MX2008009989A

MX2008009989A - Pyridin-4 -ylmethylamides for combating pests

Info

Publication number: MX2008009989A
Application number: MXMX/A/2008/009989A
Authority: MX
Inventors: Muller Bernd; Grammenos Wassilios; Rheinheimer Joachim; Michaelpuhl; Dietz Jochen; Renner Jens; Lohmann Janklaas
Original assignee: Basf Se
Priority date: 2006-02-14
Filing date: 2008-08-04
Publication date: 2008-10-03

Abstract

The present invention relates to pyridin-4-ylmethylamides of the general formula (I), where R1to R6and n are as defined in the claims and to the N-oxides and the agriculturally acceptable salts of the compounds I. The invention also relates to a process for preparing these compounds. Furthermore, the invention relates to the use of the compounds I and the N-oxides and the agriculturally acceptable salts thereof for combating phytopathogenic fungi (hereinafter referred to as harmful fungi). Furthermore the compounds I, their N-oxides and salts can be used for controlling arthropodal pests.

Description

DESCRIPTIVE MEMORY The present invention relates to pyridin-4-ylmethylamides of the general formula wherein R1 is hydrogen, C1-C6alkyl, C1-C6alkoxy, cyano-C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl, haloalkoxy Ci-C ^ -Cl-C4alkyl, di (C 1 -C 4 alkyl) amino-Ci-C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 3 -C 6 halocycloalkyl-C 1 -C 4 alkyl, (C 1 -C 4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, alkenyl C2-C6, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C5-C6 cycloalkenyl, N-heterocyclyl-saturated C4-C4 alkyl, C2-C4 cyano-alkenyl, C2-C4 haloalkenyl, Ci-C4 alkoxy -C2-C4alkenyl, C2-C4 Ci-C2-alkenyl, C2-C4alkyl, C2-C4alkenyl, (alkoxy?! - 04) carbonyl-C2-C4alkenyl, di (C1-C4alkyl) haloalkoxy; C2-C4 amino-alkenyl, C2-C6 alkynyl, C2-C4 haloalkynyl, Ci-C4 haloalkyl C2-C4 alkynyl, C2-C4 alkynyl C2-C4 alkynyl, tri (C1-C4 alkyl) silyl-C2-C4 alkynyl , di (Ci-C4 alkyl) amino, naphthylmethyl or benzyl, wherein the last two mentioned radicals can carry on the ring phenyl or naphthyl 1, 2 or 3 radical selected from cyano, halogen, Ci-C4 alkyl radical, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (Ci-C4 alkyl) carbonyl, (C1-C4 alkoxy) carbonyl and di (alkyl) C1-C4) amino; R2, R3, R4, R5 are independently selected from hydrogen, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, tri-C1-C4-alkyl, C1-C4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, S (0) pR 16 and NR 17 R 18; or R2 and R3 together with the carbon atoms to which they are attached can form a 5 or 6 membered fused carbocycle or a 5 or 6 membered fused heterocycle containing one, two or three heteroatoms as ring members, being selected from the group consisting of nitrogen, oxygen and sulfur atoms, it being possible for the fused ring to carry one or two radicals R7 and / or R8, R6 is halogen, cyano, nitro, C1-C10 alkyl, C2-C2 alkenyl, C2-alkynyl -C10, C1-C10 alkoxy, Ci-C1 haloalkyl, C1-C10 haloalkoxy, (C1-C4 alkyl) carbonyl, (Ci-C4 alkoxy) carbonyl, -C (R9) = NOR10, (C1-C4 alkyl) aminocarbonyl , di (C 1 -C 4 alkyl) aminocarbonyl, 5 or 6 membered hetaryl or hetaryloxy containing one or two heteroatoms as ring members, being selected from the group of nitrogen, oxygen and sulfur atoms, phenyl or phenoxy, wherein the phenyl or hetaryl ring in the last four radicals mentioned can carry one, two or three s radicals R; two R6 radicals together with two adjacent carbon atoms of the pyridyl ring to which they are attached may also form a 5 or 6 membered fused carbocycle which may be substituted with 1, 2 or 3 radicals R12; R1, R8 are, independently of each other, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or Ci-d haloalkoxy; n is 0, 1 6 2; R9 is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, Ci-C4 alkoxy-C1-C4 alkyl, haloalkoxy Ci-C4-C1-C4 alkyl, phenyl which can carry a cyano, halogen, C1-C4 alkoxy or haloalkoxy radical C1-C4, or benzyl which may be unsubstituted or substituted by 1, 2 or 3 radicals, selected from cyano, halogen and C1-C4 alkyl; R10 is Ci-C6 alkyl, benzyl, C2-C4 alkenyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 alkynyl or C2-C4 haloalkynyl; R11 is nitro, cyano, OH, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (Ci-C4 alkoxy) carbonyl, Ci-C4 alkylcarbonyl, CHO, CO-NH2 , C 1 -C 4 alkyl-aminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, C 1 -C 4 alkylthio, haloalkyl Cj-C 4 -thio, C 1 -C 4 alkylsulfinyl, haloalkyl C 1 -C 4 -sulfinyl, Ci-C alkyl ^ -sulfonyl, Ci-C4-haloalkyl