3-substituted phenoxyphenylamidines and use thereof as fungicides

Abstract

The present invention relates to 3-substituted phenylamidines of the general formula (I), to a process for their preparation, to the use of the amidines according to the invention for controlling unwanted microorganisms and also to a composition for this purpose, comprising the phenoxyamidines according to the invention. Furthermore, the invention relates to a method for controlling unwanted microorganisms by applying the compounds according to the invention to the microorganisms and/or their habitat.

1 . A 3-substituted phenoxyphenylamidine of formula (I) 
     
       
         
         
             
             
         
       
       in which 
       m represents an integer from 0 to 12; 
       R 1  is selected from the group consisting of hydrogen; straight-chain, branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl or cyclic C 3-12 -alkyl, C 4-12 -alkenyl, C 4-12 -alkynyl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P and S and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ represents hydrogen or a C 1-12 -alkyl group; —SH; —SR″, where R″ represents a C 1-12 -alkyl group which may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ has the above meanings; 
       R 2  is selected from the group consisting of straight-chain, branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, cyclic C 3-12 -alkyl, C 4-12 -alkenyl, C 4-12 -alkynyl or C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P and S and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and CONR′ 2 , where R′ has the above meanings; 
       R 3  is selected from the group consisting of —CN, —SH, —SR″, —OR″, —(C═O)—R″, where R″ has the above meanings; straight-chain, branched C 2-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, cyclic C 3-12 -alkyl, C 4-12 -alkenyl, C 4-12 -alkynyl or C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P and S and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and CONR′ 2 , where R′ has the above meanings; 
       or in which 
       R 2  and R 3 , 
       R 2  and R 1  or 
       R 1  and R 3  together with the atoms to which they are attached or together with further atoms selected from the group consisting of N, O, P and S may form a four- to seven-membered ring which may be substituted by one or more X, R′, OR′, SR′, NR′ 2 , SiR′ 3  groups, where R′ has the above meanings; 
       R 4  and R 5  independently of one another are selected from the group consisting of hydrogen, —X, —CN, —SH, —SR″, —OR″, —(C═O)—R″, where R″ has the above meanings; straight-chain, branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, cyclic C 3-12 -alkyl, C 4-12 -alkenyl, C 4-12 -alkynyl or C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P and S and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, halogen (—X), alkoxy (—OR′), thioether or mercapto (—SR′), amino (—NR′ 2 ), silyl (—SiR′ 3 ), carboxyl (—COOR′), cyano (—CN), and amide groups (—CONR′ 2 ), where R′ has the above meanings; 
       R 6  and R 7  independently of one another are selected from the group consisting of hydrogen, straight-chain, branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, cyclic C 3-12 -alkyl, C 4-12 -alkenyl, C 4-12 -alkynyl or C 5-18 -aryl, C 7-19 -aralkyl or C 7-19 -alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P and S and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, halogen (—X), alkoxy (—OR′), thioether or mercapto (—SR′), amino (—NR′ 2 ), silyl (—SiR′ 3 ), carboxyl (—COOR′), cyano (—CN) and amide groups (—CONR′ 2 ), where R′ has the above meanings; 
       R 8  is selected from the group consisting of hydrogen, halogen (—X), alkoxy (—OR′), thioether or mercapto (—SR′), amino (—NR′ 2 ), silyl (—SiR′ 3 ), carboxyl (—COOR′), cyano (—CN) and amide groups (—CONR′ 2 ), straight-chain, branched C 2-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, cyclic C 3-12 -alkyl, C 4-12 -alkenyl, C 4-12 -alkynyl or C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P and S and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, halogen (—X), alkoxy (—OR′), thioether or mercapto (—SR′), amino (—NR′ 2 ), silyl (—SiR′ 3 ), carboxyl (—COOR′), cyano (—CN) and amide groups (—CONR′ 2 ), where R′ has the above meanings; 
       And/or a salt thereof. 
     
