Tributyltin

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The structure of tributyltin oxide: the most common TBT compound used in marine paint Tributyltin oxide structure.svg
The structure of tributyltin oxide: the most common TBT compound used in marine paint
Biofouling on the hull of a boat Boat fouling organisms (4875278100).jpg
Biofouling on the hull of a boat

Tributyltin (TBT) is an umbrella term for a class of organotin compounds which contain the (C4H9) 3 Sn group, with a prominent example being tributyltin oxide. [1] For 40 years TBT was used as a biocide in anti-fouling paint, commonly known as bottom paint, applied to the hulls of oceangoing vessels. [2] Bottom paint improves ship performance and durability as it reduces the rate of biofouling, the growth of organisms on the ship's hull. The TBT slowly leaches out into the marine environment where it is highly toxic toward nontarget organisms. TBT toxicity can lead to biomagnification or bioaccumulation within such nontarget organisms like invertebrates, vertebrates, and a variety of mammals. TBT is also an obesogen. [3] After it led to collapse of local populations of organisms, TBT was banned. [4]

Contents

Chemical properties

TBT, or tributyltin, tributylstannyl or tributyl stannic hydride compounds are organotin compounds. They have three butyl groups covalently bonded to a tin(IV) atom. [5] A general formula for these compounds is (CH3CH2CH2CH2)3Sn−X. The −X is typically a chloride −Cl, hydroxide −OH, or a carboxylate RCO2−, where R is an organyl group. [6] TBT is also known to be an endocrine disrupting compound, which influences biological activities such as growth, reproduction and other physiological processes. [7]

TBT compounds have a low water solubility, a property that is ideal for antifouling agents. The toxicity of TBT prevents the growth of algae, barnacles, molluscs and other organisms on ships hulls. [8] When introduced into a marine or aquatic environment, TBT adheres to bed sediments. TBT has a low Log Kow of 3.19 – 3.84 in distilled water and 3.54 for sea water, this makes TBT moderately hydrophobic. TBT compounds have a high fat solubility and tend to absorb more readily to organic matter in soils or sediment. The bioaccumulation of TBT in organisms such as molluscs, oysters and dolphins, have extreme effects on their reproductive systems, central nervous systems and endocrine systems. [9] However, the adsorption of TBT to sediments is reversible and depends on pH level in the body of water.

TBT has a half-life of one or two weeks in marine water. [5] When it accumulates in sediments its half life is about 2 years. TBT often bonds to suspended material and sediments, where it can remain and be released for up to 30 years. [10] Studies have shown that 95% of TBT can be released from the sediments back into the aquatic environment. This absorption process can complicate quantification of TBT in an environment, since its concentration in the water is not representative of its availability. [1]

Uses

Tributyltin (TBT) compounds are biocides. TBT's antifouling properties were discovered in the 1950s in the Netherlands by van der Kerk and coworkers. It prevents microorganisms from settling on the hull of a ship and poisons the organisms that end up settling. By the mid-1960s, it had become the most popular anti-fouling paint around the globe. [4] TBT was mixed into paints to extend the life of antifouling coatings and ships were able to continue operations for a longer time frame. The paints ensured fuel efficiency and delayed costly ship repairs. It is also relatively inexpensive.

TBT is also an ingredient in some disinfectants, for example in combination with quaternary ammonium compounds. Additionally, TBT has been used in the fertilizer, textile, and wood industries. It has antifungal properties that make it useful for both the production of textiles and wood preservation, and in the creation of biocides for paired use with fertilizers. [11] Another use of TBT is that they were used as stabilizers in compounds like polyvinyl chlorides. [12] Due to this usage of TBT, there are a variety of consumer products where traces of TBT can be found, like in textile fabrics, plastic polymers, silicon, and many more.

