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

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

Used in Agriculture:
BUPIRIMATE is used as a systemic fungicide for the control of powdery mildew (Podosphaera leucotricha) in pome fruits, stone fruits, and glasshouse roses. It offers protective and curative control, ensuring the health and quality of the crops.
Additionally, BUPIRIMATE is used in the cultivation of berries, vines, and cucurbits, providing effective control against fungal diseases and promoting healthy plant growth.
Used in Fungal Disease Control:
BUPIRIMATE is used as a fungicide with protective and curative activity for the control of fungal diseases in various plants. By interfering with nucleic acid synthesis, it helps prevent the growth and spread of fungi, thus protecting plants from infections and maintaining their overall health.

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.

Synthetic method of bupirimate

The invention discloses a synthetic method of bupirimate. The synthetic method comprises the following steps of sequentially adding ethirimol, alkali, a solvent and water into a reaction bottle, heating to 50-80 DEG C while stirring, slowly dropwise adding N, N-dimethylsulfonyl chloride, heating until reflux reaction after finishing dropwise adding, adding organic alkali to control the pH value ofthe system to be alkaline when 5-50% of the raw materials are left, and continuously reacting until the reaction is finished, and cooling the system to 50-60 DEG C, washing with water to adjust the system to be neutral, removing the water phase, removing the solvent to obtain an oily substance, and separating out a solid at low temperature, thereby obtaining the bupirimate. The synthetic method provided by the invention has the advantages of mild conditions, simple operation, less three wastes and high yield, and is a synthetic method suitable for industrialization of bupirimate.

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.

Glyoxyl acid amides, method for producing them and their use for controlling harmful organisms

The invention relates to novel gloyoxylic acid amides, to a process for their preparation and to their use for controlling harmful organisms.

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.

Triazolopyrimidines

The invention relates to novel triazolopyrimidines of the formula 1wherein X represents halogen, Y represents a hydrogen atom or halogen, and R has the meanings given in the disclosure, to a process for the preparation of the new compounds, and to their use as microbicides.

Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides(III)

The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 3 to 10, n represents 0, 1 or 2, Y represents sulphur or oxygen, R1 represents halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl and R2 represents hydrogen, halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl, ?except for compounds where R1=alkyl, Y=oxygen and X=hydrogen, and to processes for their preparation and to their use as pesticides.

Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (I)

The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 2 to 10, n represents 0, 1 or 2, Y represents unsubstituted or substituted methylene and p represents 1, 2 or 3. and to processes for their preparation and to their use as pesticides.

Substituted imide derivatives

The present invention relates to novel substituted imide derivatives of the general formula (I) in which R1 represents optionally substituted cycloalkyl, R2 represents optionally substituted alkyl or optionally substituted cycloalkyl, R3 represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and R4 represents cyano or nitro, and to processes for their preparation and to their use for controlling animal pests and as herbicides.

Substituted 3-thiocarbamoylpyrazoles

The invention relates to novel substituted 3-thiocarbamoylpyrazoles of general formula (I), wherein m, n, R1, R2, R3and Ar have the meanings cited in the description. The invention further relates to methods for the production and use thereof as pesticides.