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ブロムコナゾール

Bromuconazole

HCID 3444
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
116255-48-2
標準SMILES
Clc1ccc(C2(Cn3cncn3)CC(Br)CO2)c(Cl)c1
InChIKey
HJJVPARKXDDIQD-UHFFFAOYSA-N
分子式
C13H12BrCl2N3O
平均分子量
377.1 g/mol
単同位体質量
374.95408

概要

Bromuconazole is 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. It has a role as an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a dichlorobenzene, a member of oxolanes, a member of triazoles, an organobromine compound, a conazole fungicide and a triazole fungicide.

名称と識別子

優先名称
Bromuconazole
IUPAC
1-[[4-bromo-2-(2,4-dichlorophenyl)oxolan-2-yl]methyl]-1,2,4-triazole
現地名
ブロムコナゾール
英語名
BROMUCONAZOLE
分子式
C13H12BrCl2N3O
分子量
377.06

名称と別名

Bromuconazole116255-48-2GRANITDTXSID9032531PHS29ZMZ81VECTRA1-((4-Bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl)methyl)-1H-1,2,4-triazoleDTXCID7012531CHEBI:819001-((2RS,4RS,2RS,4SR)-4-Bromo-2-(2,4-dichlorophenyl)tetrahydrofurfuryl)-1H-1,2,4-triazole1H-1,2,4-Triazole, 1-((4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl)methyl)-RefChem:570413
名称をさらに表示
ブロムコナゾールブロムコナゾール標準品ブロムコナゾール STANDARDブロムコナゾール標準品(異性体混合物)ブロムコナゾール Standard, 100 µg/mL in AcCN1-[[2-(2,4-ジクロロフェニル)-4-ブロモテトラヒドロフラン]-2-イルメチル]-1H-1,2,4-トリアゾールモルガン1-{[4-ブロモ-2-(2,4-ジクロロフェニル)オキソラン-2-イル]メチル}-1H-1,2,4-トリアゾールブロモコナゾールLS 8602631-((2RS,4RS2,4-triazoleBromucanozolBROMOCONAZOLE
408-060-3BromuconazolBromuconazole [ISO]1-[[4-bromo-2-(2,4-dichlorophenyl)oxolan-2-yl]methyl]-1,2,4-triazole2,5-anhydro-4-bromo-1,3,4-trideoxy-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)pentitolPentitol, 2,5-anhydro-4-bromo-1,3,4-trideoxy-2-C-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-HSDB 7419CHIPCO' Bromuconazole

物性

構造計算による物性

XLogP
3.6
極性表面積
39.9 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
3
重原子数
20
形式電荷
0
複雑度
352

実験および物理化学的性質

Pesticides · 4 件

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Bromuconazole) -> USDA PDB

LogP · 3 件

log Kow = 3.24

3.24 (20 °C)

3.24

OdorOdorless
Density · 2 件

1.72 g/mL

Density (at 20 °C): 1.72 g/cm³

Color/Form · 2 件

Colorless powder

White to off-white powder

Solubility · 4 件

Acetone 32 g/100 ml; dichloromethane 50 g/100 ml; ethyl acetate 23 g/100 ml; n-hexane 0.2 g/100ml; MeOH 30 g/100 ml; 1-octanol 6 g/100 ml; 2-propanol 6 g/100 ml; toluene 22 g/100 ml; water (distilled) 61 mg/L; water (pH 5) 52 mg/L

Moderate to high solubility in organic solvents.

In water, 50 mg/L at 25 °C

Solubility in water, mg/l at 25 °C: 50 (practically insoluble)

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling PointNo boiling point at normal pressure; decomposes at 194 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 76 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information · 4 件

Commission Regulation (EC) No 1490/2002

Bromuconazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2010/92/EU, Reg. (EU) 2024/324, Reg. (EU) No 2018/670, Reg. (EU) No 540/2011

REACH registered substance: Bromuconazole (EC: 408-060-3)

Fire HazardsLiquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
Chemical DangersDecomposes on heating and on burning. This produces toxic fumes and gases including nitrogen oxides, hydrogen chloride, hydrogen bromide and carbon monoxide.
Packaging and LabellingDo not transport with food and feedstuffs.
Hazard Classes and Categories · 2 件

Acute Tox. 4 (100%)

Acute Tox. 4 (100%)

安全と保護具

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Metabolism in animals (rat, cow, hen) is extensive. Nearly 60 different metabolites were detected in the rat, 57 of which had structures assigned. No evidence was found to suggest that the compound and/or its metabolites accumulate in the organs and tissues of those species, even following repeated administration.

用途と製造

Uses · 4 件

For Bromuconazole (USEPA/OPP Pesticide Code: 120503) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Agricultural fungicide; Ergosterol biosynthesis inhibiting triazole

Systemic fungicide generally applied by foliar spray, at a max. rate of 300 g/ha, against Ascomycetes, Basidiomycetes and Fungi Imperfecti including Alternaria, Fusarium, black and yellow Sigatoka, and Pseudocercosporella spp. in cereals, fruit, vines, vegetables, tropical crops, turf and ornamentals.

