<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2009-06-17 23:53:01 UTC</creation_date>
  <update_date>2026-05-14 19:28:38 UTC</update_date>
  <accession>T3D0942</accession>
  <common_name>Carbendazim</common_name>
  <class>SmallMolecule</class>
  <description>Carbendazim belongs to the 2-benzimidazolylcarbamic acid esters, a subclass of benzimidazoles within the organic compounds. This exogenous solid has the formula C9H9N3O2 and an average molecular weight of 191.19 g/mol. It is classified as an organoheterocyclic compound.

Carbendazim serves several roles, acting as a fungicide (PMC10979413, PMC11200900, PMC12467741), an agrochemical, and an antinematodal drug. Industrially, it is utilized as a biocide, a preservative, and as processing aids not otherwise specified. It also functions as a pesticide (PMC12452724, PMC10465560, PMC11769159). In the materials sector, it is used in polyvinyl chloride plastics.

The compound is released from 41 recorded sources across multiple sectors. These include agriculture and land management via pesticides; drinking water and water supply; household cleaning and consumer products such as soap dispensers, bleaching agents, tobacco pipes, cigar cigarettes, and tobacco smoke filters; building and construction materials including roofs, ceilings, floors, ladders, and sunshades awnings or outside screens; and electrical and electronic equipment including communication cables or conductors, antennas, coils, contacts, and electric hearing aids. It is also found in food, food processing, and cookware, specifically in food contact materials, fermentation processes for beer, molasses and treatment of molasses, and the preparation of malt, wine, or sparkling wine. Exposure occurs through oral, inhalation, and touch routes.

Biologically, carbendazim targets the tubulin beta chain (TUBB), the aryl hydrocarbon receptor (AHR), and acts as an agonist of cellular tumor antigen p53 (TP53). Health effects associated with the compound include infertility (PMC12467741).</description>
  <categories>
    <category>Pesticide</category>
    <category>Food Toxin</category>
    <category>Synthetic Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Pesticide</type>
    <type>Ether</type>
    <type>Carbamate</type>
    <type>Food Toxin</type>
    <type>Metabolite</type>
    <type>Lachrymator</type>
    <type>Synthetic Compound</type>
  </types>
  <synonyms>
    <synonym>1H-Benzimidazol-2-yl-carbamic acid, methyl ester</synonym>
    <synonym>1H-Benzimidazol-2-ylcarbamic acid methyl ester</synonym>
    <synonym>1H-Benzimidazol-2-ylcarbamic acid, methyl ester</synonym>
    <synonym>1H-Benzimidazole-2-carbamic acid, methyl ester</synonym>
    <synonym>2-(Carbomethoxyamino)benzimidazole</synonym>
    <synonym>2-(Methoxy-carbonylamino)-benzimidazol</synonym>
    <synonym>2-(Methoxycarbamoyl)benzimidazole</synonym>
    <synonym>2-(Methoxycarbonylamino)-benzimidazole</synonym>
    <synonym>2-(Methoxycarbonylamino)benzimidazole</synonym>
    <synonym>2-(Methoxycarboxamido)benzimidazole</synonym>
    <synonym>2-Benzimidazolecarbamic acid, methyl ester</synonym>
    <synonym>2-Bezimidazolecarbamic acid methyl ester</synonym>
    <synonym>2-MBC</synonym>
    <synonym>2-Methyl benzimidazolecarbamate</synonym>
    <synonym>2-[(Methoxycarbonyl)amino]benzimidazole</synonym>
    <synonym>A 118 (Pesticide)</synonym>
    <synonym>Agrizim</synonym>
    <synonym>Antibac MF</synonym>
    <synonym>Battal</synonym>
    <synonym>Bavistan</synonym>
    <synonym>Bavistin</synonym>
    <synonym>Bavistin 25SD</synonym>
    <synonym>Bavistin 3460</synonym>
    <synonym>Bavistin 50SD</synonym>
    <synonym>Bavistin FL</synonym>
    <synonym>Bavistine</synonym>
    <synonym>BCM</synonym>
    <synonym>BCM (fungicide)</synonym>
    <synonym>Bengard</synonym>
    <synonym>Benzimidazole carbamate de methyle</synonym>
    <synonym>Benzimidazole-2-carbamic acid, methyl ester</synonym>
    <synonym>Benzimidazolecarbamate methyl ester</synonym>
    <synonym>Benzimidazolecarbamic</synonym>
    <synonym>Bercema-bitosen</synonym>
    <synonym>Bitosen</synonym>
    <synonym>BMC</synonym>
