DE2263121C3 - Alkyl 2,3,3-triiodallyl ether, process for their preparation and their use in medicaments - Google Patents

Description

! ii the literature describes methods that the Alkylation of acetylenic alcohols with dialkyl sulfates (Houben-Weyl. Methods of organic Chemistry Vol VW. 1965 S 33) as well as the Treatment of the copper salt of such compounds in JodTrlofben-Weyl. Vol. V / 4, 1960, p. 554) affect. However, these methods result in the production of the contractions according to the invention no satisfactory results yet.

Some compounds of general formula II are known, for example, the 3-iodo-2-propynyl methyl ether according to R. Lespieau, Ann. Chim. (Paris), Vol.

I1 page 269 (1897), after a technically disadvantageous one Process are produced.

In the first stage of the claimed process is propargyl alcohol with an alkyl sulfate or Alkyl sulfonate, preferably in aqueous solution and in the presence of an alkali metal hydroxide, converted ». The corresponding alkyl 2-propynyl ether of the general formula HI is obtained in a very high yield. In the second stage of the process according to the invention is the alkyl 2-propynyl ether of the general formula

III monoiodiene either after prior purification by distillation or as a crude product and dissolved in an organic solvent or water. The alkyl-2-propir.yIäther is preferably mixed with a solution of 1 to 2 mol of an alkali metal hydroxide m water or a lower aliphatic alcohol and with stirring at temperatures of about 0 to 30 ⁰ C, preferably at room temperature, either with an aqueous solution treated with potassium iodide from 1 to 1.2 moles of iodine or a mixture of iodine. The corresponding alkyl 3-iodo-2-propynyl ether of the general formula II is obtained in high yield.

According to another embodiment of the process, the compound of the general formula can be used III with a copper complex salt, a copper salt? or copper (l) hydroxide into the corresponding copper convert acetylid and dies.es with iodine to alkyl iodo-2-propynyl ether implement the general formula II.

In these procedures, the same results can be obtained using a solution of an iodonium salt Iodine and potassium iodide can be obtained instead of elemental | od. In general, the solution can be carried out with tel water or a lower aliphatic alcohol.

According to the procedures described above, the alkyl-2-propiny'.äther is the general Formula III selectively monoiodinated in high yield. It is known that iodine readily adapts to the acetylenic Triple bond with formation of the corresponding alkyl 2,3-diiodallyl ether systems. As a result of activation of the terminal carbon atom by a basic catalyst such as an alkali metal hydroxide or copper ions or copper complex ions, the monoiodination proceeds according to the invention Process selectively while forming the alkyl 2,3-diiodallyl ether can be almost completely suppressed.

The monoiodination can also be achieved according to the invention by the fact that the compound general formula III reacts with iodine in liquid ammonia or an organic as a basic catalyst Amine, preferably morpholine or triethylamine, is used.

In the third stage of the process, the

2? 63

. ι £ 3 3-triiodallyl ether of the general formula I from Alky! -3-iodo-2-propynyl ethers obtained from the general Formula Il

JC ^ C-CH ₂ -OR (11)

cn reaction with iodine or an iodonium salt prepared in a minimum equivalent amount. The implementation

ms can be taken in a suitable solvent Stir the reaction mixture at temperatures of

wa 50 to 80 ⁰ C can be carried out. As a solvent _who uses the compounds that do not interact with iodine

eat. Preferred examples of these solvents

• d chloroform, dichloromethane, carbon tetrachloride, Dfoxan, lower aliphatic alcohols, acetic acid and water

The addition of iodine is carried out at low temperatures, ie room temperature when irradiated lan the reaction mixture with light, this leads to a shortening of the reaction time and to an increase in yield. The photo-catalyzed addition of iodine at low temperatures also suppresses decomposition reactions which can occur when the process is carried out with heating. The product is obtained in a very good yield.

The use of an excess of iodine, preferably 1.1 to 1.5 times the sloichiometric amount, also shortens the reaction time, but does not particularly affect the thermal decomposition reaction. The end of the reaction can be determined by titrating the unreacted iodine with a sodium thiosulphide solution.
The alkyl-3-iodo-2-propi-

nyl ethers of the general formula II can either be, for. B. by distillation under reduced pressure cleaned or used as a raw product.

