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1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol
1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-OL · b-(4-Chlorophenoxy)-a-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol · SAMET · uk199 · SUMMIT · BAYTAN · TRIADIM · kwg0519
Identifikatoren & physikalische Daten
| CAS No. | 55219-65-3 |
|---|---|
| Summenformel | C14H18ClN3O2 |
| Durchschnittliche Molmasse | 295,76 g/mol |
| Monoisotopische Masse | 295,1087545 g/mol |
| SMILES | CC(C)(C)C(O)C(Oc1ccc(Cl)cc1)n1cncn1 |
| InChIKey | BAZVSMNPJJMILC-UHFFFAOYSA-N |
| PubChem CID | 41368 |
| ChEMBL | CHEMBL520275 |
| ChEBI | CHEBI:9666 |
| EC No. | 259-537-6 |
| DTXSID | DTXSID0032493 |
| Lokaler Name | 1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 60,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 303 |
| LogP (Verteilungskoeffizient) | log Kow = 2.90 |
| Geruch | Slight non-specific odor |
| Dichte | 1.22 g/cu cm1.2990 (rough estimate) |
| Color/Form | Colorless crystalline solid |
| Löslichkeit | Soluble in alcohol, ketonesIn water, 120 mg/L at 20 °CDMSO (Slightly), Methanol (Slightly)A 62 mg l-1 (20 °C)B 33 mg l-1(20 °C) |
| Decomposition | When heated to decomposition it emits toxic vapors of /Nitrogen oxides and Chlorides/. |
| Schmelzpunkt | 118-130 °C112-117° |
| Dampfdruck | 3.1X10-10 mm Hg at 20 °CA 6 x l0-7 Pa (20 °C)B 4 x l0-7 Pa (20 °C) |
| Physical Description | Solid with a mild non-specific odor[Merck Index] Formulated as emulsifiable, soluble, and flowable concentrates and wettable powder[Reference #1] |
| Kovats Retention Index | 2078.62087.9207620842095208821042065.32063.12064.62069.92079.62062.620502066.72061.92077.120232051.8 |
| Collision Cross Section | 172.08 Ų [M+H]+177.62 Ų [M+Na]+178.1 Ų [M+HCOO]- |
| Other Experimental Properties | Diastereoisomer A(1RS, 2SR) and diastereoisomer B(1RS, 2RS) ratio of A:B is 7:3Diastereoisomer A: MP = 138.2 °CVP = 6X10-4 mPa at 20 °CSG/Density = 1.237 g/cu cm at 22 °CKow (logP) = 3.08 at 25 °CHenry's Law constant = 3X10-6 Pa cu m mol-1 at 20 °Csolubility = 62 mg/L in water at 20 °CDiastereoisomer B: MP = 133.5 °CVP = 4X10-4 mPa at 20 °CSG/Density = 1.299 g/cu cm at 22 °CKow (logP) = 3.28 at 25 °CHenry's Law constant = 4X10-6 Pa cu m mol-1 at 20 °Csolubility = 33 mg/L in water at 20 °C |
| Siedepunkt | 465.4±55.0 °C(Predicted) |
| Brechungsindex | 1.5270 (estimate) |
| Flammpunkt | 2 °C |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 13.29±0.20(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Off-White |
| Merck | 13,9667 |
| BRN | 616470 |
| Henry-Konstante | 7.6×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C14H18ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,12-13,19H,1-3H3 |
| InChIKey | BAZVSMNPJJMILC-UHFFFAOYSA-N |
| SMILES | CC(C)(C)C(O)C(Oc1ccc(Cl)cc1)n2cncn2 |
| LogP (Verteilungskoeffizient) | 2.900 |
| CAS Datenbank | 55219-65-3(CAS DataBase Reference) |
| NIST chemische Informationen | Triadimenol(55219-65-3) |
| EPA chemische Informationen | Triadimenol (55219-65-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]H360: May damage fertility or the unborn child [Danger Reproductive toxicity]H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P203, P260, P263, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.9% (1 of 114) of reports. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Reproductive ToxicityAuthoritative List - EC Annex VI CMRs - Cat. 1BReport - if used as a fragrance or flavor ingredientCommission Regulation (EC) No 1490/2002Triadimenol 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) 2022/801, Reg. (EU) No 540/2011Triadimenol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-(4-chlorophenoxy)-.alpha.-(1,1-dimethylethyl)-: Human health tier I assessmentIMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-(4-chlorophenoxy)-.alpha.-(1,1-dimethylethyl)-: Environment tier I assessment |