   
   
       2 . The 3-substituted phenoxyphenylamidine as claimed in  claim 1  where
 m represents from 0 to 2;   R 1  is selected from the group consisting of hydrogen, a mercapto group (—SH) or C 1-8 -alkyl groups;   R 2  is selected from the group consisting of straight-chain or branched C 1-8 -alkyl groups;   R 3  is selected from the group consisting of straight-chain, branched and alicyclic C 2-8 -alkyl groups;   or where   R 2  and R 3  together with the nitrogen atom to which they are attached or together with further atoms, which are selected from the group consisting of N and O, may form a five- to six-membered ring which may be substituted by one or more C 1-12 -alkyl groups;   R 4  and R 5  independently of one another are selected from the group consisting of —X, straight-chain or branched C 1-12 -alkyl groups and C 1-5 -haloalkyl groups;   R 6  and R 7  independently of one another are selected from a group consisting of hydrogen, straight-chain C 1-8 -alkyl groups;   R 8  is selected from the group consisting of hydrogen, straight-chain, branched, alicyclic or heterocyclic C 2-8 -alkyl groups, OR′-, SiR′ 3  groups, where R′ represents hydrogen or a C 1-12 -alkyl group;   And/or a salt thereof.   
   
   
       3 . The 3-substituted phenoxyphenylamidine or salt as claimed in  claim 1  where
 m represents 0 or 1;   R 1  is selected from the group consisting of hydrogen, mercapto and methyl;   R 2  is selected from the group consisting of methyl and ethyl;   R 3  is selected from the group consisting of ethyl and cyclopropyl;   or where   R 2  and R 3  together with the nitrogen atom to which they are attached form a piperidyl, pyrrolidyl or 2,6-dimethylmorpholinyl radical;   R 4  and R 5  independently of one another are selected from the group consisting of Cl and F atoms and —CF 3 , —CF 2 H and methyl groups;   R 6  and R 7  independently of one another are selected from the group consisting of hydrogen, methyl and ethyl groups;   R 8  is selected from the group consisting of tert-butyl, methoxy, ethoxy, trimethylsilyl and triethylsilyl groups,   And/or a salt thereof.   
   
