Fluazifop-P-butyl (Ref: R154875)

Fluazifop-P-butyl (Ref: R154875)	Last updated: 23/01/2021
(Also known as: PP 005; SL 118)

GENERAL INFORMATION

Description

A post-emergence herbicide used to control grass weeds mainly in broad-leaved crops

Example pests controlled

Volunteer cereals, Annual and perennial grass weeds

Example applications

Soybeans; Carrots; Spinach; Potatoes; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1981, first marketed

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Italy

Date EC 1107/2009 inclusion expires

31/12/2021

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

Australia, USA

Chemical structure

Isomerism

Fluazifop-P-butyl is the stereospecific R-isomer of the chiral herbicide fluazifop-butyl

Chemical formula

C₁₉H₂₀F₃NO₄

Canonical SMILES

CCCCOC(=O)C(C)OC1=CC=C(C=C1)OC2=NC=C(C=C2)C(F)(F)F

Isomeric SMILES

CCCCOC(=O)[C@@H](C)OC1=CC=C(C=C1)OC2=NC=C(C=C2)C(F)(F)F

International Chemical Identifier key (InChIKey)

VAIZTNZGPYBOGF-CYBMUJFWSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H20F3NO4/c1-3-4-11-25-18(24)13(2)26-15-6-8-16(9-7-15)27-17-10-5-14(12-23-17)19(20,21)22/h5-10,12-13H,3-4,11H2,1-2H3/t13-/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Aryloxyphenoxypropionate

Minimum active substance purity

900 g kg⁻¹

Known relevant impurities

EU dossier - 2-chloro-5-(trifluoromethyl)pyridine <1.5g kg⁻¹

Substance origin

Synthetic

Mode of action

Selective, absorbed through leaf surface. An acetyl CoA carboxylase inhibitor (ACCase).

CAS RN

79241-46-6

EC number

274-125-6

CIPAC number

467.205

US EPA chemical code

122809

PubChem CID

3033674

Molecular mass

383.36

PIN (Preferred Identification Name)

butyl (2R)-2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate

IUPAC name

butyl (R)-2-{4-[5-(trifluoromethyl)-2-pyridyloxy]phenoxy}propionate

CAS name

butyl (2R)-2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoate

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

Many recorded cases, Alopecurus myosuroides, Avena fatua, Avena sterilis, Digitaria sanguinalis

Physical state

Straw coloured liquid

Formulations

Property

Value

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

Fusilade Max
Greencrop Bantry

Example products using this active

Clayton
Greencrop
Syngenta

Formulation and application details

Often supplied as an emulsifiable concentrate which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.93

Low

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

Miscible

Xylene

Miscible

Acetone

Miscible

Methanol

Miscible

Toluene

Melting point (°C)

-46

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

216

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.16 X 10⁰⁴

Calculated

Log P

4.5

High

Bulk density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

Not applicable

No pka identified

Vapour pressure at 20 °C (mPa)

0.12

Low volatility

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

0.049

Non-volatile

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

207.2nm = 6160, 255.4nm = 4590, 223.7nm = 16600

Surface tension (mN m⁻¹)

66.1

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.0

Non-persistent

DT₅₀ (lab at 20 °C)

1.0

Non-persistent

DT₅₀ (field)

8.2

Non-persistent

DT₉₀ (lab at 20 °C)

3.4

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.3-3.3 days, DT₉₀ range 1.1-11.1 days, field studies DT₅₀ range: 2.1-38.0 days, DT₉₀ range 12-126 days; Other sources: DT₅₀ 15 days (DW4)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

3.9

Note

Published literature RL₅₀ range 1.3-11.0 days, leaves of 7 field crops, n=13

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

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

Value

Moderately persistent

Note

pH sensitive: stable at pH 5, DT₅₀ 29 hours at pH 9 all at 25 °C

Water-sediment DT₅₀ (days)

0.1

Fast

Water phase only DT₅₀ (days)

0.1

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

41.4

Slightly mobile

K_oc

3394

Notes and range

Data for only one soil - loamy sand

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.43

Calculated

Low leachability

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

Value

7.14 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

fluazifop-P (Ref: R156172)

Soil

0.834

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

5-trifluoromethyl-2-(1H) pyridone (Ref: R154719)
Note: Major metabolite; Molecular wt = 163

Compound X

Soil; Rat; Water

5-trifluoromethyl-pyrid-2-one

Compound 10

Soil (Hydrolysis); Water/Sediment

2-(4-hydroxyphenoxy)-5-trifluoromethyl pyridine

Compound 4; Compound 1V

Soil (Hydrolysis); Sediment

N-(1-carboxy-2-(5-trifluoromethyl-2-pyridylthio)ethyl)malonmalic acid

Compound 28

unknown

2-(4-(5-trifluoromethyl-2-pyridyloxy)phenoxy)propanol

Compound 34

unknown

2-(4-(3-hydroxy-5-trifluoromethyl-2-pyridyloxy)phenoxy propionic acid

Compound 40

unknown

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

320

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

2451

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

> 100

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

6.72

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

> 3960

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 942 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

86.8

Colinius virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 1.41

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.077

Pimephales promelas

Moderate

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

> 0.62

Daphnia magna

Moderate

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.54

Americamysis bahia 48 hour

Moderate

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)

> 1.4

Lemna gibba

Moderate

Non-target plants

37.1

Echinochloa crus-galli
Seedling emergence, ER₅₀
as g ha⁻¹

9.1

Zea mays
Vegetative vigour, ER₅₀
as g ha⁻¹

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

> 0.18

Pseudokirchneriella subcapitata

Moderate

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

0.3

Unknown species

Moderate

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

> 200

Apis mellifera

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)

> 500

Eisenia foetida corr

Moderate

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

177

Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

5.6

Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 3.75 kg ha⁻¹ 28days

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)

2451

Rat

Low

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

2110

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.2

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.01

Rat SF=100

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

0.017

Rat SF=100

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

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

0.02

Rat SF=100

Dermal penetration studies (%)

1.0-6.5

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Harmful if inhaled or ingested
Kidney, spleen and liver toxicant
May cause eye cateracts

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H361d, H373, H317

EC Risk Classification

Reproduction risk category 3: R63
Xn - Harmful: R48/22, R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S29, S36/37, S46, S60, S61

WHO Classification

III (Slightly hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fluazifop-P-butyl

French

fluazifop-P-butyl

German

Fluazifop-P-butyl

Danish

fluazifop-P-butyl

Italian

fluazifop-P-butile

Spanish

fluazifop-P-butil

Greek

fluazifop-P-butyl

Polish

fluazyfop-P butylowy

Swedish

Hungarian

fluazifop-P-butyl

Dutch

fluazifop-P-butyl

Record last updated:	23/01/2021
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