WO1989003181A1

WO1989003181A1 - Composition containing phenylpyridazinone derivatives for promoting growth and reducing fat in animals

Info

Publication number: WO1989003181A1
Application number: PCT/EP1988/000905
Authority: WO
Inventors: Klaus Euler; Peter Lechtken; Walter Kohler; Peter Paul Hoppe; Franz-Josef Schoener; Karl-Heinz Geiss; Marco Thyes
Original assignee: Basf Aktiengesellschaft
Priority date: 1987-10-17
Filing date: 1988-10-10
Publication date: 1989-04-20
Also published as: EP0401219A1; DE3735207A1

Abstract

Compositions for promoting growth, reducing fat, and improving the assimilation of fodder and protein content in animals, contain at least one phenylpyridazinone derivative or one of its biocompatible salts.

Description

Agents based on phenylpyridazinone derivatives for promoting growth and reducing fat in animals

description

The invention relates to agents based on phenylpyridazinone derivatives and their use for promoting growth, increasing feed utilization and the amount of protein and for reducing fat in animals, in particular farm and domestic animals.

The use of feed additives to achieve higher weight additions, improved feed utilization and reduced fat intake is already widely practiced in animal nutrition, especially when fattening pigs, cattle and poultry.

We have now found agents containing phenylpyridazinone derivatives of the general formula I

in which A and B either each represent a hydrogen atom or together form a bond,

D is oxygen or sulfur, the group = NCN or the group = NE, where E is a phenyl, benzyl, pyridyl, C ₁ -C ₄ -alkyl group or together with R ¹ the group - (CH ₂ ) _K NH- where K represents the number 2 or 3,

R ¹ if D is an oxygen atom:

a) a hydrogen atom or

b) a C ₁ -C ₆ alkyl group which is substituted by 1 to 3 fluorine, chlorine or bromine atoms, a hydroxy, a C ₁ -C ₃ alkoxy, a C ₂ -C ₄ alkanoyloxy, a C ₁ -C ₃ alkylsulfonyloxy, an aminocarbonyloxy, a mono- or di (C ₁ -C ₃ alkyl) aminocarbonyloxy, a mercapto, a C ₁ -C ₃ alkylmercapto, a phenylmercapto, a pyridylmercapto -, Pyridazinylmercapto, pyrimidinylmercapto, pyrazinylmercapto or a triazinyl mercapto group, a cyano, a carboxy, a (C ₁ -C ₄ alkoxy) carbonyl group, a phenyl group, which is substituted by 1 to 2 C ₁ -C ₃ alkyl radicals , 1 to 2 C ₁ -C ₃ alkoxy radicals and / or 1 to 2 fluorine, chlorine or bromine atoms may be substituted, or an imidazolyl group which may be substituted by 1 to 3 C ₁ -C ₃ alkyl groups, or a group of the formula Ia,

in which the dashed line can mean an additional bond, R ^{6 is} a hydrogen atom, a C ₁ -C ₄ alkyl group which is optionally substituted by a phenyl radical, a C ₃ -C ₅ cycloalkyl group, a phenyl group which is optionally substituted by 1 or 2 C ₁ -C ₄ alkyl groups, 1 or 2 C ₁ -C ₄ alkoxy groups or 1 or 2 halogen atoms and / or can be substituted by a nitrile, nitro or trifluoromethyl group, or

is a group of the formula R ⁸ R ⁹ N-, in which R ^{8 is} a hydrogen atom or a phenyl group which is 1 to 2 times halogen atoms, C ₁ -C ₄ -alkyl radicals, C ₁ -C ₄ -alkoxy groups and / or a nitrile and / or nitro group can be substituted, R ^{9 represents} a C ₁ -C ₄ alkanoyl or benzoyl group or R ⁸ and R ⁹ together with the nitrogen atom form a benzimidazol-2-one-1-yl group, R ^{7 can have the} same meanings as R ⁶ ,

and m represents 0, 1 or 2 or

a group of the formula Ib,

wherein R ^{10 is} a C ₁ -C ₃ hydrocarbon radical which can be substituted by a naphthyl radical or a phenyl radical, the phenyl radical optionally having 1 to 2 halogen atoms, 1 to 2 C ₁ -C ₄ alkyl radicals, 1 to 2 C ₁ -C ₄ -alkoxy radicals or a trifluoromethyl, nitro, hydroxy, C ₁ -C ₄ -alkanoyl, (C ₁ -C ₅ -alkoxy) carbonyl and / or cyano group, a naphthyl radical, a phenyl radical which may contain 1- can be substituted up to 3 times by halogen atoms, C ₁ -C ₄ alkyl radicals, C ₁ -C ₄ alkoxy groups and / or a trifluoromethyl or a C ₁ -C ₄ alkanoyl group, or a 6-membered heteroaryl radical with 1 to 2 denotes nitrogen atoms and p represents the number 2 or 3, or a group of formula Ic,

wherein R ^{11 is} a hydrogen atom, a C ₁ -C ₈ alkyl radical, optionally by a phenyl radical, the 1 to 2 C ₁ -C ₄ alkyl groups, 1 to 2 C ₁ -C ₄ alkoxy groups and / or 1 or 2 halogen atoms may contain, is substituted, a C ₃ -C ₁₂ cycloalkyl group which can be substituted by 1 to 3 methyl groups, a phenyl or benzyl radical, or a C ₇ -C ₁₀ bi- or tricyclic alkyl radical which is substituted by 1 to 3 methyl radicals may be substituted, or a benzo-fused C ₅ -C ₇ cycloalkyl group and R ^{12 is} a hydrogen atom or a

