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Clodinafop

PubChem CID
5483847
Structure
Clodinafop_small.png
Clodinafop_3D_Structure.png
Molecular Formula
Synonyms
  • Clodinafop
  • 114420-56-3
  • (R)-Clodinafop
  • Clodinafop [ISO]
  • (2R)-2-[4-[(5-Chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoic Acid
Molecular Weight
311.69 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
Clodinafop is an aromatic ether that is (R)-lactic acid in which the hydroxy group at position 2 has been converted to the corresponding p-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenyl ether. It is the parent acid of the herbicide clodinafop-propargyl. It has a role as an EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor and a phenoxy herbicide. It is a monocarboxylic acid, a member of pyridines, an aromatic ether, an organofluorine compound and an organochlorine compound.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Clodinafop.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-[4-(5-chloro-3-fluoropyridin-2-yl)oxyphenoxy]propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 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
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

YUIKUTLBPMDDNQ-MRVPVSSYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C[C@H](C(=O)O)OC1=CC=C(C=C1)OC2=C(C=C(C=N2)Cl)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C14H11ClFNO4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

105512-06-9

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

clodinafop

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
311.69 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
3.4
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
311.0360637 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
311.0360637 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
68.7 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
21
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
352
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Cream-colored odorless solid; [HSDB] light beige crystalline solid; [MSDSonline]

3.2.2 Color / Form

Colorless crystals
Meister, R.T., Sine, C; Crop Protection Handbook Volume 94. Meister Media Worldwide, Willoughby, OH 2008, p. D 115
Crystalline solid
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 398
Cream powder
USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/

3.2.3 Odor

Odorless
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 398

3.2.4 Melting Point

59.5 °C
MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)
MP: 48.2-57.1 °C /Technical/
MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)

3.2.5 Solubility

In organic solvents at 25 °C (g/L): ethanol - 92; acetone - 880; toluene - 690; n-hexane - 0.0086; n-octanol - 25
Meister, R.T., Sine, C; Crop Protection Handbook Volume 94. Meister Media Worldwide, Willoughby, OH 2008, p. D 115
Soluble in most organic solvents
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 398
In water, 2.5 ppm at 20 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 398
In water, 4.0 mg/L at 25 °C
MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)

3.2.6 Density

1.37 g/mL at 22 °C
USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/
Liquid; density: 1.076 g/mL; pH 4-6 /End-use product/
USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/

3.2.7 Vapor Pressure

0.00000002 [mmHg]
VP: 5.3X10-6 Pa at 20 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 398
2.40X10-8 mm Hg at 25 °C
MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)

3.2.8 LogP

log Kow = 3.90 at 25 °C
MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)

3.2.9 Stability / Shelf Life

Relatively stable in acidic media at 50 °C, hydrolyses in alkaline media; DT50 (25 °C) 4.8 days (pH 7), 0.07 days (pH 9).
MacBean C, ed. Clodinafop-propargyl (105512-06-9). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.

3.2.10 Optical Rotation

Specific optical rotation: +45.4 deg at 20 °C/D (c = 2 in acetone)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 398

3.2.11 Autoignition Temperature

950 °F /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf

3.2.12 pH

pH = 4.1 at 25 °C
USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/

3.2.13 Other Experimental Properties

Relatively stable in acidic media at 50 °C; hydrolyses half-life in alkaline media (25 °C): 64 hours (pH 7), 2.2 hours (pH 9)
MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)

3.3 Chemical Classes

3.3.1 Pesticides

Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Pesticides -> Herbicides, Other
Environmental transformation -> Pesticide transformation products (metabolite, successor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Transformation products, Herbicides, Plant growth regulators
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

5 Chemical Vendors

6 Agrochemical Information

6.1 Agrochemical Category

Pesticide active substances
Transformation products, Herbicides, Plant growth regulators
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

6.2 Agrochemical Transformations

CGA 193469 is a known environmental transformation product of Clodinafop.
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

6.3 EU Pesticides Data

Active Substance
clodinafop
Status
Approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/02/2007 Expiration: 15/12/2025
Legislation
06/39/EC, Reg. (EU) 2018/524, Reg. (EU) 2019/168, Reg. (EU) 2020/421, Reg. (EU) 2021/566, Reg. (EU) 2022/378, Reg. (EU) 2023/689, Reg. (EU) No 487/2014, Reg. (EU) No 540/2011
ADI
0.003 mg/kg bw/day [Dir 06/39]
ARfD
0.05 mg/kg bw [Dir 06/39]
AOEL
0.026 mg/kg bw/day [Dir 06/39]

