DE2151491A1 - Hydroxyhalobenzenesulfonanilides - Google Patents

Description

Ref. 6520 / G

L. Givaudaii & Cic Societe Anonyme, Vernier-Geneve (Switzerland)

Hydroxyhalobenzenesulfonanilides

Certain ortho-hydroxyhalobenzenesulfonanilides have already been carried out. Schraufstätter et al. (Z. Eaturforschung, 16b , 95 (1961)) and described their use as molluscicides. Previous work by Goetchius et al. (J. Lab. Clin. Med., ^ 2: 1361 (1947)) pointed out, however, that the introduction of a hydroxyl group into the plienyl ring of a bensol sulfonanilide system leads to a reduction in the activity of the product.

The new compounds of the invention have the general formula

. OH

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where X is chlorine or bromine, a 1, 2 or 3,

Y halogen, b a number from 1-4, Z trifluoromethyl, thiocyanato, nitro, lower-alkyl, lower-alkylthio

or lower-alkoxy and c is 0 or 1, and the number of substituents a + b + c is at least 4, with the exception that,

when X = Y = Z = bromine, a + b + c is at least 3.

By "lower-alkyl" in the present case, alkyl groups, straight or branched and containing 1-4 carbon atoms are included.

The new compounds of the present invention have a high degree of antibacterial and fungicidal activity and are especially effective against gram-positive bacteria. These compounds do not lose any of their antimicrobial effectiveness in the presence of soap and anionic surface-active substances. They are therefore particularly suitable as antimicrobial additives for such products, either alone or in conjunction with other antimicrobial agents. The compounds can also be used as tissue antibacterial agents.

The new compounds can be obtained by reacting the corresponding ortho-hydroxyhalogenobenzenesulfonyl halide with the corresponding Aniline can be obtained. In this reaction, the aniline component is advantageously used in excess; suitably at least 2 moles of the aniline or 1 mole of aniline and 1 mole of another organic or inorganic mild base such as a tertiary or secondary alaine, e.g. Triethylamine, piperidine or pyrrolidine or an inorganic salt, e.g. sodium or potassium carbonate or 1T & "briuiabi carbons, t, possibly but not necessarily in the presence of a loaunga with lel, cingecutat.

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Instead of the ortho-hydroxyhalogonbenzenesulfonyl halide, a corresponding derivative thereof can also be used, the hydroxyl group in this derivative, for example, being esterified, ie Vj. B. an alkanoate (acetate etc.), a bensoate, a urethane or a derivative with an etherified hydroxyl group, for example a "tetrahydropyranyl ether. When using such derivatives as starting materials, the hydroxyl group must be released again in the usual way after the reaction with the aniline component , ie in the case of the esters, for example, by saponification with the aid of a base, for example sodium or potassium hydroxide.

The ortho-hydroryhalobenzenesulfonyl halides used as starting materials can according to the method of W.L. Hall (J. Org. Chem. £ 1, (8) 2672 (1966)).

The corresponding ortho-hydroxyhalobenzenesulfonyl halide, suitably the chloride contains 1-3 halogen substituents (chlorine or bromine) in the ring. The substituents can are in any position of the ring; Of course here only one of the ortho positions of the hydroxyl group may be occupied.

The sulfonyl halides can from the corresponding Halogen or rolyhalophenol by reaction with chlorosulfonic acid are preserved and show the rest of the general Ponael

RO ₂ X

O J._ »

on,

2 O 9 8 1 7 / Ί 6 b δ

215H91

The anilines used as starting materials have the general formula

III

where Y is halogen (fluorine, bromine, chlorine, iodine), b is a number from 1-4 and Z is trifluoromethyl, Thiocyanato, nitro, lower-alkyl, lower-alkylthio or lower-alkoxy (in which the alkyl radical has 1-4 carbon atoms) and c is 0 or 1.

These anilines are either commercial products or are easily accessible by methods known per se.

As already stated above, the aniline component is advantageous in the preparation of the new compounds of the formula I used in an at least 1 molar excess. The purpose of this excess is that of the reaction to neutralize released HCl uu <i to bind. File karai

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subsequently the excess aniline was naturally recovered will; on the other hand, however, instead of Uebersolmsses in aniline component axich an equivalent of another mild one Base find use.

