The present invention relates to the use of 4-aminopyrimidines of formula R, and R2 are each independently of the other hydrogen; C,-C, alkyl which is unsubstituted or substituted by one or more halogen atoms ; biphenyl or C6-C10aryl which is unsubstituted or substituted by halogen, C,-C, alkyl, C,-C, alkoxy or by amino; a 5-to 7-membered heteroaryl radical ; or cyclo-C,-C, alkyl ; R3 is hydrogen; phenyl or C,-Csalkyl which is unsubstituted or substituted by one or more halogen atoms; R4 is hydrogen; C,-C, Oall (yi ; phenyl ; or a 5-to 7-membered heteroaryl radical ; R5 is C,-C20alkyl which is unsubstituted or substituted by one or more halogen atoms or by a heterocyclic radical or interrupted by one or more-O-or groups or by a bivalent heterocyclic radical ; NR"R'''-C1-C20alkyl which is unsubstituted or substituted by a heterocyclic radical or interrupted by one or more -O- or groups or by a bivalent heterocyclic radical ; cyclo-C5-C8allcyl ; hydroxy-C1-C20alkyl ; phenyl-C,-C3alkyl ; a heterocyclic radical ; or R4 and R,, together with the nitrogen atom linking them, form a radical of formula (1 a) R'is hydrogen; or C,-C3alkyl ; R"and R"'are each independently of the other hydrogen; C,-Csalkyl ; or hydroxy-C,-C5alkyl ; X is R""is hydrogen; C,-C4alkyl ; or heteroaryl-C,-C4alkyl ; and ni and n2 are each independently of the other from 1 to 8; in the antimicrobial treatment of surfaces.

C1-C2oAlkyl radicals are straight-chain or branched alkyl radicals, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl.

C3-CloCycloalkyl denotes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl. Those radicals may be substituted, for example by one or more identical or different C,-C4alkyl radicals, especially by methyl, and/or by hydroxy. When cycloalkyl radicals are substituted by one or more substituents, they are substituted preferably by one, two or four, especially by one or two, identical or different substituents.

C1-C5AIkoxy radicals are straight-chain or branched radicals such as, for example, methoxy, ethoxy, propoxy, butoxy or pentyloxy.

C6-C, Aryl and heteroaryl radicals may be unsubstituted or may carry one or more, for example one, two, three or four, identical or different substituents, which may be located in any positions. Examples of such substituents are, for example, C,-C4alkyl, halogen, hydroxy, C1-C4alkoxy, trifluoromethyl, cyano, hydroxycarbonyl, Cl-C4alkoxycarbonyl, aminocarbonyl, amino, C,-C4alkylamino, di-C,-C4alkylamino and Cl-C4alkylcarbonylamino.

Heteroaryl radicals are derived from heterocycles containing one, two, three or four identical or different ring hetero atoms, especially from heterocycles containing one, two or three, more especially one or two, identical or different hetero atoms. The heterocycles may be mono-or poly-cyclic, for example mono-, bi-or tri-cyclic. They are preferably mono-or bi- cyclic, especially monocyclic. The rings preferably contain 5,6 or 7 ring members. Examples of monocyclic and bicyclic heterocyclic systems from which radicals occurring in the compounds of formula (1) can be derived are, for example, pyrrole, furan, thiophene, imidazole, pyrazole, 1,2, 3-triazole, 1,2, 4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pyran, thiopyran, 1,4-dioxane, 1,2-oxazine, 1,3-oxazine, 1,4-oxazine, indole, benzo- thiophene, benzofuran, pyrrolidine, piperidine, piperazine, morpholine and thiomorpholine.

Unsaturated heterocycles may contain, for example, one, two or three unsaturated double bonds in the ring system. 5-membered rings and 6-membered rings in monocyclic and polycyclic heterocycles may also be, especially, aromatic.

Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.

In accordance with the invention, preference is given to the use of compounds of formula (1) wherein Rs is R"R"'N-C,-C20alkyl which is uninterrupted or interrupted by one or more-O-or groups or by a bivalent heterocyclic radical ; R'is hydrogen; or C,-C5alkyl ; R"and R"'are each independently of the other hydrogen; or methyl ; and R"R2, R3 and R4 are as defined for formula (1).

Very special preference is given to the use of compounds of formula (1) wherein Rs is R"R"'N-C,-Caoalkyl which is uninterrupted or interrupted by In accordance with the invention, there are furthermore used compounds of formula (1) wherein Rs is R"R"'N-C5-C20alkyl which is uninterrupted or interrupted by one or more-O-or groups; R'is hydrogen; or C,-C, alkyl ; and R"and R"'are each independently of the other hydrogen; or methyl.

Among those compounds, preference is given to those wherein Rs is R"R'''N-C5-C20alkyl ; and R"and R"'are each independently of the other hydrogen; or methyl.

Very special preference is also given to the use of compounds of formula (1) wherein R4 is hydrogen; or C,-C5alkyl ; Rs is C5-C20alkyl which is unsubstituted or interrupted by-NH- ; and R"R2 and R3 are as defined for formula (1); especially compounds of formula (1) wherein R, is hydrogen; C1-C5alkyl ; unsubstituted or C,-C4alkyl-substituted phenyl or phenyl- C1-C4alkyl ; or pyridino; R2 is hydrogen; or C,-Csalkyl ; especially methyl ; R3 is hydrogen; or C1-C5alkyl ; R4 is hydrogen ; or C1-C5alkyl ; and Rs is C5-C20alkyl ; and very especially compounds of formula (1) wherein R, is hydrogen; C1-C5alkyl, especially isopropyl or methyl ; unsubstituted or C,-C4alkyl- substituted phenyl ; or pyridino; R2 is methyl ; R3 and R4 are hydrogen; and R5 is C8-C18alkyl.

Among the last-mentioned compounds very special preference is given to the use of those wherein R5 is linear C8-C18alkyl.

Also preferably used are compounds of formula (1) wherein, in formula (la), R""is hydrogen; or pyridyl-C1-C3alkyl ; and ni and na are each 2.

Preference is also given to the use of compounds of formula (1) wherein R, and R2 are each independently of the other hydrogen; C,-Csalkyl ; phenyl which is unsubstituted or substituted by halogen, C1-C5alkyl, C1-C5alkoxy or by amino; biphenyl ; cyclo-C3-C, alkyl ; 3-pyridyl ; 4-pyridyl ; 2-thiophenyl ; 3-thiophenyl ; or thiazolyl ; or compounds of formula (1) wherein R3 is hydrogen; or phenyl ; or compounds of formula (1) wherein R4 is hydrogen.

