Hexahydro-1,2,4-triazine-3,5-dione derivatives and their use as feed additives

Claim 2

A hexahydro-1,2,4-triazine-3,5-dione of the general formula I: in which R 3 represents a hydrogen atom; an alkyl, tetrahydrofuryl or alkylsulphonyl radical; a radical in which R 4 represents an alkyl radical which is optionally substituted by a halogen atom, or by an alkoxy carbonyl or alkoxy radical; a phenyl radical substituted by one or more halogen atoms, nitro groups or lower alkyl groups; a benzyl radical substituted by one or more halogen atoms; a phenylthiomethylene or phenylaminomethylene radical substitued by one or more halogen atoms; a thienyl radical optionally substituted by one or more halogen atoms; or a -C0-hexahydro-1,2,4-triazine-3,5--dione; R 5 and R 6 are the same or different and each represents a hydrogen atom or an alkyl group, or R 6 also represents an alkali metal or alkaline earth metal atom; and A represents a group of the general formula: in which X represents one or more halogen atoms; or a group of the general formula: in which R 1 and R 2 are the same or different and each represents a hydrogen or halogen atom or a trifluoromethyl, alkyl, cyano or alkoxy radical; with the proviso that one of the substituents R 1 , R 2 , R 3 , R 5 and R 6 must be other than hydrogen.

Claim 3

A compound according to claim 1, wherein any alkyl and alkoxy groups are lower alkyl and lower alkoxy groups, straight or branched, having from 1 to 5 carbon atoms.

Claim 4

A compound according to claim 1 or claim 2, wherein any halogen atoms are chlorine or fluorine atoms.

Claim 5

A compound according to any of claims 1 to 3, wherein any alkali metal atoms are sodium or potassium.

Claim 6

A compound according to any of the preceding claims, wherein R 3 is selected from dichloroacetyl, ethoxycarbonyl and methanesulphonyl and R 1 and R 2 each represent hydrogen or one or more chlorine atoms. 6. A compound according to claim 1 which is: 2-(2'-chlorobenzyl)-hexahydro-1,2,4-triazine--3,5-dione, 2-(3'-chlorobenzyl)-hexahydro-1,2,4-triazine--3,5-dione, 2-(4'-chlorobenzyl)-hexahydro-1,2,4-triazine--3,5-dione, 2-(2',4'-dichlorobenzyl)-hexahydro-1,2,4--triazine-3,5-dione, 2-(3',4'-dichlorobenzyl)-hexahydro-1,2,4- -triazine-3,5-dione, 1-(2'-methyl-3',5'-dinitrobenzoyl)-2-(4'-chlorobenzyl)-hexahydro-1,2,4-triazine-3,5-dione, 1-chloroacetyl-2-(4'-chlorobenzyl)-hexahydro--1,2,4-triazine-3,5-dione, 2-(4'-chlorobenzyl)-4-sodium-hexmydro-1,2,4--triazine-3,5-dione, or 2-(3',4'-dichlorobenzyl)-4-sodium-hexahydro--1,2,4-triazine.

Claim 7

A compound of formula I as defined in claim 1, substantially as hereinbefore described specifically with reference to any one of Examples 1 to 20 or 24.

Claim 8

A feed pre-mix comprising one or more compounds of general formula I according to any of the preceding claims and a diluent or carrier.

Claim 9

A feed composition comprising one or more compounds of general formula I according to any of claims 1 to 7 and one or more feed ingredients or feed supplements.

Claim 10

A drinking water composition comprising water containing one or more compounds of general formula I according to any one of claims 1 to 7.

Claim 11

A composition according to claim 9 or claim 10 comprising from 50 to 300 ppm of said one or more compounds, preferably from 70 to 200 ppm of said one or more compounds.

Claim 12

A process for the preparation of a hexahydro--1,2,4-triazine-3,5-dione of the general formula I: in which R 3 represents a hydrogen atom; an alkyl, tetrahydrofuryl or alkylsulphonyl radical; a radical in which R 4 represents an alkyl radical which is optionally substituted by a halogen atom, or by an alkoxy carbonyl or alkoxy radical; a phenyl radical substituted by one or more halogen atoms, nitro groups or lower alkyl groups; a benzyl radical substituted by one or more halogen atoms; a phenylthiomethylene or phenylaminomethylene radical substituted by one or more halogen atoms; a thienyl radical optionally substituted by one or more halogen atoms; or a -CO-hexahydro-1,2,4-triazine-3,5-- d i o ne; R 5 and R 6 are the same or different and each represents a hydrogen atom or an alkyl group, or R 6 also represents an alkali metal or alkaline earth metal atom; and A represents a group of the general formula: in which X represents one or more halogen atoms; or a group of the general formula: in which R 1 and R 2 are the same or different and each represents a hydrogen or halogen atom or a trifluoromethyl, alkyl. cyano or alkoxy radical; with the proviso that one of the substituents R 1 , R 2 , R 3 , R 5 and R 6 must be other than hydrogen, which process comprises thehydrogen- ation of a compound of the general formula IV: in which A, R 5 and R 6 are as defined above for formula I, and in the case where a compound of general formula I is required in which R 3 is other than hydrogen, the corresponding compound of general formula I in which R 3 is hydrogen is first prepared and then converted into the desired compound by a method known per se.

