Sulfonamide compound

[Detailed Description of the Invention]

[Industrial Application] Especially the present invention provides a new sulfonamide compound useful as a disinfectant. [The problem that the conventional Technical collar and an invention tend to confront] Conventionally, many things are compounded about the sulfonamide compound. For example, in U.S. Pat. No. 2,588,968, it is following-expression. the sulfonamide compound denoted by (however, 1. X shows a methyl group and phenyl group-Wo example and X' indicates a hydrogen atom and a Alkyl machine to be) - it calls, and if it is the manufacturing method, it is indicated to Facial that the Sour 4 and a Amide compound are useful as synthetic materials of a high molecular compound. Although it can guess easily that it is considered that the compound shown by the above-mentioned - Formula prisoners is a styrene derivative which has a functional group, therefore it can become high molecular compound composition materials, The application as other uses, for example, Medical and agricultural chemicals, must have been expected at all, and the research on the physiology activity of a sulfo nil amide derivative denoted by the above-mentioned - Formula prisoners was not made at all until it continued [ therefore ] up to now. The means] this artificers for solving C problem inquired about the sulfonamide compound which has antibacterial high activity. As a result, it checks that it can become the disinfectant where the sulfonamide compound which has a specific structure has antibacterial activity strong against broad Bacterial species, such as coliform bacillus, an athlete's foot bacillus, and a sesame Septoria tritici bacillus, and which was excellent in it, and came to complete the present invention. That is, the present invention is - expression (1). % Formula % however -- R -- substitution -- or -- unsubstituted -- an aryl group -- or -- substitution -- or -- unsubstituted -- heteroaryl -- a machine -- being shown -- R -- one -- R -- two -- of the same kind -- or -- different species -- a hydrogen atom -- or -- Alkyl -- a machine -- being shown -- R -- three -- substitution or an unsubstituted Alkyl machine, substitution, or an unsubstituted phenyl group. Substitution or the basis denoted by a terrorism aryl group or OR5 to unsubstituted one is shown, R5 shows substitution, an unsubstituted Alkyl machine, substitution, or an unsubstituted phenyl group, R4 shows a terrorism aryl group to substitution or an unsubstituted Alkyl machine, substitution, an unsubstituted phenyl group, substitution, or unsubstituted one. It is a disinfectant which makes an active ingredient the sulfonamide compound expressed and the sulfonamide compound. Especially the aryl group of unsubstituted [ which is shown by R and R4 among the above-mentioned - expression (1) in the present invention ] or substitution can be used, without being limited. It is a phenyl group when the example of this unsubstituted Completion reel machine is shown. A naphthyl group, an anthranil, etc. are mentioned. Although the kind in particular of substitution machine of the above-mentioned substitution aryl group is not restricted, a halogen atom from ease, a Alkyl machine, a Alfoxy machine, an alkylthio group, an alkylamino group, a nitro group, a cyano group, an alkoxyalkyl group, etc. of materials acquisition are preferred. As an example of the above-mentioned halogen atom, each atom of chlorine, bromine, fluoride, and iodine is mentioned. If the example of the above-mentioned Alkyl machine is shown, the Alkyl machine of carbon @1~4, such as a methyl group, an ethyl group, n-propyl group, an 18o-propyl group, and n-butyl group, is preferred. All hydrogen may be replaced in part by substitution machines, such as a halogen atom, and these Alkyl machines are a chloromethyl group, a bromomethyl machine, and a Fluoro methyl group as the example. An iodine methyl group, a dichloro methyl group, difluoromethyl group, a Tori Cros 4 methyl group, a trifluoromethyl group, a chloro ethyl group, a Fluoro ethyl group, a cyclo p ethyl group, a trifluoroethyl machine, a cyano methyl group, a hydroxymethyl group, etc. are mentioned. Although the above-mentioned alkoxy group in particular is not restricted, either, if the example is shown, a methoxy group, a Eto 1000 Si machine, n-propoxy group, a 180-Propo cow Si machine, an n-butoxy machine, etc. are typical. If a typical thing is illustrated although the