Florpyrauxifen-benzyl (Ref: XDE-848 BE)

Florpyrauxifen-benzyl (Ref: XDE-848 BE)	Last updated: 22/08/2024
(Also known as: XR 848)

SUMMARY

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
Environmental fate High alert: Persistent; Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health Low alert

GENERAL INFORMATION

Description

A post-emergence herbicide with various applications including as a rice weed herbicide particularly in Australia

Example pests controlled

Grass weeds including barnyard grass; Sedges; Broad-leaf weeds including water plantain, starfruit, arrowhead, jerry jerry and dirty Dora

Example applications

Rice

Efficacy & activity

Shown to be highly effective in research studies

Availability status

Current

Introduction & key dates

2016, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

24/07/2029

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Italy/Austria

Date EC 1107/2009 inclusion expires

24/07/2029

EU Candidate for substitution (CfS)

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

Australia, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₂₀H₁₄Cl₂F₂N₂O₃

Canonical SMILES

COC1=C(C=CC(=C1F)C2=NC(=C(C(=C2F)N)Cl)C(=O)OCC3=CC=CC=C3)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

WNZCDFOXYNRBRB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C20H14Cl2F2N2O3/c1-28-19-12(21)8-7-11(14(19)23)17-15(24)16(25)13(22)18(26-17)20(27)29-9-10-5-3-2-4-6-10/h2-8H,9H2,1H3,(H2,25,26)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Pyridine herbicide; Picolinic acid herbicide

Minimum active substance purity

920 g kg⁻¹

Known relevant impurities

EU dossier: toluene < 3g kg⁻¹

Substance origin

Synthetic

Mode of action

CAS RN

1390661-72-9

EC number

815-125-3

CIPAC number

990.227

US EPA chemical code

PubChem CID

70495450

CLP index number

No data found

Molecular mass

439.25

PIN (Preferred Identification Name)

benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate

IUPAC name

benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate

CAS name

phenylmethyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Off-white to beige coloured solid with a mild odour

Related substances & organisms

florpyrauxifen

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Dow
Corteva Agriscience Australia Pty Ltd

Example products using this active

Rinskor
Lorant

Formulation and application details

Usually supplied as an emulsifiable concentrate for dilution and use in broadcast sprayers.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.011

Low

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

13000

Methanol

210000

Acetone

14000

Xylene

120000

Ethyl acetate

Melting point (°C)

137.1

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

286.8

Flashpoint (°C)

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

2.88 X 10⁰⁵

Calculated

Log P

5.46

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.2 X 10^-02

Low volatility

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

0.94

Moderately 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

Not readily biodegradeable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

150

Persistent

DT₅₀ (lab at 20 °C)

150.5

Persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

304.5

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

14.7

mean for flooded paddy soil system

Note

EU 2017 dossier lab studies DT₅₀ range 8.9-348 days, DT₉₀ range 30-7914 days; Flooded paddy field DT₅₀ range 8-10 days, DT₉₀ range 34-104 days

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

0.07

summer

Fast

Note

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

Value

111

Persistent

Note

pH and temperature sensitive

Water-sediment DT₅₀ (days)

4.9

Fast

Water phase only DT₅₀ (days)

3.3

Moderately fast

Sediment 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

K_d (mL g⁻¹)

804.5

Non-mobile

K_oc (mL g⁻¹)

32308

Notes and range

EU 2017 dossier K_d range 272-1377 mL g⁻¹, K_oc range 23028-47763 mL g⁻¹, Soils=5

Freundlich

K_f (mL g⁻¹)

634.8

Non-mobile

K_foc (mL g⁻¹)

22325

¹/_n

0.95

Notes and range

EU 2017 dossier, K_f range 130-1474 mL g⁻¹, K_foc range 15305-33500 mL g⁻¹, ¹/_n range 0.9-1.01, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.76

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

13.49

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

326

Threshold for concern

CT₅₀ (days)

1.3

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

florpyrauxifen (Ref: X11438848)

Major fraction

0.62

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxyphenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X11966341)

Minor fraction

0.08

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxy-6-nitrophenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X12483137)

Major fraction

0.11

benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxyphenyl)-5-fluoropyridine-2-carboxylate (Ref: X12300837)

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

florpyrauxifen (Ref: X11438848)

Not relevant

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxy-6-nitrophenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X12483137)

Not relevant

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxyphenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X11966341)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxyphenyl)-5-fluoropyridine-2-carboxylate (Ref: X12300837)

Water

benzyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (Ref: X12431091)

Plant

4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X12393505)

Water; Animal

4-amino-6-(4-chloro-2-fluoro-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-fluoropicolinic acid (Ref: X12131932)

Water; Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

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)

67.5

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose; 017-17 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

2.3

Carrot
Seedling emergence, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 105.4

Apis mellifera

Low

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

Chronic

Notes

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) as % Mortality at dose 18 g ha⁻¹

14.3

Chrysoperla carnea Larva

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

1342

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

972

Typhlodromus pyri

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)

> 0.049

Oncorhynchus mykiss

High

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)

> 0.0626

Daphnia magna

High

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.0378

Daphnia magna

Moderate

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)

0.0785

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

> 0.0461

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 0.0337

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.23

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.5

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

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.13

Dermal penetration studies (%)

0.45-11.4

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks identified

Occupational

No unacceptable risks identified

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

Elimination main via faeces (51-100%) and urine (8-42%).

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

No information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317
Environment: H410

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

florpyrauxifen-benzyl

French

florpyrauxifene-benzyle

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	22/08/2024
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