Beflubutamid-M (Ref: F4050)

Beflubutamid-M (Ref: F4050)	Last updated: 24/07/2024
(Also known as: VPF45; FMC 510363; F4050 S-enantiomer)

SUMMARY

Beflubutamid-M is the S-enantiomer of chiral beflubutamide and considered to demonstrate the most herbicidal activity of the two isomers. It has a low aqueous solubility and a low volatility. It may be persistent in soils depending upon local conditions. Risk of leaching, based on its physicochemical properties, is considered low. Its toxicity to biodiversity is low with the exception of earthworms and aquatic species where its toxicity is classified as moderate. It has a low oral mammalian toxicity but there are concerns regarding its status as a reproduction/developmental toxicant.

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: Potential for particle bound transport: High	Ecotoxicity Moderate alert: Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A phenoxy herbicide for pre- and early post-emergence control of grass and broad-leaved weeds

Example pests controlled

Chickweed; Loose silky bent; Field pansy; Scented mayweed; Wild pansy; Field speedwell; Ivy-leaved speedwell; Groundsel

Example applications

Cereals including wheat, barley, rye, triticale

Efficacy & activity

Beflubutamid-M is a new molecule of an ‘old chemistry’ known and utilised in crop protection for nearly 20 years. No resistance or tolerance in weed-populations have, to-date, been noted.

Availability status

Current

Introduction & key dates

1998, registered USA

GB regulatory status

GB COPR regulatory status

Approved - as beflubutamide

Date COPR inclusion expires

31/07/2024

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Germany/Lithuania

Date EC 1107/2009 inclusion expires

31/10/2026

EU Candidate for substitution (CfS)

Listed in EU database

Yes - as beflubutamide

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

The S-enantiomer of chiral beflubutamide. The R-enantiomer is considered inactive.

Chemical formula

C₁₈H₁₇F₄NO₂

Canonical SMILES

Isomeric SMILES

International Chemical Identifier key (InChIKey)

FFQPZWRNXKPNPX-INIZCTEOSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H17F4NO2/c1-2-16(17(24)23-11-12-6-4-3-5-7-12)25-13-8-9-15(19)14(10-13)18(20,21)22/h3-10,16H,2,11H2,1H3,(H,23,24)/t16-/m0/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Amide herbicide; Phenoxybutamide herbicide; Phenoxy herbicide

Minimum active substance purity

[GB CRD 2021 dossier: >960 g kg⁻¹]

Known relevant impurities

GB CRD 2021 dossier: R-enantiomer < 3%

Substance origin

Synthetic

Mode of action

Substance is translocated in plants. Bleaching - Carotenoid biosynthesis inhibitor.

CAS RN

113614-09-8

EC number

No data found

CIPAC number

662

US EPA chemical code

PubChem CID

69991731

CLP index number

616-165-00-2

Molecular mass

355.12

PIN (Preferred Identification Name)

(2S)-N-benzyl-2-[4-fluoro-3-(trifluoromethyl)phenoxy]butanamide

IUPAC name

(2S)-N-benzyl-2-[4-fluoro-3-(trifluoromethyl)phenoxy]butanamide

CAS name

(2S)-2-[4-fluoro-3-(trifluoromethyl)phenoxy]-N-(phenylmethyl)butanamide

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

White fluffy lipophilic powder

Related substances & organisms

beflubutamid

Formulations

Property

Value

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

FMC Agricultural Solutions, Denmark

Example products using this active

Formulation and application details

Used as a broadcast foliar application

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3.29

Low

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

3100

n-Heptane

138000

n-Octanol

250000

Dichloromethane

250000

Acetone

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

220

Flashpoint (°C)

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

2.19 X 10⁰⁴

Calculated

Log P

4.34

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.28

Dissociation constant pKa) at 25 °C

No dissociation

Vapour pressure at 20 °C (mPa)

7.1 X 10^-02

Low volatility

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

6.8 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Acidic soln: 250nm=243, 283nm=2520, 310nm=0
Neutral soln: 250nm=243, 283nm=2480, 310nm=7
Basic soln: 250nm=282, 283nm=2570, 310nm=10

Surface tension (mN m⁻¹)

67.0

at 20 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

49.7

Moderately persistent

DT₅₀ (lab at 20 °C)

49.7

Moderately persistent

DT₅₀ (field)

43.6

Moderately persistent

DT₉₀ (lab at 20 °C)

184.1

Persistent

DT₉₀ (field)