C ₁ -C ₈ alkyl radical, or

a group of formula Id,

wherein n denotes the number 1, 2 or 3 and the aromatic ring can be substituted by 1 to 2 halogen atoms, 1 to 2 C ₁ -C ₄ alkyl radicals or 1 to 2 C ₁ -C ₄ alkoxy radicals, or

a group of formula Ie,

in which G represents an oxygen or sulfur atom and the heterocyclic ring can be substituted by 1 to 2 C ₁ -C ₄ alkyl groups,

represents, or

c) denotes a C ₂ -C ₆ alkenyl group which can be substituted by 1 chlorine atom or a phenyl group, or

d) represents a C ₃ -C ₆ alkynyl group or

e) represents a C ₃ -C ₆ cycloalkyl group which can be substituted by 1 to 2 C ₁ -C ₃ alkyl groups and / or 1 to 2 fluorine, chlorine or bromine atoms and / or by 1 phenyl group, - or f) represents a phenyl group which is represented by 1 to 2 C ₁ -C ₃ alkyl groups, 1 to 2 C ₁ -C ₃ alkoxy groups, 1 to 2 fluorine, chlorine or bromine atoms, an amino group, a mono- or di- C ₁ -C ₃ alkylamino group. a C ₂ -C ₄ alkanoylamino group, a carboxy group or a C ₁ -C ₄ alkoxycarbonyl group may be substituted, or

g) represents a pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl group which is represented by 1 to 3 C ₁ -C ₃ -alkyl groups and / or a C ₁ -C ₃ -alkoxy group, a hydroxyl group, an amino group, a Mono or di-C ₁ -C ₃ alkylamine group may be substituted, or

h) represents a 5-membered aromatic heterocyclic group which contains 1 oxygen, 1 sulfur and / or 1, 2 or 3 nitrogen atoms as heteroatoms and is optionally substituted by 1 to 3 C ₁ -C ₃ -alkyl groups, or

i) represents a C ₁ -C ₆ alkoxy group which has a C ₃ -C ₆ cycloalkyl group, one or two chlorine or bromine atoms, a C ₁ -C ₃ alkoxy group or a phenyl group - which has 1 to 2 C ₁ -C ₃ alkyl, 1 to 2 C ₁ -C ₃ alkoxy, 1 to 2 fluorine, chlorine or bromine atoms, a trifluoromethyl radical or a nitro group may be substituted, or

3) represents a C ₃ -C ₆ alkenyloxy group which may be substituted by a phenyl group, or

k) represents a C ₃ -C ₆ alkynyloxy group which may be substituted by a phenyl radical, or

1) represents a C ₃ -C ₆ cycloalkyloxy group which can be substituted by 1 to 2 C ₁ -C ₃ alkyl groups and / or 1 to 2 chlorine or bromine atoms, or

m) represents a phenoxy group which can be substituted by 1 to 2 C ₁ -C ₃ -alkyl radicals, 1 to 2 C ₁ -C ₃ -alkoxy groups, 1 to 2 fluorine or chlorine atoms or a nitro group, or

n ^{) represents} a C ₁ -C ₃ alkyl mercapto group, or

0) represents the group R ¹³ R ¹ ^ N, where R ^{13 represents} a hydrogen atom, a C ₁ -C ₃ alkyl, a C ₃ -C ₄ alkenyl or a C ₃ -C ₄ alkynyl group or a phenyl group and R ^{14 represents} a hydrogen atom or a C ₁ -C ₃ alkyl group, or R ¹ , if D represents a sulfur atom, denotes a C ₁ -C ₄ alkylamino group or a di (C ₁ -C ₄ alkyl) amino group, or

R ¹ , if D represents the group -N-CN, for a hydrogen atom, a C ₁ -C ₄ alkyl group, a phenyl group, a C ₁ -C ₄ alkylamino or a di (C ₁ -C ₄ alkyl) amino group stands, or

R ¹ , if D represents the group = NE, a hydrogen atom, a C ₁ -C ₄ alkyl group, a phenyl group, a pyridyl group, a C ₁ -C ₄ alkylamino or a di (C ₁ -C ₄ alkyl) ) amino group means

R ^{2 represents} a hydrogen atom or a C _1-3 alkyl group,

or R ¹ and R ² together form a C ₂ -C ₄ alkylidene group which can be substituted by 1 to 2 C _1-3 alkyl groups and / or a phenyl group,

R ^{3 represents} a hydrogen atom, chlorine atom, bromine atom or a nitrile group or

R ¹ and R ³ together form a C ₁ -C ₃ alkylidene group which can be substituted by 1 to 2 C ₁ -C ₃ alkyl groups,

R ^{4 represents} a hydrogen atom, a methyl or a hydroxymethyl group, and

R ^{5 represents} a hydrogen atom or, if A and B represent hydrogen atoms, R ⁴ and R ⁵ together represent a C _{1 -2} alkylidene group;

and / or a phenylpyridazinone derivative of the general formula II,

in which A, B, R ⁴ and R ^{5 have} the meanings given for formula I,

R ^{15 is} a hydrogen atom, a C _1-4 alkyl radical, a phenyl, a hydroxy, a C _1-4 alkoxy or a phenoxy group, the group R ¹⁸ -NH-CH ₂ -CH (OH) -CH ₂ O-, in which R ¹⁸ isopropyl or tert. -Butyl group means a nitro, trifluoromethyl, carboxy, C ₁ -C ₄ alkoxycarbonyl, aminocarbonyl or cyano group, a fluorine, chlorine or bromine atom, an amino, C _1-4 alkylamino or di (C ₁ -C ₄ alkyl) amino group, a pyrrolidine, piperidine or morpholine residue, or the group -NH-CH2-J, where J denotes a pyridyl, furyl, thienyl or phenyl residue, the phenyl residue being through 1 to 3 radicals from the group halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, di (C ₁ -C ₄ alkyl) amino, (C ₁ -C ₄ alkoxy) carbonyl or C ₁ -C ₄ alkyl may be substituted, or a group -NHL, in which L is a 5- or 6-membered heterocyclic group, the 1 N, 0 or S atom and optionally 1 or 2 further N atoms owns

means

wherein the heterocyclic group by a radical from the group cyano, hydroxy. C ₁ -C ₄ alkoxy, amino, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, (C ₁ -C ₄ alkoxy) carbonyl, aminocarbonyl or C ₁ -C ₄ - Alkanoyl or by 1 to ³ C ₁ -C ₄ alkyl groups, one of these C ₁ -C ₄ alkyl groups by a

Hydroxy group or the radical R ¹⁹ R ²⁰ N can be substituted, where R ¹⁹ and R ²⁰ independently of one another are hydrogen atoms, C ₁ -C ₄ -alkyl radicals, benzyl or phenethyl groups or the group R ¹⁹ R ²⁰ N for a pyrrolidine, piperidine - or morpholine residue, can be substituted,

R ¹⁶ and R ¹⁷ independently of one another represent a hydrogen atom, a C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy group, a nitrile group, a fluorine, chlorine or bromine atom or

R ¹⁶ and ^R17 together represent a methylenedioxy or ethylidendioxy group,

and / or a phenylpyridazinone derivative of the general formula III,

in which R ⁴ , R ⁵ , A and B have the meaning given in formula I,

X and Y independently of one another represent an N atom or a carbon atom which is substituted by a hydrogen atom or one of the radicals R ²¹ , R ²² or R ²³ ,

