CS261816B1

CS261816B1 - N-oxides of 2,2,5-trimethyl-3-alkyloxazolidines

Info

Publication number: CS261816B1
Application number: CS871617A
Authority: CS
Inventors: Bohumil Prom Chem Steiner; Vlasta Prom Chem Sasinkova; Milan Clen Kores Csav Repas; Jan Ing Csc Novak; Vlastimil Ing Csc Peterka; Jan Ing Csc Smidrkal
Original assignee: Bohumil Prom Chem Steiner; Vlasta Prom Chem Sasinkova; Milan Clen Kores Csav Repas; Novak Jan; Peterka Vlastimil; Smidrkal Jan
Priority date: 1987-03-11
Filing date: 1987-03-11
Publication date: 1989-02-10
Also published as: CS161787A1

Abstract

Očelom riešenia sú N-oxidy '2,2,5-trimetyl- -3-alkyloxazolldínov všeobecného vzorca I, kde R představuje oktyl, decyl, dodecyl, tetradecyl, hexadecyl a oktadecyl, ktoré majú použitie v detergentných kompozíciách, pri umývaní a súčasnej dezinfekcii podláh, riadov a nástrojov, připadne pri praní textilii.The object of the solution is the N-oxides of '2,2,5-trimethyl-3-alkyloxazolidines of general formula I, where R represents octyl, decyl, dodecyl, tetradecyl, hexadecyl and octadecyl, which have use in detergent compositions, in washing and simultaneous disinfection of floors, dishes and tools, or in washing textiles.

Description

261816 3

The present invention relates to N-oxides of 2,2,5-trimethyl-3-alkyloxazolidines. More recently, more and more publications have emerged in the literature, which are concerned with the synthesis of oxazolidine derivatives and their physicochemical and biological properties. Several groups of these derivatives have been synthesized having high antimicrobial activity. 4,4-Dimethyloxazolidine derivatives have the broadest use. 4,4-Dimethyloxazolidine alone is active against some strains of influenza virus [EtS. Demers: Cosmetics. Toiletries 79 (1981)].

Another derivative, 3-hydroxymethyloxymethylene-4,4-dimethyloxazolidine, is added to the late colors as the bactericide component [U.S. Pat. No. 4,012,261; U.S. Pat. No. 4,374,124], 3-alkyloxazolidines with longer alkyls such as octyl [DE patent "2,656,342; DE pat. However, an antimicrobial derivative of oxazolidine was not soluble in water, which prevented its practical applications. Thus, they had to be solubilized in water by carrier detergents, which often reduced the antimicrobial effects of oxazolidine. Another disadvantage has been shown to be the easy hydrolyzability of oxazolidine derivatives.

The present invention overcomes these drawbacks. The present invention provides N-oxides of 2,2,5-trimethyl-3-alkyloxazolidine of the general formula I

K iC ch 3 (i) wherein R represents octyl, decyl, dodecyl, tetra-decyl, hexadecyl and octadecyl. The N-oxides of 2,2,5-trimethyl-3-alkyloxazolidinone have not been known or described so far. The production of N-oxides according to the invention is evident in the examples. The advantage of these substances is their water solubility, stability in aqueous solutions, their detergent and antimicrobial properties. Also, good compactability with commonly used anionic, cationic and non-ionic surfactants is preferred. Of 5-trimethyl-3-dodecycloxazolidine is dissolved in 20 cm @ 3 of 96 wt. percent ethanol. The solution was heated to 60 ° C. 1.25 cm @ 3 (0.011 mol) of 30 wt. % of an aqueous solution of hydrogen peroxide diluted with 10 cm 3 of distilled water. After addition of the entire hydrogen hydrogen peroxide, the reaction mixture is heated to 60 ° C for 2 hours and then allowed to stand at 25 ° C for 24 hours. After the reaction was complete, 0.02 g of platinum oxide was added to decompose the unreacted peroxide. The mixture is stirred for 24 hours, then platinum (II) oxide is filtered off (after washing with 96% ethanol, it can be reused).

The unreacted oxazolidine is removed from the reaction mixture by extraction with 10 cm 3 of butanol. After addition of an additional 10 cm 3 of butanol, the aqueous layer is azeotropically distilled off at a pressure of 40 mbar and 40 ° C. ° C to dryness. It achieves a 90% yield, ie 2.7 g of 2,2,5-trimethyl-3-dodecyloxazolidine N-oxide, which is a non-distillable pale yellow oily liquid. In aqueous solutions it is in the range of pH 5 to 9 and temperatures of up to 80 ° C. On the infra-red spectrum, these determining absorption bands are: 2,930, 2,855, 1,670, 1,380, 1,165.1,132, 1,095, 960, and 720 cm -1. The weight spectra are as follows: 283, 268, 257, 255, 199, 128 and 116.

Elemental analysis for C 18 H 37 NO 2, molecular weight 299 calculated: 72.24% C, 12.37% H, 4.68% N, found: 72.08% C, 12.43% H, 4.64% N. 2,2,5-trimethyl-3-dodecyloxazolidine oxide bacteriostatic and fungistatic activity on Staphylococcusaureus 10 mg microorganisms. dm-3, to Escherichia coli80 mg. dm'3 and 70 mg ..dm-3 on Candida albicans. Tests are carried out in an aqueous environment. Example 2

The procedure is as in Example 1, except that 2.27 g of 2,2,5-trimethyl-3-octyloxazolidine is used. The yield is 87%, ie, 1.11 g of 2,2,5-trimethyl-3-octyloxazolidine N-oxide. This compound is in the pH range 5 to 9 in aqueous solutions and is stable at temperatures up to 80 ° C. The determining absorption bandwidths on the infrared spectrum are the same as in Example 1. In the mass spectrum, the peaks are peaks: 227, 199, 149, 128 and 116.

