Phenylacetic acid derivatives, preparation thereof and intermediates therefor, and compositions containing them

Abstract

Phenylacetic acid derivatives of the formula I

We claim:  
     
       1. A phenylacetic acid derivative of the formula I                    
       where the substituents and the index have the following meanings: 
       X is oxygen or sulfur;  
       R is hydrogen or C 1 -C 4 -alkyl;  
       R 1  is hydrogen or C 1 -C 4 -alkyl;  
       R 2  is cyano, nitro, trifluoromethyl, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;  
       m is 0, 1 or 2, it being possible for the R 2  radicals to be different if m is 2;  
       R 3  is hydrogen, cyano, nitro, hydroxyl, amino, cyclopropyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 3 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino or di-C 1 -C 4 -alkylamino;  
       R 4  is hydroxyl, amino, halogen,  
       C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkenylthio, C 2 -C 6 -alkenylamino, N-C 2 -C 6 -alkenyl-N-C 1 -C 6 -alkylamino, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkynylthio, C 2 -C 6 -alkynylamino, N-C 2 -C 6 -alkynyl-N-C 1 -C 6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, aryl, aryloxy, aryl-C 1 -C 4 -alkoxy, arylthio and aryl-C 1 -C 4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio and C(═NOR 6 )—A n —R 7 ;  
       C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkylthio, C 3 -C 6 -cycloalkylamino, N-C 3 -C 6 -cycloalkyl-N-C 1 -C 6 -alkylamino, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -cycloalkenylthio, C 3 -C 6 -cycloalkenylamino, N-C 3 -C 6 -cycloalkenyl-N-C 1 -C 6 -alkylamino, aryloxy, arylthio, arylamino and N-aryl-N-C 1 -C 6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl and aryloxy;  
       R 5  is hydrogen, C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkylcarbonyl, C 2 -C 10 -alkenylcarbonyl, C 3 -C 10 -alkynylcarbonyl or C 1 -C 10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, benzyl, benzyloxy, aryl, aryloxy and arylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio or C(═NOR 6 )—A n —R 7 ;  
       aryl, arylcarbonyl and arylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl and aryloxy or C(═NOR 6 )—A n —R 7 ;  
       where  
       A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C 1 -C 6 -alkyl;  
       n is 0 or 1;  
       R 6  is hydrogen or C 1 -C 6 -alkyl and  
       R 7  is hydrogen or C 1 -C 6 -alkyl,  
       andor its saltssalt. 
     
     
       2. A compound of the formula I as claimed in  claim 1 , in which R 3 , R 4  and R 5  have the following meanings: 
       R 3  is hydrogen, hydroxyl, cyclopropyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,  
       R 4  is hydroxyl, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio,  
       R 5  is hydrogen,  
       C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkylcarbonyl, C 2 -C 10 -alkenylcarbonyl, C 3 -C 10 -alkynyl carbonyl or C 1 -C 10 -alkylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkyl amino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy and arylthio, it being possible for the aromatic radicals in turn, to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, halogen, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio or C(═NOR 6 )—A n —R 7 ;  
       aryl, arylcarbonyl, and arylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy or C(═NOR 6 )—A n —R 7 ;  
       where  
       A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C 1 -C 6 -alkyl  
       n is 0 or 1;  
       R 6  is hydrogen or C 1 -C 6 -alkyl and  
       R 7  is hydrogen or C 1 -C 6 -alkyl,  
       and its salts. 
     
     
       3. A compound of the formula I as claimed in  claim 1 , in which m is 0. 
     
     
       4. A compound of the formula I as claimed in  claim 1 , in which R 1  is methyl. 
     
     
       5. The compound defined in  claim 1 , wherein R 4  denotes one of the following: halogen, or 
       C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkenylamino, N-C 2 -C 6 -alkenyl-N-C 1 -C 6 -alkylamino, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkynylamino and N-C 2 -C 6 -alkynyl-N-C 1 -C 6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, aryl, aryloxy, aryl-C 1 -C 4 -alkoxy, arylthio and aryl-C 1 -C 4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio and C(═NOR 6 )—A n —R 7 ;  
       C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkylamino, N-C 3 -C 6 -cycloalkyl-N-C 1 -C 6 -alkylamino, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -cycloalkenylamino, N-C 3 -C 6 -cycloalkenyl-N-C 1 -C 6 -alkylamino, aryloxy, arylamino and N-aryl-N-C 1 -C 6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl and aryloxy.  
     
     
       6. The compound defined in  claim 1 , wherein R 4  denotes one of the following: 
       C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy and C 2 -C 6 -alkynyloxy, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 -cycloalkoxy, aryl, aryloxy, aryl-C 1 -C 4 -alkoxy, arylthio and aryl-C 1 -C 4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio and C(═NOR 6 )—A n —R 7 ;  
       C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkenyloxy, and aryloxy, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkulsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl and aryloxy.  
     
     
       7. The compound defined in  claim 1 , wherein R 4  denotes one of the following: 
       C 1 -C 6 -alkoxy, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 -cycloalkoxy, aryl, aryloxy, aryl-C 1 -C 4 -alkoxy, arylthio and aryl-C 1 -C 4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio and C(═NOR 6 )—A n —R 7 .  
     
     
       8. A composition against animal pests or harmful fungi, containing customary additives and an effective amount of a compound of the formula I as defined in  claim 1 . 
     
     
       9. A method for controlling animal pests or harmful fungi, which comprises treating the pests or harmful fungi, their environment of the plants, surfaces, materials or spaces to be kept free from them with an effective amount of a compound of the formula I as defined in  claim 1 .