Hexahydrotriazine compounds and insecticides

Abstract

Hexahydrotriazine compounds of the formula: are prepared by reacting a compound of the formula: with a di(monohalomethyl)amine compound or a primary amine compound in combination with formalin or paraformaldehyde, or by reacting a hexahydrotriazine derivative with a compound of the formula: R 2 CH 2 —Y—.

We claim:  
     
         1 . A hexahydrotriazine compound represented by the following general formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R stands for lower alkyl or lower alkenyl; R 1  stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by  
       
         
           
           
               
               
           
         
       
       and R 2  stands for a group indicated by  
       
         
           
           
               
               
           
         
       
     
     
         2 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         3 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl)-5-ethyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         4 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl)-5-isopropyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         5 . The hexahydrotriazine compound according to    claim 1    which is 1-( 2-chloro-5-pyridylmethyl )-5-allyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         6 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl )-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         7 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-thiazolylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         8 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl)-3-ethyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         9 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl)-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         10 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-thiazolylmethyl)-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         11 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl)-3-allyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         12 . The hexahydrotriazine compound according to    claim 1    which is 1-(2-chloro-5-pyridylmethyl)-3-propargyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         13 . The hexahydrotriazine compound according to    claim 1    which is 1,3-bis(2-chloro-5-pyridylmethyl)-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         14 . A process for preparing a hexahydrotriazine compound represented by the following general formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R stands for lower alkyl or lower alkenyl; R 1  stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by  
       
         
           
           
               
               
           
         
       
       and R 2  Stands for a group indicated by  
       
         
           
           
               
               
           
         
       
       or  
       
         
           
           
               
               
           
         
       
       comprising the step of reacting a compound represented by the general formula (II):  
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  have the same meanings defined above, with a compound represented by the general formula (III)  
       R—N(CH 2 X) 2   (III)  
       wherein R has the same meaning defined above and X stands for halogen.  
     
     
         15 . A process for preparing a hexahydrotriazine compound represented by the following general formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R stands for lower alkyl or lower alkenyl; R 1  stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by  
       
         
           
           
               
               
           
         
       
       and R 2  stands for a group indicated by  
       
         
           
           
               
               
           
         
       
       or  
       
         
           
           
               
               
           
         
       
       comprising the step of reacting a compound represented by the general formula (II):  
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  have the same meanings defined above, with a primary amine represented by the general formula (IV):  
       R—NH 2    
       wherein R has the same meaning defined above, and formalin or paraformaldehyde.  
     
     
         16 . A process for preparing a hexahydrotriazine compound represented by the following general formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R stands for lower alkyl or lower alkenyl; R 1  stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by  
       
         
           
           
               
               
           
         
       
       and R 2  stands for a group indicated by  
       
         
           
           
               
               
           
         
       
       or  
       
         
           
           
               
               
           
         
       
       comprising the step of reacting a compound represented by the general formula (V):  
       
         
           
           
               
               
           
         
       
       wherein R and R 1  have the same meanings defined above, with a compound represented by the general formula (VI):  
       R 2 CH 2 —Y  (VI)  
       wherein R 2  has the same meaning defined above and Y stands for halogen or a group indicated by —OSO 2 CH 3  or  
       
         
           
           
               
               
           
         
       
     
     
         17 . An insecticide containing a suitable carrier, and, as an active ingredient, a hexahydrotriazine compound represented by the following general formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R stands for lower alkyl or lower alkenyl; R 1  stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by  
       
         
           
           
               
               
           
         
       
       and R 2  stands for a group indicated by  
       
         
           
           
               
               
           
         
       
     
     
         18 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         19 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-ethyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         20 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-isopropyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         21 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-allyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         22 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         23 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-thiazolylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         24 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3-ethyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         25 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl )-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         26 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-thiazolylmethyl)-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         27 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3-allyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         28 . The insecticide according to    claim 17    wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3-propargyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.  
     
     
         29 . The insecticide according to    claim 17    wherein the compound is 1,3-bis(2-chloro-5-pyridylmethyl)-2-nitroiminohexahydro-1,3,5-triazine.