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Your Location：Home>Product Center >> Pesticide API and intermediates >> Tebuconazole
  • Tebuconazole
Name:Tebuconazole
CAS No:107534-96-3

PRODUCT DESCRIPTION

Name】
Tebuconazole
【CAS Registry number】
107534-96-3
【Synonyms】
Fenetrazole
BAY-HWG 1608
Tebuconazole 95%TC
LYNX
Preventol A 8
Etiltrianol
Folicur
Elite
Tebuconazole (+-)
Raxil
Terbutrazole
HWG 1608
Ethyltrianol
tebuconazolel
1-(4-chlorphenyl)-4,4-dimethyl-3-(1H-1,2,4-triazole-1-methyl)amyl-3-alcohol
Tebuconazole Technical
1,2,4-triazol-1-ylmethyl)pentan-3-ol
Tebuconazole Tech
【EINECS(EC#)】
403-640-2
【Molecular Formula】
C16H22ClN3O (Products with the same molecular formula)
【Molecular Weight】
307.81838 [g/mol]
【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
【InChIKey】
PXMNMQRDXWABCY-UHFFFAOYSA-N
【Canonical SMILES】
CC(C)(C)C(CCC1=CC=C(C=C1)Cl)(CN2C=NC=N2)O
【MOL File】
107534-96-3.mol

Chemical and Physical Properties

【Density】
1.14g/cm3
【Melting Point】
102-105 °C
【Boiling Point】
476.9°Cat760mmHg
【Vapour】
7.6E-10mmHg at 25°C
【Flash Point】
242.2 °C
【Water】
32 MG/L AT 20 oC
【Solubilities】
32 mg/L at 20 °C in water
【Color/Form】
Colorless crystals
【Storage temp】
0-6°C
【Computed Properties】
Molecular Weight:307.81838 [g/mol]
Molecular Formula:C16H22ClN3O
XLogP3:3.7
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:6
Exact Mass:307.14514
MonoIsotopic Mass:307.14514
Topological Polar Surface Area:50.9
Heavy Atom Count:21
Formal Charge:0
Complexity:326
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Cation Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:6
Conformer Sampling RMSD:0.8
CID Conformer Count:36

Safety and Handling

【Hazard Codes】
Xn: Harmful;N: Dangerous for the environment;
【Risk Statements】
R22;R51/53;R63
【Safety Statements 】
2-22-36/37-61
【Safety】

A poison by inhalation route. Moderately toxic by ingestion and skin contact routes. When heated to decomposition it emits toxic vapors of NOx and Cl?.
Hazard Codes: Xn: Harmful; N: Dangerous for the environment.
Hazard Codes:?HarmfulXn,DangerousN 
Risk Statements: 22-51/53-63?
R22:Harmful if swallowed.?
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R63:Possible risk of harm to the unborn child. 
Safety Statements: 2-22-36/37-61?
S2:Keep out of the reach of children.?
S22:Do not breathe dust.?
S36/37:Wear suitable protective clothing and gloves.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
RIDADR: UN 3077 9/PG 3 
RTECS: XZ4803270

