23947-60-6

Basic information

• Product Name: ETHIRIMOL
• Synonyms: 2-Ethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine;4(1H)-Pyrimidinone, 5-butyl-2-(ethylamino)-6-methyl-;4(3H)-Pyrimidinone, 5-butyl-2-(ethylamino)-6-methyl-;4(3H)-pyrimidinone,5-butyl-2-(ethylamino)-6-methyl-;5-butyl-2-(ethylamino)-6-methyl-4(1h)-pyrimidinon;5-Butyl-2-(ethylamino)-6-methyl-4(1H)-pyrimidinone;5-Butyl-2-(ethylamino)-6-methyl-4(1H)-pyrim-idinone;5-n-Butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine
• CAS NO: 23947-60-6
• Molecular Formula: C₁₁H₁₉N₃O
• Molecular Weight: 209.29
• EINECS: 245-949-3
• Product Categories: Alpha sort;E;E-GAlphabetic;EQ - EZPesticides;Fungicides;Pesticides&Metabolites;Pyrimidines
• Mol File: 23947-60-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 159-160°
• Boiling Point: 348.66°C (rough estimate)
• Flash Point: 139 °C
• Appearance: /
• Density: 1.2100
• Vapor Pressure: 0.000781mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Sparingly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 5
• Water Solubility: 253 mg l-1 (pH 5.2), 150 mg l-1 (pH 7.3), 153 mg l-1 (pH 9.3) at 20 °C
• Merck: 13,3776
• BRN: 882476
• CAS DataBase Reference: ETHIRIMOL(CAS DataBase Reference)
• NIST Chemistry Reference: ETHIRIMOL(23947-60-6)
• EPA Substance Registry System: ETHIRIMOL(23947-60-6)

Safety Data

• Hazard Codes: Xn
• Statements: 21
• Safety Statements: 36/37
• WGK Germany: 1
• RTECS: UW7380000
• Hazardous Substances Data: 23947-60-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 23947-60-6 differently. You can refer to the following data:
1. Fungicide.
2. Ethirimol is a systemic fungicide with both protective and curative actions. It controls mainly powdery mildew (Erysiphe gmminis) on barley, wheat and oats. Ethirimol can be applied as a seed dressing, as a foliar spray or directly to the soil in the root zone.
3. Ethirimol is a pyrimidine based fungicide with wide applications such as controlling leaf spot of sugar beet.

Definition

ChEBI: An aminopyrimidine that is 2-ethylaminopyrimidin-4-one carrying butyl and methyl substituents at positions 5 and 6 respectively. A fungicide first marketed in 1970 and used as a seed treatment for diseaases such as damping-off, it is not licensed for use w thin the European Union.

Metabolic pathway

Ethirimol is susceptible to photodegradation and it also degrades extensively in soil to yield CO2 and unextractable soil-bound residues. Metabolism in plants and animals is extensive to yield up to 16 metabolites. Elimination in animals was rapid following oral dosing. Metabolism in soil, plants and animals follows common pathways which include N-dealkylation, hydroxylation of the butyl group and conjugation.

Degradation

Ethirimol (1) is stable to hydrolytic degradation in buffered solutions at pH 5, 7 and 9 at 22°C. It degraded under aqueous photolysis test conditions with a half-life (DT50) of ca. 3 weeks. The primary photolytic degradation reactions include the opening of the pyrimidine ring to yield ethylguanidine (2), urea (3) and 4-butylpyrazolidine-3,5-dione (4) (Cavell et al., 1974c).

InChI:InChI=1/C11H19N3O/c1-4-6-7-9-8(3)13-11(12-5-2)14-10(9)15/h4-7H2,1-3H3,(H2,12,13,14,15)

Upstream product

• 503-69-5 ethyl guanidine 
• 32798-42-8 methyl α-butylacetoacetate 
• 50693-82-8 monoethylguanidine sulphate 
• 1540-29-0 ethyl 2-butylacetoacetate 
• 123-72-8 butyraldehyde 
• 5734-69-0 2-ethylamino-4-hydroxy-6-methylpyrimidine 

Downstream Products

• 41483-43-6 bupirimate 

Relevant articles and documents

Preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine

The invention discloses a preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine, which comprises the following steps: by using ethylamine and cyanamide as initial raw materials, generating N-ethylguanidine sulfate under the action of concentrated sulfuric acid, reacting with 2-n-butyl ethyl acetoacetate under the action of sodium hydroxide for 1-4 hours, and carrying out after-treatment to obtain 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine. According to the method, cheap and easily available ethylamine and cyanamide are used as initial raw materials, the method is green and environment-friendly, isomers are separated by using a preparative chromatography technology, the yield and purity of the product are relatively high, and the method has a wide industrial application prospect.

Synthetic method of hydroxypyrimidine compound

The invention discloses a synthesis method of a hydroxypyrimidine compound, which comprises the following steps: adding alkyl guanidine salt into a methanol or ethanol solvent, adding a neutralizing reagent to carry out a neutralization reaction, filtering, and removing the solvent from the filtrate to obtain the residue alkyl guanidine; mixing alkyl guanidine with alkyl alpha-alkylacetoacetate, reacting in an inert atmosphere at 90-140 DEG C until water and methanol are separated, cooling to 60-80 DEG C after the reaction is finished, adding alkyl hydrocarbon into the reaction solution, stirring for 10-30 minutes, cooling to room temperature, filtering and washing to obtain the hydroxypyrimidine compound. According to the synthesis method, no solvent reaction exists, so that the single-kettle reaction efficiency is greatly improved; in addition, dehydration and degreasing are carried out in an inert atmosphere, so that deterioration of alkyl alpha-alkylacetoacetate at high temperatureis effectively avoided, and the reaction safety is also improved. Therefore, the synthesis method disclosed by the invention has the advantages of high single-kettle reaction efficiency, high safetyand less three wastes.

Optically active 2,5-bisaryl-delta1-pyrrolines and their use as pest control agents

Novel optically active Δ1-pyrrolines of the formula (I) in which R1, R2, R1, R4, and m are each as defined in the description, a plurality of the processes for preparing these substances and their use for controlling pests.