Indian Patents. 270102:HYDROXYALKYLPYRAZOLYLCARBOXANILIDES OF THE FORMULA(IV)

Title of Invention	HYDROXYALKYLPYRAZOLYLCARBOXANILIDES OF THE FORMULA(IV)
Abstract	The present invention relates to novel pyrazolylcarboxanilides, to a plurality of processes for their preparation and to their use for controlling undesirable microorganisms.

Full Text	FORM 2 THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS RULES, 2003 COMPLETE SPECIFICATION [See Section 10; rule 13] "PYRAZOLYLCARBOXANILIDES AND PROCESS FOR PREPARATION THEREOF" BAYER AKTIENGESELLSCHAFT, a German company, of D-51368 Leverkusen, Germany The following specification particularly describes the invention and the manner in which it is to be performed: Le A 35 503-Foreign Countries Nk/li/NT 1 - Pyrazolylcarboxanilides The present invention relates to novel pyrazolylcarboxanilides, to a plurality of 5 processes for their preparation and to their use for controlling undesirable microorganisms. It is already known that numerous carboxanilides have fungicidal properties (compare WO 93-11117, EP-A 0 545 099, EP-A 0 589 301, WO 99/09013, 10 DE 198 40 322, EP-A 0 824 099, JP 63048269). Thus, N-(2-cyclohexyl)-l,3- dimethyl-5--fluoropyrazo]-4-carboxanilide, N-(2-pheny])~l,3-dimethylpyrazol-4- carboxanilide and N-[2-(2-fluorophenyl)]-l,3-dimethylpyrazol-4-carboxanilide can be used for controlling fungi. The activity of these substances is good; however, at low application rates it is sometimes unsatisfactory. 15 y^-'This invention now provides novel pyrazolylcarboxanilides of the formula (I) (D 20 in which R1 represents hydrogen, cyano, halogen, nitro, CpQ-alkyl, CrC4-haloalkyl having 1 to 5 halogen atoms, C3-C6-cycloalkyl, Cj~C4-alkoxy, CrC4-haloalkoxy having 1 to 5 halogen atoms, CrC4-alkylthio, CrC4-haloalkylthio having 1 to 5 halogen atoms or aminocarbonyl-C\|-C4-alkyl, Le A 35 503-Foreign Countries -2 R2 represents hydrogen, CrC4-alkyl, CpCg-haloalkyl having 1 to 5 halogen atoms, C2-C6-alkenyl, C3-C6-cycloalkyl, CrC4-alkyltMo-CrC4-alkyl, Cr C4-haloalkylthio-CrC4-alkyl having 1 to 5 halogen atoms, Ci-Q-alkoxy-C!-C4-alkyl or CrC4-haloalkoxy-C]-C4-alkyl having 1 to 5 halogen atoms, 5 G represents halogen or Cj-C4-alkyl, G furthermore represents Cs-C6-alkyl, 10 R3 represents unsubstituted C2-C20-alkyl or represents Gi~C2o-alkyl which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl or represents C2-C2o-alkenyl or C2-C20-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or 15 C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or Cj-C4-a]kyl and represents 0, 1 or 2. 20 If appropriate, the compounds according to the invention can be present as mixtures of different 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 as tautomers. What is claimed are both the E and the Z isomers, and the threo 25 and erythro and also the optical isomers, any mixtures of these isomers, and also the possible tautomeric forms. (Furthermore, it has been found that pyrazolylcarboxanilides of the formula (I) are obtained when 30 —c^" a) carboxylic acid derivatives of the formula (II) Le A 35 503-Foreign Countries 3- 0. R1\ V—X (H), N -.2 in which R1 and R2 are as defined above and X represents halogen, are reacted with an aniline derivative of the formula (HI) ^3~Gn (m)' H2N R3 in which G, R3 and n are as defined above, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or b) pyrazolylcarboxanilides of the formula (la) Le A 35 503-Foreign Countries (la), in which R1, R2, G and n are as defined above and R4 represents C2-C2o-alkenyl or C2-C2o-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or C]-C4-alkyl, are hydro genated, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or c) hydroxyalkylpyrazolylcarboxanilides of the formula (IV) (IV), in which Le A 35 503-Foreign Countries R1, R2, G and n are as defined above and R5 represents C2-C2o-hydroxyalkyl which is optionally additionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cr Chalky!, is dehydrated, if appropriate in the presence of a diluent and if appropriate in the presence of an acid, or d) halopyrazolylcarboxanilides of the formula (V) in which R1, R2, G and n are as defined above and Y represents bromine or iodine, are reacted with an alkyne of the formula (VI) (V), in which HC^^-R6 (VI), Le A 35 503-Foreign Countries R6 represents C2-C]g-alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C^alkyl, or an alkene of the formula (VH) R8 = R7/=\R9 (vn), in which 10 R7, R8 and R9 independently of one another each represent hydrogen or alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6- cycloalkyl, where the cycloalkyl moiety for its part may optionally be 15 substituted by halogen and/or CrC4-aIkyl and where the total number of carbon atoms of the open-chain moiety does not exceed the number 20, if appropriate in the presence of a diluent, if appropriate in the presence of an 20 acid binder and in the presence of one or more catalysts, or -^ e) ketones of the formula (VHT) (VTTD, Le A 35 503-Foreign Countries 10 in which R1, R2, G and n are as defined above and R10 represents hydrogen or C]-C]3-alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C4-alkyl, are reacted with a phosphorus compound of the general formula (IX) R11—pX (IX), in which 15 R11 represents hydrogen or Cj-Cjg-alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj- 20 C4-alkyl and Px represents a grouping -P+(C6H5)3 CI" -P+(C6H5)3 Br-, -P+(C6H5)31~ -P(=0)(OCH3)3 or-P(=0)(OC2H5)3, 25 if appropriate in the presence of a diluent. --^ ( Finally, it has been found that the novel pyrazolylcarboxanilides of the formula (T) have very good microbicidal properties and can be used for controlling undesirable microorganisms both in crop protection and in the protection of materials. Le A 35 503-Foreign Countries —^(Surprisingly, the pyrazolylcarboxanilides of the formula (I) according to the invention have considerably better fungicidal activity than the constitutionally most similar active compounds of the prior art having the same direction of action, j 5 __i> The formula (I) provides a general definition of the pyrazolylcarboxanilides according to the invention. R1 preferably represents hydrogen, cyano, halogen, nitro, CrC4-alkyl, CrC4- haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C3-C6- 10 cycloalkyl, Cj-C^alkoxy, C1-C4-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, Q-C4-alkylthio, C1-C4-haloalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms or aminocarbonyl-Ci-C4-alkyl. R2 preferably represents hydrogen, C1-C4-aIkyl, CrC6-haloalkyl having 1 to 5 15 fluorine, chlorine and/or bromine atoms, C2-C6-alkenyl, C3-C6 cycloalkyl, C1-C4-alkyIthio-C1-C4-aJkyl, CrC4-haloalky]thio-CrC4-alkyI having 1 to 5 fluorine, chlorine and/or bromine atoms, Ci-Q-alkoxy-Cj-C^-alkyl or CrC4-haloalkoxy-C1-C4-alkyl having 1 to 5 fluorine, chlorine and/or bromine atoms. 20 G preferably represents halogen or Cj-C4-aIkyl. G furthermore preferably represents Cs-Ce-alkyl. 25 R3 preferably represents unsubstituted C2-C12-alkyl or represents CrC12-alkyl which is mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl or represents C2-C12-alkenyl or C2-C12-alkynyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group 30 consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be mono- to tetrasubstituted by Le A 35 503-Foreign Countries 9- 5 identical or different substituents from the group consisting of halogen and/or CrC4-alkyl. n preferably represents 0, 1 or 2. R1 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl or trifluoroethyl. R2 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- 10 , s- or t-butyl, trifluoromethyl or trifluoroethyl. 15 G particularly preferably represents fluorine, chlorine or methyl. G furthermore particularly preferably represents ethyl or t-butyl. G furthermore particularly preferably represents 2,4-dimethylbutyl. R3 particularly preferably represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, ethenyl, 20 propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl or decynyl, each of which may be attached at any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, 25 cyclopentyl and/or cyclohexyl. n also particularly preferably represents 0, 1 or 2. A very particularly preferred group are the compounds of the formula (I), in which 30 R1 represents methyl and Le A 35 503-Foreign Countries -10- R2 represents methyl. Very particularly preferred are furthermore compounds of the formula (I), in which 5 R3 represents unsubstituted C2~C2o-alkyl (preferably C2-Ci2-alkyl, particularly preferably C2-C6-alkyl). Very particularly preferred are furthermore compounds of the formula (I), in which 10 n represents 0. Emphasis is given to compounds of the formula (I), in which 15 R1 represents methyl, R2 represents methyl, R3 represents unsubstituted C2-C2cralkyl (preferably C2-C12-alkyl, very particularly preferably C2-C6-alkyl), 20 n represents 0. 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 25 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. A plurality of radicals having the same indices, such as, for example, n radicals G for n >1, can be identical 30 or different. Le A 35 503-Foreign Countries -11- 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 represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine. 5 However, the abovementioned general or preferred radical definitions or illustrations can also be combined with one another, i.e. between the respective ranges and preferred ranges, as desired. The definitions or illustrations apply both to the end products and, correspondingly, to the precursors and intermediates. .to The definitions mentioned can be combined with one another as desired. Moreover, individual definitions may not apply. Using 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride and 2-(l- 15 methylhexy])aniline as starting materials, the process a) according to the invention can be illustrated by the following formula scheme: 20 The formula (H) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out the process a) according to the invention. In this formula (IT), R1 and R2 preferably and 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 25 preferred and particularly preferred for R1 and R2. X represents halogen, preferably chlorine. Le A 35 503-Foreign Countries -12 The carboxylic acid derivatives of the formula (H) 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). 5 The formula (III) provides a general definition of the anilines furthermore required for the starting materials for carrying out the process a) according to the invention. In this formula (in), G, R3 and n preferably and 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 and 10 particularly preferred for G, R3 and n. The aniline derivatives of the formula (HI) are known and/or can be prepared by known methods (compare, for example, Heterocycles (1989), 29(6), 1013-16; J. Med. Chem. (1996), 39(4), 892-903; Synthesis (1995), (6), 713-16; Synth. Commun. 15 (1994), 24(2), 267-72; DE 2727416; Synthesis (1994), (2), 142-4; EP 0 824 099). Using 5-fluoro-1,3-dimethyl-N-{2-[(1Z)-1 -methyl-1 -hexenyljphenyl}-lH-pyrazol-4- carboxamide and hydrogen as starting materials, and a catalyst, the course of the process b) according to the invention can be illustrated by the following formula 20 scheme: Catalyst H3C The formula (la) provides a general definition of the pyrazolylcarboxanilides required as starting materials for carrying out the process b) according to the invention. In this 25 formula (la), R1, R2, G and n preferably and 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 and particularly preferred for R1, R2, G and n. Le A 35 503-Foreign Countries R4 preferably represents C2-C12-alkenyl or C2-C12-alkynyl5 each of which is optionally mono- to tetrasubstituted by identical or different substitutents from the group consisting of fluorine, chlorine and/or C3-C6-cycloaIkyl, where the cycloalkyl moiety for its part may optionally be mono- to 5 tetrasubstituted by identical or different substituents from the group consisting of halogen and/or Ci-C4-alkyl. R4 particularly preferably represents in each case straight-chain or branched ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, 10 decenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl or decynyl, each of which may be attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. 15 The compounds of the formula (la) are compounds according to the invention and can be prepared by process a), c), d) or e). Using 5-fluoro-N-[2-(l-hydroxy-l-methylhexyl)phenyl]-l,3-dimethyl-lH-pyrazoM- 20 carboxamide as starting material and an acid, the course of the process c) according to the invention can be illustrated by the following formula scheme: Acid 25 The formula (TV) provides a general definition of the hydroxyalkylpyrazolyl- carboxanilides required as starting materials for carrying out the process c) according to the invention. In this formula (IV), R1, R2, G and n preferably and particularly preferably have those meanings which have already been mentioned in connection Le A 35 503-Foreign Countries 14 with the description of the compounds of formula (I) according to the invention as being preferred and particularly preferred for R1, R2, G and n. R5 preferably represents C2-C12-hydroxyalkyl which is optionally additionally 5 mono- to tetrasubstituted by identical or different substituents from the group consisting of chlorine, fluorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or CrC4-alkyl. 10 R5 particularly preferably represents in each case straight-chain or branched hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, hydroxynonyl or hydroxydecyl, each of which may be attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting 15 of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl. The compounds of the formula (IV) have hitherto not been known; as novel compounds, they also form part of the subject-matter of the present application. 20 25 It has also been found that the hydroxyalkylpyrazolylcarboxanilides of the formula (IV) have very good microbicidal properties and can be used for controlling undesirable microorganisms both in crop protection and in the protection of materials. The hydroxyalkylpyrazolylcarboxanilides of the formula (TV) are obtained when f) carboxylic acid derivatives of the formula (IT) Le A 35 503-Foreign Countries 15- (n), in which R1, R2 and X are as defined above, are reacted with a hydroxyalkylaniline derivative of the formula (X) H2N R in which 10 15 R3, R5, G and n are as defined above, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. Using 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride and 2-(2-aminophenyl)-2-heptanol as starting materials, the course of the process f) according to the invention can be illustrated by the following formula scheme: 20 H,Q /1 '1 CH COCI The carboxylic acid derivatives of the formula (IT) required as starting materials for carrying out the process f) according to the invention have already been described Le A 35 503-Foreign Countries -16 10 further above, in connection with the description of the process a) according to the invention. The formula (X) provides a general definition of the hydroxyalkylaniline derivatives furthermore required as starting materials for carrying out the process f) according to the invention. In this formula (X), R3, R5, G and n preferably and particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formulae (I) and (TV) according to the invention as being preferred and particularly preferred for R3, R5, G and n. The hydroxyalkylaniline derivatives of the formula (X) are known and/or can be obtained by known methods (cf., for example, US 3,917,592 or EP 0 824 099). Using 5-fluoro-N-(2-iodophenyl)-l,3-dimethyI-lH-pyrazol-4-carboxamidee and 1- 15 pentyne or alternatively 1-hexene as starting materials and in each case a catalyst and a base, the course of the process d) according to the invention can be illustrated by the two formula schemes below: HC= -CH, Catalyst, Base HI Catalyst, Base H2C CH, 20 H3C- Le A 35 503-Foreign Countries 17- The formula (V) provides a genera] definition of the halopyrazolylcarboxanilides required as starting materials for carrying out the process d) according to the invention. In this formula (V), R1, R2, G and n preferably and particularly preferably have those meanings which have already been mentioned in connection with the 5 description of the compounds of the formula (I) according to the invention as being preferred and particularly preferred for R1, R2, G and n. Y preferably represents bromine or iodine. The halopyrazolylcarboxanilides of the formula (V) have hitherto not been known; as 10 novel compounds, they also form part of the subject-matter of the present application. They are obtained when g) carboxylic acid derivatives of the formula (H) 15 20 in which R1, R2 and X are as defined above, are reacted with a haJoaniline of the formula (XT) (XI), in which Le A 35 503-Foreign Countries -18- G, n and Y are as defined above, if appropriate in the presence of an acid binder and if appropriate in the 5 presence of a diluent. Using 5-fluoro-l,3-dirnethyl-lH-pyrazol-4-carbonyl chloride and 2-iodoaniline as starting materials, the course of the process g) according to the invention can be illustrated by the following formula scheme: 10 The carboxylic acid derivatives of the formula (H) required as starting materials for carrying out the process g) according to the invention have already been described 15 further above, in connection with the description of the process a) according to the invention. The formula (XI) provides a general definition of the haloanilines further required as starting materials for carrying out the process g) according to the invention. In this 20 formula (XI), G, n and Y preferably and particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formulae (I) and (V) as being preferred and particularly preferred for G, n and Y. 25 The haloanilines of the formula (XI) are known chemicals for synthesis. The formula (VI) provides a general definition of the alkynes furthermore required as starting materials for carrying out the process d) according to the invention. Le A 35 503-Foreign Countries 19- R6 preferably represents C2-Cio-alkyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl 5 moiety for its part may optionally be substituted by halogen and/or C1-C4- alkyl. R6 particularly preferably represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each of which may be 10 attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl. 15 The alkynes of the formula (VI) are known chemicals for synthesis. The formula (VH) provides a general definition of the alkenes furthermore alternatively required as starting materials for carrying out the process d) according to the invention. 20 R7, R8 and R9 independently of one another each preferably represent hydrogen or alkyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be 25 substituted by halogen and/or C1-C4-alkyl and the total number of carbon atoms of the open-chain moiety does not exceed the number 12. R7, R8 and R9 independently of one another particularly preferably each represent hydrogen or in each case straight-chain or branched ethyl, propyl, butyl, 30 pentyl, hexyl, heptyl or octyl, each of which may be attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, Le A 35 503-Poreign Countries -20- difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl, where the total number of carbon atoms of the open-chain moiety does not exceed the number 12. 5 The alkenes of the formula (VET) are known chemicals for synthesis. Using N-(2-acetylphenyl)-5-fluoro~l,3-dimethyl-lH-pyrazol-4-carboxamide and butyl(triphenyl)-phosphonium iodide as starting materials, the course of process e) according to the invention can be illustrated by the following formula scheme: 10 The formula (VTJT) provides a general definition of the ketones required as starting materials for carrying out the process e) according to the invention. In this formula 15 (VITJ), R1, R2, G and n preferably and 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 and particularly preferred forR1, R2, G and n. 20 R10 preferably represents C2~C10-alkyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C4-alkyl. 25 R10 particularly preferably represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each of which may be attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting Le A 35 503-Foreign Countries 21 of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl. The ketones of the formula (VUI) have hitherto not been known. As novel chemical 5 compounds, they also form part of the subject-matter of the present application. They are obtained when h) carboxylic acid derivatives of the formula (H) 10 Q 15 in which R1, R2 and X are as defined above, are reacted with ketoanilines of the formula (XH) (xn), 20 in which R10, G and n are as defined above, Le A 35 503-Foreign Countries -22- if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. Using 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride and l-(2- 5 aminophenyl)ethanone as starting materials, the course of the process h) according to the invention can be illustrated by the following formula scheme: 10 The carboxylic acid derivatives of the formula (H) required as starting materials for carrying out the process h) according to the invention have already been described further above, in connection with the description of the process a) according to the invention. 15 The formula (XE) provides a general definition of the ketoanilines furthermore required as starting materials for carrying out the process h) according to the invention. In this formula (XII), R10, G and n preferably and particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formulae (I) and (VTH) according to the 20 invention as being preferred and particularly preferred for R10, G and n. The ketoanilines of the formula (XII) are generally customary chemicals for synthesis (compare, for example, J. Am. Chem. Soc. 1978, 100(15), 4842-4857 or US 4,032,573). 25 The formula (DC) provides a general definition of the phosphorus compounds furthermore required as starting materials for carrying out the process e) according to the invention. Le A 35 503-Foreign Countries 23- R11 preferably represents C2-C10-alkyI which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of chlorine, fluorine, bromine and/or C3-C6~cycIoalkyl, where the cycloalkyl 5 moiety for its part may optionally be substituted by halogen and/or C1-C4- alkyl. R11 particularly preferably represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each of which may be 10 attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl. 15 Px preferably represents a grouping -P+(C6H5)3 Cl~, -P+(G6H5)3 Bi~, -P+(C6H5)3 I- -P(=0)(OCH3)3 or -P(=0)(OC2H5)3. The phosphorus compounds of the formula (IX) are known and/or can be prepared by known processes (compare, for example, Justus Liebigs Ann. Chem. 1953, 580, 44- 20 57 or Pure Appl. Chem. 1964, 9, 307-335). Suitable fluents for carrying out the processes a), f), g) and h) 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, 25 cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; 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-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisol, or 30 amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl- formanilide, N-methylpyrrolidone or hexamethylphosphoric triamide. Le A 35 503-Foreign Countries -24- The processes a), f), g) and h) according to the invention are, 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 5 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, calcum acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as 10 trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl- benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). 