(R)-flutriafol	Last updated: 12/01/2021
(Not known by any other names)

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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 COPR regulatory status	Approved (as racemate)
Date COPR inclusion expires	31/05/2024
UK LERAP status	None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Approved (as racemate)
Dossier rapporteur/co-rapporteur	Slovakia/UK
Date EC 1107/2009 inclusion expires	31/05/2021
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes (as racemate)
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

Also used in	Australia, Brazil, South Africa, Russia, Tanzania

Chemical structure

Isomerism	(R)-flutriafol is the R-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-/m1/s1
International Chemical Identifier (InChI)	JWUCHKBSVLQQCO-MRXNPFEDSA-N
2D structure diagram/image available?	Yes

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	13309131
Molecular mass	301.29
PIN (Preferred Identification Name)	-
IUPAC name	(R)-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	flutriafol (S)-flutriafol

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
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 (mPa)		-	-	-
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
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	7.2	R4 R = Peer reviewed scientific publications 4 = Verified data	-
	Note	Published literature data range 5.2-9.2 days, 2 crops, grown undercover, fruit matrix, n=2
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		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
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		-	-	-
Potential for loss via drain flow		-	-	-

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)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
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)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
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	(R)-flutriafol
French	(R)-flutriafol
German	(R-)Flutriafol
Danish	(R)-flutriafol
Italian	(R)-flutriafol
Spanish	(R)-flutriafol
Greek	-
Polish	(R)-flutriafol
Swedish	-
Hungarian	(R)-flutriafol
Dutch	-

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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