Patent GB-1397888-A (GB)
Title: Tetrahydro-1,3,5-triazine-2,6-diones processes for their production and their use as herbicides
IPC: C07D251/46
Filed: 1973-11-05
Abstract: 1397888 Tetrahydro-1,3,5-triazine-2,6-diones; their preparation and use BAYER AG 5 Nov 1973 [6 Nov 1972 14 Nov 1972 28 July 1973] 51231/73 Heading C2C Compounds of the formula wherein R<SP>1</SP> is a saturated or unsaturated, aliphatic or cyclo-aliphatic hydrocarbon radical, an araliphatic hydrocarbon radical or an aryl radical, each of which may carry one or more substituents selected from halogen, nitro, alkyl, alkoxy, alkylmercapto, aryl, aryloxy, halogenomethyl or arylmercapto, R<SP>2</SP> is hydrogen, alkyl, cycloalkyl, aralkyl, aryl which optionally may be substituted by chlorine, hydroxy, alkoxy, acyloxy or an -NR<SP>4</SP>R<SP>5</SP> radical, wherein R<SP>4</SP> and R<SP>5</SP>, which may be identical or different, are each hydrogen, alkyl or acyl (both of which are optionally substituted by nitrile and/or hydroxy and/or halogen), or R<SP>4</SP> and R<SP>5</SP> conjointly form alkylidene (which can carry one or more substituents selected from aryl, halogenoaryl, alkoxyaryl, nitroaryl and heterocyclic radicals), or cycloalkylidene, and R<SP>3</SP> is hydrogen, alkyl, halogenoalkyl, halogen, aryloxy or an -NR<SP>6</SP>R<SP>7</SP> radical, wherein R<SP>6</SP> and R<SP>7</SP> ,which may be identical or different, are each hydrogen, alkyl, cycloalkyl, aralkyl, aryl, hydroxyl, amino or alkoxy, or R<SP>6</SP> and R<SP>7</SP> conjointly with the nitrogen atom form a heterocyclic radical, or R<SP>3</SP> is alkoxy or alkylmercapto, provided that R<SP>2</SP> is not hydrogen, may be obtained (a) by reacting a bis- (chlorocarbonyl)-amine of the formula with a compound of the formula or a salt thereof with an organic or inorganic acid, in the presence of an acid binding agent, it being possible, when R<SP>2</SP> is hydroxyl or amino, to protect said group by acylation or hydrazone formation and to liberate it again after the reaction, (b) by reacting a compound of the formula wherein R is an optionally substituted alkyl radical, with a compound of the formula R<SP>6</SP>R<SP>7</SP>NH, (c) by reacting a compound of the formula R<SP>1</SP>-NH-CO-NHR<SP>2</SP> with chlorocarbonylisocyanide dichloride of the formula Cl-CO-N=CCl 2 , optionally in the presence of an acid binding agent, to give a compound of the formula  and optionally reacting the latter with a compound of the formula R<SP>3</SP>H, in the presence of an acid-binding agent, or with a compound of the formula R<SP>3</SP>M, wherein M is an alkali metal atom or a magnesium halide moiety, or (d) by reacting a compound of the formula with an inorganic acid halide to give a compound of Formula III above, and optionally reacting the latter with a compound of the formula R<SP>3</SP>H, in the presence of an acid-binding agent, or with a compound of the formula R<SP>3</SP>M. Reactions (a)-(d) may be carried out at normal or elevated pressures in the presence of a solvent and reaction (b) may be effected in the presence of an inorganic or organic acid catalyst. Reactions (a) and (b) may be conducted at temperatures of 0-50 C., reaction (c) between -20 and 40 C., and reaction (d) between 20 and 120 C. The compounds of Formula II above which may be used as starting materials may be prepared according to process variant (a). The products possess herbicidal properties and they may be formulated and applied in a conventional manner.