Mecarbinzid (T3D0980)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-06-17 23:53:04 UTC
Update Date2014-12-24 20:23:00 UTC
Accession NumberT3D0980
Identification
Common NameMecarbinzid
ClassSmall Molecule
DescriptionMecarbinzid is a systemic benzimidazole fungicide that is selectively toxic to microorganisms and invertebrates, especially earthworms. It is not widely used anymore due to widespread fungal resistance. The in vitro antifungal activity of benzimidazole compounds was first observed in 1944. Some of the benzimidazole derivatives which have been exploited for commercial use as agricultural pesticides are carbendazim, benomyl, mecarbinzid, debacarb, fuberidazole, and rabenzazole. Of these, carbendazim, benomyl, debacarb and mecarbinzid are benzimidazole-2-carbamates. benzimidazol-2-yl carbamates like Mecarbinzid bind to microtubules, interfering with cell functions, such as meiosis and intracellular transportation. Due to the widespread use of these fungicidal agents and their specific action, resistance is common in many fungal species. For instance, strains of Botrytis which cause gray mold in ornamental crops are now largely resistant to methyl benzimidazole carbamate fungicides. Solubility problems of these compounds have contributed to their low bioavailability which has restricted their use in the treatment of fungal diseases in plants and have now lost effectiveness for many important diseases.
Compound Type
  • Carbamate
  • Ether
  • Lachrymator
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Caswell No. 075A
RCRA waste no. U271
Chemical FormulaC13H16N4O3S
Average Molecular Mass308.356 g/mol
Monoisotopic Mass308.094 g/mol
CAS Registry Number27386-64-7
IUPAC Name2-{[hydroxy(methoxy)methylidene]amino}-N-[2-(methylsulfanyl)ethyl]-1H-1,3-benzodiazole-1-carboximidic acid
Traditional Name2-{[hydroxy(methoxy)methylidene]amino}-N-[2-(methylsulfanyl)ethyl]-1,3-benzodiazole-1-carboximidic acid
SMILESCOC(O)=NC1=NC2=CC=CC=C2N1C(O)=NCCSC
InChI IdentifierInChI=1S/C13H16N4O3S/c1-20-13(19)16-11-15-9-5-3-4-6-10(9)17(11)12(18)14-7-8-21-2/h3-6H,7-8H2,1-2H3,(H,14,18)(H,15,16,19)
InChI KeyInChIKey=ZCAHBOURBFRXOT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • N-substituted imidazole
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Isourea
  • Carboximidic acid derivative
  • Azacycle
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP1.42ALOGPS
logP3.19ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)2.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.74 m³·mol⁻¹ChemAxon
Polarizability32.3 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052g-1983000000-0206c174767f47bca6d12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qc-1900000000-85af49e091533582a74b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-ee8f9ccc573b782fcc822016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052g-7920000000-ab13c6ca7d3dd3df130e2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6v-7890000000-e3b01249721c7e919ce22016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ai-2900000000-51620d48bc343059a8332016-08-04View Spectrum
Toxicity Profile
Route of ExposureInhalation (2) ; oral (2); dermal (2)
Mechanism of ToxicityMecarbinzid targets beta tubulin in actively dividing cells. It binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation (1).
MetabolismThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt 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.
Minimum Risk LevelThe MRLs for fresh produce in the European Union are between 0.1 and 0.7 mg/kg
Health EffectsMecarbinzid is a suspected endocrine disruptor. It is also a developmental toxin. Animals exposed to Mecarbinzid in the womb to have serious deformities such as lack of eyes and hydrocephalus (water on the brain). Mecarbinzid can disrupt the development of sperm and damage testicular development in adult rats.
SymptomsSkin redness and skin irritation. Fetuses exposed to high levels may exhibit microphthalmia (small eyes) or anaphthalmia (no eyes).
TreatmentFor 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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID20055210
ChEMBL IDNot Available
ChemSpider ID16736373
KEGG IDC18942
UniProt IDNot Available
OMIM ID
ChEBI ID82083
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMecarbinzid
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Clement MJ, Rathinasamy K, Adjadj E, Toma F, Curmi PA, Panda D: Benomyl and colchicine synergistically inhibit cell proliferation and mitosis: evidence of distinct binding sites for these agents in tubulin. Biochemistry. 2008 Dec 9;47(49):13016-25. doi: 10.1021/bi801136q. [19049291 ]
  2. IPCS Intox Database (1987). Antimony pentoxide. [Link]
  3. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Tubulin beta chain
General Function:
Ubiquitin protein ligase binding
Specific Function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name:
TUBB
Uniprot ID:
P07437
Molecular Weight:
49670.515 Da
References
  1. Fujimura M, Oeda K, Inoue H, Kato T. "A single amino-acid substitution in the beta-tubulin gene of Neurospora confers both carbendazim resistance and diethofencarb sensitivity.". Curr Genet. 1992 Apr;21(4-5):399-404. [1388107 ]