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CAS Number: 76-87-9 
EC Number: 200-990-6
Chemical formula: C18H16OSn
Molar mass: 367.035 g·mol−1

Triphenyltin hydroxide is an organotin compound with formula Sn(C6H5)3OH. 
Triphenyltin hydroxide is used as a fungicide for potatoes, sugar beets, and pecans. 
Triphenyltin hydroxide was first registered for use as a pesticide in the United States in 1971.

Triphenyltin hydroxide (TPTH), also known as fentin hydroxide, is a non-systemic foliar fungicide used to control early and late blight on potatoes, leaf spot on sugar beets, and select fungal diseases on pecans. 
TPTH also exhibits anti-feeding properties for some surface-feeding insects (e.g., Colorado potato beetle). 

Triphenyltin hydroxide is a restricted use pesticide (RUP) and is only registered for use on these three crops. 
There are no residential, public health, or other non-food uses of TPTH. 
In 2017, over 200,000 pounds of this active ingredient were sold in Minnesota.

Triphenyltin hydroxide is an odorless white powder. 
Stable at room temperature. 
Melting point 121-123°C. 
Moderately soluble in most organic solvents. 
Insoluble in water. 
Non corrosive. 
Triphenyltin hydroxide is used as a fungicide.

Triphentin hydroxide is an organotin compound that is triphenylstannane in which the hydrogen attached to tin is replaced by a hydroxy group. 
A fungicide used to control a variety of infections including blight on potatoes, leaf spot on sugar beet and alternaria blight on carrots. 
Triphenyltin hydroxide has a role as an acaricide and an antifungal agrochemical. 
Triphenyltin hydroxide is an organotin compound and a member of hydroxides. 
Triphenyltin hydroxide derives from a triphenylstannane.

TPTH inhibits oxidative phosphorylation (respiration) and fungal growth. 
Triphenyltin hydroxide is a Fungicide Resistance Action Committee (FRAC) code 30 fungicide which inhibits adenosine triphosphate (ATP) synthase preventing the production of ATP by cell mitochondria.

Triphenyltin hydroxide is an organotin compound with formula Sn(C6H5)3OH. 
Triphenyltin hydroxide is used as a fungicide for potatoes, sugar beets, and pecans. 
Triphenyltin hydroxide was first registered for use as a pesticide in the United States in 1971.

TPTH has low solubility in water and binds strongly to soil. 
Therefore, Triphenyltin hydroxide is not expected to leach to groundwater; however, Triphenyltin hydroxide may reach surface water through spray drift and surface run-off.

To protect nontarget organisms, product labels include application setbacks from surface waters such as rivers, streams, ponds, and lakes of 100 feet for ground boom sprayers and 300 feet for aerial applications.
TPTH is semi-volatile from dry surfaces but non-volatile from water. 
The aerobic soil half-life of TPTH is greater than 1,114 days.

Triphenyltin hydroxide is an organotin that was formerly used as a fungicide. 
Triphenyltin hydroxide is soluble in water up to 1.2 mg/L at 20 C and has a density of 1.54 g/mL. 
Triphenyltin hydroxide has an acid dissociation constant of pKa = 5.20. 
The compound is expected to have very low mobility within soil. 

If discharged to water the compound may convert to triphenyltin oxides, hydroxides or carbonates based on the acid dissociation constant. 
The anions will not adsorb to suspended solids but the cations will. 
Photolysis of the triphenyltin cation is expected to be a major fate process in water. 
Bioaccumulation in organisms is expected to be high.

The  does not currently test for TPTH in  groundwater and surface water samples. 
Analysis for this chemical cannot be incorporated into the existing procedures used by the laboratory and would require additional analytical methods or laboratory equipment. 
Monitoring conducted in the state by the US Geological Survey (USGS) between 2012 and 2019 has not detected TPTH in  groundwater or surface water samples. 

