Title of Invention	BIPHENYLCARBOXAMIDES
Abstract	1. Biphenylcarboxamides of the formula (I) in which R1 and R2 independently of one another represent hydrogen, halogen, cyano, nitro, having in each case 1 to 13 fluorine, chlorine and/or bromine atoms, m represents 1, 2, 3 or 4, where R1 represents identical or different radicals if m represents 2, 3 or 4, n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3, R3 represents hydrogen, hydroxyl, haloalkyl having 1 to 7 halogen atoms, alkylsulphenyl, haloalkylsulphenyl having 1 to 7 halogen atoms, , carbamoyl, Y represents carbonyl or represents which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, having in each case 1 to 13 fluorine, chlorine and/or bromine atoms and A represents a radical of the formula where R4 represents hydrogen, cyano, halogen, nitro, having 1 to 5 halogen atoms, cycloalkyl, having 1 to 5 halogen atoms, having 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C1-C4 alkyl and R5 represents hydrogen, halogen, cyano, alkoxy or and R6 represents hydrogen, having 1 to 5 halogen atoms, cycloalkyl, haloalkylthio- 1 to 5 halogen atoms, 1 to 5 halogen atoms or phenyl, or A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R9 represents halogen, cyano or C1-C4-alkyl or C1-C4-haloalkoxy having 1 to 5 halogen atoms, or A represents a radical of the formula R10 and R11 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R12 represents hydrogen, C1-C4-alkyl or hydrogen, or A represents a radical of the formula or R13 represents hydrogen, halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-haloalkoxy having 1 to 5 halogen atoms or C1-C4-haloalkylthio having 1 to 5 halogen atoms, represents a radical of the formula R14 represents halogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio having 1 to 5 halogen atoms, or C1-C4-haloalkoxy having 1 to 5 halogen atoms and R15 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkoxy having 1 to 5 halogen atoms, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl, or represents a radical of the formula

Title of Invention

BIPHENYLCARBOXAMIDES

Abstract

1. Biphenylcarboxamides of the formula (I) in which R1 and R2 independently of one another represent hydrogen, halogen, cyano, nitro, having in each case 1 to 13 fluorine, chlorine and/or bromine atoms, m represents 1, 2, 3 or 4, where R1 represents identical or different radicals if m represents 2, 3 or 4, n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3, R3 represents hydrogen, hydroxyl, haloalkyl having 1 to 7 halogen atoms, alkylsulphenyl, haloalkylsulphenyl having 1 to 7 halogen atoms, , carbamoyl, Y represents carbonyl or represents which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, having in each case 1 to 13 fluorine, chlorine and/or bromine atoms and A represents a radical of the formula where R4 represents hydrogen, cyano, halogen, nitro, having 1 to 5 halogen atoms, cycloalkyl, having 1 to 5 halogen atoms, having 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C1-C4 alkyl and R5 represents hydrogen, halogen, cyano, alkoxy or and R6 represents hydrogen, having 1 to 5 halogen atoms, cycloalkyl, haloalkylthio- 1 to 5 halogen atoms, 1 to 5 halogen atoms or phenyl, or A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R9 represents halogen, cyano or C1-C4-alkyl or C1-C4-haloalkoxy having 1 to 5 halogen atoms, or A represents a radical of the formula R10 and R11 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R12 represents hydrogen, C1-C4-alkyl or hydrogen, or A represents a radical of the formula or R13 represents hydrogen, halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-haloalkoxy having 1 to 5 halogen atoms or C1-C4-haloalkylthio having 1 to 5 halogen atoms, represents a radical of the formula R14 represents halogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio having 1 to 5 halogen atoms, or C1-C4-haloalkoxy having 1 to 5 halogen atoms and R15 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkoxy having 1 to 5 halogen atoms, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl, or represents a radical of the formula