R ^{21 is} a hydrogen atom, a C ₁ -C ₄ -alkyl group, a C ₁ -C ₄ -hydroxyalkyl group, a C ₁ -C ₄ -alkanoyl-, a hydroxycarbonyl, a (C ₁ -C ₄ -alkoxy) carbonyl -, an aminocarbonyl, a cyano group or a group of the formula purple

means where R ^{24 is} a C ₁ -C ₆ alkyl, a phenyl (C ₁ -C ₃ alkyl), a C ₁ -C ₄ alkanoyl, a benzoyl, a pyridinecarbonyl or a C ₁ -C ₄ -Alkylsulfonylgruppe means

R ^{25 represents} a hydrogen atom or a C ₁ -C ₆ alkyl group, or

R ²⁴ and R ²⁵ together with the N atom to which they are attached represent a pyrrolidine, piperidine or piperazine residue which can be substituted by a phenyl group and / or a hydroxy group,

R ^{26 represents} a C ₁ -C ₄ alkylidene group, and

R ²² and R ²³ independently of one another denote hydrogen atoms or C ₁ -C ₄ alkyl groups,

and / or a phenylpyridazinone derivative of the general formula IV

in which R ⁴ , R ⁵ , A and B have the meanings given in formula I and the pyridazinone radical is fixed at the 5- or 6-position of the aromatic ring,

M represents oxygen, sulfur or the group NR ²⁸ , where R ^{28 represents} a hydrogen atom, a C ₁ -C ₄ alkyl group, a C ₃ -C ₆ cycloalkyl group or a phenyl (C ₁ -C ₃ alkyl) group , and

R ^{27 is} a hydrogen atom, a trifluoromethyl, C ₁ -C ₁₁ alkyl, C ₃ -C ₇ cycloalkyl, hydroxy, mercapto, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio group, a Group of the formula -NHR ²⁹ , in which R ²⁹ denotes a hydrogen atom, a C ₁ -C ₄ alkyl, phenyl (C ₁ -C ₃ alkyl), styryl or phenyl group,

wherein the phenyl group by 1 to 3 radicals from the group fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, hydroxy, mercapto, C ₁ -C ₄ -Alkylmercapto and / or 1 to 3 di (C ₁ -C ₄ alkyl) amino may be substituted, or a 5- to 6-membered heterocyclic aromatic group with 1N, 0 or S atom and optionally 1 to

2 additional N atoms, the heterocyclic group being represented by 1 to

3 radicals from the group C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, halogen, hydroxy, mercapto, amino, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkanoylamino, nitro, hydroxycarbonyl, (C ₁ -C ₄ alkoxy) carbonyl and / or 1 to 3 cyano groups may be substituted, and / or the physiologically tolerable salts of the compounds of the general formulas I, II, III and IV. These agents are useful for promoting growth, increasing the use of feed and the amount of protein and / or for reducing fat in animals, especially in farm animals and pets.

Preferred compounds for the agent according to the invention and the use according to the invention are phenylpyridazinone derivatives of the general formula I,

in the

A and B either represent hydrogen atoms or together form a bond,

D represents an oxygen atom,

R ¹ a) is a hydrogen atom or

b) a C ₁ -C ₃ alkyl group which is substituted by a chlorine atom, a hydroxy, a methoxy, an acetoxy, a methylmercapto, a pyridylmercapto, a cyano, a carboxy, a (C _1-4 - Alkoxy) carbonyl or a phenyl group or a group of the formula Ia,

in which the dashed line can mean an additional bond,

R ^{6 is} a hydrogen atom, a methyl group, a phenyl group which may optionally be substituted by 1 or 2 methyl groups, methoxy groups or chlorine atoms, or a group of the formula R ⁸ R ⁹ N - in which R ^{8 represents} a hydrogen atom or a phenyl group is R ^{9 is} a propionyl or benzoyl group or in which R ⁸ and

R ⁹ together with the nitrogen atom form a benzimidazol-2-one-1-yl group, R ^{7 represents} a hydrogen atom, a methyl, a hydroxy, an acetyl, an ethoxycarbonyl or a cyano group, and

m stands for 1, or a group of the formula Ib,

wherein R ^{10 represents} a benzyl, a naphthyl or a phenyl radical which can be substituted 1 to 3 times by chlorine atoms, methyl and / or methoxy groups, or a pyridyl radical, and

p represents the number 2, or

a group of formula Ic,

wherein R ^{11 is} a C ₁ -C ₃ alkyl radical, which may be replaced by a

Phenylrest is substituted, and R ^{12 represents} a hydrogen atom or a methyl radical, or

a group of the formula I d,

where n is the number 2, or

a group of formula Ie,

wherein G represents an oxygen atom, may be substituted, or

c) a C ₂ -C ₄ alkenyl group which can be substituted by a phenyl group, or

d) a C ₃ -C ₄ alkynyl group or

e) a C ₃ -C ₆ cycloalkyl group which may be substituted by 1 to 2 methyl groups and / or 1 to 2 chlorine atoms and / or a phenyl group, or f) a phenyl group which can be substituted by 1 to 2 methyl groups, 1 to 2 methoxy groups, 1 to 2 chlorine atoms, a carboxy group or an ethoxycarbonyl group, or

g) a pyridyl group, which can be substituted by 1 to 3 methyl groups, or

h) a thiophenyl, furanyl, imidazolyl or oxazolyl group which is optionally substituted by 1 to 3 methyl groups, or

i) a C ₁ -C ₄ alkoxy group which can be substituted by a methoxy group or by a phenyl group, or

j) a C ₃ -C ₄ alkenyloxy group which may be substituted by a phenyl group, or

k) a C ₃ -C ₄ alkynyloxy group which may be substituted by a phenyl radical, or

l) a C ₃ -C ₆ cycloalkyloxy group or

m) a phenoxy group, or

n) a methyl mercapto group or

o) the group R ^{13 is} R ¹⁴ N, where R ^{13 is} a hydrogen atom, a methyl, an allyl or a propynyl group and R ^{14 is} a hydrogen atom or a methyl group,

R ^{2 represents} a hydrogen atom

or R ¹ and R2 together form a C ₂ -C ₄ alkylidene group which can be substituted by 1 to 2 methyl groups,