【Transport】
UN 3077 9/PG 3
【Formulations/Preparations】
Emulsifiable concentrate, flowable, seed dressing, oil-water emulsion, water dispersible granule, wettable powder, emulsion for seed treatment.
Trade Names: Folicur, Raxil, Elite, Horizon, Lynx, Matador
Selected products: Elite (spray, USA); Folicur (spray); Raxil (seed treatment); Busker; Orius. Mixtures: Horizon (+triadimenol) (spray); Matador (+triadimenol) (spray); Pronto Plus (+spiroxamine) (spray, Germany); Raxil S (+triazoxide) (seed treatment); Scenic (+fluoxastrobin +prothioconazole). Other products: Abnakis (spray, France); Calao (spray, France); Corail (spray, France); Folicur Solo (spray, Rumania); Gainer (spray, UK); Horizon arbo (spray, France); Horizont (spray, Switzerland); Libero Top (spray, Portugal); Lynx 25 (spray, USA); Maronee (spray, France); Raxil Liquido (seed treatment, Italy); Raxil R (seed treatment, South Africa); Silvacur (spray, Japan, Korea); Silvacur C (spray, Uruguay); Silvacur FH (spray, Uruguay); Tabou (spray, France); Triada (spray, France); Triade (spray, France). Mixtures: Abilis (+triadimenol) (spray, France); Agate (+prochloraz) (spray, UK); Akzent (+guazatine) (seed treatment, Germany, Switzerland); Alpha Raxil CA (+anthraquinone +captan) (seed treatment, France); Arena C (+fludioxonil) (seed treatment, Germany); Array (+spiroxamine) (spray, UK); Balaika (+prochloraz); Bayer UK 413 (+carbendazim) (spray, UK); Beam (+spiroxamine) (spray, UK); Boson (+guazatine) (seed treatment, Germany); Bronze (+spiroxamine) (spray, UK); Bufalo (+fenpropidin) (spray, Belgium); Buster (+spiroxamine) (spray, France); Cartoon (+carbendazim) (spray, France); Cosinus (+propiconazole) (spray, France); Diams (+prochloraz) (spray, France); Draco (+spiroxamine) (spray, UK); Dubelt Jeczmien (+triazoxide) (seed treatment, Poland); Endeavour (+propiconazole) (spray, UK); ?pop?e (+prochloraz) (spray, France); Falcon (+spiroxamine +triadimenol) (spray); Folicur BT (+triadimefon) (spray, E Europe); Folicur C (+carbendazim) (spray, S. Africa); Folicur Combi (+sulfur) (spray, Italy); Folicur Combi (+dichlofluanid) (spray, Spain); Folicur E (+dichlofluanid) (spray, E. Europe); Folicur EM (+tolylfluanid) (spray, Germany); Folicur Forte (+fenpropidin) (spray, Ireland); Folicur Multi (+tolylfluanid) (spray); Folicur Top (+triadimefon) (spray, Hungary); Garnet (+triadimenol) (spray, UK); Gaucho Orge (+imidacloprid +triazoxide) (seed treatment, France, Belgium); Gaucho Rx 246 FS (+imidacloprid) (seed treatment, Sudan, Ethiopia, Latin America); Hattrick (+tolylfluanid) (spray, Czech Republic, Slovakia); Hudson (+spiroxamine) (spray, France); Inca (+carbendazim) (spray, Belgium); Lib?ro (+carbendazim) (spray, France, Belgium); Monicle (+fenpropidin) (spray, UK); N?braska (+prochloraz) (spray, France); Orca (+spiroxamine) (spray, Belgium, France); Raxil (+thiram) (seed treatment, E Europe); Raxil (+imazalil) (seed treatment, East Europe); Raxil C (+cypermethrin) (seed treatment, Australia); Raxil Complex Liquido (+imazalil) (seed treatment, Italy); Raxil Extra (+thiram) (seed treatment, Poland); Raxil Flow (+thiram) (seed treatment, Chile); Raxil G (+guazatine) (seed treatment); Raxil Gel 206 (+thiram) (seed treatment, Poland); Raxil IM (+imazalil) (seed treatment); Raxil Plus (+thiram) (seed treatment, Uruguay); Raxil Secur (+imidacloprid +triazoxide) (seed treatment, UK); Raxil T (+triflumuron) (seed treatment, Australia); Raxil T (+thiram) (seed treatment, E Europe); Raxil TM Liquido (+thiram) (seed treatment, Italy); Raxil Vital (+thiram) (seed treatment, E Europe); Rush (+fenpropidin) (spray, France); Sage (+spiroxamine) (spray, UK); Silvacur (+triadimenol) (spray, UK); Silvacur (+dichlofluanid) (spray, Israel); Silvacur Combi (+triadimenol) (spray, Central America); Soleil (+bromuconazole) (spray, France); Tiebreak (+fenhexamid); Toreador (+carbendazim) (spray, S. Africa); Tricur (+carbendazim); Turfsiba (+pencycuron) (spray, Japan); Veto F (+triadimenol) (spray, UK); Cabestor (+propiconazole) (spray, France); Celeste Orge (+anthraquinone +cyprodinil +fludioxonil) (seed treatment, France); Cogito (+propiconazole) (spray); Gaucho XT (+imidacloprid +metalaxyl); Gladio (+fenpropidin +propiconazole) (spray, Germany); Landor CT (+difenoconazole +fludioxonil) (seed treatment, Germany); Masterlin PTS (+gamma-HCH) (seed treatment, Rumania); Raxil MD Extra (+imazalil +metalaxyl); Raxil-Thiram (+thiram) (seed treatment, USA); Solit?r (+cyprodinil +fludioxonil) (seed treatment); Young-gune (+fenhexamid) (spray, Korea). Discontinued products: Halt (spray, UK); Raxil Dry' (seed treatment, Australia); Raxil Flowable (seed treatment, Australia). Mixtures: Allicur (+tridemorph) (spray, UK); Arena (+fenpiclonil) (seed treatment, Germany); Aurore (+tridemorph) (spray, France); Dipper (+tridemorph); Ferial Orge (+imidacloprid +triazoxide) (seed treatment, France); Folicur Bayfidan (+triadimenol) (spray, Switzerland); Pronto (+fenpropidin) (spray, Germany); Ranger (+fenpropimorph) (spray, Germany); Raxil (+triazoxide) (seed treatment, Norway); Raxil Combi (+triazoxide) (seed treatment, Spain); Raxil WS (+imazalil) (seed treatment, E Europe); Larin (+fenpiclonil +imazalil) (seed treatment, Germany).
【Specification】

?Tebuconazole , its cas register number is 107534-96-3. It also can be called?(+/-)-alpha-(2-(4-chlorophenyl)ethyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazol-1-ethanol ; Elite ; Folicur 1.2 EC ; GWG 1609 ; HWG 1608 ; Lynx 1.2 ; Raxil .

