Diphenylamine

Diphenylamine	Last updated: 17/01/2021
(Also known as: DPA; anilinobenzene)

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

Unknown

Introduction & key dates

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 Directive 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

Also used in

Chemical structure

Isomerism

Chemical formula

C₁₂H₁₁N

Canonical SMILES

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

Isomeric SMILES

No data

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 group

Amine

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

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not known

Fungicide Resistance Classification (FRAC)

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

No Scald DPA 31

Example products using this active

Cerexagri SA

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)

Not expected to self ignite; Not highly flammable

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

6.61 X 10⁰³

Calculated

Log P

3.82

High

Bulk density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

1.03

Strong acid

Vapour pressure at 20 °C (mPa)

0.852

Low volatility

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

0.321

Moderately volatile

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

4104

Notes and range

Literature values range 1212-6590 mL g⁻¹

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

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

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

carbazole

Water (Photolysis)

hydroxydiphenylamine

Water (Photolysis)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

2.2

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.71

Oncorhynchus mykiss

Moderate

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

1.2

Daphnia magna

Moderate

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

> 0.38

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)

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)

0.30

Pseudokirchneriella subcapitata

Moderate

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

0.04

Selenastrum capricornutum

Moderate

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)

> 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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Dog

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 Code is usually 9 or 6.1

CLP classification 2013

Health: H315, H317
Environment: H413

EC Risk Classification

T - Toxic: R23, R24, R25, R33
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S28, S36/37, S45, S60, S61

WHO Classification

NL (Not listed)

UN Number

Usualy 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

diphenylamine

French

German

Danish

Italian

Spanish

difenilamina

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	17/01/2021
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