Clodinafop-propargyl (Ref: CGA 184927)

Clodinafop-propargyl (Ref: CGA 184927)	Last updated: 12/01/2021
(Also known as: clodinafoppropargyl)

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

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/Germany

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

Australia

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 group

Aryloxyphenoxypropionate

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. Inhibition of acetyl CoA carboxylase (ACCase)

CAS RN

105512-06-9

EC number

CIPAC number

683.225

US EPA chemical code

125203

PubChem CID

92431

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 Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

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

pinoxaden

trifluralin

cloquintocet-mexyl

clodinafop

Formulations

Property

Value

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

Topik
Cowboy
Antilope
Dynofop
Clodinafop 240

Example products using this active

Teliton
Syngenta
Kingtai Chemicals
Goldengrass

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)

Not expected to self ignite; Not highly flammable

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

7.94 X 10⁰³

Calculated

Log P

3.9

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

88.4

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.225

Major fraction, Relevant

clodinafop (Ref: CGA 193469)

Soil

0.95

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-(5-chloro-3-fluoro-2-pyridinyloxy)phenol (Ref: CGA 193468)
Note: DT50(soil) > 0.68days; Moderately mobile

Water/sediment; Plant; Soil

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

Plant

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

II2 metabolite

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)

CGA 193469-pentanoic acid

Animal (Meat, Eggs)

5-OH-CGA 193469

Animal (Meat, Milk, Eggs)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

0.5

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

Colinius virginianus NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.21

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.10

Lepomis macrochirus

Moderate

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

0.77

Crassostrea virginica

Moderate

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

0.23

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)

1.2

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

Non-target plants

> 60

Carrot Lettuce
Seedling emergence, ER₅₀
as g ha⁻¹

> 60

Carrot Lettuce
Vegetative vigour, ER₅₀
as g ha⁻¹

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

> 1.6

Scenedemus subspicatus

Moderate

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

Unknown species

Low

Honeybees (Apis spp.)

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

40.9

Apis mellifera

Moderate

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

> 93.7

Apis mellifera

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

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

1.6

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

3.1

48 hour
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

7 day
Typhlodromus pyri protonymph

% Effect

Soil micro-organisms

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

Dose: 1.1 mg kg⁻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)

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

Notes

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible ovaries, prostrate and blood toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

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

EC Risk Classification

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

EC Safety Classification

S2, S24, S36/37, S46, S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

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

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