Title of Invention	"N-SUBSTITUTED PYRAZOLYLCARBOXANILIDES OF FORMULA (I) AND PROCESS FOR PREPARATION THEREOF"
Abstract	N-substituted pyrazolylcarboxanilides of the formula (I) In which R1 represents methyl or trifluoromethyl R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, a) R3 represents hydrogen, R4 represents C1-C8-alkyl,C1-C4alkoxy-C1-C4-alkyl, or -C(=O)C(=O)R5 b) R3 represents C1-C8-alkyl R4 represents C1-C8 alkyl, C1-C4-alkoxy- C1-C4-alkyl, (C1-C8-alkyl)carbonyl,-C(=O)C(=O)R5, R5 represents C1-C8-alkoxy.

Title of Invention

"N-SUBSTITUTED PYRAZOLYLCARBOXANILIDES OF FORMULA (I) AND PROCESS FOR PREPARATION THEREOF"

Abstract

N-substituted pyrazolylcarboxanilides of the formula (I) In which R1 represents methyl or trifluoromethyl R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, a) R3 represents hydrogen, R4 represents C1-C8-alkyl,C1-C4alkoxy-C1-C4-alkyl, or -C(=O)C(=O)R5 b) R3 represents C1-C8-alkyl R4 represents C1-C8 alkyl, C1-C4-alkoxy- C1-C4-alkyl, (C1-C8-alkyl)carbonyl,-C(=O)C(=O)R5, R5 represents C1-C8-alkoxy.

