FLORASULAM Chemical Properties

Melting point:

220-221° (dec) (Van Heertum); also reported as 193.5-230.5° (Thompson)

Density 

1.75±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

4.54(at 25℃)

Appearance

White to off-white Solid

InChIKey

QZXATCCPQKOEIH-UHFFFAOYSA-N

LogP

1.290 (est)

EPA Substance Registry System

[1,2,4]Triazolo[1,5-c]pyrimidine-2- sulfonamide, N-(2,6-difluorophenyl)-8-fluoro-5-methoxy- (145701-23-1)

Safety Information

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

2

Hazardous Substances Data

145701-23-1(Hazardous Substances Data)

Toxicity

LD50 in rat, quail (mg/kg): >6000, 1046 orally; percutaneously in rabbit: >2000 mg/kg; LC50 in rainbow trout, bluegill (96 hr): >96, >98 mg/l (Thompson)

FLORASULAM Usage And Synthesis

Description

Florasulam is a kind of selective triazolopyrimidine sulfonanilide post-emergent herbicide. It is absorbed by the foliage or roots of the plants. It acts as a systemic herbicide, being able to disrupt the internal growth processes of the weeds and causes their death in several weeks. It can be used for the control of broadleaf weeds in cereals. Its mechanism of action is through inhibiting the acetolactate synthase (ALS) in plants. The enzyme is present in the chloroplast and participates into the biosynthesis of branch chain amino acids such as valine, leucine and isoleucine. Through this mechanism, it can suppress plant cell division, plant growth and ultimately cause plant death. 

References

http://msdssearch.dow.com/PublishedLiteratureDOWCOM/dh_07cf/0901b803807cfdd2.pdf?filepath=productsafety/pdfs/noreg/233-00436.pdf&fromPage=GetDoc
http://www.agropages.com/AgroData/Detail-640.htm

Uses

Herbicide.

Definition

ChEBI: Florasulam is a sulfonamide.

Synthesis

B. Add 5.1 g (40 mmol) of 2,6-difluoroaniline, 10 mL of alcohol solvent, and a small amount of naphthalene crystals (as an internal standard for liquid chromatography) to a 50 mL flask, and heat the mixture to 40 °C. Under nitrogen protection and stirring conditions, 2.67 g (10 mmol) of 2-chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine solid was slowly added until the chlorosulfonyl feedstock completely disappeared (monitored by high-pressure liquid chromatography). After completion of the reaction, the mixture was cooled to room temperature and the solid product was collected by filtration. The solid was washed with 10 mL of 2-propanol followed by water and dried. The resulting N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide was more than 99% pure (results are shown as Runs 4 through 6 in the table below).

References

[1] Patent: EP1066289, 2003, B1. Location in patent: Page/Page column 6
[2] Patent: EP1066289, 2003, B1. Location in patent: Page/Page column 6;7
[3] Patent: EP1066289, 2003, B1. Location in patent: Page/Page column 6
[4] Patent: EP1066289, 2003, B1. Location in patent: Page/Page column 6
[5] Patent: EP1066289, 2003, B1. Location in patent: Page/Page column 6

FLORASULAM(145701-23-1)Related Product Information

• Dimethyltetrachloro
• Glufosinate-ammonium
• Fluroxypyr
• MCPA SODIUM
• Flumetsulam
• Penoxsulam
• PYROXSULAM
• CLORANSULAM-METHYL
• DICLOSULAM
• [1,2,4]TRIAZOLO[1,5-C]PYRIMIDIN-5-OL
• FLORASULAM