7 Pharmacology and Biochemistry

7.1 Absorption, Distribution and Excretion

Clodinafop-propargyl is rapidly and for at least for 75% absorbed in males (based on radiolabel recovered in urine, tissues, cage wash and residual carcass) within 168 hours. Oral absorption in females is higher (> or = 92%). The excretion is also rapid, mainly in the urine. Total excretion after 168 hours is higher in females (92-96%) than in males (66-85%). It is widely distributed and the highest concentration was found in fat, muscle, liver, blood and kidneys. Residues were higher in males than in females. There was a potential for accumulation in fat. Elimination from ovaries, pancreas, thymus and thyroid was slow.
European Food Safety Authority (EFSA); Conclusion on the Peer Review of Clodinafop; EFSA Scientific Report 34:1-78 (2005). Available from, as of June 16, 2011: https://www.efsa.europa.eu/en/efsajournal/pub/34ar.htm

7.2 Metabolism / Metabolites

/In animals,/ hydrolyzed to the corresponding acid, which is excreted in urine and feces. ... In plants, rapidly degraded to the acid derivative as major metabolite.
MacBean C, ed. Clodinafop-propargyl (105512-06-9). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
In a rat metabolism study, two (14)C-labeled variants of clodinofop-propargyl (one labeled on the 2 pyridil carbon & the other uniformly labeled on the phenyl ring, purity >98%) were admin to groups of male Tif:RAI f (SPF) rats, approx 7 wk of age by gavage at concns of 25.2 mg/kg ( [2-14C]pyridil) & 24.6 mg/kg ([U-14C]phenyl). In the urine, the major metabolite was determined to be (R)-2-[4-(5-chloro-3-fluoro-2-pyridinyloxy)-phenoxy]-propionic acid, reference material CGA-193469, accounting for 36.7% to 39.1% of the admin dose (AD). Metabolite fraction U3 hydrolysed to yield fraction U7 (i.e., CGA-193469), when treated with NaOH or HCl. Unchanged clodinofop-propargyl was not identified. In the feces, the major metabolite (fraction F*7) corresponded to the urinary metabolite U7 (CGA 193469), accounting for 15.7% to 16.9% of the AD. Metabolite fraction F*8 was determined to be unchanged clodinofop-propargyl, accounting for 0.4% to 1.7% of the AD. In the fat, all metabolites were reportedly acylglycerides, the majority of which were hybrid di- & triacylglycerides, (i.e., approx 3.5% & 17.0% of the AD, respectively).
USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Clodinafop-propargyl (Conditional Registration), p11 (June 6, 2000). Available from, as of June 16, 2011: https://www.epa.gov/opprd001/factsheets/
Clodinafop-propargyl is extensively metabolized (<0.3% remaining as clodinafop-propargyl). The major metabolites evident in the excreta were clodinafop (CGA 193469) and its taurine conjugate. The metabolites in fat were diacylglycerides and triacylglycerides of clodinafop.
European Food Safety Authority (EFSA); Conclusion on the Peer Review of Clodinafop; EFSA Journal 34:1-78 (2005). Available from, as of June 16, 2011: https://www.efsa.europa.eu/en/efsajournal/pub/34ar.htm

