17804-35-2 | Carbamic acid, N-​[1-​[(butylamino)​carbonyl]​-​1H-​benzimidazol-​2-​yl]​-​, methyl ester

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$34.00	$24.00
5g	95%	in stock	$66.00	$46.00
10g	95%	in stock	$99.00	$70.00

Description

• Catalog Number: AI67460
• Chemical Name: Carbamic acid, N-​[1-​[(butylamino)​carbonyl]​-​1H-​benzimidazol-​2-​yl]​-​, methyl ester
• CAS Number: 17804-35-2
• Molecular Formula: C14H18N4O3
• Molecular Weight: 290.31772
• MDL Number: MFCD00084636
• SMILES: CCCCNC(=O)n1c(NC(=O)OC)nc2c1cccc2
• NSC Number: 263489

Computed Properties

• Complexity: 377
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 21
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 5
• XLogP3: 2.1

Literature

• Benomyl-induced effects of ORMDL3 overexpression via oxidative stress in human bronchial epithelial cells.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20161201

• Ziram and sodium N,N-dimethyldithiocarbamate inhibit ubiquitin activation through intracellular metal transport and increased oxidative stress in HEK293 cells.

  Chemical research in toxicology 20150420

• Antiandrogenic mechanisms of pesticides in human LNCaP prostate and H295R adrenocortical carcinoma cells.

  Toxicological sciences : an official journal of the Society of Toxicology 20150101

• Deleterious effects of benomyl and carbendazim on human placental trophoblast cells.

  Reproductive toxicology (Elmsford, N.Y.) 20150101

• Influence of the carbamate fungicide benomyl on the gene expression and activity of aromatase in the human breast carcinoma cell line MCF-7.

  Environmental toxicology and pharmacology 20150101

• Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor.

  Scientific reports 20140101

• Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones.

  Bioorganic & medicinal chemistry 20121115

• Chemically enhanced phytoextraction of lead-contaminated soils.

  International journal of phytoremediation 20120801

• Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.

  Journal of agricultural and food chemistry 20111026

• Potential of an in vitro toolbox combined with exposure data as a first step for the risk assessment of dietary chemical contaminants.

  Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20110901

• Global analysis of core histones reveals nucleosomal surfaces required for chromosome bi-orientation.

  The EMBO journal 20110817

• Global analysis for functional residues of histone variant Htz1 using the comprehensive point mutant library.

  Genes to cells : devoted to molecular & cellular mechanisms 20110501

• The War against a Regional Disease in Japan A History of the Eradication of Schistosomiasis japonica.

  Tropical medicine and health 20110301

• Localisation of the benzimidazole fungicide binding site of Gibberella zeae β2-tubulin studied by site-directed mutagenesis.

  Pest management science 20110201

• The reconstruction of condition-specific transcriptional modules provides new insights in the evolution of yeast AP-1 proteins.

  PloS one 20110101

• Determination of carbendazim, thiophanate, thiophanate-methyl and benomyl residues in agricultural products by liquid chromatography-tandem mass spectrometry.

  Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20110101

• Loss-of-function of Constitutive Expresser of Pathogenesis Related Genes5 affects potassium homeostasis in Arabidopsis thaliana.

  PloS one 20110101

• Chamomile (Matricaria chamomilla L.): An overview.

  Pharmacognosy reviews 20110101

• Aspergillus myosin-V supports polarized growth in the absence of microtubule-based transport.

  PloS one 20110101

• Individual lysine acetylations on the N terminus of Saccharomyces cerevisiae H2A.Z are highly but not differentially regulated.

  The Journal of biological chemistry 20101217

• Effects of some pesticides on the vital organs of juvenile rainbow trout (Oncorhynchus mykiss).

  Tissue & cell 20101201

• Deleterious effects of arsenic, benomyl and carbendazim on human endometrial cell proliferation in vitro.

  Taiwanese journal of obstetrics & gynecology 20101201

• Influence of benomyl and prometryn on the soil microbial activities and community structures in pasture grasslands of Slovakia.

  Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20101001

• New capabilities for Mycosphaerella graminicola research.

  Molecular plant pathology 20100901

• Pesticide use and cutaneous melanoma in pesticide applicators in the agricultural heath study.

  Environmental health perspectives 20100601

• Effects of fungicides on in vitro spore germination and mycelial growth of the phytopathogens Leptosphaeria maculans and L. biglobosa (phoma stem canker of oilseed rape).

  Pest management science 20100401

• Pesticide use and thyroid disease among women in the Agricultural Health Study.

