53112-28-0

Basic information

• Product Name: Pyrimethanil
• Synonyms: Mytho;PYRIMETHANIL PESTANAL, 250 MG;2-Pyrimidinamine, 4,6-dimethyl-N-phenyl-;4,6-DIMETHYL-N-PHENYL-2-PYRIMIDINAMINE(PYRIMETHANIL);Dynmethanil;Pyrimethanil Standard;Hsdb 6916;Pyrimethanil [iso]
• CAS NO: 53112-28-0
• Molecular Formula: C₁₂H₁₃N₃
• Molecular Weight: 199.25
• EINECS: 414-220-3
• Mol File: 53112-28-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 96°C
• Boiling Point: 362.8 °C at 760 mmHg
• Flash Point: 173.2 °C
• Appearance: White powder
• Density: 1.15
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: 0-6°C
• PKA: 3.52
• Water Solubility: 0.121 g/L (25 ºC)
• BRN: 151589
• CAS DataBase Reference: Pyrimethanil(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimethanil(53112-28-0)
• EPA Substance Registry System: Pyrimethanil(53112-28-0)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 60
• RIDADR: UN 3077
• WGK Germany: 2
• Hazardous Substances Data: 53112-28-0(Hazardous Substances Data)

Usage

Chemical Properties

Pyrimethanil is a white to light yellow crystalline powder which is sparingly soluble in water but soluble in most organic solvents. Commercial product is available as a brown emulsifiable concentrate.

Uses

Different sources of media describe the Uses of 53112-28-0 differently. You can refer to the following data:
1. Pyrimethanil is a broad spectrum anilino-pyrimidine foliar fungicide. Pyrimethanil functions by inhibiting the biosynthesis of methionine in Botrytis cinerea.
2. Pyrimethanil provides both protective and curative control of fungal diseases in pome fruits (leaf scab caused by Venturiu inaequalis), vines, fruits, vegetables and ornamentals (grey mould)

Preparation

Pyrimethanil is produced by reaction of 2-bromo-4,6-dimethylpyrimidine with aniline.

Definition

ChEBI: Pyrimethanil is a member of the class of aminopyrimidines that is N-phenylpyrimidin-2-amine carrying two additional methyl substituents at positions 4 and 6. A fungicide used to control grey mould on fruit, vegetables and ornamentals as well as leaf scab on pome fruit. Also commonly employed to control Botrytis cinerea throughout the winemaking process in grapes, must, fermenting must and wine. It has a role as an aryl hydrocarbon receptor agonist, an environmental contaminant, a xenobiotic and an antifungal agrochemical. It is an aminopyrimidine, a secondary amino compound and an anilinopyrimidine fungicide.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 30, p. 1942, 1982 DOI: 10.1248/cpb.30.1942

General Description

Pyrimethanil is an anilino-pyrimidine, broad spectrum fungicide primarily used for the control of gray mould and leaf scab on fruits, vegetables and ornamentals. Its mode of action involves inhibition of the secretion of hydrolytic enzymes by the fungi during the infection process, thus stopping the further development of the disease.

Agricultural Uses

Fungicide: Used on grapes, strawberries, tomatoes, onions, beans, cucumbers, eggplant, and ornamental.

Trade name

SCALA?; SN 100309?

Potential Exposure

A pyrimidine fungicide used on grapes, strawberries, tomatoes, onions, beans, cucumbers, eggplant, and ornamental plants.

Metabolic pathway

Limited data are available in the open literature. Information presented in this summary is abstracted from the data evaluation published by the Pesticide Safety Directorate (PSD, 1995). Hydroxylation at the methyl, phenyl or pyrimidine moiety is the primary metabolic pathway of pyrimethanil in soil, plants and animals. Cleavage of the aniho-pyrimidine linkage was observed as a minor metabolic reaction. The formation of nitro- analogues of pyrimethanil is a novel nitration reaction observed in the soil metabolism study (Scheme 1).

Shipping

UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Degradation

Pyrimethanil (1) is stable to hydrolytic degradation in the environmentally relevant pH range (5-9) at 22-50 °C. Pyrimethanil degraded rapidly at pH 4 and 30 °C (DT50 1 day) when the sterile buffered solution was exposed to mercury arc lamp (200-500 nm). The DT50 of pyrimethanil in pH 7 solution under the same photolysis test conditions was ca.77 days. There is no information on the chemical nature of pyrimethanil aqueous photolysis products.

Waste Disposal

Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. If this material cannot be disposed of according to label instruc- tions, it may be dissolved or mixed with a combustible sol- vent and burned in a chemical incinerator equipped with an afterburner and scrubber. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.

InChI:InChI=1/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15)

Upstream product

• 14001-64-0 4,6-dimethyl-2-methylsulfanyl-pyrimidine 
• 62-53-3 aniline 
• 2002-16-6 1-phenylguanidine 
• 123-54-6 acetylacetone 
• 2498-49-9 N-phenylguanidinium sulfate 
• 420-04-2 CYANAMID 
• 42016-93-3 2-chloro-4-iodoaniline 
• 4472-44-0 2-chloro-4,6-dimethylpyrimidine 
• 80426-58-0 2-anilino-4,6-dimethylpyrimidine 1-oxide 
• 74360-10-4 4,6-dimethyl-1-phenylpyrimidine-2(1H)-thione 

Downstream Products

• 218765-43-6 pyrimethanil laurate 
• 767-15-7 2-Amino-4,6-dimethylpyrimidine 
• 21202-05-1 2-acetamidobenzimidazole 

Relevant articles and documents

Synthesis and fungicidal evaluation of some new anilinopyrimidine derivatives

New series of anilinopyrimidine and pyrimido[4,5-c]azepine derivatives were synthesized to evaluate their in vitro antifungal activities. N-acetyl anilinopyrimidine derivative 7 showed similar fungicidal activity against Aspergillus niger compared to the reference fungicidal pyrimethanil 2. In addition, it exhibits shorter bursting time (2.5 μg/ml in 9 h) than fungicidal drug 2 (2.5 μg/ml in 12 h). The brominated pyrimidine derivative 5 displayed higher fungicidal activity than those of the cyano derivative 6 and the 6-bromoalkyl analogs 4. The fused pyrimido[4,5-c]azepine derivative 10 showed lower activity toward A. niger. A new application for the pyridinium bromochromate as a selective brominating agent on the pyrimidine ring rather on the side chain methyl group was studied.

PROCESS FOR PREPARING (4,6-DIMETHYLPYRIMIDIN-2-YL)PHENYLAMINE (PYRIMETHANIL)

A process for preparing (4,6-dimethylpyrimidin-2-yl)phenylamine (pyrimethanil) of the formula by reacting aniline with cyanamide in the presence of an aqueous acid to give the corresponding phenylguanidinium salt and reacting the phenylguanidinium salt with acetylacetone in the presence of an aqueous base, wherein the process is performed as a one-pot process, by not isolating the phenylguanidinium salt formed as an intermediate.

A novel hydride-mediated reductive rearrangement of amide: a facile synthesis of pyrimidyl and triazinyl amines

LiAlH4 and NaBH4 were found to mediate the conversion of 2-(pyrimidyl-2-ylsulfanyl)-N-arylbenzamides and 2-(triazinyl-2-ylsulfanyl)-N-arylbenzamides into pyrimidyl and triazinyl amines under notably mild conditions via a novel reductive rearrangement mechanism. These reactions invent a new route to prepare amines, which are a kind of important biologically active compounds and provide the first insight into a novel hydride-promoted reductive rearrangement of amides.