15 When carrying out the processes a), f), g) and h) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures of from 0°C to 150°C, preferably at temperatures from 0°C to 80°C. 20 For carrying out the process a) according to the invention for preparing compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of aniline derivatives of the formula (IH) are employed per mole of the carboxylic acid derivative of the formula (H). 25 For carrying out the process f) according to the invention for preparing compounds of the formula (IV), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of hydroxyalkylaniline derivatives of the formula (X) are employed per mole of the carboxylic acid derivative of the formula (II). 30 , For carrying out the process g) according to the invention for preparing compounds of the formula (V), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of Le A 35 503-Foreipn Countries -26- 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 decaline; halogenated hydrocarbons, 5 such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroetahen; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisol; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile, 10 propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N- methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; sulfones, such as sulpholane; alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert- 15 butanol, ethanediol, propane- 1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water. The process c) according to the invention is, if appropriate, carried out in the 20 presence of an acidJ Suitable acids are all inorganic and organic protic acids and also Lewis acids, and also all polymeric acids. These include, for example, hydrogen chloride, sulphuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulphonic acid, trifluoromethanesulphonic acid, toluenesulphonic acid, boron trifluoride (also as etherate), boron tribromide, aluminium trichloride, titanium 25 tetrachloride, tetrabutylorthotitanate, zinc chloride, iron(UI) chloride, antimony pentachloride, acidic ion exchangers, acidic alumina and acidic silica gel. 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 30 carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from 0°C to 80°C. Le A 35 503-Foreign Countries -27- The processes c) and b) according to the invention can also be carried out in a tandem reaction ("One-pot reaction"). To this end, a compound of the formula (TV) is reacted, if appropriate in the presence of a diluent (suitable diluents as for process c)), and if appropriate in the presence of an acid (suitable acids as for process c)) and in 5 the presence of triethylsilane. Suitable diluents for carrying out the process d) according to the invention are all inert organic solvents. These preferably include nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, or amides, such as N,N- 10 dimethylformamide, N,N-dimethylacetamide, N-rrethylformanilide, N- methylpyrrolidone or hexamethylphosphoric triamide. 15 20 25 If appropriate, the process d) according to the invention is 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, calcium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). The process d) according to the invention is carried out in the presence of one or more catalysts. 30 Suitable catalysts are in particular palladium salts or complexes. Preferably suitable for this purpose are palladium chloride, palladium acetate, tetrakis(triphenyl-phosphine)palladium or bis(triphenylphosphine)palladium dichloride. It is also Le A 35 503-Foreign Countries -28- possible to generate a palladium complex in the reaction mixture by adding a palladium salt and a complex ligand separately to the reaction. Suitable ligands are preferably organophosphorus compounds. Examples which may 5 be mentioned are: triphenylphosphine, tri-o-tolylphosphine, 2,2'-bis(diphenyl- phosphino)-l,l '-binaphthyl, dicyclohexylphosphinebiphenyl, l,4-bis(diphenyl- phosphino)butane, bisdiphenylphosphinoferrocene, di(tert-butylphosphino)biphenyl, di(cyclohexylphosphino)biphenyl, 2-dicyclohexylphosphino-2'-N,N-dimethylamino- biphenyl, tricyclohexylphosphine, tri-tert-butylphosphine. However, it is also 10 possible to dispense with ligands. The process d) according to the invention is furthermore, if appropriate, carried out in the presence of a further metal salt, such as copper salts, for example copper(I) iodide. 15 When carrying out the process d) 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 20°C to 180°C, preferably at temperatures of from50°Ctol50°C. 20 For carrying out the process d) according to the invention for preparing compounds of the formula (I), in general from 1 to 5 mol, preferably from 1 to 2 mol, of alkyne of the formula (VI) or alkene of the formula (VH) are employed per mole of the halopyrazolylcarboxanilide of the formula (V). 25 Suitable diluents for carrying out the process e) 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 decaline; halogenated hydrocarbons, 30 such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, Le A 35 503-Foreign Countries -29- 1,2-dimethoxyetbane, 1,2-diethoxyethane or anisol; nitriles, such as acetonitriJe, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N- dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N- methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate 5 or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; sulphones, such as sulpholane; alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane- 1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether. 10 The process e) according to the invention is, if appropriate, carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary strong bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides or alkali metal hydrocarbon compounds, such as, for example, sodium hydride, sodium hydroxide, potassium hydroxide, sodium amide, 15 lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert- butoxide, methyl lithium, phenyl lithium or butyl lithium. When carrying out the process e) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is 20 carried out at temperatures of from -80°C to 150°C, preferably at temperatures of from -30°C to 80°C. For carrying out the process e) according to the invention for preparing compounds of the formula (I), in general from 1 to 5 mol, preferably from 1 to 2 mol, of 25 phosphorus compound of the formula (IX) are employed per mole of the ketone of the formula (Vm). 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 ~ 30 in general between 0.1 bar and 10 bar. Le A 35 503-Foreign Countries -30- The substances according to the invention have potent microbicidal activity and can be employed for controlling undesirable microorganisms, such as fungi and bacteria, in crop protection and in the protection of material. 5 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, 10 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: 15 Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans; 20 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; 25 Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Podosphaera species, such as, for example, Podosphaera leucotricha; Venturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea 30 (conidia form: Drechslera, syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium); Le A 35 503-Foreign Countries -31- Uromyces species, such as, for example, Uromyces appendicular^; Puccinia species, such as, for example, Puccinia recondita; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Tilletia species, such as, for example, Tilletia caries; 5 Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; 10 Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; and Pseudocercosporella species, such as, for example, Pseudocercosporella 15 herpotrichoides. / The active^compounds according to the invention also have very good fortifying Action in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms. 20 In the present context, plant-fortifying (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defence system of plants such that, when the treated plants are subsequently inoculated with undesirable microorganisms, they show substantia] resistance against these 25 microorganisms. In the present case, undesirable microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Accordingly, the substances according to the invention can be used to protect plants for a certain period after the treatment 30 against attack by the pathogens mentioned. The period for which protection is provided generally extends over 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds. Le A 35 503-Foreign Countries -32- 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. 5 The active compounds according to the invention can be used with particularly good results for controlling cereal diseases, such as, for example, agairist Pyrenophora species, and diseases in viticulture, and in fruit and vegetable growing, such as, for example, against Altemaria or Podosphaera species. 10 The active compounds according to the invention are also suitable for increasing the jj yield of crops. In addition, they show reduced toxicity and are well tolerated by v plants. 15 At certain concentrations and application rates, the active compounds according to the invention can also be used as herbicides, for influencing plant growth and for controlling animal pests. They can also be used as intermediates and precursors for the synthesis of further active compounds. 20 The active compounds according to the invention can be used to treat all plants and parts of plants. By plants are understood here 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 25 combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by varietal property rights. 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 30 and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds. Le A 35 503-Foreign Countries -33- The treatment of the plants and the parts of plants with the active compounds according to the invention is>carried out directly or by action on their surroundings, habitat or storage space, according to customary treatment methods, for example by 5 dipping, spraying, evaporating, atomizing, broadcasting, spreading-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating. In the protection of materials, the compounds according to the invention can be. 10 employed for protecting industrial materials against infection with, and destruction by, undesired 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 15 materials which are intended to be protected by active compounds according to the invention from microbial change or destruction can be adhesives, 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 20 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 adhesives, sizes, paper and board, leather, wood, paints, cooling lubricants and heat-transfer liquids particularly preferably wood. 25 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), 30 and against slime organisms and algae. Microorganisms of the following genera may be mentioned as examples: Le A 35 503-Forejgn Countries -34- Alternaria, such as Altemaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, 5 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, 10 Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, and Staphylococcus, such as Staphylococcus aureus. 15 Depending on their particular physical and/or chemical properties, the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, 20 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 surfactants, that is 25 emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons 30 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 isobuty] ketone or cyclohexanone, strongly polar solvents such as Le A 35 503-Foreign Countries -35- dimethylformarnide 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 5 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 carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or 10 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 foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, 15 arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignosulphite waste liquors and methylcellulose. Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and 20 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, 25 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 percent by weight of active ] 30 compound, preferably between 0.5 and 90%. ] Le A 35 503-Foreign Countries -36- The active compounds according to the invention can be used as such or in their formulations, also 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, 5 i.e. the activity of the mixture is greater than the activity of the- individual components. Examples of suitable mixing components are the following: 10 Fungicides: aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos, 15 binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate, calcium polysulphide, carpropamide, capsimycin, captafol, captan, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, 20 cyproconazole, cyprodinil, cyprofuram, debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, 25 edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamide, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulphamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl- 30 sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole, Le A 35 503-Foreign Countries -37 imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione, iprovalicarb, irumamycin, isoprothiolane, isovaledione, kasugamycin, kresoxim-methy], copper preparations, such as: copper hydroxide, 5 copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture, mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin, 10 nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin, paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, pyraclostrobin, 15 pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, quinconazole, quintozene (PCNB), quinoxyfen, sulphur and sulphur preparations, spiroxamines, tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, 20 tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole, validamycin A, vinclozolin, viniconazole, zarilamide, zineb, ziram and also 25 Dagger G, OK-8705, OK-8801, a-( 1,1 -dimethylethy])~(3-(2-phenoxyethy])-1H-1,2,4-triazole-1 -ethanol, a-(2,4-dichlorophenyl)-(3-fluoro-(3-propyl-lH-l,2,4-triazole-l-ethanol, a-(2,4-dichlorophenyl)-P-methoxy-a-methyl-lH-l,2,4-triazole-l-ethanol, a-(5-methyl-l,3-dioxan-5-yl)-p-[[4-(trifluoromethyl)-pheny]]-methylene]-lH-l,2,4- 30 triazole-1-ethanol, (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(lH-l,2,4-triazol-l-yl)-3-octanone, Le A 35 503-Foreign Countries -38 (E)-a-(methoxyimino)-N-methyI-2~phenoxy-phenyIacetamide, l-(2,4-dichlorophenyl)-2-(lH-l,2,4-triazol-l-yl)-ethanoneO-(phenylmethyl)-oxime, l~(2~methyM~naphthaIenyI)-lH-pyrrole-2,5-dione, l-(3,5-dichIorophenyl)-3-(2-propenyl)~2,5-pyiro]idinedione, 5 l~[(diiodomethy])-su]phony]]-4-methy]-benzene, l-[[2-(2,4-dich]orophenyl)-l,3-dioxolan-2-yl]-methyl]-lH-imidazo]e, l-[[2-(4-chlorophenyl)-3-phenyloxiranyl]'methylj-lH-l,2,4-triazo]e, l-[l-[2-[(2,4-dichlorophenyl)'methoxy]-pheny]]-etheny]]-lH-imidazole, l-methy]-5-nony]-2-(pheny]methy])-3-pyrroIidino]e, 10 2' ,6' -dibromo-2-methyl-4' -trifluoromethoxy-4' -trifluoro-methyl- i ,3-thiazole- 5-carboxanj]ide, 2,6-dichloro-5-(methy]thio)-4-pyrimidiny]-thiocyanate, 2,6-dichloro-N-(4-trifluoromethy]benzy])-benzamide, 2,6-dichJoro-N-f[4-(trifluoromethyl)-pheny]]-methy]]~benzarnide, 15 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole, 2-[(l-methylethy])'SulphonyI]-5-(trichloromethyl)-l,3,4-thJadiazole, 2-[[6-deoxy-4-0-(4-0-methyl-(3-D-g]ycopyranosy])-a-D-glucopyranosyl]-amino]-4- raethoxy-lH-pyrro]o[2,3-d]pyrimidine-5-carbonitrile, 2-aminobutane, 20 2-bromo-2-(bromomethy])-pentanedinitrile, 2-chloro-N-(2,3-dihydro-l,l,3~trimethyl~lH-inden-4-yl)-3-pyridinecarboxamide, 2-chloro-N-(2,6-dimethylpheny])-N-(isothiocyanatomethyl)~acetamide, 2-pheny]pheno] (OPP), 3,4-dich]oro-l-[4-(dif]uoromethoxy)-phenyl]-lH-pyrro]e-2,5-dione, 25 3,5-dich]oro-N-[cyano[(l-methy]~2'propyny])-oxy]-methyl]-benzamide, 3-(l,l-dimethyIpropyl-l'Oxo-lH-indene-2-carbonitri]e, 3-[2-(4-chlorophenyl)~5'ethoxy-3-isoxazolidinyl]-pyridine, 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-lH-imidazo]e-l-sulphonamide, 4-methyl-tetrazolo[l,5-a]quinazolin-5(4H)-one, 30 8-hydroxyquinoline sulphate, 9H-xanthene~2-[(phenylamino)-carbony]]-9~carboxylic hydrazide, Le A 35 503-Foreign Countries -39- bis-(l-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate, cis-l-(4-chlorophenyl)-2-(lH-l,2,4~triazol-l-yl)-cycloheptanol, cis-4-[3-[4-(l,l-dimethylpropy])-pheny]-2-methy]propyl]-2,6-dimethyl-morpholine- hydrochloride, 5 ethyl [(4-chlorophenyl)-azo]-cyanoacetate, potassium hydrogen carbonate, methanetetrathiol sodium salt, methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yI)-lH-imidazoIe-5-carboxylate, methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)~DL-alaninate, 10 methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)'DL-aIaninate, N-(2,6-dimethy]phenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide, N-(2,6-dimethylpheny])-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide, N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide, N-(4-cyclohexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine, 15 N-(4-hexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine, N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2~oxo-3-oxazolidinyl)-acetamide, N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide, N-[2,2,2-trichloro-l-[(chloroacetyl)-amino]-ethyl]-benzamide, N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N'-methoxy-methanimidamide, 20 N-forrrryl-N-hydroxy-DL-alanine-sodium salt, 0,0-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate, O-methyl S-phenyl phenylpropylphosphoramidothioate, S-methyl 1,2,3-benzothiadiazole-7-carbothioate, spiro[2H]-1 ~benzopyrane-2,1 '(3 'H)-isobenzofuran]-3 '-one, 25 4-[(3,4-dimethoxyphenyl)-3~(4-fluorophenyl)-acryloyl]-morpholine. -Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, 30 octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. Le A 35 503-ForeiCT Countries -40- Insecticides / acaricides / nematicides: abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb, aldoxycarb, alpha- cypermethrin, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, 5 azamethiphos, azinphos A, azinphos M, azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiemis, baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin, bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, 10 butathiofos, butocarboxim, butylpyridaben, cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chloifenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin, clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos, 15 cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlorvos, dicofol, diflubenzuron, dimethoat, dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn, 20 eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole, etrimfos, fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron, 25 flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox, furathiocarb, granulosis viruses, nalofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene, imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin, 30 nuclear polyhidrosis viruses, lambda-cyhalothrin, lufenuron, Le A 35 503-Foreign Countries -41- malathion, mecarbam, metaldehyde, methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, methidathion, methiocarb, methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, monocrotophos, 5 naled, nitenpyram, nithiazine, novaluron, omethoate, oxamyJ, oxydemethon M, Paecilomyces fumosoroseus, parathion A, parathion M, permethrin, phenthoate, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos A, pinmiphos M, profenofos, promecarb, propargite, propoxur, prothiofos, prothoat, 10 pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen, pyriproxyfen, quinalphos, ribavirin, salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, 15 tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, tetradifon theta- cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb, 20 vamidothion, vaniliprole, Verticilhum lecanii, YI5302, Zeta-cypermethrin, Zoiaprofos (lR-cis)-[5-(pheny]methy])-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)- furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxyIate, (3-phenoxyphenyl)-niethyl-2,2,3,3-tetramethylcyclopropanecarboxylate, 25 l-[(2-chloro-54hiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-l,3,5-triazine- 2(lH)-imine, 2-(2-chloro-6-fluoropheny])-4-[4-(l,l-dimethylethyl)phenyl]-4,5-dihydro-oxazole, 2-(acetyloxy)-3-dodecyl-l,4-naphthalenedione, 2-chloro-N-[[[4-(l-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide, 30 2-chloro-N-[[t4-(2,2-dich]oro-l,l-difluoroethoxy)-phenyl]-amino]-carbonyl]- benzamide, 3-methylphenyl propylcarbamate Le A 35 503-Foreign Countries -42- 4-[4-(4-ethoxyphenyl)-4-methylpentyl]~l-fluoro-2-phenoxy-benzene, 4-chloro-2-(l,l-dimethylethy])-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyIJthio]- 3(2H)-pyridazinone, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)- 5 pyridazinone, 4-ch]oro-5-[(6-chloro-3-pyridiny3)methoxy]-2-(3,4-dichlorophenyl)-3(2H)- pyridazinone, Bacillus thuringiensis strain EG-2348, [2-benzoyl-l-(l,l-dimethylethyl)-hydrazinobenzoic acid, 10 2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-l-oxaspiro[4.5Jdec-3-en~4~yl butanoate, [3-[(6-ch]oro-3-pyridiny])methyl]-2-thiazolidiny]idene]~cyanamide, dihydro-2-(nitromethylene)-2H-I,3-thiazine-3(4H)-carboxaldehyde, ethyl [2-[[l,6-dihydro-6-oxo-l-(phenylmethy])-4-pyridaziny]]oxy]ethyl]-carbamate, N-(3,4,4-trifluoro-l-oxo-3"buteny])-glycine, 15 N-(4-chloropheny])-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-lH- pyrazole-1-carboxamide, N-[(2-chloro-5~thiazolyl)methyl]-N'-methyl-N"-nitro-guanidine, N-methyl-N'-(I-methyl-2-propenyl)-l,2-hydrazinedicarbothioamide, N-methyl-N'-2-propenyl-l,2-hydrazinedicarbothioamide, 20 0,0-diethyl [2~(dipropylamino)-2-oxoethyl]-ethy]phosphoraniidothioate, N-cyanomethyl-4-trifluoromethyl-nicotinamide, 3,5-dichloro~l-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifIuoromethy]pyridine-2-yloxy)-propoxy]-benzene. 25 A mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators, 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 30 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 Le A 35 503-Foreign Countries -43- Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi by no means limits the mycotic spectrum covered, but is only for illustration. 5 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, wettable 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 10 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 15 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 20 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 with active compounds according to the invention. In a preferred embodiment, wild plant 25 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 genetical engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of 30 plants" or "plant parts" has been explained above. Le A 35 503-Foreign Countries „44_ 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 5 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, 10 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 15 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) 20 which are preferably 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, 25 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 30 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, Le A 35 503-Foreign Countries -45- cotton, 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 and oilseed rape. Traits that are emphasised are in particular increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), CryHA, CrylUA, CryHIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasised are the increased defence of the plants to 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 sulphonylurea, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plants 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 formula (I) according to the Le A 35 503-Foreipn Countries -46- invention. The preferred ranges stated above for the active compounds also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds specifically mentioned in the present text. Le A 35 503-Foreign Countries 47 Preparation Examples Example 1 ^^s (M) Process (a): A mixture of 382.6 mg (2 mmol) of 2-(l,3,3-trimethy]butyl)aniline, 353.2 mg 10 (2 mmol) of 5-fIuoro-l,3-dimethyl-IH-pyrazol-4-carbonyI chloride and 276.4 mg (2 mmol) of potassium carbonate in 25 ml of acetonitrile is stirred at room temperature overnight. 