tebuconazole (Ref: HWG 1608) ** fenetrazole ** terbuconazole ** terbutrazole ** ethyltrianol ** Translations

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GENERAL INFORMATION

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

Introduction: 1986, first reported; 1988, first introduced South Africa

EC Directive 1107/2009 (repealing 91/414):

Status	Annex 1
Dossier rapporteur/co-rapporteur	Denmark
Date inclusion expires	31/08/2019

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia

General status:

Pesticide type	Fungicide
Substance group	Triazole
Substance origin	Synthetic
Mode of action	Systemic with protective, curative and eradicant action. Disrupts membrane function.
CAS RN	107534-96-3
EC number	403-640-2
CIPAC number	494
US EPA chemical code	-
Chemical formula	C16H22ClN3O
SMILES	Clc1ccc(cc1)CCC(O)(C(C)(C)C)Cn2ncnc2
International Chemical Identifier (InChI)	InChI=1/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
Molecular mass (g mol-1)	307.82
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	-
Herbicide Resistance Classification (HRAC)	Not applicable
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	3
Physical state	Colourless crystals
Related substances & organisms	N,N-dimethyl capramide clothianidin triazoxide prochloraz prothioconazole

Formulations:

Property	Value
Example manufacturers of products using this active	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

Property		Value	Source/Quality Score/Other Information	Interpretation
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 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		No data	A3	-
		Note: Very weak base
Vapour pressure at 25oC (mPa)		1.30 X 10-03	A5	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		1.00 X 10-05	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		5.14 X 10-09	K3	Non-volatile
GUS leaching potential index		2.00	Calculated	Transition state
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	7.94 X 10-02	Calculated	-
	Note	-
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		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	62	B5	Moderately persistent
	DT50 (lab at 20oC)	365	A5	Very persistent
	DT50 (field)	55.8	A5	Moderately persistent
	DT90 (lab at 20oC)	-	-	-
	DT90 (field)	177	A5	-
	Note	EU dossier lab studies DT50 >365 days, Field studies DT50 range 19.9-91.6 days, DT90 range 66-304 days; Other sources: DT50 610 days (DW4)
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	Stable
	Note	No significant photolytic degradation
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	Very persistent
	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		Value	Source/Quality Score/Other Information	Interpretation
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	91/414 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

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	78	A5 Whole fish	Low potential
	CT50 (days)	2		-
Bioaccumulation potential		-	Calculated	Low
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	-
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	-
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
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 - Acute 48 hour LD50 (µg bee-1)		> 83.05	A5 Contact	Moderate
Earthworms - Acute 14 day LC50 (mg kg-1)		1381	A5 Eisenia foetida	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		10	A4 Eisenia foetida, 8 week	Moderate
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	62.5	62.5A5 Aphidius rhopalosiphi	Moderately harmful at 1 kg ha-1
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	58.0	A5 Typhlodromus pyri	Moderately harmful at 1 kg ha-1
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect	A5 Dose: 6.25 kg/ha	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
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, 4hr (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 Mice, SF=300	-
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]
Examples of European MRLs (mg kg-1)	Value	Barley, Oats: 2.0; Grapes: 0.2; Wheat, Rye: 0.05
	Note	[A5 EU dossier proposals] For the EU pesticides database click here
Drinking Water MAC (µg l-1)		0.1	EU Dir 89/778/EC limit; A5	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
	-	-
General human health issues		[Targets liver/blood system]

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

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		[Not explosive or oxidising], [IMDG Transport Code is usually 9]
EC Risk Classification		[Reproduction risk category 3: R63], [Xn - Harmful: R22], [N - Dangerous for the environment: R51, R53]
EC Safety Classification		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		[Usually Packaging Group III (minor danger)]

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