| InChI=1S/C13H12BrCl2N3O/c14-9-4-13(20-5-9,6-19-8-17-7-18-19)11-2-1-10(15)3-12(11)16/h1-3,7-9H,4-6H2 |
| HJJVPARKXDDIQD-UHFFFAOYSA-N |
| N1(N=CN=C1)CC2(CC(CO2)Br)C=3C(=CC(=CC3)Cl)Cl |
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antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of EC 1.14.13.70 (sterol 14alpha-demethylase).
fungicide
A substance used to destroy fungal pests.
(via triazole fungicide )
(via conazole fungicide )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via triazole antifungal agent )
(via conazole antifungal agent )
ergosterol biosynthesis inhibitor
Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.
(via conazole antifungal agent )
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antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
fungicide
A substance used to destroy fungal pests.
(via triazole fungicide )
(via conazole fungicide )
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View more via ChEBI Ontology
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2,5-anhydro-4-bromo-1,3,4-trideoxy-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)pentitol
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1-((4-Bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl)methyl)-1H-1,2,4-triazole
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ChemIDplus
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97
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PPDB
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bromuconazole
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Alan Wood's Pesticides
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C18704
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KEGG COMPOUND
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EP258161
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Patent
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| View more database links |
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116255-48-2
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CAS Registry Number
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KEGG COMPOUND
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116255-48-2
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CAS Registry Number
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ChemIDplus
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8393967
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Reaxys Registry Number
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Reaxys
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Bowyer P, Denning DW (2014)
Environmental fungicides and triazole resistance in Aspergillus.
Pest management science 70, 173-178 [PubMed:23616354]
[show Abstract]
Fungal diseases are problematic in both human health and agriculture. Treatment options are limited and resistance may emerge. The relatively recent recognition of triazole resistance in Aspergillus fumigatus has prompted questioning of the origin of resistance. While multiple mechanisms are described in clinical isolates from triazole-treated patients, some de novo resistance is also recognised, especially attributable to TR34 /L98H. Such strains probably arose in the environment, and, indeed, multiple studies have now demonstrated TR(34) /L98H triazole resistance strains of A. fumigatus from soil. Docking and other in vitro studies are consistent with environmental resistance induction through exposure to certain triazole fungicides, notably difenoconazole, propiconazole, epoxiconazole, bromuconazole and tebuconazole. This article addresses the potential implications of this issue for both human health and food security. | Zhang H, Qian M, Wang X, Wang X, Xu H, Wang Q, Wang M (2012)
HPLC-MS/MS enantioseparation of triazole fungicides using polysaccharide-based stationary phases.
Journal of separation science 35, 773-781 [PubMed:22532344]
[show Abstract]
The enantiomeric separation of 21 triazole fungicides was carried out on four polysaccharide-derived chiral stationary phases in the reversed phase separation mode using high performance liquid chromatography coupled with tandem mass spectrometry. All fungicides were detected in electrospray ionization (ESI) positive mode with selected reaction monitoring (SRM). Complete enantioseparation was achieved for 21 fungicides except for difenoconazole based on cellulose tris (3,5-dimethylphenylcarbamate) and cellulose tris (3-chloro-4-methylphenyl carbamate) columns by optimizing experimental conditions including mobile phase and column temperature. Mobile phase was 0.1% formic acid aqueous solution mixed with methanol or acetonitrile in different proportions. Among all the fungicides, 15 with two enantiomers and three with four stereoisomers (bitertanol, bromuconazole, and cyproconazole) were successfully separated at 25°C. Enantioseparation for the other three fungicides (propiconazole, triadimenol, and difenoconazole) with four stereoisomers could be achieved by changing the column temperature from 10 to 40°C. Propiconazole and triadimenol were enantioseparated on baseline at 40 and at 35°C, respectively, and difenoconazole was enantioseparated partially with the R(s) > 1.1 at 25°C. Moreover, linearities and limits of detection (LODs) of 21 fungicides except for difenoconazole were studied, showing coefficients of determination (R(2)) higher than 0.99 and LODs lower than 2.5 μg/L. | Wan Ibrahim WA, Warno SA, Aboul-Enein HY, Hermawan D, Sanagi MM (2009)
Simultaneous enantioseparation of cyproconazole, bromuconazole, and diniconazole enantiomers by CD-modified MEKC.