The starting materials can be reacted in the presence or absence of a solvent. as Any inert solvent can be used. However, ethers have proven to be particularly suitable such as ethyl ether or isopropyl ether, or hydrocarbons, such as toluene.

The starting materials can be reacted in a temperature range from room temperature (for example 25-3O ⁰ C) to the reflux temperature of the reaction mixture. The reaction time can be about 1 to about 72 hours. The most favorable reaction times and temperatures can vary somewhat depending on the starting material.

Examples of compounds of general formula I are the following:

I 2-hydroxy-3,3 ', 4', 5-tetrachlorobenzenesulfonanilide;

II 2-hydroxy-3> 3 ' , 5,5 '-tetrachlorobenzenesulfonanilide;

III 2-hydroxy-3,3 ', 5 , 6-tetrachlorobenzenesulfonanilide;

IV 4'-bromo-2-hydroxy-3, 5, 6-trichlorobenzenesulfonanilide;

V 2-hydroxy-4'-iodine -3,5,6-trichlorobenzenesulfonanilide;

VI 3,5-dibromo-3 ', 4'-dichloro-2-hydroxybenzenesulfonanilide;

VII 2-Hydroxy-3,4 ^f , 5-trichloro-3 '- (trifluoromethyl) -benzenesulfonanilide;

VIII 2-hydroxy-3t5,6-triohlor-3 '- (trifluoromethyl) -benzenesulfonanilide;

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IX 3,5-dibromo-2-hydroxy-2 ', 4', 5'-trichlorobenzenesulfonanilide;

X 2-hydroxy-4'-methyl-3> 3 ' _f 5-trichlorobenzenesulfonanilide;

XI 2-hydroxy-4'-isopropyl-3,5 »6-trichlorobenzenesulfonanilide;

XII 2-hydroxy-4'-methylthio-3,5,6-trichlorobenzenesulfonanilide;

XIII 4'-ethoxy-2-hydroxy-3,5,6-trichlorobenzene silver onanilid;

XIV 2-hydroxy-3,3 ', 4 ^f , 5, 5 '-pentachlorobenzenesulfonanilide;

XV 2-Hydroxy ~ 2 ', 3,4', 5,5'-pentachlorobenzenesulfonanilide;

XVI 2-Hydroxy-3,3 ', 4', 5,6-peirtachlorobenzenesulfonanilide ;

XVII 2-hydroxy-3,3 ', 5,5 ^f , 6-pentachlorobenzenesulfonanilide;

XVIII 2-hydroxy-3,4 ', 5,6-tetrachloro-3' - (trifluoromethyl) benzenesulfonanilide;

XIX 2-hydroxy-3 »3 ', 5,6-tetrachloro-4'-thiocyanatobenzene olefinanilide;

XX 2-hydroxy-2 ^f , 3,4 ' _f 5-tetrabromobenzenesulfonanilide; XXI 2-hydroxy-> 2 ', 3 ₁ 5.5'-tetrabromobenzenesulfonanilide;

XXII 3,3 ', 4', 5,5 ', 6-hexaehloro-2-hydro: scybenzenesulionanilide;

XXIII 2 ', 3,4', 5,5S 6-hexachloro-2-hydroxybenzenesulfonanilide ;

XXIV 2-hydroxy-3, 4 '"5-tribrombenzol3ulfonaniljd;

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XXV 2 ~ hydroxy-4'-methy1-3, 3 ', 5,6-tetrachlorobenzenesulfonanilide;

XXVI 2 ~ hydroxy-4 '~ nitro ~ -3, 5 ₁ 6-trichlorobenzenesulfonanilide;

XXVII 4'-fluoro-1-hydroxy-S, 5,6-trichlorobenzenesulfonanilide;

XXVIII 4'-n-butyl - ^ - hydroxy- ?, 5,6-trichlorobenzenesulfonanilide;

XXIX 2-Hydroxy-2 ', 4', 5,5 '-tetraclilobenzenesilf onanilide.

It is known that many are bacteriostatically active Agents, especially those of the quaternary ammonium salt type, inactivated in the presence of anionic capillary or surface-active substances such as soaps or detergents. The bacteriostatic activity of the new compounds of the formula I, on the other hand, is made anionic by a large number of known compounds surface-active substances are not significantly reduced. For this reason these new compounds of formula I are special useful in conjunction with such capillary-active materials.

