FENTIN HYDROXIDE
Fentin hydroxide is an organotin compound used as a non-systemic foliar fungicide to control early and late blight on potatoes, leaf spot on sugar beets, and select fungal diseases on pecans.
Fentin hydroxide inhibits ATP synthase in fungal cells, preventing energy production and disrupting respiration, making it an effective fungicide.
Fentin hydroxide has low water solubility, binds strongly to soil, and is not expected to leach into groundwater, though it may reach surface water through spray drift and runoff.
CAS Number: 76-87-9
EC Number: 200-990-6
Chemical formula: C18H16OSn
Molar mass: 367.035 g·mol−1
Synonyms: Triphenyltin hydroxide, FENTIN HYDROXIDE, Triphenylstannanol, Fentin, 76-87-9, Tptoh, Vancide ks, Hydroxytriphenyltin, Hydroxytriphenylstannane, Erithane, Fenolovo, Tenhide, Stannane, hydroxytriphenyl-, Duter extra, Triphenyltin oxide, Dowco 186, Du-Ter, Suzu H, Haitin, Stannol, triphenyl-, Fintin hydroxid, TPTH, Fintin hydroxyde, Fintin idrossido, Phenostat-H, Sunitron H, Fintine hydroxyde, Tin, hydroxytriphenyl-, Du-Ter W-50, Trifenyl-tinhydroxyde, Triphenyl-zinnhydroxid, Flo-Tin 4L, Triphenylstannium hydroxide, NCI-C00260, Hydroxyde de triphenyl-etain, Idrossido di stagno trifenile, ENT 28009, Trifenylstanniumhydroxid, K 19, OMS 1017, NSC 113243, K19, Tpth Technical, Du-Ter Fungicide, Triple Tin 4l, Vito Spot Fungicide, Flo Tin 4l, Du-Tur Flowable-30, Caswell No. 896E, Duter, 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, CCRIS 612, Triphenyltinhydroxide, Trifenyl-tinhydroxyde, Brestan H 47.5 WP fungicide, Triphenyl-zinnhydroxid, Trifenylstanniumhydroxid, 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, C18H16OSn, BRN 4139186, Haitin WP 20 (fentin hydroxide 20%), Haitin WP 60 (fentin hydroxide 60%), Idrossido di stagno trifenile, Super Tin 4L Gardian Flowable Fungicide, Farmatin, Ashlade flotin, AI3-28009, Fentin-hydroxide, Super-tin, Sn(OH)Ph3, fentin hydroxide (ISO), hydroxy(triphenyl)stannane, DSSTox_CID_1409, [Sn(OH)Ph3], triphenylstannylium hydroxide, DSSTox_RID_76145, WLN: Q-SN-R&R&R, DSSTox_GSID_21409, SCHEMBL70052, triphenylstannanylium;hydroxide, DTXSID1021409, CHEBI:30473, Tox21_300754, MFCD00013928, NSC113243, AKOS015960675, ZINC169876287, NSC-113243, CAS-76-87-9, NCGC00163909-01, NCGC00163909-02, NCGC00163909-03, NCGC00163909-04, NCGC00254659-01, O595, C18729, Fentin hydroxide, PESTANAL(R), analytical standard, Q7843285
Fentin hydroxide is an organotin compound with formula Sn(C6H5)3OH.
Fentin hydroxide is used as a fungicide for potatoes, sugar beets, and pecans.
Fentin hydroxide was first registered for use as a pesticide in the United States in 1971.
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.
Fentin hydroxide also exhibits anti-feeding properties for some surface-feeding insects (e.g., Colorado potato beetle).
Fentin 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 Fentin hydroxide.
In 2017, over 200,000 pounds of this active ingredient were sold in Minnesota.
Fentin hydroxide is an odorless white powder.
Fentin hydroxide is stable at room temperature.
Fentin hydroxide's melting point 121-123°C.
Fentin hydroxide moderately soluble in most organic solvents.
Fentin hydroxide is insoluble in water.
Fentin hydroxide is non corrosive.
Fentin 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.
Fentin hydroxide used to control a variety of infections including blight on potatoes, leaf spot on sugar beet and alternaria blight on carrots.
Fentin hydroxide has a role as an acaricide and an antifungal agrochemical.
Fentin hydroxide is an organotin compound and a member of hydroxides.
Fentin hydroxide derives from a triphenylstannane.
Fentin hydroxide inhibits oxidative phosphorylation (respiration) and fungal growth.
Fentin 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.
Fentin hydroxide is an organotin compound with formula Sn(C6H5)3OH.
Fentin hydroxide is used as a fungicide for potatoes, sugar beets, and pecans.