The alkyl 2,3,3-triiodallyl ethers of the general formula I can be isolated in a customary manner after the reaction has ended.

According to another embodiment of the process according to the invention, the alkyl 2,3,3-triiodallyl ethers of the general formula I also by reacting propargyl alcohol with iodine in the presence of an alkali metal hydroxide in a solvent inert to iodine, preferably chloroform, dichloromethane, Carbon tetrachloride or dioxane, and conversion of the 2,3,3-triiodoallyl alcohol obtained into a polar aprotic solvent, preferably dimethylformamide or dimethyl sulfoxide, with the corresponding Alkylicruiigmittel be prepared. The 2,3,3-triiodallyl alcohol can also initially in a activated, (reactive) derivative, e.g. B. a 2,3,3-triiodallyl halide or pseudo-halide in the presence of a base, transferred and then with the corresponding alkali metal alcoholate or the corresponding alcohol reacted in the presence of a base will.

The alkyl 2,3,3-triiodallyl ethers of the general formula I are valuable drugs. They are antibiotics with broad antimicrobial spectrum and valuable Disinfectants. The compounds of general formula I can also be used as additives in poultry feed as well as for the treatment of Schweineruhr.

In Table I, the antimicrobial activity of 2,3,3-triiodoallyl methyl ether is more positive than gram and gram-negative bacteria.

Table 1

Tribes

Minimum inhibitory concentration V / ml

Ver Ver Ver

tie P) tie 2 *) tie 3 *) tie 4 *)

Staphylococcus aureus 209-p S. aureus CH-91
S. aureus DH-18S
Streptococcus haemolyticus Cook Diplococcus pneumoniae Type 1 Bacillus subtilis PCI 219 Salmonella typhi O-901-W Escherichia coli Communis 0-16
O-20
0-78
Ο-83
0-135
0-138
O-139
Ο-142
P-55
S-54 R6

Mycobacterium tuberculosis H 37 RV
El-tor vibrio

Trichophyton asteroides Aspergillus fumigatus Saito Candida albicans Totuka Crvntococcus neoformans 301

6.25

12.5

12.5

12.5

10-1

10-1

3.12

10-1

6.25

0.78

3.12

12.5

3.12

3.12

12.5

6.25

12.5

12.5

10-1

3.12 1.56 3.12 3.12 0.78 50
100
100

50

25th

25th

100

25th

100

100

50

50

25th

100

50

50

100

50

50 100 25th 50 50 100 100 200 25th 100 100 100 100 200 100 100 100 100

continuation Mindcsthcmmkon / eniraiion
• // ml
Pre-Ver
binding t *) binding 2 *) 100
50
200
200 Ver
binding 3 *) Ver
binding 4 *) Tribes 6.25
12.5
100
100 100
100
200
200 100
100
200
200 S. typhymurium 1325
S. typhymurium 4-2
PS. aerginosa 2-3
PS. aerginosa 15

*) Compound 1: 2,3,3-triiodallyl methyl ether.
Compound 2: 2,3,3-triiodallylyl ether.
Compound 3: 2,3,3-triiodallyiisopropyl ether. Compound 4: 2.3.3-Triiodallyl-n-propyl ether.

The compound 2,3,3-triiodallyl methyl ether has an effect on poultry, pigs and mice low toxicity. When administered orally to mice, the LD50 is more than 100 mg / kg, when administered intraperitoneally Administration 50 to 100 mg / kg.

It was also found that 2,3,3-triiodallylme-ethyl ether added to poultry feed, has excellent growth effects in poultry, is practically not absorbed by the gastrointestinal tract of the animals, does not accumulate in the body and does not generate cross-resistance. _, ₀

It is known to use feed containing small amounts of various antibiotics in poultry farming contains to suppress diseases and increase the growth of animals. Numerous of the for However, antibiotics used for these purposes are mainly used to treat diseases of the People used. It is known that the prolonged use of such antibiotics in poultry feed Eur development of resistant bacterial strains that excreted along with the extremes. will. Antibiotics that are not used in human medicine are also from the undesirable for the same reason if they create cross-resistance. Unless such antibiotics are in the meat of the If poultry are left, they can cause allergies in 4s humans. The use of steroid hormones in poultry feed for growth stimulation was banned after it was found that the Residues accumulate in the body of animals and so have adverse effects on the human body can evoke.

