BUPIRIMATE Property

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)

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

Hazard Codes 

Xn

Risk Statements 

21

Safety Statements 

36/37

WGK Germany 

2

RTECS 

WO5970000

Toxicity

LD50 orally in rats: 4000 mg/kg (Finney)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H312Harmful in contact with skin

H317May cause an allergic skin reaction

H351Suspected of causing cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

BUPIRIMATE Chemical Properties,Usage,Production

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).