Patent GB-1093376-A (GB)
Title: Substituted 1,3,5-triazine compounds and pesticidal preparations containing them
IPC: C07D251/40
Filed: 1964-11-19
Abstract: The invention comprises compounds of the formula <FORM:1093376/C2/1> where R1 is halogen, azido, an aliphatic radical of up to 18 carbon atoms, or a group -ZX (where Z is O or S and X is an aliphatic radical of up to 18 carbon atoms or a 6-membered cycloaliphatic radical), and R2 is an aliphatic radical of up to 18 carbon atoms, a group -ZX (as defined above), or a group -NA1A, where A1 is an aliphatic radical of up to 18 carbon atoms, a cycloaliphatic 3- to 12-membered radical, or an alkoxyalkyl, hydroxyalkyl, cyanoalkyl or alkylthioalkyl radical of up to 6 carbon atoms, and A2 is hydrogen or a radical as defined for A1, or A1, A2 and the nitrogen atom represent a 6-membered heterocyclic radical.  These compounds may be prepared by reacting a compound <FORM:1093376/C2/2> OR <FORM:1093376/C2/3> where X4 is halogen or a qunatenary ammonium group, with an alkali metal azide, e.g. in the presence of a solvent; or by reacting a compound <FORM:1093376/C2/4> where Y is hydrazino, with nitrous acid or a nitrous acid donor such as a nitrous acid salt in aqueous acid or an alkyl nitrite in alcoholic solution. Intermediates: (T = 1,3,5-triazine).  2,4 - Difluoro - 6 - isobutylamino - T was prepared from cyanuric fluoride and isobutyl amine.  2,4-Dibromo-6-isobutylamino-T was prepared similarly.  2 - Chloro - 4 - isopropylamino-6-methyl-T was prepared from 2,4-dichloro - 6 - methyl - T and isopropylamine, and was reacted with trimethylamine to give 6 - (2 - isopropylamino - 4 - methyl - 1,3,5 - triazinyl) - trimethyl ammonium chloride.  2-Chloro - 4 - isobutylamino - 6 - methylmercapto-T was prepared from isobutylamine and 2,4-dichloro - 6 - methylmercapto - T; other alkylmercapto compounds were obtained analogously.  6 - (2 - Sec - butyl mercapto - 4 - isopropylaminotriazinyl) - trimethyl ammonium chloride was prepared from trimethylamine and 2-sec -butylmercapto - 4 - chloro - 6 - isopropylamino-T (itself prepared as above). 2-Ethylamino-4-hydrazino - 6 -methylmercapto - T was prepared from hydrazine hydrate and 2-ethylamino - 4 - chloro - 6 - methylmercapto - T. 2 - Chloro - 4 - ethylamino - 6 - methoxy - T was obtained from ethylamine and 2,4-dichloro-6-methoxy-T; other alkoxy compounds were prepared analogously.  6 - (2 - Isopropylamino - 4 - methoxy - 1,3,5-triazinyl) trimethyl ammonium chloride was prepared from trimethylamine and 2-chloro-4-isopropylamino - 6 - methoxy - T (itself prepared as above).  2 - Cyclohexylamino - 4 - hydrazino - 6 - methoxy-T was prepared from hydrazine hydrate and 2 - chloro - 4 - cyclohexylamino - 6 - methoxy - T. 2 - Chloro - 4,6 - diazido - T was prepared from cyanuric chloride and sodium azide.  2 - Chloro - 4,6 - dimethylmercapto - T was prepared from methyl mercaptan and 2,4-dichloro - 6 - methylmercapto - T; similarly prepared were 2 - isobutylmercapto -, 2 - methoxy - and 2 - isobutoxy - 4 - chloro - 6 - methylmercapto - T. 2,4- Dichloro - 6 - (21 - methylcyclohex - 4 - enylmethoxy) - T was prepared from cyanuric chloride and 2-methyl-cyclohex-4-enyl methanol.  The compounds of the invention are pesticides (see Division A5).ALSO:Pesticidal compositions contain a compound of formula:  <FORM:1093376/A5-A6/1> where R1 is halogen, azido, an aliphatic radical of up to 18 carbon atoms, or a group -ZX (where Z is O or S, and X is an aliphatic radical of up to 18 carbon atoms or a 6-membered cycloaliphatic radical) and R2 is an aliphatic radical of up to 18 carbon atoms, a group -ZX (as defined above) or a group -NA1A2, where A1 is an aliphatic radical of up to 18 carbon atoms, a cycloaliphatic 3- to 12-membered radical, or an alkoxyalkyl, hydroxyalkyl, cyanoalkyl or alkylthioalkyl radical of up to 6 carbon atoms, and A2 is hydrogen or a radical as defined for A1, or A1, A2 and the nitrogen atom form a 6-membered heterocyclic radical (see Division C2), together with a suitable carrier; there may be present a solvent, diluent, dispersant, an adhesive and/or another pesticide, and examples of the first three are given.