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Bicyclopyrone (Ref: NOA449280)
Last updated: 03/09/2023
(Not known by any other names)
SUMMARY
Bicyclopyrone is a broad-spectrum herbicide. It is highly soluble in water and non-volatile. It can be persistent in both soil and aquatic systems. It is moderately toxic to fish, aquatic invertebrates and aquatic plants but presents a low risk to honeybees. Its oral mammalian toxicity is low but there are some concerns that it may be a reproduction/developmental toxin.
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
 
Ecotoxicity
Moderate alert:
Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate
Warning:
Significant data are missing
Human health
High alert:
Mammals chronic toxicity: High; Reproduction/development effects
GENERAL INFORMATION
Description
A broad-spectrum herbicide, sometimes used in mixtures, for the pre- and post-emergence control of grass and dicot weeds mainly in corn
Example pests controlled
Foxtail; Wild buckwheat; Common ragweed
Example applications
Field corn; Seed corn; Sweetcorn; Popcorn; Silage corn; Sugarcane; Cereals including wheat and barley
Efficacy & activity
-
Availability status
Current
Introduction & key dates
2014, first registered USA
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
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
-
Chemical structure
Isomerism
Substance is racemic.
Chemical formula
C₁₉H₂₀F₃NO₅
Canonical SMILES
COCCOCC1=C(C=CC(=N1)C(F)(F)F)C(=C2C(=O)C3CCC(C3)C2=O)O
Isomeric SMILES
COCCOCC1=C(C=CC(=N1)C(F)(F)F)C(=C2C(=O)[C@@H]3CC[C@@H](C3)C2=O)O
International Chemical Identifier key (InChIKey)
AIAYSXFWIUNXRC-PHIMTYICSA-N
International Chemical Identifier (InChI)
InChI=1S/C19H20F3NO5/c1-27-6-7-28-9-13-12(4-5-14(23-13)19(20,21)22)18(26)15-16(24)10-2-3-11(8-10)17(15)25/h4-5,10-11,24H,2-3,6-9H2,1H3
2D structure diagram/image available?
Yes
General status
Pesticide type
Herbicide
Substance groups
Triketone herbicide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor - causes plant bleaching
CAS RN
352010-68-5
Alternative/old CAS RN
365400-11-9
EC number
688-487-1
CIPAC number
None allocated
US EPA chemical code
018986
PubChem CID
11188745
CLP index number
No data found
Molecular mass
399.36
PIN (Preferred Identification Name)
rac-(1R,5R)-4-hydroxy-3-{2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridine-3-carbonyl}bicyclo[3.2.1]oct-3-en-2-one
IUPAC name
4-hydroxy-3-{2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridylcarbonyl}bicyclo[3.2.1]oct-3-en-2-one
CAS name
4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one
Other status information
Possible groundwater contaminant
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Class (HRAC MoA class)
F2
Herbicide Resistance Class (WSSA MoA class)
27
Insecticide Resistance Class (IRAC MoA class)
Not applicable
Fungicide Resistance Class (FRAC MOA class)
Not applicable
Examples of recorded resistance
None identified
Physical state
White powdery solid
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Syngenta
Example products using this active
  • Acuron
  • Talinor
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
1200
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
500000
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Acetone		 -
500000
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Ethyl acetate		 -
91000
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Toluene		 -
8999
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Hexane		 -
Melting point (°C)
65.3
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
 -
Boiling point (°C)
489.5
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
249.9
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 -
Octanol-water partition coefficient at pH 7, 20 °C
P
6.31 X 10-02 Calculated -
Log P
-1.2
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
 Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.503
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
 -
Dissociation constant pKa) at 25 °C
3.06
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
 -
-
Vapour pressure at 20 °C (mPa)
5.0 X 10-03
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
1.7 X 10-08
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
 Non-volatile
Volatilisation as max % of applied dose lost
From plant surface
- - -
From soil surface
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
213.2
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 Persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
Dissipation rate RL₅₀ (days) on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ (days) on and in plant matrix
Value
- - -
Note
-
Aqueous photolysis DT₅₀ (days) at pH 7
Value
43
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 Stable
Note
DT₅₀ given as between 11 and 75 days
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 Stable
Note
Stable at all relevant pH values
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
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
Kd (mL g⁻¹)
- - -
Koc (mL g⁻¹)
-
Notes and range
-
Freundlich
Kf (mL g⁻¹)
0.59
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 -
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated - -
Note
-
Potential for particle bound transport index
- - -
Potential for loss via drain flow
- - -
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk
- - -
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
6-(trifluoromethyl)pyridine-2,3-dicarboxylic acid (Ref: SYN 504810)
Major fraction - -
(1S,3R)-cyclopentane-1,3-dicarboxylic acid (Ref: NOA 412101)
Major fraction - -
[3-(2-hydroxy-4-oxo-bicyclo[3.2.1]oct-2-ene-3-carbonyl)-6-trifluoromethyl- pyridine-2-yl-methyloxy]-acetic acid (Ref: SYN 545859)
Major fraction - -
6-(trifluoromethyl)pyridin-3-ol-2-carboxylic acid (Ref: SYN 545680)
Major fraction - -
2-(2-methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid (Ref: SYN 503780)
Major fraction - -
2-(hydroxymethyl)-6-trifuoromethyl-nicotinic acid (Ref: CSAA 806573)
Major fraction - -
4-hydroxy-3-(2-(2-methoxy-ethoxymethyl)-6-(trifluoromethyl)-pyridine-3-carbonyl]-bicyclo [3.2.1]oct-3-en-2-one (Ref: NOA 449280)
Major fraction - -
Known groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
6-(trifluoromethyl)pyridine-2,3-dicarboxylic acid (Ref: SYN 504810) CSCC 163768 Water -
Ref: SYN 545859 CSCD 642512 Water -
6-(trifluoromethyl)pyridin-3-ol-2-carboxylic acid (Ref: SYN 545680) CSCD 656832 Water -
2-(2-methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid SYN 503780 Water -
- CSAA 806573 Water -
Ref: SYN 503780 CSAA 794148 Water -
4-hydroxy-3-(2-(2-methoxy-ethoxymethyl)-6-(trifluoromethyl)-pyridine-3-carbonyl]-bicyclo [3.2.1]oct-3-en-2-one NOA 449280 Water -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Rat		 Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
0.72
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Rat		 High
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
780.0
E4 E = Manufacturers safety data sheets
4 = Verified data
 Low
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
784.4
E4 E = Manufacturers safety data sheets
4 = Verified data
 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)
- - -
Beneficial insects (Predatory mites)
- - -
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)
46.9
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Unknown species		 Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
46.7
E4 E = Manufacturers safety data sheets
4 = Verified data
Daphnia magna		 Moderate
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
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)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)
- - -
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)
0.013
E4 E = Manufacturers safety data sheets
4 = Verified data
Lemna gibba		 Moderate
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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)
> 5000
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Rat		 Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
5000
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 5.2
P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.01
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Rabbit US data		 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
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
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
?Possibly, status not identified
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
✓Yes, known to cause a problem
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
XNo, known not to cause a problem
XNo, known not to cause a problem
Eye irritant Phototoxicant  
?Possibly, status not identified
 No data found  
General human health issues
Published studies concluded that bicyclopyrone is carcinogenic in rats, but not in mice
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H360D
Environment: H400, H410
WHO Classification
U (Unlikely to present an acute hazard)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
bicyclopyrone
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 03/09/2023
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