DE2145733A1 - Thienyl iodonium salts - as antimicrobial agents - Google Patents

Abstract

Cpds. (I): (where R is naphthyl, phenyl mono substd. by NO2, F, Cl, Br, alkyl, alkoxy, CF3, Ph or PhO or phenyl disubstd. by F, Cl, Br, alkyl or alkoxy and R' circled negative is F, Cl, Br, I, F3C. COO, alkanoate, NOE or BF4"alkyl" and "alkoxy" contain 1-4 4) are prepd. by reacting TFA, tiophen and R-I = (OCOCH3)2 to give (I; R'- is CF3COO2) then exchanging R' circled negative = TFA for Hal circled negative and then reacting with a silver salt for other values of R1 circled negative.

Description

The invention relates to new chemical .Verbindungen, methods for their preparation and compositions containing the new compounds. the In particular, the invention relates to thiebnyliodonium salts which are used as antimicrobial agents and anti-microbial agents and for the control of many bacterial organisms such as gram-negative and gram-positive species, mold, meltau, fungi and slime are suitable are.

They are of particular value to paper, plaster baw. Material, fibreboard, woven and non-woven materials, textiles, cooling water, softeners, latex, Polymers, resins, adhesives, printing inks, paints, fuels, cutting oils, lubricants, To collect seeds, terrestrial plants, detergents, soaps, shampoos and wood or to sohützen.

Many chemical compounds are considered valuable antimicrobials Means and suggested as a preservative. The ones proposed so far However, materials could only find a limited use because they have one or more Disadvantages showed such as low toxicity to the bacterial organisms, toxicity compared to relatively few types of organisms. Toxicity to the gram-positive Species, but not unfavorable to the gram-negative types of bacterial organisms Toxicity to water or terrestrial or earth plants, unfavorable toxicity to mammals and lack of toxicity in the presence of detergents or Soap. The compounds of the invention and methods in which they are used as antibiotics used have a special combination of properties. they show low toxicity to fish, mammals and earth plants and parts of plants and they show high toxicity to microbes including gram-negative ones and gram-positive types, and this is true of many types of environment including.

the soaps and detergents such as a fatty acid, anionic and nonionic soaps and detergents. Another advantage is the instability of the compounds in essentially alkaline, aqueous conditions where. the compounds tend to degrade and therefore they are degradable. The new compounds according to the invention are thienyliodonium salts of the general formula where R is naphthyl, fluorophenyl, chlorophenyl, bromophenyl, alkylphenyl, alkoxyphenyl, nitrophenyl, trifluoromethylphenyl, phenylphenyl, phenoxyphenyl or disubstituted phenyl, the substituents being fluorine, chloro, bromine> alkyl or alkoxy, and where R 'fluoride is chloride, bromide, iodine , Trifluoroacetate, alkanoate, nitrate or tetrafluoroborate means.

The terms "alkyl", "alkoxy" and "alkanoate" mean groups that Contain 1 to 4 carbon atoms, such as methyl, ethyl, propyl, butyl, Methoxy, ethoxy, Propoxy, butoxy, acetate, propionate or butyrate Compounds are crystalline, solid materials that are in common organic solvents and are somewhat soluble in water.

The invention also relates to a process which consists in treating microbes in inanimate, plant and external animal locations with an antimicrobial amount of a 2-2hienyliodonium salt of the formula where R is naphthyl, thienyl, phenyl, phenyl, monosubstituted by nitro, fluorine, chlorine, bromine, alkyl, alkoxy, g fluoromethyl, phenyl or phenoxy, or phenyl, disubstituted by fluorine, chlorine, bromine, alkyl or lower-alkoxy, and where R 'is fluoride, chloride, bromide, iodide, trifluoroacetate, alkanoate, nitrate or tetrafluoroborate and where the alkyl, alkoxy and alkanoate groups contain 1 to 4 carbon atoms. The invention further relates to compositions containing an inanimate material capable of harboring microbes and an antimicrobial amount of a 2-thienyliodonium salt as defined above.

