Quinoxyfen (Ref: DE 795)

Quinoxyfen (Ref: DE 795)	Last updated: 08/03/2021
(Also known as: quinoline)

GENERAL INFORMATION

Description

A fungicide used mainly to control powdery mildew in cereals and other crops

Example pests controlled

Powdery mildew

Example applications

Cereals; Grapes; Curcubits; Mangoes; Tomato

Efficacy & activity

Wheat/Mildew=Low; Mildew=Low for protection, no data for eradication

Availability status

Current

Introduction & key dates

1996, Europe

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

UK/Austria

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
	✓		✓	✓	✓			✓

Also used in

Australia, Chile, USA

Chemical structure

Isomerism

Chemical formula

C₁₅H₈Cl₂FNO

Canonical SMILES

C1=CC(=CC=C1OC2=C3C(=CC(=CC3=NC=C2)Cl)Cl)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

WRPIRSINYZBGPK-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H8Cl2FNO/c16-9-7-12(17)15-13(8-9)19-6-5-14(15)20-11-3-1-10(18)2-4-11/h1-8H

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Quinoline

Minimum active substance purity

99.7%

Known relevant impurities

EU 2003 dossier - 4,5,7-trichloroquinoline

Substance origin

Synthetic

Mode of action

Systemic with protective properties, translocates and inhibits appressoria development stopping infections. Signal transduction

CAS RN

124495-18-7

EC number

CIPAC number

566

US EPA chemical code

055459

PubChem CID

3391107

Molecular mass

308.13

PIN (Preferred Identification Name)

5,7-dichloro-4-(4-fluorophenoxy)quinoline

IUPAC name

5,7-dichloro-4-quinolyl 4-fluorophenyl ether

CAS name

5,7-dichloro-4-(4-fluorophenoxy)quinoline

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

Off-white solid

Related substances & organisms

propylene glycol

cyproconazole

fenpropimorph

Formulations

Property

Value

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

Apres
Excelsior
Fortress
Orka
Legend
proxima

Example products using this active

Dow AgroSciences

Formulation and application details

Often supplied as a soluble 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)

0.047

Low

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

9640

Hexane

21500

Methanol

272000

Toluene

116000

Acetone

Melting point (°C)

103

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.26 X 10⁰⁵

Calculated

Log P

5.1

High

Bulk density (g ml⁻¹)

1.56

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.012

Low volatility

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

3.08 X 10^-02

Non-volatile

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

Maxima at 298nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

308

Persistent

DT₅₀ (lab at 20 °C)

308

Persistent

DT₅₀ (field)

169.3

Persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

2270

DT₅₀ modelling endpoint

Note

EU 2017 lab studies DT₅₀ range 110-560 days, Soils = 12, Field studies DT₅₀ range 14.7-588 days, DT₉₀ range 391 - >10,000 days, Soils =10; EU 2003 dossier Lab studies DT₅₀ range 224-508 days, field study DT₅₀ range 13-190 days (EU), DT₉₀ range 380-750 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

7.2

Note

Grape berries, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.8

Fast

Note

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

Value

Stable

Note

pH and temperature sensitive: DT₅₀ 75 days at pH 5 and 25 °C, 7 days at pH 5 and 50 °C, stable pH 7 and pH 9

Water-sediment DT₅₀ (days)

127

Slow

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

Non-mobile

K_foc

22929

¹/_n

Notes and range

EU Dossier K_foc range 18339 – 28897 mL g⁻¹

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.80

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3-hydroxy-quinoxyfen (Ref: 3-OH DE-795)

Soil

0.270

Major fraction; Not significant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

5,7-dichloro-4-(4-fluorophenoxy)quinoline-N-oxide

DE-795 n-oxide; quinoxyfen n-oxide

4-fluorophenol

Animal; Plamt

5,7-dichloro-4-hydroxyquinoline
Note: Minor metabolite

DCHQ

Soils (acidic)

0.064

2-chloro-10-fluoro[1]benzopyrano[2,3,4-de-quinoline

CFBPQ

Water (Photolysis)

5,7-dichloro-4-(4-fluorophenoxy)-2-oxo-quinoline

2-oxo DE-795; 2-oxoquinoxyfen

Plant; Soil (Aerobic)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

5040

High potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

> 10

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

100

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.27

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.014

Oncorhynchus mykiss

Moderate

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

0.08

Daphnia magna

High

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

0.028

Daphnia magna

Moderate

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)

0.128

Chironomus riparius emergence

Moderate

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

0.548

Chironomus riparius

Moderate

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

1.85

Lemna gibba

Moderate

Non-target plants

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

0.027

Raphidocelis subcapitata 120 hour

Moderate

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

0.026

Unknown species

Moderate

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)

> 923

Eisenia foetida

Moderate

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

2.67

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

63 / -85

Mortality / Parasitism [Dose: Not stated]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

-93.3

Beneficial capacity [Dose: Not stated]
Typhlodromus pyri adult

Soil micro-organisms

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

Dose: 5.3 mg kg⁻¹ soil

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.38

Rat

Other Mammal toxicity endpoints

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

0.2

Dog SF=100

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)

0.14

Dog 1 year SF=100

Dermal penetration studies (%)

10.0

Dangerous Substances Directive 76/464

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)

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

Possible liver, kidney and blood toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S24, S37, S46, S60, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

quinoxyfen

French

quinoxyfen

German

Quinoxyfen

Danish

quinoxyfen

Italian

quinoxifen

Spanish

quinoxifen

Greek

quinoxyfen

Polish

quinoxyfen

Swedish

Hungarian

quinoxifen

Dutch

quinoxyfen

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