  American journal of epidemiology 20100215

• Characterization of the cytotoxic properties of the benzimidazole fungicides, benomyl and carbendazim, in human tumour cell lines and primary cultures of patient tumour cells.

  Anti-cancer drugs 20100101

• Benomyl-resistant mutant strain of Trichoderma sp. with increased mycoparasitic activity.

  Folia microbiologica 20100101

• Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.

  Bioorganic & medicinal chemistry letters 20091201

• Rhinitis associated with pesticide exposure among commercial pesticide applicators in the Agricultural Health Study.

  Occupational and environmental medicine 20091101

• Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi.

  Journal of agricultural and food chemistry 20090708

• Contrasting short-term antibiotic effects on respiration and bacterial growth compromises the validity of the selective respiratory inhibition technique to distinguish fungi and bacteria.

  Microbial ecology 20090701

• Liquid chromatographic determination of benomyl in water samples after dispersive liquid-liquid microextraction.

  Journal of separation science 20090701

• Utility of six fungicides for selective isolation of Evlachovaea sp. and Tolypocladium cylindrosporum.

  Mycopathologia 20090601

• Benomyl induction of brain aromatase and toxic effects in the zebrafish embryo.

  Journal of applied toxicology : JAT 20090501

• Bioactivity-guided fractionation and GC/MS fingerprinting of Angelica sinensis and Angelica archangelica root components for antifungal and mosquito deterrent activity.

  Journal of agricultural and food chemistry 20090128

• Benomyl and colchicine synergistically inhibit cell proliferation and mitosis: evidence of distinct binding sites for these agents in tubulin.

  Biochemistry 20081209

• [Determination of benomyl, carbendazim and thiabendazole in apple juice concentrate using solid-phase extraction coupled with ion exchange chromatography].

  Se pu = Chinese journal of chromatography 20080901

• Spectrofluorimetric determination of benzoimidazolic pesticides: effect of p-sulfonatocalix[6]arene and cyclodextrins.

  Analytica chimica acta 20080822

• Fungicide tests on adult alfalfa leafcutting bees (Hymenoptera: Megachilidae).

  Journal of economic entomology 20080801

• Foraging and nesting behavior of Osmia lignaria (Hymenoptera: Megachilidae) in the presence of fungicides: cage studies.

  Journal of economic entomology 20080601

• Laboratory bioassays to evaluate fungicides for chalkbrood control in larvae of the alfalfa leafcutting bee (Hymenoptera: Megachilidae).

  Journal of economic entomology 20080601

• Genetic stabilization of Saccharomyces cerevisiae oenological strains by using benomyl.

  International microbiology : the official journal of the Spanish Society for Microbiology 20080601

• Effects of three pesticides on the avoidance behavior of earthworms in laboratory tests performed under temperate and tropical conditions.

  Environmental pollution (Barking, Essex : 1987) 20080501

• Rapid tip-directed movement of Golgi equivalents in growing Aspergillus nidulans hyphae suggests a mechanism for delivery of growth-related materials.

  Microbiology (Reading, England) 20080501

• A novel yeast-based tool to detect mutagenic and recombinogenic effects simultaneously.

  Mutation research 20080329

• Effects of possible endocrine disruptors on MyD88-independent TLR4 signaling.

  FEMS immunology and medical microbiology 20080301

• Toxic effects of carbendazim and n-butyl isocyanate, metabolites of the fungicide benomyl, on early development in the African clawed frog, Xenopus laevis.

  Environmental toxicology 20080201

• Genome adaptation to chemical stress: clues from comparative transcriptomics in Saccharomyces cerevisiae and Candida glabrata.

  Genome biology 20080101

• Benomyl resistance of Colletotrichum acutatum is caused by enhanced expression of beta-tubulin 1 gene regulated by putative leucine zipper protein CaBEN1.

  Fungal genetics and biology : FG & B 20071201

• Survival in the presence of antifungals: genome-wide expression profiling of Aspergillus niger in response to sublethal concentrations of caspofungin and fenpropimorph.

  The Journal of biological chemistry 20071109

• Effects of the fungicide benomyl on earthworms in laboratory tests under tropical and temperate conditions.

  Archives of environmental contamination and toxicology 20071101

• Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.

  Journal of agricultural and food chemistry 20071017

• Formulation factors that can reduce the formation of the phytotoxic impurity, N,N'-dibutylurea, from benomyl.

  Chemosphere 20070701

• In vitro susceptibility to fungicides by invertebrate-pathogenic and saprobic fungi.

