Triadimefon	Last updated: 23/05/2019
(Also known as: triadimefone; triadimenol metabolite M01)

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GENERAL INFORMATION

Description	A common fungicide used to control fungal infections in many crops. It is also a pesticide transformation product
Example pests controlled	Powdery mildew; Leaf rust; Stripe rust; Speckled leaf blotch; Septoria; Leaf scald
Example applications	Cereals including Wheat and barley; Peas; Grapevines; Curcubits; Sugarcane
Efficacy & activity	-
Availability status	Current
Introduction & key dates	1976

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
UK LERAP status	No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Not approved
Dossier rapporteur/co-rapporteur	Not applicable
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	Not applicable
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

Also used in	Australia, USA

Chemical structure

Isomerism	A chiral molecule with one chiral centre. There is little notable difference in the biological activities of the different enantiomeric forms
Chemical formula	C₁₄H₁₆ClN₃O₂
Canonical SMILES	CC(C)(C)C(=O)C(N1C=NC=N1)OC2=CC=C(C=C2)Cl
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	WURBVZBTWMNKQT-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C14H16ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,13H,1-3H3
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
triadimefon	Unstated isomer

General status

Pesticide type	Fungicide, Metabolite
Metabolite Type	Soil
Substance group	Triazole
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Systemic with protective, curative and eradicant action. Disrupts membrane function. Sterol biosynthesis inhibitor.
CAS RN	43121-43-3
EC number	256-103-8
CIPAC number	352
US EPA chemical code	109901
PubChem CID	39385
Molecular mass	293.8
PIN (Preferred Identification Name)	rac-(1R)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one
IUPAC name	(RS)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one
CAS name	1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone
Other status information	-
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	Colourless crystals
Related substances & organisms	silica

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Triadimefon 500WG Bayleton Amiral
Example products using this active	Bayer CropScience Mobay
Formulation and application details	Usually formulated as an emulsifiable concentrate or wettable powder

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		70	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)		200000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Toluene	-
		200000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Dichloromethane	-
		99000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Isopropanol	-
		6300	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Hexane	-
Melting point (°C)		82.3	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Boiling point (°C)		Decomposes before boiling	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		72	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.51 X 1003	Calculated	-
	Log P	3.18	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data	High
Bulk density (g ml⁻¹)		1.28	P4 P = Other governments and regulators 4 = Verified data	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		0.02	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		9.00 X 10-05	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Non-volatile
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)	26	W4 W = French database provided by ARVALIS-Institut du Végétal 4 = Verified data	Non-persistent
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Best available data
Dissipation rate RL₅₀ on plant matrix	Value	3.9	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	-
	Note	Ryegrass blades, n=1
Dissipation rate RL₅₀ on and in plant matrix	Value	4.3	R4 R = Peer reviewed scientific publications 4 = Verified data	-
	Note	Published literature RL₅₀ range 1.6-16.0 days, 14 field & undercover grown crops, various matrices, n=17; RL₅₀ grapes in cold storage = 216 days
Aqueous photolysis DT₅₀ (days) at pH 7	Value	0.8	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Fast
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	Stable	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Stable
	Note	Stable pH 3 to pH 9, 22 °C
Water-sediment DT₅₀ (days)		43	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source	Moderately fast
Water phase only DT₅₀ (days)		12	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source	Moderately fast

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	G3 G = Extension Toxicology network database EXTOXNET (click here ) 3 = Unverified data of known source	Moderately mobile
	Koc	300
	Notes and range	-
Freundlich	Kf	10.16	R4 R = Peer reviewed scientific publications 4 = Verified data	Slightly mobile
	Kfoc	749
	1/n	0.750
	Notes and range	Literature data: Kf range 1.33-22.0 mL g⁻¹, Kfoc range 344-2095 mL g⁻¹, 1/n range 0.71-0.77, Soils=8
pH sensitivity		No

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		1.59	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	4.12 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		Low	Calculated	-
Potential for loss via drain flow		Moderately mobile	Calculated	-

Key metabolites

Metabolite	Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
triadimenol (Ref: BAY KWG 0519)	Soil	0.9	Major fraction; Relevant

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	64.0	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	Low potential
	CT₅₀ (days)	0.6		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		300	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Rat 2 year	-
	(ppm diet)	300		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		> 2000	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 Colinus virginianus	Low
Birds - Short term dietary (LC₅₀/LD₅₀)		> 880 mg kg bw⁻¹ day⁻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 Colinus virginianus	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		4.08	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 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		0.017	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 Pimephales promelas	Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		7.16	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 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		0.1	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 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)		-	-	-
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)		2.01	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 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)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	> 25	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data	Moderate
	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)		> 50	P2 P = Other governments and regulators 2 = Unverified data of unknown source Eisenia foetida	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	-	-	-
	% 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)		300	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		5000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		3.27	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		0.03	F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 5 = Verified data used for regulatory purposes JMPR 2004	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		0.08	F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 5 = Verified data used for regulatory purposes JMPR 2004	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Routes	Public	-
	Occupational	-
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 ?Possibly, status not identified A3 A = Chromosome aberration (EFSA database) 3 = Negative ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E3 E = Unspecified genotoxicity type (miscellaneous data source) 3 = Negative ?Possibly, status not identified Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ✓Yes, known to cause a problem XNo, known not to cause a problem ?Possibly, status not identified Respiratory tract irritant Skin irritant Skin sensitiser No data found ✓Yes, known to cause a problem ?Possibly, status not identified Eye irritant Phototoxicant   ?Possibly, status not identified No data found
General human health issues		Liver and thyroid toxicant Estrogenic USEPA - possible human carcinogen Endocrine issues - Estrogenic effect

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	Health: H302, H317 Environment: H411
EC Risk Classification	Xn - Harmful: R22, R43 N - Dangerous for the environment: R51, R53
EC Safety Classification	S2, S24, S37, S61
WHO Classification	II (Moderately hazardous)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	triadimefon
French	triadimefon
German	Triadimefon
Danish	triadimefon
Italian	triadimefon
Spanish	triadimefon
Greek	-
Polish	triadimefon
Swedish	triadimefon
Hungarian	triadimefon
Dutch	triadimefon

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Record last updated:	23/05/2019
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