Elemental analysis for C 14 H 29 NO 2, molecular weight 243, calculated: 69.14% C, 11.93% H, 5.76% N, found * 69.10% G, 11.98% H, 5.70% N. N- 2,2,5-trimethyl-3-octyloxazolidine oxide has bacteriostatic and fungistatic activity 2 6 1 5 1. 6

S for Staphylococcus aureus 70 mg. dm-3, on Escherichia coli 100 mg dm-3 and on Gandida albicans 120 mg. Figure 3

The procedure is as in Example 1, except that 2.55 g of 2,2,5-trimethyl-3-decyloxazolidine is used. The yield is 85%, i.e. 2.30 g of 2,2,5-trimethyl-3-decyloxazolidine N-oxide. This compound is in the pH range of 5 to 9 in aqueous solutions and is stable at temperatures up to 80 ° C. The determining absorption bands on the infrared spectrum are the same as in Example 1. In the mass spectrum, the peaks are peaks: 25.5, 227, 199, 128 and 116.

Elemental analysis for C 16 H 33 NO 2, molecular weight 271 calculated: 70.85% C, 12.18% H, 5.17% N, found: 70.19% C, 12.44% H, 5.14% N. N-oxide 2,2,5-trimethyl-3-decyloxazolidine bacteriostatic and fungistatic activity on Staphylococcusaureus 12 mg. dm-3, Escherichia coli70 mg dm-3 and Candida albicans 90 mg-dm-3.

The procedure is as in Example 1, except that 3.11 g of 2,2,5-trimethyl-3-tetradecyloxazolidine is used. The yield is 91%, i.e. 2.98 g of 2,2,5-trimethyl-3-tert-tradecyloxazolidine N-oxide. The compound is stable in aqueous solutions in the pH range of 5 to 9 and temperatures up to 80 ° C. The determining absorption bands on the infrared spectrum are the same as in Example 1. In the mass spectra, these determining peaks are: 311, 283, 199, 128 and 116.

Elemental analysis for C 20 H 41 NO 2, MW 327, calculated: 73.38% C, 12.54% H, 4.28% N, found: 73.29% C, 12.60% H, 4.25% N. 2,2,5-trimethyl-3-tetradecyloxazolidine oxide has bacteriostatic and fungistatic activity on Staphylococcusaureus 10 mg microorganisms. dm-3, to Escherichia coli70 mg. dm-3 and to 60 mg of Candida albicans dm-3. Example 5

The procedure is as in Example 1, except that 3.39 g of 2,2,5-trimethyl-6-3-hexadecyloxazolidine is used. Yield 88%, i.e. 3.12 g of 2,2,5-trimethyl-3-hexadecyloxazolidine N-oxide. The compound is stable in aqueous solutions in the pH range of 5 to 9 and temperatures up to 80 ° C. The determining absorption bands on the infrared spectrum are the same as in Example 1. In the mass spectra, these determining peaks are: 339, 311, 199, 128, and 116.

Elemental analysis for C 22 H 45 NO 2, MW 355, C, 74.34; H, 12.68; N, 3.94. Found: C, 74.26; H, 12.77; 2,2,5-trimethyl-3-hexadecyloxazolidine oxide has bacteriostatic and fungistatic activity on Staphylococcusaureus 30 mg microorganisms. dm "3, on Escherichia coli600 mg. dm" 3 and on Candida albicans 120 µg. dm "3. Example 6

The procedure of Example 1 is followed, except that 3.67 g of 2,2,5-trimethyl-3-octadecyloxazolidine are used. The yield is 81%, i.e. 3.1 g of 2,2,5-trimethyl-3-octadecyl-oxazolidine N-oxide. The compound is in the aqueous solution in the pH range of 5-9 and the temperature is up to 80 ° C. The determining absorption bands in the infrared spectrum are the same as in Example 1. In the mass spectrum, the peaks are: 367, 339, 199, 128, and 116.

Elemental analysis for C 24 H 49 NO 2, MW 383, calculated: 75.20% C, 12.79% H, 3.66% N, found: 75.09% C, 12.87% H, 3.62% N. 2,2,5-trimethyl-3-octadecyl azazolidine oxide has bacteriostatic and fungistatic activity on Staphylococcusaureus 60 mg microorganisms. dm "3, on Escherichia coli1000 mg, dm" 3 and on Candida albicans 200 milligrams. dm-3. Example 7

The procedure is as in Example 1, except that the reaction temperature is 50 ° C and the reaction time is 3 hours. The yield is 85%, i.e. 2.54 g of 2,2,5-trimethyl-3-dodecyloxazolidine N-oxide. N-oxides of 2,2,5-trimethyl-3-alkyloxazolidine can find widespread use in the formation of detergent compositions! with antimicrobial agents suitable for washing and simultaneous disinfection, e.g., floors, dishwashers, and fabric washing.

Claims

The N-oxides of 2,2,5-trimethyl-3-alkyloxazolidines of the general Formula I R is octyl, decyl, dodecyl, tetra, decyl, hexadecyl and octadecyl. -R- i J '- G .. h ^ C γ.Η, "a) Severografia, n. P. Plant 7, Most Price 2,40 Kčs