Description
Carbendazim is the degradation product and active ingredient of the carbamate fungicide benomyl. Carbendazim (100 μM) disrupts the growth of
S. cerevisiae by inhibiting microtubule polymerization. It impairs meiosis and steroidogenesis in an
ex vivo rat model of seminiferous tubules and increases prostate weight in rats when administered at a dose of 100 mg/kg but does not affect other testosterone-dependent or estrogen-dependent tissues.
Chemical Properties
Colorless crystalline solid or light-gray powder. Commercially supplied as dry concentrate that is
mixed with water for spraying.
Uses
Carbendazim is the most widely used active ingredient in the
benzimidazole class of fungicides. It is a systemic fungicide with both
protective and curative activities against a wide range of fungal diseases,
especially caused by most Ascomycetes spp. and some Basidiomycetes
and Deuteromycetes spp. in a wide variety of crop and ornamental uses.
Definition
ChEBI: A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomy
etes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.
General Description
Light gray or beige powder.
Air & Water Reactions
Insoluble in water. Carbendazim slowly decomposes in alkaline solution. .
Reactivity Profile
Carbendazim is a carbamate ester-amine. Amines behave as chemical bases. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition Carbendazim emits toxic fumes of NOx.
Fire Hazard
Literature sources indicate that Carbendazim is probably nonflammable.
Agricultural Uses
Fungicide: Carbendazim is a systemic fungicide used as a drench to control a broad range of fungi in cereals, vegetables, oilseed rape, sugar beets, grapes, tomatoes, pome fruit and stone fruit. It is also used in post-harvest storage and as treatment in seed pre-planting, frequently in combination with other fungicides. In some areas, it has been used to combat Dutch elm disease.
Trade name
ABACOL®; AIMCOZIM; BAS® 3460; BAS® 67054; BATTAL®; BAVISTIN®; BENDAZIM®; CARBATE®; CARBENDAZIME®; CARBENDAZOL®; CARBENDAZOLE®; CARBENDAZYM®; CARBENDOR; CEKUDAZIM®; CORBEL; CTR® 6669; CUSTOS®; DEFENSOR®; DELSENE®; DEROSAL®; E-965®; DERROPRENE®; EQUITDAZIN®; FUNGISOL®; HOE 17411®; LIGNASAN®; IMISOL®; KEMDAZIN®; MERGAL®; PILLARSTIN®; POLYPHASE®; RODAZIM®; STEMPOR®; SUPERCARB, TRITICOL®; TRITICOL®; U-32.104®
Biochem/physiol Actions
B-cell maturation antigen (BCMA) or tumor necrosis factor receptor superfamily member 17 (TNFRSF17) plays an important role in B cell development, function and regulation. BCMA also has the capability to activate nuclear factor-κB (NF-κB), janus kinase (JNK) and mitogen activated protein kinases (MAPKs). The protein is expressed in certain cancers like glioblastoma, chronic lymphocytic leukemia, Hodgkin lymphoma and multiple myeloma. It has a role in the maintenance of survival of long-lived plasma cells in bone marrow.
Safety Profile
Moderately toxic by
skin contact. Mildly toxic by ingestion. An
experimental teratogen. Experimental
reproductive effects. Human mutation data
reported. An agricultural chemical and
pesticide. When heated to decomposition it
emits toxic fumes of NOx. See also
CARBAMATES.
Potential Exposure
Carbendazim is a benzimidazole/carbamate systemic fungicide used as a drench to control a
broad range of fungi in cereals, vegetables, oilseed rape,
sugar beets, grapes, tomatoes, pome fruit, and stone fruit. It
is also used in postharvest storage and as treatment in seed
preplanting, frequently in combination with other fungicides. In some areas, it has been used to combat Dutch Elm
disease.
Metabolic pathway
When the mites are exposed to 14C-carbendazim, the
major carbendazim metabolite identified in the bulb
mites is 5-hydroxy-2-aminobenzimidazole. Low levels
of 2-aminobenzimidazole and 5-hydroxy-2-
benzimidazole carbamate are also identified.
Shipping
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
Degradation
Carbendazim (MBC, 1) was stable in acidic and neutral solutions (pH 5-7,
DT
50≥57 days at 22°C), but decomposed rapidly with a DT
50 of 22
days (WHO, 1993b) to yield 2-aminobenzimidazole (2, Watluns, 1976;
Zbozinek, 1984) under alkaline conditions (pH 9). An increase in the
salinity of the water accelerated the degradation rate of MBC in water
(Deshpande and Patil, 1987).
Photolysis of MBC in natural sunlight is not a significant dissipation
mechanism in the environment. Significant degradation did not occur
either on leaf surfaces exposed to natural sunlight or in unamended dilute
aqueous solution. Degradation occurred in solution under natural sunlight
if photoinitiators such as riboflavin or acetone were present (Fleeker
and Lacy, 1977).
Incompatibilities
Carbamates are incompatible with reducing agents, strong acids, oxidizing acids, peroxides, and
bases. Contact with active metals or nitrides cause the release
of flammable, and potentially explosive, hydrogen gas.
Waste Disposal
Do not discharge into drains
or sewers. Dispose of waste material as hazardous waste
using a licensed disposal contractor to an approved landfill.
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with
effluent gas scrubbing is recommended. Containers must be
disposed of properly by following package label directions
or by contacting your local or federal environmental control
agency, or by contacting your regional EPA office.