Full Text	FORM 2 THE PATENTS ACT 1970 [39 OF 1970] COMPLETE SPECIFICATION [See Section 10] "BIPHENYLCARBOXAMIDES" BAYER CROPSCIENCE AKTIENGESELLSCHAFT, a German company of Alfred-Nobel-Str. 50, 40789 Monheim, Germany, The following specification particularly describes the nature of the invention and the manner in which it is to be performed :- The present invention relates to novel biphenylcarboxamides, to a plurality of processes for their preparation and to their use for controlling unwanted micro-organisms. It is already known that numerous carboxanilides have fungicidal properties (compare WO 93/11 117, WO 99/09 013, WO 00/14 071, EP-A 0 545 099 and EP-A 0 589 301). The activity of these substances is good; however, in some cases, for example at low application rates, it is unsatisfactory. This invention now provides novel biphenylcarboxamides of the formula (I) in which independently of one another represent hydrogen, halogen, cyano, nitro, alkoxy or having in each case 1 to 13 fluorine, chlorine and/or bromine atoms, m represents 1, 2, 3 or 4, where R1 represents identical or different radicals if m represents 2, 3 or 4, n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3, Le A 35 963-Foreign Countries R3 represents hydrogen, hydroxyl, having 1 to 7 halogen atoms, sulphenyl having 1 to 7 halogen atoms, carbamoyl, Y represents carbonyl or represents which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, haloalkyl, having in each case 1 to 13 fluorine, chlorine and/or bromine atoms and A represents a radical of the formula R4 represents hydrogen, cyano, halogen, nitro, haloalkyl having 1 to 5 halogen atoms, alkoxy, having 1 to 5 halogen atoms, alkylthio, having 1 to 5 halogen atoms, aminocar- bonyl or aminocarbonyl- R5 represents hydrogen, halogen, cyano, R6 represents hydrogen, having 1 to 5 halogen atoms, alkyl, having 1 to 5 halogen atoms, having 1 to 5 halogen atoms or phenyl, or A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, halogen, alkyl or having 1 to 5 halogen atoms and R9 represents halogen, cyano or having 1 to 5 halogen atoms, or A represents a radical of the formula R10 and R11 independently of one another represent hydrogen, halogen, having 1 to 5 halogen atoms and R12 represents hydrogen,' or A represents a radical of the formula R13 represents hydrogen, halogen, hydroxyl, cyano, haloalkyl having 1 to 5 halogen atoms, having 1 to 5 halogen atoms or having 1 to 5 halogen atoms, or A represents a radical of the formula R14 represents halogen, hydroxyl, cyano, having 1 to 5 halogen atoms, haloalkylthio having 1 to 5 halogen atoms, or having 1 to 5 halogen atoms and R15 represents hydrogen, halogen, cyano, having 1 to 5 halogen atoms, haloalkoxy having 1 to 5 halogen atoms, or or R16 represents having 1 to 5 halogen atoms and R17 represents X1 represents a sulphur atom, represents SO, p represents 0,1 or 2, where R17 represents identical or different radicals if p represents 2, or A represents a radical of the formula where R18 represents having 1 to 5 halogen atoms, or A represents a radical of the formula where or R19 represents having 1 to 5 halogen atoms, Le A 35 963-Foreign Countries -5- A represents a radical of the formula R20 represents halogen, cyano, having 1 to 5 halogen atoms, 5 R21 represents hydrogen, halogen, having 1 to 5 halogen atoms and R22 represents hydrogen, cyano, having 1 to 5 halogen atoms, 10 carbonyl or optionally substituted phenylsulphonyl or benzoyl, or A represents a radical of the formula R23 and R24 independently of one another represent hydrogen, halogen, 15 amino, having 1 to 5 halogen atoms and R25 represents hydrogen, halogen, having 1 to 5 halogen atoms, or 20 A represents a radical of the formula R26 and R27 independently of one another represent hydrogen, halogen, amino, nitro, having 1 to 5 halogen atoms and Le A 35 963-Foreign Countries R28 represents hydrogen, halogen, having 1 to 5 halogen atoms, or A represents a radical of the formula R29 represents hydrogen, halogen, amino, alkyl)amino, cyano, having 1 to 5 halogen atoms and R30 represents halogen, having 1 to 5 10 halogen atoms, or A represents a radical of the formula R31 represents hydrogen, halogen, amino, 15 alkyl)amino, cyano, having 1 to 5 halogen atoms and R32 represents halogen, having 1 to 5 halogen atoms, or 20 A represents a radical of the formula R33 represents halogen, having 1 to 5 halogen atoms, or 25 A represents a radical of the formula Le A 35 963-Foreign Countries R34 represents hydrogen or C1-C4-alkyl and R35 represents halogen or C1-C4-alkyl, or 5 A represents a radical of the formula R36 represents having 1 to 5 halogen atoms, or 10 A represents a radical of the formula where R37 represents hydrogen, halogen or Depending on the nature of the substituents, the compounds of the formula (I) can be 15 present as geometrical and/or optical isomers or isomer mixtures of varying com- positions. The invention relates both to the use of the pure isomers and to that of the isomer mixture. Furthermore, it has been found that biphenylcarboxamides of the formula (I) are 20 obtained when a) carboxylic acid derivatives of the formula (II) Le A 35 963-Foreign Countnes 8- A is as defined above and G represents halogen, hydroxyl or C1-C6-alkoxy, are reacted with aniline derivatives of the formula (HI) (in) in which R1, R2, m, n, R3 and Y are as defined above, or b) if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, carboxamide derivatives of the formula (IV) in which R1, m, R3 and A are as defined above, are reacted with boronic acid derivatives of the formula (V) in which Le A 35 963-Foreign Countries -9- R2, n and Y are as defined above and G1 and G2 each represent hydrogen or together represent tetramethylethylene, in the presence of a catalyst, if appropriate in the presence of an acid binder 5 and if appropriate in the presence of a diluent, or c) carboxamide boronic acid derivatives of the formula (VI) in which 10 R1, m, R3 and A are as defined above and G1 and G2 each represent hydrogen or together represent tetramethylethylene, are reacted with phenyl derivatives of the formula (VII) 15 in which R2, n and Y are as defined above, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, 20 or d) carboxamide derivatives of the formula (IV) Le A 35 963-Foreign Countries in which R1, m, R3 and A are as defined above, are reacted with phenyl derivatives of the formula (VII) in which R2, n and Y are as defined above, in the presence of a palladium or platinum catalyst and in the presence of 4,4,4',4,,5,5,5',5'-octamethyl-2,2'-bis-l,3,2-dioxaborolane, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. Finally, it has been found that the novel biphenylcarboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials. Surprisingly, the biphenylcarboxamides of the formula (I) according to the invention have considerably better fungicidal activity than the constitutionally most similar active compounds of the prior art having the same direction of action. The formula (I) provides a general definition of the biphenylcarboxamides according to the invention. Preference is given to biphenylcarboxamides of the formula (I) in which R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, haloalkyl, having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, Le A 35 963-Foreign Countries m represents 1, 2 or 3, where R1 represents identical or different radicals if m represents 2 or 3, n represents 1, 2 or 3, where R2 represents identical or different radicals if n 5 represents 2 or 3, R3 represents hydrogen, hydroxy], having 1 to 5 halogen atoms, 10 sulphenyl having 1 to 5 halogen atoms, Y represents carbonyl or represents which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, 15 alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy and/or C1-C4-haloalkylthio having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, and A represents a radical of the formula where 20 R4 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, amino- 25 carbonyl, aminocarbonylmethyl or aminocarbonylethyl, R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and Le A 35 963-Foreign Countries R6 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl, or A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and 10 R9 represents fluorine, chlorine, bromine, cyano, methyl, ethyl or C1-C2- haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula 15 R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or 20 A represents a radical of the formula where R13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-haloalkoxy having 1 to 5 fluorine, , Le A 35 963-Foreign Countries 13 chlorine and/or bromine atoms or C1-C2-haloalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms, or represents a radical of the formula where R14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4 alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio or C1-C2-haloalkoxy having 1 to 5 fluorine, 10 chlorine and/or bromine atoms and R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, C1-C2- haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, 15 C1 -C2-alkylsulphinyl or C1-C2-alkylsulphonyl, or A represents a radical of the formula where R16 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, 20 chlorine and/or bromine atoms and R17 represents methyl or ethyl, X1 represents a sulphur atom, represents SO, SO2 or CH2 and p represents 0,1 or 2, where R17 represents identical or different radicals if p represents 2, 25 or A represents a radical of the formula , Le A 35 963-Foreign Countries where R18 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or 5 A represents a radical of the formute where R19 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or 10 A represents a radical of the formula R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, 15 R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R22 represents hydrogen, methyl, ethyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-alkoxy-C1-C2-alkyl, 20 hydroxymethyl, hydroxyethyl, methylsulphonyl or dimethylamino- sulphonyl, or A represents a radical of the formula Le A 35 963-Foreign Countries R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula where R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or 15 C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula where 20 R29 represents hydrogen, fluorine, chlorine, bromine, amino,C1-C4- alkylamino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2 haloalkyl having I to 5 fluorine, chlorine and/or bromine atoms and R30 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, , Le A 35 963-Foreign Countries or A represents a radical of the formula R31 represents hydrogen, fluorine, chlorine, bromine, amino, C1-C4-alkyl-amino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R32 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or 10 A represents a radical of the formula R33 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2- haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or 15 A represents a radical of the formula where R34 represents hydrogen, methyl or ethyl and R35 represents fluorine, chlorine, bromine, methyl or ethyl, or 20 A represents a radical of the formula where R36 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, Le A 35 963-Foreign Countries R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl. 5 Particular preference is given to biphenylcarboxamides of the formula (I) in which R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s- butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, 10 trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifiuoromethoxy, trifluoromethylthio, difluorochloromethylthio, m represents 1 or 2, where R1 represents identical or different radicals if m represents 2, 15 n represents 1 or 2, where R2 represents identical or different radicals if n represents 2, R3 represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, 20 t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, methoxymethyl, cyanomethyl, difluoromethyl, methylsulphenyl, trichloro-methylsulphenyl or acetyl, Y represents carbonyl or represents -CH2- or -(CH2)2-, each of which is 25 optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, i- propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t- butylthio, trifluoromethyl, trifiuoromethoxy and trifluoromethylthio, and 30 A represents a radical of the formula Le A 35 963-Foreign Countries R4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio and R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and R6 represents hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl, or A represents a radical of the formula R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and R9 represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy, or A represents a radical of the formula Le A 35 963-Foreign Countries difluorochloromethyl or trichloromethyl and R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula R13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichlo¬ romethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, 10 trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluoro- chloromethylthio or trichloromethylthio, or A represents a radical of the formula 15 R14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichlorome¬thyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, tri¬fluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloro- 20 methoxy or trichloromethoxy and R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, 25 difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulphonyl, or , Le A 35 963-Foreign Countries R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro- chloromethyl or trichloromethyl and R17 represents methyl or ethyl, X1 represents a sulphur atom, represents SO, SO2 or CH2 and p represents 0,1 or 2, where R17 represents identical or different radicals if p represents 2, or 10 A represents a radical of the formula where R18 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro- chloromethyl or trichloromethyl, or 15 A represents a radical of the formula where R19 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or 20 A represents a radical of the formula Le A 35 963-Foreign Countries R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloro-methyl, R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tri¬fluoromethyl, difluoromethyl or trichloromethyl and R22 represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl, or A represents a radical of the formula 10 R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tri- 15 fluoromethyl, difluoromethyl, difluorochloromethyl or trichloro- methyl, or A represents a radical of the formula 20 R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloro- 25 methyl, or Lg_A 35 963-Foreign Countnes represents a radical of the formula R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R30 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R32 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula R33 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula , Le A 35 963-Foreign Countries R34 represents hydrogen, methyl or ethyl and R35 represents fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula 10 R36 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro-chloromethyl or trichloromethyl, or A represents a radical of the formula R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl. Very particular preference is given to biphenylcarboxamides of the formula (I) in which 15 R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifiuoromethoxy, trifluoromethylthio, 20 m represents 1 or 2, where R1 represents identical or different radicals if m represents 2, n represents 1, 25 R3 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, t-butyl, cyclo- propyl, cyclopentyl or cyclohexyl, Le A 35 963-Foreign Countries Y represents carbonyl or represents -CH2- or -(CH2)2-, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, methyl, i-propyl, t-butyl, methoxy, i- propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl, 5 trifluoromethoxy and trifluoromethylthio, and A represents a radical of the formula R4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, i- 10 propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluoro- chloromethyl or trichloromethyl and R5 represents hydrogen, fluorine, chlorine, bromine, iodine or methyl and R6 represents hydrogen, methyl, trifluoromethyl or phenyl, or 15 A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl and 20 R9 represents fluorine, chlorine, bromine, methyl or trifluoromethoxy, or A represents a radical of the formula Le A 35 963-Foreign Countries R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difiuoromethyl, trifluoromethyl or trichloromethyl and R12 represents hydrogen, fluorine, chlorine, bromine or methyl, or A represents a radical of the formula where R13 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difiuoromethyl, trifluoromethyl or trichloromethyl, 10 or A represents a radical of the formula where R14 represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difiuoromethyl or trichloromethyl and 15 R15 represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, i- propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difiuoro¬methyl, trichloromethyl, methylsulphinyl or methylsulphonyl, or A represents a radical of the formula 20 R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and R17 represents methyl or ethyl, X1 represents a sulphur atom, represents SO, SO2 or CH2 and 25 p represents 0,1 or 2, where R17 represents identical or different radicals if p represents 2, Le A 35 963-Foreign Countries or A represents a radical of the formula R18 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula where R19 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or 10 A represents a radical of the formula R20 represents fluorine, chlorine, bromine, methyl, i-propyl, trifluoro¬ methyl, difluoromethyl or trichloromethyl, R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, 15 trifluoromethyl, difluoromethyl or trichloromethyl and R22 represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl, 20 R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and Le A 35 963-Foreign Countries R25 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoro¬methyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and R28 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoro- 10 methyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, 15 dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloro- methyl and R30 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, 20 R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloro¬methyl and Le A 35 963-Foreign Countries R32 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula 10 R33 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula R34 represents hydrogen, methyl or ethyl and R35 represents fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula 15 R36 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula 20 R37 represents hydrogen, fluorine, chlorine, bromine or methyl. Especially preferred are biphenylcarboxamides of the formula (I) in which R1 represents hydrogen, fluorine, chlorine, methyl, Le A 35 963-Foreign Countries R2 represents hydrogen, m represents 1 or 2, where R1 represents identical or different radicals if m represents 2, n represents 1, R3 represents hydrogen, Y represents and A represents a radical of the formula R4 represents methyl, monofluoromethyl, difluoromethyl or trifluoromethyl and R5 represents hydrogen, fluorine, chlorine or methyl and R6 represents methyl, or A represents a radical of the formula R7 and R8 represent hydrogen and R9 represents methyl, or A represents a radical of the formula R10 and R11 represent hydrogen and R12 represents methyl, or Le A 35 963-Foreign Countries A represents a radical of the formula where R13 represents iodine, methyl, difluoromethyl or trifluoromethyl, or A represents a radical of the formula R20 represents methyl, trifiuoromethyl or difluoromethyl, R21 represents hydrogen, fluorine, chlorine, methyl, trifiuoromethyl or difluoromethyl and R22 represents hydrogen, methyl, ethyl, trifiuoromethyl or methoxymethyl, or A represents a radical of the formula R23 and R24 represent hydrogen and R25 represents methyl, or A represents a radical of the formula R26 and R27 represent hydrogen and R28 represents methyl, or Le A 35 963-Foreign Countries A represents a radical of the formula R29 represents amino, methylamino, dimethylamino, methyl or trifluoromethyl and 5 R30 represents methyl, trifluoromethyl or difluoromethyl, or A represents a radical of the formula R31 represents amino, methylamino, dimethylamino, methyl or 10 trifluoromethyl and R32 represents methyl, trifluoromethyl or difluoromethyl, or A represents a radical of the formula 15 R36 represents methyl or trifluoromethyl. Moreover, emphasis is given to compounds of the formula (I) in which R3 represents hydrogen. Moreover, emphasis is given to compounds of the formula (I) in which R2 represents 20 hydrogen. Moreover, emphasis is given to compounds of the formula (I) in which Y represents Moreover, emphasis is given to compounds of the formula (I) in which R1 represents hydrogen, fluorine, chlorine or methyl and especially hydrogen or fluorine. Le A 35 963-Foreign Countries Moreover, emphasis is given to compounds of the formula (I) in which m represents 0,1 or 2. Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula where R4, R5 and R6 are as defined above. Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula 5 10 15 where R7, R8 and R9 are as defined above. Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula where R13 is as defined above. Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula 20 where R29 and R30 are as defined above. Le A 35 963-Foreign Countries Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula where R36 is as defined above. 5 Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, even in combination with heteroatoms, such as, for example, in alkoxy. 10 Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitutions the substituents can be identical or different. Halogen-substituted radicals, such as, for example, haloalkyl, are mono- or polyhalogenated. In the case of polyhalogenation, the halogen atoms can be identical 15 or different. Here, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine. However, the general or preferred radical definitions or illustrations listed above can also be combined with one another as desired, i.e. including combinations between 20 the respective ranges and preferred ranges. They apply to the end products and, correspondingly, to precursors and intermediates. Moreover, individual definitions may not apply. Using 2-methyl-4-trifluoromethyl-l,3-thiazole-5-carbonyl chloride and (2,2-difluoro- 25 l,3-benzodioxol-5-yl)phenylamine as starting materials, the course of the process (a) according to the invention can be illustrated by the formula scheme below. Le A 35 963-Foreign Countries Using N-(2-bromophenyl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide and 2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxin-6-ylboronic acid as starting materials and a catalyst, the course of the process (b) according to the invention can be illustrated by the formula scheme below. 10 Using 2- {[(5-fluoro-l ,3-dimethyI-l//-pyrazol-4-yl)carbonyl]amino}phenylboronic acid and 6-bromo~2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxine as starting materials and a catalyst, the course of the process (c) according to the invention can be illustrated by the formula scheme below. 15 Using N-(2-bromophenyl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide and 6-bromo-2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxine as starting materials and a catalyst and 4,4,4,,4,,5,5,5,,5'-octamethyl-2,2'-bis-l,3,2-dioxaborolane, the course of the process (d) according to the invention can be illustrated by the formula scheme below. Le A 35 963-Foreign Countries Explanation of the processes and intermediates The formula (II) provides a general definition of the carboxylic acid derivatives 5 required as starting materials for carrying out the process (a) according to the invention. In this formula, A preferably has those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals. G preferably represents chlorine, 10 bromine, hydroxyl, methoxy or ethoxy, particularly preferably chlorine, hydroxy or methoxy. The carboxylic acid derivatives of the formula (II) are known or can be prepared by known processes (cf. WO 93/11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 15 0 589 313). The formula (HI) provides a general definition of the aniline derivatives required as reaction components for carrying out the process (a) according to the invention. In this formula, R1, R2, m, n, R3 and Y preferably have those meanings which have 20 already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. The aniline derivatives of the formula (III) are novel. Some of them can be prepared 25 by known methods (cf. EP-A 0 545 099 and EP-A 0 589 301). Moreover, aniline derivatives of the formula (in) are obtained by t Le A 35 963-Foreign Countries e) reacting 2-haloaniline derivatives of the general formula (VIII) in which R1, m and R3 are as defined above and Hal represents halogen, with boronic acid derivatives of the formula (V) (V) in which R2, n, Y, G1 and G2 are as defined above, if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent, and if appropriate in the presence of a catalyst, or f) reacting anilineboronic acids of the formula (IX) in which R1, m, R3, G1 and G2 are as defined above, with phenyl derivatives of the formula (VII) Le A 35 963-Foreign Countries in which R2, n and Y are as defined above, 5 if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent, and if appropriate in the presence of a catalyst. 10 15 The formula (VIII) provides a general definition of the 2-haloaniline derivatives required as reaction components for carrying out the process (e) according to the invention. In this formula, R1, m and R3 preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. Hal preferably represents fluorine, chlorine or bromine, particularly preferably chlorine or bromine. The 2-haloaniline derivatives of the formula (VIII) are known and/or can be prepared from the corresponding nitro compounds by reduction. If R3 does not represent 20 hydrogen, the compounds of the formula (VIII) can be obtained by known derivatizations of the resulting aniline derivatives. The boronic acid derivatives of the formula (V) furthermore required as starting materials for carrying out the process (e) according to the invention are illustrated in 25 more detail below, in connection with the process (b) according to the invention. The formula (IX) provides a general definition of the anilineboronic acids required as reaction components for carrying out the process (f) according to the invention. In Le A 35 963-Foreign Countries this formula, R1, m and R3 preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. G1 and G2 5 preferably each represent hydrogen or together represent tetramethylethylene. The anilineboronic acids of the formula (IX) are known and/or can be obtained by known methods. 10 The phenyl derivatives of the formula (VII) furthermore required as starting materials for carrying out the process (f) according to the invention are illustrated in more detail below, in connection with the process (d) according to the invention. The formula (IV) provides a general definition of the carboxamide derivatives 15 required as starting materials for carrying out the process (b) and (d) according to the invention. In this formula, R1, m, R3 and A preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. 20 The carboxamide derivatives of the formula (IV) are known or can be prepared by known processes (cf., for example, WO 91/01311, EP-A 0 371 950). The formula (V) provides a general definition of the boronic acid derivatives required 25 as starting materials for carrying out the processes (b) and (e) according to the invention. In this formula, R2, n and Y preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. G1 30 and G2 preferably each represent hydrogen or together represent tetramethylethylene. The boronic acid derivatives of the formula (V) are known and/or can be prepared by Le A 35 963-Foreign Countries known processes (cf., for example, WO 01/90084 and US 5,633,218). They are obtained, for example, by g) reacting phenyl derivatives of the formula (VII) in which R2, n and Y are as defined above, with boric acid esters of the formula (X) 10 15 in the presence of magnesium, if appropriate in the presence of a diluent (for example tetrahydrofuran). The formula (X) provides a general definition of the boric acid esters required as reaction components for carrying out the process (g) according to the invention. In 20 this formula, R38 preferably represents methyl, ethyl, n- or i-propyl, particularly preferably methyl or ethyl. The boric acid esters of the formula (X) are known chemicals for synthesis. 25 The formula (VI) provides a general definition of the carboxamide boronic acid derivatives required as reaction components for carrying out the process (c) according to the invention. In this formula, R1, m, R3 and A preferably have those meanings which have already been mentioned in connection with the description of Le A 35 963-Foreign Countries the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. G1 and G2 preferably each represent hydrogen or together represent tetramethylethylene. 5 The carboxamide boronic acid derivatives of the formula (VI) are known and/or can be prepared by known processes. The formula (VII) provides a general definition of the phenyl derivatives required as 10 starting materials for carrying out the processes (c), (d), (f) and (g) according to the invention. In this formula, R2, n and Y preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. 15 The phenyl derivatives of the formula (VII) are known or can be prepared by known processes (cf. Synth. Commun. 2000, 30, 665-669, Synth. Commun. 1999. 29, 1697-1701). 20 Suitable acid binders for carrying out the processes (a), (b), (c), (d), (e) and (f) according to the invention are in each case all inorganic and organic bases customary for such reactions. Preference is given to using alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or else ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, 25 potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, tributyl-amine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylamino-pyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicyclo- 30 undecene (DBU). However, it is also possible to work in the absence of an additional acid binder, or to employ an excess of the amine component so that it simultaneously acts as acid binder. , Le A 35 963-Foreign Countries Suitable diluents for carrying out the processes (a), (b), (c), (d), (e) and (f) according to the invention are in each case all customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, 5 such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as 10 acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethylsulphoxide, or sulphones, such as sulpholane. 15 When carrying out the processes (a), (b), (c), (d), (e) and (f) according to the invention, the reaction temperatures can in each case be varied within a relatively wide range. In general, the processes are carried out at temperatures between 0°C and 140°C, preferably between 10°C and 120°C. 20 The processes (a), (b), (c), (d), (e) and (f) according to the invention are generally each carried out under atmospheric pressure. However, in each case it is also possible to operate under elevated or reduced pressure. When carrying out the process (a) according to the invention, in general 1 mol or else 25 an excess of aniline derivative of the formula (HI) and from 1 to 3 mol of acid binder are employed per mole of acid halide of the formula (H). However, it is also possible to employ the reaction components in other ratios. Work-up is carried out by customary methods. In general, water is added to the reaction mixture and the organic phase is separated off and, after drying, concentrated under reduced pressure. The 30 residue that remains may, if appropriate, be freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization. Le A 35 963-Foreign Countries When carrying out the process (b) according to the invention, in general 1 mol or else an excess of boronic acid derivative of the formula (V) and from 1 to 5 mol of acid binder are employed per mole of carboxamide of the formula (IV). However, it is also possible to employ the reaction components in other ratios. Work-up is carried 5 out by customary methods. In general, water is added to the reaction mixture and the precipitate is separated off and dried. The residue that remains may, if appropriate, be freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization. 10 When carrying out the process (c) according to the invention, in general 1 mol or else an excess of phenyl derivative of the formula (VII) and from 1 to 10 mol of acid binder and from 0.5 to 5 mol% of a catalyst are employed per mole of carboxamide boronic acid derivative of the formula (VI). However, it is also possible to employ the reaction components in other ratios. Work-up is carried out by customary 15 methods. In general, water is added to the reaction mixture and the precipitate is separated off and dried. The residue that remains may, if appropriate, be freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization. 20 When carrying out the process (d) according to the invention, in general 1 mol or else an excess of phenyl derivative of the formula (VII) and from 1 to 5 mol of acid binder and from 1 to 5 mol of a catalyst are employed per mole of carboxamide derivative of the formula (IV). However, it is also possible to employ the reaction components in other ratios. Work-up is carried out by customary methods. In general, 25 water is added to the reaction mixture and the precipitate is separated off and dried. The residue that remains may, if appropriate, be freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization. The substances according to the invention have potent microbicidal activity and can 30 be employed for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials. Le A 35 963-Foreign Countries Fungicides can be employed in crop protection for controlling Plasmodiophoro-mycetes, Oomycetes, Chytndiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. 5 Bactericides can be employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae. Some pathogens causing fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation: 10 Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans; 15 Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara species, such as, for example, Plasmopara viticola; Bremia species, such as, for example, Bremia lactucae; Peronospora species, such as, for example, Peronospora pisi or P. brassicae; 20 Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Podosphaera species, such as, for example, Podosphaera leucotricha; Venturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea 25 (conidia form: Drechslera, syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita; 30 Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Tilletia species, such as, for example, Tilletia caries; Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Le A 35 963-Foreign Countries Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; 5 Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; and Pseudocercosporella species, such as, for example, Pseudocercosporella 10 herpotrichoides. The active compounds according to the invention also show a strong invigorating action in plants. Accordingly, they are suitable for mobilizing the internal defences of the plant against attack by unwanted microorganisms. 15 In the present context, plant-invigorating (resistance-inducing) compounds are to be understood as meaning substances which are capable of stimulating the defence system of plants such that, when the treated plants are subsequently inoculated with unwanted microorganisms, they display substantial resistance to these 20 microorganisms. In the present case, unwanted microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. The compounds according to the invention can thus be used to protect plants "within a certain period of time after 25 treatment against attack by the pathogens mentioned. The period of time for which this protection is achieved generally extends for 1 to 10 days, preferably 1 to 7 days, from the treatment of the plants with the active compounds. The fact that the active compounds are well tolerated by plants at the concentrations 30 required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. Le A 35 963-Foreign Countries The active compounds according to the invention are also suitable for increasing the yield of crops. In addition, they show reduced toxicity and are well tolerated by plants. If appropriate, the active compounds according to the invention can, at certain 5 concentrations and application rates, also be employed as herbicides, for regulating plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates or precursors in the synthesis of other active compounds. According to the invention, it is possible to treat all plants and parts of plants. Plants 10 are to be understood here as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant 15 cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested material 20 and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds. The treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or 25 storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating. 