7.3 Mechanism of Action

Mechanistic studies were conducted to elucidate the mechanisms involved in the increased incidence of neoplastic lesions in liver in rats and mice and to assess the human relevance of these effects. Clodinafop-propargyl was shown to cause peroxisome proliferation in rodent studies. Peroxisome proliferation is a consequence of expression and activation of the alpha subtype of the peroxisome proliferator-activated receptor (PPAR-alpha). The activation of this receptor has been shown to be associated with several responses typical for peroxisome proliferators, such as hepatocellular hypertrophy, stimulation of peroxisomal fatty acid alpha-oxidation, induction of cytochrome P450 isoenzymes of subfamily CYP4A, and hepatocellular proliferation. Several studies were performed to confirm these effects. The mechanistic in vitro and in vivo studies in rodents confirm that clodinafop-propargyl causes a peroxisome proliferative response in rodents, ultimately leading to the formation of liver tumours, as observed in chronic toxicity studies with clodinafop-propargyl. Based on the non-genotoxic characteristics of clodinafop-propargyl and the peroxisome proliferative properties of clodinafop-propargyl, a threshold approach is applicable for the liver tumour formation in rats and mice.
European Food Safety Authority (EFSA); Conclusion on the Peer Review of Clodinafop; EFSA Journal 34:1-78 (2005). Available from, as of June 16, 2011: https://www.efsa.europa.eu/en/efsajournal/pub/34ar.htm
Aryloxyphenoxypropionates, inhibitors of the plastid acetyl-CoA carboxylase (ACC) of grasses, also inhibit Toxoplasma gondii ACC. Clodinafop, the most effective of the herbicides tested, inhibits growth of T. gondii in human fibroblasts by 70% at 10 microM in 2 days & effectively eliminates the parasite in 2-4 days at 10-100 microM. Clodinafop is not toxic to the host cell even at much higher concns. Parasite growth inhibition by different herbicides is correlated with their ability to inhibit ACC enzyme activity, suggesting that ACC is a target for these agents. Fragments of genes encoding the biotin carboxylase domain of multidomain ACCs of T. gondii, Plasmodium falciparum, Plasmodium knowlesi, & Cryptosporidium parvum were sequenced. One T. gondii ACC (ACC1) amino acid sequence clusters with P. falciparum ACC, P. knowlesi ACC, & the putative Cyclotella cryptica chloroplast ACC. Another sequence (ACC2) clusters with that of C. parvum ACC, probably the cytosolic form.
Zuther E, et al; Proc Natl Acad Sci USA 96 (23): 13387-13392 (1999)

7.4 Transformations

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used as oxyphenoxy acid ester herbicide for spring wheat; [Reference #1]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
For clodinafop-propargyl (USEPA/OPP Pesticide Code: 125203) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
National Pesticide Information Retrieval System's USEPA/OPP Chemical Ingredients Database on Clodinafop-propargyl (105512-06-9). Available from, as of May 23, 2011: https://npirspublic.ceris.purdue.edu/ppis/
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Clodinafop-propargyl (105511-96-4). Available from, as of April 1, 2002: https://npirspublic.ceris.purdue.edu/ppis/
Herbicide registered for use on spring wheat.
USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. June 6, 2000. Available from, as of Mar, 2002: https://www.epa.gov/opprd001/factsheets/
Used for post-emergence control of annual grasses, including Avena, lolium, Setaria, Phalaris and Alopecurus spp. and in cereals ...
MacBean C, ed. Clodinafop-propargyl (105512-06-9). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.

8.1.1 Use Classification

Environmental transformation -> Pesticide transformation products (metabolite, successor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Transformation products, Herbicides, Plant growth regulators
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

8.2 Methods of Manufacturing

Clodinafop-propargyl can be made by reaction of 2-fluoro-4-chloropyridine with propynyl 2-(4-chlorophenoxy)propionate
Muller F, Appleby A; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2011). New York, NY: John Wiley & Sons; Weed Control, 2. Individual Herbicides. Online Posting Date: September 15, 2010

8.3 Formulations / Preparations

Emulsifiable concentrate, wettable powder.
Mester, R.T.,Sine, C. (eds.) Crop Protection Handbook Volume 97. Meisterpro. Willoughby,OH. 2011, p. 303
Mester, R.T.,Sine, C. (eds.) Crop Protection Handbook Volume 97. Meisterpro. Willoughby,OH. 2011, p. 303
97.5% technical product; 22.3% end use product (Discover Herbicide)
USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. June 6, 2000. Available from, as of Mar, 2002: https://www.epa.gov/opprd001/factsheets/
Discover Herbicide (Syngenta Crop Protection, LLC) Clodinafop-propargyl 22.3%
Purdue University; National Pesticide Information Retrieval System, Clodinafop-Propargyl PC Code 125203. Available from, as of June 7, 2011: https://npirspublic.ceris.purdue.edu/ppis/
For more Formulations/Preparations (Complete) data for CLODINAFOP-PROPARGYL (6 total), please visit the HSDB record page.

