2-phenylphenol

2-phenylphenol	Last updated: 12/01/2021
(Also known as: O-phenylphenol; 2-hydroxybiphenyl; phenyl-2 phenol; o-xenol; OPP)

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

Availability status

Current

Introduction & key dates

circa 1930

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

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

31/12/2021

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
				✓

Also used in

New Zealand, Canada, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₂H₁₀O

Canonical SMILES

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

Isomeric SMILES

No data

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 constituent type

Disinfectant, Preservative

Substance group

Phenol

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

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not known

Examples of recorded resistance

Physical state

Colourless to lilac coloured flaky crystalline solid

Related substances & organisms

propylene glycol

Formulations

Property

Value

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

Dowicide 1

Example products using this active

Dow
Chemos GmbH

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)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.51 X 10⁰³

Calculated

Log P

3.18

High

Bulk density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

9.4

Weak acid

Vapour pressure at 20 °C (mPa)

474

at 906 mPa 25 °C

Highly volatile

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

0.14

Moderately volatile

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

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

0.11

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

0.36

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab data: DT₅₀ 0.11 days and DT₉₀ 0.36 days for sandy loam and aerobic conditions: Other literature estimate DT₅₀ between 1-7 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

8.68

Moderately mobile

K_foc

347

¹/_n

0.82

Notes and range

EU dossier K_f range 7.47-11.66 mL g⁻¹, K_foc range 252-393 mL g⁻¹, ¹/_n range 0.784-0.870

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.40

Calculated

Low leachability

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

Value

1.03 X 10^-05

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

21.7

Low potential

CT₅₀ (days)

Not available

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)

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

4.0

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.036

Pimephales promelas

Moderate

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

2.7

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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

Non-target plants

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

0.85

Scenedemus subspicatus

Moderate

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

Honeybees (Apis 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)

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

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 pollinators (1)

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

Mode of exposure

Other pollinators (2)

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

Mode of exposure

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

99.1

Eisenia foetida corr

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

Mesocosm study data

NOEAEC mg l⁻¹

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)

Not allocated

JMPR 2001

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

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

0.4

Rat SF=100

Dermal penetration studies (%)

100

default

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Bladder, kidney and liver toxicant
May damage corneals
Endocrine issues - Estrogen agonist

Handling issues

Property

Value and interpretation

General

Very corrosive
Combustable
Hygroscopic
IMDG Transport Code is usually 9

CLP classification 2013

Health: H315, H319, H335
Environment: H400

EC Risk Classification

Xi - Irritant: R36/37/38
N - Dangerous for the environment: R50

EC Safety Classification

S2, S22, S61

WHO Classification

III (Slightly hazardous)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

2-phenylphenol

French

biphenyle-2-ol

German

Biphenyl-2-ol

Danish

Italian

Spanish

ortofenilfenol

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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