Special preference is given to the use of compounds of formula wherein X is-0-; or R'is hydrogen; or C1-C3alkyl ; n is 1-3; and m is 1-3; and Rl, R2 and R3 are as defined for formula 1.

The Table that follows lists, by way of example, further 4-aminopyrimidines according to the invention : Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm formula /1 3 j ß XNH, 64 72 N NH Comp. of Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H2N NH N 4 37 96 W nu W/NH 5 5 nu2 7 NH// NAH N 6 od eN 92 97 NH2 W M "f N nu Ici N F NH F 82 93 F Comp. of Structural formula Purity [%] Purity [%] formula 254 nm 280 nm formula OH r) n 9 94 98 N F F N HAN lN H 75 89 10 49 59 I w N w i i Fi N _ NH N 75 89 I \ N I \ H2N/NI/NH < NW 12 N 95 97 I \ N I \ // H2N N 13 \ V 94 99 I \ N I \ -N cl 91 97 N ho 14 N Comp. Purit % Purit % of Structural formula Y Y formula S 15 N 91 98 /91 98 N H N- 16 HNt< 42 44 F F F H 17 39 43 F F F 18 N HzN H 42 51 F F F Han- 19 64 70 F \/ F F Comp... ___ Purit % Purit % of Structural formula Purity [%] Purity [%] formula \/ 20 N 63 77 H F F F F H 70 82 NHZ/\-F F F 22 N 22 51 65 H2N U F F hein F Hi- 2 3 \ 6 7 8 2 23 67 82 - F F F VIZ 24" 95 97 NHZ Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm formu) a \/ N Hts =r 26 \N 81'90 O 27 88 93 N- H V 28 86 93 \H X /\. \/ V H 29 61 62 HAN Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H H 30 85 72 X N \ I F N11N FF No-_rN 31 N 45 42 N%/ N N H N 32 69 64 NH H Hsc N CH3 NEZ N 33 94 93 NJ N NON 34 89 89 NON N y Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H N N N 35 92 88 ZON /N H N N 36 82 73 N No mA N/N 37 82 66 ZON H N N 38 56 34 N H H3c-f"'YN CH3 NON 39 67 46 iN N 40 H 43 44 Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H N N N 4'I 81 77 N , N 42 91 92 N 6 N N fN' 43 72 68 N N lyN 44 C Nf 88 84 NoyN 45 N1 82 83 NH \ 1 46 N---7 88 88 ..... Comp. of Structural formula Purity [%] Purity [%] formula 254 nm 280 nm formula N/N 1 47 N 72 67 NH ZON I I 48 N 81 85 nu N (DON 49 N1 92 84 k, NH N I\ N/N I 50 N 84 86 0 0 N Nu 51 ? 77 73 NH po Comp. Purit % Purit % of Structural formula Pu formula 254 nm 280 nm I formula 1 52 N 88 91 /\ N N. 11 N 53 87 89 54 90 91 N NNor 55 N 85 87 OH OH N<Nt 56 N 87 84 N Coma. of 5tructurai formula tY L y [ formula 254 nm 280 nm formula 57 99 99 N 58 58 78 moN o~ Non 78 I N \N oP~/ 59 34 64 s N N _-_ N N N 60 46 32 H _-- N N N 61 90 87 F NON N N iV 62 66 61 . N N sZ S 66 t 6 Coma. of Structural formula Pur ty o Purity [%] formula 254 nm 280 nm _ n N N 63 99 95 .... N N N 64 80 80 r H N 65 N N 96 92 N N MM N N 66 X 90 95 XI ly 67 NiN 48 44 N N 68 N mcNs~ 37 38 NN N ss N\ Comp. Purit % Purit % Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm formula H NON 70 71 82 Lk N N 71 xi 88 88 H N / N N 72 79 52 zu H /I N N N 73 90 96 N N 74 79 39 H /1 N I N N 74 79 39 mgNw/_ H NON 75 92 89 75 92 89 F Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm formula H 76 97 95 N N NN N N N 77 86 90 N N H N 78 nul 90 94 N N N N N N 79 92 95 N H N 80 non 54 50 A H /I N 81 N w N 40 42 N N / N N s s Coma. Comp. Structural formula Purity [%] Purity [%] 254 nm 280 nm formula H N NEZ N 83 77 72 F H- N Nez N 84 93 91 w H H N moNs m NaioN 85 < 83 80 N N N N N N 86 92 Es W N N N 87 95 94 i Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H N N N N N. N 88 95 94 N H H H C N CH 89 Nn'l 92 90 CH3 N N. N N N 90 54 33 NH, H N nN N 91 ß 89 95 i H N 92 NajoN 52 48 H N 93 NaioN 40 39 N N N 94 65 80 p Comp. Purit % Puri % of formula 254 nm 280 nm H N NON 95 82 83 F H N NajoN N N 96 78 85 w N 97 31 26 N NEZ N 97 \ 31 26 H N N N 98 79 60 W} W N N N 99 93 90 i Comp. of Structural formula Purity [%] Purity [%] formula 254 nm 280 nm formula H N N 100 71 59 N H H N 10 1 NxN 87 78 NON N N N N N 102 49 25 NH2 H N N N 103 89 89 « Nom H N 104 NIN 54 41 H N 1 OS N w N 33 38 _.. Comp. Purit % Purit % Comp. Structural formula Purity [% Purity [%] formula 254 nm 280 nm formula H N N 106 65 75 s H N NON 107 80 82 F N N N 108 r) 1 87 96 i N N N N N N 109 87 g7 N N'N H 110 90 94 s i Comp. Purit %. Purit % Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H N N 111 94 92 HCY-ly NON 112 Y 87 90 N N N 87 90 N H N 113 lu 92 85 H N N N 114 41 28 NHZ XcNsw N tcN ~ 115 J. 93 96 i 116 NIN 58 46 H N, N H N 117 N \ N 39 40 Comp. Purit % Purit % Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H N N N 118 54 70 Nu y N N 119 82 87 JAZZ NON N N 120 42 3S ... N nC N N 121 87 90 X NAIN 122 ß 78 87 j-S N NON 123 68 73 i Coma. of Structural formula Purity [%] Purity [%] formula 254 nm 280 nm mc1, N 124 N N 93 96 aM W N N 125 93 93 N N 126 < ~ 87 86 I YY.. 127 nit 65 69 A N 128 46 52 zu N N N N 129 58 69 N I N N 130 A 82 83 I F Coma. Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H N N N N 131 8 g 73 74 N N N N 132 88 90 N N N N N N 133 94 93 non H N N N 134 loo 89 H N N 135 N 92 91 N N NN 136 92 92 i Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H N 1 37 NaioN 49 44 H N 138 N N 9 41 41 H N N IN 139 50 66 N N N IN 140 100 80 F H N ion N\ N 141 74 71 i H N NN 142 100 83 H N 143 X 1§4 79 Comp. Structural formula Purity [%] Purity [%] formula 254 nm 280 nm H H nNooX NN' 144 d 62 54 i I 145 N N nz 43 39 H y 146 N 34 35 H N N N IN 147 61 73 N\ ssNom my N N IN Yy N/N 148 72 70 . F 149 N 91 89 N HN Comp. Pu of Structural formula Y C l y ( formula 254 nm 280 nm formuia ISO 97 89 150 N 87 88 N N H N 151 N 88 86 W.. w 152 91 83 N H 153 zf 89 85 i S 3 N \ 89 85 HN N ¢W"N sgt 154 N X 94 85 N "VN 155 N 85 81 N r 1 56 sC 86 82 HNom Comp. Purit % Purit % of Structural formula Y Y L formula 254 nm 280 nm N 'LN 157 N 62 63 HN N 158 N 86 92 HNt aN 159 N 89 91 HN v 160 N I 8 92 N J I/iN \ I 161 Nt 88 92 HNI__ .. 162 N'J 67 88 HNsm HN ^ Coma. of Structural formula Purity [%], Purity [%] formula 254 nm 280 nm formula 163 N 67 66 r f HN 164 ! ! J 85 92 N Nu OU . 165 nu 81 92 N HN ~OH N 166 ¢4, 68 75 HNro,,, N 167 NH90 zNf 92 89 r r /j \ 'LkJ 168 N 72 73 Han ^ Comp. of Structural formula Purity [% Purity 1%) formula 254 nm 280 nm formula form _.... N 169 87 83 HN C zizi i if 77 85 170 < 77 85 Han HAN ZON 171 N 86 81 HN t Nazi O /rN 172 (yN 87 72 N N aN 173 N 69 67 /N 174 N 66 87 N, Structural formula Purity [%] Purity formula 254 nm 280 nm N i 175 N 69 64 NU "VN 176 N 82 57 N N 177 N 87 92 Nu Zou N 178 N 77 69 N C 179 N 77 85 I HN oN soNH2 The 4-aminopyrimidines used in accordance with the invention are prepared by methods known per se (J. Org. Chem.; 1967,32, 1591). For that purpose, a cyano compound (R,-C=-N) is reacted, in a suitable solvent such as, for example, methanol, ethanol, isopropanol, DMF, tetrahydrofuran etc. , with ammonium acetate or ammonium chloride at a temperature of from-10°C to 100°C over a period of from 1 hour to 24 hours to form the corresponding amidine compound The amidine compound is then condensed with an appropriate-keto ester using an auxiliary base such as, for example, sodium carbonate, potassium hydroxide, sodium ethanolate, sodium methanolate, potassium tert-butanolate etc. , in a suitable solvent such as, for example, methanol, ethanol, butanol, tert-butanol, THF, DMF, acetonitrile, toluene, xylene etc. , over a period of from 1 to 24 hours at a temperature of from 40 to 120°C.