It has been found that the compounds are effective against many bacterial organisms or plants including gram-negative and gram-positive species such as Staphylococcus aureus, Salmonella typhosa, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Candida pelliculosa, Aspergillus terreus, Aerobacter aerogenes, Penicillium chrysogenum, Aspergillus nigery Chaetomium globosum, Penicillium digitatum, Phomopsis citri, Diplodia natalensis, Alternaria solani, Erwinia amylovora or Rhizoctonia solani have high toxicity. The connections have low toxicity to terrestrial plants and they can up many plants that are infested with bacteria, and on their locations in bactericidal effective amounts can be applied, giving excellent control of the microbial organisms that contain the seeds, roots or parts that are above the Earth lying, which attack terrestrial plants. By such a process Terrestrial plants and seeds are protected and the harvest yield and emergence and the growth of the seedlings are improved. It has also been found that the compounds in adhesives, cooling water, printing inks, plasticizers, latices, resinous, polymeric materials, fuels, greases, soaps, detergents, shampoos, Cutting oils and oil or latex paints can be incorporated to irnd mold Meltau and the breakdown of such products caused by microbial attack will prevent. The term "resinous, polymeric materials" includes natural ones and synthetic resinous polymers and plastic compositions or plastic ones Compositions and films made therefrom.

The compounds can also be beneficial in natural and synthetic Materials or fabrics are used in paper and other cellulose-containing products can be incorporated, or they can be used to cut wood, timber or

Lumber, fibreboard and cement impregnate to make these products from attack by putrefactive, mold and meltau bacterial organisms and from degradation to protect.

The Thieiiyliodoniumtrifluoroacetate can be prepared by adding together trifluoroacetic acid, thiophene and an iodosodiacetate of the formula implements. The reaction is preferably carried out in an organic solvent such as methylene chloride, ethylene dichloride, carbon tetrachloride, methyl chloroform, heptane or methylcyclohexane and expediently in acetic anhydride or in a mixture of acetic anhydride and trifluoroacetic acid. The reaction takes place with each quantitative ratio of the reagents used. In the reaction, the reagents are consumed in substantially equimolar amounts, and the use of amounts corresponding to approximately equimolar proportions is preferred. The reaction takes place at temperatures from -30 to + 40 ° C and is preferably carried out at a temperature of -20 ° to 40 ° C. After the reaction has ended, the desired thienyliodonium trifluoroacetate is separated off by known methods.

In the event of an expedient procedure for carrying out the implementation trifluoroacetic acid and iodosodiacetate are reacted together in the reaction medium and the thiophene reagent is added portionwise with stirring. The implementation is exothermic and runs easily with the addition of the thiophene. The temperature of the Reaction mixture can be controlled by adjusting the rate of addition of thiophenes and by cooling externally. The implementation is essential terminated when the addition of the thiophene is complete. When you look at the resulting reaction mixture If left to stand for some time at slightly elevated temperatures, improved ones are often obtained Exploit. After completion of the reaction, the reaction mixture can under reduced Distilled under pressure, some of the low-boiling components being removed is and where the desired Thienyljodoniuu-trifllloracetat as crystalline Residue receives. This residue can further result from crystallization organic solvents or from aqueous organic solvents such as acetone, Ethyl acetate, heptane or mixtures thereof.

The thienyl iodonium chlorides, bromides and iodides can be selected from the corresponding Thienyliodonium trifluoroacetates by treating the trifluoroacetate with a suitable gaseous or aqueous hydrogen halide are produced. the Reaction of the trifluoroacetate with the hydrogen halide is preferably carried out in liquid Reaction medium, expediently in acetone or ethyl acetate, carried out The amount the reagent that is used is not critical as it is part of what is desired Thienyliodonium halide is always obtained, regardless of the parts in which the reagents used. As in the reaction, however, the reagents essentially are used in equimolar proportions, the use of the reagents in amounts which correspond to such proportions are preferred. Implementation takes place quickly at temperatures from 0 to 500C instead, the desired thienyliodonium halide and the trifluoroacetic acid are formed. The halide salt generally falls during the reaction the reaction mixture as a crystalline solid. After implementation, the Reaction mixture can be distilled at reduced pressure, being low-boiling Components are removed and the desired salt product precipitates.