30 In the protection of materials, the compounds according to the invention can be employed for protecting industrial materials against infection with, and destruction by, unwanted microorganisms. Le A 35 963-Foreign Countries Industrial materials in the present context are understood as meaning non-living materials which have been prepared for use in industry. For example, industrial materials which are intended to be protected by active compounds according to the invention from microbial change or destruction can be tackifiers, sizes, paper and 5 board, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be infected with, or destroyed by, microorganisms. Parts of production plants, for example cooling-water circuits, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials which may be mentioned within the 10 scope of the present invention are preferably tackifiers, sizes, paper and board, leather, wood, paints, cooling lubricants and heat-transfer liquids, particularly preferably wood. Microorganisms capable of degrading or changing the industrial materials which may 15 be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms. The active compounds according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae. 20 Microorganisms of the following genera may be mentioned as examples: Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, 25 Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, 30 Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, and Le A 35 963-Foreign Countries Staphylococcus, such as Staphylococcus aureus. Depending on their particular physical and/or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, 5 emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations. These formulations are produced in a known manner, for example by mixing the 10 active compounds with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or 15 alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as 20 dimethylformamide or dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such 25 as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic 30 material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for , Le A 35 963-Foreign Countries example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, aryl-sulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignosulphite waste liquors and methylcellulose. 5 Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils. 10 It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. 15 The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can, as such or in their 20 formulations, also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to broaden, for example, the activity spectrum or to prevent development of resistance. In many cases, synergistic effects are obtained, i.e. the activity of the mixture is greater than the activity of the individual components. 25 Suitable mixing components are, for example, the following compounds: Fungicides: 2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl; aldimorph; amidofklumet; ampropylfos; ampropylfos-potas- 30 sium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl; benzamacril; benzamacril- isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole; Le A 35 963-Foreign Countries bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvone; chinomethionat; chlobenthiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid; cymoxanil; 5 cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; diclo- mezine; dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap; diphenyl- amine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon; 10 edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fen- hexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulphamide; flutolanil; 15 flutriafol; folpet; fosetyl-Al; fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole; imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tris(albesil); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; 20 isoprothiolane; isovaledione; kasugamycin; kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl; metalaxyl-M; metconazole; methasulphocarb; methmroxam; metiram; metominostrobin; met- sulphovax; mildiomycin; myclobutanil; myclozolin; 25 natamycin; nicobifen; nitrothal-isopropyl; noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen; phthalide; pic- oxystrobin; piperalin; polyoxins; polyoxorim; probenazole; prochloraz; procymidone; 30 propamocarb; propanosine-sodium; propiconazole; propineb; proquinazid; pro- thioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil; pyroquilon; pyroxyfur; pyrrolenitrine; Le A 35 963-Foreign Countries quinconazole; quinoxyfen; quintozene; simeconazole; spiroxamine; sulphur; tebuconazole; tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid; tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide; tricyclamide; tri- 5 cyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole; uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide; (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl] ethyl] -3- methyl-2-[(methylsulphonyl)amino]butanamide; 1 -(1 -naphthalenyl)-1 H-pyrrole-2,5-dione; 10 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; actinovate; cis-1 -(4-chlorophenyl)-2-( 1H-1,2,4-triazol-1 -yl)cycloheptanol; 15 methyl 1-(2,3-dihydro-2,2-dimethyl-1 H-inden-1 -yl)-1 H-imidazole-5-carboxylate; monopotassium carbonate; N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide; N-butyl-8-( 1,1 -dimethylethyl)-1 -oxaspiro[4.5]decane-3-amine; sodium tetrathiocarbonate; 20 and copper salts and preparations, such as Bordeaux mixture; copper hydroxide; copper naphthenate; copper oxychloride; copper sulphate; cufraneb; copper oxide; mancopper; oxine-copper. Bactericides: 25 bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, teclofta¬lam, copper sulphate and other copper preparations. Insecticides / acaricides / nematicides: 30 abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole, acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb, aldoxycarb, allethrin, allethrin lR-isomers, alpha-cypermethrin (alphamethrin), amidoflumet, aminocarb, Le A 35 963-Foreign Countries amitraz, avermectin, AZ-60541, azadirachtin, azamethiphos, azinphos-methyl, azin-phos-ethyl, azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus 5 thuringiensis strain NCTC-11821, baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthrin, beta-cyper-methrin, bifenazate, bifenthrin, binapacryl, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, bistrifluron, BPMC, brofen-prox, bromophos-ethyl, bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG- 10 505, bufencarb, buprofezin, butathiofos, butocarboxim, butoxycarboxim, butyl- pyridaben, cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap, CGA-50439, chinomethionat, chlordane, chlordimeform, chloethocarb, chlor-ethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloro- 15 benzilate, chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl), chlovaporthrin, chromafenozide, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin, clothiazoben, codlemone, couma-phos, cyanofenphos, cyanophos, cycloprene, cycloprothrin, Cydia pomonella, cy-fluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin (lR-trans-isomer), 20 cyromazine, DDT, deltamethrin, demeton-S-raethyl, demeton-S-methylsulphone, diafenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos, dicofol, dicrotophos, dicyclanil, diflu-benzuron, dimethoate, dimethylvinphos, dinobuton, dinocap, dinotefuran, diofenolan, disulphoton, docusat-sodium, dofenapyn, DOWCO-439, 25 eflusilanate, emamectin, emamectin-benzoate, empenthrin (lR-isomer), endosulphan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb, ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos, famphur, fenamiphos, fenazaquin, fenbutatin oxide, fenfluthrin, fenitrothion, fenobu-carb, fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, 30 fenpyroximate, fensulphothion, fenthion, fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim, fluazuron, flubenzimine, flubrocythrinate, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flumethrin, flupyrazofos, flutenzin (flufenzine), Le A 35 963-Foreign Countries fluvalinate, fonofos, formetanate, formothion, fosmethilan, fosthiazate, fubfenprox (fluproxyfen), furathiocarb, gamma-HCH, gossyplure, grandlure, granulosis viruses, halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexy- 5 thiazox, hydramethylnone, hydroprene, IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos, iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin, japonilure, kadethrin, nuclear polyhedrosis viruses, kinoprene, lambda-cyhalothrin, lindane, lufenuron, 10 malathion, mecarbam, mesulphenfos, metaldehyde, metam-sodium, methacrifos, methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin, MTI-800, 15 naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine, niten- pyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, novaluron, novi-flumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate, oxamyl, oxydemeton-methyl, 20 Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl), permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (lR-trans isomer), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl, pirimiphos-ethyl, prallethrin, profenofos, promecarb, propaphos, propargite, propetamphos, propoxur, prothiofos, prothoate, protrifenbute, 25 pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphen- thion, pyridathion, pyrimidifen, pyriproxyfen, quinalphos, resmethrin, RH-5849, ribavirin, RU-12457, RU-15525, S-421, S-1833, salithion, sebufos, SI-0009, silafluofen, spinosad, spirodiclofen, spiromesifen, sulphluramid, sulphotep, sulprofos, SZI-121, 30 tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, temivinphos, terbam, terbufos, tetrachlorvinphos, tetradifon, tetramethrin, tetramethrin (lR-isomer), tetrasul, theta-cypermethrin, thiacloprid, thiamethoxam, Le A 35 963-Foreign Countries thiapronil, thiatriphos, thiocyclam hydrogenoxalate, thiodicarb, thiofanox, thiometon, thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, trans- fluthrin, triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb, 5 vamidothion, vaniliprole, verbutin, Verticillium lecanii, WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, xylylcarb, ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901, the compound 3-methylphenyl propylcarbamate (tsumacide Z), the compound 3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]- 10 octane-3-carbonitrile (CAS-Reg. No. 185982-80-3) and the corresponding 3-endo- isomer (CAS-Reg. No. 185984-60-5) (cf. WO-96/37494, WO-98/25923), and preparations which comprise insecticidally active plant extracts, nematodes, fungi or viruses. 15 A mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators, safeners and/or semiochemicals is also possible. In addition, the compounds of the formula (I) according to the invention also have 20 very good antimycotic activity. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, 25 Microsporon species such as Microsporon canis and audouinii. The list of these fungi does by no means limit the mycotic spectrum which can be covered, but is only for illustration. The active compounds can be used as such, in the form of their formulations or the 30 use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. Application is carried out in a customary manner, for example by watering, spraying, atomizing, broadcasting, , Le A 35 963-Foreign Countries dusting, foaming, spreading, etc. It is furthermore possible to apply the active compounds by the ultra-low volume method, or to inject the active compound preparation or the active compound itself into the soil. It is also possible to treat the seeds of the plants 5 When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the kind of application. For the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000g/ha, preferably between 10 and 10 1000 g/ha. For seed dressing, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. For the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5,000 g/ha. 15 As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in 20 combination with conventional methods (Genetically Modified Organisms), and parts thereof, are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. Particularly preferably, plants of the plant cultivars which are in each case 25 commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having new properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes. 30 Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, Le A 35 963-Foreign Countries reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased 5 flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected. 10 The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferably to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased 15 tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and 20 microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus 25 fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are emphasized are in particular increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, 30 CryIIIA, CryIHB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses Le A 35 963-Foreign Countries by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, 5 glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), 10 KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to 15 phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned also include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars which have these 20 genetic traits or genetic traits still to be developed, and which will be developed and/or marketed in the future. The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula (I) or the active 25 compound mixtures according to the invention. The preferred ranges stated above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text, 30 The preparation and the use of the active compounds according to the invention is illustrated by the examples below. * Le A 35 963-Foreign Countries Preparation examples Example 1 10 9.77 g of cesium carbonate and 2 ml of water are added to a solution of 3.12 g of N-(2-bromophenyl)-5-fluoro-1,3-dimethyl-lH-pyrazoIe-4-carboxamide and 3.28 g of 2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxin-6-ylboronic acid (V-l) in 10 ml of n-butanol. With stirring and under an atmosphere of argon, 60 mg of tetrakis-(triphenylphosphine)palladium(0) are added. The reaction mixture is stirred at 80°C for 8 h. For work-up, the mixture is poured into water and extracted with ethyl acetate and the extract is dried and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 2:1). This gives 4.00 g (83% of theory) of 5-fluoro-l,3-dimethyl-N-[2-(2,2,3,3-tetrafluoro- 15 2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-1 H-pyrazole-4-carboxamide in the form of a colourless solid [logP (pH 2.3) - 3.77]. Example 2 Le A 35 963-Foreign Countries 10 Under argon, 0.37 g (1.6 mmol) of 5-bromo-2,2-difluoro-l,3-benzodioxoIe, 0.4g (1.6mmol) of 4,4,4',4',5,5,5,,5,-octamethyl-2,2'-bis-l,3,2-dioxaborolane and 0.42 g (4.3 mmol) of potassium acetate are suspended in 5 ml of dimethyl sulphoxide, and 0.05 g (0.07 mmol) of l,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride is added. After 2 h at 80°C, the mixture is cooled to room temperature, and 0.51 g (1.3 mmol) of N-(2-iodophenyl)-l-methyl-3-(trifluoromethyl)-lH-pyrazol-4-carbox-amide (IV-1), 3.25 ml of a 2 M solution of sodium carbonate and a further 0.05 g (0.07 mmol) of l,r-bis(diphenylphosphino)ferrocenepalladium(H) chloride are added. After 45 min at 70°C, the mixture is diluted with 5 ml of water and extracted 3 times with in each case 50 ml of ethyl acetate. The extracts are dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product is taken up in diethyl ether and chromatographed on silica gel (cyclohexane/ethyl acetate 3:1). 15 This gives 0.23 g (41% of theory) of N-[2-(2,2-difluoro-l,3-benzodioxol-5-yl)- phenyl]-l-methyl-3-(trifluoromethyl)-lH-pyrazol-4-carboxamide [logP (pH 2.3) = 3.37]. The biphenylcarboxamides of the formula (I) listed in Table 1 below are likewise 20 prepared analogously to Examples 1 and 2 described above and in accordance with the general descriptions of the processes. Table 1 Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Preparation of starting materials of the formula (IV) 5 Example (IV-1) 6.57g (30.0 mmol) of 2-iodoaniline and 6.1 g (60.0 mmol) of triethylamine are dissolved in 100 ml of tetrahydrofuran and, at room temperature, 7.65 g (36.0 mmol) 10 of l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carbonyl chloride are added slowly. The reaction solution is heated at 50°C for 16 h. For work-up, the mixture is concentrated under reduced pressure and the crude product is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1), This gives 10.0 g (85% of theory) of N-(2-iodophenyl)-l-methyl-3-(trifluoromethyl)- 15 lH-pyrazole-4-carboxamide [logP (pH 2.3) = 2.46]. Le A 35 963-Foreign Countries Preparation of starting materials of the formula (V) Example (V-l) A few grains of iodine are added to a suspension of 4.86 g of magnesium turnings in 20 ml of tetrahydrofuran (anhydrous), and 57.4 g of 6-bromo-2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxine in 60 ml of tetrahydrofuran are then added dropwise under an atmosphere of argon. By adjusting the rate of the dropwise addition, the 10 exothermic reaction is maintained close to the boiling point. After the dropwise addition has ended, the mixture is stirred under reflux for 30 min and then cooled to room temperature. The solution of the Grignard reagent is, together with a solution of 29.2 g of triethyl borate in 60 ml of tetrahydrofuran, added dropwise, at -10°C and over a period of 30 min, to 100 ml of tetrahydrofuran. The mixture is then stirred at 15 -10°C for another 1 h and then warmed to room temperature and stirred for another 30 min. For work-up, the reaction solution is, at -10°C, hydrolysed with 14 ml of water and adjusted to pH 4 using 80 ml of 10% strength sulphuric acid. The mixture is extracted with diethyl ether and the aqueous phase is saturated with sodium chloride and extracted with diethyl ether. The combined ether phases are, together 20 with 200 ml of water, concentrated. The solid residue is triturated with a little methylene chloride, filtered off with suction and dried. This gives 47.3 g (75% of theory) of 2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzo-dioxin-6-yl-boronic acid [logP (pH 2.3) = 2.49]. Le A 35 963-Foreign Countries The logP values given in the Preparation Examples were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C 18). Temperature: 43°C. Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile. Calibration was carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones). The lambda max values were determined in the maxima of the chromatographic signals using the UV spectra from 200 nm to 400 nm. Le A 35 963-Foreign Countries Use examples Example A 5 Podosphaera test (apple) / protective Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether 10 To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration. 15 To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha. The plants are then placed in a greenhouse at about 23 °C and a relative atmospheric humidity of about 70%. 20 Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 25 Active compounds, application rates and test results are shown in the table below. Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Example B Sphaerotheca test (cucumber) / protective 5 Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active 10 compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the 15 plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at about 23°C and a relative atmospheric humidity of about 70%. Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which 20 corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. Active compounds, application rates and test results are shown in the table below. Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Example C Venturia test (apple) / protective 5 Solvents: 24.5 parts by eight of cetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active 10 compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the 15 plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain in an incubation cabin at about 20°C in 100% relative atmospheric humidity for 1 day. The plants are then placed in a greenhouse at about 21°C and a relative atmospheric 20 humidity of about 90%. Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 25 Active compounds, application rates and test results are shown in the table below. Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Example D Alternaria test (tomato) / protective 5 Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the 10 concentrate is diluted with water to the desired concentration. To test for protective activity, young tomato plants are sprayed with the preparation of active compound at the stated application rate. 1 day after the treatment, the plants are inoculated with a spore suspension of Alternaria solani and then remain at 100% 15 relative humidity and at 20°C for 24 h. The plants then remain at 96% relative atmospheric humidity and a temperature of 20°C. Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no 20 infection is observed. Active compounds, application rates and test results are shown in the table below. Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Example E Puccinia test (wheat) / protective 5 Solvent: 25 parts by weight of N,N-dimethylacetamide Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the 10 concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain 15 in an incubation cabin at 20°C and 100% relative atmospheric humidity for 48 hours. The plants are then placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of 80% to promote the development of rust pustules. 20 Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. Active compounds, application rates and test results are shown in the table below. 25 Le A 35 963-Foreign Countries Le A 35 963-Foreign Countries Example F Inhibitory test using a giant colony of Basidiomycetes Mycelium pieces were punched out of a giant colony of the Basidiomycetes species Coriolus versicolor and incubated at 26°C on a nutrient agar medium containing malt extract peptone. The inhibition of the growth of the fungal threads on active-compound-containing nutrient media was compared to the longitudinal growth on nutrient media without added active compound and rated as inhibition in per cent. In this test, for example, the following compounds according to the invention of the Preparation Examples show good activity: Le A 35 963-Foreign Countries WE CLAIM; 1. Biphenylcarboxamides of the formula (I) in which R1 and R2 independently of one another represent hydrogen, halogen, cyano, nitro, having in each case 1 to 13 fluorine, chlorine and/or bromine atoms, m represents 1, 2, 3 or 4, where R1 represents identical or different radicals if m represents 2, 3 or 4, n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3, R3 represents hydrogen, hydroxyl, haloalkyl having 1 to 7 halogen atoms, alkylsulphenyl, haloalkylsulphenyl having 1 to 7 halogen atoms, , carbamoyl, Y represents carbonyl or represents which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, having in each case 1 to 13 fluorine, chlorine and/or bromine atoms and A represents a radical of the formula where R4 represents hydrogen, cyano, halogen, nitro, having 1 to 5 halogen atoms, cycloalkyl, having 1 to 5 halogen atoms, having 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C1-C4 alkyl and R5 represents hydrogen, halogen, cyano, alkoxy or and R6 represents hydrogen, having 1 to 5 halogen atoms, cycloalkyl, haloalkylthio- 1 to 5 halogen atoms, 1 to 5 halogen atoms or phenyl, or A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R9 represents halogen, cyano or C1-C4-alkyl or C1-C4-haloalkoxy having 1 to 5 halogen atoms, or A represents a radical of the formula R10 and R11 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R12 represents hydrogen, C1-C4-alkyl or hydrogen, or A represents a radical of the formula or R13 represents hydrogen, halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-haloalkoxy having 1 to 5 halogen atoms or C1-C4-haloalkylthio having 1 to 5 halogen atoms, represents a radical of the formula R14 represents halogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio having 1 to 5 halogen atoms, or C1-C4-haloalkoxy having 1 to 5 halogen atoms and R15 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkoxy having 1 to 5 halogen atoms, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl, or represents a radical of the formula R16 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R17 represents C1-C4-alkyl, X1 represents a sulphur atom, represents SO, SO2 or CH2, p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2, or A represents a radical of the formula R18 represents Ci-C4-alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula R19 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, A represents a radical of the formula R20 represents halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, R21 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R22 represents hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkylsulphonyl, di(C1 -C4-alkyl)-aminosulphonyl, C1-C6-alkylcarbonyl or optionally substituted phenylsulphonyl or benzoyl, or A represents a radical of the formula R23 and R24 independently of one another represent hydrogen, halogen, amino, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R25 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula R26 and R27 independently of one another represent hydrogen, halogen, amino, nitro, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R28 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, Or A represents a radical of the formula R29 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R30 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula R31 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and R32 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula R33 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, or R34 represents hydrogen or C1-C4-alkyl and A represents a radical of the formula R35 represents halogen or C1-C4-alkyl, or A represents a radical of the formula R36 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula R37 represents hydrogen, halogen or C1-C4-alkyl. 2. Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6- alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, m represents 1, 2 or 3, where R1 represents identical or different radicals if m represents 2 or 3, n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3, R3 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4- alkoxy, C1-C3-alkoxy-C1-C2-alkyl, cyano-C1-C4-alkyl, C1-C4- haloalkyl having 1 to 5 halogen atoms, C1-C4-aminoalkyl, C1-C4- alkylsulphenyl, C1-C4-haloalkylsulphenyl having 1 to 5 halogen atoms, (C1-C4-alkyl)carbonyl, Y represents carbonyl or represents C1-C2-alkylene which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4- alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy and/or C1-C4-haloalkylthio having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, and A represents a radical of the formula R4 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, methylthio, ethylthio, or trifluoromethylthio, di-fluoromethylthio aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl, R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and R6 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl, or represents a radical of the formula R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R9 represents fluorine, chlorine, bromine, cyano, methyl, ethyl or C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, represents a radical of the formula R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2 haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula R13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms or C1-C2-haloalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms, or represents a radical of the formula R14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio or C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms and R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-alkylsulphinyl or C1-C2-alkylsulphonyl, or A represents a radical of the formula R16 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R17 represents methyl or ethyl, X1 represents a sulphur atom, represents SO, SO2 or CH2 and p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2, or A represents a radical of the formula R18 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula R19 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula where R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R22 represents hydrogen, methyl, ethyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-alkoxy-C1-C2-alkyl, hydroxymethyl, hydroxyethyl, methyl sulphonyl or dimethylaminosulphonyl, or A represents a radical of the formula R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or represents a radical of the formula R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula R29 represents hydrogen, fluorine, chlorine, bromine, amino, C1-C4-alkylamino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R30 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2- haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, A represents a radical of the formula R31 represents hydrogen, fluorine, chlorine, bromine, amino, C1 -C4-alkylamino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and R32 represents fluorine, chlorine, bromine, methyl, ethyl or haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula R33 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2- haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula R34 represents hydrogen, methyl or ethyl and R35 represents fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula R36 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl. Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i- propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio, m represents 1 or 2, where R1 represents identical or different radicals if m represents 2, n represents 1 or 2, where R2 represents identical or different radicals if n represents 2, R3 represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, methoxymethyl, cyanomethyl, difluoromethyl, methylsulphenyl, trichloromethylsulphenyl or acetyl, represents carbonyl or represents -CH2- or -(CH2)2-, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio, and A represents a radical of the formula R4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclo- propyl methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio and R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and R6 represents hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl, or A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoro-methyl difluorochloromethyl or trichloromethyl and R9 represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy, or A represents a radical of the formula R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula or R13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl, di- fluorochloromethyl, trichloromethyl, trifluoromethoxy, di fluoromethoxy difluorochloromethoxy, trichloromethoxy, tri- fluoromethylthio difluoromethylthio, di- fluorochloromethylthio or trichloromethylthio, represents a radical of the formula R14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s- butyl, t-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio trifluoromethylthio, trifluoromethoxy, difluoro methoxy, difluorochloromethoxy or trichioromethoxy and R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoro methyl difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulphonyl, or A represents a radical of the formula R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R17 represents methyl or ethyl, X1 represents a sulphur atom, represents SO, S02 or CH2 and p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2, or A represents a radical of the formula R18 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula R19 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and R22 represents hydrogen, methyl, ethyl, trifluoromethyl, methoxy-methyl, ethoxymethyl, hydroxymethyl or hydroxyethyl, or A represents a radical of the formula R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difiuoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R30 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichioromethyl, or A represents a radical of the formula R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R32 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoro-methyl difluoromethyl, difluorochloromethyl or trichloro- methyl, or A represents a radical of the formula R33 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or R34 represents hydrogen, methyl or ethyl and A represents a radical of the formula R35 represents fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula R36 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl. 4. Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, trifluoromethylthio, m represents 1 or 2, where R1 represents identical or different radicals if m represents 2, n represents 1, R3 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, t-butyl, cyclopropyl, cyclopentyl or cyclohexyl, Y represents carbonyl or represents -CH2- or -(CH2)2-, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, methyl, i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio, and A represents a radical of the formula R4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and R5 represents hydrogen, fluorine, chlorine, bromine, iodine or methyl and R6 represents hydrogen, methyl, trifluoromethyl or phenyl, or A represents a radical of the formula R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl and R9 represents fluorine, chlorine, bromine, methyl or trifluoro methoxy, or A represents a radical of the formula R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl and R12 represents hydrogen, fluorine, chlorine, bromine or methyl, or A represents a radical of the formula R13 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl, or A represents a radical of the formula R14 represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and R15 represents hydrogen, fluorine, chlorine, bromine, iodine, n- propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulphinyl or methylsulphonyl, or represents a radical of the formula R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and R17 represents methyl or ethyl, X1 represents a sulphur atom, represents SO, SO2 or CH2 and p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2, or A represents a radical of the formula R18 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula R19 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or represents a radical of the formula where R20 represents fluorine, chlorine, bromine, methyl, i-propyl, trifluoromethyl, difluoromethyl or trichloromethyl, R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and R22 represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl, or A represents a radical of the formula R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and R28 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and R30 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or represents a radical of the formula R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and R32 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula R33 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or R34 represents hydrogen, methyl or ethyl and R35 represents fluorine, chlorine, bromine, methyl or ethyl, A represents a radical of the formula or A represents a radical of the formula R36 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula R37 represents hydrogen, fluorine, chlorine, bromine or methyl. 5. Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein R1 represents hydrogen, fluorine, chlorine, methyl, R2 represents hydrogen, m represents 1 or 2, where R1 represents identical or different radicals if m represents 2, n represents 1, R3 represents hydrogen, Y represents and A represents a radical of the formula R4 represents methyl, monofluoromethyl, difluoromethyl or trifluoromethyl and R5 represents hydrogen, fluorine, chlorine or methyl and R6 represents methyl, or A represents of the formula R7 and R8 represent hydrogen and R9 represents methyl, or A represents a radical of the formula R10 and R11 represent hydrogen and R12 represents methyl, or A represents a radical of the formula R13 represents iodine, methyl, difluoromethyl or trifluoromethyl, or A represents a radical of the formula R20 represents methyl, trifluoromethyl or difluoromethyl, R21 represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl or difluoromethyl and R22 represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl, or A represents a radical of the formula R23 and R24 represent hydrogen and R25 represents methyl, or A represents a radical of the formula R26 and R27 represent hydrogen and R28 represents methyl, or A represents a radical of the formula R29 represents amino, methylamino, dimethylamino, methyl or trifluoromethyl and R30 represents methyl, trifluoromethyl or difluoromethyl, or A represents a radical of the formula R31 represents amino, methylamino, dimethylamino, methyl or trifluoromethyl and R32 represents methyl, trifluoromethyl or difluoromethyl, or A represents a radical of the formula R36 represents methyl or trifluoromethyl. Process for preparing biphenylcarboxamides of the formula (I) as claimed in claim 1, wherein said process comprises a) carboxylic acid derivatives of the formula (II) in which A is as defined in Claim 1 and G represents halogen, hydroxyl or C1-C6-alkoxy, are reacted with aniline derivatives of the formula (III) in which R1, R2, m, n, R3 and Y are as defined in Claim 1, if appropriate in the presence of a catalyst, if appropriate in the 5 presence of an acid binder and if appropriate in the presence of a diluent, b) carboxamide derivatives of the formula (IV) or in which R1, m, R3 and A are as defined in Claim 1, are reacted with boronic acid derivatives of the formula (V) in which R2, n and Y are as defined in Claim 1 and G1 and G2 each represent hydrogen or together represent tetramethyl ethylene, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, c) carboxamide boronic acid derivatives of the formula (VI) in which R1, m, R3 and A are as defined in Claim 1 and G1 and G2 each represent hydrogen or together represent tetramethyl ethylene, are reacted with phenyl derivatives of the formula (VII) in which R2, n and Y are as defined in Claim 1, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or d) carboxamide derivatives of the formula (IV) in which R1, m, R3 and A are as defined in Claim 1, are reacted with phenyl derivatives of the formula (VII) in which R2, n and Y are as defined in Claim 1, in the presence of a palladium or platinum catalyst and in the presence of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis- 1,3,2-dioxaborolane, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. 7. Compositions for controlling unwanted microorganisms, wherein said composition comprises from 0.1 to 95wt% of at least one biphenylcarboxamide of the formula (I) as claimed in claim 1, in addition to extenders and/or surfactants. 8. Biphenylcarboxamides of the formula I as defined in claim 1 substantially as hereinbefore described with reference to the foregoing examples. 9. Process for preparing biphenylcarboxamides of the formula I as defined in claim 1 substantially as hereinbefore described with reference to the foregoing examples. Dated this 17th day of April, 2003. [DEEPAK KUMAR] OF REMFRY & SAGAR ATTORNEY FOR THE APPLICANTS]