| Gefahrenübersicht | Commercial material is mixture of two diastereoisomers[Merck Index] Increased liver enzyme activity (ALT and AST) and histopathological liver changes observed in 13-week feeding study of rats at the three highest doses tested (500, 1,500, and 4,500 ppm)A 15-day dermal study of rabbits produced a NOAEL greater than highest tested dose (250 mg/kg/day)Teratogenic effects seen in tadpoles (branchial arches) and cultured rat embryos (cranial nerve and ganglia)No evidence of mutagenicity[HSDB] Not irritating to skin or eyes of rabbitsNot sensitizing to guinea pig skinNo adverse effects to reproductive performance observed in 2-generation study of ratsNo evidence of primary embryotoxic or teratogenic effects in rats or rabbits administered by gavage in the most sensitive stage of gestationNo evidence of carcinogenicity in rats or mice[IUCLID] Repeated dose studies have shown the liver to be the target organ of toxicity (enlargement with corresponding changes in clinical chemistry)Chronic studies of rats and mice also demonstrated hepatotoxicityMultigenerational studies produced reduced pup survival during lactation and decreased fertility index in all generations in one studyAcute triadimefon (structurally and metabolically similar fungicide) neurotoxicity studies of rats showed reversible hyperactivity and increased motor and locomotor activity without neuropathological changesSub-chronic studies produced consistent effects with no increase in severity observedDoes not possess potential for mutagenicity or carcinogenicity[EFSA] See Triadimefon. |
| Special Reports | USEPA/Office of Prevention, Pesticides and Toxic SubstancesReregistration Eligibility Decision Document for Triadimefon and Tolerance Reassessment for Triadimenol EPA 738-R-06-003 (August 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 27, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]California Environmental Protection Agency/Department of Pesticide RegulationToxicology Data Review Summary for Triadimenol (55219-65-3).[Available from, as of May 13, 2009: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]USEPA, Office of Prevention, Pesticides, and Toxic SubstancesRevised HED Human Health Risk Assessment for Triadimenol (52219-65-3) (February 2006). EPA Docket No.: EPA-HQ-OPP-2006-0038-0005.European Chemicals BureauIUCLID Dataset, Triadimenol (55219-65-3) (2000 CD-ROM edition).[Available from, as of May 8, 2009: http://esis.jrc.ec.europa.eu/] |
| FIFRA-Anforderungen | Tolerances are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7396]Tolerances with regional registrations, as defined in part 180.1(m), are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7397]Triadimenol, a metabolite of triadimefon, is also a registered fungicide. Triadimenol was first registered after 1984 and is not subject to reregistration under the 1988 amendments to FIFRA. Triadimenol is, however, subject to tolerance reassessment under the FFDCA, as amended by FQPA. Based on its evaluation of combined exposures from the uses of triadimefon, triadimenol, and their metabolites, the Agency has determined that the tolerances for triadimefon and triadimenol are considered to be reassessed under FFDCA.New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Triadimenol is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 127201Type of Pesticide: conventional - fungicideUse Site: food use, turf, ornamentalsYear: 1989. |
| Hazard Classes and Categories | Acute Tox. 4 (99.1%)Acute Tox. 4 (34.2%)Repr. 1B (26.3%)Lact. (27.2%)Aquatic Chronic 2 (27.2%)Aquatic Chronic 3 (34.2%)Acute toxicity - category 4Reproductive toxicity - category 1BReproductive toxicity - effects on or via lactationHazardous to the aquatic environment (chronic) - category 2Aquatic Chronic 2 |
| Skin, Eye, and Respiratory Irritations | An eye irritant, and causes a mild skin dermal irritation. |
| Reinigungsverfahren | SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. |
| Preventive Measures | SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them.Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet.For more Preventive Measures (Complete) data for Triadimenol (13 total), please visit the HSDB record page. |
