2-phenylphenol

2-phenylphenol	Last updated: 24/10/2024
(Also known as: O-phenylphenol; 2-hydroxybiphenyl; phenyl-2 phenol; o-xenol; OPP; ortho-phenylphenol)

SUMMARY

2-phenylphenol is a broad-spectrum fungicide used to protect crops in storage. It is highly soluble in water, moderately volatile but is not expected to be persistent in the environment. 2-phenylphenol has a moderate to low toxicity to biodiversity. This substance has a low oral mammalian toxicity, a neurotoxin and is a recognised irritant.

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 Moderate alert: Drainflow: Moderately mobile	Ecotoxicity High alert: Daphnia chronic ecotoxicity: High	Human health High alert: Genotoxic; Endocrine disrupter; Neurotoxicant

GENERAL INFORMATION

Description

Waxy substance used as a coating agent impregnated into wrappers and storage systems, to protect a variety of crops from storage diseases. Indoor use.

Example pests controlled

Microbial damage; Canker

Example applications

Fruit including apples, pears, citrus

Efficacy & activity

Efficacy demostrated by extensive global use, field and lab trials.

Availability status

Current

Introduction & key dates

circa 1930, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/Greece

Date EC 1107/2009 inclusion expires

15/11/2027

EU Candidate for substitution (CfS)

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

New Zealand, Canada, USA, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₂H₁₀O

Canonical SMILES

C1=CC=C(C=C1)C2=CC=CC=C2O

Isomeric SMILES

International Chemical Identifier key (InChIKey)

LLEMOWNGBBNAJR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
2-phenylphenol	-

General status

Pesticide type

Fungicide, Other substance

Other bioactivity & uses

Disinfectant, Preservative, Biocide, Algicide

Substance groups

Phenolic fungicide

Minimum active substance purity

998 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Broad-spectrum, contact

CAS RN

90-43-7

EC number

201-993-5

CIPAC number

246

US EPA chemical code

064103

PubChem CID

7017

CLP index number

604-020-00-6

Molecular mass

170.21

PIN (Preferred Identification Name)

[1,1'-biphenyl]-2-ol

IUPAC name

biphenyl-2-ol

CAS name

[1,1'-biphenyl]-2-ol

Other status information

PAN listed Highly Hazardous Chemical

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)

BM01

Examples of recorded resistance

Physical state

Colourless to lilac coloured flaky crystalline solid with slight musty odour

Related substances & organisms

sodium ortho-phenylphenoxide

Formulations

Property

Value

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

Dow
Chemos GmbH

Example products using this active

Dowicide 1

Formulation and application details

Fruit are usually packed in boxes and placed in a drenching cabinet. One application post-harvest is made.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

560

High

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

5900000

Ethanol

250000

Ethyl acetate

50300

Heptane

250000

Acetone

Melting point (°C)

56.7

Boiling point (°C)

287

Degradation point (°C)

No decomposition below boiling point

Flashpoint (°C)

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

1.51 X 10⁰³

Calculated

Log P

3.18

at 22.5 °C

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

9.4

Weak acid

Vapour pressure at 20 °C (mPa)

474

Highly volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

0.14

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

245nm = 12800, 287nm = 8200

Surface tension (mN m⁻¹)

58.72

20 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Substance readily biodegrades

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.14

Non-persistent

DT₅₀ (lab at 20 °C)

0.14

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

0.36

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab data: DT₅₀ (normalised) 0.14 days and DT₉₀ (measured) 0.46 days for sandy loam and dark aerobic conditions: Other literature estimate DT₅₀ between 1-7 days

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

0.3

Fast

Note

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

Value

Stable

Note

Stable pH 5-9 upto 50 °C

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

8.65

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

8.68

Moderately mobile

K_foc (mL g⁻¹)

347

¹/_n

0.82

Notes and range

EU 2021 dossier K_f range 7.04-11.66 mL g⁻¹, K_foc range 252-393 mL g⁻¹, ¹/_n range 0.784-0.870, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.25

Calculated

Low leachability

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

Value

1.49 X 10^-05

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

21.7

Low potential

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

2733

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

761

Rat 13-week

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

99.1

Eisenia foetida corr

Moderate

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

62.5

Eisenia foetida corr

Moderate

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)

> 100

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)

4.0

Salmo gairdneri

Moderate

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

0.036

Pimephales promelas

Moderate

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

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

2.7

Daphnia magna

Moderate

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

0.006

Daphnia magna

High

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

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

0.32

Mysidopsis bahia

Moderate

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

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

1.85

Chironomus riparius

Moderate

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

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

6.2

Lemna gibba

Moderate

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

0.85

Scenedesmus subspicatus

Moderate

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)

2733

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.036

Rat

Other Mammal toxicity endpoints

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

0.4

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

None allocated

JMPR 2001

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

None allocated

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

0.4

Rat SF=100

Dermal penetration studies (%)

25-70

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No exposure expected

Occupational

Acceptable risks for the proposed uses when used as prescribed

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

Relatively rapid and almost complete elimination via urine.

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Bladder, kidney and liver toxicant
May damage corneals
Endocrine issues - Estrogen agonist
Corrosive
WHO - unlikely to be carcinogenic; Some published studies suggest carcinogenicity; US EPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Very corrosive
Combustable
Not expected to auto-ignite
Hygroscopic
IMDG Transport Hazard Class 9
Not oxidising or explosive

CLP classification 2013

Health: H315, H319, H335
Environment: H400

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

2-phenylphenol

French

biphenyle-2-ol

German

Biphenyl-2-ol

Danish

Italian

Spanish

ortofenilfenol

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	24/10/2024
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