The thienyl iodonium halides produced in this way can be decanted off or filtration, and they can be separated by recrystallization from different organic solvents or from aqueous organic solvents such as acetone; Ethyl acetate, n-pentane, heptane or mixtures thereof can be further purified.

The xhienyl iodonium acetate, propionate, butyrate, nitrate and tetrafluoroborate can from the corresponding thienyl iodonium halides, expedient from the corresponding chloride. With such procedures, the corresponding thienyl iodonium halide with silver nitrate, silver tetrafluoroborate or treated with the silver salt of an alkanecarboxylic acid in water as the reaction medium. the Implementation takes place quickly, with the desired hien.ylsodonium salt and silver halide are formed.

The procedures, how to react the reagents and the reaction conditions are exactly as described in the previous section. After completion After the reaction, the desired salt is separated off by decanting or filtration.

The thienyliodonium fluoride salts can be prepared in a similar manner by adding thienyl iodonium chloride with silver fluoride in water as the reaction medium implements. The reaction takes place quickly, producing the desired thienyliodonium fluoride salt and silver chloride are formed. The procedures for converting the reagents and the reaction conditions are the same as described in the previous section became. After the completion of the reaction, the desired fluoride salt is removed from the reaction medium separated by decanting or filtration.

The iodosodiacetates used as starting materials can be prepared by known methods.

In this process, a dichloride of the general formula R-ICI2 reacted with lead acetate (0H30OO-Pb-O0C0113).

The reaction takes place quickly at room temperature, whereby the desired diacetate and lead chloride are formed. The one in such implementations The dichlorides used are conveniently chlorinated according to known methods eier iodine compound (R-I) produced.

Another method can use all but the nitro-aodosodiacetates Manufacture by making iodine aromatic compounds, RI, with peracetic acid in acetic acid and acetic anhydride solution. This reaction is conveniently carried out at room temperature carried out. In these reactions, the desired products are found to be crystalline Solids are isolated and they are separated and purified according to known methods.

You can get good control of the microbes when you look at the toxic ones Connections to the parts of terrestrial plants that lie above the earth, applied at a dose of 1.12 to 11.2 or more, kg / ha (1 to 10 pounds / acre). When used on soil to control microbes attacking roots, good results are obtained when the salt compounds are used in an amount of 11.2 to 112 kg / ha or more (10 to 100 pounds / acre). With the general For field applications, it is generally preferred that the compounds up to be distributed to a depth of at least 5 cm (2 inches) below the surface of the earth.

When protecting and preserving printing inks, adhesives, Soaps, detergents, lubricating greases, fuels, cutting oils, textiles, fabrics, Latices, resinous plasticizers, polymeric materials and paper are obtained good results when the compounds in such products in an amount of at least 0.0005% by weight are incorporated. Good results are obtained when protecting seeds, when the seeds with the compounds in a dose of 0.03 wt.%, calculated on the weight of the semen, to be treated. When preserving wood, wood fiber panels and plaster of paris give excellent results when the connections are through usual treatment of these products in an amount of 0.0016 g / cc or more (0.1 pound or more per cubic foot). When treating fruit good results are obtained by washing with liquids that are at least 5 ppm in terms of the weight of the salt compound.

For the preservation and protection of oil and latex paints and stains the compounds are preferred against decomposition caused by bacteria Used in concentrations of at least 0.05% by weight.

The inventive method can be carried out by unmodified compounds are used or by making liquid or dusty ones Uses compositions that contain the toxins. With such use the compounds with one or a plurality of additives or adjuvants including water, organic solvents, petroleum oils, petroleum distillates, Naphthas or other liquid carriers, polymeric thickeners, urea, modified surface-active dispersants and finely divided inert solids. In admixtures in which the adjuvant or excipient is a finely divided Solid, a surfactant, or a mixture of a surfactant Agent and a liquid diluent, the carrier acts together with the active ingredient, and improved results can be obtained.

