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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
Structure of TRIADIMENOL

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

HIDE SMILES / InChI

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.

CNS Activity

Curator's Comment: Rats exposed to 48 mg/kg triadimenol elicited an excitatory effect.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Effects of organonitrogen, carbamate pesticides and others on beta-hexosaminidase release from rat basophilic leukemia cells (RBL-2H3)].
2001 Aug
Behavior of triadimefon in two Lebanese soils.
2001 Nov
Monitoring of pesticide residues on cucumber, tomatoes and strawberries in Gaza Governorates, Palestine.
2002 Feb
On-line preconcentration and enantioselective separation of triadimenol by electrokinetic chromatography using cyclodextrins as chiral selectors.
2003 Jan 15
Sequence variation in the CYP51 gene of Blumeria graminis associated with resistance to sterol demethylase inhibiting fungicides.
2005 Aug
Teratogenic effects of two antifungal triazoles, triadimefon and triadimenol, on Xenopus laevis development: craniofacial defects.
2005 Jul 30
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
Comparative enantioseparation of seven triazole fungicides on (S,S)-Whelk O1 and four different cellulose derivative columns.
2006 Aug
Inhibition of rainbow trout (Oncorhynchus mykiss) P450 aromatase activities in brain and ovarian microsomes by various environmental substances.
2006 Nov
Determination of triadimenol based on the quenching effect on resonance light scattering from the triadimenol-deoxyribonucleic acid-hydrochloric acid system.
2007 May
Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants.
2008 Jul 4
Fungicide-driven evolution and molecular basis of multidrug resistance in field populations of the grey mould fungus Botrytis cinerea.
2009 Dec
Photocatalytic degradation of eight pesticides in leaching water by use of ZnO under natural sunlight.
2009 Dec 30
Stereoselective degradation of fungicide triadimenol in cucumber plants.
2010 Feb
Solarization and biosolarization enhance fungicide dissipation in the soil.
2010 Mar
Interaction between vine pesticides and bovine serum albumin studied by nuclear spin relaxation data.
2010 Oct 13
Patents

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
Triadimenol was identified as weak oestrogen receptor agonist, which at 10 uM induces 1.9-fold increase in proliferation of human MCF7 breast cancer cells (E3 clone).
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:30:05 GMT 2023
Edited
by admin
on Sat Dec 16 00:30:05 GMT 2023
Record UNII
NFR7MRD9NM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIADIMENOL
HSDB   ISO   MI  
Common Name English
TRIADIMENOL, (±)-
Common Name English
.BETA.-(4-CHLOROPHENOXY)-.ALPHA.-(1,1-DIMETHYLETHYL)-1H-1,2,4-TRIAZOLE-1-ETHANOL
Systematic Name English
BAYFIDAN
Brand Name English
TRIADIMENOL [HSDB]
Common Name English
VYDINE
Brand Name English
TRIADIMENOL [MI]
Common Name English
1H-1,2,4-TRIAZOLE-1-ETHANOL, .BETA.-(4-CHLOROPHENOXY)-.ALPHA.-(1,1-DIMETHYLETHYL)-
Systematic Name English
TRIADIMENOL [ISO]
Common Name English
SPINNAKER
Brand Name English
(±)-TRIADIMENOL
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 127201
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
Code System Code Type Description
HSDB
7733
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
259-537-6
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY
MERCK INDEX
m11025
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID0032493
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY
ALANWOOD
triadimenol
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY
FDA UNII
NFR7MRD9NM
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY
PUBCHEM
41368
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY
CAS
55219-65-3
Created by admin on Sat Dec 16 00:30:05 GMT 2023 , Edited by admin on Sat Dec 16 00:30:05 GMT 2023
PRIMARY