Diclofop (Ref: AE F021079)

Diclofop (Ref: AE F021079)	Last updated: 12/01/2021
(Also known as: diclofop acid; diclofop free acid; HOE 021079)

GENERAL INFORMATION

Description

Post-emergence herbicide usually used as the methyl variant. Also a pesticide transformation product

Example pests controlled

Wild oats; Crowsfoot grass; Annual ryegrass; Common barbgrass

Example applications

Vegetables including brassicas, beans, carrots, peas, parsnips, onions; Sugarbeet; Cereals including barley, wheat; Oilseed rape; Potatoes

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1982

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Portugal/France

Date EC 1107/2009 inclusion expires

31/05/2021

EU Candidate for substitution (CfS)

Yes - low ADI / ARfD / AOEL

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

A chiral molecule. The technical material is an isomeric mixture.

Chemical formula

C₁₅H₁₂Cl₂O₄

Canonical SMILES

CC(C(=O)O)OC1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

OOLBCHYXZDXLDS-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H12Cl2O4/c1-9(15(18)19)20-11-3-5-12(6-4-11)21-14-7-2-10(16)8-13(14)17/h2-9H,1H3,(H,18,19)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
diclofop-methyl	Derivative

General status

Pesticide type

Herbicide, Metabolite

Metabolite Type

Soil

Substance group

Aryloxyphenoxypropionate

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, absorbed by leaves and inhibits fatty acid synthesis. Inhibition of acetyl CoA carboxylase (ACCase)

CAS RN

40843-25-2

EC number

CIPAC number

358

US EPA chemical code

110902

PubChem CID

38687

Molecular mass

327.16

PIN (Preferred Identification Name)

rac-(2R)-2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid

IUPAC name

(RS)-2-[4-(2,4-dichlorophenoxy)phenoxy]propionic acid

CAS name

2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid

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

Pale yellow solid

Related substances & organisms

diclofop-phenol

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

diclofop-methyl

Soil

0.87

Formulations

Property

Value

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

Hoe-Grass
Hoelon 3EC
Illoxan
One-shot

Example products using this active

Bayer CropScience
Bayer Environmental

Formulation and application details

Usually supplied as an emulsion that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

122700

High

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

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

4.07 X 10⁰¹

Calculated

Log P

1.61

Low

Bulk density (g ml⁻¹)

1.4

Dissociation constant pKa) at 25 °C

3.43

Weak acid

Vapour pressure at 20 °C (mPa)

0.0000031

Low volatility

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

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)

23.9

Non-persistent

DT₅₀ (field)

35.2

Moderately persistent

DT₉₀ (lab at 20 °C)

84.7

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 5.1-74.0 days, DT₉₀ range 23.3-246 days, Field studies DT₅₀ range 25.7-52.2 days ; General literature DT₅₀ range 10 days (sand) - 30 days (sandy clay)

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)

58.3

Moderately fast

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

6.3

Moderately mobile

K_foc

289

¹/_n

0.882

Notes and range

EU dossier kf range 0.76-13.54 mL g⁻¹, kfoc range 148-505.5 mL g⁻¹, ¹/_n range 0.819-0.913, Soils=6

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.38

Calculated

Transition state

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

Value

1.24 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)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 586

Rat

Moderate

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)

> 10000

Phasianidae

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)

> 100

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

16.0

Oncorhynchus mykiss

Low

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

Daphnia magna

Moderate

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

0.0156

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)

Chironomus riparius

Moderate

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)

10.4

Pseudokirchneriella subcapitata

Low

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

as methyl variant

Low

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

> 131

as methyl variant

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)

> 500

Eisenia foetida corr

Moderate

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)

> 586

Rat

Moderate

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

0.001

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

0.03

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.003

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Readily absorbed through the gastrointestinal tract

MRLs

European

EU MRL pesticide database

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Kidney and liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H302, H317
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22, R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S24, S37, S60, S61

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

diclofop

French

German

Danish

Italian

Spanish

Greek

Polish

dichlofop

Swedish

Hungarian

Dutch

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