Clodinafop propargyl (Ref: CGA 184927)

Clodinafop propargyl (Ref: CGA 184927)	Last updated: 21/08/2024
(Also known as: clodinafoppropargyl)

SUMMARY

Clodinafop-propargyl is a commonly used herbicide. It has a low aqueous solubility and is not volatile. It tends not to be environmentally persistent and is not expected to leach to groundwater. It is moderately toxic to most biodiversity. It has a moderate mammalian toxicity and is a possible carcinogen. It is also a skin, eye and respiratory irritant.

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: Slightly mobile	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Possible Carcinogen; Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

A herbicide for annual grass weed control in a range of crops

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

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2029

GB LERAP status

Cat B

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Greece/Germany

Date EC 1107/2009 inclusion expires

15/12/2025

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
		✓	✓	✓	✓

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, Morocco

Chemical structure

Isomerism

Clodinafop-propargyl is the R-enantiomer of a chiral molecule

Chemical formula

C₁₇H₁₃ClFNO₄

Canonical SMILES

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

Isomeric SMILES

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

International Chemical Identifier key (InChIKey)

JBDHZKLJNAIJNC-LLVKDONJSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H13ClFNO4/c1-3-8-22-17(21)11(2)23-13-4-6-14(7-5-13)24-16-15(19)9-12(18)10-20-16/h1,4-7,9-11H,8H2,2H3/t11-/m1/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
clodinafop propargyl	-

General status

Pesticide type

Herbicide

Substance groups

Aryloxyphenoxypropionate herbicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic, contact acting. Inhibits fatty acid synthesis. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

CAS RN

105512-06-9

EC number

600-662-6

CIPAC number

683.225

US EPA chemical code

125203

PubChem CID

92431

CLP index number

607-625-00-3

Molecular mass

349.8

PIN (Preferred Identification Name)

prop-2-yn-1-yl (2R)-2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoate

IUPAC name

prop-2-ynyl (R)-2-[4-(5-chloro-3-fluoro-2-pyridyloxy)phenoxy]propionate

CAS name

2-propynyl (2R)-2-(4-((5-chloro-3-fluoro-2-pyridinyl)oxy)phenoxy)propanoate

Other status information

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

Alopecurus myosuroides, Avena fatua, Avena sterilis, Cynosurus echinatus

Physical state

Colourless to light beige coloured crystals

Related substances & organisms

clodinafop

Formulations

Property

Value

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

Teliton
Syngenta
Kingtai Chemicals
Goldengrass
BOC Sciences
Conquest Crop Protection Pty Ltd

Example products using this active

Topik
Cowboy
Antilope
Dynofop
Clodinafop 240
Discover Ng Herbicide
Mpower Clodinafop Herbicide
Conquest Snooker

Formulation and application details

Usually supplied as an emulsifiable concentrate that is mixed with water and applied as a spray

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)

500000

Acetone

500000

Ethyl acetate

7500

Hexane

21000

Octanol

Melting point (°C)

59.5

Boiling point (°C)

100.6

Degradation point (°C)

285

Flashpoint (°C)

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

7.94 X 10⁰³

Calculated

Log P

3.9

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.35

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.19 X 10^-03

Low volatility

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

2.79 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

Neutral solution: 226nm = 15982, 279nm = 4910, 290nm = 3550
Acidic solution: 226nm = 18988, 279nm = 6382
Basic solution: 227nm = 19045, 280nm = 6745

Surface tension (mN m⁻¹)

69.6

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.8

Non-persistent

DT₅₀ (lab at 20 °C)

0.8

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

2.5

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

1.0

Note

EU dossier lab studies DT₅₀ range 0.7-1.5 days, DT₉₀ range 0.1-4.9 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

1.0

Note

Wheat, whole plant, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

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

Value

4.8

Non-persistent

Note

pH sensitive: DT₅₀ 17.9 days at pH 4, 26.8 days at pH 5, 0.07 days at pH 9

Water-sediment DT₅₀ (days)