Full Text

FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]
"BIPHENYLCARBOXAMIDES"

BAYER CROPSCIENCE AKTIENGESELLSCHAFT, a German company of Alfred-Nobel-Str. 50, 40789 Monheim, Germany,
The following specification particularly describes the nature of the invention and the manner in which it is to be performed :-

The present invention relates to novel biphenylcarboxamides, to a plurality of processes for their preparation and to their use for controlling unwanted micro-organisms.
It is already known that numerous carboxanilides have fungicidal properties (compare WO 93/11 117, WO 99/09 013, WO 00/14 071, EP-A 0 545 099 and EP-A 0 589 301). The activity of these substances is good; however, in some cases, for example at low application rates, it is unsatisfactory.
This invention now provides novel biphenylcarboxamides of the formula (I)

in which
independently of one another represent hydrogen, halogen, cyano, nitro,

alkoxy or having in each case 1 to 13 fluorine, chlorine
and/or bromine atoms,
m represents 1, 2, 3 or 4, where R1 represents identical or different radicals if m represents 2, 3 or 4,
n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3,

Le A 35 963-Foreign Countries
R3 represents hydrogen, hydroxyl,
having 1 to 7 halogen atoms, sulphenyl having 1 to 7 halogen atoms, carbamoyl,
Y represents carbonyl or represents which is optionally mono-
or polysubstituted by identical or different substituents from the group
consisting of halogen,
haloalkyl, having in each case 1
to 13 fluorine, chlorine and/or bromine atoms and A represents a radical of the formula

R4 represents hydrogen, cyano, halogen, nitro, haloalkyl having 1 to 5 halogen atoms, alkoxy, having 1 to 5 halogen atoms,
alkylthio, having 1 to 5 halogen atoms, aminocar-
bonyl or aminocarbonyl-
R5 represents hydrogen, halogen, cyano,

R6 represents hydrogen, having 1 to 5
halogen atoms, alkyl, having 1 to 5 halogen atoms,
having 1 to 5 halogen atoms or phenyl,
or

A represents a radical of the formula

R7 and R8 independently of one another represent hydrogen, halogen,
alkyl or having 1 to 5 halogen atoms and
R9 represents halogen, cyano or having
1 to 5 halogen atoms, or A represents a radical of the formula

R10 and R11 independently of one another represent hydrogen, halogen,
having 1 to 5 halogen atoms and
R12 represents hydrogen,' or A represents a radical of the formula

R13 represents hydrogen, halogen, hydroxyl, cyano,
haloalkyl having 1 to 5 halogen atoms, having 1 to
5 halogen atoms or having 1 to 5 halogen atoms,
or
A represents a radical of the formula

R14 represents halogen, hydroxyl, cyano, having 1 to 5 halogen atoms,

haloalkylthio having 1 to 5 halogen atoms, or having 1 to 5 halogen atoms and R15 represents hydrogen, halogen, cyano, having 1 to 5 halogen atoms, haloalkoxy having 1 to 5 halogen atoms, or

or

R16 represents having 1 to 5 halogen atoms
and R17 represents
X1 represents a sulphur atom, represents SO,
p represents 0,1 or 2, where R17 represents identical or different radicals
if p represents 2,
or

A represents a radical of the formula
where
R18 represents having 1 to 5 halogen
atoms, or A represents a radical of the formula

where

or

R19 represents having 1 to 5 halogen
atoms,

Le A 35 963-Foreign Countries
-5-
A represents a radical of the formula

R20 represents halogen, cyano, having 1 to
5 halogen atoms,
5 R21 represents hydrogen, halogen, having
1 to 5 halogen atoms and R22 represents hydrogen, cyano, having 1 to
5 halogen atoms,

10 carbonyl or optionally substituted phenylsulphonyl or benzoyl,
or
A represents a radical of the formula

R23 and R24 independently of one another represent hydrogen, halogen,
15 amino, having 1 to 5 halogen atoms
and R25 represents hydrogen, halogen, having
1 to 5 halogen atoms,
or
20 A represents a radical of the formula

R26 and R27 independently of one another represent hydrogen, halogen, amino, nitro,
having 1 to 5 halogen atoms and

Le A 35 963-Foreign Countries

R28 represents hydrogen, halogen, having 1 to 5
halogen atoms, or A represents a radical of the formula

R29 represents hydrogen, halogen, amino,
alkyl)amino, cyano, having 1 to 5
halogen atoms and R30 represents halogen, having 1 to 5
10 halogen atoms,
or A represents a radical of the formula

R31 represents hydrogen, halogen, amino,
15 alkyl)amino, cyano, having 1 to 5
halogen atoms and R32 represents halogen, having 1 to 5
halogen atoms,
or
20 A represents a radical of the formula

R33 represents halogen, having 1 to 5
halogen atoms,
or
25 A represents a radical of the formula

Le A 35 963-Foreign Countries

R34 represents hydrogen or C1-C4-alkyl and
R35 represents halogen or C1-C4-alkyl,
or
5 A represents a radical of the formula

R36 represents having 1 to 5 halogen
atoms,
or
10 A represents a radical of the formula
where
R37 represents hydrogen, halogen or
Depending on the nature of the substituents, the compounds of the formula (I) can be
15 present as geometrical and/or optical isomers or isomer mixtures of varying com-
positions. The invention relates both to the use of the pure isomers and to that of the isomer mixture.
Furthermore, it has been found that biphenylcarboxamides of the formula (I) are
20 obtained when
a) carboxylic acid derivatives of the formula (II)

Le A 35 963-Foreign Countnes
8-
A is as defined above and
G represents halogen, hydroxyl or C1-C6-alkoxy,
are reacted with aniline derivatives of the formula (HI)

(in)
in which
R1, R2, m, n, R3 and Y are as defined above,

or b)

if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,
carboxamide derivatives of the formula (IV)

in which
R1, m, R3 and A are as defined above,
are reacted with boronic acid derivatives of the formula (V)

in which

Le A 35 963-Foreign Countries
-9-
R2, n and Y are as defined above and
G1 and G2 each represent hydrogen or together represent tetramethylethylene,
in the presence of a catalyst, if appropriate in the presence of an acid binder
5 and if appropriate in the presence of a diluent,
or c) carboxamide boronic acid derivatives of the formula (VI)

in which
10 R1, m, R3 and A are as defined above and
G1 and G2 each represent hydrogen or together represent tetramethylethylene,
are reacted with phenyl derivatives of the formula (VII)

15 in which
R2, n and Y are as defined above,
in the presence of a catalyst, if appropriate in the presence of an acid binder
and if appropriate in the presence of a diluent,
20 or

d) carboxamide derivatives of the formula (IV)