The new compounds of formula I can be used as antibacterial agents on their own or together with a large number of capillary or surface-active materials such as audVSoap can be used. Examples of such materials are salts of sulfated alcohols such as sodium lauryl sulfate, Salts of sulfated and sulfonated alkyl acid amides ("Igepon T")> salts of alkylarylsulphonates, e.g. sodium dodecylbenzene sulphonate, Alkylnaphthalenesulfonic acids and their salts ("local") »Salts of sulfonated alkylaryl polyether alcohols ("Triton 720") and many other such products, detergents and emulsifiers.

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A more detailed description of such capillary or surface-active agents can be found in the Encyclopedia of Surface-Active Agents, I.P. Sisley, Chemical Publishing Go ,, Inc., Hew York, N.Y., and Surface Active Agents, A.M. Schwartz and I.V. Perry, Interscience Publishers, Inc., New York, N.Y.

Furthermore, the new compounds of the present Invention together with powdered carriers such as starch or talc, and if desired together with medicinal Active ingredients are used. They can also be incorporated into pressed plague bodies »Solutions of the new" compounds of formula I in suitable solvents can be used in cosmetic products such as sticks, pastes, jellies, creams, Lotions, roll-ons or aerosols can be incorporated. The connections can also be finely ground using conventional methods be incorporated into ointments. Solutions or dispersions of the new compounds can also be used for cleaning medical Instruments, devices for food production, or in general for cleaning surfaces are used, on which bacterial growth is to be prevented.

The new bacteriostatic compounds can be used in such antibacterial compositions as soaps or other surfactants, or agents containing detergents, in relatively small amounts. Nice. Amounts of 0.1 to 1 % of the total weight of the agent can be used, although concentrations of 1 to 3 ° are preferably used. Amounts less than 0.1 io generally prove to be of little use, since the effectiveness achieved thereby is too low. Although quantities of 5% or more are also possible, the upper limit results from considerations of usefulness. In general, increasing the concentration of the active ingredient increases the germicidal effectiveness of the agent. At higher concentrations, however, on the one hand the

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Ratio of the cost of the bactericide to the end product is uneconomical, on the other hand, such high concentrations can reduce the properties of the latter adversely affect.

When used in soap, the active ingredients can be more suitable May be added during the mechanical production process of the soap, e.g. during the grinding process. It must ensure that the active ingredient is evenly distributed in the soap. Me active ingredients can be used for this purpose, e.g. in be dissolved in a small amount of a suitable solvent; this even distribution can also be achieved with the help of a suitable dispersing or wetting agent. Every method comes with a fine distribution of the active ingredient Allowed in the end product, in embossing.

The new bacteriostatic compounds can be cosmetic in concentrations similar to those given above for soap Agents and agents containing detergents other than soap are incorporated, each being incorporated during manufacture such means conventional methods can be used.

The ranges given above for the total concentrations of bacteriostatic active ingredients also apply if the compounds of the formula I are mixed with other bacteriostatic substances Substances such as bacteriostatic phenols, bisphenols, obanilides, salicylanilides etc. can be used.

Serial dilutions were made of various compounds of the formula I prepared, given the appropriate solutions on agar and with Staphylococcus aureus, Escherichia coli and Aspergillus niger inoculated. A trypticase glucose extract was used for the antibacterial tests (S. aureua and E. coli) Agar medium and for the fungicidal experiments (A. niger) were used a Schimntel medium.

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-IG-

Composition:

Sodium nitrate

Kaliumpho sphat

Magne s iumsulf at

Potassium chloride

glucose

Agar

water

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25th ε 1 25th 8th ο, S. ο, G 10 G 10 G

1,000 g

In the case of the bacteria, growth was stopped after a 48 hour incubation period and in the case of the fungi after Measured 7 days. The results can be seen from Table I:

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Table I.