9 Identification

9.1 Analytic Laboratory Methods

The petitioner has proposed residue analytical methods for tolerance enforcement that use both normal and reverse phase liquid chromatography with UV detection.
65 FR 38775 (6/22/2000)
Residues in soil by HPLC/UV, LC/MS or GC/MS
MacBean C, ed. Clodinafop-propargyl (105512-06-9). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
HPLC determination in ... plant samples.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 398

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 4
View All
Pictogram(s)
Irritant
Health Hazard
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 211 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

Skin Sens. 1 (100%)

STOT RE 2 (100%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

Acute Tox. 4 (100%)

Eye Irrit. 2 (100%)

Aquatic Chronic 2 (100%)

10.1.3 Hazards Summary

May cause irritation; May cause skin sensitization; Caused no irritation to the skin or eyes of rabbits; [MSDSonline]

10.2 Safety and Hazard Properties

10.2.1 Flammable Limits

Lower 1.0%; Upper 7.0% /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf

10.3 Fire Fighting

10.3.1 Fire Fighting Procedures

Use appropriate extinguishing media for combustibles in the area. Wear full protective clothing and self-contained breathing apparatus. Evacuate nonessential personnel from the area to prevent human exposure to fire, smoke, fumes or products of combustion. Prevent use of contaminated buildings, area, and equipment until decontaminated. Water runoff can cause environmental damage. If water is used to fight fire, dike and collect runoff. /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf
Combustible liquid. Can release vapors that form explosive mixtures at temperatures at or above the flash point. Heavy vapors can flow along surfaces to distant ignition sources and flash back. /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf
During a fire, irritating and possibly toxic gases may be generated by thermal decomposition or combustion. /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf

10.4 Accidental Release Measures

10.4.1 Cleanup Methods

Do not contaminate water when disposing of equipment wash water or rinsate. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
Control the spill at its source. Contain the spill to prevent from spreading or contaminating soil or from entering sewage and drainage systems or any body of water. Clean up spills immediately, ... . Cover entire spill with absorbing material and place into compatible disposal container. Scrub area with hard water detergent (e.g. commercial products such as Tide, Joy, Spic and Span). Pick up wash liquid with additional absorbent and place into compatible disposal container. Once all material is cleaned up and placed in a disposal container, seal container and arrange for disposition. /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf

10.4.2 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
Do not reuse empty container. Triple rinse (or equivalent), puncture, and dispose of empty container in a sanitary landfill, or by incineration, or, if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

10.4.3 Preventive Measures

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
Do not apply directly to water, to areas where surface water is present, or to intertidal areas below the mean high water mark. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
Do not enter or allow worker entry into treated areas during the restricted-entry interval (REI) of 12 hours. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
For more Preventive Measures (Complete) data for CLODINAFOP-PROPARGYL (9 total), please visit the HSDB record page.

10.5 Handling and Storage

10.5.1 Storage Conditions

Do not contaminate water, food, or feed by storage or disposal. Do not use in animal feeds. Store in a cool, dry place. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
Store the material in a well-ventilated, secure area out of reach of children and domestic animals. Do not store food, beverages or tobacco products in the storage area. Prevent eating, drinking, tobacco use, and cosmetic application in areas where there is a potential for exposure to the material. Wash thoroughly with soap and water after handling. /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf

10.6 Exposure Control and Personal Protection

10.6.1 Allowable Tolerances

Tolerances are established for combined residues of clodinafop-propargyl (propanoic acid, 2-[4-(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-,2-propynyl ester, (2R)-) and its acid metabolite (propanoic acid, 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-, (2R)-), in or on /the following food commodities/ :
Commodity
Wheat, forage
Parts per million
0.1
Commodity
Wheat, grain
Parts per million
0.1
Commodity
Wheat, hay
Parts per million
0.1
Commodity
Wheat, straw
Parts per million
0.5
40 CFR 180.559 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of April 21, 2011: https://www.ecfr.gov

10.6.2 Personal Protective Equipment (PPE)

Personal Protective Equipment ... Applicators and other handlers must wear: Coveralls over short-sleeved shirt and short pants; Chemical-resistant gloves, such as barrier laminate or viton; Chemical-resistant footwear plus socks; Chemical-resistant apron when cleaning equipment, mixing, or loading. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
... Restricted-entry interval (REI) of 12 hours. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water is: Coveralls over short-sleeved shirt and short pants; Chemical-resistant gloves, such as barrier laminate or viton; Chemical-resistant footwear plus socks. /Discover Herbicide/
Syngenta Crop Protection, Inc; Product Label Discover Herbicide (2004). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP907AL1E0404n.pdf
... Chemical-resistant gloves ... Protective eyewear.
Mester, R.T.,Sine, C. (eds.) Crop Protection Handbook Volume 97. Meisterpro. Willoughby,OH. 2011, p. 304