Le A 35 963-Foreign Countries
in which R1, m, R3 and A are as defined above,
are reacted with phenyl derivatives of the formula (VII)
in which
R2, n and Y are as defined above,
in the presence of a palladium or platinum catalyst and in the presence of 4,4,4',4,,5,5,5',5'-octamethyl-2,2'-bis-l,3,2-dioxaborolane, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Finally, it has been found that the novel biphenylcarboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials.
Surprisingly, the biphenylcarboxamides of the formula (I) according to the invention have considerably better fungicidal activity than the constitutionally most similar active compounds of the prior art having the same direction of action.
The formula (I) provides a general definition of the biphenylcarboxamides according to the invention.
Preference is given to biphenylcarboxamides of the formula (I) in which
R1 and R2 independently of one another represent hydrogen, fluorine, chlorine,
bromine, cyano, nitro,
haloalkyl, having in each case 1 to 9
fluorine, chlorine and/or bromine atoms,

Le A 35 963-Foreign Countries

m represents 1, 2 or 3, where R1 represents identical or different radicals if m represents 2 or 3,
n represents 1, 2 or 3, where R2 represents identical or different radicals if n
5 represents 2 or 3,
R3 represents hydrogen, hydroxy],
having 1 to 5
halogen atoms,
10 sulphenyl having 1 to 5 halogen atoms,
Y represents carbonyl or represents which is optionally mono-
or polysubstituted by identical or different substituents from the group
consisting of fluorine, chlorine, bromine,
15 alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy and/or C1-C4-haloalkylthio
having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
and
A represents a radical of the formula

where
20 R4 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine,
methyl, ethyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, amino-
25 carbonyl, aminocarbonylmethyl or aminocarbonylethyl,
R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and

Le A 35 963-Foreign Countries

R6 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl,
or
A represents a radical of the formula

R7 and R8 independently of one another represent hydrogen, fluorine,
chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5
fluorine, chlorine and/or bromine atoms and
10 R9 represents fluorine, chlorine, bromine, cyano, methyl, ethyl or C1-C2-
haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents a radical of the formula

15 R10 and R11 independently of one another represent hydrogen, fluorine,
chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5
fluorine, chlorine and/or bromine atoms and
R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl,
or
20 A represents a radical of the formula
where
R13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-haloalkoxy having 1 to 5 fluorine,

, Le A 35 963-Foreign Countries
13
chlorine and/or bromine atoms or C1-C2-haloalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
represents a radical of the formula

where

R14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4
alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine
atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio,
trifluoromethylthio or C1-C2-haloalkoxy having 1 to 5 fluorine,
10 chlorine and/or bromine atoms and
R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano,
C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or
bromine atoms, methoxy, ethoxy, methylthio, ethylthio, C1-C2-
haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms,
15 C1 -C2-alkylsulphinyl or C1-C2-alkylsulphonyl,
or A represents a radical of the formula

where
R16 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine,
20 chlorine and/or bromine atoms and
R17 represents methyl or ethyl,
X1 represents a sulphur atom, represents SO, SO2 or CH2 and
p represents 0,1 or 2, where R17 represents identical or different radicals
if p represents 2,
25 or
A represents a radical of the formula

, Le A 35 963-Foreign Countries

where
R18 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine,
chlorine and/or bromine atoms,
or
5 A represents a radical of the formute

where

R19 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
10 A represents a radical of the formula

R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl
or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine
atoms,
15 R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or
C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms
and
R22 represents hydrogen, methyl, ethyl, C1-C2-haloalkyl having 1 to 5
fluorine, chlorine and/or bromine atoms, C1-C2-alkoxy-C1-C2-alkyl,
20 hydroxymethyl, hydroxyethyl, methylsulphonyl or dimethylamino-
sulphonyl, or A represents a radical of the formula

Le A 35 963-Foreign Countries

R23 and R24 independently of one another represent hydrogen, fluorine,
chlorine, bromine, amino, methyl, ethyl or C1-C2-haloalkyl having 1 to
5 fluorine, chlorine and/or bromine atoms and R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or
C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine
atoms,
or
A represents a radical of the formula

where

R26 and R27 independently of one another represent hydrogen, fluorine,
chlorine, bromine, amino, nitro, methyl, ethyl or C1-C2-haloalkyl
having 1 to 5 fluorine, chlorine and/or bromine atoms and
R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or
15 C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine
atoms, or A represents a radical of the formula

where

20 R29 represents hydrogen, fluorine, chlorine, bromine, amino,C1-C4-
alkylamino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2 haloalkyl having I to 5 fluorine, chlorine and/or bromine atoms and R30 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,

, Le A 35 963-Foreign Countries

or
A represents a radical of the formula

R31 represents hydrogen, fluorine, chlorine, bromine, amino, C1-C4-alkyl-amino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and
R32 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
10 A represents a radical of the formula

R33 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2-
haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
15 A represents a radical of the formula
where
R34 represents hydrogen, methyl or ethyl and
R35 represents fluorine, chlorine, bromine, methyl or ethyl,
or
20 A represents a radical of the formula

where
R36 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,

Le A 35 963-Foreign Countries

R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl. 5
Particular preference is given to biphenylcarboxamides of the formula (I) in which
R1 and R2 independently of one another represent hydrogen, fluorine, chlorine,
bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-
butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl,
10 trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy,
trifiuoromethoxy, trifluoromethylthio, difluorochloromethylthio,
m represents 1 or 2, where R1 represents identical or different radicals if m
represents 2, 15
n represents 1 or 2, where R2 represents identical or different radicals if n
represents 2,
R3 represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-,
20 t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy,
methoxymethyl, cyanomethyl, difluoromethyl, methylsulphenyl, trichloro-methylsulphenyl or acetyl,
Y represents carbonyl or represents -CH2- or -(CH2)2-, each of which is
25 optionally mono- to tetrasubstituted by identical or different substituents
from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, i-
propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t-
butylthio, trifluoromethyl, trifiuoromethoxy and trifluoromethylthio,
and
30 A represents a radical of the formula

Le A 35 963-Foreign Countries

R4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio and
R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and
R6 represents hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl, or A represents a radical of the formula

R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,
R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and R9 represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy, or A represents a radical of the formula

Le A 35 963-Foreign Countries

difluorochloromethyl or trichloromethyl and R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or A represents a radical of the formula

R13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl,
cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl,
t-butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichlo¬
romethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,
10 trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluoro-
chloromethylthio or trichloromethylthio, or A represents a radical of the formula

15 R14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano,
methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichlorome¬thyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, tri¬fluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloro-
20 methoxy or trichloromethoxy and
R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy,
25 difluorochloromethoxy, trichloromethoxy, methylsulphinyl or
methylsulphonyl, or

, Le A 35 963-Foreign Countries

R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro-
chloromethyl or trichloromethyl and R17 represents methyl or ethyl,
X1 represents a sulphur atom, represents SO, SO2 or CH2 and
p represents 0,1 or 2, where R17 represents identical or different radicals
if p represents 2,
or
10 A represents a radical of the formula
where
R18 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro-
chloromethyl or trichloromethyl,
or
15 A represents a radical of the formula

where

R19 represents methyl, ethyl, trifluoromethyl, difluoromethyl,
difluorochloromethyl or trichloromethyl,
or
20 A represents a radical of the formula

Le A 35 963-Foreign Countries

R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloro-methyl, R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tri¬fluoromethyl, difluoromethyl or trichloromethyl and R22 represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl, or A represents a radical of the formula

10
R23 and R24 independently of one another represent hydrogen, fluorine,
chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl,
difluorochloromethyl or trichloromethyl and
R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tri-
15 fluoromethyl, difluoromethyl, difluorochloromethyl or trichloro-
methyl, or A represents a radical of the formula

20 R26 and R27 independently of one another represent hydrogen, fluorine,
chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl,
difluoromethyl, difluorochloromethyl or trichloromethyl and
R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,
trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloro-
25 methyl,
or

Lg_A 35 963-Foreign Countnes

represents a radical of the formula
R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and R30 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a radical of the formula

R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R32 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or
A represents a radical of the formula

R33 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,
or
A represents a radical of the formula

, Le A 35 963-Foreign Countries

R34 represents hydrogen, methyl or ethyl and
R35 represents fluorine, chlorine, bromine, methyl or ethyl,
or
A represents a radical of the formula

10

R36 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro-chloromethyl or trichloromethyl, or A represents a radical of the formula

R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.

Very particular preference is given to biphenylcarboxamides of the formula (I) in
which
15 R1 and R2 independently of one another represent hydrogen, fluorine, chlorine,
bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifiuoromethoxy, trifluoromethylthio,
20 m represents 1 or 2, where R1 represents identical or different radicals if m
represents 2,
n represents 1,
25 R3 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, t-butyl, cyclo-
propyl, cyclopentyl or cyclohexyl,

Le A 35 963-Foreign Countries

Y represents carbonyl or represents -CH2- or -(CH2)2-, each of which is
optionally mono- to tetrasubstituted by identical or different substituents from
the group consisting of fluorine, methyl, i-propyl, t-butyl, methoxy, i-
propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl,
5 trifluoromethoxy and trifluoromethylthio,
and
A represents a radical of the formula

R4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, i-
10 propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluoro-
chloromethyl or trichloromethyl and
R5 represents hydrogen, fluorine, chlorine, bromine, iodine or methyl and
R6 represents hydrogen, methyl, trifluoromethyl or phenyl,
or
15 A represents a radical of the formula

R7 and R8 independently of one another represent hydrogen, fluorine,
chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or
trichloromethyl and
20 R9 represents fluorine, chlorine, bromine, methyl or trifluoromethoxy,
or A represents a radical of the formula

Le A 35 963-Foreign Countries

R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difiuoromethyl, trifluoromethyl or trichloromethyl and R12 represents hydrogen, fluorine, chlorine, bromine or methyl, or A represents a radical of the formula
where
R13 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl,
difiuoromethyl, trifluoromethyl or trichloromethyl,
10 or
A represents a radical of the formula

where

R14 represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl,
difiuoromethyl or trichloromethyl and
15 R15 represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, i-
propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difiuoro¬methyl, trichloromethyl, methylsulphinyl or methylsulphonyl, or A represents a radical of the formula

20
R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl or
trichloromethyl and R17 represents methyl or ethyl,
X1 represents a sulphur atom, represents SO, SO2 or CH2 and
25 p represents 0,1 or 2, where R17 represents identical or different radicals
if p represents 2,

Le A 35 963-Foreign Countries

or
A represents a radical of the formula
R18 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula
where
R19 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
10 A represents a radical of the formula

R20 represents fluorine, chlorine, bromine, methyl, i-propyl, trifluoro¬
methyl, difluoromethyl or trichloromethyl,
R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,
15 trifluoromethyl, difluoromethyl or trichloromethyl and
R22 represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl,

20 R23 and R24 independently of one another represent hydrogen, fluorine,
chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and

Le A 35 963-Foreign Countries

R25 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoro¬methyl, difluoromethyl or trichloromethyl,
or
A represents a radical of the formula

R26 and R27 independently of one another represent hydrogen, fluorine,
chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or
trichloromethyl and
R28 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoro-
10 methyl, difluoromethyl or trichloromethyl,
or A represents a radical of the formula

R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
15 dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloro-
methyl and
R30 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl,

20

R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloro¬methyl and

Le A 35 963-Foreign Countries

R32 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula

10

R33 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl, or A represents a radical of the formula

R34 represents hydrogen, methyl or ethyl and
R35 represents fluorine, chlorine, bromine, methyl or ethyl,
or
A represents a radical of the formula

15
R36 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
A represents a radical of the formula

20 R37 represents hydrogen, fluorine, chlorine, bromine or methyl.
Especially preferred are biphenylcarboxamides of the formula (I) in which R1 represents hydrogen, fluorine, chlorine, methyl,

Le A 35 963-Foreign Countries

R2 represents hydrogen,
m represents 1 or 2, where R1 represents identical or different radicals if m
represents 2,
n represents 1,
R3 represents hydrogen,
Y represents
and
A represents a radical of the formula

R4 represents methyl, monofluoromethyl, difluoromethyl or trifluoromethyl and
R5 represents hydrogen, fluorine, chlorine or methyl and
R6 represents methyl, or A represents a radical of the formula

R7 and R8 represent hydrogen and
R9 represents methyl, or A represents a radical of the formula

R10 and R11 represent hydrogen and R12 represents methyl,
or

Le A 35 963-Foreign Countries

A represents a radical of the formula
where

R13 represents iodine, methyl, difluoromethyl or trifluoromethyl,
or
A represents a radical of the formula

R20 represents methyl, trifiuoromethyl or difluoromethyl,
R21 represents hydrogen, fluorine, chlorine, methyl, trifiuoromethyl or
difluoromethyl and R22 represents hydrogen, methyl, ethyl, trifiuoromethyl or methoxymethyl,
or
A represents a radical of the formula

R23 and R24 represent hydrogen and R25 represents methyl,
or
A represents a radical of the formula

R26 and R27 represent hydrogen and R28 represents methyl,
or

Le A 35 963-Foreign Countries

A represents a radical of the formula
R29 represents amino, methylamino, dimethylamino, methyl or
trifluoromethyl and
5 R30 represents methyl, trifluoromethyl or difluoromethyl,
or A represents a radical of the formula

R31 represents amino, methylamino, dimethylamino, methyl or
10 trifluoromethyl and
R32 represents methyl, trifluoromethyl or difluoromethyl, or A represents a radical of the formula

15 R36 represents methyl or trifluoromethyl.
Moreover, emphasis is given to compounds of the formula (I) in which R3 represents hydrogen.
Moreover, emphasis is given to compounds of the formula (I) in which R2 represents
20 hydrogen.
Moreover, emphasis is given to compounds of the formula (I) in which Y represents

Moreover, emphasis is given to compounds of the formula (I) in which R1 represents hydrogen, fluorine, chlorine or methyl and especially hydrogen or fluorine.

Le A 35 963-Foreign Countries

Moreover, emphasis is given to compounds of the formula (I) in which m represents 0,1 or 2.
Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula

where R4, R5 and R6 are as defined above.
Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula
5

10

15

where R7, R8 and R9 are as defined above.
Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula

where R13 is as defined above.
Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula

20

where R29 and R30 are as defined above.

Le A 35 963-Foreign Countries

Moreover, emphasis is given to compounds of the formula (I) in which A represents a radical of the formula

where R36 is as defined above. 5
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, even in combination with heteroatoms, such as, for example, in alkoxy.
10 Optionally substituted radicals can be mono- or polysubstituted, where in the case of
polysubstitutions the substituents can be identical or different.
Halogen-substituted radicals, such as, for example, haloalkyl, are mono- or
polyhalogenated. In the case of polyhalogenation, the halogen atoms can be identical
15 or different. Here, halogen represents fluorine, chlorine, bromine and iodine, in
particular fluorine, chlorine and bromine.
However, the general or preferred radical definitions or illustrations listed above can
also be combined with one another as desired, i.e. including combinations between
20 the respective ranges and preferred ranges. They apply to the end products and,
correspondingly, to precursors and intermediates. Moreover, individual definitions may not apply.
Using 2-methyl-4-trifluoromethyl-l,3-thiazole-5-carbonyl chloride and (2,2-difluoro-
25 l,3-benzodioxol-5-yl)phenylamine as starting materials, the course of the process (a)
according to the invention can be illustrated by the formula scheme below.

Le A 35 963-Foreign Countries

Using N-(2-bromophenyl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide and 2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxin-6-ylboronic acid as starting materials and a catalyst, the course of the process (b) according to the invention can be illustrated by the formula scheme below.

10

Using 2- {[(5-fluoro-l ,3-dimethyI-l//-pyrazol-4-yl)carbonyl]amino}phenylboronic acid and 6-bromo~2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxine as starting materials and a catalyst, the course of the process (c) according to the invention can be illustrated by the formula scheme below.

15

Using N-(2-bromophenyl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide and 6-bromo-2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxine as starting materials and a catalyst and 4,4,4,,4,,5,5,5,,5'-octamethyl-2,2'-bis-l,3,2-dioxaborolane, the course of the process (d) according to the invention can be illustrated by the formula scheme below.

