| Identification | Back Directory | [Name]
BUPIRIMATE | [CAS]
41483-43-6 | [Synonyms]
-4-ol
pp588
NIMROD
nimrodt
BUPIRAMATE
BUPIRIMATE
Bupirimate 25%
Nimrod (Bupirimate)
Bupirimate Standard
Ethyl phenol sulfonate
bupirimate (bsi,iso,ansi)
BUPIRIMATE PESTANAL, 250 MG
BupirimateSolution,100mg/L,1ml
Bupirimate@1000 μg/mL in Methanol
Bupirimate @100 μg/mL in Methanol
2-aethylamino-5-butyl-4-yl-dimethylsulfamat
5-Butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate
5-BUTYL-2-ETHYLAMINO-6-METHYLPYRIMIDIN-4-YL-DIMETHYLSULPHAMATE
dimethyl-sulfamicaci5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinylester
dimethylsulfamicacid5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinylester
n,n-dimethyl-sulfamicaciesterwith5-butyl-2-ethylamino-6-methylpyrimidin
Dimethylsulfamic acid 5-butyl-2-ethylamino-6-methylpyrimidin-4-yl ester
N,N-Dimethylsulfamic acid 5-butyl-2-(ethylamino)-6-methylpyrimidin-4-yl ester
Sulfamic acid, dimethyl-, 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl ester
Sulfamic acid, N,N-dimethyl-, 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl ester
N,N-Dimethylamidosulfuric acid 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl ester | [EINECS(EC#)]
255-391-2 | [Molecular Formula]
C13H24N4O3S | [MDL Number]
MFCD00055518 | [MOL File]
41483-43-6.mol | [Molecular Weight]
316.42 |
| Chemical Properties | Back Directory | [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) | [Fp ]
100 °C | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly) | [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 | [color ]
White to Pale Beige | [Merck ]
13,1482 | [BRN ]
758056 | [Henry's Law Constant]
6.9×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [InChI]
1S/C13H24N4O3S/c1-6-8-9-11-10(3)15-13(14-7-2)16-12(11)20-21(18,19)17(4)5/h6-9H2,1-5H3,(H,14,15,16) | [InChIKey]
DSKJPMWIHSOYEA-UHFFFAOYSA-N | [SMILES]
CCCCc1c(C)nc(NCC)nc1OS(=O)(=O)N(C)C | [LogP]
2.700 | [EPA Substance Registry System]
Bupirimate (41483-43-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
21 | [Safety Statements ]
36/37 | [WGK Germany ]
2 | [RTECS ]
WO5970000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Aquatic Chronic 1
Carc. 2
Skin Sens. 1B | [Toxicity]
LD50 orally in rats: 4000 mg/kg (Finney) |
| Hazard Information | Back Directory | [Description]
A pyrimidine fungicide active against powdery mildew. It has a moderate aqueous solubility and a low volatility. Depending on local conditions, bupirimate may be moderately persistent in both soil and aquatic systems. It is moderately toxic to most fauna and flora species. It has a low oral toxicity to mammals and is a skin and eye irritant. | [Uses]
Bupirimate is a pyrimidine based fungicide with protective and curative activity for the control of fungal diseases by interfearing with nucleic acid synthesis. | [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]
Fungicide. | [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. | [Production Methods]
The commercial synthesis of bupirimate, a pyrimidine-based fungicide, typically begins with the reaction of ethirimol and N,N-dimethylsulfonyl chloride in the presence of potassium carbonate, ethyl acetate, and a catalytic amount of 18-crown-6 ether. This mixture is heated and refluxed to facilitate sulfonation. Once the reaction reaches partial completion, hexamethylenetetramine is added to adjust the pH to around 10, promoting further conversion. After several hours of continued reaction, the mixture is cooled, washed to neutralize, and the organic phase is separated. The solvent is removed, and the product is precipitated at low temperature, dried, and purified to yield bupirimate. | [Mechanism of action]
Systemic with curative and protectant action. Nucleic acid synthesis - adenosin-deaminase. | [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). | [Pesticide Type]
Fungicide |
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