U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H7N3S
Molecular Weight 189.237
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICYCLAZOLE

SMILES

CC1=CC=CC2=C1N3C=NN=C3S2

InChI

InChIKey=DQJCHOQLCLEDLL-UHFFFAOYSA-N
InChI=1S/C9H7N3S/c1-6-3-2-4-7-8(6)12-5-10-11-9(12)13-7/h2-5H,1H3

HIDE SMILES / InChI

Molecular Formula C9H7N3S
Molecular Weight 189.237
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tricyclazole is a systemic fungicide for control of Pyricularia oryzae on rice. Tricyclazole protects plants from infection by P. oryzae by preventing penetration of the epidermis by the fungus. The compound acts by inhibiting melanization within the appressorium, thus causing a lack of rigidity in the appressorial wall. Tricyclazole has no apparent effect on spore germination although sporulation is reduced. Tricyclazole is not curative but is protective in its activity. Tricyclazole can influence the pathogenic ability of aspergillus aculeatus by damaging the cell structure of hyphae and conidia, reducing the melanin production, and altering the expression of pathogenic-related gene. Tricyclazole toxin can impair testosterone secretion and the testicular structure in mice, leaving an adversely effect on sperm production system.

Approval Year

PubMed

PubMed

TitleDatePubMed
Appressorium turgor pressure of Colletotrichum kahawae might have a role in coffee cuticle penetration.
2010-12-15
Determination of triazole fungicides in environmental water samples by high performance liquid chromatography with cloud point extraction using polyethylene glycol 600 monooleate.
2010-11-08
Ecotoxicological effects of rice field waters on selected planktonic species: comparison between conventional and organic farming.
2010-11
PdeH, a high-affinity cAMP phosphodiesterase, is a key regulator of asexual and pathogenic differentiation in Magnaporthe oryzae.
2010-05-06
Identification, Cloning, and Characterization of l-Phenylserine Dehydrogenase from Pseudomonas syringae NK-15.
2010-03-25
Melanin in Fonsecaea pedrosoi: a trap for oxidative radicals.
2010-03-16
Melanin is an essential component for the integrity of the cell wall of Aspergillus fumigatus conidia.
2009-08-24
Physiological effects of tricyclazole on zebrafish (Danio rerio) and post-exposure recovery.
2009-07
Melanin synthesis by Sclerotinia sclerotiorum.
2009-06-20
Daily variation of pesticides in surface water of a small river flowing through paddy field area.
2009-06
Growth conditions influence melanization of Brazilian clinical Sporothrix schenckii isolates.
2009-04
Multiresidue analysis of 47 pesticides in cooked wheat flour and polished rice by liquid chromatography with tandem mass spectrometry.
2009-04
Two homologous fungal carbonyl reductases with different substrate specificities.
2009-03-16
Behavior of sprayed tricyclazole in rice paddy lysimeters.
2009-02
Conidiation color mutants of Aspergillus fumigatus are highly pathogenic to the heterologous insect host Galleria mellonella.
2009
The negative interaction between the degradation of phenanthrene and tricyclazole in medium, soil and soil/compost mixture.
2008-09
Simulated rainfall removal of tricyclazole sprayed on rice foliage.
2008-05
Adaptation of extremely halotolerant black yeast Hortaea werneckii to increased osmolarity: a molecular perspective at a glance.
2008
The influence of ortho- and para-diphenoloxidase substrates on pigment formation in black yeast-like fungi.
2008
Synthetic pyrazole derivatives as growth inhibitors of some phytopathogenic fungi.
2007-12-12
Ionizing radiation changes the electronic properties of melanin and enhances the growth of melanized fungi.
2007-05-23
Organic amendments affecting sorption, leaching and dissipation of fungicides in soils.
2006-12
Univariate near infrared methods for determination of pesticides in agrochemicals.
2006-10-02
