Aclonifen (Ref: AE F068300)

Aclonifen (Ref: AE F068300)	Last updated: 12/01/2021
(Also known as: aclonifene; RPA 099795)

SUMMARY

Aclonifen is a herbicide that is currently not approved for EU use. It is not highly soluble in water but is in many organic solvents. It is non-volatile and is not expected to leach to groundwater. It is moderately persistence in soil systems and can be very persistent in aquatic systems under certain conditions. It has a low mammalian toxicity and may bioaccumulate. It is a recognised skin irritant. It is relatively non-toxic to birds and honeybees but more so to most aquatic organisms.

GENERAL INFORMATION

Description

A nitrophenyl ether herbicide used for the pre-emergence control of grass and broad-leaved weeds

Example pests controlled

Buckwheat; Carpetweed; Cocklebur; Lady's thumb; Morning glory; Moonflower; Nighshade; Pigweed; Waterhelp; Foxtails

Example applications

Soybeans; Peanuts; Beans and peas: Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1983

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2025

UK LERAP status

Crop over 5m DRT - See Authorisation for Crop LERAP Details

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Germany

Date EC 1107/2009 inclusion expires

31/07/2022

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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

C₁₂H₉ClN₂O₃

Canonical SMILES

C1=CC=C(C=C1)OC2=C(C(=C(C=C2)[N+](=O)[O-])N)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

DDBMQDADIHOWIC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H9ClN2O3/c13-11-10(18-8-4-2-1-3-5-8)7-6-9(12(11)14)15(16)17/h1-7H,14H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Diphenyl ether

Minimum active substance purity

Known relevant impurities

EU dossier - Phenol

Substance origin

Synthetic

Mode of action

Systemic and selective. Inhibition of carotenoid biosynthesis.

CAS RN

74070-46-5

EC number

277-704-1

CIPAC number

498

US EPA chemical code

PubChem CID

92389

Molecular mass

264.66

PIN (Preferred Identification Name)

2-chloro-6-nitro-3-phenoxyaniline

IUPAC name

2-chloro-6-nitro-3-phenoxyaniline

CAS name

2-chloro-6-nitro-3-phenoxybenzenamine

Other status information

PAN listed Highly Hazardous Chemical

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

Yellow powder or crystals

Formulations

Property

Value

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

Bandur
Mikado

Example products using this active

Formulation and application details

Usually supplied as a suspension concentrate that is mixed with water and applied as a spary

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.4

Low

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

4800

n-Hexane

442000

Toluene

49200

Methanol

730000

Acetone

Melting point (°C)

81.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

297

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.34 X 10⁰⁴

Calculated

Log P

4.37

High

Bulk density (g ml⁻¹)

1.46

Dissociation constant pKa) at 25 °C

-3.15

Very strong acid

Vapour pressure at 20 °C (mPa)

0.016

Low volatility

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

3.03 X 10^-03

Non-volatile

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

Neutral solution: 238nm = 18987, 310nm = 8431, 390nm = 6143

Surface tension (mN m⁻¹)

72.0

20 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

117

Persistent

DT₅₀ (lab at 20 °C)

62.3

Moderately persistent

DT₅₀ (field)

80.4

Moderately persistent

DT₉₀ (lab at 20 °C)

364

Persistent

DT₉₀ (field)

316

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 29.5-93.6 days, DT₉₀ range 107-740 days; field studies DT₅₀ range 13-195 days, DT₉₀ range 104-649 days

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

197

Stable

Note

Not a major route of degradation. Calculated values range 9-1040 days depending on sunlight levels and temp

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

Value

Stable

Note

Stable between pH 5 and pH 9, 22-70 °C

Water-sediment DT₅₀ (days)

14.3

Fast

Water phase only DT₅₀ (days)

4.2

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

138.1

Non-mobile

K_foc

7126

¹/_n

0.922

Notes and range

K_f range 58.5-265.3, K_foc range 5318-10612 mL g⁻¹, ¹/_n range 0.878-1.003, Soils=3

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.28

Calculated

Low leachability

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

Value

7.54 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-amino-2-chloro-4-nitrophenol (Ref: RPA 508285)

Plant

4-(3-amino-2-chloro-4-nitrophenoxy)phenol (Ref: RPA 407074)

Plant

3-chloro-4-phenoxybenzene-1,2-diamine (Ref: RPA 407291)

Plant

3,4-diamino-2-chlorophenol (Ref: RPA 407288)

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

2896

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 50

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

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)

0.67

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.005

Pimephales promelas

High

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

1.2

Daphnia magna

Moderate

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

0.016

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)

0.472

Chironomus riparius

Moderate

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

32.0

Chironomus riparius

Moderate

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

0.006

Lemna gibba

High

Non-target plants

13.7

Brassica napus
Vegetative vigour, ER₅₀
as g ha⁻¹

25.7

Brassica napus
Seedling emergence, ER₅₀
as g ha⁻¹

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

0.47

Navicula pelliculosa

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

Apis mellifera

Low

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

> 107

Apis mellifera

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)

150

Eisenia foetida corr

Moderate

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

Eisenia andrei corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

126.2

Hypoaspis aculeifer

Chronic NOEC (mg kg⁻¹)

13.3

Hypoaspis aculeifer

Other arthropod (1)

LR₅₀ g ha⁻¹

2930

>, 48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

102

7 day, Mortality
Typhlodromus pyri

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect [Dose: 15 kg ha⁻¹, 28 days]
Carbon mineralisation: 8% Effect sand [Dose: 3 kg ha⁻¹, 28 days]
Carbon mineralisation: 22% Effect loam [Dose: 15 kg ha⁻¹, 28 days]

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

5.06

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.07

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)

0.07

Rat SF=100

Dermal penetration studies (%)

2-10

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Risk of exposure to bystanders from spray drift, but acceptable risk level for proposed used
Very low risk of exposure via diet

Occupational

Main risk from dermal absorption during preparation and mixing
Acceptable risk level for proposed uses

European MRLs

EU MRL pesticide database

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible kidney toxicant

Handling issues

Property

Value and interpretation

General

No information available
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317, H351
Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

aclonifen

French

aclonifene

German

Aclonifen

Danish

aclonifen

Italian

aclonifen

Spanish

aclonifen

Greek

Polish

aklonifen

Swedish

aklonifen

Hungarian

Dutch

aclonifen

Record last updated:	12/01/2021
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