Substituted Phenyl(Oxy/Thio)Alkanol Derivatives

Abstract

The present invention relates to novel substituted phenyl(oxy/thio)alkanol derivatives, to processes for preparing these compounds, to compositions comprising these compounds and to their use as biologically active compounds, in particular for controlling harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.

1 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         in which: 
         X represents 1H-1,2,4-triazol-1-ylmethyl, 3-pyridinyl, 1H-1,3-imidazol-1-ylmethyl or 2,4-dihydro-3H-1,2,4-triazole-3-thion-1-ylmethyl, 
         Y represents O, S, SO, SO 2  or CH 2 , 
         Z 1  represents bromine, iodine or trifluoromethyl, 
         Z 2  and Z 3  independently of one another represent halogen, methyl or trifluoromethyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio, 
         n represents 0 or 1, 
         R represents tert-butyl, isopropyl, 1-halocyclopropyl, 1-(C 1 -C 4 -alkyl)cyclopropyl, 1-(C 1 -C 4 -alkoxy)cyclopropyl or 1-(C 1 -C 4 -alkylthio)cyclopropyl, 
         and the agrochemically active salts thereof, 
         except for the compounds 
         1-(3-bromo-2-chlorophenoxy)-3,3-dimethyl-2-(1H-1,2,4-triazol-1-ylmethyl)butan-2-ol, 
         1-(4-bromo-2-chlorophenoxy)-3,3-dimethyl-2-(1H-1,2,4-triazol-1-ylmethyl)butan-2-ol, 
         4-(3-bromo-4-fluorophenyl)-2-(1-chlorocyclopropyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, 
         1-[3,5-bis(trifluoromethyl)phenyl]-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol. 
       
     
     
         2 . The compound of formula (I) according to  claim 1   
       in which:
 X represents 1H-1,2,4-triazol-1-ylmethyl, 3-pyridinyl or 2,4-dihydro-3H-1,2,4-triazole-3-thion-1-ylmethyl, 
 Y represents O, S or CH 2 , 
 Z 1  represents bromine or iodine, 
 Z 2  represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, trifluoromethoxy or trifluoromethylthio, 
 Z 3  represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, trifluoromethoxy or trifluoromethylthio, and 
 R represents tert-butyl, isopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl, 1-methoxycyclopropyl or 1-methylthiocyclopropyl. 
 
     
     
         3 . (canceled) 
     
     
         4 . The compound of  claim 1  having formula (I-c) 
       
         
           
           
               
               
           
         
         in which Y, Z 1 , Z 2 , Z 3 , n and R have the meanings as defined in  claim 1 . 
       
     
     
         5 . The compound of  claim 1  having formula (I-e) 
       
         
           
           
               
               
           
         
         in which Y, Z 1 , Z 2 , Z 3 , n and R have the meanings as defined in  claim 1 . 
       
     
     
         6 . A method for controlling phytopathogenic harmful fungi, characterized in that a compound of formula (I) according to  claim 1  is applied to the phytopathogenic harmful fungi, their habitat or a combination thereof. 
     
     
         7 . A composition for controlling phytopathogenic harmful fungi, characterized in that it comprises at least one compound of formula (I) according to  claim 1 , and an extender, a surfactant or combination thereof. 
     
     
         8 . (canceled) 
     
     
         9 . A process for preparing compositions for controlling phytopathogenic harmful fungi, characterized in that a compound of formula (I) according to  claim 1  is mixed with an extender, a surfactant, or combinations thereof. 
     