The 4-hydroxy-2-pyrimidine compound thereby obtained is then converted into the corresponding 4-chloro-2-pyrimidine compound by conventional methods using phosphorus oxychloride.

The substituted 4-aminopyrimidines are obtained by reacting the 4-chloro-2- pyrimidine compound with a primary or secondary amine (R4R5NH) in a suitable solvent such as, for example, DMF, dioxane, toluene, xylene, ethanol, butanol, and an auxiliary base such as, for example, triethylamine, DIEA, sodium carbonate, potassium hydroxide etc. , or using an excess of amine at from 40 to 130°C over a period of from 1 to 24 hours.

The entire reaction proceeds according to the following scheme: 0 0 0 NH, Ct NH'' NH4CI NH R2 Ri N R2 3 Ri NH2 auxiliary base Noir3 rua OH OH POCI3 Ri N R2 R4R5NH R N R2 zNo Cl zu ce '*'N R4 Ru R1, R2, R3, R4 and Rs being as defined for formula (1).

Preparation of the compounds of formula (2) is carried out by reacting an excess of from 2 to 10 equivalents of the diamine compound H2N (CH2) nX (CH2) mNH2 in, for example, DMF, dichloromethane, THF or dioxane with trityl chloride polystyrene resin at a temperature of from 10 to 50°C over a period of from 0.5 to 24 hours. From 2 to 10 equivalents of the appropriately substituted 4, 6-dichloropyrimidines are then reacted, in a suitable solvent such as, for example, dichloromethane, DMF, THF or toluene, with the polymer-bound diamines at from 10 to 120°C over a period of from 2 to 48 hours. The 4- chloropyrimidines are reacted with from 2 to 10 equivalents of various boronic acids, from 1 to 10 % of palladium catalyst and from 2 to 10 equivalents of auxiliary base such as, for example, CaCO3 and NaCO3, in, for example, THF, DMF or dioxane. After washing the resin to remove the excess, the target compounds are split off using from 1 to 30 % trifluoroacetic acid (TFA) in dichloromethane (DCM) at 25°C over a period of from 1 to 5 hours. For the purpose of further purification, the substances are freeze-dried from tBuOH/water 4 : 1 with from 1 to 10 % HOAc and once from tBuOH/water 4: 1.

The entire reaction proceeds according to the following scheme: - H2N (CH2) X (CHg) NH2/, (TCP\-C)--'------ (TCPNH (CHX (CH, LNH, R N ci N R3 CI R2B (OH) 2 R Pd cat. auxiliary N TFA/DCM base R3 cri R3 R3 CI NH- (CH2) nX (CH2) mNH2 RI, R2, R3, X, m and n being as defined for formula (2).

Some of the 4-aminopyrimidines used in accordance with the invention are known from the literature and some are novel compounds. The invention relates also to those novel compounds.

