ChemicalBook--->CAS DataBase List--->3878-19-1

3878-19-1

3878-19-1 Structure

3878-19-1 Structure
IdentificationMore
[Name]

FUBERIDAZOLE
[CAS]

3878-19-1
[Synonyms]

2-(2-FURANYL)-1H-BENZIMIDAZOLE
2-(2-FURYL)-1H-BENZOIMIDAZOLE
2-(2'-FURYL)BENZIMIDAZOLE
AKOS BC-1550
FUBERIDAZOL
FUBERIDAZOLE
VORONIT(R)
1H-Benzimidazole, 2-(2-furanyl)-
2-(2-furanyl)-1h-benzimidazol
2-(2-Furyl)-1H-benzimidazole
2-(2-furyl)-benzimidazol
B-33172
BAY 33172
bay33172
Bayer 33172
bayer33172
Benzimidazole, 2-(2-furyl)-
Fuberidatol
Fuberisazol
Fubridazole
[EINECS(EC#)]

223-404-0
[Molecular Formula]

C11H8N2O
[MDL Number]

MFCD00055496
[Molecular Weight]

184.19
[MOL File]

3878-19-1.mol
Chemical PropertiesBack Directory
[Appearance]

Fuberidazole is a crystalline powder.
[Melting point ]

310-312℃
[Boiling point ]

318.14°C (rough estimate)
[density ]

1.1820 (rough estimate)
[vapor pressure ]

<1 x 10-3Pa (20 °C)
[refractive index ]

1.5300 (estimate)
[storage temp. ]

0-6°C
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

neat
[pka]

4.6 (base)
[Water Solubility ]

200 mg l-1 (pH 4), 71 mg l-1 (pH 7) at 20 °C
[color ]

Off-White to Pale Beige
[BRN ]

153833
[Henry's Law Constant]

1.9×105 mol/(m3Pa) at 25℃, Ebert et al. (2023)
[Major Application]

agriculture
environmental
[InChI]

1S/C11H8N2O/c1-2-5-9-8(4-1)12-11(13-9)10-6-3-7-14-10/h1-7H,(H,12,13)
[InChIKey]

UYJUZNLFJAWNEZ-UHFFFAOYSA-N
[SMILES]

c1ccc2[nH]c(nc2c1)-c3ccco3
[LogP]

2.670
[CAS DataBase Reference]

3878-19-1(CAS DataBase Reference)
[EPA Substance Registry System]

Fuberidazole (3878-19-1)
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)Health Hazard (GHS08)Environment (GHS09)
GHS06,GHS08,GHS09
[Signal word ]

Danger
[Hazard statements ]

H302-H311-H317-H330-H351-H373-H410
[Precautionary statements ]

P201-P273-P280-P301+P312-P302+P352+P312-P304+P340+P310
[Hazard Codes ]

Xn,N
[Risk Statements ]

R22:Harmful if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
[Safety Statements ]

S22:Do not breathe dust .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
[RIDADR ]

2588
[WGK Germany ]

3
[RTECS ]

DD9010000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29339900
[Storage Class]

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
[Hazard Classifications]

Acute Tox. 2 Inhalation
Acute Tox. 3 Dermal
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Carc. 2 Inhalation
Skin Sens. 1
STOT RE 2
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium bisulfite-->o-Phenylenediamine-->Sodiumhydroxymethylenesulfonate-->1H-Benzimidazole, 2-(2-furanyl)-1-(2-furanylmethyl)--->Benzenamine, N-(2-furanylmethylene)--->alpha-Furfuryliden-alpha-furylmethylamine-->2-(Bromomethyl)furan-->2-Furaldehyde oxime-->1,2-Dinitrobenzene-->Furfuryl alcohol-->Furfurylamine-->2-Nitroaniline-->Furfural
Hazard InformationBack Directory
[General Description]

Crystalline powder. Used in cereal seed dressing and fungicidal non-mercurial seed dressing with special action against fusarium. Not registered as a pesticide in the U.S.
[Reactivity Profile]

FUBERIDAZOLE is a benzimidazole and behaves as an amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides
[Health Hazard]