Feed additives for growth stimulation preferably have an effect on those bacterial populations which are normally present in the gastrointestinal tract. From Table I it can be seen that 2,3,3-triiodine ss allyl methyl ether is effective against such bacteria. Fs is that the growth-stimulating effect is achieved when using small amounts of the additive in the Geflügelfuttcr and that even large amounts of no adverse effects hervorru- (> o fen. Since the acute Toxiziiät (1.D ₅₀₎ of 2,3.3-Trijodallyimethyläthcrs further desired, when administered orally to mice is more than 1000 mg / kg, this compound is a safe and excellent luiter / usai /. Kine! .Di ,, from 50 to 100 mg / kg when administered directly to mice means a relatively low toxicity / Since the 2,3,3-triiodallylmethyläthcr is absorbed only very poorly from the matien intestinal tract, the LD50 for oral administration is 10 to 10 times higher than for intraperitoneal administration.

The poor absorption from the gastrointestinal tract As a result, no residues of this compound accumulate in the meat of the animals.

The 2,3,3-triiodallyl meth} ether is usually used Feed in an amount of 1 to 200 g / ton and evenly mixed with it.

The 2,3,3 triiodallyl meth \ lether can also be used as an active ingredient are used in drugs for the treatment of pork clock. The connection does not interfere with Medicinal substances that are used in human medicine, it does not cause cross-resists /, is from The pig's gastrointestinal tract is practically not absorbed and no residues accumulate in the pig Pork meat.

It is well known that the pig clock causes great damage in pig breeding. There were in the Antibiotics used in human medicine, which are effective against pathogenic Coli bacilli, for suppression and treatment of Schweineruhr used. However, this has the disadvantage that resistant bacterial strains are formed and released into the environment with the excrement. The 2,3,3-triiodallyl methyl ether does not have these disadvantages and can effectively and safely be used to treat pig osteoarthritis can be used.

The crystalline 2,3,3-triiodallyl methyl ether is converted into a fine powder for the production of pharmaceuticals grind and either diluted with gelatin to an active ingredient content of about 10 percent by weight and coated or diluted with ten times the amount of lactose. The drug is used in an amount of at least about 10 mg / kg body weight administered to pigs in a single dose. The dose may vary depending on the severity of the disease will be increased. Usually the medicinal preparations are used twice on the first day and thereafter administered once daily during the third and fourth days. The disease is general subsided within about 5 days.

example 1
Production of 2,3,3-triiodallyl methyl ether

Ib g of 3-iodo-2-propynyl methyl ether are dissolved in 80 ml of chloroform and mixed with 25.4 g of powdered iodine. The mixture is heated for 3 hours under reflux at a bath temperature of 70 ^Q C and then allowed to stand for 15 to 18 hours at room temperature.

The mixture is then heated to 70 ° C. and gradually shaken with 1 η aqueous sodium thiosulfate solution until the iodine color has disappeared. The aqueous solution is separated off, the Chloroform solution washed with water and evaporated under reduced pressure. It will be about 30 g crystalline crude product obtained. After recrystallization from methanol, 29.5 g (79 percent of the Theory) almost colorless columnar to platelet-shaped crystals with a melting point of 43.5 to 44.5 ° C echo.

C ₄ H ₅ OJ ₃ (MgW. 450):

Calculated: C 10.07, H 1.12;
found: C 9.62, H 1.31.

NMR (CCl ₄ ) ή (ppm); 3.32 (singlet, 3H, CH ₃ O-), 4.04 (singlet, 2H. - CH ₂ -O -). Tetramethylsilane is used as standard.

