INTERNATIONAL UNION
   OF PURE AND APPLIED
   CHEMISTRY
contact
tebuconazole (Ref: HWG 1608)
** fenetrazole ** terbuconazole ** terbutrazole ** ethyltrianol ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for tebuconazole

Description: A fungicide effective against various foliar diseases in cereals and other field crops

Example pests controlled: Smut; Bunt; Stripe rust; Yellow leaf spot; Powdery mildew; Scelerotinia rot; Black spot; Net blotch

Example applications: Cereals including wheat, barley, oat, rye; Grapes; Peanuts; Vegetables including onions, peas, pepper; Bananas; Sugarcane

Efficacy & activity: Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=High; Wheat/Ear blight=Moderate; Barley/Rhynchosporium=Low; Barley/Net blotch=Low; Barley/Ramularia=Low; Corn/Northern leaf blight=High; Corn/Rust=Low

Availability status: Current

Introduction & key dates: 1986, first reported; 1988, first introduced South Africa

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK/Denmark
Date inclusion expires 31/08/2019
EU Candidate for substitution (CfS) Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A chiral molecule. The technical material is an isomeric mixture of the (S-) and (R-) isomers. The R-form is more biologically active than the S-form.
Chemical formula C16H22ClN3O
Canonical SMILES CC(C)(C)C(CCC1=CC=C(C=C1)Cl)(CN2C=NC=N2)O
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) PXMNMQRDXWABCY-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C16H22ClN3O/c1-15(2,3)16(21,10-20-12-18-11-19-20)9-8-13-4-6-14(17)7-5-13/h4-7,11-12,21H,8-10H2,1-3H3
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide, Plant growth regulator
Substance group Triazole
Minimum active substance purity 950 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Systemic with protective, curative and eradicant action. Disrupts membrane function. Sterol biosynthesis inhibitor.
CAS RN 107534-96-3
EC number 403-640-2
CIPAC number 494
US EPA chemical code 128997
PubChem CID 86102
Molecular mass (g mol-1) 307.82
PIN (Preferred Identification Name) rac-(3R)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol
IUPAC name (RS)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol
CAS name α-(2-(4-chlorophenyl)ethyl)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol
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 Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • AgriGuard
  • Bayer CropScience
  • Headland
  • Makhteshim-Agan
  • Nufarm
  • Syngenta
Example products using this active
  • Alpha Tebuconazole
  • Bezel
  • Cello
  • Coronet
  • Folicur
  • Grail
  • Kestrel
  • Mystique
  • Nativo
  • Riza
  • Sage
  • Silvacur
  • Raxil S
UK LERAP status None (may vary with mixtures)
Formulation and application details Often supplied as an oil in water emulsion or concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE

for tebuconazole

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 36 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 200000 A5 - Dichloromethane -
80 A5 - n-Hexane -
57000 A5 - Toluene -
96000 A5 - Octanol -
Melting point (oC) 105 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 350 A4 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 5.01 X 1003 Calculated -
Log P 3.7 A5 High
Bulk density (g ml-1)/Specific gravity 1.25 A5 -
Dissociation constant (pKa) at 25oC 5.0 R4 -
Note: 2013 Peer reviewed literature 5.0
Vapour pressure at 20oC (mPa) 1.30 X 10-03 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.00 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 2.85 Calculated High leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 2.77 X 10-01 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 Neutral solution: 221.4nm = 11980, 262.0nm = 304, 268.5nm = 408, 276.5nm = 368, 290.0nm <10 A5 -
Surface tension (mN m-1) 64.26 A5 at 20oC, 28.8 mg l-1 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 63 B5 Moderately persistent
DT50 (lab at 20oC) 365 A5 Very persistent
DT50 (field) 47.1 A5 Moderately persistent
DT90 (lab at 20oC) - - -
DT90 (field) 177 A5 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 >365 days, Field studies DT50 range 25.8-91.6 days, DT90 range 66-304 days; Other sources: DT50 610 days (DW4)
Dissipation rate RL50 on plant matrix Value 2.3 R4 -
Note Published literature RL50 range 1.4-3.3 days, fruit from 2 field grown crops, n=2
Dissipation rate RL50 on and in plant matrix Value 13.6 R4 -
Note Published literature RL50 range 4.1-59.4 days, 15 field & undercover grown crops, various matrices, n=19; RL50 peppers in cold storage = 106 days
Aqueous photolysis DT50 (days) at pH 7 Value Stable A5 -
Note No significant photolytic degradation
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 9, at 25 degC, 28 days
Water-sediment DT50 (days) 365 A5 Stable
Water phase only DT50 (days) 42.6 A5 Stable