Toxicity

The effects of antifouling paint go beyond the organisms that it is intended to kill. By poisoning barnacles, algae, and other organisms at the bottom of the food chain, the bioaccumulation of TBT increases over time affecting more and more of the bottom feeders of the aquatic food web environment, which are mainly invertebrates and are affected by TBT. There is a slight biomagnification of TBT that has been demonstrated in the lower part of the marine food chain (i.e., planktonic organisms, invertebrates, and fishes). However, the biomagnification of TBT into larger marine animals such as marine mammals is debatable. [13] Toxic effects in some species occur at 1 nanogram per liter of water. Air pollution from TBT has not been noticed or considered significant enough to effect the environment. In the water, photodegradation and microorganisms can break down TBT and leach into the soil sediments. [12]

Bioaccumulation and biomagnification

As TBT is most often used as a biofouling agent, it bioaccumulates in marine wildlife such as molluscs, with levels being higher in organisms and sediments in and around areas of high maritime activity, such as ports and harbours. [12] The bioaccumulation increases over time, leading to a biomagnification in organisms higher up the food chain, although the biomagnification is not that considerable in size. [14] As TBT can remain in the environment for up to 30 years due to often bonding to suspended material and sediments, it can remain in an ecosystem for a very long time. This means that bioaccumulation readily occurs in marine environments, which can lead to very high amounts of TBT being accumulated, especially in smaller organisms at the bottom of the food chain, which in turn has various health effects.

Invertebrates

Exposure to organotin compounds causes the development of male accessory sex organs in female prosobranch gastropods. This phenomenon has been termed imposex. TBT has been shown to affect invertebrate development. Marine snails, such as the dog whelk (Nucella lapillus), has often been used as an indicator species. [15] In gastropods, the normal process of accessory sex organ development is retinoid dependent, as has been proven by the effect 9cisRA has on male penises. TBTs mimic the endogenous ligand of Retinoid X Receptor (9cisRA), and thus activates the signalling cascades that are retinoid acid dependent, promoting female penis growth. [16] [17] [18] [19]

There have been many theories as to why molluscs are affected by TBT. For example, previous literature has stated that TBT would cause the inhibition of aromatase which would lead to an increase in testosterone and therefore, causing imposex. [20] It was theorized that TBT disrupts endocrine system by inhibiting cytochrome P450 molecule. Among its myriad functions, P450 converts androgen, which has male-hormone properties, into oestrogen, which has female hormone properties. It was theorized that the high concentration of androgen lead to the masculinization of females. [21] Another indicator species is Chironomus riparius , a species of non-biting midge, which has been used to test the effects of TBT on development and reproduction at sublethal concentrations found in marine environments. Higher concentrations of TBT were found to increase the female population and the results are interesting because unlike the masculinization of the stengoglassan gastropods, feminization was present. [6]

Vertebrates

Vertebrates become affected by the waters contaminated with TBT, as well as by consuming organisms that have already been poisoned. Oryzias latipes, commonly called Japanese rice fish, has been used as a model vertebrate organism to test for effects of TBT at developmental stages of the embryo. It was observed that developmental rate was slowed by TBT in a concentration-related manner and that tail abnormalities occurred. Illustrating the infiltration of TBT in the food chain, one study showed that most samples of skipjack tuna tested positive for presence of TBT. Tuna from waters around developing Asian nations had particularly high levels of TBT. Regulation of TBT is not enforced in Asia as rigorously as in Europe or US. [22] Studies have shown that TBT is detrimental to the immune system. Research shows that TBT reduces resistance to infection in fish which live on the seabed and are exposed to high levels of TBT. These areas tend to have silty sediment like harbours and estuaries. [8] TBT compounds have been described to interfere with glucocorticoid metabolism in the liver by inhibiting the activity of the enzyme 11beta-hydroxysteroiddehydrogenase type 2, which converts cortisol to cortisone. [6]