sulfonyl, (Ci-C4 alkyl> amino, di (Ci-C4 alkyl) amino, tri (Ci-C) alkylsilyl, -C (R13) = NOR14, C2-C4 alkenyl or C2-C4 alkynyl, two R11 radicals together with two adjacent atoms of the phenyl ring to which they are attached can form a 5 or 6 membered fused carbocycle or a 5 or 6 membered fused heterocycle containing one, two or three heteroatoms as members of the ring, being selected from the group consisting of nitrogen, oxygen and sulfur atoms, it being possible for the fused ring to carry 1, 2 or 3 radicals R12a; R12, R12a are independently selected from halogen, cyano, nitro, Ci-Cs alkyl, C1-C8 haloalkyl, Ci-Cg alkoxy, Ci-Ce haloalkoxy, (C1-C alkyl) carbonyl, (C1 alkoxy) -C4) carbonyl, -C (R13a) = NOR14a, (Cj-C alkyl) aminocarbonyl, di (Ci-C4 alkyl) aminocarbonyl, phenyl and phenoxy, wherein the ring in the last two mentioned radicals can carry one, two or three groups R15; R13, R13a are independently selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy-C1-C4 alkyl, phenyl which may be unsubstituted or may be substituted substituted with 1, 2 or 3 radicals, selected from cyano, halogen, C1-C alkoxy and C 1 -C 4 haloalkoxy, or benzyl which may be unsubstituted or substituted by 1, 2 or 3 radicals, selected from cyano, Halogen and C 1 -C 4 alkyl R 14, R 14a are independently selected from C 1 -C 6 alkyl, benzyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl and C 2 - haloalkynyl C4; R 15 is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, haloalkyl Ci or haloalkoxy d; R16 is C1-C4 alkyl or C1-C4 haloalkyl and p is 0, 1 or 2; and R17, R1B are independently selected from hydrogen, Ci-C6 alkyl or R17 and R18 together with the nitrogen atom to which they are attached, form a saturated heterocycle of five to eight members which is attached through a nitrogen and which may contain one, two more three heteroatoms or groups of heteroatoms of the group consisting of O, N, S, S (O) and S (O) 2 as ring members, it being possible for the heterocycle to carry 1, 2, 3 or 4 substituents selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or halogen; and the N-oxides and the agriculturally acceptable salts of compounds I. WO 2005/33081 describes 4-pyridylmethylamides of benzenesulfonic acid compounds and their use for combating harmful fungi. However, the action of the disclosed compounds is not always completely satisfactory. Accordingly, it was an object of the present invention to provide compounds that have a better action and / or a broader spectrum of action against harmful fungi. It was found that this object is achieved by means of the compounds of the general formula I, their N-oxides and salts, as defined herein. In comparison with the known compounds, the compounds of the formula I have a higher efficacy against harmful fungi. Therefore, the invention relates to compounds of the general formula I, their N-oxides and their salts. The invention also relates to a process for preparing these compounds. On the other hand, the invention relates to the use of the compounds I and the N-oxides and their salts acceptable in agriculture for combating phytopathogenic fungi (hereinafter referred to as harmful fungi). Accordingly, the invention also provides a method for combating phytopathogenic fungi comprising the treatment of fungi or materials, plants, soil or seeds to be protected from a fungal attack with an effective amount of at least one pyridine-4. -ylmethyl-amide of the formula I and / or an N-oxide or one of its acceptable salts in agriculture. Accordingly, the invention also provides agricultural compositions, preferably in the form of solutions, directly sprayable emulsions, pastes, oil dispersions, powders, dispersion materials, powders or in the form of granules, comprising an amount of pesticidal efficacy of minus one compound I, and / or one of its N-oxides or one of its salts, and at least one carrier which may be liquid and / or solid and which is preferably acceptable in agronomy, and / or at least one surfactant. On the other hand, it was found that compounds I, their N-oxides and salts can be used to control or control arthropod pests. The compounds I, their N-oxides and salts are useful in particular for controlling insects. Also, compounds I, their N-oxides and salts are useful, in particular, to combat arachnids. The term "combating an arthropod pest" as used herein comprises controlling, i.e., killing said pests and also protecting plants, non-living materials or seeds from attack or infestation by