30 ml of saturated ammonium chloride solution are added, and the mixture is extracted with 30 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated under reduced pressure. 15 The residue is chromatographed on silica gel using cyclohexane/ethyl acetate (starting with pure cyclohexane and finally with 80% ethyl acetate). This gives 280 mg (42% of theory) of 5-fluoro-l,3-dimethy]-N-[2-(l,3,3-trimethylbutyl)phenyI]-lH-pyrazol-4-carboxamide of melting point 78 - 80°C. Le A 35 503-Foreign Countries -48- Example 2 (1-2) Process (b) 10 In the presence of 500 mg of 5% Pd/C, 540 mg (1.792 mmol) of N-[2-(l-ethenylpropyl)phenyl]-5-fluoro-l ,3-dimethyl-lH-pyrazol-4-carboxamide (1-24) in 50 ml of methanol are hydrogenated under a hydrogen pressure of 100 bar at 80°C for 5 hours. The catalyst is filtered off, the filter residue is washed with 2 x 50 ml of methanol and the motherliquor is concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate 4:1. 15 This gives 150 mg (30% of theory) of N»[2-(l-ethy]propyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide as pale yellow crystals. HPLC: logP = 3.01 Le A 35 SOS-Foreign Countries -49 Example 3 N CH3 CH, CH, 5 Processes (c) and (b) as tandem reaction At room temperature, 450 mg (1.41 mmol) of N-[2-(l-ethyl-l-hydroxypropy])~ pheny]]-5-fluoro-l,3-dimethy]-lH-pyrazo]-4~carboxamide (IV-l) in 10 ml of dichloromethane are, after addition of 1.6g (14.1 mmol) of trifluoroacetic acid and 10 0.16 g (1.41 mmol) of triethylsilane, stirred for 1 hour. The reaction solution is adjusted to pH 7 using saturated sodium bicarbonate solution and the organic phase is separated off, dried over magnesium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate 4:1. 15 This gives 120 mg (20% of theory) of N-[2~(l-ethylpropyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide as pale yellow crystals. HPLC: logP = 3.01 20 Le A 35 503-Foreign Countries -50-Example 4 5 Process (d) 0.718 g (2mmol) of the iodoanilide 5-fluoro-N~(2-iodophenyl)-l,3-dimethyl-lH-pyrazoJ-4-carboxamide, 0.25 g (2.5 mmol) of l,l-difluoro~2-viny]cyc}opropane and 0.33 ml (2.4 mmol) of triethylarnine are dissolved in 4 ml of dimethylformamide, and 10 argon is then passed through the reaction solution for 5 minutes. 20 mg (0.09 mmol) of palladium acetate are then added, and the mixture is stirred at 100°C in a closed airtight vessel for 16 hours. After the reaction has ended, the mixture is applied to a silica cartridge and eluted with ethyl acetate. The eluate is admixed with activated carbon, filtered and concentrated under reduced pressure. The residue is 15 chromatographed on silica gel using cyclohexane/ethyl acetate (3:1 to 1:1). This gives 154 mg (23% of theory) of N-{2-[2-(2,2-difluorocyclopropyl)ethenyl]-phenyl}-5-fluoro-l ,3-dimethyl-lH-pyrazol-4-carboxamide. 20 HPLC: logP = 2.59 Le A 35 503-Foreign Countries 51 Example 5 (1-4) 5 Process (e): 227 mg (0.55 mmol) of n-butyltriphenylphosphonium bromide are suspended in 2 ml of tetrahydrofuran and, at ~30°C, 0.34 m] (0.55 mmol) of an n-BuLi solution in hexane are added and the mixture is stirred at this temperature for 20 min. A 10 suspension of 138 mg (0.5 mmol) of N-(2-acetylphenyl)-5-fluoro-l,3-dimethyl-lH- pyrazol-4-carboxamide in 2 ml of tetrahydrofuran is then added, and the mixture is stirred without further cooling for 16 hours. 3 ml of water are added, and the mixture is extracted 3 times with in each case 20 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated under reduced pressure. 15 The residue is chromatographed on silica gel using cyclohexane/ethyl acetate (5:1 to 1:1). This gives 17 mg (10% of theory) of 5-fluoro-l,3-dimethy]-N-[2-(l-methyl-l-hexenyl)phenyl] -1 H-pyrazol -4-carboxami de. 20 HPLC: logP = 4.36 Le A 35 503-Foreign Countries -52- The compounds of the formula (I) listed in Table 1 below are obtained analogously to Examples 1 to 5 and in accordance with the statements in the general descriptions of the processes. Ex. No. Compound logP m.p. (°C) 1-5 1-6 114 HaC-N' 1-7 92-94 1-8 Le A 35 503-Foreign Countries 53 Ex. No. Compound logP m.p. (°C) 1-9 4.36 132-134 1-10 3.37 109-111 1-11 1-12 97 1-13 143 Le A 35 503-Foreign Countries 54- Ex. No. Compound logP m.p, (°C) H3C-N 1-14 H3C CH3 151 1-15 CH, M6 4.11 155-157 1-17 3.01 84-87 Le A 35 503-Foreign Countries -55- Le A 35 503-Foreign Countries 56 Ex. No. Compound JogP m.p. (°C) 1-23 2.57 1-24 -CH, 3.45 1-25 3.82 111-13 CH3 o 1-26 3.67 Le A 35 503-Foreign Countries -57- Ex. No . Compound logP m.p. (°C) 1-27 CH3 o H3C F yCH3 3.82 1-28 CH3 0 H3C F H3C" t ^1 CH3 ^CH3 3.73 1-29 CH3 0 \|M A JL A^ H3C^N^F ^^Y CH3 H3C 3.74 1-30 H3C v r tH3 5.29 1-31 CH3O rj^N H3C F ^> A r CH3 H3C .-— - — — — 3.85 Le A 35 503-Foreign Countries -58- Le A 35 503-Foreign Countries -59- Le A 35 503-Foreign Countries -60- Le A 35 503-Foreign Countries -61- Le A 35 503-Foreign Countries -62- Le A 35 503-Foreign Countries 63 Preparation of the intermediates Example (IV-1) H3C Process (f): At room temperature, 358.5 mg (2 mmol) of 3~(2-aminophenyI)-3-pentanol and 10 353.2 mg (2 mmol) of 5-fluoro-lt3-dimethyl-lH-pyrazol-4-carbonyl chloride are stirred with 276.4 mg (2 mmol) of potassium carbonate in 15 ml of acetonitrile for 16 hours. 30 ml of saturated ammonium chloride solution are added, and the mixture is then extracted with 30 ml of ethyl acetate. The combined organic phases are washed with 30 ml of concentrated sodium chloride solution, dried over magnesium sulphate 15 and concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate (starting with pure cyclohexane and finally with 80% ethyl acetate). 20 This gives 350 mg (45% of theory) of N-[2-(l-ethyl- 1-hydroxypropyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide as colourless crystals. HPLC: logP = 2.47 Le A 35 503-Foreign Countries 64- The compounds of the formula (IV) listed in Table 2 below are obtained analogously to Example (IV-l) and in accordance with the statements in the general descriptions of the process. Ex. No. Compound logP m.p. (°C) IV-2 2.4 158 O IV-3 H3Q h NN^ ^F H3C -CK 3.13 CH, IV-4 3.1 227 Le A 35 503-Foreign Countries -65- Le A 35 503-Foreign Countries -66- -67 Le A 35 503-Foreign Countries Example (V-l) 5 Process (g): A mixture of 5.86 g (42 mmol) of potassium carbonate and 6.2 g (28.3 mmol) of 2-iodoaniline in 100 ml of acetonitrile is stirred at room temperature for 10 min. A solution of 5 g (28.3 mmol) of 5-fIuoro-l,3-dimethyI-lH-pyrazoI-4-carbonyl chloride 10 in 10 ml of acetonitrile is added slowly, and the mixture is stirred under reflux for 16 hours. The reaction mixture is concentrated under reduced pressure, and 200 ml of ethyl acetate and 100 ml of water are added. The organic phase is separated off and the aqueous phase is extracted 3 times with 200 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated under reduced 15 pressure. The residue is stirred in 50 ml of ether. This gives 4.78 g (47% of theory) of 5-fluoro-N-(2-iodophenyl)-l,3-dimethyl-lH-pyrazol-4-carboxamide. 20 HPLC: logP = 2.44 68- Le A 35 503-Foreign Countries Example (Vffl-1) 5 Process (h): A solution of 8g (45 mmol) of 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride in 30 ml of acetonitrile is added to a mixture of 10.4 g (76 mmol) of potassium carbonate and 5.1 g (38 mmol) of 2-aminoacetophenone in 40 ml of 10 acetonitrile, and the mixtured is stirred at 80°C for 16 hours. The reaction mixture is concentrated under reduced pressure, and 200 ml of ethyl acetate and 70 ml of water are added. The organic phase is separated off and the aqueous phase is extracted 3 times with 200 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated under reduced pressure. The residue is filtered 15 through a silica gel cartridge using dichloromethane, the filtrate is concentrated under reduced pressure and the crude product is saturated with diisopropyl ether. This gives 2.5 g (24% of theory) of N-(2-acetylphenyl)-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide. 20 HPLC:logP = 2.15 Le A 35 503-Foreign Countries -69- The JogP values given in the preparation examples and tables above are determined in accordance with EEC Directive 79/831 Annex VA8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C 18). Temperature: 43°C. 5 The determination is carried out in the acidic range at pH 2.3 using the mobile phases 0.1% aqueous phosphoric acid and acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile. The calibration is carried out using unbranched alkan-2-ones (having 3 to 16 carbon 10 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 detennined in the maxima of the chromatographic signals using the UV spectra from 200 nm to 400 nm. 15 Le A 35 503-Foreign Countries -70-Use examples: Example A 5 Pyrenophora teres test (barley) / protective Solvent: 25 parts by weight of N,N-dimethylacetamide Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether 10 To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. (.Tojest for protective activity, young plants are sprayed with the preparation of active 15 compound at the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain in an incubation cabin at 20°C and 100% relative atmospheric humidity for 48 hours. The plants are then placed in a greenhouse at a temperature of about 20°C and a relative 20 atmospheric humidity of about 80%. Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 25 In this test, for example, the compounds 16 and 17 of the Preparation Examples exhibit, at an application rate of 250 g/ha, an efficacy of 95% or more. j Le A 35 503-Foreign Countries 71 Table A Pyrenophora teres test (barley) / protective Active compound according to the invention Application rate of active compound in g/ha Efficacy in% (16) 250 100 (17) 250 100 Le A 35 503-Foreign Countries -72-Example B Podosphaera test (apple) / protective 5 Solvent: 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 10 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, the plants 15 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 carried out 10 days after the inoculation. 0% means an efficacy which 20 corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. -J In this test, for example, the compounds 9, 16, 17 and 18 of the Preparation Examples exhibit, at an application rate of 100 g/ha, an efficacy of 90% or more. 25 Le A 35 503-Foreien Countries 73 Table B Podosphaera test (apple) / protective Active compound according to the invention Application rate of active compound ing/ha Efficacy in% . (9) 100 90 (16) 100 100 (17) 100 100 Le A 35 503-Foreign Countries -74- Podosphaera test (apple) / protective Active compound according to the invention Application rate of active compound ing/ha Efficacy in% (18) 100 100 Le A 35 503-Foreign Countries -75-Example C Alternaria test (tomato) / protective 5 Solvent: 49 parts by weight of N,N-dimethylformarnide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the 10 concentrate is diluted with water to the desired concentration. To test for protective activity, young tomato plants are sprayed with the preparation of active compound at the stated application rate. 1 day after the treatment, the plants are inoculated with a spore suspension of Alternaria solani and then remain at 100% rel. 15 humidity and 20°C for 24 h. The plants then remain at 96% rel. atmospheric humidity and a temperature of 20°C. Evaluation was carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection 20 is observed. In this test, for example, the compounds 16, 17 and 20 of the Preparation Examples exhibit, at an application rate of 750 g/ha, an efficacy of 90% or more. 1 \ ^ - Le A 35 503-Foreign Countries 76 Table C Alternaria test (tomato) / protective Active compound Application rate Efficacy of active compound ing/ha in % (16) 750 95 (H) 750 95 (20) 750 100 Le A 35 503-Foreign Countries 77 Patent claims 1. Pyrazolylcarboxanilides of the formula (I) 5 (I), in which R1 represents hydrogen, cyano, halogen, nitro, Cj-C4-alkyl, Cj~C4- haloalkyl having 1 to 5 halogen atoms, C3-C6-cycloalkyl, Cj-C,^- 10 alkoxy, CrC4-haloalkoxy having 1 to 5 halogen atoms, CrC4- alkylthio, Cj-C4-haloalkylthio having 1 to 5 halogen atoms or aminocarbonyl-C]"C4-alkyl, R2 represents hydrogen, Ci-C4-alkyl, Cj-Cg-haloalkyl having 1 to 5 15 halogen atoms, C2-C6-alkenyl, C3-C6-cycloalky], Ci-C4-alkylthio-Cj- C4-alkyl, Ci-C4-haloalkylthio-CrC4-alkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy-Ci-C4-alkyl or CpQ-haloalkoxy-Cj-C^-alkyl having 1 to 5 halogen atoms, 20 G represents halogen or CrC4-alkyl, G furthermore represents Cs-C^-alkyl, R3 represents unsubstituted C^^rj-alkyl or represents Ci-C2n-alkyl 25 which is mono- or polysubstituted by identical or different substituents Le A 35 503-Foreign Countries -78- from the group consisting of halogen and/or C3-C6-cycloalkyl or represents C2-C2o-alkenyl or C2-C2o-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C5-cycloalkyl, where the cycloalkyl moiety for its part may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or Cj-C^alkyl and 10 n represents 0, 1 or 2. 2. Pyrazolylcarboxanilides of the formula (I) according to Claim 1, in which G represents halogen or CrC4-alkyl, 15 andR],R2,R3and n are as defined in Claim 1. 3. Pyrazolylcarboxanilides of the formula (I) according to Claim 1, in which R1 represents hydrogen, cyano, halogen, nitro, Cj-C^alkyl, CrC4- 20 haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C3- Cg-cycloalky], Cj-C4-alkoxy, CpC^haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, Ci-Q^-alkylthio, C]-C4-haloalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms or aminocarbonyl-Cj-C4-alkyl, 25 R2 represents hydrogen, Ci-C4-alkyl, C]-C6-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C2-C6-alkenyl, C3-C6 cycloalkyl, C1-C4-alkylthio-C1-C4-alkyl, CrC4-haloalkylthio-CrC4- alky] having 1 to 5 fluorine, chlorine and/or bromine atoms, Cj-C4- 30 alkoxy-Ci-C4-alkyl or Ci-C4-haloalkoxy-Cj-C4-alkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, Le A 35 503-Foreign Countries -79- G represents halogen or C j-C4-alkyl, G furthermore represents Cs-Ce-alkyl, 5 R3 represents unsubstituted C2-C12-a]kyl or represents C2-C]2-a]ky] which is mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6- cycloalkyl or represents C2-Cj2-a]kenyl or C2-Cj2-alkynyl, each of which is optionally mono- to tetrasubstituted by identical or different 10 substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the moiety for its part may optionally be mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen and/or Cj-C4-alkyl, 15 n represents 0, 1 or 2. 4. Pyrazolylcarboxanilides of the formula (I) according to Claim 3, in which G represents halogen of Ci-Chalky], 20 1 -\ -i andR\Rz,RJand n are as defined in Claim 3. 5. Pyrazolylcarboxanilides of the formula (I) according to Claim 1, in which 25 R1 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl or trifluoroethyl, R2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl or trifluoroethyl, 30 G represents fluorine, chlorine or methyl, Le A 35 503-Foreign Countries -80- G furthermore represents ethyl or t-butyl, G furthermore represents 2,4-dimethylbutyl, R3 represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl or decynyl, each of which may be attached at any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl, n represents 0, 1 or 2. 6. Pyrazolylcarboxanilides of the formula (I) according to Claim 5, in which G represents fluorine, chlorine or methyl, and R1, R2, R3 and n are as defined in Claim 5. 7. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims 1 to 6 in which R1 represents methyl and R2 represents methyl. 8. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims 1 to 7, in which Le A 35 503-Foreign Countries 81- R3 represents unsubstituted C2-C2o-alkyl (preferably C2-C12-alkyl, particularly preferably C2-C6~alkyl). 9. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims 5 1 to 8, in which n represents 0. 10. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims 10 1 to 9, in which R1 represents methyl, R2 represents methyl, 15 20 R3 represents unsubstituted C2-C2o-alkyl (preferably C2-Ci2-alkyl, very particularly preferably C2-C6-alkyl), n represents 0. 11. Process for preparing compounds of the formula (I) according to Claim 1, characterized in that a) carboxylic acid derivatives of the formula (II) 25 (n), in which Le A 35 503-Foreign Countries 82 R1 and R2 are as defined in Claim 1 and X represents halogen, are reacted with an aniline derivative of the formula (HI) in which 10 G, R3 and n are as defined in Claim 1, r ■■ ,-2A lus^-p ■ if appropriate in the presence of an acid binderand if appropriate in the presence of a diluenu or (£p 15 0 b) pyrazolylcarboxanilides of the formula (la) & >_ da). ^f F u R in which 20 Hf^ RJ,R2, G and n are as defined in Claim 1, ,>■•;-/",'" Le A 35 503-Foreign Countries 83 R4 represents C2-C2o-alkenyl or C2-C20-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C4-alkyl, are hydrogenated, if appropriate in the presence of a diluent and if f appropriate in the presence of a catalyst, or - A 6 10 c) hydroxyalkylpyrazolylcarboxanilidesof the formula (IV) (IV), in which 15 R1, R2, G and n are as defined in Claim 1, R5 represents C2-C20-hydroxyalkyl which is optionally additionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3- 20 Cg-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C^alkyl, ' -■'■■ .,../. : //.Y^-V^ , /') «■ r r'i S -"'iiwvY / ; is dehydrated, if appropriate in the presence of a diluenWand if appropriate in the presence of an acid or $f t./ 25 Le A 35 503-Foreign Countries -84 d) halopyrazolylcarboxanilides of the formula (V) in which 5 R1, R2, G and n are as defined in Claim 1, Y represents bromine or iodine, 10 are reacted with an alkyne of the formula (VI) HC^—R6 (VI), in which 15 R6 represents C2-Ci8-a]kyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C^alkyl, 20 or an alkene of the formula (VH) Le A 35 503-Foreign Countries 85 in which R7, R8 and R9 independently of one another each represent hydrogen or alky] which is optionally mono- or polysubstituted by 5 identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalky], where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C4-alkyl and where the total number of carbon atoms of the open-chain moiety does not exceed the number 20, if appropriate in the presence of a diluent, if appropriate in the presence of an acid binder/jand in the presence of one or more catalysts, or ,1 ) & 15 e) ketones of the formula (VET) (Vm), in which 20 R1, R2, G and n are as defined in Claim 1, R10 represents hydrogen or Ci-Cjg-alkyl which is optionally mono-or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-Cg-cycloalkyl, Le A 35 503-Foreign Countries -86 where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or CrC4-alkyl, are reacted with a phosphorus compound of the general formula (IX) 5 R^—PX (IX), in which R11 represents hydrogen or Cj-Cjg-alky] which is optionally mono 10 or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cyc]oalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C4-a]ky] and 15 Px represents a grouping -P+(C6H5)3 CI", -P+(C6H5)3 Br-, -P+(C6H5)31, -P(=0)(OCH3)3 or -P(=0)(OC2H5)3, if appropriate in the presence of a diluent,^) / •, ^!-.-- :-: ty" U,A,^ ■-■^t>-& ;\& "•■- • 12. Compositions for controlling undesirable microorganisms, characterized in 20 that they comprise at least one pyrazolylcarboxanilide of the formula (I) according to Claim 1, in addition to extenders and/or surfactants. 13. Use of pyrazolylcarboxanilides of the formula (I)~~a~ccording to Claim 1 for controlling undesirable microorganisms. 25 14. Method for controlling undesirable microorganisms, characterized in that pyrazolylcarboxanilides of the formula-CIXaccording to Claim 1 are applied to the microorganisms and/or their habitat. Le A 35 503-Foreign Countries 87 15. Process for preparing compositions for controlling undesirable microorganisms, characterized in that pyrazolylcarboxanilides of the formula (I) according to Claim 1 are mixed with extenders and/or surfactants. 16. Hydroxyalkylpyrazolylcarboxanilides of the formula (IV) (IV), in which 10 R1, R2, G and n are as defined in one or more of Claims 1 to 7 and R5 represents C2-C2o-hydroxyalkyl which is optionally additionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the 15 cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C^alkyl. 17. Process for preparing hydroxyalkylpyrazolylcarboxanilides of the formula (IV) according to Claim 13, characterized in that 20 f) carboxylic acid derivatives of the formula (II) Le A 35 503-Foreign Countries 88 (II), in which R1 and R2 are as defined in Claim 1 and X represents halogen, are reacted with a hydroxyalkylanihne derivative of the formula (X) in which R3, G and n are as defined in Claim 1, R5 represents C2-C2rj-hydroxyaIkyl which is optionally additionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-Cg-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C4-alkyl, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. 18. Halopyrazolylcarboxanilides of the formula (V) Le A 35 503-Foreign Countries -89 5 10 ■l„K « R2 in which R1, R2, G and n are as defined in one or more of Claims 1 to 7 and Y represents bromine or iodine. 19. Process for preparing halopyrazolyicarboxanilides of the formula (V) according to Claim 14, characterized in that g) carboxylic acid derivatives of the formula (II) in which 15 R1 and R2 are as defined in Claim 1, X represents halogen, 20 are reacted with a haloaniline of the formula (XI) Le A 35 503-Foreign Countries -90 (XI), in which G and n are as defined in Claim 1, Y represents bromine or iodine, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. 10 20. Ketones of the formula (VIH) (VUI), in which 15 R1, R2, G and n are as defined in one or more of Claims 1 to 7 and R10 represents hydrogen or Cj-Ci8-alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group 20 consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cp C4-alkyl. Le A 35 503-Foreign Countries -91- 21. Process for preparing ketones of the formula (VAT) according to Claim 17, characterized in that h) carboxylic acid derivatives of the formula (IF) cn). R in which 10 R1 and R2 are as defined in Claim 1, X represents halogen, are reacted with ketoanilines of the formula (XII) 15 20 in which G and n are as defined in Claim 1, R10 represents hydrogen or Cj-C^-alkyl which is optionally mono-or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3~C6-cycloalkyl, Le A 35 503-Foreign Countries -92- where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or CpC^alkyl, if appropriate in the presence of an acid binder and if appropriate in 5 the presence of a diluent. 93 22. Pyrazolylcarboxanilides of the formula I substantially as herein described with reference to the foregoing examples. Dated this on 03rd day of December, 2008 (PA$AL KALRA) OF REMFRY AND SAGAR ATTORNEY FOR THE APPLICANTS

