CS270449B2 - Method of carbazates production - Google Patents

Abstract

3-Acylcarbazate esters of formula ACONHNHCOOR (I) and their acid-addn. salts are new, where: A=3-10C alkyl, 3-10C alkenyl, 2-10C haloalkyl, CF3, phenyl(1-3C)alkyl, phenyl(2-3C)alkenyl, naphthyl(1-3C)alkyl, phenyl(opt. substd. by 1-4C alkyl, halogen, 1-4C alkoxy and/or OH), (3-7C)cycloalkyl(1-3C)alkyl, nitrofuryl, diphenylhydroxymethyl, or indazolyl opt. mono- or polysubstd. by alkoxy; R=1-4C alkyl; provided that A is not t-Bu when R=Et. Animal feeds or animal feed supplements or concentrates contg. cpds. (I), including (I; A=t-Bu, R=Et), are also new.

Description

A particularly preferred embodiment of the compounds of formula (I) is methyenylpropionyl) carbazate.

The process according to the invention consists in reducing a compound of the formula I in which A is phenyl-C1-4alkenyl and R is as defined above.

The reduction may be carried out by catalytic hydrogenation, for example in the presence of a palladium or platinum catalyst, or by a complex metal hydride, for example sodium hydride. This reaction may be carried out in an inert organic solvent as the reaction medium.

The compounds of formula (I) may be used in cattle breeding. These substances have the valuable effect of increasing weight gains while significantly increasing feed utilization in domestic animals, particularly pigs, poultry and ruminants, especially lambs.

The effect of weight gain on the compounds of formula I is illustrated by the following test, the results of which are summarized in Table 1. The test was performed on lambs, fed for 40 days and the test compound was administered at a dose of 50 mg / kg. Results are mean values from three experiments. The table shows the increase in weight gain and feed utilization value. Methyl 3- (B-phenylpropionyl) carbazate was used as the test compound.

Table 1

Values untreated control methyl 3- (Q-phenylpropionyl) carbazate average starting weight, kg 16.3 16.3 average final weight, kg 27.2 , 29.5 average daily weight gain, g 270 330 average daily weight gain, relative to control,% 100 ALIGN! 122.2 average daily food consumption, g 1097 950 use of feed, kg 4.2 3.3 the use of feed in relation to control, 100 ALIGN! 78.6

CS 270 449 B2

The compounds produced by the process of the invention do not have antibiotic effects and therefore do not have adverse side effects of antibiotics.

The compounds of formula I have the excellent property of not having a mutagenic effect. This is very important in livestock farming, since a large number of known weight gain promoters cannot be added to the feed at all or only in a very limited amount, since these active substances have a mutagenic effect.

From the above data, it is apparent that the weight gains of the animals fed the feed containing the compounds of formula I are significantly higher than those of the control group. In doing so, the same weight gains can be achieved with a significantly reduced amount of feed if the feed contains a compound of formula I. This is evidence of improved feed utilization.

The following exemplary embodiment illustrates the invention without limiting it in any way.

EXAMPLE Methyl 3- (8-phenylpropionyl) carbazate

22.0 g (0.1 mol) of methyl 3- (O-phenylacryloyl) carbazate are dissolved in 300 ml of methanol and the solution is hydrogenated in the presence of 0.2 g of palladium on carbon catalyst. The solution was evaporated. 21.8 g of white crystalline compound are obtained, yield 98.2%, m.p. 118 ° C. .

Claims (1)

1. A process for the preparation of carbazates of the formula I C II o NH NH OR (I) wherein Ar is phenyl-C ₂ _ ₃ alkyl, and C ₁ _ ₄ alkyl, wherein the C ₂ _ ^ alkenyl, and R has the above defined reducing compound. wherein A is phenyl2. nací The method of item 1, or a complex metal hydride. characterized by That the reduction is carried out by catalytic hydroge3. 2. The method of claim 1, wherein methyl 3- (O-phenylacryloyl) carbazate is reduced.