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GET ADDITIONAL DATA HERE!

cyflufenamid (Ref: NF 149)
** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for cyflufenamid

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

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Germany/Austria
Date inclusion expires 31/03/2023
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Chemical structure: Click here for further information on the general chemical status information used on this site
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: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Amidoxine
Minimum active substance purity 980 g/kg
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 (g mol-1) 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) U6
Examples of recorded resistance -
Physical state White solid
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Certis
Example products using this active
  • Cyflamid
  • Takumi SC
UK LERAP status None
Formulation and application details Often supplied as oil suspensions which are mixed with water and applied as a spray.


ENVIRONMENTAL FATE

for cyflufenamid

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.52 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 15700 A5 - n-Heptane -
18600 A5 - n-Hexane -
198000 A5 - Methanol -
217000 A5 - Xylene -
Melting point (oC) 62 A5 -
Boiling point (oC) 257 A5 -
Degradation point (oC) 140 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 5.01 X 1004 Calculated -
Log P 4.7 A5 High
Bulk density (g ml-1)/Specific gravity 1.35 A5 -
Dissociation constant (pKa) at 25oC 12.08 A5 -
Note: Strong base
Vapour pressure at 20oC (mPa) 0.0354 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 2.81 X 10-02 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.85 Calculated Transition state
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 6.81 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
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 A5 -
Surface tension (mN m-1) 66.5 A5 at 20oC -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 33.8 A5 Moderately persistent
DT50 (lab at 20oC) 210 A2 Persistent
DT50 (field) 25.3 A3 Non-persistent
DT90 (lab at 20oC) 282 A3 -
DT90 (field) 120 A5 -
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 R4 -
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 A5 Stable
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 9, up to 50 degC
Water-sediment DT50 (days) 77.2 A5 Moderately fast
Water phase only DT50 (days) 4.3 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 28.5 A5 Slightly mobile
Kfoc 1592
1/n 0.93
Notes and range EU dossier Kf range 12.7-56.5 mL/g, Kfoc range 1000-2354 mL/g, 1/n range 0.87-0.96, Soils=4
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
N-cyclopropylmethoxy-2,3-difluoro-6-trifluoromethylbenzamidine (Ref: 149-F) This metabolite may cause environmental pollution, click here for further information Soil   0.347   Major fraction, Relevant
((Z)-N-(alpha-cylcopropylmethoxyimino-2,3-difluoro-6-trifluoromethylbenzyl)carbamoylacetic acid (Ref: 149-F11) This metabolite may cause environmental pollution, click here for further information Soil   0.185   Major fraction, Relevant
2,3-difluoro-6-trifluoromethylbenzamidine (Ref: 149-F1) This metabolite may cause environmental pollution, click here for further information 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 Š-(‚-glucopyranosylimino)benzyl]}-2-phenylacetamide 149-F4B-Glu Plant - -


ECOTOXICOLOGY

for cyflufenamid

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 528 A5 Threshold for concern
CT50 (days) 1.3 -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) > 75 A5 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 743 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 1.04 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.024 A5 Pimephales promelas Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 1.73 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.041 A5 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 A5 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 A5 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 A5 Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 100 A5 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 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 50 48 hour
A5 Aphidius rhopalosiphi, adult
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 50 >; 7 day
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.294 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for cyflufenamid

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 4.76 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.04 A5 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.05 A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.03 A5 -
Dermal penetration studies (%) 1-8 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public No unacceptable risks to bystanders identified
Minimal risk of dietary exposure
Occupational -
European MRLs Click here for the 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; A5 -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A3; B3; C3; D0; E0

-

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

General human health issues Kidney and liver toxicant
USEPA - some evidence to suggest possible human carcinogen
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Environment: H411
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S60, S61
WHO Classification NL - Not listed
UN Number Usually 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for cyflufenamid

Language Name
English cyflufenamid
French cyclufénamid
German Cyflufenamid
Danish cyflufenamid
Italian ciflufenamid
Spanish ciflufenamid
Greek -
Slovenian ciflufenamid
Polish cyflufenamid
Swedish cyflufenamid
Hungarian -
Dutch -

Record last updated: Tuesday 25 June 2019
Contact: aeru@herts.ac.uk