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 8297	9.29 µM [IC50]
P450 sterol 14-alpha-demethylase 1 Target ID: CHEMBL2366431 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23350742	Binding Agent 1064
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28637041	Inhibitor 8297	58.73 µM [IC50]
3-alpha-hydroxysteroid dehydrogenase 1 Target ID: CHEMBL1075221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28812018	Inhibitor 8297	26.0 µM [IC50]

PubMed

Title	Date	PubMed
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
Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles.	2006 Dec 15	17008103
Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss).	2006 Dec 30	17118468
Triadimefon causes branchial arch malformations in Xenopus laevis embryos.	2006 Jul	16910123
Inhibition of rainbow trout (Oncorhynchus mykiss) P450 aromatase activities in brain and ovarian microsomes by various environmental substances.	2006 Nov	17081805
Effect of conazole fungicides on reproductive development in the female rat.	2006 Nov	16914289
Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles.	2006 Nov 10	16989930
Metabolism of myclobutanil and triadimefon by human and rat cytochrome P450 enzymes and liver microsomes.	2006 Sep	16971344
Toxic effects of two pesticides, Imazalil and Triadimefon, on the early development of the ascidian Phallusia mammillata (Chordata, Ascidiacea).	2006 Sep 12	16863662
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 Sep 25	17723703
Analyses of pesticide residues in fruit-based baby food by liquid chromatography/electrospray ionization time-of-flight mass spectrometry.	2007	17551990
Changes in biochemical constituents and induction of early sprouting by triadimefon treatment in white yam (Dioscorea rotundata Poir.) tubers during storage.	2007 Apr	17444605
Alterations in lipid peroxidation, electrolyte leakage, and proline metabolism in Catharanthus roseus under treatment with triadimefon, a systemic fungicide.	2007 Dec	18068649
Induction of cytochrome P450 enzymes in rat liver by two conazoles, myclobutanil and triadimefon.	2007 Feb	17484520
Antifungal triazole derivative triadimefon induces ectopic maxillary cartilage by altering the morphogenesis of the first branchial arch.	2007 Feb	17187389
Disruption of testosterone homeostasis as a mode of action for the reproductive toxicity of triazole fungicides in the male rat.	2007 Jan	17018648
Gene expression in Xenopus laevis embryos after Triadimefon exposure.	2007 Jan	16875885
Toxicogenomic study of triazole fungicides and perfluoroalkyl acids in rat livers predicts toxicity and categorizes chemicals based on mechanisms of toxicity.	2007 Jun	17383973
Krox20 is down-regulated following triazole in vitro embryonic exposure: a polycompetitor-based assay.	2007 Mar 30	17343997
Determination of triadimenol based on the quenching effect on resonance light scattering from the triadimenol-deoxyribonucleic acid-hydrochloric acid system.	2007 May	17377777
[Application of binding spectra in DMIs fungicide screening].	2007 Nov	18257249
Comparative effects of different triazole compounds on growth, photosynthetic pigments and carbohydrate metabolism of Solenostemon rotundifolius.	2007 Nov 15	17669636
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 Nov-Dec	17875381
Raman spectroscopy-based metabolomics for differentiating exposures to triazole fungicides using rat urine.	2007 Oct 1	17718537
Changes in carbohydrate metabolism by triazole growth regulators in cassava (Manihot esculenta Crantz); effects on tuber production and quality.	2007 Sep	17720581
Growth and photosynthetic pigments responses of two varieties of Catharanthus roseus to triadimefon treatment.	2008 Apr	18355749
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Comparative effects of different triazole compounds on antioxidant metabolism of Solenostemon rotundifolius.	2008 Apr 1	18065211
Cross-species comparison of conazole fungicide metabolites using rat and rainbow trout (Onchorhynchus mykiss) hepatic microsomes and purified human CYP 3A4.	2008 Feb 1	18323127
[Determination of triadimenol residue in foods with dispersive solid phase extraction cleanup by gas chromatography-negative chemical ionization mass spectrometry].	2008 Jul	18959253
Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants.	2008 Jul 4	18343389
Osmoregulation and antioxidant metabolism in drought-stressed Helianthus annuus under triadimefon drenching.	2008 Jun	18510994
Transcriptional responses in thyroid tissues from rats treated with a tumorigenic and a non-tumorigenic triazole conazole fungicide.	2008 Mar 15	18164361
Fungicide (Rubigan) overdose mimicking organophosphate poisoning.	2008 Nov	19070292
Endogenous hormonal and enzymatic responses of Catharanthus roseus with triadimefon application under water deficits.	2008 Nov	18940699
Mechanistic investigation of the noncytochrome P450-mediated metabolism of triadimefon to triadimenol in hepatic microsomes.	2008 Oct	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 Sep	19295087
Enantiomer separation of triazole fungicides by high-performance liquid chromatography.	2009 Apr	18570307
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 Jan 1	18976680
Three conazoles increase hepatic microsomal retinoic acid metabolism and decrease mouse hepatic retinoic acid levels in vivo.	2009 Jan 15	19010342
Discrimination of tumorigenic triazole conazoles from phenobarbital by transcriptional analyses of mouse liver gene expression.	2009 Jul	19363144
Toxicogenomic effects common to triazole antifungals and conserved between rats and humans.	2009 Jul 1	19409404
Chronic toxicity of five structurally diverse demethylase-inhibiting fungicides to the crustacean Daphnia magna: a comparative assessment.	2009 Jun	19132812
Compensation for matrix effects in gas chromatography-tandem mass spectrometry using a single point standard addition.	2009 Jun 5	19406413
In vivo mutagenicity of conazole fungicides correlates with tumorigenicity.	2009 Mar	19028983
Descriptive and mechanistic toxicity of conazole fungicides using the model test alga Dunaliella tertiolecta (Chlorophyceae).	2010 Jun	19382186

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 00:32:25 GMT 2023` Edited by `admin` on `Sat Dec 16 00:32:25 GMT 2023`
Record UNII	1HW039CJF0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIADIMEFON

Common 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

AZOCENE

Brand Name

English

BAY 6681 F

Brand Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

109901