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triadimenol
ethanol, 2-(4-chlorophenoxy)-1-tert-butyl-2-(1H-1,2,4-triazole-1-yl)-

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CAS Number: 55219-65-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:259-537-6
FDA UNII: NFR7MRD9NM
Nikkaji Web:J11.445F
Beilstein Number:616470
MDL:MFCD00055507
XlogP3:3.10 (est)
Molecular Weight:295.76886000
Formula:C14 H18 Cl N3 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:herbicides / pesticides
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 124.00 °C. @ 760.00 mm Hg
Boiling Point: 465.40 °C. @ 760.00 mm Hg (est)
Vapor Pressure:3.100000 mmHg @ 20.00 °C. (est)
Flash Point: 456.00 °F. TCC ( 235.30 °C. ) (est)
logP (o/w): 2.900
Soluble in:
 water, 120 mg/L @ 20 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Triadimenol 98%
Odor: characteristic
Use: Triadimenol is a agricultural fungicide that is systemically active against powdery mildews and rusts of grains. lt is a systemic fungicide with a broad spectrum. It inhibits the ergosterol - and gibberellin - biosynthesis. Triadimenol is a agricultural fungicide that is systemically active against powdery mildews and rusts of grains.
Santa Cruz Biotechnology
For experimental / research use only.
Triadimenol ≥96%
Sigma-Aldrich
For experimental / research use only.
Triadimenol PESTANAL®, analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-chicken LD50 > 2000 mg/kg
"Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A402, Pg. 1985

unreported-chicken LDLo > 2000 mg/kg
Defense des Vegetaux. Vol. 39(235), Pg. 2, 1985.

oral-mouse LD50 3250 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(9), Pg. 40, 1990.

oral-quail LD50 > 10000 mg/kg
"Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A402, Pg. 1985

unreported-quail LDLo > 10000 mg/kg
Defense des Vegetaux. Vol. 39(235), Pg. 2, 1985.

oral-rabbit LD50 1500 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(9), Pg. 40, 1990.

oral-rat LD50 3800 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(9), Pg. 40, 1990.

Dermal Toxicity:
skin-rat LD50 > 5000 mg/kg
Pesticide Manual. Vol. 9, Pg. 833, 1991.

Inhalation Toxicity:
inhalation-mouse LC50 3000 mg/m3
BEHAVIORAL: MUSCLE WEAKNESS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(9), Pg. 40, 1990.

inhalation-rat LC50 3060 mg/m3
BEHAVIORAL: MUSCLE WEAKNESS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(9), Pg. 40, 1990.

 
Safety in Use Information:
Category:
herbicides / pesticides
Recommendation for triadimenol usage levels up to:
 not for fragrance use.
 
Recommendation for triadimenol flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Outcome of the consultation with Member States, the applicant and EFSA on the pesticide risk assessment of confirmatory data for the active substance triadimenol
View page or View pdf

Retrospective analysis of the immunotoxic effects of plant protection products as reported in the Draft Assessment Reports for their peer review at EU level
View page or View pdf

Review of the existing maximum residue levels for triadimenol according to Article 12 of Regulation (EC) No 396/2005
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :41368
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol
Chemidplus:0055219653
RTECS:KK2200000 for cas# 55219-65-3
 
References:
 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):41368
Pubchem (sid):135002790
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C11127
HMDB (The Human Metabolome Database):Search
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•registered formulations include emulsifiable concentrate (ec) (5% active ingredient), wettable powder (wp)(25% active ingredient), soluble concentrate (sc) (13.33% active ingredient), and flowable concentrate (flc) (28.3 - 30% active ingredient). •emulsifiable concentrate, flowable, granule, seed dressing, water dispersible granule, water-oil emulsion, wettable powder. •baytan technical; active ingredient 98.30% triadimenol •gustafson rtu-baytan-thiram fungicide; active ingredients 15.30% thiram and 5.00% triadimenol •gustafson baytan 30 fungicide; active ingredient 30.00% triadimenol •trilex advanced pak; active ingredients 28.35% metalaxyl, 30.00% triadimenol, and 22.00% trifloxystrobin •trilex advanced 300; active ingredients 12.82% metalaxyl, 4.27% triadimenol, and 8.55% trifloxystrobin
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 bay kwg 0519
 bayfidan
 bayfrdan EW
 baytan
 baytan 15
 baytan TF 3479B
alpha-tert-butyl-beta-(4-chlorophenoxy)-1H-1,2,4-triazole-1-ethanol
2-(4-chlorophenoxy)-1-tert-butyl-2-(1H-1,2,4-triazole-1-yl)ethanol
1-(4-chlorophenoxy)-3,3-dimethyl-1-(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
(1RS,2RS,1RS,2SR)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1h-1,2,4-triazole-1-ethanol
alpha-(4-chlorophenoxy)-beta-(1,1-dimethyl ethyl)-1H-1,2,4-triazole-1-ethanol
alpha-(4-chlorophenoxy)-beta-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol
 ethanol, 2-(4-chlorophenoxy)-1-tert-butyl-2-(1H-1,2,4-triazole-1-yl)-
 spinnaker
 triafol
 triaphol
1H-1,2,4-triazole-1-ethanol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-
 