FUBERIDAZOLE is classified as moderately toxic. Its probable oral lethal dose in humans is 0.5-5 g/kg or between 1 ounce and 1 pint for a150 lb. person.
[Potential Exposure]

Fuberidazole, a benzimidazole, uses include cereal seed dressing; and fungicidal, nonmercurial seed dressing with special action against fusarium. Not reg istered as a pesticide in the U.S.A.
[Fire Hazard]

When heated to decomposition, FUBERIDAZOLE emits toxic fumes of nitrogen oxides.
[First aid]

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respira tion with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with run ning water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
[Shipping]

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
[Description]

Fuberidazole is a crystalline powder.Molecular weight=184.21; Melting point=285℃(decomposition). Hazard Identification (based on NFPA-704 M Rating System): Health 2, Flammability 1,Reactivity 0. Very slightly soluble in water.
[Chemical Properties]

Fuberidazole is a crystalline powder.
[Waste Disposal]

In accordance with 40CFR 165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by follow ing package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
[Uses]

Fuberidazole is a benzimidazole based fungicide used as a fungicidal seed treatment of barley.
[Uses]

Fuberidazole is a systemic fungicide used in cereal seed dressing to control a variety of soil and seed borne diseases caused by Fusarium spp. It is also used as an anthelmintic and an inhibitor of enteroviruses.
[Definition]

ChEBI: A ring assembly consisting of benzimidazole substituted at position 2 by a 2-furyl group. A fungicide used as a seed treatment to control Fusarium spp. in cereals.
[Production Methods]

Fuberidazole is commercially produced through a two-step synthesis involving o-phenylenediamine and furfural. Production begins with the condensation of ortho-phenylenediamine and furfural in aqueous solution. This reaction is typically catalysed by sodium hydrogen sulphite and carried out under reflux conditions to promote cyclization and formation of the benzimidazole ring. The resulting product, 2-(furan-2-yl)-1H-benzimidazole, precipitates upon cooling and is collected by vacuum filtration. The crude solid is washed with water and dried under vacuum to yield high-purity fuberidazole.
[Agricultural Uses]

Fungicide, Seed treatment: Uses include cereal seed dressing; and fungicidal non-mercurial seed dressing with special action against fusarium. Not registered as a pesticide for use in the U.S. Registered for use in EU countries.
[Trade name]

BAYCOR®; BAYER 33172®; BAYTAN®; BAYTAN® FS; ICI BAYTAN®; NEOVORONIT®; SIBUTOL®; SIBUTROL®; VORONIT®; VORONITE®; W VII/117®
[Mechanism of action]

Systemic with specific action against Fusarium spp. Inhibition of mitosis and cell division (Beta-tubulin assembly in mitosis).
[Metabolic pathway]

Limited information is available describing the degradation and metabolic fate of fuberidazole. Information presented below was abstracted mainly from the Pesticide Manual (PM). The major degradation pathways observed include rearrangement of the fury1 moiety under UV light irradiation, hydrolysis and hydroxylation reactions in mammalian systems.
[storage]

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, wellventilated area.
[Degradation]

Fuberidazole (1) is stable to hydrolysis in pure water and sensitive to light with a half-life (DT50) of ca. 15 min (PM).
Photolysis (at 313 nm using a high pressure Hg lamp) of fuberidazole was much faster for the protonated state as compared to the neutral state (Melo et al., 1994), probably via a cyclopropanyl ketone intermediate (see Scheme 1). Reaction of this intermediate with either water or methanol yielded benzimidazole-2-carboxylic acid (2) or its methyl ester (3), methyl 4-oxo-4-(benzimidazol-2-yl)crotonate( 4, both the cis and trans isomers) and 1-methoxybenzimidazole (5) as major degradates (Melo et al., 1992). Benzimidazole (6) and 2,2'-bibenzimidazole (7) were also detected.
[Incompatibilities]

Incompatible with acid halides, anhydrides, epoxides, halogenated organics, isocyanates, peroxides, phenols (acidic).
[Pesticide Type]

Fungicide
Spectrum DetailBack Directory
[Spectrum Detail]

FUBERIDAZOLE(3878-19-1)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

3878-19-1(sigmaaldrich)
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