methyl sulfanilylcarbamate

methyl [(4-aminophenyl)sulfonyl]carbamate

C₈H₁₀N₂O₄S

Colourless crystals.

142-144 ℃ (decomp.)

<1 mPa (20 ℃)

℃ In water 5 g/l (20-25 ). In dimethylformamide >800, acetone 340, methanol 280, methyl ethyl ketone 280, ethanol 120, hydrocarbons and chlorinated hydrocarbons <20 (all in g/l, 20-25 ℃). Other salts: in water, potassium >400, ammonium >400, calcium >200, magnesium >400 (all in g/l, 20-25 ℃)

Stable in boiling water ≥ 6h. Stable >4 y (pH 8.5, room temperature).

4.82, forming water-soluble salts.

Inhibition of dihydropteroate synthase.

Selective systemic herbicide, absorbed by the leaves, shoots, and roots, with translocation in both the symplastic and apoplastic systems to other parts of the plant. Causes a slow chlorosis in susceptible plants.

Control of annual and perennial grasses and broad-leaved weeds in spinach, oilseed poppies, alfalfa, some ornamentals, sugar cane, bananas, coffee, tea, cocoa, coconuts, rubber, etc.; wild oats in flax; docks (Rumex spp.) in grassland, fruit trees and bushes, and on non-crop land; and bracken (Pteridium aquilinum) in grassland, non-crop land, and forestry. Application rates from 1-10 kg/ha, depending on crop.

M. A. Gallo et al., Effect of asulam in wildlife species, residues and toxicity in bobwhite quail after prolonged exposure, Bull. Environ. Contam. Toxicol., 1975, 13(2), 200-205. B. Ingham & M. A. Gallo, Effect of asulam in wildlife species - acute toxicity to birds and fish, Proc. Northeast Weed Control Conf., 1975, (1), 194-199.

Acute oral LD₅₀ for rats, mice, rabbits, and dogs >4000 mg/kg.

Acute percutaneous LD₅₀ for rats >1200 mg/kg.

LC₅₀ (6 h) for rats >1.8 mg/l air.

In 90 d feeding trials, rats receiving 400 mg/kg diet showed no significant ill-effects. No effect observed when fed to cows at 800 ppm over 8 w, or to sheep at 50 mg/kg over 10 d. Non-teratogenic.

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

Acute oral LD₅₀ for mallard ducks, pheasants, and pigeons >4000 mg/kg.

LC₅₀ (96 h) for rainbow trout, channel catfish, and goldfish >5000, bluegill sunfish >3000, harlequin fish >1700 mg/l.

In rats, following oral administration, 85-96% of the dose is eliminated, predominantly in the urine, within 3 days.

Has a short persistence in soil, DT₅₀ c. 6-14 d. Soil metabolism is by loss of amino group, cleavage of carbamate group, or acetylation of amino group.

analysis by rplc (CIPAC Handbook, 1998, H, 26; A. Guardigli et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 197) or by hydrolysis with colorimetry of a derivative (C. H. Brockelsby & D. F. Muggleton, ibid., 1973, 7, 497).