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(S)-flutriafol
Last updated: 25/06/2019
(Not known by any other names)

GENERAL INFORMATION
Description
A specific isomer of a curative and preventative conazole fungicide used to control leaf and ear diseases usually in cereals
Example pests controlled
Leaf and ear diseases
Example applications
Cereals including corn; Soybeans; Apples
Efficacy & activity
Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=Low; Soybean/Anthracnose=High; Soybean/Brown spot=High; Soybean/Leaf blight=Moderate; Soybean/Rust=High; Soybean/White mould=Moderate
Availability status
Current
Introduction & key dates
1981
UK regulatory status
UK approval status
Approved
EC Regulation 1107/2009 (repealing 91/414)
EC Directive 91/414 Status
Approved (as racemate)
Dossier rapporteur/co-rapporteur
Slovakia/UK
Date inclusion expires
31/05/2021
EU Candidate for substitution (CfS)
No
Listed in EU database
Yes (as racemate)
Approved for use (✓) or known to be used (#) in the following EU-27 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
Also used in
Australia, Brazil, South Africa, Russia, Tanzania
Chemical structure
Isomerism
(S)-flutriafol is the S-isomer of chiral flutriafol
Chemical formula
C₁₆H₁₃F₂N₃O
Canonical SMILES
C1=CC=C(C(=C1)C(CN2C=NC=N2)(C3=CC=C(C=C3)F)O)F
Isomeric SMILES
C1=CC=C(C(=C1)[C@](CN2C=NC=N2)(C3=CC=C(C=C3)F)O)F
International Chemical Identifier key (InChIKey)
InChI=1S/C16H13F2N3O/c17-13-7-5-12(6-8-13)16(22,9-21-11-19-10-20-21)14-3-1-2-4-15(14)18/h1-8,10-11,22H,9H2/t16-/m0/s1
International Chemical Identifier (InChI)
JWUCHKBSVLQQCO-INIZCTEOSA-N
2D structure diagram/image available?
No
General status
Pesticide type
Fungicide
Substance group
Triazole
Minimum active substance purity
920 g kg⁻¹
Known relevant impurities
EU dossier - dimethyl sulphate: <0.01%; dimethylformamide:<0.1%; methanol: <0.1%
Substance origin
Synthetic
Mode of action
Broad-spectrum, systemic, contact action with eradicant and protective properties. Sterol biosynthesis inhibitor.
CAS RN
76674-21-0
EC number
-
CIPAC number
436
US EPA chemical code
128940
PubChem CID
25034156
Molecular mass
301.29
PIN (Preferred Identification Name)
-
IUPAC name
(S)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol
CAS name
α-(2-fluorophenyl)-α-(4-fluorophenyl)-1H-1,2,4-triazole-1-ethanol
Other status information
A marine pollutant
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)
3
Examples of recorded resistance
-
Physical state
White crystalline solid
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Beret Multi
  • Consul
  • Impact Excel
  • Pointer
Example products using this active
  • Headland
  • Syngenta
UK LERAP status
None
Formulation and application details
Often supplied as a soluble concentrate that is 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)
- - -
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
- - -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
- - -
Log P
- - -
Bulk density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C
- - -
Henry's law constant at 25 °C
- - -
GUS leaching potential index
- - -
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated - -
Note
-
Potential for particle bound transport index
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
8.4
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
Published literature data range 4.8-10.2 days, 3 field & glasshouse crops, fruit and leaves, n=3
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)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
- - -
Koc
-
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
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)
> 1140
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Rat as isomer mix
Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Birds - Acute LD₅₀ (mg kg⁻¹)
616
A3 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
3 = Unverified data of known source
Alectoris rufa as isomer mix
Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
33.0
A4 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
4 = Verified data
Lepomis macrochirus as isomer mix
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic invertebrates - Chronic 21 day NOEC (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)
- - -
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)
- - -
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)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
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)
- - -
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
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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)
> 1140
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Rat as isomer mix
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
1000
A4 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
4 = Verified data
Rat as isomer mix
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
-
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
-
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.01
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
UK ACP 1999
-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.05
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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)
0.05
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Dog SF=100
-
Dermal penetration studies (%)
0.3-10.0
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
concentration dependent
-
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
Acceptable risk for proposed uses
Occupational
Acceptable risk for proposed uses
European MRLs
EU MRL pesticide database 
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
B3 B = DNA damage/repair (EFSA database)
3 = Negative
;
C3 C = Gene mutation (EFSA database)
3 = Negative
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
?Possibly, status not identified
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
Yes, known to cause a problem
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
?Possibly, status not identified
?Possibly, status not identified
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
Possible liver toxicant
May cause anaemia
Endocrine issues - Weak estrogen inhibition
Handling issues
Property
Value and interpretation
General
Prevent generation of mists
Not explosive or oxidising
IMDG Transport Code 9
CLP classification 2013
Health: H340, H360fd
Environment: H400, H410
EC Risk Classification
Reproduction risk category 3: R63
Xn - Harmful: R20/21/22
N - Dangerous for the environment: R52, R53
EC Safety Classification
S22, S24, S25
WHO Classification
II (Moderately hazardous)
UN Number
3077
Waste disposal & packaging
Packaging Group III (minor danger)
TRANSLATIONS
Language
Name
English
(S)-flutriafol
French
(S)-flutriafol
German
(S)-Flutriafol
Danish
(S)-flutriafol
Italian
(S)-flutriafol
Spanish
(S)-flutriafol
Greek
-
Polish
(S)-flutriafol
Swedish
-
Hungarian
(S)-flutriafol
Dutch
-

Record last updated: 25/06/2019
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