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Bicyclopyrone (Ref: NOA449280)
Last updated: 25/06/2021
(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 honey bees. 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
                 
Additional information
Also used in
-
Chemical structure
Isomerism
Isomeric
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 group
Triketone
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
-
CIPAC number
-
US EPA chemical code
018986
PubChem CID
11188745
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 Classification (HRAC)
F2
Herbicide Resistance Classification (WSSA)
27
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
None identified
Physical state
White powdery solid
Related substances & organisms
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 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 governments and regulators
5 = Verified data used for regulatory purposes
Acetone
-
500000
P5 P = Other governments and regulators
5 = Verified data used for regulatory purposes
Ethyl acetate
-
91000
P5 P = Other governments and regulators
5 = Verified data used for regulatory purposes
Toluene
-
8999
P5 P = Other governments and regulators
5 = Verified data used for regulatory purposes
Hexane
-
Melting point (°C)
65.3
P5 P = Other governments and regulators
5 = Verified data used for regulatory purposes
-
Boiling point (°C)
489.5
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
-
Degradation point (°C)
- - -
Flashpoint (°C)
249.9
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
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 governments and regulators
5 = Verified data used for regulatory purposes
Low
Bulk density (g ml⁻¹)
1.503
P5 P = Other governments and regulators
5 = Verified data used for regulatory purposes
-
Dissociation constant pKa) at 25 °C
3.06
P5 P = Other governments and regulators
5 = Verified data used for regulatory purposes
-
-
Vapour pressure at 20 °C (mPa)
5.0 X 10-08
P5 P = Other 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 governments and regulators
5 = Verified data used for regulatory purposes
Non-volatile
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 (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 on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ 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 (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 (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)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
- - -
Koc
-
Notes and range
-
Freundlich
Kf
0.59
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
-
Kfoc
-
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
- - -
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
6-(trifluoromethyl)pyridine-2,3-dicarboxylic acid (Ref: SYN 504810) CSCC 163768 Water; Soil - -
(1S,3R)-cyclopentane-1,3-dicarboxylic acid (Ref: NOA 412101) CSAA 589691 Soil - -
Ref: SYN 545859 CSCD 642512 Water; Soil - -
6-(trifluoromethyl)pyridin-3-ol-2-carboxylic acid (Ref: SYN 545680) CSCD 656832 Water; Soil - -
2-(2-methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid SYN 503780 Soil; Water - -
- CSAA 806573 Soil; 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 Soil; Water - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
P5 P = Other 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 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)
- - -
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
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
46.7
E4 E = Manufacturers safety data sheets
4 = Verified data
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (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
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
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)
- - -
Bumblebees (Bombus spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Mason bees (Osmia spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Other pollinators (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other pollinators (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
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 governments and regulators
5 = Verified data used for regulatory purposes
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
5000
P5 P = Other governments and regulators
5 = Verified data used for regulatory purposes
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 5.2
P5 P = Other 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 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)
- - -
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
No further information available
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
-
EC Risk Classification
-
EC Safety Classification
-
WHO Classification
NL (Not listed)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
bicyclopyrone
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 25/06/2021
Contact: aeru@herts.ac.uk
Please cite as: Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242