Full Text	"N- SUBSTITUTED PYRAZOLYLCARBOXANILIDES OF FORMULA (I) AND PROCESS FOR PREPARATION THEREOF" The present invention relates to novel (N-substituted) pyrazolylcarboxanilides, to a plurality of processes for their preparation and to their use for controlling unwanted microorganisms. It is already known that numerous carboxanilides have fungicidal properties (cf. WO 93/11117, EP-A 0 545 099, EP-A 0 824099, JP 63-48269, WO 02/059086 and JP 8-176112). N-[2-(l,3-Dimethyl-butyl)phenyl]-5-fluoro-l-methyl-N-prop-2-yn-1-yl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide and N-aceryl-N-[2-(l,3-dimethylburyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4- carboxamide (WO 02/059086) may be mentioned by way of example. The activity of these com¬pounds is good; however, at low application rates it is sometimes unsatisfactory. This invention now provides novel N-substituted pyrazolylcarboxanilides of the formula (!) .1 (Formula Removed) in which R1 represents methyl, trifluoromethyl or difluoromethyl, R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, a) R3 represents hydrogen, R4 represents C1-C8-alkyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy- C1- C4-alkyl, C3-C8-cycloalkyl; CrC6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsul- phinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo- alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1 - C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C,- C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C3-C8-cycloalkyl)carbonyl; (C3-C8-halocycloalkyl)carbonyl having 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=0)C(=0)R5, -CONRV or -CH2NRER9, b) R3 represents halogen, C1-C8-alkyl or C1-C8-haloalkyl, R4 represents C1-C8-aIkyl, CrC6-a]kylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy-Cr C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsul-phinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo-alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C3-C8-cycloalkyl)carbonyl; (C3-C8-halocycloalkyl)carbonyl having 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=0)C(=0)R5, -CONR6R7 or -CH2NR8R9, b) R3 represents halogen, C1-C8-alkyl or C1-C8-haloalkyl, R4 represents C1-C8-alkyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsul-phinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo-alkyl having in each case I to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1- C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C1- C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-cycloalkyl)carbonyl; (C1-C6-haloalkyl)carbonyl, (C1-C6-haloalkoxy)carbonyl, (halo-C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=0)R5, -CONR6R7 or -CH2NR8R9, R5 represents hydrogen, C1-C8-alkyl,C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C6-haloalkoxy, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, R6 and R7 independently of one another, each represent hydrogen, C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C8-haloalkyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo-alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, R6 and R7 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C1-C4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR1 , R8 and R9 independently of one another, represent hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl; C1-C8-halo- alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, R8 and R9 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and Ci-C4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR10, R10 represents hydrogen or C1-C6-alkyl. If appropriate, the compounds according to the invention can be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also of tautomers. What is claimed are both the E and Z isomers, and the threo and erythrp and also the optical isomers, any mixtures of these isomers and the possible tautomeric forms. Furthermore, it has been found that N-substituted pyrazolylcarboxanilides of the formula (I) are obtained when a) carboxylic acid derivatives of the formula (II)O. R" N I CH, in which R1 is as defined above and X1 represents halogen or hydroxyl are reacted with an aniline derivative of the formula (III) (Figure Removed) (ffl) or b) in which R2, R3 and R4 are as defined above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, pyrazolylcarboxanilides of the formula (IV) (Figure Removed) or c) in which R1, R2, R3 and R4 are as defined above are hydrogenated, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, pyrazolylcarboxanilides of the formula (la) (Figure Removed) in which R1, R2 and R3 are as defined above are reacted with halides of the formula (V) R— *' (V) in which R1 is as defined above and X' represents chlorine, bromine or iodine in the presence of a base and in the presence of a diluent. Finally, it has been Ibund that the novel N-substituted pyrazolylcarboxanilides 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. The formula (I) provides a general definition of the N-substituted pyrazolylcarboxanilides according to the invention. Preferred radical definitions of the formulae mentioned above and below are given below. These definitions apply to the end products of the formula (I) and likewise to all intermediates. R1 tolerably represents methyl. R1 furthermore preferably represents trifluoromethyl. R1 furthermore pjeferably represents difluoromethyl. R2 preferably represents hydrogen. R2 furthermore preferably represents fluorine, where fluorine is particularly preferably located in the 4-, 5- or 6-position, veryjrarjjcularlyjjreferably in the 4- or 6-position, especially in the 4-position, of the anilide radical [cf. formula (I) above]. R2 furthermore preferably represents chlorine, where chlorine is particularly preferably located in the 5-position of the anilide radical [cf. formula (I) above]. R2 furthermore preferably represents methyl, where methyl is particularly preferably located in the 3-position of the anilide radical (cf. formula (I) above]. R2 furthermore preferably represents trifluoromethyl, where trifluoromethyl is particularly preferably located in the 4- or 5-position of the anilide radical [cf. formula (I) above]. If R3 represents hydrogen, R4 preferably represents CrC6-alkyl, CrC4-alkylsulphinyl, CrC4-alkylsulphonyl, CrC3-alkoxy-C,-C3-alkyl, C3-C6-cycloalkyl; CrC4-haloalkyl, C,-C4-haloalkylthio, CrC4-haloalkylsulphi-nyl, CrC4-haloalkylsulphonyl, halo-Ci-C3-alkoxy-Ci-C3-alkyl, C3-C6-halocycloalkyl having m each case 1 to 9 iluonne, chlonne and/or bromine atoms; formyl, formyl-Ci-C3-alkyl, (Cr Cj-alkyl)carbonyl-C,-C3-alkyl, (CrC3-alkoxy)carbonyl-CrC3-alkyl; halo-(C,-C3-alkyl)carbo-nyl-Cj-Cj-alkyl, halo-(Ci-C3-alkoxy)carbonyl-CrC3-alkyl having in each case 1 to 13 fluorine, chlonne and/or bromine atoms; (C3-C5-cycloalkyl)carbonyl; (C3-C6-halocycloalkyl)carbonyl having 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR'R7 or -CH2NR8R9. If R3 represents hydrogen, R4 particularly preferably represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hcxyl, methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-, sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or isopropylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopro- pyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethyl- thio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphmyl, rrifluorome- thylsulphonyl, trifluoromethoxymethyl; formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3, -(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(C1I2)2-CO,CH,, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CH2-CO-CClt, -CH2-CO-CH2CF3, -CH2-CO-CH2CC13, -(CH2)2-CO-CH2CF3, -(CH2)2-CO-CH2CC13, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CC13, -OH2-C02CC]2CC13, -(CH2)2-C02CH2CF3, -(CH2)2-C02CF2CF3, -(CH2)2-CO2CH2CC13, -(CH2)2-CO,CC12('C13; cyclopropylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl or -C(=O)C(=O)R5, CONR6R7 or -CH2NR8R9. If R3 represents hydrogen, R4 very ^pai^iculadY ^rjejierably represents methyl, methoxymethyl, formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -C(=O)CHO, -C(=O)C(=O)CH3, -C(=O)C(==O)CH2OCH3, -C(=O)CO2CH3, -C(=O)CO2CH2CH3. If R3 preferably represents fluorine, chlorine, bromine, iodine, CrC6-alkyl or CrC6-haloalkyl having 1 to 13 fluorine, chlorine and/or bromine atoms, particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl or Ci-C4-haloalkyl having 1 to 9 fluorine, chlorine and/or bromine atoms, y.^_B.articjJ.larly--pieferab-ly represents methyl, ethyl, fluorine, chlorine, trifluoromethyl, then R4 preferably represents C]-C6-alkyl, Ci-C4-alkylsulphinyl, CrC4-alkylsulphonyl, CrC3-alkoxy-CrCj-alkyl, CrC6-cycloalkyl; Ci-C4-haloalkyl, Ci-C4-haloalkylthio, CrC4-haloalkylsulphi-nyl, CrC4-haloalkylsulphonyl, halo-CrC3-alkoxy-Ci-C3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-CrC3-alkyl, (Cr C3-alkyl)carbonyl-Ci-C3-alkyl, (CrC3-alkoxy)carbonyl-CrC3-alkyl; halo-(Ci-C3-alkyl)carbo-nyl-CrC3-alkyl, halo-(CrC3-alkoxy)carbonyl-Ci-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (CrC6-alkyl)carbonyl, (CrC6-alkoxy)carbonyl, (CrC3-alkoxy-CrC3-alkyl)carbonyl, (C3-C6- cycloalkyl)carbonyl; (CrC4-haloalkyl)carbonyl, (C\|-C4-haloalkoxy)carbonyl, (halo-C]-C3- alkoxy-CrCj-alkyl)carbonyl, (C3-C6-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR6R7 or -CH2NR8R9, particularly preferably represents methyl, ethyl, n- or isopropyl, n-, iso, sec- or tert-butyl, pentyl or hexyl, methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-, sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or isopropylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopro- pyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethyl- thio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphmyl, trifluorome- thylsulphonyl, trifluoromethoxymethyl; formyl, -CH2-CHO, -CH2CH2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3, -(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CH2)2-CO2CH3, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CHz-CO-CCl.,, -CH2-CO-CH2CF3, -CH2-CO-CH2CC13, -(CH2)2-CO-CH2CF3, -(CH2)2-CO-CH2CC13, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CC13, -CH2-C02CC12CC13, -(CH2)2-C02CH2CF3, -(CH2)2-CO2CF2CF3, -(CH2)2-CO2CH2CC13, -(CH2)2-C02CC12CC13; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl; trifluoro-methylcarbonyl, trifluoromethoxycarbonyl, or -C(=O)C(=O)R5, -CONR6R7 or -CH2NR8R9, YgQL_BglllCMiiEly==.Ptefersbly represents methyl, methoxymethyl, formyl, -CH2-CHO, -(CII2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -C(=O)CHO, -C(=0)C(=0)CH3, -C(=O)C(=O)CH2OCH3, -C(=O)CO2CH3, -C(=O)CO2CH2CH3. R5 preferably represents hydrogen, Q-Ce-alkyl, C,-C4-alkoxy, Ci-C3-alkoxy-Ci-C3-alkyl, C3-C6-cycloalkyl; CrC4-haloalkyl, C,-C4-haloalkoxy, halo-Ci-C3-alkoxy-CrC3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms. R5 particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, tert-butyl, methoxy, elhoxy, n- or isopropoxy, tert-butoxy, cyclopropyl; trifluoromethyl, tri fluoromethoxy. R6 and R; independently of one another, preferably represent hydrogen, CrC6-alkyl, CrC3-alkoxy-CrQ-alkyl, C3-C6-cycloalkyl; C,-C4-haloalkyl, halo-C,-C3-alkoxy-Ci-C3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms. R6 and R7 furthermore together with the nitrogen atom to which they are attached preferably form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen and CrC4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR10. R6 and R7 independently of one another, particularly preferably represent hydrogen, methyl, ethyl, n-or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxy-ethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, tri fluoromethoxymethyl. R6 and R' furthermore together with the nitrogen atom to which they are attached particularly preferably form a saturated heterocycle from the group consisting of morpholme, thiomor-pholine and piperazine which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl, where the piperazine may be substituted by R10 on the second nitrogen atom. R8 and R9 independently of one another, preferably represent hydrogen, CrC6-alkyl, C3-C6-cyclo-alkyl; Ci-C4-haloalkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms. R8 and R9 furthermore together with the nitrogen atom to which they are attached preferably form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen and Ci~C4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR10. R8 and R9 independently of one another, particularly preferably represent hydrogen, methyl, ethyl, n-or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxy-ethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, tri fluoromethoxymethyl. R8 and R9 furthermore together with the nitrogen atom to which they are attached particularly preferably form a saturated heterocycle from the group consisting of morpholine, thiomorpholine and piperazme which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl, where the piperazine may be substituted by R10 on the second nitrogen atom. R10 preferably represents hydrogen or C]-C4-alkyl. RU) particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl. Emphasis is given to compounds of the formula (I) in which R4 represents formyl. Emphasis is furthermore given to compounds of the formula (I) in which R4 represents -C(=O)C(=O)R5, where R5 is as defined above. Emphasis is furthermore given to N-substituted pyrazolylcarboxanilides of the formula (Ib) (Figure Removed) in which R4A represents CrC8-alkyl, CrC6-alkylsulphinyl, C,-C6-alkylsulphonyl, CrC4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; CrC6-haloalkyl, d-C4-haloalkylthio, CrC4-haloalkylsulphinyl, Cr Q-haloalkylsulphonyl, halo-Ci-C4-alkoxy-CrC4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-CrC3-alkyl, (CrC3-alkyl)carbonyl-C,-C3-alkyl, (C1-C3-alkoxy)carbonyl-C]-C3-alkyl; halo-(CrC3-alkyl)carbonyl-C\|-C3-alkyl, halo-(C\|-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C3-C8-cycloalkyl)carbonyl; (C3-C8-halocycloalkyl)carbonyl having 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR'Tl7 or -CH2NR8R9, and R1, R2, R5, R6, R7, R8 and R9 are as defined above. Emphasis is furthermore given to N-substituted pyrazolylcarboxanilides of the formula (Ic) (Figure Removed) in which R3B represents halogen, CrC8-alkyl or Ci-C8-haloalkyl, R4B represents CrCg-alkyl, CrC6-alkylsulphinyl, Ci-C6-alkylsulphonyl, CrC4-alkoxy-CrC4-alkyl, CyCVcycloalkyl; CrC6-haloalkyl, CrC4-haloalkylthio, CrC4-haloalkylsulphinyl, Cr C'4-haloalkylsulphonyl, halo-Ci-C4-alkoxy-C]-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, fbrmyl-CrC3-alkyl, (CrC3-alkyl)carbonyl-CrC3-alkyl, (Ci-C3-alkoxy)carbonyl-CrC3-alkyl; halo-(CrC3-alkyl)carbonyl-CrC3-alkyl, halo-(Ci-C3-alkoxy)carbonyl-Ci-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (CrC8-alkyl)carbonyl, (CrC8-alkoxy)carbonyl, (Ci-C4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C8-cycloalkyl)carbonyl; (C'i-C6-haloalkyl)carbonyl, (CrC6-haloalkoxy)carbonyl, (halo-CrC4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C8-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR6R7 or -CH2NR8R9, and R1, R2, R5, R6, R7, R8 and Ry are as defined above. 