Le A 35 963-Foreign Countries

Explanation of the processes and intermediates
The formula (II) provides a general definition of the carboxylic acid derivatives
5 required as starting materials for carrying out the process (a) according to the
invention. In this formula, A preferably has those meanings which have already been
mentioned in connection with the description of the compounds of the formula (I)
according to the invention as being preferred, particularly preferred, very particularly
preferred or especially preferred for these radicals. G preferably represents chlorine,
10 bromine, hydroxyl, methoxy or ethoxy, particularly preferably chlorine, hydroxy or
methoxy.
The carboxylic acid derivatives of the formula (II) are known or can be prepared by
known processes (cf. WO 93/11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A
15 0 589 313).
The formula (HI) provides a general definition of the aniline derivatives required as
reaction components for carrying out the process (a) according to the invention. In
this formula, R1, R2, m, n, R3 and Y preferably have those meanings which have
20 already been mentioned in connection with the description of the compounds of the
formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices.
The aniline derivatives of the formula (III) are novel. Some of them can be prepared
25 by known methods (cf. EP-A 0 545 099 and EP-A 0 589 301). Moreover, aniline
derivatives of the formula (in) are obtained by

t Le A 35 963-Foreign Countries

e) reacting 2-haloaniline derivatives of the general formula (VIII)

in which
R1, m and R3 are as defined above and
Hal represents halogen,
with boronic acid derivatives of the formula (V)

(V)

in which
R2, n, Y, G1 and G2 are as defined above,
if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent, and if appropriate in the presence of a catalyst,
or
f) reacting anilineboronic acids of the formula (IX)

in which
R1, m, R3, G1 and G2 are as defined above,
with phenyl derivatives of the formula (VII)

Le A 35 963-Foreign Countries

in which
R2, n and Y are as defined above,
5 if appropriate in the presence of an acid binder, and if appropriate in the
presence of an inert organic diluent, and if appropriate in the presence of a catalyst.
10
15
The formula (VIII) provides a general definition of the 2-haloaniline derivatives required as reaction components for carrying out the process (e) according to the invention. In this formula, R1, m and R3 preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. Hal preferably represents fluorine, chlorine or bromine, particularly preferably chlorine or bromine.
The 2-haloaniline derivatives of the formula (VIII) are known and/or can be prepared
from the corresponding nitro compounds by reduction. If R3 does not represent
20 hydrogen, the compounds of the formula (VIII) can be obtained by known
derivatizations of the resulting aniline derivatives.
The boronic acid derivatives of the formula (V) furthermore required as starting
materials for carrying out the process (e) according to the invention are illustrated in
25 more detail below, in connection with the process (b) according to the invention.
The formula (IX) provides a general definition of the anilineboronic acids required as reaction components for carrying out the process (f) according to the invention. In

Le A 35 963-Foreign Countries

this formula, R1, m and R3 preferably have those meanings which have already been
mentioned in connection with the description of the compounds of the formula (I)
according to the invention as being preferred, particularly preferred, very particularly
preferred or especially preferred for these radicals or these indices. G1 and G2
5 preferably each represent hydrogen or together represent tetramethylethylene.
The anilineboronic acids of the formula (IX) are known and/or can be obtained by known methods.
10 The phenyl derivatives of the formula (VII) furthermore required as starting materials
for carrying out the process (f) according to the invention are illustrated in more detail below, in connection with the process (d) according to the invention.
The formula (IV) provides a general definition of the carboxamide derivatives
15 required as starting materials for carrying out the process (b) and (d) according to the
invention. In this formula, R1, m, R3 and A preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. 20
The carboxamide derivatives of the formula (IV) are known or can be prepared by known processes (cf., for example, WO 91/01311, EP-A 0 371 950).
The formula (V) provides a general definition of the boronic acid derivatives required
25 as starting materials for carrying out the processes (b) and (e) according to the
invention. In this formula, R2, n and Y preferably have those meanings which have
already been mentioned in connection with the description of the compounds of the
formula (I) according to the invention as being preferred, particularly preferred, very
particularly preferred or especially preferred for these radicals or these indices. G1
30 and G2 preferably each represent hydrogen or together represent tetramethylethylene.
The boronic acid derivatives of the formula (V) are known and/or can be prepared by

Le A 35 963-Foreign Countries

known processes (cf., for example, WO 01/90084 and US 5,633,218). They are obtained, for example, by
g) reacting phenyl derivatives of the formula (VII)

in which
R2, n and Y are as defined above,
with boric acid esters of the formula (X)
10

15 in the presence of magnesium, if appropriate in the presence of a diluent (for
example tetrahydrofuran).
The formula (X) provides a general definition of the boric acid esters required as
reaction components for carrying out the process (g) according to the invention. In
20 this formula, R38 preferably represents methyl, ethyl, n- or i-propyl, particularly
preferably methyl or ethyl.
The boric acid esters of the formula (X) are known chemicals for synthesis.
25 The formula (VI) provides a general definition of the carboxamide boronic acid
derivatives required as reaction components for carrying out the process (c) according to the invention. In this formula, R1, m, R3 and A preferably have those meanings which have already been mentioned in connection with the description of

Le A 35 963-Foreign Countries

the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. G1 and G2 preferably each represent hydrogen or together represent tetramethylethylene. 5
The carboxamide boronic acid derivatives of the formula (VI) are known and/or can be prepared by known processes.
The formula (VII) provides a general definition of the phenyl derivatives required as
10 starting materials for carrying out the processes (c), (d), (f) and (g) according to the
invention. In this formula, R2, n and Y preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred, very particularly preferred or especially preferred for these radicals or these indices. 15
The phenyl derivatives of the formula (VII) are known or can be prepared by known processes (cf. Synth. Commun. 2000, 30, 665-669, Synth. Commun. 1999. 29, 1697-1701).
20 Suitable acid binders for carrying out the processes (a), (b), (c), (d), (e) and (f)
according to the invention are in each case all inorganic and organic bases customary for such reactions. Preference is given to using alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or else ammonium hydroxide, alkali metal carbonates, such as sodium carbonate,
25 potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkali metal or
alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, tributyl-amine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylamino-pyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicyclo-
30 undecene (DBU). However, it is also possible to work in the absence of an additional
acid binder, or to employ an excess of the amine component so that it simultaneously acts as acid binder.

, Le A 35 963-Foreign Countries

Suitable diluents for carrying out the processes (a), (b), (c), (d), (e) and (f) according
to the invention are in each case all customary inert organic solvents. Preference is
given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons,
5 such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene,
toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane,
chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as
diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,
tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as
10 acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-
dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethylsulphoxide, or sulphones, such as sulpholane.
15 When carrying out the processes (a), (b), (c), (d), (e) and (f) according to the
invention, the reaction temperatures can in each case be varied within a relatively wide range. In general, the processes are carried out at temperatures between 0°C and 140°C, preferably between 10°C and 120°C.
20 The processes (a), (b), (c), (d), (e) and (f) according to the invention are generally
each carried out under atmospheric pressure. However, in each case it is also possible to operate under elevated or reduced pressure.
When carrying out the process (a) according to the invention, in general 1 mol or else
25 an excess of aniline derivative of the formula (HI) and from 1 to 3 mol of acid binder
are employed per mole of acid halide of the formula (H). However, it is also possible
to employ the reaction components in other ratios. Work-up is carried out by
customary methods. In general, water is added to the reaction mixture and the organic
phase is separated off and, after drying, concentrated under reduced pressure. The
30 residue that remains may, if appropriate, be freed of any impurities that may still be
present using customary methods, such as chromatography or recrystallization.

Le A 35 963-Foreign Countries

When carrying out the process (b) according to the invention, in general 1 mol or else
an excess of boronic acid derivative of the formula (V) and from 1 to 5 mol of acid
binder are employed per mole of carboxamide of the formula (IV). However, it is
also possible to employ the reaction components in other ratios. Work-up is carried
5 out by customary methods. In general, water is added to the reaction mixture and the
precipitate is separated off and dried. The residue that remains may, if appropriate, be freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization.
10 When carrying out the process (c) according to the invention, in general 1 mol or else
an excess of phenyl derivative of the formula (VII) and from 1 to 10 mol of acid binder and from 0.5 to 5 mol% of a catalyst are employed per mole of carboxamide boronic acid derivative of the formula (VI). However, it is also possible to employ the reaction components in other ratios. Work-up is carried out by customary
15 methods. In general, water is added to the reaction mixture and the precipitate is
separated off and dried. The residue that remains may, if appropriate, be freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization.
20 When carrying out the process (d) according to the invention, in general 1 mol or else
an excess of phenyl derivative of the formula (VII) and from 1 to 5 mol of acid binder and from 1 to 5 mol of a catalyst are employed per mole of carboxamide derivative of the formula (IV). However, it is also possible to employ the reaction components in other ratios. Work-up is carried out by customary methods. In general,
25 water is added to the reaction mixture and the precipitate is separated off and dried.
The residue that remains may, if appropriate, be freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization.
The substances according to the invention have potent microbicidal activity and can
30 be employed for controlling unwanted microorganisms, such as fungi and bacteria, in
crop protection and in the protection of materials.

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Fungicides can be employed in crop protection for controlling Plasmodiophoro-mycetes, Oomycetes, Chytndiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
5 Bactericides can be employed in crop protection for controlling Pseudomonadaceae,
Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Some pathogens causing fungal and bacterial diseases which come under the generic
names listed above may be mentioned as examples, but not by way of limitation:
10 Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
15 Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
20 Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
25 (conidia form: Drechslera, syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus
(conidia form: Drechslera, syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
30 Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;

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Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
5 Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae; and
Pseudocercosporella species, such as, for example, Pseudocercosporella
10 herpotrichoides.
The active compounds according to the invention also show a strong invigorating action in plants. Accordingly, they are suitable for mobilizing the internal defences of the plant against attack by unwanted microorganisms.
15
In the present context, plant-invigorating (resistance-inducing) compounds are to be understood as meaning substances which are capable of stimulating the defence system of plants such that, when the treated plants are subsequently inoculated with unwanted microorganisms, they display substantial resistance to these
20 microorganisms.
In the present case, unwanted microorganisms are to be understood as meaning
phytopathogenic fungi, bacteria and viruses. The compounds according to the
invention can thus be used to protect plants "within a certain period of time after
25 treatment against attack by the pathogens mentioned. The period of time for which
this protection is achieved generally extends for 1 to 10 days, preferably 1 to 7 days, from the treatment of the plants with the active compounds.
The fact that the active compounds are well tolerated by plants at the concentrations
30 required for controlling plant diseases permits the treatment of above-ground parts of
plants, of propagation stock and seeds, and of the soil.

Le A 35 963-Foreign Countries

The active compounds according to the invention are also suitable for increasing the yield of crops. In addition, they show reduced toxicity and are well tolerated by plants.
If appropriate, the active compounds according to the invention can, at certain
5 concentrations and application rates, also be employed as herbicides, for regulating
plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates or precursors in the synthesis of other active compounds.
According to the invention, it is possible to treat all plants and parts of plants. Plants
10 are to be understood here as meaning all plants and plant populations, such as desired
and undesired wild plants or crop plants (including naturally occurring crop plants).
Crop plants can be plants which can be obtained by conventional breeding and
optimization methods or by biotechnological and genetic engineering methods or
combinations of these methods, including the transgenic plants and including plant
15 cultivars which can or cannot be protected by plant breeders' certificates. Parts of
plants are to be understood as meaning all above-ground and below-ground parts and
organs of plants, such as shoot, leaf, flower and root, examples which may be
mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds
and also roots, tubers and rhizomes. Parts of plants also include harvested material
20 and vegetative and generative propagation material, for example seedlings, tubers,
rhizomes, cuttings and seeds.
The treatment of the plants and parts of plants according to the invention with the
active compounds is carried out directly or by action on their environment, habitat or
25 storage area according to customary treatment methods, for example by dipping,
spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating.
30 In the protection of materials, the compounds according to the invention can be
employed for protecting industrial materials against infection with, and destruction by, unwanted microorganisms.

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Industrial materials in the present context are understood as meaning non-living
materials which have been prepared for use in industry. For example, industrial
materials which are intended to be protected by active compounds according to the
invention from microbial change or destruction can be tackifiers, sizes, paper and
5 board, textiles, leather, wood, paints and plastic articles, cooling lubricants and other
materials which can be infected with, or destroyed by, microorganisms. Parts of
production plants, for example cooling-water circuits, which may be impaired by the
proliferation of microorganisms may also be mentioned within the scope of the
materials to be protected. Industrial materials which may be mentioned within the
10 scope of the present invention are preferably tackifiers, sizes, paper and board,
leather, wood, paints, cooling lubricants and heat-transfer liquids, particularly preferably wood.
Microorganisms capable of degrading or changing the industrial materials which may
15 be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms.
The active compounds according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
20 Microorganisms of the following genera may be mentioned as examples:
Alternaria, such as Alternaria tenuis,
Aspergillus, such as Aspergillus niger,
Chaetomium, such as Chaetomium globosum,
Coniophora, such as Coniophora puetana,
25 Lentinus, such as Lentinus tigrinus,
Penicillium, such as Penicillium glaucum,
Polyporus, such as Polyporus versicolor,
Aureobasidium, such as Aureobasidium pullulans,
Sclerophoma, such as Sclerophoma pityophila,
30 Trichoderma, such as Trichoderma viride,
Escherichia, such as Escherichia coli,
Pseudomonas, such as Pseudomonas aeruginosa, and

Le A 35 963-Foreign Countries

Staphylococcus, such as Staphylococcus aureus.
Depending on their particular physical and/or chemical properties, the active
compounds can be converted into the customary formulations, such as solutions,
5 emulsions, suspensions, powders, foams, pastes, granules, aerosols and
microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
These formulations are produced in a known manner, for example by mixing the
10 active compounds with extenders, that is liquid solvents, liquefied gases under
pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or
15 alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such
as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as
20 dimethylformamide or dimethyl sulphoxide, or else water. Liquefied gaseous
extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such
25 as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous
earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic
30 material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable
emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for

, Le A 35 963-Foreign Countries

example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, aryl-sulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
5 Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the
form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
10
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
15
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
The active compounds according to the invention can, as such or in their
20 formulations, also be used in a mixture with known fungicides, bactericides,
acaricides, nematicides or insecticides, to broaden, for example, the activity spectrum
or to prevent development of resistance. In many cases, synergistic effects are
obtained, i.e. the activity of the mixture is greater than the activity of the individual
components. 25
Suitable mixing components are, for example, the following compounds:
Fungicides:
2-phenylphenol; 8-hydroxyquinoline sulphate;
acibenzolar-S-methyl; aldimorph; amidofklumet; ampropylfos; ampropylfos-potas-
30 sium; andoprim; anilazine; azaconazole; azoxystrobin;
benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl; benzamacril; benzamacril-
isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole;

Le A 35 963-Foreign Countries

bupirimate; buthiobate; butylamine;
calcium polysulphide; capsimycin; captafol; captan; carbendazim; carboxin;
carpropamid; carvone; chinomethionat; chlobenthiazone; chlorfenazole; chloroneb;
chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid; cymoxanil;
5 cyproconazole; cyprodinil; cyprofuram;
Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; diclo-
mezine; dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;
dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap; diphenyl-
amine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;
10 edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;
famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fen-
hexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam;
fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromide;
fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulphamide; flutolanil;
15 flutriafol; folpet; fosetyl-Al; fosetyl-sodium; fuberidazole; furalaxyl; furametpyr;
furcarbanil; furmecyclox;
guazatine; hexachlorobenzene; hexaconazole; hymexazole;
imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tris(albesil);
iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin;
20 isoprothiolane; isovaledione;
kasugamycin; kresoxim-methyl;
mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl; metalaxyl-M;
metconazole; methasulphocarb; methmroxam; metiram; metominostrobin; met-
sulphovax; mildiomycin; myclobutanil; myclozolin;
25 natamycin; nicobifen; nitrothal-isopropyl; noviflumuron; nuarimol;
ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxycarboxin;
oxyfenthiin;
paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen; phthalide; pic-
oxystrobin; piperalin; polyoxins; polyoxorim; probenazole; prochloraz; procymidone;
30 propamocarb; propanosine-sodium; propiconazole; propineb; proquinazid; pro-
thioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil; pyroquilon;
pyroxyfur; pyrrolenitrine;

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quinconazole; quinoxyfen; quintozene; simeconazole; spiroxamine; sulphur;
tebuconazole; tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole;
thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid; tolclofos-methyl;
tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide; tricyclamide; tri-
5 cyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole;
uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide;
(2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl] ethyl] -3-
methyl-2-[(methylsulphonyl)amino]butanamide;
1 -(1 -naphthalenyl)-1 H-pyrrole-2,5-dione;
10 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;
2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;
2-chloro-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridinecarboxamide;
3,4,5-trichloro-2,6-pyridinedicarbonitrile;
actinovate; cis-1 -(4-chlorophenyl)-2-( 1H-1,2,4-triazol-1 -yl)cycloheptanol;
15 methyl 1-(2,3-dihydro-2,2-dimethyl-1 H-inden-1 -yl)-1 H-imidazole-5-carboxylate;
monopotassium carbonate;
N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide;
N-butyl-8-( 1,1 -dimethylethyl)-1 -oxaspiro[4.5]decane-3-amine;
sodium tetrathiocarbonate;
20 and copper salts and preparations, such as Bordeaux mixture; copper hydroxide;
copper naphthenate; copper oxychloride; copper sulphate; cufraneb; copper oxide;
mancopper; oxine-copper.
Bactericides:
25 bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin,
octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, teclofta¬lam, copper sulphate and other copper preparations.
Insecticides / acaricides / nematicides:
30 abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole, acrinathrin,
AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb, aldoxycarb, allethrin, allethrin lR-isomers, alpha-cypermethrin (alphamethrin), amidoflumet, aminocarb,