The novel compounds correspond to formula Ri and R2 are each independently of the other hydrogen; C1-C5alkyl which is unsubstituted or substituted by one or more halogen atoms; biphenyl or C6-C10aryl which is unsubstituted or substituted by halogen, C,-Csalkyl, C,-Csalkoxy or by amino; a 5-to 7-membered heteroaryl radical ; or cyclo-C3-C7alkyl ; R3 is hydrogen; phenyl or C,-Csalkyl which is unsubstituted or substituted by one or more halogen atoms; R4 is hydrogen; C1-C10alkyl ; phenyl ; or a 5-to 7-membered heteroaryl radical ; Rs is C1-C20alkyl which is unsubstituted or substituted by one or more halogen atoms or by a heterocyclic radical or interrupted by one or more-O-or groups or by a bivalent heterocyclic radical ; NR"R'''-C1-C20alkyl which is unsubstituted or substituted by a heterocyclic radical or interrupted by one or more-O-or groups or by a bivalent heterocyclic radical ; cyclo-Cs-C8alkyl ; hydroxy-C1-C20alkyl ; phenyl-C,-C, alkyl ; a heterocyclic radical ; or R, and R,, toaether with the nitroaen atom linking them, form a radical of formula (1 a) R'is hydrogen; or C,-C3alkyl ; R"and R"'are each independently of the other hydrogen; C,-Csalkyl ; or hydroxy-C,-Csalkyl ; X is R""is hydrogen; C,-C4alkyl ; or heteroaryl-C1-C4alkyl ; and ni and n2 are each independently of the other from 1 to 8; not including compounds of formula (1') wherein simultaneously R, is C6-C, oaryl ; or C1-C4alkyl ; and Rs is C1-C7alkyl.

The 4-aminopyrimidines used in accordance with the invention exhibit pronounced antimicrobial action, especially against pathogenic gram-positive and gram-negative bacteria and against bacteria of the skin flora, and also against yeasts and moulds. They are accordingly suitable especially for disinfection, deodorisation, and for general and antimicrobial treatment of the skin and mucosa and of integumentary appendages (hair), more especially for the disinfection of hands and wounds.

They are accordingly suitable as antimicrobial active substances and preservatives in personal care preparations such as, for example, shampoos, bath additives, haircare preparations, liquid and solid soaps (based on synthetic surfactants and salts of saturated and/or unsaturated fatty acids), lotions and creams, deodorants, other aqueous or alcoholic solutions, e. g. cleansing solutions for the skin, moist cleaning cloths, oils or powders.

The invention accordingly relates also to a personal care preparation comprising at least one compound of formula (1) and cosmetically tolerable carriers or adjuvants.

The personal care preparation according to the invention contains from 0.01 to 15 % by weight, preferably from 0.1 to 10 % by weight, based on the total weight of the composition, of a compound of formula (1), and cosmetically tolerable adjuvants.

Depending upon the form of the personal care preparation, it comprises, in addition to the 4-aminopyrimidine of formula (1), further constituents such as, for example, sequestering agents, colorants, perfume oils, thickeners or solidifiers (consistency regulators), emollients, UV-absorbers, skin protective agents, antioxidants, additives that improve the mechanical properties, such as dicarboxylic acids and/or aluminium, zinc, calcium or magnesium salts of C14-C22fatty acids, and, optionally, preservatives.

The personal care preparation according to the invention may be in the form of a water-in-oil or oil-in-water emulsion, an alcoholic or alcohol-containing formulation, a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, a gel, a solid stick or an aerosol formulation.

As a water-in-oil or oil-in-water emulsion, the cosmetically tolerable adjuvant contains preferably from 5 to 50 % of an oil phase, from 5 to 20 % of an emulsifier and from 30 to 90 % water. The oil phase may comprise any oil suitable for cosmetic formulations such as, for example, one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol. Preferred mono-or poly-ols are ethanol, isopropanol, propylene glycol, hexylen glycol, glycerol and sorbitol.

Cosmetic formulations according to the invention are used in various fields. There come into consideration, for example, especially the following preparations: - skin-care preparations, e. g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, synthetic detergents or washing pastes, - bath preparations, e. g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e. g. bath cubes and bath salts ; - skin-care preparations, e. g. skin emulsions, multi-emulsions or skin oils ; - cosmetic personal care preparations, e. g. facial make-up in the form of day creams or powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care preparations, e. g. eyeshadow preparations, mascaras, eyeliners, eye creams or eye-fix creams; lip-care preparations, e. g. lipsticks, lip gloss, lip contour pencils, nail-care preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle removers; intimate hygiene preparations, e. g. intimate washing lotions or intimate sprays; foot-care preparations, e. g. foot baths, foot powders, foot creams or foot balsams, special deodorants and antiperspirants or callus-removing preparations; light-protective preparations, such as sun milks, lotions, creams or oils, sun-blocks or tropicals, pre-tanning preparations or after-sun preparations; skin-tanning preparations, e. g. self-tanning creams; depigmenting preparations, e. g. preparations for bleaching the skin or skin-lightening preparations; insect-repellents, e. g. insect-repellent oils, lotions, sprays or sticks; deodorants, such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons ; antiperspirants, e. g. antiperspirant sticks, creams or roll-ons ; preparations for cleansing and caring for blemished skin, e. g. synthetic detergents (solid or liquid), peeling or scrub preparations or peeling masks; hair-removal preparations in chemical form (depilation), e. g. hair-removing powders, liquid hair-removing preparations, cream-or paste-form hair-removing preparations, hair- removing preparations in gel form or aerosol foams; shaving preparations, e. g. shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, preshave preparations for dry shaving, aftershaves or aftershave lotions ; fragrance preparations, e. g. fragrances (eau de Cologne, eau de toilette, eau de parfum, parfum de toilette, perfume), perfume oils or perfume creams; dental care, denture-care and mouth-care preparations, e. g. toothpastes, gel toothpastes, tooth powders, mouthwash concentrates, anti-plaque mouthwashes, denture cleaners or denture fixatives; cosmetic hair-treatment preparations, e. g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e. g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e. g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair- setting preparations, hair foams, hairsprays, bleaching preparations, e. g. hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colorants, preparations containing self-oxidising dyes, or natural hair colorants, such as henna or camomile.

An antimicrobial soap has, for example, the following composition: 0.01 to 5 % by weight of a compound of formula (1) 0.3 to 1 % by weight titanium dioxide, 1 to 10 % by weight stearic acid, soap base ad 100 %, e. g. a sodium salt of tallow fatty acid or coconut fatty acid, or glycerol.

A shampoo has, for example, the following composition: 0.01 to 5 % by weight of a compound of formula (1), 12.0 % by weight sodium laureth-2-sulfate, 4.0 % by weight cocamidopropyl betaine, 3.0 % by weight NaCI and water ad 100 %.

A deodorant has, for example, the following composition: 0.01 to 5 % by weight of a compound of formula (1), 60 % by weight ethanol, 0.3 % by weight perfume oil, and water ad 100 The invention relates also to an oral composition containing from 0.01 to 15 % by weight, based on the total weight of the composition, of a compound of formula (1), and orally tolerable adjuvants.

