DE1228501B - Use of bis- (5-nitrofurfurylidene) -acetonguanyl-hydrazones as supplementary feed - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

Int. CL:

A23k

GERMAN

PATENT OFFICE German class: 53 g - 4/04

EDITORIAL

BLOLIOTHEK

of the German

PATBiTANTES

Number:
File number:
Registration date:
Display day:

1228 501
T 23381IV a / 53 g
January 25, 1963
November 10, 1966

The invention has the use of bis (5 - nitrofurfurylidene) - acetone - guanylhydrazones as Complementary feed, especially for young pets including poultry, such as. B. chicks, turkeys, Ducks and the like on the subject. The active ingredient can also be used to feed young cattle, horses, pigs, Dogs and sheep can be used.

According to the invention, the growth of young pets by the administration of the invention Active ingredients accelerated. Rapid growth is very important economically, especially in so rapidly growing domestic animals, such as poultry, such as z. B. chicks, turkeys, ducks and the like. The faster the growth is, the greater is the portion of fodder turned into meat. It became this one Purpose so far different antibiotics with a small spectrum of activity, such. B. penicillin, bacitracin, Streptomycin, and broad spectrum antibiotics such as tetracycline, oxytetracycline or Chlortetracycline and the like have been proposed. When mixed with animal feed, these effect compounds weight gain in appropriate amounts under certain circumstances.

The present invention relates to the use of animal feed containing the usual nutrient components contain, as well as an effective amount of the growth-promoting substances specified in more detail below Complementary feed. In addition, the animal feed in addition to the active ingredients according to the invention. substances one or more valuable antibiotics with the use of bis- (5-nitrofurfurylidene) -acetonguanyl-hydrazones as supplementary feed

Applicant:

Toyama Kagaku Kogyo Kabushiki Kaisha, Tokyo

Representative:

Dr. F. Zumstein, Dr. E. Assmann

and Dr. R. Koenigsberger, patent attorneys,

Munich 2, Bräuhausstr. 4th

Named as inventor:
Yutaka Kodama, Toyama;
Tsutao Fujiwara, Tokyo;
Tatsumi Inagaki, Toyama (Japan)

Claimed priority:

Japan January 26, 1962 (2179)

broad spectrum, such as chlortetracycline, tetracycline or oxytetracycline can be added.

The present invention thus relates to the use of bis (5-nitrofurfurylidene) acetone guanylhydrazones or of their acid addition salts, especially of their hydrochlorides, the formula

O ₂ N -

Ri
CH = C - C - CH = CH

NO ₂

HN

NHR ₂

NH

where Ri is a hydrogen or halogen atom or a lower alkyl group, R _{2 is} a hydrogen atom or a lower alkyl group, X is an acidic group and η is the number 1, 2 or 3, where n = \ when X is the radical of a monobasic acid , η = 1 or 2 when X is the residue of a dibasic acid, and η = 1, 2 or 3 when X is a residue of a tribasic acid, as with the usual,

nutritionally balanced feed or compound feed, in particular poultry feed, or supplementary feed which can be administered with the drinking water in amounts of about 5 to mg, in particular 10 to 100 mg per kilogram of feed. The unsubstituted derivative, in which Ri and R _{2 are} hydrogen and X is chlorine, is referred to below as "substance P" for abbreviation.

6U9 710/82

The .Beifuttermittel of the present invention can be used in very different amounts, e.g. B. from about 5 to 500 ppm can be used. Optimal results are obtained, especially with chicks a concentration of about 25 ppm (mg / kg feed).

An advantage of the present invention is that at optimal concentrations, a shows stronger growth-stimulating effect than with the previously used antibiotics; another ro The advantage is that the active ingredient does not need to be used alone, since it can be used together with antibiotics, such as chlortetracycline, and the use of such combined feedstuffs is also the subject of the invention.

By means of comparative tests it could be established that the well-known preparation "Furazolidon" the following formula

O ₂ N

20th

CH = N - N ■

CH ₂

C = O
O

Table I.

Chick growth after administration of

"Substance P", furazolidone and chlorotetracycline hydrochloride

(Weight after 4 weeks in grams)

CH ₂

which is similar in structure to the active ingredients used according to the invention, not growth-promoting Has an effect. For those carried out under the conditions of Example 3 below Experiments gave the results shown in the following table:

Chlortetracycline
hydrochloride
ppm 100 average Without further
additive 12.5
"Substance P" ppm
Furazolidone _o j 484
502
474 522
510
533 1 200 i 487 522 [ 515
503
513 Ui U) ul
U) K) I— ¹
KJ K> K) 510 522 514
494
498 533
503
542 502 526 500 523 477
498
490 488 537
513
483 511 505
502
502 503 501

The effect of the N-methylated "substance P", ie the compound according to the invention with R ₂ = methyl and X = HCl, on the growth of chicks was also examined under the same conditions. The results are given in the following table:

Table II

Chick growth after administration of "substance P", "N-methyl-substance P"

and chlortetracycline hydrochloride

(Weight after 20 days in grams)

Chlortetracycline HCl

ppm

Without further
additions

12.5 ppm

"Substance P"

"N-methyl-P" 25 ppm

"Substance P" "N-Methyl-P"

50 ppm

"Substance P"

"N-Methyl-P"

0
100

270
293

305
331

319

322.5

The results show that the "N-methylated substance P" of the unsubstituted "substance P" in comparable to the growth-promoting effect and even at low doses (12.5 and 25 ppm) is superior and clearly works better than furazolidone.

