BROMUCONAZOLE

BROMUCONAZOLE Basic information
Product Name:BROMUCONAZOLE
Synonyms:BROMOCONAZOLE;BROMUCONAZOL;BROMUCONAZOLE;GRANIT;VECTRA;1-((2rs,4rs,2rs,4sr)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofurfuryl)-1h-1,;1-((4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl)methyl)-1h-1,2,4-tria;1h-1,2,4-triazole,1-((4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl)methy
CAS:116255-48-2
MF:C13H12BrCl2N3O
MW:377.06
EINECS:
Product Categories:ConazolesOrganic Building Blocks;A-BAlphabetic;Alpha sort;B;BI - BZPesticides;Fungicides;Nitrogen Compounds;Others;Pesticides&Metabolites
Mol File:116255-48-2.mol
BROMUCONAZOLE Structure
BROMUCONAZOLE Chemical Properties
Melting point 84℃
Boiling point 504.3±60.0 °C(Predicted)
density 1.71
vapor pressure 50 mg 1-1
refractive index 1.6110 (estimate)
solubility Chloroform (Slightly), Methanol (Slightly)
pka2.75±0.10(Predicted)
form neat
BRN 8393967
LogP3.240
EPA Substance Registry SystemBromuconazole (116255-48-2)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
RIDADR UN 3077 9 / PGIII
WGK Germany 3
RTECS XZ4130000
HazardClass 6.1
PackingGroup III
Hazardous Substances Data116255-48-2(Hazardous Substances Data)
ToxicityLD50 orally in rats, mice: 365, 1151 mg/kg; LD50 dermally in rats: >2000 mg/kg; LD50 by inhalation in rabbits: >5 mg/l; LC50(96 hr) in rainbow trout, bluegill sunfish (mg/l): 1.7, 3.1 (Pepin)
MSDS Information
BROMUCONAZOLE Usage And Synthesis
UsesAgricultural fungicide.
UsesBromuconazole is used on winter wheat and barley for the control of foliar mildews, rusts and other diseases.
DefinitionChEBI: A member of the class of oxolanes carrying 1,2,4-triazol-ylmethyl and 2,4-dichlorophenyl substituents at position 2 as well as a bromo substituent at position 4. A foliar applied conazole fungicide for a range of crops including cereals, fruit, vegetables and vines.
Metabolic pathwayBromuconazole is a relatively stable compound which is not readily hydrolysed, is quite persistent in soil and is subject to relatively slow photodegradation. It is metabolised in plants but the parent compound tends to be the major residue. However, bromuconazole is almost completely metabolised in animals and birds (chickens) and its metabolites are rapidly eliminated.
As with many other triazole fungicides, metabolism is very complex. Bromuconazole exists in four forms (two diastereoisomeric pairs). There are numerous sites available for biotransformation (lack of regioselectivity) and there is also a lack of stereoselectivity at most sites. For example, there are also four forms of metabolite 5 (4-hydroxybromuconazole) (two diastereoisomeric pairs as with bromuconazole itself). Oxidation of secondary alcohols to ketones and the thiolation of certain sites further complicate the picture. Thiolation presumably occurs via the involvement of glutathione but mercapturic acid conjugates (N-acetylcysteines) do not appear to have been isolated.
Bromuconazole has been the subject of an evaluation by the Pesticide Safety Directorate of UK MAFF. All of the information presented below is derived from this source (PSD, 1996). All reported radiolabelled studies were conducted using [14C-phenyl]bromuconazole.

DegradationBromuconazole was found to be stable in buffer at pH 5,7 and 9 at 25 °C over 30 days.
Aqueous photolysis using filtered light to simulate mid-summer sun at 50" N conducted at 25 °C and pH 4 caused slow photodegradation. The DT50 of bromuconazole was 18.2 days. Over 28 days a 10% yield of CO2 was obtained and six or more photoproducts were detected with none accounting for more than 8% of the total. No degradation occurred in dark controls.
BROMUCONAZOLE Preparation Products And Raw materials
Propiconazole Diniconazole Flutriafol Tebuconazole Penconazole TRITICONAZOLE SIMECONAZOLE Triadimenol Cyproconazole IMIBENCONAZOLE 1-[[(2S,3S)-3-(2-Chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole Ethychlozate Xiwojunan tetrahydrofurfuryl-2-methylamine Benzyl 2-bromoethyl ether 3-BROMOTETRAHYDROFURAN ALPHA-(2,4-DICHLOROPHENYL)-1H-1,2,4-TRIAZOLE-1-ETHANOL BROMUCONAZOLE

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