Mammals

TBT can enter the diet of humans and other mammals such as whales, dolphins, dugongs, and sea otters. As of 2008 high levels of tributyltin have been detected in the livers of sea otters (Enhydra lutris) and stranded bottlenose dolphins. [23] [24] Otters dying of infectious causes tended to have higher levels of tissue butyltins than those dying of trauma or other causes. It was also reported by scientists that sea otters typically stay near boats and closed off marinas, which may have led to these organisms experiencing higher levels of butyltins. [25] TBT has been shown to lead to immunosuppression in sea-otters and dolphins. TBT has also been linked to hearing loss in mammalian top predators such as toothed whales. [26] In rats, the hypothalamus-pituitary-adrenal (HPA) axis can be affected by TBT. In the pituitary and adrenal glands, there have been findings of morphophysiological changes within rats affected by TBT. [27] TBT can also affect humans as well. Humans can be exposed to these compounds and potentially experience headaches, fatigue, respiratory issues, and more. Long-term exposure can also lead to damage of some internal organs such as the kidneys and liver. [28]

Regulation

Bans on TBT on boats less than 25 metres long first started in the 1980s. In 1990, the Marine Environment Protection Committee adopted Resolution MEPC 46(30), which recommended that the Government eliminate the use of TBT-containing antifouling paints on smaller vessels. This resolution was intended to be a temporary restriction until the International Maritime Organization could implement a ban of TBT anti-fouling agents for ships. Several countries followed and in 1997, Japan banned the production of TBT-based anti-fouling paints. The IMO began to use an Assembly resolution in 1999 that essentially wanted the MPEC to fix the severe environmental effects of the anti-fouling systems. This led to a worldwide ban on organotin compound applications on ships starting in 2003. [8] In 2008, organotin compounds acting as biocide like TBT compounds were banned entirely in anti-fouling paint and included in the Rotterdam Convention and have been banned by the International Convention on the Control of Harmful Anti-fouling Systems on Ships of the International Maritime Organization. [8] [29] It states that ships cannot bear organotin compounds on their hulls or external parts or surfaces, unless there is a coating that forms a barrier so that organotin compounds cannot leach out to reduce exposure by allowing recovery to occur. [1]

Violations of the ban on TBT

Although the ban on TBT use was proved to be effective on reducing the negative effects on the environment, some people that supplied them were still producing and selling them to other countries for a profit. Even though banned by some international agencies like the International Maritime Organization, TBT anti-fouling paints are still used in countries with poor regulation enforcement to this day, with the Caribbean being a prime example. [7]

U.S. Violations

In November 2018, the US Department of Justice announced that three people they had charged and arrested in New Jersey for manufacturing and selling tributyltin based marine paint had pleaded guilty. The sentencing of these people was scheduled for February 2019. [30]

See also

Related Research Articles

<span class="mw-page-title-main">Tin</span> Chemical element, symbol Sn and atomic number 50

Tin is a chemical element; it has symbol Sn and atomic number 50. A silvery-colored metal, tin is soft enough to be cut with little force, and a bar of tin can be bent by hand with little effort. When bent, the so-called "tin cry" can be heard as a result of twinning in tin crystals.

Bioaccumulation is the gradual accumulation of substances, such as pesticides or other chemicals, in an organism. Bioaccumulation occurs when an organism absorbs a substance faster than it can be lost or eliminated by catabolism and excretion. Thus, the longer the biological half-life of a toxic substance, the greater the risk of chronic poisoning, even if environmental levels of the toxin are not very high. Bioaccumulation, for example in fish, can be predicted by models. Hypothesis for molecular size cutoff criteria for use as bioaccumulation potential indicators are not supported by data. Biotransformation can strongly modify bioaccumulation of chemicals in an organism.

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

<span class="mw-page-title-main">Biogenic substance</span> Product made by or of life forms

A biogenic substance is a product made by or of life forms. While the term originally was specific to metabolite compounds that had toxic effects on other organisms, it has developed to encompass any constituents, secretions, and metabolites of plants or animals. In context of molecular biology, biogenic substances are referred to as biomolecules. They are generally isolated and measured through the use of chromatography and mass spectrometry techniques. Additionally, the transformation and exchange of biogenic substances can by modelled in the environment, particularly their transport in waterways.

<span class="mw-page-title-main">Anti-fouling paint</span> Specialized paint for ship hulls

Anti-fouling paint is a specialized category of coatings applied as the outer (outboard) layer to the hull of a ship or boat, to slow the growth of and facilitate detachment of subaquatic organisms that attach to the hull and can affect a vessel's performance and durability. It falls into a category of commercially available underwater hull paints, also known as bottom paints.