The following examples illustrate the invention. Varying amounts of "substance P" are involved mixed into various animal feeds.

example 1

A typical commercial feed is used with the following composition:

component

Ground yellow corn 51.4%

Soybean meal (solvent -

extracted) (44%) 30.0%

Menhaden fish meal (60%) 5.0%

325
326

318 326

306 315

50

55

60

Corn gluten flour (41%) 5.0%

Dried alfalfa flour (17%)

(100,000 A) 2.0%

Stabilized fat 4.0%

Dicalcium phosphate 1.2%

Ground calcite limestone

(33% Ca ++) 0.5%

Sodium chloride 0.3%

Trace minerals (so-called

"Delamix" + 2% Zn ++ "> 0.1%

Vitamin-amino acid premix 0.5%

The diet alone is used as a reference, and various amounts of "Substance P" as well various amounts of procaine penicillin and chlortetracycline hydrochloride are added. at each group will be Peterson crossbreed broiler chicks used, namely six males and six females per group. Feed and

Any amount of water is given. The results are given in the table below.

Table 1

additive Growth in%, based on
the comparison experiment 1 2 3 1 4th Age in week 100 100 100 100 118 109 109 106 Comparative experiment ....... 97 98 100 97 100 ppm "substance P" .... 109 104 103 100 100 ppm procaine penicillin 100 ppm chlortetracycline
hydrochloride

ί Growth in%, based on Age in 0 12.5 ppm 50 100 link »Substance Ρ« \ the comparison attempt Weeks 100 116 25th 111 120 ί 1 100
100 105
105 127 106
102 107
104 [ 2
3 100 105 116
112 103 103 Procaine- J 4th 100 111 110 107 131 Penicillin 1 1 100 100 119 103 116 { 2 100 97 107 102 105 "3 100 98 103 103 104 4th 101

From the table it can be seen that the optimal amount of "substance P" is about 25 ppm and at this concentration gives considerably better results than any concentration of the antibiotics after 4 weeks. Even if 100 ppm "Substance P" was used in the same amount, i. H. the optimal amount When comparing penicillin, the results are not significantly different after 4 weeks. With In other words, "Substance P" is just as effective as penicillin and at the preferred concentration, which is lower, more effective.

Example 3

The experiments of Example 2 are repeated, with the difference that a comparative experiment is carried out and the experiments at each concentration of "substance P" with the addition of certain Quantities of chlortetracycline hydrochloride were performed. Table 3 shows the results; the comparative experiment is referred to as 100% as in Example 2.

Table 3

It can be seen that 100 ppm "Substance P" at points in time alone gives better results than each of the two antibiotics.

Example 2

The effect of varying amounts of "substance P" and procaine penicillin was tested; the diet used in Example 1 was used for comparison; the active ingredients were in separate Trials added in amounts of 12.5, 25, 50 and 100 ppm. The following table shows the Results:

Table 2

f 0 I. 50
50 I. Growth in ° / o based on the 0 Substance P «ppm 50 100 Chlortetracycline ί [ Comparative experiment 100 25th 118 107 ' hydrochloride 100 \ Age in > 100 108 115 108 ppm I. Weeks 100 109 111 108 ί 1 100 106 113 112 200 y 2 114 110 111 115 ι 3 106 123 108 110 4th 103 115 106 108 1 106 110 111 111 2 113 111 129 116 3 108 126 109 109 4th 105 112 107 105 1 108 113 110 107 2 110 115 101 113 3 106 109 101 109 4th 103 111 100 107 1 106 108 106 111 2 112 3 4th

The table shows that the combined feedstuffs gave valuable results and that "Substance P" is very valuable in promoting the growth of chicks. The statistical analysis these values show that the growth effect of chlortetracycline by adding "substance P" is improved. "Substance P" and chlorotetracycline hydrochloride are believed to be useful in stimulating chick growth act in different ways.

Example 4

The following experiment was carried out to show that "Substance P" also when used another basic feed works in a valuable way. In this experiment a purified Casein cane sugar feed is used with the following composition:

component

Cane sugar 60.4%

Casein 20.0%

Gelatin 8.0%

Calcium gluconate 5.0%

Salt mixture No. 1 2.0%

Bone ash 2.0%

Vitamins in Cerelose * 1.0%

Cystine 0.4%

Choline chloride 0.2%

Vitamins A, D and E in corn oil .. 1.0%

Folic acid 5 mg / kg

Biotin 0.2 mg / kg

Vitamin B12 50 mcg / kg

* Cerelose is a trade name for a dried carbohydrate that is used in animal feed.

The following table shows the weight increase in percent based on the comparison test:

ppm "Substance Tabel 4th eichsve
100 such (I
100 Diet)
100 Forg
100 136 127 108 100 Ρ «.... 154

Claims (3)

Patent claims: 1. Use of bis (5-nitrofurfurylidene) acetone guanylhydrazones or of their acid addition salts, in particular of their hydrochlorides, of the formula O ₂ N CH = C - C - CH = CH NO ₂ NH where Ri is a hydrogen or halogen atom or a lower alkyl group, R _{2 is} a hydrogen atom or a lower alkyl group, X is an acidic group and η is the number 1, 2 or 3, where H = I when X is the radical of a monobasic acid , η = 1 or 2 when X is the residue of a dibasic acid, and η = 1, 2 or 3 when X is the residue of a tribasic acid, than with the usual, nutritionally balanced feed or compound feed, especially poultry feed , or with the drinking water in amounts of about 5 to 500 mg, in particular 10 to 100 mg per kilogram of feedstuff that can be administered. 2. Use of the active ingredients according to claim 1 in an amount of about 25 ppm, based on the feed. 3. Use of the active ingredients according to claim 1 or 2 with the addition of chlortetracycline, tetracycline and / or oxy tetracycline. Considered publications:
British Patent No. 816 886.