Full Text

FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
&
THE PATENTS RULES, 2003
COMPLETE SPECIFICATION
[See Section 10; rule 13]
"PYRAZOLYLCARBOXANILIDES AND PROCESS FOR PREPARATION THEREOF"

BAYER AKTIENGESELLSCHAFT, a German company, of D-51368 Leverkusen, Germany
The following specification particularly describes the invention and the manner in which it is to be performed:

Le A 35 503-Foreign Countries Nk/li/NT
1 -
Pyrazolylcarboxanilides
The present invention relates to novel pyrazolylcarboxanilides, to a plurality of
5 processes for their preparation and to their use for controlling undesirable
microorganisms.
It is already known that numerous carboxanilides have fungicidal properties
(compare WO 93-11117, EP-A 0 545 099, EP-A 0 589 301, WO 99/09013,
10 DE 198 40 322, EP-A 0 824 099, JP 63048269). Thus, N-(2-cyclohexyl)-l,3-
dimethyl-5--fluoropyrazo]-4-carboxanilide, N-(2-pheny])~l,3-dimethylpyrazol-4-
carboxanilide and N-[2-(2-fluorophenyl)]-l,3-dimethylpyrazol-4-carboxanilide can be used for controlling fungi. The activity of these substances is good; however, at low application rates it is sometimes unsatisfactory.
15
y^-'This invention now provides novel pyrazolylcarboxanilides of the formula (I)

(D

20

in which
R1 represents hydrogen, cyano, halogen, nitro, CpQ-alkyl, CrC4-haloalkyl having 1 to 5 halogen atoms, C3-C6-cycloalkyl, Cj~C4-alkoxy, CrC4-haloalkoxy having 1 to 5 halogen atoms, CrC4-alkylthio, CrC4-haloalkylthio having 1 to 5 halogen atoms or aminocarbonyl-C|-C4-alkyl,

Le A 35 503-Foreign Countries
-2
R2 represents hydrogen, CrC4-alkyl, CpCg-haloalkyl having 1 to 5 halogen atoms, C2-C6-alkenyl, C3-C6-cycloalkyl, CrC4-alkyltMo-CrC4-alkyl, Cr C4-haloalkylthio-CrC4-alkyl having 1 to 5 halogen atoms, Ci-Q-alkoxy-C!-C4-alkyl or CrC4-haloalkoxy-C]-C4-alkyl having 1 to 5 halogen atoms, 5
G represents halogen or Cj-C4-alkyl,
G furthermore represents Cs-C6-alkyl,
10 R3 represents unsubstituted C2-C20-alkyl or represents Gi~C2o-alkyl which is
mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl or represents C2-C2o-alkenyl or C2-C20-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or
15 C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be
mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or Cj-C4-a]kyl and
represents 0, 1 or 2.
20
If appropriate, the compounds according to the invention can be present as mixtures
of different 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 as tautomers. What is claimed are both the E and the Z isomers, and the threo
25 and erythro and also the optical isomers, any mixtures of these isomers, and also the
possible tautomeric forms.
(Furthermore, it has been found that pyrazolylcarboxanilides of the formula (I) are
obtained when
30