TPTH has been detected in surface water samples from other upper Midwest states including Iowa and North Dakota.
The overall detection frequency in surface waters in the US has been low, less than <1% of surface water samples.

TPTH is very highly toxic to fish and aquatic invertebrates on an acute exposure basis. 
The Environmental Protection Agency (EPA) Office of Pesticide Programs aquatic life benchmarks are 3550 and 65 ppt for acute and chronic exposure, respectively.
EPA categorizes TPTH as moderately toxic to birds and mammals from acute oral exposure (mallard duck LD50 = 378 mg ai/kg; Norway rat LD50 = 156 mg ai/kg). 
Some vascular plants are also sensitive to high rates of this fungicide. 
Triphenyltin hydroxide is considered practically nontoxic to bees on an acute contact basis.

General Manufacturing Information of Triphenyltin hydroxide:    

Industry Processing Sectors:
Pesticide, fertilizer, and other agricultural chemical manufacturing

Analytic Laboratory Methods of Triphenyltin hydroxide:
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.

Physical Description of Triphenyltin hydroxide:    
Triphenyltin hydroxide is an odorless white powder. 
Stable at room temperature. 
Melting point 121-123°C. 
Moderately soluble in most organic solvent. 
Insoluble in water. 
Non corrosive. 
Triphenyltin hydroxide is used as a fungicide.

Other Experimental Properties of Triphenyltin hydroxide:
Thermally decomp to phenyltin, phenyltin oxide and water.
Dehydration to oxide occurs on heating above 45 °C.
Triorganotin hydroxides behave not as alcohols, but more like inorganic bases, although strong bases remove the proton in certain triorganotin hydroxides since tin is amphoteric.

Pharmacology and Biochemistry of Triphenyltin hydroxide:

Absorption, Distribution and Excretion of Triphenyltin hydroxide:    
Several studies have shown that TPTH orally admin to rats is eliminated mainly via the feces, with smaller amounts in the urine. 
Metabolites found in feces included di- & monophenyltin as well as a significant portion of non-extractable bound residues (the sulfate conjugates of hydroquinone, catechol, & phenol). 
In feces, the major substance present was unchanged parent compound.

Seven days after oral admin to rats, TPTH residues (approx 3% of the admin dose) were distributed mainly in the kidneys, followed by liver, brain, & heart.

Application of Triphenyltin hydroxide:
Reactant involved in transmetalation reactions with Ir clusters

Reactant involved in synthesis of:
(E)-(Nitrophenyl)propenoic acid organotin(IV) carboxylates with antitumor activity
Triorganotin chrysanthemumates for larvicidal studies

Polynuclear organotin(IV) carboxylates containing ferrocenyl moieties for antitumor investigation
Organotin(IV) aminophenylacrylate complexes
4-Biphenylcarboxylic acid derivatives for in vitro cytotoxicity studies

Labelled analogue of Triphenyltin Hydroxide, an organotin compound. 
Triphenyltin Hydroxide is used as a fungicide and antifeeding compound for insect control. 
Recent studies show that Triphenyltin Hydroxide may have adverse effects on the reproductive and immune systems and may disrupt the endocrine system.

Uses of Triphenyltin hydroxide:
Tin is found in many forms, including stannous oxide (SnO), triethyltin (Sn(C2H3))3, and triphenyltin hydroxide (Sn(C6H6)OH). 
Tin compounds have many uses, including protective coatings, tin plate, and cans. 
Alloys such as bronze, brass, and solders also contain tin. 

Minor uses include dyes, ceramics, flame retardants, and pigments. 
Stannous fluoride is often used in toothpaste to prevent cavities. 
Organotin compounds have been used as marine antifouling agents (a use now abandoned), as pesticides, and as stabilizers in plastics.

Triphenyltin hydroxide is used in insecticides, non-systemic fungicides (potatoes, sugar beets, nuts, rice, beans, and vegetables), and antifouling paints; Not currently registered with the EPA for use in the US.