R ^{3 represents} a hydrogen atom, bromine atom or nitrile group or

R ¹ and R ³ together form a C ₁ -C ₃ alkylidene group which can be substituted by 1 to 2 methyl groups,

R ^{4 represents} a hydrogen atom or, if A and B represent hydrogen atoms, a methyl group, and

R ^{5 represents} a hydrogen atom or, if A and B represent hydrogen atoms, R ⁴ and R ⁵ together represent a methylidene radical and / or a phenylpyridazinone of the general formula II,

in the

A and B represent hydrogen atoms or together form a bond,

R ^{4 represents} a hydrogen atom or, if A and B represent hydrogen atoms, a methyl group,

R ^{5 represents} a hydrogen atom or, if A and B are hydrogen atoms,

R ⁴ and R ⁵ together represent a methylidene radical,

R ^{15 is} a hydroxyl, a methoxy, a carboxy, a C ₁ -C ₄ alkoxycarbonyl or a cyano group, a chlorine atom, an amino, a C ₁ -C ₄ -

Alkylamino or a di (C ₁ -C ₄ alkyl) amino group, the group -NH-CH ₂ -J, where J represents a pyridyl, furyl, thienyl or phenyl radical, or the group -NHL, in which L represents a pyridyl or a thiazolyl radical, where the pyridyl and the thiazolyl radical can be substituted by 1 to 2 methyl groups, and

R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom, a methoxy group, a nitrile group, a chlorine atom or a bromine atom,

and / or a phenylpyridazinone of the formula III,

in the

A and B represent hydrogen atoms or together form a bond,

R ^{5 represents} a hydrogen atom or, if A and B represent hydrogen atoms, together with R ^{4 represents} a methylidene group, and the rest

an imidazol-1-yl radical which can be substituted by 1 to 3 methyl groups or a hydroxymethyl group,

a 1,2,4-triazol-l-yl radical, a pyrazol-1-yl radical or a pyrrol-1-yl radical which is represented by a hydroxymethyl group, a formyl group, an acetyl group, a group of the formula purple,

in which R ^{24 represents} a C ₁ -C ₃ alkyl, a benzyl, a C ₁ -C ₄ alkanoyl or a benzoyl group, R ^{25 represents} a hydrogen atom or a C _1-6 alkyl group or

R ²⁴ and R ₂₅ together with the N atom

represent a piperidine or piperazine residue which is substituted by a phenyl group and R ^{28 is} a methylidene residue,

and / or 1 to 2 methyl groups can be substituted

and / or a phenylpyridazinone of the formula IV,

where A, 8 and R ^{5 are} hydrogen atoms, R ^{4 is} a methyl group, the pyridazinone radical is fixed at the 5- or 6-position of the phenyl ring news,

M represents the group NR ²⁸ , wherein R ^{28 represents} a hydrogen atom, a methyl or a benzyl group, and

R ^{27 represents} a phenyl group which can be substituted by 1 to 2 methoxy groups,

and the physiologically tolerable salts of the compounds of the general formulas I, II, III and IV.

Phenylpyridazinones of the general formulas I, II, III and IV, in which A, B and R ^{5 represent} a hydrogen atom and R ^{4 represents} a methyl group, are particularly preferred. Particularly preferred radicals R ¹ in general formula I are the radicals mentioned in sections a), b), f), g), h), i) and o).

Compounds of the formula I are particularly preferred in which R ¹ and R ³ together form a C ₂ -C ₃ alkylidene radical which can be substituted by 1 to 2 methyl groups.

If R ¹ in formula I is an optionally substituted C ₁ -C ₃ alkyl group, a particularly suitable substituent is a chlorine atom, a hydroxy group, a methoxy group, a cyano group or a group of the formula Ia, Ib or Id.

Manufacturing processes for compounds of this type are known and are described, for example, in the following references:

a) M. Thyes, H.D. Lehmann, J. Gries, H. König, R. Kretschmar, J. Kunze, R. Lebkücher and D. Lenke, J. Med. Chem. 26, 800-807 (1983)

b) 3. Med. Chem. 17, 273-281 (1974)

c) J. Med. Chem. 17, 281-286 (1974)

d) J. Heterocycl. Chem. 11, 755-761 (1974)

e) EP-A-117 403 and publications and patents cited therein

f) EP-A-59 688

g) US-A-4,397,854

h) US-A-4 404 203

i) JA-A-58 008 015

j) DE-A-2 459 468

k) JA-A-54 019 987

1) EP-A-10 156

m) EP-A-199 465

n) EP-A-84 250 o) EP-A-85 985 p) JA-A-57 046 966 r) EP-A-145 019 s) AU-A-86 54 286 t) EP-A-197 664 u) BE-A-830 030

EP-A-83 91 w) DE-A-3 006 671 x) EP-A-196 005 y) DE-A-3 535 609 z) DE-A-3 505 609 aa) EP-A-75 436 ab ) DE-A-3 212 304 ac) US-A-4 353 905 ad) DE-A-3 321 012 ae) WO-A-87 02 587 af) EP-A-167 995 ag) DE-A-3 600 275 ah) DE-A-2 845 220 ai) J. Med. Chem. 29, 1832-1840 (1986) aj) JA-A-58 203 978 ak) WO-A-83 01 447 As far as the compounds of formulas I, II, III and IV are known, they show pronounced cardiovascular and vascular effects in a known manner. In particular, they improve the flow properties of the blood.

The effects are described, for example, in EP-A-117 403 and in references a) to z) and aa) to ak) mentioned in the production processes.

It has now been found, surprisingly and unpredictably, that the compounds of the general formulas I, II, III and IV have a growth-promoting and fat-reducing effect.

The active ingredients can be used in all areas of animal breeding as a means of promoting and accelerating growth, improving feed conversion, reducing the amount of fat and increasing the amount of protein in healthy and sick animals.

The effectiveness of the active ingredients is largely independent of the type and gender of the animals. The active ingredients are particularly valuable in the rearing and keeping of young and fattening animals. Examples of animals in which the active ingredients can be used to promote and accelerate growth and to improve feed conversion include the following useful and ornamental animals:

Warm-blooded animals such as cattle, pigs, horses, sheep, goats, cats, dogs, rabbits, fur animals, e.g. Mink and chinchilla, poultry e.g. Chickens, geese. Ducks, turkeys, pigeons, parrots and canaries and cold-blooded animals such as fish, e.g. Carp, trout and reptiles, e.g. Snakes.