Articles:

PubMed:Method Development for Simultaneous Determination of 41 Pesticides in Rice Using LC-MS/MS Technique and Its Application for the Analysis of 60 Rice Samples Collected from Tehran Market.
PubMed:[Determination of 18 pesticide residues in red wine by ultra high performance liquid chromatography-high resolution mass spectrometry with isotope dilution technique].
PubMed:Determination of 28 pesticides applied on two tomato cultivars with a different surface/weight ratio of the berries, using a multiresidue GC-MS/MS method.
PubMed:Stereoselective metabolism, distribution, and bioaccumulation brof triadimefon and triadimenol in lizards.
PubMed:Stereoselective bioaccumulation and metabolite formation of triadimefon in Tubifex tubifex.
PubMed:Enantioseparation of new triadimenol antifungal active compounds by electrokinetic chromatography and molecular modeling study of chiral recognition mechanisms.
PubMed:Chiral fungicide triadimefon and triadimenol: Stereoselective transformation in greenhouse crops and soil, and toxicity to Daphnia magna.
PubMed:Molecularly imprinted fibers with renewable surface for solid-phase microextraction of triazoles from grape juice samples followed by gas chromatography mass spectrometry analysis.
PubMed:Stereoselective transformation of triadimefon to metabolite triadimenol in wheat and soil under field conditions.
PubMed:Stereoselective degradation and microbial epimerization of triadimenol in soils.
PubMed:Effects of mixtures of azole fungicides in postimplantation rat whole-embryo cultures.
PubMed:Effect on enzymes and histopathology in earthworm (Eisenia foetida) induced by triazole fungicides.
PubMed:Assessment of silicone as support to investigate the transformation routes of organic chemicals under environmental conditions and UV exposure. Application to selected fungicides.
PubMed:Carbonyl reduction of triadimefon by human and rodent 11β-hydroxysteroid dehydrogenase 1.
PubMed:[Determination of eight pesticide residues in tea by liquid chromatography-tandem mass spectrometry and its uncertainty evaluation].
PubMed:Investigation of pesticide residues in vegetables and fruits grown in various regions of Hatay, Turkey.
PubMed:Study on the interaction of triadimenol with calf thymus DNA by multispectroscopic methods and molecular modeling.
PubMed:Evaluation of developmental toxicants and signaling pathways in a functional test based on the migration of human neural crest cells.
PubMed:HPLC-MS/MS enantioseparation of triazole fungicides using polysaccharide-based stationary phases.
PubMed:Residues behavior of some fungicides applied on two greenhouse tomato varieties different in shape and weight.
PubMed:Computer-aided molecular modeling study of enantioseparation of iodiconazole and structurally related triadimenol analogues by capillary electrophoresis: chiral recognition mechanism and mathematical model for predicting chiral separation.
PubMed:A non-destructive method for testing two components of the behaviour of soil-applied agricultural chemicals over a long period.
PubMed:Stereoselective separation and determination of triadimefon and triadimenol in wheat, straw, and soil by liquid chromatography-tandem mass spectrometry.
PubMed:Molecular modelling of the emergence of azole resistance in Mycosphaerella graminicola.
PubMed:Development and application of a physiologically based pharmacokinetic model for triadimefon and its metabolite triadimenol in rats and humans.
PubMed:Synthesis and application of a novel molecularly imprinted polymer-coated stir bar for microextraction of triazole fungicides in soil.
PubMed:Enantioselective degradation, abiotic racemization, and chiral transformation of triadimefon in soils.
PubMed:Microbial transformation of triadimefon to triadimenol in soils: selective production rates of triadimenol stereoisomers affect exposure and risk.
PubMed:Reducing the impact of pesticides on biological control in Australian vineyards: pesticide mortality and fecundity effects on an indicator species, the predatory mite Euseius victoriensis (Acari: Phytoseiidae).
PubMed:Use of farming and agro-industrial wastes as versatile barriers in reducing pesticide leaching through soil columns.
PubMed:Mechanism of binding of prothioconazole to Mycosphaerella graminicola CYP51 differs from that of other azole antifungals.
PubMed:Application of dispersion-solidification liquid-liquid microextraction for the determination of triazole fungicides in environmental water samples by high-performance liquid chromatography.
PubMed:Interaction between vine pesticides and bovine serum albumin studied by nuclear spin relaxation data.
PubMed:Sensitivities to DMI fungicides in populations of Podosphaera fusca in south central Spain.
