| clodinafop-propargyl (Ref: CGA 184927) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for clodinafop-propargyl
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
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Greece/Germany |
| Date inclusion expires | 30/04/2019 |
| EU Candidate for substitution (CfS) | No |
| Listed in EU database | Yes |
Approved for use (
) or known to be used (
) in the following European countries: 
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
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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 |
General status:
| Pesticide type | Herbicide | |
| Substance group | Aryloxyphenoxypropionate | |
| Minimum active substance purity | 950 g/kg | |
| 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 (g mol-1) | 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) | A | |
| Herbicide Resistance Classification (WSSA) | 1 | |
| 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 | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | None | |||
| Formulation and application details | Usually supplied as an emulsifiable concentrate that is mixed with water and applied as a spray. | |||
ENVIRONMENTAL FATE
for clodinafop-propargyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 4 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 500000 | A5 - Acetone | - | |
| 500000 | A5 - Ethyl acetate | - | ||
| 7500 | A5 - Hexane | - | ||
| 21000 | A5 - Octanol | - | ||
| Melting point (oC) | 59.5 | A5 | - | |
| Boiling point (oC) | 100.6 | A5 | - | |
| Degradation point (oC) | 285 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 7.94 X 1003 | Calculated | - |
| Log P | 3.9 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.35 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 3.19 X 10-03 | B5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.79 X 10-04 | A5 | Non-volatile | |
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 |
- | Calculated | Low | |
| 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 | A5 | - | |
| Surface tension (mN m-1) | 69.6 | A5 at 20oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | Not readily biodegradable |
| Soil degradation (days) (aerobic) | DT50 (typical) | 0.8 |
A5 | Non-persistent |
| DT50 (lab at 20oC) | 0.8 | A5 | Non-persistent | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | 2.5 | A5 | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | 1.0 | A4 | - | |
| 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 | R3 | - |
| Note | Wheat, whole plant, n=1 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 24 | A5 | Slow |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 4.8 | A5 | 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 | A5 | Fast | |
| Water phase only DT50 (days) | 0.2 | A5 | Fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 88.4 | A5 | Slightly mobile |
| Kfoc | 1466 | |||
| 1/n | 0.92 | |||
| Notes and range | EU dossier kf range 2.4-311, Kfoc range 252-2364 mL/g, 1/n range 0.80-1.04, Soils=5 | |||
| pH sensitivity | No | |||
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 |
| 2-[4-(6-chloro-3-fluoro-5 hydroxy-2-pyridinyloxy) phenoxy]-propanoic acid | II2 metabolite | Plant | - | - |
| - | CGA 193469-pentanoic acid | Animal (Meat, Eggs) | - | - |
| - | 5-OH-CGA 193469 | Animal (Meat, Milk, Eggs) | - | - |
| 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-(5-chloro-3-hydroxy-pyridin-2-yloxy)-phenoxy]propionic acid (Ref: CGA 215010) |
- | Animal (Milk) | - | - |
| 2-(2-[4-(5-chloro-3-fluoro-pyridin-2-yloxy)-phenoxy]propionylamino)-ethanesulfonic acid (Ref: NOA 428715) |
- | Animal (Meat, Milk) | - | - |
ECOTOXICOLOGY
for clodinafop-propargyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 34 | A4 | Low potential |
| CT50 (days) | 0.5 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 1392 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 1 | B5 Rat | High |
| (ppm diet) | 15 | - | ||
| Birds - Acute LD50 (mg kg-1) | 1363 | A5 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | > 980 mg kg bw-1 day-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.21 | A5 Lepomis macrochirus | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.10 | A5 Lepomis macrochirus | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.77 | A4 Crassostrea virginica | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.23 | A5 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 | A4 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 | A5 Lemna gibba | Moderate | |
| Non-target plants | > 60 | A5 Carrot, Lettuce Seedling emergence, ER50 as g/ha |
- | |
| > 60 | A5 Carrot, Lettuce Vegetative vigour, ER50 as g/ha |
- | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 1.6 | A5 Scenedemus subspicatus | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 62 | Q2 Unknown species | Low | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 40.9 | A5 | Moderate |
| Oral acute 48 hour LD50 (μg bee-1) | > 93.7 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 197 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 3.1 | 48 hour A5 Aphidius rhopalosiphi, adult |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 20 | 7 day A5 Typhlodromus pyri, protonymph |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: Up to -39% effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.1 mg kg-1, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for clodinafop-propargyl
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | 1392 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 2.32 | A5 Rat (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.003 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.05 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.026 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 2.5-10.0 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | PPE/PPC recommended to reduce exposure risk | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Possible ovaries, prostrate and blood toxicant | |||||||
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H302, H317, H373 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R22, R43, R48/22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S24, S36/37, S46, S60, S61 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | No consensus across products | - | - | |
| UN Number | Usually 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for clodinafop-propargyl
| Language | Name |
| English | clodinafop-propargyl |
| French | clodinafop-propargyl |
| German | Clodinafop |
| Danish | clodinafop-propargyl |
| Italian | clodinafop-propargyl |
| Spanish | clodinafop-propargil |
| Greek | - |
| Slovenian | klodinafop-propargil |
| Polish | klodinafop propargilowy |
| Swedish | - |
| Hungarian | klodinafop-propargil |
| Dutch | - |
Record last updated: Friday 14 September 2018
Contact: aeru@herts.ac.uk