Example of an oral composition: 10 % by weight sorbitol, 10 % by weight glycerol, 15 % by weight ethanol, 15 % by weight propylene glycol, 0.5 % by weight sodium lauryl sulfate, 0.25 % by weight sodium methylcocyl taurate, 0.25 % by weight polyoxypropylene/polyoxyethylene block copolymer, 0.10 % by'weight peppermint flavouring, 0.1 to 0.5 % by weight of a compound of formula (1), and 48.6 % by weight water.

The oral composition according to the invention may be, for example, in the form of a gel, a paste, a cream or an aqueous preparation (mouthwash).

The oral composition according to the invention may also comprise compounds that release fluoride ions which are effective against the formation of caries, for example inorganic fluoride salts, e. g. sodium, potassium, ammonium or calcium fluoride, or organic fluoride salts, e. g. amine fluorides, which are known under the trade name Olafluor.

The 4-aminopyrimidines of formula (1) used in accordance with the invention are also suitable for treating, especially preserving, textile fibre materials. Such materials are undyed and dyed or printed fibre materials, for example of silk, wool, polyamide or polyurethanes, and especially cellulosic fibre materials of all kinds. Such fibre materials are, for example, natural cellulose fibres, such as cotton, linen, jute and hemp, as well as cellulose and regenerated cellulose. Preferred suitable textile fibre materials are made of cotton.

The 4-aminopyrimidines according to the invention are suitable also for treating, especially imparting antimicrobial properties to or preserving, plastics such as, for example, poly- ethylene, polypropylene, polyurethane, polyester, polyamide, polycarbonate, latex etc..

Fields of use therefor are, for example, floor coverings, plastics coatings, plastics containers and packaging materials; kitchen and bathroom utensils (e. g. brushes, shower curtains, sponges, bathmats), latex, filter materials (air and water filters), plastics articles used in the field of medicine such as, for example, dressing materials, syringes, catheters etc., so-called "medical devices", gloves and mattresses.

Paper, for example papers used for hygiene purposes, may also be provided with antimicrobial properties using the 4-aminopyrimidines according to the invention.

It is also possible for nonwovens such as, for example, nappies/diapers, sanitary towels, panty liners, and cloths for hygiene and household uses, to be provided with antimicrobial properties in accordance with the invention.

The 4-aminopyrimidines of formula (1) are also used in washing and cleaning formulations such as, for example, liquid or powder washing agents or softeners.

The 4-aminopyrimidines of formula (1) can also be used especially in household and general-purpose cleaners for cleaning and disinfecting hard surfaces.

A cleaning preparation has, for example, the following composition: 0.01 to 5 % of a compound of formula (1) 3. 0 % octyl alcohol 4EO 1.3 % fatty alcohol Cg-Ciopoiygiucoside 3.0 % isopropanol water ad 100 %.

In addition to preserving cosmetic and household products, the preservation of technical products, the provision of technical products with antimicrobial properties and use as a biocide in technical processes are also possible, for example in paper treatment, especially in paper treatment liquors, printing thickeners of starch or cellulose derivatives, surface- coatings and paints.

The 4-aminopyrimidines of formula (1) are also suitable for the antimicrobial treatment of wood and for the antimicrobial treatment of leather, the preserving of leather and the provision of leather with antimicrobial properties.

The compounds according to the invention are also suitable for the protection of cosmetic products and household products from microbial damage.

The following Examples illustrate, but do not limit, the present invention.

Implementation Examples : General work procedure for parallel synthesis of 4-aminopyrimidines : Example 1: Reaction Scheme 0 0 0- NH4C'Ri NH 2 Ri N R2 '3 Ri NH2 auxiliary base N/ OH OH POCI3 Rr R2 R4R5NH 1) 3 zNs Cl OH CL Fizz -V.

Preparation of 4-chloro-6-methyl-2-phenylpvrimidine 2.2 g of benzamidine hydrochloride (14.05 mmol) are reacted, in 10 mi of absolute EtOH, with 5.43 ml (14.05 mmol) of 20 % sodium ethanolat solution and then condensed with 1.66 g of methyl acetoacetate (14.29 mmol) for 4 hours at 90°C.

The crude product is concentrated by evaporation and taken up in 30 ml of toluene.

4.31 g of phosphorus oxychloride (28.1 mmol) are added and the reaction mixture is heated at 120°C for 3 hours. After cooling to 20°C, the excess is neutralised with sodium hydroxide solution, and the mixture is diluted with ethyl acetate and then washed with water and saturated sodium chloride solution.

The product solution is dried over sodium sulfate and concentrated by evaporation.

2.2 g of 4-chloro-6-methyl-2-phenylpyrimidine (77.7 % of theory) are obtained.

Example 2: Reaction of 4-chloro-6-methyl-2-phenylpyrimidine with monoamines 20.5 mg of 4-chloro-6-methyl-2-phenylpyrimidine (0.1 mmol) are heated with 3 equivalents of monoamines (0.3 mmol) in 0.5 ml of absolute dioxane at 100°C for 20 hours. After cooling, the products are concentrated in vacuo, taken up in t-BuOH/water 4/1 and freeze- dried. The end products are analysed by LC-MS.

Example 3: Loading of trityl chloride polystyrene resin with N, N-bis (3-aminopropyl) methyl- amines and reaction with 4, 6-dichloro-2 5-diphenylpyrimidine In each case, 50 mg of resin (1.29 mmol/g) are shaken in 1 ml of DMF with 94 mg of N, N- bis (3-aminopropyl) methylamine (0.645 mmol) at 25°C for 3 hours. The resin is filtered off and washed with DCM, MeOH, THF, MeOH and DCM and dried in vacuo.

The resin is shaken in 1 ml of DMF with 0.194 g of 4, 6-dichloro-2, 5-diphenylpyrimidine (0.645 mmol) and 90 ul of triethylamine (0.645 mmol) at 25°C for 3 hours.

The resin is filtered off and washed with DCM, MeOH, THF, MeOH, DCM and MeOH and dried in vacuo.

Example 4: Parallel reaction of 4-amino-6-ch) oro-1, 5-diphenyipyrimidine-TCP resins with various boronic acids and splitting The resin is heated with 126.1 g of caesium carbonate (6 eq., 0. 387 mmol) and 300 zizi of a toluene solution of 0.1 eq. of a palladium catalyst (WO 01/16057) at 95°C for 15 minutes.

After adding 3 eq. of a boronic acid, dissolved in 700 gl of toluene solution, the mixture is heated at 90°C for 1 hour.

After cooling, the resin is filtered off and washed with DMF, MeOH, THF, MeOH and DCM and dried in vacuo.