10.7 Stability and Reactivity

10.7.1 Hazardous Reactivities and Incompatibilities

Combustible liquid. Can release vapors that form explosive mixtures at temperatures at or above the flash point. Heavy vapors can flow along surfaces to distant ignition sources and flash back. /Discover Herbicide/
Syngenta Crop Protection, Inc; MSDS, Discover Herbicide (Revision Date: 10/19/2010). Available from, as of June 15, 2011: https://www.syngentacropprotection.com/pdf/msds/03_1913210192010.pdf

10.8 Regulatory Information

Status Regulation (EC)
06/39/EC, Reg. (EU) 2018/524, Reg. (EU) 2019/168, Reg. (EU) 2020/421, Reg. (EU) 2021/566, Reg. (EU) 2022/378, Reg. (EU) 2023/689, Reg. (EU) No 487/2014, Reg. (EU) No 540/2011
New Zealand EPA Inventory of Chemical Status
Clodinafop-propargyl: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

10.8.1 FIFRA Requirements

Tolerances are established for combined residues of clodinafop-propargyl (propanoic acid, 2-[4-(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-,2-propynyl ester, (2R)-) and its acid metabolite (propanoic acid, 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-, (2R)-), in or on /the following food commodities/ :
Commodity
Wheat, forage
Commodity
Wheat, grain
Commodity
Wheat, hay
Commodity
Wheat, straw
40 CFR 180.559 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of April 21, 2011: https://www.ecfr.gov
Herbicide registered for use on spring wheat.
USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. June 6, 2000. Available from, as of Mar, 2002: https://www.epa.gov/opprd001/factsheets/

10.9 Other Safety Information

10.9.1 Special Reports

USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Clodinafop-propargyl (June 6, 2000).[Available from, as of June 1, 2011: http://www.epa.gov/opprd001/factsheets/]

11 Toxicity

11.1 Toxicological Information

11.1.1 RAIS Toxicity Values

Oral Acute Reference Dose (RfDoa)(mg/kg-day)
0.05
Oral Acute Reference Dose Reference
OPP
Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.0032
Oral Chronic Reference Dose Reference
OPP

11.1.2 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Acute or One Day PAD (RfD) [mg/kg/day]
0.05
Acute or One Day HHBPs [ppb]
1000
Acute HHBP Sensitive Lifestage/Population
Females 13-49 yrs
Chronic or One Day PAD (RfD) [mg/kg/day]
0.0032
Chronic or One Day HHBPs [ppb]
19
Chronic HHBP Sensitive Lifestage/Population
General Population

11.1.3 Evidence for Carcinogenicity

Cancer Classification: Suggestive Evidence of Carcinogenic Potential
USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch: "Chemicals Evaluated for Carcinogenic Potential" (April 2006)

11.1.4 Adverse Effects

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

11.1.5 Toxicity Data

LC50 (rat) > 2,325 mg/m3/4h

11.1.6 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

11.1.7 Human Toxicity Excerpts

/CASE REPORTS/ Three cases of adverse effects /to clodinafop-propargyl/ were reported: feeling of empty head and sleepiness, and stinging in the eyes.
European Food Safety Authority (EFSA); Conclusion on the Peer Review of Clodinafop; EFSA Journal 34:1-78 (2005). Available from, as of June 16, 2011: https://www.efsa.europa.eu/en/efsajournal/pub/34ar.htm
/CASE REPORTS/ In one plant accidental exposure to clodinafop-propargyl was reported. The injury was described as chemical burn on the skin.
European Food Safety Authority (EFSA); Conclusion on the Peer Review of Clodinafop; EFSA Journal 34:1-78 (2005). Available from, as of June 16, 2011: https://www.efsa.europa.eu/en/efsajournal/pub/34ar.htm