Fungicide; For use on cereals, fruit, tropical crops, vegetables, vines, turf, ornamentals.

Methods of Manufacturing · 2 件

A. Greiner, R. Pepin, European Patent Office patent 258,161(1988 to Rhone-Poulenc)

Produced by reaction of 1-bromomethoxyacetylene in toluene with ethylmagnesium bromide in THF, followed by the addition of 2,4-dichlorobenzoylmethyl chloride to give 2,4-dichlorophenyl-2'-chloromethyl-2'-hydroxy-2'-bromomethoxyacetylene. The product is then hydrogenated and treated with 4-methylphenylsulfonic acid in toluene to give 2-chloromethyl-2-(2,4-dichlorophenyl)-2,5-dihydrofuran, which is treated with 1,2,4-triazole in N-methylpyrrolidone in the presence of potassium carbonate

Formulations/Preparations · 3 件

Emulsifiable concentrate, granule, suspension concentrate.

Technical is > or =96% pure.

Trade names: Granit, Vectra (Rhone-Poulenc)

Use ClassificationEnvironmental transformation -> Pesticides (parent, predecessor)

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
116255-48-2
PubChem CID
3444
DTXSID
DTXSID9032531
ChEMBL
CHEMBL271579
ChEBI
CHEBI:81900
UNII
PHS29ZMZ81
EC Number
408-060-3、601-417-6
Nikkaji
J705.362B
Decomposition · 2 件

When heated to decomposition it emits toxic vapors of /nitrogen oxides, hydrogen bromide, and hydrogen chloride/.

The substance decomposes on burning producing toxic gases/fumes including nitrogen oxides, hydrogen chloride, hydrogen bromide, carbon monoxide.

Melting Point · 2 件

84 °C

84 °C

Vapor Pressure · 2 件

3X10-8 mm Hg at 25 °C

Vapor pressure at 25 °C: negligible

Henry's Law ConstantHenry's Law constant = 8.2X10-11 atm-cu m/mole at 25 °C

物理化学的性質

融点
84 ℃ · 84℃
沸点
504.3 · 504.3±60.0 °C(Predicted)
比重(密度)
1.71 · 1.71
蒸気圧
50 mg · 50 mg 1-1
屈折率
1.611 · 1.6110 (estimate)
貯蔵温度
-20 °C · -20°C
溶解性
Chloroform (Slightly), Methanol (Slightly)
酸解離定数(Pka)
2.75 · 2.75±0.10(Predicted)
BRN
8393967 · 8393967
Henry's Law Constant
3.3 · 3.3×104 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
主な用途
農業環境
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
InChIKey
HJJVPARKXDDIQD-UHFFFAOYSA-N
SMILES
Clc1ccc(c(Cl)c1)C2(CC(Br)CO2)Cn3cncn3
LogP
3.24 · 3.240
EPAの化学物質情報
Bromuconazole (116255-48-2)
Fire Fighting
In case of fire in the surroundings, use appropriate extinguishing media.
First Aid Measures · 4 件

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

Safe StorageSeparated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Fire Fighting ProceduresIn case of fire in the surroundings: all extinguishing agents allowed.
Storage ConditionsProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed.
Cleanup MethodsDo NOT wash away into sewer. Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place.
Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 件

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Eye PreventionWear safety spectacles.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached when dispersed.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT DISPERSION OF DUST!

毒性情報

Ecotoxicity Values · 5 件

LD50 Anas platyrhynchos (Mallard duck) oral >2150 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

LC50 Anas platyrhynchos (Mallard duck) diet >5000 ppm/8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

LC50 Colinus virginianus (Bobwhtie quail) diet >5000 ppm/8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

LD50 Colinus virginianus (Bobwhite quail) oral >2150 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

For more Ecotoxicity Values (Complete) data for BROMUCONAZOLE (14 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1380(SRC), determined from a log Kow of 3.24(2) and a regression-derived equation(3), indicates that bromomuconazole is expected to have low mobility in soil(SRC). Volatilization of bromomuconazole from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 8.2X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 3X10-8 mm Hg(2), and water solubility, 50 mg/L(2). Bromomuconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation data were not available (SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1380(SRC), determined from a log Kow of 3.24(2) and a regression-derived equation(3), indicates that bromomuconazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) to be an important fate process(SRC) given a Henry's Law constant of 8.2X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 3X10-8 mm Hg(2), and water solubility, 50 mg/L(2). According to a classification scheme(4), an estimated BCF of 62(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegrdation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromomuconazole, which has a vapor pressure of 3X10-8 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bromomuconazole may be removed from the air by wet and dry deposition(SRC). Under simulated sunlight degradation of bromuconazole is pH dependent. Bromuconazole had a reported half-life of 18 days under acidic conditions(2).

