ETHIRIMOL Chemical Properties

Melting point:

159-160°

Boiling point:

348.66°C (rough estimate)

Density 

1.2100

vapor pressure 

2.7 x 10^-4 Pa at 25 °C

refractive index 

1.5700 (estimate)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Sparingly), Ethanol (Slightly), Methanol (Slightly)

pka

5

Water Solubility 

253 mg l^-1 (pH 5.2), 150 mg l^-1 (pH 7.3), 153 mg l^-1 (pH 9.3) at 20 °C

color 

White to Off-White

Merck 

13,3776

BRN 

882476

InChI

InChI=1S/C11H19N3O/c1-4-6-7-9-8(3)13-11(12-5-2)14-10(9)15/h4-7H2,1-3H3,(H2,12,13,14,15)

InChIKey

BBXXLROWFHWFQY-UHFFFAOYSA-N

SMILES

C1(NCC)=NC(C)=C(CCCC)C(=O)N1

EPA Substance Registry System

Ethirimol (23947-60-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

21

Safety Statements 

36/37

WGK Germany 

1

RTECS 

UW7380000

Toxicity

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

ETHIRIMOL Usage And Synthesis

Chemical Properties

White crystal. Melting point 159-160°C. Vapor pressure at 25°C is 0.267×10-3Pa. Solubility in water at 25°C is 200mg/L. Soluble in chloroform, trichloroethylene, strong acid and strong alkali solution, slightly soluble in ethanol, almost insoluble in acetone, stable to heat.

Uses

Ethirimol is a systemic fungicide with both protective and curative actions. It controls mainly powdery mildew (Erysiphe gmminis) on barley, wheat and oats. Ethirimol can be applied as a seed dressing, as a foliar spray or directly to the soil in the root zone.

Uses

Ethirimol is a pyrimidine based fungicide with wide applications such as controlling leaf spot of sugar beet.

Uses

Fungicide.

Definition

ChEBI: An aminopyrimidine that is 2-ethylaminopyrimidin-4-one carrying butyl and methyl substituents at positions 5 and 6 respectively. A fungicide first marketed in 1970 and used as a seed treatment for diseaases such as damping-off, it is not licensed for use w thin the European Union.

Metabolic pathway

Ethirimol is susceptible to photodegradation and it also degrades extensively in soil to yield CO2 and unextractable soil-bound residues. Metabolism in plants and animals is extensive to yield up to 16 metabolites. Elimination in animals was rapid following oral dosing. Metabolism in soil, plants and animals follows common pathways which include N-dealkylation, hydroxylation of the butyl group and conjugation.

Degradation

Ethirimol (1) is stable to hydrolytic degradation in buffered solutions at pH 5, 7 and 9 at 22°C. It degraded under aqueous photolysis test conditions with a half-life (DT₅₀) of ca. 3 weeks. The primary photolytic degradation reactions include the opening of the pyrimidine ring to yield ethylguanidine (2), urea (3) and 4-butylpyrazolidine-3,5-dione (4) (Cavell et al., 1974c).

ETHIRIMOL(23947-60-6)Related Product Information

• ar-ethoxybenzamide
• Ethionamide
• ETHIRIMOL
• 2-Pyrimidinamine, N-methyl- (9CI)
• 2-Amino-6-methyl-4-pyrimidinol
• 5-ETHYL-2-PYRIMIDINAMINE
• 5-METHYLPYRIMIDIN-4-OL
• BUPIRIMATE
• 4-Hydroxy-6-methylpyrimidine
• 2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE
• 2-Pyrimidinamine, 5-methyl- (9CI)
• 2-AMINO-5-ETHYL-6-METHYLPYRIMIDIN-4-OL
• 5-PROPYL-2-PYRIMIDINAMINE
• 5,6-DIMETHYL-PYRIMIDIN-4-OL
• 6-METHYL-5-PROPYL-4(1H)-PYRIMIDINONE
• CHEMBRDG-BB 9072033
• 4(1H)-Pyrimidinone, 2-amino-5-methyl- (7CI,8CI,9CI)
• 5-ethylpyrimidin-4-ol