Clodinafop (Ref: CGA 193469)

Clodinafop (Ref: CGA 193469)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A herbicide for annual grass weed control usually used as the propargyl variant

Example pests controlled

Wild oats; Paradoxa grass; Canary grass; Annual ryegrass

Example applications

Cereals including wheat, triticale and rye

Efficacy & activity

Availability status

Current

Introduction & key dates

1989, first reported; 1990, first marketed

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Greece/Denmark

Date EC 1107/2009 inclusion expires

30/04/2021

EU Candidate for substitution (CfS)

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.

Chemical formula

C₁₄H₁₁ClFNO₄

Canonical SMILES

CC(C(=O)O)OC1=CC=C(C=C1)OC2=NC=C(C=C2F)Cl

Isomeric SMILES

C[C@H](C(=O)O)OC1=CC=C(C=C1)OC2=NC=C(C=C2F)Cl

International Chemical Identifier key (InChIKey)

YUIKUTLBPMDDNQ-MRVPVSSYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H11ClFNO4/c1-8(14(18)19)20-10-2-4-11(5-3-10)21-13-12(16)6-9(15)7-17-13/h2-8H,1H3,(H,18,19)/t8-/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide, Metabolite, Plant growth regulator

Metabolite Type

Soil

Substance group

Aryloxyphenoxypropionate

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Systemic, contact acting. Inhibits fatty acid synthesis. Inhibition of acetyl CoA carboxylase (ACCase)

CAS RN

114420-56-3

EC number

CIPAC number

683

US EPA chemical code

PubChem CID

5483847

Molecular mass

311.69

PIN (Preferred Identification Name)

(2R)-2-(4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy)propanoic acid

IUPAC name

(R)-2-[4-(5-chloro-3-fluoro-2-pyridyloxy)phenoxy]propionic acid

CAS name

(2R)-2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]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

Related substances & organisms

clodinafop-propargyl

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

clodinafop-propargyl

Soil

0.95

Major fraction, Relevant

Formulations

Property

Value

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

Example products using this active

Syngenta
Novartis

Formulation and application details

Formulations normally use the propargyl variant

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

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

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.63 X 10^-01

Calculated

Log P

-0.44

Low

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

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

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

12.35

Non-persistent

DT₅₀ (lab at 20 °C)

12.35

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

38.3

non-normalised worse case

Note

EU 2017 dossier lab studies DT₅₀ range 6.3-50.4 days, DT₉₀ range 16-127 days, Field studies DT₅₀ range 4.6-13 days (Germany), 19-33 days (UK)

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

Stable

Note

Stable pH 4- pH 8.8 at 50 °C

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

K_oc

Notes and range

Freundlich

K_f

1.18

Mobile

K_foc

57.1

¹/_n

0.819

Notes and range

EU dossier kf range 0.217-2.23 mL g⁻¹, K_foc range 25.3-81.0 mL g⁻¹, ¹/_n range 0.73-0.99, Soils=9

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.97

Calculated

High leachability

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

Value

2.14 X 10^-01

Calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

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)

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)

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 76.0

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

4.1

Pimephales promelas

Moderate

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

> 10

Daphnia magna

Moderate

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

0.16

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)

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

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

4.5

Lemna gibba

Moderate

Non-target plants

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

2.0

Scenedemus subspicatus

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)

40.9

as propargyl variant

Moderate

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

> 93.7

as propargyl variant

Moderate

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)

197

Eisenia foetida as propargyl variant

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

251

Folsomia candida EC10

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)

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)

0.003

EU 2006

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

0.05

EU 2006

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

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

0.026

EU 2006

Dermal penetration studies (%)

2.5-10.0

EU 2006 concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

; ; ; ;

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

No information available

CLP classification 2013

Health: H302, H317, H373
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22, R48/22, R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S24, S36/37, S60, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

clodinafop

French

German

Danish

Italian

Spanish

Greek

Polish

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