<span class="mw-page-title-main">Persistent organic pollutant</span> Organic compounds that are resistant to environmental degradation

Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic chemicals that adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released.

<span class="mw-page-title-main">Biofouling</span> Growth of marine organisms on surfaces

Biofouling or biological fouling is the accumulation of microorganisms, plants, algae, or small animals where it is not wanted on surfaces such as ship and submarine hulls, devices such as water inlets, pipework, grates, ponds, and rivers that cause degradation to the primary purpose of that item. Such accumulation is referred to as epibiosis when the host surface is another organism and the relationship is not parasitic. Since biofouling can occur almost anywhere water is present, biofouling poses risks to a wide variety of objects such as boat hulls and equipment, medical devices and membranes, as well as to entire industries, such as paper manufacturing, food processing, underwater construction, and desalination plants.

<span class="mw-page-title-main">Biomagnification</span> Process of progressive accumulation in food chain

Biomagnification, also known as bioamplification or biological magnification, is the increase in concentration of a substance, e.g a pesticide, in the tissues of organisms at successively higher levels in a food chain. This increase can occur as a result of:

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

<span class="mw-page-title-main">Tributyltin oxide</span> Chemical compound

Tributyltin oxide (TBTO) is an organotin compound chiefly used as a biocide (fungicide and molluscicide), especially a wood preservative. Its chemical formula is [(C4H9)3Sn]2O. It is a colorless viscous liquid. It is poorly soluble in water (20 ppm) but highly soluble in organic solvents. It is a potent skin irritant.

<span class="mw-page-title-main">Tetrabutyltin</span> Chemical compound

Tetrabutyltin is the organotin compound with the molecular formula Sn(CH2CH2CH2CH3)4 or SnBu4, where Bu is butyl −CH2CH2CH2CH3. Sometimes abbreviated TTBT, it is a colorless, lipophilic oil.

Imposex is a disorder in sea snails caused by the toxic effects of certain marine pollutants. These pollutants cause female sea snails to develop male sex organs such as a penis and a vas deferens.

<span class="mw-page-title-main">Obesogen</span> Foreign chemical compound that disrupts lipid balance causing obseity

Obesogens are certain chemical compounds that are hypothesised to disrupt normal development and balance of lipid metabolism, which in some cases, can lead to obesity. Obesogens may be functionally defined as chemicals that inappropriately alter lipid homeostasis and fat storage, change metabolic setpoints, disrupt energy balance or modify the regulation of appetite and satiety to promote fat accumulation and obesity.

<span class="mw-page-title-main">Environmental effects of paint</span>

The environmental effects of paint can vary depending on the type of paint used and mitigation measures. Traditional painting materials and processes can have harmful effects on the environment, including those from the use of lead and other additives. Measures can be taken to reduce its environmental effects, including accurately estimating paint quantities so waste is minimized, and use of environmentally preferred paints, coating, painting accessories, and techniques.

Tin poisoning refers to the toxic effects of tin and its compounds. Cases of poisoning from tin metal, its oxides, and its salts are "almost unknown"; on the other hand, certain organotin compounds are almost as toxic as cyanide.

A biomimetic antifouling coating is a treatment that prevents the accumulation of marine organisms on a surface. Typical antifouling coatings are not biomimetic but are based on synthetic chemical compounds that can have deleterious effects on the environment. Prime examples are tributyltin compounds, which are components in paints to prevent biofouling of ship hulls. Although highly effective at combatting the accumulation of barnacles and other problematic organisms, organotin-containing paints are damaging to many organisms and have been shown to interrupt marine food chains.

Persistent, bioaccumulative and toxic substances (PBTs) are a class of compounds that have high resistance to degradation from abiotic and biotic factors, high mobility in the environment and high toxicity. Because of these factors PBTs have been observed to have a high order of bioaccumulation and biomagnification, very long retention times in various media, and widespread distribution across the globe. Most PBTs in the environment are either created through industry or are unintentional byproducts.