| Allowable Tolerances | Tolerances are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7394]Tolerances with regional registrations, as defined in part 180.1(m), are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7395] |
| Personal Protective Equipment (PPE) | Water soluble packets when used correctly qualify as a closed mixing/loading system under the Worker Protection Standard for Agricultural Pesticides [40 CFR 170.240(d)(4)]. Mixers and loaders using water soluble packets must: wear the personal protective equipment required on this labeling for mixers and loaders, and be provided, have immediately available, and wear in an emergency, such as a broken package, spill, or equipment breakdown: chemical resistant footwear and a NIOSH-approved respirator equipped with a dust/mist filter with MSHA/NIOSH approval number prefix TC-21C or any N, R, P, or HE filter.Mixers, loaders, applicators, flaggers, and other handlers must wear long sleeved shirt and long pants, shoes plus socks, and chemical resistant gloves when mixing/loading, when applying using handheld equipment or handheld nozzles, or when handling treated seed (including spreading, drying, raking, bagging, and sewing seed bags). |
| Wechselwirkungen | ... Doses of 15 and 60 mg/kg /triadimenol/ potentiated the effect of amphetamine while doses of 12 to 48 mg/kg antagonized the reserpin response. Triadimenol also prolonged the hexobartital sleeping time at 15 and 60 mg/kg.... Rats exposed to 48 mg/kg triadimenol elicited an excitatory effect. A comparison with caffeine (doses of 2.5 and 10 mg/kg) showed that the effect of 2.5 mg/kg caffeine corresponded approximately to that of 12 to 15 mg/kg KWG 0519, in the amphetamine potentiation test 2.5 mg/kg caffeine elicited a similar response as 4 mg/kg KWG 0519, while in the antagonism of ptosis 10 mg/kg caffeine and 12 mg/kg KWG 0519 were comparable. The noeffect dose was 1 mg/kg for caffeine. The findings of this study point to a potential for stimulation of Central Nervous System (CNS). |
| Ökotoxizitätswerte | LC50Species: Anas platyrhynchos (Mallard duck, age 13 days) diet >5000 ppm for 8 daysSpecies: Colinus virginianus (Northern bobwhite) diet >2000 ppm for 8 daysSpecies: Colinus virginianus (Northern bobwhite, age 16 days) diet >5000 ppm for 8 daysLD50Species: Serinus canaria (Island canary) oral >1000 mg/kgFor more Ecotoxicity Values (Complete) data for Triadimenol (11 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 211(2) to 992(3) indicate that triadimenol is expected to have moderate to low mobility in soil(SRC). Volatilization of triadimenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-12 atm-cu m/mole(SRC), based upon its vapor pressure, 3.1X10-10 mm Hg(4), and water solubility, 120 mg/L(5). Triadimenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure(4). In soil, triadimefon degraded with a half life of 15 days to form triadimenol, which was found to be fairly persistent in accord with other compounds that contain triazole groups(6).TERRESTRIAL FATE: Numerous field studies indicated the presence of triadimenol following the application of triadimefon. Triadimenol residues in soil have been detected after several years of application. Based on one apple orchard trial, triadimenol can consist of 0.13-0.65 mg/kg in the 0-10 cm layer soil during 5 years. The half-life value for triadimenol was determined to range from 3-months to 500 days and consequently thought of as a persistent compound in soil. Often triadimefon and triadimenol are quantified togetherhowever, crop studies specifically detected triadimenol in apples, grapes, melons, strawberries, tomatoes, and wheat at levels up to 0.52 mg/kg at 42 days. 14-C-Radiolabeling studies of 14-C triadimefon treated crops indicated a triadimenol 14-C recovery of 0-1% from barley, 6-23% from wheat, and 25% from apples(1).AQUATIC FATE: Based on a classification scheme(1), Koc values of 211(2) to 992(3), indicate that triadimenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.3X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 3.1X10-10 mm