The exact concentration of toxins used in the treatment compositions is not critical and can vary widely provided that the required dose of active agent is present, the concentration of Toxin in liquid compositions is generally in the range of 0.0001 up to 50 wt. Concentrations of up to 95 wt / c are often expediently used. In the case of dusts or powders, the concentration of toxin can range from approximately 0.1 to 95% by weight. In the case of compositions that are used as concentrates, can the toxins are present in a concentration of 5 to 98 wt.

In further embodiments, the salt compounds are as they can be used in the present invention, or compositions containing the Contain salt compounds, preferably according to the invention with one or more pesticidal agents or preservatives mixed together, one being products with improved properties. In such an embodiment, the pesticidal or preservative compound either as an additional toxin, used as an additive or as an adjuvant. Examples of pesticidal or preservative acting compounds include substituted phenols, oresols, substituted Cresols and their heavy metal salts, bisphenols and thiobisphenols, halogenated Salicylanilides, organic sulfur compounds, carbamate compounds, quaternaries Ammonium compounds, organometallic compounds, inorganic salts and various other compounds such as phenol, cresol, trichlorophenols, tetrachlorophenols, pentachlorophenol, p-chloro-m-cresol, di- and tribrominated salicylanilides, 2,2'-methylenebis (3,4,6-trichlorophenol), 2,2'-thiobis- (4,6-dichlorophenol), 1- (3-chloroallyl) -3,5,7-triaza-1-azoniaadamantane chloride, Halo (alkylsulfonyl) pyridines, halo (alkylsulfinyl) pyridines, 2,4 ', 5-tribromosalicylanilide, 2-chloro-4-cyclohexylphenol, 2-chloro-4-cyclopentylphenol, 2,2'-bis (3,4,6-trichlorophenyl) methane, 2,2'-bis (5-chloro-2-hydroxyphenyl) methane, halogenated trifluoromethylsalicylanilide, Zinc dimethyldithiocarbamate, 2-mercaptobenzothiazole, 3,5-dimethyltetrahydro-1,3,5,2H-thiadiazine-2-thione, 2,3-dinitro-1,4-dithiaanthraquinone, dodecylpyridinium chloride, alkyldimethylbenzylammonium chloride, Dialkyldimethylammonium chloride, phenyl mercury (II) acetate, phenyl mercury (II) oleate, Phenyl mercury (II) propionate, chloromethoxyacetoxy mercury (II) propane, bis-tributyltin oxide, Bis-tripropylsinnoxyd, copper pentachlorophenate, Copper 8-hydroxyquinolate, Mercury (II) chloride, boric acid, sodium borate, ethylmercury (II) chloride, 9-undecylenic acid or 10,10'-oxybisphenoxarsine and 1,4-bromobisacetobutene.

The following examples illustrate the invention without, however, ADDING it restrict.

Example 1 4-chlorophenyl-2-thienyliodonium trifluoroacetate 4-chloroiodosobenzene diacetate (17.3 g, 0.05 mol) were added to a mixture of 15 ml each of acetic anhydride and trifluoroacetic acid and a solution of thiophene (8.4 g, 0.10 mol) in 60 ml of acetic anhydride slowly. The addition was carried out with stirring for 55 minutes at -2OQ0. The mixture was stirred for a further 65 minutes at -200 ° C. and heated the reaction mixture then and kept it at 3 ° C with stirring for 15 hours, to be sure that the implementation went through to the end. The reaction mixture was then by fractional distillation under reduced pressure up to 500C concentrated and the resulting residue was with. 100 ml of diethyl ether diluted.

During the dilution, the 4-chlorophenyl-2-thienylfodonium trifluoroacetate separated as a crystalline residue and was separated off by filtration. The solid was recrystallized from a mixture of acetone and n-pentane, melting point 156 to 157.5 ° C.

