53112-28-0

Usage

Uses

Used in Agriculture:
Pyrimethanil is used as a fungicide for both protective and curative control of fungal diseases in various crops, including pome fruits, vines, fruits, vegetables, and ornamentals.
Used in Pome Fruits:
Pyrimethanil is used as a fungicide for controlling leaf scab caused by Venturia inaequalis in pome fruits.
Used in Vines, Fruits, Vegetables, and Ornamentals:
Pyrimethanil is used as a fungicide for managing grey mould in vines, fruits, vegetables, and ornamentals.

Preparation

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

Synthesis Reference(s)

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

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

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

Downstream Products

• 107923-94-4 N,N-diethyl-N'-(4,6-dimethyl-pyrimidin-2-yl)-N'-phenyl-ethylenediamine 
• 116389-21-0 (4,6-dimethyl-pyrimidin-2-yl)-nitroso-phenyl-amine 
• 767-15-7 2-Amino-4,6-dimethylpyrimidine 
• 25513-98-8 2,4-dimethylpyrimido<1,2-a>benzimidazole 
• 1449337-59-0 C₉H₁₁N₃O 
• 1449337-60-3 C₁₂H₁₃N₃ 
• 1449337-61-4 C₁₂H₁₁N₃O 
• 1449337-62-5 C₁₂H₁₃N₃O 
• 62-53-3 aniline 

Relevant academic research and scientific papers

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.

Microwave-assisted simple synthesis of 2-anilinopyrimidines by the reaction of 2-chloro-4,6-dimethylpyrimidine with aniline derivatives

A series of 2-anilinopyrimidines including novel derivatives has been obtained from 2-chloro-4,6-dimethylpyrimidine by aromatic nucleophilic substitution with differently substituted anilines under microwave conditions. The substituents had a significant impact on the course and efficiency of the reaction. The results reported herein demonstrate the efficacy of microwaves in the synthesis of the title heterocyclic compounds as compared to the results obtained with conventional heating. The 2-anilinopyrimidines described are of potential bioactivity.

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.

One-pot two-step solvent-free rapid and clean synthesis of 2-(substituted amino)pyrimidines by microwave irradiation

abs A series of diversely 2-(substituted amino)pyrimidines (along with ring substitution) has been synthesized under solvent- and catalyst-free microwave conditions from substituted guanidines and β-diketones. The substituted guanidines are synthesized from (S)-methylisothiourea sulfate and different amines (various alkyl, aryl, or heterocyclic and also chiral amines) under microwave irradiation. These two-step reactions are performed in one-pot without isolating any intermediate. This protocol has been successfully applied for the synthesis of bisaminopyrimidines and 2-substituted aminopyrimidines containing chiral moiety where chirality remains undisturbed.

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.

Substituted imide derivatives

The present invention relates to novel substituted imide derivatives of the general formula (I) in which R1 represents optionally substituted cycloalkyl, R2 represents optionally substituted alkyl or optionally substituted cycloalkyl, R3 represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and R4 represents cyano or nitro, and to processes for their preparation and to their use for controlling animal pests and as herbicides.

Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides

The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.

Photosynthesis and properties of halomethyl derivatives of azinobenzimidazoles

Photocyclization of 2-(pentafluoroanilino)-, 2-(4-chloro-2-iodoanilino)-, and 2-(2-chloro-4-iodoanilino)-4,6-dimethylpyrimidines, as well as 2-(2-chloro-3-methylanilino)pyridine was used to prepare condensed azinobenzimidazoles, including previously unknown 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole and 9-methylpyrido[1,2-a]benzimidazole. With isomeric chloroiodoanilinopyrimidines as example it was shown that the iodine atom affects photocyclization direction. Quaternization of 6,7,8,9-tetrafluoro-1,3-dimethylpyrimido[1,2-a]benzimidazole, 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole, and 9-methylpyrido[1,2-a]benzimidazole with alkylating agents and C-H activity of alkyl groups in the quaternary salts in reactions with orthoformic ester were studied.

Sulfonyl benzazolones

Sulphonylbenzazolones of the formula in whichR1, R2, R3, R4, R5 and Q are each as defined in the description.a process for preparing these compounds and their use as microbicides in crop protection and in the protection of materials.

2-and 2,5-substituted phenylketoenols

PCT No. PCT/EP97/03973 Sec. 371 Date Jan. 28, 1999 Sec. 102(e) Date Jan. 28, 1999 PCT Filed Jul. 23, 1997 PCT Pub. No. WO98/05638 PCT Pub. Date Feb. 12, 1998The invention relates to novel phenyl-substituted cyclic ketoenols of the formula (I) in which Het represents one of the groups in which A, B, D, G, X and Z are each as defined in the description, to a plurality of processes and intermediates for their preparation, and to their use as pesticides.