—c^"

a) carboxylic acid derivatives of the formula (II)

Le A 35 503-Foreign Countries
3-
0.
R1\ V—X
(H),
N
-.2
in which
R1 and R2 are as defined above and
X represents halogen,
are reacted with an aniline derivative of the formula (HI)
^3~Gn (m)'
H2N
R3 in which
G, R3 and n are as defined above,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
b) pyrazolylcarboxanilides of the formula (la)

Le A 35 503-Foreign Countries

(la),

in which
R1, R2, G and n are as defined above and
R4 represents C2-C2o-alkenyl or C2-C2o-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or C]-C4-alkyl,
are hydro genated, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or
c) hydroxyalkylpyrazolylcarboxanilides of the formula (IV)

(IV),

in which

Le A 35 503-Foreign Countries
R1, R2, G and n are as defined above and
R5 represents C2-C2o-hydroxyalkyl which is optionally additionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cr Chalky!,
is dehydrated, if appropriate in the presence of a diluent and if appropriate in the presence of an acid, or
d) halopyrazolylcarboxanilides of the formula (V)

in which
R1, R2, G and n are as defined above and
Y represents bromine or iodine,
are reacted with an alkyne of the formula (VI)

(V),

in which

HC^^-R6 (VI),

Le A 35 503-Foreign Countries
R6 represents C2-C]g-alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C^alkyl,
or an alkene of the formula (VH)

R8
= R7/=\R9 (vn),

in which
10
R7, R8 and R9 independently of one another each represent hydrogen or alkyl
which is optionally mono- or polysubstituted by identical or different
substituents from the group consisting of halogen and/or C3-C6-
cycloalkyl, where the cycloalkyl moiety for its part may optionally be
15 substituted by halogen and/or CrC4-aIkyl and where the total number
of carbon atoms of the open-chain moiety does not exceed the number 20,
if appropriate in the presence of a diluent, if appropriate in the presence of an
20 acid binder and in the presence of one or more catalysts, or
-^ e) ketones of the formula (VHT)

(VTTD,

Le A 35 503-Foreign Countries

10

in which
R1, R2, G and n are as defined above and
R10 represents hydrogen or C]-C]3-alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C4-alkyl,
are reacted with a phosphorus compound of the general formula (IX)
R11—pX (IX),
in which

15
R11 represents hydrogen or Cj-Cjg-alkyl which is optionally mono- or
polysubstituted by identical or different substituents from the group
consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl
moiety for its part may optionally be substituted by halogen and/or Cj-
20 C4-alkyl and
Px represents a grouping -P+(C6H5)3 CI" -P+(C6H5)3 Br-, -P+(C6H5)31~ -P(=0)(OCH3)3 or-P(=0)(OC2H5)3,
25 if appropriate in the presence of a diluent.
--^ ( Finally, it has been found that the novel pyrazolylcarboxanilides of the formula (T) have very good microbicidal properties and can be used for controlling undesirable microorganisms both in crop protection and in the protection of materials.
Le A 35 503-Foreign Countries
—^(Surprisingly, the pyrazolylcarboxanilides of the formula (I) according to the invention have considerably better fungicidal activity than the constitutionally most similar active compounds of the prior art having the same direction of action, j
5 __i> The formula (I) provides a general definition of the pyrazolylcarboxanilides according to the invention.
R1 preferably represents hydrogen, cyano, halogen, nitro, CrC4-alkyl, CrC4-
haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C3-C6-
10 cycloalkyl, Cj-C^alkoxy, C1-C4-haloalkoxy having 1 to 5 fluorine, chlorine
and/or bromine atoms, Q-C4-alkylthio, C1-C4-haloalkylthio having 1 to 5
fluorine, chlorine and/or bromine atoms or aminocarbonyl-Ci-C4-alkyl.
R2 preferably represents hydrogen, C1-C4-aIkyl, CrC6-haloalkyl having 1 to 5
15 fluorine, chlorine and/or bromine atoms, C2-C6-alkenyl, C3-C6 cycloalkyl,
C1-C4-alkyIthio-C1-C4-aJkyl, CrC4-haloalky]thio-CrC4-alkyI having 1 to 5 fluorine, chlorine and/or bromine atoms, Ci-Q-alkoxy-Cj-C^-alkyl or CrC4-haloalkoxy-C1-C4-alkyl having 1 to 5 fluorine, chlorine and/or bromine atoms. 20
G preferably represents halogen or Cj-C4-aIkyl.
G furthermore preferably represents Cs-Ce-alkyl.
25 R3 preferably represents unsubstituted C2-C12-alkyl or represents CrC12-alkyl
which is mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl or represents C2-C12-alkenyl or C2-C12-alkynyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group
30 consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the
cycloalkyl moiety for its part may optionally be mono- to tetrasubstituted by

Le A 35 503-Foreign Countries
9-

5

identical or different substituents from the group consisting of halogen and/or CrC4-alkyl.
n preferably represents 0, 1 or 2.
R1 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl or trifluoroethyl.

R2 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-
10 , s- or t-butyl, trifluoromethyl or trifluoroethyl.

15

G particularly preferably represents fluorine, chlorine or methyl. G furthermore particularly preferably represents ethyl or t-butyl. G furthermore particularly preferably represents 2,4-dimethylbutyl.

R3 particularly preferably represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, ethenyl,
20 propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl,
ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl or decynyl, each of which may be attached at any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl,
25 cyclopentyl and/or cyclohexyl.
n also particularly preferably represents 0, 1 or 2.
A very particularly preferred group are the compounds of the formula (I), in which
30
R1 represents methyl and

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R2 represents methyl.
Very particularly preferred are furthermore compounds of the formula (I), in which
5 R3 represents unsubstituted C2~C2o-alkyl (preferably C2-Ci2-alkyl, particularly
preferably C2-C6-alkyl).
Very particularly preferred are furthermore compounds of the formula (I), in which
10 n represents 0.
Emphasis is given to compounds of the formula (I), in which
15
R1 represents methyl,
R2 represents methyl,
R3 represents unsubstituted C2-C2cralkyl (preferably C2-C12-alkyl, very particularly preferably C2-C6-alkyl),
20
n represents 0.
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
25 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. A plurality of radicals
having the same indices, such as, for example, n radicals G for n >1, can be identical
30 or different.

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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 represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine. 5
However, the abovementioned general or preferred radical definitions or illustrations can also be combined with one another, i.e. between the respective ranges and preferred ranges, as desired. The definitions or illustrations apply both to the end products and, correspondingly, to the precursors and intermediates.
.to
The definitions mentioned can be combined with one another as desired. Moreover, individual definitions may not apply.
Using 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride and 2-(l-
15 methylhexy])aniline as starting materials, the process a) according to the invention
can be illustrated by the following formula scheme:

20 The formula (H) provides a general definition of the carboxylic acid derivatives
required as starting materials for carrying out the process a) according to the invention. In this formula (IT), R1 and R2 preferably and 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
25 preferred and particularly preferred for R1 and R2. X represents halogen, preferably
chlorine.

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The carboxylic acid derivatives of the formula (H) 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).
5 The formula (III) provides a general definition of the anilines furthermore required
for the starting materials for carrying out the process a) according to the invention. In
this formula (in), G, R3 and n preferably and 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 and
10 particularly preferred for G, R3 and n.
The aniline derivatives of the formula (HI) are known and/or can be prepared by
known methods (compare, for example, Heterocycles (1989), 29(6), 1013-16; J. Med.
Chem. (1996), 39(4), 892-903; Synthesis (1995), (6), 713-16; Synth. Commun.
15 (1994), 24(2), 267-72; DE 2727416; Synthesis (1994), (2), 142-4; EP 0 824 099).
Using 5-fluoro-1,3-dimethyl-N-{2-[(1Z)-1 -methyl-1 -hexenyljphenyl}-lH-pyrazol-4-
carboxamide and hydrogen as starting materials, and a catalyst, the course of the
process b) according to the invention can be illustrated by the following formula
20 scheme:

Catalyst
H3C
The formula (la) provides a general definition of the pyrazolylcarboxanilides required
as starting materials for carrying out the process b) according to the invention. In this
25 formula (la), R1, R2, G and n preferably and 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 and particularly preferred for R1, R2, G and n.

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R4 preferably represents C2-C12-alkenyl or C2-C12-alkynyl5 each of which is
optionally mono- to tetrasubstituted by identical or different substitutents
from the group consisting of fluorine, chlorine and/or C3-C6-cycloaIkyl,
where the cycloalkyl moiety for its part may optionally be mono- to
5 tetrasubstituted by identical or different substituents from the group consisting
of halogen and/or Ci-C4-alkyl.
R4 particularly preferably represents in each case straight-chain or branched
ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl,
10 decenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl,
nonynyl or decynyl, each of which may be attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. 15
The compounds of the formula (la) are compounds according to the invention and
can be prepared by process a), c), d) or e).
Using 5-fluoro-N-[2-(l-hydroxy-l-methylhexyl)phenyl]-l,3-dimethyl-lH-pyrazoM-
20 carboxamide as starting material and an acid, the course of the process c) according
to the invention can be illustrated by the following formula scheme:

Acid

25 The formula (TV) provides a general definition of the hydroxyalkylpyrazolyl-
carboxanilides required as starting materials for carrying out the process c) according to the invention. In this formula (IV), R1, R2, G and n preferably and particularly preferably have those meanings which have already been mentioned in connection

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14
with the description of the compounds of formula (I) according to the invention as being preferred and particularly preferred for R1, R2, G and n.
R5 preferably represents C2-C12-hydroxyalkyl which is optionally additionally
5 mono- to tetrasubstituted by identical or different substituents from the group
consisting of chlorine, fluorine, bromine and/or C3-C6-cycloalkyl, where the
cycloalkyl moiety for its part may optionally be substituted by halogen and/or
CrC4-alkyl.
10 R5 particularly preferably represents in each case straight-chain or branched
hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, hydroxynonyl or hydroxydecyl, each of which may be attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting
15 of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or
cyclohexyl.
The compounds of the formula (IV) have hitherto not been known; as novel compounds, they also form part of the subject-matter of the present application.

20
25

It has also been found that the hydroxyalkylpyrazolylcarboxanilides of the formula (IV) have very good microbicidal properties and can be used for controlling undesirable microorganisms both in crop protection and in the protection of materials.
The hydroxyalkylpyrazolylcarboxanilides of the formula (TV) are obtained when f) carboxylic acid derivatives of the formula (IT)

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(n),

in which
R1, R2 and X are as defined above,
are reacted with a hydroxyalkylaniline derivative of the formula (X)
H2N

R
in which
10

15

R3, R5, G and n are as defined above,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Using 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride and 2-(2-aminophenyl)-2-heptanol as starting materials, the course of the process f) according to the invention can be illustrated by the following formula scheme:

20

H,Q
/1
'1
CH

COCI

The carboxylic acid derivatives of the formula (IT) required as starting materials for carrying out the process f) according to the invention have already been described

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10

further above, in connection with the description of the process a) according to the invention.
The formula (X) provides a general definition of the hydroxyalkylaniline derivatives furthermore required as starting materials for carrying out the process f) according to the invention. In this formula (X), R3, R5, G and n preferably and particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formulae (I) and (TV) according to the invention as being preferred and particularly preferred for R3, R5, G and n.
The hydroxyalkylaniline derivatives of the formula (X) are known and/or can be obtained by known methods (cf., for example, US 3,917,592 or EP 0 824 099).

Using 5-fluoro-N-(2-iodophenyl)-l,3-dimethyI-lH-pyrazol-4-carboxamidee and 1-
15 pentyne or alternatively 1-hexene as starting materials and in each case a catalyst and
a base, the course of the process d) according to the invention can be illustrated by the two formula schemes below:

HC=

-CH,

Catalyst, Base
HI

Catalyst, Base
H2C

CH,

20

H3C-

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The formula (V) provides a genera] definition of the halopyrazolylcarboxanilides
required as starting materials for carrying out the process d) according to the
invention. In this formula (V), R1, R2, G and n preferably and particularly preferably
have those meanings which have already been mentioned in connection with the
5 description of the compounds of the formula (I) according to the invention as being
preferred and particularly preferred for R1, R2, G and n. Y preferably represents bromine or iodine.
The halopyrazolylcarboxanilides of the formula (V) have hitherto not been known; as
10 novel compounds, they also form part of the subject-matter of the present application.
They are obtained when
g) carboxylic acid derivatives of the formula (H)

15
20

in which
R1, R2 and X are as defined above,
are reacted with a haJoaniline of the formula (XT)

(XI),

in which

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G, n and Y are as defined above,
if appropriate in the presence of an acid binder and if appropriate in the
5 presence of a diluent.
Using 5-fluoro-l,3-dirnethyl-lH-pyrazol-4-carbonyl chloride and 2-iodoaniline as starting materials, the course of the process g) according to the invention can be illustrated by the following formula scheme: 10

The carboxylic acid derivatives of the formula (H) required as starting materials for
carrying out the process g) according to the invention have already been described
15 further above, in connection with the description of the process a) according to the
invention.
The formula (XI) provides a general definition of the haloanilines further required as
starting materials for carrying out the process g) according to the invention. In this
20 formula (XI), G, n and Y preferably and particularly preferably have those meanings
which have already been mentioned in connection with the description of the compounds of the formulae (I) and (V) as being preferred and particularly preferred for G, n and Y.
25 The haloanilines of the formula (XI) are known chemicals for synthesis.
The formula (VI) provides a general definition of the alkynes furthermore required as starting materials for carrying out the process d) according to the invention.

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R6 preferably represents C2-Cio-alkyl which is optionally mono- to
tetrasubstituted by identical or different substituents from the group consisting
of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl
5 moiety for its part may optionally be substituted by halogen and/or C1-C4-
alkyl.
R6 particularly preferably represents in each case straight-chain or branched
ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each of which may be
10 attached in any position and each of which is optionally mono- to
tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl.
15 The alkynes of the formula (VI) are known chemicals for synthesis.
The formula (VH) provides a general definition of the alkenes furthermore alternatively required as starting materials for carrying out the process d) according to the invention.
20
R7, R8 and R9 independently of one another each preferably represent hydrogen or alkyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be
25 substituted by halogen and/or C1-C4-alkyl and the total number of carbon
atoms of the open-chain moiety does not exceed the number 12.
R7, R8 and R9 independently of one another particularly preferably each represent
hydrogen or in each case straight-chain or branched ethyl, propyl, butyl,
30 pentyl, hexyl, heptyl or octyl, each of which may be attached in any position
and each of which is optionally mono- to tetrasubstituted by identical or
different substituents from the group consisting of fluorine, cyclopropyl,

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difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl, where the total number of carbon atoms of the open-chain moiety does not exceed the number 12.
5 The alkenes of the formula (VET) are known chemicals for synthesis.
Using N-(2-acetylphenyl)-5-fluoro~l,3-dimethyl-lH-pyrazol-4-carboxamide and butyl(triphenyl)-phosphonium iodide as starting materials, the course of process e) according to the invention can be illustrated by the following formula scheme: 10

The formula (VTJT) provides a general definition of the ketones required as starting
materials for carrying out the process e) according to the invention. In this formula
15 (VITJ), R1, R2, G and n preferably and 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 and particularly preferred forR1, R2, G and n.
20 R10 preferably represents C2~C10-alkyl which is optionally mono- to
tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C4-alkyl.
25
R10 particularly preferably represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each of which may be attached in any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting

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21
of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl.
The ketones of the formula (VUI) have hitherto not been known. As novel chemical
5 compounds, they also form part of the subject-matter of the present application.
They are obtained when
h) carboxylic acid derivatives of the formula (H)
10

Q
15

in which
R1, R2 and X are as defined above,
are reacted with ketoanilines of the formula (XH)

(xn),

20

in which
R10, G and n are as defined above,

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if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Using 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride and l-(2-
5 aminophenyl)ethanone as starting materials, the course of the process h) according to
the invention can be illustrated by the following formula scheme:

10 The carboxylic acid derivatives of the formula (H) required as starting materials for
carrying out the process h) according to the invention have already been described further above, in connection with the description of the process a) according to the invention.
15 The formula (XE) provides a general definition of the ketoanilines furthermore
required as starting materials for carrying out the process h) according to the invention. In this formula (XII), R10, G and n preferably and particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formulae (I) and (VTH) according to the
20 invention as being preferred and particularly preferred for R10, G and n.
The ketoanilines of the formula (XII) are generally customary chemicals for synthesis (compare, for example, J. Am. Chem. Soc. 1978, 100(15), 4842-4857 or US 4,032,573). 25
The formula (DC) provides a general definition of the phosphorus compounds furthermore required as starting materials for carrying out the process e) according to the invention.