11.1.8 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Non-irritating to eyes & skin (rabbits). May cause skin sensitization (guinea pigs).
MacBean C, ed. Clodinafop-propargyl (105512-06-9). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 28 day dermal toxicity study, the systemic NOAEL for rats was 50 mg/kg/day. The systemic LOAEL was 200 mg/kg/day for rats based on dose-related increases in liver weights and clinical signs (piloerection and hunched posture) in male rats. The dermal NOAEL was 1000 mg/kg/day. /From table/
USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Clodinafop-propargyl (Conditional Registration), p5 (June 6, 2000). Available from, as of June 16, 2011: https://www.epa.gov/opprd001/factsheets/
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90 day oral toxicity study, the NOAEL for male dogs was 0.346 mg/kg/day and 1.89 mg/kg/day for female dogs. The LOAEL was 1.73 mg/kg/day for male dogs and 7.16 mg/kg/day for female dogs based on occurrence of skin lesions. /From table/
USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Clodinafop-propargyl (Conditional Registration), p4 (June 6, 2000). Available from, as of June 16, 2011: https://www.epa.gov/opprd001/factsheets/
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 13 week oral toxicity study, the NOAEL for male mice was 0.9 mg/kg/day and 1.1 mg/kg/day for female mice. The LOAEL was 7.3 mg/kg/day for male mice and 8.6 mg/kg/day for female mice based on clinical chemistry; glucose, sodium, and chloride increases and hepatocellular hypertrophy in males and females. /From table/
USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Clodinafop-propargyl (Conditional Registration), p4 (June 6, 2000). Available from, as of June 16, 2011: https://www.epa.gov/opprd001/factsheets/
For more Non-Human Toxicity Excerpts (Complete) data for CLODINAFOP-PROPARGYL (19 total), please visit the HSDB record page.

11.1.9 Non-Human Toxicity Values

LD50 Rat percutaneous >2000 mg/kg
MacBean C, ed. Clodinafop-propargyl (105512-06-9). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
LC50 Rat inhalation 2.325 mg/L air/ 4 hr
MacBean C, ed. Clodinafop-propargyl (105512-06-9). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
LD50 Rat (male) oral 1392 mg/kg /Clodinafor-propargyl technical/
US EPA; Pesticide Fact Sheet. Clodinafop-propargyl. Conditional Registration. August 22, 2000. Washington, DC: USEPA, Off Prev Pest Tox Sub (7501C). Available from, as of April 1, 2002: https://www.epa.gov/opprd001/factsheets/clodinafop.pdf
LD50 Rat (female) oral 2271 mg/kg /Clodinafop-propargyl technical/
US EPA; Pesticide Fact Sheet. Clodinafop-propargyl. Conditional Registration. August 22, 2000. Washington, DC: USEPA, Off Prev Pest Tox Sub (7501C). Available from, as of April 1, 2002: https://www.epa.gov/opprd001/factsheets/clodinafop.pdf
For more Non-Human Toxicity Values (Complete) data for CLODINAFOP-PROPARGYL (8 total), please visit the HSDB record page.

11.2 Ecological Information

11.2.1 Ecotoxicity Values

LC50; Species: Anas platyrhynchos (Mallard Duck, age 7 days) diet >5230 ppm for 8 days
USEPA/OPP, EFED; Pesticide Ecotoxicity Database (2000) as cited in the ECOTOX database. Available from, as of May 12, 2011: https://cfpub.epa.gov/ecotox/
LC50; Species: Colinus virginianus (Northern Bobwhite Quail, age 14 days) diet >5120 ppm for 8 days
USEPA/OPP, EFED; Pesticide Ecotoxicity Database (2000) as cited in the ECOTOX database. Available from, as of May 12, 2011: https://cfpub.epa.gov/ecotox/
LD50; Species: Anas platyrhynchos (Mallard Duck, age 16 weeks) oral via capsule >2000 mg/kg
USEPA/OPP, EFED; Pesticide Ecotoxicity Database (2000) as cited in the ECOTOX database. Available from, as of May 12, 2011: https://cfpub.epa.gov/ecotox/
LD50; Species: Colinus virginianus (Northern Bobwhite Quail, age 16 weeks) oral via capsule 1455 mg/kg (95% confidence interval: 1205-1908 mg/kg)
USEPA/OPP, EFED; Pesticide Ecotoxicity Database (2000) as cited in the ECOTOX database. Available from, as of May 12, 2011: https://cfpub.epa.gov/ecotox/
For more Ecotoxicity Values (Complete) data for CLODINAFOP-PROPARGYL (19 total), please visit the HSDB record page.

