Carbendazim

Carbendazim Basic information
Product Name:Carbendazim
Synonyms:1h-benzimidazol-2-ylcarbamicacidmethylester;1h-benzimidazol-2-yl-carbamicacimethylester;2-(Methoxycarbonylamino)benzimidazde;2-(methoxy-carbonylamino)-benzimidazol;(CARBENDAZIM 50%);a118;agrizim;1h-benzimidazole-2-carbamic acid methyl ester
CAS:10605-21-7
MF:C9H9N3O2
MW:191.19
EINECS:234-232-0
Product Categories:Amines;Heterocycles;2000/60/EC;CA - CGMethod Specific;Intermediates & Fine Chemicals;Pharmaceuticals;BenzimidazolesPesticides&Metabolites;CarbamatesEPA;Method 631Method Specific;2000/60/ECMore...Close...;600 Series Wastewater Methods;Alpha sort;C;CA - CGPesticides;BENZIMIDAZOLE;Organics;FUNGICIDE;CAlphabetic;European Community: ISO and DIN;Fungicides;Pesticides;BenzimidazolesAlphabetic;pharmaceutical intermediates;1
Mol File:10605-21-7.mol
Carbendazim Structure
Carbendazim Chemical Properties
Melting point >300 °C (lit.)
Boiling point 326.92°C (rough estimate)
density 1.4500
vapor pressure 1.5 x 10-4 Pa (25 °C)
refractive index 1.6500 (estimate)
Fp 11 °C
storage temp. -20°C
solubility pyridine: soluble1%, clear, very faintly brownish-yellow
form neat
pka4.48(at 25℃)
Water Solubility <0.1 g/100 mL at 21 ºC
Merck 13,1799
BRN 649044
InChIKeyTWFZGCMQGLPBSX-UHFFFAOYSA-N
LogP1.4-1.5 at 25℃ and pH5-9
CAS DataBase Reference10605-21-7(CAS DataBase Reference)
EPA Substance Registry SystemCarbendazim (10605-21-7)
Safety Information
Hazard Codes T,N,F,Xn
Risk Statements 46-60-61-50/53-39/23/24/25-23/24/25-11-52/53
Safety Statements 53-45-60-61-36/37-16
RIDADR UN 3077 9/PG 3
WGK Germany 3
RTECS DD6500000
HS Code 29339900
Hazardous Substances Data10605-21-7(Hazardous Substances Data)
ToxicityLD50 oral in rabbit: 8160mg/kg
MSDS Information
Carbendazim Usage And Synthesis
DescriptionCarbendazim 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 PropertiesColorless crystalline solid or light-gray powder. Commercially supplied as dry concentrate that is mixed with water for spraying.
UsesCarbendazim 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.
DefinitionChEBI: 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 DescriptionLight gray or beige powder.
Air & Water ReactionsInsoluble in water. Carbendazim slowly decomposes in alkaline solution. .
Reactivity ProfileCarbendazim 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 HazardACUTE/CHRONIC HAZARDS: When heated to decomposition Carbendazim emits toxic fumes of NOx.
Fire HazardLiterature sources indicate that Carbendazim is probably nonflammable.
Agricultural UsesFungicide: 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 nameABACOL®; 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 ActionsB-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 ProfileModerately 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 ExposureCarbendazim 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 pathwayWhen 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.
ShippingUN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
DegradationCarbendazim (MBC, 1) was stable in acidic and neutral solutions (pH 5-7, DT50≥57 days at 22°C), but decomposed rapidly with a DT50 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).
IncompatibilitiesCarbamates 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 DisposalDo 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.
Albendazole Methyl Alkyl benzimidazole Methyl 2-(methylamino)benzoate Benzimidazole Lithium bis(trimethylsilyl)amide Methyl carbamate Tribenuron methyl Carbendazim Kresoxim-methyl Thiophanate-methyl Pirimiphos-methyl 5-Amino-1,3-dihydro-2H-benzimidazol-2-one CARBAMIC ACID Methyl salicylate Methyl acrylate Methyl formate Phenyl carbamate

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