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R11 preferably represents C2-C10-alkyI which is optionally mono- to
tetrasubstituted by identical or different substituents from the group consisting
of chlorine, fluorine, bromine and/or C3-C6~cycIoalkyl, where the cycloalkyl
5 moiety for its part may optionally be substituted by halogen and/or C1-C4-
alkyl.
R11 particularly preferably represents in each case straight-chain or branched
ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each of which may be
10 attached in any position and each of which is optionally mono- to
tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl.
15 Px preferably represents a grouping -P+(C6H5)3 Cl~, -P+(G6H5)3 Bi~,
-P+(C6H5)3 I- -P(=0)(OCH3)3 or -P(=0)(OC2H5)3.
The phosphorus compounds of the formula (IX) are known and/or can be prepared by
known processes (compare, for example, Justus Liebigs Ann. Chem. 1953, 580, 44-
20 57 or Pure Appl. Chem. 1964, 9, 307-335).
Suitable fluents for carrying out the processes a), f), g) and h) 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,
25 cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; 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-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisol, or
30 amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-
formanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.

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The processes a), f), g) and h) according to the invention are, 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
5 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, calcum acetate,
ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate,
sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as
10 trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-
benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
15 When carrying out the processes a), f), g) and h) according to the invention, the
reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures of from 0°C to 150°C, preferably at temperatures from 0°C to 80°C.
20 For carrying out the process a) according to the invention for preparing compounds
of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of aniline derivatives of the formula (IH) are employed per mole of the carboxylic acid derivative of the formula (H).
25 For carrying out the process f) according to the invention for preparing compounds of
the formula (IV), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of hydroxyalkylaniline derivatives of the formula (X) are employed per mole of the carboxylic acid derivative of the formula (II).
30 , For carrying out the process g) according to the invention for preparing compounds of the formula (V), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of

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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 decaline; halogenated hydrocarbons,
5 such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform,
carbon tetrachloride, dichloroethane or trichloroetahen; ethers, such as diethyl ether,
diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane, 1,2-diethoxyethane or anisol; ketones, such as acetone,
butanone, methyl isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile,
10 propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-
dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-
methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate
or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; sulfones, such as
sulpholane; alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-
15 butanol, ethanediol, propane- 1,2-diol, ethoxyethanol, methoxyethanol, diethylene
glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.
The process c) according to the invention is, if appropriate, carried out in the
20 presence of an acidJ Suitable acids are all inorganic and organic protic acids and also
Lewis acids, and also all polymeric acids. These include, for example, hydrogen
chloride, sulphuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic
acid, methanesulphonic acid, trifluoromethanesulphonic acid, toluenesulphonic acid,
boron trifluoride (also as etherate), boron tribromide, aluminium trichloride, titanium
25 tetrachloride, tetrabutylorthotitanate, zinc chloride, iron(UI) chloride, antimony
pentachloride, acidic ion exchangers, acidic alumina and acidic silica gel.
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
30 carried out at temperatures of from 0°C to 150°C, preferably at temperatures of from
0°C to 80°C.

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The processes c) and b) according to the invention can also be carried out in a tandem
reaction ("One-pot reaction"). To this end, a compound of the formula (TV) is
reacted, if appropriate in the presence of a diluent (suitable diluents as for process c)),
and if appropriate in the presence of an acid (suitable acids as for process c)) and in
5 the presence of triethylsilane.
Suitable diluents for carrying out the process d) according to the invention are all
inert organic solvents. These preferably include nitriles, such as acetonitrile,
propionitrile, n- or i-butyronitrile or benzonitrile, or amides, such as N,N-
10 dimethylformamide, N,N-dimethylacetamide, N-rrethylformanilide, N-
methylpyrrolidone or hexamethylphosphoric triamide.
15
20
25
If appropriate, the process d) according to the invention is 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, calcium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
The process d) according to the invention is carried out in the presence of one or more catalysts.
30 Suitable catalysts are in particular palladium salts or complexes. Preferably suitable
for this purpose are palladium chloride, palladium acetate, tetrakis(triphenyl-phosphine)palladium or bis(triphenylphosphine)palladium dichloride. It is also

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possible to generate a palladium complex in the reaction mixture by adding a palladium salt and a complex ligand separately to the reaction.
Suitable ligands are preferably organophosphorus compounds. Examples which may
5 be mentioned are: triphenylphosphine, tri-o-tolylphosphine, 2,2'-bis(diphenyl-
phosphino)-l,l '-binaphthyl, dicyclohexylphosphinebiphenyl, l,4-bis(diphenyl-
phosphino)butane, bisdiphenylphosphinoferrocene, di(tert-butylphosphino)biphenyl,
di(cyclohexylphosphino)biphenyl, 2-dicyclohexylphosphino-2'-N,N-dimethylamino-
biphenyl, tricyclohexylphosphine, tri-tert-butylphosphine. However, it is also
10 possible to dispense with ligands.
The process d) according to the invention is furthermore, if appropriate, carried out in the presence of a further metal salt, such as copper salts, for example copper(I) iodide. 15
When carrying out the process d) 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 20°C to 180°C, preferably at temperatures of from50°Ctol50°C. 20
For carrying out the process d) according to the invention for preparing compounds of the formula (I), in general from 1 to 5 mol, preferably from 1 to 2 mol, of alkyne of the formula (VI) or alkene of the formula (VH) are employed per mole of the halopyrazolylcarboxanilide of the formula (V). 25
Suitable diluents for carrying out the process e) 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 decaline; halogenated hydrocarbons,
30 such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform,
carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran,

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1,2-dimethoxyetbane, 1,2-diethoxyethane or anisol; nitriles, such as acetonitriJe,
propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-
dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-
methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate
5 or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; sulphones, such as
sulpholane; alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane- 1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether.
10 The process e) according to the invention is, if appropriate, carried out in the
presence of a suitable acid acceptor. Suitable acid acceptors are all customary strong bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides or alkali metal hydrocarbon compounds, such as, for example, sodium hydride, sodium hydroxide, potassium hydroxide, sodium amide,
15 lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-
butoxide, methyl lithium, phenyl lithium or butyl lithium.
When carrying out the process e) according to the invention, the reaction
temperatures can be varied within a relatively wide range. In general, the process is
20 carried out at temperatures of from -80°C to 150°C, preferably at temperatures of
from -30°C to 80°C.
For carrying out the process e) according to the invention for preparing compounds
of the formula (I), in general from 1 to 5 mol, preferably from 1 to 2 mol, of
25 phosphorus compound of the formula (IX) are employed per mole of the ketone of
the formula (Vm).
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 ~
30 in general between 0.1 bar and 10 bar.

Le A 35 503-Foreign Countries
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The substances according to the invention have potent microbicidal activity and can be employed for controlling undesirable microorganisms, such as fungi and bacteria, in crop protection and in the protection of material.
5 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,
10 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:
15 Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
20 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;
25 Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
30 (conidia form: Drechslera, syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);

Le A 35 503-Foreign Countries
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Uromyces species, such as, for example, Uromyces appendicular^;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
5 Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
10 Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae; and
Pseudocercosporella species, such as, for example, Pseudocercosporella
15 herpotrichoides.
/ The active^compounds according to the invention also have very good fortifying
Action in plants. Accordingly, they can be used for mobilizing the defences of the
plant against attack by undesirable microorganisms. 20
In the present context, plant-fortifying (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defence system of plants such that, when the treated plants are subsequently inoculated with undesirable microorganisms, they show substantia] resistance against these
25 microorganisms.
In the present case, undesirable microorganisms are to be understood as meaning
phytopathogenic fungi, bacteria and viruses. Accordingly, the substances according
to the invention can be used to protect plants for a certain period after the treatment
30 against attack by the pathogens mentioned. The period for which protection is
provided generally extends over 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.

Le A 35 503-Foreign Countries
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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. 5
The active compounds according to the invention can be used with particularly good results for controlling cereal diseases, such as, for example, agairist Pyrenophora species, and diseases in viticulture, and in fruit and vegetable growing, such as, for example, against Altemaria or Podosphaera species. 10
The active compounds according to the invention are also suitable for increasing the jj yield of crops. In addition, they show reduced toxicity and are well tolerated by v plants.
15 At certain concentrations and application rates, the active compounds according to
the invention can also be used as herbicides, for influencing plant growth and for controlling animal pests. They can also be used as intermediates and precursors for the synthesis of further active compounds.
20 The active compounds according to the invention can be used to treat all plants and
parts of plants. By plants are understood here 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
25 combinations of these methods, including the transgenic plants and including the
plant varieties which can or cannot be protected by varietal property rights. 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
30 and also roots, tubers and rhizomes. Parts of plants also include harvested plants and
vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

Le A 35 503-Foreign Countries
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The treatment of the plants and the parts of plants with the active compounds
according to the invention is>carried out directly or by action on their surroundings,
habitat or storage space, according to customary treatment methods, for example by
5 dipping, spraying, evaporating, atomizing, broadcasting, spreading-on and, in the
case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.
In the protection of materials, the compounds according to the invention can be.
10 employed for protecting industrial materials against infection with, and destruction
by, undesired 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
15 materials which are intended to be protected by active compounds according to the
invention from microbial change or destruction can be adhesives, 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
20 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 adhesives, sizes, paper and board, leather, wood, paints, cooling lubricants and heat-transfer liquids particularly preferably wood. 25
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),
30 and against slime organisms and algae.
Microorganisms of the following genera may be mentioned as examples:

Le A 35 503-Forejgn Countries
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Alternaria, such as Altemaria tenuis,
Aspergillus, such as Aspergillus niger,
Chaetomium, such as Chaetomium globosum,
5 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,
10 Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, and Staphylococcus, such as Staphylococcus aureus. 15
Depending on their particular physical and/or chemical properties, the active
compounds can be converted to the customary formulations, such as solutions,
emulsions, suspensions, powders, foams, pastes, granules, aerosols and
microencapsulations in polymeric substances and in coating compositions for seeds,
20 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 surfactants, that is
25 emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it
is also possible to employ, for example, organic solvents as auxiliary solvents.
Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or
alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such
as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons
30 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 isobuty] ketone or cyclohexanone, strongly polar solvents such as

Le A 35 503-Foreign Countries
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dimethylformarnide 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
5 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 carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or
10 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 foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,
15 arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example
lignosulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the
form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and
20 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,
25 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 percent by weight of active ]
30 compound, preferably between 0.5 and 90%. ]

Le A 35 503-Foreign Countries
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The active compounds according to the invention can be used as such or in their
formulations, also 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,
5 i.e. the activity of the mixture is greater than the activity of the- individual
components.
Examples of suitable mixing components are the following:
10 Fungicides:
aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole,
azoxystrobin,
benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos,
15 binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate,
buthiobate,
calcium polysulphide, carpropamide, capsimycin, captafol, captan, carbendazim,
carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, chloroneb,
chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil,
20 cyproconazole, cyprodinil, cyprofuram,
debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran,
diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,
diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon,
dodemorph, dodine, drazoxolon,
25 edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,
famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamide, fenitropan,
fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,
ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol,
flusilazole, flusulphamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-
30 sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
furconazole-cis, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole,

Le A 35 503-Foreign Countries
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imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione, iprovalicarb, irumamycin, isoprothiolane, isovaledione,
kasugamycin, kresoxim-methy], copper preparations, such as: copper hydroxide,
5 copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper
and Bordeaux mixture,
mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl,
metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,
mildiomycin, myclobutanil, myclozolin,
10 nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,
ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,
paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin,
pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone,
propamocarb, propanosine-sodium, propiconazole, propineb, pyraclostrobin,
15 pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,
quinconazole, quintozene (PCNB), quinoxyfen, sulphur and sulphur preparations, spiroxamines,
tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole, thiabendazole,
thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl,
20 tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole,
tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole,
validamycin A, vinclozolin, viniconazole,
zarilamide, zineb, ziram and also
25 Dagger G, OK-8705, OK-8801,
a-( 1,1 -dimethylethy])~(3-(2-phenoxyethy])-1H-1,2,4-triazole-1 -ethanol,
a-(2,4-dichlorophenyl)-(3-fluoro-(3-propyl-lH-l,2,4-triazole-l-ethanol,
a-(2,4-dichlorophenyl)-P-methoxy-a-methyl-lH-l,2,4-triazole-l-ethanol,
a-(5-methyl-l,3-dioxan-5-yl)-p-[[4-(trifluoromethyl)-pheny]]-methylene]-lH-l,2,4-
30 triazole-1-ethanol,
(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(lH-l,2,4-triazol-l-yl)-3-octanone,

Le A 35 503-Foreign Countries
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(E)-a-(methoxyimino)-N-methyI-2~phenoxy-phenyIacetamide,
l-(2,4-dichlorophenyl)-2-(lH-l,2,4-triazol-l-yl)-ethanoneO-(phenylmethyl)-oxime,
l~(2~methyM~naphthaIenyI)-lH-pyrrole-2,5-dione,
l-(3,5-dichIorophenyl)-3-(2-propenyl)~2,5-pyiro]idinedione,
5 l~[(diiodomethy])-su]phony]]-4-methy]-benzene,
l-[[2-(2,4-dich]orophenyl)-l,3-dioxolan-2-yl]-methyl]-lH-imidazo]e,
l-[[2-(4-chlorophenyl)-3-phenyloxiranyl]'methylj-lH-l,2,4-triazo]e,
l-[l-[2-[(2,4-dichlorophenyl)'methoxy]-pheny]]-etheny]]-lH-imidazole,
l-methy]-5-nony]-2-(pheny]methy])-3-pyrroIidino]e,
10 2' ,6' -dibromo-2-methyl-4' -trifluoromethoxy-4' -trifluoro-methyl- i ,3-thiazole-
5-carboxanj]ide,
2,6-dichloro-5-(methy]thio)-4-pyrimidiny]-thiocyanate,
2,6-dichloro-N-(4-trifluoromethy]benzy])-benzamide,
2,6-dichJoro-N-f[4-(trifluoromethyl)-pheny]]-methy]]~benzarnide,
15 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,
2-[(l-methylethy])'SulphonyI]-5-(trichloromethyl)-l,3,4-thJadiazole,
2-[[6-deoxy-4-0-(4-0-methyl-(3-D-g]ycopyranosy])-a-D-glucopyranosyl]-amino]-4-
raethoxy-lH-pyrro]o[2,3-d]pyrimidine-5-carbonitrile,
2-aminobutane,
20 2-bromo-2-(bromomethy])-pentanedinitrile,
2-chloro-N-(2,3-dihydro-l,l,3~trimethyl~lH-inden-4-yl)-3-pyridinecarboxamide, 2-chloro-N-(2,6-dimethylpheny])-N-(isothiocyanatomethyl)~acetamide, 2-pheny]pheno] (OPP),
3,4-dich]oro-l-[4-(dif]uoromethoxy)-phenyl]-lH-pyrro]e-2,5-dione,
25 3,5-dich]oro-N-[cyano[(l-methy]~2'propyny])-oxy]-methyl]-benzamide,
3-(l,l-dimethyIpropyl-l'Oxo-lH-indene-2-carbonitri]e, 3-[2-(4-chlorophenyl)~5'ethoxy-3-isoxazolidinyl]-pyridine,
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-lH-imidazo]e-l-sulphonamide,
4-methyl-tetrazolo[l,5-a]quinazolin-5(4H)-one,
30 8-hydroxyquinoline sulphate,
9H-xanthene~2-[(phenylamino)-carbony]]-9~carboxylic hydrazide,

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bis-(l-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,
cis-l-(4-chlorophenyl)-2-(lH-l,2,4~triazol-l-yl)-cycloheptanol,
cis-4-[3-[4-(l,l-dimethylpropy])-pheny]-2-methy]propyl]-2,6-dimethyl-morpholine-
hydrochloride,
5 ethyl [(4-chlorophenyl)-azo]-cyanoacetate,
potassium hydrogen carbonate, methanetetrathiol sodium salt,
methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yI)-lH-imidazoIe-5-carboxylate,
methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)~DL-alaninate,
10 methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)'DL-aIaninate,
N-(2,6-dimethy]phenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,
N-(2,6-dimethylpheny])-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,
N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,
N-(4-cyclohexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine,
15 N-(4-hexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine,
N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2~oxo-3-oxazolidinyl)-acetamide,
N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,
N-[2,2,2-trichloro-l-[(chloroacetyl)-amino]-ethyl]-benzamide,
N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N'-methoxy-methanimidamide,
20 N-forrrryl-N-hydroxy-DL-alanine-sodium salt,
0,0-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,
O-methyl S-phenyl phenylpropylphosphoramidothioate,
S-methyl 1,2,3-benzothiadiazole-7-carbothioate,
spiro[2H]-1 ~benzopyrane-2,1 '(3 'H)-isobenzofuran]-3 '-one,
25 4-[(3,4-dimethoxyphenyl)-3~(4-fluorophenyl)-acryloyl]-morpholine.
-Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin,
30 octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin,
tecloftalam, copper sulphate and other copper preparations.