For example 2 4-chlorophenyl-2-thienyliodonium chloride 4-chlorophenyl-2-thienyliodonium trifluoroacetate (7 g, 0.0161 mol) was in 8 ml of an 88 wt. % solution of formic acid in water dispersed and a saturated aqueous solution of hydrogen chloride (12 nl) became added with stirring at room temperature. During the encore divorced 4-chlorophenyl-2-thienyliodonium chloride is in the form of a crystalline solid off, it was filtered and washed with ether and water and twice from ethanol recrystallized. The product melted at 217-21,800.

Example ~ 3 4-Methylphenyl-2-thienyliodonium trifluoroacetate 4-iodosotoluene diacetate (1.01 g, 0.3 mol) was added to a mixture of 250 ml of acetic anhydride and 90 ml Trifluoroacetic acid dispersed and the resulting mixture was cooled to -20 ° C. A solution of thiophene (50.5 g, 0.6 mol) in 300 ml of acetic anhydride was under Stirring added over a period of 1.5 hours. About more were stirred 2 hours at -200C and then 16 hours at -3 ° C. The reaction mixture was taking distilled under reduced pressure, the temperature being gradually increased to 600C and 4-methylphenyl-2-thienyliodonium trifluoroacetate was obtained as a residue. The residue was washed with ether and successively from ethyl acetate and a Recrystallized mixture of acetone and n-hexane. The product melted at 153 bis 154,500.

Example 4 1-Naphthyl-2-thienyliodonium trifluoroacetate 1- (diacetoxyiodine) naphthalene (372 g, 0.1 mol) was dissolved in 150 ml of acetic anhydride and 30 ml of trifluoroacetic acid dispersed uiid thiophene (16.8 g, 0.2 mol), dissolved in 100 ml acetic anhydride, was added at 2000 with stirring over a period of 50 minutes. One stirred an additional 1.5 hours while maintaining the temperature at -20 ° C and then stirred one for 16 hours at -3 ° C. The reaction mixture was at 60 ° C at 1 to 2 mm distilled to remove low-boiling components, and where the 1-naphthyl-2-thienyliodonium trifluoroacetate in the form of a crystalline Received arrears. The residue was washed with ether and recrystallized from acetone. The product melted at 161 to 16200.

Example 5 4-Nitrophenyl-2-thienyliodonium trifluoroacetate 4-Nitroiodosobenzene diacetate (90 g, 0.245 mol) was dissolved in 250 ml of acetic anhydride and 75 ml of trifluoroacetic acid didispersed and thiophene (41.2 g, 0.49 mol), dissolved in 300 ml of acetic anhydride, was added at 2000 over 2.5 hours. The temperature was left Reaction mixture rise to -5 ° C. and then stirred for a further 14 hours.

The reaction mixture was then fractionated to 6000 at 1 to 2 mm distilled to remove low-boiling components, the 4-nitrophenyl-2-thienylj odonium trifluoroacetate was obtained as a crystalline residue. The residue was with Washed ether and recrystallized from a mixture of ethyl acetate and acetone. The recrystallized product melted at 150-15200.

EXAMPLE 6 Phenyl-2-thienyliodonium tetrafluoroborate Phenyl-2-thienyliodonium iodide (8.15 g, 0.0197 mol) is in a mixture of 150 ml of water and 25 ml of ethanol suspended and 7.9 g (0.019 mol) of a proprietary aqueous silver fluoroborate solution that 7.9 g (0.019 mol) of silver fluoroborate is added thereto. The mix will Stirred at 50 to 60 ° C for 1/2 hour, cooled and filtered to remove the silver iodide, that was formed as a by-product to remove the filtrate is then mixed with animal charcoal treated, filtered and concentrated by heating at 45 ° C under reduced pressure, wherein the phenyl-2-thienyliodonium tetrafluoroborate is in the form of a colorless solid Residue remains. The solid product is rubbed with ethyl ether, filtered and dried to obtain a purified product which decomposes at 124 ° C melts.