Tissue residue is the concentration of a chemical or compound in an organism's tissue or in a portion of an organism's tissue. Tissue residue is used in aquatic toxicology to help determine the fate of chemicals in aquatic systems, bioaccumulation of a substance, or bioavailability of a substance, account for multiple routes of exposure, and address an organism's exposure to chemical mixtures. A tissue residue approach to toxicity testing is considered a more direct and less variable measure of chemical exposure and is less dependent on external environmental factors than measuring the concentration of a chemical in the exposure media.

Ultra-low fouling is a rating of a surface's ability to shed potential contamination. Surfaces are prone to contamination, which is a phenomenon known as fouling. Unwanted adsorbates caused by fouling change the properties of a surface, which is often counter-productive to the function of that surface. Consequently, a necessity for anti-fouling surfaces has arisen in many fields: blocked pipes inhibit factory productivity, biofouling increases fuel consumption on ships, medical devices must be kept sanitary, etc. Although chemical fouling inhibitors, metallic coatings, and cleaning processes can be used to reduce fouling, non-toxic surfaces with anti-fouling properties are ideal for fouling prevention. To be considered effective, an ultra-low fouling surface must be able to repel and withstand the accumulation of detrimental aggregates down to less than 5 ng/cm2. A recent surge of research has been conducted to create these surfaces in order to benefit the biological, nautical, mechanical, and medical fields.

<span class="mw-page-title-main">Dichlorooctylisothiazolinone</span> Chemical compound

Dichlorooctylisothiazolinone, DCOIT or DCOI, is the organic compound with the formula SC(Cl)=C(Cl)C(O)NC7H15. It is a white solid that melts near room temperature. It is an isothiazolinone, a class of heterocyclic compounds used as biocides. DCOIT has attracted attention as an antifouling compound. It is a replacement for organotin compounds that have been largely banned for causing environmental damage. DCOIT however is itself controversial.