    <synonym>BMC?</synonym>
    <synonym>BMK</synonym>
    <synonym>BMK (fungicide)</synonym>
    <synonym>Carbamic acid, 1H-benzimidazol-2-yl-, methyl ester</synonym>
    <synonym>Carbamic acid, 1H-benzimidazolyl-, methyl ester</synonym>
    <synonym>Carbamic acid, N-1H-benzimidazol-2-yl-, methyl ester</synonym>
    <synonym>Carben VL</synonym>
    <synonym>Carbendazime</synonym>
    <synonym>Carbendazin</synonym>
    <synonym>Carbendazine</synonym>
    <synonym>Carbendazol</synonym>
    <synonym>Carbendazol, JMAF</synonym>
    <synonym>Carbendazole</synonym>
    <synonym>Carbendazym</synonym>
    <synonym>Carbendazyme</synonym>
    <synonym>Custos</synonym>
    <synonym>Delsene</synonym>
    <synonym>Delsene 10</synonym>
    <synonym>Derosal</synonym>
    <synonym>Derosal 60PM</synonym>
    <synonym>Equitdazin</synonym>
    <synonym>Falicarben</synonym>
    <synonym>Funaben</synonym>
    <synonym>Funaben 3</synonym>
    <synonym>Funaben 50</synonym>
    <synonym>Fungisol</synonym>
    <synonym>Fungoxan</synonym>
    <synonym>Garbenda</synonym>
    <synonym>Ipo y</synonym>
    <synonym>Jkatein</synonym>
    <synonym>Jkstein</synonym>
    <synonym>Karben</synonym>
    <synonym>Karben flo stefes</synonym>
    <synonym>Karben stefes flo</synonym>
    <synonym>Kemdazin</synonym>
    <synonym>Kid pest project (carbendazim) (see also carbendazim)</synonym>
    <synonym>Kolfugo</synonym>
    <synonym>Kolfugo 25 FW</synonym>
    <synonym>Kolfugo 25FW</synonym>
    <synonym>Kolfugo extra</synonym>
    <synonym>MBC</synonym>
    <synonym>Mecarzole</synonym>
    <synonym>Medamine</synonym>
    <synonym>Mekarzole</synonym>
    <synonym>Methoxybenzimidazole-2-carbamic acid</synonym>
    <synonym>Methyl 1H-benzimidazol-2-ylcarbamate</synonym>
    <synonym>Methyl 1H-benzimidazol-2-ylcarbamate (9CI)</synonym>
    <synonym>Methyl 1H-benzimidazol-2-ylcarbamate, 9CI</synonym>
    <synonym>Methyl 1H-benzimidazole-2-carbamate</synonym>
    <synonym>Methyl 1H-benzimidazolylcarbamate</synonym>
    <synonym>Methyl 2-benzimidazil carbamate</synonym>
    <synonym>Methyl 2-benzimidazolecarbamate</synonym>
    <synonym>Methyl 2-benzimidazolylcarbamate</synonym>
    <synonym>Methyl benzimidazol-2-ylcarbamate</synonym>
    <synonym>Methyl benzimidazolecarbamate</synonym>
    <synonym>Methyl benzimidazolylcarbamate</synonym>
    <synonym>methyl N-(1H-1,3-benzodiazol-2-yl)carbamate</synonym>
    <synonym>Methyl N-2-benzimidazolecarbamate</synonym>
    <synonym>Methyl-2-benzimidazole carbamate</synonym>
    <synonym>Methyl-N-(2-benzimidazolyl)carbamate</synonym>
    <synonym>Methylbenzimidazole-2-ylcarbamate</synonym>
    <synonym>MYCO</synonym>
    <synonym>Olgin</synonym>
    <synonym>Olgin (fungicide)</synonym>
    <synonym>Pillarstin</synonym>
    <synonym>Preparation G 665</synonym>
    <synonym>Preventol BCM</synonym>
    <synonym>Protek</synonym>
    <synonym>Sarfun</synonym>
    <synonym>SPIN</synonym>
    <synonym>Spin (pesticide)</synonym>
    <synonym>Stein</synonym>
    <synonym>Stempor</synonym>
    <synonym>Subeej</synonym>
    <synonym>Supercarb</synonym>
    <synonym>Thicoper</synonym>
    <synonym>Triticol</synonym>
    <synonym>Zhiweiling</synonym>
  </synonyms>
  <chemical_formula>C9H9N3O2</chemical_formula>
  <average_molecular_weight>191.1867</average_molecular_weight>
  <monisotopic_moleculate_weight>191.069476547</monisotopic_moleculate_weight>
  <iupac_name>methyl N-(1H-1,3-benzodiazol-2-yl)carbamate</iupac_name>
  <traditional_iupac>carbendazim</traditional_iupac>
  <cas_registry_number>10605-21-7</cas_registry_number>
  <smiles>COC(=O)NC1=NC2=CC=CC=C2N1</smiles>
  <inchi>InChI=1S/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13)</inchi>
  <inchikey>TWFZGCMQGLPBSX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzimidazoles</class>
    <sub_class>2-benzimidazolylcarbamic acid esters</sub_class>
    <direct_parent>2-benzimidazolylcarbamic acid esters</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbamate esters</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organic carbonic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-benzimidazolylcarbamic acid ester</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbamic acid ester</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Carbamate fungicides</descriptor>
