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)

Flash point:

11 °C

storage temp. 

-20°C

solubility 

pyridine: soluble1%, clear, very faintly brownish-yellow

pka

4.48(at 25℃)

form 

Solid

color 

White to off-white

biological source

human

Water Solubility 

<0.1 g/100 mL at 21 ºC

Merck 

13,1799

BRN 

649044

InChIKey

TWFZGCMQGLPBSX-UHFFFAOYSA-N

LogP

1.4-1.5 at 25℃ and pH5-9

CAS DataBase Reference

10605-21-7(CAS DataBase Reference)

EPA Substance Registry System

Carbendazim (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 Data

10605-21-7(Hazardous Substances Data)

Toxicity

LD50 oral in rabbit: 8160mg/kg

MSDS

• Language:English Provider:1H-Benzimidazole-2-carbamic acid methyl ester
• Language:English Provider:SigmaAldrich

Carbendazim Usage And Synthesis

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, 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).

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.

References

[1] JEAN P. ROUCHAUD. Metabolism of benomyl in carrot, strawberry and apple[J]. Pest Management Science, 1977, 8 1: 23-30. DOI: 10.1002/ps.2780080104
[2] HAN SOL LEE . An effective methodology for simultaneous quantification of thiophanate-methyl, and its metabolite carbendazim in pear, using LC-MS/MS[J]. Journal of Chromatography B, 2018, 1095: Pages 1-7. DOI: 10.1016/j.jchromb.2018.07.010
[3] MIKIO CHIBA  Darrell F V. Fate of benomyl and its degradation compound methyl 2-benzimidazolecarbamate on apple foliage[J]. Journal of Agricultural and Food Chemistry, 1981, 29 3: 588-590. DOI: 10.1021/jf00105a038
[4] NICHOLAS T AMPONSAH. Evaluation of fungicides for the management of Botryosphaeria dieback diseases of grapevines[J]. Pest Management Science, 2012, 68 5: 676-683. DOI: 10.1002/ps.2309
[5] R A QUINLAN  K G  C I Pogson. The influence of the microtubule inhibitor, methyl benzimidazol-2-yl-carbamate (MBC) on nuclear division and the cell cycle in Saccharomyces cerevisiae.[J]. Journal of cell science, 1980, 46: 341-352. DOI: 10.1242/jcs.46.1.341
[6] CéDRIC PISANI. Ex vivo assessment of testicular toxicity induced by carbendazim and iprodione, alone or in a mixture.[J]. Altex-Alternatives To Animal Experimentation, 2016, 33 4: 393-413. DOI: 10.14573/altex.1601253
[7] ELKIANE MACEDO RAMA . Reproductive and possible hormonal effects of carbendazim[J]. Regulatory Toxicology and Pharmacology, 2014, 69 3: Pages 476-486. DOI: 10.1016/j.yrtph.2014.05.016
[8] YASSINE MAKNI . Optimisation and implementation of QuEChERS-based sample preparation for identification and semi-quantification of 694 targeted contaminants in honey, jam, jelly, and syrup by UHPLC-Q/ToF high-resolution mass spectrometry[J]. Food Chemistry, 2023, 425: Article 136448. DOI: 10.1016/j.foodchem.2023.136448

Carbendazim(10605-21-7)Related Product Information

• Methyl 2-(methylamino)benzoate
• Phenyl carbamate
• Methyl anthranilate
• Cyclamic acid
• Tribenuron methyl
• Lithium bis(trimethylsilyl)amide
• Kresoxim-methyl
• Benzimidazole
• Methyl formate
• Methyl acrylate
• 5-Amino-1,3-dihydro-2H-benzimidazol-2-one
• Methyl salicylate
• Methyl carbamate
• Pirimiphos-methyl
• Methyl 4-aminobenzoate
• Molasses
• Thiophanate-methyl
• METSULFURON METHYL