Tebuconazole

307.81800

307.82

600-834-0

DTXSID9032113

Colorless crystals

2933990015

50.94000

3.34150

1.14g/cm3

102.4 °C

476.9ºC at 760mmHg

242.2ºC

1.564

H2O: 32 mg/L at 20 ºC

0-6ºC

7.6E-10mmHg at 25°C

Henry's Law constant = 1.45X10-10 atm-cu m/mole at 20 °C (est)

pKa = 2.3 (est)

167.37 Ų [M+H]+ [CCS Type: TW]|183.95 Ų [M+Cl]-

Hydroxyl radical reaction rate constant = 1.1 X10-11 cu cm/molec-sec at 25 °C (est)

III

9

UN 3077 9/PG 3

3

R22; R51/53; R63

2-22-36/37-61

XZ4803270

Xn; N

Stable to elevated temperatures, and to photolysis and hydrolysis in pure water, under sterile conditions .

P273-P281

H302-H361d-H411

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.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 234 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 314 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P260, P264, P270, P271, P281, P284, P304+P340, P305+P351+P338, P308+P313, P309+P311, P310, P314, P320, P337+P313, P403+P233, P405, and P501

LD50 Rat oral >5000 mg/kg|LD50 Mouse oral 1615 mg/kg|LD50 Rabbit oral >1000 mg/kg|LD50 Dog oral 625 mg/kg|For more Non-Human Toxicity Values (Complete) data for TEBUCONAZOLE (7 total), please visit the HSDB record page.

Tebuconazole's production may result in its release to the environment through various waste streams; it's use as a fungicide(1) will result in its direct release to the environment(SRC).

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 °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).

Tebuconazole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1) and has been shown to be stable to hydrolysis(2). Tebuconazole does not contain chromophores that absorb at wavelengths >290 nm and has been shown to be stable to photolysis by direct sunlight(2).

An estimated BCF of 140 was calculated for tebuconazole(SRC), using a log Kow of 3.7(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

Using column chromatography, the mean Koc of tebuconazole was calculated to be 1,023(1). In a similar study, a log Koc 2.67 corresponding to a Koc of about 470 was determined using a column loaded with 14 g of soil and assayed via HPLC(2). Using soil thin layer chromatography, a log Koc of 3.7 corresponding to a Koc of 6,000 was determined(3). According to a classification scheme(4), Koc values of 150 to 500 suggest moderate mobility, 500 to 2,000 are low mobility, and values >5,000 are considered to be immobile in soil.

The Henry's Law constant for tebuconazole is estimated as 1.4X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 1.3X10-8 mm Hg(1), and water solubility, 36 mg/L (1). This Henry's Law constant indicates that tebuconazole is expected to be essentially nonvolatile from moist soil and water surfaces(2). Tebuconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Tebuconazole was detected but not quantified in FDA pesticide monitoring studies from 1995, 2000, 2002 and 2003(1-4). These studies analyzed residue in grains, dairy, fish, fruits, vegetables and animal feeds from both the US and foreign sources.

Occupational exposure to tebuconazole may occur through dermal contact with this compound at workplaces where tebuconazole is produced or used. The general population may be exposed to tebuconazole through dermal contact with crops treated with this fungicide or from ingestion of contaminated food. (SRC)

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

/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.|For more Absorption, Distribution and Excretion (Complete) data for TEBUCONAZOLE (6 total), please visit the HSDB record page.

Biotransformation proceeded by oxidation reactions, resulting in hydroxy, carboxy, triol and ketoacid metabolites and conjugates as well as triazole.|Among the metabolites identified, oxidation of the #5 carbon of the pentane chain to an alcohol and then to a carboxyl group was the primary pathway. These metabolites were then further conjugated to either sulfate or glucuronide. The metabolic profile was altered at the higher dose level with a shift to a greater percentage of the alcohol in comparison to the carboxyl containing metabolite. The treatment with the labeled triazole moiety resulted in largely the same metabolic profile except for the recovery of labeled triazole in the urine.|...Rats were treated with tebuconazole labelled with 14C either in the phenyl ring or in the 3,5-triazole ring, with or without pretreatment with unlabelled compound, the main metabolites were the oxidation products of one of the methyl groups of the tertiary butyl moiety, i.e. the alcohol and the carboxylic acid. Metabolism in female animals resulted preferentially in simple oxidation products (eg, hydroxy and carboxy metabolites) and then conjugation to the glucuronide and sulfate, with only minor cleavage of the triazole moiety. In male animals, the primary oxidation products were further oxidized to triol and keto acid derivatives; in addition, cleavage of triazole occurred, as indicated in trials with triazole-labelled compound. The free triazole accounted for about 5% in the urine of the males and 1.5% in that of females. Parent compound was found in only minor amounts.|In a study /with/ lactating goats, the metabolic pathway was similar to that found in rats. The major metabolite identified was the tert-butyl alcohol derivative and its conjugate; the parent compound was also found.|In a study /with/ laying hens ... , hydroxylation of the tert-butyl group followed by conjugation to the sulfate was the major metabolic pathway.

5.89 Days

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

(RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1- ylmethyl)pentan-3-ol

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); Épopée (+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); Libéro (+carbendazim) (spray, France, Belgium); Monicle (+fenpropidin) (spray, UK); Nébraska (+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); Solitär (+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).

Method: AOAC 997.01; Procedure: capillary gas chromatographic method; Analyte: tebuconazole; Matrix: technical material and solid and liquid formulations containing tebuconazole as the only active ingredient; Detection Limit: not provided.

Agrochemicals -> Fungicides|Fungicides, Plant growth regulators|Environmental transformation -> Pesticides (parent, predecessor)

Tebuconazole has known environmental transformation products that include 1,2,4 triazole, 1,2,4 triazole acetic-acid, HWG 1608-4-hydroxy (M05), HWG 1608-5-enol (M08), HWG 1608-5-keto (M09), HWG 1608-desbutyl (M15), HWG 1608-ketodesbutyl (M16), HWG 1608-lactone (M17), HWG 1608-pentanoic acid, HWG 1608-triazole-pinacoline (M18), Hydroxy-triazole (M29), keto-form predominant tautomer, and Triazole alanine.