Fluquinconazole (Ref: AE C597265)

Fluquinconazole (Ref: AE C597265)	Last updated: 28/01/2021
(Also known as: SN 597265)

GENERAL INFORMATION

Description

A selective protectant and curative fungicide used to control various endophytic diseases mainly on cereals

Example pests controlled

Septoria leaf spot, Septoria glume blotch, Yellow rust, Prown rust, Powdery mildew

Example applications

Cereals including wheat

Efficacy & activity

Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=Moderate

Availability status

Current

Introduction & key dates

circa 1995

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

UK/Slovakia

Date EC 1107/2009 inclusion expires

31/12/2021

EU Candidate for substitution (CfS)

Yes - low ADI ARfD / AOEL; two 'Persistent-Bioaccumulative-Toxic' criteria

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

Chemical formula

C₁₆H₈Cl₂FN₅O

Canonical SMILES

C1=CC2=C(C=C1F)C(=O)N(C(=N2)N3C=NC=N3)C4=C(C=C(C=C4)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

IJJVMEJXYNJXOJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H8Cl2FN5O/c17-9-1-4-14(12(18)5-9)24-15(25)11-6-10(19)2-3-13(11)22-16(24)23-8-20-7-21-23/h1-8H

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Triazole

Minimum active substance purity

955 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Absorbed through foliage. Systemic with protectant and eradicant activity. Disrupts membrane function. Sterol biosynthesis inhibitor.

CAS RN

136426-54-5

EC number

411-960-9

CIPAC number

474

US EPA chemical code

PubChem CID

86417

Molecular mass

376.17

PIN (Preferred Identification Name)

IUPAC name

3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one

CAS name

3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)-4(3H)-quinazolinone

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

Cream to white crystalline solid depending upon purity

Related substances & organisms

prochloraz

Formulations

Property

Value

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

Jockey
Galmano
Sahara, Flamenco

Example products using this active

BASF
Bayer CropScience
Aventis

Formulation and application details

Often supplied as a soluble concentrate which is mixed with water and applied as a spray. Other formulations include those specific for seed treatments.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.15

Low

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

44000

Acetone

34000

Ethyl acetate

3480

Ethanol

114

Hexane

Melting point (°C)

191

Boiling point (°C)

Degradation point (°C)

320

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.74 X 10⁰³

Calculated

Log P

3.24

High

Bulk density (g ml⁻¹)

1.58

Dissociation constant pKa) at 25 °C

0.9

Strong acid, pKa(2) -4.4, Very strong acid

Vapour pressure at 20 °C (mPa)

6.40 X 10^-06

Low volatility

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

2.90 X 10^-06

Non-volatile

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

Neutral solution: 307nm = 4928
Acidic solution: 307nm = 4894
Basic solution: 321nm = 3876

Surface tension (mN m⁻¹)

70.91

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

350

Persistent

DT₅₀ (lab at 20 °C)

324.1

Persistent

DT₅₀ (field)

147.3

Persistent

DT₉₀ (lab at 20 °C)

1079.2

Very persistent

DT₉₀ (field)

489.4

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 186-441 days (normalised), DT₉₀ range 620-1466 days, field studies DT₅₀ range 64-344 days (normalised), DT₉₀ range 212-1151 days; Other studies: lab DT₅₀ range 211-562 days, field range 300-400 days (B5)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

22.2

Note

Published literature RL₅₀ range 16.0-32.0 days, apple fruit, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

21.9

Non-persistent

Note

pH sensitive: DT₅₀ 194 days at pH 4, 2024 days at pH 5, 0.4 days at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

13.7

Fast

Water phase only DT₅₀ (days)

3.5

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

14.8

Slightly mobile

K_foc

870

¹/_n

0.891

Notes and range

EU dossier K_f range 5.3-25.9, K_foc range 750-1153 mL g⁻¹, ¹/_n range 0.836-0.921, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.30

Calculated

Transition state

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

Value

1.26 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3-(2,4-dichlorophenyl)-6-fluoro-quinazolin-2,4(3H)-dione (Ref: AE C596912)

Soil

0.287

Major fraction, Relevant

1,2,4-triazole (Ref: CGA 71019)

Soil

0.189

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-(1H-1,2,4-triazol-1-yl)-DL-alanine

triazolyl alanine

Plant

1H-1,2,4-triazol-1-ylacetic acid

triazolyl acetic acid

Plant

2-{[(2,4-dichlorophenyl)carbamoyl]amino}-5-fluorobenzoic acid

SN 616368

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

0.25

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

112

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.36

Rat

High

(ppm diet)

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

6.8

Unknown species Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5200 mg kg feed⁻¹

Anas platyrhynchos

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

1.9

Colinius virginianus DDD

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.9

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.3

Oncorhynchus mykiss

Moderate

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

> 5.0

Daphnia magna

Moderate

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

0.648

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)

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

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

1.4

Lemna minor

Moderate

Non-target plants

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

0.046

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

Ais mellifera

Low

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

> 100

Ais 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)

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

149.4

<, Mortality
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

149.4

<, Mortality
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 2.5 kg ha⁻¹

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)

112

Rat

Moderate

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

625

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.514

Rat 4 hr (head only)

Other Mammal toxicity endpoints

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

0.002

Dog SF=100

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

0.02

Dog SF=100

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

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

0.001

Dog SF=167

Dermal penetration studies (%)

1-4

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Risk to bystanders acceptable for proposed uses

Occupational

Possible risk to operators and other farm workers - PPE/PPC advised

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=0.9 µg l⁻¹

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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 kidney & liver toxicant

Handling issues

Property

Value and interpretation

General

Prevent generation of mists
Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H301, H312, H315, H331, H372
Environment: H400, H410

EC Risk Classification

T - Toxic: R23/25, R48/25
Xn - Harmful: R21
Xi - Irritant: R38
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S36/37/39, S38, S45, S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fluquinconazole

French

fluquinconazole

German

Fluquinconazol

Danish

fluquinconazol

Italian

fluquinconazolo

Spanish

fluquinconazol

Greek

Polish

fluchinkonazol

Swedish

Hungarian

fluquinkonazol

Dutch

Record last updated:	28/01/2021
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