MXPA06008883A - Haloalkyl carboxamides for controlling micro-organisms - Google Patents

Abstract

The invention relates to novel haloalkyl carboxamides of formula (I), in which R, R1, R2, R3, R4, M and A are defined as cited in the description, to several methods for producing said substances and to their use for controlling undesirable micro-organisms. The invention also relates to novel intermediate products and to the production of the latter.

Description

HALOGENOALQUILCARBOXAMIDAS FOR THE FIGHT AGAINST MICROORGANISMS FIELD OF THE INVENTION The present invention relates to novel haloalkylcarboxylates, various processes for their preparation and their use for the control of undesirable microorganisms. BACKGROUND OF THE INVENTION It is already known that a large number of carboxamides have fungicidal properties - (see publications, for example WO 03/010149, WO-02/059086, EP-A 0 824 099, EP-0 737 682, EP-A 0 591 699, EP-A 0 * 589 301, EP-A 0 545 099, DE-A 24 09 011, DE-A 20 06 472, JP-A 2001-302605, JP-A 10-251240, JP-A 8-176112, JP-A 8-92223 and JP-A 53-72823). Thus, a large number of alkylcarboxamides, which are not substituted in the alkyl part, are already known, such as, for example, N-allyl-N- [2- (1,3-dimethylbutyl) phenyl] -l-methyl -3- (trifluoromethyl) -lH-pyrazole-4-carboxamide by the publication WO 02/059086, N- [2- (1,3-dimethylbutyl) phenyl] -2,4-dimethyl-l, 3-thiazole- 5-carboxamide by EP-A 0 824 099 and 5-fluoro-1,3-dimethyl-N- [2- (1,3,3-trimethylbutyl) phenyl] -lH-pyrazole-4-carboxamide by the WO 03/010149. The activity of these products is good, however it leaves much to be desired in some cases, for example on occasion of small quantities REF: 174780 application. DETAILED DESCRIPTION OF THE INVENTION New haloalkylcarboxamides of the formula (I) have now been found wherein R means hydrogen or halogen, R 1 signifies hydrogen or methyl, R 2 signifies methyl, ethyl or halogenoalkyl with 1 to 4 carbon atoms, with 1 to 9 fluorine, chlorine and / or bromine atoms, R 3 means halogen or halogenalkyl with 1 to 4 carbon atoms, with 1 to 9 fluorine, chlorine and / or bromine atoms, R4 means hydrogen, alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) Caryl-C 1 -alkyl 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-alkyl- with 1 to 3 carbon atoms, halogen- (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl, respectively 1 to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 8 alkyl) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C akalkyl) 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms) carbonyl, (halogencycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R5, -CONR6R7 or -CH2NR8R9, means hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms- alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, "R7" means, independently of each other, hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms; carbon, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms, with, respectively, 1 to 9 fluorine atoms, chlorine and / or bromine, R7, together with the nitrogen atom, with which they are bound, form a saturated heterocycle, with 5 to 8 atoms in the substituted ring, optionally one or more times, in the same way or in different forms by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle comprising 1 or 2 more heteroatoms, non-contiguous, of the series consisting of oxygen, sulfur or NR 10, R 8 and R 9 mean, independently of each other, hydrogen, alkyl having 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms, with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R8 and R9 also form, together with the nitrogen atom , with which they are bound, a saturated heterocycle, with 5 to 8 atoms in the substituted ring, optionally one or more times, in the same or in different forms by halogen or by alkyl with 1 to 4 carbon atoms, contain the heterocycle 1 or 2 heteroatoms more, not contiguous, of the series formed by oxygen, sulfur or NR10, R10 means hydrogen or alkyl having 1 to 6 carbon atoms, M means a ring of phenyl, pyridine or pyrimidine, pyridazine or pyrazine monosubstituted, respectively, by R11 or means a thiazole ring substituted by R1: L "A7 R11 means hydrogen, fluorine, chlorine, methyl, iso-propyl, methylthio or trifluoromethyl, R11_A means hydrogen, methyl, methylthio or trifluoromethyl, A means the rest of the formula (Al) R 12 denotes hydrogen, cyano, halogen, nitro, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cycloalkyl with "-" 3 to 6 atom. carbon, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-alkyl with 1 to 4 carbon atoms carbon, R13 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms, R14 means hydrogen, alkyl with 1 to 4 carbon atoms, hydroxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, haloalkyl or with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or phenyl, or A means the rest of the formula (A2) R15 and R16 stand for hydrogen independently, halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, R17 is halogen, cyano or alkyl having 1 to 4 carbon atoms; carbon, or halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the remainder of the formula (A3) R18 and R19 are independently hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R20 is hydrogen, halogen, alkyl having 1 to 4 carbon atoms; carbon or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A4) R21 means hydrogen, halogen, hydroxy, cyano, alkyl with 1 to 6 carbon atoms, halogen alkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to - ''. carbon or halogenalkylthio atoms with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the remainder of the formula (A5) R22 means halogen, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 atoms of carbon or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R23 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, alkylsulfinyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 atoms of carbon, or A means the rest of the formula (A6) R24 means -alkyl with 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R25 means alkyl with 1 to 4 carbon atoms, Q1 means S (sulfur), O (oxygen) , SO, S02 or CH2, p means 0, 1 or 2, meaning R25 identical or different residues, when p means 2, or A means the rest of the formula (A7) R2S means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of formula (A8) R27 means alkyl with 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or means the remainder of the formula (A9) R28 and R29 mean, independently of one another, hydrogen, halogen, amino, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, R30 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or means the remainder of the formula (AlO) R31 and R32 mean, independently of one another, hydrogen, halogen, amino, nitro, alkyl having 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms, with 1 to 5 halogen atoms, R33 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (All) R34 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) amino, cyano, alkyl with "1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms. carbon with 1 to 5 halogen atoms, R35 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A12) R36 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (C 1 -C 4 -alkyl) amino, cyano, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R37 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A13) R38 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A14) R39 means hydrogen or alkyl having 1 to 4 carbon atoms, R40 means halogen or alkyl having 1 to 4 carbon atoms, or A means the remainder of the formula (A15) R41 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A16) CC (A16), in which R42 means hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, or means the remainder of the formula (A17) R43 means halogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, haloalkylthio with 1 to 4 carbon atoms. carbon or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the remainder of the formula (A18) R44 means hydrogen, cyano, alkyl with 1 to 4 carbon atoms, halogen alkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms, hydroxy-alkyl having 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms) aminosulfonyl, alkylcarbonyl with 1 to 6 carbon atoms or means substituted phenylsulfonyl or benzoyl respectively, if appropriate, R4S means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R46 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R47 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means rest of the formula (A19) R48 means alkyl with 1 to 4 carbon atoms. It has also been found that the haloalkylcarboxamides of the formula (I) are obtained, if a) carboxylic acid derivatives of the formula (II) or AX (II) are reacted in which A has the meanings indicated above and X 1 means halogen or hydroxy, with an aniline derivative of the formula (III) in which R, R 1, R 2, R 3, R 4 and M have the meanings given above, optionally in the presence of a catalyst, optionally in the presence of a condensation agent, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or b) hexylcarboxanilides of the formula (Ia) are reacted wherein R, R1, R2, R3, M and A have the meanings given above, with halides of the formula (IV) R4 ^ -Y2 RX (IV) in which X2 means chlorine, bromine or iodine, R "A means alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms carbon, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-alkyl with 1 a 3 carbon atoms, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-alkyl with, respectively, 1 to 13 fluorine, chlorine and / or bromine atoms; (alkyl with 1 to 8 carbon atoms) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 4 alkoxy-alkyl with 1 to 4 carbon atoms) carbonyl, (cycloalkyl with 3 to 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms) carbonyl, (halogenocycloalkyl with 3 a 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R5, -C0NR6R7 or -CH2NR8R9. having R5, R6, R7, R8 and R9 the meanings indicated above, in the presence of a base and in the presence of a diluent. Finally, it has been found that the novel haloalkylcarboxamides of the formula (I) have very good microbicidal properties and that they can be used for combating undesirable microorganisms both in the protection of plants and in the protection of materials. The compounds according to the invention can optionally be present as mixtures of the various possible isomeric forms, especially stereoisomers, such as, for example, the E and Z isomers, threo and erythro, as well as the optical isomers. , if necessary, however, also of tautomers. Both the E isomers and also the Z isomers are claimed, as well as the threo and erythro isomers, as well as the optical isomers, arbitrary mixtures of these isomers, as well as the possible tautomeric forms.

The haloalkylcarboxamides, according to the invention, are generally defined by the formula (I). The definitions of the preferred residues of the preceding formulas and cited below have been given below. These definitions are valid in an equivalent way for the final products of the formula (I) as well as for all the intermediate products. R preferably means hydrogen, fluorine, chlorine or bromine. R is particularly preferably hydrogen.

