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.
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.
Uses
Fuberidazole is a benzimidazole based fungicide used as a fungicidal seed treatment of barley.
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.
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.
Fire Hazard
When heated to decomposition, FUBERIDAZOLE emits toxic fumes of nitrogen oxides.
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).
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.
First aid
: If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
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.
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.
Degradation
Fuberidazole (1) is stable to hydrolysis in pure water and sensitive to
light with a half-life (DT
50) 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).
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.
