Benomyl
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Basic Info
| Common Name | Benomyl(F03962) |
| 2D Structure | |
| 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. |
| FRCD ID | F03962 |
| CAS Number | 17804-35-2 |
| PubChem CID | 28780 |
| Formula | C14H18N4O3 |
| IUPAC Name | methyl N-[1-(butylcarbamoyl)benzimidazol-2-yl]carbamate |
| InChI Key | RIOXQFHNBCKOKP-UHFFFAOYSA-N |
| InChI | InChI=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) |
| Canonical SMILES | CCCCNC(=O)N1C2=CC=CC=C2N=C1NC(=O)OC |
| Isomeric SMILES | CCCCNC(=O)N1C2=CC=CC=C2N=C1NC(=O)OC |
| Synonyms |
BENOMYL
Fungochrom
Benlate
17804-35-2
Fundazol
Agrocit
Uzgen
Benlate 50
Arbortrine
Fundasol
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzimidazoles |
| Subclass | 2-benzimidazolylcarbamic acid esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 2-benzimidazolylcarbamic acid esters |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 290.323 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 377 |
| Monoisotopic Mass | 290.138 |
| Exact Mass | 290.138 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7517 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.6250 |
| P-glycoprotein Substrate | Substrate | 0.6297 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5885 |
| Non-inhibitor | 0.6385 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8744 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4754 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7871 |
| CYP450 2D6 Substrate | Non-substrate | 0.8159 |
| CYP450 3A4 Substrate | Non-substrate | 0.5388 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6810 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7747 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8252 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6078 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8671 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6171 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9098 |
| Non-inhibitor | 0.6722 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.8909 |
| Fish Toxicity | High FHMT | 0.9106 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9207 |
| Honey Bee Toxicity | Low HBT | 0.6939 |
| Biodegradation | Not ready biodegradable | 0.9668 |
| Acute Oral Toxicity | IV | 0.6140 |
| Carcinogenicity (Three-class) | Non-required | 0.6388 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.8178 | LogS |
| Caco-2 Permeability | 0.7477 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.4944 | LD50, mol/kg |
| Fish Toxicity | 1.4723 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4475 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Others (2) | 0242990 | European Union | 0.1* | 01/01/2012 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.2 | 01/01/2012 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.2 | 01/01/2012 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.7 | 01/01/2012 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.7 | 01/01/2012 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.7 | 01/01/2012 | |
| Others (2) | 0110990 | European Union | 0.1* | 01/01/2012 | |
| Tree nuts | 0120000 | European Union | 0.1* | 01/01/2012 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 01/01/2012 | |
| Brazil nuts | 0120020 | European Union | 0.1* | 01/01/2012 | |
| Cashew nuts | 0120030 | European Union | 0.1* | 01/01/2012 | |
| Chestnuts | 0120040 | European Union | 0.1* | 01/01/2012 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 01/01/2012 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 01/01/2012 | |
| Macadamias | 0120070 | European Union | 0.1* | 01/01/2012 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.1* | 01/01/2012 | |
| Pistachios | 0120100 | European Union | 0.1* | 01/01/2012 | |
| Walnuts | 0120110 | European Union | 0.1* | 01/01/2012 | |
| Others (2) | 0120990 | European Union | 0.1* | 01/01/2012 | |
| Apples (Crab apples/wild apples, Tejocotes,) | 0130010 | European Union | 0.2 | 01/01/2012 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| [Simultaneous determination of three benzimidazole fungicides in fruits andvegetables by capillary electrophoresis based on bacterial cellulose]. | Se Pu | 2017 Dec 8 | 29372782 |
| Molecular characterization, fitness and mycotoxin production of Fusarium graminearum laboratory strains resistant to benzimidazoles. | Pestic Biochem Physiol | 2016 Mar | 26969433 |
| Antifungal and Herbicidal Effects of Fruit Essential Oils of Four Myrtus communisGenotypes. | Chem Biodivers | 2016 Jan | 26765354 |
| Benomyl-induced effects of ORMDL3 overexpression via oxidative stress in humanbronchial epithelial cells. | Food Chem Toxicol | 2016 Dec | 27784618 |
