TRIADIMEFON

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H16ClN3O2
Molecular Weight	293.749
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)C(=O)C(OC1=CC=C(Cl)C=C1)N2C=NC=N2

InChI

InChIKey=WURBVZBTWMNKQT-UHFFFAOYSA-N

InChI=1S/C14H16ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,13H,1-3H3

HIDE SMILES / InChI

Molecular Formula	C14H16ClN3O2
Molecular Weight	293.749
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19128860	Inhibitor 8504	9.29 µM [IC50]
P450 sterol 14-alpha-demethylase 1 Target ID: CHEMBL2366431 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23350742	Binding Agent 1076
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28637041	Inhibitor 8504	58.73 µM [IC50]
3-alpha-hydroxysteroid dehydrogenase 1 Target ID: CHEMBL1075221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28812018	Inhibitor 8504	26.0 µM [IC50]

PubMed

Title	Date	PubMed
Descriptive and mechanistic toxicity of conazole fungicides using the model test alga Dunaliella tertiolecta (Chlorophyceae).	2010-06	19382186
Toxicogenomic effects common to triazole antifungals and conserved between rats and humans.	2009-07-01	19409404
Discrimination of tumorigenic triazole conazoles from phenobarbital by transcriptional analyses of mouse liver gene expression.	2009-07	19363144
Compensation for matrix effects in gas chromatography-tandem mass spectrometry using a single point standard addition.	2009-06-05	19406413
Chronic toxicity of five structurally diverse demethylase-inhibiting fungicides to the crustacean Daphnia magna: a comparative assessment.	2009-06	19132812
Enantiomer separation of triazole fungicides by high-performance liquid chromatography.	2009-04	18570307
In vivo mutagenicity of conazole fungicides correlates with tumorigenicity.	2009-03	19028983
Three conazoles increase hepatic microsomal retinoic acid metabolism and decrease mouse hepatic retinoic acid levels in vivo.	2009-01-15	19010342
Molecular mechanism of teratogenic effects induced by the fungicide triadimefon: study of the expression of TGF-beta mRNA and TGF-beta and CRABPI proteins during rat in vitro development.	2009-01-01	18976680
Fungicide (Rubigan) overdose mimicking organophosphate poisoning.	2008-11	19070292
Endogenous hormonal and enzymatic responses of Catharanthus roseus with triadimefon application under water deficits.	2008-11	18940699
Mechanistic investigation of the noncytochrome P450-mediated metabolism of triadimefon to triadimenol in hepatic microsomes.	2008-10	18763812
Triadimefon pretreatment protects newly assembled membrane system and causes up-regulation of stress proteins in salinity stressed Amaranthus lividus L. during early germination.	2008-09	19295087
Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants.	2008-07-04	18343389
[Determination of triadimenol residue in foods with dispersive solid phase extraction cleanup by gas chromatography-negative chemical ionization mass spectrometry].	2008-07	18959253
Osmoregulation and antioxidant metabolism in drought-stressed Helianthus annuus under triadimefon drenching.	2008-06	18510994
Comparative effects of different triazole compounds on antioxidant metabolism of Solenostemon rotundifolius.	2008-04-01	18065211
Growth and photosynthetic pigments responses of two varieties of Catharanthus roseus to triadimefon treatment.	2008-04	18355749
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Transcriptional responses in thyroid tissues from rats treated with a tumorigenic and a non-tumorigenic triazole conazole fungicide.	2008-03-15	18164361
Cross-species comparison of conazole fungicide metabolites using rat and rainbow trout (Onchorhynchus mykiss) hepatic microsomes and purified human CYP 3A4.	2008-02-01	18323127
Alterations in lipid peroxidation, electrolyte leakage, and proline metabolism in Catharanthus roseus under treatment with triadimefon, a systemic fungicide.	2007-12	18068649
Comparative effects of different triazole compounds on growth, photosynthetic pigments and carbohydrate metabolism of Solenostemon rotundifolius.	2007-11-15	17669636
[Application of binding spectra in DMIs fungicide screening].	2007-11	18257249
Raman spectroscopy-based metabolomics for differentiating exposures to triazole fungicides using rat urine.	2007-10-01	17718537
