Diphenylamine

Diphenylamine	Last updated: 21/08/2024
(Also known as: DPA; anilinobenzene)

SUMMARY

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 Low alert: Drainflow: Non-mobile Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

Used mainly to control post-harvest disease and damage in apples and pears via both pre- and post-harvest treatments

Example pests controlled

Fruit skin scald

Example applications

Fruit including apples, pears

Efficacy & activity

Availability status

Introduction & key dates

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

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

Ireland

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

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

C₁₂H₁₁N

Canonical SMILES

C1=CC=C(C=C1)NC2=CC=CC=C2

Isomeric SMILES

International Chemical Identifier key (InChIKey)

DMBHHRLKUKUOEG-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
diphenylamine	-

General status

Pesticide type

Plant Growth Regulator, Fungicide, Insecticide

Substance groups

Amide herbicide

Minimum active substance purity

987 g kg⁻¹

Known relevant impurities

EU dossier - Aniline <5 mg kg⁻¹, 4-aminobiphenyl <2 mg kg⁻¹, 2-aminobiphenyl 6.5 mg kg⁻¹

Substance origin

Synthetic

Mode of action

An inhibitor of polyene and isoprene biosynthesis

CAS RN

122-39-4

EC number

204-539-4

CIPAC number

460

US EPA chemical code

038501

PubChem CID

11487

CLP index number

612-026-00-5

Molecular mass

169.23

PIN (Preferred Identification Name)

N-phenylaniline

IUPAC name

diphenylamine

CAS name

N-phenylbenzenamine

Other status information

WFD - phs; Chemical subject to PIC regulations

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 known

Fungicide Resistance Class (FRAC MOA class)

Not known

Examples of recorded resistance

Physical state

White to tan coloured crystalline powder

Formulations

Property

Value

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

Cerexagri SA

Example products using this active

No Scald DPA 31

Formulation and application details

Usually supplied as an emulsifiable concentrate that is diluted with water and used as a post-harvest drench.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

25.8

Low

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

37000

n-Hexane

450000

Methanol

1000000

Acetone

1000000

Ethyl acetate

Melting point (°C)

Boiling point (°C)

298.8

Degradation point (°C)

Flashpoint (°C)

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

6.61 X 10⁰³

Calculated

Log P

3.82

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

1.03

Strong acid

Vapour pressure at 20 °C (mPa)

85.20

at 25 °C

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)

0.321

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral solution: 204nm = 4.49, 284nm = 4.32
Acidic solution: 204nm = 4.75, 284nm = 4.57
Basic solution: 204nm = 4.37, 284nm = 4.37

Surface tension (mN m⁻¹)

71.8

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

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

0.2

Fast

Note

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

Value

353

Persistent

Note

pH variable: 316 days at pH 5, 352 days at pH 7, 359 days at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

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)

Non-mobile

K_oc (mL g⁻¹)

4104

Notes and range

Literature values range 1212-6590 mL g⁻¹

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

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

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

0.642

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

carbazole

Water (Photolysis)

hydroxydiphenylamine

Water (Photolysis)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 15000

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

Colinus virginianus

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)

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)

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)

2.2

Oncorhynchus mykiss

Moderate

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

0.71

Oncorhynchus mykiss

Moderate

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

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

1.2

Daphnia magna

Moderate

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

> 0.38

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

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

0.30

Pseudokirchneriella subcapitata

Moderate

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

0.04

Selenastrum capricornutum

Moderate

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)

> 15000

Rat

Low

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

7500

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

0.075

Rat SF=100

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

None allocated

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

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

0.1

Dog 90day SF=100

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to the public and consumers

Occupational

Potential exposure via dermal contact - PPC advised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Dog

Mammalian dose elimination route and rate

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

Eye irritant

Phototoxicant

No data found

General human health issues

Gastrointestinal, cardiovascular, kidney and liver toxicant
May cause methemoglobinemia
Maycause splenic congestion

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H315, H317
Environment: H413

WHO Classification

Not listed (Not listed)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

diphenylamine

French

German

Danish

Italian

Spanish

difenilamina

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	21/08/2024
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