The products are split off using 1.5 ml of a 5 % TFA/DCM solution at room temperature for 3 hours. The resin is then washed with 1 ml of DCM and 1 ml of MeOH, and the combined solutions are concentrated to dryness by evaporation. The end products are analysed by LC-MS.

Example 5: Preparation of 4-chloro-6-methyl-2-tvlpyrimidine 2.5 g of 4-methyl-benzamidine hydrochloride (14.65 mmol) are reacted in 10 mi of absolute EtOH with 5.66 mi of a 20 % solution of sodium ethanolat (14.65 mmol) and then condensed with 1.73 g of methyl acetoacetate (14.88 mmol) at 90°C for 4 hours. The crude product is concentrated by evaporation and taken up in 30 ml of toluene. 6.74 g of phosphorus oxychloride (44.0 mmol) are added and the reaction mixture is heated at 120°C for 3 hours. After cooling to 20°C, the excess is neutralised with sodium hydroxide solution, and the mixture is diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate solution and then with water. The product solution is concentrated by evaporation and separated by column chromatography (hexane/EE : 5/1). 2.1 g of 4-chloro- 6-methyl-2-tolylpyrimidine (66. 5 % of theory) are obtained.

NMR: 1 H (ppm in DMSO): 2.4, s, 3H; 2. 55, s, 3H; 7. 3, d, 2H; 7.5, s, 1 H ; 8.25, d, 2H Example 6: Reaction of 4-chloro-6-methyl-2- (4-methyl)-phenylpyrimidine with monoamines 21.9 mg of 4-chloro-6-methyl-2- (4-methyl)-phenylpyrimidine (0.1 mmol) are heated with 3 eq. of monoamines (0.3 mmol) in 0.5 ml of absolute dioxane at 100°C for 20 hours. After cooling, the products are concentrated in vacuo, taken up in t-BuOH/water 4/1 and freeze- dried. The end products are analysed by LC-MS.

Example 7: Reaction of 4-chloro-6-methyl-2-(4-methyl)-phenylpyrimidine with octylamin 1.36 g of 4-chloro-6-methyl-2- (4-methyl)-phenylpyrimidine (6.23 mmol) are heated with 886 mg of octylamine (6. 85 mmol) and 2.58 g of potassium carbonate (18. 68 mmol) in 10 g of dioxane at 100°C for 48 hours. After cooling, the product is taken up in 100 ml of ethyl acetate and washed with sodium hydroxide solution 0.5 mol/l, saturated sodium hydrogen carbonate solution and water. The product is concentrated in vacuo, taken up in t-BuOH/water4/1 andfreeze-dried.

1.92 g of 4-chloro-6-methyl-2- (4-methyl)-phenylpyrimidine (6. 15 mmol, 98.7 % of theory) are obtained.

The end product is analysed by NMR, GC-MS and GC.

NMR 1H (ppm in DMSO) : 0.9, t, 3H; 1. 25, m, 12H ; 1. 55, m, 2H; 2.25, s, 3H; 2.3, s, 3H; 6.4, s, 1H ; 7.1, m, 1H ; 7.2, d, 2H; 8.2, d, 2H; (m/z = 311) ; GC: 95 % purity Example 8: Preparation of 4-chloro-2-isopropyl-6-methylpyrimidine 76.1 g of 2-isopropyl-6-methyl-4-pyrimidinol [2814-20-2] (500 mmol) are dissolved in 300 ml of toluene at 90°C. 80.5 g of phosphorus oxychloride (525 mmol) are added dropwise thereto at from 90 to 103°C, and the reaction mixture is heated at 110°C for 2 hours. After cooling to 20°C, the reaction mixture is adjusted to pH 8 using 4M sodium hydroxide solution, with cooling. The aqueous phase is separated off and extracted with 100 ml of toluene. The combined organic phases are washed three times with 100 ml of water each time and dried at RT under 2 mbar. 89.7 g (105 %; contains toluene) are obtained.

Example 9: Preparation of 4-dodecylamino-2-isopropyl-6-methylpyrimidine (compound of formula (93)) 79.2 g of 4-chloro-2-isopropyl-6-methylpyrimidine (464.1 mmol) are heated in 100 mi of dioxane at 100°C. A heated solution of 189.3 g of dodecylamine (1021 mmol, 2.2 eq) in 30 ml of dioxane is added dropwise thereto over the course of 2 hours, and the reaction mixture is further heated for 2 hours at 100°C and for 9 hours at 109°C. After cooling, 400 ml of ethyl acetate and 150 mi of 4M sodium hydroxide solution (600 mmol) are added thereto and the mixture is stirred at 50°C for 10 minutes. The lower, aqueous phase is discarded, the organic phase is washed with 300 ml of water, and 10 ml of saturated NaCI solution are added thereto. The organic phase is separated off and concentrated, and the excess dodecylamine is distilled in vocuo up to a bath temperature of 160°C.

136.1 g (91.8 %); GC purity: 98 % NMR 1 H (ppm in CDCI3) : 0.7, t, 3H; 1. 1, m, 24H; 1.4, m, 2H; 2.15, s, 3H; 2. 75, Q, 1 H; 3.05, m, 2H ; 4.9, s, 1 H ; 5.8, s, 1 H Example 10: Determination of the minimum inhibitory concentration (MIC value) in microtitre plates Nutrient medium: Casein/soymeal peptone broth for preparation of pre-cultures of test bacteria and yeast.

Examples of test organisms : Bacteria: Pseudomonas aeruginosa CIP A-22 (=PA) Escherichia coli NCTC 8196 (= EC) Staphylococcus aureus ATCC 9144 (= SA) Candida albicans ATCC 10231 (= CA) Procedure: The test substances are pre-dissolved in dimethyl sulfoxide (DMSO) and tested in a dilution series of 1: 2.

Bacteria and yeast are cultured overnight in CASO broth.

All the test organism suspensions are adjusted to an organism count of 1-5 x 106 CFU/ml using 0.85 % sodium chloride solution.

The test substances are pre-pipetted into microtitre plates in amounts of 8 gl per well.

The pre-adjusted organism suspensions are diluted 1: 100 in CASO broth and are added in amounts of 192 µl per well to the test substances.

The test batches are incubated for 48 hours at 37°C.

After incubation, the growth is determined on the basis of the turbidity of the test batches (optical density) at 620 nm in a microplate reader.

The minimum inhibitory concentration (MIC value) is the concentration of substance at which (compared to the growth of the control) an appreciable inhibition of growth ( : 20 % growth) of the test organisms is observed.

Three microtitre plates are used for each test organism and substance concentration. All the substances are tested in duplicate.