Minima. 3 hemmko na ent rati ons ei ch
racf; / nil)

A. niger:

Connection iTo .: 8. aureus: JSo coil: I. 0.6-3 384-1920 II 0.6-3 76-384 III 0.6-3 76-384 IV 0.6-3 76-384 V 0.6-3 76-384 VI 0.6-3 76-384 VII 0.6-3 384-1920 VIII 0.6-3 76-384 IX 0.1-0.6 15-76 X 0.6-3 384-1920 XI 0.6-3 384-1920 XII 0.6-3 > 1920 XIII 0.6-3 > 1920 XIV 0.1-0.6 76-384 XV 0.1-0.6 15-76 XVI 0.6-3.0 76-384 XVII 0.1-0.6 15-76 XVIII 0.1-0.6 76-384 XIX 0.6-3 76-384 XXII 0.1-0.6 15-76 XXIII 0.03-0.1 15-76 XXIV 0.6-3.0 384-1920

76-384 15- 76

> 192O
76-384 76-384 76-384 15- 76 76-384 15- 76 76-384

> 1920

> 192O

15- 76 15- 76 15- 76 15- 76 15- 76> 1920
15- 76 15- 76 76-384

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The following experiments carried out in Soife serve to illustrate the antibacterial properties of the new compounds. These bacteriostatic experiments in vitro were carried out as follows: A compound was converted into a: · :; A suitable solvent, usually dimethylformamide, dissolved at a concentration of 6 #. Half a liter of it was added to 100 ml of a 3% solution of bar soap. The soap used was a neutral, white toilet soap (made from a mixture of 85 % tallow fatty acids and 15 pounds of coconut oil fatty acids).

This gave an aqueous soap solution containing 30 ¹ OOO mcg / ml soap and 300 mcg / inl active ingredient contained. The ratio of soap to compound I was accordingly 100: 1. Two dilution series were now made, for which sterile distilled water was used and the final volume in the test tubes was 2 ml each. 28 ml of melted trypticase glucose agar were then added to each test tube. The contents of the test tubes were then placed in sterile Petri dishes, allowed to harden and inoculated with Staphylococcus aureus. The highest final concentration of active ingredient was 20 mcg / ml.

The results of these experiments with the new compounds of the formula I are shown in Table II.

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Table II Minimum concentration range

II 1.25-2.5

Y 1.25-2.5

VI 1.25-2.5

VII 1.25-2.5

XV 1.25-0.6

XVl 0.6-1.25

XVII 0.6-1.25

XVIII 0.6-1.25

XIX 0.6-1.25

XXII 0.3-0.6

XXIII 0.15-0.3

The compounds of the formula I were also tested on fabrics for their antibacterial activity. Samples of full tissue weighing 57 g were immersed in ethyl alcohol solvents, the latter 0.1 fo, 0.01 <fo _t or 0.001 ^ / wt. various compounds of Porsiel I contained. The tissue samples were air-dried and then 2.5 cin slices thereof were placed on the surface of agar media (composition see above) which had been inoculated with 3. aureus. After 4½ incubation periods, the Henci zones were measured from the edge of the tissue to the edge of the zone around the tissue sample. The results of these experiments are shown in Table III.

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Tafcello III

He- the ie (kjh) 0.001> i Con aentrat.lon ⁰ I. alcoholic'-; trace
0
2 0.1 J 5
4th
6th 01 £ 18th
11
3.6

Verbixidun.? ITo:

XVII

XXII

XXIII

XIX 7.5 2 0

In the following examples the temperatures are in Degrees Celsius.

example 1

In a suitable reaction vessel "the ml ~ 'c stirrer, reflux condenser, thermometer and dropping funnel a ^- as, ~ is erüstet, we added 300 ml of chlorosulfonic acid. To this end, 120 g of 2,4,5-trichlorophenol are added with stirring over a period of 20 minutes at room temperature. The resection vessel is heated to 60-62 ° and is kept at this temperature for 1 hour. It is then cooled to room temperature and the water is poured. Contents of the vessel on 5 kg of ice. The precipitated solid is filtered off, washed with water, dried and recrystallized from petroleum ether. This gives 2-I-4'aro.xy-3,5 »6-trichlorobenzenesulfuryl chloride, melting point 85.

Example 2

In a suitable Reakf.ionsgeiäj-s are added 130 ml of chlorosulfonic acid and cools the vessel to O ^J from _e sub Eülix-cn is then added at a ^ r ^^^ rerator of 0 Ilbrr a Zeitranni of 1 hour 76 g _2> 4 -2i ''> - '"^;--r'phenol to. The reaction is usually stirred for one hour at room temperature. Or = J. hiorau_; Poured onto 1 kg of ice * I> as white Lx ^ s-salline lrod ^ .l: t viird ab

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filtered, washed ruit V / ascer and crystallized from hexane u ^. Kan receives in this way 5 »5-dibro: n-2-hyaro ::: yboiisolsuliuiiylchlorid front oclinel point 102-103.

