O-benzyloxime ethers and crop protection agents containing these compounds

Abstract

O-Benzyloxime ethers of the formula Iwherein5 x is substituted or unsubstituted CH2, NOalkylY is O, S, NR5R1, R2, R5 are H, alkylZ1, Z2 are H, halogen, methyl, methoxy, cyanoR3, R4 are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl substituted or unsubstituted benzyloxycarbonyl,N(R6)2, where R6 is H, alkyl, substituted or unsubstituted phenyl,-CO-N(R7)2, where R7 is H, substituted or unsubstituted alkyl,substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyloxy,R3 and R4 together may form a carbocyclic or heterocyclic ring which is substituted or unsubstituted, andR3 or R4 may be halogen, ormay bewheren is an integer from 1 to 4, andR8 is, or, when n>1, the R8's are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,and crop protection agents containing these compounds.

We claim:  
     
       1. O-benzyloxime ether of the formula I                    
       where 
       X is N—C 1 -C 4 alkoxy,  
       Y is O or NR 5 ,  
       R 1 , R 2  and R 5  are H or C 1 -C 4 -alkyl,  
       Z 1  and Z 2  are identical or different and each is H, halogen, methyl, methoxy or cyano,  
       R 3  and R 4  are identical or different and each is hydrogen, cyano, straight-chain or branched C 1 -C 10 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, arylthio-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 5 -haloalkenyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 4 -alkylthio, benzylthio, C 1 -C 4 -alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C 1 -C 4 -alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C 1 -C 4 -alkyl, substituted or unsubstituted aryl-C 2 -C 4 -alkenyl, substituted or unsubstituted aryloxy-C 1 -C 4 -alkyl, or substituted or unsubstituted arylthio-C 1 -C 4 -alkyl,  
       N(R 6 ) 2 , where the radicals R 6  are identical or different and each is H, C 1 -C 6 -alkyl or substituted or unsubstituted phenyl,  
       —CO—N(R 7 ) 2 , where the radicals R 7  are identical or different and each is H or C 1 -C 4 -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 10 -alkoximino-C 1 -C 2 -alkyl, aryl, aryloxy, benzyloxy, or C 3 -C 6 -cycloalkyl, or  
       R 3  and R 4  together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, idanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or  
       R 3  and R 4  may be halogen;  
       and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.  
     
     
       2. O-Benzyloxime ethers of the formula III                    
       where the radicals R 3  and R 4  have the meanings given in  claim 1 . 
     
     
       3. A compound of the formula I as set forth in  claim 1 , wherein 
       X is NOCH 3  or NOC 2 H 5 ,  
       Y is 0,  
       R 1  is C 1 -C 4 -alkyl,  
       R 2  is H or C 1 -C 2 -alkyl,  
       R 3  and R 4  are identical or different and each is hydrogen, cyano, straight-chain or branched C 1 -C 10 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 4 -alkyl, arylthio-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 2 -C 4 -haloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C 1 -C 4 -alkyl, or substituted or unsubstituted aryl-C 2 -C 4 -alkenyl,  
       N(R 6 ) 2 , where R 6  is identical or different and each is H, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or substituted or unsubstituted phenyl,  
       CO—N(R 7 ) 2 , where R 7  is identical or different and each is H or C 1 -C 4 -alkyl; or  
       R 3  and R 4  together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl, or fluorenyl, each of which may be substituted by the radicals given under substituted or unsubstituted, or R 3  or R 4  may be halogen; Z 1  and Z 2  are each hydrogen;  
       and substituted or unsubstituted and aryl have the meanings given in  claim 1 .  
     
     
       4. A fungicidal composition comprising in inert carrier and a fungicidally effective amount of an O-benzyloxime ether of the formula I                    
       according to  claim 1 . 
     
     
       5. A process for combating fungi, wherein the fungi, or the materials, plants or seed threatened by fungus attack, or the soil, are treated with a fungicidally effective amount of a compound of the formula I                    
       according to  claim 1 . 
     
     
       6. A compound of the formula I as set forth in  claim 1 , wherein R 1  is methyl, R 2  is H, R 3  is CN, R 4  is cyclopropyl, X is N—OCH 3 , Y is O, and Z 1  and Z 2  are hydrogen. 
     
     
       7. A compound according to  claim 1 , wherein Y is NR 5 . 
     
     
       8. A compound according to claim  7   10 , wherein R 1  is methyl, Z 1 , Z 2 , R 2  and R 5  are hydrogen, X is NOCH 3 , R 3  is methyl, and R 4  is 3,5-dichlorophenyl. 
     