Hg(5) and water solubility, 120 mg/L(6). According to a classification scheme(7), an estimated BCF of 21(SRC), from a log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triadimenol adsorbed on sediments of a pond had a half-life 110-375 days(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triadimenol, which has a vapor pressure of 3.1X10-10 mm Hg at 25 deg(2) is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase triadimenol may be removed from the air by wet or dry deposition(SRC). Triadimenol contains chromophores that absorb at wavelengths >290 nm(3)it undergoes some photodegradation upon solar radiation, at a rate of 2.8X10-2 umol/sq cm-hr(4). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ Conazole fungicides are commonly used to prevent fungal growth on turf grass and agricultural crops. As many of these sites are adjacent to coastal waterways and estuaries, there exists the potential for nontarget effects of runoff on marine organisms. This study reports 96 hr EC(50) values for four selected conazole fungicides (triadimefon = 5.98 mg/Ltriadimenol = 5.51 mg/Lpropiconazole = 2.33 mg/Lhexaconazole = 0.91 mg/L) to the model test alga Dunaliella tertiolecta. We further investigated possible mechanisms of toxicity by examining sublethal effects of exposure on cell morphology, osmoregulatory function, and lipid composition. These mechanistic studies revealed that conazole exposure does not inhibit synthesis of the cell's glycerol osmolyte, but does result in an overall increase in cellular volume and total lipid content. Both fungi and chlorophytes rely on ergosterol to maintain membrane structure and fluidity, and we provide evidence that the sterol-inhibiting conazoles may interfere with ergosterol biosynthesis in the cell membrane of Dunaliella. .../AQUATIC SPECIES/ ... A rainbow trout (Oncorhynchus mykiss) microsomal aromatase assay /was optimized/ to measure the effects of 43 substances ... on brain and ovarian aromatase activities in vitro. ... 12 compounds were able to inhibit brain and ovarian aromatase activities in a dose-dependent manner with IC50 values ranging from the low nM to the high uM range depending on the substance: steroidal and non steroidal inhibitors of aromatase (4-hydroxyandrostenedione, androstatrienedione, aminogluthethimide), imidazole fungicides (clotrimazole, imazalil, prochloraz), triazole fungicides (difenoconazole, fenbuconazole, propiconazole, triadimenol), the pyrimidine fungicide fenarimol and methylmercury... |
| Plant Concentrations | At Kentville, Nova Scotia, Canada, seeds of Lennox winter wheat were treated with triadimenol at the rate of 0.3 g a.i./kg, and planted on September 18. Samples of green foliage were taken November 23 and analyzed for triadimenol on May 7 and June 14 of the following year. Residues of triadimenol at the first, second and third sampling dates averaged 0.05, 0.02 and 0.02 ppm, respectively. In another study, Lennox winter wheat treated with triadimenol at the rate of 0.3 g a.i./kg seed on August 26, was planted on September 4samples of foliage taken November 16 found 0.03 ppm triadimenol in the foliage(1).Residues of triadimefon, including triadimenol, have been determined in extensive trials on growing cereal plants, e.g. barley, oat and wheat. The majority of residue is in the converted triadimenol form at day 14(1). |
| Soil Adsorption/Mobility | In Germany, triadimenol sediment was sampled at depths of 0-15 cm depth from the pond and analyzedKf = 8.3, Kd = 7.6, and Koc = 211 were calculated for triadimenol(1). Koc values were estimated for triadimenol using soil samples from various European sites as follows: Sicily, Italy (992, clay), Peloponnesos, Greece (161, silt loam), Wales, U.K. (231, loam), Normandy, France (150, silt), and Schleswig-Holstein, Germany (568, loamy sand)(2). According to a classification scheme(3), these Koc values suggest that triadimenol is expected to have low to moderate mobility in soil. |
