Diphenamid (Ref: L 34314)

Diphenamid (Ref: L 34314)	Last updated: 15/09/2021
(Also known as: diphenamide; diphenylamide; difenamide)

SUMMARY

Diphenamid is a selective herbicide for annual grasses and some broad-leaved weeds. It is moderatly soluble in water and has a low volatility. It is expected to moderately persistent in soils. There are significant gaps in ecotoxicological data but diphenamid is highly toxic to aquatic invertebrates, moderately toxic to fish, and has a low avian and honeybee toxicity. The susbtance has a moderate oral mammalian toxicity.

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: GUS: Transition state; Drainflow: Moderately mobile Warning: Significant data are missing	Ecotoxicity High alert: Daphnia acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate

GENERAL INFORMATION

Description

A herbicide used for pre-emergence control of annual grasses and some broad-leaved weeds

Example pests controlled

Annual bluegrass; Annual sedge; Barnyard grass; Crabgrass; Foxtail; Nettles; Chickweed

Example applications

Peanuts; Tobacco; Sweet potatoes; Cotton; Soybeans; Fruit including apple, peach, orange, lime, cherry; Ornamental lawns

Efficacy & activity

Availability status

Introduction & key dates

circa 1960

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

Not applicable

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

C₁₆H₁₇NO

Canonical SMILES

CN(C)C(=O)C(C1=CC=CC=C1)C2=CC=CC=C2

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

QAHFOPIILNICLA-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H17NO/c1-17(2)16(18)15(13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12,15H,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Alkanamide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective, systemic, absorbed through roots. Inhibition of VLCFA (inhibition of cell division).

CAS RN

957-51-7

EC number

213-482-4

CIPAC number

372

US EPA chemical code

036601

PubChem CID

13728

Molecular mass

239.31

PIN (Preferred Identification Name)

N,N-dimethyl-2,2-diphenylacetamide

IUPAC name

N,N-dimethyldiphenylacetamide

CAS name

N,N-dimethyl-α-phenylbenzeneacetamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Colourless crystals

Formulations

Property

Value

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

Elanco
UpJohn

Example products using this active

Dymid
Enide

Formulation and application details

Supplied in a variety of formulations including wettable powders, liquid dispersions and granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

260

Moderate

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

189000

Acetone

50000

Xylene

Melting point (°C)

135

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.48 X 10⁰²

Calculated

Log P

2.17

Low

Bulk density (g ml⁻¹)

1.17

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

3.04 X 10^-03

at 25 °C

Low volatility

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

3.68 X 10^-06

at 25 °C

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)

Moderately 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

Moderately mobile

K_oc

210

Notes and range

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

2.48

Calculated

Transition state

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

Value

1.35 X 10^-01

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)

Estimated

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

970

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(ppm diet)

2000

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

Birds - Acute LD₅₀ (mg kg⁻¹)

30000

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)

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.058

Daphnia magna

High

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)

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)

2432

Low

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)

970

Rat

Moderate

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

225

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

Occupational

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

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Prevent generation of dust

CLP classification 2013

Health: H302
Environment: H412

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R52, R53

EC Safety Classification

S2, S61

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

diphenamid

French

difenamide

German

Diphenamid

Danish

diphenamid

Italian

difenamide

Spanish

difenamida

Greek

diphenamid

Polish

difenamid

Swedish

Hungarian

Dutch

difenamide

Record last updated:	15/09/2021
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