PubMed:Solarization and biosolarization enhance fungicide dissipation in the soil.
PubMed:Gender and species differences in triadimefon metabolism by rodent hepatic microsomes.
PubMed:Photocatalytic degradation of eight pesticides in leaching water by use of ZnO under natural sunlight.
PubMed:Mechanistic approach to understanding the toxicity of the azole fungicide triadimefon to a nontarget aquatic insect and implications for exposure assessment.
PubMed:Pesticide residues in apples grown under a conventional and integrated pest management system.
PubMed:Determination of stereoselective interaction between enantiomers of chiral gamma-aryl-1H-1,2,4-triazole derivatives and Penicillium digitatum.
PubMed:New mathematic model for predicting chiral separation using molecular docking: mechanism of chiral recognition of triadimenol analogues.
PubMed:Stereoselective degradation of fungicide triadimenol in cucumber plants.
PubMed:Integration of metabolomics and in vitro metabolism assays for investigating the stereoselective transformation of triadimefon in rainbow trout.
PubMed:Descriptive and mechanistic toxicity of conazole fungicides using the model test alga Dunaliella tertiolecta (Chlorophyceae).
PubMed:[Determination of triadimenol residue in foods with dispersive solid phase extraction cleanup by gas chromatography-negative chemical ionization mass spectrometry].
PubMed:Effects of acibenzolar-s-methyl and ethirimol on the composition of a laboratory population of barley powdery mildew.
PubMed:Mechanistic investigation of the noncytochrome P450-mediated metabolism of triadimefon to triadimenol in hepatic microsomes.
PubMed:Application of hollow fibre liquid phase microextraction for the multiresidue determination of pesticides in alcoholic beverages by ultra-high pressure liquid chromatography coupled to tandem mass spectrometry.
PubMed:Evaluation of the effects of chemical versus biological control on Botrytis cinerea agent of gray mould disease of strawberry.
PubMed:Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants.
PubMed:[Application of binding spectra in DMIs fungicide screening].
PubMed:Combining TiO2-photocatalysis and wetland reactors for the efficient treatment of pesticides.
PubMed:Citral, an inhibitor of retinoic acid synthesis, attenuates the frequency and severity of branchial arch abnormalities induced by triazole-derivative fluconazole in rat embryos cultured in vitro.
PubMed:Falcon 460 EC in the control of foliage diseases of some ornamentals.
PubMed:Determination of triadimenol based on the quenching effect on resonance light scattering from the triadimenol-deoxyribonucleic acid-hydrochloric acid system.
PubMed:[Screening method for the determination of 199 pesticides in agricultural products by gas chromatography/ion trap mass spectrometry (GC/MS/MS)].
PubMed:Inhibition of rainbow trout (Oncorhynchus mykiss) P450 aromatase activities in brain and ovarian microsomes by various environmental substances.
PubMed:Comparative enantioseparation of seven triazole fungicides on (S,S)-Whelk O1 and four different cellulose derivative columns.
PubMed:Determination of 22 triazole compounds including parent fungicides and metabolites in apples, peaches, flour, and water by liquid chromatography/tandem mass spectrometry.
PubMed:Teratogenic effects of two antifungal triazoles, triadimefon and triadimenol, on Xenopus laevis development: craniofacial defects.
PubMed:Determination of azolic fungicides in wine by solid-phase extraction and high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry.
PubMed:Sequence variation in the CYP51 gene of Blumeria graminis associated with resistance to sterol demethylase inhibiting fungicides.
PubMed:Study on the common teratogenic pathway elicited by the fungicides triazole-derivatives.
PubMed:Fate of pesticides during the winemaking process in relation to malolactic fermentation.
PubMed:Evaluation of Several Approaches to Manage Meloidogyne incognita and Cotton Seedling Disease Complexes in the High Plains of Texas.
PubMed:Factors affecting triadimefon degradation in soils.
PubMed:Evaluation of a method based on liquid chromatography/electrospray tandem mass spectrometry for analyzing eight triazolic and pyrimidine fungicides in extracts of processed fruits and vegetables.
PubMed:Estimation of estrogenic and antiestrogenic activities of selected pesticides by MCF-7 cell proliferation assay.
PubMed:Surface photochemistry of pesticides: an approach using diffuse reflectance and chromatography techniques.
PubMed:The determination of deoxyribonucleic acids with triadimenol based on the enhancement of resonance light scattering.
PubMed:Coupling solid-phase microextraction and high-performance liquid chromatography for direct and sensitive determination of halogenated fungicides in wine.
