Beflubutamid (Ref: UBH 820)

Beflubutamid (Ref: UBH 820)	Last updated: 12/01/2021
(Also known as: UR50601)

SUMMARY

Beflubutamid is a selective herbicide used to control broad-leaved weeds in cereals. It has a low aqueous solubility and is quite volatile. There is a low risk of groundwater contamination and it is non-persistent in soil. However it can be quite persistent in water bodies. It has a moderate oral toxicity to mammals and has been shown to cause reproduction or development issues in humans. It is moderately toxic to birds, earthworms and most aquatic organisms. It has a low toxicity to honeybees.

GENERAL INFORMATION

Description

An amide herbicide for pre- and early post-emergence control of 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

Availability status

Current

Introduction & key dates

1998, USA

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

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

31/07/2021

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
			✓				✓

Also used in

Chemical structure

Isomerism

A chiral molecule. The racemate mixture is normally comprised of equimolar amounts of R- and S-beflubutamid.

Chemical formula

C₁₈H₁₇F₄NO₂

Canonical SMILES

CCC(C(=O)NCC1=CC=CC=C1)OC2=CC(=C(C=C2)F)C(F)(F)F

Isomeric SMILES

CC[C@H](Oc1ccc(F)c(c1)C(F)(F)F)C(=O)NCc2ccccc2

International Chemical Identifier key (InChIKey)

FFQPZWRNXKPNPX-UHFFFAOYSA-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)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Amide

Minimum active substance purity

970 G/Kg

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Bleaching: inhibition of carotenoid biosynthesis.

CAS RN

113614-08-7

EC number

CIPAC number

662

US EPA chemical code

PubChem CID

6451159

Molecular mass

355.12

PIN (Preferred Identification Name)

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

IUPAC name

(RS)-N-benzyl-2-(α,α,α,4-tetrafluoro-m-tolyloxy)butyramide

CAS name

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

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White fluffy powder

Related substances & organisms

isoproturon

Formulations

Property

Value

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

Herbaflex

Example products using this active

Formulation and application details

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)

600000

Acetone

571000

Ethyl acetate

473000

Methanol

2180

n-Heptane

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

128

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.91 X 10⁰⁴

Calculated

Log P

4.28

High

Bulk density (g ml⁻¹)

1.33

Dissociation constant pKa) at 25 °C

N/a

Unlikely to dissociate

Vapour pressure at 20 °C (mPa)

1.10 X 10^-02

Low volatility

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

1.10 X 10^-04

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)

29.6

Non-persistent

DT₅₀ (lab at 20 °C)

29.6

Non-persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

197

Persistent

DT₉₀ (field)

182

DT₅₀ modelling endpoint

Note

EU dossier lab studies 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 on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable at pH 5 to pH 9 for up to 5 days

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

23.6

Slightly mobile

K_foc

1171

¹/_n

0.908

Notes and range

EU dossier K_f 8.5-43.0 mL g⁻¹, K_foc range 496-1793 mL g⁻¹, ¹/_n 0.86-0.93, Soils=3

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.62

Calculated

Low leachability

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

Value

4.71 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

phenoxybutyric acid (Ref: UR-50604)

Soil

0.261

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

230

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(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)

> 5200 ppm

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.86

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.11

Pimephales promelas

Moderate

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

1.64

Daphnia magna

Moderate

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

0.455

Daphnia magna

Moderate

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)

0.02

Lemna gibba

Moderate

Non-target plants

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

69.2

Selenastrum capricornutum

Low

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)

> 200

Low

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

> 200

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)

366

corr

Moderate

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

< 0.17

Eisenia foetida,corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

160

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

8.0

Mortality
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Mortality
Aphidius rhopalosiphi

Soil micro-organisms

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

Dose: 0.6 kg ha⁻¹

Mesocosm study data

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

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat

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)

0.3

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver, kidney and thyroid toxicant

Handling issues

Property

Value and interpretation

General

Not explosive

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50/53

EC Safety Classification

S60, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

beflubutamid

French

beflubutamide

German

Beflubutamid

Danish

beflubutamid

Italian

beflubutamid

Spanish

beflubutamid

Greek

Polish

beflubutamid

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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