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Triadimefon
(Also known as: triadimefone; triadimenol metabolite M01)
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
High alert:
Fish chronic ecotoxicity: High
Human health
High alert:
Endocrine distrupter; 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
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
                 
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 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
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
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 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; 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
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (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 -
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 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)
- - -
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
- - -
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
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)
- - -
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
- - -
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
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
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
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Italian
triadimefon
Spanish
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Greek
-
Polish
triadimefon
Swedish
triadimefon
Hungarian
triadimefon
Dutch
triadimefon
Norwegian
-
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