   
       4 . The 3-substituted phenoxyphenylamidine and/or salt as claimed in  claim 1  selected from the group consisting of N-ethyl-N′-{4-[3-(1-methoxy-1-methylethyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (1), N-ethyl-N′-{4-[3-(1-hydroxybutyl)phenoxy]-2,5-dimethylphenyl}-N-methyl-imidoformamide (2), N-ethyl-N′-{4-[3-(1-hydroxy-1-methylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (3), N-ethyl-N′-{4-[3-(1-hydroxy-1-methyl-prop-2-yn-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimido-formamide (4), N-ethyl-N′-{4-[3-(1-hydroxy-1-phenylethyl)phenoxy]-2,5-dimethylphenyl}-N-methylimido-formamide (5), N′-{2,5-dimethyl-4-[3-(1-methylenepropyl)phenoxy]phenyl}-N-ethyl-N-methylimidoformamide (6-1), N′-(2,5-dimethyl-4-{3-[(1e/Z)-1-methylprop-1-en-1-yl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide (6-2), N′-{2,5-dimethyl-4-[3-(1,1,2-trimethylpropyl)phenoxy]phenyl}-N-ethyl-N-methylimidoformamide (7), N-ethyl-N′-{4-[3-(1-methoxy-1-methylpropyl)phenoxy]-2,5-dimethylphenyl}-N-methylimido-formamide (8), N-ethyl-N′-{4-[3-(1-methoxy-1,2-dimethylpropyl)phenoxy]-2,5-dimethylphenyl}-N-methyl-imidoformamide (9), N-ethyl-N′-{4-[3-(1-methoxy-1,3-dimethylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (10), N-ethyl-N′-{4-[3-(1-methoxy-1-methylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (11), N-ethyl-N′-{4-[3-(1-methoxy-1-phenylethyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (12), N′-{4-[3-(1-ethoxy-1,2-dimethylpropyl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (13), N′-{4-[3-(1-ethoxy-1-methylbutyl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methyl-imidoformamide (14), N′-{4-[3-(1-ethoxy-1,3-dimethylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (15), N′-{4-[3-(1-ethoxy-1-methyl-but-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (16), N′-{4-[3-(1-ethoxy-1-methylprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (17), N-ethyl-N′-{4-[3-(1-methoxy-2,2-dimethylpropyl)-phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (18), N-ethyl-N′-{4-[3-(1-hydroxy-1,2,2-trimethyl-propyl)phenoxy]-2,5-dimethylphenyl}-N-methylimido-formamide (19), N′-(4-{3-[1-(allyloxy)-1,3-dimethylbut-3-en-1-yl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide (20), N′-(4-{3-[1-(allyloxy)-1-methylbutyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide (21), N′-(4-{3-[1-(allyloxy)-1-methylprop-2-en-1-yl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide (22), N′-{4-[3-(1-butoxy-1,3-dimethylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (23), N′-{4-[3-(1-butoxy-1-methylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (24), N-ethyl-N′-{4-[3-(1-ethyl-1-hydroxypropyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (25), N-ethyl-N′-{4-[3-(1-ethyl-1-hydroxyprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (26), N′-{2,5-dimethyl-4-[3-(2,2,2-trifluoro-1-methoxyethyl)phenoxy]phenyl}-N-ethyl-N-methylimidoformamide (27), N-ethyl-N′-{4-[3-(1-methoxyprop-2-yn-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methyl-limidoformamide (28), N′-{4-[3-(1-ethoxy-1-methylpropyl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (29), N′-{4-[3-(1-chloro-2,2-dimethylpropyl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (30), N′-(4-{3-[1-(allyloxy)-1-phenylethyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyl-imidoformamide (31), N′-{4-[3-(1-butoxy-1-methylprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimido-formamide (32), N-ethyl-N′-{4-[3-(1-hydroxy-2-methylpropyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (33), N-ethyl-N′-{4-[3-(hydroxymethyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (34), N-ethyl-N′-{4-[3-(1-hydroxybut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methyl-imidoformamide (35), N′-{2,5-dimethyl-4-[3-(2,2,2-trifluoro-1-hydroxyethyl)phen-oxy]phenyl}-N-ethyl-N-methylimidoformamide (36), N-ethyl-N′-{4-[3-(1-hydroxyprop-2-yn-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (37), N-ethyl-N′-{4-[3-(1-hydroxyprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (38), N′-{2,5-dimethyl-4-[3-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenoxy]phenyl}-N-ethyl-N-methylimidoformamide (39), N-ethyl-N′-{4-[3-(1-methoxybut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (40), N′-{2,5-dimethyl-4-[3-(2,2,2-trifluoro-1-methoxy-1-methylethyl)phenoxy]phenyl}-N-ethyl-N-methylimidoformamide (41), N′-[2,5-dimethyl-4-(3-{2,2,2-trifluoro-1-[(trimethylsilyl)-oxy]ethyl}phenoxy)phenyl]-N-ethyl-N-methylimidoformamide (42), N′-[2,5-dimethyl-4-(3-{2,2,2-trifluoro-1-methyl-1-[(trimethylsilyl)oxy]ethyl}phenoxy)phenyl]-N-ethyl-N-methylimidoformamide (43), N′-{2,5-dimethyl-4-[3-(2,2,2-trichloro-1-hydroxyethyl)-phenoxy]phenyl}-N-ethyl-N-methylimidoformamide (44), N′-{2,5-dimethyl-4-[3-(2,2,2-trichloro-1-methoxyethyl)phenoxy]phenyl}-N-ethyl-N-methylimidoformamide (45), N′-{4-[3-(1-ethoxyethyl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (46-1), N′-{4-[3-(1-methoxyethyl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methyl-imidoformamide (46-2), N-ethyl-N′-{4-[3-(1-hydroxyethyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (47), N-ethyl-N′-{4-[3-(1-hydroxy-1-methylbutyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (48), N-ethyl-N′-{4-[3-(1-hydroxy-1-methylprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methyl-imidoformamide (49), N-ethyl-N′-{4-[3-(1-hydroxy-1,3-dimethylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (50), N-ethyl-N′-{4-[3-(1-methoxy-1-methylprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (51), N-ethyl-N′-{4-[3-(1-methoxy-1,2-dimethylpropyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (52), N-ethyl-N′-{4-[3-(1-methoxyprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (53-1), N-ethyl-N′-{4-[3-(1-methoxyprop-2-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamideinium oxalate (53-2), N-ethyl-N′-{4-[3-(1-hydroxy-1-methylethyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (54), N-ethyl-N′-(4-{3-[hydroxy(phenyl)methyl]phenoxy}-2,5-dimethylphenyl)-N-methylimidoformamide (55), N-ethyl-N′-(4-{3-[methoxy-(phenyl)methyl]phenoxy}-2,5-dimethylphenyl)-N-methylimidoformamide (56-1), N-ethyl-N′-(4-{3-[methoxy(phenyl)methyl]phenoxy}-2,5-dimethylphenyl)-N-methylimido-formamideinium mesylate (56-2), N-ethyl-N′-(4-{3-[methoxy(phenyl)methyl]phenoxy}-2,5-dimethylphenyl)-N-methylimidoformamideinium oxalate (56-3), N-ethyl-N′-(4-{3-[methoxy(phenyl)methyl]phenoxy}-2,5-dimethylphenyl)-N-methylimidoformamideinium chloroide (56-4), N-ethyl-N′-{4-[3-(3-hydroxypropyl)phenoxy]-2,5-dimethylphenyl}-N-methylimidoformamide (57-1), N′-{4-[3-(3-hydroxypropyl)phenoxy]-2,5-di-methylphenyl}-N-isopropyl-N-methylimidoformamide (57-2), N′-{4-[3-(1-ethoxy-1-methylbut-3-en-1-yl)phenoxy]-2,5-dimethylphenyl}-N-isopropyl-N-methylimido-formamide (58), N′-{4-[3-(1-hydroxy-1-methylbut-3-en-1-yl)phenoxy]-2,5-dimethyl-phenyl}-N-isopropyl-N-methylimido-formamide (59), 2-[3-(2,5-dimethyl-4-{[(1e)-piperidin-1-ylmethylene]amino}-phenoxy)phenyl]pent-4-en-2-ol (60), N′-[2-chloro-4-(3-isopropylphenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide (61-1), N′-[2-chloro-4-(3-isopropylphenoxy)-5-methylphenyl]-N-isopropyl-N-methylimidoformamide (61-2), 2-chloro-4-(3-isopropyl-phenoxy)-5-methyl-N-[(1e)-piperidin-1-ylmethylene]-aniline (61-3), 2-chloro-4-(3-isopropylphenoxy)-5-methyl-N-[(1e)-(2-methylpiperidin-1-yl)methylene]anilin (61-4), N′-{4-[3-(2,2-dimethylpropyl)phenoxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide (62), N′-(2,5-dimethyl-4-{3-[(trimethylsilyl)methyl]-phenoxy}phenyl)-N-ethyl-N-methyl-imidoformamide (63), N′-[4-(3-cyclo-propylphenoxy)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide (64), N′-{4-[3-(1-methoxy-1-methylethyl)phenoxy]-2,5-dimethylphenyl}-N-methyl-N-propylimido-formamide (65-1), N-[(1e)-(2,6-dimethylmorpholin-4-yl)methylene]-4-[3-(1-methoxy-1-methylethyl)-phenoxy]-2,5-dimethylaniline, and N-ethyl-N′-[4-(3-isopropylphenoxy)-5-methyl-2-(trifluoromethyl)phenyl]-N-methylimidoformamide (66). 
   