The dose of active substance which is administered to the animals in order to achieve the desired effect can be varied largely because of the favorable properties of the active substances. It is preferably about 0.01 to 100, in particular 0.1 to 10 mg / kg of feed. The duration of administration can range from a few hours or days to several years. The appropriate amount of the active ingredient and the appropriate duration of administration depend in particular on the type, age, gender, state of health and the type of keeping and feeding the animals and are easy to determine by any person skilled in the art.

The active substances are administered to the animals according to the usual methods. The method of administration depends in particular on the type, behavior and state of health of the animals. So the administration can be administered orally once or several times a day at regular or irregular intervals or parenterally. For reasons of convenience, oral administration is preferred in most cases, particularly in the rhythm of the animals' food and / or drink intake.

The active ingredients can be used as a pure mixture or in formulated form, i.e. in a mixture with non-toxic inert carriers of any kind, e.g. with carriers and in formulations as are customary in nutritional preparations.

The active ingredients are optionally administered in a formulated form together with pharmaceutical active ingredients, mineral salts, trace elements, vitamins, protein substances, fats, colorings and / or flavorings in a suitable form.

Oral administration together with the feed and / or drinking water is recommended, the active ingredient being added to the total amount or only parts of the feed and / or drinking water as required.

The active substances are added to the feed and / or drinking water by simple mixing as a pure substance mixture, preferably in finely divided form or in formulated form in a mixture with edible non-toxic carrier substances, optionally in the form of a premix or a feed concentrate.

The feed and / or drinking water can, for example, contain the active substances in a weight concentration of approximately 0.01 to 100, in particular 0.1 to 10 ppm. The optimum level of the concentration of the active substances in the feed and / or drinking water depends in particular on the amount of feed and / or drinking water intake by the animals and can be easily determined by any person skilled in the art.

The type of feed and its composition are irrelevant. All common or special feed compositions can be used, which preferably contain the usual balance of energy and building materials including vitamins and minerals necessary for a balanced diet. The feed can be composed, for example, of vegetable substances, for example hay, beets, cereals, grain by-products, animal substances, for example meat, fats, bone meal, fish products, vitamins, for example vitamin A, D complex and B complex, proteins, amino acids, for example DL-methionine and inorganic substances such as lime and table salt. Feed concentrates contain the active ingredients in addition to edible substances, such as rye flour, corn flour, soybean meal or lime, optionally with other nutrients and builders as well as proteins, mineral salts and vitamins. They can be produced using the usual mixing methods.

Preferably in premixes and feed concentrates, the active ingredients can optionally also be covered by suitable agents covering their surface, e.g. protected from air, light and / or moisture with non-toxic waxes or gelatin.

The invention is explained further in the following examples.

example 1

Example of the composition of a chick rearing feed containing an active ingredient according to the invention:

Corn Soy Ration Barley Oat Tapioca Ration

Components%%

Corn 48.0

Oats 20.00

Barley 10.0 24.49

Tapioca 13.00 soybean meal 31.0 31.00

Soybean oil 3.0 5.00

Fish meal 2.9 3.00

Cefkaphos 1.76 1.76 carbon. Feed lime 1.2 1.20 Livestock salt 0.25 0.25

Trace element VM 0.025 0.025

Vitamin VM 0.025 0.025

Choline chloride 0.1 0.10

Methionine 0.15 0.15 Wheat semolina 1.59

100.00 100.00 Nutrient levels

Maize soy ration barley oat tapioca ration

(Lufa Kiel) (calculated)

Crude protein: 21.8% 21.6% Crude fat: 6.6%

Crude fiber: 3.3%

MJ ME: 12.4 12.3

EZG: 82.5

Ca: 1.1% 1.02% P: 0.84% 0.88%

Na: 0.11% 0.15%

Lysine: 1.22% 1.23%

Methionine: 0.66% 0.51%

Example 2

Example of the composition of a pig rearing feed containing an active ingredient according to the invention:

Composition of the feed mixtures (g / kg)

Piglet rearing fattening pigs

Corn 350 300

Barley 153.3 270 tapioca - 100

Oats - 100

Soybean meal 120 150

Fish meal - 40

Wheat 100 - skimmed milk powder 100 -

Wheat bran 80 4.65

Animal meal 40 -

Soybean oil 30 -

Cefkaphos 6.83 11 kohlens. Feed lime 8.0 14.2

Cattle salt 2.79 1.3

Trace element VM 0.8 0.6

Vitamin VM 3.0 4.0

Lysine 2.5 1.0 methionine 1.0 2.0

Choline chloride 0.8 0.25

Cr ₂ O ₃ 1.0 1.0 The specified feed mixtures are preferably matched for rearing and fattening chicks or pigs, but they can also be used in the same or a similar composition for rearing and fattening other animals, such as sheep and cattle.

Several feed and metabolism studies were carried out with the active compounds according to the invention.

Example 3

Evaluation of test compounds as growth promoters and body fat reducing substances in animal nutrition - rat tests

a) Animal characteristics and feed

Rats, male, SPF-Wistar (Fa. Thomae) 300 animals / experiment (30 × 10) Weight at the start of the experiment: 55 - 65 g Weight at the end of the experiment: 185 - 220 g

Food: Diet for rats with the following composition:

salary

95% dry matter

5% raw ash

13.8% crude protein

5.3% crude fat

Raw nutrients and vitamins

15.1% casein 10.0% sugar 3.0% cellulose 5.0% soybean oil

6.0% mineral VM 2.0% vitamin VM 0.2% methionine 58.7% corn swell 100% b) treatment of animals

After arrival of the animals, these 3 days are adapted to the test conditions and then randomized.

Randomization example

body weight

Group number mean standard deviation

1 10 55.5 2.12

2 10 55.5 2.27

3 10 55.6 2.22

4 10 55.6 2.27 5 10 55.5 2.27

6 10 55.5 2.17

7 10 55.5 2.22

8 10 55.6 2.27

9 10 55.6 2.27 10 10 55.5 2.27

11 10 55.5 2.07

12 10 55.5 2.12

13 10 55.5 2.07

14 10 55.4 2.01 15 10 55.5 2.17

16 10 55.6 2.17

17 10 55.7 2.21

18 10 55.6 2.22

19 10 55.5 2.17 20 10 55.5 2.22

21 10 55.5 2.07

22 10 55.4 2.22

23 10 55.6 2.17

24 10. 55.5 2.17 25 10 55.5 2.07

26 10 55.5 2.17

27 10 55.5 2.17

28 10 55.6 2.07

29 10 55.6 1.96 30 10 55.4 2.06

Total 300 55.5 2.06

Dele 55 55.3 5.09 The subsequent test period is 21 days. The animals are fed ad libitum and / or rationed (1st week 90 g; 2nd week 110 g; 3rd week 130 g).

