Quizalofop-P-tefuryl (Ref: UBI C4874 )

Quizalofop-P-tefuryl (Ref: UBI C4874 )	Last updated: 08/03/2021
(Also known as: pantera)

GENERAL INFORMATION

Description

A herbicide for the control of annual grass and broad-leaved weeds in a variety of 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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/11/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Hungary/UK

Date EC 1107/2009 inclusion expires

30/11/2021

EU Candidate for substitution (CfS)

Yes - toxic for reproduction

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

Chemical structure

Isomerism

A chiral molecule. Quizalofop-P-tefuryl is the more biologically active enantimer of the racemate quizalofop-tefuryl.

Chemical formula

C₂₂H₂₁CIN₂O₅

Canonical SMILES

CC(C(=O)OCC1CCCO1)OC2=CC=C(C=C2)OC3=CN=C4C=C(C=CC4=N3)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

BBKDWPHJZANJGB-IKJXHCRLSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H21ClN2O5/c1-14(22(26)28-13-18-3-2-10-27-18)29-16-5-7-17(8-6-16)30-21-12-24-20-11-15(23)4-9-19(20)25-21/h4-9,11-12,14,18H,2-3,10,13H2,1H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Aryloxyphenoxypropionate

Minimum active substance purity

926 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic, absorbed through leaves and translocated. An acetyl CoA carboxylase inhibitor (ACCase).

CAS RN

119738-06-6

EC number

414-200-4 (601-628-3)

CIPAC number

US EPA chemical code

PubChem CID

86175

Molecular mass

428.89

PIN (Preferred Identification Name)

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

IUPAC name

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

CAS name

(tetrahydro-2-furanyl)methyl (2R)-2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)propanoate

Other status information

Severe Marine Pollutant

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

Echinochloa crus-galli, Sorghum sudanese

Physical state

Technical materrial is a thick yellow liquid

Formulations

Property

Value

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

Panarex
Pantera

Example products using this active

Certis
Crompton Specialties

Formulation and application details

Often supplied as an emulsifiable concentrate that is 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)

3.13

at 25 °C

Low

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

652000

Toluene

12000

Hexane

64000

Methanol

221000

Acetone

Melting point (°C)

58.3

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

211

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.09 X 10⁰⁴

Calculated

Log P

4.32

High

Bulk density (g ml⁻¹)

1.28

Dissociation constant pKa) at 25 °C

-1.25

Strong acid, 25 DegC

Vapour pressure at 20 °C (mPa)

7.90 X 10^-03

Low volatility

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

9.0 X 10^-04

Non-volatile

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

Neutral solution 238nm = 15171
Acidic solution 238 nm = 15169
Basic solution 238 nm= 15081

Surface tension (mN m⁻¹)

69.3

at 20°C 1.73 mg l⁻¹

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.2

Non-persistent

DT₅₀ (lab at 20 °C)

0.17

Non-persistent

DT₅₀ (field)

0.82

Non-persistent

DT₉₀ (lab at 20 °C)

0.68

Non-persistent

DT₉₀ (field)

6.26

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.04-0.62 days (normalised), DT₉₀ range 0.2-3.1 days; field studies DT₅₀ range 0.5-2.5 days [From DAR], DT₉₀ 2-13 days

Dissipation rate RL₅₀ on plant matrix

Value

0.6

Note

Mung bean, whole plant, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

3.1

Note

Published literature RL₅₀ range 0.7-5.6 days, 2 field grown crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.0

Moderately fast

Note

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

Value

18.2

Non-persistent

Note

pH sensitive: DT₅₀ 8.2 days at pH 5.1, 7.2 hours at pH 9.2, all at 22 °C

Water-sediment DT₅₀ (days)

0.08

Fast

Water phase only DT₅₀ (days)

0.11

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

477

Notes and range

EU dossier - substance degrades rapidly in aerobic soils to the acid.

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

-0.11

Calculated

Low leachability

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

Value

1.97 X 10^-04

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

quizalofop (Ref: CGA 287422)

Soil

1.00

Major fraction, Relevant

hydroxy quizalofop (Ref: CGA 294972)

Soil

0.21

Major fraction, Relevant

dihydroxy quinoxaline (Ref: CGA 294970)

Soil

0.180

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

hydroxy-quinoxaline

CHQ

Soil

0.058

tetrahydrofurfuryl alcohol

Soil

tetrahydrofuroic acid

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

340

Whole fish

Threshold for concern

CT₅₀ (days)

0.9

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1012

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 125

Rat

Moderate

(ppm diet)

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

16.9

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2150

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 258.6 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

68.7

Anas platyrhynchos NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.23

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 1.51

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)

2.1

Lemna gibba

Moderate

Non-target plants

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

> 1.9

Pseudokirchneriella subcapitata

Moderate

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)

> 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)

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

100

<, Mortality
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

100

<, Mortality
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 0.133 mg kg⁻¹ soil 28 days

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)

1012

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.9

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.013

Rat SF=100

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

0.1

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

Rat SF=100

Dermal penetration studies (%)

18-28

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders

Occupational

Operators should use PPE
Negligible risk to other works for proposed conditions of use

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

; ; ; ;

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

Moderately toxic
Liver toxicant

Handling issues

Property

Value and interpretation

General

Not flammable, explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H302, H341, H360, H373
Environment: H400, H411

EC Risk Classification

Reproduction risk category 2 and 3: R61, R62
T - Toxic: R68
Xn - Harmful: R48/22, R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S45, S53, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

quizalofop-P-tefuryl

French

quizalofop-P-tefuryl

German

Quizalofop-P-tefuryl

Danish

quizalofop-P-tefuryl

Italian

quizalofop-P-tefuryl

Spanish

quizalofop-P-teruril

Greek

Polish

kwizalofop-P-tefurylowy

Swedish

Hungarian

quinzalofop-P-tefuril

Dutch

Record last updated:	08/03/2021
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