183

DT₅₀ modelling endpoint

109

worst case lab value

Note

GB CRD 2023 Dossier: Lab studies DT₅₀ (normalised) range 15.8-267 days, DT₉₀ (measured) range 52.6-445 days, Soils=6; Field studies DT₅₀ (measured) range 10.5-109 days, DT₉₀ (measured) range 34.9-765 days, Soil=5; EU 2002 dossier lab studies as unresolved beflubutamid DT₅₀ range 5-118 days, DT₉₀ range 16-365 days, field studies DT₅₀ range 15-103 days, DT₉₀ range 49-343 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

Note

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

Value

Note

Water-sediment DT₅₀ (days)

177.3

Slow

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

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

Slightly mobile

K_foc (mL g⁻¹)

1229.9

¹/_n

0.92

Notes and range

GB CRD 2023 Dossier: K_foc range 757-17775 mL g⁻¹, ¹/_n range 0.867-0.996, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.49

Calculated

Low leachability

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

Value

3.88 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

230

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

(RS)-2-(4-fluoro-3-trifluoromethylphenoxy)butanoic acid (Ref: UR-50604)

Major fraction

0.261

(RS)-2-(4-fluoro-3-trifluoromethylphenoxy)butanamide (Ref: UR-50624)

Major fraction

0.113

2-fluoro-5-2-fluoro-5-hydroxybenzotrifluoride (Ref: IN-VJP08)

Minor fraction

0.038

Transient metabolite

4-fluoro-3-trifluoromethyl anisole (Ref: IN-XNK91)

Major fraction

0.263

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

RS)-N-benzyl-2-(4-fluoro-3-trifluoromethylphenoxy)-4-hydroxybutanamide (Ref: UR-50615)

Rat

(RS)-N-(4-hydroxybenzyl)-2-(4-fluoro-3-trifluoromethylphenoxy)butanamide (Ref: UR-50617)

Livestock; Plant; Rat

(RS)-N-(3-hydroxybenzyl)-2-(4-fluoro-3-trifluoromethylphenoxy)butanamide (Ref: UR-50618)

Livestock; Plant; Rat

(RS)-N-(2-hydroxybenzyl)-2-(4-fluoro-3-trifluoromethylphenoxy)butanamide (Ref: UR-50619; IN-VLJ55)

Plant; Rat

(RS)-2-(4-fluoro-3-trifluoromethylphenoxy)butanamide (Ref: UR-50624)

Plant; Surface water; Sediment

N-benzoyl-glycine

Hippuric acid

Livestock; Rat

2,2,2-trifluoroacetic acid (Ref: IN-V0206)

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)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 2600 mg kg feed⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

366

as unresolved beflubutamid corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

30.7

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect

Dose: 0.125 kg ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

160

Folsomia candida as unresolved beflubutamid corr

Non-target plants

> 250.1

Oat Corn Ryegrass Onion Tomato Soybean
Vegetative vigour, 21 day ER₅₀
as g ha⁻¹

> 250.1

Oat Corn OSR Soybean Sugarbeet
Seedling emergence, 21 day ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 198.5

Apis mellifera

Low

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

> 196.8

Apis mellifera

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)

> 793.2

Bombus terrestris

Low

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

> 732.6

Bombus terrestris

Low

Mason bees (Osmia spp.)

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

> 198.1

Osmia bicornis

Low

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 250 g ha⁻¹

6.0

Chrysoperla carnea Larva

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

> 255

Aphidius rhopalosiphi

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

> 255

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 250 g ha⁻¹

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 176.5

Oncorhynchus mykiss

Low

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

0.11

Pimephales as unresolved beflubutamid

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

2.00

Daphnia magna

Moderate

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

0.455

Daphnia magna as unresolved beflubutamid

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)

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

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

0.066

Lemna minor

Moderate

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

> 3.56

Anabaena flos-aquae

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.25

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.02

Rat SF=100

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)

0.24

Rat SF=100

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Risks acceptable for intended uses

Occupational

Risks acceptable for intended uses

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

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible liver, kidney and thyroid toxicant

Handling issues

Property

Value and interpretation

General

Not explosive
Not expected to auto-ignite; Not highly flammable. IMDG Transport Clss 9

CLP classification 2013

Health: H373
Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

beflubutamid-M

French

beflubutamide-M

German

Beflubutamid-M

Danish

beflubutamid-M

Italian

beflubutamid-M

Spanish

beflubutamid-M

Greek

Polish

beflubutamid-M

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	24/07/2024
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