| Human Toxicity Excerpts | /SURVEILLANCE/ ... Of the 46 non-occupational exposures /reported to the Poison Control Center between 1993 and 1998/, 13 occurred in children under six years of age. Of the total 20 cases with medically determined outcome, 11 reported minor medical outcome. Of the total 54 exposures to triadimefon/triadimenol, just four were seen in a health care facility and none required hospitalization. A review of symptoms revealed almost exclusively irritation effects (including rash and erythema) to skin, mouth, throat, and eyes. These effects were reported a total of 24 times with some patients reporting two or more of these symptoms. There were four cases reporting headache and two reported cough. No other significant symptoms were reported./SURVEILLANCE/ /According to the California Department of Pesticide Regulation, following exposure to triadmefon/triadimnol/ foliar residues accounted for half of the illnesses and nearly half of the systemic illnesses. Although most of the symptoms appeared to be minor, skin and eye irritation, and rash were among the most common topical symptoms. The most common systemic effects included nausea, headache, sneezing, congestion, difficulty breathing and other allergic-type reactions. There were three reports of vomiting./ENDOCRINE MODULATION/ Estrogenic activities of 20 selected pesticides ... were examined by estrogen receptor (ER)-dependent MCF-7 cell proliferation assay. Among them, chlordecone, dicofol, methoxychlor, gamma-HCH, fenarimol, EPN, triadimefon, and triadimenol had estrogenic activities, all of which were suppressed by the addition of pure antiestrogen ICI 182,780. ... The antiestrogenic activity of a compound was examined by estimating its suppressive effect on cell proliferation induced by 30 pM 17beta-estradiol. Strongly suspected antiestrogens were captan and myclobutanil ... . Antiestrogenic activities of nitrofen, fenitrothion, fenarimol and triadimefon were also suggested... |
| Artificial Pollution Sources | Triadimenol's production may result in its release to the environment through various waste streamsits use as a systemic fungicide(1) will result in its direct release to the environment(SRC). In soil, triadimefon degraded with a half-life of 15 days to form triadimenol(2). |
| Environmental Biodegradation | ANAEROBIC: Triadimenol adsorbed on sediments of a pond had a half-life of 110-375 days(1). |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Environmental Bioconcentration | An estimated BCF of 21 was calculated for triadimenol (SRC), using its log Kow of 2.90(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | 2588 |
| Zollcode | 29339900 |
| RTECS-Nr. | KK2200000 |
| R-Sätze (R) | 22-52/53-36-20/21/22-11-23-20/22 |
| Toxizität | LD50 in male, female rats (mg/kg): 1161, 1105 orally>5000 dermally, 24-hrLD50 in quail: >10000 mg/kg (Frohberger) |
| Gefahrensymbole | Xn,F,T |
| Sicherheitshinweise (S) | 22-61-36-26-45 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralAquatic Chronic 2Lact.Repr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 55219-65-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Triadimenol is a metabolite of triadimefon , a broad-spectrum chiral triazole fungicide, that is formed by reduction of a carbonyl group to the corresponding alcohol. It is teratogenic, inducing cranial nerve and ganglia abnormalities in a rat post-implantation whole embryo culture model when used at concentrations ranging from 12.5 to 125 μM. In vivo, triadimenol induces embryotoxicity in rats and rabbits when administered orally at doses of 100 and 40 mg/kg, respectively. Embryonic exposure to triadimenol (3-3,000 μg/L) induces embryonic mortality as well as decreases fertility and increases the number of female offspring in medaka fish (O. latipes).
Verwenden
Triadimenol is used for the control of powdery mildews, rusts and Rhynchosporium in cereals, and also as a seed treatment to control bunt, smut and other cereal diseases. It is also used on vines, hops, coffee, tomatoes, vegetables, fruit, tobacco, sugar cane, ornamentals and other crops, mainly against powdery mildews, rusts and various leaf spot diseases.