Quizalofop-P-ethyl (Ref: DPX 79376)

Quizalofop-P-ethyl (Ref: DPX 79376)	Last updated: 21/08/2024
(Also known as: quizalofop-P; NC-302-acid)

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 Moderate alert: Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

An post-emergence annual and perennial grass weed herbicide in sugerbeet and other crops

Example pests controlled

Bentgrass; Volunteer cereals; Perennial ryegrass; Italian ryegrass; Couch

Example applications

Sugarbeet; Fodder beet; Winter and spring OSR; Potatoes; Combining peas; Field beans; Other pulses; Linseed; Sunflowers

Efficacy & activity

Availability status

Current

Introduction & key dates

1989, introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/11/2029

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Finland/Sweden

Date EC 1107/2009 inclusion expires

28/02/2027

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
✓	✓	✓	✓	✓	✓	✓	✓	✓

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, Morocco

Chemical structure

Isomerism

A chiral molecule. Quizalofop-P-ethyl is the more biologically active (+) enantimer of the racemate quizalofop-ethyl.

Chemical formula

C₁₉H₁₇ClN₂O₄

Canonical SMILES

CCOC(=O)C(C)OC1=CC=C(C=C1)OC2=CN=C3C=C(C=CC3=N2)Cl

Isomeric SMILES

CCOC(=O)[C@@H](C)OC1=CC=C(C=C1)OC2=CN=C3C=C(C=CC3=N2)Cl

International Chemical Identifier key (InChIKey)

OSUHJPCHFDQAIT-GFCCVEGCSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H17ClN2O4/c1-3-24-19(23)12(2)25-14-5-7-15(8-6-14)26-18-11-21-17-10-13(20)4-9-16(17)22-18/h4-12H,3H2,1-2H3/t12-/m1/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
quizalofop-P-ethyl	-
quizalofop-ethyl	-

General status

Pesticide type

Herbicide

Substance groups

Aryloxyphenoxypropionate herbicide

Minimum active substance purity

95%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

CAS RN

100646-51-3

EC number

600-119-3

CIPAC number

641.202

US EPA chemical code

PubChem CID

1617113

CLP index number

No data found

Molecular mass

372.81

PIN (Preferred Identification Name)

ethyl (2R)-2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate

IUPAC name

ethyl (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate

CAS name

ethyl (2R)-2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)propanoate

Other status information

Severe Marine Pollutant

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

Bromus rigidus

Physical state

White crystalline powder

Related substances & organisms

quizalofop

quizalofop-ethyl

quizalofop-P-tefuryl

Formulations

Property

Value

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

Adama
Makhteshim
Nissan
FCC
Kingtai Chemicals
BOC Sciences

Example products using this active

Leopard EC
Pilot Ultra
Targa Super
Matador

Formulation and application details

Often supplied as emulsifiable or soluble concentrates that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.61

Low

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

250000

Acetone

250000

Ethyl acetate

250000

Xylene

34870

Methanol

Melting point (°C)

75.0

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

320

Flashpoint (°C)

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

4.07 X 10⁰⁴

Calculated

Log P

4.61

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.301

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.10 X 10^-04

Low volatility

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

6.70 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

0.3

24 hr

Volatilisation is not considered critical for air pollution

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

Neutral solution 343nm = 6342
Acidic solution 343nm = 6356
Basic solution 343nm = 6242

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)

0.4

Non-persistent

DT₅₀ (field)

1.8

Non-persistent

DT₉₀ (lab at 20 °C)

Non-persistent

DT₉₀ (field)

5.7

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.1-1.1 days (normalised), DT₉₀ range 1.1-3.5 days; field studies DT₅₀ range 0.55-8.2 days, DT₉₀ range 1.8-27.4 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.6

Note

OSR straw, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

38.3

Stable

Note

Data for continuous light, DT₅₀ 40.2 days in natural light 40 deg N

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

Value

112

Persistent

Note

pH and temperature sensitive: Stable at pH 4 and 50 °C, DT₅₀ 10.7 days at pH 7 and 40 °C, 4 days at pH 7 and 50 °C, unstable at pH 9 and 50 °C

Water-sediment DT₅₀ (days)

1.51

Fast

Water phase only DT₅₀ (days)

1.55

Moderately 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

Freundlich

K_f (mL g⁻¹)

49.9

Slightly mobile

K_foc (mL g⁻¹)

1816

¹/_n

0.86

Notes and range

EU dossier K_f range 15.4-99.3, K_foc range 1024-3078 mL g⁻¹, ¹/_n range 0.83-0.88, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.19

Calculated

Low leachability

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

Value

4.67 X 10^-04

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

4.5

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

380

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

hydroxy quizalofop (Ref: CGA 294972)

Major fraction

0.157

Adama verified

dihydroxy quinoxaline (Ref: CGA 294970)

Major fraction

0.137

Adama verified

quizalofop (Ref: CGA 287422)

Major fraction

0.876

Adama verified

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

hydroxy quizalofop (Ref: CGA 294972)

Relevancy unknown

dihydroxy quinoxaline (Ref: CGA 294970)

Relevancy unknown

quizalofop (Ref: CGA 287422)

Relevancy unknown

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1182

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

7.7

Rat 2 yr

High

(ppm diet)

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

37.8

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Anas platyrhynchos NOEC

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

250

Eisenia foetida corr

Low

Soil micro-organisms

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

Dose: 925 g ha⁻¹ 60 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

52.31

Zea mays
Seedling emergence, ER₅₀
as g ha⁻¹

5.46

Zea mays
Vegetative vigour, ER₅₀
as g ha⁻¹

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 LR₅₀ g ha⁻¹

48.5

Aphidius rhopalosiphi

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

25.0

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.21

Lepomis macrochirus

Moderate

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

0.044

Oncorhynchus mykiss

Moderate

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

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

0.29

Daphnia magna

Moderate

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

0.023

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)

0.098

Lemna gibba

Moderate

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

0.021

Pseudokirchneriella subcapitata

Moderate

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

Unknown species

Moderate

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)

1182

Rat

Moderate

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

5000

Rat (racemate)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

5.8

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.009

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)

0.01

Dermal penetration studies (%)

18-28

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders

Occupational

Operators require PPE

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Combustiable
IMDG Transport Hazard Class 9
Not expected to auto-ignite

CLP classification 2013

Health: H302, H312
Environment: H400, H410, H413

WHO Classification

Not listed (Not listed)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Store at -20 DegC

TRANSLATIONS

Language

Name

English

quizalofop-P-ethyl

French

quizalofop-P-ethyl

German

Quizalofop-P-ethyl

Danish

quizalofop-P-ethyl

Italian

quizalofop-etile-isomero D

Spanish

quizalofop-P-etil

Greek

Polish

kwizalofop-P-etylowy

Swedish

Hungarian

quinzalofop-P-etil

Dutch

Norwegian

Record last updated:	21/08/2024
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