Triadimefon	Last updated: 22/08/2024
(Also known as: triadimefone; triadimenol metabolite M01)

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SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Drainflow: Moderately mobile Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health High alert: Endocrine disrupter; Reproduction/development effects

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, introduced

GB regulatory status

GB COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
GB LERAP status	No UK approval for use as a plant protection agent

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
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries	ISIceland NONorway

Additional information

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 groups	Triazole fungicide; Conazole fungicide
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
CLP index number	606-037-00-4
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 Class (HRAC MoA class)	Not applicable
Herbicide Resistance Class (WSSA MoA class)	Not applicable
Insecticide Resistance Class (IRAC MoA class)	Not applicable
Fungicide Resistance Class (FRAC MOA class)	3
Examples of recorded resistance	-
Physical state	Colourless crystals

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Bayer CropScience Mobay
Example products using this active	Triadimefon 500WG Bayleton Amiral
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. Dataset is no longer available. 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; Chemspider; PubChem. (ChemID ) 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. Available online but no longer updated. (click here ) 4 = Verified data	High
Fat solubility of residues	Solubility	Soluble	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	-
	Data type	Regulatory data - observed in metabolism and farm animal feeding studies	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	-
Density (g ml⁻¹)		1.28	P4 P = Other non-EU, UK or US 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
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
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. Dataset no longer available. 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 (days) 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 (days) 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; these datasets no longer available). Norman Ecotoxicology database. (click here ) 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 data from online sources 2 = Unverified data of unknown source	Moderately fast
Water phase only DT₅₀ (days)		12	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source	Moderately fast
Sediment phase only DT₅₀ (days)		-	-	-
Air degradation		As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here ) 3 = Unverified data of known source	Moderately mobile
	Koc (mL g⁻¹)	300
	Notes and range	-
Freundlich	Kf (mL g⁻¹)	10.16	R4 R = Peer reviewed scientific publications 4 = Verified data	Slightly mobile
	Kfoc (mL g⁻¹)	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	-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk		-	-	-
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		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
triadimenol (Ref: BAY KWG 0519)	Major fraction	0.9	-

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		300	G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (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 yr	-
	(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)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		> 50	P2 P = Other non-EU, UK or US Governments and Regulators 2 = Unverified data of unknown source Eisenia foetida	Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Soil micro-organisms		-	-	-
Collembola	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Non-target plants		-	-	-
		-	-	-
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	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Apis mellifera	Moderate
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Chronic	-	-	-
	Notes	-
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 bee species (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other bee species (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Beneficial insects (Ladybirds)		-	-	-
Beneficial insects (Lacewings)		-	-	-
Beneficial insects (Parasitic wasps)		-	-	-
Beneficial insects (Predatory mites)		-	-	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Temperate Freshwater 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
Temperate Freshwater 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
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		9.41	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data Danio rerio	Moderate
Temperate Freshwater 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
Temperate Freshwater 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
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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 (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)		-	-	-
Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)		-	-	-
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)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-
Marine bivalves		-	-	-

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. Available online but no longer updated. (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	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	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		0.08	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	-
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	-
MRLs	European	EU MRL pesticide database
	Great Britain	GB MRL Register
	Notes	-
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-
Mammalian dose elimination route and rate		-	-	-

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 ✓Yes, known to cause a problem 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 US EPA - 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
WHO Classification	II (Moderately hazardous)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

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

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Record last updated:	22/08/2024
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