Carbendazim
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Basic Info
| Common Name | Carbendazim(F03974) |
| 2D Structure | |
| Description | Carbendazim is a widely used, broad-spectrum benzimidazole fungicide. It is also a metabolite of benomyl (another widely used fungicide). It is also employed as a casting worm control agent in amenity turf situations such as golf greens and tennis courts. Carbendazim is used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, pineapples, and pomes. It is also used in Queensland, Australia on macadamia plantations. Carbendazim is absorbed through the roots and green tissues. It acts by inhibiting beta-tubulin synthesis, inhibiting development of germ tubes and the growth of mycelia. It is compatible with most of the insecticides. It is used for the control of blast, sheath blight, brown spot, powdery mildew, scab, anthracnose and leaf spot diseases in various crops. The primary source of carbendazim exposure for the public at large is dietary intake. |
| FRCD ID | F03974 |
| CAS Number | 10605-21-7 |
| PubChem CID | 25429 |
| Formula | C9H9N3O2 |
| IUPAC Name | methyl N-(1H-benzimidazol-2-yl)carbamate |
| InChI Key | TWFZGCMQGLPBSX-UHFFFAOYSA-N |
| 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) |
| Canonical SMILES | COC(=O)NC1=NC2=CC=CC=C2N1 |
| Isomeric SMILES | COC(=O)NC1=NC2=CC=CC=C2N1 |
| Synonyms |
Carbendazim
10605-21-7
Carbendazole
Mecarzole
Bavistin
Carbendazime
Carbendazol
Bavistan
Derosal
Thicoper
|
| 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 - Benzenoid - Azole - Imidazole - Carbamic acid ester - Heteroaromatic compound - Carbonic acid derivative - Azacycle - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - 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 | 191.19 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 222 |
| Monoisotopic Mass | 191.069 |
| Exact Mass | 191.069 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| 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+ | 0.9523 |
| Human Intestinal Absorption | HIA+ | 0.9939 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Non-substrate | 0.7100 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7799 |
| Non-inhibitor | 0.6748 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8799 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5978 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7673 |
| CYP450 2D6 Substrate | Non-substrate | 0.7815 |
| CYP450 3A4 Substrate | Non-substrate | 0.6791 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9220 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9628 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8693 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9444 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9012 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9225 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9516 |
| Non-inhibitor | 0.9276 | |
| AMES Toxicity | AMES toxic | 0.6958 |
| Carcinogens | Non-carcinogens | 0.9438 |
| Fish Toxicity | High FHMT | 0.8206 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9032 |
| Honey Bee Toxicity | Low HBT | 0.5634 |
| Biodegradation | Not ready biodegradable | 0.9849 |
| Acute Oral Toxicity | IV | 0.6133 |
| Carcinogenicity (Three-class) | Non-required | 0.5691 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2275 | LogS |
| Caco-2 Permeability | 1.2569 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6060 | LD50, mol/kg |
| Fish Toxicity | 1.8878 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1752 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Celery | Malaysia | 20mg/kg | |||
| Rye | CAC | 0.05mg/kg | |||
| Pepper | CAC | 2mg/kg | |||
| Carrot | CAC | 0. 2mg/kg | |||
| Broad Beans | Australia | 0.5mg/kg | |||
| Vegetable | Austria | see eu mrls | |||
| Avocado | Australia | 3mg/kg | |||
| Fruit | Austria | see eu mrls | |||
| Vegetable | Belgium | see eu mrls | |||
| Simazine | Australia | 0.1mg/kg | |||
| Citrus Fruits | Australia | 10mg/kg | |||
| Fruit | Belgium | see eu mrls | |||
