FENTRAZAMIDE Chemical Properties

Melting point:

79°

Boiling point:

434.4±47.0 °C(Predicted)

Density 

d20 1.30

vapor pressure 

0-0Pa at 20-25℃

storage temp. 

0-6°C

pka

-1.03±0.20(Predicted)

LogP

3.6 at 20℃

Surface tension

66-69mN/m at 700-1800μg/L and 20℃

Safety Information

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN3077 9/PG 3

WGK Germany 

2

Toxicity

LD50 in rats (mg/kg): >5000 orally, >5000 dermally; LC50 in rats (mg/m3): >5000 by inhalation; LC50 (48 hr) in carp, rainbow trout (mg/l): 3.2, 3.4 (Yasui)

FENTRAZAMIDE Usage And Synthesis

Uses

Fentrazamide is a useful herbicide for proteomics research.

Uses

Herbicide.

Definition

ChEBI: Fentrazamide is a member of tetrazoles.

Preparation

The synthetic pathway employed in the production of fentrazamide is shown in Figure 6. The reaction of 2-chlorophenyl isocyanate 8 and sodium azide in the presence of a catalytic amount of aluminum trichloride in dimethylformamide produces 1-(2-chlorophenyl)-5(4H)-tetrazolinone 9 in high yields. The tetrazolinone 9 is then mixed with N-cyclohexyl-N-ethylcarbamoyl chloride 10 in the presence of potassium carbonate and a catalytic amount of 1-dimethylaminopyridine (DMAP) in toluene to afford fentrazamide in high yields.
Following the disclosure of fentrazamide, several companies entered the herbicidal tetrazolinone chemistry race, and as a consequence many compounds of this class were prepared. The main agents included carbamoyl tetrazolinones with either a heterocycle group, a cycloalkyl group, or a heterocycle methyloxy group at the 1-position of the tetrazolinone ring, thiocarbamoyl tetrazolinones, carbamoyl tetrazolinones with tetrahydro-2H-pyran-4-yl group in the carbamoyl moiety, and hydrazine carbamoyl tetrazolinones. To date, none of these compounds have achieved commercial status.

Agricultural Uses

Fentrazamide is highly effective in the control of annual grass weeds (Echinochloa spp., C. difformis, S. juncoides) and broadleaf weeds (L. pyxidaria, M. vaginalis). It controls barnyard grass of zero- to three-leaf stage at application rates of 200– 300 g ha−1. This compound is also characterized by a long-term residual activity and shows excellent safety toward both transplanted rice and seeded paddy rice. Indeed, based on these properties, fentrazamide became the first paddy herbicide to be used as simultaneous treatment at the time of transplanting. The mixture partners of fentrazamide in one-shot paddy herbicides include sulfonylureas such as bensulfuron-methyl (Innova®) or pyrazosulfuron-ethyl (Doublestar®) and 4-HPPD inhibitors such as benzobicyclon (Smart®). In Southeast Asian countries, fentrazamide is used as a mixture with propanil (Lecspro®) to treat direct-seeded rice.

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