   
       5 . A process for preparing a 3-substituted phenoxyphenylamidine and/or salt as claimed in  claim 1  which comprises at least one of the following steps (a) to (j):
 (a) reaction of nitrobenzene derivatives of the formula (III) with 3-substituted phenols of the formula (II) according to the reaction scheme below:   
     
       
         
         
             
             
         
       
       (b) reaction of nitrophenol derivatives of the formula (V) with 3-substituted phenyl derivatives of the formula (IV) according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       (c) reaction of anilines of the formula (VII) with 3-substituted phenols of the formula (II) according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       (d) reaction of aminophenols of the formula (XII) with 3-substituted phenyl derivatives of the formula (IV) according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       (e) reduction of the nitrophenyl ethers of the formula (VI) to aniline ethers of the formula (VIII) according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       (f) reaction of the aniline ethers of the formula (VIII) with
 (i) aminoacetals of the formula (XIII) or 
 (ii) with amides of the formula (XIV) or 
 (iii) with amines of the formula (XV) in the presence of ortho esters of the formula (XVI) 
 
       according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       (g) reaction of the aminophenols of the formula (XII) with
 (i) aminoacetals of the formula (XIII) or 
 (ii) with amides of the formula (XIV) or 
 (iii) with amines of the formula (XV) in the presence of ortho esters of the formula (XVI) 
 
       according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       (h) reaction of the aminophenols of the formula (VII) with
 (i) aminoacetals of the formula (XIII) or 
 (ii) with amides of the formula (XIV) or 
 (iii) with amines of the formula (XV) in the presence of ortho esters of the formula (XVI) according to the reaction scheme below: 
 