Example 3

In a suitable reaction vessel provided with a reflux condenser, Ti-orftrieLter- and RUlirer there are 7.3 g (0.04 Hol) 2,4,5-Tr. chloraniline, dissolved in 75 ml of ethyl ether, 5.2 g (0.02 hol) of 3,5-dichloro-2-hydroxybenesulphonyl chloride (dissolved in 50 μl of ethyl ether) are added dropwise over a period of 30 minutes. The reaction mixture is kept at the reflux temperature for 18 hours, then cooled and filtered. The ether is then removed on a rotary evaporator and the residue is recrystallized from a mixture of benzene / hexane (1: 1). You ge-.rinnt to this '' else 2-Hydro3y-2 ', 3' 4 ', 5,5' -pentachlorbencolsulfonanilid of melting point 160-161 _#

Example 4

16.2 g 3f4-Dichloraniliii and 17.5 g of 3,5-Dibroai-2-hydrOxybensolsulfo> i5 ^r lelilorid be reacted according to Example 3. FIG. By recrystallization from ethylene dichloride 3 , 5-dibromo-3 ', 4'-dichloro-2-} iydroxyben3olsulfonanilid with melting peak 216 ° is obtained »

Example 5

8 g of 2,4-dibromaniline and 5 »6 g of 3» S-Di bensolsulfonyl chloride are reacted according to Example 3. This is done by recrystallization from benzene 2-Hydroxy-2 ■, 3,4 ', 5-tetrabromobensol sulfonanilide of melting point 153-154 ° preserved.

Example 6
9.8 g (0.05 J- "ol) 2.4 _f 5 ~ xrichlcraniline are x in a.

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heated to 100 in a suitable reaction vessel. To this, 9> 7 g (0.025 mol) are added with stirring over a period of 15 minutes 3,5-Mbromo-2-hydroxybenzenesulfonyl chloride. The reaction vessel is heated 30 minutes to 110 ° and then cools down again. The contents of the vessel are then used for steam distillation subjected and the residue recrystallized from benzene / hexane. In this way 3> 5-dibromo-2-hydroxy-2 ', 4', 5 '-trichlorobenzenesulfonanilide is obtained from melting point 162-163.

Example 7

A mixture of 20 g of 2,4,5-trichloroaniline and 15 g of 2-hydroxy-3 _f 5 »6-trichlorobenzenesulfonyl chloride is kept in a suitable reaction vessel with stirring at a temperature of 150-190 ° for 6 hours. The G-vessel is then cooled to room temperature and the contents are dissolved in 300 ml of acetone. The resulting solution is filtered and the piltrate is added to 2 liters of water. The resulting precipitate is filtered, washed with water, dried and first recrystallized from toluene and then from ethanol. In this way 2 ', 3> 4 ¹ , 5>5', 6-hexachloro-hydroxybenzenesulfonanilide with a melting point of 164-165 are obtained.

Example 8

First, 15 g of 3-chloro-4-thiocyanatoaniline in 500 ml of dry toluene are added to a suitable reaction vessel thereupon 11.9 g of 2-hydroxy-3,5,6-trichlorobenzenesulfonyl chloride. The reaction mixture is first stirred for 4 hours at room temperature and then for 8 hours at reflux temperature held. The toluene is then distilled off under reduced pressure and the residue with a mixture of 20 ml concentrated hydrochloric acid and 500 ml v / ater. The product obtained is filtered off, washed with water and dried it and recrystallized it from toluene. The 2-hydroxy-3,3 ', 5,6-tetrachloro-4'-thiocyanatobensolsul-

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fonanilid "melts" at 199-201.5 °.

Example 9

According to Example 8, 10 g of 4-ethoxyaniline and 11.9 g 2 ~ Bydroxy-3,5 »6-trichlorobenzenesulfonyl chloride in 100 ml of toluene implemented. In this way (after recrystallization from a mixture of hexane / toluene 1: 1) 4'-ethoxy-2-hydroxy-3> 5,6-trichlorobenzenesulfonanilide is obtained with a melting point of 141.5-143.5.