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, including in combination with heteroatoms, such as, for example, in alkoxy. Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution 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 or different. Here, halogen denotes fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine. However, the general or preferred radical definitions or illustrations given above can also be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. The definitions apply both to the end products and, correspondingly, to the precursors and intermediates. The definitions mentioned can be combined with one another as desired. Moreover, individual definitions may not apply. Preference, particular preference or very particular preference is given to compounds of the formula (I) which carry the substituents mentioned as preferred, particularly preferred and very particularly preferred, respectively. Using 5-fluoro-l,3-dimethyl-lH-pyrazole-4-carbonyl chloride and N-(methoxymethyl)-2-(l,3,3-trimethylpentyl)anilme as starting materials, the process (a) according to the invention can be illustrated by the following formula scheme: (Figure Removed) The formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out the process (a) of the invention. In this formula (II), R1 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 for R1. X1 preferably represents chlorine, bromine or hydroxyl The carboxylic acid derivatives of the formula (II) are known and/or can be prepared by known processes (cf. WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313). The formula (III) provides a general definition of the anilines furthermore required as starting materials for carrying out the process (a) according to the invention. In this formula (III), R2, R3 and R4 preferably, particularly preferably and very particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals. The aniline derivatives of the formula (III) are novel. They can be prepared by d) reacting alkylamlines of the formula (VI) (Figure Removed) in which R2 and R3 are as defined above with halides of the formula (V) R4— X' in which is as defined above and XJ represents chlorine, bromine or iodine, if appropriate in the presence of a base and if appropriate in the presence of a diluent. The formula (VI) provides a general definition of the alkylanilines required as starting materials for carrying out the process (d) according to the invention. In this formula (VI), R2 and R3 preferably, particularly preferably and very particularly 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 and very particularly preferred, respectively, for these radicals. The alkylanilines of the formula (VI) are known and/or can be obtained by known methods (cf. WO 03/010149). The formula (V) provides a general definition of the halides furthermore required as starting matenals for carrying out the process (d) according to the invention. In this formula (V), R4 preferably, particularly preferably and very particularly preferably has those meanings which have already been given in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for R4, Halides of the formula (V) are known. Using N-aceryl-5-fluoro-1,3-dimethyl-N-(2-[(lZ)-l,3,3-tnmethylbut-l-en-1 -yl]phenyl}-1 H-pyrazole-4-carboxamide and hydrogen as starting matenals and a catalyst, the course of the process (b) according to the invention can be illustrated by the following formula scheme: (Figure Removed) The formula (IV) provides a general definition of the pyrazolylcarboxanilides required as starting materials for carrying out the process (b) according to the invention. In this formula (IV), R1, R2, R3 and R4 preferably, particularly preferably and very particularly preferably have those meanings which have already been given in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals. rfhe compounds of the formula (IV) are novel. They can be prepared by e) reacting pyrazolylcarboxanilides of the formula (VII) (Figure Removed) in which R1, R2 and R3 are as defined above with halides of the formula (V) in which R4 is as defined above arid X2 represents chlorine, bromine or iodine, if appropriate in the presence of a base and if appropriate in the presence of a diluent. The formula (VII) provides a general definition of the pyrazolylcarboxanilides required as starting materials for carrying out the process (e) according to the invention. In this formula (VII), R1, R2 and R3 preferably, particularly preferably and very particularly preferably have those meanings which have already been given m connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals. The pyrazolylcarboxanilides of the formula (VII) are known (cf. WO 03/010149). The halides of the formula (V) furthermore required as starting materials for carrying out the process (e) according to the invention have already been described in connection with the process (d) according to the invention. Using 5-fluoro-l ,3-dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide and ethyl chloro(oxo)acetate as starting materials, the course of the process (c) according to the invention can be illustrated by the following formula scheme: (Figure Removed) Formula (la) provides a general definition of the pyrazolylcarboxanilides required as starting materials for carrying out the process (c) according to the invention. In this formula (la), R1, R2 and R3 preferably, particularly preferably and very particularly 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 and very particularly preferred, respectively, for these radicals. The pyrazolylcarboxanilides of the formula (la) are known (cf. WO 03/010149). The halides of the formula (V) furthermore required as starting materials for carrying out the process (c) according to the invention have already been described in connection with the process (d) according to the invention. Suitable diluents for carrying out the process (a) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloro-methane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-bulyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide. The process (a) according to the invention is, if appropriate, carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as tnmethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopy-ridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). When carrying out the process (a) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from 0°C to 80°C. For carrying out the process (a) according to the invention for preparing the compounds of the formula (I), in general from 0.2 to 5 rnol, preferably from 0.5 to 2 mol, of aniline derivatives of the formula (III) are employed per mole of the carboxylic acid derivative of the formula (H). Suitable diluents for carrying out the process (b) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; 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, or alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxy-ethanol, methoxyethanol, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether. The process (b) according to the invention is, if appropriate, carried out in the presence of a catalyst. Suitable catalysts are all catalysts which are customarily used for hydrogenations. Examples which may be mentioned are: Raney nickel, palladium or platinum, if appropriate on a support, such as, for example, activated carbon. Instead of in the presence of hydrogen in combination with a catalyst, the hydrogenation in the process (b) according to the invention can also be carried out in the presence of triethylsilane. When carrying out the process (b) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from 0°C to 80°C. Suitable diluents for carrying out the process (c) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloro-methane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide. The process (c) according to the invention is carried out in the presence of a base. Suitable bases are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassum tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tnbutylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholme, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBIJ). When carrying out the process (c) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from 20°C to 110°C. For carrying out the process (c) according to the invention for preparing the compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of halide of the formula (V) are employed per mole of the pyrazolylcarboxanilide of the formula (la). Unless indicated otherwise, all processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure - in general between 0.1 bar and 10 bar. The substances according to the invention have potent microbicidal activity and can be employed for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of matenals. Fungicides can be employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. 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: Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; Envinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans; 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; Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Podosphaera species, such as, for example, Podosphaera leucotricha; Ventiiria species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (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; 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; Pellicularia species, such as, for example, Pellicularia sasakii; Pyriculana species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, tor example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens; Alternana species, such as, for example, Alternaria brassicae; and Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides, Rhizoctonia species, such as, for example, Rhizoctonia solani. 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. 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 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 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 required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. The active compounds according to the invention can be used with particularly good results for controlling cereal diseases, such as, for example, against Puccinia species, and diseases in viticulture and the cultivation of fruits and vegetables, such as, for example, against Botrytis, Venturia or Altemaria species. 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 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 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 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 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 storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushmg-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating. 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. 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 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 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 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. Microorganisms of the following genera may be mentioned as examples: Alternana, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, 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, 'rnchoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, and 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, 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 active compounds with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surf actants, that is emulsiflers 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 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 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 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 earners 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 material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foarn formers are: for example nonionic and anionic emulsiflers, such as polyoxy-ethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example Hgnosulphite waste liquors and methylcellulose. Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gurn 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. 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. 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 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. Suitable mixing components are, for example, the following compounds: Fungicides: 2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl; aldimorph; amidoflumet; am-propylfos; ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; beno-danil; benomyl; benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole; bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvone; chinome-thionat; chlobenthiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon; cyazofa-mid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlo-fluamd; dichlone; dichlorophen; diclocymet; diclomezine; dicloran; diethofencarb; difenoconazole; diflumetonm; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap; diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon; edifenphos; epoxiconazole; ethaboxam; ethinmol; etndiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfiiram; fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin; fluquincon-azole; flurprimidol; flusilazole; flusulphamide; flutolanil; flutriafol; folpet; fosetyl-Al; fosetyl-sodium; fubendazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachloro- benzene; hexaconazole; hymexazole; imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tns(albesil); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin; kresoxim-methyl; mancozeb; maneb; mefenmzone; mepanipyrim; me-pronil; metalaxyl; metalaxyl-M; metconazole; methasulphocarb; methfuroxam; metiram; metomino-strobin; metsulphovax; mildiomycin; myclobutanil; myclozolin; natamycin; nicobifen; mtrothal-iso-propyl; noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxy-carboxin; oxyfenthim; paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen; phthalide; picoxystrobm; piperalin; polyoxins; polyoxorim; probenazole; prochloraz; procymidone; propamo-carb; propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil; pyroquilon; pyroxyfur; pyrrolenitrine; quinconazole; quinoxy-fen; quintozene; simeconazole; spiroxamine; sulphur; tebuconazole; tecloftalam; tecnazene; tetcycla-cis; tetraconazole; thiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid; tol-clofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobm; triflumizole; triforine; triticonazole; uniconazole; validamycin A; vinclo-zolin; zineb; ziram; zoxamide; (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphe-nyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide; 1 -(1 -naphthalenyl)-1 H-pyrrole-2,5-di-one; 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarbox-amide; 2-chloro-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridinecarboxamide; 3,4,5-trichlo-ro-2,6-pyridinedicarbomtnle; actmovate; cis-l-(4-chlorophenyl)-2-(lH-l,2,4-triazol-l-yl)cyclohepta-nol; methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazole-5-carboxylate; monopotassium carbonate; N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide; N-butyl-8-( 1,1 -dimethylethyl)-1 -oxaspiro[4.5]decane-3-amme; sodium tetrathiocarbonate; and copper salts and preparations, such as Bordeaux mixture; copper hydroxide; copper naphthenate; copper oxychloride; copper sulphate; cufraneb; copper oxide; mancopper; oxine-copper. Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. Insecticides / acaricides / nematicides: abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole, acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb, aldoxycarb, allethrin, allethrin IR-isomers, alpha-cyper-methrin (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ-60541, azadirachtin, aza-methiphos, azinphos-methyl, azinphos-ethyl, azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, baculoviruses, Beauveria bassiana, Beauvena tenella, benclothiaz, bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthnn, beta-cypermethnn, bifenazate, bifenthrin, binapacryl, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomcthnn, biopermethrin, bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl, bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb, buprofezin, butathiofos, butocarboxim, butoxycarboxim, butylpyridaben, cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap, CGA-50439, chinomethionat, chlordane, chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloro-benzilate, chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl), chlovaporthrin, chromafenozlde, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cloethocarb, clofente-zine, clothianidm, clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene, cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin (1R-trans-isomer), cyromazine, DDT, deltamethrin, demeton-S-methyl, demeton-S-methylsulphone, dia-fenthmron, diahfos, diazinon, dichlofenthion, dichlorvos, dicofol, dicrotophos, dicyclanil, diflubenz-uron, dimefluthrin, dimethoate, dimethylvinphos, dinobuton, dinocap, dinotefuran, diofenolan, di-sulphoton, docusat-sodium, dofenapyn, DOWCO-439, eflusilanate, emamectin, emamectin-benzoate, empenthnn (1 R-isomer), endosulphan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb, ethi-prole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos, famphur, fenamiphos, fenazaquin, fen-butatin oxide, fenfluthrin, femtrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb, fenpropa-thrin, fenpyrad, fenpyrithnn, fenpyroximate, fensulphothion, fenthion, fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim, iluazuron, flubenzimine, flubrocythrinate, flucycloxuron, flu-cythrmate, flufenenm, flufenoxuron, flufenprox, flumethnn, flupyrazofos, flutenzin (flufenzine), flu-valinate, fonofbs, formetanate, formothion, fosmethilan, fosthiazate, fubfenprox (fluproxyfen), fura-thiocarb, garnma-cyhalothrin, gamma-HCH, gossyplure, grandlure, granulosis viruses, halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexythiazox, hydramethylnone, hydroprene, IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos, iprobenfos, isazofos, iso-fenphos, isoprocarb, isoxathion, ivermectin, japonilure, kadethrin, nuclear polyhedrosis viruses, kinoprene, lambda-cyhalothrin, lindane, lufenuron, malathion, mecarbam, mesulphenfos, metaldehyde, metam-sodium, methacrifos, methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthnn, rnetolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin, MTI-800, naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, novaluron, noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate, oxamyl, oxydemeton-methyl, Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl), permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (IR-trans isomer), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimi-phos-methyl, pirimiphos-ethyl, potassium oleate, prallethrin, profenofos, profluthrin, promecarb, propaphos, propargite, propetamphos, propoxur, prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphenthion, pyridathion, pyrimidi-fen, pyriproxyfen, quinalphos, resmethrin, RH-5849, ribavinn, RU-12457, RU-15525, S-421, S-1833, salithion, sebufos, Sl-0009, silafluofen, spinosad, spirodiclofen, spiromesifen, sulphluramid, sulpho-tep, sulprofos, SZI-121, tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, te-fluthrin, temephos, temivinphos, terbam, terbufos, tetrachlorvinphos, tetradifon, tetramethrin, tetra-methrin (IR-isomer), tetrasul, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogenoxalate, thiodicarb, thiofanox, thiometon, thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, transfluthrin, triarathene, triazamate, triazophos, triazuron, tri-chlophemdine, tnchlorfon, Trichoderma atroviride, triflumuron, trimethacarb, vamidothion, vamhprole, verbutin, Verticillium lecanii, WL-108477, WL^0027, Yl-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]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 msecticidally active plant extracts, nematodes, fungi or viruses. 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 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, 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 use forms prepared therefrom, such as ready-to-use solutions, suspensions, wertable powders, pastes, soluble powders, dusts and granules. Application is carried out in a customary manner, for example by watering, spraying, atomizing, broadcasting, 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. 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 10,000 g/ha, preferably between 10 and 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 5000 g/ha. 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 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 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. 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, 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 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. 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 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 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 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, arachnids, nematodes and slugs and snails 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 CrylA(a), CrylA(b), CrylA(c), CryllA, CryfflA, CryfflB2, Cry9c, Cry2Ab, CrySBb and CrylF 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 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, 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), 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 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 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 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. The preparation and the use of the active compounds according to the invention is illustrated by the examples below. (Figure Removed) At room temperature, 56.0 mg (2.3 mmol) of sodium hydride are added to a solution of 300.0 mg (0.78 mmol) of 5-fluoro-l-methyl-3-(trifluoromethyl)-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide in 10.0ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 min, and 366.6 mg (4.7 mmol) of acetyl chloride and 2.2 g (21.2 mmol) of acetic anhydride are added. After 16 h of heating under reflux, the reaction mixture is added to 100 ml of methanol and 3 ml of triethylamine, and the mixture is filtered and concentrated under reduced pressure. Recrystallization from cyclohexane gives 182 mg (54.7% of theory) of N-acetyl-5-fiuoro-l-methyl-3-(trifluoromethyl)-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide of logP (pH 2.3) = 4.63. Example 2 (Figure Removed) 1.66 g (5.0 mmol) of 5-fluoro-l,3-dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole^-carboxamide and 1.02g (7.4 mmol) of ethyl chloro(oxo)acetate were dissolved in 20ml of carbon tetrachloride and stirred under reflux for 4 h. The reaction mixture was cooled to room temperature and concentrated. This gave 2g (93% of theory) of ethyl {[(5-fluoro-l,3-dimethyl-lH-pyrazol-4-yl)carbonyl][2-(l,3,3-trimethylbutyl)phenyl]amino}(oxo)acetate of logP (pH 2.3) = 4.40. The compounds of the formula (I) listed in table 1 below are obtained analogously to examples 1 and 2 and in accordance with the instructions in the general descriptions of the processes. Table 1 (Table Removed) Preparation of starting materials of the formula (III) Example OH-1) (Figure Removed) 243 mg (3.1 mmol) of acetyl chloride were added slowly to a solution of 500 mg (2.8mmol) of 2-(l,3-dimethylbutyl)phenylamine in 35 ml of acetonitrile. The reaction mixture was stirred at room temperature for 1 h and then poured onto water. After extraction with ethyl acetate, the organic phases were dried over sodium sulphate and concentrated under reduced pressure. This gave 600 mg (98% of theory) of N-[2-(l,3-dimeihylbutyl)phenyl]acetamide of logP (pH 2.3) = 2.65. The compounds of the formula (HI) listed in table 2 below are obtained analogously to example (HI-1) and in accordance with the instructions in the general descriptions of the processes. (Figure Removed) The logP values given in the preparation examples and tables above are determined in accordance with EEC Directive 79/831 Annexe V.A8 by HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C 18). Temperature: 43°C. The determination in the acidic range is carried out at pH 2.3 using the mobile phases 0.1% aqueous phosphoric acid and acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile. Calibration was earned out using unbranched alkan-2-ones (with 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. Use examples: Example A Podosphaera test (apple) / protective Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide 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 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 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%. Evaluation is earned 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. (Table Removed) Example B Venturia test (apple) / protective Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide 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 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 plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain in an incubation cabinet at about 20°C and 100% relative atmospheric humidity for one day. The plants are then placed in a greenhouse at about 21°C and a relative atmospheric 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. Table B Venturia test (apple) / protective (Table Removed) Example C Botrytis test (bean) / protective Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide 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 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, 2 small pieces of agar colonized by Botrytis cinerea are placed onto each leaf. The inoculated plants are placed in a dark chamber at about 20°C and 100% relative atmospheric humidity. 2 days after the inoculation, the size of the infected areas on the leaves is evaluated. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. Table C Botrytis test (bean) / protective (Table Removed) Puccinia test (wheat) / protective Solvent: 25 parts by weight of N,N-dimethylacetamide Emulsifler: 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 emulsifler, 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 plants are sprayed with a conidia suspension of Puccima recondita. The plants remain in an incubation cabinet 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. Evaluation is earned 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. Table D Puccinia test (wheat) / protective (Table Removed) Example E Sphaerotheca test (cucumber) / protective Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifler: 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 emulsifler, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young cucumber 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 Sphaerotheca fuliginea. The plants are then placed in a greenhouse at 70% relative atmospheric humidity and a temperature of 23°C. Evaluation is earned 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 infection is observed. (Table Removed) We claim; 1. N-substituted pyrazolylcarboxanilides of the formula (I) (Formula Removed) In which R1 represents methyl or trifluoromethyl R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, a) R3 represents hydrogen, R4 represents C1-C8-alkyI, C1-C4 alkoxy-C1-C4-alkyl, or -C(=0)C(=0)R5 b) R3 represents C1-C8-alkyl R4 represents C1-C8 alkyl, C1-C4-alkoxy- C1-C4-alkyl, (C1-C8-alkyl)carbonyl,-C(=0)C(=0)R5, R5 represents C1-C8-alkoxy. 2 N-substituted pyrazolylcarboxanilides of the formula (I) as claimed in claim 1 in which R1 represents methyl or trifluoromethyl R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, a) R3 represents hydrogen, R4 represents C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkyl, or -C(=0)C(=0)R5 b) R3 represents C1-C6-alkyl R4 represents C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkyl, or -C(=0)C(=0)R5 R5 represent C1-C4-alkoxy, 3. N-substituted pyrazolylcarboxanilides of the form (lb) as claimed in claim 1 or 2. (Formula Removed) in which R4A represents C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl, or -C(=0)C(=0)R5 and R1, R2 and R5 are as defined in Claim 1. 4. N-substituted pyrazolylcarboxanilides of the formula (Ic) as claimed in claim 1 or 2. (Formula Removed) in which R3B representsC1-C8-alkyl R4B represents C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl or -C(=0)C(=0)R5, and R1, R2 and R5 are as defined in Claim 1. 5. N-substituted pyrazolylcarboxanilides of the formula (I) as claimed in claim 1 in which R4 represents formyl. 6. N. substituted pyrazolylcarboxanilides of the formula (I) as claimed in claim 1 in which R4 represents -C(=O)C(=0)R5 and R5 is as defined in Claim 1. 7. Process for preparing compounds of the formula (I) as claimed in claim 1, where in a) carboxylic acid derivatives of the formula (II) (Formula Removed) in which E1 is as defined above and X1 represents halogen or hydroxyl are reacted with as aniline derivative of the formula (III) (Formula Removed) in which R2, R3 and R4 are as defined above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent as hereinbefore described. 8. Compositions for controlling unwanted microorganisms, as and when prepared by using N-substituted pyrazolylcarboxanilides of formula (I) as claimed in claim 1.