     
       9. O-benzyloxime ether of the formula I                    
       where 
       X is N—C 1 -C 4 -alkoxy,  
       Y is O,  
       R 1  is C 1 -C 4 -alkyl,  
       R 2 , Z 1  and Z 2  are H,  
       R 3  is hydrogen, methyl, ethyl, propyl or cyano,  
       R 4  is hydrogen, cyano, straight-chain or branched C 1 -C 10 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, arylthio-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 5 -haloalkenyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 4 -alkylthio, benzylthio, C 1 -C 4 -alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C 1 -C 4 -alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, aryl substituted by C 1 -C 10 -alkoximino-C 1 -C 2 -alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C 1 -C 4 -alkyl, substituted or unsubstituted aryl-C 2 -C 4 -alkenyl, substituted or unsubstituted aryloxy-C 1 -C 4 -alkyl, or substituted or unsubstituted arylthio-C 1 -C 4 -alkyl, N(R 6 ) 2 , where the radicals R 6  are identical or different and each is H, C 1 -C 6 -alkyl or substituted or unsubstituted phenyl,  
       —CO—N(R 7 ) 2 , where the radicals R 7  are identical or different and each is H or C 1 -C 4 -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 10 -alkoximino-C 1 -C 2 -alkyl, aryl, aryloxy, benzyloxy, or C 3 -C 6 -cycloalkyl, or  
       R 3  and R 4  together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or  
       R 3  or R 4  may be halogen,  
       and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.  
     
     
       10. O- benzyloxime ether of the formula I                     
       
         where  
       
         X is N—C   1   -C   4 - alkoxy    
         Y is NR   5 ,  
       
         R 
         1 
         , R 
         2  
         and R 
         5  
         are  
       
         H or C   1   -C   4 - alkyl,    
       
         Z 
         1  
         and Z 
         2  
         are  
       
       
         identical or different and each is H, halogen, methyl, methoxy or cyano,  
       
       
         R 
         3  
         and R 
         4  
         are  
       
       
         identical or different and each is hydrogen, cyano,  
       
         straight - chain or branched C   1   -C   10 - alkyl, C   1   -C   4 - haloalkyl,    
         C   3   -C   6 - cycloalkyl,    
         C   3   -C   6 - halocycloalkyl,    
         C   3   -C   6 - cycloalkyl - C   1   -C   4 - alkyl,    
         C   1   -C   4 - alkoxy - C   1   -C   4 - alkyl,    
         C   1   -C   4 - alkylthio - C   1   -C   4 - alkyl, arylthio - C   1   -C   4 - alkyl,    
         C   2   -C   6 - alkenyl, C   2   -C   5 - haloalkenyl,    
         C   3   -C   6 - cycloalkenyl, C   3   -C   6 - halocycloalkenyl,    
         C   2   -C   6 - alkynyl, C   1   -C   6 - alkoxy, C   1   -C   6 - haloalkoxy,    
         C   1   -C   4 - alkylthio, benzylthio,    
         C   1   -C   4 - alkylcarbonyl substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl,    
         C   1   -C   4 - alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl,    
         substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl - C   1   -C   4 - alkyl, substituted or unsubstituted aryl - C   2   -C   4 - alkenyl, substituted or unsubstituted aryloxy - C   1   -C   4 - alkyl, or substituted or unsubstituted arylthio - C   1   -C   4 - alkyl, N ( R   6 ) 2   , where the radicals R   6    are identical or different and each is H, C   1   -C   6 - alkyl or substituted or unsubstituted phenyl,    
         —CO—N ( R   7 ) 2   , where the radicals R   7    are identical or different and each is H or C   1   -C   4 - alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C   1   -C   4 - alkyl, C   1   -C   4 - alkoxy, C   1   -C   4 - haloalkyl, C   1   -C   4 - haloalkoxy, C   1   -C   10 - alkoximino - C   1   -C   2 - alkyl, aryl, aryloxy, benzyloxy, or C   3   -C   6 - cycloalkyl, or    
       
         R 
         3  
         and R 
         4  
         together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted or  
       
       
         R 
         3  
         or R 
         4  
         may be halogen;  
       
       
         and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl. 
       
     
     
       11. The O- benzyloxime ether of    claim 10   , wherein R   2    is hydrogen.   
     
     
       12. O- Benzyloxime ethers of the formula II                     
       
         where  
       
       
         X is N—C 
         1 
         -C 
         4  
         alkoxy,  
       
         R   1    and R   5    are H or C   1   -C   4 - alkyl,    
       
         Z 
         1  
         and Z 
         2  
         are identical or different and each is H, halogen, methyl, methoxy or cyano,  
       
       
         R 
         3  
         is cyano, and  
       
         R   4    is substituted or unsubstituted phenyl or naphthyl, and the substituents on the phenyl or naphthyl are halogen, cyano, nitro, C   1   -C   4 - alkyl, C   1   -C   4 - alkoxy, C   1   -C   4 - haloalkyl, C   1   -C   4 - haloalkoxy, C   1   -C   10 - alkoximino - C   1   -C   2 - alkyl, aryl, aryloxy, benzyloxy, or C   3   -C   6 - cycloalkyl.   
     
     
       13. A fungicidal composition comprising an inert carrier and a fungicidally effective amount of an O- benzyloxime ether of the formula I                     
       
         according to  
         claim 10 
         . 
       
     
     
       14. A process for combating fungi, wherein the fungi, or the materials, plants, or seed threatened by fungus attack or the soil, are treated with a fungicidally effective amount of a compound of the formula I                   
       
         according to  
         claim 10 
         .