Details
| Stereochemistry | MIXED |
| Molecular Formula | C14H18ClN3O2 |
| Molecular Weight | 295.765 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)C(O)C(OC1=CC=C(Cl)C=C1)N2C=NC=N2
InChI
InChIKey=BAZVSMNPJJMILC-UHFFFAOYSA-N
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
| Molecular Formula | C14H18ClN3O2 |
| Molecular Weight | 295.765 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Triadimenol is a triazole-type fungicide that is identified as weak estrogen receptor agonist. Triadimenol is a systemic fungicide with protective, curative and eradicant action. Absorbed by the roots and leaves, with ready translocation in young growing tissues, but less ready translocation in older, woody tissues. Triadimenolis used for controlling of powdery mildews, rusts and Rhynchosporium in cereals, and, when applied as a seed treatment, control of bunt, smuts, Typhula spp., seedling blight, leaf stripe, net blotch and other cereal diseases. Also used on vegetables, ornamentals, coffee, hops, vines, fruit, tobacco, sugar cane, bananas and other crops, mainly against powdery mildews, rusts and various leaf spot diseases.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro activities of two new antifungal azoles. | 1984 Mar |
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| [Effects of organonitrogen, carbamate pesticides and others on beta-hexosaminidase release from rat basophilic leukemia cells (RBL-2H3)]. | 2001 Aug |
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| Plant sterol 14 alpha-demethylase affinity for azole fungicides. | 2001 Jun 15 |
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| High-performance chiral separation of fourteen triazole fungicides by sulfated beta-cyclodextrin-mediated capillary electrophoresis. | 2001 Mar 30 |
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| Behavior of triadimefon in two Lebanese soils. | 2001 Nov |
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| Monitoring of pesticide residues on cucumber, tomatoes and strawberries in Gaza Governorates, Palestine. | 2002 Feb |
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| Isogamous, hermaphroditic inheritance of mitochondrion-encoded resistance to Qo inhibitor fungicides in Blumeria graminis f. sp. tritici. | 2002 Jul |
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| Effects of sensitizers on the photodegradation of the systemic fungicide triadimenol. | 2003 Apr |
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| On-line preconcentration and enantioselective separation of triadimenol by electrokinetic chromatography using cyclodextrins as chiral selectors. | 2003 Jan 15 |
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| Separation of triadimefon and triadimenol enantiomers and diastereoisomers by supercritical fluid chromatography. | 2003 Jan 31 |
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| Effects of acibenzolar-s-methyl and ethirimol on the composition of a laboratory population of barley powdery mildew. | 2003 Mar |
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| Coupling solid-phase microextraction and high-performance liquid chromatography for direct and sensitive determination of halogenated fungicides in wine. | 2003 May 2 |
|
| The determination of deoxyribonucleic acids with triadimenol based on the enhancement of resonance light scattering. | 2004 |
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| 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. | 2004 Jul-Aug |
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| Estimation of estrogenic and antiestrogenic activities of selected pesticides by MCF-7 cell proliferation assay. | 2004 May |
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| Surface photochemistry of pesticides: an approach using diffuse reflectance and chromatography techniques. | 2004 May 15 |
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| Fate of pesticides during the winemaking process in relation to malolactic fermentation. | 2005 Apr 20 |
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| Sequence variation in the CYP51 gene of Blumeria graminis associated with resistance to sterol demethylase inhibiting fungicides. | 2005 Aug |
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| Factors affecting triadimefon degradation in soils. | 2005 Jan 12 |
|
| Teratogenic effects of two antifungal triazoles, triadimefon and triadimenol, on Xenopus laevis development: craniofacial defects. | 2005 Jul 30 |
|
| Evaluation of Several Approaches to Manage Meloidogyne incognita and Cotton Seedling Disease Complexes in the High Plains of Texas. | 2005 Mar |
|
| Determination of azolic fungicides in wine by solid-phase extraction and high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. | 2005 May 27 |
|
| Study on the common teratogenic pathway elicited by the fungicides triazole-derivatives. | 2005 Sep |
|
| Determination of 22 triazole compounds including parent fungicides and metabolites in apples, peaches, flour, and water by liquid chromatography/tandem mass spectrometry. | 2005 Sep-Oct |
|
| Falcon 460 EC in the control of foliage diseases of some ornamentals. | 2006 |
|
| Comparative enantioseparation of seven triazole fungicides on (S,S)-Whelk O1 and four different cellulose derivative columns. | 2006 Aug |
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| Pesticide exposure: the hormonal function of the female reproductive system disrupted? | 2006 May 31 |
|
| Inhibition of rainbow trout (Oncorhynchus mykiss) P450 aromatase activities in brain and ovarian microsomes by various environmental substances. | 2006 Nov |
|
| [Screening method for the determination of 199 pesticides in agricultural products by gas chromatography/ion trap mass spectrometry (GC/MS/MS)]. | 2006 Oct |
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| Evaluation of the effects of chemical versus biological control on Botrytis cinerea agent of gray mould disease of strawberry. | 2007 |
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| Determination of triadimenol based on the quenching effect on resonance light scattering from the triadimenol-deoxyribonucleic acid-hydrochloric acid system. | 2007 May |
|
| [Application of binding spectra in DMIs fungicide screening]. | 2007 Nov |
|
| 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 |
|
| [Determination of triadimenol residue in foods with dispersive solid phase extraction cleanup by gas chromatography-negative chemical ionization mass spectrometry]. | 2008 Jul |
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| Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants. | 2008 Jul 4 |
|
| Combining TiO2-photocatalysis and wetland reactors for the efficient treatment of pesticides. | 2008 Mar |
|
| Mechanistic investigation of the noncytochrome P450-mediated metabolism of triadimefon to triadimenol in hepatic microsomes. | 2008 Oct |
|
| 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. | 2008 Oct 24 |
|
| New mathematic model for predicting chiral separation using molecular docking: mechanism of chiral recognition of triadimenol analogues. | 2009 Jul |
|
| Mechanistic approach to understanding the toxicity of the azole fungicide triadimefon to a nontarget aquatic insect and implications for exposure assessment. | 2009 Jul 15 |
|
| 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). | 2010 Dec |
|
| Stereoselective degradation of fungicide triadimenol in cucumber plants. | 2010 Feb |
|
| Integration of metabolomics and in vitro metabolism assays for investigating the stereoselective transformation of triadimefon in rainbow trout. | 2010 Feb |
|
| Descriptive and mechanistic toxicity of conazole fungicides using the model test alga Dunaliella tertiolecta (Chlorophyceae). | 2010 Jun |
|
| Solarization and biosolarization enhance fungicide dissipation in the soil. | 2010 Mar |
|
| Gender and species differences in triadimefon metabolism by rodent hepatic microsomes. | 2010 Mar 1 |
|
| Interaction between vine pesticides and bovine serum albumin studied by nuclear spin relaxation data. | 2010 Oct 13 |
|
| Azole drugs are imported by facilitated diffusion in Candida albicans and other pathogenic fungi. | 2010 Sep 30 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Rats exposed to 48 mg/kg triadimenol elicited an excitatory effect. https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+55219-65-3
Rats: Acute oral LD50=721 mg/kg
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 00:30:05 GMT 2023
by
admin
on
Sat Dec 16 00:30:05 GMT 2023
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| Record UNII |
NFR7MRD9NM
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
127201
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admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
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7733
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259-537-6
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m11025
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PRIMARY | Merck Index | ||
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DTXSID0032493
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triadimenol
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NFR7MRD9NM
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41368
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55219-65-3
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