Claim 13

A process for the preparation of a hexahydro--1,2,4-triazine-3,5-dione of the general formula I: in which R 3 represents a hydrogen atom; an alkyl, tetrahydrofuryl or alkylsulphonyl radical; a radical in which R 4 represents an alkyl radical which is optionally substituted by a halogen atom, or by an alkoxy carbonyl or alkoxy radical; a phenyl radical substituted by one or more halogen atoms, nitro groups or lower alkyl groups; a benzyl radical substituted by one or more halogen atoms; a phenylthiomethylene or phenylaminomethylene radical substituted by one or more halogen atoms; a thienyl radical optionally substituted by one or more halogen atoms; or a -CO-hexahydro-1,2,4-triazine-3,5-- d i o ne; R 5 and R 6 are the same or different and each represents a hydrogen atom or an alkyl group, or R 6 also represents an alkali metal or alkaline earth metal atom; and A represents a group of the general formula: in which X represents one or more halogen atoms; or a group of the general formula: in which R 1 and R 2 are the same or different and each represents a hydrogen or halogen atom or a trifluoromethyl, alkyl. cyano or alkoxy radical; with the proviso that one of the substituents R 1 , R 2 , R 3 , R 5 and R 6 must be other than hydrogen, which process comprises thehydrogen- ation of a compound of the general formula IV: in which A, R 5 and R 6 are as defined above for formula I, and in the case where a compound of general formula I is required in which R 3 is other than hydrogen, the corresponding compound of general formula I in which R 3 is hydrogen is first prepared and then converted into the desired compound by a method known per se.

Claim 14

A process according to claim 1, wherein the hydrogenation is performed with zinc and acetic acid in an inert solvent.

Claim 15

A process according to claim 2, wherein either said inert solvent is selected from benzene, pyridine, acetone, dimethoxyethane and tetrahydrofuran or an excess of acetic acid serves as inert solvent.

Claim 16

A process according to any of the preceding claims, wherein the reaction is performed at a temperature in the range of from 50°C to the boiling point of the solvent.

Claim 17

A process according to any of the preceding claims, in which: (a) R 3 represents an alkyl group and the compound of general formula I obtained after hydrogenation in which R 3 is hydrogen is reacted with a suitable dialkyl sulphate under neutral or acidic conditions in an inert solvent, (b) R 3 represents an alkyl sulphonyl radical and the compound of general formula I obtained after hydrogenation in which R 3 is hydrogen is reacted with a suitable alkane sulphonyl halide in an inert basic solvent at ambient temperature, or (c) R 3 represents a -COR 4 radical and the compound of general formula I obtained after hydrogenation in which R 3 is hydrogen is reacted with a suitable acyl anhydride or halide, preferably a chloride.

Claim 18

A process according to claim 5, wherein said reaction (c) is performed at reflux temperature in an inert solvent.

Claim 19

A process according to any of the preceding claims in which: (i) in the thus-produced compound of formula I R 4 represents -CH 2 Cl and the compound is further reacted with HSC 6 H 5 or H2NC6H5, to obtain a compound of general formula I in which R 3 represents phenylthiomethylene or phenylaminomethylene, (ii) in the thus-produced compound of formula I R 6 represents hydrogen and the compound is further reacted with a suitable dialkyl sulphate under basic conditions to obtain a compound of general formula I in which R 6 represents an alkyl radical, or (iii) in the thus-produced compound of formula I R 6 represents hydrogen and the compound is further reacted with a suitable base to obtain a compound of general formula I in which R 6 represents an alkali metal or alkaline earth metal atom.

Claim 20

A process according to any of claims 1 to 4 when used to prepare: 2-(2'-chlorobenzyl)-hexahydro-1,2,4-triazine--3,5-dione, 2-(3'-chlorobenzyl)-hexahydro-1,2,4-triazine--3,5-dione, 2-(4'-chlorobenzyl)-hexahydro-1,2,4-triazine--3,5-dione, 2-(2',4'-dichlorobenzyl)-hexahydro-1,2,4--triazine-3,5-dione, 2-(3',4'-dichlorobenzyl)-hexahydro-1,2,4--triazine-3,5-dione, 1-(2'-methyl-3',5'-dinitrobenzoyl)-2-(4'--chlorobenzyl)-hexahydro-1,2,4-triazine-3,5--dione, 1-chloroacetyl-2-(4'-chlorobenzyl)-hexahydro--1,2,4-triazine-3,5-dione, 2-(4'-chlorobenzyl)-4-sodium-hexahydro-1,2,4--triazine-3,5-dione, or 2-(3',4'-dichlorobenzyl)-4-sodium-hexahydro--1,2,4-triazine.

Claim 21

A process according to claim 1 substantially as hereinbefore described specifically, in particular with reference to any one of Examples 1 to 20 or 24.

Claim 22

A process according to any of the preceding claims, wherein the compound is subsequently mixed with a diluent or carrier and/or one or moe feed ingredients or feed supplements and/or water.