11.2.2 Ecotoxicity Excerpts

/AQUATIC SPECIES/ Zebrafish (Danio rerio) ... Embryos were exposed to a range of concentrations from 0.2 uM to 5 uM starting at late cleavage stage (2 hr postfertilization, (hpf)) or late gastrulation stage (10 hpf). The results showed that the two exposure strategies had the same minimum teratogenic concentration of 0.6 uM but caused different groups of morphogenetic malformations. When exposure was initiated at 2 hpf, clodinafop-propargyl caused various embryonic phenotypes, including embryos with a fin gap in the ventral tail and embryos with coiled tail. When exposure was initiated at 10 hpf, clodinafop-propargyl resulted in failure of the tail to detach, in which the ventral tissues failed to grow out but instead adhered to the yolk extension, and the defect differed to various degrees among embryos. Similar effects were observed for embryos exposed to clodinafop, the metabolite of clodinafop-propargyl. Because these defects were mainly confined to the posterior and ventral region that derived from ventral blastoderm cells, we have evaluated the expression of the ventral mesoderm marker gene gata-1 and ventral ectoderm marker gene gata-3. No significant alteration was seen in gata-1 expression except for the expanded blood islands, whereas the expression of gata-3 was significantly reduced. Our findings showed that clodinafop-propargyl exposure disturbed embryonic patterning and fate specification of ventrally derived gastrula ectoderm cells.
Gui W et al; Environ Toxicol Chem 30 (7): 1576-81 (2011)
/OTHER TERRESTRIAL SPECIES/ In the present study, DNA damage caused by clodinafop-propargyl was evaluated in silkworm, Bombyx mori, by the alkaline single-cell gel electrophoresis (SCGE). The second, fourth and fifth instar larvae of silkworm were exposed to clodinafop-propargyl by oral feeding with mulberry leaves treated using the different concentration of 30, 60, 120, 240, 480 mg/L, respectively. The results showed that comet percentage, the head DNA percentage, tail DNA percentage, tail length, tail moment and olive moment of the five tested groups were significantly different from the controlled group (P<0.01). A statistically significant (olive tail moment, P<0.01) dose-dependent increase in DNA damage was observed in silkworm. In addition, the significant dose-dependent reduce in percentage of cocooning and pupating was found in the second instar larvae of silkworm exposed to clodinafop-propargyl. ...
Yin XH et al; Environ Toxicol Pharmacol 26 (2): 162-6 (2008)

11.2.3 Environmental Fate / Exposure Summary

Clodinafop-propargyl's production may result in its release to the environment through various waste streams; its use as a herbicide will result in its direct release to the environment. If released to air, a vapor pressure of 2.4X10-8 mm Hg at 25 °C indicates clodinafop-propargyl will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase clodinafop-propargyl will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 5 hours. Particulate-phase clodinafop-propargyl will be removed from the atmosphere by wet or dry deposition. Clodinafop-propargyl does not contain chromophores that absorb at wavelengths >290 nm, and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, clodinafop-propargyl is expected to have slight mobility based upon an estimated Koc of 2,000. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.8X10-9 atm-cu m/mole. Clodinafop-propargyl may not volatilize from dry soil surfaces based upon its vapor pressure. A biodegradation half-life in soil of 0.5 to 1.5 days suggests that biodegradation may be an important environmental fate process in soil and water. If released into water, clodinafop-propargyl is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 170 suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism. The hydrolysis half-lives are 184 days at pH 5, 2.7 days at pH 7, and 2.2 hours at pH 9; therefore, hydrolysis will be an important environmental fate process under alkaline conditions. Occupational exposure to clodinafop-propargyl may occur through inhalation and dermal contact with this compound at workplaces where clodinafop-propargyl is produced or used. (SRC)

11.2.4 Artificial Pollution Sources

Clodinafop-propargyl's production may result in its release to the environment through various waste streams; its use as a herbicide(1) will result in its direct release to the environment(SRC).
(1) MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)

11.2.5 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2,000(SRC), determined from a log Kow of 3.90(2) and a regression-derived equation(3), indicates that clodinafop-propargyl is expected to have slight mobility in soil(SRC). Volatilization of clodinafop-propargyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.4X10-8 mm Hg(2), and water solubility, 4 mg/L(2). Clodinafop-propargyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). A biodegradation half-life in soil of 0.5 to 1.5 days(4) suggests that biodegradation may be an important environmental fate process in soil(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jul 7, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,000(SRC), determined from a log Kow of 3.90(2) and a regression-derived equation(3), indicates that clodinafop-propargyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 2.8X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.4X10-8 mm Hg(2), and water solubility, 4.0 mg/L(2). According to a classification scheme(5), an estimated BCF of 170(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). The aqueous chemical hydrolysis half-life of clodinafop-propargyl is 184 days at pH 5, 2.7 days at pH 7, and 2.2 hours at pH 9(6). A biodegradation half-life in soil of 0.5 to 1.5 days(6) suggests that biodegradation may be an important environmental fate process in water(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jul 7, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), clodinafop-propargyl, which has a vapor pressure of 2.40X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase clodinafop-propargyl is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase clodinafop-propargyl may be removed from the air by wet or dry deposition(SRC). Clodinafop-propargyl does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