R is also particularly preferably fluorine or chlorine. R1 preferably means hydrogen. R1 also means methyl preferably. R2 preferably means methyl, ethyl or means methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. - butyl substituted, respectively, once or several times, in the same or in different ways by fluorine, chlorine or bromine. R 2 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, fluoro-methyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluoride-chloromethyl, difluoro-chloromethyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2, 2, 2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2-chloro-2, 2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl. R 2 very particularly preferably means methyl, ethyl or trifluoromethyl. R 2 is particularly preferably methyl. R2 also means ethyl acetate in particular. R2 also means, in a particularly preferred manner, trifluoromethyl. R3 preferably means fluorine, chlorine, bromine, iodine or means methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. -butyl substituted, respectively, one or several times, in the same or different ways by fluorine, chlorine or bromine. R3 means especially preferred forraa means fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, fluoro-methyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluoride-chloromethyl, difluoro-chloromethyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2, 2 , 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2-chloro-2, 2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, 1 -chlorobutyl, heptafluor-n-propyl or heptafluoroisopropyl. R3 is chloro or trifluoromethyl very particularly preferred. R3 is particularly preferably chlorine. R3 is also, particularly preferably, trifluoromethyl. R4 it preferably means hydrogen, alkyl having 1 to 6 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 _ carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms-alkyl with 1 at 3 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) Caryl-C 1 -alkyl 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-alkyl with, respectively, 1 up to 13 volumes of fluorine, chlorine and / or bromine; (C 1 -C 6 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl) carbonyl, (C 3 -C 3) -alkyl 6 carbon atoms) carbonyl; (halogenalkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 6 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R5, -CONR6R7 or -CH2NR8R9. - especially preferred hydrogen, methyl, ethyl, n- or iso-propyl, n- refers to forraa, iso-, sec.- or tere. -butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, * n-, iso-, sec.- or tere. -butylsulfinyl, methylsulfonyl, ethylsulphonyl, n- or iso-propylsulfonyl, n-, iso-, sec.- or tere. -butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethyl-sulphonyl, trifluoromethyl-sulfonyl, trifluoromethoxymethyl.; formyl, -CH2-CHO, - (CH2) 2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH (CH3) 2, - (CH2) 2-CO-CH3, - (CH2) 2-CO-CH2CH3, - (CH2) 2-CO-CH (CH3) 2, -CH2-C02CH3, -CH2-C02CH2CH3, -CH2-C02CH (CH3 ) 2, - (CH2) 2-C02CH3, - (CH2) 2-C02CH2CH3, - (CH2) 2-C02CH (CH3) 2, -CH2-CO-CF3, -CH2-C0-CC13, -_ -CH2- CO-CH2CF3, -CH2-C0-CH2CC13, - (CH2) 2-CO-CH2CF3, - (CH2) 2-C0-CH2CC13, -CH2-C02CH2CF3, -CH2-C02CF2CF3, -CH2-C02CH2CC13, -CH2-C02CC12CC13, - (CH2) 2-C02CH2CF3, - ( CH2) 2-C02CF2CF3, - (CH2) 2-C02CH2CCl3, - (CH2) 2-C02CC12CC13; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, tere. -butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tere. -butoxycarbonyl, cyclopropylcarbonyl; trifluoromethylcarbonyl, trifluoromethoxycarbonyl, or -C (= 0) C (= 0) R5, -C0NRsR7 or -CH2NR8R9. very particularly preferably hydrogen, methyl, methoxymethyl, formyl, -CH2-CH0, - (CH2) 2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-C0-CH (CH3) 2, -C (= 0) CH0, -C (= 0) C (= 0) CH3, -C (= 0) C (= 0) CH2OCH3, -C (= 0) C02CH3, -C (= 0) C02CH2CH3. it preferably means hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms. R5 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tere. -butyl, methoxy, ethoxy, n- or iso-propoxy, tere. -butoxy, methoxymethyl, cyclopropyl; trifluoromethyl, trifluoromethoxy. Re and R7 stand for each other preferably hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl having 1 to 3 carbon atoms, cycloalkyl having 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine atoms and / or bromine. R6 and R7 also form, together with the nitrogen atom, with which they are bonded, preferably a saturated heterocycle, with 5 or 6 atoms in the substituted ring, optionally, from one to four times, in the same or different forms by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms more non-contiguous, of the series formed by oxygen, sulfur or NR10. R6 and R7 signify independently, particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere. -butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R6 and R7 also form, together with the nitrogen atom, with which they are linked, with particular preference. a saturated heterocycle, of the series consisting of morpholine, thiomorpholine or piperazine, optionally substituted, one to four times, in the same or different forms by fluorine, chlorine, bromine or methyl, the piperazine being substituted on the second nitrogen atom by R. R8 and R9 are independently, preferably independently, hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms, with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms. R8 and R9 also form, together with the nitrogen atom, with which they are linked, preferably a saturated heterocycle, with 5 or 6 ring atoms, optionally substituted one or more times, in the same or in different ways by halogen or by alkyl having 1 to 4 carbon atoms, the heterocycle comprising 1 or 2 more, non-contiguous heteroatoms of the series formed by oxygen, sulfur or NR10. R8 and R9 mean, independently of one another, especially preferably hydrogen, methyl, ethyl, n- or iso-propyl, Ti-, iso-, sec.- or tere. -butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R8 and R9 also form, together with the nitrogen atom, with which they are bonded, a particularly preferred saturated heterocycle of the series consisting of morpholine, thiomorpholine or piperazine, optionally substituted from one to four times, the same or in different forms by fluorine, chlorine, bromine or methyl, the piperazine being able to be substituted on the second nitrogen atom by R10. R10 preferably denotes hydrogen or alkyl having 1 to 4 carbon atoms. R 10 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. - Butyl M preferably means one of the following cycles M-l M-2 M-3 M-4 M-5 M-6 M-7 M-8 M-9 M-10 M-ll the linkage marked with "*" being linked to the amide, the bond marked "#" with the halogenoalkyl moiety.

M is particularly preferably a cycle selected from M-1, M-2, M-3, M-6, M-7 and M-8. M means very particularly preferably the cycle M-l. M also means, very particularly preferably, the heterocycle M-2. M also means, very particularly preferably, the heterocycle M-3. M also means, very particularly preferably, the heterocycle M-6. M also means, very particularly preferably, the heterocycle M-7. M also means, very particularly preferably, the heterocycle M-8. R11 preferably means hydrogen, fluorine, chlorine, methyl or trifluoromethyl. R 11 is particularly preferably hydrogen or chlorine. R11 means, in the case where M means M-2, M-3, M-4 or M-5, more preferably fluorine, the fluorine being particularly preferably in the 6-position (M-2, M-3) or in position 3 (M-4, M-5). R11 means, in the case where M means M-2, M-3, M-4 or M-5, in addition, preferably chlorine, the chlorite being particularly preferred in "position 6 (M-2, M- 3) or in position 3 (M-4, M-5) R11 means, in the case where M means M-2, M-3, M-4 or M-5, in addition, preferably methyl, being the methyl is particularly preferably in the 4-position (M-2) or in the 3-position (M-3, M-4, M-5) .R11 means, in the case where M means M-6, in addition, preferably methyl, with methyl being particularly preferred in the 3-position. R 11 in the case where M means M-6, in addition, preferably trifluoromethyl, the trifluoromethyl being particularly preferably in the 3-position. R 11 means, in the case in which M means M-9, moreover, preferably methyl, with the especially preferred forrane methyl in the 4-position.

R11 means, in the case where M means M-9, in addition, preferably trifluoromethyl, wherein the forrane trifluoromethyl is especially preferred in the 4-position. R11 means, in the case where M means M-10, in addition, preferably methyl, methyl is particularly preferably in the 3-position, R11 signifies, in the case where M means M-10, in addition, preferably trifluoromethyl, the trifluoromethyl being particularly preferably in the 3-position. R11 means, in the case of M is also M-11, preferably methyl, with methyl being particularly preferred in the 3-position. R11, in the case where M means M-II, is also preferably trifluoromethyl, with trifluoromethyl being particularly preferred. in position 3. R1: L ~ A preferably means hydrogen. R1: L "A moreover preferably denotes methyl • ßii-A further denotes, preferably trifluoromethyl A preferably means one of the residues Al, A2, A3, A4, A5, A6, A9, AlO, All, A12, A16, A17 or A18. A is particularly preferably one of the radicals Al, A2, A3, A4, A5, A6, A9, All, A16, A17, A18. Al very particularly preferably means the radical Al. In addition, very particularly preferably means the radical A2. In addition, very particularly preferably means the remainder A3. In addition, from a very particularly preferred fora means the remainder A4. In addition, very particularly preferably means the rest A5. In addition, very particularly preferably means the rest A6. In addition, very particularly preferably means the rest A9. In addition, from a very especially preferred fora means the remainder All. In addition, very particularly preferably means the rest A16. In addition, from a very especially preferred forra, means the rest A17. In addition, from very especially preferred fora means the remainder A18. R12 preferably denotes hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, halogenalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl atoms.

R12 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl / methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio. R12 very particularly preferably means hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R12 particularly preferably means methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl. R 13 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio.

R 13 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine or methyl. R13 very particularly preferably means hydrogen, fluorine, chlorine or methyl. R 14 preferably denotes hydrogen, methyl, ethyl, n-propyl, iso-propyl, halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl. R 14 is particularly preferably hydrogen, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl. R 14 very particularly preferably means hydrogen, methyl, trifluoromethyl or phenyl. R 14 is methyl preferably particularly preferred. R1S and R1S stand for, independently of one another, preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R15 and R16 mean, independently of one another, of especially preferred forra, hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R15 and R16 signify, independently of one another, very especially preferred forra, meaning hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 15 and R 16 are particularly preferably hydrogen. R17 preferably denotes fluorine, chlorine, bromine, cyano, methyl, ethyl, halogenalkyl having 1 to 2 carbon atoms or halogenalkoxy having 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms . R 17 is particularly preferably fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R 17 very particularly preferably means fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy. R 17 is methyl in particular preferred. R18 and R19 independently of each other preferably means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R18 and R19 signify independently, particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R18 and R19 mean independently, very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluonomethyl or trichloromethyl. R18 and R19 are particularly preferably hydrogen.

R20 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R20 means especially preferred forraa means hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl. R20 is methyl, especially highly preferred. R21 is preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, halogen with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms or halogenalkylthio with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms. R2X is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluorothoxy, difluorochloromethoxy, trieloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio. R21 is particularly preferred for hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl. R21 is particularly preferably iodo, methyl, difluoromethyl or trifluoromethyl. R22 preferably denotes fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2. carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms. R22 is especially preferred fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec. -butyl, tere. - butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R22 very particularly preferably means fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 23 is preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with , respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, alkylsulfinyl with 1 to 2 carbon atoms or alkylsulfonyl with 1 to 2 carbon atoms.

R 23 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, iso-propyl, n-butyl, iso-butyl, sec. -butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulfonyl. R 23 very particularly preferably means hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, iso-butyl, sec. -butyl, tere. -butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulfinyl or methylsulfonyl. R23 is particularly preferably hydrogen. R 24 is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 24 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 25 is preferably methyl or ethyl. R 25 is methyl preferably especially preferred. Q1 preferably means S (sulfur), S02 or CH2.

Q1 means especially preferred forrae S (sulfur) or CH2 Q1 very particularly preferably means S (sulfur). p preferably means 0 or 1. p is particularly preferably 0. R2S is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R2e means methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl especially from forra. R 26 very particularly preferably means methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R27 is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 27 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R27 is methyl, trifluoromethyl, difluoromethyl or trichloromethyl especially highly preferred. R28 and R29 mean, independently of one another, preferably hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R28 and R29 mean, independently of one another, especially preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R28 and R29 signify independently, very particularly preferably, hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R28 and R29 are particularly preferably hydrogen. R 30 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms. R 30 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 30 very particularly preferably means hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 30 is particularly preferably methyl. R 31 and R 32 stand for, independently of one another, preferably hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 31 and R 32 independently of each other are especially preferably hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R31 and R32 are independently, very particularly preferably, hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R 31 and R 32 are particularly preferably hydrogen. R33 means hydrogen preferentially, fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenoalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R33 is particularly preferably hydrogen, fluorine, chlorine, bromine , iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R33 very particularly preferably means hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R33 means methyl preferably particularly preferred. R34 is preferably hydrogen, fluorine, chlorine, bromine, amino, alkylamino having 1 to 4 carbon atoms, di (alkyl having 1 to 4 carbon atoms) amino, cyano, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R34 is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R34 is particularly preferred for hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R34 means forraa particularly ... preferred amino, methylamino, dimethylamino, methyl or trifluoromethyl. R 35 is preferably fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R3? particularly preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 35 very particularly preferably means fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R3B means methyl, trifluoromethyl or difluoromethyl particularly preferred forra.

R36 preferably represents hydrogen, fluorine, chlorine, bromine, amino, alkylamino having 1 to 4 carbon atoms, di (alkyl having 1 to 4 carbon atoms), amino, cyano, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R3e is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R3e means, very particularly preferably, hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R3e is particularly preferably amino, methylamino, dimethylaraine, methyl or trifluoromethyl. R 37 is preferably fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R37 is especially preferred fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 37 very particularly preferably means fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R 37 is particularly preferably methyl, trifluoromethyl or difluoromethyl. R38 is preferably fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R38 is especially preferred for fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R38 stands for fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl very particularly preferably. R39 preferably denotes hydrogen, methyl or ethyl. R 39 is particularly preferably methyl. R 40 is preferably fluorine, chlorine, bromine, methyl or ethyl, R 40 is particularly preferably fluorine, chlorine or methyl. R41 is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R41 is especially preferred methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R41 is methyl, trifluoromethyl, difluoromethyl or trichloromethyl, especially highly preferred.

