Cyflufenamid (Ref: NF 149)

Cyflufenamid (Ref: NF 149)	Last updated: 31/10/2024
(Not known by any other names)

SUMMARY

Cyflufenamid is a preventative and curative fungicide. It has a low aqueous solubility and s non-volatile. It may be persistent in some soil and water systems depending on local conditions. The risk of leaching to groundwater is low. It is moderately toxic to aquatic organisms, but less so to birds and honeybees. It has a low oral mammalian toxicity and is an irritant.

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; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate

GENERAL INFORMATION

Description

An amidoxine fungicide for the control of powdery mildew in cereals and other crops

Example pests controlled

Powdery mildew

Example applications

Curcubits including cucumber, courgette, melon & summer squash; Cereals

Efficacy & activity

Wheat/Mildew=High; Barley/Mildew=Moderate for protection & eradication

Availability status

Current

Introduction & key dates

2002, registered Japan

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2031

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Germany/Austria

Date EC 1107/2009 inclusion expires

30/06/2027

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

Morocco

Chemical structure

Isomerism

Isomeric - exists in the Z- and E- forms

Chemical formula

C₂₀H₁₇F₅N₂O₂

Canonical SMILES

C1CC1CONC(=NC(=O)CC2=CC=CC=C2)C3=C(C=CC(=C3F)F)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ACMXQHFNODYQAT-TWGOXAJXNA-N

International Chemical Identifier (InChI)

InChI=1S/C20H17F5N2O2/c21-15-9-8-14(20(23,24)25)17(18(15)22)19(27-29-11-13-6-7-13)26-16(28)10-12-4-2-1-3-5-12/h1-5,8-9,13H,6-7,10-11H2,(H,26,27,28)/f/h26H/b27-19-

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Amide fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Preventative and curative activity, acts by inhibiting the infection process

CAS RN

180409-60-3

EC number

605-896-2

CIPAC number

759

US EPA chemical code

555550

PubChem CID

9844539

Molecular mass

412.36

PIN (Preferred Identification Name)

N-{(Z)-[(cyclopropylmethoxy)imino][2,3-difluoro-6-(trifluoromethyl)phenyl]methyl}-2-phenylacetamide

IUPAC name

(Z)-N-[α-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)benzyl]-2-phenylacetamide

CAS name

[N(Z)]-N-[[(cyclopropylmethoxy)amino][2,3-difluoro-6-(trifluoromethyl)phenyl]methylene]benzeneacetamide

Other status information

PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

U06

Examples of recorded resistance

Physical state

White solid

Formulations

Property

Value

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

Certis

Example products using this active

Cyflamid
Takumi SC

Formulation and application details

Often supplied as oil suspensions which are mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.52

Low

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

15700

n-Heptane

18600

n-Hexane

198000

Methanol

217000

Xylene

Melting point (°C)

Boiling point (°C)

257

Degradation point (°C)

140

Flashpoint (°C)

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

5.01 X 10⁰⁴

Calculated

Log P

4.7

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data

Density (g ml⁻¹)

1.35

Dissociation constant pKa) at 25 °C

12.08

Strong base

Vapour pressure at 20 °C (mPa)

0.0354

Low volatility

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

2.81 X 10^-02

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral solution: 207nm = 20800, 238nm = 12900
Acidic solution: 207nm = 21100, 238nm = 13200, 361nm = 178
Basic solution: 220nm = 13000, 240nm = 11800

Surface tension (mN m⁻¹)

66.5

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

33.8

Moderately persistent

DT₅₀ (lab at 20 °C)

210

Persistent

DT₅₀ (field)

25.3

Non-persistent

DT₉₀ (lab at 20 °C)

282

Persistent

DT₉₀ (field)

120

DT₅₀ modelling endpoint

Note

Lab studies DT₅₀ range 7.1-412 days, DT₉₀ range 23.6-1369 days; field study DT₅₀ range 10.2-91.0 days European soils, DT₉₀ range 35-301 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

1.2

Note

Published literature RL₅₀ range 0.4-2.6 days, field grown squash, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

339

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9, up to 50 °C

Water-sediment DT₅₀ (days)

77.2

Moderately fast

Water phase only DT₅₀ (days)

4.3

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)

28.5

Slightly mobile

K_foc (mL g⁻¹)

1592

¹/_n

0.93

Notes and range

EU dossier K_f range 12.7-56.5 mL g⁻¹, K_foc range 1000-2354 mL g⁻¹, ¹/_n range 0.87-0.96, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.12

Calculated

Low leachability

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

Value

2.21 X 10^-02

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

20.5

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)

528

Threshold for concern

CT₅₀ (days)

1.3

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

N-cyclopropylmethoxy-2,3-difluoro-6-trifluoromethylbenzamidine (Ref: 149-F)

Major fraction

0.347

((Z)-N-(alpha-cylcopropylmethoxyimino-2,3-difluoro-6-trifluoromethylbenzyl)carbamoylacetic acid (Ref: 149-F11)

Major fraction

0.185

2,3-difluoro-6-trifluoromethylbenzamidine (Ref: 149-F1)

Major fraction

0.229

2,3-difluoro-6-(trifluoromethyl)benzamide (Ref: 149-F6)

Minor fraction

0.09

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)

2,3-difluoro-6-trifluoromethylbenzamidine (Ref: 149-F1)

Not relevant

2,3-difluoro-6-(trifluoromethyl)benzamide (Ref: 149-F6)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-{(Z)-[(cyclopropylmethoxy)imino][2,3-difluoro-6-(trifluoromethyl)phenyl]methyl}-2-(2-hydroxyphenyl)acetamide

149-F2-OH-B

Plant

N-{(Z)-[(cyclopropylmethoxy)imino][2,3-difluoro-6-(trifluoromethyl)phenyl]methyl}-2-(4-hydroxyphenyl)acetamide

149-F4-OH-B

Plant; Animal

N-{(Z)-[(cyclopropylmethoxy)imino][2,3-difluoro-6-(trifluoromethyl)phenyl]methyl}-2-hydroxy-2-phenylacetamide

149-Falpha-OH-B

Plant; Animal

N-{(Z)- [2,3-difluoro-6-trifluoromethy á-(â-glucopyranosylimino)benzyl]}-2-phenylacetamide

149-F4B-Glu

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 75

Rat

High

(ppm diet)

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

> 57

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 743 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Colinus virginianus NOEC

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

0.667

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 0.294 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

> 0.0178

Folsomia candida

Non-target plants

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) as % Mortality at dose <50 g ha⁻¹

8.0

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹ 48 hr

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

> 50

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 50 g ha⁻¹

3.3

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

1.04

Oncorhynchus mykiss

Moderate

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

0.024

Pimephales promelas

Moderate

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

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

> 1.73

Daphnia magna

Moderate

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

0.041

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)

1.0

Chironomus riparius

Moderate

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

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

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

> 0.828

Pseudokirchneriella subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

> 4.76

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.04

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

0.05

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

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

0.03

Dermal penetration studies (%)

1-8

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified
Minimal risk of dietary exposure

Occupational

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Amendments to GB authorisations for cyflufenamid/hops from June 2023.

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=51 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

Kidney and liver toxicant
US EPA - weak evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H332
Environment: H400, H410, H411

WHO Classification

Not listed (Not listed)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

cyflufenamid

French

cyclufénamid

German

Cyflufenamid

Danish

cyflufenamid

Italian

ciflufenamid

Spanish

ciflufenamid

Greek

Polish

cyflufenamid

Swedish

cyflufenamid

Hungarian

Dutch

Norwegian

Record last updated:	31/10/2024
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