4151-50-2

Usage

Uses

Used in Pest Control:
Sulfluramid is used as an insecticide for controlling various pests, particularly ants and roaches in households. It is also utilized for managing the red imported fire ant in wider situations.
Used in Agriculture:
In the agricultural industry, Sulfluramid serves as an insecticide, acaricide, and termiticide. It is commonly used as bait in ant, roach, and termite traps. However, it is not listed for use in EU countries and is actively registered for use in the U.S. According to the Fluoride Action Network, this chemical is not registered for use on food or crops and is scheduled to be phased out by 2016.

Trade name

FINITRON?; FIRSTLINE?; FLUORGUARD?; GX-071?; MICRO-GEN ANT REACTOR?; VOLCANO?

Metabolic pathway

Sulfluramid is a highly fluorinated sulfonamide which was introduced relatively recently for the control of ants and roaches. It is also used now for the control of the red imported fire ant (Solenupsis invicta). Its fate in rats has been studied but, due to its limited use pattern, there appears to be no information yet published on its environmental fate nor on its metabolism in plants. It is biotransformed by N-de-ethylation to an insecticidally active and toxic metabolite.

Degradation

Sulfluramid is stable for more than 90 days at 50 °C and it is similarly stable in light under glass. Though a weak acid, it is highly lipophilic due to the perfluorooctyl group.

InChI:InChI=1/C10H6F17NO2S/c1-2-28-31(29,30)10(26,27)8(21,22)6(17,18)4(13,14)3(11,12)5(15,16)7(19,20)9(23,24)25/h28H,2H2,1H3

Synthetic route

perfluorooctyl sulfofluorure (307-35-7) + ethylamine (75-04-7) → N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2)

Conditions	Yield
Stage #1: perfluorooctyl sulfofluorure; ethylamine With triethylamine In diethyl ether at 0 - 20℃; for 17h; Stage #2: With sodium hydrogencarbonate In diethyl ether for 3h; Heating; Further stages.;	56%
In diethyl ether anhydr. ether, at -5 to 0°C, 2.75 h;
With triethylamine In di-isopropyl ether for 4h; Reflux;
In diethyl ether anhydr. ether, at -5 to 0°C, 2.75 h;

perfluorooctanesulphonyl chloride (423-60-9) + tri-n-butylamine hydrofluoride (25152-55-0, 60435-94-1, 73602-62-7, 127322-37-6, 130089-03-1) + ethylamine (75-04-7) → N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + N,N-dibutyl perfluorooctanesulfonamide

Conditions	Yield
In various solvent(s)	A 0.05 mol B 0.005 mol

perfluorooctanesulphonyl chloride (423-60-9) + ethylamine (75-04-7) → N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + C8HF17O2S + C8HF17O2S*C2H7N

Conditions	Yield
In dichloromethane Product distribution; var. solv, investigated;

perfluorooctyl sulfofluorure (307-35-7) + ethylamine (75-04-7) → hydrogen fluoride ethylamine (65756-36-7) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2)

Conditions	Yield
In diethyl ether at -30-0°C,2.75 h;
In diethyl ether at -30-0°C,2.75 h;

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + 2-bromoethanol (540-51-2) → N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide (1691-99-2)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 48h; Heating;	99%

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + 2-(tert-butyldimethylsilyloxy)ethanol (102229-10-7) → 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonic acid [2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amide (1017593-64-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In diethyl ether at 0 - 25℃; Mitsunobu reaction; sonication;	98%

bromoethyl acetate (927-68-4) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → 2-(N-ethyl-perfluorooctylsulfonamido)ethyl acetate (1017593-63-3)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 36h; Heating;	92%

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + bromoacetic acid methyl ester (96-32-2) → methyl 2-(N-ethyl-perfluorooctanesulfonamido) acetate (87988-69-0)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 3h; Heating;	90%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-(4,6-dichloro-1,3,5-triazin-2-yl)-N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide

Conditions	Yield
Stage #1: N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide With sodium In ethanol for 0.5h; Metallation; Stage #2: 1,3,5-trichloro-2,4,6-triazine In acetone at -78 - 20℃; for 2h; Substitution;	72%

glycolic acid methyl ester (96-35-5) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → methyl 2-(N-ethyl-perfluorooctanesulfonamido) acetate (87988-69-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In diethyl ether at 0 - 25℃; Mitsunobu reaction; sonication;	67%

trifluoro-[1,3,5]triazine (675-14-9) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-(4,6-difluoro-1,3,5-triazin-2-yl)-N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide

Conditions	Yield
Stage #1: N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide With sodium In methanol for 1h; Metallation; Stage #2: trifluoro-[1,3,5]triazine In acetone at -78℃; for 3h; Substitution;	31%

vinyl chloroacetate (2549-51-1) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-ethyl-N-(heptadecafluoro-octane-1-sulfonyl)-glycine vinyl ester (678-36-4)

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide (1691-99-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / potassium carbonate; NaI / acetone / 36 h / Heating 2: 93 percent / aq. potassium hydroxide / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 98 percent / diisopropyl azodicarboxylate; triphenylphosphine / diethyl ether / 0 - 25 °C / sonication 2: 96 percent / aq. HCl / methanol / 48 h / 25 °C View Scheme
With potassium hydroxide und Erwaermen des Reaktionsprodukts mit 2-Chlor-aethanol;