Fentin hydroxide was first registered for use as a pesticide in the United States in 1971.
Fentin hydroxide has low solubility in water and binds strongly to soil.
Therefore, Fentin hydroxide is not expected to leach to groundwater; however, Fentin 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.
Fentin hydroxide is semi-volatile from dry surfaces but non-volatile from water.
The aerobic soil half-life of Fentin hydroxide is greater than 1,114 days.
Fentin hydroxide is an organotin that was formerly used as a fungicide.
Fentin hydroxide is soluble in water up to 1.2 mg/L at 20 C and has a density of 1.54 g/mL.
Fentin hydroxide has an acid dissociation constant of pKa = 5.20.
Fentin hydroxide 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 Fentin hydroxide 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 Fentin hydroxide in groundwater or surface water samples.
Fentin hydroxide 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.
Fentin hydroxide 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 Fentin hydroxide 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.
Fentin hydroxide is considered practically nontoxic to bees on an acute contact basis.
Fentin hydroxide is a chemical compound that reacts with an enzyme called glutathione reductase.
Fentin hydroxide has been shown to have genotoxic effects in the galleria mellonella, which is a type of insect commonly used as a model organism for studies on genetic toxicity.
Fentin hydroxide has also been shown to be toxic to mammalian cells.
The mechanism of this reaction and the inhibition of glutathione reductase by Fentin hydroxide is not fully understood and may involve reactive oxygen species production.
Fentin hydroxide can react with other molecules in order to form new compounds, such as methoxyFentin hydroxide, which has been shown to be an effective anti-cancer compound.
Fentin hydroxide can also react with fluoroacetic acid to form triphenyltin fluoride, which has been shown to be an effective herbicide.
Uses of Fentin hydroxide:
Fentin hydroxide is used in insecticides, non-systemic fungicides (potatoes, sugar beets, nuts, rice, beans, and vegetables), and antifouling paints.
Antifeeding compounds for insect pest control; nonsytemic fungicide.
Fentin hydroxide is used as fungicide.
Fentin hydroxide is used 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.
Fentin hydroxide is used as agricultural fungicides in crop protection.
They are employed to control potato, celery, sugar beet, coffee, and rice against fungal disease.
Fentin hydroxide is also used as a biocide in antifouling paints.
Fentin hydroxide is a non-systemic foliar fungicide used to control early and late blight on potatoes; leaf spot on sugar beets; and scab, brown leaf spot and other diseases on pecans.
Fentin hydroxide is only registered for use on these three crops.
There are no residential, public health or other non-food uses of Fentin hydroxide.
Fentin hydroxide comes in liquid and wettable powder (in water soluble packaging) formulations, and its use is restricted to certified applicators.
Fentin hydroxide is applied by ground equipment, chemigation, airblast spray, and aircraft.
Fentin hydroxide labels require mechanical transfer for liquids, and a closed mixing/loading system for aerial applications.
Handlers are required to wear coveralls, waterproof gloves, chemical resistant footwear, protective eyewear, chemical resistant headgear for overhead exposure, and chemical resistant apron when cleaning equipment, mixing, or 2 loading.
These protective measures may be reduced or modified as specified by the Worker Protection Standard (WPS) when closed systems or enclosed cabs are used.
Industry Uses:
Other (specify)
Consumer Uses:
Other (specify)
Manufacturing of Fentin hydroxide:
Production from triphenyltin chloride by hydrolysis with aqueous sodium hydroxide.
General Manufacturing Information:
Industry Processing Sectors:
Pesticide, fertilizer, and other agricultural chemical manufacturing
Action Mode of Fentin hydroxide:
Fentin hydroxide inhibits oxidative phosphorylation (respiration) and fungal growth.
Fentin 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.
Structure of Fentin hydroxide:
While Fentin hydroxide is often depicted as a monomer, Fentin 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.
Analytic Laboratory Methods of Fentin 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.
Experimental Properties of Fentin 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 Fentin hydroxide:
Absorption, Distribution and Excretion:
Several studies have shown that Fentin hydroxide 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, Fentin hydroxide residues (approx 3% of the admin dose) were distributed mainly in the kidneys, followed by liver, brain, & heart.
Handling and Storage of Fentin hydroxide:
Precautions for safe handling:
Advice on safe handling:
Work under hood.
Do not inhale substance/mixture.
Hygiene measures:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with substance.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Tightly closed.
Dry.
Keep in a well-ventilated place.
Keep locked up or in an area accessible only to qualified or authorized persons.
Storage class:
Storage class (TRGS 510): 6.1A: Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
Stability and Reactivity of Fentin hydroxide:
Reactivity:
The following applies in general to flammable organic substances and mixtures:
In correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.