Full Text

"N- SUBSTITUTED PYRAZOLYLCARBOXANILIDES OF FORMULA (I) AND PROCESS FOR PREPARATION THEREOF"
The present invention relates to novel (N-substituted) pyrazolylcarboxanilides, to a plurality of processes for their preparation and to their use for controlling unwanted microorganisms.
It is already known that numerous carboxanilides have fungicidal properties (cf. WO 93/11117, EP-A 0 545 099, EP-A 0 824099, JP 63-48269, WO 02/059086 and JP 8-176112). N-[2-(l,3-Dimethyl-butyl)phenyl]-5-fluoro-l-methyl-N-prop-2-yn-1-yl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide and N-aceryl-N-[2-(l,3-dimethylburyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-
carboxamide (WO 02/059086) may be mentioned by way of example. The activity of these com¬pounds is good; however, at low application rates it is sometimes unsatisfactory.
This invention now provides novel N-substituted pyrazolylcarboxanilides of the formula (!) .1
(Formula Removed)
in which
R1 represents methyl, trifluoromethyl or difluoromethyl,
R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
a) R3 represents hydrogen,
R4 represents C1-C8-alkyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy- C1-
C4-alkyl, C3-C8-cycloalkyl; CrC6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsul-
phinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo-
alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl,
formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1 -
C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C,-
C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms;
(C3-C8-cycloalkyl)carbonyl; (C3-C8-halocycloalkyl)carbonyl having 1 to 9 fluorine,
chlorine and/or bromine atoms; or -C(=0)C(=0)R5, -CONRV or -CH2NRER9,
b) R3 represents halogen, C1-C8-alkyl or C1-C8-haloalkyl,
R4 represents C1-C8-aIkyl, CrC6-a]kylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy-Cr C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsul-phinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo-alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl,
formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C3-C8-cycloalkyl)carbonyl; (C3-C8-halocycloalkyl)carbonyl having 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=0)C(=0)R5, -CONR6R7 or -CH2NR8R9,
b) R3 represents halogen, C1-C8-alkyl or C1-C8-haloalkyl,
R4 represents C1-C8-alkyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsul-phinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo-alkyl having in each case I to 9 fluorine, chlorine and/or bromine atoms; formyl,

formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-
C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C1-
C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms;
(C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl,
(C3-C8-cycloalkyl)carbonyl; (C1-C6-haloalkyl)carbonyl, (C1-C6-haloalkoxy)carbonyl,
(halo-C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-halocycloalkyl)carbonyl having in
each case 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=0)R5,
-CONR6R7 or -CH2NR8R9,
R5 represents hydrogen, C1-C8-alkyl,C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl;
C1-C6-haloalkyl, C1-C6-haloalkoxy, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, R6 and R7 independently of one another, each represent hydrogen, C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C8-haloalkyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocyclo-alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, R6 and R7 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C1-C4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR1 , R8 and R9 independently of one another, represent hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl; C1-C8-halo-
alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, R8 and R9 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and Ci-C4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR10, R10 represents hydrogen or C1-C6-alkyl.
If appropriate, the compounds according to the invention can be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also of tautomers. What is claimed are both the E and Z isomers, and the threo and erythrp and also the optical isomers, any mixtures of these isomers and the possible tautomeric forms.
Furthermore, it has been found that N-substituted pyrazolylcarboxanilides of the formula (I) are obtained when

a)
carboxylic acid derivatives of the formula (II)O. R"
N I CH,
in which
R1 is as defined above and
X1 represents halogen or hydroxyl
are reacted with an aniline derivative of the formula (III)
(Figure Removed)
(ffl)
or b) in which R2, R3 and R4 are as defined above,
if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing
agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a
diluent,
pyrazolylcarboxanilides of the formula (IV) (Figure Removed)
or
c)
in which R1, R2, R3 and R4 are as defined above
are hydrogenated, if appropriate in the presence of a diluent and if appropriate in the presence
of a catalyst,
pyrazolylcarboxanilides of the formula (la)
(Figure Removed)

in which R1, R2 and R3 are as defined above are reacted with halides of the formula (V)
R— *' (V)
in which
R1 is as defined above and X' represents chlorine, bromine or iodine in the presence of a base and in the presence of a diluent.
Finally, it has been Ibund that the novel N-substituted pyrazolylcarboxanilides 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.
The formula (I) provides a general definition of the N-substituted pyrazolylcarboxanilides according to the invention. Preferred radical definitions of the formulae mentioned above and below are given below. These definitions apply to the end products of the formula (I) and likewise to all intermediates.
R1 tolerably represents methyl.
R1 furthermore preferably represents trifluoromethyl.
R1 furthermore pjeferably represents difluoromethyl.
R2 preferably represents hydrogen.
R2 furthermore preferably represents fluorine, where fluorine is particularly preferably located
in the 4-, 5- or 6-position, veryjrarjjcularlyjjreferably in the 4- or 6-position, especially in the
4-position, of the anilide radical [cf. formula (I) above]. R2 furthermore preferably represents chlorine, where chlorine is particularly preferably located
in the 5-position of the anilide radical [cf. formula (I) above]. R2 furthermore preferably represents methyl, where methyl is particularly preferably located in
the 3-position of the anilide radical (cf. formula (I) above]. R2 furthermore preferably represents trifluoromethyl, where trifluoromethyl is particularly
preferably located in the 4- or 5-position of the anilide radical [cf. formula (I) above].
If R3 represents hydrogen,
R4 preferably represents CrC6-alkyl, CrC4-alkylsulphinyl, CrC4-alkylsulphonyl, CrC3-alkoxy-C,-C3-alkyl, C3-C6-cycloalkyl; CrC4-haloalkyl, C,-C4-haloalkylthio, CrC4-haloalkylsulphi-nyl, CrC4-haloalkylsulphonyl, halo-Ci-C3-alkoxy-Ci-C3-alkyl, C3-C6-halocycloalkyl having
m each case 1 to 9 iluonne, chlonne and/or bromine atoms; formyl, formyl-Ci-C3-alkyl, (Cr Cj-alkyl)carbonyl-C,-C3-alkyl, (CrC3-alkoxy)carbonyl-CrC3-alkyl; halo-(C,-C3-alkyl)carbo-nyl-Cj-Cj-alkyl, halo-(Ci-C3-alkoxy)carbonyl-CrC3-alkyl having in each case 1 to 13 fluorine, chlonne and/or bromine atoms;
(C3-C5-cycloalkyl)carbonyl; (C3-C6-halocycloalkyl)carbonyl having 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR'R7 or -CH2NR8R9.
If R3 represents hydrogen,
R4 particularly preferably represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,
pentyl or hcxyl, methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-, sec- or
tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or isopropylsulphonyl, n-, iso-, sec-
or tert-butylsulphonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopro-
pyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethyl-
thio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphmyl, rrifluorome-
thylsulphonyl, trifluoromethoxymethyl; formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3,
-CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3,
-(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2,
-(C1I2)2-CO,CH,, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3,
-CH2-CO-CClt, -CH2-CO-CH2CF3, -CH2-CO-CH2CC13, -(CH2)2-CO-CH2CF3,
-(CH2)2-CO-CH2CC13, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CC13, -OH2-C02CC]2CC13, -(CH2)2-C02CH2CF3, -(CH2)2-C02CF2CF3, -(CH2)2-CO2CH2CC13, -(CH2)2-CO,CC12('C13;
cyclopropylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl or -C(=O)C(=O)R5, CONR6R7 or -CH2NR8R9.
If R3 represents hydrogen,
R4 very ^pai^iculadY ^rjejierably represents methyl, methoxymethyl, formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -C(=O)CHO, -C(=O)C(=O)CH3, -C(=O)C(==O)CH2OCH3, -C(=O)CO2CH3, -C(=O)CO2CH2CH3.
If
R3 preferably represents fluorine, chlorine, bromine, iodine, CrC6-alkyl or CrC6-haloalkyl having 1 to 13 fluorine, chlorine and/or bromine atoms,
particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl or Ci-C4-haloalkyl having 1 to 9 fluorine, chlorine and/or bromine atoms, y.^_B.articjJ.larly--pieferab-ly represents methyl, ethyl, fluorine, chlorine, trifluoromethyl,
then

R4 preferably represents C]-C6-alkyl, Ci-C4-alkylsulphinyl, CrC4-alkylsulphonyl, CrC3-alkoxy-CrCj-alkyl, CrC6-cycloalkyl; Ci-C4-haloalkyl, Ci-C4-haloalkylthio, CrC4-haloalkylsulphi-nyl, CrC4-haloalkylsulphonyl, halo-CrC3-alkoxy-Ci-C3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-CrC3-alkyl, (Cr C3-alkyl)carbonyl-Ci-C3-alkyl, (CrC3-alkoxy)carbonyl-CrC3-alkyl; halo-(Ci-C3-alkyl)carbo-nyl-CrC3-alkyl, halo-(CrC3-alkoxy)carbonyl-Ci-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms;
(CrC6-alkyl)carbonyl, (CrC6-alkoxy)carbonyl, (CrC3-alkoxy-CrC3-alkyl)carbonyl, (C3-C6-
cycloalkyl)carbonyl; (CrC4-haloalkyl)carbonyl, (C|-C4-haloalkoxy)carbonyl, (halo-C]-C3-
alkoxy-CrCj-alkyl)carbonyl, (C3-C6-halocycloalkyl)carbonyl having in each case 1 to 9
fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR6R7 or -CH2NR8R9,
particularly preferably represents methyl, ethyl, n- or isopropyl, n-, iso, sec- or tert-butyl,
pentyl or hexyl, methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-, sec- or
tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or isopropylsulphonyl, n-, iso-, sec-
or tert-butylsulphonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopro-
pyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethyl-
thio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphmyl, trifluorome-
thylsulphonyl, trifluoromethoxymethyl; formyl, -CH2-CHO, -CH2CH2-CHO, -CH2-CO-CH3,
-CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3,
-(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2,
-(CH2)2-CO2CH3, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3,
-CHz-CO-CCl.,, -CH2-CO-CH2CF3, -CH2-CO-CH2CC13, -(CH2)2-CO-CH2CF3,
-(CH2)2-CO-CH2CC13, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CC13, -CH2-C02CC12CC13, -(CH2)2-C02CH2CF3, -(CH2)2-CO2CF2CF3, -(CH2)2-CO2CH2CC13, -(CH2)2-C02CC12CC13;
methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl; trifluoro-methylcarbonyl, trifluoromethoxycarbonyl, or -C(=O)C(=O)R5, -CONR6R7 or -CH2NR8R9, YgQL_BglllCMiiEly==.Ptefersbly represents methyl, methoxymethyl, formyl, -CH2-CHO, -(CII2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -C(=O)CHO, -C(=0)C(=0)CH3, -C(=O)C(=O)CH2OCH3, -C(=O)CO2CH3, -C(=O)CO2CH2CH3.
R5 preferably represents hydrogen, Q-Ce-alkyl, C,-C4-alkoxy, Ci-C3-alkoxy-Ci-C3-alkyl, C3-C6-cycloalkyl; CrC4-haloalkyl, C,-C4-haloalkoxy, halo-Ci-C3-alkoxy-CrC3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms.