  Mycopathologia 20070701

• Determination of benomyl residues in shiitake mushrooms (Lentinula edodes) by liquid chromatography with UV detection.

  Journal of chromatographic science 20070701

• Microtubule disruption stimulates P-body formation.

  RNA (New York, N.Y.) 20070401

• Pesticide exposure and self-reported Parkinson's disease in the agricultural health study.

  American journal of epidemiology 20070215

• A new environmentally resistant cell type from Dictyostelium.

  Microbiology (Reading, England) 20070201

• Inhibition of aldehyde detoxification in CNS mitochondria by fungicides.

  Neurotoxicology 20070101

• Replacement of the essential Dictyostelium Arp2 gene by its Entamoeba homologue using parasexual genetics.

  BMC genetics 20070101

• Alkyl, aryl, alkylarylquinoline, and related alkaloids.

  The Alkaloids. Chemistry and biology 20070101

• Unidentified inert ingredients in pesticides: implications for human and environmental health.

  Environmental health perspectives 20061201

• Effects of possible endocrine disrupting chemicals on bacterial component-induced activation of NF-kappaB.

  Biological & pharmaceutical bulletin 20061001

• Chemical composition and antifungal activity of Salvia macrochlamys and Salvia recognita essential oils.

  Journal of agricultural and food chemistry 20060906

• Suppression of microtubule dynamics by benomyl decreases tension across kinetochore pairs and induces apoptosis in cancer cells.

  The FEBS journal 20060901

• Activation of alpha- and beta-estrogen receptors by persistent pesticides in reporter cell lines.

  Life sciences 20060815

• The Saccharomyces cerevisiae orthologue of the human protein phosphatase 4 core regulatory subunit R2 confers resistance to the anticancer drug cisplatin.

  The FEBS journal 20060701

• Characterization of a Kluyveromyces lactis mutant with altered regulation of mitochondrial alcohol dehydrogenases.

  FEMS yeast research 20060501

• Autophagic fungal cell death is necessary for infection by the rice blast fungus.

  Science (New York, N.Y.) 20060428

• Neural tube defects and maternal residential proximity to agricultural pesticide applications.

  American journal of epidemiology 20060415

• Nitrile glove permeation of benomyl.

  Archives of environmental contamination and toxicology 20060401

• Production of Trichoderma strains with pesticide-polyresistance by mutagenesis and protoplast fusion.

  Antonie van Leeuwenhoek 20060101

• Combined bromodeoxyuridine immunocapture and terminal-restriction fragment length polymorphism analysis highlights differences in the active soil bacterial metagenome due to Glomus mosseae inoculation or plant species.

  Environmental microbiology 20051201

• Terrestrial avoidance behaviour tests as screening tool to assess soil contamination.

  Environmental pollution (Barking, Essex : 1987) 20051101

• Controlling fungal contamination in Chlamydomonas reinhardtii cultures.

  BioTechniques 20051001

• Minutosides A and B, antifungal sulfated steroid xylosides from the patagonian starfish Anasterias minuta.

  Journal of natural products 20050801

• Accelerated degradation of N, N'-dibutylurea (DBU) upon repeated application.

  Biodegradation 20050601

• Prediction of genotoxicity of chemical compounds by statistical learning methods.

  Chemical research in toxicology 20050601

• Functional genomics may allow accurate categorization of the benzimidazole fungicide benomyl: lack of ability to act via steroid-receptor-mediated mechanisms.

  Toxicology and applied pharmacology 20050515

• Avoidance behaviour of Enchytraeus albidus: effects of benomyl, carbendazim, phenmedipham and different soil types.

  Chemosphere 20050401

• Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species.

  Journal of agricultural and food chemistry 20050309

• The effects of fungicide benomyl (benlate) on growth and mitosis in onion (Allium cepa L.) root apical meristem.

  Acta biologica Hungarica 20050101

• Potential teratogenic effects of benomyl in rat embryos cultured in vitro.

  Reproductive toxicology (Elmsford, N.Y.) 20050101

• Flow-through fluorescence-based optosensor with on-line solid-phase separation for the simultaneous determination of a ternary pesticide mixture.

  Journal of AOAC International 20050101

• Gene function prediction from congruent synthetic lethal interactions in yeast.

  Molecular systems biology 20050101

• Oxidative stress and mitochondrial aldehyde dehydrogenase activity: a comparison of pentaerythritol tetranitrate with other organic nitrates.

  Molecular pharmacology 20041201

• A novel nonradioactive method for measuring aromatase activity using a human ovarian granulosa-like tumor cell line and an estrone ELISA.

