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Tebuconazole
TEBUCONAZOL · -ol · ELITE · 1-ethanol · (RS)-1-p-Chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol · LYNX · TERBUCONAZOLE · tebuconazole 97%TC
Identifikatoren & physikalische Daten
| CAS No. | 107534-96-3 |
|---|---|
| Summenformel | C16H22ClN3O |
| Durchschnittliche Molmasse | 307,82 g/mol |
| Monoisotopische Masse | 307,14514 g/mol |
| SMILES | CC(C)(C)C(O)(CCc1ccc(Cl)cc1)Cn1cncn1 |
| InChIKey | PXMNMQRDXWABCY-UHFFFAOYSA-N |
| PubChem CID | 86102 |
| ChEMBL | CHEMBL487186 |
| ChEBI | CHEBI:83779 |
| EC No. | 403-640-2 |
| DTXSID | DTXSID9032113 |
Chemische & physikalische Eigenschaften
| XLogP | 3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 50,9 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 326 |
| Pestizide | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: ApprovedPesticides -> FungicidesBiocideEnvironmental transformation -> Pesticides (parent, predecessor)Fungicides, Plant growth regulators |
| LogP (Verteilungskoeffizient) | log Kow = 3.7 |
| Color/Form | Colorless crystals |
| Löslichkeit | In water, 36 mg/L at pH 5-9, 20 °CChloroform: Slightly SolubleMethanol: Slightly Soluble32 mg/L at 20 ºC |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits toxic vapors of /hydrogen chloride and nitrogen oxides/. |
| Schmelzpunkt | 105 °C102-105°C |
| Dampfdruck | 0.00000001 [mmHg]1.7X10-6 Pa (1.3X10-8 mm Hg) at 20 °C1.7 x l0-6 Pa (20 °C) |
| Physical Description | Colorless solid[Merck Index] Technical product: White to beige solid[eChemPortal: ESIS] White powder[MSDSonline] |
| Stability/Shelf Life | Stable to elevated temperatures, and to photolysis and hydrolysis in pure water, under sterile conditions... . |
| Collision Cross Section | 166.8 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID9032113]167.37 Ų [M+H]+ [CCS Type: TW]166.25 Ų [M+H]+ [CCS Type: TWIonization: GC-APCI+] |
| Siedepunkt | 476.9±55.0 °C(Predicted) |
| Dichte | 1.25 |
| Brechungsindex | 1.5800 (estimate) |
| Flammpunkt | 100 °C |
| Lagerbedingungen | Sealed in dry,2-8°C |
| pKa (Säurekonstante) | 13.70±0.29(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Almost white |
| Merck | 14,9092 |
| Henry-Konstante | 7.0×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | agriculturecleaning productscosmeticsenvironmentalfood and beveragespersonal care |
| InChI | 1S/C16H22ClN3O/c1-15(2,3)16(10-21,20-12-18-11-19-20)9-8-13-4-6-14(17)7-5-13/h4-7,11-12,21H,8-10H2,1-3H3 |
| InChIKey | PXMNMQRDXWABCY-UHFFFAOYSA-N |
| SMILES | CC(C)(C)C(CO)(CCc1ccc(Cl)cc1)n2cncn2 |
| LogP (Verteilungskoeffizient) | 3.700 |
| CAS Datenbank | 107534-96-3(CAS DataBase Reference) |
| NIST chemische Informationen | Tebuconazole(107534-96-3) |
| EPA chemische Informationen | Tebuconazole (107534-96-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Regulation (EC) No 1107/2009 (amended)Tebuconazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/125, Reg. (EU) 2019/707, Reg. (EU) 2020/1160, Reg. (EU) 2021/745, Reg. (EU) 2022/708, Reg. (EU) 2023/1446, Reg. (EU) No 540/2011, Reg. (EU) No 921/2014Status: Cease Manufacture Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/4163Tebuconazole: HSNO Approval: HSR002879 Approved with controls |
| Gefahrenübersicht | Harmful if swallowedCaused hypertrophy of the adrenal glands in a 1-year dog studyNot a skin sensitizerNot genotoxicNot likely to cause cancer in humansPossible risk of harm to the unborn child[EFSA: Tebuconazole - 2008] May cause irritation[MSDSonline] |
| FIFRA-Anforderungen | Tolerances are established for residues of the fungicide tebuconazole (alpha-[2-(4-chlorophenyl)-ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol) in or on the following raw agricultural commodities: [Table#7098]Tolerances are established for the combined residues of the fungicide, tebuconazole and its 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazole-1-yl-methyl)-pentane-3,5-diol metabolite. [Table#7099]Time-limited tolerances are established for residues of the fungicide tebuconazole (alpha-[2-(4-chlorophenyl)-ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol) in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specified in the following table. [Table#7100]Time-limited tolerances are established for the combined residues of the fungicide tebuconazole (alpha-[2-(4-chlorophenyl)-ethyl)-ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol) and its 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazole-1-yl-methyl)-pentane-3,5-diol metabolite in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specified in the following table. [Table#7101]New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128997Type of Pesticide:Conventional- FungicideUse Site:Food useYear: 1994. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Reproductive toxicity - category 2Acute toxicity (Inhalation: Dusts and mists) - Category 2Carcinogenicity - Category 1BRepr. 2 |