[1,3]-dioxolan-2-one (96-49-1) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide (1691-99-2)

Conditions	Yield
With pyridine at 176℃;

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → 2-(N-ethyl-perfluorooctane sulfonamido) acetic acid (2991-50-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / potassium carbonate; sodium iodide / acetone / 3 h / Heating 2: 40 percent / aq. NaOH / dioxane / 2 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1: 67 percent / diisopropyl azodicarboxylate; triphenylphosphine / diethyl ether / 0 - 25 °C / sonication 2: 40 percent / aq. NaOH / dioxane / 2 h / 65 °C View Scheme

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → adipic acid bis-{2-[ethyl-(heptadecafluoro-octane-1-sulfonyl)-amino]-ethyl ester} (599-58-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / und Erwaermen des Reaktionsprodukts mit 2-Chlor-aethanol View Scheme

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + allyl bromide (106-95-6) → C13H10F17NO2S (24924-36-5)

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 14.5 - 16.5h;

Upstream product

• 423-60-9 perfluorooctanesulphonyl chloride 
• 25152-55-0 tri-n-butylamine hydrofluoride 
• 75-04-7 ethylamine 
• 307-35-7 perfluorooctyl sulfofluorure 

Downstream Products

• 1691-99-2 N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide 
• 24924-36-5 C₁₃H₁₀F₁₇NO₂S 
• 2991-50-6 2-(N-ethyl-perfluorooctane sulfonamido) acetic acid 

Relevant academic research and scientific papers

Synthesis and surface activities of organic solvent-soluble fluorinated surfactants

A variety of fluorinated surfactants soluble in organic solvent were prepared, including C8F17SO2NHCnH2n+1 (n = 2, 4, 6, 8, 10), C8F17SO2NHR (R = C6H11, C6H5), C8F17SO2N(CnH2n+1 )2 (n = 1, 2, 3, 4) and C8F17SO2NH(CH2)nN HO2SC8F17 (n = 6, 10). Their surface activities in various organic solvents were determined by surface tension measurement. The results showed that these fluorinated surfactants can reduce the surface tension of both polar and non-polar organic solvents. In general, organic solvents with strong polarity or long alkyl chain are beneficial to increase the surface activity of these polar fluorinated surfactants. By comparing fluorinated surfactants with the same fluorocarbon segment and connecting group, C8F17SO2N(CnH2n+1 )2 (n = 1, 2, 3, 4) showed lower surface activity in organic solvents than C8F17SO2NHCnH2n+1 (n = 2, 4, 6, 8) with an equal carbon number of the solvophilic group. Through surface tension vs. concentration curves given for N-octyl perfluorooctanesulfonamide in various organic solvents, a break point like the critical micelle concentration of ordinary surfactants in aqueous solutions was observed, and the effect of the different types of organic solvents on adsorption and aggregation behavior was also studied.

Synthesis and structure of environmentally relevant perfluorinated sulfonamides

Alkylated perfluorooctanesulfonamides are compounds of environmental concern. To make these compounds available for environmental and toxicological studies, a series of N-alkylated perfluorooctanesulfonamides and structurally related compounds were synthesized by reaction of the corresponding perfluoroalkanesulfonyl fluoride with a suitable primary or secondary amine. Perfluoroalkanesulfonamidoethanols were obtained from the N-alkyl perfluoroalkanesulfonamides either by direct alkylation with bromoethanol or alkylation with acetic acid 2-bromo-ethyl ester followed by hydrolysis of the acetate. N-Alkyl perfluorooctanesulfonamidoacetates were synthesized in an analogous way by alkylation of N-alkyl perfluoroalkanesulfonamides with a bromo acetic acid ester, followed by basic ester hydrolysis. Alternatively, N-alkyl perfluoroalkanesulfonamides can be alkylated with an appropriate alcohol using the Mitsunobu reaction. Perfluorooctanesulfonamide was synthesized from the perfluorooctanesulfonyl fluoride via the azide by reduction with Zn/HCl. All perfluorooctanesulfonamides contained linear as well as branched C8F17 isomers, typically in a 10:1 to 30:1 ratio. The crystal structures of N-ethyl and N,N-diethyl perfluorooctanesulfonamide show that the S-N bond has considerable double bond character. This double bond character results in a significant rotational barrier around the S-N bond (ΔG≠ = 62-71 kJ mol-1) and a preferred solid state and solution conformation in which the N-alkyl groups are oriented opposite to the perfluorooctyl group to minimize steric crowding around the S-N bond.

Method for exterminating termites

A method for exterminating termites comprising using an entomopathogenic nematode together with an inset-growth regulator or a slow-acting insecticide, wherein insecticidal effects are reinforced compared with the cases using singly the entomopathogenic nematode and the insect-growth regulator or the slow-acting insecticide, respectively, and a bait station for exterminating termites that contains an entomopathogenic nematode with an insect-growth regulator or a slow-acting insecticide. According to the invention, emission of harmful chemicals to environment can be suppressed. The invention is nonpoisonous for human being and livestock, and is useful for indoor or outdoor extermination of termites.