【Octanol/Water Partition Coefficient】
log Kow = 3.7
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

G. Holmwood et al., European patent 40,345 ... US patent 4,723,984 (1981, 1988 both to Bayer)
Produced by opening the 2-tert-butyl-2-(4-chlorophenethyl) oxirane with 1,2,4-triazole in the presence of a base.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
/In animals/ after three days, elimination was almost complete (>99%). Tebuconazole was excreted with the urine and the feces.
(Phenyl-U-14C)-/tebuconazole/ (specific activity: 84.4 mCi/mg; radiochemical purity:> 99%) was administered to 5 rats/sex/group at single doses of 2 or 20 mg/kg or after repeated dosing of 2 mg/kg with non-radiolabeled test material for 14 days, a single dose of labeled material at 2 mg/kg. Radiolabeled material was assayed in the plasma, urine, and feces of all groups and in the bile and expired CO2 of one group each. Maximum relative plasma concentrations ranged from 0.11 to 0.20 and were achieved 0.33 to 1.7 hours after administration of the test material. After 72 hours, % excreted ranged from 91 to 98%. A difference in sex-related excretion of the test material was noted with males having a urine/feces ratio of 16/78 in contrast to the females which excreted at a ratio of 30/62. Biliary excretion was only measured in males. Ninety percent of the radiolabel was recovered in the bile after a single pass through the liver. Only 0.03% of the radiolabel was recovered in the expired air. Residual label in the tissues (excluding the gastrointestinal tract) ranged from 0.21 to 0.67% of the administered dose after 72 hours.
(Phenyl-U-14C)-/tebuconazole/ (specific activity: 84.4 mCi/mg; radiochemical purity: > 99%) was administered to 5 rats/sex/group at single doses of 2 or 20 mg/kg or after repeated dosing of 2 mg/kg with non-radiolabeled test material for 14 days, a single dose of labelled material at 2 mg/kg. (Triazole-3,5-14C)-/tebuconazole/ (specific activity: 56.5 mCi/mg; radiochemical purity-98.4%) was administered to 5 rats/sex at a single dose of 20 mg/kg. Radiolabeled material was assayed in the urine, and feces of all groups for up to 72 hours. The chemical structures of specific radiolabeled metabolites were identified. Females showed a higher renal elimination rate than males (26 to 35% vs. 15 to 18%, respectively). Conversely, males exhibited a higher portion of excreted radioactivity in the feces (77 to 80% vs. 60 to 67%, respectively).
After oral administration of tebuconazole to rats, 65-80% of the dose was eliminated by the biliary and fecal route, whereas elimination in urine amounted to about 16-35%. Males had a greater biliary and fecal elimination than females. Biotransformation proceeded by oxidation reactions, resulting in hydroxy, carboxy, triol and ketoacid metabolites and conjugates as well as triazole.
Groups of rats were treated dermally with doses of 0.01, 0.1, 1 or 10 mg/rat of 14C-tebuconazole in ethanol, corresponding to actual doses of 0.604, 5.86, 52.4 or 547 ug/sq m. Radioactivity was measured in the urine, feces, blood and carcass and at the application site 0.5, 1, 2, 4, 8 and 24 hr after treatment to provide an estimate of skin absorption. At doses up to 52.4 ug/sq m, about 60% of the applied dose was absorbed within 24 hr; at the highest dose, about 12% was absorbed through the skin. Most of the dose was absorbed within the first few hours of application.
The permeability of human and rat skin in vitro to a series of 25% w/w EC formulations of tebuconazole was determined using 14C-tebuconazole and two reference compounds, (4-14C)-hydrocortisone and (4-14C)-testosterone. Within 24 h, up to 37% of a dose of 1.25 g/L tebuconazole in water had permeated human skin,as compared with about 22% of testosterone and up to 5% of hydrocortisone. In the rat, permeation by tebuconazole was lower than that by testosterone but higher than that by hydrocortisone.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 470 to 6,000(2-4), indicate that tebuconazole is expected to have moderate to no mobility in soil(SRC). Volatilization of tebuconazole from moist soil is not expected to be an important fate process(SRC) given an estimated Henry's Law of 1.4X10-10 atm-cu m/mole derived from its vapor pressure 1.3X10-8 mm Hg(5), and water solubility, 36 mg/L(5). Tebuconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Biodegradation data were not available (SRC, 2006).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 470-6000(2-4), indicate that tebuconazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 1.4X10-10 atm-cu m/mole derived from its vapor pressure, 1.3X10-8 mm Hg(6), and water solubility, 36 mg/L(6). According to a classification scheme(7), an estimated BCF of 140(SRC), from its log Kow of 3.7(6) and a regression-derived equation(8) suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data were not available(SRC, 2006).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tebuconazole, which has a vapor pressure of 1.3x10-8 mm Hg at 20 deg C(2) is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tebuconazole may be removed from the air by wet or dry deposition(SRC). Tebuconazole does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(2).

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