For early and late blight on potatoes, leaf spot on sugar beets, peanuts, scab, and several other diseases on pecans. 
Fungal diseases on rice, beans, garlic, onion, pepper, tomato. 
Exhibits antifeeding properties for surface-feeding insects. 

Triphenyl tin compounds are used as agricultural fungicides in crop protection. 
They are employed to control potato, celery, sugar beet, coffee, and rice against fungal disease. 
Triphenyltin hydroxide is also used as a biocide in antifouling paints.


Triphenyltin hydroxide is uses for Classification:
Agrochemicals: Fungicides, Herbicides

EU Pesticides Database:
Health Hazards: Teratogens

NJDOH RTK Hazardous Substance List

Foods, Materials, Technologies and Risks of Triphenyltin hydroxide:

Copper compounds are also allowed to be used in the so called ‘organic’ farming. 
Scarce data are available on the amount of copper compounds used. 
In the UK there was an increase from an average yearly use of 27 t in the 1990s to a little more than 40 t in the last 10 years.

Cyhexatin, azocyclotin, triphenyltin (fentin) acetate, and triphenyltin (fentin) hydroxide are no longer registered in the EU and USA. 
However, their use still persist in other parts of the world. 
For this reason, a brief description isprovided below. 
Only data for fentin (hydroxide and acetate) are available from the UK showing that approximately 45 t year−1 were used in early 1990s down to approximately 30 t in 2003 when Triphenyltin hydroxide was banned.

Bismuth compounds have been used in the past in certain crops against foliar diseases, but Triphenyltin hydroxide use is now discontinued.

Mercuric chloride and organomercury compounds are no longer used as pesticides, at least in all developed countries. 
In view of this fact, and because mercury is discussed in other chapters of the encyclopedia, Triphenyltin hydroxide will not be discussed in this article.

Industry Uses of Triphenyltin hydroxide:    

Consumer Uses of Triphenyltin hydroxide:    
Non-TSCA use

Manufacturing of Triphenyltin hydroxide:    
Production from triphenyltin chloride by hydrolysis with aqueous sodium hydroxide.

Structure of Triphenyltin hydroxide:
While triphenyltin hydroxide is often depicted as a monomer, Triphenyltin hydroxide crystallizes as a polymer with a bridging hydroxide groups.
The Sn-O distances are 2.18 and 2.250 Å. 
Many organotin compounds engage in similar aggregation equilibria.

Safe Storage of Triphenyltin hydroxide:    
Provision to contain effluent from fire extinguishing. 
Separated from food and feedstuffs. 
Store in an area without drain or sewer access.

Storage Conditions of Triphenyltin hydroxide:    
Provision to contain effluent from fire extinguishing. 
Store separated from food & feedstuffs.

Nonfire Spill Response of Triphenyltin hydroxide:
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. 
Triphenyltin hydroxide is uses absorbent paper dampened with acetone to pick up any remaining material. 

Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. 
Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. 
Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. 

STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store Triphenyltin hydroxide in a refrigerator.

Industrial Processes with risk of exposure:
Painting (Pigments, Binders, and Biocides) 
Farming (Pesticides) 

First Aid of Triphenyltin hydroxide:
EYES: First check the victim for contact lenses and remove if present. 
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. 
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. 
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. 

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. 
Gently wash all affected skin areas thoroughly with soap and water. 
IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. 
IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. 

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. 
IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 
Provide proper respiratory protection to rescuers entering an unknown atmosphere. 
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. 

INGESTION: Some heavy metals are VERY TOXIC POISONS, especially if their salts are very soluble in water (e.g., lead, chromium, mercury, bismuth, osmium, and arsenic). 
IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. 
Also locate Ipecac syrup or a glass of salt water in case the medical advisor recommends inducing vomiting. 
Usually, this is NOT RECOMMENDED outside of a physician's care. 

If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. 
If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. 
IMMEDIATELY transport the victim to a hospital.

Fire Fighting of Triphenyltin hydroxide:
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher.