References

  1. 1 2 3 Antizar-Ladislao, Blanca (Feb 2008). "Environmental levels, toxicity and human exposure to tributyltin (TBT)-contaminated marine environment. A review". Environment International. 34 (2): 292–308. doi:10.1016/j.envint.2007.09.005. PMID   17959247. Archived from the original on 2019-12-23. Retrieved 2019-12-14.
  2. ↑ Ofoegbu, Pearl U.; Simão, Fátima C. P.; Cruz, Andreia; Mendo, Sónia; Soares, Amadeu M. V. M.; Pestana, João L. T. (2016-04-01). "Toxicity of tributyltin (TBT) to the freshwater planarian Schmidtea mediterranea". Chemosphere. 148: 61–67. Bibcode:2016Chmsp.148...61O. doi:10.1016/j.chemosphere.2015.12.131. ISSN   0045-6535. PMID   26802264.
  3. ↑ Pereira-Fernandes, Anna; Vanparys, Caroline; Hectors, Tine L.M.; Vergauwen, Lucia; Knapen, Dries; Jorens, Philippe G.; Blust, Ronny (2013). "Unraveling the mode of action of an obesogen: Mechanistic analysis of the model obesogen tributyltin in the 3T3-L1 cell line". Molecular and Cellular Endocrinology. 370 (1–2): 52–64. doi:10.1016/j.mce.2013.02.011. PMID   23428407. S2CID   196815.
  4. 1 2 Konstantinou, Ioannis (Feb 22, 2006). Antifouling Paint Biocides . Springer. pp.  1.
  5. 1 2 Davies, Alwyn George. (2004) Organotin Chemistry, 2nd Edition Weinheim: Wiley-VCH. ISBN   978-3-527-31023-4
  6. 1 2 3 Mora, Stephen J. De, ed. (1996). Tributyltin : case study of an environmental contaminant (1. publ. ed.). Cambridge [u.a.]: Cambridge Univ. Press. ISBN   978-0521470469.
  7. 1 2 Beyer, Jonny; Song, You; Tollefsen, Knut Erik; Berge, John Arthur; Tveiten, Lise; Helland, Aud; Øxnevad, Sigurd; Schøyen, Merete (2022-07-01). "The ecotoxicology of marine tributyltin (TBT) hotspots: A review". Marine Environmental Research. 179: 105689. doi: 10.1016/j.marenvres.2022.105689 . hdl: 11250/3020219 . ISSN   0141-1136. PMID   35777303. S2CID   250001156.
  8. 1 2 3 4 "Anti-fouling Systems". www.imo.org. Archived from the original on 2017-06-11. Retrieved 2020-09-16.
  9. ↑ Evans, S.M (August 1999). "Tributyltin Pollution: the Catastrophe that Never Happened". Marine Pollution Bulletin. 38 (8): 629–636. doi:10.1016/S0025-326X(99)00040-5.
  10. ↑ Champ, Michael (Sep 30, 1996). Organotin: Environmental Fate and Effects. Springer. p. 469. ISBN   9780412582400.
  11. ↑ "Tributyltin - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2022-09-27.
  12. 1 2 3 Tributyltin compounds (TBT). Miljøstyrelsen. 2013. ISBN   978-87-93026-80-3. OCLC   1158613513.
  13. ↑ Sham, Ronia Chung-tin; Tao, Lily Shi Ru; Mak, Yanny King Yan; Yau, Jason Kin Chung; Wai, Tak Cheung; Ho, Kevin King Yan; Zhou, Guang-Jie; Li, Yongyu; Wang, Xinhong; Leung, Kenneth Mei Yee (April 2020). "Occurrence and trophic magnification profile of triphenyltin compounds in marine mammals and their corresponding food webs". Environment International. 137: 105567. doi: 10.1016/j.envint.2020.105567 . PMID   32087482.
  14. ↑ Takahashi, S.; Tanabe, S.; Takeuchi, I.; Miyazaki, N. (1999-07-01). "Distribution and Specific Bioaccumulation of Butyltin Compounds in a Marine Ecosystem". Archives of Environmental Contamination and Toxicology. 37 (1): 50–61. doi:10.1007/s002449900489. ISSN   0090-4341. PMID   10341042. S2CID   24705167.
  15. ↑ Gibbs, P. E.; Bryan, G. W.; Pascoe, P. L.; Burt, G. R. (11 May 2009). "The use of the dog-whelk, Nucella lapillus, as an indicator of tributyltin (TBT) contamination". Journal of the Marine Biological Association of the United Kingdom. 67 (3): 507. doi: 10.1017/S0025315400027260 . S2CID   85059840.
  16. ↑ Holdich, D.M.; Reynolds, J.D.; Souty-Grosset, C.; Sibley, P.J. (2009). "A review of the ever increasing threat to European crayfish from non-indigenous crayfish species". Knowledge and Management of Aquatic Ecosystems (394–395): 11. doi: 10.1051/kmae/2009025 . ISSN   1961-9502.
  17. ↑ Olden, Julian D.; McCarthy, Julia M.; Maxted, Jeffrey T.; Fetzer, William W.; Vander Zanden, M. Jake (December 2006). "The rapid spread of rusty crayfish (Orconectes rusticus) with observations on native crayfish declines in Wisconsin (U.S.A.) over the past 130 years". Biological Invasions. 8 (8): 1621–1628. doi:10.1007/s10530-005-7854-2. ISSN   1387-3547. S2CID   11304533.