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amitraz, avermectin, AZ-60541, azadirachtin, azamethiphos, azinphos-methyl, azin-phos-ethyl, azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis,
Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus
5 thuringiensis strain NCTC-11821, baculoviruses, Beauveria bassiana, Beauveria
tenella, bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthrin, beta-cyper-methrin, bifenazate, bifenthrin, binapacryl, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, bistrifluron, BPMC, brofen-prox, bromophos-ethyl, bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-
10 505, bufencarb, buprofezin, butathiofos, butocarboxim, butoxycarboxim, butyl-
pyridaben,
cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap, CGA-50439, chinomethionat, chlordane, chlordimeform, chloethocarb, chlor-ethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloro-
15 benzilate, chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl),
chlovaporthrin, chromafenozide, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin, clothiazoben, codlemone, couma-phos, cyanofenphos, cyanophos, cycloprene, cycloprothrin, Cydia pomonella, cy-fluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin (lR-trans-isomer),
20 cyromazine,
DDT, deltamethrin, demeton-S-raethyl, demeton-S-methylsulphone, diafenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos, dicofol, dicrotophos, dicyclanil, diflu-benzuron, dimethoate, dimethylvinphos, dinobuton, dinocap, dinotefuran, diofenolan, disulphoton, docusat-sodium, dofenapyn, DOWCO-439,
25 eflusilanate, emamectin, emamectin-benzoate, empenthrin (lR-isomer), endosulphan,
Entomopthora spp., EPN, esfenvalerate, ethiofencarb, ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,
famphur, fenamiphos, fenazaquin, fenbutatin oxide, fenfluthrin, fenitrothion, fenobu-carb, fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,
30 fenpyroximate, fensulphothion, fenthion, fentrifanil, fenvalerate, fipronil, flonicamid,
fluacrypyrim, fluazuron, flubenzimine, flubrocythrinate, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flumethrin, flupyrazofos, flutenzin (flufenzine),

Le A 35 963-Foreign Countries

fluvalinate, fonofos, formetanate, formothion, fosmethilan, fosthiazate, fubfenprox (fluproxyfen), furathiocarb,
gamma-HCH, gossyplure, grandlure, granulosis viruses,
halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexy-
5 thiazox, hydramethylnone, hydroprene,
IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos, iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin, japonilure, kadethrin, nuclear polyhedrosis viruses, kinoprene, lambda-cyhalothrin, lindane, lufenuron,
10 malathion, mecarbam, mesulphenfos, metaldehyde, metam-sodium, methacrifos,
methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin, MTI-800,
15 naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine, niten-
pyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, novaluron, novi-flumuron,
OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate, oxamyl, oxydemeton-methyl,
20 Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl), permethrin (cis-,
trans-), petroleum, PH-6045, phenothrin (lR-trans isomer), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl, pirimiphos-ethyl, prallethrin, profenofos, promecarb, propaphos, propargite, propetamphos, propoxur, prothiofos, prothoate, protrifenbute,
25 pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphen-
thion, pyridathion, pyrimidifen, pyriproxyfen, quinalphos, resmethrin, RH-5849, ribavirin, RU-12457, RU-15525, S-421, S-1833, salithion, sebufos, SI-0009, silafluofen, spinosad, spirodiclofen, spiromesifen, sulphluramid, sulphotep, sulprofos, SZI-121,
30 tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin,
temephos, temivinphos, terbam, terbufos, tetrachlorvinphos, tetradifon, tetramethrin, tetramethrin (lR-isomer), tetrasul, theta-cypermethrin, thiacloprid, thiamethoxam,

Le A 35 963-Foreign Countries

thiapronil, thiatriphos, thiocyclam hydrogenoxalate, thiodicarb, thiofanox, thiometon,
thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, trans-
fluthrin, triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon,
triflumuron, trimethacarb,
5 vamidothion, vaniliprole, verbutin, Verticillium lecanii,
WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, xylylcarb,
ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901,
the compound 3-methylphenyl propylcarbamate (tsumacide Z),
the compound 3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]-
10 octane-3-carbonitrile (CAS-Reg. No. 185982-80-3) and the corresponding 3-endo-
isomer (CAS-Reg. No. 185984-60-5) (cf. WO-96/37494, WO-98/25923),
and preparations which comprise insecticidally active plant extracts, nematodes, fungi or viruses. 15
A mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators, safeners and/or semiochemicals is also possible.
In addition, the compounds of the formula (I) according to the invention also have
20 very good antimycotic activity. They have a very broad antimycotic activity spectrum
in particular against dermatophytes and yeasts, moulds and diphasic fungi (for
example against Candida species such as Candida albicans, Candida glabrata) and
Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and
Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes,
25 Microsporon species such as Microsporon canis and audouinii. The list of these fungi
does by no means limit the mycotic spectrum which can be covered, but is only for illustration.
The active compounds can be used as such, in the form of their formulations or the
30 use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable
powders, pastes, soluble powders, dusts and granules. Application is carried out in a
customary manner, for example by watering, spraying, atomizing, broadcasting,

, Le A 35 963-Foreign Countries

dusting, foaming, spreading, etc. It is furthermore possible to apply the active compounds by the ultra-low volume method, or to inject the active compound preparation or the active compound itself into the soil. It is also possible to treat the seeds of the plants 5
When using the active compounds according to the invention as fungicides, the
application rates can be varied within a relatively wide range, depending on the kind
of application. For the treatment of parts of plants, the active compound application
rates are generally between 0.1 and 10,000g/ha, preferably between 10 and
10 1000 g/ha. For seed dressing, the active compound application rates are generally
between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. For the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5,000 g/ha.
15 As already mentioned above, it is possible to treat all plants and their parts according
to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in
20 combination with conventional methods (Genetically Modified Organisms), and parts
thereof, are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
Particularly preferably, plants of the plant cultivars which are in each case
25 commercially available or in use are treated according to the invention. Plant
cultivars are to be understood as meaning plants having new properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
30 Depending on the plant species or plant cultivars, their location and growth
conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example,

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reduced application rates and/or a widening of the activity spectrum and/or an
increase in the activity of the substances and compositions which can be used
according to the invention, better plant growth, increased tolerance to high or low
temperatures, increased tolerance to drought or to water or soil salt content, increased
5 flowering performance, easier harvesting, accelerated maturation, higher harvest
yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.
10 The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering)
which are preferably to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased
15 tolerance to drought or to water or soil salt content, increased flowering performance,
easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and
20 microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or
viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus
25 fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes,
cotton, tobacco and oilseed rape. Traits that are emphasized are in particular increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA,
30 CryIIIA, CryIHB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations
thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses

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by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and
resistance genes and correspondingly expressed proteins and toxins. Traits that are
furthermore particularly emphasized are the increased tolerance of the plants to
certain herbicidally active compounds, for example imidazolinones, sulphonylureas,
5 glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart
the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans),
10 KnockOut® (for example maize), StarLink® (for example maize), Bollgard®
(cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to
15 phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and
STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned also include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars which have these
20 genetic traits or genetic traits still to be developed, and which will be developed
and/or marketed in the future.
The plants listed can be treated according to the invention in a particularly
advantageous manner with the compounds of the general formula (I) or the active
25 compound mixtures according to the invention. The preferred ranges stated above for
the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text,
30 The preparation and the use of the active compounds according to the invention is
illustrated by the examples below.

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Preparation examples
Example 1

10

9.77 g of cesium carbonate and 2 ml of water are added to a solution of 3.12 g of N-(2-bromophenyl)-5-fluoro-1,3-dimethyl-lH-pyrazoIe-4-carboxamide and 3.28 g of 2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxin-6-ylboronic acid (V-l) in 10 ml of n-butanol. With stirring and under an atmosphere of argon, 60 mg of tetrakis-(triphenylphosphine)palladium(0) are added. The reaction mixture is stirred at 80°C for 8 h. For work-up, the mixture is poured into water and extracted with ethyl acetate and the extract is dried and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 2:1).

This gives 4.00 g (83% of theory) of 5-fluoro-l,3-dimethyl-N-[2-(2,2,3,3-tetrafluoro-
15 2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-1 H-pyrazole-4-carboxamide in the form of
a colourless solid [logP (pH 2.3) - 3.77].

Example 2

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10

Under argon, 0.37 g (1.6 mmol) of 5-bromo-2,2-difluoro-l,3-benzodioxoIe, 0.4g (1.6mmol) of 4,4,4',4',5,5,5,,5,-octamethyl-2,2'-bis-l,3,2-dioxaborolane and 0.42 g (4.3 mmol) of potassium acetate are suspended in 5 ml of dimethyl sulphoxide, and 0.05 g (0.07 mmol) of l,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride is added. After 2 h at 80°C, the mixture is cooled to room temperature, and 0.51 g (1.3 mmol) of N-(2-iodophenyl)-l-methyl-3-(trifluoromethyl)-lH-pyrazol-4-carbox-amide (IV-1), 3.25 ml of a 2 M solution of sodium carbonate and a further 0.05 g (0.07 mmol) of l,r-bis(diphenylphosphino)ferrocenepalladium(H) chloride are added. After 45 min at 70°C, the mixture is diluted with 5 ml of water and extracted 3 times with in each case 50 ml of ethyl acetate. The extracts are dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product is taken up in diethyl ether and chromatographed on silica gel (cyclohexane/ethyl acetate 3:1).

15 This gives 0.23 g (41% of theory) of N-[2-(2,2-difluoro-l,3-benzodioxol-5-yl)-
phenyl]-l-methyl-3-(trifluoromethyl)-lH-pyrazol-4-carboxamide [logP (pH 2.3) = 3.37].
The biphenylcarboxamides of the formula (I) listed in Table 1 below are likewise
20 prepared analogously to Examples 1 and 2 described above and in accordance with
the general descriptions of the processes.

Table 1

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Preparation of starting materials of the formula (IV)
5 Example (IV-1)

6.57g (30.0 mmol) of 2-iodoaniline and 6.1 g (60.0 mmol) of triethylamine are dissolved in 100 ml of tetrahydrofuran and, at room temperature, 7.65 g (36.0 mmol)
10 of l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carbonyl chloride are added slowly.
The reaction solution is heated at 50°C for 16 h. For work-up, the mixture is concentrated under reduced pressure and the crude product is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1), This gives 10.0 g (85% of theory) of N-(2-iodophenyl)-l-methyl-3-(trifluoromethyl)-
15 lH-pyrazole-4-carboxamide [logP (pH 2.3) = 2.46].

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Preparation of starting materials of the formula (V)
Example (V-l)

A few grains of iodine are added to a suspension of 4.86 g of magnesium turnings in 20 ml of tetrahydrofuran (anhydrous), and 57.4 g of 6-bromo-2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzodioxine in 60 ml of tetrahydrofuran are then added dropwise under an atmosphere of argon. By adjusting the rate of the dropwise addition, the
10 exothermic reaction is maintained close to the boiling point. After the dropwise
addition has ended, the mixture is stirred under reflux for 30 min and then cooled to room temperature. The solution of the Grignard reagent is, together with a solution of 29.2 g of triethyl borate in 60 ml of tetrahydrofuran, added dropwise, at -10°C and over a period of 30 min, to 100 ml of tetrahydrofuran. The mixture is then stirred at
15 -10°C for another 1 h and then warmed to room temperature and stirred for another
30 min. For work-up, the reaction solution is, at -10°C, hydrolysed with 14 ml of water and adjusted to pH 4 using 80 ml of 10% strength sulphuric acid. The mixture is extracted with diethyl ether and the aqueous phase is saturated with sodium chloride and extracted with diethyl ether. The combined ether phases are, together
20 with 200 ml of water, concentrated. The solid residue is triturated with a little
methylene chloride, filtered off with suction and dried.
This gives 47.3 g (75% of theory) of 2,2,3,3-tetrafluoro-2,3-dihydro-l,4-benzo-dioxin-6-yl-boronic acid [logP (pH 2.3) = 2.49].

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The logP values given in the Preparation Examples were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C 18). Temperature: 43°C.
Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
Calibration was carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones).
The lambda max values were determined in the maxima of the chromatographic signals using the UV spectra from 200 nm to 400 nm.

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Use examples
Example A
5 Podosphaera test (apple) / protective
Solvents: 24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether
10
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.
15 To test for protective activity, young plants are sprayed with the preparation of active
compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha. The plants are then placed in a greenhouse at about 23 °C and a relative atmospheric humidity of about 70%.
20
Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
25 Active compounds, application rates and test results are shown in the table below.

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Example B
Sphaerotheca test (cucumber) / protective
5 Solvents: 24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active
10 compound is mixed with the stated amounts of solvents and emulsifier, and the
concentrate is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the preparation of active
compound at the stated application rate. After the spray coating has dried on, the
15 plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea.
The plants are then placed in a greenhouse at about 23°C and a relative atmospheric humidity of about 70%.
Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which
20 corresponds to that of the control, whereas an efficacy of 100% means that no
infection is observed.
Active compounds, application rates and test results are shown in the table below.

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Example C
Venturia test (apple) / protective
5 Solvents: 24.5 parts by eight of cetone
24.5 parts by weight of dimethylacetamide
Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active
10 compound is mixed with the stated amounts of solvents and emulsifier, and the
concentrate is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the preparation of active
compound at the stated application rate. After the spray coating has dried on, the
15 plants are inoculated with an aqueous conidia suspension of the apple scab pathogen
Venturia inaequalis and then remain in an incubation cabin at about 20°C in 100% relative atmospheric humidity for 1 day.
The plants are then placed in a greenhouse at about 21°C and a relative atmospheric
20 humidity of about 90%.
Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 25
Active compounds, application rates and test results are shown in the table below.

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Example D
Alternaria test (tomato) / protective
5 Solvent: 49 parts by weight of N,N-dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active
compound is mixed with the stated amounts of solvent and emulsifier, and the
10 concentrate is diluted with water to the desired concentration.
To test for protective activity, young tomato plants are sprayed with the preparation
of active compound at the stated application rate. 1 day after the treatment, the plants
are inoculated with a spore suspension of Alternaria solani and then remain at 100%
15 relative humidity and at 20°C for 24 h. The plants then remain at 96% relative
atmospheric humidity and a temperature of 20°C.
Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which
corresponds to that of the control, whereas an efficacy of 100% means that no
20 infection is observed.
Active compounds, application rates and test results are shown in the table below.