The animals are kept individually and weighed at weekly intervals.

After the end of the experiment, the rats are killed with CO ₂ .

For whole-body analysis, the animals in a test group are autoclaved and then homogenized with a cutter.

c) results

The data obtained are shown in a table below.

Claims

1. Means for increasing the performance of animal nutrition in cold-blooded and warm-blooded animals, containing at least either

a phenylpyridazinone derivative of the general formula I,

in which A and B either each represent a hydrogen atom or together form a bond,

R ¹ if D is an oxygen atom:

a) a hydrogen atom or

b) a C ₁ -C ₆ alkyl group which is substituted by 1 to 3 fluorine, chlorine or

Bromine atoms, a hydroxy, a C ₁ -C ₃ alkoxy, a C2-C ₄ alkanoyloxy, a C ₁ -C ₃ alkylsulfonyloxy, an aminocarbonyloxy, a mono- or di- (C ₁ -C ₃ alkyl) aminocarbonyloxy, a mercapto, a C ₁ -C ₃ alkyl mercapto, a phenyl mercapto, a pyridyl mercapto, pyridazinyl mercapto, pyrimidinyl mercapto,

Pyrazinylmercapto or a triazinyl mercapto group, a cyano, a carboxy, a (C ₁ -C ₄ alkoxy) carbonyl group, a phenyl group through 1 to 2 C ₁ -C ₃ alkyl radicals. 1 to 2 C ₁ -C ₃ alkoxy radicals and / or 1 to 2 fluorine, chlorine or bromine atoms can be substituted, or an imidazolyl group which can be substituted by 1 to 3 C ₁ -C ₃ alkyl groups, or

a group of the formula Ia,

in which the dashed line can mean an additional bond, R ^{6 is} a hydrogen atom, a C ₁ -C ₄ alkyl group which is optionally substituted by a phenyl radical, a C ₃ -C ₆ cycloalkyl group, a phenyl group which is optionally substituted by 1 or 2 C ₁ -C ₄ alkyl groups, 1 or 2 C ₁ -C ₄ alkoxy groups or 1 or 2 halogen atoms and ^ or can be substituted by a nitrile, nitro or trifluoromethyl group, or

a group of the formula R ⁸ R ⁹ N-, in which R ^{8 is} a hydrogen atom or a phenyl group, which is 1 to 2 times

Halogen atoms, C ₁ -C ₄ alkyl radicals, C ₁ -C ₄ alkoxy groups and / or a nitrile and / or nitro group, R ⁹ can be substituted

C ₁ -C ₄ alkanoyl or benzoyl group or R ⁸ and R ⁹ together with the nitrogen atom form a benzimidazol-2-one-1-yl group, R ^{7 can have the} same meanings as R ⁶ ,

and m represents 0, 1 or 2 or

a group of the formula Ib,

wherein R ^{10 is} a C ₁ -C ₃ hydrocarbon radical which can be substituted by a naphthyl radical or a phenyl radical, the phenyl radical optionally having 1 to 2 halogen atoms, 1 to 2 C ₁ -C ₄ alkyl radicals, 1 to 2 C ₁ -C ₄ -alkoxy radicals or a trifluoromethyl, nitro, hydroxy, C ₁ -C ₄ -alkanoyl, (C ₁ -C ₅ -alkoxy) carbonyl and / or cyano group, a naphthyl radical, a phenyl radical, the 1st - Can be substituted up to 3 times by halogen atoms, C ₁ - C ₄ alkyl radicals, C ₁ -C ₄ alkoxy groups and / or a trifluoromethyl or a C ₁ -C ₄ alkanoyl group, or a 6-membered heteroaryl radical with 1 means up to 2 nitrogen atoms and p represents the number 2 or 3, or

a group of formula Ic,

wherein R ^{11 is} a hydrogen atom, a C ₁ -C ₈ alkyl radical, optionally by a phenyl radical, the 1 to 2 C ₁ -C ₄ alkyl groups, 1 to 2 C ₁ -C ₄ alkoxy groups and / or 1 or 2 halogen atoms may contain, is substituted, a C ₃ -C ₁ 2-cycloalkyl group which may be substituted by 1 to 3 methyl groups, a phenyl or benzyl radical, or a C ₇ -C ₁₀ bi- or tricyclic alkyl radical with 1 to 3 Methyl radicals may be substituted, or a benzo-fused C ₅ -C ₇ cycloalkyl group and R ^{12 represents} a hydrogen atom or a C ₁ -C ₈ alkyl radical, or

a group of formula Id.

where n is the number 1, 2 or 3 and the aromatic ring by 1 to 2 halogen atoms, 1 to 2 C ₁ -C ₄ alkyl radicals or 1 to

2 C ₁ -C ₄ alkoxy radicals can be substituted, or

a group of formula Ie,

represents, or

d) represents a C ₃ -C ₆ alkynyl group or

e) represents a C ₃ -C ₆ cycloalkyl group which can be substituted by 1 to 2 C ₁ -C ₃ alkyl groups and / or 1 to 2 fluorine, chlorine or bromine atoms and / or by 1 phenyl group, or f) represents a phenyl group which is formed by 1 to 2 C ₁ -C ₃ alkyl groups, 1 to 2 C ₁ -C ₃ alkoxy groups, 1 to 2 fluorine, chlorine or bromine atoms, an amino group, a mono- or Di-C ₁ -C ₃ alkylamino group, a C ₂ -C ₄ alkanoylamino group, a carboxy group or a C ₁ -C ₄ alkoxycarbonyl group may be substituted, or

g) represents a pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl group which is represented by 1 to 3 C ₁ -C ₃ alkyl groups and / or a C ₁ -C ₃ alkoxy group, a hydroxyl group, an amino group, a mono- or Di-C ₁ -C ₃ alkylamino group, or

i) represents a C ₁ -C ₆ alkoxy group which is a C ₃ -C ₆ cycloalkyl group, one or two chlorine or bromine atoms, a C ₁ -C ₃ alkoxy group or a phenyl group which is substituted by 1 to 2 C ₁ - C ₃ alkyl, 1 to 2 C ₁ -C ₃ alkoxy, 1 to 2 fluorine, chlorine or bromine atoms, a trifluoromethyl radical or a nitro group may be substituted, or

