Haloxyfop (Ref: DOWCO 453)

Haloxyfop (Ref: DOWCO 453)	Last updated: 13/07/2020
(Not known by any other names)

GENERAL INFORMATION

Description

A post-emergence herbicide used to control annual and perennial grass weeds. Also pesticide transformation product.

Example pests controlled

Annual and perennial grass weeds

Example applications

Sugarbeet; Oilseed rape; Potatoes; Onions; Leafy vegetables; Strawberries; Sunflower

Efficacy & activity

Availability status

Unknown

Introduction & key dates

circa 1980

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

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

Also used in

Chemical structure

Isomerism

Haloxyfop is a chiral molecule. The haloxyfop technical material is an isomeric mixture but it is only the R-isomer that is herbicidally active.

Chemical formula

C₁₅H₁₁ClF₃NO₄

Canonical SMILES

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

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

GOCUAJYOYBLQRH-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H11ClF3NO4/c1-8(14(21)22)23-10-2-4-11(5-3-10)24-13-12(16)6-9(7-20-13)15(17,18)19/h2-8H,1H3,(H,21,22)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide, Metabolite

Metabolite Type

Soil

Substance group

Aryloxyphenoxypropionate

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective, absorbed by roots and foliage. Inhibition of acetyl CoA carboxylase (ACCase)

CAS RN

69806-34-4

EC number

CIPAC number

438

US EPA chemical code

PubChem CID

50895

Molecular mass

361.70

PIN (Preferred Identification Name)

rac-(2R)-2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid

IUPAC name

(RS)-2-{4-[3-chloro-5-(trifluoromethyl)-2-pyridyloxy]phenoxy}propionic acid

CAS name

2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acid

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

Colourless crystals

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

haloxyfop-etotyl

Soil

0.4

Formulations

Property

Value

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

Verdict
Gallant
Zellek

Example products using this active

DowElanco

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.6

Low

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

1000000

Acetone

518000

Ethyl acetate

74000

Xylene

170

Hexane

Melting point (°C)

107

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

Log P

Bulk density (g ml⁻¹)

1.64

Dissociation constant pKa) at 25 °C

2.9

Strong acid

Vapour pressure at 20 °C (mPa)

0.00133

Low volatility

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

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)

Non-persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Other data DT₅₀ 3.78-6.96 days (R3)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

5.0

Note

Onion leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

Notes and range

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

3.70

Calculated

High leachability

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

Value

7.63 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

337

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)

> 2150

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 800

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 96.4

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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)

Non-target plants

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

> 106.5

Unknown species

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)

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

> 100

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)

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

% Effect

Harmful

[Dose: 1500 g ha⁻¹]
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Harmless

[Dose: 1500 g ha⁻¹]
Chrysoperla carnea

Soil micro-organisms

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)

337

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

0.00065

EU 2006

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

0.075

EU 2006

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

EU 2006

Dermal penetration studies (%)

7-12

EU 2006 concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Occupational

European MRLs

EU MRL pesticide database

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Harmful by inhalation and if swallowed
Liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302, H318
Environment: H412

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S22, S36, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

haloxyfop

French

haloxyfop

German

Haloxyfop

Danish

haloxyfop

Italian

haloxyfop

Spanish

haloxifop

Greek

Polish

haloksyfop

Swedish

Hungarian

haloxyfop

Dutch

Record last updated:	13/07/2020
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