Substituted propargylamines

Abstract

The present invention relates to the use of substituted aryl- and heteroarylpropargylamines of the formula (I) where a) R 1 is heteroaryl or aryl, unsubstituted or mono- or polysubstituted by identical or different radicals, b) A is a group CR 4 R 5 or C═O, where R 4 is hydrogen, halogen or alkyl; R 5 is hydrogen, halogen or a substituted or unsubstituted hydrocarbon radical; c) R 2 and R 3 together with the nitrogen atom to which they are attached form N-heteroaryl or N-heterocyclyl, unsubstituted or mono- or polysubstituted by identical or different radicals, if appropriate also as N-oxide or salt, as pesticide against arthropods and helminths for protecting plants and animals.

1 . A method for controlling harmful arthropods and/or helminths, which comprises applying to these or to the plants or animals, areas or substrates infected by them an effective amount of a compound of the formula (I)  
     
       
         
         
             
             
         
       
     
     or an N-oxide or salt thereof, wherein: 
 a) R 1  is heteroaryl, unsubstituted or mono- or polysubstituted by identical or different radicals;  
 b) A is a group CR 4 R 5  or C═O, wherein: 
 R 4  is hydrogen or alkyl; and  
 R 5  is hydrogen or a hydrocarbon radical; and  
 
 c) R 2  and R 3  together with the nitrogen atom to which they are attached form N-heteroaryl or N-heterocyclyl, unsubstituted or mono- or polysubstituted by identical or different radicals.  
 
   
   
       2 . A compound of the formula (I)  
     
       
         
         
             
             
         
       
     
     or its N-oxide or salt, wherein: 
 a) R 1  is heteroaryl which is unsubstituted or mono- or polysubstituted by identical or different radicals;  
 b) A is a group CR 4 R 5  or C═O, wherein 
 R 4  is hydrogen or alkyl; and  
 R 5  is hydrogen or a hydrocarbon radical; and  
 
 c) R 2  and R 3  together with the nitrogen atom to which they are attached form a piperidine radical which is unsubstituted or mono- or polysubstituted by identical or different radicals.  
 
   
   
       3 . A process for preparing a compound of the formula (I) as claimed in  claim 2 , which comprises reacting a compound of the formula (II)  
       R 1 —X  (II)  wherein:    X is —O—SO 2 —CF 3  or halogen and    R 1  is as defined in formula (I) as claimed in  claim 2     in the presence of a palladium catalyst, a base and a copper(I) salt with a compound of the formula (III)                          wherein A, R 2  and R 3  are as defined in formula (I) as claimed in  claim 2 .    
   
   
       4 . A pesticidal composition, comprising at least one compound of the formula (I) as claimed in  claim 2  and at least one formulation auxiliary.  
   
   
       5 . A pesticidal composition for application as an insecticidal, acaricidal or nematicidal composition comprising an insecticidally, acaricidally or nematicidally effective amount of at least one compound of the formula (I) as claimed in  claim 2  together with additives or auxiliaries customary for this application.  
   
   
       6 . A pesticidal composition, comprising an insecticidally, acaricidally or nematicidally effective amount of at least one compound of the formula (I) as claimed in  claim 2  and at least one further active compound together with auxiliaries and additives customary for this application.  
   
   
       7 . A pesticidal composition for application in the protection of wood or as a preservative in sealants, in paints, in cooling lubricants for metal working or in drilling and cutting oils, comprising an insecticidally, acaricidally or nematicidally effective amount of at least one compound of the formula (I) as claimed in  claim 2  together with auxiliaries and additives customary for these applications.  
   
   
       8 . A veterinary medicament comprising an insecticidally, acaricidally or nematicidally effective amount of a compound as claimed in  claim 2  together with at least one additive or auxiliary customary for veterinary administration.  
   
   
       9 . A seed, treated or coated with an insecticidally, acaricidally or nematicidally effective amount of a compound of the formula (I) as claimed in  claim 2 .  
   
   
       10 . A seed, treated or coated with an insecticidally, acaricidally or nematicidally effective amount of a composition as claimed in  claim 4 .  
   
   
       11 . A method for controlling harmful arthropods and/or helminths, which comprises applying to these or to the plants or animals, areas or substrates infected by them an arthropodicidally or helminthicidally effective amount of a compound of the formula (I) as claimed in  claim 2.