above-mentioned alkylthio group in particular is not restricted, either, they will be a methylthio group, an ethyl thio group, and n-Brovilthio machine *. A 1so-propyl thio group etc. are mentioned. If the example of the above-mentioned alkylamino group is shown, a methylamino machine, a dimethylamino group, a diethylamino machine, etc. will be mentioned. The above-mentioned alkoxyalkyl group in particular is not restricted again, either. If the example is shown, a methoxymethyl machine, methoxy ethyl group, methoxy propyl group, and ethoxymethyl machine etc. will be mentioned. As for the number of the substitution machines of the substitution aryl group shown by R and R4, it is preferred that it is 1~3 from the ease of materials acquisition. When the number of substitution machines is plurality, each substitution machine may be of the same kind or different species mutually. The above-mentioned - expression (especially the heteroaryl machine of unsubstituted or substitution shown by R, R3, and R4 can be used among 1], without being limited.) It is a frill machine when the example of a terrorism aryl group is shown to full unsubstituted. A thienyl group, a pyrrolyl machine, a pyridyl group, a benzofrill machine, a benzothienyl group, the India Lil machine, a quinolyl machine, a pyrazolyl machine, etc. are mentioned. The kind of substitution machine illustrated by the substitution aryl group which described above the kind of substitution machine of a terrorism aryl group and its number, and its number are adopted similarly to the above-mentioned substitution. Among the above-mentioned - expression (1), the Alkyl machine in particular shown by R'+R2+R3+R' and R5 is not restricted, but the thing of straight chain shape or the shape of a branch school is used. Although the carbon number in particular is not restricted, either, it is preferred that they are ease power 1~6 of materials acquisition. It is a methyl group when the example of the Al Gil machine is shown. ethyl group and n-propyl &+ an IBo-propyl group, n-butyl group, n-hexyl group, etc. -- mentioning -- To. As a Alkyl machine of the substitution shown by R3, R4, and R5, all or a part of hydrogen in the above-mentioned unsubstituted Alkyl machine is a halogen atom, an alkoxy group, and an alkylthio group. What was replaced with a cyano group, an alkenyl group, an alkenyloxy machine, an aryl group, or a heteroaryl machine is preferred. When the example of such a substitution Alkyl machine is shown, they are a chloromethyl group, a bromomethyl machine, a Fluoro methyl group, an iodine methyl group, a dichloro methyl group, a chlorodifluoromethyl group, difluoromethyl group, a trichloromethyl machine, and a trifluoromethyl group. A chloro ethyl group, a Bromo ethyl group, a Fluoro ethyl group, a dichloro ethyl group, A dibromo ethyl group, a Different sculpture ethyl group, a trichloroethyl machine, a trifluoroethyl machine, It is a cow Schill machine to a perfluoro ethyl group, a perfluoro butyl group, and perfluoro, A methoxymethyl machine, ethoxymethyl machine, methoxy ethyl group, and ethoxyethyl machine, methoxy propyl group, and allyloxy ethyl group, a Methylthio ethyl group, a Ethylthio ethyl group, a cyano methyl group, a cyano methyl group. Although an allyl group, a phenylmethyl machine, a frill methyl group, a thienyl methyl group, etc. are mentioned, In the case of the Alkyl machine replaced with the above-mentioned phenylmethyl machine, a frill methyl group, a thienyl methyl group ring, Aryl, or a heteroaryl machine, a substitution machine may be one of the Aryl or heteroaryl machines, and the conditions of the substitution machine of the substitution aryl group shown with above R and R4 can apply as it is. The conditions of substitution Aryl shown also in the substitution machine of the substitution phenyl group shown by R3 and R5 with above R and R4 can apply as it is. The above-mentioned - expression of the present invention (the Sour Pons amidating Compound shown in 1] can check the structure by the following means.) (A) Absorption based on [ by measuring an infrared absorption spectrum (IR) ] the carbonyl binding of an amide machine to 1750~1650-cm-." The absorption, 1370~1320alpha-1, and 1180~] based on a double bond of 1650~1600alpha-1 vinyl group The absorption based on sulfo nil combination of a sulfonamide group, etc. are observable to I 50 on-'. As an example of representation, the IR spectrum about N-methoxy carbonyl N-(2 