R41 is particularly preferably methyl or trifluoromethyl. R42 preferably denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or . _. bromine. R42 is particularly preferred for hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl. R43 preferably denotes fluorine, chlorine, bromine, iodine,:. hydroxy, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine atoms , chlorine and / or bromine. R 43 is particularly preferably fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec. -butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R43 is particularly preferred as fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R44 preferably denotes hydrogen, methyl, ethyl, halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, alkoxy with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms , hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl. R44 is particularly preferably hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl. R44 is methyl or methoxymethyl very particularly preferred. R45 preferably means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 45 is particularly preferred for hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl. R45 is hydrogen or methyl, which is very particularly preferred. R46 preferably denotes hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 4 S is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 4 S very particularly preferably means hydrogen, methyl, difluoromethyl or trifluoromethyl. R47 preferably denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R47 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl. R47 very particularly preferably means hydrogen. R48 is preferably methyl, ethyl, n-propyl or isopropyl. R48 is particularly preferably methyl or ethyl. Preference is given to those compounds of the formula (I), in which all the radicals have, respectively, the meanings indicated above in a preferred manner. Especially preferred are those compounds of the formula (I), in which all the radicals have, respectively, the meanings indicated above, with particular preference. Preferably and, respectively, as a partial quantity of the aforementioned compounds of the formula (I), the following groups of the novel carboxamides are to be understood: Group 1: haloalkylcarboxamides of the formula (I-a) wherein R, R1, R2, R3, M and A have the meanings indicated above. Group 2: haloalkylcarboxamides of the formula (I-b) wherein R, R1, R2, R3, R4_A, M and A have the meanings indicated above. R 4"A preferably denotes alkyl having 1 to 6 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms, alkylsulfonyl having 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl having 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 with 3 carbon atoms-C 1 -C 3 -alkyl, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms: formyl, formyl-alkyl with 1 to 3 carbon atoms, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-C 1 -C 3 -alkyl; alkyl with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 át carbon atoms, halogen- (C 1 -C 3 alkoxy) carbonyl-C 1 -C 3 -alkyl with, respectively, 1 to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 6 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl) carbonyl, (C 3 -C 3) -alkyl 6 carbon atoms) carbonyl; (halogenalkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 6 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R5, -CONRsR7 or -CH2NR8R9. R 4"A" is particularly preferably methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere-butyl, pentyl or hexyl, methylsulphinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tere. -butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethyl-sulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; formyl, -CH2-CHO, - (CH2) 2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH (CH3) 2, - (CH2) 2-CO-CH3, - (CH2) 2-CO-CH2CH3, - (CH2) 2-CO-CH (CH3) 2, -CH2-C02CH3, -CH2-C02CH2CH3, -CH2-C02CH (CH3 ) 2, - (CH2) 2-C02CH3, - (CH2) 2-C02CH2CH3, - (CH2) 2-C02CH (CH3) 2, -CH2-CO-CF3, -CH2-C0-CC13, -CH2-CO- CH2CF3, -CH2-C0-CH2CC13, - (CH2) 2-CO-CH2CF3, - (CH2) 2-C0-CH2CC13, -CH2-C02CH2CF3, -CH2-C02CF2CF3, -CH2-C02CH2CC13, -CH2-C02CC12CC13, - (CH2) 2-C02CH2CF3, - ( CH2) 2-C02CF2CF3, - (CH2) 2-C02CH2CCl3, - (CH2) 2-C02CC12CC13; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, tere. -butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tere. -butoxycarbonyl, cyclopropylcarbonyl; trifluoromethylearbonyl, trifluoromethoxycarbonyl, or -C (= 0) C (= 0) R5, -C0NRsR7 or -CH2NR8R9.

R4"A stands for especially highly preferred forraa means methyl, methoxymethyl, formyl, -CH2-CH0, - (CH2) 2 -CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH ( CH3) 2, -C (= 0) 010, -C (= 0) C (= 0) CH3, -C (= 0) C (= 0) CH2OCH3, -C (= 0) C02CH3, -C (= 0) C02CH2CH3 Group 3: haloalkylcarboxamides of the formula (Ic) wherein R, R1, R2- ,; R3, R4, R11 and A have the meanings indicated above. Preference is given to haloalkylcarboxamides of the formula (I-c), in which R 4 is hydrogen. Preference is given to the haloalkylcarboxamides of the formula (I-c), in which R 11 is hydrogen. Preference is given to the haloalkylcarboxamides of the formula (I-c), in which R 4 and R 11 are hydrogen, respectively. Group 4: haloalkylcarboxamides of the formula (I-d) wherein R, R1, R2, R3, R4, R11 and A have the meanings indicated above.

Preference is given to the haloalkylcarboxamides of the formula (I-d), in which R 4 is hydrogen. Preference is given to the haloalkylcarboxamides of the formula (I-d), in which R 11 is hydrogen. Preference is given to haloalkylcarboxamides of the formula (I-d), in which R 4 and R 11 are hydrogen, respectively. Group 5: haloalkylcarboxamides of the formula (I-e) wherein R, R1, R2, R3, R4, R11 and A have the meanings indicated above. Preference is given to the haloalkylcarboxamides of the formula (I-e), in which R 4 is hydrogen. Preference is given to haloalkylcarboxamides of the formula (I-e), in which R 11 is hydrogen. Preference is given to haloalkylcarboxamides of the formula (I-e), in which R 4 and R 11 are hydrogen, respectively. Group 6: haloalkylcarboxamides of the formula (I-f) (I-f) in which R, R1, R2, R3, R4, R11 and A have the meanings indicated above. Preference is given to the haloalkylcarboxamides of the formula (I-f), in which R 4 is hydrogen. Preference is given to the haloalkylcarboxamides of the formula (I-f), in which R 11 is hydrogen. Preference is given to haloalkylcarboxamides of the formula (I-f), in which R 4 and R 11 are hydrogen, respectively. Group 7: haloalkylcarboxamides of the formula (I-g) wherein R, R1, R2, R3, R4, R11-A and A have the meanings indicated above. Preference is given to haloalkylcarboxamides of the formula (I-g), in which R 4 is hydrogen. Preference is given to haloalkylcarboxamides of the formula (I-g), in which R 11 is hydrogen. Preference is given to the haloalkylcarboxamides of the formula (I-g), in which R 4 and R 1: L "A stand for hydrogen, respectively Group 8: haloalkylcarboxamides of the formula (I-h) (I-h) in which R, R1, R2, R3, R4, RX1 'and A have the meanings indicated above. Preferred are the haloalkylcarboxamides of the formula (I-h), wherein R 4 is hydrogen. Preference is given to the haloalkylcarboxamides of the formula (I-h), in which R 11 is hydrogen. Preference is given to the haloalkylcarboxamides of the formula (Ih), in which R4 and R?:? "A" respectively represent hydrogen The compounds of the formula (I) (and also of the groups 1 to 8) must be mentioned, Figure imgf000014_0001 Figure imgf000010_0001 Figure imgf000012_0001 Figure imgf000012_0001 Figure imgf000012_0001 Figure imgf000012_0001 Figure imgf000012_0001 Figure imgf000012_0001 Figure imgf000032_0001 Figure imgf000032_0001 Figure imgf000032_0001 Figure imgf000032_0001 Figure imgf000014_0001 Figure imgf000046_0001 1 to 8), wherein R 4 means -C (= 0) C (= 0) R 5, R 5 having the meanings indicated above The saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can be, even in combination with heteroatoms, such as, for example, in alkoxy, respectively straight-chain or branched chain, as far as possible The substituted radicals can be mono- or polysubstituted, the substituents being the same or different in the case of polysubstitutions. All the dialkylamino definition also embraces an amino group substituted asymmetrically by alkyl such as for example methyl ethylamino. The radicals substituted by halogen, such as, for example, halogenoalkyl, are mono- or polyhalogenated.In the case of several halogenations, the halogen atoms can be the same or different, in this case halogen means fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine The definitions of the remains or the explanations indicated above in a general manner or indicated in the preferred ranges can be combined arbitrarily between the corresponding intervals and the preferred ranges., correspondingly, for the starting products and for the intermediate products. In particular, the compounds mentioned in groups 1 to 6 can be combined both with the general meanings as well as with the preferred, especially preferred, meanings, etc., all combinations between the preferred ranges being also possible here in each case. Description of the process, according to the invention, for the preparation of the hexylcarboxanilides of the formula (I) as well as the intermediates. Procedure (a) If 2-trifluoromethylbenzoyl chloride and 4-chloro-2- ( 4, 4, 4-trifluoro-3-methyl-butyl) -phenylamine as starting materials, the process (a) according to the invention can be represented by means of the following formula scheme: The carboxylic acid derivatives, which are necessary as starting materials for carrying out process (a), according to the invention, are defined, in general, by means of formula (II). preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned for A as preferred, as being especially preferred or very particularly preferred in connection with the description of the compounds, according to the invention, of the formula (I) Preferably X1 means chlorine, bromine or hydroxy The carboxylic acid derivatives of the formula (II) are for the most part known and / or can be prepared according to processes known per se (see WO publications). 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313). The aniline derivatives, which are also necessary as starting materials for carrying out process (a), according to the invention, are defined, in general, by means of formula (III). In this formula (III), R, R1, R2, R3, R4 and M preferably have, preferably or very particularly preferably those meanings which have already been mentioned for these residues as preferred, especially preferred or as very particularly preferred in relation to the description of the compounds of the formula (I), according to the invention. The aniline derivatives of the formula (III) are new. The aniline derivatives of the formula (Ill-a) in which R, R1, R2, R3, R4"A and M have the meanings indicated above, are obtained, if c) are reacted aniline derivatives of the formula (Ill-b) wherein R, R1, R2, R3 and M have the meanings indicated above, with halides of the formula (IV) R "A-X2 (IV) in which R4" A and X2 have the meanings indicated above, in the presence from a base and in the presence of a diluent. The aniline derivatives of the formula (III-c) wherein R, R1, R2 and R3 have the meanings indicated above, if (d) aniline derivatives of the formula (Ill-d) are reacted; in which R, R, R and R have the meanings indicated above, R 11"-5 denotes fluorine or chlorine, in the presence of a reducing agent, a catalyst and a diluent The aniline derivatives of the formula (Ill-e) ) wherein R, R2 and R3 have the meanings indicated above, R11"0" means fluorine, chlorine, methyl, iso-propyl, methylthio or trifluoromethyl, if (e) haloalkanoalkanones of the formula (V) are reacted wherein R, R2, R3 and R11"0 have the meanings given above, with hydrazine or hydrazine hydrate in the presence of a base (for example alkali metal or alkaline earth metal hydroxides such as sodium hydroxide or potassium hydroxide) and, if appropriate, in the presence of a diluent The halogenoalkanonanilines of the formula (V) wherein R, R2, R3 and R11-c have the meanings given above, are obtained, if f) protected halogenoalkanonanilines of the formula (VI) are reacted (VI) in which R, R2, R3 and R1: L ~ C have the meanings given above, SG means a protective group, preferably Piv (tere.-butylcarbonyl), Boc (tere.-butoxycarbonyl), Cbz (benzyloxycarbonyl), trifluoroacetyl, Fmoc (9-fluorenylmethoxycarbonyl) or Troc (2,2,2-trichloroethoxycarbonyl), in the presence of an acid (for example hydrochloric acid) and, if appropriate, in the presence of a diluent. The protected halogenoalkanonanilines of the formula (VI) in which R, R2, R3, R11-c and SG have the meanings indicated above, there is obtained, if g) protected anilines of the formula (VII) are reacted wherein R11_c and SG have the meanings indicated above, with an ester of the formula (VIII) in which R, R2 and R3 have the meanings indicated above, R49 means alkyl with 1 to 4 carbon atoms, preferably methyl or ethyl , in the presence of a diluent and organometallic bases. The protected anilines of the formula (VII) and the esters of the formula (VIII) are known. The aniline derivatives of the formula (Ill-f) wherein R, R2, R3 and R11"0 have the meanings given above, are obtained, if h) alkenes of the formula (IX) are hydrogenated wherein R, R2, R3 and R11"0 have the meanings indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst.

