Fentin hydroxide

Fentin hydroxide	Last updated: 28/08/2024
(Also known as: organotin; triphenyltin hydroxide)

SUMMARY

Fentin hydroxide is an obsolete organotin fungicide. It has a low aqueous solubility and low volatility. Evidence suggests it is not persistent in soil systems but may be more so in aquatic systems. Based on its physico-chemical properties it is not expected to leach to groundwater. Ecotoxicological data is limited but acute oral ecotoxicity tends to be high to moderate. It is moderately toxic to mammals via the oral route.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Possible Carcinogen; Endocrine disrupter; Reproduction/development effects

GENERAL INFORMATION

Description

A non-systemic fungicide used to control a variety of infections including blight on potatoes, leaf spot on sugar beet and alternaria blight on carrots

Example pests controlled

Early and late blight; Septoria leaf spot; Rusts; Scab

Example applications

Potatoes; Celery and celeriac; Onions; Sugarbeet; Peanuts; Wheat; Coffee; Pecans

Efficacy & activity

Availability status

Introduction & key dates

1960, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₈H₁₆OSn

Canonical SMILES

C1=CC=C(C=C1)[Sn](C2=CC=CC=C2)C3=CC=CC=C3.O

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

BFWMWWXRWVJXSE-UHFFFAOYSA-M

International Chemical Identifier (InChI)

InChI=1S/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

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Organometal fungicide; Organotin fungicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Curative and protective action. Inhibitor of mitochondrial ATP synthase.

CAS RN

76-87-9

EC number

200-990-6

CIPAC number

490

US EPA chemical code

083601

PubChem CID

6327657

CLP index number

050-004-00-1

Molecular mass

367.0

PIN (Preferred Identification Name)

triphenylstannanol

IUPAC name

triphenyltin hydroxide

CAS name

triphenylstannylium hydroxide

Other status information

OSPAR soc; Severe Marine Pollutant; Chemical subject to PIC regulations; Subject to the provisions of the UK Poisons Act 1972

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

Colourless crystals

Related substances & organisms

fentin acetate

fentin chloride

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Barclay
Duphar
Schering
Nitoo Kasei
Hoechst

Example products using this active

Du-Ter
Duter
Haitin
Tubotin

Formulation and application details

Usually formulated as a wettable powder or suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

50000

Acetone

10000

Ethanol

74000

1,2-Dichloroethane

171000

Diethyl ether

Melting point (°C)

123

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

174

Octanol-water partition coefficient at pH 7, 20 °C

2.69 X 10⁰³

Calculated

Log P

3.43

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.54

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.047

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

4.30 X 10^-02

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Moderately persistent

Note

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Moderately fast

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

3104

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.95

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

1.91 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Bio-concentration factor

BCF (l kg⁻¹)

4300

Threshold for concern

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

108

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

377.6

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

114.8

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.05

Cyprinidae spp.

High

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

< 0.00021

Cyprinodon variegatus

High

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.021

Danio rerio EC₅₀ Embryo

High

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.0165

Daphnia magna

High

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.01

Ceriodaphnia dubia

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0037

Americamysis bahia

High

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.008

Lemna gibba 7 day

High

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.0000024

Scenedesmus acutus

High

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

108

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

127.0

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.06

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.0004

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.001

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List I

Exposure Routes

Public

Occupational

Occupational exposure may occur through inhalation and dermal contact

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

CLP data - suspected carcingen; US EPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301, H311, H315, H318, H330, H335, H351, H361d, H372
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2786

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

fentin hydroxide

French

fentine hydroxyde

German

Fentinhydroxid

Danish

fentin hydroxid

Italian

fentin idrossido

Spanish

hidróxido de fentin

Greek

Polish

wodorotlenek fentinu

Swedish

Hungarian

fentin hidroxid

Dutch

fentinhydroxide

Norwegian

Record last updated:	28/08/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242