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381586

Sigma-Aldrich

Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate

95%

Synonym(s):

Benomyl, NSC 263489

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About This Item

Empirical Formula (Hill Notation):
C14H18N4O3
CAS Number:
17804-35-2
Molecular Weight:
290.32
Beilstein:
825455
EC Number:
241-775-7
MDL number:
MFCD00084636
UNSPSC Code:
12352100
PubChem Substance ID:
24863827
NACRES:
NA.22

Assay

95%

form

solid

mp

>300 °C (lit.)

SMILES string

CCCCNC(=O)n1c(NC(=O)OC)nc2ccccc12

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)

InChI key

RIOXQFHNBCKOKP-UHFFFAOYSA-N

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General description

Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate (Benomyl) is widely employed for the treatment of various fungal diseases in agriculture. It has been reported as an active constituent of DuPont Benlate fungicidal formulations. Kinetics of the degradation of benomyl in various organic solvents has been investigated by spectrophotometric methods. N,N′-Dibutylurea (DBU) has been reported as the major metabolite of benomyl.

Application

Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate may be used as standard reagent for the HPLC quantification of benomyl in water, sediment and biota samples.

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Analysis of benomyl by liquid chromatography/time-of-flight mass spectrometer and its occurrence in the environment.
Seo YC, et al.
Bull. Korean Chem. Soc., 23(3), 432-436 (2002)
Kamlesh Gupta et al.
Biochemistry, 43(21), 6645-6655 (2004-05-26)
The antifungal agent benomyl [methyl-1-(butylcarbamoyl)-2-benzimidazolecarbamate] is used throughout the world against a wide range of agricultural fungal diseases. In this paper, we investigated the interaction of benomyl with mammalian brain tubulin and microtubules. Using the hydrophobic fluorescent probe 1-anilinonaphthalene-8-sulfonic acid
Jayne Aiken et al.
Cytoskeleton (Hoboken, N.J.), 77(3-4), 40-54 (2019-10-02)
The neuronal cytoskeleton performs incredible feats during nervous system development. Extension of neuronal processes, migration, and synapse formation rely on the proper regulation of microtubules. Mutations that disrupt the primary α-tubulin expressed during brain development, TUBA1A, are associated with a
A L Loyd et al.
PloS one, 13(7), e0199738-e0199738 (2018-07-19)
Ganoderma is a large, diverse and globally-distributed genus in the Basidiomycota that includes species causing a white rot form of wood decay on a variety of tree species. For the past century, many studies of Ganoderma in North America and
Kinetic study of reversible conversion of methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl) to methyl 2-benzimidazolecarbamate (MBC) and n-butyl isocyanate (BIC) in organic solvents.
Chiba M and Cherniak EA.
Journal of Agricultural and Food Chemistry, 26(3), 573-576 (1978)
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