The alkenes of the formula (IX) wherein R, R2, R3 and R11-0 have the meanings indicated above, are obtained, if i) dehydrogenated hydroxyalkylanilines of the formula (X) wherein R, R 2, R 3 and R 11"0 have the meanings given above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid The hydroxyalkylanilines of the formula (X) wherein R, R2, R3 and R11-c have the above-indicated meanings, if (k) haloalkanoalkonanilines of the formula (V) are reacted in which R, R2, R3 and R11'0 have the meanings stated above indicated, with organometallic compounds (for example methylmagnesium halides) in the presence of a diluent. The aniline derivatives of the formula (Ill-g) wherein R, R1, R2 and R3 have the meanings given above, MA means, a ring of pyridine or pyrimidine monosubstituted, respectively, by R11 or means a thiazole ring monosubstituted by R11_A, can be obtained analogously or in accordance with known procedures (see EP-A 0 737 682). Procedure (b) If 3- (difluoromethyl) -1-methyl-N- [2- (4,4,4-trifluoro-3-methylbutyl) phenyl] -lH-pyrazole-4-carboxamide and chlorine ( oxo) ethyl acetate as starting materials, the development of process (b), according to the invention, can be represented by means of the following formula scheme: The hexylcarboxanilides, necessary as starting materials for carrying out process (b), according to the invention, are defined, in general, by means of formula (I-a). In this formula (Ia), R, R1, R2, R3, M and A preferably have, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, as being especially preferred or very particularly preferred. Preferred for these residues in relation to the description of the compounds of the formula (I), according to the invention. The hexylcarboxanilides of the formula (I-a) are also compounds according to the invention and constitute the subject of this application. These can be obtained according to process (a), according to the invention, (with R1 = hydrogen). The halides, which are also necessary as starting materials for carrying out process (b), according to the invention, are defined, in general, by means of formula (IV). In this formula (IV), R 4"A preferably has, particularly preferably or very particularly preferably those meanings which have already been mentioned as being preferred, as being especially preferred or very particularly preferred for the latter in connection with the Description of the compounds of the formula (Ib), 'according to the invention Preferably X 2 means chlorine or bromine The halides of the formula (IV) are known Reaction conditions As diluents for carrying out the process (a) All inert organic solvents are suitable according to the invention, preferably aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane. , benzene, toluene, xylene or decalin, halogenated hydrocarbons, such as for example chloroben for example, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl-tert. -butyl ether, methyl-tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide. Process (a), according to the invention, is carried out, if appropriate, in the presence of a suitable acid acceptor. As such, all usual inorganic or organic bases are suitable. These include, preferably, hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, tere. -potassium butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate as well as tertiary amines, such as 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). The process (a), according to the invention, is carried out, if appropriate, in the presence of a suitable condensation agent. As such, all the condensation agents which are usually usable for this type of amidation reactions are suitable. Examples which may be mentioned are acyl halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentacyanide, phosphorus oxychloride or thionyl chloride.; anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N, N '-dicyclohexylcarbodiimide (DCC) or other usual condensation agents, such as phosphorus pentoxide, polyphosphorous acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride or bromo-tripyrrolidinophosphonium hexafluorophosphate.

The process (a), according to the invention, is carried out in the presence of a catalyst if necessary. Examples which may be mentioned are 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide. The reaction temperatures in carrying out the process (a), according to the invention, can vary within wide limits. In general, temperatures are from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.

For carrying out the process (a), according to the invention, for the preparation of the compounds of the formula (I), per mole of the carboxylic acid derivative of the formula (II), in general, from 0 to 2 to 5 moles, preferably from 0.5 to 2 moles of aniline derivative of the formula "(III). As diluents for carrying out the processes (b) and (c), in accordance with the invention, they enter These include all inert organic solvents, preferably aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene. or decalin, halogenated hydrocarbons, such as for example chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane, ethers, such as diethyl ether, diisopropyl ether, methyl-tert. -butyl ether, methyl-tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, -dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide. The processes (b) and (c), according to the invention, are carried out, if necessary, in the presence of a base. As such, all usual inorganic or organic bases are suitable. These include, preferably, the hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of the alkaline earth metals or alkali metals, such as, for example, sodium hydride, sodium araide, sodium methylate, sodium ethylate, tere. -potassium butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate as well as tertiary amines, such as 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). The reaction temperatures in the carrying out of processes (b) and (c), according to the invention, can vary within wide limits. In general, temperatures are from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 110 ° C. For carrying out the process (b), according to the invention, for the preparation of the compounds of the formula (I), per mol of the hexylcarboxanilide of the formula (Ia), in general, from 0.2 are used. up to 5 moles, preferably from 0.5 to 2 moles of halide of the formula (IV). For carrying out the process (c), according to the invention, for the preparation of the compounds of the formula (Ill-a), are used, per mole of the aniline derivative of the formula (Ill-b), in general, from 0.2 to 5 moles, preferably from 0.5 to 2 moles of halide of the formula (IV). Suitable diluents for carrying out process (d), according to the invention, are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin.; the ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; the amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide; sulfoxides, such as dimethylsulfoxide; sulfones such as sulfolane; alcohols, such as methanol, ethanol, n- or iso-propanol, n-, iso-, sec.- or tere. - butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol, their mixtures with water or pure water. Process (d), according to the invention, is carried out in the presence of a metal. As such, transition metals, such as, for example, palladium, platinum, rhodium, nickel, iron, cobalt, ruthenium, iridium or osmium, are suitable. The metals can be bonded onto carrier materials, such as, for example, coals, resins, zeolites, alkali or alkaline earth sulfates. Process (d), according to the invention, is carried out in the presence of a reducing agent. Suitable as such are preferably elemental hydrogen, formate salts, preferably salts of alkali formates, such as, for example, sodium formate, as well as ammonium formate or even metal hydrides (hydrodehalogenation). The process (d), according to the invention, can be carried out in the presence of acids. Suitable as such are preferably organic acids, such as, for example, formic acid, acetic acid, ascorbic acid as well as mineral acids, such as, for example, hydrochloric acid or sulfuric acid. The process (d), according to the invention, can be carried out in the presence of bases. As such, preference is given to organic bases, such as, for example, pyridine, as well as aqueous solutions of alkali metal or alkaline earth metal hydroxides, such as, for example, sodium hydroxide or the barium hydroxide. The reaction temperatures, in the embodiment of the process (d), according to the invention, can vary within wide limits.In general, temperatures are from -80 ° C to 300 ° C, preferably at temperatures from 0 ° C to 200 ° C. When elemental hydrogen is used, the process (d), according to the invention, will be carried out under a hydrogen pressure comprised between 0.5 and 200 bar, preferably between 1 and 100 bar For carrying out the process (d), according to the invention, for the preparation of the compounds of the formula (III-c), per mole of the aniline derivative of the formula (Ill-d), generally, from 0.8 to 1000 moles, preferably from 1 to 500 moles of the reducing agent (ammonium formate, hydride, etc.) As diluents for carrying out the process (e), according to the invention, all are suitable the organic solvents These are preferably aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or the like. the decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; the ethers, such as the diethyl ether, the diisopropyl ether, the methyl-t-butyl ether, the methyl-tert. -amyl ether, dioxane, tetrahydrofuran, 1,2'-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones, such as acetone, butanone, the raethyl-isobutyl ketone or the cyclohexanone; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; the amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide; sulfoxides, such as dimethylsulfoxide; sulfones such as sulfolane; alcohols, such as methanol, ethanol, n- or isopropanol, n-, iso-, sec.- or tere. -butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol, their mixtures with water or pure water.

