Amicarbazone Chemical Properties

Melting point:

137.5°

Boiling point:

350℃ at 101.3kPa

Density 

1.12

vapor pressure 

0-0Pa at 20-25℃

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

17.04±0.20(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Air Sensitive

Major Application

agriculture
environmental

InChI

1S/C10H19N5O2/c1-6(2)7-13-15(9(17)14(7)11)8(16)12-10(3,4)5/h6H,11H2,1-5H3,(H,12,16)

InChIKey

ORFPWVRKFLOQHK-UHFFFAOYSA-N

SMILES

NN1C(C(C)C)=NN(C(NC(C)(C)C)=O)C1=O

LogP

1.18 at 25℃

Surface tension

62mN/m at 1g/L and 20℃

EPA Substance Registry System

Amicarbazone (129909-90-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/22

WGK Germany 

WGK 1

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Inhalation
Acute Tox. 4 Oral

Hazardous Substances Data

129909-90-6(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): 1015 orally; >2000 dermally; LC50 in rats (4 hr): 2.242 mg/l air; LC50 in bluegill sunfish, rainbow trout (96 hr): >129, >120 mg/l (Philbrook)

Amicarbazone Usage And Synthesis

Uses

Herbicide.

Definition

ChEBI: A member of the class of triazoles that is 4,5-dihydro-1H-1,2,4-triazol-5-one which is substituted at position 1 by a tert-butylaminocarbonyl group and at position 3 by an isopropyl group. A selective herbicide for pre- and ost-emergence control of annual dicotyledonous weeds and grasses, it is not approved for use within the European Union.

Synthesis

Amicarbazone is synthesized in four steps. 1) Synthesis of tert-butyl isocyanate: tert-Butylamine reacts with phosgene in o-dichlorobenzene in the presence of NaOH. Distillation yields the product. 2) Synthesis of diazolone: Isobutyric acid reacts with hydrazine hydrate in toluene. Titanium isopropoxide catalyst is added for reflux to remove water. After filtration, phosgene is introduced. Desolvation under reduced pressure gives the product. 3) Synthesis of triazolone: Hydrazine hydrate is heated with NaOH solution under reflux. Diazolone is added dropwise. After cooling, pH is adjusted. Filtration, washing, and drying yield the product. 4) Synthesis of amicarbazone: Triazolone, KOH, and LiCl in methyl acetate are heated. tert-Butyl isocyanate is added dropwise under reflux. After cooling, filtration, desolvation, and drying give the product.

Amicarbazone(129909-90-6)Related Product Information

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