General Description
Light gray or beige powder.
Reactivity Profile
CARBENDAZIM(10605-21-7) 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.
Air & Water Reactions
Insoluble in water. This compound slowly decomposes in alkaline solution. .
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of NOx.
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.
Fire Hazard
Literature sources indicate that this chemical is probably nonflammable.
First aid
Speed in removing material from eyes and skin
is of extreme importance. Eyes: Eye contact can cause dangerous amounts of these chemicals to be quickly absorbed
through the mucous membrane into the bloodstream.
Immediately and gently flush eyes with plenty of warm or
cold water (NO hot water) for at least 15 minutes, occasionally lifting the upper and lower eye lids. Get medical
aid immediately. Skin: Get medical aid. Dermal contact can
cause dangerous amounts of these chemicals to be absorbed
into the bloodstream. Wearing the appropriate PPE equipment and respirator for carbamate pesticides, immediately
flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Shampoo hair promptly if contaminated; protect eyes.
Ingestion: Call poison control. Loosen all clothing. Never
give anything by mouth to an unconscious person. Get
medical aid. Do NOT induce vomiting. If conscious,
alert, and able to swallow, rinse mouth and have victim
drink 4 to 8 oz of water. Check to see if poison control
instructs you to use ipecac syrup, otherwise administer
slurry of activated charcoal (2 oz in 8 oz of water). If victim is UNCONSCIO United States OR HAVING
CONVULSIONS, do nothing except keep victim warm. In
some cases you may be specifically instructed by poison
control to induce vomiting by way of 2 tablespoons of syrupof ipecac (adult) washed down with a cup of water. Do NOT
give activated charcoal before or with ipecac syrup.
Inhalation: Get medical aid. Do not contaminate yourself.
Wearing the appropriate PPE equipment and respirator for
carbamate pesticides, immediately remove the victim from
the contaminated area to fresh air. If the victim is not breathing, administer artificial respiration. Do not use mouth-tomouth method if victim ingested or inhaled the substance;
give artificial respiration with the aid of a pocket mask
equipped with a one-way valve or other proper respiratory
medical device. If breathing is difficult, administer oxygen
through bag/mask apparatus until medical help arrives. Do
not leave victim unattended.
Shipping
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
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.
Description
Carbendazim is the degradation product and active ingredient of the carbamate fungicide benomyl.
1,2 Carbendazim (100 μM) disrupts the growth of
S. cerevisiae by inhibiting microtubule polymerization.
1 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.
3,4
Chemical Properties
Colorless crystalline solid or light-gray powder. Commercially supplied as dry concentrate that is
mixed with water for spraying.
Chemical Properties
White Solid
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.
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.
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.
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.
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).
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