Isolation and Evacuation of Triphenyltin hydroxide:
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.

Spillage Disposal of Triphenyltin hydroxide:    
Personal protection: face shield, chemical protection suit and particulate filter respirator adapted to the airborne concentration of the substance. 
Sweep spilled substance into covered containers. 
If appropriate, moisten first to prevent dusting. 
Carefully collect remainder. 
Then store and dispose of according to local regulations. 
Do NOT let this chemical enter the environment.

Cleanup Methods of Triphenyltin hydroxide:    
The compounds should not be allowed to enter drains or watercourses.

Do not wash away into sewer. 
Carefully collect remainder, then remove to safe place.

Disposal Methods of Triphenyltin hydroxide:    
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.

Identifiers of Triphenyltin hydroxide:
CAS Number: 76-87-9 
ChEBI: CHEBI:30473
ChEMBL: ChEMBL506538 
ChemSpider: 21106510
ECHA InfoCard: 100.000.901 
EC Number: 200-990-6
Gmelin Reference: 7194
KEGG: C18729
PubChem CID: 9907219
RTECS number: WH8575000
UNII: KKL46V5313
UN number: 2786 2588
CompTox Dashboard (EPA): DTXSID50215768 
SMILES: O[Sn](c1ccccc1)(c2ccccc2)c3ccccc3

Properties of Triphenyltin hydroxide:
Chemical formula: C18H16OSn
Molar mass: 367.035 g·mol−1

Quality Level: 100
mp: 124-126 °C (lit.)
SMILES string: O[Sn](c1ccccc1)(c2ccccc2)c3ccccc3
InChI: 1S/3C6H5.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1-5H;1H2;/q;;;;+1/p-1

Compound Formula: C18H16OSn
Molecular Weight: 376.03
Appearance: Beige solid
Melting Point: 124-126 °C
Boiling Point: N/A
Density: N/A
Solubility in H2O: N/A
Exact Mass: 368.022 g/mol
Monoisotopic Mass: 368.022 g/mol

Molecular Weight: 368.0
Hydrogen Bond Donor Count: 1    
Hydrogen Bond Acceptor Count: 1    
Rotatable Bond Count: 3    
Exact Mass: 369.030143    
Monoisotopic Mass: 369.030143    
Topological Polar Surface Area: 1 Ų    
Heavy Atom Count: 20    
Formal Charge: 0    
Complexity: 207    
Isotope Atom Count: 0    
Defined Atom Stereocenter Count: 0    
Undefined Atom Stereocenter Count: 0    
Defined Bond Stereocenter Count: 0    
Undefined Bond Stereocenter Count: 0    
Covalently-Bonded Unit Count: 2    
Compound Is Canonicalized: Yes

Specifications of Triphenyltin hydroxide:
Color: White
Melting Point: 122°C to 124°C
Linear Formula: (C6H5)3SnOH
UN Number: UN3146
Merck Index: 14,9745
Quantity: 25g
Solubility Information: Slightly soluble in alcohol, toluene
Formula Weight: 367.01
Physical Form: Powder
Chemical Name or Material: Triphenyltin hydroxide

Names of Triphenyltin hydroxide:

Regulatory process names of Triphenyltin hydroxide:
Fentin hydroxide
Fentin hydroxide
fentin hydroxide
fentin hydroxide (ISO)
fentin hydroxide (ISO)
triphenyltin hydroxide