Chemical stability:
Fentin hydroxide is chemically stable under standard ambient conditions (room temperature).
Possibility of hazardous reactions:
No data available
Conditions to avoid:
no information available
Incompatible materials:
Strong oxidizing agents
First Aid Measures of Fentin hydroxide:
General advice:
First aiders need to protect themselves.
Show this material safety data sheet to the doctor in attendance.
If inhaled:
After inhalation:
Take a fresh air.
Immediately call in physician.
If breathing stops:
Immediately apply artificial respiration, if necessary also oxygen.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Call a physician immediately.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Immediately call in ophthalmologist.
Remove contact lenses.
If swallowed:
Give water to drink (two glasses at most).
Seek medical advice immediately.
In exceptional cases only, if medical care is not available within one hour, induce vomiting (only in persons who are wide awake and fully conscious), administer activated charcoal (20 - 40 g in a 10% slurry) and consult a doctor as quickly as possible.
Indication of any immediate medical attention and special treatment needed:
No data available
Firefighting Measures of Fentin hydroxide:
Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Special hazards arising from the substance or mixture:
Carbon oxides
Tin/tin oxides
Combustible.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
Further information
Suppress (knock down) gases/vapors/mists with a water spray jet.
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental Release Measures of Fentin hydroxide:
Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel:
Avoid generation and inhalation of dusts in all circumstances.
Avoid substance contact.
Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up carefully.
Dispose of properly.
Clean up affected area.
Avoid generation of dusts.
Exposure Controls/Personal Protection of Fentin hydroxide:
Personal protective equipment:
Eye/face protection:
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Tightly fitting safety goggles.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:KCL 741 Dermatril® L
Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested: KCL 741 Dermatril® L
Body Protection:
protective clothing
Respiratory protection:
required when dusts are generated.
Our recommendations on filtering respiratory protection are based on the following standards: DIN EN 143, DIN 14387 and other accompanying standards relating to the used respiratory protection system.
Recommended Filter type: Filter type P3
The entrepeneur has to ensure that maintenance, cleaning and testing of respiratory protective devices are carried out according to the instructions of the producer.
These measures have to be properly documented.
Control of environmental exposure
Do not let product enter drains.
Identifiers of Fentin 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
InChI:
InChI=1S/3C6H5.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1-5H;1H2;/q;;;;+1/p-1
Key: BFWMWWXRWVJXSE-UHFFFAOYSA-M
InChI=1/3C6H5.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1-5H;1H2;/q;;;;+1/p-1/rC18H16OSn/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
Key: BFWMWWXRWVJXSE-OLMCWIPIAE
SMILES: O[Sn](c1ccccc1)(c2ccccc2)c3ccccc3
CAS: 76-87-9
Molecular Formula: C18H18OSn
Molecular Weight (g/mol): 369.05
MDL Number: MFCD00013928
InChI Key: ZJIGGMIMCKZRRB-UHFFFAOYSA-N
PubChem CID: 6327657
IUPAC Name: triphenyltin;hydrate
SMILES: O.C1=CC=C(C=C1)[SnH](C1=CC=CC=C1)C1=CC=CC=C1
Properties of Fentin 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
InChI key: BFWMWWXRWVJXSE-UHFFFAOYSA-M
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
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 Fentin 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: Fentin hydroxide
Names of Triphenyltin Hydroxide:
Regulatory process names:
Fentin hydroxide
Fentin hydroxide
fentin hydroxide
fentin hydroxide (ISO)
fentin hydroxide (ISO)
triphenyltin hydroxide
Translated names:
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:
Stannane
hydroxytriphenyl-
Alternate Chemical Names:
BRESTANID
DOWCO 186
DU-TER
DU-TER W-50
DUTER
ENT 28009
ERITHANE
FENOLOVO
FENTIN HYDROXIDE
HAITIN
HYDROXYTRIPHENYLSTANNANE
HYDROXYTRIPHENYLTIN
K 19
NCI-C00260
OMS 1017
SUNITRON H
SUZU H
TENHIDE
TPTH
TPTOH
TRIPHENYL(HYDROXO)STANNANE
TRIPHENYLHYDROXYTIN
TRIPHENYLSTANNANOL
TRIPHENYLSTANNIUM HYDROXIDE
TRIPHENYLSTANNYL HYDROXIDE
TRIPHENYLTIN HYDROXIDE
TRIPHENYLTIN OXIDE
TUBOTIN
VANCIDE KS
Preferred IUPAC name:
Triphenylstannanol
IUPAC names:
fentin hydroxide (ISO); triphenyltin hydroxide
triphenylstannanol
Triphenyltin Hydroxide
triphenyltin(IV) hydroxide
triphenyltin;hydrate
