Dichlorophen

Dichlorophen	Last updated: 11/01/2021
(Also known as: antiphen; anthifen)

SUMMARY

Dichlorophen is a fungicide, herbicide, bactericide and algicide that is not approved for use in the EU. It has a low aqueous solubility and, based on its chemical properties, it is unlikely to leach to groundwater. It is not usually persistent in soils. Dichlorophen has a low mammalian toxicity but is moderately toxic to fish, aquatic invertebrates and algae.

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: Potential for particle bound transport: Medium Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate Warning: Significant data are missing	Human health Moderate alert: Possible Carcinogen; Possible Reproduction/development effects

GENERAL INFORMATION

Description

A multiple purpose pesticide used to control various infections in agricultural and horticultural crops as well as in non-crop situations . Also has some applications as a veterinary treatment.

Example pests controlled

Red thread; Fusarium patch; Stem canker; Angular leaf spot; Cucumber wilt; Damping off; Root rot; Bulb riot; Web blotch

Example applications

Cotton; Peanuts; Potatoes; Vegetables including beans, onions, garlic; Tomatoes; Cucumbers; Ornamentals; Non-crop situations

Efficacy & activity

Availability status

Unknown

Introduction & key dates

First patented 1944 USA

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Ireland

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

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₃H₁₀Cl₂O₂

Canonical SMILES

C1=CC(=C(C=C1Cl)CC2=C(C=CC(=C2)Cl)O)O

Isomeric SMILES

Clc1cc(c(O)cc1)Cc2cc(Cl)ccc2O

International Chemical Identifier key (InChIKey)

MDNWOSOZYLHTCG-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H10Cl2O2/c14-10-1-3-12(16)8(6-10)5-9-7-11(15)2-4-13(9)17/h1-4,6-7,16-17H,5H2

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
dichlorophen	-

General status

Pesticide type

Fungicide, Algicide, Bactericide, Veterinary substance

Substance group

Hetrocyclic

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Contact

CAS RN

97-23-4

EC number

202-567-1

CIPAC number

325

US EPA chemical code

055001

PubChem CID

3037

Molecular mass

269.1

PIN (Preferred Identification Name)

2,2'-methylenebis(4-chlorophenol)

IUPAC name

4,4'-dichloro-2,2'-methylenediphenol

CAS name

2,2'-methylenebis[4-chlorophenol]

Other status information

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 crystals

Formulations

Property

Value

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

Sindar

Example products using this active

Preventol

Formulation and application details

Usually supplied as an emulsifiable concentrate from crop protection purposes. As an animal insecticide formulations include cutaneous sprays, tablets for oral administration and shampoos

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)

800000

Acetone

530000

Ethanol

540000

Isopropanol

Melting point (°C)

177.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.70 X 10⁰³

Calculated

Log P

3.23

High

Bulk density (g ml⁻¹)

1.42

Dissociation constant pKa) at 25 °C

7.6

pKa(2) 11.6, Weak acid

Vapour pressure at 20 °C (mPa)

1.30 X 10^-05

Low volatility

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

1.17 X 10^-07

Non-volatile

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)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

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

Note

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

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

4103

Notes and range

Estimated

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.43

Calculated

Low leachability

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

Value

8.36 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

45.4

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

2690

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

2000

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

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.54

Oncorhynchus mykiss 48 hour

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 0.154

Pimephales promelas

Moderate

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

6.2

Daphnia magna

Moderate

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

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

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)

Non-target plants

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

Unknown species

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)

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)

2690

Rat

Low

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

1000

Mouse

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Intravenous DT₅₀ = 17.0 mg kg⁻¹

Rat

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

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

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

Exposure Routes

Public

Low risk to Europeans as no longer approved for use

Occupational

Low risk to Europeans as no longer approved for use

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

Moderately toxic

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302, H319
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22
Xi - Irritant: R36 N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S26, S60, S61

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

dichlorophen

French

dichlorophene

German

Dichlorophen

Danish

dichlorophen

Italian

diclorofene

Spanish

diclorofen

Greek

dichlorophen

Polish

dichlorofen

Swedish

Hungarian

Dutch

dichlorofeen

Record last updated:	11/01/2021
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