0.2

Fast

Water phase only DT₅₀ (days)

0.2

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

88.4

Slightly mobile

K_foc (mL g⁻¹)

1466

¹/_n

0.92

Notes and range

EU dossier kf range 2.4-311, K_foc range 252-2364 mL g⁻¹, ¹/_n range 0.80-1.04, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.08

Calculated

Low leachability

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

Value

1.04 X 10^-04

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

4.82

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

0.5

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

2-hydroxy-3-fluoro-5-chloro-pyridine (Ref: CGA 302371)

Major fraction

0.225

clodinafop (Ref: CGA 193469)

Major fraction

0.952

4-(5-chloro-3-fluoro-2-pyridinyloxy)phenol (Ref: CGA 193468)

Major fraction

0.107

DT50(soil) > 0.68days; Moderately mobile

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

4-(5-chloro-3-fluoro-2-pyridinyloxy)phenol (Ref: CGA 193468)

Water/sediment; Plant

(R)-2-[4-(6-chloro-3-fluoro-5-hydroxy-2-pyridnyloxy) phenoxy] propanoic acid

Animal (Meat, Milk, Eggs); Plant

(R)-2-(4-hydroxy-phenoxy)propionate (Ref: CGA 214111)

Plant

2-[4-(6-chloro-3-fluoro-5 hydroxy-2-pyridinyloxy) phenoxy]-propanoic acid

Plant

2-(2-[4-(5-chloro-3-fluoro-pyridin-2-yloxy)-phenoxy]propionylamino)-ethanesulfonic acid (Ref: NOA 428715)

Animal (Meat, Milk)

2-[4-(5-chloro-3-hydroxy-pyridin-2-yloxy)-phenoxy]propionic acid (Ref: CGA 215010)

Animal (Milk)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1392

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

> 68.5

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

1363

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 980 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

47.1

Colinus virginianus NOEC

Moderate

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

197

Eisenia foetida

Moderate

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

Soil micro-organisms

Nitrogen mineralisation: Up to -39% effect
Carbon mineralisation: No significant adverse effect

Dose: 1.1 mg kg⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

1.6

Folsomia candida corr

Non-target plants

> 60

Carrot Lettuce
Seedling emergence, ER₅₀
as g ha⁻¹

> 60

Carrot Lettuce
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)

> 104

Apis mellifera

Low

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

Chronic

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 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 48 hr

3.1

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

Typhlodromus pyri Protonymph

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)

0.21

Lepomis macrochirus

Moderate

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

0.10

Lepomis macrochirus

Moderate

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

0.11

Danio rerio EC₅₀ Embryo

Moderate

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

0.77

Crassostrea virginica

Moderate

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

0.23

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

0.146

Chironomus riparius

Moderate

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

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

> 1.4

Lemna gibba

Moderate

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

> 1.6

Scenedesmus subspicatus

Moderate

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

Unknown species

Low

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

1392

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.32

Rat (nose only)

Other Mammal toxicity endpoints

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

0.003

Rat SF=100

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

0.05

Rat 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)

0.026

Dog SF=100

Dermal penetration studies (%)

2.5-10.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

PPE/PPC recommended to reduce exposure risk

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

Complete metabolised and excreted via urine and faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible ovaries, prostrate and blood toxicant
US EPA - likely to be human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

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

WHO Classification

Not listed (Not listed)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions. Limied shelf-life. Store at 0-6 DegC

TRANSLATIONS

Language

Name

English

clodinafop propargyl

French

clodinafop-propargyl

German

Clodinafop

Danish

clodinafop-propargyl

Italian

clodinafop-propargyl

Spanish

clodinafop-propargil

Greek

Polish

klodinafop propargilowy

Swedish

Hungarian

klodinafop-propargil

Dutch

Norwegian

Record last updated:	21/08/2024
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