In a similar way, the following compounds were made: 4-chlorophenyl-2-thienyliodonium iodide, mp 121-124 ° C; 4-methylphenyl-2-thienyliodonium chloride, M.p. at 225 to 22700, and iodide, m.p. at 130 to 131.5 ° C; 1-raphthyl-2-thienyliodonium chloride, Mp 169 to 171 ° C; 3,4-dichlorophenyl-2-thisnyliodonium trifluoroacetate, m.p. 152 to 15400; 3,4-dichlorophenyl-2-thienyliodonium chloride, m.p. at 152 to 154 ° C, and bromide, m.p. 174.5 to 176 ° C; 4-fluorophenyl-2-thienyliodonium trifluoroacetate, Mp at 127 to 128 ° C; 4-fluorophenyl-2-thienyliodinium bromide, mp 172-173 ° C; 3-chlorophenyl-2-thienyliodonium trifluoroacetate, m.p. at 108 ° C; 3-chlorophenyl-2-thienyliodonium chloride, Mp at 224 ° C; 4-nitrophenyl-2-thienyliodonium chloride, m.p. at 161 to 162 ° C, and bromide, m.p. 149 to 151 ° C; 4-bromophenyl-2-thienyliodonium trifluoroacetate, m.p. at 177 to 179 ° C; 4-bromophenyl-2-thienyliodonium chloride, m.p. at 230 to 232 ° C; 3-methylphenyl-2-thienyliodonium trifluoroacetate. M.p. 85 to 8600; 3-methylphenyl-2-thienyliodonium chloride, Mp 213-215 ° C; 2,5-dimethylphenyl-2-thienyliodonium trifluoroacetate, m.p. at 159.5 to 16100; 3,4-Dimethylphenyl-2-thienyliodonium trifluoroacetate, m.p. 127 to 130 ° C; 2,5-dimethylphenyl-2-thienyliodonium chloride, m.p. at 155.5 to 15700; 3,4-Dimethylphenyl-2-thienyliodonium chloride, m.p. 147 bis 150 ° C; Phenyl-2-thienyliodonium trifluoroacetate, m.p. 158 to 16,000; 4-phenoxyphenyl-2-thienyliodonium trifluoroacetate, Mp 123.5 to 125.0 ° C; 2-Biphenyl-2-thienyliodonium trifluoroacetate, m.p. 146 to 1480C; 2-biphenyl-2-thienyliodonium chloride, m.p. 175 to 17800; 4-ethoxyphenyl-2-thienyliodonium trifluoroacetate, Mp at 148 to 150 ° C; 4-Ethoxyphenyl-2-thienyliodonium chloride, m.p. 188 to 190 ° C; 3-Trifluoromethylphenyl-2-thienyliodonium trifluoroacetate, m.p. 108 to 109 ° C; 3-trifluoromethylphenyl-2-thienyliodionium chloride, m.p. at 1880 ° C. with decomposition; 3-Trifluoromethylphenyl-2-thienyliodonium tetrafluoroborate, m.p. at 137-138 ° C.

