Difenoxuron (Ref: C3470)

Difenoxuron (Ref: C3470)	Last updated: 29/06/2019
(Not known by any other names)

SUMMARY

Difenoxuron is a selective, post-emergence herbicide that is no longer approved for use in many countries including the EU. It has a low aqueous solubility, moderately mobile but not usually persistent in soil systems. However, it may persist in some water systems depending upon conditions. It is moderately toxic to mammals but knot known to cause any chronic health issues unless ingested at very high doses. It is moderately toxic to fish, aquatic invertebrates and algae. It is not considered to be toxic to honeybees.

GENERAL INFORMATION

Description

An obsolete selective, post-emergence herbicide that was used to control annual broad-leaved weeds in alliums.

Example pests controlled

Nettles; Docks; Chickweed; Charlock

Example applications

Onions; Garlic; Shallots; Leeks

Efficacy & activity

Availability status

Obsolete

Introduction & key dates

1964, first reported

UK regulatory status

UK approval status

Not approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes

Approved for use (✓) or known to be used (#) in the following EU-27 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

C₁₆H₁₈N₂O₃

Canonical SMILES

CN(C)C(=O)NC1=CC=C(C=C1)OC2=CC=C(C=C2)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

AMVYOVYGIJXTQB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H18N2O3/c1-18(2)16(19)17-12-4-6-14(7-5-12)21-15-10-8-13(20-3)9-11-15/h4-11H,1-3H3,(H,17,19)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Phenylurea

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibition of photosynthesis, absorbed by roots and translocated.

CAS RN

14214-32-5

EC number

238-068-0

CIPAC number

8108

US EPA chemical code

551400

PubChem CID

26576

Molecular mass

286.33

PIN (Preferred Identification Name)

N'-[4-(4-methoxyphenoxy)phenyl]-N,N-dimethylurea

IUPAC name

3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea

CAS name

N'-[4-(4-methoxyphenoxy)phenyl]-N,N-dimethylurea

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not known

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Colourless crystalline solid

Formulations

Property

Value

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

Lironion
Pinoran

Example products using this active

Ciba-Geigy
Novartis

UK LERAP status

No UK approval for use as a pesticide under EC Regulation 1107/2009

Formulation and application details

Usually supplied as a wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Low

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

156000

Dichloromethane

63000

Acetone

8000

Benzene

Hexane

Melting point (°C)

138

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.58 X 10⁰²

Calculated

Log P

2.2

Low

Bulk density (g ml⁻¹)

1.19

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C

1.20 X 10⁰³

Highly volatile

Henry's law constant at 25 °C

1.28 X 10^-07

Non-volatile

GUS leaching potential index

2.14

Calculated

Transition state

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

Value

7.21 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

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)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Lierature data DT₅₀ 10-20 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

0.12

Fast

Note

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

Value

950

Very persistent

Note

Water-sediment DT₅₀ (days)

Moderately fast

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

199

Notes and range

Best available data

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

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)

> 1000

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

10.7

Unknown species

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

Unknown species

Moderate

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)

0.03

Unknown species

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)

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)

Non-toxic

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)

> 1000

Rat

Moderate

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

2150

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.66

Rat

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

Low risk to Europeans as no longer approved for use

Occupational

Low risk to Europeans as no longer approved for use

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302, H331

EC Risk Classification

Xn - Harmful: R22

EC Safety Classification

Health: H301, H311

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

difenoxuron

French

difenoxuron

German

Difenoxuron

Danish

difenoxuron

Italian

difenoxuron

Spanish

difenoxuron

Greek

Polish

difenoksuron

Swedish

Hungarian

Dutch

difenoxuron

Record last updated:	29/06/2019
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