Exposure RoutesThe substance can be absorbed into the body by inhalation of dust and by ingestion.
ICSC Environmental DataThe substance is very toxic to aquatic organisms. Avoid release to the environment in circumstances different to normal use.
Soil Adsorption/Mobility · 1 件

The Koc of bromomuconazole is estimated as 1380(SRC), using a log Kow of 3.24(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bromomuconazole is expected to have low mobility in soil.

Artificial Pollution SourcesBromomuconazole's production may result in its release to the environment through various waste streams; its use as an agricultural fungicide(1) will result in its direct release to the environment(SRC).
Environmental Bioconcentration · 1 件

An estimated BCF of 62 was calculated for bromomuconazole(SRC), using a log Kow of 3.24(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for bromomuconazole is estimated as 8.2X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 3X10-8 mm Hg(1), and water solubility, 50 mg/L (1). This Henry's Law constant indicates that bromomuconazole is expected to be essentially nonvolatile from moist soil and water surfaces(2). Bromomuconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Non-Human Toxicity Excerpts · 5 件

/LABORATORY ANIMALS: Acute Exposure/ Non-irritating to eyes and skin of rabbits. Non-sensitising to skin of guinea pigs.[Tomlin CDS, ed. Bromuconazole (116255-48-2). In: The e-Pesticide Manual, 13th Edition Version 3.2 (2005-06). Surrey UK, British Crop Protection Council.]

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Rats /were administered/ 0, 40, 200, 1000, or 5000 ppm via the diet /for thirteen weeks/. NOAEL: 200 ppm (M: 13.8 mg/kg/day; F: 15.1 mg/kg/day) LOAEL: 1000 ppm (M: 68.1 mg/kg/day; F: 74.5 mg/kg/day) based on decreased body weight gains in females, changes in hematology/blood chemistry parameters and in the incidence of microscopic lesions consistent with liver toxicity, and increased liver weight gain in both sexes.[USEPA/Office of Prevention Pesticides and Toxic Substances; Pesticide Fact Sheet on Bromuconazole. Available from, as of July 13, 2006: http://www.epa.gov/opprd001/factsheets/bromuconazole.pdf]

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Rats were dosed at 20, 150, 1000, 2000 ppm in the diet; NOAEL: 20 ppm (0.88 mg/kg/day); LOAEL: 150 ppm (6.48 mg/kg/day) based on non-neoplastic lesions; Not oncogenic under the conditions of the study.[USEPA/Office of Prevention Pesticides and Toxic Substances; Pesticide Fact Sheet on Bromuconazole. Available from, as of July 13, 2006: http://www.epa.gov/opprd001/factsheets/bromuconazole.pdf]

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Mice were dosed at 0, 100, 1000, and 3000 ppm in the diet. NOAEL 100 ppm (M:12.3 mg/kg/day; F: 10.9 mg/kg/day); LOAEL 1000 ppm (F:134.5 mg/kg/day) based on decreased body weight gains.[USEPA/Office of Prevention Pesticides and Toxic Substances; Pesticide Fact Sheet on Bromuconazole. Available from, as of July 13, 2006: http://www.epa.gov/opprd001/factsheets/bromuconazole.pdf]

For more Non-Human Toxicity Excerpts (Complete) data for BROMUCONAZOLE (13 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 件

Bromomuconazole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Bromuconazole is susceptible to photolysis(SRC). This reaction is enhanced under acidic conditions; a photolysis half-life for bromomuconazole of 18 days under acidic conditions has been reported(2).

Probable Routes of Human ExposureOccupational exposure to bromomuconazole may occur through dermal contact with this compound at workplaces where bromomuconazole is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 件

Bromomuconazole's production may result in its release to the environment through various waste streams; its use as an agricultural fungicide will result in its direct release to the environment. If released to air, a vapor pressure of 3X10-8 mm Hg at 25 °C indicates bromomuconazole will exist solely in the particulate phase in the atmosphere. Particulate-phase bromomuconazole will be removed from the atmosphere by wet and dry deposition. Bromuconazole is susceptible to pH dependent photolysis. A photolysis half-life of 18 days has been reported for bromuconazole under acidic conditions. If released to soil, bromomuconazole is expected to have low mobility based upon an estimated Koc of 1380. Volatilization from water and moist soil surfaces is not expected to be an important fate process based upon a Henry's Law constant of 8.2X10-11 atm-cu m/mole. Bromomuconazole is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, bromomuconazole is expected to adsorb to suspended solids and sediment based upon the estimated Koc. An estimated BCF of 62 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to bromomuconazole may occur through dermal contact with this compound at workplaces where bromomuconazole is produced or used. (SRC)

安全データ

wgk
3
rtecs
XZ4130000
ridadr
UN 3077 9 / PGIII
毒性
LD50 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)
risk_code
22
hazard_code
Xn
safety_code
36
hazard_class
6.1
packing_group
III
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2
ストレージクラス
11 - Combustible Solids
有毒物質データの
116255-48-2(Hazardous Substances Data)

応用分野

使用Bromuconazole is used on winter wheat and barley for the control of foliar mildews, rusts and other diseases.

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補足説明 · 1 件

定義ChEBI: 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.