| One-Step Fabrication of a Multifunctional Magnetic Nickel Ferrite/Multi-walledCarbon Nanotubes Nanohybrid-Modified Electrode for the Determination of Benomylin Food. | J Agric Food Chem | 2015 May 20 | 25947038 |
| Causes of genome instability: the effect of low dose chemical exposures in modernsociety. | Carcinogenesis | 2015 Jun | 26106144 |
| Enhancement of Shelf Life of Button Mushroom, Agaricus bisporus (HigherBasidiomycetes) by Fumigant Application of Lippia alba Essential Oil. | Int J Med Mushrooms | 2015 | 25746409 |
| Combined effects of benomyl and environmental factors on growth and expression of the fumonisin biosynthetic genes FUM1 and FUM19 by Fusarium verticillioides. | Int J Food Microbiol | 2014 Nov 17 | 25217721 |
| Effects of ozone microbubble treatment on removal of residual pesticides andquality of persimmon leaves. | Food Chem | 2013 May 1 | 23265500 |
| Molecular characterization, fitness and mycotoxin production of benzimidazole-resistant isolates of Penicillium expansum. | Int J Food Microbiol | 2013 Apr 1 | 23454814 |
| Efficiency of selected mutagens in generating Xanthophyllomyces dendrorhousstrains hyperproducing astaxanthin. | Pol J Microbiol | 2013 | 23829079 |
| Identification and biocontrol efficacy of Streptomyces miharaensis producingfilipin III against Fusarium wilt. | J Basic Microbiol | 2012 Apr | 22460913 |
| Potential of an in vitro toolbox combined with exposure data as a first step for the risk assessment of dietary chemical contaminants. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011 Sep | 21762035 |
| Disease control effect of strevertenes produced by Streptomyces psammoticusagainst tomato fusarium wilt. | J Agric Food Chem | 2011 Mar 9 | 21314121 |
| Determination of carbendazim, thiophanate, thiophanate-methyl and benomylresidues in agricultural products by liquid chromatography-tandem massspectrometry. | Shokuhin Eiseigaku Zasshi | 2011 | 21720119 |
| Concentration dependent effects of commonly used pesticides on activation versus inhibition of the quince (Cydonia Oblonga) polyphenol oxidase. | Food Chem Toxicol | 2010 Mar | 20060877 |
| Simultaneous direct analysis of benzimidazole fungicides and relevant metabolitesin agricultural products based on multifunction dispersive solid-phase extractionand liquid chromatography-mass spectrometry. | J Chromatogr A | 2010 Jul 16 | 20541210 |
| Functional genomics analysis of the Saccharomyces cerevisiae iron responsivetranscription factor Aft1 reveals iron-independent functions. | Genetics | 2010 Jul | 20439772 |
| Reducing the impact of pesticides on biological control in Australian vineyards: pesticide mortality and fecundity effects on an indicator species, the predatory mite Euseius victoriensis (Acari: Phytoseiidae). | J Econ Entomol | 2010 Dec | 21309226 |
| Benomyl induction of brain aromatase and toxic effects in the zebrafish embryo. | J Appl Toxicol | 2009 May | 19058295 |
Targets
- General Function:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 Da
- Mechanism of Action:
- Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Lemaire G, Mnif W, Mauvais P, Balaguer P, Rahmani R: Activation of alpha- and beta-estrogen receptors by persistent pesticides in reporter cell lines. Life Sci. 2006 Aug 15;79(12):1160-9. Epub 2006 Mar 27. [16626760 ]
- General Function:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General 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.
- Specific Function:
- Gtp binding
- Gene Name:
- TUBA1A
- Uniprot ID:
- Q71U36
- Molecular Weight:
- 50135.25 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d 24-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- 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
- Gupta K, Bishop J, Peck A, Brown J, Wilson L, Panda D. "Antimitotic antifungal compound benomyl inhibits brain microtubule polymerization and dynamics and cancer cell proliferation at mitosis, by binding to a novel site in tubulin.". Biochemistry. 2004 Jun 1;43(21):6645-55. [15157098 ]
- General Function:
- Virus receptor activity
- Specific Function:
- Binds LDL, the major cholesterol-carrying lipoprotein of plasma, and transports it into cells by endocytosis. In order to be internalized, the receptor-ligand complexes must first cluster into clathrin-coated pits.(Microbial infection) Acts as a receptor for hepatitis C virus in hepatocytes, but not through a direct interaction with viral proteins (PubMed:10535997, PubMed:12615904). Acts as a receptor for vesicular stomatitis virus (PubMed:23589850). In case of HIV-1 infection, may function as a receptor for extracellular Tat in neurons, mediating its internalization in uninfected cells (PubMed:11100124).
- Gene Name:
- LDLR
- Uniprot ID:
- P01130
- Molecular Weight:
- 95375.105 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]