Heterocyclic compounds

Abstract

Novel heterocyclic compounds of the formula wherein, R 1 represents a hydrogen atom or an alkyl group, A represents an ethylene group which may be substituted by alkyl or a trimethylene group which may be substituted by alkyl, X represents an oxygen or sulfur atom or the group in which R 2 represents a hydrogen atom of an optionally substituted alkyl, an alkenyl, an alkynyl or an acyl group, and R 3 represents a hydrogen atom or an alkyl group, and Z represents an optionally substituted 5- or 6-membered heterocyclic group which contains at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms, or an optionally substituted 3- or 4-pyridyl group. The above defined novel heterocyclic compounds of formula (I) exhibit powerful insecticidal properties.

1. A heterocyclic compound of the formula 
                   
       wherein
 R 1  represents a hydrogen atom or a methyl group,  
 A represents an ethylene group which may be substituted by methyl  
 X represents an oxygen or sulfur atom or the group 
                 
 
 in which R 2  represents a hydrogen atom, a C 1 -C 4  alkyl group which may be substituted by a substituent selected from halogens, C 1 -C 4  alkoxy groups, C 1 -C 4  alkylthio groups and cyano, a C 2 -C 4  alkenyl group, a C 2 -C 4  alkynyl group, a pyridylmethyl group which may be substituted by halogen and/or methyl, a benzyl group which may be substituted by halogen and/or methyl, a formyl group, an alkylcarbonyl group having 1 to 2 carbon atoms in the alkyl moiety which may be substituted by halogen, a phenylcarbonyl group which may be substituted by halogen and/or methyl, an alkoxy or alkylthiocarbonyl group having 1 to 4 carbon atoms in the alkyl moiety, a phenoxycarbonyl group, a C 1 -C 4  alkylsulfonyl group which may be substituted by halogen or a phenylsulfonyl group which may be substituted by methyl,  
 R 3  represents a hydrogen atom or a C 1 -C 7  alkyl group, and  
 Z represents a 3-pyridyl group or a 4-pyridyl group optionally substituted by at least one substituent selected from halogen atoms, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkylthio groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, haloalkoxy groups having 1 to 4 carbon atoms, alkysulfonyl groups having 1 to 4 carbon atoms, a cyano group and a nitro group.  
 
     
     
       2. A compound according to  claim 1 , wherein
 R 1  represents a hydrogen atom,    A represents an ethylene group,    X represents a sulfur atom or the group 
                 
   
       and
 Z represents a 3-pyridyl group or a 4-pyridyl group optionally substituted by at least one substituent selected from a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a methylthio group, a trifluoromethyl group, a trifluoromethoxy group, a methylsulfonyl group, a cyano group and a nitro group.  
 
     
     
       3. A compound according to  claim 1 , wherein such compound is 1-(2-chloro-5-pyridylmethyl)-2-cyanoiminoimidazolidine of the formula 
                   
       
        
       
     
     
       4. A compound according to  claim 1 , wherein such compound is 1-(2-fluoro-5-pyridylmethyl)-2-cyanoiminoimidazolidine of the formula 
                   
       
        
       
     
     
       5. A compound according to  claim 1 , wherein such compound is 1-(2-methyl-5-pyridylmethyl)-2-cyanoiminoimidazolidine of the formula 
                   
       
        
       
     
     
       6. A compound according to claim  1 , wherein such compound is 1-(2-chloro-5-pyridylmethyl)-2-cyanoiminothiazolidine of  10 , which has the formula 
                 
 
     
     
       7. An insecticidal composition comprising an insecticidally effective amount of a compound according to  claim 1  and a diluent. 
     
     
       8. A method of combating insects which comprises applying to such insects or to an insect habitat an insecticidally effective amount of a compound according to claim  1   10 . 
     
     
       9. The method according to  claim 8 , wherein such compound is:
 1-(2-chloro-5-pyridylmethyl)-2-cyanoiminoimidazolidine,  
 1-(2-fluoro-5-pyridylmethyl)-2-cyanoiminoimidazolidine,  
 1-(2-chloro-5-pyridylmethyl)-2-cyanoiminotetrahydropyrimidine,  
 1-(2-methyl-5-pyridylmethyl)-2-cyanoiminoimidazolidine,  
 1-(2-chloro-5-thiazolylmethyl)-2-cyanoiminoimidazolidine,  
 1-(2-chloro-5-thiazolylmethyl)-2-cyanoiminotetrahydropyrimidine,  
 1-(2-methyl-5-pyrazinylmethyl)-2-cyanoiminoimidazoline,  
 1-(2-chloro-5-pyridylmethyl)-2-cyanoiminothiazolidine,  
 1-(2-chloro-5-pyridylmethyl)-2-cyanoiminotetrahydro-2H-1,3-thiazine  
 1-(2-chloro-5-thiazolylmethyl)-2-cyanoiminothiazolidine,  
 1-(2-methyl-5-pyrazinylmethyl)-2-cyanoiminothiazolidine,  
 1-(2-methyl-5-thiazolylmethyl)-2-cyanoiminothiazolidine, or  
 1-(1,2,5-thiaziazol-3-ylmethyl)-2-cyanoiminothiazolidine .  
 
     
     
       10. A heterocyclic compound of the formula 
                   
       
         wherein  
         
           R 
           1  
           represents a hydrogen atom or a methyl group,  
         
         
           A represents an ethylene group which may be substituted by methyl,  
         
         
           X represents a sulfur atom  
         
           Z represents a  3   - pyridyl group or a  4   - pyridyl group, each of which is optionally substituted by at least one substituent selected from halogen atoms, alkoxy groups having  1  to  4  carbon atoms, alkylthio groups having  1  to  4  carbon atoms, haloalkyl groups having  1  to  4  carbon atoms, haloalkoxy groups having  1  to  4  carbon atoms, alkylsulfonyl groups having  1  to  4  carbon atoms, a cyano group and a nitro group.    
       
     
     
       11. A compound according to  claim 10 , wherein
   R   1    represents a hydrogen atom,        A represents an ethylene group, and        Z represents a  3   - pyridyl group or a  4   - pyridyl group, each of which is optionally substituted by at least one substituent selected from a fluorine atom, a chlorine atom, a bromine atom, a methoxy group, a methylthio group, a trifluoromethyl group, a trifluoromethoxy group, a methylsulfonyl group, a cyano group and a nitro group.      
     
     
       12. An insecticidal composition comprising an insecticidally effective amount of a compound according to  claim 10  and a diluent.  
     
     
       13. A method of combatting insects which comprises applying to such insects or to an insect habitat an insecticidally effective amount of  1 -(   2   - chloro -   5   - pyridylmethyl )-   2   - cyanoiminotetrahydro -   2 H -   1 , 3   - thiazine.