Cyflufenamid (Ref: NF 149)

Cyflufenamid (Ref: NF 149)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A new 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, Japan

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2026

UK LERAP status

None

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

31/03/2023

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

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 group

Amidoxine

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

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 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

White solid

Formulations

Property

Value

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

Cyflamid
Takumi SC

Example products using this active

Certis

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)

Not expected to self ignite; Not highly flammable

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

5.01 X 10⁰⁴

Calculated

Log P

4.7

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

28.5

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.347

Major fraction, Relevant

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

Soil

0.185

Major fraction, Relevant

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

Soil

0.229

Major fraction, Relevant

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

Soil

0.09

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

528

Threshold for concern

CT₅₀ (days)

1.3

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)

Colinius virginianus NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.04

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.024

Pimephales promelas

Moderate

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

> 1.73

Daphnia magna

Moderate

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

0.041

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)

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)

Non-target plants

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

> 0.828

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

Low

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

> 100

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

48 hour
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

>; 7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 0.294 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)

> 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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=51 µg l⁻¹

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
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H332
Environment: H400, H410, H411

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

cyflufenamid

French

cyclufénamid

German

Cyflufenamid

Danish

cyflufenamid

Italian

ciflufenamid

Spanish

ciflufenamid

Greek

Polish

cyflufenamid

Swedish

cyflufenamid

Hungarian

Dutch

Record last updated:	12/01/2021
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