Le A 35 503-ForeiCT Countries
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Insecticides / acaricides / nematicides:
abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb, aldoxycarb, alpha-
cypermethrin, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin,
5 azamethiphos, azinphos A, azinphos M, azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiemis,
baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb,
bensultap, benzoximate, betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin,
biopermethrin, bistrifluron, BPMC, bromophos A, bufencarb, buprofezin,
10 butathiofos, butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb,
chlorethoxyfos, chloifenapyr, chlorfenvinphos, chlorfluazuron, chlormephos,
chlorpyrifos, chlorpyrifos M, chlovaporthrin, chromafenozide, cis-resmethrin,
cispermethrin, clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,
15 cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin,
cyromazine,
deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon,
dichlorvos, dicofol, diflubenzuron, dimethoat, dimethylvinphos, diofenolan,
disulfoton, docusat-sodium, dofenapyn,
20 eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp., esfenvalerate,
ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,
fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim,
fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate,
fipronil, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,
25 flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,
furathiocarb, granulosis viruses,
nalofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,
imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
30 nuclear polyhidrosis viruses,
lambda-cyhalothrin, lufenuron,

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malathion, mecarbam, metaldehyde, methamidophos, Metharhizium anisopliae,
Metharhizium flavoviride, methidathion, methiocarb, methoprene, methomyl,
methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin,
monocrotophos,
5 naled, nitenpyram, nithiazine, novaluron,
omethoate, oxamyJ, oxydemethon M,
Paecilomyces fumosoroseus, parathion A, parathion M, permethrin, phenthoate,
phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos A,
pinmiphos M, profenofos, promecarb, propargite, propoxur, prothiofos, prothoat,
10 pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion,
pyrimidifen, pyriproxyfen, quinalphos, ribavirin,
salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep, sulprofos,
tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron,
15 tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, tetradifon theta-
cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam
hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,
triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon,
triflumuron, trimethacarb,
20 vamidothion, vaniliprole, Verticilhum lecanii,
YI5302, Zeta-cypermethrin, Zoiaprofos
(lR-cis)-[5-(pheny]methy])-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-
furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxyIate,
(3-phenoxyphenyl)-niethyl-2,2,3,3-tetramethylcyclopropanecarboxylate,
25 l-[(2-chloro-54hiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-l,3,5-triazine-
2(lH)-imine,
2-(2-chloro-6-fluoropheny])-4-[4-(l,l-dimethylethyl)phenyl]-4,5-dihydro-oxazole, 2-(acetyloxy)-3-dodecyl-l,4-naphthalenedione,
2-chloro-N-[[[4-(l-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,
30 2-chloro-N-[[t4-(2,2-dich]oro-l,l-difluoroethoxy)-phenyl]-amino]-carbonyl]-
benzamide, 3-methylphenyl propylcarbamate

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4-[4-(4-ethoxyphenyl)-4-methylpentyl]~l-fluoro-2-phenoxy-benzene,
4-chloro-2-(l,l-dimethylethy])-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyIJthio]-
3(2H)-pyridazinone,
4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-
5 pyridazinone,
4-ch]oro-5-[(6-chloro-3-pyridiny3)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-
pyridazinone,
Bacillus thuringiensis strain EG-2348,
[2-benzoyl-l-(l,l-dimethylethyl)-hydrazinobenzoic acid,
10 2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-l-oxaspiro[4.5Jdec-3-en~4~yl butanoate,
[3-[(6-ch]oro-3-pyridiny])methyl]-2-thiazolidiny]idene]~cyanamide,
dihydro-2-(nitromethylene)-2H-I,3-thiazine-3(4H)-carboxaldehyde,
ethyl [2-[[l,6-dihydro-6-oxo-l-(phenylmethy])-4-pyridaziny]]oxy]ethyl]-carbamate,
N-(3,4,4-trifluoro-l-oxo-3"buteny])-glycine,
15 N-(4-chloropheny])-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-lH-
pyrazole-1-carboxamide,
N-[(2-chloro-5~thiazolyl)methyl]-N'-methyl-N"-nitro-guanidine,
N-methyl-N'-(I-methyl-2-propenyl)-l,2-hydrazinedicarbothioamide,
N-methyl-N'-2-propenyl-l,2-hydrazinedicarbothioamide,
20 0,0-diethyl [2~(dipropylamino)-2-oxoethyl]-ethy]phosphoraniidothioate,
N-cyanomethyl-4-trifluoromethyl-nicotinamide,
3,5-dichloro~l-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifIuoromethy]pyridine-2-yloxy)-propoxy]-benzene.
25 A mixture with other known active compounds, such as herbicides, or with fertilizers
and growth regulators, 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
30 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

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Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi by no means limits the mycotic spectrum covered, but is only for illustration.
5 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, wettable
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
10 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
15 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
20 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 with active compounds according to the invention. In a preferred embodiment, wild plant
25 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 genetical engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of
30 plants" or "plant parts" has been explained above.

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„44_
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
5 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,
10 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
15 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)
20 which are preferably 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,
25 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
30 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,

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cotton, 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 and oilseed rape. Traits that are emphasised are in particular increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), CryHA, CrylUA, CryHIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasised are the increased defence of the plants to 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 sulphonylurea, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plants 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 formula (I) according to the

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invention. The preferred ranges stated above for the active compounds also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds specifically mentioned in the present text.

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47
Preparation Examples
Example 1

^^s

(M)

Process (a):
A mixture of 382.6 mg (2 mmol) of 2-(l,3,3-trimethy]butyl)aniline, 353.2 mg
10 (2 mmol) of 5-fIuoro-l,3-dimethyl-IH-pyrazol-4-carbonyI chloride and 276.4 mg
(2 mmol) of potassium carbonate in 25 ml of acetonitrile is stirred at room
temperature overnight. 30 ml of saturated ammonium chloride solution are added,
and the mixture is extracted with 30 ml of ethyl acetate. The combined organic
phases are dried over magnesium sulphate and concentrated under reduced pressure.
15 The residue is chromatographed on silica gel using cyclohexane/ethyl acetate
(starting with pure cyclohexane and finally with 80% ethyl acetate).
This gives 280 mg (42% of theory) of 5-fluoro-l,3-dimethy]-N-[2-(l,3,3-trimethylbutyl)phenyI]-lH-pyrazol-4-carboxamide of melting point 78 - 80°C.

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Example 2

(1-2)

Process (b)

10

In the presence of 500 mg of 5% Pd/C, 540 mg (1.792 mmol) of N-[2-(l-ethenylpropyl)phenyl]-5-fluoro-l ,3-dimethyl-lH-pyrazol-4-carboxamide (1-24) in 50 ml of methanol are hydrogenated under a hydrogen pressure of 100 bar at 80°C for 5 hours. The catalyst is filtered off, the filter residue is washed with 2 x 50 ml of methanol and the motherliquor is concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate 4:1.

15

This gives 150 mg (30% of theory) of N»[2-(l-ethy]propyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide as pale yellow crystals.

HPLC: logP = 3.01

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Example 3

N CH3 CH,
CH,

5 Processes (c) and (b) as tandem reaction
At room temperature, 450 mg (1.41 mmol) of N-[2-(l-ethyl-l-hydroxypropy])~
pheny]]-5-fluoro-l,3-dimethy]-lH-pyrazo]-4~carboxamide (IV-l) in 10 ml of
dichloromethane are, after addition of 1.6g (14.1 mmol) of trifluoroacetic acid and
10 0.16 g (1.41 mmol) of triethylsilane, stirred for 1 hour. The reaction solution is
adjusted to pH 7 using saturated sodium bicarbonate solution and the organic phase is separated off, dried over magnesium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate 4:1.
15
This gives 120 mg (20% of theory) of N-[2~(l-ethylpropyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide as pale yellow crystals.
HPLC: logP = 3.01
20

Le A 35 503-Foreign Countries
-50-Example 4

5 Process (d)
0.718 g (2mmol) of the iodoanilide 5-fluoro-N~(2-iodophenyl)-l,3-dimethyl-lH-pyrazoJ-4-carboxamide, 0.25 g (2.5 mmol) of l,l-difluoro~2-viny]cyc}opropane and 0.33 ml (2.4 mmol) of triethylarnine are dissolved in 4 ml of dimethylformamide, and
10 argon is then passed through the reaction solution for 5 minutes. 20 mg (0.09 mmol)
of palladium acetate are then added, and the mixture is stirred at 100°C in a closed airtight vessel for 16 hours. After the reaction has ended, the mixture is applied to a silica cartridge and eluted with ethyl acetate. The eluate is admixed with activated carbon, filtered and concentrated under reduced pressure. The residue is
15 chromatographed on silica gel using cyclohexane/ethyl acetate (3:1 to 1:1).
This gives 154 mg (23% of theory) of N-{2-[2-(2,2-difluorocyclopropyl)ethenyl]-phenyl}-5-fluoro-l ,3-dimethyl-lH-pyrazol-4-carboxamide.
20 HPLC: logP = 2.59

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51
Example 5

(1-4)

5 Process (e):
227 mg (0.55 mmol) of n-butyltriphenylphosphonium bromide are suspended in 2 ml of tetrahydrofuran and, at ~30°C, 0.34 m] (0.55 mmol) of an n-BuLi solution in hexane are added and the mixture is stirred at this temperature for 20 min. A
10 suspension of 138 mg (0.5 mmol) of N-(2-acetylphenyl)-5-fluoro-l,3-dimethyl-lH-
pyrazol-4-carboxamide in 2 ml of tetrahydrofuran is then added, and the mixture is stirred without further cooling for 16 hours. 3 ml of water are added, and the mixture is extracted 3 times with in each case 20 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated under reduced pressure.
15 The residue is chromatographed on silica gel using cyclohexane/ethyl acetate (5:1 to
1:1).
This gives 17 mg (10% of theory) of 5-fluoro-l,3-dimethy]-N-[2-(l-methyl-l-hexenyl)phenyl] -1 H-pyrazol -4-carboxami de.
20
HPLC: logP = 4.36

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The compounds of the formula (I) listed in Table 1 below are obtained analogously to Examples 1 to 5 and in accordance with the statements in the general descriptions of the processes.

Ex. No.

Compound

logP

m.p. (°C)

1-5

1-6

114

HaC-N'
1-7

92-94

1-8

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53

Ex. No.

Compound

logP

m.p. (°C)

1-9

4.36

132-134

1-10

3.37

109-111

1-11

1-12

97

1-13

143

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Ex. No.

Compound

logP

m.p, (°C)

H3C-N
1-14

H3C CH3

151

1-15

CH,

M6

4.11

155-157

1-17

3.01

84-87

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56

Ex. No.

Compound

JogP

m.p. (°C)

1-23

2.57

1-24

-CH,

3.45

1-25

3.82

111-13

CH3 o
1-26

3.67

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Ex. No . Compound logP m.p. (°C)
1-27 CH3 o H3C F yCH3 3.82
1-28 CH3 0
H3C F
H3C" t ^1
CH3 ^CH3 3.73
1-29 CH3 0 |M A JL A^
H3C^N^F ^^Y CH3
H3C 3.74
1-30 H3C v r
tH3 5.29
1-31 CH3O rj^N
H3C F ^> A
r CH3
H3C
.-— - — — — 3.85

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63
Preparation of the intermediates
Example (IV-1)

H3C

Process (f):
At room temperature, 358.5 mg (2 mmol) of 3~(2-aminophenyI)-3-pentanol and
10 353.2 mg (2 mmol) of 5-fluoro-lt3-dimethyl-lH-pyrazol-4-carbonyl chloride are
stirred with 276.4 mg (2 mmol) of potassium carbonate in 15 ml of acetonitrile for 16
hours. 30 ml of saturated ammonium chloride solution are added, and the mixture is
then extracted with 30 ml of ethyl acetate. The combined organic phases are washed
with 30 ml of concentrated sodium chloride solution, dried over magnesium sulphate
15 and concentrated under reduced pressure. The residue is chromatographed on silica
gel using cyclohexane/ethyl acetate (starting with pure cyclohexane and finally with 80% ethyl acetate).

20

This gives 350 mg (45% of theory) of N-[2-(l-ethyl- 1-hydroxypropyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide as colourless crystals.

HPLC: logP = 2.47

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The compounds of the formula (IV) listed in Table 2 below are obtained analogously to Example (IV-l) and in accordance with the statements in the general descriptions of the process.

Ex. No.

Compound

logP

m.p. (°C)

IV-2

2.4

158

O
IV-3

H3Q
h
NN^ ^F

H3C

-CK

3.13

CH,

IV-4

3.1

227

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-67
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Example (V-l)

5 Process (g):
A mixture of 5.86 g (42 mmol) of potassium carbonate and 6.2 g (28.3 mmol) of 2-iodoaniline in 100 ml of acetonitrile is stirred at room temperature for 10 min. A solution of 5 g (28.3 mmol) of 5-fIuoro-l,3-dimethyI-lH-pyrazoI-4-carbonyl chloride
10 in 10 ml of acetonitrile is added slowly, and the mixture is stirred under reflux for 16
hours. The reaction mixture is concentrated under reduced pressure, and 200 ml of ethyl acetate and 100 ml of water are added. The organic phase is separated off and the aqueous phase is extracted 3 times with 200 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated under reduced
15 pressure. The residue is stirred in 50 ml of ether.
This gives 4.78 g (47% of theory) of 5-fluoro-N-(2-iodophenyl)-l,3-dimethyl-lH-pyrazol-4-carboxamide.
20 HPLC: logP = 2.44

68-
Le A 35 503-Foreign Countries
Example (Vffl-1)

5 Process (h):
A solution of 8g (45 mmol) of 5-fluoro-l,3-dimethyl-lH-pyrazol-4-carbonyl chloride in 30 ml of acetonitrile is added to a mixture of 10.4 g (76 mmol) of potassium carbonate and 5.1 g (38 mmol) of 2-aminoacetophenone in 40 ml of
10 acetonitrile, and the mixtured is stirred at 80°C for 16 hours. The reaction mixture is
concentrated under reduced pressure, and 200 ml of ethyl acetate and 70 ml of water are added. The organic phase is separated off and the aqueous phase is extracted 3 times with 200 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated under reduced pressure. The residue is filtered
15 through a silica gel cartridge using dichloromethane, the filtrate is concentrated under
reduced pressure and the crude product is saturated with diisopropyl ether.
This gives 2.5 g (24% of theory) of N-(2-acetylphenyl)-5-fluoro-l,3-dimethyl-lH-pyrazol-4-carboxamide. 20
HPLC:logP = 2.15

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The JogP values given in the preparation examples and tables above are determined in accordance with EEC Directive 79/831 Annex VA8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C 18). Temperature: 43°C.
5 The determination is carried out in the acidic range at pH 2.3 using the mobile phases
0.1% aqueous phosphoric acid and acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
The calibration is carried out using unbranched alkan-2-ones (having 3 to 16 carbon
10 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 detennined in the maxima of the chromatographic signals using the UV spectra from 200 nm to 400 nm. 15

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-70-Use examples: Example A
5 Pyrenophora teres test (barley) / protective
Solvent: 25 parts by weight of N,N-dimethylacetamide
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether
10 To produce a suitable preparation of active compound, 1 part by weight of active
compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
(.Tojest for protective activity, young plants are sprayed with the preparation of active
15 compound at the stated application rate. After the spray coating has dried on, the plants
are sprayed with a conidia suspension of Pyrenophora teres. The plants remain in an incubation cabin at 20°C and 100% relative atmospheric humidity for 48 hours.
The plants are then placed in a greenhouse at a temperature of about 20°C and a relative
20 atmospheric humidity of about 80%.
Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 25
In this test, for example, the compounds 16 and 17 of the Preparation Examples exhibit, at an application rate of 250 g/ha, an efficacy of 95% or more. j

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Table A
Pyrenophora teres test (barley) / protective

Active compound according to the invention Application rate
of active compound in
g/ha Efficacy in%

(16)

250

100

(17)

250

100

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-72-Example B
Podosphaera test (apple) / protective
5 Solvent: 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
10 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, the plants
15 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 carried out 10 days after the inoculation. 0% means an efficacy which
20 corresponds to that of the control, whereas an efficacy of 100% means that no infection
is observed.
-J
In this test, for example, the compounds 9, 16, 17 and 18 of the Preparation Examples exhibit, at an application rate of 100 g/ha, an efficacy of 90% or more.
25

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73
Table B Podosphaera test (apple) / protective

Active compound according to the invention Application rate
of active compound
ing/ha Efficacy in%
.