and 2-Dimethyl- 1-phenyl) Ethynyl trifluoro methanesulfon amide was shown in Drawing 1. (Ro) It asks for the composition formula which measures mass Speckle (MS) and is equivalent to each peak (be expressed with m/e which generally Removal(ed) mass m of ion with number of charges e of ion number) observed, Molecular site of the compound with which measurement was presented, and the bonding pattern of each atom group in the molecule can be known. That is, it is general formula % type % about the sample with which measurement was presented. Since it comes out, and a molecule ion beak (it is written as M(i) below) is generally observed when expressed, the molecular weight of the compound with which measurement was presented can be determined. yP -- < -- or in addition to MO+1, M■-R4, M■-8 O□R', and an M phi-COR 3 * peak can know the bonding pattern of the molecule in observation. G' When 'H-a Magnetic fi measures 111 Skill ('H-NMR), the bonding pattern of the hydrogen atom which exists in the compound of the present invention denoted by the above-mentioned - expression can be known. as the example of representation of lH-NMR (delta11Io: tetramethyl Silane machine St pile chloroform solvent) of the compound -- " about N-methoxy carbonyl N-(2 *2-Dimethyl- 1-phenyl) Ethynyl trifluoro methanesulfon amide -- a H-NMR figure is shown in Drawing 2. It is as follows when the analysis result is shown. That is, the single line which is equivalent to 1.781JP and 1.92 KM at the proton for three pieces, respectively is accepted, and it can belong with what is depended on methyl group (b) and (C). The single line equivalent to the proton for three pieces is observed in 39 04, and 4@ Genus can do with what is depended on the methyl group of (&). 7. The single line equivalent to the proton for five pieces is observed in 23u, and it can belong with what is depended on the proton replaced by the benzene ring (d). Into) By ultimate analysis, they are carbon, hydrogen, and nitrogen. every of sulfur (halogen when [ And ] halogen is included) -- by asking for mW% and also subtracting the sum of superposition % of each recognized element from 100, the amount % of M of oxygen can be computed, therefore the composition formula of the compound can be determined. Although the sulfonamide compound of the present invention differs in the quality according to the kind of RIR'~R4 in the above-mentioned - expression, generally, in normal temperature normal pressure, it is colorlessness, light yellow, a solid of light brown, or a fluid, and is in the tendency which will be decomposed if it becomes more than a certain constant temperature. The compounds of the present invention are benzene and ether. Acetone, alcohol, chloroform, acetonitrile, N, and N-Dimethylform amide. Although it is meltable in common organic solvents, such as dimethyl sulfoxide, it hardly melts into water. The manufacturing method in particular of the sulfonamide compound shown with the above-mentioned - expression (1) of the present invention may not be limited, and what kind of manufacturing method may be sufficient as it. It is as follows when a suitable manufacturing method is shown especially. \/ R-C-NH8OR' .... (2) (]3) (However, Sulfone amide as which R, R1, and R2 and R4 are expressed in the above-mentioned - expression (1) and - expression R3C0Z) ----- By making the acid halide or the acid anhydride denoted by (3) (however, R3 is the same as the above-mentioned - expression (1), and 2 shows a halogen atom or 0COR3.) react, the sulfonamide compound denoted by the above-mentioned - expression (1) can be obtained. In the reaction, although a sulfonamide compound, fli Para Ito, or the preparation molar ratio with an acid anhydride may be determined suitably if needed, it is common to use a little Mol, such as usual, or acid halide for an excess. Good Massey To, Hensen, acetone, methylene chloride, chloroform, N, and N-Dimethylform amide etc. are used suitably, and also using an organic solvent for a reaction generally can make it react also in underwater. In a reaction, since hydrogen halide or carboxylic acid carries out subraw, it is preferred to make these capture agents usually live together in the system of reaction. Although a capture agent in particular is not limited but a publicly known thing can be used, As a capture agent generally used suitably, trialkylamine; pyridine; diazabicyclo octane; sodium Arco lard; sodium carbonate, such as trimethylamine and