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BUPIRIMATE

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BUPIRIMATE Basic information

Product Name:
BUPIRIMATE
Synonyms:
  • Bupirimate 25%
  • BUPIRIMATE PESTANAL, 250 MG
  • Sulfamic acid, dimethyl-, 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl ester
  • bupirimate (bsi,iso,ansi)
  • BUPIRAMATE
  • 5-Butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate
  • 5-BUTYL-2-ETHYLAMINO-6-METHYLPYRIMIDIN-4-YL-DIMETHYLSULPHAMATE
  • BUPIRIMATE
CAS:
41483-43-6
MF:
C13H24N4O3S
MW:
316.42
EINECS:
255-391-2
Product Categories:
  • BI - BZBuilding Blocks
  • PyrimidinesPesticides
  • A-BAlphabetic
  • Alpha sort
  • B
  • Fungicides
  • Heterocyclic Building Blocks
  • Pesticides&Metabolites
  • Pyrimidines
Mol File:
41483-43-6.mol
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BUPIRIMATE Chemical Properties

Melting point:
50-51°
Boiling point:
463.2±55.0 °C(Predicted)
Density 
1.2120 (rough estimate)
vapor pressure 
1.0 x 10-4 Pa at 25 °C
refractive index 
1.6200 (estimate)
Flash point:
100 °C
storage temp. 
0-6°C
form 
neat
pka
5
Water Solubility 
22 mg l-1 (pH 5.2), 18 mg l-1 (pH 7.3), 17 mg l-1 (pH 9.3) at 25 °C
Merck 
13,1482
BRN 
758056
InChIKey
DSKJPMWIHSOYEA-UHFFFAOYSA-N
EPA Substance Registry System
Bupirimate (41483-43-6)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
21
Safety Statements 
36/37
WGK Germany 
2
RTECS 
WO5970000
Toxicity
LD50 orally in rats: 4000 mg/kg (Finney)
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BUPIRIMATE Usage And Synthesis

Uses

Fungicide.

Uses

Bupirimate is a systemic fungicide that provides protective and curative control of powdery mildew (Podosphaera leucotricha) mainly in pome fruits, stone fruits and glasshouse roses. Other uses include berries, vines and cucurbits.

Uses

Bupirimate is a pyrimidine based fungicide with protective and curative activity for the control of fungal diseases by interfearing with nucleic acid synthesis.

Definition

ChEBI: A member of the class of aminopyrimidines that is 2-ethylaminopyrimidine carrying methyl, butyl and dimethylaminosulfooxy substituents at posiitons 4, 5 and 6 respectively.

Metabolic pathway

Bupirimate degrades rapidly when exposed to sunlight. Minimal penetration of bupirimate residues in treated apples was observed. Degradation of bupirimate in/on fruit surfaces was mainly due to photolytic processes. Metabolism in plants and animals is similar and includes the initial cleavage of the dimethylsulfamate-pyrimidine linkage to yield ethirimol which is also an active fungicide. Numerous degradation products were generated from N-dealkylation, hydroxylation and conjugation reactions and the opening of the pyrimidine ring (Scheme 1).

Degradation

Bupirimate (1) is stable in dilute alkaline solution, but readily hydrolysed in dilute acidic solution. Bupirimate was rapidly decomposed in aqueous solution when exposed to sunlight (Hassall, 1982). Cleavage of the dimethylsulfamate-pyrimidine linkage yielded ethirimol [5-butyl-2- ethylamino-6-methylpyrimidin-4-ol (2)] as the major product. Ethirimol, an active fungicide, was degraded slowly under these test conditions. Four additional minor products were also detected. Three of these products were identified aS isomers of bupirimate, resulting from the migration of the dimethylsulfamate moiety to the various nitrogen molecules (compounds 3, 4 and 5; Cavell and Lincoln, 1974; Teal and Skidmore, 1976).

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