11.2.6 Environmental Biodegradation

AEROBIC: The aerobic soil metabolism half-life of clodinafop-propargyl is reported as 0.5 to 1.5 days. Clodinafop-propargyl's major metabolite, CGA-193469, has an aerobic soil metabolism half-life of 33.6 days(1).
(1) USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/
ANAEROBIC: The anaerobic aquatic metabolism half-life of clodinafop-propargyl is reported as 513 days(1).
(1) USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/

11.2.7 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of clodinafop-propargyl with photochemically-produced hydroxyl radicals has been estimated as 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of clodinafop-propargyl with ozone has been estimated as 3.0X10-19 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 380 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). The aqueous chemical hydrolysis half-life of clodinafop-propargyl is 184 days at pH 5, 2.7 days at pH 7, and 2.2 hours at pH 9(3). Clodinafop-propargyl does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). There is no readily apparent photolysis of clodinafop-propargyl on soil surfaces(3).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Atkinson R, Carter WPL; Chem Rev 84: 437-70 (1984)
(3) USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

11.2.8 Environmental Bioconcentration

An estimated BCF of 170 was calculated in fish for clodinafop-propargyl(SRC), using a log Kow of 3.90(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).
(1) MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jul 7, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.9 Soil Adsorption / Mobility

The Koc of clodinafop-propargyl is estimated as 2,000(SRC), using a log Kow of 3.90(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that clodinafop-propargyl is expected to have slight mobility in soil. Clodinafop-propargyl is mobile in low organic soil to immobile in high organic soil(4).
(1) MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jul 7, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Swann RL et al; Res Rev 85: 17-28 (1983)
(4) USEPA; Pesticide Fact Sheet - Clodinafop-propargyl. Conditional Registration. June 6, 2000. Washington, DC: US EPA, Off Prevent Pest Toxic Sub. Available from, as of July 7, 2011: https://www.epa.gov/opprd001/factsheets/

11.2.10 Volatilization from Water / Soil

The Henry's Law constant for clodinafop-propargyl is estimated as 2.8X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.4X10-8 mm Hg(1), and water solubility, 4.0 mg/L(1). This Henry's Law constant indicates that clodinafop-propargyl is expected to be essentially nonvolatile from water and moist soil surfaces(2). Clodinafop-propargyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
(1) MacBean C, ed; The e-Pesticide Manual, 15th ed, Version 5.0.1. Surrey UK, British Crop Protection Council. Clofinafop-propargyl (105512-06-9) (2010)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

11.2.11 Probable Routes of Human Exposure

Occupational exposure to clodinafop-propargyl may occur through inhalation and dermal contact with this compound at workplaces where clodinafop-propargyl is produced or used. (SRC)

12 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 UN GHS Classification

16.5 NORMAN Suspect List Exchange Classification

16.6 EPA DSSTox Classification

16.7 PFAS and Fluorinated Organic Compounds in PubChem

16.8 EPA Substance Registry Services Tree

16.9 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. EPA Safe Drinking Water Act (SDWA)
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    Propanoic acid, 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-, (2R)-
    https://echa.europa.eu/substance-information/-/substanceinfo/100.111.897
    Propanoic acid, 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-, (2R)- (EC: 601-312-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/27639
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  9. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  10. ChEBI
  11. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  12. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  13. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  14. EU Pesticides Database
  15. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Clodinafop
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  16. Hazardous Chemical Information System (HCIS), Safe Work Australia
  17. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
  18. Japan Chemical Substance Dictionary (Nikkaji)
  19. Springer Nature
  20. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  21. Wikidata
  22. PubChem
  23. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  24. GHS Classification (UNECE)
  25. EPA Substance Registry Services
  26. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  27. PATENTSCOPE (WIPO)
CONTENTS