R5 particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, tert-butyl, methoxy, elhoxy, n- or isopropoxy, tert-butoxy, cyclopropyl; trifluoromethyl, tri fluoromethoxy.
R6 and R; independently of one another, preferably represent hydrogen, CrC6-alkyl, CrC3-alkoxy-CrQ-alkyl, C3-C6-cycloalkyl; C,-C4-haloalkyl, halo-C,-C3-alkoxy-Ci-C3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms.
R6 and R7 furthermore together with the nitrogen atom to which they are attached preferably form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen and CrC4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR10.
R6 and R7 independently of one another, particularly preferably represent hydrogen, methyl, ethyl, n-or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxy-ethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, tri fluoromethoxymethyl.
R6 and R' furthermore together with the nitrogen atom to which they are attached particularly preferably form a saturated heterocycle from the group consisting of morpholme, thiomor-pholine and piperazine which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl, where the piperazine may be substituted by R10 on the second nitrogen atom.
R8 and R9 independently of one another, preferably represent hydrogen, CrC6-alkyl, C3-C6-cyclo-alkyl; Ci-C4-haloalkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms.
R8 and R9 furthermore together with the nitrogen atom to which they are attached preferably form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen and Ci~C4-alkyl, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR10.
R8 and R9 independently of one another, particularly preferably represent hydrogen, methyl, ethyl, n-or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxy-ethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, tri fluoromethoxymethyl.
R8 and R9 furthermore together with the nitrogen atom to which they are attached particularly preferably form a saturated heterocycle from the group consisting of morpholine, thiomorpholine

and piperazme which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl, where the piperazine may be substituted by R10 on the second nitrogen atom.
R10 preferably represents hydrogen or C]-C4-alkyl.
RU) particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl.
Emphasis is given to compounds of the formula (I) in which R4 represents formyl.
Emphasis is furthermore given to compounds of the formula (I) in which R4 represents
-C(=O)C(=O)R5, where R5 is as defined above.
Emphasis is furthermore given to N-substituted pyrazolylcarboxanilides of the formula (Ib)
(Figure Removed)

in which
R4A represents CrC8-alkyl, CrC6-alkylsulphinyl, C,-C6-alkylsulphonyl, CrC4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; CrC6-haloalkyl, d-C4-haloalkylthio, CrC4-haloalkylsulphinyl, Cr Q-haloalkylsulphonyl, halo-Ci-C4-alkoxy-CrC4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-CrC3-alkyl, (CrC3-alkyl)carbonyl-C,-C3-alkyl, (C1-C3-alkoxy)carbonyl-C]-C3-alkyl; halo-(CrC3-alkyl)carbonyl-C|-C3-alkyl, halo-(C|-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms;
(C3-C8-cycloalkyl)carbonyl; (C3-C8-halocycloalkyl)carbonyl having 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR'Tl7 or -CH2NR8R9,
and R1, R2, R5, R6, R7, R8 and R9 are as defined above.
Emphasis is furthermore given to N-substituted pyrazolylcarboxanilides of the formula (Ic)
(Figure Removed)

in which
R3B represents halogen, CrC8-alkyl or Ci-C8-haloalkyl,
R4B represents CrCg-alkyl, CrC6-alkylsulphinyl, Ci-C6-alkylsulphonyl, CrC4-alkoxy-CrC4-alkyl, CyCVcycloalkyl; CrC6-haloalkyl, CrC4-haloalkylthio, CrC4-haloalkylsulphinyl, Cr C'4-haloalkylsulphonyl, halo-Ci-C4-alkoxy-C]-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, fbrmyl-CrC3-alkyl, (CrC3-alkyl)carbonyl-CrC3-alkyl, (Ci-C3-alkoxy)carbonyl-CrC3-alkyl; halo-(CrC3-alkyl)carbonyl-CrC3-alkyl, halo-(Ci-C3-alkoxy)carbonyl-Ci-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms;
(CrC8-alkyl)carbonyl, (CrC8-alkoxy)carbonyl, (Ci-C4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C8-cycloalkyl)carbonyl; (C'i-C6-haloalkyl)carbonyl, (CrC6-haloalkoxy)carbonyl, (halo-CrC4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C8-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R5, -CONR6R7 or -CH2NR8R9,
and R1, R2, R5, R6, R7, R8 and Ry are as defined above.
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, including in combination with heteroatoms, such as, for example, in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution 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 or different. Here, halogen denotes fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
However, the general or preferred radical definitions or illustrations given above can also be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. The definitions apply both to the end products and, correspondingly, to the precursors and intermediates.
The definitions mentioned can be combined with one another as desired. Moreover, individual definitions may not apply.
Preference, particular preference or very particular preference is given to compounds of the formula (I) which carry the substituents mentioned as preferred, particularly preferred and very particularly preferred, respectively.

Using 5-fluoro-l,3-dimethyl-lH-pyrazole-4-carbonyl chloride and N-(methoxymethyl)-2-(l,3,3-trimethylpentyl)anilme as starting materials, the process (a) according to the invention can be illustrated by the following formula scheme:
(Figure Removed)
The formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out the process (a) of the invention. In this formula (II), R1 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 for R1. X1 preferably represents chlorine, bromine or hydroxyl
The carboxylic acid derivatives of the formula (II) are known and/or can be prepared by known processes (cf. WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313).
The formula (III) provides a general definition of the anilines furthermore required as starting materials for carrying out the process (a) according to the invention. In this formula (III), R2, R3 and R4 preferably, particularly preferably and very particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals.
The aniline derivatives of the formula (III) are novel. They can be prepared by d) reacting alkylamlines of the formula (VI)
(Figure Removed)
in which R2 and R3 are as defined above with halides of the formula (V)
R4— X'
in which
is as defined above and
XJ represents chlorine, bromine or iodine,
if appropriate in the presence of a base and if appropriate in the presence of a diluent.
The formula (VI) provides a general definition of the alkylanilines required as starting materials for carrying out the process (d) according to the invention. In this formula (VI), R2 and R3 preferably, particularly preferably and very particularly 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 and very particularly preferred, respectively, for these radicals.
The alkylanilines of the formula (VI) are known and/or can be obtained by known methods (cf. WO 03/010149).
The formula (V) provides a general definition of the halides furthermore required as starting matenals for carrying out the process (d) according to the invention. In this formula (V), R4 preferably, particularly preferably and very particularly preferably has those meanings which have already been given in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for R4,
Halides of the formula (V) are known.
Using N-aceryl-5-fluoro-1,3-dimethyl-N-(2-[(lZ)-l,3,3-tnmethylbut-l-en-1 -yl]phenyl}-1 H-pyrazole-4-carboxamide and hydrogen as starting matenals and a catalyst, the course of the process (b) according to the invention can be illustrated by the following formula scheme:
(Figure Removed)

The formula (IV) provides a general definition of the pyrazolylcarboxanilides required as starting materials for carrying out the process (b) according to the invention. In this formula (IV), R1, R2, R3 and R4 preferably, particularly preferably and very particularly preferably have those meanings which have already been given in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals.
rfhe compounds of the formula (IV) are novel. They can be prepared by e) reacting pyrazolylcarboxanilides of the formula (VII)
(Figure Removed)
in which R1, R2 and R3 are as defined above with halides of the formula (V)
in which
R4 is as defined above arid
X2 represents chlorine, bromine or iodine,
if appropriate in the presence of a base and if appropriate in the presence of a diluent.
The formula (VII) provides a general definition of the pyrazolylcarboxanilides required as starting materials for carrying out the process (e) according to the invention. In this formula (VII), R1, R2 and R3 preferably, particularly preferably and very particularly preferably have those meanings which have already been given m connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals.
The pyrazolylcarboxanilides of the formula (VII) are known (cf. WO 03/010149).
The halides of the formula (V) furthermore required as starting materials for carrying out the process (e) according to the invention have already been described in connection with the process (d) according to the invention.
Using 5-fluoro-l ,3-dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide and ethyl chloro(oxo)acetate as starting materials, the course of the process (c) according to the invention can be illustrated by the following formula scheme:
(Figure Removed)

