometry yielded nonreproducible results; therefore an alternate titration method was developed using the OTC as the titrant. The standard potentials,E0, and ionization constants,Keq, were determined by extrapolating the potentiometric titration data to 1.0Mconcentration. The extrapolation yielded twoE0values for the two different species in the solution. The titrations yielded a different end point potentials for anion ligands attached to the same OTC moiety, yet all the equilibrium ionization constants for a given organotin moiety, e.g., Bu3Sn or Bu2Sn, were approximately the same (approximately TBT = 10−3and DBT = 10−4). This suggests a difference in the energy level of the cation species for the accepting of an electron but a dissociation constant which is independent of anion moiety. The twoE0potentials for each of the OTC in methanol are as follows: tri-n-butyltin fluoride, 0.02 and 0.07; tri-n-butyltin chloride, 0.13 and 0.17; tri-n-butyltin bromide, 0.17 and 0.23; tri-n-butyltin iodide, 0.21 and 0.22; tri-n-butyltin laurate, +0.01 and 0.03; tri-n-butyltin naphthalate, −0.01 and 0.00; tri-n-butyltin benzoate, 0.08 and 0.10; di-n-butyltin fluoride, 0.07 and 0.10; di-n-butyltin chloride, 0.22 and 0.49; di-n-butyltin bromide, 0.24, and 0.29; and diphenyltin chloride, 0.21 and 0.33.

Sampling method of organotin compounds in air using a quartz-fibre filter and an activated carbon-fibre filter for gas chromatographic determination

A sampling method using quartz-fibre filters and an activated carbon-fibre filter was developed for gas chromatographic determination of organotin compounds in air. The organotin compounds investigated were dibutyltin chloride (DBTC), tributyltin chloride (TBTC), diphenyltin chloride (DPTC) and triphenyltin chloride (TPTC). The chlorides collected on filters were extracted ultrasonically with benzene and converted into propyl derivatives using propylmagnesium bromide. The derivatives were analysed by capillary gas chromatography (GC) equipped with a flame photometric detector adjusted for tin detection. The collection efficiencies and recoveries of the organotin compounds were quantitative. The minimum detectable concentrations were 0.2 ng/m 3 for DBTC and TBTC, 0.3 ng/m 3 for DPTC and 0.4 ng/m 3 for TPTC. This method was successfully applied to the determination of organotin compounds in indoor air.

Synthesis and spectroscopic studies of thienyl triorganotin(IV) compounds. Crystal structures of [2-(4,4-dimethyl-2-oxazolinyl)-3-thienyl]dimethyltin N, N-dimethyldithiocarbamate and [2-(4,4-dimethyl-2-oxazolinyl)-3-thienyl]diphenyltin chloride

Two series of stannylated thiophenes of formula ( Z-C 4H 2SnR 2X ( Z = 3-(2-pyridyl) and 2-(4,4-dimethyl-2-oxazolinyl); R = Me, nBu, Ph, p-tolyl and cHex; X = Cl, Br, I, OH, SC(S)NMe 2, and 8-quinolinolyl) have been prepared and their structures established by 119 m Sn Mössbauer and NMR ( 13C and 119Sn) spectral analyses. A pronounced C, N-chelate bonding mode is inferred for the 3-(2-pyridyl)-2-thienyl ligand in the first series, the tin atoms thus being essentially five-coordinate with trans-C 3SnNX trigonal bipyramidal geometries. Crystal structure determinations on two products in the second series, namely [2-(4,4-dimethyl-2-oxazolinyl)-3-thienyl]dimethyltin N, N-dimethyldithiocarbamate ( 1) and [2-(4, 4-dimethyl-2-oxazolinyl)-3-thienyl]diphenyltin chloride ( 2), confirmed the spectroscopic indications of pentacoordinate trigonal bipyramidal tin environments and revealed that the oxazolinyl nitrogen is the intramolecularly coordinated donor atom in each case and is located in an apical position with respect to the C 3Sn trigonal girdle; the Sn-N bond length in 2 (2.580(8); 2.525(7) Å) is relatively shorter than in 1 (2.720(3) Å). The apical angle for 1 (162.12(7)°) shows the molecule to be more distorted than 2 (168.4(2) and 169.9(2)°).

