Patent GB-1107225-A (GB)
Title: Triazepine compounds
Inventor: STRYCKER STANLEY JULIAN
IPC: C07D255/02
Filed: 1966-08-03
Abstract: A plant growth stimulant comprises a compound of the formula <FORM:1107225/C1/1> wherein R represents naphthyl; pyridyl; phenyl optionally containing one or more substituents selected from halo, lower-alkyl, lower-alkoxy, lower-alkylthio, cyano, thiocyanato, carboxylic acid, carboxylic acid lower alkyl ester, hydroxy, acetoxy and acetyl; alkyl having from 1 to 10 carbon atoms and a substituent moiety selected from halo, lower alkoxy, cyano, carboxylic acid alkali metal, ammonium or amine salts, carbamoyl, sulpho, alkali metal oxysulphonyl, hydroxy and mercapto; cyclopropylmethyl; furylmethyl; (tetrahydrofuryl) methyl; thenyl; tetrahydrothenyl; 5-norbornen-2-yl-methyl; and tetrahydropyran-2-yl-methyl; wherein each lower alkyl or lower alkoxy has from 1 to 4 carbon atoms and each R1 represents hydrogen or methyl in admixture with one or more specified inert carriers.  Compositions may be prepared by conventional means in the form of dusts, suspensions, liquids or concentrates optionally containing specified surface active agents. Numerous compounds corresponding to the above general formula are described (see Division C2].ALSO:Compounds of the formula <FORM:1107225/C2/1> wherein R represents naphthyl; pyridyl; phenyl optionally containing one or more substituents selected from halo, lower-alkyl, lower-alkoxy, lower-alkylthio, cyano, thiocyanato, carboxylic acid, carboxylic acid lower alkyl ester, hydroxy, acetoxy and acetyl; alkyl having from 1 to 10 carbon atoms and a substituent moiety selected from halo, lower-alkoxy, cyano, carboxylic acid, carboxylic acid lower alkyl ester, carboxylic acid alkali metal, ammonium or amine salts, carbamoyl, sulpho, alkali metal oxysulphonyl, hydroxy and mercapto; cyclopropylmethyl; furylmethyl; (tetrahydrofuryl)-methyl; thenyl; tetrahydrothenyl; 5-norbornen-2-yl-methyl; and tetrahydropyran-2-yl-methyl; wherein each lower alkyl or lower alkoxy has from 1 to 4 carbon atoms and each R1 represents hydrogen or methyl are prepared by reacting a N,N1-dinitrodiamine of the formula <FORM:1107225/C2/2> with formaldehyde and an amine of the formula R.NH2. Preferably the diamine is first reacted with formaldehyde from a conventional source optionally in specified inert liquid media and the amine reactant is subsequently added at a temperature in the range of - 15 DEG  to 100 DEG  C.  3 - p - Tolyl,- 3 - (2 - carboxyethyl) -, 3 - (1 - naphthyl)- and 3-furfuryl-substituted 1,5-dinitro - hexahydro - 1H - 1,3,5 - triazepine are prepared.  3 - (p - Chlorophenyl) -, 3 - (2 - hydroxyethyl) -, 3 - phenyl -, 3 - (2 - hydroxypropyl) -, 3 - (3 - carboxypropyl) -, 3 - (p - methoxyphenyl) -, 3 - (p - bromophenyl) -, 3 - (ethoxycarbonylmethyl) -, 3 - (2 - naphthyl) -, 3 - (10 - carboxydecyl) -, 3 - (2 - methoxyethyl)-, 3 - (m - chlorophenyl) -, 3 - (2 - methoxy - 1 - methylethyl) -, 3 - (o - chlorophenyl) -, 3 - (2,4 - dichlorophenyl) -, 3 - (3 - methoxypropyl) -, 3 - (p - ethoxyphenyl) -, 3 - (2 - pyridyl) -, 3 - (p - isopropylphenyl), 3 - (3 - isoproxypropyl) -, 3 - (p - hydroxyphenyl) -, 3 - (2,4 - xylyl) -, 3 - (tetrahydropyran - 2 - ylmethyl) -, 3 - (p - thiocyanatophenyl) -, 3 - (5 - norbornen - 2 - ylmethyl) -, 3 - [p - (methylthio)phenyl] -, 3 - (tetrahydrofurfuryl) -, 3 - (cyclopropylmethyl)- and the sodium salts of 3-(carboxymethyl)- and 3 - (3 - sulphopropyl) - substituted 1,5 - dinitro - hexahydro - 1H - 1,3,5 - triazepine are described. Numerous other 3-substituted 1,5-dinitro - hexahydro - 1H - 1,3,5-triazepines, some bearing 6-methyl-and 6,7-dimethyl substituents are also mentioned.