| Peanuts | Australia | 0. 2mg/kg | |||
| Litchis | Australia | 10mg/kg | |||
| Mangoes | Australia | 5mg/kg | |||
| Pineapples | CAC | 5mg/kg | |||
| Mushrooms | Australia | 10mg/kg | |||
| Grape | Australia | 3mg/kg | |||
| Strawberry | Switzerland | 3mg/kg | |||
| Beans | Switzerland | 0. 2mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Cyto-genotoxic consequences of carbendazim treatment monitored by cytogeneticalanalysis using Allium root tip bioassay. | Environ Monit Assess | 2018 Mar 21 | 29564638 |
| Rapid determination of carbendazim in complex matrices by electrospray ionizationmass spectrometry with syringe filter needle. | J Mass Spectrom | 2018 Mar | 29314422 |
| Activity of the pterophyllins 2 and 4 against postharvest fruit pathogenic fungi.Comparison with a synthetic analog and related intermediates. | Fitoterapia | 2018 Mar | 29288027 |
| Statistical analysis of wheat under different seed treatments: development of adiscriminative model based on physicochemical and rheological properties. | J Sci Food Agric | 2018 Jun | 29205367 |
| [Simultaneous determination of seven high risk pesticide residues in royal jelly by high performance liquid chromatography-tandem mass spectrometry]. | Se Pu | 2018 Feb 8 | 29582599 |
| Method development, matrix effect, and risk assessment of 49 multiclasspesticides in kiwifruit using liquid chromatography coupled to tandem massspectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2018 Feb 15 | 29406026 |
| Occurrence of imidacloprid, carbendazim, and other biocides in Italian housedust: Potential relevance for intakes in children and pets. | J Environ Sci Health B | 2017 Sep 2 | 28679077 |
| "Carbon Assimilation" Inspired Design and Divergent Synthesis of DrimaneMeroterpenoid Mimics as Novel Fungicidal Leads. | J Agric Food Chem | 2017 Oct 18 | 28949528 |
| Revealing Pesticide Residues Under High Pesticide Stress in Taiwan's AgriculturalEnvironment Probed by Fresh Honey Bee (Hymenoptera: Apidae) Pollen. | J Econ Entomol | 2017 Oct 1 | 28981672 |
| Selection and Characterization of DNA Aptamers for Electrochemical Biosensing of Carbendazim. | Anal Chem | 2017 Mar 7 | 28264568 |
| Determination of trace thiophanate-methyl and its metabolite carbendazim withteratogenic risk in red bell pepper (Capsicumannuum L.) by surface-enhanced Ramanimaging technique. | Food Chem | 2017 Mar 1 | 27719947 |
| Determination of a broad spectrum of endocrine-disrupting pesticides in fishsamples by UHPLC-MS/MS using the pass-through cleanup approach. | J Sep Sci | 2017 Mar | 28098419 |
| LC-MS/MS determination of pesticide residues in fruits and vegetables. | J Environ Sci Health B | 2017 Jul 3 | 28353394 |
| Chemometric-assisted QuEChERS extraction method for post-harvest pesticidedetermination in fruits and vegetables. | Sci Rep | 2017 Feb 22 | 28225030 |
| Simultaneous Electrochemical Detection of Benzimidazole Fungicides Carbendazimand Thiabendazole Using a Novel Nanohybrid Material-Modified Electrode. | J Agric Food Chem | 2017 Feb 1 | 28068083 |
| Simultaneous removal of structurally different pesticides in a biomixture:Detoxification and effect of oxytetracycline. | Chemosphere | 2017 Feb | 27898329 |
| [Simultaneous determination of three benzimidazole fungicides in fruits andvegetables by capillary electrophoresis based on bacterial cellulose]. | Se Pu | 2017 Dec 8 | 29372782 |
| Occurrence of pesticide residues in Spanish beeswax. | Sci Total Environ | 2017 Dec 15 | 28679118 |
| Botrytis fragariae, a New Species Causing Gray Mold on Strawberries, Shows HighFrequencies of Specific and Efflux-Based Fungicide Resistance. | Appl Environ Microbiol | 2017 Apr 17 | 28235878 |
| Phosphorus-doped helical carbon nanofibers as enhanced sensing platform forelectrochemical detection of carbendazim. | Food Chem | 2017 Apr 15 | 27979227 |
Targets
- Gene Name:
- TP53
- Uniprot ID:
- P04637
- Molecular Weight:
- 43652.79 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
- 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 ]