The process (e), according to the invention, is carried out in the presence of a base. Suitable as such are the hydroxides of the alkaline earth metals or alkali metals, such as, for example, sodium hydroxide, potassium hydroxide, ammonium hydroxide. The reaction temperatures in carrying out the process (e), according to the invention, can vary within wide limits. In general, temperatures are from 10 ° C to 300 ° C, preferably at temperatures from 150 ° C to 250 ° C. For carrying out the process (e), according to the invention, for the preparation of the compounds of the formula (Ill-e), per mole of the halogenoalkanonaniline of the formula (V) are used. in general, from 0.2 to 5 moles, preferably from 0.5 to 3 moles of hydrazine or hydrazine hydrate. As diluents for carrying out the procedure (f), in accordance with the invention, all inert organic solvents come into consideration. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; the ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl tert. - amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile, propionitrile, "n- or i-butyronitrile or benzonitrile, amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N- methylpyrrolidone or hexamethylphosphorotriamide, sulphoxides, such as dimethyl sulfoxide, sulphones such as sulfolane, alcohols, such as methanol, ethanol, n- or iso-propanol, n-, iso-, sec.- tere. -butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol, their mixtures with water or pure water. As such, they preferably include mineral acids, such as, for example, hydrochloric acid, hydroiodic acid or hydrobromic acid, sulfuric acid and also organic acids, for example trifluoroacetic acid, trifluoromethanol acid The temperatures of the reaction in carrying out the process (f), according to the invention, can vary within wide limits. In general, temperatures are from 0 ° C to 300 ° C, preferably at temperatures from 20 ° C to 200 ° C. For carrying out the process (f), according to the invention, for the preparation of the compounds of the formula ## STR4 ## (V), the molar protected halogen of the formula (VI) is used per mole of the halogenalkanonaniline. generally, from 0.1 to 10,000 moles, preferably from 1 to 2,000 moles of acid. As, diluents for carrying out the procedure (g), in accordance with the invention, all inert organic solvents come into consideration. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; the ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole. The process (g), according to the invention, is carried out in the presence of an organometallic compound. As such, the organic compounds of lithium, such as n-, sec- or tere, are preferably included. -butyllithium, phenyllithium or methyl-lithium. The reaction temperatures in the process (g), according to the invention, can vary within wide limits. In general, work is carried out at temperatures between -120 ° C and 100 ° C, preferably at temperatures from -80 ° C to 20 ° C. For carrying out the process (g), according to the invention, for the preparation of the compounds of the formula (VI), the molar, of the protected aniline, of the formula (VII) is used, in general, from 0.2 to 5 moles, preferably from 0.5 to 2 moles of ester of the formula (VIII). Suitable diluents for carrying out the process (h) according to the invention are all inert organic solvents. These preferably include aliphatic or alicyclic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; the ethers, such as diethyl ether, diisopropyl ether, methyl tert. -butyl ether, methyl-tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; alcohols, such as methanol, ethanol, n- or isopropanol, n-, iso-, sec.- or tere. -butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol, their mixtures with water or pure water. The process (h), according to the invention, is carried out in the presence of a catalyst. All catalysts, which are usually used for the hydrogenations, are considered as such. Examples which may be mentioned are: Raney nickel, palladium or platinum, optionally on a carrier material, such as, for example, activated carbon. The hydrogenation in the process (h), according to the invention, can be carried out in the presence of hydrogen in combination with a catalyst also in the presence of triethylsilane. The temperatures of the reaction in the carrying out of the process (h), according to the invention, can vary within wide limits. In general, temperatures are from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 100 ° C. The process (h) is carried out under a hydrogen pressure comprised between 0.5 and 200 bar, preferably between 2 and 50 bar, particularly preferably between 3 and 10 bar. Suitable diluents for carrying out process (i), according to the invention, are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; the ethers, such as diethyl ether, diisopropyl ether, methyl tert. -butyl ether, methyl-tert. - amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide; esters such as methyl acetate or ethyl acetate; sulfoxides, such as dimethylsulfoxide; sulfones such as sulfolane; alcohols, such as methanol, ethanol, n- or isopropanol, n-, iso-, sec.- or tere. -butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water. The process (i), according to the invention, is carried out in the presence of an acid. As such, all inorganic and organic protonic acids as well as Lewis acids are suitable, in the same way as all polymeric acids. These include, for example, hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, toluenesulfonic acid., boron trifluoride (also as etherate), boron tribromide, aluminum trichloride, titanium tetrachloride, tetrabutyl orthotitanate, zinc chloride, ferric chloride-III, antimony pentachloride, ion exchangers acids, acid clays and acid silica gel. The reaction temperatures in carrying out the process (i), according to the invention, can vary within wide limits. In general, temperatures are from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C. The processes (i) and (h), according to the invention, can also be carried out in a tandem reaction ("reaction in a single vessel"). For this, a compound of the formula (X) is reacted, if appropriate, in the presence of a diluent (suitable solvents for the process (i)), optionally in the presence of an acid (suitable acids as in the case of procedure (i)) and in the presence of triethylsilane. Suitable diluents for carrying out the process (k), in accordance with the invention, are all inert organic solvents, preferably aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, the petroleum, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; the ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole. The process (k), according to the invention, is carried out in the presence of an organometallic compound. Preferred as such are methylmagnesium chloride, bromide or iodide or methyl lithium. The reaction temperatures in carrying out the process (k), according to the invention, can vary within wide limits. In general, temperatures are from -120 ° C to 200 ° C, preferably at temperatures from -80 ° C to 100 ° C. For carrying out the process (k), according to the invention, for the preparation of the compounds of the formula (X), per mole of the halogenoalkanonaniline of the formula (V), in general, from 0.8 to 10 moles, preferably from 1 to 5 moles of organometallic compound. When nothing else is said, all procedures will be carried out, in accordance with the invention, in general, under normal pressure. However, it is also possible to work under higher pressure or at lower pressure, generally between 0.1 bar and 10 bar. The products, in accordance with the invention, have a potent microbicidal effect and can be used in practice to combat undesirable microorganisms, such as fungi and bacteria, in the protection of plants and in the protection of materials. Fungicidal agents are used in the protection of plants for the fight against plasmodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes. Bactericidal agents are used in the protection of plants to combat pseudoraonadaceos, rizobiaceos, enterobacteriaceos, corinebacteriaceos and streptomycetaceae. Some pathogens of fungal and bacterial diseases, which fall within the general definitions listed above, may be cited by way of example, but without any limiting character: types of Xanthomonas, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas types, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia types, such as, for example, Erwinia amylovora; Pythium types, such as for example Pythium ultimun; types of Phytophthora, such as for example Phytophthora infestans; Pseudoperonospora types, such as for example Pseudoperonospora humuli or Pseudoperonospora cubensis; types of Plasmopara, such as for example Plasmopara viticola; Bremia types, such as, for example, Bremia lactucae; Peronospora types, such as, for example, Peronospora pisi or P. brassicae; Erysiphe types, such as for example Erysiphe graminis; Sphaerotheca types, such as for example Sphaerotheca fuliginea; Podosphaera types, such as, for example, Podosphaera leucotricha; Venturia types, such as, for example, Venturia inaequalis; types of Pyrenophora, such as, for example, Pyrenophora teres or P. gramínea; (form of conidia, Drechslera, synonym: Helminthosporium); Cocliobolus types, such as, for example, Cochliobolus sativus (conidia form, Drechslera, synonym: Helminthosporium); Uromyces types, such as, for example, Uromyces appendiculatus; Puccinia types, such as Puccinia recondita; Sclerotinia types, such as, for example, Sclerotinia sclerotiorum; types of Tilletia, such as for example Tilletia caries; types of Ustilago, such as for example Ustilago nuda or Ustilago avenae; Pellicularia types, such as, for example, Pellicularia sasakii; types of Pyricularia, such as, for example, Pyricularia oryzae; Fusarium types, such as for example Fusarium culmorum; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of Lentosphaeria, such as for example Leptosphaeria nodorum, -types of Cercospora, such as for example Cercospora canescens, -types of Alternaria, such as for example Alternaria brassicae; types of Pseudocercosporella, such as for example Pseudocercosporella herpotrichoides, types of Rhizoctonia, such as for example Rhizoctonia solani .. The active compounds, according to the invention, also have a potent reinforcing effect on plants.

These are suitable, therefore, to mobilize the resistance forces of plants against the attack of undesirable microorganisms. In this context, plant-reinforcing products (resistance inducers) will be understood to be those substances that are capable of stimulating the immune system of plants in such a way that the treated plants develop a broad resistance against microorganisms when a subsequent inoculation occurs. with these undesirable microorganisms. It should be understood by undesirable microorganisms, in the present case, phytopathogenic fungi, bacteria and viruses. The products, according to the invention, can be used, therefore, to generate resistance in the plants, within a certain period of time from the treatment, against the attack due to the aforementioned pathogens. The time lapse, within which resistance is caused, extends, in general, from 1 to 10 days, preferably from 1 to 7 days from the treatment of the plants with the active products. The good compatibility of the active products with the plants at the concentrations necessary for the control of plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil.