Example 10

According to Example 8, 13 g of 3-chloro-p-toluidine and 13.2 g of 2-hydroxy-3,5,6-trichlorobenzenesulfonyl chloride reacted in 100 ml of toluene. The product obtained is crystallized out Ethanol and receives 2-hydroxy-4'-methyl-3,3 ', 5 »6-tetrachlorobenzenesulfonanilide from melting point 171-173

Example 11

G-emäss Example 8 luoranilin 8.9 g of 4-i ¹ and 11.9 g of 2-hydroxy-3,5,6-trichlorobenzenesulfonyl reacted in 70 ml of toluene. The crude product obtained is ^{recrystallized from toluene and 4 l} -fluoro-2-hydroxy-3,5,6-trichlorobenzenesulfonanilide with a melting point of 180-182 ° is obtained.

Example 12

According to Example 8, 8.4 g of p-nitroaniline and 10.3 g of 2-II-hydroxy-3,5,6-trichlorobenzenesulfonyl chloride are reacted in 100 ml of toluene. The crude product obtained is recrystallized from a mixture of toluene and ethanol to give 2-hydroxy-4'-n.itro-3,5,6-t:
keep*

3 »5,6-trichlorobenzenesulfonanilide with a melting point of 211-213

Example 13
A mixture of

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11.8 g of 4-chloro-3- (trifluoromethyl) aniline, 8.9 g of 2-hydroxy-3,5,6-trichlorobenzenesulfonyl chloride and 150 ml of isopropyl ether for 12 hours held at reflux temperature. The isopropyl ether is then removed under reduced pressure and the residue with a mixture of 50 ml of concentrated hydrochloric acid and 150 ml Treated water. The reaction mixture is filtered, washed with water, dried and recrystallized from toluene. Man obtained in this way 2-hydroxy-3,4 ', 5,6-tetrachloro-3' - (trifluoromethyl) benzenesulfonanilide from melting point 185-186.5 °.

Example 14

8.1 g of 4-isopropylaniline and 8.9 g of 2-hydroxy-J, 5,6-trichlorobenzenesulfonyl chloride are reacted according to Example 13 in 120 ml of isopropyl ether. The crude product obtained is recrystallized from toluene and then the 2-hydroxy-4'-isopropy1-3,5,6-trichlorobenzenesulfonanilide obtained with a melting point of 151.5-152.2 °.

Example 15

According to the method of Example 3, further compounds of the general formula I are obtained. The corresponding Details can be found in Table IV below.

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Table IV Raw materials

NJ O CO CO

aniline I. 3,4-dichloro I.
I. 4-chloro-3-tri- 2-hydrocybene No. formula calculated C. H Cl 64 found C. H Cl (Substituents fluoromethyl zolsulfonyl M.p. ⁰ C 37.24 1.82 - 37.45 1.71 - ten groups) 3,5'-dichloro 4-methyl-3-chloro chloride 7th (Substituents 37.24 1.82 36, 37.48 1.74 36.37 3-chlorine ten groups) 3,5-dichloro I. C ₁₂ H ₇ Cl ₄ HO ₅ S 37.2 1.82 36, 37.6 2.11 36.3 4-bromine 193-194 3,5 dichloro II C ₁₂ H ₇ Cl ₄ NO ₃ S 33.5 1.63 «Μ 34.0 1.62 - 4-iodine 199-200 3,5,6-trichloro III C ₁₂ H ₇ Cl ₄ NO ₅ S 30.12 1.47 mm 30.36 1.57 - 3,4-dichloro 154-155 3,5,6-trichloro 17th C ₁₂ H ₇ BrCl ₅ NO ₅ S 30.28 1.48 MB 30.53 1.46 - 166.5-169 O 3,5,6-trichloro V C ₁₂ H ₇ Cl ₅ INO ₅ S 37.1 1.67 «Μ 36.7 1.51 - 177-178 3,5-dibromo VI C ₁₂ H ₇ Br ₂ Cl ₂ NO ₅ S 42.6 2.75 29 42.7 2.84 28.96 216 3,5 dichloro VII C H ClPNO S 161-163 3,5 dichloro X C-, "Η _{Ί n} Ol_HO-S
I ^ 10 3 3 151-153