PubMed:Effects of sensitizers on the photodegradation of the systemic fungicide triadimenol.
PubMed:Separation of triadimefon and triadimenol enantiomers and diastereoisomers by supercritical fluid chromatography.
PubMed:On-line preconcentration and enantioselective separation of triadimenol by electrokinetic chromatography using cyclodextrins as chiral selectors.
PubMed:Isogamous, hermaphroditic inheritance of mitochondrion-encoded resistance to Qo inhibitor fungicides in Blumeria graminis f. sp. tritici.
PubMed:Monitoring of pesticide residues on cucumber, tomatoes and strawberries in Gaza Governorates, Palestine.
PubMed:[Effects of organonitrogen, carbamate pesticides and others on beta-hexosaminidase release from rat basophilic leukemia cells (RBL-2H3)].
PubMed:Behavior of triadimefon in two Lebanese soils.
PubMed:Plant sterol 14 alpha-demethylase affinity for azole fungicides.
PubMed:High-performance chiral separation of fourteen triazole fungicides by sulfated beta-cyclodextrin-mediated capillary electrophoresis.
PubMed:Solid-phase microextraction for the determination of systemic and non-volatile pesticides in river water using gas chromatography with nitrogen-phosphorous and electron-capture detection.
PubMed:Simultaneous chiral separation of triadimefon and triadimenol by sulfated beta-cyclodextrin-mediated capillary electrophoresis.
PubMed:Robustness testing of a reversed-phase high-performance liquid chromatographic assay: comparison of fractional and asymmetrical factorial designs.
PubMed:Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro.
PubMed:Effects of benzimidazole and triazole fungicide use on epigeic species of Collembola in wheat.
PubMed:Screening of selected pesticides for oestrogen receptor activation in vitro.
PubMed:Pesticide residues in grapes, wine, and their processing products.
PubMed:Investigation on fungicide residues in greenhouse-grown strawberries.
PubMed:In vitro teratogenic potential of two antifungal triazoles: triadimefon and triadimenol.
PubMed:Determination of polar pesticides with atmospheric pressure chemical ionisation mass spectrometry-mass spectrometry using methanol and/or acetonitrile for solid-phase desorption and gradient liquid chromatography.
PubMed:Multiresidue determination of 19 fungicides in processed fruits and vegetables by capillary gas chromatography after gel permeation chromatography.
PubMed:Expression, purification, reconstitution and inhibition of Ustilago maydis sterol 14 alpha-demethylase (CYP51; P450(14DM)).
PubMed:[Toxic kinetics of triadimenol after single administration to albino rats].
PubMed:Distributions of Sensitivities to Three Sterol Demethylation Inhibitor Fungicides Among Populations of Uncinula necator Sensitive and Resistant to Triadimefon.
PubMed:A mutation in the 14 alpha-demethylase gene of Uncinula necator that correlates with resistance to a sterol biosynthesis inhibitor.
PubMed:[Toxicokinetics of triadimenol and monochlorpinacoline in chronic experiments in white rats].
PubMed:Triadimefon and triadimenol: effects on monoamine uptake and release.
PubMed:The direct separation of the diastereoisomers and enantiomers of the fungicide triadimenol by micellar electrokinetic capillary chromatography.
PubMed:A structure-activity relationship for the neurotoxicity of triazole fungicides.
PubMed:[Effect of the fungicide matador (tebuconazole/triadimenol) on mycotoxin production by Fusarium culmorum].
PubMed:[Gas-chromatographic determination of triadimenol in the environment and biological materials].
PubMed:[Formation and degradation of triademinol after the use of triadimefon in a wheat monoculture].
PubMed:Residue analysis of triadimefon, triadimenol, and the BAY KWG 1342 diol and BAY KWG 1323 hydroxylated metabolites in winter wheat.
PubMed:Stereoselective interaction of an azole antifungal agent with its target, lanosterol 14 alpha-demethylase (cytochrome P-45014DM): a model study with stereoisomers of triadimenol and purified cytochrome P-45014DM from yeast.
PubMed:Residue characterization of triadimefon in grapes by gas chromatography and mass spectrometry/mass spectrometry.
PubMed:Biochemical approaches to selective antifungal activity. Focus on azole antifungals.
PubMed:Interaction of azole antifungal agents with cytochrome P-45014DM purified from Saccharomyces cerevisiae microsomes.
PubMed:Combined application of low temperature preparation and electron microscopic autoradiography for the localization of systemic fungicides.
PubMed:The metabolism of fungicides.
PubMed:A simple physical model for fungicide induced hexagonal clustering of intramembrane particles in the plasmalemma of Ustilago avenae.
 
Notes:
None found
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