Formula (la) provides a general definition of the pyrazolylcarboxanilides required as starting materials for carrying out the process (c) according to the invention. In this formula (la), R1, R2 and R3 preferably, particularly preferably and very particularly 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 and very particularly preferred, respectively, for these radicals.
The pyrazolylcarboxanilides of the formula (la) are known (cf. WO 03/010149).
The halides of the formula (V) furthermore required as starting materials for carrying out the process (c) according to the invention have already been described in connection with the process (d) according to the invention.
Suitable diluents for carrying out the process (a) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloro-methane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-bulyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
The process (a) according to the invention is, if appropriate, carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as tnmethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopy-ridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
When carrying out the process (a) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from 0°C to 80°C.
For carrying out the process (a) according to the invention for preparing the compounds of the formula (I), in general from 0.2 to 5 rnol, preferably from 0.5 to 2 mol, of aniline derivatives of the formula (III) are employed per mole of the carboxylic acid derivative of the formula (H).
Suitable diluents for carrying out the process (b) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; 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, or alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxy-ethanol, methoxyethanol, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether.
The process (b) according to the invention is, if appropriate, carried out in the presence of a catalyst. Suitable catalysts are all catalysts which are customarily used for hydrogenations. Examples which may be mentioned are: Raney nickel, palladium or platinum, if appropriate on a support, such as, for example, activated carbon.
Instead of in the presence of hydrogen in combination with a catalyst, the hydrogenation in the process (b) according to the invention can also be carried out in the presence of triethylsilane.
When carrying out the process (b) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from 0°C to 80°C.
Suitable diluents for carrying out the process (c) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloro-methane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
The process (c) according to the invention is carried out in the presence of a base. Suitable bases are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example,
sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassum tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tnbutylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholme, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBIJ).
When carrying out the process (c) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from 20°C to 110°C.
For carrying out the process (c) according to the invention for preparing the compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of halide of the formula (V) are employed per mole of the pyrazolylcarboxanilide of the formula (la).
Unless indicated otherwise, all processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure - in general between 0.1 bar and 10 bar.
The substances according to the invention have potent microbicidal activity and can be employed for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of matenals.
Fungicides can be employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
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:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans;
Envinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
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;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Ventiiria species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
(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;
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;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyriculana species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, tor example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternana species, such as, for example, Alternaria brassicae; and
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides,
Rhizoctonia species, such as, for example, Rhizoctonia solani.
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.
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 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 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 required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
The active compounds according to the invention can be used with particularly good results for controlling cereal diseases, such as, for example, against Puccinia species, and diseases in viticulture and the cultivation of fruits and vegetables, such as, for example, against Botrytis, Venturia or Altemaria species.
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 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 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 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 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 storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushmg-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating.
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.
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 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 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 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.
Microorganisms of the following genera may be mentioned as examples:
Alternana, such as Alternaria tenuis,
Aspergillus, such as Aspergillus niger,
Chaetomium, such as Chaetomium globosum,
Coniophora, such as Coniophora puetana,
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, 'rnchoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, and 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, 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 active compounds with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surf actants, that is emulsiflers 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 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 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 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 earners 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 material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foarn formers are: for example nonionic and anionic emulsiflers, such as polyoxy-ethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example Hgnosulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gurn 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.
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.
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 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.
Suitable mixing components are, for example, the following compounds: Fungicides:
2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl; aldimorph; amidoflumet; am-propylfos; ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; beno-danil; benomyl; benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole; bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvone; chinome-thionat; chlobenthiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon; cyazofa-mid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlo-fluamd; dichlone; dichlorophen; diclocymet; diclomezine; dicloran; diethofencarb; difenoconazole; diflumetonm; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap; diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon; edifenphos; epoxiconazole; ethaboxam; ethinmol; etndiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfiiram; fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin; fluquincon-azole; flurprimidol; flusilazole; flusulphamide; flutolanil; flutriafol; folpet; fosetyl-Al; fosetyl-sodium; fubendazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachloro-
benzene; hexaconazole; hymexazole; imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tns(albesil); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin; kresoxim-methyl; mancozeb; maneb; mefenmzone; mepanipyrim; me-pronil; metalaxyl; metalaxyl-M; metconazole; methasulphocarb; methfuroxam; metiram; metomino-strobin; metsulphovax; mildiomycin; myclobutanil; myclozolin; natamycin; nicobifen; mtrothal-iso-propyl; noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxy-carboxin; oxyfenthim; paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen; phthalide; picoxystrobm; piperalin; polyoxins; polyoxorim; probenazole; prochloraz; procymidone; propamo-carb; propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil; pyroquilon; pyroxyfur; pyrrolenitrine; quinconazole; quinoxy-fen; quintozene; simeconazole; spiroxamine; sulphur; tebuconazole; tecloftalam; tecnazene; tetcycla-cis; tetraconazole; thiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid; tol-clofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobm; triflumizole; triforine; triticonazole; uniconazole; validamycin A; vinclo-zolin; zineb; ziram; zoxamide; (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphe-nyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide; 1 -(1 -naphthalenyl)-1 H-pyrrole-2,5-di-one; 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarbox-amide; 2-chloro-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridinecarboxamide; 3,4,5-trichlo-ro-2,6-pyridinedicarbomtnle; actmovate; cis-l-(4-chlorophenyl)-2-(lH-l,2,4-triazol-l-yl)cyclohepta-nol; methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazole-5-carboxylate; monopotassium carbonate; N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide; N-butyl-8-( 1,1 -dimethylethyl)-1 -oxaspiro[4.5]decane-3-amme; sodium tetrathiocarbonate; and copper salts and preparations, such as Bordeaux mixture; copper hydroxide; copper naphthenate; copper oxychloride; copper sulphate; cufraneb; copper oxide; mancopper; oxine-copper.
Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
Insecticides / acaricides / nematicides:
abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole, acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb, aldoxycarb, allethrin, allethrin IR-isomers, alpha-cyper-methrin (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ-60541, azadirachtin, aza-methiphos, azinphos-methyl, azinphos-ethyl, azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis
strain GC-91, Bacillus thuringiensis strain NCTC-11821, baculoviruses, Beauveria bassiana, Beauvena tenella, benclothiaz, bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthnn, beta-cypermethnn, bifenazate, bifenthrin, binapacryl, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomcthnn, biopermethrin, bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl, bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb, buprofezin, butathiofos, butocarboxim, butoxycarboxim, butylpyridaben, cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap, CGA-50439, chinomethionat, chlordane, chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloro-benzilate, chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl), chlovaporthrin, chromafenozlde, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cloethocarb, clofente-zine, clothianidm, clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene, cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin (1R-trans-isomer), cyromazine, DDT, deltamethrin, demeton-S-methyl, demeton-S-methylsulphone, dia-fenthmron, diahfos, diazinon, dichlofenthion, dichlorvos, dicofol, dicrotophos, dicyclanil, diflubenz-uron, dimefluthrin, dimethoate, dimethylvinphos, dinobuton, dinocap, dinotefuran, diofenolan, di-sulphoton, docusat-sodium, dofenapyn, DOWCO-439, eflusilanate, emamectin, emamectin-benzoate, empenthnn (1 R-isomer), endosulphan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb, ethi-prole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos, famphur, fenamiphos, fenazaquin, fen-butatin oxide, fenfluthrin, femtrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb, fenpropa-thrin, fenpyrad, fenpyrithnn, fenpyroximate, fensulphothion, fenthion, fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim, iluazuron, flubenzimine, flubrocythrinate, flucycloxuron, flu-cythrmate, flufenenm, flufenoxuron, flufenprox, flumethnn, flupyrazofos, flutenzin (flufenzine), flu-valinate, fonofbs, formetanate, formothion, fosmethilan, fosthiazate, fubfenprox (fluproxyfen), fura-thiocarb, garnma-cyhalothrin, gamma-HCH, gossyplure, grandlure, granulosis viruses, halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexythiazox, hydramethylnone, hydroprene, IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos, iprobenfos, isazofos, iso-fenphos, isoprocarb, isoxathion, ivermectin, japonilure, kadethrin, nuclear polyhedrosis viruses, kinoprene, lambda-cyhalothrin, lindane, lufenuron, malathion, mecarbam, mesulphenfos, metaldehyde, metam-sodium, methacrifos, methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthnn, rnetolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin, MTI-800, naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, novaluron, noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate, oxamyl, oxydemeton-methyl, Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl), permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (IR-trans isomer), phenthoate, phorate,
phosalone, phosmet, phosphamidon, phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimi-phos-methyl, pirimiphos-ethyl, potassium oleate, prallethrin, profenofos, profluthrin, promecarb, propaphos, propargite, propetamphos, propoxur, prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphenthion, pyridathion, pyrimidi-fen, pyriproxyfen, quinalphos, resmethrin, RH-5849, ribavinn, RU-12457, RU-15525, S-421, S-1833, salithion, sebufos, Sl-0009, silafluofen, spinosad, spirodiclofen, spiromesifen, sulphluramid, sulpho-tep, sulprofos, SZI-121, tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, te-fluthrin, temephos, temivinphos, terbam, terbufos, tetrachlorvinphos, tetradifon, tetramethrin, tetra-methrin (IR-isomer), tetrasul, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogenoxalate, thiodicarb, thiofanox, thiometon, thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, transfluthrin, triarathene, triazamate, triazophos, triazuron, tri-chlophemdine, tnchlorfon, Trichoderma atroviride, triflumuron, trimethacarb, vamidothion, vamhprole, verbutin, Verticillium lecanii, WL-108477, WL^0027, Yl-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]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 msecticidally active plant extracts, nematodes, fungi or viruses.
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 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, 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 use forms prepared therefrom, such as ready-to-use solutions, suspensions, wertable powders, pastes, soluble powders, dusts and granules. Application is carried out in a customary manner, for example by watering, spraying, atomizing, broadcasting, 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.
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 10,000 g/ha, preferably between 10 and 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 5000 g/ha.
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 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 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.
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, 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 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.
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 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 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 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, arachnids, nematodes and slugs and snails 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 CrylA(a), CrylA(b), CrylA(c), CryllA, CryfflA, CryfflB2, Cry9c, Cry2Ab, CrySBb and CrylF 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 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, 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), 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 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 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 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.
The preparation and the use of the active compounds according to the invention is illustrated by the examples below.
(Figure Removed)
At room temperature, 56.0 mg (2.3 mmol) of sodium hydride are added to a solution of 300.0 mg (0.78 mmol) of 5-fluoro-l-methyl-3-(trifluoromethyl)-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide in 10.0ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 min, and 366.6 mg (4.7 mmol) of acetyl chloride and 2.2 g (21.2 mmol) of acetic anhydride are added. After 16 h of heating under reflux, the reaction mixture is added to 100 ml of methanol and 3 ml of triethylamine, and the mixture is filtered and concentrated under reduced pressure. Recrystallization from cyclohexane gives 182 mg (54.7% of theory) of N-acetyl-5-fiuoro-l-methyl-3-(trifluoromethyl)-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide of logP (pH 2.3) = 4.63.
Example 2
(Figure Removed)