Determination of mono‐, di‐ and tri‐substituted butyltin, phenyltin and methyltin compounds as free halides using gas chromatography with flame photometric detection

AbstractA simple chromatographic procedure has been developed for the sensitive determination of mono‐, di‐ and tri‐substituted butyltin, phenyltin, and methyltin compounds as halides. The organotin compounds were separated on a DB‐1 capillary column and detected by flame photometric detection (FPD) equipped with a 611.5 nm filter.Pretreatment of the capillary column with an ethyl acetate solution of hydrobromic acid, or doping of standard solutions with hydrobromic acid, was found to be necessary if reproducibly sharp peaks of organotin halides were to be obtained. Column treatment and acid doping did not cause any background problems or undesirable degradation of the organotin compounds.Three different standard solutions in ethyl acetate had to be Jrepared, because undesirable degradation of the organotin halides was observed when all the compounds were dissolved in the same solution. The first, standard solution I, contained tri‐n‐butyltin chloride (TBTCI) and trimethyltin chloride (TMTCI), the second, standard solution II, contained triphenyltin chloride (TPTCI), and the third, standard solution III, contained hydrogen bromide and the other organotin compounds: di‐n‐butyltin chloride (DBTCI), mono‐n‐butyltin chloride (MBTCI), dimethyltin chloride (DMTCI), monomethyltin chloride (MMTCI), diphenyltin chloride (DPTCI), and monophenyltin chloride (MPTCI). An ethyl acetate solution containing hydrobromic acid (20 × 10−3 mol/I) was used for column treatment.

Comparative toxicity of organotin compounds to rainbow trout ( Oncorhynchus mykiss) yolk sac fry

The comparative toxicity of various organotin compounds was investigated in early life stages of the rainbow trout. Beginning with yolk sac fry, trout were continuously exposed for 110 days to tributyl- (TBTC), triphenyl- (TPhTC) or tricyclohexyltin chloride (TCHTC) at concentrations of 0.12−15 n M, to trimethyltin chloride (TMTC) at concentrations of 3.−75 n M or to dibutyl- (DBTC) or diphenyltin chloride (DPhTC) at 160−4000 n M. The diorganotin compounds DBTC and DPhTC were about three orders of magnitude less toxic than the triorganotin homologs TBTC and TPhTC. Both for DBTC and DPhTC, a no-observable-effect concentration (NOEC) of 160 n M was established, corresponding to 40 and 60 ppb, respectively. Of the triorganotin compounds, TCHTC appeared to be the most toxic, inducing 100% mortality within 1 week at a concentration of 3 n M. Only a few trout survived exposure to 0.6 n M TCHTC for 110 days. TBTC and TPhTC caused acute mortality at a concentration of 15 n M. For both TBTC and TPhTC a NOEC of 0.12 n M was established, corresponding to water concentrations of 40 and 50 ppt, respectively. Histopathological examination revealed depletion of glycogen in liver cells of both di- and triorganotin exposed fish, except in the case of TMTC. No signs of toxicity were observed in fish exposed to up to 75 n M TMTC, the highest concentration tested. Atrophy of the thymus, the most prominent sign of toxicity of di- and tributyltin compounds in mammalian species, was not observed in early life stages of rainbow trout. Tail melanization was observed in the groups exposed to 3 n M TPhTC, 3 n M TBTC, 800 n M DBTC and 800 n M DPhTC. At the end of the exposure period, resistance to infection was examined by an intraperitoneal challenge with Aeromonas hydrophila, a secondary pathogenic bacterium to fish. Resistance of bacterial challenge was found to be decreased even at the lowest-effect concentration of both di- and triorganotin compounds.

