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Bromuconazole

Bromuconazole structure

Bromuconazole 

structure
  • CAS No:

    116255-48-2

  • Formula:

    C13H12BrCl2N3O

  • Chemical Name:

    Bromuconazole

  • Synonyms:

    Pentitol,2,5-anhydro-4-bromo-1,3,4-trideoxy-2-C-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-;2,5-Anhydro-4-bromo-1,3,4-trideoxy-2-C-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)pentitol;LS 860263;Bromuconazole;Granit (pesticide);Vectra;Granit;1H-1,2,4-Triazole,1-[[4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl]methyl]-;188992-37-2

  • Categories:

    Agrochemicals  >  Fungicides

Description

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.


COLOURLESS CRYSTALS OR WHITE POWDER.


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, an organobromine compound, a member of oxolanes, a member of triazoles, a conazole fungicide and a triazole fungicide.

Bromuconazole Basic Attributes

377.06

377.06

408-060-3

PHS29ZMZ81

1264

3077

DTXSID9032531

Colorless powder|White to off-white powder

Characteristics

39.9

3.12/3.48

1.7 g/cm3

84 °C

504.3±60.0 °C(Predicted)

258.8ºC

1.6110 (estimate)

Solubility in water, g/100ml: 0.05

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed.

Vapour pressure at 25°C: negligible

Oral-rat LD50: 365 mg/kg; Oral-Mouse LD50: 1151 mg/kg

Thermal decomposition emits toxic nitrogen oxide, bromide and chloride fumes

Odorless

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

168.75 Ų [M+H]+

Hydroxyl radical reaction rate constant = 8.7X10-12 cu cm/molecule-sec at 25 °C (est)

Safety Information

UN 3077 9 / PGIII

3

22

36

XZ4130000

Xn

The warehouse is ventilated, dry and low temperature; stored separately from food materials

In water, stable in the dark at acidic, basic or neutral pH values. Under simulated sunlight, degradation is pH-dependent: bromuconazole is degraded especially in acidic conditions, DT50 18 days.

P273

H302-H400

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.

Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, and P501|Aggregated GHS information provided by 228 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

In case of fire in the surroundings: all extinguishing agents allowed.

Do 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.

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.

Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached when dispersed.

The substance may have effects on the liver. This may result in impaired functions. Animal tests show that this substance possibly causes toxicity to human reproduction or development.

PREVENT DISPERSION OF DUST!

Avoid inhalation of dust and mist. Use local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

Toxicity

highly toxic

LD50 Rat oral 365 mg/kg|LD50 Rat dermal >2000 mg/kg|LD50 Mouse oral 1151 mg/kg|LC50 Rabbit inhalation >5 mg/L/4 hr|LC50 Rat inhalation >5 mg/L air/4 hr

Bromomuconazole'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).

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).

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).

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).

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.

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).

Occupational exposure to bromomuconazole may occur through dermal contact with this compound at workplaces where bromomuconazole is produced or used. (SRC)

Drug Information

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.

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.

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

bromuconazole

The substance can be absorbed into the body by inhalation of dust and by ingestion.

Bromuconazole Use and Manufacturing

Methods of Manufacturing

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

Uses

Agricultural fungicide.

Emulsifiable concentrate, granule, suspension concentrate.|Technical is > or =96% pure.|Trade names: Granit, Vectra (Rhone-Poulenc)

Agrochemicals -> Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Bromuconazole has known environmental transformation products that include LS 860551, LS-870353, LS802050, LS860976, LS861590, MWt 257, and RPA 401527.

Computed Properties

Molecular Weight:377.1
XLogP3:3.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:374.95408
Monoisotopic Mass:374.95408
Topological Polar Surface Area:39.9
Heavy Atom Count:20
Complexity:352
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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