  Toxicological sciences : an official journal of the Society of Toxicology 20041201

• Subcutaneous phaeohyphomycosis caused by Lasiodiplodia theobromae and successfully treated surgically.

  Medical mycology 20041201

• The yeast rRNA biosynthesis factor Ebp2p is also required for efficient nuclear division.

  Yeast (Chichester, England) 20041030

• Endocrine-disrupting activity in carbendazim-induced reproductive and developmental toxicity in rats.

  Journal of toxicology and environmental health. Part A 20041008

• Pesticide patch test series for the assessment of allergic contact dermatitis among banana plantation workers in panama.

  Dermatitis : contact, atopic, occupational, drug 20040901

• Exploration of essential gene functions via titratable promoter alleles.

  Cell 20040709

• Sequence divergence of Entamoeba histolytica tubulin is responsible for its altered tertiary structure.

  Biochemical and biophysical research communications 20040702

• 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 20040601

• Structure-activity relationships of derivatives of fusapyrone, an antifungal metabolite of Fusarium semitectum.

  Journal of agricultural and food chemistry 20040519

• Development of a single fluorescence-based optosensor for rapid simultaneous determination of fungicides benomyl and thiabendazole in waters and commercial formulations.

  Journal of agricultural and food chemistry 20040421

• A benzimidazole fungicide, benomyl, and its metabolite, carbendazim, induce aromatase activity in a human ovarian granulose-like tumor cell line (KGN).

  Endocrinology 20040401

• Genetic interactions of DST1 in Saccharomyces cerevisiae suggest a role of TFIIS in the initiation-elongation transition.

  Genetics 20040301

• Assessing N,N'-Dibutylurea (DBU) formation in soils after application of n-butylisocyanate and benlate fungicides.

  Journal of agricultural and food chemistry 20040225

• Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors.

  Analytical and bioanalytical chemistry 20040201

• Chemically induced supernumerary lumbar ribs in CD-1 mice: size distribution and dose response.

  Birth defects research. Part B, Developmental and reproductive toxicology 20040201

• Integration of chemical-genetic and genetic interaction data links bioactive compounds to cellular target pathways.

  Nature biotechnology 20040101

• Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae.

  Journal of natural products 20040101

• Degradation of N,N'-dibutylurea (DBU) in soils treated with only DBU and DBU-fortified benlate fungicides.

  Journal of environmental quality 20040101

• Antagonistic effects of several bacteria on Fusarium oxysporum, the causal agent of root and crown rot of onion under field conditions.

  Communications in agricultural and applied biological sciences 20040101

• Genotoxicity of benomyl and its residues in somatic and germ cells of mice fed on treated stored wheat grains.

  Archives of toxicology 20031201

• Biological control of Fusarium wilt of pigeonpea Cajanus cajan (L.) Millsp with chitinolytic Alcaligenes xylosoxydans.

  Indian journal of experimental biology 20031201

• Mutations in a beta-tubulin disrupt spindle orientation and microtubule dynamics in the early Caenorhabditis elegans embryo.

  Molecular biology of the cell 20031101

• Comparative study of the antioxidant effect of ardisin and epigallocatechin gallate in rat hepatocytes exposed to benomyl and 1-nitropyrene.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20031101

• Effect of common pesticides used in the Niger Delta basin of southern Nigeria on soil microbial populations.

  Environmental monitoring and assessment 20031101

• Does nitric oxide mediate the vasodilator activity of nitroglycerin?

  Circulation research 20031031

• The fungicide benomyl inhibits differentiation of neural tissue in the Xenopus embryo and animal cap explants.

  Environmental toxicology 20031001

• Oxidation of 4-hydroxy-2-nonenal by succinic semialdehyde dehydrogenase (ALDH5A).

  Journal of neurochemistry 20030701

• Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.

  Journal of agricultural and food chemistry 20030212

• Chemical composition, plant genetic differences, and antifungal activity of the essential oil of Helichrysum italicum G. Don ssp. microphyllum (Willd) Nym.

  Journal of agricultural and food chemistry 20030212

• Parasexual genetics of Dictyostelium gene disruptions: identification of a ras pathway using diploids.

  BMC genetics 20030101

• Homologous expression of a mutated beta-tubulin gene does not confer benomyl resistance on Trichoderma virens.

  Journal of applied microbiology 20030101

• Comparison of solid-phase extraction and micro-solid-phase extraction for liquid chromatography/mass spectrometry analysis of pesticides in water samples.