Electrophoresis 30, 1976-1982 [PubMed:19517438]
[show Abstract]
An efficient method for the simultaneous enantioseparation of cyproconazole, bromuconazole, and diniconazole enantiomers was developed by CD-modified MEKC using a dual mixture of neutral CDs as chiral selector. Three neutral CDs namely hydroxypropyl-beta-CD, hydroxypropyl-gamma-CD, and gamma-CD were tested as chiral selectors at different concentrations ranging from 10, 20, 30 and 40 mM, but enantiomers of the studied fungicides were not completely separated. The best dual chiral recognition mode for the simultaneous separation of cyproconazole, bromuconazole, and diniconazole enantiomers was achieved with a mixture of 27 mM hydroxypropyl-beta-CD and 3 mM hydroxypropyl-gamma-CD in 25 mM phosphate buffer (pH 3.0) containing 40 mM SDS to which methanol-acetonitrile (10%:5% v/v) was added as organic modifiers. The best separation was based on the appearance of 10 peaks simultaneously, with good resolution (R(s) 1.1-15.9), and peak efficiency (N>200,000). Good repeatabilities in the migration time, peak area, and peak height were obtained in terms of RSD ranging from (0.72 to 1.06)%, (0.39 to 3.49)%, and (1.90 to 4.84)%, respectively. | Mazur CS, Kenneke JF, Tebes-Stevens C, Okino MS, Lipscomb JC (2007)
In vitro metabolism of the fungicide and environmental contaminant trans-bromuconazole and implications for risk assessment.
Journal of toxicology and environmental health. Part A 70, 1241-1250 [PubMed:17573638]
[show Abstract]
trans-Bromuconazole is a chiral chemical representative of a class of triazole derivatives known to inhibit specific fungal cytochrome P-450 (CYP) reactions. Kinetic measurements and delineation of metabolic pathways for triazole chemicals within in vitro hepatic microsomes are needed for accurate risk assessment and predictive in vivo physiological modeling. The studies described here were conducted with rat liver microsomes to determine Michaelis-Menten saturation kinetic parameters (Vmax and KM) for trans-bromuconazole using both substrate depletion and product formation reaction velocities. Kinetic parameters determined for trans-bromuconazole depletion at varying protein levels incubated at physiological temperature 37 degrees C resulted in a KM value of 1.69 microM and a Vmax value of 1398 pmol/min/mg protein. The concomitant linear formation of two metabolites identified using liquid chromatography/time-of-flight mass spectrometry (LC/MS-TOF) and LC-MS/MS indicated hydroxylation of the trans-bromuconazole dichlorophenyl ring moiety. KM values determined for the hydroxylated metabolites were 0.87 and 1.03 microM, with Vmax values of 449 and 694 pmol/min/mg protein, respectively. Chemical inhibition assays and studies conducted with individual purified human recombinant enzymes indicated the CYP3A subfamily was primarily responsible for biotransformation of the parent substrate. Additionally, trans-bromuconazole was found to undergo stereoselective metabolism as evidenced by a change in the enantiomeric ratio (trans-/trans+) with respect to time. | Reuveni M (2006)
Inhibition of germination and growth of Alternaria alternata and mouldy-core development in Red Delicious apple fruit by Bromuconazole and Sygnum
Crop Protection. 25, 253-258 [Agricola:IND43838427]
[show Abstract]
Alternaria alternata is the predominant fungal pathogen responsible for mouldy-core in Red Delicious strains of apple. This study reports on the effects of sygnum (a premix fungicide containing pyraclostrobin+nicobifen), and the sterol biosynthesis inhibitor bromuconazole on spore germination, mycelial growth, decay on detached fruits, and control of mouldy-core caused by A. alternata. Germination was more sensitive to sygnum than to bromuconazole. The 50% and 90% effective concentrations (EC50, and EC90) for in vitro inhibition of conidial germination of the fungus of sygnum were 20 and 79 μg ml-1, respectively, whereas those of bromuconazole were 57 and 735 μg ml-1, respectively. Mycelial growth in vitro of A. alternata was more sensitive to sygnum (EC50 and EC90 values of 2 and 4 μg ml-1, respectively) than to bromuconazole (EC50 and EC90 values of 47 and 95 μg ml-1, respectively). Decay formation by A. alternata on mature detached fruits was also more affected by sygnum: it was completely inhibited by sygnum and bromuconazole at concentrations of 5 and 50 μg ml-1, respectively. Three foliar applications of bromuconazole and sygnum, between the beginning of bloom and petal fall, reduced the number of infected fruits by 55-70% and 45-80%, respectively, compared with control non-treated trees. In the field, bromuconazole and sygnum were as effective as or better than difenoconazole. The inhibitory effects of bromuconazole and sygnum on one or more stages of the life cycle of A. alternata, on decay development in detached fruits, and on mouldy-core in the field indicate that a control programme based on spray applications of bromuconazole and sygnum during the bloom period can effectively reduce mouldy-core on Red Delicious. |
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