     
     
       
         
         
             
             
         
       
       (i) reaction of amidines of the formula (XI) with 3-substituted phenols of the formula (II) according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       (j) reaction of amidines of the formula (XI) with 3-substituted phenyl derivatives of the formula (IV) according to the reaction scheme below: 
     
     
       
         
         
             
             
         
       
       where in the above schemes 
       Z represents a leaving group; 
       M is 0 to 12, 
       R 1  to R 9  have the above meanings; 
       and 
       R 10  to R 12  independently of one another are selected from the group consisting of hydrogen, C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl or C 5-18 -aryl or C 7-19 -arylalkyl, C 7-19 -alkylaryl groups and in each case R 10  with R 12 , R 10  with R 11  or R 11  with R 12  together with the atom to which they are attached, if appropriate with further carbon, nitrogen, oxygen or sulfur atoms, may form a five-, six- or seven-membered carbo- or heterocyclic ring; 
       R 13  and R 14  independently of one another independently of one another are selected from the group consisting of hydrogen, C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl or C 5-18 -aryl or C 7-19 -arylalkyl groups and together with the atom to which they are attached may form a five-, six- or seven-membered ring. 
     
   
   
       6 . A 3-substituted nitrophenyl ether of formula (VI); 
     
       
         
         
             
             
         
       
       in which 
       m and R 4  to R 8  have the above meanings. 
     
   
   
       7 . A 3-substituted phenoxyphenylamidine and/or salt thereof prepared using a 3-substituted nitrophenyl ether of  claim 6 . 
   
   
       8 . A 3-substituted aniline ether of formula (VIII) 
     
       
         
         
             
             
         
       
       in which 
       m and R 4  to R 8  have the above meanings. 
     
   
   
       9 . A 3-substituted phenoxyphenylamidine and/or salt thereof prepared using a 3-substituted nitrophenyl ether of the formula (VIII), as claimed in  claim 7 . 
   
   
       10 . An aminoacetal of formula (XIII) 
     
       
         
         
             
             
         
       
       in which 
       R 1  to R 3  have the above meanings, 
       R 13  and R 14  independently of one another are selected from the group consisting of hydrogen, C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl or C 5-18 -aryl or C 7-19 -arylalkyl groups and together with the oxygen atoms to which they are attached may form a five-, six- or seven-membered ring. 
     
   
   
       11 . A composition for controlling unwanted microorganisms, comprising at least one 3-substituted phenoxyphenylamidine and/or salt thereof as claimed in  claim 1 . 
   
   
       12 . A composition comprising a 3-substituted phenoxyphenylamidine and/or salt thereof as claimed in  claim 1  and/or mixtures thereof for controlling unwanted microorganisms. 
   
   
       13 . A method for controlling unwanted microorganisms, wherein the at least one 3-substituted phenoxyphenylamidine and/or salt thereof as claimed in  claim 1  is applied to the microorganisms and/or a habitat thereof. 
   
   
       14 . Seed treated with at least one 3-substituted phenoxyphenylamidine and/or salt thereof as claimed in  claim 1 . 
   
   
       15 . A method for treating seed comprising using 3-substituted phenoxyphenylamidines as claimed in  claim 1 . 
   
   
       16 . A method for treating a transgenic plant comprising using a 3-substituted phenoxyphenylamidine and/or salt thereof as claimed in  claim 1 . 
   
   
       17 . A method for treating seed of a transgenic plant comprising using a 3-substituted phenoxyphenylamidines and/or salt thereof as claimed  claim 1 . 
   
   
       18 . A method for protecting seed against unwanted microorganisms by using seed treated with at least one 3-substituted phenoxyphenylamidine as claimed in  claim 1 .