Fungicidal mixtures based on morpholine or piperidine derivatives and oxime ether derivatives

Abstract

Fungicidal mixtures, comprising as active components a) a morpholine or piperidine derivative I selected from the group of the compounds Ia, Ib, Ic and Id b) compounds of the formula II where the substituents X 1 to X 5 and R 1 to R 4 are as defined below: X 1 is C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or halogen; X 2 to X 5 are, independently of one another, hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; R 1 is C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkyl-C 3 -C 7 -cycloalkyl, C 1 -C 4 -alkyl-C 3 -C 7 -cycloalkenyl, where these radicals may carry substituents selected from the group consisting of halogen, cyano and C 1 -C 4 -alkoxy, R 2 is a phenyl radical or a 5- or 6-membered saturated or unsaturated heterocyclyl radical having at least one heteroatom selected from the group consisting of N, O and S, where the cyclic radicals may have one to three substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxy-C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy-C 2 -C 4 -alkynyl, R 3 and R 4 are, independently of one another, hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, N-C 1 -C 4 -alkylamino, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy in a synergistically effective amount are described.

1 . A fungicidal mixture, comprising as active components 
 a) a compound of the formula Id                          and    b) one or more compounds of the formula II                          where the substituents X 1  to X 5  and R 1  to R 4  are as defined below:    X 1  is C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or halogen;    X 2  to X 5  are, independently of one another, hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,    R 1  is C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkyl-C 3 -C 7 -cycloalkyl, where these radicals may carry substituents selected from the group consisting of halogen, cyano and C 1 -C 4 -alkoxy,    R 2  is a phenyl radical or a 5- or 6-membered saturated or unsaturated heterocyclyl radical having at least one heteroatom selected from the group consisting of N, O and S, where the cyclic radicals may have one to three substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxy-C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy-C 2 -C 4 -alkynyl,    R 3  and R 4  are, independently of one another, hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, N-C 1 -C 4 -alkylamino, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy    in a synergistically effective amount.    
   
   
       2 . A fungicidal mixture as claimed in  claim 1 , where in the one or more compounds II, R 1  is C 1 -C 4 -alkyl or C 1 -C 4 -alkylene-C 3 -C 7 -cycloalkyl.  
   
   
       3 . A fungicidal mixture as claimed in  claim 1 , where in the one or more compounds II, R 2  is phenyl, thienyl, pyrazolyl, pyrrolyl, imidazolyl, thiazolyl, furyl, pyridazinyl or pyrimidinyl, and these radicals may be substituted by halogen, C 1 -C 4 -alkoxy or C 1 -C 4 -alkyl.  
   
   
       4 . A fungicidal mixture as claimed in  claim 1 , where in the one or more compounds II, R 3  or R 4  are independently of one another hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, thiomethyl or N-methyamino.  
   
   
       5 . A fungicidal mixture as claimed in  claim 1 , where in the one or more compounds II, X 1  is halo-C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkoxy or halogen.  
   
   
       6 . A fungicidal mixture as claimed in  claim 1 , where in the one or more compounds II, X 2  or X 3  are hydrogen or halogen.  
   
   
       7 . A fungicidal mixture as claimed in  claim 1 , where in the one or more compounds II, X 4  is hydrogen, chlorine, fluorine, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy.  
   
   
       8 . A fungicidal mixture as claimed in  claim 1 , where in the one or more compounds II, X 5  is hydrogen, chlorine, fluorine, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy.  
   
   
       9 . A fungicidal mixture as claimed in  claim 1 , which is conditioned in two parts, where one part comprises the compound Id in a solid or liquid carrier and the other part comprises the one or more compounds of the formula II in a solid or liquid carrier.  
   
   
       10 . A method for controlling harmful fungi, which comprises treating the fungi, their habitat or the materials, plants, seeds, soils, areas or spaces to be protected against fungal attack with a fungicidal mixture as claimed in  claim 1 , where the compound Id and the one or more compounds of the formula II can be applied simultaneously, that is either together or separately, or successively.  
   
   
       11 . A fungicidal mixture as claimed in  claim 1 , wherein in the one or more compounds of the formula II 
 X 1  is C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy;    X 2  is hydrogen or C 1 -C 4 -alkyl;    X 3  is hydrogen or C 1 -C 4 -alkyl;    X 4  is halogen;    X 5  is halogen;    R 1  is methylenecyclopropyl, methylenecyclopentyl, methylenecyclohexyl or methylenecyclohexenyl;    R 2  is phenyl which is optionally substituted by halogen, C 1 -C 4 -alkoxy or C 1 -C 4 -alkyl;    R 3  and R 4  are, independently of one another, hydrogen or C 1 -C 4 -alkyl.    
   
   
       12 . The mixture defined in  claim 11 , wherein R 1  is methylenecyclopropyl.  
   
   
       13 . The mixture defined in  claim 11 , wherein R 2  is phenyl.  
   
   
       14 . The mixture defined in  claim 11 , wherein R 3 or R 4 is hydrogen.  
   
   
       15 . The mixture defined in  claim 11 , wherein R 3  and R 4  are hydrogen.  
   
   
       16 . The mixture defined in  claim 1   1 , wherein X 2  or X 3  is hydrogen.  
   
   
       17 . The mixture defined in  claim 11 , wherein X 2  and X 3  are hydrogen.  
   
   
       18 . The mixture defined in  claim 11 , wherein X 4  is chlorine or fluorine.  
   
   
       19 . The mixture defined in  claim 11 , wherein X 5  is chlorine or fluorine.  
   
   
       20 . The mixture defined in  claim 11 , wherein 
 X 2  is hydrogen;    X 3  is hydrogen;    R 1  is methylenecyclopropyl;    R 2  is phenyl; and    R 3  and R 4  are hydrogen.    
   
   
       21 . The mixture defined in  claim 12 , which is conditioned in two parts, wherein one part comprises the compound Id in a solid or liquid carrier and the other part comprises the one or more compounds of the formula II in a solid or liquid carrier.  
   
   
       22 . A method for controlling harmful fungi, which comprises treating the fungi, their habitat or the materials, plants, seeds, soils, areas or spaces to be protected against fungal attack with the mixture defined in  claim 12 , where the compound Id and the one or more compounds of the formula II are applied simultaneously, that is either together or separately, or successively.  
   
   
       23 . The mixture defined in  claim 11 , wherein in the one or more compounds of the formula II 
 X 1  is trifluoromethyl or difluoromethoxy;    X 2  is hydrogen;    X 3  is hydrogen;    X 4  is chlorine or fluorine;    X 4  is chlorine or fluorine;    R 1  is methylenecyclopropyl;    R 2  is phenyl; and    R 3  and R 4  are hydrogen.    
   
   
       24 . The mixture defined in  claim 11 , which comprises the compound Id and the one or more compounds of the formula II in a ratio by weight of from 20:1 to 1:20.  
   
   
       25 . The method of  claim 22 , wherein the compound Id and the one or more compounds of the formula II are applied in a ratio by weight of from 20:1 to 1:20.  
   
   
       26 . The method of  claim 22 , wherein the mixture is applied in an amount of from 0.0 1 to 10 kg/ha.  
   
   
       27 . The method of  claim 22 , wherein the mixture is applied to seeds in an amount of from 0.001 to 250 g/kg.  
   
   
       28 . The method of  claim 22 , wherein the compound Id is applied in an amount of from 0.01 to 2.5 kg/ha.  
   
   
       29 . The method of  claim 22 , wherein the one or more compounds of the formula II is applied in an amount of from 0.01 to 2 kg/ha