40778-16-3

Basic information

• Product Name: PIRIMICARB-DESAMIDO
• Synonyms: 2-(dimethylamino)-5,6-dimethyl-4(3H)-pyrimidinone;2-(dimethylamino)-5,6-dimethyl-1H-pyrimidin-4-one;ddhp;4,5-DIMETHYL-2-(DIMETHYLAMINO)-6-HYDROXYPYRIMIDINE;2-(dimethylamino)-5,6-dimethylpyrimidin-4-ol;2-dimethylamino-4-hydroxy-5，6-dimetyhl pyrimidine;2-(Dimethylamino)-5,6-dimethylpyrimidin-4(1H)-one;5,6-Dimethyl-2-(dimethylamino)pyrimidin-4-ol
• CAS NO: 40778-16-3
• Molecular Formula: C₈H₁₃N₃O
• Molecular Weight: 167.20832
• EINECS: 255-074-9
• Mol File: 40778-16-3.mol

Chemical Properties

• Boiling Point: 243.1°Cat760mmHg
• Flash Point: 100.8°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 0.0326mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: PIRIMICARB-DESAMIDO(CAS DataBase Reference)
• NIST Chemistry Reference: PIRIMICARB-DESAMIDO(40778-16-3)
• EPA Substance Registry System: PIRIMICARB-DESAMIDO(40778-16-3)

Safety Data

• Hazardous Substances Data: 40778-16-3(Hazardous Substances Data)

Usage

Metabolic pathway

Photolysis of solutions of methylene blue and 2- dimethylamino-5,6-dimethylpyrimidin-4-ol in CDCl3 and d6-acetone in an NMR sample tube with irradiation from a 600 W tungsten ? halogen lamp while dry oxygen is bubbled through the solution202 Not a pesticide: hydrolysis product of pirimicarb fungicide Photolysis of solutions of methylene blue and 2- dimethylamino-5,6-dimethylpyrimidin-4-ol gives the photolysis product of the zwitterion which is stable in solution at ambient temperature. It is suggested that, when the zwitterion is in contact with the silica gel of the TLC plate, it gives some degradation products, and if the zwitterion were to be formed in the environment on photooxidation of the pyrimidinol, and in contact with plant and soil surfaces, then it would react or break down to give further products.

InChI:InChI=1/C8H13N3O/c1-5-6(2)9-8(11(3)4)10-7(5)12/h1-4H3,(H,9,10,12)

Upstream product

• 23103-98-2 pirimicarb 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 311-77-3 1,1-dimethylguanidine dihydrogensulfate 
• 6145-42-2 N,N-Dimethyl-guanidine 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 598-65-2 N,N-dimethylguanidine sulfate 
• 19810-73-2 2-dimethylamino-6-methyl-3H-pyrimidin-4-one 

Relevant articles and documents

Emission and absorption spectra of some substituted 4-hydroxypyrimidines

The fluorescence, phosphorescence and absorption spectra of 5,6-dimethyl-2-dimethylamino-4-hydroxypyrimidine (1), 5-n-butyl-2-dimethylamino-4-hydroxypyrimidine (2), and 5-n-butyl-2-ethylamino-4-hydroxypyrimidine (3) have been obtained in organic media and in aqueous solution at different pH values.The spectra reveal that the pyrimidines exist principally as cations at low pH, neutral species at pH values around 7 and as anions at high pH.The pK values for the ground state of compounds (1)-(3) have been measured as have the pK* values for the first excited singlet state.

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.

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%.

Environmental application of an industrial waste as catalyst for the electro-Fenton-like treatment of organic pollutants

The application of acid mine drainage sludge (AMDS), an industrial waste with high metal content, as catalyst for the electro-Fenton-like technology on the treatment of organic polluted effluents has been investigated. The study has demonstrated the potential use of this waste using dye Lissamine Green B as a model contaminant, which allowed the optimization of sludge dosage and pH. AMDS proved to perform a high decoloration rate at pH 2, however, acidic conditions favored metal leaching. Alginate gel beads were selected to immobilize AMDS and to avoid metal release and the wash out of the reactor operating in continuous mode. This developed catalyst showed high reliability and efficiency in successive batches. The efficacy of the established treatment was also verified on the degradation of pesticide pirimicarb and a degradation pathway was determined by LC-MS studies.

Photocatalytic oxidation of pirimicarb in aqueous slurries containing binary and ternary oxides of zinc and titanium

The photocatalytic degradation of pirimicarb in pure water has been studied using zinc oxide (ZnO), titanium dioxide (TiO2) and zinc titanates (Zn2TiO4 and ZnTiO3) under artificial light (300-460 nm) irradiation. Comparison of catalysts showed that TiO2 is the most efficient for the removal of pirimicarb and their transformation products. To obtain a better understanding of the mechanistic details of these ZnO-TiO2-assisted photodegradation of pirimicarb, the transformation products of the processes were identified by liquid chromatography tandem mass spectrometry (LC-MS2) and liquid chromatography time of flight mass spectrometry (LC-TOF/MS) techniques. The probable photodegradation pathways are proposed and discussed. The main steps involved: N-dealkylation of the 2-dimethylamino group to form the carbamate and decarbamoylation of the carbamate moiety with further N-dealkylation of the 2-dimethylamino group to have the hydroxypyrimidines.

Photodegradation of Pesticides. Photolysis Rates and Half-Life of Pirimicarb and Its Metabolites in Reactions in Water and in Solid Phase

The photodegradation of Pirimicarb under three different artificial lights and sunlight was studied in water solutions (buffers pH 5, 6, and 7) and in solid phase. Five photocompounds were formed in solution and two in solid phase. Pirimicarb undergoes fast degradation under all conditions. In buffer solutions it first gave three compounds with a kinetic parallel process. These compounds were assigned the structures of 2-[(methylformyl)amino]-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (II), 2-(methylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (III), and 2-(dimethylamino)-5,6-dimethyl-4-hydroxypyrimidine (V). V and II were stable to further photolysis (the latter with t1/2 = 849 h) whereas III undergoes further degradation to 2-amino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (IV), and to 2-(formylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (IX). Both compounds were photodegraded to undetectable species, and IX shows a very high t1/2 (48 h). A different behavior was found in solid phase, and only II and III were formed. A kinetic parallel process was demonstrated. The environmental t1/2 and t1/100 calculated for Pirimicarb and its photoproducts suggest their reduced persistence in natural waters.

Manufacture of 2-(alkyl)amino-4-hydroxy-5-alkylpyrimidines

Reaction of a 2-amino-, 2-alkylamino- or 2-dialkylamino-4-hydroxypyrimidine, preferably also containing a methyl group at the 6 position, with an aldehyde R--CHO in presence of hydrogen and a hydrogenation catalyst introduces an alkyl group R--CH2 -- into the 5 position. The reaction is preferably carried out under superatmospheric pressure at a temperature between 80° and 180°C and is aided by metal salts, acids, amines, amine salts or basic ion-exchange resins.