O-cyclopropyl-carboxanilides and their use

Abstract

A compound of formula (I): Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R 4 , R 5 and R 6 ; R 1 is hydrogen or halo; R 2 is hydrogen or halo; R 3 is optionally substituted C 2-12 alkyl, optionally substituted C 2-12 alkenyl, optionally substituted C 2-12 alkynyl, optionally substituted C 3-12 cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl; and R 4 , R 5 and R 6 are, independently, selected from hydrogen, halo, cyano, nitro, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy(C 1-4 )alkyl and C 1-4 haloalkoxy(C 1-4 )alkyl, provided that at least one of R 4 , R 5 and R 6 is not hydrogen. The compounds of formula (I) have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms.

1 . A compound of formula (I): 
       
         
           
           
               
               
           
         
         Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R 4 , R 5  and R 6 ; R 1  is hydrogen or halo; R 2  is hydrogen or halo; R 3  is optionally substituted C 2-12  alkyl, optionally substituted C 2-12  alkenyl, optionally substituted C 2-12  alkynyl, optionally substituted C 3-12  cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl; and R 4 , R 5  and R 6  are, independently, selected from hydrogen, halo, cyano, nitro, C 1-4  alkyl, C 1-4  haloalkyl, C 1-4  alkoxy(C 1-4 )alkyl and C 1-4  haloalkoxy(C 1-4 )alkyl, provided that at least one of R 4 , R 5  and R 6  is not hydrogen. 
       
     
     
         2 . A compound of formula (I) as claimed in  claim 1  where Het is pyrrolyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, thiophenyl, furyl, isothiazolyl or isoxazolyl, each being substituted by groups R 4 , R 5  and R 6 . 
     
     
         3 . A compound of formula (I) as claimed in  claim 1  where R 1  is hydrogen or fluoro. 
     
     
         4 . A compound of formula (I) as claimed in  claim 1  where R 2  is hydrogen or fluoro. 
     
     
         5 . A compound of formula (I) as claimed in  claim 1  where R 3  is C 2-6  alkyl, optionally substituted C 3-8  cycloalkyl, phenyl, thienyl or furyl. 
     
     
         6 . A compound of formula (I) as claimed in  claim 1  where R 4 , R 5  and R 6  are, independently, selected from hydrogen, halogen, C 1-4  alkyl, C 1-4  haloalkyl and C 1-4  alkoxy(C 1-4 )alkyl; provided that at least one of R 4 , R 5  and R 6  is not hydrogen. 
     
     
         7 . A compound of formula (II): 
       
         
           
           
               
               
           
         
         where R 3  is as defined in  claim 1 . 
       
     
     
         8 . A process for preparing a compound of formula (II) as claimed in  claim 7  which comprises a step using a Pd(II)catalyst-ligand-system where the ligand is selected from a suitable sterically demanding phosphine to react a compound of formula (XI) 
       
         
           
           
               
               
           
         
         with benzophenone imine optionally in the presence of a base to produce a compound of formula (XII) 
       
       
         
           
           
               
               
           
         
         where Hal is bromo or iodo; and R 3  is as defined in  claim 7 . 
       
     
     
         9 . A composition for controlling microorganisms and preventing attack and infestation of plants therewith, wherein the active ingredient is a compound of formula (I) as claimed in  claim 1  together with a suitable carrier. 
     
     
         10 . A method of controlling or preventing infestation of cultivated plants by phytopathogenic microorganisms by application of a compound of formula (I) as claimed in  claim 1  to plants, to parts thereof or the locus thereof.