Example 2

Production of 2,3,3-triiodallyl ethyl ether

16 g of 3-iodo-2-propinyläthyläther (Kp. ₄ 50 to 52 ⁰ C) are dissolved in 100 ml of chloroform and treated with 20 g of iodine. The mixture is irradiated while stirring with light from a 500 watt tungsten filament lamp for photographic purposes. During the reaction, the Reaklionsgemisch is maintained by cooling with ice at a temperature below 10 ⁰ C. As soon as the iodine color has almost disappeared. 1N aqueous sodium thiosulfate solution is added to the mixture and the mixture is stirred. The chloroform solution is separated off, washed with water and dried over sodium sulfate. The solvent is distilled off. 32 g of the practically pure compound remain as an oil. The oil can be purified by distillation under reduced pressure.

Kp.o.27l08bisll0 ⁰ C

NMR (CDCh). 6 (ppm): 1.36 (triplet. J = 7 Hz. 3H, -CH ₃ ), 4.19 (singlet, 2H ₁ -O-CH ₂ -).

Example 3
Production of 2,3,3-triiodallyl isopropyl ether

45

2.8 g of 3-iodo-2-propinylisopropyläther (Kp. ₆ 63 to 65 ⁰ C) are dissolved in 30 ml of chloroform and treated with 3.2 g of iodine. The mixture is reacted and worked up according to Example 2. The chloroform extract is evaporated. 4.65 g (77.5 percent of theory) of crystalline product remain. After recrystallization from methanol, 3.25 g of colorless crystals with a melting point of 433 to 44 ° C. are obtained.

Ce, H9Oj3 (Mgw.477.8): Calculated: C 07/15. H 130: found: C, 15.07. H 1.82.

55

Example 4 Production of 233-triiodallyl-n-propyl ether

60

8.4 g of S-iodo ^ -propynyl-n-propyl ether (Kp.5.2 69-70 ⁰ Q are dissolved in 50 ml of chloroform and treated with 9.5 g of iodine The mixture is reacted and worked up according to Example 2. Finally, the chloroform extract evaporated 173 g of an oil remain, which is crystallized with methanol, giving 12.8 g of pale yellow crystals with a melting point of 33.5 to 34 ° C.

C "HqOJ ₃ (Mgw.447.8):

Calculated: C 15.07, H 1.90;
found: C, 15.05. H 1.89.

The 3-iodopropynyl ethers required are as follows made: 44.8 g propargyl alcohol and

93.4 g of 96 percent potassium hydroxide are dissolved in 80 ml of water. 100.8 g of dimethyl sulfate are added dropwise to the aqueous solution at about 15 ° C. with stirring over a period of about 1 hour. Then the mixture is heated an additional hour at 6O ⁰ C. The mixture is then heated to about 60 ° C. with stirring and distilled. Finally, the bath temperature is increased to about 8O ⁰ C. 61 g of distillate with a boiling point of 58 to 65 ^° C. are obtained. The product is identified as a methyl propargylic ether. The purity is about 78 percent and the yield is 96 percent. A small amount of methanol can be seen in the gas chromatogram and in the NMR spectrum.

NMR (CDCl ₃ ) ό (ppm): 4.07 (doublet, J = 2 Hz, 2H, -CH ₂ -O-), 3.36 (singlet, 3H, -O-CH3), 2.48 (triplet : J = 2 Hz, IH, HC = C-). The NMR spectrum also shows a signal at 3.27 ppm which can be assigned to the protons of the methyl group of methanol.

7 g of the methyl propargyl ether obtained (methanol content about 22 percent) are mixed with a solution of 11.2 g of potassium hydroxide in 20 ml of water. The mixture is stirred vigorously at room temperature and 25.4 g of iodine are added in several portions. When the addition is complete, the mixture is stirred for about 1 hour at room temperature and then the product is extracted with 50 ml of chloroform. The chloroform extract is washed with water, dried over sodium sulfate and evaporated. 15 g of almost pure 3-) od-2-propynyl methyl ether remain as a colorless, transparent liquid. In the further purification by distillation under reduced pressure, 13 g (85.5 percent of theory) are obtained of a liquid of boiling point. ₂ 39-40 ⁰ C.

