Bicyclopyrone (Ref: NOA449280)-Pesticide database

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Bicyclopyrone (Ref: NOA449280)

(Not known by any other names)

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.

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

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

Introduction & key dates

2014, first registered USA

UK regulatory status

UK COPR regulatory status

Date COPR inclusion expires

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

EU Candidate for substitution (CfS)

Listed in EU database

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

Chemical structure

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?

Substance groups

Triketone herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor - causes plant bleaching

Alternative/old CAS RN

US EPA chemical code

CLP index number

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

4-hydroxy-3-{2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridylcarbonyl}bicyclo[3.2.1]oct-3-en-2-one

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)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

None identified

White powdery solid

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

Source; quality score; and other information

Solubility - In water at 20 °C (mg l⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Solubility - In organic solvents at 20 °C (mg l⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Melting point (°C)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Boiling point (°C)

V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source

Degradation point (°C)

Flashpoint (°C)

V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source

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

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Fat solubility of residues

Density (g ml⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Dissociation constant pKa) at 25 °C

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Vapour pressure at 20 °C (mPa)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Source; quality score; and other information

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

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

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Dissipation rate RL₅₀ on plant matrix

Dissipation rate RL₅₀ on and in plant matrix

Aqueous photolysis DT₅₀ (days) at pH 7

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

DT₅₀ given as between 11 and 75 days

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

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 at all relevant pH values

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Source; quality score; and other information

Notes and range

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

Notes and range

Source; quality score; and other information

GUS leaching potential index

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Cannot be calculated

Potential for particle bound transport index

Potential for loss via drain flow

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known soil metabolites

Major/Minor fraction

Estimated maximum occurrence fraction

6-(trifluoromethyl)pyridine-2,3-dicarboxylic acid (Ref: SYN 504810)

(1S,3R)-cyclopentane-1,3-dicarboxylic acid (Ref: NOA 412101)

[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)

6-(trifluoromethyl)pyridin-3-ol-2-carboxylic acid (Ref: SYN 545680)

2-(2-methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid (Ref: SYN 503780)

2-(hydroxymethyl)-6-trifuoromethyl-nicotinic acid (Ref: CSAA 806573)

4-hydroxy-3-(2-(2-methoxy-ethoxymethyl)-6-(trifluoromethyl)-pyridine-3-carbonyl]-bicyclo [3.2.1]oct-3-en-2-one (Ref: NOA 449280)

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

6-(trifluoromethyl)pyridine-2,3-dicarboxylic acid (Ref: SYN 504810)

Ref: SYN 545859

6-(trifluoromethyl)pyridin-3-ol-2-carboxylic acid (Ref: SYN 545680)

2-(2-methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid

Ref: SYN 503780

4-hydroxy-3-(2-(2-methoxy-ethoxymethyl)-6-(trifluoromethyl)-pyridine-3-carbonyl]-bicyclo [3.2.1]oct-3-en-2-one

Terrestrial ecotoxicology

Source; quality score; and other information

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Mammals - Short term dietary NOEL

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

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

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)

E4 E = Manufacturers safety data sheets
4 = Verified data

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

E4 E = Manufacturers safety data sheets
4 = Verified data

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 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

Source; quality score; and other information

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

E3 E = Manufacturers safety data sheets
3 = Unverified data of known source

Unknown species

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

E4 E = Manufacturers safety data sheets
4 = Verified data

Daphnia magna

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)

E4 E = Manufacturers safety data sheets
4 = Verified data

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

Source; quality score; and other information

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Mammals - Inhalation LC₅₀ (mg l⁻¹)

P5 P = Other non-EU, UK or US Governments and Regulators
5 = Verified data used for regulatory purposes

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified 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

EU MRL pesticide database

GB MRL Register

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Specific human health issues

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

Reproduction / development effects

Acetyl cholinesterase inhibitor

✓Yes, known to cause a problem

XNo, known not to cause a problem

XNo, known not to cause a problem

Respiratory tract irritant

Skin sensitiser

XNo, known not to cause a problem

XNo, known not to cause a problem

?Possibly, status not identified

General human health issues

No further information available

Handling issues

Value and interpretation

No information available

CLP classification 2013

WHO Classification

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

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