Propanil (Ref: FW 734)

Propanil (Ref: FW 734)	Last updated: 26/08/2024
(Also known as: DCPA; 3,4-DCPA; propanamide)

SUMMARY

Propanil is a post-emergence herbicide. It is moderately soluble in water and has a low volatility. It is not expected to leach to groundwater and is not usually persistent in soil or water systems. It is moderately toxic to mammals and no evidence of serious human health impact have been identified. It is, however, moderately toxic to most fauna and flora.

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: Drainflow: Moderately mobile	Ecotoxicity High alert: Fish chronic ecotoxicity: High	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

Description

A post-emergence herbicide used for broad-leaved and annual grass weed control in rice and other crops

Example pests controlled

Barnyard grass; Morning glory; Crabgrass; Annual sedges; Late watergrass; Junglerice; Prickly grass

Example applications

Rice; Potatoes; Wheat

Efficacy & activity

Has been used extensively in agriculture for many years. Efficiacy tested via field trials.

Availability status

Current

Introduction & key dates

1960, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK 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

Italy

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

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

Australia, USA

Chemical structure

Isomerism

None

Chemical formula

C₉H₉Cl₂NO

Canonical SMILES

CCC(=O)NC1=CC(=C(C=C1)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

LFULEKSKNZEWOE-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H9Cl2NO/c1-2-9(13)12-6-3-4-7(10)8(11)5-6/h3-5H,2H2,1H3,(H,12,13)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
propanil	-

General status

Pesticide type

Herbicide

Substance groups

Anilide herbicide

Minimum active substance purity

>984 g/Kg

Known relevant impurities

EU dossier: 2,3-DCA <0.5g kg⁻¹; 3,4-DCA <2.7g kg⁻¹; TCBA <2mg kg⁻¹; TCAOB <0.9 mg kg⁻¹

Substance origin

Synthetic

Mode of action

Selective with contact action, inhibition of photosynthesis

CAS RN

709-98-8

EC number

211-914-6

CIPAC number

205

US EPA chemical code

028201

PubChem CID

4933

CLP index number

616-009-00-3

Molecular mass

218.08

PIN (Preferred Identification Name)

IUPAC name

3',4'-dichloropropionanilide

CAS name

N-(3,4-dichlorophenyl)propanamide

Other status information

Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Echinochloa colona

Physical state

Brown crystalline solid

Formulations

Property

Value

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

Rohm & Haas
Monsanto
Bayer
Vertac
BOC Sciences

Example products using this active

Arrosol
Stampede
Strel
Propanilo
Surcopur

Formulation and application details

Often supplied as emulsifiable concentrates or ULV

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

95.0

Moderate

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

664000

Acetone

650000

Methanol

34510

Xylene

598000

Ethyl acetate

Melting point (°C)

Boiling point (°C)

351

Degradation point (°C)

Greater than boiling point

Flashpoint (°C)

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

1.95 X 10⁰²

Calculated

Log P

2.29

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.412

Dissociation constant pKa) at 25 °C

19.1

Does not dissociate

Vapour pressure at 20 °C (mPa)

0.193

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

4.4 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Acid: 251nm=18471, 290nm=910
Neutral: 251nm=20037, 290nm=1374
Basic: 251nm=18659, 290nm=1033

Surface tension (mN m⁻¹)

70.4

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.4

Non-persistent

DT₅₀ (lab at 20 °C)

0.4

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

1.44

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2017 Dossier Lab studies with flooded soil (dark paddy conditions) DT₅₀ range 0.25-1.76 days; EU 2011 dossier DT₅₀ lab studies range 0.2-0.8 days; DT₉₀ range 0.6-2.8 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

37.8

Note

Kentucky bluegrass thatch, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

23.6

Slow

Note

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

Value

Stable

Note

Stable at pH 4, 7 & 9

Water-sediment DT₅₀ (days)

1.25

Fast

Water phase only DT₅₀ (days)

1.2

Moderately fast

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)

Moderately mobile

K_oc (mL g⁻¹)

149

Notes and range

DW3

Freundlich

K_f (mL g⁻¹)

6.95

Slightly mobile

K_foc (mL g⁻¹)

535

¹/_n

0.92

Notes and range

EU 2017 dossier K_f range 2.32-11.7 mL g⁻¹, K_foc range 239-800 mL g⁻¹, ¹/_n range 0.82-1.18, Soils=4

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.51

Calculated

Low leachability

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

Value

5.61 X 10^-05

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

67.90

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

Substance of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

111

Pimephales promelas

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3,4-dichloroaniline

Major fraction

0.833

Flooded soil

3,4-dichloronitrobenzene

Major fraction

0.182

Aerobic

3,3’,4,4’-tetrachloroazobenzene

Minor fraction

0.036

Aerobic

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3,4-dichloroacetanilide

Plant

3,4-dichloroglucosylamine

N-3,4-dichlorophenyl-glucosylamine; N-(3,4-dichlorophenyl)-â-D-glucopyranosylamine

Plant

3,4-dichloronitrobenzene

DCNB

Water

3,3’,4,4’-tetrachloroazoxybenzene

TCAOB

Impurity

n-hydroxy-3,4-dichloroaniline

Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

960

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

400

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

Birds - Acute LD₅₀ (mg kg⁻¹)

196

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

2792 mg kg feed⁻¹

Colinus virginianus

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

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

734

Eisenia foetida

Moderate

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

12.5

Eisenia foetida 56 day

Moderate

Soil micro-organisms

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

Dose: 91.2 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

2.25

Folsomia candida corr

Non-target plants

294.2

Brassica oleracea
Vegetative vigour, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 94.3

Apis mellifera

Moderate

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

> 246.12

Apis mellifera

Bumblebees (Bombus spp.)

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

> 100

Bombus terrestris

Low

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) as Mortality LR₅₀ g ha⁻¹

> 13700

Aphidius rhopalosiphi corr

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 950

Typhlodromus pyri corr

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)

5.4

Oncorhynchus mykiss

Moderate

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

0.0004

Pimephales promelas

High

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

> 1.76

Danio rerio EC₅₀ Embryo

Moderate

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

2.39

Daphnia magna

Moderate

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

0.086

Daphnia magna

Moderate

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

> 0.1

Ceriodaphnia dubia LC₅₀

Moderate

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

> 0.35

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

1.9

Chironomus riparius

Moderate

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

16.0

Chironomus riparius

Moderate

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

5.8

Lemna gibba

Moderate

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

0.11

Selenastrum capricornutum

Moderate

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

0.916

Chlamydomonas moewusii

Moderate

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)

960

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.25

Rat 4 hr

Other Mammal toxicity endpoints

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

0.02

Dog SF=300

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

0.07

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)

0.02

Dog SF=300

Dermal penetration studies (%)

2-12.4

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Risk to bystanders are minimal when used as proposed

Occupational

Potential risks - PPE/PPC required

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapid and extensive mainly via urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

Possible liver, kidney, spleen and testes toxicant
US EPA - weak evidence to suggest possible human carcinogen
Endocrine issues - Increase of cellular response to estrogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302
Environment: H400

WHO Classification

II (Moderately hazardous)

UN Number

UN3077

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Store at -20 DegC

TRANSLATIONS

Language

Name

English

propanil

French

propanil

German

Propanil

Danish

propanil

Italian

propanil

Spanish

propanil

Greek

propanil

Polish

propanil

Swedish

Hungarian

Dutch

propanil

Norwegian

Record last updated:	26/08/2024
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