j) represents a C ₃ -C ₆ alkenyloxy group which may be substituted by a phenyl group, or

l) represents a C ₃ -C ₆ cycloalkyloxy group which is represented by 1 to

2 C ₁ -C ₃ alkyl groups and / or 1 to 2 chlorine or bromine atoms can be substituted, or

m) represents a phenoxy group which has 1 to 2 C ₁ -C ₃ -alkyl radicals,

1 to 2 C ₁ -C ₃ alkoxy groups, 1 to 2 fluorine or chlorine atoms or a nitro group may be substituted, or

n) represents a C ₁ -C ₃ alkyl mercapto group, or

o) the group R ¹³ R ¹⁴ N, where R ^{13 represents} a hydrogen atom, a C ₁ -C ₃ alkyl, a C ₃ -C ₄ alkenyl or a C ₃ -C ₄ alkynyl group or a phenyl group and R ^{14 represents} a hydrogen atom or a C ₁ -C ₃ alkyl group, or R ¹ , if D represents a sulfur atom, denotes a C ₁ -C ₄ alkylamino group or a di (C ₁ -C ₄ alkyl) amino group, or

R ¹ , if D represents the group = N-CN, for a hydrogen atom, a C ₁ -C ₄ alkyl group, a phenyl group, a C ₁ -C ₄ alkylamino or a di (C ₁ -C ₄ alkyl) amino group stands, or

R ¹ , if D represents the group = NE, a hydrogen atom, a C ₁ -C ₄ alkyl group, a phenyl group, a pyridyl group, a C ₁ -C ₄ alkylamino or a di (C ₁ -C ₄ -Alkyl) -amino group means

R ^{2 represents} a hydrogen atom or a C _{1 -3} alkyl group,

or R ¹ and R ² together form a C2-C ₄ alkylidene group which can be substituted by 1 to 2 C _{1 -3} alkyl groups and / or a phenyl group,

R ^{4 represents} a hydrogen atom, a methyl or a hydroxymethyl group, and

R ^{5 represents} a hydrogen atom or, if A and B represent hydrogen atoms, R ⁴ and R ⁵ together represent a C _1-2 alkylidene group;

and / or a phenylpyridazinone derivative of the general formula II,

in which A, B, R ⁴ and R ^{5 have} the meanings given for formula I,

R ^{15 is} hydrogen, C _1-4 alkyl, phenyl, one

Hydroxy-, a C _1-4 -alkoxy-, a phenoxy group, the group R ¹⁸ -NH-CH ₂ -CH (OH) -CH ₂ O-, in which R ^{18 represents} the isopropyl or tert-butyl group, a Nitro, trifluoromethyl, carboxy, C ₁ -C ₄ alkoxycarbonyl, aminocarbonyl or cyano group, a fluorine, chlorine or bromine atom, an amino, C _1-4 alkylamino or di (C ₁ - C ₄ - Alkyl) amino group, a pyrrolidine, piperidine or morpholine residue, or the group -NH-CH ₂ -J, where J denotes a pyridyl, furyl, thienyl or phenyl residue, the phenyl residue being derived from 1 to 3 residues Halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, di (C ₁ -C ₄ alkyl) amino, (C ₁ -C ₄ alkoxy) carbonyl or C ₁ -C ₄ alkyl group may be substituted ,

or a group -NHL, in which L is a 5- or 6-membered heterocyclic group which has 1 N, 0 or S atom and optionally 1 to 2 further N atoms, the heterocyclic group consisting of a radical the group cyano, hydroxy, C ₁ -C ₄ alkoxy, amino, C ₁ -C ₄ alkyllao, di- (C1-C ₄ alkyl) amino, (C ₁ -C ₄ alkoxy) carbonyl, aminocarbonyl or C ₁ -C ₄ alkanoyl or by 1 to 3 C ₁ -C ₄ alkyl groups, where one of these C ₁ -C ₄ alkyl groups can be substituted by a hydroxyl group or the radical R ¹⁹ R ²⁰ N, where R ¹⁹ and R ²⁰ independently of one another represent hydrogen atoms, C ₁ -C ₄ -alkyl radicals, benzyl or phenethyl groups or the group R ¹⁹ R ²⁰ N represents a pyrrolidine, piperidine or morpholine radical, can be substituted,

R ¹⁶ and R ¹⁷ independently represent a hydrogen atom, a

C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy group, nitrile group, a fluorine, chlorine or bromine atom or

R ¹⁶ and R ¹⁷ together represent a methylenedioxy or ethylidendioxy group,

and / or a phenylpyridazinone derivative of the general formula III,

in which R ⁴ , R ⁵ , A and B have the meaning given in formula I,

X and Y independently of one another represent an N atom or a carbon atom which is substituted by a hydrogen atom or one of the radicals R ²¹ , R ²² or R ²³ , R ^{21 is} a hydrogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ hydroxyalkyl group, a C ₁ -C ₄ alkanoyl-, a hydroxycarbonyl, a (C ₁ -C ₄ alkoxy) carbonyl-, a Aminocarbonyl, a cyano group or a group of the formula purple

means where

R ^{24 is} a C ₁ -C ₆ alkyl, a phenyl (C ₁ -C ₃ alkyl), a C ₁ -C ₄ alkanoyl, a benzoyl, a pyridinecarbonyl or a C ₁ -C ₄ Means alkylsulfonyl group,

R ^{25 represents} a hydrogen atom or a C ₁ -C ₆ alkyl group, or

R ²⁴ and R25 together with the N atom to which they are attached mean a pyrrolidine, piperidine or piperazine residue which is represented by a

Phenyl group and / or a hydroxyl group can be substituted,

R ^{28 represents} a C ₁ -C ₄ alkylidene group, and

and / or a phenylpyridazinone derivative of the general formula IV

R ^{27 is} a hydrogen atom, a trifluoromethyl, C ₁ -C ₁₁ alkyl, C ₃ -C ₇ cycloalkyl, hydroxy, mercapto, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio group, a Group of the formula -NHR ²⁹ , in which R ²⁹ denotes a hydrogen atom, a C ₁ -C ₄ alkyl, phenyl (C ₁ -C ₃ alkyl), styryl or phenyl group, wherein the phenyl group by 1 to 3 radicals from the group fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl. Hydroxy, mercapto. C ₁ -C ₄ -Alkylmercapto and / or 1 to 3 di (C ₁ -C ₄ -alkyl) amino may be substituted, or a 5- to 6-membered heterocyclic aromatic group with 1N, 0 or S atom and optionally 1 to 2 additional N atoms, the heterocyclic group being replaced by 1 to 3 radicals from the group C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, halogen, hydroxy, mercapto , Amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkanoylamino, nitro, hydroxycarbonyl, (C ₁ -C ₄ alkoxy) carbonyl and / or 1 up to 3 cyano groups can be substituted means

and / or the physiologically tolerable salts of the compounds of the general formulas I, II, III and IV.