In this case, the active compounds according to the invention can be used with particularly good success in the control of cereal diseases, such as, for example, against types of Puccinia and diseases of vineyard plantations, of fruit trees and vegetables, such as, for example, against types of Botrytis, Venturia or Alternaria. The active products, according to the invention, are also suitable for increasing the yield of the crops. It also has a low toxicity and have good compatibility with plants. The active products, according to the invention, they can be used, if appropriate, in certain concentrations and amounts of application, also as herbicides, to influence the growth of plants, as well as for the control against animal pests. These can also be used, if appropriate, as intermediates and as starting materials for the synthesis of other active products. In accordance with the invention, all plants and parts of plants can be treated. By plants, all plants and plant populations, such as desired and unwanted wild plants (including crop plants of natural origin), will be understood in this case. Crop plants can be plants which can be obtained by conventional methods of breeding and optimization or by biotechnological methods and genetic engineering, including transgenic plants and including plant varieties protectable or not by means of the right of protection of varieties - ".-- plants." By parts of the plants should be understood all the parts and aerial and subterranean organs of the plants, such as buds, leaves, flowers and roots, being able to indicate in an exemplary way leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. at plant parts also include harvested 'as material and vegetative and generative reproduction, for example seedlings, tubers , rhizomes, layers and seeds The treatment, according to the invention, of plants and parts of plants with the products assets is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporation, fogging, scattering, painting on and, in the case of the reproduction material, especially in the case of the seeds, also by coating with one or several layers. The products, according to the invention, can be used in the protection of industrial materials against the attack and destruction due to undesirable microorganisms. Industrial materials in the present context will be understood as non-living materials, which have been prepared for use in the art. For example technical materials, which would be protected from microbial change or destruction by active compounds, in accordance with the invention are adhesives, sizes, paper and cardboard, textiles, leather, wood, paints and articles material synthetic, cold lubricants and other materials. In the field of the materials to be protected, parts of production facilities, for example closed cooling water circuits, which may be adversely affected by the multiplication of microorganisms may also be mentioned. Within the scope of the present invention, adhesives, glues, paper and paperboard, leather, wood, paints, cold lubricants and heat transfer liquids, preferably wood, can be mentioned as technical materials. As microorganisms, which can cause the decomposition or modification of technical materials, examples of bacteria, fungi, yeasts, algae and mucilaginous organisms can be cited. Preferably, the active compounds, according to the invention, act against fungi, especially against molds, coloring fungi and wood destroyers (Basidiomycetes) as well as against mucilaginous organisms and algae. As an example may be mentioned microorganisms of the following types: Alternaria, such as Alternaria tenuis such, Aspergillus, such as Aspergillus niger, Chaetomium, Chaetomium globosum as, Coniophora, such as Coniophora puetana such, "Lentinus, Lentinus tigrinus as, Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, - Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa , Staphylococcus, such as Staphylococcus aureus. The active compounds can be converted, depending on their respective physical and / or chemical properties, into the customary formulations such as solutions, emulsions, suspensions, powders, sprays, pastes, granules, aerosols, microencapsulations in polymeric materials and in coating compositions. seeds, as well as formulations of cold fogging and hot in ultra-low volume (ULV). These formulations are prepared in a known manner, for example by mixing the active ingredients with spreading agents, that is to say liquid solvents, liquefied gases, which are under pressure and / or solid support materials, optionally with the use of surfactants, that is, emulsifiers and / or dispersants and / or foam generating agents. In the case of the use of water as an extender, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum, alcohols, such as butanol or glycol, as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide as well as water. By liquefied gaseous extenders or support materials are meant those which are gaseous at normal temperature and under normal pressure, for example propellant gases for aerosol, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid support materials are, for example, natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth and synthetic mineral flours, such as highly dispersed silicic acid, aluminum and silicates. Suitable solid support materials for granulates are, for example, broken minerals and fractions such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules formed from inorganic and organic flours as well as granules formed from organic material. such as sawdust, coconut shell husks, corn ears and tobacco stems. Suitable emulsifying and / or foam generating agents are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol ethers, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, arylsulfonates, and hydrolysates. of albumin. Suitable dispersants are, for example, sulfite lignin blends and methylcellulose. In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granular or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate as well as natural phospholipids, such as cefaliña and lecithin and synthetic phospholipids can be used. Other additives can be mineral and vegetable oils. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanide blue and organic colorants such as metallic alizarin, azo and phthalocyanine dyes and trace nutrient materials, may be employed., such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts. The formulations generally contain between 0.1 and 95 weight percent active product, preferably between 0.5 and 90%. The active compounds according to the invention can be present as such or in their formulations also in a mixture of known fungicides, bactericides, acaricides, nematicides or insecticides, in order to extend, for example, the spectrum of activity or the development of the resistance. In many cases synergistic effects are obtained, that is to say that the activity of the mixture is greater than the activity of the individual components. Examples of suitable mixing components are the following compounds: Fungicides: 2-phenylphenol; 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampropylfs; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Benalaxyl-M; Benodanil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; Bilanafos; Binapacryl; Biphenyl; Bitertanol; Blasticidin-S; Bromuconazole; Bupirimate; Buthiobate; Butylamine; calcium polysulfide; Capsimycin; Captafol; Captan; Carbendazim Carboxin; 'Carpropamid; Carvone; Chinomethionat Chlobenthiazone; Chlorfenazole; Chloroneb; Chiorothalonil Chlozolinate; Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil Cyproconazole; Cyprodinil; Cyprofuram; Dagger G; Debacarb Dichiofluanid; Dichlone; Dichlorophen; Diclocymet Diclomezine; They diclored; Diethofencarb; Difenoconazole Difiumetorim; Dimethirimol; Dimethomorph; Dimoxystrobin Diniconazole; Diniconazole-M; Dinocap; diphenylamine Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon Edifenphos; Epoxiconazole; Ethaboxam; Ethyrimol; Etridiazole Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole Fenfuram; Fenhexaraid; Fenitropan; Fenoxanil; Fenpiclonil Fenpropidin; Fenpropimorph; Ferbam; Fluazinam; Flubenzimine Fludioxonil; Flumetover; Flumorph; Fluoromide; Fluoxastrobin Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide Flutolanil; Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil; Furmecyclox Guazatine; hexachlorobenzene; Hexaconazole; Hymexazole Imazalil; Imibenconazole; Iminoctadine triacetate Iminoctadine tris (albesilate); Iodocarb; Ipconazole Iprobenfos; Iprodione; Iprovalicarb; Irumamycin Isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl Mancozeb; Maneb; Meferimzone; Mepanipyrim; Mepronil Metalaxyl; Metalaxyl-M; Metconazole; Methasulfocarb Methfuroxam; Metiram; Methominostrobin; Metsulfovax Mildioraycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen Nitrothal-isopropyl; Noviflumuron; Nuarimol; Ofurace Orysastrobin; Oxadixyl; oxolinic acid; Oxpoconazole Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefurazoate Penconazole; Pencycuron; Phosdiphen; Phthalide; Picoxystrobin Piperalin; Polyoxins; Polyoxorim; Probenazole, - Prochloraz Procyraidone; Propamocarb; Propanosine-sodium; Propiconazole Propineb; Proquinazid; Prothioconazole; Pyraclostrobin Pyrazophos; Pyrifenox; Pyrimethanil; Pyroquilon; Pyroxyfur Pyrrolnitrine; Quinconazole, - Quinoxyfen; Quintozene Simeconazole; Spiroxamine; Sulfur; Tebuconazole; Tecloftalam Tecnazene; Tetcyclacis; Tetraconazole; Thiabendazole Thicyofen; Thifluzamide; Thiophanate-methyl; Thiram; Thioxymid Tolclofos-methyl; Tolylfluanid; Triadimefon; Triadimenol Triazbutyl; Triazoxide; Tricyclamide; Tricyclazole Tridemorph; Trifloxystrobin; Triflumizole; Triforine Triticonazole; Uniconazole; Validamycin A; Vinclozolin; Zineb Ziram; Zoxamide; (2S) -N- [2- [4- [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [(methyl-sulfonyl) amino] -butanoamide; 1- (1-naphthalenyl) -lH-pyrrole-2, 5-dione; 2, 3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-1- (4-chlorophenyl) -2- (1 H-1,2,4-triazol-1-yl) -cycloheptanol; l- (2,3-dihydro-2, 2-dimethyl-lH-inden-l-yl) -lH-imidazole-5-carboxylic acid methyl ester; monopotassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [.5] decan-3-amine; sodium tetrathiocarbonate; as well as copper salts and copper preparations, such as Bordeaux blends; copper hydroxide; copper naphthenate; Copper oxychloride; copper sulphate; Cufraneb; copper oxide; Mancopper; copper oxine. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, Probenazole, Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematisides: 1. Acetylcholine esterase inhibitors (AChE) 1.1 Carbamates (for example Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Chloethocarb, Coumaphos, Cyanofenphos, Cyanophos, Dimetilan, Ethiophencarb, Phenoxycarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb , Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb) 1.2 Organogosphates (for example Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (- methyl), Butathiophos, Cadusafos, Carbophenothion, Chlorethoxyphos, Chiorfenvinphos, Chlormephos, Chlorpyrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chiorfenvinphos, Demeton-S-methyl, Deraeton-S-methylsulfone, Dialiphos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimphos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Fl upyrazophos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazophos, Isofenphos, O-isopropyl salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, Propetamphos, Prothiophos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrac lorvinphos, Thiometon, Triazophos, Trichlorphon, Vamidothion) 2. Sodium channel modulators / blockers of the sodium channel as a function of tension 2.1 Pyrethroids (for example Acrinathrin, Allethrin ( d-cis-trans, d-trans), Beta-Cyfluthrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, Chlovaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrm (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Deltamethrin, Empenthrin (isomer) IR), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma-Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (cis-, trans-), Phenothrin (IR-trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (IR isomer), Tralomethrin, Transfluthrin, ZXI 8901, Pyrethrins (pyrethrum)) 2.2 Oxadiazines (for example Indoxacarb) 3. Agonists / acetylcholine receptor agonists 3.1 Cloronicotinyl / neonicotinoids (for example Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Ni thiazine, Thiacloprid, Thiamethoxam) 3.2 Nicotine, Bensultap, Cartap 4. Acetylcholine receptor modulators 4.1 Spinosids (eg Spinosad) 5. Chloride channel antagonists controlled by GABA 5.1 Cyclodienic organochlorides (eg Camphechlor, Chlordane, Endosulfan, Gamma -HCH, HCH, Heptachlor, Lindane, Methoxychlor 5.2 Fiproles (for example Acetoprole, Ethiprole, Fipronil, Vaniliprole) 6. Activators of the chloride channel 6.1 Mectinase (for example Abamectin, Avermectin, Emamectin, Emamectin-benzoate, Ivermectin, Milbemectin, Milbemycin) 7"Juvenile hormone mimetics (eg, Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene) 8. Ecdysonic disruptors / disruptors 8.1 Diacylhydrazines (eg Chromafenozide) , -Halophenozide, Methoxyfenozide, Tebufenozide) 9. Chitin biosynthesis inhibitors 9.1 Benzoylureas (for example Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Triflumuron) 9.2 Buprofezin 9.3 Cyromazine 10. Inhibitors of oxidative phosphorylation, ATP disruptors 10.1 Diafenthiuron 10.2 Organotins (for example Azocyclotin, Cyhexatin, Fenbutatin-oxide) 11. Decouplers of oxidative phosphorylation by proton gradient interruption of H 11.1 Pyrroles (for example Chlorfenapyr) 11.2 Dinitrophenols (for example Binapacyrl, Dinobuton, Dinocap, DNO C) 12. Inhibitors of electronic transport on the I side 12.1 The "METI (for example ^ Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad) .. 12.2 Hydramethylnone 12.3 Dicofol 13. Inhibitors of electronic transport on the side II 13.1 Rotenone 14. Inhibitors of electronic transport on side III 14.1 Acequinocyl, Fluacrypyrim 15. Microbial disruptors of intestinal membrane of insects strains of Bacillus thuringiensis 16. Inhibitors of synthesis of fats 16. 1 Tetronic acids (eg Spirodiclofen, Spiromesifen) 16.2 Tetramic acids [eg 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (aka: Carbonic acid, 3- (2, 5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS-Reg. -Do not. : 382608-10-8) and. Carbonic acid, cis -3- (2, 5-dimethylphenyl) -8- methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS-Reg. -No .: 203313 -25-1)] 27. Carboxyamides (for example Flonicamid) 18. Octopaminergic agonists (for example Amitraz) 19. Magnesium-stimulated ATPase inhibitors (for example Propargite) 20. Phthalamides (for example N2- [1, -dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N 1 - [2-methyl-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS-Reg.-No .: 272451-65-7)) 21. Nereistoxin analogues (eg Thiocyclam hydrogen oxalate, Thiosultap-sodium) 22. Biologicals, hormones or pheromones (eg Azadirachtin, Bacillus spec., Beauveria spec., Codlemone, Metarrhizium spec., Paecilomyces spec., Thuringiensin, Verticillium spec.) 23. Active products with unknown or non-specific actuation mechanisms 23.1 Agents for gasification (eg aluminum phosphide, methyl bromide, sulfuryl fluoride) 23.2 Selective intake inhibitors (eg Cryolite, Flonicamid, Pymetrozine) 23.3 Inhibitors of growth of mites (for example Clofentezine, Etoxazole, Hexythiazox) 23.4 Amidoflumet, Benclothiaz, Benzoxiraate, Bifenazate, Bromopropylate, Buprofezin, Chinomethionat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim , Flutenzin, __ Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, plus the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z ), the compound 3- (5-chloro-3-pyridinyl) -8- (2, 2, 2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS-Reg. -Nr. 185982-80-3) and the corresponding 3-endo-isomer (CAS-Reg. -Nr 185984-60-5) (see publication WO-96/37494, WO-98/25923), as well as preparations, which they contain plant extracts of insecticidal action, nematodes, fungi or viruses. A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, protective or semi-chemical products is also possible.

In addition, the compounds according to the invention of formula (I) also have very good antifungal effects. They have a very broad spectrum of antifungal activity, especially against dermatophytes and blastomycetes, molds and against diphasic fungi (for example against Candida species, such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigas, Trichophyton species, such as Trichophyton mentagrophytes, microspore species, such as Microsporon canis and audouiníi. The enumeration of these fungi does not represent in any way a limitation of the fungal spectrum to be considered but it has only an orientative character. The active compounds can be used in the form of their formulations or in the application forms prepared therefrom, such as solutions, suspensions, sprayable powders, pastes, soluble powders, powders and granules ready for use. The application is carried out in the usual manner, for example by watering, spraying, dusting, spreading, sprinkling, foaming, brush application, etc. It is also possible to apply the active products according to the ultra-low volume process or to inject the preparation of the active product or the active product itself into the soil. The seeds of the plants can also be treated.

When the active compounds according to the invention are used as fungicides, the application rates can vary within wide limits in accordance with the type of application. When the parts of the plants are treated, the application quantities of the active product are, in general, between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of the treatment of the seeds, the application amounts of the active compound are, in general, between 0.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seeds. In the case of the treatment of the land, the application quantities of active product are, in general, between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha. As already indicated above, all plants and their parts can be treated according to the invention. In a preferred embodiment plants and plant varieties are treated as well as their parts of wild origin or that are obtained by conventional methods of biological culture, such as crossing or fusion of protoplasts. In another preferred embodiment, plants and varieties of transgenic plants, which have been obtained according to genetic engineering methods if opriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The expression "parts" or "parts of plants" or "components of plants" has been previously explained. Particularly preferred are plants, according to the invention, of the plant varieties customary in the market or which are in use. Plant varieties are understood as plants with new properties ("characteristics"), which have been cultivated either by conventional culture, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes or genotypes. According to the types of plants or the varieties of the plants, their location and the growing conditions (soil, climate, vegetation period, feeding) can also be presented by means of the treatment, in accordance with the invention, sobreaditivos ("synergists"). In this way, for example, smaller amounts of ication and / or enlargements of the activity spectrum and / or a strengthening of the effect of the employable products are possible, in accordance with the invention, improve plant growth, greater tolerance to temperatures. high or low, greater tolerance against drought or against the salt content of water or soil, greater floral yield, easier harvesting, acceleration of maturation, higher crop yields, higher quality and / or higher nutritive value of the products collected, greater storage capacity and / or transformation of the products collected, which go beyond the expected effect itself. The plants or varieties of transgenic plants (obtained by genetic engineering), to be treated preferably, according to the invention, belong to all plants, which have acquired genetic material through modification by genetic engineering, which provide these plants with valuable properties especially advantageous ("characteristics"). Examples of such properties are, better plant growth, greater tolerance to high or low temperatures, greater tolerance to drought or against the salt content of water or soil, higher floral yield, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, greater storage capacity and / or transformation of the products harvested. Other examples, especially noteworthy for such properties are the greater resistance of plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as a greater tolerance of plants against certain active herbicide products. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rape, as well as fruit tree plantations (with the fruits e, pear, citrus and grape). , especially corn, soybeans, potatoes, cotton, tobacco and rapeseed. Corao properties ("characteristics") will be noted especially the greater resistance of plants against insects, arachnids, nematodes and snails by means of the toxins generated in plants, especially those that are generated in plants by genetic material from of Bacillus Thuringiensis (for example by means of the genes Cry? A (a), Cry? A (b), Cry? A (c), CrylIA, CrylIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations ), (referred to below as "Bt plants"). As properties ("characteristics") should be noted in addition, especially, the greater resistance of plants against fungi, bacteria and viruses through systemic acquired resistance(SAR), systemin, phytoalexin, elicitors as well as resistance genes and corresponding expressed proteins and toxins.

