41483-43-6

Basic information

• Product Name: BUPIRIMATE
• Synonyms: NIMROD;2-aethylamino-5-butyl-4-yl-dimethylsulfamat;-4-ol;dimethyl-sulfamicaci5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinylester;dimethylsulfamicacid5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinylester;n,n-dimethyl-sulfamicaciesterwith5-butyl-2-ethylamino-6-methylpyrimidin;nimrodt;pp588
• CAS NO: 41483-43-6
• Molecular Formula: C₁₃H₂₄N₄O₃S
• Molecular Weight: 316.42
• EINECS: 255-391-2
• Product Categories: BI - BZBuilding Blocks;PyrimidinesPesticides;A-BAlphabetic;Alpha sort;B;Fungicides;Heterocyclic Building Blocks;Pesticides&Metabolites;Pyrimidines
• Mol File: 41483-43-6.mol
• Article Data: 45

Chemical Properties

• Melting Point: 50-51°
• Boiling Point: 463.2 °C at 760 mmHg
• Flash Point: 100 °C
• Appearance: Emulsifiable liquid
• Density: 1.2120 (rough estimate)
• Vapor Pressure: 9.29E-09mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 5
• Water Solubility: 22 mg l-1 (pH 5.2), 18 mg l-1 (pH 7.3), 17 mg l-1 (pH 9.3) at 25 °C
• Merck: 13,1482
• BRN: 758056
• CAS DataBase Reference: BUPIRIMATE(CAS DataBase Reference)
• NIST Chemistry Reference: BUPIRIMATE(41483-43-6)
• EPA Substance Registry System: BUPIRIMATE(41483-43-6)

Safety Data

• Hazard Codes: Xn
• Statements: 21
• Safety Statements: 36/37
• WGK Germany: 2
• RTECS: WO5970000
• Hazardous Substances Data: 41483-43-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 41483-43-6 differently. You can refer to the following data:
1. Fungicide.
2. Bupirimate is a systemic fungicide that provides protective and curative control of powdery mildew (Podosphaera leucotricha) mainly in pome fruits, stone fruits and glasshouse roses. Other uses include berries, vines and cucurbits.
3. Bupirimate is a pyrimidine based fungicide with protective and curative activity for the control of fungal diseases by interfearing with nucleic acid synthesis.

Definition

ChEBI: A member of the class of aminopyrimidines that is 2-ethylaminopyrimidine carrying methyl, butyl and dimethylaminosulfooxy substituents at posiitons 4, 5 and 6 respectively.

Metabolic pathway

Bupirimate degrades rapidly when exposed to sunlight. Minimal penetration of bupirimate residues in treated apples was observed. Degradation of bupirimate in/on fruit surfaces was mainly due to photolytic processes. Metabolism in plants and animals is similar and includes the initial cleavage of the dimethylsulfamate-pyrimidine linkage to yield ethirimol which is also an active fungicide. Numerous degradation products were generated from N-dealkylation, hydroxylation and conjugation reactions and the opening of the pyrimidine ring (Scheme 1).

Degradation

Bupirimate (1) is stable in dilute alkaline solution, but readily hydrolysed in dilute acidic solution. Bupirimate was rapidly decomposed in aqueous solution when exposed to sunlight (Hassall, 1982). Cleavage of the dimethylsulfamate-pyrimidine linkage yielded ethirimol [5-butyl-2- ethylamino-6-methylpyrimidin-4-ol (2)] as the major product. Ethirimol, an active fungicide, was degraded slowly under these test conditions. Four additional minor products were also detected. Three of these products were identified aS isomers of bupirimate, resulting from the migration of the dimethylsulfamate moiety to the various nitrogen molecules (compounds 3, 4 and 5; Cavell and Lincoln, 1974; Teal and Skidmore, 1976).

InChI:InChI=1/C13H24N4O3S/c1-6-8-9-11-10(3)15-13(14-7-2)16-12(11)20-21(18,19)17(4)5/h6-9H2,1-5H3,(H,14,15,16)

Upstream product

• 13360-57-1 dimethylamino sulfonyl chloride 
• 23947-60-6 ethirimol 

Relevant articles and documents

Synthesis method of bupirimate

The invention discloses a synthesis method of bupirimate. The method comprises the following steps: dissolving ethirimol in a polar solvent, adding alkali into the solution, and stirring to react for1-2 hours; after stirring is finished, evaporating the polar solvent to dryness, adding an organic solvent and N,N-Dimethylsulfamoyl chloride into a reaction system, heating the system for reflux reaction, and evaporating the organic solvent to dryness after the reaction is finished; adding petroleum ether into the system, cooling the system to-5 DEG C to 0 DEG C, stirring to separate out a product, and filtering to obtain the bupirimate. According to the preparation method disclosed by the invention, through a strategy of salifying the ethirimol and then reacting the ethirimol with the N,N-Dimethylsulfamoyl chloride, the problems of incomplete ethirimol reaction, unstable reaction yield and easiness in product decomposition due to the fact that HCl generated in the reaction cannot be fully neutralized are avoided; the problem that the ethirimol cannot be completely converted due to the fact that the N,N-Dimethylsulfamoyl chloride is decomposed by adding water into the system is also avoided, so that the synthesis method is complete in raw material reaction, stable in yield and more suitable for industrial production.

SUBSTITUTED SPIROCYCLIC KETOENOLS

The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.

Use of oxabicyclo[2.2.1]heptane derivatives as pesticidal agents

7-oxabicyclo[2.2.1]heptane derivatives of formula (I) in which X, R1, R2, R3 and R4 have the meanings set forth in the specification, are very suitable for controlling undesired microorganisms and animal pests. New 7-oxabicyclo[2.2.1]heptane derivatives of formula (Ia) in which X, R1, R2, R3 and R14 have the meanings set forth in the specification, and a process for the preparation of the new compounds.