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Example E
Puccinia test (wheat) / protective
5 Solvent: 25 parts by weight of N,N-dimethylacetamide
Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active
compound is mixed with the stated amounts of solvent and emulsifier, and the
10 concentrate is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the preparation of active
compound at the stated application rate. After the spray coating has dried on, the
plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain
15 in an incubation cabin at 20°C and 100% relative atmospheric humidity for 48 hours.
The plants are then placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of 80% to promote the development of rust pustules.
20 Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which
corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
25

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Example F
Inhibitory test using a giant colony of Basidiomycetes
Mycelium pieces were punched out of a giant colony of the Basidiomycetes species Coriolus versicolor and incubated at 26°C on a nutrient agar medium containing malt extract peptone. The inhibition of the growth of the fungal threads on active-compound-containing nutrient media was compared to the longitudinal growth on nutrient media without added active compound and rated as inhibition in per cent.
In this test, for example, the following compounds according to the invention of the Preparation Examples show good activity:

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WE CLAIM;
1. Biphenylcarboxamides of the formula (I)

in which
R1 and R2 independently of one another represent hydrogen, halogen, cyano, nitro,
having in each case 1 to 13 fluorine, chlorine and/or bromine atoms,
m represents 1, 2, 3 or 4, where R1 represents identical or different radicals if m represents 2, 3 or 4,
n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3,
R3 represents hydrogen, hydroxyl,

haloalkyl having 1 to 7 halogen atoms,
alkylsulphenyl, haloalkylsulphenyl having 1 to 7 halogen
atoms, , carbamoyl,

Y represents carbonyl or represents which is
optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen,

having in each case 1 to 13 fluorine, chlorine and/or bromine atoms and
A represents a radical of the formula
where
R4 represents hydrogen, cyano, halogen, nitro,
having 1 to 5 halogen atoms, cycloalkyl, having 1 to 5
halogen atoms, having 1
to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C1-C4 alkyl and
R5 represents hydrogen, halogen, cyano, alkoxy or and
R6 represents hydrogen, having 1
to 5 halogen atoms,
cycloalkyl, haloalkylthio- 1 to 5 halogen atoms,

1 to 5 halogen atoms or phenyl,

or
A represents a radical of the formula
R7 and R8 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and
R9 represents halogen, cyano or C1-C4-alkyl or C1-C4-haloalkoxy having 1 to 5 halogen atoms,
or
A represents a radical of the formula

R10 and R11 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and
R12 represents hydrogen, C1-C4-alkyl or hydrogen,
or
A represents a radical of the formula

or

R13 represents hydrogen, halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-haloalkoxy having 1 to 5 halogen atoms or C1-C4-haloalkylthio having 1 to 5 halogen atoms,
represents a radical of the formula

R14 represents halogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio having 1 to 5 halogen atoms, or C1-C4-haloalkoxy having 1 to 5 halogen atoms and
R15 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkoxy having 1 to 5 halogen atoms, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl,
or
represents a radical of the formula

R16 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and
R17 represents C1-C4-alkyl,
X1 represents a sulphur atom, represents SO, SO2 or CH2,
p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2,
or
A represents a radical of the formula

R18 represents Ci-C4-alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms,
or
A represents a radical of the formula

R19 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,

A represents a radical of the formula

R20 represents halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
R21 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and
R22 represents hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkylsulphonyl, di(C1 -C4-alkyl)-aminosulphonyl, C1-C6-alkylcarbonyl or optionally substituted phenylsulphonyl or benzoyl,
or
A represents a radical of the formula

R23 and R24 independently of one another represent hydrogen, halogen, amino, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and

R25 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
or
A represents a radical of the formula

R26 and R27 independently of one another represent hydrogen, halogen, amino, nitro, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and
R28 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
Or
A represents a radical of the formula

R29 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and
R30 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,

or
A represents a radical of the formula

R31 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms and
R32 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
or A represents a radical of the formula

R33 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
or
R34 represents hydrogen or C1-C4-alkyl and

A represents a radical of the formula

R35 represents halogen or C1-C4-alkyl,
or
A represents a radical of the formula

R36 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
or
A represents a radical of the formula

R37 represents hydrogen, halogen or C1-C4-alkyl.
2. Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein
R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6- alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
m represents 1, 2 or 3, where R1 represents identical or different radicals if m represents 2 or 3,

n represents 1, 2 or 3, where R2 represents identical or different radicals if n represents 2 or 3,
R3 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4- alkoxy, C1-C3-alkoxy-C1-C2-alkyl, cyano-C1-C4-alkyl, C1-C4- haloalkyl having 1 to 5 halogen atoms, C1-C4-aminoalkyl, C1-C4- alkylsulphenyl, C1-C4-haloalkylsulphenyl having 1 to 5 halogen atoms, (C1-C4-alkyl)carbonyl,
Y represents carbonyl or represents C1-C2-alkylene which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4- alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy and/or C1-C4-haloalkylthio having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
and
A represents a radical of the formula

R4 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, methylthio, ethylthio,

or

trifluoromethylthio, di-fluoromethylthio aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl,
R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and
R6 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl,
or
represents a radical of the formula
R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and
R9 represents fluorine, chlorine, bromine, cyano, methyl, ethyl or C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms,
represents a radical of the formula

R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2 haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and
R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl,
or
A represents a radical of the formula

R13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms or C1-C2-haloalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
represents a radical of the formula

R14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio or C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms and
R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, C1-C4-alkyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, C1-C2-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-alkylsulphinyl or C1-C2-alkylsulphonyl,
or
A represents a radical of the formula

R16 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and
R17 represents methyl or ethyl,

X1 represents a sulphur atom, represents SO, SO2 or CH2 and
p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2,
or
A represents a radical of the formula

R18 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
A represents a radical of the formula

R19 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
A represents a radical of the formula

where

R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and
R22 represents hydrogen, methyl, ethyl, C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C1-C2-alkoxy-C1-C2-alkyl, hydroxymethyl, hydroxyethyl, methyl sulphonyl or dimethylaminosulphonyl,
or
A represents a radical of the formula

R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms
and

R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
represents a radical of the formula
R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and
R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
A represents a radical of the formula

R29 represents hydrogen, fluorine, chlorine, bromine, amino, C1-C4-alkylamino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and

R30 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2- haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
A represents a radical of the formula

R31 represents hydrogen, fluorine, chlorine, bromine, amino, C1 -C4-alkylamino, di(C1-C4-alkyl)amino, cyano, methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms and
R32 represents fluorine, chlorine, bromine, methyl, ethyl or haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
A represents a radical of the formula

R33 represents fluorine, chlorine, bromine, methyl, ethyl or C1-C2- haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,

or
A represents a radical of the formula

R34 represents hydrogen, methyl or ethyl and
R35 represents fluorine, chlorine, bromine, methyl or ethyl,
or
A represents a radical of the formula

R36 represents methyl, ethyl or C1-C2-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
A represents a radical of the formula

R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.
Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein
R1 and R2 independently of one another represent hydrogen,
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-
propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy,
methylthio, ethylthio, trichloromethyl, trifluoromethyl,
difluoromethyl, difluorochloromethyl, difluoromethoxy,
trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio,
m represents 1 or 2, where R1 represents identical or different radicals if m represents 2,
n represents 1 or 2, where R2 represents identical or different radicals if n represents 2,
R3 represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, methoxymethyl, cyanomethyl, difluoromethyl, methylsulphenyl, trichloromethylsulphenyl or acetyl,
represents carbonyl or represents -CH2- or -(CH2)2-, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine,

bromine, methyl, ethyl, i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio,
and
A represents a radical of the formula

R4 represents hydrogen, fluorine, chlorine, bromine, iodine,
methyl, ethyl, i-propyl, monofluoromethyl, difluoromethyl,
trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclo-
propyl methoxy, ethoxy, trifluoromethoxy, trichloromethoxy,
methylthio, ethylthio, trifluoromethylthio or
difluoromethylthio and
R5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio and
R6 represents hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl,
or
A represents a radical of the formula

R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoro-methyl difluorochloromethyl or trichloromethyl and
R9 represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy,
or
A represents a radical of the formula

R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and
R12 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl,
or
A represents a radical of the formula

or

R13 represents hydrogen, fluorine, chlorine, bromine, iodine,
hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl,
i-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl, di-
fluorochloromethyl, trichloromethyl, trifluoromethoxy, di
fluoromethoxy difluorochloromethoxy, trichloromethoxy, tri-
fluoromethylthio difluoromethylthio, di-
fluorochloromethylthio or trichloromethylthio,
represents a radical of the formula
R14 represents fluorine, chlorine, bromine, iodine, hydroxyl,
cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-
butyl, t-butyl, trifluoromethyl, difluoromethyl,
difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio trifluoromethylthio, trifluoromethoxy, difluoro methoxy, difluorochloromethoxy or trichioromethoxy and
R15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,

trifluoro methyl difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulphonyl,
or
A represents a radical of the formula

R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R17 represents methyl or ethyl,
X1 represents a sulphur atom, represents SO, S02 or CH2 and
p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2,
or
A represents a radical of the formula

R18 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,
or
A represents a radical of the formula

R19 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,
or
A represents a radical of the formula

R20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl,
i-propyl, trifluoromethyl, difluoromethyl,
difluorochloromethyl or trichloromethyl,
R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and

R22 represents hydrogen, methyl, ethyl, trifluoromethyl, methoxy-methyl, ethoxymethyl, hydroxymethyl or hydroxyethyl,
or
A represents a radical of the formula

R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difiuoromethyl, difluorochloromethyl or trichloromethyl,
or
A represents a radical of the formula

R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl,

trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,
or
A represents a radical of the formula

R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R30 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichioromethyl,
or
A represents a radical of the formula

R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R32 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoro-methyl difluoromethyl, difluorochloromethyl or trichloro- methyl,
or
A represents a radical of the formula

R33 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,
or
R34 represents hydrogen, methyl or ethyl and

A represents a radical of the formula

R35 represents fluorine, chlorine, bromine, methyl or ethyl,
or
A represents a radical of the formula

R36 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,
or
A represents a radical of the formula

R37 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.
4. Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein
R1 and R2 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, trifluoromethylthio,

m represents 1 or 2, where R1 represents identical or different radicals if m represents 2,
n represents 1,
R3 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, t-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
Y represents carbonyl or represents -CH2- or -(CH2)2-, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, methyl, i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio,
and
A represents a radical of the formula

R4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and
R5 represents hydrogen, fluorine, chlorine, bromine, iodine or methyl and
R6 represents hydrogen, methyl, trifluoromethyl or phenyl,

or
A represents a radical of the formula

R7 and R8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl and
R9 represents fluorine, chlorine, bromine, methyl or trifluoro methoxy,
or
A represents a radical of the formula

R10 and R11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl and
R12 represents hydrogen, fluorine, chlorine, bromine or methyl,
or
A represents a radical of the formula

R13 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl,
or
A represents a radical of the formula

R14 represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and
R15 represents hydrogen, fluorine, chlorine, bromine, iodine, n-
propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,
trifluoromethyl, difluoromethyl, trichloromethyl,
methylsulphinyl or methylsulphonyl,
or
represents a radical of the formula

R16 represents methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and

R17 represents methyl or ethyl,
X1 represents a sulphur atom, represents SO, SO2 or CH2 and
p represents 0, 1 or 2, where R17 represents identical or different radicals if p represents 2,
or
A represents a radical of the formula

R18 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
A represents a radical of the formula

R19 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
represents a radical of the formula

where

R20 represents fluorine, chlorine, bromine, methyl, i-propyl, trifluoromethyl, difluoromethyl or trichloromethyl,
R21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl and
R22 represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl,
or
A represents a radical of the formula

R23 and R24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl,

R26 and R27 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and
R28 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
A represents a radical of the formula

R29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and
R30 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or

represents a radical of the formula

R31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl and
R32 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
A represents a radical of the formula

R33 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
R34 represents hydrogen, methyl or ethyl and
R35 represents fluorine, chlorine, bromine, methyl or ethyl,

A represents a radical of the formula

or
A represents a radical of the formula

R36 represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl,
or
A represents a radical of the formula

R37 represents hydrogen, fluorine, chlorine, bromine or methyl.
5. Biphenylcarboxamides of the formula (I) as claimed in claim 1 wherein
R1 represents hydrogen, fluorine, chlorine, methyl,
R2 represents hydrogen,
m represents 1 or 2, where R1 represents identical or different radicals if m represents 2,
n represents 1,

R3 represents hydrogen,
Y represents and A represents a radical of the formula

R4 represents methyl, monofluoromethyl, difluoromethyl or trifluoromethyl and
R5 represents hydrogen, fluorine, chlorine or methyl and
R6 represents methyl,
or
A represents of the formula

R7 and R8 represent hydrogen and R9 represents methyl,
or

A represents a radical of the formula

R10 and R11 represent hydrogen and R12 represents methyl,
or
A represents a radical of the formula

R13 represents iodine, methyl, difluoromethyl or trifluoromethyl,
or
A represents a radical of the formula

R20 represents methyl, trifluoromethyl or difluoromethyl,

R21 represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl or difluoromethyl and
R22 represents hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl,
or
A represents a radical of the formula

R23 and R24 represent hydrogen and R25 represents methyl,
or
A represents a radical of the formula

R26 and R27 represent hydrogen and R28 represents methyl,

or
A represents a radical of the formula

R29 represents amino, methylamino, dimethylamino, methyl or trifluoromethyl and
R30 represents methyl, trifluoromethyl or difluoromethyl,
or
A represents a radical of the formula

R31 represents amino, methylamino, dimethylamino, methyl or trifluoromethyl and
R32 represents methyl, trifluoromethyl or difluoromethyl,
or

A represents a radical of the formula

R36 represents methyl or trifluoromethyl.
Process for preparing biphenylcarboxamides of the formula (I) as claimed in claim 1, wherein said process comprises
a) carboxylic acid derivatives of the formula (II)

in which A is as defined in Claim 1 and G represents halogen, hydroxyl or C1-C6-alkoxy,
are reacted with aniline derivatives of the formula (III)

in which
R1, R2, m, n, R3 and Y are as defined in Claim 1,
if appropriate in the presence of a catalyst, if appropriate in the 5 presence of an acid binder and if appropriate in the presence of a diluent,

b) carboxamide derivatives of the formula (IV)
or

in which
R1, m, R3 and A are as defined in Claim 1,
are reacted with boronic acid derivatives of the formula (V)

in which
R2, n and Y are as defined in Claim 1 and
G1 and G2 each represent hydrogen or together represent tetramethyl ethylene,
in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,

c) carboxamide boronic acid derivatives of the formula (VI)

in which
R1, m, R3 and A are as defined in Claim 1 and
G1 and G2 each represent hydrogen or together represent tetramethyl ethylene,
are reacted with phenyl derivatives of the formula (VII)

in which
R2, n and Y are as defined in Claim 1,
in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,
or
d) carboxamide derivatives of the formula (IV)

in which
R1, m, R3 and A are as defined in Claim 1,
are reacted with phenyl derivatives of the formula (VII)

in which
R2, n and Y are as defined in Claim 1,
in the presence of a palladium or platinum catalyst and in the presence of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis- 1,3,2-dioxaborolane, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
7. Compositions for controlling unwanted microorganisms, wherein said composition comprises from 0.1 to 95wt% of at least one biphenylcarboxamide of the formula (I) as claimed in claim 1, in addition to extenders and/or surfactants.
8. Biphenylcarboxamides of the formula I as defined in claim 1 substantially as hereinbefore described with reference to the foregoing examples.

9. Process for preparing biphenylcarboxamides of the formula I as defined in claim 1 substantially as hereinbefore described with reference to the foregoing examples.
Dated this 17th day of April, 2003.
[DEEPAK KUMAR] OF REMFRY & SAGAR ATTORNEY FOR THE APPLICANTS]

Documents:

377-mum-2003-cancelled pages(26-12-2006).pdf

377-mum-2003-claims(granted)-(26-12-2006).pdf

377-mum-2003-correspondence(31-01-2007).pdf

377-mum-2003-correspondence(ipo)-(01-02-2006).pdf

377-mum-2003-form 1(17-04-2003).pdf

377-mum-2003-form 1(27-05-2003).pdf

377-mum-2003-form 18(30-04-2005).pdf

377-mum-2003-form 2(granted)-(26-12-2006).pdf

377-mum-2003-form 3(17-04-2003).pdf

377-mum-2003-form 3(22-05-2003).pdf

377-mum-2003-form 5(17-04-2003).pdf

377-mum-2003-power of authority(17-04-2003).pdf

377-mum-2003-power of authority(26-12-2006).pdf

377-mumn-2003-claims(granted)-(26-12-2006).doc

377-mumn-2003-form 2(granted)-(26-12-2006).doc

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Patent Number

208356

Indian Patent Application Number

377/MUM/2003

PG Journal Number

32/2007

Publication Date

10-Aug-2007

Grant Date

24-Jul-2007

Date of Filing

17-Apr-2003

Name of Patentee

BAYER CROPSCIENCE AKTIENGESELLSCHAFT

Applicant Address

ALFRED-NOBEL-STR.50, 40789 MONHEIM, GERMANY.

Inventors:

#	Inventor's Name	Inventor's Address
1	RALF DUNKEL	KRISCHER STR. 22, 40789 MONHEIM, GERMANY.
2	HANS-LUDWIG ELBE	DASNOCKEL 59, 42329 WUPPERTAL, GERMANY.
3	HEIKO RIECK	14 20 RUE PIERRE BAIZET, 69009 LYON, FRANCE.
4	ROBERT MARKERT	SILESIUSSTR. 82, 51065 KOLN, GERMANY.
5	ULRIKE WACHENDORFF-NEUMANN	OBERER MARKENWEG 85, 56566 NEUWIED, GERMANY.
6	ASTRID MAULER-MACHNIK	NEUENKAMPER WEG 48, 42799 LEICHLINGEN, GERMANY.
7	KARL-HEINZ KUCK	PASTOR-LOEH-STR. 30A, 40764 LANGENFELD, GERMANY.
8	MARTIN KUGLER	AM KLOSTER 47, 42799 LEICHLINGEN, GERMANY.
9	THOMAS JAETSCH	INNERE KANALSTR.220, 50670 KOLN, GERMANY.

PCT International Classification Number

A01N43/78

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	10219035.6	2002-04-29	Germany