Yield 84.5 percent of theoretical), 3-] od-2-propinylisopropyläther (Kp.e, 63 to 65 °; In an analogous manner there is obtained 3-) od-2-propinyläthyläther (Kp.4 50 to 52 ^C C C:. yield 51 percent of theory) and 3-iodo-2-propynyl-n-propyl ether (bp "69-70 ⁰ C; yield

74.5 percent of theory).

Example 5
Production of 233-triiodallyl methyl ether

1.15 g 233-Trijodallyljodid (b.p. 80-81 ⁰ C;. Prepared by addition of iodine in 13-Dijodpropin) are dissolved in 35 ml of methanol, the solution with 2 ml of a 1.05 η solution of potassium hydroxide in methanol, and then 24 Left to stand at 30 ^{° C. for hours.} Thereafter, the mixture under reduced pressure is evaporated at a temperature below 40 ⁰ C, the residue treated with 10 ml of water and left standing for 15 to 18 hours at 0 ° C. At first an oil is formed which gradually crystallizes. Yield 890 mg of crude crystals. After recrystallization from methanol, 496 mg (52 percent of theory) of light yellow crystals with a melting point of 42 to 433 ° C. are obtained.

10

Example 6
Production of 2,3,3-TrijodaIlyimethyläther

8.72 g of 2,3,3-Trijodallylalkohoi (mp 152 to 153 ° C; prepared by reacting propargyl alcohol with iodine in the presence of a base) are dissolved in 20 ml of dimethylformamide and within 1 hour at a temperature of 15 to 20 ⁰ C. 3.8 g of dimethyl sulfate and a solution of 1.3 g of sodium hydroxide in 5 ml of water are added dropwise to C with external cooling with water. After the addition has ended, the mixture is stirred at 25 ° C. for a further 30 minutes. Then 60 ml of ice water are added. The precipitated crystals are filtered off, washed first with water and then with a little ice-cold methanol. Yield 7.5 g (83.3 percent of theory) of product with a melting point of 42 to 43 ° C.

Example 7
Production of 2.3.3-triiodallyl methyl ether

4.36 g of 2,3,3-triiodoallyl alcohol are dissolved in 10 ml of dimethylformamide and 4.26 g of methyl iodide and a solution of 0.8 g of sodium hydroxide in 3 ml of water are added dropwise within about 30 minutes, while cooling with ice and stirring. When the addition is complete, the mixture is ^{stirred at 25 °} C. for 5 hours, then 50 ml of ice water are added, and the precipitated crystals are filtered off, initially with water and

'5 then washed with a little ice-cold methanol. Yield 3.9 g (86.7 percent of theory) light yellow Crystals from M.p. 42 to 43 ° C.

Example 8
Production of 2,3,3-triiodallyl methyl ether

5.9 g of 2,3,3-triiodoallyl-p-toluenesulfonate (F. 114 bis 116 ° C; produced by reacting 3-iodo-2-propynyl-p-toluenesulfonate with iodine or by reacting p-toluenesulfonyl chloride with 2.3.3-triiodallyl alcohol in Presence of a base) are dissolved in 10 ml of dimethylformamide and with ice-cooling and stirring with 0.55 g Sodium methylate added. The mixture is then cooled with ice for 30 minutes and for a further hour Stirred at 25 ° C. and then treated with 60 ml of ice water. The precipitated crystals are filtered off, initially washed with water and then with a little ice-cold methanol. Yield 4.1 g (91 percent of theory) light yellow crystals with a melting point of 42 to 43 ° C.

The effects of the compound according to the invention as a feed additive are shown below.

The amount of 2,3,3-triiodallyl methyl ether given in Table II is evenly mixed into a ton of poultry feed. The 2,3,3-triiodallyl methyl ether was previously mixed with 100 times the weight of defatted rice bran. With this compound feed 20 chicks are fed for 10 weeks. The increase in body weight is compiled in Table II.