  18. ↑ Edgerton, Brett F.; Henttonen, Paula; Jussila, Japo; Mannonen, Ari; Paasonen, Pietari; Taugbøl, Trond; Edsman, Lennart; Souty-Grosset, Catherine (December 2004). "Understanding the Causes of Disease in European Freshwater Crayfish: Disease in European Crayfish". Conservation Biology. 18 (6): 1466–1474. doi:10.1111/j.1523-1739.2004.00436.x. S2CID   84099445.
  19. ↑ Novotny, Ladislav; Sharaf, Leyla; Abdel-Hamid, Mohammed E.; Brtko, Julius (2018). "Stability studies of endocrine disrupting tributyltin and triphenyltin compounds in an artificial sea water model". General Physiology and Biophysics. 37 (1): 93–99. doi: 10.4149/gpb_2017051 . ISSN   1338-4325. PMID   29424354.
  20. ↑ Castro, L. Filipe C.; Lima, D.; Machado, A.; Melo, C.; Hiromori, Y.; Nishikawa, J.; Nakanishi, T.; Reis-Henriques, M.A.; Santos, M.M. (November 2007). "Imposex induction is mediated through the Retinoid X Receptor signalling pathway in the neogastropod Nucella lapillus". Aquatic Toxicology. 85 (1): 57–66. doi:10.1016/j.aquatox.2007.07.016. PMID   17875330.
  21. ↑ Bettin, C.; Oehlmann, J.; Stroben, E. (September 1996). "TBT-induced imposex in marine neogastropods is mediated by an increasing androgen level". Helgoländer Meeresuntersuchungen. 50 (3): 299–317. Bibcode:1996HM.....50..299B. doi: 10.1007/BF02367105 . ISSN   0174-3597.
  22. ↑ Down, Steve. "Tuna is attuned to tin". Ezine. Archived from the original on 2014-04-28. Retrieved 2014-04-28.
  23. ↑ Murata S, Takahashi S, Agusa T, Thomas NJ, Kannan K, Tanabe S (April 2008). "Contamination status and accumulation profiles of organotins in sea otters (Enhydra lutris) found dead along the coasts of California, Washington, Alaska (USA), and Kamchatka (Russia)". Marine Pollution Bulletin. 56 (4): 641–9. doi:10.1016/j.marpolbul.2008.01.019. PMID   18304586.
  24. ↑ Harino, Hiroya; Ohji, Madoka; Wattayakorn, Gullaya; Adulyanukosol, Karnjana; Arai, Takaomi; Miyazaki, Nobuyuki (2008-01-01). "Accumulation of Organotin Compounds in Tissues and Organs of Dolphins from the Coasts of Thailand". Archives of Environmental Contamination and Toxicology. 54 (1): 145–153. doi:10.1007/s00244-007-9005-5. ISSN   1432-0703. PMID   17687583. S2CID   5693655.
  25. ↑ Kannan; et al. (1998). "Butyltin residues in Southern sea otters (Enhydra lutris nereis) found dead along California coastal waters". Environ. Sci. Technol. 32 (9): 1169–1175. Bibcode:1998EnST...32.1169K. doi:10.1021/es970914u.
  26. ↑ Santos-Sacchi Joseph; Song Lei; Zheng Jiefu; Nuttall Alfred L (2006-04-12). "Control of Mammalian Cochlear Amplification by Chloride Anions". Journal of Neuroscience. 26 (15): 3992–3998. doi:10.1523/JNEUROSCI.4548-05.2006. PMC   6673883 . PMID   16611815.
  27. ↑ Merlo, Eduardo; Podratz, Priscila L.; Sena, Gabriela C.; de Araújo, Julia F. P.; Lima, Leandro C. F.; Alves, Izabela S. S.; Gama-de-Souza, Letícia N.; Pelição, Renan; Rodrigues, Lívia C. M. (2016). "The Environmental Pollutant Tributyltin Chloride Disrupts the Hypothalamic-Pituitary-Adrenal Axis at Different Levels in Female Rats". Endocrinology. 157 (8): 2978–2995. doi: 10.1210/en.2015-1896 . PMID   27267847.
  28. ↑ "High school student paper: The Effects of Tributyltin on the Marine Environment". seagrant.uaf.edu. Retrieved 2022-11-28.
  29. ↑ FAO., Secretariat of the Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals and Pesticides in International Trade. United Nations Environment Programme. (2015). Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals and Pesticides in International Trade : text and annexes. Rotterdam Convention Secretariat. OCLC   1248029257.
  30. ↑ "Three New Jersey Men Plead Guilty to the Illegal Production and Distribution Of Pesticides". www.justice.gov. 2018-11-14. Retrieved 2022-10-28.
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