As properties ("characteristics"), in particular, the greater tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, Glyphosate or Phosphinotricin (for example gene "PAT") must be pointed out. The genes that provide the respective desired properties ("characteristics") may also be present in combinations with each other in the transgenic plants. Examples of "Bt plants" include corn varieties, cotton varieties, soya varieties and potato varieties, which are marketed under the trademarks YIELD GARD® (for example corn, cotton, soybean), KnockOut® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide tolerant plants include corn varieties, cotton varieties and soybean varieties, which are marketed under the trademarks Roundup Ready® (tolerance against Glyphosate, eg corn, cotton, soy), Liberty Link® ( tolerance against 'Phosphinothricin, for example rapeseed oil), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas for example corn). As herbicide-resistant plants (conventionally grown in relation to herbicide tolerance), the varieties marketed for the name Clearfield® (eg corn) can also be cited. Obviously these statements are valid also for varieties of plants developed in the future or that are marketed or developed in the future with these genetic properties ("characteristics"). The stated plants can be treated in a particularly advantageous manner, according to the invention, with the compounds of the general formula (I) or of the mixtures of the active compounds according to the invention. The preferred sectors, mentioned above, in the case of active products or mixtures, are also valid for the treatment of these plants. It should be noted in a special way the treatment of the plants with the compounds or with the mixtures indicated especially in the present text. The obtaining and use of the active products, according to the invention, are derived from the following examples. Preparation examples Example 1 They are added to a solution consisting of 275.3 mg (1.3 mmol) of 2-trifluoromethylbenzoyl chloride and 0.22 ml (1.6 mmol) of triethylamine in 10 ml of tetrahydrofuran, 302.0 mg (1 ml). , 2 mmoles) of 4-chloro-2- (4,4,4-trifluoro-3-methyl-butyl) -phenylamine in 2 ml of tetrahydrofuran. The reaction solution is stirred for 90 minutes at 60 ° C, filtered through silica gel and concentrated in vacuo. 505 mg (99% of theory) of N- [4-chloro-2- (4,4, 4-trifluoro-3-methyl-butyl) -phenyl] -2-trifluoromethyl-benzamide [logP (pH 2.3) = 4.08]. Example 2 They are added to a suspension of 264.2 mg (1.5 mmol) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid, in 9 ml of dichloromethane, 0.14 ml (1.7 mmol) of oxalyl dichloride and 4 drops of dimethylformamide. The reaction mixture is stirred for 2 hours at room temperature and then combined with a solution consisting of 325.9 mg (1.5 mmol) of 2- (4,4,4-trifluoro-3-methyl) -butyl) -phenylamine and 0.29 ml (2.1 mmol) of triethylamine in 9 ml of dichloromethane. The reaction mixture is stirred for 16 hours at room temperature. For working up, add 7 ml of 2N hydrochloric acid, stir for 10 minutes at room temperature, separate the organic phase, dry over magnesium sulfate, filter and concentrate in vacuo. 525.0 mg (89% of theory) of 3-difluoromethyl-1-methyl-1H- [2- (4,4,4-trifluoro-3-methyl-butyl) -phenyl] -amide is obtained. pyrazole-4-carboxylic acid [lopP (pH 2.3) = 2.93]. In a manner analogous to that of Examples 1 and 2, as well as according to the indications of the general description of the obtaining procedures, according to the invention, (a) to (h) the compounds of the formula are also obtained (I) indicated in the following table 1: Table 1 Nr. R R3 M logP The linkage, marked with "*" is linked to the amide, the linkage, marked with "#" is linked to the haloalkyl moiety.

Obtaining the starting products of the formula (III) Example (III-l) A solution of 7.0 g of 1- (2-amino-5-chlorophenyl) -4,4-trifluoro-3-methyl-butan-1-one (26 mmoles), 4.0 g of potassium hydroxide (60 mmoles) and 3.0 g hydrazine hydrate (60 mmoles) in 67 ml of triethylene glycol, for 6 hours at 210 ° C. After cooling to room temperature, water and ethyl acetate are added, the phases are separated and the organic phase is washed again with water, dried over magnesium sulfate and freed from the solvent. 4.9 g- (73% of theory) of 4-chloro-2- (4,4, 4-trifluoro-3-methyl-butyl) -phenylamine are obtained. XH-NMR (DMSO): d = 6.93 (m, 2 H), 6.62 (d, 1 H), 5.05 (s, 2 H), 2.56 (m, 1 H), 2 , 48-2.34 (m, 2 H), 1.85 (m, 1 H), 1.47 (, 1 H), 1.11, (d, 3 H). Example (III-2) A solution of 2.3 g of 4-chloro-2- (4,4,4-trifluoro-3-methyl-butyl) -phenylamine (III-1) (9 mol), 1.15 g of formate is stirred. of ammonium (18 mmoles) and 2.0 g of Pd / C (5%, 0.9 mmoles) in 21 ml of methanol, for 1 hour at room temperature. The solution of the reaction is then subjected to suction filtration through celite, washed further with methanol and the filtrate is concentrated on a rotary evaporator. The agitation of the residue, after removal of the solvent, with pentane provides a solid product, which is filtered off by suction and dried. 1.7 g (86% of theory) of 2- (4,4,4-trifluoro-3-methyl-butyl) -phenylamine are obtained .. XH-NMR (DMSO) rd = 6.89 (m, 2 H), 6.61 (m, 1 H), 6.49 (m, 1 H), 4.83 (s, 2 H), 2.57 (m, 1 H), 2.48-2, 30 (m, 2 H), 1.85 (m, 1 H), 1.46 (m, 1 H), 1.13 (d, 3 H). Obtaining the starting materials of the formula (V) Example (V-1) A solution of 10.0 g (29 mmol) of the N- [4-chloro-2- (4,4,4-trifluoro-3-methyl-butyryl) -phenyl] is heated under reflux for 2 days. 2, 2-dimethyl-propionamide in 366 ml of 37% hydrochloric acid. After cooling to room temperature, it is neutralized with 45% sodium hydroxide solution and the aqueous phase is extracted with dichloromethane. Drying the organic phase over sodium sulfate and removing the solvent provide 7.1 g (93% of theory) of the l- (2-amino-5-chloro-phenyl) -4,4,4-trifluoride -3-methyl-butan-1-one. aH-NMR (DMSO): d = 7.80 (d, i H), 7.34 (s, 2 H), 7.29 (dd, 1 H), 6.82 (dd, 1 H), 3 , 28 (dd, 1 H), 3.14 (dd, 1 H), 3.00 (m, 1 H), 1.08 (d, 3 H). Obtaining the starting products of the formula (VI) - Example (VI-1) A solution of 15.4 g of N- (4-chlorophenyl) -2,2-dimethyl-propioamide (73 mmol) in 100 ml of dry tetrahydrofuran, at 0 ° C, is added dropwise with a solution of n-butyl lithium in hexane (1.6 M, 100 ml, 160 mmol) and stirred for 2 hours at this temperature. This solution is then added dropwise at -70 ° C to a solution of 13.4 g of ethyl (3-trifluoromethyl) butyrate (73 mmol) in 250 ml of dry tetrahydrofuran and the mixture of the reaction is continued stirring for 1 hour at this temperature. After heating to room temperature, stirring is continued for 16 hours. The hydrolysis with 100 ml of water, the concentration by evaporation, the residue in dichloromethane / water and the extraction of the aqueous phase with dichloromethane provide, after the drying of the in¬ organic over sodium sulfate, a product / product mixture, which can be separated by column chromatography on silica gel with cyclohexane / ethyl acetate (9: 1) as eluent. 10.3 g (40% of theory) of N- [4-chloro-2- (4,4, 4-trifluoro-3-methyl-butyryl) -phenyl] -2,2-dimethyl-propionamide are obtained. . XH-NMR (DMSO): d = 11.15 (s, 1 H), 8.39 (d, 1 H), 8.11 (d, 1 H), 7.67 (dd, 1 H), 3 , 47 (dd, 1 H), 3.30 (dd, 1 H), 2.99 (m, 1 H), 1.25 (s, 9 H), 1.15 (d, 3 H). The determination of the logP values was carried out in accordance with EEC Directive 79/831 annex V.A8 by HPLC (high performance liquid chromatography) on a column with phase inversion (C 18). Temperature 43 ° C. Eluents for the determination in the acid range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile. The calibration was carried out with unbranched alcan-2-ones (with 3 to 16 carbon atoms), whose LogP values are known (determination of the logP values by means of the retention times by linear interpolation between two successive alkanones) . The maximum lambda values were determined by means of the UV spectra from 200 nm to 400 nm at the maximums of the chromatography signals.

Application examples; Example A Test with Sphaerotheca (cucumber) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether.

To obtain a suitable active preparation, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are inoculated with an aqueous suspension of spores of the pathogen Sphaerotheca fuliginea. The plants are then placed in the greenhouse at approximately 23 ° C and with a relative humidity of about 70%. The evaluation is carried out 7 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed.

Table A Test with Sphaerotheca (cucumber) / protector Active product, in accordance with the applied quantity of. Degree of invention, active product in g / ha activity in% Example B Tested with Venturia (apple tree) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether.

To obtain a suitable active preparation, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test the protective activity, young cucumber plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the spray-applied coating, the plants are inoculated with an aqueous suspension of conidia of the anthracnose of the apple tree Venturia inaequalis and they remain for 1 day at approximately 20 ° C and with a relative humidity of 100% in an incubation chamber. The plants are then placed in the greenhouse at approximately 21 ° C and with a relative humidity of about 90%. The evaluation is carried out 10 days after inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed. Table B Venturia (apple) / protector test Active product, in accordance with the Quantity applied of Degree of invention, active product in g / ha activity in% Active product, in accordance with the Quantity applied of the Degree of the invention, active product in g / ha activity in% Active product, in accordance with the Quantity applied of Degree of invention, active product in g / ha activity in% Example C Test with Botrytis (beans) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether.

To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with li¬ the indicated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, 2 pieces of agar coated with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at approximately 20 ° C and with a relative humidity of 100%. The evaluation is carried out 2 days after the inoculation by means of the magnitude of the spots produced by the attack. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed. Table C Test with Botrytis (beans) / protector Active product, in accordance with the applied Quantity of Degree of invention, active product in g / ha activity in% Test with Botrytis (beans) / protector Example D Assay with Puccinia (wheat) / protector Solvent: 50 parts by weight of N; N-dimethylacetamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable active preparation, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are inoculated with a conidial suspension of recondite Puccinia. The plants remain 48 hours at 20 ° C and with a relative humidity of 100%. The plants are then placed in a greenhouse at a temperature of approximately 20 ° C and with a relative humidity of 80% to favor the development of rust pustules. The evaluation is carried out 10 days after inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed. Table D Test with Pucinia (wheat) / protector Active product, in accordance with the Quantity applied of Degree of "nvention, active product in g / ha activity in% Example E Alternating Test (Tomato) / Protector Solvent: 49 Parts by Weight of N, N-dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After 1 day, from the treatment, the plants are inoculated with a suspension of alternaria solani spores and then allowed to stand for 24 hours with a relative air humidity of 100% and at 20 ° C. Then leave the plants with a relative humidity of 96 ° C and at a temperature of 20 ° C. The evaluation is carried out 7 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed. Table E Test with Alternaria (tomato) / protector Active product, in accordance with the Quantity applied of the Degree of the invention, active product in g / ha activity in% Test with Alternaria (tomato) / protector Active product, in accordance with the applied Quantity of Degree of invention, active product in g / ha activity in% It is noted that, with reference to this date, the best method known to the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention.