O CO OO

2-hydroxybene
zolsulfonyl
chloride
(Substituents
ten groups) ITo. formula
M.p. ⁰ C Portetzunff calculated C. H Cl C. Table IV H Cl , 5 aniline
(Substituents
tengrappen) 3,5,6-trichloro XII C ₁₅ H ₁₀ Cl ₃ NO ₃ S ₂ 39.2 2.5 26.7 39 found 2.5 26th 4-kethylthio 164.5-167.2 , 81 3,5 dichloro XIV C ₁₂ H ^ CIc-ITO-S 34.88 1.43 42.1 34 , 2 1.24 41 3,4,5-trichloro _L.C \ JJ ^
219-221 3,5-di bromine XXI C ₁₂ H ₇ Br ₄ HO ₃ S 25.52 1.25 - 25th , 4 1.12 2,5-dibroma 135-136 , 35 3,5,6-trichloro XXII C ₁₂ H Cl ₆ HO S - - 46.65 , 57 - 46 3,4,5-trichloro almL *. ^ / \ J ^
181-182 - 3,5-dibromo XXIY C ₁₂ H ₈ Br-HO-S
'** ^ ^ J 29.66 1.66 - 29 1.62 4-Brora 179-180 , 5 3,5,6-trichloro XXYII C, _o H "Cl ^ PlT0" S - - 28.7 , 49 - 28 4-fluoro 179.5-182 , 4 3,5,6-trichloro YIII C ₁₃ H ₇ Cl ₃ F ₃ P ₃ NO ₃ S 37.1 1.7 25.3 37 - 1.9 25th , 2 3-trifluoromethyl I 3,5,6-trichloro XYI 0 _Ί ^ Gl ₁ -H ¹ OS
Sd D 0 j> 34.2 1.4 42.1 34 1.6 42 , 6 3,4-dichloro 3,5,6-trichloro XYII C ₁₂ H ₆ Cl ₅ NO ₃ S 34.2 1.4 42.1 34 , 6 1.7 41 , 7 3,5 dichloro 3,5,6-trichloro XXYIII ^C 16 ^H l6 ^G1 3 ^iT0 3 ^S - 26.0 , 2 25th 4-n-lutyl , 6 -

Claims (31)

