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Asulam

Basic information Safety Supplier Related

Asulam Basic information

Product Name:
Asulam
Synonyms:
  • UPPERCUT
  • Asulon
  • methyl sulphanilylcarbamate
  • ASULAM, 1GM, NEAT
  • mb 9057
  • METHYL SULFANILYLCARBAMATE
  • Methyl [(4-aminophenyl)sulfonyl]carbamate
  • METHYL 4-AMINOPHENYLSULPHONYLCARBAMATE
CAS:
3337-71-1
MF:
C8H10N2O4S
MW:
230.24
EINECS:
222-077-1
Product Categories:
  • Agro-Products
  • Amines
  • HERBICIDE
  • Aromatics
  • Sulfur & Selenium Compounds
  • Other APIs
Mol File:
3337-71-1.mol
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Asulam Chemical Properties

Melting point:
142-144°C (dec.)
Density 
1.4655 (rough estimate)
refractive index 
1.5690 (estimate)
storage temp. 
0-6°C
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
4.82(at 25℃)
color 
Pale Brown to Light Brown
Water Solubility 
5g/L(room temperature)
Merck 
13,862
BRN 
2697523
LogP
-0.270
NIST Chemistry Reference
Asulam(3337-71-1)
EPA Substance Registry System
Asulam (3337-71-1)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
FD1190000
HS Code 
29350090
Hazardous Substances Data
3337-71-1(Hazardous Substances Data)
Toxicity
LD50 in rats, mice, dogs, rabbits (mg/kg): >5000, >5000, >5000, >2000 orally; in rats (mg/kg): >1200 dermally (Brockelsby)

MSDS

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Asulam Usage And Synthesis

Description

Asulam is a sulfonamide and can be formulated as a sodium salt. It is very water soluble and is a very systemic herbicide following foliar and root uptake, owing to its physicochemical properties (Table 1). The Log P (Kow) of 1.01 and pKa of 4.82 are optimal for phloem mobility in the plant (4). These properties contribute to the herbicidal effectiveness against perennial weeds where translocation to underground meristematic organs is essential for effective control.

Chemical Properties

Light Brown Solid

Uses

Systemic, pre- and postemergence herbicide used to control several perennial grasses and certain broad-leaved weeds such as brackenfern, crabgrass, itchgrass, paragrass, tansy ragwort, and wild mustard, in alfalfa, uncropped land, certain ornamentals and turf.

Uses

Carbamate herbicide; folic acid biosynthesis inhibitor.

Uses

Herbicide.

Definition

ChEBI: A carbamate ester that is methyl carbamate substituted by a (4-aminophenyl)sulfonyl group at the nitrogen atom.

Health Hazard

Low order of toxicity; no adverse effect onskin reported; ingestion of large dose couldproduce cholinergic effects.
LD50 oral (rat): 2000 mg/kg.

Pharmacology

Asulam-induced growth inhibition of carrot cell cultures was reversed by 4-aminobenzoic acid (8), and depletion of folate derivatives in treated plants (7) provides further evidence that the synthesis of folic acid is the primary target of asulam. Furthermore, asulam is structurally related to sulfonilamide and to sulfonamide antimicrobial drugs, which are competitive inhibitors of 7,8-dihydropteroate synthase (DHPS) (5,9).

Environmental Fate

Soil. It is not persistent in soils since its half-life is approximately 6–14 days (Hartley and Kidd, 1987). The short persistence time is affected by soil temperature and moisture content. The half-life of asulam in a heavy clay soil having a moisture content of 34% and maintained at 20°C was 7 days (Smith and Walker, 1977). In soil, sulfanilamide was reported as a product of hydrolysis. In non-sterile soils, this compound further degraded to unidentifiable products (Smith, 1988) which may include substituted anilines (Bartha, 1971).
Photolytic. The reported photolytic half-lives for asulam in water at pH 3 and 9 were 2.5 and 9 days, respectively (Humburg et al., 1989)
Chemical/Physical. Forms water-soluble salts (Hartley and Kidd, 1987). When heated to 75°C, asulam decomposed to sulfanilic acid, carbamic acid and sulfanilamide. At 90°C, 4-nitro- and 4-nitrosobenzene sulfonic acids were released (Rajagopal et a

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