      <descriptor>benzimidazole fungicide</descriptor>
      <descriptor>benzimidazoles</descriptor>
      <descriptor>benzimidazolylcarbamate fungicide</descriptor>
      <descriptor>carbamate ester</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Extracellular</cellular_location>
    <cellular_location>Membrane</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>302 - 307°C</value>
    </property>
    <property>
      <kind>solubility</kind>
      <value>0.029 mg/mL at 24°C [TOMLIN,C (1994); pH4]</value>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.52</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.25e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl N-(1H-1,3-benzodiazol-2-yl)carbamate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>191.1867</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>191.069476547</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC(=O)NC1=NC2=CC=CC=C2N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9N3O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TWFZGCMQGLPBSX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>67.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure>Inhalation  (L793) ; oral (L793); dermal (L793)</route_of_exposure>
  <mechanism_of_toxicity>Carbendazim targets beta tubulin in actively dividing cells. It binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation (A15332).

Acute oral LD50 for rats is &gt;15000 mg/kg and &gt;2500 mg/kg for dogs</mechanism_of_toxicity>
  <metabolism>The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)</metabolism>
  <toxicity>Acute oral LD50 for rats is &gt;15000 mg/kg and &gt;2500 mg/kg for dogs</toxicity>
  <lethaldose/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use_source>It is a systemic fungicide that is selectively toxic to microorganisms and invertebrates. It is also employed as a casting worm control agent in amenity turf situations such as golf greens and tennis courts. It is also used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, pineapples, and pomes.</use_source>
  <min_risk_level>The MRLs for fresh produce in the European Union are now between 0.1 and 0.7 mg/kg</min_risk_level>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7223254f80&gt;</health_effects>
  <symptoms>Skin redness and skin irritation.  Fetuses exposed to high levels may exhibit microphthalmia (small eyes) or anaphthalmia (no eyes).&#13;
</symptoms>
  <treatment>For acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.</treatment>
  <drugbank_id>DB13009</drugbank_id>
  <hmdb_id>HMDB31769</hmdb_id>
  <pubchem_compound_id>25429</pubchem_compound_id>
  <chembl_id>CHEMBL70971</chembl_id>
  <chemspider_id>23741</chemspider_id>
  <kegg_id>C10897</kegg_id>
  <uniprot_id/>
  <omim_id/>
  <chebi_id>3392</chebi_id>
  <biocyc_id/>
  <ctd_id>C006698</ctd_id>
  <stitch_id>Carbendazim</stitch_id>
  <actor_id>5785</actor_id>
  <pdb_id/>
  <wikipidia/>
  <general_references>
    <reference>
      <pubmed_id>18062653</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>19049291</pubmed_id>
    </reference>
    <reference>
      <reference_text>Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman &amp; Hall/CRC.</reference_text>
    </reference>
    <reference>
      <reference_text>IPCS Intox Database (1987). Antimony pentoxide. : http://www.intox.org/databank/documents/chemical/antpenta/ukpid36.htm</reference_text>
    </reference>
    <reference>
      <reference_text>Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088</reference_text>
    </reference>
  </general_references>
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      <references/>
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          <constant_type>AC50</constant_type>
          <value>7.36</value>
          <units>uM</units>
          <assay_type>APR_p53Act_72h_up</assay_type>
          <assay_source>Apredica</assay_source>
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</compound>