| Entsorgungsverfahren | 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. |
| Allowable Tolerances | Tolerances are established for residues of the fungicide tebuconazole (alpha-[2-(4-chlorophenyl)-ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol) in or on the following raw agricultural commodities: [Table#7094]Tolerances are established for the combined residues of the fungicide, tebuconazole and its 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazole-1-yl-methyl)-pentane-3,5-diol metabolite. [Table#7095]Time-limited tolerances are established for residues of the fungicide tebuconazole (alpha-[2-(4-chlorophenyl)-ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol) in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specified in the following table. [Table#7096]Time-limited tolerances are established for the combined residues of the fungicide tebuconazole (alpha-[2-(4-chlorophenyl)-ethyl)-ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol) and its 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazole-1-yl-methyl)-pentane-3,5-diol metabolite in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specified in the following table. [Table#7097] |
| Ökotoxizitätswerte | LC50 Anas platyrhynchos (Mallard duck) diet >4816 ppm/8 days[USEPA, Office of Pesticide ProgramsPesticide Ecotoxicity Database (2000) on alpha-LD50 Colinus virginianus (Bobwhtie quail, age 20 weeks) oral 1988 mg/kg[USEPA, Office of Pesticide ProgramsLC50 Colinus virginianus (Bobwhtie quail, age 13 days) diet >5000 ppm/12 days[USEPA, Office of Pesticide ProgramsLC50 Americamysis bahia (Opossum shrimp, age <24 hr) 0.49 ppm/96 hr (95% confidence limit: 0.32-0.66 ppm)flow through /96.3% AI formulated product/[USEPA, Office of Pesticide ProgramsFor more Ecotoxicity Values (Complete) data for TEBUCONAZOLE (11 total), please visit the HSDB record page. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 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. |
| Unerwünschte Wirkungen | Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment. |
| Soil Adsorption/Mobility | 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. |
| Artificial Pollution Sources | Tebuconazole's production may result in its release to the environment through various waste streamsit's use as a fungicide(1) will result in its direct release to the environment(SRC). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/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). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ The symptoms of acute poisoning described in rats consisted of sedation, locomotor incoordination, spastic gait and emaciation.[WHO/FAOJoint Meeting on Pesticide Residues on Tebuconazole (107534-96-3). Available from, as of July 6, 2006: http://www.inchem.org/pages/jmpr.html]/LABORATORY ANIMALS: Acute Exposure/ Non-irritating to skinmild irritant to eyes (rabbits).[Tomlin CDS, ed. Tebuconazole (107534-96-3). In: The e-Pesticide Manual, 13th Edition Version 3.2 (2005-06). Surrey UK, British Crop Protection Council.]/LABORATORY ANIMALS: Acute Exposure/ Tebuconazole did not reveal skin-sensitizing potential in a maximization test in guinea-pigs.[WHO/FAO/LABORATORY ANIMALS: Acute Exposure/ Tebuconazole did not irritate the skin of rabbits, and administration of 50 mg into the conjunctival sac did not induce irritation of the eye. In another study, instillation of 100 mg into the conjunctival sac of rabbits caused slight irritation of the conjunctiva.[WHO/FAOFor more Non-Human Toxicity Excerpts (Complete) data for TEBUCONAZOLE (34 total), please visit the HSDB record page. |
| Evidence for Carcinogenicity | Cancer Classification: Group C Possible Human Carcinogen |
| Environmental Abiotic Degradation | 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). |
| Probable Routes of Human Exposure | 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) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 3077 9/PG 3 |
| Zollcode | 29339900 |
| RTECS-Nr. | XZ4803270 |
| R-Sätze (R) | 22-51/53-63 |
| Toxizität | bird - domestic,LD50,oral,> 1gm/kg (1000mg/kg),Pesticide Manual. Vol. 9, Pg. 785, 1991. |
| Gefahrensymbole | XnN,N,Xn |
| Sicherheitshinweise (S) | 2-22-36/37-61 |
| Gefahrenklasse | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 107534-96-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Tebuconazole used as a seed dressing is effective against various smut and bunt diseases of cereals. Used as a spray it controls numerous pathogens in various crops: rust species, powdery mildew, Rhyncosporum secalis, Sqtoria spp., Pyrenophora spp., Fusarium spp. in cereals, Mycosphaerella spp. in bananas, Pucciniu spp. and Sclerufium roIfsii in peanuts.