(9)

100

90

(16)

100

100

(17)

100

100

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-74-
Podosphaera test (apple) / protective

Active compound according to the invention Application rate
of active compound
ing/ha Efficacy in%

(18)

100

100

Le A 35 503-Foreign Countries
-75-Example C
Alternaria test (tomato) / protective
5 Solvent: 49 parts by weight of N,N-dimethylformarnide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active
compound is mixed with the stated amounts of solvent and emulsifier, and the
10 concentrate is diluted with water to the desired concentration.
To test for protective activity, young tomato plants are sprayed with the preparation of
active compound at the stated application rate. 1 day after the treatment, the plants are
inoculated with a spore suspension of Alternaria solani and then remain at 100% rel.
15 humidity and 20°C for 24 h. The plants then remain at 96% rel. atmospheric humidity
and a temperature of 20°C.
Evaluation was carried out 7 days after the inoculation. 0% means an efficacy which
corresponds to that of the control, whereas an efficacy of 100% means that no infection
20 is observed.
In this test, for example, the compounds 16, 17 and 20 of the Preparation Examples exhibit, at an application rate of 750 g/ha, an efficacy of 90% or more. 1 \ ^ -
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Table C
Alternaria test (tomato) / protective

Active compound Application rate Efficacy
of active compound ing/ha in %

(16)

750

95

(H)

750

95

(20)

750

100

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77
Patent claims
1. Pyrazolylcarboxanilides of the formula (I)

5

(I),

in which
R1 represents hydrogen, cyano, halogen, nitro, Cj-C4-alkyl, Cj~C4-
haloalkyl having 1 to 5 halogen atoms, C3-C6-cycloalkyl, Cj-C,^-
10 alkoxy, CrC4-haloalkoxy having 1 to 5 halogen atoms, CrC4-
alkylthio, Cj-C4-haloalkylthio having 1 to 5 halogen atoms or aminocarbonyl-C]"C4-alkyl,
R2 represents hydrogen, Ci-C4-alkyl, Cj-Cg-haloalkyl having 1 to 5
15 halogen atoms, C2-C6-alkenyl, C3-C6-cycloalky], Ci-C4-alkylthio-Cj-
C4-alkyl, Ci-C4-haloalkylthio-CrC4-alkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy-Ci-C4-alkyl or CpQ-haloalkoxy-Cj-C^-alkyl having 1 to 5 halogen atoms,
20 G represents halogen or CrC4-alkyl,
G furthermore represents Cs-C^-alkyl,
R3 represents unsubstituted C^^rj-alkyl or represents Ci-C2n-alkyl
25 which is mono- or polysubstituted by identical or different substituents

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from the group consisting of halogen and/or C3-C6-cycloalkyl or represents C2-C2o-alkenyl or C2-C2o-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C5-cycloalkyl, where the cycloalkyl moiety for its part may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or Cj-C^alkyl and
10
n represents 0, 1 or 2.
2. Pyrazolylcarboxanilides of the formula (I) according to Claim 1, in which
G represents halogen or CrC4-alkyl,
15 andR],R2,R3and n are as defined in Claim 1.
3. Pyrazolylcarboxanilides of the formula (I) according to Claim 1, in which
R1 represents hydrogen, cyano, halogen, nitro, Cj-C^alkyl, CrC4-
20 haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C3-
Cg-cycloalky], Cj-C4-alkoxy, CpC^haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, Ci-Q^-alkylthio, C]-C4-haloalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms or aminocarbonyl-Cj-C4-alkyl, 25
R2 represents hydrogen, Ci-C4-alkyl, C]-C6-haloalkyl having 1 to 5
fluorine, chlorine and/or bromine atoms, C2-C6-alkenyl, C3-C6
cycloalkyl, C1-C4-alkylthio-C1-C4-alkyl, CrC4-haloalkylthio-CrC4-
alky] having 1 to 5 fluorine, chlorine and/or bromine atoms, Cj-C4-
30 alkoxy-Ci-C4-alkyl or Ci-C4-haloalkoxy-Cj-C4-alkyl having 1 to 5
fluorine, chlorine and/or bromine atoms,

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G represents halogen or C j-C4-alkyl,
G furthermore represents Cs-Ce-alkyl,
5 R3 represents unsubstituted C2-C12-a]kyl or represents C2-C]2-a]ky]
which is mono- to tetrasubstituted by identical or different substituents
from the group consisting of fluorine, chlorine, bromine and/or C3-C6-
cycloalkyl or represents C2-Cj2-a]kenyl or C2-Cj2-alkynyl, each of
which is optionally mono- to tetrasubstituted by identical or different
10 substituents from the group consisting of fluorine, chlorine, bromine
and/or C3-C6-cycloalkyl, where the moiety for its part may optionally be mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen and/or Cj-C4-alkyl,
15 n represents 0, 1 or 2.
4. Pyrazolylcarboxanilides of the formula (I) according to Claim 3, in which
G represents halogen of Ci-Chalky],
20
1 -\ -i
andR\Rz,RJand n are as defined in Claim 3.
5. Pyrazolylcarboxanilides of the formula (I) according to Claim 1, in which
25 R1 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
trifluoromethyl or trifluoroethyl,
R2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl or trifluoroethyl, 30
G represents fluorine, chlorine or methyl,

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G furthermore represents ethyl or t-butyl,
G furthermore represents 2,4-dimethylbutyl,
R3 represents in each case straight-chain or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl or decynyl, each of which may be attached at any position and each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl,
n represents 0, 1 or 2.
6. Pyrazolylcarboxanilides of the formula (I) according to Claim 5, in which
G represents fluorine, chlorine or methyl,
and R1, R2, R3 and n are as defined in Claim 5.
7. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims
1 to 6 in which
R1 represents methyl and
R2 represents methyl.
8. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims
1 to 7, in which

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R3 represents unsubstituted C2-C2o-alkyl (preferably C2-C12-alkyl, particularly preferably C2-C6~alkyl).
9. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims
5 1 to 8, in which
n represents 0.
10. Pyrazolylcarboxanilides of the formula (I) according to one or more of Claims
10 1 to 9, in which
R1 represents methyl,
R2 represents methyl,

15
20

R3 represents unsubstituted C2-C2o-alkyl (preferably C2-Ci2-alkyl, very particularly preferably C2-C6-alkyl),
n represents 0.
11. Process for preparing compounds of the formula (I) according to Claim 1, characterized in that
a) carboxylic acid derivatives of the formula (II)

25

(n),

in which

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82
R1 and R2 are as defined in Claim 1 and
X represents halogen,
are reacted with an aniline derivative of the formula (HI)

in which
10
G, R3 and n are as defined in Claim 1,

r *■■
,-2A
lus^-p ■ if appropriate in the presence of an acid binder*and if appropriate in
the presence of a diluenu or (£p
15 0
b) pyrazolylcarboxanilides of the formula (la)

& >_ da).
^f F
u
R
in which
20 Hf^
RJ,R2, G and n are as defined in Claim 1, ,>■•;-/",'"

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83

R4 represents C2-C2o-alkenyl or C2-C20-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C4-alkyl,
are hydrogenated, if appropriate in the presence of a diluent and if
f
appropriate in the presence of a catalyst, or - A
6

10 c) hydroxyalkylpyrazolylcarboxanilidesof the formula (IV)

(IV),

in which
15 R1, R2, G and n are as defined in Claim 1,
R5 represents C2-C20-hydroxyalkyl which is optionally
additionally mono- or polysubstituted by identical or different
substituents from the group consisting of halogen and/or C3-
20 Cg-cycloalkyl, where the cycloalkyl moiety for its part may
optionally be substituted by halogen and/or Cj-C^alkyl,
' -■'■■ .,../. : //.Y^-V^ , /') «■
r
r'i S
-"'iiwvY
/ ;
is dehydrated, if appropriate in the presence of a diluenWand if
appropriate in the presence of an acid or *$f t./
25

Le A 35 503-Foreign Countries
-84
d) halopyrazolylcarboxanilides of the formula (V)

in which 5
R1, R2, G and n are as defined in Claim 1,
Y represents bromine or iodine,
10 are reacted with an alkyne of the formula (VI)
HC^—R6 (VI), in which
15 R6 represents C2-Ci8-a]kyl which is optionally mono- or
polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C^alkyl,
20
or an alkene of the formula (VH)

Le A 35 503-Foreign Countries
85
in which
R7, R8 and R9 independently of one another each represent hydrogen
or alky] which is optionally mono- or polysubstituted by
5 identical or different substituents from the group consisting of
halogen and/or C3-C6-cycloalky], where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Cj-C4-alkyl and where the total number of carbon atoms of the open-chain moiety does not exceed the number 20,
if appropriate in the presence of a diluent, if appropriate in the
presence of an acid binder/jand in the presence of one or more
catalysts, or ,1 )
&
15 e) ketones of the formula (VET)

(Vm),

in which
20 R1, R2, G and n are as defined in Claim 1,
R10 represents hydrogen or Ci-Cjg-alkyl which is optionally mono-or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-Cg-cycloalkyl,

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-86
where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or CrC4-alkyl,
are reacted with a phosphorus compound of the general formula (IX)
5
R^—PX (IX),
in which
R11 represents hydrogen or Cj-Cjg-alky] which is optionally mono
10 or polysubstituted by identical or different substituents from
the group consisting of halogen and/or C3-C6-cyc]oalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C4-a]ky] and
15 Px represents a grouping -P+(C6H5)3 CI", -P+(C6H5)3 Br-,
-P+(C6H5)31*, -P(=0)(OCH3)3 or -P(=0)(OC2H5)3, if appropriate in the presence of a diluent,^)
/ •, ^!-.-- :-: ty" U,A,^ ■-■^t>-& ;\& "•■- •
12. Compositions for controlling undesirable microorganisms, characterized in
20 that they comprise at least one pyrazolylcarboxanilide of the formula (I)
according to Claim 1, in addition to extenders and/or surfactants.
13. Use of pyrazolylcarboxanilides of the formula (I)~~a~ccording to Claim 1 for
controlling undesirable microorganisms.
25
14. Method for controlling undesirable microorganisms, characterized in that pyrazolylcarboxanilides of the formula-CIXaccording to Claim 1 are applied to the microorganisms and/or their habitat.

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87
15. Process for preparing compositions for controlling undesirable microorganisms, characterized in that pyrazolylcarboxanilides of the formula (I) according to Claim 1 are mixed with extenders and/or surfactants.
16. Hydroxyalkylpyrazolylcarboxanilides of the formula (IV)

(IV),
in which
10 R1, R2, G and n are as defined in one or more of Claims 1 to 7 and
R5 represents C2-C2o-hydroxyalkyl which is optionally additionally
mono- or polysubstituted by identical or different substituents from the
group consisting of halogen and/or C3-C6-cycloalkyl, where the
15 cycloalkyl moiety for its part may optionally be substituted by halogen
and/or Cj-C^alkyl.
17. Process for preparing hydroxyalkylpyrazolylcarboxanilides of the formula (IV) according to Claim 13, characterized in that

20

f) carboxylic acid derivatives of the formula (II)

Le A 35 503-Foreign Countries
88

(II),
in which
R1 and R2 are as defined in Claim 1 and
X represents halogen,
are reacted with a hydroxyalkylanihne derivative of the formula (X)

in which
R3, G and n are as defined in Claim 1,
R5 represents C2-C2rj-hydroxyaIkyl which is optionally additionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3-Cg-cycloalkyl, where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or Ci-C4-alkyl,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
18. Halopyrazolylcarboxanilides of the formula (V)

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-89

5
10

■l„K «
R2
in which
R1, R2, G and n are as defined in one or more of Claims 1 to 7 and
Y represents bromine or iodine.
19. Process for preparing halopyrazolyicarboxanilides of the formula (V) according to Claim 14, characterized in that
g) carboxylic acid derivatives of the formula (II)

in which

15
R1 and R2 are as defined in Claim 1,
X represents halogen,
20 are reacted with a haloaniline of the formula (XI)

Le A 35 503-Foreign Countries
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(XI),
in which
G and n are as defined in Claim 1,
Y represents bromine or iodine,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.

10
20. Ketones of the formula (VIH)

(VUI),

in which
15
R1, R2, G and n are as defined in one or more of Claims 1 to 7 and
R10 represents hydrogen or Cj-Ci8-alkyl which is optionally mono- or
polysubstituted by identical or different substituents from the group
20 consisting of halogen and/or C3-C6-cycloalkyl, where the cycloalkyl
moiety for its part may optionally be substituted by halogen and/or Cp C4-alkyl.

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21. Process for preparing ketones of the formula (VAT) according to Claim 17, characterized in that
h) carboxylic acid derivatives of the formula (IF)

cn).
R in which
10 R1 and R2 are as defined in Claim 1,
X represents halogen,
are reacted with ketoanilines of the formula (XII) 15

20

in which
G and n are as defined in Claim 1,
R10 represents hydrogen or Cj-C^-alkyl which is optionally mono-or polysubstituted by identical or different substituents from the group consisting of halogen and/or C3~C6-cycloalkyl,

Le A 35 503-Foreign Countries
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where the cycloalkyl moiety for its part may optionally be substituted by halogen and/or CpC^alkyl,
if appropriate in the presence of an acid binder and if appropriate in
5 the presence of a diluent.

93
22. Pyrazolylcarboxanilides of the formula I substantially as herein described with reference to the foregoing examples.
Dated this on 03rd day of December, 2008
(PA$AL KALRA)
OF REMFRY AND SAGAR
ATTORNEY FOR THE APPLICANTS

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Patent Number

270102

Indian Patent Application Number

2533/MUM/2008

PG Journal Number

49/2015

Publication Date

04-Dec-2015

Grant Date

27-Nov-2015

Date of Filing

03-Dec-2008

Name of Patentee

BAYER AKTIENGESELLSCHAFT

Applicant Address

D-51368 LEVERKUSEN, GERMANY.

Inventors:

#	Inventor's Name	Inventor's Address
1	HANSLUDWIG ELBE	DASNOCKEL 59, 42329 WUPPERTAL, GERMANY.
2	RALF DUNKEL	KRISCHER STR. 22, 40789 MONHEIM, GERMANY.
3	ASTRID MAULER MACHNIK	NEUENKAMPER WEG 48, 42799 LEICHLINGEN, GERMANY.
4	KARL HEINZ KUCK	PASTOR-LOH-STR, 30A, 40764 LANGENFELD, GERMANY.
5	HEIKO RIECK	GUDRUNSTR. 4, 40764 LANGENFELD, GERMANY.
6	QIN ZHU OHLBACH	ERFTSTR. 28, 40219 DUSSELDORF, GERMANY.
7	ULRIKE WACHENDORFF NEUMANN	OBERER MARKENWEG 85, 56566 NEUWIED, GERMANY.

PCT International Classification Number

A61K31/415; A61P31/04; C07D231/14

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	101 36065.7	2001-07-25	Germany