The microbiological test results are compiled in Table 2: Table 2 : Com. of Purity% Purit % MC SA MIC EC MIC PA MIC CA formula 254 nm 280 nm 3 64 72 7.5 15 >120 7.5 4 37 96 7. 5 30 >120 15 5 83 97 7.5 >120 >120 >120 Table 2: Comp. of Purity [%] Purity [%] MIC SA MIC EC MIC PA MIC CA ormula 254 nm 280 nm 6 92 97 7. 5 60 >120 >120 7 43 48 15 15 >120 30 8 82 93 30 30 >120 120 9 94 98 15 15 >120 30 10 49 59 15 30 >120 30 11 75 89 7.5 15 >120 7.5 12 95 97 7. 5 3. 75 7. 5 7. 5 13 94 99 15 15 >120 30 14 91 97 15 3.75 30 15 15 91 98 15 >120 >120 >120 16 42 44 7.5 15 >120 15 17 39 43 15 30 >120 15 18 42 51 30 30 120 60 19 64 70 7.5 15 >120 8 20 63 77 15 30 >120 15 21 70 82 7.5 <3.75 7.5 <3.75 22 51 65 15 15 >120 7.5 23 67 82 15 7.5 30 7.5 24 95 97 30 15 30 30 25 88 96 >120 60 >120 120 26 81 90 60 60 >120 >120 27 88 93 30 30 >120 60 28 86 93 <3.75 >120 >120 >120 29 61 62 15 30 >120 30 30 85 72 60 30 >120 15 31 45 42 60 >120 >120 120 32 69 64 60 120 >120 60 33 94 93 30 >120 >120 60 34 89 89 7.5 120 >120 30 Table 2: Comp. of Purity [%] Purity [%] MIC SA MIC EC MIC PA MIC CA formula 254 nm 280 nm 35 92 88 15 30 120 30 36 82 73 7.5 15 60 7.5 37 82 66 7.5 15 >120 7.5 38 56 34 <3.75 7.5 >120 <3.75 39 67 46 <3.75 30 >120 15 40 43 44 60 >120 >120 120 41 81 77 30 >120 >120 60 42 91 92 <3.75 120 >120 30 43 72 68 60 >120 >120 120 44 88 84 120 >120 >120 120 45 82 83 60 >120 >120 120 46 88 88 120 >120 >120 120 47 72 67 120 >120 >120 >120 48 81 85 30 >120 >120 60 49 92 84 120 >120 >120 >120 50 84 86 120 >120 >120 >120 51 77 73 30 >120 >120 >120 52 88 91 30 >120 >120 120 53 87 89 60 >120 >120 120 54 90 91 15 >120 >120 120 55 85 87 120 >120 >120 >120 56 87 84 60 >120 >120 120 57 99 99 60 >120 >120 120 58587815120>12060 59 34 64 15 60 >120 60 60 46 32 120 >120 >120 120 61908730120>120lYo 62 66 61 60 120 >120 120 63 99 95 15 30 >120 60 Table 2 : Comp. of Purity [%] Purity [%] MIC SA MIC EC MIC PA MIC CA formula 254 nm 280 nm 64 80 80 7. 5 30 >120 15 65 96 92 30 60 >120 15 669095<3. 753012030 67 48 44 7.5 30 >120 7.5 68 37 38 15 30 >120 15 69 64 79 <3. 75 30 >120 7. 5 70 71 82 <3. 75 15 >120 7. 5 71 88 88 7.5 15 >120 7.5 72 79 52 7. 5 15 >120 7. 5 73 90 96 <3.75 7.5 >120 <3.75 74 79 39 <3. 75 7. 5 >1 20 <3. 75 75 92 89 7. 5 15 >120 7. 5 76 97 95 15 60 >120 30 77 86 90 7. 5 60 >1 20 15 78 90 94 <3.75 7.5 >120 <3. 75 79 92 95 <3. 75 <3. 75 >120 <3. 75 80 54 50 <3.75 7.5 >120 7.5 81 40 42 <3.75 <3.75 >120 <3.75 82 67 84 <3.75 15 >120 7.5 83 77 72 <3. 75 7.5 >120 <3. 75 84 93 91 15 15 >120 7.5 85 83 80 15 7.5 >120 7.5 86 92 92 15 15 >120 7. 5 87 95 94 15 15 >120 7.5 88 95 94 15 15 >120 7.5 89 92 90 <3. 75 <3.75 >120 <3.75 90 54 33 7.5 15 >120 <3. 75 91 89 95 30 30 >120 15 92 52 48 <3.75 15 >120 7.5 Table 2 : Comp. of Purity [%] Purity [%] MIC SA MIC EC MIC PA MIC CA formula 254 nm 280 nm 93 40 39 <3.75 15 >120 7.5 94 65 80 <3.75 15 >120 7.5 95 82 83 15 30 >120 15 96 78 85 15 30 >120 15 97 31 26 7.5 15 >120 15 98 79 60 15 15 >120 15 99 93 90 15 15 >120 30 100 71 59 15 15 >120 15 101 87 78 7.5 7.5 >120 7.5 102 49 25 7.5 30 >120 15 103 89 89 15 60 >120 30 104 54 41 <3.75 7.5 >120 7.5 105 33 38 7.5 15 >120 7.5 106 65 75 <3. 75 15 >120 15 107 80 82 7.5 15 >120 15 108 87 96 30 >120 >120 >120 109 87 87 15 60 >120 30 110 90 94 60 >120 >120 120 111 94 92 7.5 120 >120 60 112 87 90 15 120 >120 30 113 92 85 7.5 120 >120 30 114 41 28 15 >120 >120 30 115 93 96 7.5 >120 >120 120 116 58 46 7. 5 60 >120 15 117 39 40 15 120 >120 30 118 54 70 7.5 60 >120 15 119 82 87 7.5 >120 >120 120 120 42 35 30 120 >120 30 121 87 90 30 >120 >120 >120 Table 2 : Comp. of Purity [%] Purity [%] MIC SA MIC EC MIC PA MIC CA formula 254 nm 280 nm 122 78 87 30 >120 >120 120 123 68 73 120 >120 >120 >120 124 93 96 60 120 >120 60 125 93 93 120 >120 >120 120 126 87 86 120 >120 >120 120 127 65 69 60 >120 >120 60 128 46 52 120 >120 >120 129 58 69 120 >120 >120 130 82 83 120 >120 >120 >120 131 73 74 120 >120 >120 >120 132 88 90 60 >120 >120 >120 133 94 93 15 >120 >120 >120 134 100 89 7. 5 >120 >120 120 135 92 91 60 120 >120 30 136 92 92 5 >120 >120 60 137 49 44 15 30 >120 15 138 41 41 30 60 >120 30 139 50 66 7.560 >120 30 140 100 80 15 >120 >120 120 141 74 71 120 >120 >120 >120 142 100 83 30 >120 >120 120 143 84 79 >120 >120 >120 120 144 62 54 60 >120 >120 120 145 43 39 >120 >120 >120 120 146 34 35 >120 >120 >120 120 147 61 73 60 >120 >120 120 148 72 70 120 >120 >120 >120 Example 11: Agar incorporation test CG128e Medium: Casein/soymeal peptone agar (Merck) *Sabouraud 4 % glucose agar (Merck) Diluent : Sterile 0.85 % NaCl solution Incubation : 24 hours at 37°C *3 days at 28°C Test solution : 1 % stock solutions of all the test substances are prepared in a suitable solvent and diluted in serial dilutions to end concentrations of from 1000 ppm to 10 ppm.

