Dicloran (Ref: RD 6584)

Dicloran (Ref: RD 6584)	Last updated: 11/01/2021
(Also known as: ditranil; dichloran; CAN; U 2069; SN 107682; DCNA)

SUMMARY

Dicloran is a fungicide that is not approved for use in the EU. It has a low aqueous solubility and is volatile. Based on its chemical properties, is may leach to groundwater. It can also be quite persistent in soils but not usually so in water. It is moderately toxic to mammals but is not expected to bioaccumulate. Exposure may damage reproduction and/or development. Dicloran is moderately toxic to most aquatic organisms, birds, honeybees and earthworms.

GENERAL INFORMATION

Description

An aromatic fungicide used for a variety of pre- and post-harvest diseases on fruit and vegetables

Example pests controlled

Yeasts; Moulds; Brown rot; Powdery mildew

Example applications

Fruit including apricots, nectarines, oranges, grapes, peaches, plums, cherries, rhubarb; vegetables including beans, celery, onions, shallots; Sweet potatoes; Tomatoes; Ornamentals including Christmas trees

Efficacy & activity

Availability status

Current

Introduction & key dates

1960, first reported; 1993, first marketed

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Spain

Date EC 1107/2009 inclusion expires

Not applicable

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

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₆H₄Cl₂N₂O₂

Canonical SMILES

C1=C(C=C(C(=C1Cl)N)Cl)[N+](=O)[O-]

Isomeric SMILES

Clc1cc(cc(Cl)c1N)[N+]([O-])=O

International Chemical Identifier key (InChIKey)

BIXZHMJUSMUDOQ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C6H4Cl2N2O2/c7-4-1-3(10(11)12)2-5(8)6(4)9/h1-2H,9H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Chlorophenyl

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - trace polychlorinated dibenzo-p-dioxins, dibenzofurans & polychlorinated biphenyls; 2, 6-dichloro-p-phenylenediamine. 0.2 g kg⁻¹; 2-chloro-4-nitrobenzeneamine 10 g kg⁻¹

Substance origin

Synthetic

Mode of action

Protective, contact action, thought to act by inhibiting respiration inhibiting spore germination. Lipid peroxidation inhibitor.

CAS RN

99-30-9

EC number

202-746-4

CIPAC number

150

US EPA chemical code

031301

PubChem CID

7430

Molecular mass

207.01

PIN (Preferred Identification Name)

2,6-dichloro-4-nitroaniline

IUPAC name

2,6-dichloro-4-nitroaniline

CAS name

2,6-dichloro-4-nitrobenzenamine

Other status information

Potential groundwater contaminant; Chemical subject to PIC regulations

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)

Examples of recorded resistance

Physical state

Yellow crystals or powder

Formulations

Property

Value

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

Botran
Fumite
Sclerosan
Allisan
Resinan

Example products using this active

Gowan Company
Upjohn
FBC

Formulation and application details

Often formulated as wettable powders, dusts or as flowable concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

6.4

at 25 °C

Low

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

200

n-Heptane

6400

p-Xylene

6700

Methanol

41800

Acetone

Melting point (°C)

193.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

202

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

6.31 X 10⁰²

Calculated

Log P

2.8

Moderate

Bulk density (g ml⁻¹)

1.57

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.261

Low volatility

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

8.44 X 10^-03

Non-volatile

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

217nm = 15760, 325nm = 12750

Surface tension (mN m⁻¹)

68.7

at 20.3 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

401

Very persistent

DT₅₀ (lab at 20 °C)

258

Persistent

DT₅₀ (field)

18.7

Non-persistent

DT₉₀ (lab at 20 °C)

985

Very persistent

DT₉₀ (field)

202

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 144-617 days, DT₉₀ range 481-1892 days; field studies DT₅₀ 18.4-18.9 days; Other sources: DT₅₀ 10.0 days (DW4)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

23.4

Note

Lettuce leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.3

Moderately fast

Note

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

Value

Stable

Note

Stable at all relevant pH's

Water-sediment DT₅₀ (days)

3.84

Fast

Water phase only DT₅₀ (days)

2.94

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

12.33

Slightly mobile

K_foc

812

¹/_n

0.739

Notes and range

EU dossier K_f range 3.65-26.25 mL g⁻¹, K_foc range 441-1188 mL g⁻¹, ¹/_n range 0.645-0.803, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.39

Calculated

Low leachability

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

Value

2.91 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2,6-dichloro-1,4-phenylenediamine (Ref: CI 37020 )

Soil

0.118

Major fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

DCHA-sulfate

Rat (Urinary)

DCHA-glucuronide

Rat (Urinary)

4-amino-3,5-dichlorophenol

DCHA

Rat (Urinary); Water/sediment

DCAP

Rat (Urinary)

DCNAP

Rat (Urinary)

2,6-dichlorobenzoic acid

2,6-DCBA

Water/sediment

0.089

4-amino-3,5-dichloracetanilide

Water/sediment

0.075

2,6-dichloro-4-nitrophenol

Water/sediment

3,5-dichloro-4-hydroxyacetanilide
Note: Minor metabolite

Water/sediment

3,5-dichloro-4-aminoacetanilide
Note: Minor metabolite

DCAA

Water/sediment

2,6-dichloro-1,4-phenylenediamine
Note: Minor metabolite

DCPD

Water/sediment

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

1.5

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

286

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

164.3 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.48

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.05

Oncorhynchus mykiss

Moderate

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

2.07

Daphnia magna

Moderate

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

0.032

Daphnia magna

Moderate

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)

0.6

Chironomus riparius

Moderate

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

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

Non-target plants

> 1000

worst case for ten species
Seedling emergence, ER₅₀
as g ha⁻¹

> 1000

worst case for ten species
Vegetative vigour, ER₅₀
as g ha⁻¹

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

1.2

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)

> 100

Low

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

> 113

Low

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)

> 885

Eisenia foetida

Moderate

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

77.8

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

3000

>, 48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

374

7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 3.4 kg ha⁻¹

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 21.6

Rat

Other Mammal toxicity endpoints

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

0.005

Dog SF=500

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

0.025

Dog SF=100

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

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

0.005

Dog SF=500

Dermal penetration studies (%)

1-9

Dangerous Substances Directive 76/464

Exposure Routes

Public

Risk acceptable and below the AOEL

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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

Possible liver & spleen toxicant
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Emits irritating or toxic fumes in a fire
Not explosive or oxidising
IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H300, H310, H330, H373
Environment: H411

EC Risk Classification

N - Dangerous for the environment: R53

EC Safety Classification

WHO Classification

III (Slightly hazardous)

UN Number

Usually 2811

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

dicloran

French

dicloran

German

Dicloran

Danish

dicloran

Italian

dicloran

Spanish

dicloran

Greek

Polish

dichloran

Swedish

Hungarian

Dutch

dichloran

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