Table 11 2 weeks 4th week 6th week 8th week 10th week Weight Addition, g / t increase Index*) 120.4 357.4 682.4 1084.4 1329 7 109.9 1 125.9
147.6
120.4
124.3
128.2
106.5
116.4
127.3 362.1
388.0
350.2
359.4
349.8
343.2
341.2
374.6 706.2
764.0
647.3
671.3
663.1
686.3
611.6
664.2 1099.3
1150.7
990.7
1030.5
946.7
1039.6
926.7
1012.9 1408.4
1512.1
1303.1
1382.2
1223.7
1298.3
1209.7
1324.0 116.4
125.0
109.7
114.3
101.2
107.3
100.0
109.5 5
10
20th
50
100
200
No addition
Procaine penicillin G.
20 g

*) Based on the control group (index = 100).

From table I! it can be seen that all test groups which were treated with the 233-triiodallyl methyl ether were fed an increase in body weight after 10 weeks compared to the control group showed that no feed containing 233-triiodallyl methyl ether was given. Self with the naked eye it could be determined that those with 10 g of 233-triiodallyl methyl ether per ton Food-fed chicks were larger than the control chicks. The addition of large amounts of 233 triiodallyl methyl ether does not reduce body weight. This shows that the Compound in the gastrointestinal tract is practically not absorbed and does not cause any side effects

Its use as a medicinal product is supported by the

the following statements on the effect against Schweineruhr shown.

2,33-triiodallyl methyl ether is put in a mortar finely ground and then diluted with ten times the weight of lactose. With this preparation 41 pigs suffering from dysentery are treated

Jt V ^"Pre P ^{arat w} i""d twice on the first day and during the third and fourth day orally once administered The results are summarized in Table HI in this table, the letters A, B, C and D have the following meaning · A = watery excrement

B = muddy excrement C- = soft excrement

Π = normal excrement

Ii

12th

Table IU (a)

animal Ge old body Singles- Clinical picture 2 day 3rd day 4th day 5th day evaluation bad Weight dose D. mg of drug D. fabric / kg D. body B. C. D. No. Days kg Weight I. day B. D. 1 m 21 5 60 B. B. D. cured 2 m 21 5 60 C. C. C. D. cured 3 W. 21 5 60 A. A. C. D. cured 4th m 26th 7th 43 C. C. D. cured 5 W. 26th 7th 43 C. B. D. cured 6th m 26th 7th 43 C. C. D. cured 7th m 7th 3 100 B. C. C. C. D. cured 8th W. 7th 3 100 C. D. cured 9 W. 13th 4th 75 B. D. cured 10 W. 13th 4th 75 C. A. D. cured 11th m 12th 2 150 A. A. D. cured 12th m 12th 2 ! 50 A. C. D. cured 13th m 27 8th 100 B. C. D. cured 14th m 28 8th 100 B. D. cured 15th W. 22nd 5 60 C. C. D. cured 16 m 10 4th 75 B. C. D. cured 17th W. 10 3 100 A. D. cured 18th W. 10 3 100 B. D. cured 19th fil 10 4th 75 C. D. cured 20th W. 15th 3 100 C. D. cured 21 W. 15th 3 100 C. B. D. cured 22nd W. 9 2.5 120 B. A. B. Ει D. cured 23 W. 9 1.5 200 B. A. B. c: D. cured 24 m 9 1.5 2on B. B. D. cured 25th W. 8th 2 15 (i A. C. D. cured 26th m 34 5.5 35 B. C. D. cured 27 m 55 10.1 50 A. C. D. cured 28 m 54 6.1 41 A. C. D. cured 29 m 56 13.8 51 A. A. B. B. D. cured 30th m 35 4.1 49 B. C. D. cured 31 W. 35 4.3 47 B. A. B. D. cured 32 W. 35 4.1 49 * B. C. D. cured 33 m 34 6th 42 B. B. D. cured 34 W. 26th 2.7 56 A. B. D. cured 35 m 55 10 50 B. B. D. cured 36 W. 28 4th 50 A. B. D. cured 37 m 28 5 50 B. cured 38 W. 40 5.3 47 B. cured 39 m 38 6.5 46 B. cured 40 m ⁿ .9 5.9 42 B. cured 41 m 38 6.7 44 B. cured

Table 111 (b)

