Pyrimethanil
- Product Name
- Pyrimethanil
- CAS No.
- 53112-28-0
- Chemical Name
- Pyrimethanil
- Synonyms
- Pyrimethani;Mytho;SCALA;MYTHOS;Penbotec;Hsdb 6916;Dynmethanil;PYRIMETHANIL;Pyrimethanil 0;Pyrimethanil [iso]
- CBNumber
- CB4473703
- Molecular Formula
- C12H13N3
- Formula Weight
- 199.25
- MOL File
- 53112-28-0.mol
Pyrimethanil Property
- Melting point:
- 96°C
- Boiling point:
- 362.8±45.0 °C(Predicted)
- Density
- 1.15
- vapor pressure
- 2.2 x l0-5 Pa (25 °C)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- DMSO: 130 mg/mL (652.45 mM)
- pka
- 3.52
- form
- Solid
- color
- White to off-white
- Water Solubility
- 0.121 g/L (25 ºC)
- BRN
- 151589
- InChI
- InChI=1S/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)
- InChIKey
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N
- SMILES
- C1(NC2=CC=CC=C2)=NC(C)=CC(C)=N1
- CAS DataBase Reference
- 53112-28-0(CAS DataBase Reference)
- EPA Substance Registry System
- Pyrimethanil (53112-28-0)
Safety
- Hazard Codes
- N
- Risk Statements
- 51/53
- Safety Statements
- 60
- RIDADR
- UN 3077
- WGK Germany
- 2
- HS Code
- 2933599590
- Hazardous Substances Data
- 53112-28-0(Hazardous Substances Data)
- Toxicity
- LD50 (mg/kg): 4061-5358 orally in mice; 4150-5971 orally in rats; >5000 dermally in rats; LC50 (96 hr) in mirror carp, rainbow trout (mg/l): 35.36, 10.56 (Neumann)
N-Bromosuccinimide Price
- Product number
- 31577
- Product name
- Pyrimethanil
- Purity
- PESTANAL
- Packaging
- 250mg
- Price
- $139
- Updated
- 2025/07/31
- Product number
- 40947
- Product name
- Pyrimethanil
- Purity
- certified reference material, TraceCERT?
- Packaging
- 50mg
- Price
- $185
- Updated
- 2024/03/01
- Product number
- P997250
- Product name
- Pyrimethanil
- Packaging
- 10g
- Price
- $1165
- Updated
- 2021/12/16
- Product number
- 42138
- Product name
- Pyrimethanil
- Packaging
- 10g
- Price
- $1460
- Updated
- 2021/12/16
- Product number
- 074289
- Product name
- 4,6-Dimethyl-N-phenyl-2-pyrimidinamine
- Purity
- 95+%
- Packaging
- 10g
- Price
- $215
- Updated
- 2021/12/16
Pyrimethanil Chemical Properties,Usage,Production
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
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)
Uses
Pyrimethanil is a broad spectrum anilino-pyrimidine foliar fungicide. Pyrimethanil functions by inhibiting the biosynthesis of methionine in Botrytis cinerea.
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®
Synthesis
420-04-2
62-53-3
123-54-6
53112-28-0
First, aniline and 50% aqueous cyanamide were added sequentially in an inert atmosphere reactor protected by nitrogen. Subsequently, 32% hydrochloric acid solution was added dropwise to adjust the pH of the reaction system to 2.5, after which the reaction mixture was gradually heated up from 45°C to 95°C within 2 hours, and the pH was maintained at 2.5 by adding hydrochloric acid during the heating process. 80°C was reached, acetylacetone was added dropwise to the reaction system, and at the same time, 50% sodium hydroxide solution was added dropwise to adjust the pH of the reaction system to 7.9, and the reaction was stirred and stirred for 1 hour to keep the temperature at this level. The reaction was maintained at this temperature and stirred for 1 h. At the end of the reaction, the reaction was allowed to stand and stratified, and the lower aqueous phase was separated and discarded. The upper organic phase was distilled at 750-35 mbar under reduced pressure, controlling the temperature at the bottom of the tower not to exceed 125°C, and recovering the excess acetylacetone for subsequent use. At the end of the distillation, the residue was cooled to 80 °C and diluted with the addition of isopropanol. The mixture was then slowly cooled to 0°C to precipitate a solid product, which was collected by filtration through a glass sand core funnel. The reactor was washed with a small amount of water and the washings were combined into the filtrate. The product was washed twice with isopropanol and placed in a vacuum drying oven and dried at 70 °C and 10 mbar. Finally, 324 g (1.626 mol) of 4,6-dimethyl-N-phenylpyrimidin-2-amine was obtained in 81.3% yield of the theoretical value, with 97.6% purity by HPLC (internal standard method) or 99.9% purity by GC (area normalization method). GC analysis conditions: 30 m DB-1701 capillary column (0.32 mm I.D., 0.25 μm film thickness), inlet temperature of 250 ℃, detector (FID) temperature of 300 ℃, injection volume of 0.2 μl (0.1 g/l methanol solution), programmed heating: 50 ℃ was held for 2 min, and then increased to 250 ℃ at 10 ℃/min for 8 min. HPLC analysis conditions: Agilent 1100 series high performance liquid chromatograph; Nucleosil 120-5 C18 column (250×4 mm); injection volume 5 μl, flow rate 1 ml/min, room temperature detection, column pressure 90 bar, detection wavelength 268 nm, running time 8 min; mobile phase: 250 mL Millipore water+ 750 mL acetonitrile+ 1 g of methanol solution. 750 mL acetonitrile + 1 g ammonium acetate; sample solvent: 250 mL Millipore water + 750 mL acetonitrile; quantitative analysis was carried out using pyrimethamine standards of known concentration.
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.
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
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.
References
[1] Patent: US2011/137033, 2011, A1. Location in patent: Page/Page column 2
Pyrimethanil Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Pyrimethanil manufacturers
- Product
- Pyrimethanil 53112-28-0
- Price
- US $10.00/KG
- Min. Order
- 100KG
- Purity
- 99%
- Supply Ability
- 100 mt
- Release date
- 2024-11-21
- Product
- Pyrimethanil 53112-28-0
- Price
- US $0.00/kg
- Min. Order
- 100kg
- Purity
- 10%
- Supply Ability
- 20tons
- Release date
- 2024-07-03
- Product
- Pyrimethanil 53112-28-0
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99
- Supply Ability
- 1000 Kilogram/Kilograms per Month
- Release date
- 2021-08-13