Haloxyfop-P-methyl (Ref: DE 535)

Haloxyfop-P-methyl (Ref: DE 535)	Last updated: 24/07/2024
(Also known as: haloxyfop-R-methyl; haloxyfop-P-methyl ester; haloxyfop-R-methyl ester; haloxyfop-R-ME; haloxyfop-P-ME)

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 Low alert: Non-persistent; Potential for particle bound transport: Low Warning: Significant data are missing	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate

GENERAL INFORMATION

Description

A post-emergence herbicide used to control annual and perennial grass weeds

Example pests controlled

Annual and perennial grass weeds

Example applications

Orchards; Soybeans; Sugarbeet; Oilseed rape; Sunflower; Cotton; Bananas; Non-crop situations; Forestry

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1993, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Hungary/Czech Republic

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Chemical structure

Isomerism

Haloxyfop-P-methyl is the herbicidally active R-isomer of haloxyfop-methyl. The parent haloxyfop is a chiral molecule.

Chemical formula

C₁₆H₁₃ClF₃NO₄

Canonical SMILES

CC(C(=O)OC)OC1=CC=C(C=C1)OC2=C(C=C(C=N2)C(F)(F)F)Cl

Isomeric SMILES

C[C@H](C(=O)OC)OC1=CC=C(C=C1)OC2=C(C=C(C=N2)C(F)(F)F)Cl

International Chemical Identifier key (InChIKey)

MFSWTRQUCLNFOM-SECBINFHSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H13ClF3NO4/c1-9(15(22)23-2)24-11-3-5-12(6-4-11)25-14-13(17)7-10(8-21-14)16(18,19)20/h3-9H,1-2H3/t9-/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Aryloxyphenoxypropionate herbicide

Minimum active substance purity

940 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, absorbed by roots and foliage. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

CAS RN

72619-32-0

EC number

406-250-0

CIPAC number

526

US EPA chemical code

PubChem CID

13363033

CLP index number

607-335-00-7

Molecular mass

375.7

PIN (Preferred Identification Name)

methyl (2R)-2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate

IUPAC name

methyl (R)-2-{4-[3-chloro-5-(trifluoromethyl)-2-pyridyloxy]phenoxy}propionate

CAS name

methyl (2R)-2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoate

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

Many recorded cases, Alopecurus myosuroides, Avena fatua, Bromus diandrus, Hordeum leporinum

Physical state

Light amber coloured liquid

Related substances & organisms

haloxyfop-P

Formulations

Property

Value

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

Example products using this active

Gallant Super
Eloge
Gallant Winner
Gallant S

Formulation and application details

Usually supplied as an emulsifiable concentrate applied in aqueous solution by broadcast sprayer

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

7.9

Low

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

Miscible

Acetone

Miscible

Toluene

Miscible

Hexane

Miscible

Ethyl acetate

Melting point (°C)

-12.4

Boiling point (°C)

437

Degradation point (°C)

Flashpoint (°C)

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

1.00 X 10⁰⁴

Calculated

Log P

4.0

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.37

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.055

Low volatility

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

0.0012

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

20.0

24 hr

Volatilisation is potentially a concern for short and long range air transport

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

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

Acidic solution: 274.8nm = 64100, 223.5nm = 16300, 202.0nm = 19500

Surface tension (mN m⁻¹)

58.97

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.5

Non-persistent

DT₅₀ (lab at 20 °C)

0.5

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

0.98

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.001-0.6 days, DT₉₀ range 0.0033 – 1.8 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.0

Note

Cabbage head, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

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

Value

Moderately persistent

Note

pH sensitive: stable at pH 4, DT₅₀ 0.63 days at pH 9

Water-sediment DT₅₀ (days)

0.22

Fast

Water phase only DT₅₀ (days)

0.25

Fast

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

No data for ester due to rapid hydrolysis

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Calculated

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

14.90

Calculated using the Atkinson method, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4-(3-chloro-5-trifluoromethyl-2-pyridyloxyphenol)

Major fraction

0.33

3-chloro-5-trifluoromethylpyridin-2-ol

Major fraction

0.72

3-chloro-1-methyl-5-(trifluoromethyl)-2(1H)-pyridinone

Major fraction

0.26

haloxyfop-P (Ref: DE 535 acid)

Major fraction

0.91

4-(3-chloro-5-trifluoromethyl-2-pyridyloxyphenol)

Major fraction

0.33

3-chloro-5-trifluoromethylpyridin-2-ol

Major fraction

0.72

3-chloro-1-methyl-5-(trifluoromethyl)-2(1H)-pyridinone

Major fraction

0.26

haloxyfop-P (Ref: DE 535 acid)

Major fraction

0.91

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

>= 300

Rat

Moderate

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)

1159

Unknown species

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Anas platyrhynchos

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

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

> 672

Eisenia foetida corr

Moderate

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

Soil micro-organisms

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

Dose: 16 x field rate 28 Day

Collembola

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)

> 100

Apis mellifera

Low

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

> 100

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)

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) as % Mortality at dose 0.108 kg ha⁻¹

100

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as % Mortality at dose 0.108 kg ha⁻¹

91.0

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 0.108 hg 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)

0.088

Lepomis macrochirus

High

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

0.0052

Oncorhynchus mykiss

High

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

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

12.3

Daphnia magna

Moderate

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

0.509

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)

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

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

3.1

Lemna minor

Moderate

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

1.72

Navicula pelliculosa

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)

>= 300

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

0.00065

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

0.075

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

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

0.005

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to workers 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

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

Harmful if swallowed

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

haloxyfop-P-methyl

French

haloxyfop-R-methyle

German

Haloxyfop-R-methyl

Danish

haloxyfop-R-methyl

Italian

haloxyfop-R-metile

Spanish

haloxyfop-R-metil

Greek

haloxyfop-R-methyl

Polish

haloksyfop-R metylu

Swedish

Hungarian

haloxyfop-R-methyl

Dutch

haloxyfop-R-methyl

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