53112-28-0 Usage
Description
Pyrimethanil is a broad-spectrum anilino-pyrimidine foliar fungicide that functions by inhibiting the biosynthesis of methionine in Botrytis cinerea.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 53112-28-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,1,1 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 53112-28:
(7*5)+(6*3)+(5*1)+(4*1)+(3*2)+(2*2)+(1*8)=80
80 % 10 = 0
So 53112-28-0 is a valid CAS Registry Number.
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)
53112-28-0Relevant articles and documents
Synthesis and fungicidal evaluation of some new anilinopyrimidine derivatives
Waly, Mohamed A.,Bader-Eldien, Eman T.,Aboudobarah, Mohamed E.,Aboumosalam, El-Shahat T.
, p. 5267 - 5273 (2013)
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)
-
Page/Page column 2, (2011/06/24)
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
Chen, Xiang,Wu, Jun,Shang, Zhicai,Chen, Meifeng,Sun, Yanping,Lv, Jing,Lei, Meikang,Zhang, Peizhi
, p. 495 - 499 (2008/04/13)
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.
