(R)-1-(ethylcarbamoyl)ethyl carbanilate

(R)-N-ethyl-2-[[(phenylamino)carbonyl]oxy]propanamide

C₁₂H₁₆N₂O₃

Colourless crystals.

119 ℃; (tech., >110 ℃)

Negligible (20 ℃)

In water c. 3.5 g/l (20 ℃). In acetone 900, dimethylformamide 1500, ethanol 850, methanol 1400, cyclohexane 0.3 (all in g/l).

Stable under normal storage conditions. 
 

Mitosis inhibitor (microtubule organisation).

Selective herbicide, absorbed principally by the roots, and also by the leaves.

Control of annual grasses (including volunteer cereals) and some broad-leaved weeds, at 2 kg/ha, in clover, alfalfa, sainfoin, brassicas, field beans, peas, lentils, sugar beet, oilseed rape, chicory, endive, sunflowers, caraway, strawberries, vines, and fruit orchards.

Acute oral LD₅₀ for rats >2000, mice 1720, dogs 900 mg/kg.

Acute percutaneous LD₅₀ for rabbits >500 mg/kg. Non-irritating to eyes (rabbits).

LC₅₀ (4 h) for rats >0.13 mg/l air.

 In 90 d feeding trials, no effect observed with rats receiving 3200 mg/kg diet, or dogs receiving 12 800 mg/kg diet.

WHO (a.i.) U; EPA (formulation) IV

Acute oral LD₅₀ for bobwhite quail >2000 mg/kg.

LC₅₀ (96 h) for rainbow trout and common carp >100 mg/l.

 EC₅₀ (48 h) 36.5 mg/l.  Bees Not hazardous to bees when used as directed.

LC₅₀ 600 mg/kg soil. 

Rapidly metabolised, leaving no residues in the plant.

Microbially degraded in soil; DT₅₀ c. 1 mo. Duration of activity at low temperatures is c. 2-3 mo. Kd ranges from 0.10 (0.01% o.m., pH 6.6) to 7.92 (16.9% o.m., pH 6.8) (H. J. Pedersen et al., Pestic. Sci., 44, 131 (1995)). 

analysis by hplc (CIPAC Handbook, 1992, E, 28) or by titration of the ethylamine liberated on hydrolysis (J. Desmoras et al., Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 509).