Claims where X is chlorine or bromine, a 1, 2 or 3, Y halogen, b a number from 1-4 »Z trifluoromethyl, Thiocyanato, nitro, lower-allsyl, lower-alkylthio or lower-alkoxy and c is 0 or 1, and the number of substituents a + b + c is at least 4, with the exception, that if X = Y = Z = bromine, a + b + c is at least 3, characterized in that-one connects the general a formula Xa- _with a compound of the general formula 20981.7 / 1655 22-2151A91 wherein O R is a free, esterified or etherified hydroxyl group represents and X, Y, Z, a, b and c have the above meaning converts, and, if 0 R, an esterified or etherified hydroxyl group represents, the hydroxyl group in the reaction product is released again. 2) Process according to claim 1, characterized in that at least 2 moles of the compound III to 1 mole of the compound II begins. 3) Process according to claim 1, characterized in that at least 1 mole of the compound III and 1 mole of one mild base per mole of compound II is used. 4) Method according to one of claims 1-3, characterized characterized in that one has 3r5-diclilor-2-hydroxybenzenesulfonyl chloride reacts with 2,4,5-trichloroaniline * 5) Process according to any one of claims 1-3, characterized in that 3,5,6-trichloro-2-hydroxybenzenesulfonyl chloride reacts with 3,5-dichloroaniline " 6) Process according to any one of claims 1-3, characterized in that 2-hydroxy-3 _f 5,6-trichlorobenzenesulfonyl chloride is reacted with 4-chloro-3- (trifluoromethyl) aniline, 209817/1655 215H91 7) Method according to one of claims 1-3 »thereby characterized that there is 2 ~ hydroxy-3> 5,6-trichlorobenzenesulfonyl chloride with 3 »4-dichloroaniline. 8) Process according to one of claims 1-3 _f dadiirch that 2-hydroxy-3 _t 5 _f 6-trichlorobenzenesulfonyl chloride is reacted with 3 »4,5-trichloroaniline. 9) Process according to any one of claims 1-3 »characterized in that 2-hydroxy-3» 5,6-trichlorobenzenesulfonyl chloride reacts with 2,4,5-trichloroaniline. 209817/1655 10) Means with antibacterial properties, thereby characterized in that it is a compound of the general formula where X is chlorine or bromine, a I, 2 or 3 » Y halogen, b a number from 1-4, Z trifluoromethyl, thiocyanato, nitro, lower-alkyl, lower-alkylthio or lower-alkoxy and c is 0 or 1, and the number of substituents a + b + c is at least 4, with the exception that when X = Y = Z = bromine, a + b + c is at least 3, and includes a carrier. 11) means according to claim 10, characterized in that that it is a compound of the formula I 2-hydroxy-2 ', 3,4' »5,5'-pentachlorobenzenesulfonanilide contains. 12) Agent according to claim 10, characterized in that it is 2 ~ hydroxy-3,3 ', 5,5', 6-pentachlorobenzenesulfonanilide as a compound of the formula I contains. 13) Agent according to claim 10, characterized in that it is 2 ~ hydroxy-3,4 ', 5,6-tetrachloro-3' - (trifluoromethyl) -benzenesulfonanilide as a compound of the formula I contains. 14) means according to claim 10, characterized in that 209817/1655 that it contains 2-hydroxy ~ 3.3 ^f , 4 '»5,6-pentachlorobenzenesulfonanilide as a compound of the formula I. 15) means according to claim 10, characterized in that that there is a compound of formula I 3,3 ', 4', 5,5 ', 6-hexachloro-2-hydroxybenzenesulfonanilide contains. 16) means according to claim 10, characterized in that that it is a compound of the formula I 2 ', 3,4', 5,5 ', 6-hexachloro-2-hydroxybenzenesulfonanilide contains. 17) Soap with antibacterial properties, characterized by a content of at least 0.1% by weight of one Compound of the general formula SO ₂ MH where X is chlorine or bromine, a I, 2 or 3, Y is halogen, b is a number from 1-4, Z is trifluoromethyl, Thiocyanato, ifitro, lower-alkyl, lower-alkylthio or lower-alkoxy and c is 0 or 1, and the number of substituents a + b + c is at least 4, with the exception that, when X = Y = Z = bromine, a + b + c is at least 3. 209817/1655 -26-215H91 18) Use of a compound of the formula OH Xa wherein X is chlorine or bromine, a I, 2 or 3> Y halogen, b is a number from 1-4, Z triiluomethyl, ψ thiocyanato, ITitro, lower-alkyl, lower-alkylthio or lower-alkoxy and c is 0 or 1, and the number of substituents a + b + c is at least 4, with the exception that when X = Y = Z = bromine, a + b + c is at least 3, as an antibacterial and / or fungicidal active ingredient in cleansing and / or cosmetic agents. 19) Use of 2-hydroxy-2 ', 3 ₁ 4'> 5 , 5'-pentachlorobenzenesulfonanilide according to claim 18. 20) Use of 2-hydroxy-3,3 ', 5 , 5', 6-pentachlorobenzenesulfonanilide according to claim 18. 21) Use of 2-hydroxy-3,4 ', 5 »6-" fcetrachlor-3' - (trifluoromethyl) -benzenesulfonanilide according to claim 18. 22) Use of 2-hydroxy-3,3 ', 4', 5 ₁ 6-pentachlorobenzenesulfonanilide according to claim 18. 23) Use of 3,3 ', 4', 5,5 ', 6 ~ hexachloro-2-hydroxybenzenesulfonanilide according to claim 18. 209817/1655 24) Use of 2, 3,4 ', 5,5', 6-hexachloro-2-hydroxybenzenesulfonanilide according to claim 18. 209817/1655 215U91 25) compounds of the general formula SO ₂ NH wherein X is chlorine or bromine, a 1, -2 or 3 »Y halogen, b is a number from 1-4, Z trifluoromethyl, Thiocyanato, nitro, lower-alkyl, lower-allylthio or lower-alkoxy and c is 0 or 1, and the number of substituents a + b + c is at least 4, with the exception that when X = Y = Z = bromine, a + b + c is at least 5. 26) 2-Hydroxy-2 ', 3,4', 5,5 '-pentachlorobenzenesulfonanilide. 27) 2-Hydroxy-3, 3 ', 5 , 5 ^f , 6-pentachlorobenzenesulfonanilide. 28) 2-Hydroxy-3,4 ', 5,6-tetrachloro-3' - (trifluoromethyl) -benzenesulfonanilide. 29) 2-Hydroxy-3 »3 ', 4', 5,6-pentachlorobenzenesulfonanilide. 30) 3,3 ', 4', 5,5 ', δ-hexachloro ^ -hydroxybenzenesulfonanilide . 31) 2 ', 3,4 ·, 5,5', 6-hexachloro-2-hydroxybenzenesulfonanilide. 209817/1655