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

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

Used in Agricultural Industry:
ETHIRIMOL is used as a systemic fungicide for controlling various fungal diseases in crops. It provides both protective and curative actions, making it a valuable asset in the agricultural sector.
ETHIRIMOL is used as a fungicide for controlling powdery mildew (Erysiphe gmminis) on barley, wheat, and oats. Its application can be in the form of a seed dressing, a foliar spray, or directly to the soil in the root zone.
Used in Sugar Beet Industry:
ETHIRIMOL is used as a fungicide for controlling leaf spot in sugar beet crops, ensuring the health and quality of the produce.

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 
• 1540-29-0 ethyl 2-butylacetoacetate 
• 32798-42-8 methyl α-butylacetoacetate 
• 50693-82-8 monoethylguanidine sulphate 
• 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.

Continuous synthesis method of hydroxypyrimidine compound

The invention discloses a continuous synthesis method of a hydroxypyrimidine compound. The method comprises the steps: carrying out continuous reaction on organic amine and a 50% cyanamide aqueous solution in a micro-reactor, introducing the reaction solution into a liquid separator for continuous phase splitting, carrying out continuous ring closing on a guanidine solution and alpha-alkyl acetoacetate in a second micro-reactor, washing the reaction solution with water, and desolventizing to obtain a target product. The method is based on the concept of green chemistry, the comprehensive costof raw materials is far lower than that of traditional methods, no salt-containing wastewater is generated, and treatment is easy; traditional solid-liquid separation is avoided, automatic productionis facilitated, and the safety and environmental protection level of the device is improved; continuous synthesis is adopted, decomposition of an intermediate is avoided, the total yield is larger than 82%, and the product content reaches 98%.

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.

Preparation method of hydroxypyrimidine compound

The invention discloses a preparation method of a hydroxypyrimidine compound, and the method comprises the following steps of: taking alkyl guanidine salt as a reaction raw material, reacting with sodium hydroxide, potassium hydroxide, sodium methoxide or sodium ethoxide in a methanol solvent or an ethanol solvent, filtering and desolventizing to obtain kettle bottom residue, namely correspondingalkyl guanidine, then adding cosolvent toluene or xylene, adding dehydrating and dealcoholizing agent cyclohexane, n-hexane or n-heptane, and reacting with alpha-alkyl acetoacetate alkyl ester to dehydrate and dealcoholize to obtain the hydroxypyrimidine compound. In the invention, neutralization of the alkyl guanidine salt is carried out first, and then an inorganic salt is filtered, and the waste water amount is greatly reduced; the cyclohexane, the n-hexane or the n-heptane is used as the dehydration and dealcoholization agent, and the toluene or the xylene is used as the cosolvent, so thatgenerated water and alcohols are well separated from the reaction solvent, and the dosage of the reaction solvent and the reaction temperature are reduced. The alpha-alkyl acetoacetate alkyl ester istaken as a reference raw material, and the reaction process is convenient to monitor. And that yield of the hydroxypyrimidine compound is more than 90%.

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.

Delta1-pyrrolines used as pesticides

Novel Δ1-pyrrolines of the formula (I) in which Ar1, Ar2 and Q are each as defined in the description, a plurality of processes for preparing these substances and their use for controlling pests.

Delta 1-pyrrolines used as pesticides

Novel Δ1-pyrrolines of the formula (I) in which R1, R2, R3, m and Q have the meanings given in the description, a plurality of processes for preparing these substances and their use for controlling pests.

Glyoxylic acid derivatives

The invention concerns novel glyoxylic acid derivatives, a process for their preparation and their use as pesticides.

Halogen pyrimidinyl aryl (thio)ethers as pesticides

The invention relates to novel halogenopyrimidines, to two processes for their preparation and to their use as pesticides.

NEW AMINOPYRIMIDINONIC DERIVATIVES WITH POTENTIAL BIOLOGICAL ACTIVITY

In the industrial synthesis of fungicide, ethyrimol (I) (5-butyl-2-ethylamino-6-methyl-4-pyrimidinol), starting from ethylguanidine nitrate and butylacetoacetic ester, a by product (15 percent of the main product) was also formed: the 2-amino-5-butyl-3-ethyl-4-pyrimidinone (II). In order to render valuable this by-product by means of some of its potentially biologic active derivatives, its 2-amino function was used. By acylation with phenoxyacetyl chlorides, tosyl chloride, p-acetylaminobenzenesulfonic chloride, the corresponding amides were obtained. The amino function was also replaced by the hydroxyl and chlorine groups. With phosgene the N,N-disubstituted urea was obtained. The new compounds were characterized by means of 1H-NMR and IR spectra, some of them proving a biological activity.