  Journal of AOAC International 20030101

• Risk assessment of biocontrol products: a semi-selective medium for improving quantitative isolation of Paecilomyces lilacinus (strain 251) from soil.

  Communications in agricultural and applied biological sciences 20030101

• Topoisomerase I and II enzyme inhibitory aqueous extract of Ardisia compressa and ardisin protect against benomyl oxidation of hepatocytes.

  Journal of agricultural and food chemistry 20021218

• The yeast ubiquitin protease, Ubp3p, promotes protein stability.

  Genetics 20021101

• Inhibition of Paracoccidioides brasiliensis by pesticides: is this a partial explanation for the difficulty in isolating this fungus from the soil?

  Medical mycology 20021001

• Investigation of deaths in an area of groundnut plantations in Casamance, South of Senegal after exposure to Carbofuran, Thiram and Benomyl.

  Journal of exposure analysis and environmental epidemiology 20020901

• A survey of EPA/OPP and open literature on selected pesticide chemicals. III. Mutagenicity and carcinogenicity of benomyl and carbendazim.

  Mutation research 20020901

• Antifungal stilbenoids from Stemona collinsae.

  Journal of natural products 20020601

• Heterozygosity in MAT locus affects stability and function of microtubules in yeast.

  Biology of the cell 20020601

• Overexpression of B-type cyclins alters chromosomal segregation.

  Oncogene 20020327

• Fungicidal activity of essential oils of Cinnamomum zeylanicum (L.) and Syzygium aromaticum (L.) Merr et L.M. Perry against crown rot and anthracnose pathogens isolated from banana.

  Letters in applied microbiology 20020101

• Phosphorylation of gamma-tubulin regulates microtubule organization in budding yeast.

  Developmental cell 20011101

• [Elimination of carbendazim from fruit conditioning waters by adsorption on different materials].

  Environmental technology 20010701

• Degradation of benomyl, picloram, and dicamba in a conical apparatus by zero-valent iron powder.

  Chemosphere 20010601

• Mutagenesis of beta-tubulin cysteine residues in Saccharomyces cerevisiae: mutation of cysteine 354 results in cold-stable microtubules.

  Cell motility and the cytoskeleton 20010601

• Characterizing the production of a wild-type and benomyl-resistant Fusarium lateritium for biocontrol of Eutypa lata on grapevine.

  Journal of industrial microbiology & biotechnology 20010301

• Effect of enzyme inhibitors on protein quaternary structure determined by on-line size exclusion chromatography-microelectrospray ionization mass spectrometry.

  Journal of the American Society for Mass Spectrometry 20010101

• Incidence and severity of frogeye leaf spot and associated yield losses in soybeans in agroecological zone II of Zambia.

  Mycopathologia 20010101

• Responses of two ladybeetles to eight fungicides used in Florida citrus: implications for biological control.

  Journal of insect science (Online) 20010101

• S-methyl N-butylthiocarbamate sulfoxide: selective carbamoylating agent for mouse mitochondrial aldehyde dehydrogenase.

  Biochemical pharmacology 19991101

• Mechanism for benomyl action as a mitochondrial aldehyde dehydrogenase inhibitor in mice.

  Chemical research in toxicology 19980501

• Biochemical characterization of benomyl inhibition on endometrial growth during decidualization in rats.

  Advances in experimental medicine and biology 19980101

• In vitro susceptibilities of the AIDS-associated microsporidian Encephalitozoon intestinalis to albendazole, its sulfoxide metabolite, and 12 additional benzimidazole derivatives.

  Antimicrobial agents and chemotherapy 19971201

• Effect of pesticide mixtures on in vitro nervous cells: comparison with single pesticides.

  Toxicology 19960430

• Beta-tubulin genes from the parasitic nematode Haemonchus contortus modulate drug resistance in Caenorhabditis elegans.

  Journal of molecular biology 19950303

• In vitro susceptibility of the opportunistic fungus Cryptococcus neoformans to anthelmintic benzimidazoles.

  Antimicrobial agents and chemotherapy 19940201

• Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants.

  Reproductive toxicology (Elmsford, N.Y.) 19920101

• Effects on the fetal rat eye of maternal benomyl exposure and protein malnutrition.

  Current eye research 19910701

• [Contact eczema caused by pesticides in East Germany].

  Dermatologische Monatschrift 19890101

• Combined high performance liquid chromatography mass spectrometry.

  Biomedical mass spectrometry 19810901

• Bacterial breakdown of benomyl. I. Pure cultures.

  Antonie van Leeuwenhoek 19780101