Translated names of Triphenyltin hydroxide:
fencín-hydroxid (ISO) (sk)
fentiinhüdroksiid (ISO) (et)
fentin hidroksid (ISO) (hr)
fentin hidroksid (ISO) (sl)
fentin hydroxide (ISO) (cs)
fentin hydroxide (ISO)· (el)
fentin idrossido (ISO) (it)
fentin-hidroxid (ISO) (hu)
fentinahydroksidi (ISO) (fi)
fentinhidroksidas (ISO) (lt)
fentinhidroksīds (ISO) (lv)
fentinhydroksid (no)
fentinhydroxid (ISO) (da)
Fentinhydroxid (ISO) (de)
fentinhydroxid [ISO] (sv)
fentinhydroxide (ISO) (nl)
fentyny wodorotlenek (ISO) (pl)
hidroxid de fentin (ISO) (ro)
hidroxid de trifenilstaniu (ro)
hidróxido de fentina (ISO) (es)
hidróxido de fentina (ISO) (pt)
hidróxido de trifenilestanho (pt)
hidróxido de trifenilestaño (es)
hydroxyde de fentine (ISO);hydroxyde de triphénylétain (fr)
hydroxyde de triphénylétain (fr)
idrossido di trifenilstagno (it)
idrossidu tal-fentin (ISO) (mt)
idrossidu tat-trifeniltin (mt)
trifenilalavo hidroksidas (lt)
trifenilalvas hidroksīds (lv)
trifenilkositrov hidroksid (hr)
trifenilkositrov hidroksid (sl)
trifeniltin-hidroxid (hu)
trifenyl(hydroxyl)stannan (cs)
trifenylcín- hydroxid (cs)
trifenylstanium-hydroxid (sk)
trifenyltennhydroxid (sv)
trifenyltinhydroxide (nl)
trifenyltinnhydroksid (no)
trifenyylitinahydroksidi (fi)
trifenüültinahüdroksiid (et)
triphenyltinhydroxid (da)
Triphenylzinnhydroxid (de)
wodorotlenek trifenylocyny (pl)
υδροξείδιο του τριφαινυλοκασσιτέρου (el)
трифенилкалаен хидроксид (bg)
фентин хидроксид (ISO) (bg)

CAS names of Triphenyltin hydroxide:

Alternate Chemical Names of Triphenyltin hydroxide:
ENT 28009
K 19
OMS 1017

Preferred IUPAC name of Triphenyltin hydroxide:

IUPAC names of Triphenyltin hydroxide:
fentin hydroxide (ISO); triphenyltin hydroxide
Triphenyltin Hydroxide
triphenyltin(IV) hydroxide

Synonyms of Triphenyltin hydroxide:
Triphenyltin hydroxide
Vancide ks
Stannane, hydroxytriphenyl-
Duter extra
Triphenyltin oxide
Dowco 186
Suzu H
Stannol, triphenyl-
Fintin hydroxid
Fintin hydroxyde
Fintin idrossido
Sunitron H
Fintine hydroxyde
Tin, hydroxytriphenyl-
Du-Ter W-50
Flo-Tin 4L
Triphenylstannium hydroxide
Hydroxyde de triphenyl-etain
Idrossido di stagno trifenile
ENT 28009
K 19
OMS 1017
NSC 113243
Tpth Technical
Du-Ter Fungicide
Triple Tin 4l
Vito Spot Fungicide
Flo Tin 4l
Du-Tur Flowable-30
Caswell No. 896E
Fentin hydroxide
Ida, Imc Flo-Tin 4L
Fintin hydroxid
Fintin hydroxyde 
Fintine hydroxide
Triphenyltin(IV) hydroxide
Du-Ter PB-47 Fungicide
Fintin idrossido
Fintine hydroxide 
Fintine hydroxyde 
Brestan H 47.5 WP fungicide
Du-Ter Fungicide Wettable Powder
HSDB 1784
K 19 (VAN)
EINECS 200-990-6
Hydroxyde de triphenyl-etain
EPA Pesticide Chemical Code 083601
Wesley Technical Triphenyltin Hydroxide
BRN 4139186
Haitin WP 20 (fentin hydroxide 20%)
Haitin WP 60 (fentin hydroxide 60%)
Idrossido di stagno trifenile
Super Tin 4L Gardian Flowable Fungicide
Ashlade flotin
fentin hydroxide (ISO)
triphenylstannylium hydroxide
Fentin hydroxide, PESTANAL(R), analytical standard

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