Test principle : 0.3 mi of each dilution step is mixed with 15 ml of nutrient medium while the latter is still liquid. After the nutrient medium has solidified, 10 pi of each of the following organism dilutions of the test strains in 0.85 % NaCI solution are spotted onto the agar medium: Microorganisms used: Staphylococcus aureus ATCC 6538 Staphylococcus aureus ATCC 9144 Staphylococcus epidermidis ATCC 12228 Corynebacterium xerosis * ATCC 373 C. minutissimum ATCC 23348 Propionibacterium acnes (*) ATCC 6919 Escherichia coli NCTC 8196 Escherichia coli ATCC 10536 Proteus vulgaris ATCC 6896 Klebsiella pneumoniae ATCC 4352 Salmonella choleraesuis ATCC 9184 Pseudomonas aeruginosa ATCC 15442 Candida albicans ATCC 10231 Aspergillus niger ATCC 6275 The plates are incubated at 37°C for 24 hours (A. niger at 28°C for 3 days) and then the highest dilution (lowest concentration) of the test substance at which growth is just no longer discernible (corresponds to the MIC) is determined.

The results are shown in Table 3.

Table 3: Compound of formula Microorganism (36) (89) (93) Staphylococcus aureus ATCC 6538 120 7. 5 3. 75 Staphylococcus aureus ATCC 9144 120 7.5 3.75 Staphylococcus epidermidis ATCC 12228 > 120 120 3.75 Corynebacterium xerosis * ATCC 373 60 3.75 1. 88 * C. minutissimum ATCC 23348 30 3.75 1. 88 Propionibacterium acnes (*) ATCC 6919 60 3.75 3.75 (*) Escherichia coli NCTC 8196 120 120 120 Escherichia coli ATCC 10536 > 120 > 120 120 Proteus vulgaris ATCC 6896 > 120 60 > 120 Klebsiella pneumoniae ATCC 4352 60 ** > 120 60 Salmonella choleraesuis ATCC 9184 > 120 > 120 120 Pseudomonas aeruginosa ATCC 15442 >120 >120 >120 Candida albicans ATCC 10231 > 120 > 120 > 120 Aspergillus niger ATCC 6275 > 120 > 120 > 120 Example 12 :"Microbicidal activitv"suspension test CG 161/EN1040 Test method: Nutrient medium: Casein/soymeal peptone broth for preparation of pre-cultures of test bacteria Examples of test organisms: Staphylococcus aureus ATCC 6538 Escherichia coli ATCC 10536 Actynomyces viscosus ATCC 43146 Procedure : \ The test substances are dissolved in dimethyl sulfoxide (DMSO) and tested in a concentration of 120 ugimí.

Bacteria are incubated overnight in CASO broth and adjusted to an organism count of 1-5 x 105 CFU/ml using 0.85 % sodium chloride solution.

The test substances are pre-pipetted into microtitre plates in amounts of 8 jii per well.

The adjusted test organism suspensions are added in amounts of 192 it per well to the test substances and mixed. After defined contact times, the test batches are mixed, an aliquot is withdrawn and diluted in several steps in a dilution series of 1: 10 in a suitable inactivation medium.

The test plates are incubated for 24 hours at 37°C. After incubation, the growth is determined on the basis of the turbidity of the test batches (optical density) at 620 nm in a microplate reader.

On the basis of the number of steps in the dilution series that exhibit growth, the reduction in the test organism concentration is determined in powers of ten (log value).

One microtitre plate is used for each test organism.

All the substances are tested in duplicate.

The results (log reduction) are shown in Table 4: Table 4 Compound of formula Organism Contact time (93 ? 93 (89) (89) 0. 12% 120ppm 0. 12% 120ppm S. aureus 5 min >5 1.4 <1 S. aureus 30 min >5 3. 8 1. 7 E. coli 5 min >5 >5 4.6 E. coli 30 min >5 >5 >5 Table 4 Compound of formula Organism Contact time (93) (93) (89) (89 0. 12% 120ppm 0. 12 % 120 ppm A. viscosus 5 min >5 2 4. 9 3.9 A. viscosus 30 min >5 4 >5 4.3 Example 13: Determination of the minimum inhibitory concentration (MIC value) in microtitre lates Nutrient medium and test procedure correspond to Example 10.

As test organisms there are used: Staphylococcus aureus ATCC 6538 Escherichia coli ATCC 10536 Actynomyces viscosus ATCC 43146 The microbiological test results are compiled in Table 5: Table 5 Comp. of Purity [%] Purity [%] MIC SA MIC EC MIC AV formula 254 nm 280 nm 149 91 89 120 >120 15 150 87 88 120 >120 60 151 88 86 120 >120 15 152 91 83 30 >120 15 153 89 85 120 >120 30 154 94 85 120 120 30 155 85 81 30 30 7.5 156 86 82 7.5 15 <3. 75 157 62 63 15 >120 <3.75 158 86 92 >120 >120 7.5 159 89 91 120 >120 30 160 gag 92 120 >120 15 Table 5 Comp. of Purity [%] Purity [%] MIC SA MIC EC MIC AV formula 254 nm 280 nm 87 92 120 >120 30 162 67 88 120 >120 30 163 67 66 >120 >120 60 164 85 92 120 >120 30 165 81 92 >120 >120 30 166 68 75 >120 >120 30 167 92 89 120 120 15 168 7273>120 >12015 169 87 83 >120 >120 30 170 77 85 >120 >120 15 171 86 81 120 >120 30 172 87 72 60 >120 15 173 69 67 60 60 15 174 66 87 120 >120 60 175 69 64 120 120 30 176 82 57 30 30 7. 5 177 87 92 120 >120 30 178 77 69 120 120 30 179 77 85 120 120 30