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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:
Molecular Weight:
290.32
Beilstein:
825455
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

solid

mp

>300 °C (lit.)

functional group

amine

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

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J K Tolson et al.
Journal of agricultural and food chemistry, 47(3), 1217-1222 (1999-12-20)
Benomyl [methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate] is the active ingredient in DuPont Benlate fungicides. The formation of N, N'-dibutylurea (DBU), a phytotoxic degradation product of benomyl, in Benlate formulations was evaluated by analyzing Benlate samples maintained under simulated storage conditions and assessing the
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)
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
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)
Stephen A Sassman et al.
Journal of agricultural and food chemistry, 52(4), 747-754 (2004-02-19)
N,N'-Dibutylurea (DBU) is a breakdown product of benomyl [methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate], the active ingredient in Benlate fungicides, and has been proposed as one cause for crop damage that growers claim to have occurred from the use of Benlate 50 DF

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