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

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)

form 

Solid

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

InChIKey

DSKJPMWIHSOYEA-UHFFFAOYSA-N

LogP

2.700

EPA Substance Registry System

Bupirimate (41483-43-6)

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)

BUPIRIMATE Usage And 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

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

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.

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).

BUPIRIMATE(41483-43-6)Related Product Information

• CYCLOPROTHRIN
• ALDEHYDE DEHYDROGENASE
• 2,4-DIMETHYL, 1,3-DIOXALONE
• Ethyl glyoxalate
• Glyoxylic acid
• Cinnamyl acetate
• Butyl acetate
• Amyl acetate
• Abiraterone acetate
• PEG6-(CH2CO2H)2
• BETA-ESTRADIOL 17-ACETATE
• 2-Pyrimidinamine, N-methyl- (9CI)
• Sulfamic acid
• ETHIRIMOL
• 2-Amino-6-methyl-4-pyrimidinol
• METHYLSULFAMIC ACID
• 5-METHYLPYRIMIDIN-4-OL
• Bupirimate PESTANAL