Mefentrifluconazole (Ref: BAS 750F)

Mefentrifluconazole (Ref: BAS 750F)	Last updated: 18/02/2021
(Not known by any other names)

SUMMARY

Mefentrifluconazole is a relatively new conazole fungicide used to control disease on cereals. It has a low aquesous solubility, low volatility and, based on its its chemical properties, it would not be expected to leach to groundwater. However, it may peersist in some soil systems. Mefentrifluconazole has a low mamalian toxicity. No significant health effects have been identified but it may be a skin sensitiser. It demonstrates a moderate level of toxicity to most species, the main exception is honeybees where the txicity is low.

GENERAL INFORMATION

Description

A novel conazole fungicide

Example pests controlled

Septoria tritici

Example applications

Cereals

Efficacy & activity

Shown to be effective for its proposed uses in experimental trials.

Availability status

Current

Introduction & key dates

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

20/03/2029

UK LERAP status

Possible - check label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

UK/France & Austria

Date EC 1107/2009 inclusion expires

20/03/2029

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
			✓			✓

Also used in

Chemical structure

Isomerism

Chemical formula

C₁₈H₁₅ClF₃N₃O₂

Canonical SMILES

CC(CN1C=NC=N1)(C2=C(C=C(C=C2)OC3=CC=C(C=C3)Cl)C(F)(F)F)O

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

JERZEQUMJNCPRJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H15ClF3N3O2/c1-17(26,9-25-11-23-10-24-25)15-7-6-14(8-16(15)18(20,21)22)27-13-4-2-12(19)3-5-13/h2-8,10-11,26H,9H2,1H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Conazole

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU 2017 dossier: dimethylformamide max: 0.5 g kg⁻¹

Substance origin

Synthetic

Mode of action

A sterol biosynthesis inhibitor

CAS RN

1417782-03-6

EC number

None allocated

CIPAC number

US EPA chemical code

PubChem CID

71230671

Molecular mass

397.78

PIN (Preferred Identification Name)

rac-(2R)-2-(4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

IUPAC name

(2RS)-2-(4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

CAS name

α-(4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)-a-methyl-1H-1,2,4-triazole-1-ethanol

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)

Not known

Examples of recorded resistance

Physical state

White crystalline powder

Formulations

Property

Value

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

Revysol

Example products using this active

BASF

Formulation and application details

Usually supplied as an emulsifiable concentrate and used as a foliar spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.81

Low

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

93200

Acetone

116200

Ethyl acetate

8500

Xylene

55300

1,2-Dichloroethane

Melting point (°C)

126

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

300

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.51 X 10⁰³

Calculated

Log P

3.4

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

3.0

Calculated

Vapour pressure at 20 °C (mPa)

3.2 X 10^-03

Low volatility

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

1.6 X 10^-03

Non-volatile

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

at pH 6.1: 202nm=37761; at pH 6.4: 194nm=54636; at pH 1.4: 199nm=43245, at pH 12.2: 231nm=16668

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

268

Persistent

DT₅₀ (lab at 20 °C)

268

Persistent

DT₅₀ (field)

200

Persistent

DT₉₀ (lab at 20 °C)

1000

Very persistent

DT₉₀ (field)

891

DT₅₀ modelling endpoint

846.6

Actual measured max aerobic conditions EU locations

Note

EU 2017 dossier Lab studies: DT₅₀ range 104-477 days, DT₉₀ >1000 days, Soils=5; Field studies DT₅₀ range 96.5-611 days, DT₉₀ range 616->1000 days, Soils=6

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Note

Water-sediment DT₅₀ (days)

163.2

Slow

Water phase only DT₅₀ (days)

7.2

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

39.93

Slightly mobile

K_foc

3456

¹/_n

0.975

Notes and range

EU 2017 dossier K_f range 24.53-126.14 mL g⁻¹, K_foc range 2010-4931 mL g⁻¹, ¹/_n range 0.92-1.02, Soils=8

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.06

Calculated

Low leachability

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

Value

2.26 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.051

Minor fraction; Relevant

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)

> 2000

Rat

Low

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)

816

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.532

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.944

Daphnia magna

Moderate

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

0.016

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

1.30

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

> 97.0

Chironomus dilutus 10day

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

> 1.158

Chironomus riparius

Moderate

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

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

2.02

Lemna gibba growth

Moderate

Non-target plants

> 1.5

across all tested species incl. lettuce tomato cabbage soybean wheat
Vegetative vigour, ER₅₀
as L product ha⁻¹

> 1.5

across all tested species incl. lettuce tomato cabbage soybean wheat
Seedling emergence, ER₅₀
as L product ha⁻¹

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

1.352

Pseudokirchneriella subcapitata

Moderate

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

0.103

Pseudokirchneriella subcapitata 72hr

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)

> 200

Bombus terrestris

Low

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

> 195.4

Bombus terrestris

Low

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

769

Typhlodromus pyri as product

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

95.4

Aphidius rhopalosiphi as product

% Effect

Soil micro-organisms

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

Dose: 2.53 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)

> 2000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.31

Rat (nose only)

Other Mammal toxicity endpoints

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

0.035

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

0.15

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

0.15

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

0.035

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable risk for the proposed uses

Occupational

Acceptable risk for the proposed uses

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

Potential liver toxicant
May cause an allergic skin reaction

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317
Environment: H400, H410

EC Risk Classification

EC Safety Classification

WHO Classification

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

mefentrifluconazole

French

mefentrifluconazole

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	18/02/2021
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