Benomyl (CHEM000790)

Record Information
Version1.0
Creation Date2009-06-17 23:53:01 UTC
Update Date2026-08-19 06:29:41 UTC
Accession NumberCHEM000790
Identification
Common NameBenomyl
ClassSmall Molecule
Description
Benomyl (also marketed as Benlate) is a fungicide introduced in 1968 by DuPont. It is a systemic benzimidazole fungicide that is selectively toxic to microorganisms and invertebrates, especially earthworms. Benomyl binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation. The selective toxicity of benomyl as a fungicide is possibly due to its heightened effect on fungal rather than mammalian microtubules. Due to the development and worldwide prevalence of resistance of parasitic fungi to benomyl, it and similar pesticide compounds became largely ineffective.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Carbamate
  • Ester
  • Ether
  • Food Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(Butylcarbamoyl)-2-benzimidazol-methylcarbamatChEBI
1-(Butylcarbamoyl)-2-benzimidazolecarbamic acid, methyl esterChEBI
1-(N-Butylcarbamoyl)-2-(methoxy-carboxamido)-benzimidazolChEBI
BenlateChEBI
Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamateChEBI
Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamateChEBI
Methyl N-(1-butylcarbamoyl-2-benzimidazole)carbamateChEBI
1-(Butylcarbamoyl)-2-benzimidazolecarbamate, methyl esterGenerator
Benlic acidGenerator
Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamic acidGenerator
Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamic acidGenerator
Methyl N-(1-butylcarbamoyl-2-benzimidazole)carbamic acidGenerator
AgrocitHMDB
ArbortrineHMDB
ArilateHMDB
BBCHMDB
BenexHMDB
BenlatHMDB
Benlate 50HMDB
Benlate 50 WHMDB
Benlate 50WHMDB
BenomilHMDB
Benomyl 50WHMDB
Benomyl-imexHMDB
BenosanHMDB
BNMHMDB
Chinoin-fundazolHMDB
Du pont 1991HMDB
Dupont 1991HMDB
FibenzolHMDB
FundasolHMDB
FundazolHMDB
Fundazol 50WPHMDB
Fungicide 1991HMDB
Fungicide D-1991HMDB
FungochromHMDB
KribenomyHMDB
KribenomylHMDB
MBCLHMDB
Methyl 1-(butylcarbamoyl)-2-benzimidazolylcarbamateHMDB
Methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamateHMDB
Methyl 1-[(butylamino)carbonyl]-1H-benzimidazol-2-ylcarbamate, 9ciHMDB
Methyl [1-(butylcarbamoyl)-1H-benzimidazol-2-yl]carbamateHMDB
NS 02 (Fungicide)HMDB
Tersan 1991HMDB
UzgenHMDB
Chemical FormulaC14H18N4O3
Average Molecular Mass290.318 g/mol
Monoisotopic Mass290.138 g/mol
CAS Registry Number17804-35-2
IUPAC NameN-butyl-2-{[hydroxy(methoxy)methylidene]amino}-1H-1,3-benzodiazole-1-carboximidic acid
Traditional Namebenomyl
SMILESCCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12
InChI IdentifierInChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)
InChI KeyRIOXQFHNBCKOKP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub Class2-benzimidazolylcarbamic acid esters
Direct Parent2-benzimidazolylcarbamic acid esters
Alternative Parents
Substituents
  • 2-benzimidazolylcarbamic acid ester
  • Imidazole-1-carbonyl group
  • N-substituted imidazole
  • Benzenoid
  • Azole
  • Imidazole
  • Carbamic acid ester
  • Heteroaromatic compound
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point140°C
Boiling PointNot Available
Solubility0.0038 mg/mL at 20°C
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.32ALOGPS
logP3.68ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)2.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.49 m³·mol⁻¹ChemAxon
Polarizability31.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4); dermal (4)
Mechanism of ToxicityBenomyl targets beta tubulin in actively dividing cells. It binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation (3). Benomyl binds to brain tubulin with a dissociation constant of 11.9 +/- 1.2 microM. Further, benomyl binds to a novel tubulin beta binding site, distinct from the well-characterized colchicine and vinblastine binding sites. Benomyl inhibits the polymerization of brain tubulin into microtubules, with 50% inhibition occurring at a concentration of 70-75 microM (2)
MetabolismNot Available
Toxicity ValuesBenomyl is of such a low toxicity to mammals, it has been impossible to administer doses large enough to establish an LD50. It has an arbitrary LD50 of "greater than 10,000 mg/kg/day for rats".
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 Occupational Safety and Health Administration has set a permissible exposure limit of 15 mg/m3 for total exposure over an eight-hour time-weighted average.
Health EffectsSkin irritation may occur through industrial exposure, and florists, mushroom pickers and floriculturists have reported allergic reactions to benomyl. Benomyl is a potential teratogen. Studies have shown eye defects can occur at relatively high doses. A test in which rats were dosed orally demonstrated evidence of microphthalmia at dose levels of 62.5 mg/kg and above. In 1996, a Miami jury awarded US$ 4 million to a child whose mother was exposed in pregnancy to Benomyl. The child was born without eyes. The mother had been exposed to an unusually high dose of Benomyl through her occupation, during pregnancy.
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.
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0031767
FooDB IDFDB008440
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenomyl
Chemspider ID26771
ChEBI ID3015
PubChem Compound ID28780
Kegg Compound IDC10896
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15813220
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16903866
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19049291
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24693254
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24782104
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25045800
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25104429
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25145128
9. Edlind TD, Bartlett MS, Smith JW: Characterization of the beta-tubulin gene of Pneumocystis carinii. J Protozool. 1991 Nov-Dec;38(6):62S-63S.
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.