Effects of tricyclazole (5-methyl-1,2,4-triazol[3,4] benzothiazole), a specific DHN-melanin inhibitor, on the morphology of Fonsecaea pedrosoi conidia and sclerotic cells.
2006-09
Effects of disrupting the polyketide synthase gene WdPKS1 in Wangiella [Exophiala] dermatitidis on melanin production and resistance to killing by antifungal compounds, enzymatic degradation, and extremes in temperature.
2006-06-19
Mercury(II) ion-selective polymeric membrane sensors for analysis of mercury in hazardous wastes.
2006-06
Emerging antifungal azoles and effects on Magnaporthe grisea.
2006-06
Studies on the interaction of tricyclazole with beta-cyclodextrin and human serum albumin by spectroscopy.
2006-05
Monitoring tricyclazole residues in rice paddy watersheds.
2006-01
Inhibition of melanin synthesis pathway by tricyclazole increases susceptibility of Fonsecaea pedrosoi against mouse macrophages.
2005-12-15
Isolation and antifungal activity of 4-phenyl-3-butenoic acid from Streptomyces koyangensis strain VK-A60.
2005-10-05
Changes in dissolved organic carbon of soil amendments with aging: effect on pesticide adsorption behavior.
2004-09-08
Characterization of the melanin pigment of a cosmopolitan fungal endophyte.
2004-08
Identification of 1,8-dihydroxynaphthalene melanin in Monosporascus cannonballus and the analysis of hexaketide and pentaketide compounds produced by wild-type and pigmented isolates of the fungus.
2004-06-30
The disruption of a Galpha subunit sheds new light on the pathogenicity of Stagonospora nodorum on wheat.
2004-05
Synthesis and antifungal action of new tricyclazole analogues.
2004-04-07
Evidence for 1,8-dihydroxynaphthalene melanin in three halophilic black yeasts grown under saline and non-saline conditions.
2004-03-19
[Techniques of diseases, insect pests and weeds control and their efficacy in bio-rational rice production].
2004-01
Melanin biosynthesis in the fungus Curvularia lunata (teleomorph: Cochliobolus lunatus).
2003-02
Development of new fungicides against Magnaporthe grisea: synthesis and biological activity of pyrazolo[3,4-d][1,3]thiazine, pyrazolo[1,5-c][1,3,5]thiadiazine, and pyrazolo[3,4-d]pyrimidine derivatives.
2002-08-14
The role of melanin in the antagonistic interaction between the apple scab pathogen Venturia inaequalis and Microsphaeropsis ochracea.
2002-04
1,8-Dihydroxynaphthalene monoglucoside, a new metabolite of Sclerotinia sclerotiorum, and the effect of tricyclazole on its production.
2002-04
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:55:30 GMT 2025
Edited
by admin
on Mon Mar 31 18:55:30 GMT 2025
Record UNII
R7U3MEU7VR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICYCLAZOLE
ISO  
Common Name English
BEAM
Preferred Name English
2,7,8,9-TRICYCLAZOLE
Common Name English
TRICYCLAZOLE [ISO]
Common Name English
TRICYCLAZONE
Common Name English
TRICYCLAZOLE [MI]
Common Name English
5-METHYL-1,2,4-TRIAZOLO(3,4-B)BENZOTHIAZOLE
Systematic Name English
EL-291
Code English
5-METHYL-1,2,4-TRIAZOLO(3,4-B)(1,3)BENZOTHIAZOLE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 120201
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
Code System Code Type Description
MESH
C041191
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
FDA UNII
R7U3MEU7VR
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
255-559-5
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
CAS
41814-78-2
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
DRUG BANK
DB02891
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
ALANWOOD
tricyclazole
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
EVMPD
SUB180339
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID7037478
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
PUBCHEM
39040
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
MERCK INDEX
m11744
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY
SMS_ID
100000166271
Created by admin on Mon Mar 31 18:55:30 GMT 2025 , Edited by admin on Mon Mar 31 18:55:30 GMT 2025
PRIMARY