5221-53-4

Basic information

• Product Name: DIMETHIRIMOL
• Synonyms: 'LGC' (1633);DIMETHIRIMOL;MILCURB;2-dimethylamino-4-hydroxy-5-n-butyl-6-methylpyrimidine;2-dimethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine;5-butyl-2-(dimethylamino)-6-methyl-4(1h)-pyrimidinone;5-butyl-2-(dimethylamino)-6-methyl-4-pyrimidinol;5-butyl-2-dimethylamino-6-methyl-4-pyrimidino
• CAS NO: 5221-53-4
• Molecular Formula: C₁₁H₁₉N₃O
• Molecular Weight: 209.29
• EINECS: 226-021-7
• Mol File: 5221-53-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 103℃
• Boiling Point: 348.66°C (rough estimate)
• Flash Point: 132.9°C
• Appearance: /
• Density: 1.0465 (rough estimate)
• Vapor Pressure: 0.00147mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 0-6°C
• PKA: 5
• Water Solubility: 1.2 g l-1 (25 °C)
• CAS DataBase Reference: DIMETHIRIMOL(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHIRIMOL(5221-53-4)
• EPA Substance Registry System: DIMETHIRIMOL(5221-53-4)

Safety Data

• Hazard Codes: Xn
• Statements: 21-52
• Safety Statements: 36/37
• Hazardous Substances Data: 5221-53-4(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
DIMETHIRIMOL is used as a systemic fungicide for both protective and curative control of powdery mildew (Sphaeratheca fulginea) in cucurbits. It is effective in preventing and treating fungal infections in crops such as tobacco, tomatoes, and ornamentals.
Used in Fungicide Industry:
DIMETHIRIMOL is used as a fungicide to prevent powdery mildew and other fungal infections in crops. It was widely utilized in glasshouses to control powdery mildew, but its use has been discontinued within the European Union due to regulatory changes.

Metabolic pathway

Information presented in this summary is abstracted from unpublished data in the 1971 ICI dimethirimol petition submitted to the Canadian authority. Dimethirimol is rapidly metabolised in both plants and animals. Primary metabolic reactions in soils, plants and animals are N-dealkylation, hydroxylation of the butyl group and the direct conjugation of dimethirimol in plants (glucosides) and animals (glucuronides). Metabolic pathways are shown in Scheme 1.

Degradation

Dimethirimol (1) is stable to heat and in acid and alkahe solutions. It is decomposed rather rapidly in aqueous solution when exposed to sunlight with an observed DT50 of 7 days.

InChI:InChI=1/C11H19N3O/c1-5-6-7-9-8(2)12-11(14(3)4)13-10(9)15/h5-7H2,1-4H3,(H,12,13,15)

Upstream product

• 32798-42-8 methyl α-butylacetoacetate 
• 311-77-3 1,1-dimethylguanidine dihydrogensulfate 

Downstream Products

• 28216-96-8 sodium salt of 2-dimethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine 
• 28216-95-7 potassium salt of 2-dimethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine 

Relevant articles and documents

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.

Iminooxy-substituted benzyl phenyl ethers, processes and intermediates for their preparation, compositions comprising them, and their use for controlling harmful fungi

Iminooxy-substituted benzyl phenyl ethers of the formula I in which the substituents and the index are as defined below: Y is H, CH3, F or Cl; Q is C(═CHOCH3)—COOCH3, C(═CHCH3)—COOCH3, C(═NOCH3)—COOCH3, C(═NOCH3)—CONHCH3 or N(—OCH3)—COOCH3; X is hydrogen, halogen, alkyl, alkoxy or CF3; m is 1 or 2, where the radicals X may be different if m=2; R1 is alkyl and R2 is hydrogen or alkyl; or R1 and R2 together are cyclopropyl, cyclopentyl or cyclohexyl; R3 is alkyl or CF3; and R4 is alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl; processes and intermediates for their preparation, compositions comprising them, and their use, are described.

2-(Pyrazolyloxy) -pyridin-3-ylacetic acid derivatives, agents containing the same and use thereof against noxious fungi and animal parasites

Compounds of the formula I and salts thereof, in which the substituents and the index n have the following meanings: Q is —C(═CHCH3)—COOCH3, —C(═CHOCH3)—COOCH3, —C(═NOCH3)—COOCH3or —C(═NOCH3)—CONH(CH3); R1is hydrogen, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy or C1-C2-haloalkoxy; R2is halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy; n is 0, 1 or 2, where the substituents R2may be different if n=2; R3is phenyl, pyridyl or pyrimidyl, compositions comprising them and the use of the compounds I and the compositions for controlling harmful fungi and animal pests are described.

Bisimino-substituted phenyl compounds and their use as pesticides

Imino-substituted phenyl compounds of the formula I where the substituents have the following meanings:z is a group A or B ?where? denotes the bond with the phenyl ring and?Ra is halogen, alkyl or alkoxy;y is halogen, alkyl, haloalkyl or alkoxy;n is 0, 1 or 2, it being possible for the radicals Y to be different if n=2;R1 is halogen, haloalkyl or alkoxy;R2 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;R3 is cyano, alkyl, haloalkyl, alkoxy, cycloalkoxy, alkoxyalkyl;?unsubstituted or substituted cycloalkyl, aryl, aryloxy or arylmethylene, heteroaryl, heterocyclyl,?C(R3a)=N—OR3b or C(R3a)=CR3cR3d, whereR3a, R3b, R3c, R3d independently of one another are hydrogen, alkyl or unsubstituted or substituted phenyl,processes for their preparation, and their use.

Method for combating harmful fungi

A method for control of harmful fungi is provided by treating the fungi, or the materials, plants, the soil or seeds to be protected against fungal infection, with an effective amount of a bisoxime of the formula I or a salt or adduct thereof, the index and the substituents having the following meanings: R1is halogen, alkyl or haloalkyl; R2is cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, alkylaminocarbonyl, substituted or unsubstituted phenyl, phenoxy or phenylthio; n is 0, 1, 2 or 3; R3is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl or phenylalkyl.

P-hydroxyaniline derivatives, their preparation and their use

p-Hydroxyaniline derivatives of the formula I STR1 where the substituents have the following meanings: R1 is unsubstituted or substituted bicycloalkyl or bicycloalkenyl; R2 and R3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; R4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, OR5 or NR5 R6, where R5 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, and R6 is hydrogen or alkyl, and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests are described.

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.

Triazolylthiophosphoric acid esters

Triazolylthiophosphonic esters corresponding to the formula SPC1 Wherein R1 represents a phenyl radical which is substituted by one or more fluorine, bromine and/or iodine atoms, by lower alkyl, lower alkoxy, lower alkylthio, lower trihalogenoalkyl, lower alkyl-SO, lower alkyl-SO2 or O2 N groups, which may be the same or different, or by at least one chlorine and at least one fluorine, bromine or iodine atom, one lower alkyl, lower alkoxy, lower alkylthio, lower trihalogenoalkyl, lower alkyl-SO, lower alkyl-SO2 or O2 N group, or represents an unsubstituted or halogenated and/or alkoxylated phenyl-lower alkyl radical or diphenylmethyl, and one of the symbols R2 and R3 represents hydrogen or a lower alkyl radical and the other represents the radical EQU1 wherein R4 represents a lower alkyl radical or the phenyl radical and R5 represents a lower alkyl radical their manufacture and their use in pest control.

Condensation products

Formamidine compounds of the formula EQU1 or WHEREIN R1 represents a substituted or unsubstituted phenyl radical, R2 represents hydroogen, alkyl, alkenyl or alkinyl and R3 represents acyl their manufacture and their use in pest control.