Agent according to claim 1, comprising at least either a phenylpyridazinone derivative of the general formula I,

in which A and B either each represent a hydrogen atom or together form a bond,

D represents an oxygen atom,

R ¹ a) is a hydrogen atom or

b) a C ₁ -C ₃ alkyl group which is substituted by a chlorine atom, a hydroxy, a methoxy, an acetoxy, a methylmercapto, a pyridylmercapto, a cyano, a carboxy, a (C _{1 -4} Alkoxy) carbonyl or a phenyl group or a group of the formula Ia,

in which the dashed line can mean an additional bond, and R ^{6 is} a hydrogen atom, a methyl group, a phenyl group which may be replaced by 1 or 2 methyl, methoxy groups or chlorine atoms, or a group of the formula R ⁸ R ⁹ N, in which R ^{8 is} a hydrogen atom or a phenyl group and R ^{9 is} a propionyl or benzoyl group or R ⁸ and R ⁹ together with the nitrogen atom are a benzimidazole Form 2-one-1-yl group, R ^{7 represents} a hydrogen atom, a methyl, a hydroxy, an acetyl, an ethoxycarbonyl or a cyano group,

m stands for 1 or

a group of formula Ib

wherein R ^{10 is} a benzyl, a naphthyl or a phenyl radical which can be substituted 1 to 3 times by chlorine atoms, methyl and / or methoxy groups, or a pyridyl radical and

p represents the number 2, or

a group of formula Ic,

wherein R ^{11 is} a C ₁ -C ₃ alkyl radical, which is optionally substituted by a phenyl radical, and R ^{12 represents} a hydrogen atom or a methyl radical, or

a group of the formula I d,

where n is the number 2, or

a group of formula Ie,

wherein G represents an oxygen atom, may be substituted, or c) a C ₂ -C ₄ alkenyl group which can be substituted by a phenyl group, or

d) a C ₃ -C ₄ alkynyl group or

e) a C ₃ -C ₆ cycloalkyl group which can be substituted by 1 to 2 methyl groups and / or 1 to 2 chlorine atoms and / or a phenyl group, or

f) a phenyl group formed by 1 to 2 methyl groups, 1 to 2

Methoxy groups, 1 to 2 chlorine atoms, a carboxy group or an ethoxycarbonyl group may be substituted, or

g) a pyridyl group, which can be substituted by 1 to 3 methyl groups, or

l) a C ₃ -C ₆ cycloalkyloxy group or

m) a phenoxy group or

n) a methyl mercapto group or

o) the group R ^{13 is} R ¹⁴ N-, where R ^{13 is} a hydrogen atom, a methyl, an allyl or a propynyl group and R ^{14 is} a hydrogen atom or a methyl group,

R ^{2 represents} a hydrogen atom

or R ¹ and R ² together form a C ₂ -C ₄ alkylidene group which can be substituted by 1 to 2 methyl groups, R ^{3 represents} a hydrogen atom, bromine atom or a nitrile group or

R ^{5 represents} a hydrogen atom or, if A and B represent hydrogen atoms, R ⁴ and R ⁵ together form a methylidene radical

and / or a phenylpyridazinone of the general formula II,

in which A and B represent hydrogen atoms or together form a bond,

R ^{5 represents} a hydrogen atom or, if A and B are hydrogen atoms,

R ⁴ and R ⁵ together represent a methylidene radical,

R ^{15 is} a hydroxy, a methoxy, a carboxy, a C ₁ -C ₄ alkoxycarbonyl or a cyano group, a chlorine atom, an amino group, a

C ₁ -C ₄ alkylamino or a di (C ₁ -C ₄ alkyl) amino group, the group NH-CH ₂ -J, where 3 is a pyridyl, furyl, thionyl or phenyl radical, or the group NHL, wherein L represents a pyridyl or a thiazolyl radical, the pyridyl and the thiazolyl radical being

1 to 2 methyl groups can be substituted, means and

R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom, a methoxy group, a nitrile group, a chlorine atom or bromine atom, and / or a phenylpyridazinone of the formula III,

in which A and B represent hydrogen atoms or together form a bond,

or a 1, 2,4-triazol-1-yl radical, a pyrazol-1-yl radical or a pyrrol-1-yl radical which is represented by a hydroxymethyl group, a formyl group, an acetyl group or a group of the formula purple ,

in which R ^{24 represents} a C ₁ -C ₃ alkyl, a benzyl, a C ₁ -C ₄ alkanoyl or a benzoyl group, R ^{25 represents} a hydrogen atom or a C _1-6 alkyl group or R ²⁴ and R ²⁵ together with the N atom represent a piperidine or piperazine residue which is substituted by a phenyl group and R ^{26 is} a methylidene residue,

and / or 1 to 2 methyl groups can be substituted,

and / or a phenylpyridazinone of the formula IV,

where A, B and R ^{5 are} hydrogen atoms, R ^{4 is} a methyl group, the pyridazinone radical is fixed at the 5- or 6-position of the phenyl ring,

M represents the group NR ²⁸ , in which R ^{28 represents} a hydrogen atom, a methyl or a benzyl group, and

and / or physiologically tolerable salts of the compounds of the general formulas I, II, III and IV.

3. Composition according to claim 1, containing at least one phenylpyridazinone derivative of the general formulas I, II, II and / or IV, wherein A, B and

R ^{5 represents} hydrogen atoms and R4 represents a methyl group.

4. Composition according to one of claims 1, 2 or 3 in the form of animal feed, drinking water for animals, additives for animal feed and drinking water or premixes.

5. Use of the phenylpyridazinone derivatives of the general formulas I, II, III and IV according to one of claims 1 to 4 for increasing the performance in animal breeding, in particular for promoting growth, improving feed utilization, increasing the protein content and

Reduction in fat in animals.