     
         10 . A process for preparing a compound of formula (I) according to  claim 1 , characterized in that
 (A) if X represents 1-H-1,2,4-triazol-1-ylmethyl or 1H-1,3-imidazol-1-ylmethyl, oxirane derivatives of the formula (II)   
       
         
           
           
               
               
           
         
         in which Y, Z 1 , Z 2 , Z 3 , n and R have the meanings as defined in  claim 1 ,
 are reacted with 1,2,4-triazole or 1,3-imidazole of formula (III) 
 
       
       
         
           
           
               
               
           
         
         in which A represents CH or N,
 in the presence of a diluent; or 
 
         (B) if X represents 1H-1,2,4-triazol-1-ylmethyl, 1H-1,3-imidazol-1-ylmethyl, or 3-pyridinyl,
 oxirane derivatives of formula (IV) 
 
       
       
         
           
           
               
               
           
         
         are reacted with a (thio)phenol of formula (V) 
       
       
         
           
           
               
               
           
         
         in which Y, Z 1 , Z 2 , Z 3 , n and R have the meanings as defined in  claim 1 , and X 2  is 1H-1,2,4-triazol-1-ylmethyl, 1H-1,3-imidazol-1-ylmethyl, or 3-pyridinyl,
 in the presence of a diluent; or 
 
         (C) if X represents 3 pyridinyl,
 phenyl(oxy/thio)ketones of formula (VI) 
 
       
       
         
           
           
               
               
           
         
         in which Y, Z 1 , Z 2 , Z 3 , n and R have the meanings as defined in  claim 1 ,
 are reacted with a halide of formula (VII)
   Hal-X 3   (VII)
 
 
 
          in which Hal represents halogen and X 3  is 3-pyridinyl, 
          in the presence of a diluent and in the presence of an organic alkali metal compound; or 
         (D) if X represents 3 pyridinyl,
 in a first step, bromides of formula (VIII) 
 
       
       
         
           
           
               
               
           
         
         are reacted with a (thio)phenol of formula (V) 
       
       
         
           
           
               
               
           
         
         in the presence of a diluent, and the phenyl(oxy/thio)ketones of formula (IX) obtained in this manner 
       
       
         
           
           
               
               
           
         
         are reacted in a second step with organometal compounds of the formula (X)
   R-M  (X)
 
 
          in which Y, Z 1 , Z 2 , Z 3 , n and R have the meanings as defined in  claim 1 , X 4  is 3-pyridinyl, and M represents metal, 
          in the presence of a diluent and in the presence of an organic alkali metal compound; or 
         (E) a compound of formula (I-c) 
       
       
         
           
           
               
               
           
         
         in which Y, Z 1 , Z 2 , Z 3 , n and R have the meanings given in  claim 1 , are reacted with sulphur. 
       
     
     
         11 . A compound of formula (II) 
       
         
           
           
               
               
           
         
         in which Y, Z 1 , Z 2 , Z 3 , n and R have meanings as defined in  claim 1 , except for the compound 2-{2-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-tert-butyloxirane. 
       
     
     
         12 . A compound of formula (IV-a) 
       
         
           
           
               
               
           
         
         in which: 
         R a  represents isopropyl, 1-halocyclopropyl, 1-(C 1 -C 4 -alkyl)cyclopropyl, 1-(C 1 -C 4 -alkoxy)cyclopropyl or 1-(C 1 -C 4 -alkylthio)cyclopropyl, and 
         A represents CH or N. 
       
     
     
         13 . A compound of formula (IV-b) 
       
         
           
           
               
               
           
         
         in which: 
         R has the meanings as defined in  claim 1  and 
         A represents CH or N, 
         where R does not represent tert-butyl if A represents CH. 
       
     
     
         14 . A compound of formula (IX) 
       
         
           
           
               
               
           
         
         in which X 4  represents 5-pyrimidinyl or 3-pyridinyl and Y, Z 1 , Z 2 , Z 3 , n and R have the meanings as defined in  claim 1 . 
       
     
     
         15 . A method for controlling phytopathogenic harmful fungi, characterized in that a compound of formula (I) according to  claim 2  is applied to the phytopathogenic harmful fungi, their habitat or a combination thereof. 
     
     
         16 . A composition for controlling phytopathogenic harmful fungi, characterized in that it comprises at least one compound of formula (I) according to  claim 2 , and an extender, a surfactant or combination thereof. 
     
     
         17 . A process for preparing compositions for controlling phytopathogenic harmful fungi, characterized in that a compound of formula (I) according to  claim 2  is mixed with an extender, a surfactant, or combinations thereof.