Claims (1)

CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. Halogenoalkylcarboxamides of the formula (I) characterized in that R represents hydrogen or halogen, R1 signifies hydrogen or methyl, R2 signifies methyl, ethyl or halogenoalkyl having 1 to 4 carbon atoms, with 1 to 9 fluorine, chlorine and / or bromine atoms, R3 means halogen or haloalkyl with 1 to 4 carbon atoms, with 1 to 9 fluorine, chlorine and / or bromine atoms, R4 means hydrogen, alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) Caryl-C 1 -alkyl 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-alkyl with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 8 alkyl) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C akalkyl) 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R, -CONR6tR, 7 or -CH2NR8R9, R5 means hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 atoms carbon-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, Rd and R7 stand for, independently of each other respectively, hydrogen, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 atoms carbon, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms, with, respectively, 1 to 9 fluorine atoms, chlorine and / or bromine, R6 and R7 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle, with 5 to 8 atoms in the ring, optionally substituted one or more times, of Likewise or in different forms by halogen or by alkyl having 1 to 4 carbon atoms, the heterocycle may contain 1 or 2 more heteroatoms, not contiguous, of the series formed by oxygen, sulfur or NR10, R8 and R9 mean, independently yes, hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms, with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R8 and R9 also form, together with the nitrogen atom , with which they are bound, a saturated heterocycle, with 5 to 8 atoms in the substituted ring, optionally one or more times, in the same or in different forms by halogen or by alkyl with 1 to 4 carbon atoms, contain the heterocycle 1 or 2 heteroatoms more, not contiguous, of the series formed by oxygen, sulfur or NR10, R10 means hydrogen or alkyl having 1 to 6 carbon atoms, M means a ring of phenyl, pyridine or pyrimidine, pyridazine or pyrazine monosubstituted, respectively, by R11 or means a thiazole ring substituted by R1: L "A, R1X means hydrogen, fluorine, chlorine, methyl, iso-propyl, methylthio or trifluoromethyl, R1: L ~ A means hydrogen, methyl, methylthio or trifluoromethyl, A means the rest of the formula (Al) R 12 denotes hydrogen, cyano, halogen, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or - halogenoalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-alkyl with 1 to 4 carbon atoms, R13 means hydrogen , halogen, cyano, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms, R14 means hydrogen, alkyl with 1 to 4 carbon atoms, hydroxy-alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, haloalkyl with-1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or phenyl, or A means the rest of the formula (A2) R15 and R16 stand for hydrogen independently, halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, R17 is halogen, cyano or alkyl having 1 to 4 carbon atoms; carbon, or halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the remainder of the formula (A3) R, 18"and tR-, 19 mean, independently of one another, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R20 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A4) a (A4), wherein R21 R21 means hydrogen, halogen, hydroxy, cyano, alkyl with 1 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the remainder of the formula (A5) R22 means halogen, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with , respectively, 1 to 5 halogen atoms, R23 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenoalkoxy having 4 carbon atoms with, respectively, 1 to 5 halogen atoms, alkylsulfinyl having 1 to 4 carbon atoms or alkylsulfonyl having 1 to 4 carbon atoms, or A means the remainder of the formula (A6) ) R24 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R25 means alkyl with 1 to 4 carbon atoms, Q1 means S (sulfur), O (oxygen), SO, S02 or CH2, p means 0, 1 or 2, meaning R25 identical or different residues, when p means 2, or A means the rest of the formula (A7) R26 means alkenyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A8) R27 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of formula (A9) R28 and R29 signify, independently of each other, "hydrogen, halogen, amino, alkyl having 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R30 signifies hydrogen, halogen, alkenyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (AlO) R31 and R32 mean, independently of one another, hydrogen, halogen, amino, nitro, alkyl having 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms, with 1 to 5 halogen atoms, R33 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (All) R34 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (C1-C4 alkyl) amino, cyano, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R3? means halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A12) R36 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (C 1 -C 4 -alkyl) amino, cyano, alkyl with 1 to 4 carbon atoms or halogen alkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R37 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A13) R38 means halogen, alkenyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A14) R39 means hydrogen or alkyl having 1 to 4 carbon atoms, R40 means halogen or alkyl having 1 to 4 carbon atoms, or A means the remainder of the formula (A15) R41 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, A means the remainder of the formula (A16) R42 denotes hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A17) R43 means halogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogen alkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the rest of the formula (A18) R44 means hydrogen, cyano, alkyl with 1 to 4 carbon atoms, halogen alkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms, hydroxy-alkyl having 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms) aminosulfonyl, alkylcarbonyl with 1 to 6 carbon atoms or means phenylsulphonyl or benzoyl substituted respectively where appropriate, R45 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R4S means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, "R47 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the rest of the formula (A19) * R48 means alkyl with 1 to 4 carbon atoms. 2. Halogen alkylcarboxamides of the formula (1) according to claim 1, characterized in that R means hydrogen, fluorine, chlorine or bromine, -, R means hydrogen or methyl, R 2 signifies methyl, ethyl or means methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. -butyl substituted one or more times, in the same or in different ways, by fluorine, chlorine or bromine, R3 means fluorine, chlorine, bromine, iodine or means methyl, ethyl, n- or iso-propyl, n- , iso-, sec.- or tere. -butyl substituted one or more times, in the same or different manner by fluorine, chlorine or bromine, R 4 is hydrogen, alkyl having 1 to 6 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl having 1 to 3 carbon atoms, cycloalkyl having 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms-alkyl with 1 at 3 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-alkyl with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 6 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl) carbonyl, (C 3 -C 3) -alkyl 6 carbon atoms) carbonyl; (halogenalkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms) carbonyl, (halogencycloalkyl with 3 to 6 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R5, -C0NR6R7 or -CH2NR8R9, R5 means hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon rings -alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R6 and R7 respectively mean, independently of one another hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, "halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine atoms, chlorine and / or bromine, Re and R7 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle, with 5 or 6 atoms in the substituted ring, if appropriate, "from one to four times, in the same or in different ways, by halogen or by alkyl having 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, which are not contiguous in the series consisting of oxygen, sulfur or NR10, can contain R8 and R9. , independently of one another, hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R8 and R9 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle, with 5 or 6 ring atoms, optionally substituted one or more times, in the same or different manner by halogen or by alkyl with 1 to 4 carbon atoms, contain the heterocycle 1 or 2 heteroatoms more, not contiguous, of the series formed by oxygen, sulfur or NR 10, R 10 means hydrogen or alkyl having 1 to 4 carbon atoms, M means one of the following cycles the bond being linked with "*" to the amide, the bond marked "#" being linked to the haloalkyl moiety, R '11 meaning hydrogen, fluorine, chlorine, methyl or trifluoromethyl, RII-A is hydrogen, methyl or trifluoromethyl, A means the rest of the formula (Al) R12 means hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, halogenalkyl with 1 to 2 carbon atoms, haloalkoxy- with 1 to 2. carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl atoms, R 13 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio, - - R14 means hydrogen, methyl, ethyl, n-propyl, isopropyl, halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl, or A means the rest of the formula (A2) R15 and R16 are independently hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R17 means fluorine, chlorine, bromine, cyano, methyl, ethyl, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A3) R18 and R19 mean, independently of one another, -hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R20 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A4) R21 means hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, halogen with 1 to 2 carbon atoms, halogen with 1 to 2 carbon atoms or halogenalkylthio with 1 to 2 carbon atoms carbon with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A5) R22 means fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 atoms of carbon with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, R 23 denotes hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, alkylsulfinyl with 1 to 2 carbon atoms or alkylsulfonyl with 1 to 2 carbon atoms, or A means the rest of the formula (A6) R24 means methyl, ethyl or haloalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R25 means methyl or ethyl, Q1 means S (sulfur), SO2 or CH2, p means 0 or 1, or A means the rest of the formula (A7) to R26 (A7), in which R2d means methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A8) R27 means methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A9) R28 and R29 mean, independently of one another, hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R30 means hydrogen , fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenoalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (AlO) R31 and R32 mean, independently of one another, hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R33 means hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, A means the remainder of the formula (All) R34 means hydrogen, fluorine, chlorine, bromine, amino, alkylamino with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms) amino, cyano, methyl, ethyl or halogenoalkyl with 1 to 2 carbon atoms with 1 up to 5 fluorine, chlorine and / or bromine atoms, R35 means fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the rest of the formula (A12) (A12), wherein R3e means hydrogen, fluorine, chlorine, bromine, amino, alkylamino with 1 to 4 carbon atoms, di (C1-C4 alkyl) amino, cyano, methyl, ethyl or haloalkyl with 1 at 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R37 means fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine atoms, chlorine and / or bromine, or A means the rest of the formula (A13) R38 means fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A14) (Alé), wherein R 39 means hydrogen, methyl or ethyl, R 40 means fluorine, chlorine, bromine, methyl or ethyl, or A means the remainder of the formula (A 15) R4X means methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A16) R42 denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A17) R, 3 means fluorine, chlorine, bromine, iodine, hydroxy, alkyl with 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 atoms of carbon with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A18) R44 means hydrogen, methyl, ethyl, halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, alkoxy with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl, R45 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R4S means hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or halogenalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, P47 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A19) R48 means methyl, ethyl, n-propyl or iso-propyl. 3. Process for the preparation of haloalkylcarboxamides of the formula (I) according to claim 1, characterized in that a) carboxylic acid derivatives of the formula (II) O are reacted A X (II) wherein A has the above indicated meanings and X 1 means halogen or hydroxy, with an aniline derivative of the formula (III) wherein R, R1, R2, R3, R4 and M have the meanings indicated in claim 1, optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of a acid acceptor and, if appropriate, in the presence of a diluent, or b) hexylcarboxanilides of the formula (Ia) are reacted wherein R, R1, R2, R3, M and A have the indicated meanings-- in claim 1, with halides of the formula (IV) r, 4-A v2 R -X (IV) wherein = _X2 means chlorine, bromine or iodine, - R4_A means alkenyl with 1 to 8 carbon atoms, alkylsulfinyl. with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) Caryl-C 1 -alkyl 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) carbonylalkyl with 1 to 3 carbon atoms with, respectively, 1 a 13 fluorine, chlorine and / or bromine atoms; (alkyl with 1 to 8 carbon atoms) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms) carbonyl, (cycloalkyl with 3 to 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or C (= 0) C (= 0) R5, -CONR6R7 or -CH2NR8R9. having R5, R6, R7, R8 and R9 the meanings indicated above, in the presence of a base and in the presence of a diluent. 4. - Agents for the fight against undesirable microorganisms, characterized in that they have a content in at least one haloalkylcarboxamide of the formula (I), according to claim 1, together with extenders and / or surfactants. 5. Use of the haloalkylcarboxamides of the formula (I), according to claim 1, for the control against undesirable microorganisms. 6. - Procedure for the fight against undesirable microorganisms, characterized in that halogenoalkylcarboxamides of the formula (I) are applied, according to claim 1, on the microorganisms and / or on their environment. 7. - Procedure for obtaining agents for the fight against undesirable microorganisms, characterized in that haloalkylcarboxamides of the formula are mixed (I), according to claim 1, with extender agents and / or surfactant products. 8.- Aniline derivatives of the formula (III), characterized in that R, R1, R2, R3, R4 and M in accordance with claim

1.