72178-02-0

Basic information

• Product Name: Fomesafen
• Synonyms: FLEX;FLEX(R);FLEXSTAR;5-[2-CHLORO-4-(TRIFLUOROMETHYL)PHENOXY]-N-(METHYLSULFONYL)-2-NITROBENZAMIDE;5-[2-Chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulphonyl)-2-nitrobenzamide;REFLEX;REFLEX(R);5(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-n-mesyl-2-nitrobenzamide
• CAS NO: 72178-02-0
• Molecular Formula: C₁₅H₁₀ClF₃N₂O₆S
• Molecular Weight: 438.76
• EINECS: 276-439-9
• Product Categories: Agro-Chemicals;Amide;HERBICIDE
• Mol File: 72178-02-0.mol

Chemical Properties

• Melting Point: 220-221°C
• Appearance: White crystalline solid
• Density: 1.7075 (rough estimate)
• Refractive Index: 1.5660 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Acetonitrile (Slightly), DMSO
• PKA: 23-25(at 25℃)
• BRN: 8165046
• CAS DataBase Reference: Fomesafen(CAS DataBase Reference)
• NIST Chemistry Reference: Fomesafen(72178-02-0)
• EPA Substance Registry System: Fomesafen(72178-02-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 2
• WGK Germany: 1
• RTECS: CV2475000
• Hazardous Substances Data: 72178-02-0(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Fomesafen is used as a herbicide for controlling weeds in soybean crops, white, kidney, and snap beans. It is registered for use in the United States but not approved for use in European Union countries. After July 25, 2003, flumesafen was not permitted in many countries to be used as an active ingredient on crops except for the mentioned purposes.

Reactivity Profile

Fomesafen is incompatible with acids.

Trade name

BAS 530 04?; FASTER?; FLEX?; FLEXSTAR; FOMESAFEN? SODIUM; PP 021?; REFLEX?; REFLEX? 2LC Herbicide (sodium salt); TORNADO?[C]; TWISTE?[C]; TYPHOON?

InChI:InChI=1/C15H10ClF3N2O6S/c1-28(25,26)20-14(22)10-7-9(3-4-12(10)21(23)24)27-13-5-2-8(6-11(13)16)15(17,18)19/h2-7H,1H3,(H,20,22)

Upstream product

• 72178-12-2 3-(2-chloro-α,α,α-trifluoro-4-tolyloxy)-N-(methylsulphonyl)benzamide 
• 3144-09-0 methanesulfonamide 
• 50594-66-6 acifluorfen 

Downstream Products

• 132151-05-4 N,N-bis[5-(2-chloro-4-(trifluoromethyl) phenoxy)-2-nitrobenzoyl]methane sulfonamide 

Relevant articles and documents

Process for the preparation of diphenyl ether compounds

A process for producing fomesafen from acifluorfen comprises the steps of (a) converting acifluorfen to its acid chloride, (b) coupling the acid chloride so formed with methanesulphonamide to form crude fomesafen and (c) purifying the crude fomesafen, characterized in that each of the steps is carried out in a single common solvent, which is preferably a chloroalkane. Preferably the steps are telescoped together so that there is no isolation of the product for any step until fomesafen is obtained

Herbicidal mixtures having a synergistic effect

PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.

Process for the nitration of diphenylethers

A process for the preparation of a compound of general formula I: wherein: R1 is hydrogen or C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, any of which may optionally be substituted with one or more substituents selected from halogen and OH; or COOR4, COR6, CONR4R5 or CONHSO2R4; R4 and R5 are each independently hydrogen or C1-C4 alkyl optionally substituted with one or more halogen atoms; R6 is a halogen atom or a group R4; R2 is hydrogen or halo; R3 is C1-C4 alkyl, C2-C4 alkenyl or C2-C4 alkynyl, any of which may optionally be substituted with one or more halogen atoms; or halo; the process comprising reacting a compound of general formula II: wherein R1, R2 and R3 are as defined for general formula I; with a nitrating agent comprising nitric acid or a mixture of nitric and sulphuric acids in the presence of an organic solvent and in the presence of acetic anhydride, characterized in that the molar ratio of acetic anhydride to compound of general formula II is from about 1:1 to 3:1.

Nitration process

A process for the nitration of an aromatic or heteroaromatic compound with a nitrating agent comprising nitric acid or a mixture of nitric and sulphuric acids, characterised in that nitration is performed in a solvent comprising at least 50% v/v of a C1 -C6 alkyl ester of a C1 -C4 carboxylic acid. The process is of particular use for the nitration of diphenyl ethers to give compounds which are useful as herbicides or as intermediates in the synthesis of herbicides.

Process for phosgenation in the presence of acetonitrile

Phosgenation of carboxylic acids to the corresponding carboxylic acid chlorides in conducted in the presence of a solvent comprising acetonitrile.

Alkylsiloxanes as adjuvants for agriculture

Linear alkylsilicone compounds of the formula STR1 wherein x=0 to 20, preferably 0 to 10, most preferably 0 to 1; y=1 to 10, preferably 1 to 5, most preferably 1; and R is an alkyl or alkyl ester group containing 6 to 16 carbons, or cyclic alkylsilicone compounds of the formula STR2 where m is 0 to 4, preferably 0 to 2, most preferably 0, and n is 1 to 5, preferably 3 to 5, most preferably 4, provided that m+n=3 to 5, are adjuvants for agricultural applications of oil-containing compositions. Especially preferred alkylsilicone compounds have a degree of polymerization of ≤6 and an alkyl content of ≤50% by weight. The compounds potentiate spreading of mineral or vegetable oils or oil-containing emulsions in dormant spray oils, crop oil concentrates, pesticides, and the like on difficult-to wet surfaces such as waxy leaf cuticles and arthropod exoskeletons.

Process for phosgenation in the presence of acetonitrile

Phosgenation of carboxylic acids to the corresponding carboxylic acid chlorides in conducted in the presence of a solvent comprising acetonitrile.

Herbicidal N-halo-5(substituted-phenoxy or -pyridyloxy)-2-substituted benzoic acid sulfonamides and sulfamates

N-halo-5-(substituted-phenoxy or -pyridyloxy)-2-substituted benzoic acid sulfonamides and sulfamates, their preparation and use as herbicides are disclosed.

Substituted diphenyl ethers

A compound of the formula: STR1 and salts and esters thereof, useful as intermediates for the preparation of compounds of the formula STR2 wherein R1 is an alkyl group optionally substituted by one or more fluorine atoms or by an optionally substituted phenyl group R2 is No2 or Cl and R6 is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms.

Selective herbicides

Herbicidal diphenyl ether compounds of the formula STR1 wherein R1 is an alkyl group optionally substituted by halogen or phenyl; R2 is hydrogen, halogen or nitro; R3 is hydrogen, halogen, alkyl, trifluoromethyl or cyano; R4 is hydrogen, halogen, or trifluoromethyl; R5 is halogen or trifluoromethyl; and R6 is hydrogen, or C1 -C4 alkyl. These compounds are useful as selective herbicides in a range of crops, for example, cotton, soya bean, peas, maize, wheat and rice.