1.66 g (5.0 mmol) of 5-fluoro-l,3-dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole^-carboxamide and 1.02g (7.4 mmol) of ethyl chloro(oxo)acetate were dissolved in 20ml of carbon tetrachloride and stirred under reflux for 4 h. The reaction mixture was cooled to room temperature and concentrated. This gave 2g (93% of theory) of ethyl {[(5-fluoro-l,3-dimethyl-lH-pyrazol-4-yl)carbonyl][2-(l,3,3-trimethylbutyl)phenyl]amino}(oxo)acetate of logP (pH 2.3) = 4.40.
The compounds of the formula (I) listed in table 1 below are obtained analogously to examples 1 and 2 and in accordance with the instructions in the general descriptions of the processes.

Table 1
(Table Removed)
Preparation of starting materials of the formula (III)
Example OH-1)

(Figure Removed)

243 mg (3.1 mmol) of acetyl chloride were added slowly to a solution of 500 mg (2.8mmol) of 2-(l,3-dimethylbutyl)phenylamine in 35 ml of acetonitrile. The reaction mixture was stirred at room temperature for 1 h and then poured onto water. After extraction with ethyl acetate, the organic phases were dried over sodium sulphate and concentrated under reduced pressure. This gave 600 mg (98% of theory) of N-[2-(l,3-dimeihylbutyl)phenyl]acetamide of logP (pH 2.3) = 2.65.
The compounds of the formula (HI) listed in table 2 below are obtained analogously to example (HI-1) and in accordance with the instructions in the general descriptions of the processes.
(Figure Removed)
The logP values given in the preparation examples and tables above are determined in accordance with EEC Directive 79/831 Annexe V.A8 by HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C 18). Temperature: 43°C.
The determination in the acidic range is carried out at pH 2.3 using the mobile phases 0.1% aqueous phosphoric acid and acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
Calibration was earned out using unbranched alkan-2-ones (with 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.
Use examples:
Example A
Podosphaera test (apple) / protective
Solvents: 24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
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 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 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%.
Evaluation is earned 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.
(Table Removed)
Example B
Venturia test (apple) / protective
Solvents: 24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
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 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 plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain in an incubation cabinet at about 20°C and 100% relative atmospheric humidity for one day.
The plants are then placed in a greenhouse at about 21°C and a relative atmospheric 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.

Table B
Venturia test (apple) / protective
(Table Removed)
Example C
Botrytis test (bean) / protective
Solvents: 24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
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 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, 2 small pieces of agar colonized by Botrytis cinerea are placed onto each leaf. The inoculated plants are placed in a dark chamber at about 20°C and 100% relative atmospheric humidity.
2 days after the inoculation, the size of the infected areas on the leaves is evaluated. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Table C
Botrytis test (bean) / protective
(Table Removed)
Puccinia test (wheat) / protective
Solvent: 25 parts by weight of N,N-dimethylacetamide
Emulsifler: 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 emulsifler, 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 plants are sprayed with a conidia suspension of Puccima recondita. The plants remain in an incubation cabinet 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.
Evaluation is earned 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.

Table D
Puccinia test (wheat) / protective
(Table Removed)
Example E
Sphaerotheca test (cucumber) / protective
Solvent: 49 parts by weight of N,N-dimethylformamide
Emulsifler: 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 emulsifler, and the concentrate is diluted with water to the desired concentration.
To test for protective activity, young cucumber 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 Sphaerotheca fuliginea. The plants are then placed in a greenhouse at 70% relative atmospheric humidity and a temperature of 23°C.
Evaluation is earned 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 infection is observed. (Table Removed)

We claim;
1. N-substituted pyrazolylcarboxanilides of the formula (I)

(Formula Removed)
In which
R1 represents methyl or trifluoromethyl
R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
a) R3 represents hydrogen,
R4 represents C1-C8-alkyI, C1-C4 alkoxy-C1-C4-alkyl, or -C(=0)C(=0)R5
b) R3 represents C1-C8-alkyl
R4 represents C1-C8 alkyl, C1-C4-alkoxy- C1-C4-alkyl,
(C1-C8-alkyl)carbonyl,-C(=0)C(=0)R5, R5 represents C1-C8-alkoxy.
2 N-substituted pyrazolylcarboxanilides of the formula (I) as claimed in
claim 1 in which
R1 represents methyl or trifluoromethyl
R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
a) R3 represents hydrogen,
R4 represents C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkyl, or -C(=0)C(=0)R5
b) R3 represents C1-C6-alkyl
R4 represents C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkyl, or
-C(=0)C(=0)R5 R5 represent C1-C4-alkoxy,
3. N-substituted pyrazolylcarboxanilides of the form (lb) as claimed in claim
1 or 2.

(Formula Removed)
in which

R4A represents C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl, or -C(=0)C(=0)R5 and R1, R2 and R5 are as defined in Claim 1.
4. N-substituted pyrazolylcarboxanilides of the formula (Ic) as claimed in
claim 1 or 2.
(Formula Removed)
in which
R3B representsC1-C8-alkyl
R4B represents C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl or -C(=0)C(=0)R5,
and R1, R2
and R5 are as defined in Claim 1.
5. N-substituted pyrazolylcarboxanilides of the formula (I) as claimed in claim 1 in which R4 represents formyl.
6. N. substituted pyrazolylcarboxanilides of the formula (I) as claimed in claim 1 in which R4 represents -C(=O)C(=0)R5 and R5 is as defined in Claim 1.
7. Process for preparing compounds of the formula (I) as claimed in claim 1, where in
a) carboxylic acid derivatives of the formula (II)
(Formula Removed)
in which
E1 is as defined above and
X1 represents halogen or hydroxyl
are reacted with as aniline derivative of the formula (III)

(Formula Removed)
in which R2, R3 and R4 are as defined above,
if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent as hereinbefore described.
8. Compositions for controlling unwanted microorganisms, as and when prepared by using N-substituted pyrazolylcarboxanilides of formula (I) as claimed in claim 1.

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Patent Number

223016

Indian Patent Application Number

1801/DEL/2004

PG Journal Number

38/2008

Publication Date

19-Sep-2008

Grant Date

03-Sep-2008

Date of Filing

23-Sep-2004

Name of Patentee

BAYER CROPSCIENCE AG

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	JORG NICO GREUL	AM SANDBERG 30A, 42799 LEICHLINGEN, GERMANY.
4	BENOIT HARTMANN	FARBERSTR. 1, 40764 LANGENFELD, GERMANY.
5	ULRIKE WACHENDORFF-NEUMANN	OBERER MARKENWEG 85, 56566 NEUWIED, GERMANY.
6	PETER DAHMAN	ALTEBRUCKER STR. 61, 41470 NEUSS, GERMANY.
7	KARL-HEINZ KUCK	PASTOR-LOH-STR. 30A, 40764 LANGENFELD, GERMANY.

PCT International Classification Number

CO 7D 233/00

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	10349497.9	2003-10-23	Germany