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 12.69 A5 Slightly mobile
Kfoc 769
1/n 0.84
Notes and range EU dossier Kf range 7.67-15.86 mL/g, Kfoc range 102-1249 mL/g, 1/n range 0.711-1.179; Other literature: Mean of 4 soils. Sandy loam - Sand 67% Silt 27% Clay 6% OC=1.4% pH=5.2 Kf=12.7; Silt - Sand 2% Silt 89% Clay 9% OC=1.8% pH=5.3 Kf=16.4; Sand - Sand 87.8% Silt 8.7% Clay 3.5% OC=0.75% pH=5.6 Kf=7.69; Sandy loam - Sand 58.6% Silt 28.1% Clay 13.2% OC=1.27% p
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
1,2,4-triazole (Ref: CGA 71019) Soil   0.09   Minor fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
5-(4-chlorophenyl)-2,2-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentane-1,3-diol hydroxy-tebuconazole Plant - -
2-chloro-5-[4-hydroxy-5,5-dimethyl-3-(1H-1,2,4-triazol-1-yl)hexyl]phenol tebuconazole-m-hydroxy Plant - -
(R,S)-2-amino-3-(1H-1,2,4-triazol-1-yl)propanoic acid, or 3-(1H-1,2,4-triazol-1-yl)-D,L-alanine triazole alanine Plant - -
2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoic acid triazole lactic acid Plant - -
1H-1,2,4-triazol-1-ylacetic acid triazole acetic acid Plant - -
5-(4-chlorophenyl)-3-hydroxy-2,2-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentanoic acid tebuconazole-carboxylic acid Animal - -
5-tert-butyl-5-(1H-1,2,4-triazol-1-ylmethyl)dihydrofuran-2(3H)-one HWG 1608-lactone Water (Photolysis); Water/sediment - -
4-hydroxy-5,5-dimethyl-4-(1H-1,2,4-triazol-1-ylmethyl)hexanoic acid HWG 1608-pentanoic acid Water (Photolysis); Water/sediment - -
sodium 5-(4-chlorophenyl)-3-hydroxy-2,2-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentyl sulfate hydroxy-tebuconazole-sulphate Animal - -


ECOTOXICOLOGY

for tebuconazole

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 78 A5 Whole fish Low potential
CT50 (days) 2 -
Mammals - Acute oral LD50 (mg kg-1) 1700 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) > 10.8 B5 Rat High
(ppm diet) > 100 -
Birds - Acute LD50 (mg kg-1) 1988 A5 Colinus virginianus Moderate
Birds - Short term dietary (LC50/LD50) > 703 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 4.4 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.012 A4 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 2.79 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.01 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.46 A5 Mysidopsis bahia Moderate
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 2.51 A3 Chironomus riparius, EC15 Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.144 A5 Lemna gibba Moderate
Non-target plants > 750 A5 Lepidium sativum
Seedling emergence, ER50
as kg/ha
-
> 10.5 A5 Lepidium sativum
Vegetative vigour, ER50
as kg/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 1.96 A5 Scenedemus subspicatus Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.1 Q2 Unknown species Moderate
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 200 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 83.05 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 1381 A5 Eisenia foetida Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 10 A5 Eisenia foetida, 56 days Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 62.5 Mortality
A5 Aphidius rhopalosiphi
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 58.0 Mortality
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 6.25 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for tebuconazole

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) 1700 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.09 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.03 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.03 A5 Mouse, SF=300 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.03 A5 Dog, SF=100 -
Dermal penetration studies (%) 13 A5 -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Acceptable risk for bystanders
Occupational Operator and other worker exposure acceptable for proposed uses
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) 0.1 EU Dir 89/778/EC limit; A5 -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Targets liver/blood system
USEPA - possible human carcinogen

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H302, H361d
Environment: H411
EC Risk Classification Click here to view information omn the EU risk phrases Reproduction risk category 3: R63
Xn - Harmful: R22
N - Dangerous for the environment: R51, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S22, S36/37, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II, III - Warning - Moderately toxic, Caution - Slightly toxic
UN Number Usually 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for tebuconazole

Language Name
English tebuconazole
French tebuconazole
German Tebuconazol
Danish tebuconazol
Italian tebuconazolo
Spanish tebuconazol
Greek -
Slovenian tebukonazol
Polish tebukonazol
Swedish tebukonazol
Hungarian tebukonazol
Dutch tebuconazool

Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk
© University of Hertfordshire