Comparative experiment, effect of Kanamycn sulfate against Schwe.neruhr

Ge Aller

bad

Days

body weight

Singles- Clinical picture 2 day 3rd day 4th day 5th day Valuation dose B. C. D. mg of drug B. B. C. D. fabric / kg C. C. C. D. body
Weight 1 day B. B. C. D. 150 B. D. cured 145 B. dcsgl 135 C. D. the same 130 A. B. C. D. the same 130 C. desgi 75 B. Death! OK B. go" 120 B. the same

1 m 17th 2 W. 17th 3 rn 17th 4th m IS 5 W. 18th 6th W. 16 7th m 22nd 8th IV 22nd

2.0 ZI 22 23 2J 4.0 Z7 23

13th

Continuation Gc- Aher Body Rinzcl- Clinical picture 2nd day 3rd lay ■). lay 5th day evaluation animal Schleehi gcwk'lil dose B. C. D. mg Ar / nci- C. C. D. Moff.'kg C. C. D. Days kg body
Weight 1 day B. B. B. C. Ni. \ v 19th 3.0 100 A. the same 9 m 19th 2.6 115 B. I) the same 10 W. 15th 2.6 115 C. C. C. D. the same 11th m 15th 2.3 130 B. D. treatment 12th D. aborted W. 15th 2.4 125 B. D. cured 13th W. 15th 3.0 100 C. B. C. C. D. the same 14th m 16 3.0 100 C. D. the same 15th W. 19th 2.8 105 B. A. B. B. B. the same 16 W. 23 4.6 65 C. the same 17th m 23 3.0 K) O B. B. C. C. C. the same 18th VV 23 4.5 67 C. 13th B. C. C. the same 19th W. 24 3.5 85 13th B. C. C. D. treatment 20th C. C. D. aborted ITi 7th 2.0 150 B. A. B. D. the same 21 W. 9 3.0 100 C. A. C " D. the same 22nd m 15th 5.0 60 B. cured 23 m 15th 5.0 60 H the same 24 W. 13th 4.0 75 B. the same 25th m 12th 4.0 75 C. the same 26th

Table Hi shows the superiority of 2.3.3-Tiiiodallylmeihvlather / for the treatment of black diarrhea versus kanamycin sulfate.

Claims (3)

Patent claims: 1. The general alkyl 23,3-triiodailyl ethers formula C = C-CH ₁ -OR / I
YY in which R is a methyl, ethyl, n-propyl or isopropyl group. 2. Process for the preparation of the alkyl 2,3,3-triiodallyl ethers according to Claim 1, characterized in that one is carried out in a manner known per se a) Propargyl alcohol with an alkyl sulfate or alkyl sulfonate with 1 to 3 carbon atoms alkylated, the resulting alkyl 2-propynyl ether or its copper salt is reacted with iodine and the resulting alkyl 3-iodo-2-propynyl ether with iodine in at least an equivalent amount implements or b) Propargyl alcohol with iodine in the presence of an alkali metal hydroxide in an inert solvent reacted and the 2,3,3-triiodallyl alcohol obtained was alkylated. 3. Medicaments containing a compound according to claim 1 and customary carriers and or or diluents and / or auxiliaries. 35 The invention relates to alkyl 2,3,3-triiodallyl ethers of the general formula I. 40 C = C-CH ₂ -OR (1) J J in which R is a methyl, ethyl, n-propyl or isopropyl group. The invention relates to furthermore a process for their production by, in a manner known per se, e (a) Propargyl alcohol with an alkyl sulfate or alkyl sulfonate having 1 to 3 carbon atoms alkylated, the resulting alkyl 2-propynyl ether of the general formula 55 HCsC-CH ₂ -OR (111) or its copper salt is reacted further with iodine and the resulting alkyl-3-iodo-2-propynyl ether general formula II JC = C-CH ₂ -OR (ID with iodine in at least an equivalent amount, or (b) propargyl alcohol with iodine in the presence of an alkali metal hydroxide in an inert solvent and the resulting 2,3,3-triiodallyl alcohol is alkylated. The invention also relates to the use of the compounds of general formula I in medicaments