triethyl amine, potassium carbonate, etc. are mentioned. In the reaction, in order to improve the reactivity of Sulfone amide denoted by - expression (2), the method of making it change and react to an alkaline metal place is also used suitably. As an alkaline metal-ized trial agent generally used suitably, Hydrogenate IJ Umu, lithium hydride, metallic sodium, sodium amide, lithium amide, sodium hydroxide, a potassium hydrate, etc. are mentioned. The above-mentioned - expression which dissolved the Sulfone amide generally shown in a solvent with the above-mentioned - expression (2), was taught to the reaction machine and dissolved in the solvent although an addition order in particular of the materials in the reaction was not limited (good [ to add under churning the acid halide or the acid anhydride shown by 3] ]) Of course, materials can be continuously added to the system of reaction, and the generated reaction thing can also be continuously taken out from the system of reaction. If reaction temperature can be chosen from the wide range and is generally chosen in the range of 120degreeC~150degreeC, preferably O degrees C~100 degreeC, it is enough. Although it changes also with kinds of materials, reaction time is enough if it usually chooses out of the range of 1~50 hours for 5 minutes ~ ten days desirable. Agitating in a reaction is preferred. The object output from the system of reaction, i.e., the above-mentioned - expression, (the sulfonamide compound method in particular of carrying out isolation generation shown by]] is not limited, but a publicly known method can be used for it.) For example, it is the residual substance after Deletion(ing) a superfluous reaction reagent and the generated salt from reaction liquid Benzene, toluene, and chloroform e 77 An organic solvent extracts. About the organic layer, after drying with driers, such as Glauber's salt and a calcium chloride, an organic solvent is A dog(ed), and an object is obtained. A refining means is a re-crystal although it may carry out if needed. Chromatography, vacuum distillation, etc. can use it conveniently. Since the sulfonamide compound shown with the above-mentioned - expression (1) of the present invention has strong antibacterial activity to fungi, such as plant pathogenic microbes, such as a sesame Septoria tritici bacillus and Wilt disease, bacillus subtlis, an athlete's foot bacillus, and coliform bacillus, it is useful as a disinfectant. a sulfonamide compound with these publicly known characteristics -- eye Introduction -- , -- there is no Listen. the compound of the present invention is broadly applicable to Basidient fungi and the variety disease germ which fungi and a child get so and belongs to fungi, fungi imperfecti, bacteria, etc., for example. the operating mode in particular of the sulfonamide compound shown with the above-mentioned - expression (1) of the present invention is not limited -- the operating mode of a publicly known weed killer -- the -- it can Up one time. For example, it can be used for arbitrary dosage forms, such as a grain agent, a powder agent, an emulsion, wettable powder 2 tablet, aerosol, and Smoking agent, using an inactive solid carrier, a fluid carrier, an emulsification dispersing agent, etc., carrying out. Of course, the auxiliary agent metaphor on a tablet can also blend a spreading agent, a diluent, a surface-active agent, etc. suitably. [Example] In order to explain the present invention still more concretely, an example is given and described hereafter, but the present invention is not limited to these examples. Example I Sodium carbonate (0, 13, 9) was added to the acetone solution (11) of N-(2 and 2-Dimethyl- 1-phenyl) Ethynyl trifluoro methanesulfon amide (0, 7g), and Krol methyl formate (0, 29&) was dropped. The sediment was filtered after agitating at - evening and room temperature then. o27i When ffl Shrunken refined Filtrate and silica gel column chromatography (benzene) refined the residual substance, colorless viscous liquid was obtained. The result of having measured IR of this thing is as being shown in Drawing 1. C46 and 32%, the ultimate analysis value is H4, 27 arcs, H4, and 14%, and was well in agreement in C46.29% which is a calculated value over composition formula C13H□4F3No4S, and H4 and H [ 18% of ] 4 or 15%. When MS was measured, peak pm/ezo4 corresponding to MO-COOCH3 was used peak +m/6129 corresponding to MO-8 O□CF3 the peak corresponding to MO+1 to m /e 