Changes in carbohydrate metabolism by triazole growth regulators in cassava (Manihot esculenta Crantz); effects on tuber production and quality.	2007-09	17720581
Toxicogenomic study of triazole fungicides and perfluoroalkyl acids in rat livers predicts toxicity and categorizes chemicals based on mechanisms of toxicity.	2007-06	17383973
Determination of triadimenol based on the quenching effect on resonance light scattering from the triadimenol-deoxyribonucleic acid-hydrochloric acid system.	2007-05	17377777
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.	2007-04-11	17875381
Changes in biochemical constituents and induction of early sprouting by triadimefon treatment in white yam (Dioscorea rotundata Poir.) tubers during storage.	2007-04	17444605
Krox20 is down-regulated following triazole in vitro embryonic exposure: a polycompetitor-based assay.	2007-03-30	17343997
Induction of cytochrome P450 enzymes in rat liver by two conazoles, myclobutanil and triadimefon.	2007-02	17484520
Antifungal triazole derivative triadimefon induces ectopic maxillary cartilage by altering the morphogenesis of the first branchial arch.	2007-02	17187389
Disruption of testosterone homeostasis as a mode of action for the reproductive toxicity of triazole fungicides in the male rat.	2007-01	17018648
Gene expression in Xenopus laevis embryos after Triadimefon exposure.	2007-01	16875885
Analyses of pesticide residues in fruit-based baby food by liquid chromatography/electrospray ionization time-of-flight mass spectrometry.	2007	17551990
Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss).	2006-12-30	17118468
Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles.	2006-12-15	17008103
Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles.	2006-11-10	16989930
Inhibition of rainbow trout (Oncorhynchus mykiss) P450 aromatase activities in brain and ovarian microsomes by various environmental substances.	2006-11	17081805
Effect of conazole fungicides on reproductive development in the female rat.	2006-11	16914289
Microwave-assisted extraction through an aqueous medium and simultaneous cleanup by partition on hexane for determining pesticides in agricultural soils by gas chromatography: a critical study.	2006-09-25	17723703
Toxic effects of two pesticides, Imazalil and Triadimefon, on the early development of the ascidian Phallusia mammillata (Chordata, Ascidiacea).	2006-09-12	16863662
Metabolism of myclobutanil and triadimefon by human and rat cytochrome P450 enzymes and liver microsomes.	2006-09	16971344
Triadimefon causes branchial arch malformations in Xenopus laevis embryos.	2006-07	16910123
Falcon 460 EC in the control of foliage diseases of some ornamentals.	2006	17390861
Toxicity profiles in rats treated with tumorigenic and nontumorigenic triazole conazole fungicides: Propiconazole, triadimefon, and myclobutanil.	2006	17178690
Transcriptional profiles in liver from rats treated with tumorigenic and non-tumorigenic triazole conazole fungicides: Propiconazole, triadimefon, and myclobutanil.	2006	17178689
Transcriptional profiles in liver from mice treated with hepatotumorigenic and nonhepatotumorigenic triazole conazole fungicides: Propiconazole, triadimefon, and myclobutanil.	2006	17178688
Toxicity profiles in mice treated with hepatotumorigenic and non-hepatotumorigenic triazole conazole fungicides: Propiconazole, triadimefon, and myclobutanil.	2006	17178687

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:37:22 GMT 2025` Edited by `admin` on `Mon Mar 31 20:37:22 GMT 2025`
Record UNII	1HW039CJF0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIADIMEFON

Common Name

English

AZOCENE

Preferred Name

English

TRIADIMEFON [MI]

Common Name

English

TRIADIMEFON, (±)-

Common Name

English

2-BUTANONE, 1- (4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)-

Systematic Name

English

TRIADIMEFON [HSDB]

Common Name

English

1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)-2-BUTANONE

Systematic Name

English

TRIADIMEFON [ISO]

Common Name

English

1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-ONE

Systematic Name

English

NSC-303303

Code

English

(±)-TRIADIMEFON

Common Name

English

FENXIUNIN

Brand Name

English

BAYLETON

Brand Name

English

BAY 6681 F

Brand Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

109901