Example 7 Various thienyl iodoium salts were melted in Nutrient agar dispersed to produce culture media containing 0.001% by weight of one of the salt compounds contained. Such molten media were then poured into petri dishes and the solidified surface of each dish was filled with a culture broth for 24 hours inoculated either organisms of Staphylococcus aureus or of 2almonella typhosa contained. In a comparative experiment Petri dishes, which contained unmodified nutrient agar, each individually in the same way inoculated to the organisms mentioned. After 2 days of incubation at 35 ° C, the The nutrient medium in each dish is examined individually for microbial growth. The exam showed that the agar surfaces in the dishes containing the Ghienyliodonium salts, were free from bacterial growth. Towards the end of the experiments one observed a strong growth of the two organisms mentioned on the comparison dishes. The thienyl iodonium salts obtained according to the procedure previously described were as follows: PhenyS-2-thienyliodonium chloride 2,2'-bisthienyliodonium chloride 4-chlorophenyl-2-thienyliodonium chloride, 4-chlorophenyl-2-thienyliodonium iodide, 4-nitrophenyl-2-thienyliodonium chloride 4-fluorophenyl-2-thienyliodonium trifluoroacetate 1-naphthyl-2-thienyliodonium chloride 2,2'-bisthienyliodonium iodide, 4-methylphenyl-2-thienyliodonium chloride, 2,2'-bisthienyliodonium bromide 2,5-dimethylphenyl-2-thienyliodonium trifluoroacetate 2-trifluoromethylphenyl-2-thienylj odonium trifluoroacetate 3,4-dichlorophenyl-2-thienyliodonium trifluoroacetate 4-chlorophenyl-2-thienyliodonium chloride 2,2'-bisthienyliodonium trifluoroacetate, 1-naphthyl-2-thienyliodonium trifluoroacetate Phenyl-2-thienyliodonium bromide phenyl-2-thienyliodonium trifluoroacetate 3-chlorophenyl-2-thienyliodonium chloride Phenyl-2-thienyliodonium tetrafluoroberate, 4-ethoxyphenyl-2-thienyliodonium trifluoroacetate.

B e i s p i e l 8 4-chlorophenyl-2-thienyliodonium chloride is used in a Color composition used to keep the color against the attack and the subsequent one Degradation by mold and Meltau: -protect organisms. In this procedure the salt compound in the latex paint in an amount of 0.3% by weight, based on the finished color composition, dispersed and incorporated.

The parbe used in these procedures is made by making a pigment dispersion with a mixture of materials, which is a synthetic Latex, a copolymer of ethyl acrylate, methyl methacrylate, acrylic acid and Methacrylic acid, contains, well mixed. The color has the following composition: Pigment Dispersion 'approximately g / L (lbs. Per 100 gallons) of water 168 (140) potassium tripolyphosphate 1.8 (1.5) xitane dioxide 288 (240) mica (equivalent to a sieve with a clear Mesh size of 0.045 mm; 325 mesh) 60 (50) calcium carbonate 24 (20) clay (finely ground) 24 (20) propylene glycol (molecular weight 1200) 4.8 (4) material mixture methyl cellulose 180 (150) synthetic latex 607 (506) antifoam agent 12 (10) wood panels were made then with the modified compositions and with the unmodified scar coated. The plates were dried and then placed in a tropical for 2 months. Chamber at a relative humidity of 95% and one temperature Preserved by 280C (820F). The wooden panels were then examined to determine whether growth of the microorganisms was obtained. The exam showed a complete Control of the growth of mold and meltau organisms.

The comparison plates, those with unmodified composition were coated, showed at the time of the test a strong growth of mold and meltau organisms covering approximately 75% of the painted surface.-B e i s p i e l 9 phenyl-2-thienyliodonium chloride, 2,2-bisthienyliodonium chloride and for comparison purposes diphenyliodonium chloride were individually dispersed in ivory soap, whereby concentrates were prepared containing 1% by weight of iodonium salt to 50 parts by weight of soap contained. The soap concentrates were serially with liquid nutrient agar 42 ° C dispersed and diluted to obtain culture media that different Contained concentrations of one of the iodonium salts. The culture media became uniform inoculated with Staphylococcus aureus and placed in Petri dishes. The inoculation is carried out with Eulturnutrients of the specified organisms, which approximately 5. x 108 Organisms / ml, with a ratio of 1/10 ml bacterial culture per 20 ml of culture medium containing the test compound worked. In a comparative experiment will. Culture medium containing the same amount of Ivory soap, similar to the inoculated from the same organisms. After 2 days of incubation at 3700, the plates were examined for their microbial growth. The test showed that the plates that 2.5 parts per million by weight, ppm, phenyl-2-thienyliodonium chloride and 5 parts by weight 2,2'-bisthienyliodonium chloride per million, completely free from bacterial growth of Staphylococcus aureue (indicated in the table as 100% death ), while the plates containing 500 wt. 2 parts per million diphenyliodonium chloride, and the control plates, which did not contain the iodonium salt, were strong, uniform Exhibited growth of the test organism.

