Spiroketal-Substituted Cyclic Ketoenols

Abstract

The invention relates to novel spiroketal-substituted cyclic ketoenols of the formula (I) in which A, B, Q 1 , Q 2 , D, G, W, X, Y, and Z are as defined above, to processes and intermediates for their preparation and to their use as pesticides and/or microbicides and/or herbicides. Moreover, the invention relates to selective herbicidal compositions comprising, firstly, spiroketal-substituted cyclic ketoenols and, secondly, a crop plant compatibility-improving compound.

1 - 18 . (canceled) 
     
     
         19 . A compound of the formula (II) 
       
         
           
           
               
               
           
         
         in which 
         W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano, 
         X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano, 
         Y and Z independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano, nitro, or represents in each case optionally substituted aryl or heteroaryl, 
       
       with the proviso that at least one of the radicals W or Z is different from hydrogen if X and Y represent methyl,
 A and B and the carbon atom to which they are attached represent a five- to seven-membered ketal, thioketal or dithioketal which is optionally interrupted by a further heteroatom, each of which radicals is optionally substituted by alkyl, haloalkyl, alkoxy, alkoxyalkyl or optionally substituted phenyl, 
 Q 1  and Q 2  independently of one another represent hydrogen, alkyl, haloalkyl or alkoxy, and 
 R 8  represents alkyl. 
 
     
     
         20 . A compound of the formula (III) 
       
         
           
           
               
               
           
         
         in which 
         W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano,
 X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano, 
 Y and Z independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano, nitro, or represents in each case optionally substituted aryl or heteroaryl, 
 
         with the proviso that at least one of the radicals W or Z is different from hydrogen if X and Y represent methyl,
 A and B and the carbon atom to which they are attached represent a five- to seven-membered ketal, thioketal or dithioketal which is optionally interrupted by a further heteroatom, each of which radicals is optionally substituted by alkyl, haloalkyl, alkoxy, alkoxyalkyl or optionally substituted phenyl, 
 Q 1  and Q 2  independently of one another represent hydrogen, alkyl, haloalkyl or alkoxy, and 
 R 8  represents alkyl. 
 
       
     
     
         21 . A compound of the formula (XVIII) 
       
         
           
           
               
               
           
         
         in which 
         W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano, 
         X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano, 
         Y and Z independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano, nitro, or represents in each case optionally substituted aryl or heteroaryl, 
       
       with the proviso that at least one of the radicals W or Z is different from hydrogen if X and Y represent methyl,
 A and B and the carbon atom to which they are attached represent a five- to seven-membered ketal, thioketal or dithioketal which is optionally interrupted by a further heteroatom, each of which radicals is optionally substituted by alkyl, haloalkyl, alkoxy, alkoxyalkyl or optionally substituted phenyl, and 
 Q 1  and Q 2  independently of one another represent hydrogen, alkyl, haloalkyl or alkoxy. 
 
     
     
         22 . A compound of the formula (XXI) 
       
         
           
           
               
               
           
         
         in which 
         W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano, 
         X represents halogen, alkyl, alkenyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano, 
         Y and Z independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano, nitro, or represents in each case optionally substituted aryl or heteroaryl, 
       
       with the proviso that at least one of the radicals W or Z is different from hydrogen if X and Y represent methyl,
 A and B and the carbon atom to which they are attached represent a five- to seven-membered ketal, thioketal or dithioketal which is optionally interrupted by a further heteroatom, each of which radicals is optionally substituted by alkyl, haloalkyl, alkoxy, alkoxyalkyl or optionally substituted phenyl, and 
 Q 1  and Q 2  independently of one another represent hydrogen, alkyl, haloalkyl or alkoxy. 
 
     
     
         23 . A compound of the formula (XXII) 
       
         
           
           
               
               
           
         
         in which 
         A and B and the carbon atom to which they are attached represent a five- to seven-membered ketal, thioketal or dithioketal which is optionally interrupted by a further heteroatom, each of which radicals is optionally substituted by alkyl, haloalkyl, alkoxy, alkoxyalkyl or optionally substituted phenyl, 
         Q 1  and Q 2  independently of one another represent hydrogen, alkyl, haloalkyl or alkoxy, and 
         R 8  represents alkyl. 
       
     
     
         24 . A compound of the formula (XVI′) 
       
         
           
           
               
               
           
         
       
       or a salt thereof, in which
 Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, 
 q represents 1, 2 or 3, and 
 R 8  is alkyl. 
 
     
     
         25 . A compound of the formula (XVI″) 
       
         
           
           
               
               
           
         
       
       or a salt thereof, in which
 Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, 
 q represents 0, 1, 2 or 3, and 
 R 8  represents alkyl. 
 
     
     
         26 . A compound of the formula (XVI′″) 
       
         
           
           
               
               
           
         
       
       or a salt thereof, in which
 Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, 
 q represents 0, 1, 2 or 3, and 
 R 8  represents alkyl. 
 
     
     
         27 . A compound of the formula (XIX′) 
       
         
           
           
               
               
           
         
         in which 
         Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, and 
         q represents 1, 2 or 3. 
       
     
     
         28 . A compound of the formula (XIX″) 
       
         
           
           
               
               
           
         
         in which 
         Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, and 
         q represents 0, 1, 2 or 3. 
       
     
     
         29 . A compound of the formula (XIX′″) 
       
         
           
           
               
               
           
         
         in which 
         Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, and 
         q represents 0, 1, 2 or 3. 
       
     
     
         30 . A compound of the formula (XXIII′) 
       
         
           
           
               
               
           
         
         in which 
         Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, and 
         q represents 1, 2 or 3. 
       
     
     
         31 . A compound of the formula (XXIII″) 
       
         
           
           
               
               
           
         
         in which 
         Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, and 
         q 0, 1, 2 or 3. 
       
     
     
         32 . A compound of the formula (XXIII′″) 
       
         
           
           
               
               
           
         
         in which 
         Q 3  represents C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, and 
         q represents 0, 1, 2 or 3. 
       
     
     
         33 . A compound of the formula (XIV) 
       
         
           
           
               
               
           
         
         in which 
         W represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, alkenyloxy, haloalkyl, haloalkoxy or cyano, 
         X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano, 
         Y and Z independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano, nitro, or represents in each case optionally substituted aryl or heteroaryl, 
       
       with the proviso that at least one of the radicals W or Z is different from hydrogen if X and Y represent methyl,
 D represents NH or oxygen, 
 Q 1  and Q 2  independently of one another represent hydrogen, alkyl, haloalkyl or alkoxy, 
 G represents hydrogen (a), or 
 
       
         
           
           
               
               
           
         
         
           in which 
           E represents a metal ion or an ammonium ion, 
           L represents oxygen or sulphur, 
         
         M represents oxygen or sulphur, 
         R 1  represents in each case optionally halogen- or cyano-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, or represents in each case optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl, or represents in each case optionally substituted phenyl, phenylalkyl, heteroaryl, phenoxyalkyl or heteroaryloxyalkyl, 
         R 2  represents in each case optionally halogen- or cyano-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl, 
         R 3 , R 4  and R 5  independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, and 
         R 6  and R 7  independently of one another represent hydrogen, in each case optionally halogen- or cyano-substituted alkyl, cycloalkyl, alkenyl, alkoxy, or alkoxyalkyl, or represent in each case optionally substituted phenyl or benzyl, or R 6  and R 7  together with the N atom to which they are attached form an optionally substituted cycle which optionally contains oxygen or sulphur.