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

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
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

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