The procedure described above is repeated while taking the concentrations of 4-chlorophenyl-2-thienyliodonium chloride, 3,4-dichlorophenyl-2-thienyliodonium chloride varies and for comparison purposes bis (4-chlorophenyl) iodonium chloride, phenyl-4-chlorophenyl and bis (2, 4-dichlorophenyl) iodonium chloride used in a series of experiments, in which the culture media - individually inoculated with the organism Aerobacter aerogenes became. The results obtained are summarized in Table 1.

Table I Compound Concentration% Death (ppm) of A. aerogenes According to the invention 4-chlorophenyl-2-thienyliodonium chloride 1 100 3,4-dichlorophenyl-2-thienylj odonium chloride 1 100 comparison bis (4-chlorophenyl) iodonium chloride 100 0 phenyl-4-chlorophellylj odonium chloride 10 0 bis (2,4-dichlorophenyl) iodonium chloride 10 0 the one described above The procedure is repeated again in a series of experiments in which the culture media individually inodulated with the organism Salmonella typhosa and where the Culture medium contained different concentrations of one of the iodonium salts, like it in the Table II below is given. The bowls showed the results given in Table II when tested.

Table II Compound Concentration% Death (pPm) @ of S.tyPhosa According to the invention 2,2'-bisthienyliodonium chloride 5,100 phenyl-2-thienyliodonium chloride 2.5 100 4-chlorophenyl-2-thienyl iodonium chloride 1 100 4-bromophenyl-2-thlenyl iodonium chloride 5 100 3,4-dichlorophenyl-2-thienyl sodonium chloride 1 100 Comparison diphenyl iodonium chloride 500 0 phenyl-4-chlorophenyl iodonium chloride 10 0 bis (4-bromophenyl) iodonium chloride 10 0 bis (4-bromophenyl) iodonium bromide 10 0 bis (2,4-dichlorophenyl) iodonium chloride 10 0 The process described above is repeated again, each 2,2'-bisthienyl iodonium chloride, Phenyl-2-thienyliodonium chloride, 4-bromophenyl-2-thienyliodonium chloride, bis- (4-bromophenyl) iodonium chloride and bis (4-bromophenyl) iodonium bromide have been used in a number of experiments which the culture media individually with the organism Aerobacter aerogenes individually be inoculated.

The results obtained are summarized in Table III below.

Table III Compound concentration clo death (ppm) of A. aerogenes According to the invention 2,2'-bisthienyliodonium chloride 5,100 phenyl-2-thienyliodonium chloride 2.5 100 4-bromophenyl-2-thienyliodonium chloride 5 100 Ver,;, leich bis (4-bromophenyl) iodonium chloride 10 0 bis (4-bromophenyl) iodonium bromide 10 0

Claims (2)

Claims 1. Antimicrobial agent, characterized in that it is a 2-thienyliodonium salt of the formula contains, wherein R is naphthyl, thienyl, phenyl, monosub £; substituted phenyl in which the substituent is nitro, fluorine, chlorine, bromine, alkyl, alkoxy, trifluoromethyl, phenyl or phenoxy, or disubstituted phenyl in which the substituents are fluorine, chlorine , Bromine, alkyl or alkoxy, and R 'are fluoride, chloride, bromide, iodide, trifluoroacetate, alkanoate, nitrate or tetrafluoroborate and wherein the alkyl, alkoxy and alkanoate groups contain 1 to 4 carbon atoms. 2. Antimicrobial agent according to claim 1, characterized in that that the active agent is phenyl-2-thienyliodonium chloride, 2,2'-bisthienyliodonium chloride, 4-chlorophenyl-2-thienyliodonium chloride, 4-chlorophenyl-2-thienyliodonium trifluoroacetate, 4-methylphenyl-2-thienyliodonium chloride or 3,4-dichlorophenyl-2-thienyliodonium chloride is.