33 B, and m/e277. moreover -- The result of having measured 'H:NMR (delta: Sir; one-fold tetramethyl Silane standard chloroform solvent) was shown in Drawing 2. The analysis result was as follows. dJ Under [ the single line for three protons is shown in 1.78PI11 and 1.92 4, respectively and equivalent to the methyl proton of (b) and (C) ]. The single line for three protons is shown in 3.90PP (bottom [ equivalent to the methyl proton of - ]), Under [ the single line for five protons is shown in 7.23 f and equivalent to the proton of the benzene ring of (theta) ]. Isolation output became clear [ that it is N-Carbo methoxy N-(2 and 2-Dimethyl- 1-phenyl) Ethynyl trifluoro methanesulfon amide ] from the above-mentioned result. yield was 31.8%. Example 2 (2,2-Dimethyl- 1-phenyl) 1,4-Giazapi cyclo C2, 2, and 2 octane (0, 64g) is added to the chloroform fluid (10 m) of Ethynyl trifluoro methanesulfon amide (1,0!i-9), The chloroform fluid (5-) of Acetyl chloride (045g) was dropped. - Reaction liquid was poured into cold water after churning at an evening and room temperature, and chloroform extracted. When chloroform was distilled off for chloroform N' after dryness with anhydrous sodium sulfate and silica gel chromatography (benzene) refined the residual substance, 0 or 87.9 light brown fluids were obtained. The result of having measured IR of this thing is as being shown in Drawing 3. The ultimate analysis value, C48, and 38%, it is H4 and 34 arc, H4, and 14%, and is a calculated value over composition formula C13H14F3N03S. It was well in agreement in C48 and H [ H / 59% of / 4 or 39% of ] 436%. When MS was measured, the peak corresponding to MO-8O2CF3 and the m/e beak were shown in the peak corresponding to MO+1, and m / e 279 at the peak corresponding to MO-COCH3, and m/e1ss m / o 322. The result of having measured 'H-NMR (delta:P.; tetramethyl Silane standard double chloroform solvent) was shown in Drawing 4. The analysis result was as follows. Under [ the single line for three protons is shown in 1.87111 m and 1.93IP, respectively and equivalent to the methyl proton of (b) and (c) ]. Under [ the single line for three protons is shown in z35ppH and equivalent to the methyl proton of (a) ]. 7. Under [ the single line for five protons is shown in 19IP and equivalent to the proton of the benzene ring of (d) ]. Isolation output became clear [ that it is N-Acetyl- N-(2 and 2-Dimethyl- 1-phenyl) Ethynyl trifluoro methanesulfon amide ] from the above-mentioned result. yield was 7.19%. Example 3 Example]

And the compound shown with various following-expression by the same method as example 2 grade was compounded. yield of the compound compound, and an ultimate analysis value -- the -- the [ 1a table and ] -- it was shown in 1b table (the case of R3=OR is Table ])

b). the -- the [ 1a table and ] -- the brief sketch in 1b table is as being shown below, respectively. Et; an ethyl group, n A P rp Normal propyl group, 18 o-PrJ isopropyl group, n-Bu; Normal butyl group. Example 4 of a use After heat-sterilizing the nutrition culture medium which contains agar 1.5% by 121 degreeC for 15 minutes, it cooled to 50degreeC, and what was suspended to aseptic water in the mycelia cake or spore which this was made to grow beforehand could be put in, and it mixed, it poured into the petri dish, and made it solidify monotonously. A circle type mouth paper board 8 n in diameter was dipped in the methanol solution containing 15 A of compounds compounded in example 1. example 2 and Example 3, and it placed on the agar medium solidified except for a part for a surplus on the mouth paper board. The diameter of the prevention circle was measured after 24~48-hour cultivation by about 30 degreeC. As #1m of contrast, and mold, Etcher Litzea Cori B (Esaherichia) coli B Cochliobolus Mabeanas: EC+ Bacillus subtilis (Batillua 5 u-btilis: BS) # -- Aspergillus niger (Aapergillus nigor: AN) (Cochliobolua) + m1yabeanus : CM+ Ricoh Phu Thong Le Bram (Trichophyton rubrum : TR) + It carried out using 7 Salium oxysporum (Fuaariumoxyaporum : FO). Conflict of anti-Examinations was done to the 2nd table. The thing which indicates all the sample-offering bacilli of the 2nd table by a cable address, and is ineffective or-less 1ii1: - showed the thing of Trial.

[Brief Description of the Drawings]

Drawings 1 and 2 are Examples 1, and Drawings 3 and 4 show IR and the IH-NMR spectrum of a sulfonamide compound which were obtained in Example 2, respectively.