Direct and Indirect Assessment of the Aneuploidy-inducing Potency of Organotin Compounds

The spindle-inhibiting and aneuploidy-inducing potency of in vitro exposure of PHA-stimulated human lymphocytes to organotin compounds has been studied indirectly by quantitation of chromosomal contraction and directly by determination of the frequency of aneuploidy by chromosome counting. The effects of trimethyltin chloride (TMT), dimethyltin chloride (DMT), tributyltin chloride (TBT), dibutyltin chloride (DBT), triphenyltin chloride (TPhT), and diphenyltin chloride (DPhT) on chromosal contraction were studied at concentrations of 10-3-10 9M, by measurement of the average length of chromosome 1 from asynchronous cultures of human peripheral lymphocytes. TMT, TBT, TPhT and DPhT appear to be very strong inducers of chromosomal supercontraction, indicating that these compounds are possible spindle inhibitors, while DMT and DBT seem to be ineffective. TMT, TBT, TPhT and DPhT gave rise to a little more than 100% increase in the number of hyperdiploid cells, all the increases being statistically significant except for that induced by TBT, indicating that organotin compounds are capable of inducing aneuploidy, probably by affecting spindle function.

Determination of butyltin and phenyltin compounds in biological and sediment samples by electron-capture gas chromatography

A method is described for the gas chromatographic determination of nanogram amounts of mono-, di- and tributyltin compounds and mono-, di- and triphenyltin compounds in biological and sediment samples. These compounds are converted into the corresponding chlorides with hydrochloric acid, extracted with ethyl acetate and hydrogenated with sodium tetrahydroborate. The corresponding hydrides, mono- n-butyltin hydride, di- n-butyltin hydride, tri- n-butyltin hydride, monophenyltin hydride, diphenyltin hydride triphenyltin hydride, are detected by electron-capture gas chromatography after clean-up by silica gel column chromatography. The detection limits are 10–20 ng/g for mono- n-butyltin chloride, 0.5–1 ng/g for di- n-butyltin chloride, 1–2 ng/g for tri- n-butyltin chloride and diphenyltin chloride and 2.5–5 ng/g for monophenyltin chloride and triphenyltin chloride, in biological and sediment samples.

Some exchange reactions involving phenyltin hydrides and organotin halides

Reaction of diphenyltin dihydride with diphenyltin dichloride or diphenyltin dibromide in a 1 : 1 mole ratio gives good conversion to diphenyltin chloride hydride and diphenyltin bromide hydride, respectively. Triphenyltin hydride with diphenyltin dichloride or diphenyltin dibromide in a 1 : 1 mole ratio gives fair conversion to the corresponding halide hydrides but less than in the case of diphenyltin dihydride. Diphenyltin dihydride reacts with dialkyltin dichloride in a 1 : 1 mole ratio to give a preponderance of organotin chloride hydride along with diphenyltin dihydride but no dialkyltin dihydride. However, triphenyltin hydride did not appear to react with dialkyltin dihidides in a 1 : 1 mole ratio to yield either the dialkyltin halide hydride or the dialkyltin dihydride. Reactions attempted between triphenyltin hydride and several trialkyltin chlorides confirm the tendency of the hydride hydrogen to become attached to the triphenyltin moiety rather than the trialkyltin or the dialkylchlorotin moieties.

Functionally substituted organotin compounds : V. Beckmann rearrangement of oximes containing organotin substituents

The structures of the oximes formed from (4-oxopentyl)triphenyltin and (4-oxopentyl)diphenyltin chloride have been determined using IR, PMR and Mössbauer spectroscopy. Beckmann rearrangement of (4-oximinopentyl)diphenyltin chloride with phosphorus pentachloride gave the amide resulting from exchange of syn groups. Treatment of the second oxime with phosphorus pentachloride caused other reactions but the O-tosyl derivative was rearranged under mild conditions to give a mixture of amides.

Functionally substituted organotin compounds. Part IV. The use of protecting groups in the formation of 4-oxopentyltin compounds

Protection of the carbonyl group in 1-chloropentan-4-one by dioxolan formation has enabled preparation of a series of 4-oxopentyltin compounds via the Grignard reagent. I.r., n.m.r., and Mögssbauer spectroscopy have been used to aid structure assignments: in many of the-compounds the carbonyl group is intramolecularly co-ordinated to tin. Stereochemical assignments have been made for (4-oxopentyl)diphenyltin chloride and di(4-oxopentyl)tin dibromide.