said pests. Therefore, the invention relates to the use of compounds I and N-oxides and their salts acceptable in agriculture, to combat arthropod pests. On the other hand, the invention provides a method for combating said pests, comprising contacting said pests, their habitat, nutrient soil, food supply, plant, seed, soil, area, material or environment where arthropod pests grow or they may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from an attack or infestation by said pest, with a pesticidally effective amount of at least one pyridin-4-ylmethyl-amide compound of the formula I, and / or one of its N-oxides or salts, or with a composition comprising at least one pyridin-4-ylmethyl-amide compound of the formula I, and / or N-oxide, or one of its acceptable salts in agriculture, as defined herein. The invention provides in particular a method for protecting crops, including seeds, of attack or infestation by arthropod pests and / or phytopathogenic fungal infection, which method comprises contacting a culture with an effective amount of at least one compound of formula I and / or its N-oxide or salt, as defined herein. The invention also provides seeds, which comprise at least one pyridin-4-ylmethyl-amide compound of the formula I, and / or an N-oxide or an agriculturally acceptable salt thereof, preferably in an amount of about 0, 1 g to 10 kg per 100 kg of seed. The invention also provides a method for protecting non-living materials from attack or infestation by the aforementioned harmful pests and / or fungi, which method comprises contacting the non-living material with a pesticidally effective amount of at least one compound of the invention. Formula I as defined herein, with one of its trioxides or one of its salts. Suitable compounds of the formula I include all possible stereoisomers (cis / trans isomers, enantiomers) that can be present and their mixtures. The stereoisomeric centers are, for example, the carbon and nitrogen atom of the radical -C (R9) = NOR10, as well as asymmetric carbon atoms in the radicals R1, R2, R3, R4 and / or R5 etc. The present invention provides both the enantiomers and the pure diastereomers or mixtures thereof, the pure cis and trans isomers and mixtures thereof. The compounds of the general formula I can also exist in the form of different tautomers. The invention comprises individual tautomers, if separable, as well as mixtures of tautomers. The present invention includes both the (R) and (S) isomer of the compounds of the formula I with chiral centers, as well as their mixtures, in particular their racemates. The salts of the compounds of the formula I and the N-oxides of the formula I are acceptable in agriculture. They can be formed by conventional methods, for example, by reacting the compound with an acid of the anion in question when the compound of formula I has a basic functionality or by reaction with an acidic compound of formula I with an appropriate base. Suitable salts useful in agriculture include the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have an adverse effect on the action of the compounds according to the present invention. Suitable cations are, in particular, the alkali metal ions, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4 +) and substituted ammonium, wherein one to four of the hydrogen atoms are replaced by C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, Ci-Cj alkoxy, C 1 -C 4 alkoxy, hydroxy-C 1 alkoxy, C4-C1-C4 alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium. dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyethoxy) ethylammonium, bis (2-hydroxyethyl) ammonium, benzyltrimethylammonium and benzyltriethylammonium, also phosphonium ions, sulfonium ions, preferably tri (C1 -C4) sulfonium, and sulfoxonium ions, preferably tri (C1-C4 alkyl) sulfoxonium. The anions of salts by addition of useful acids are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the C1-C4 alkanoic acid anions, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formula I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. The organic residues mentioned in the above definitions of the variables are -as the term halogen- collective terms for individual lists of members of the individual group. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group. Halogen: fluorine, chlorine, bromine and iodine; Alkyl and all alkyl residues in alkylcarbonyl, tri (alkyl) silyl, dialkylamino, dialkylaminocarbonyl: straight or branched chain saturated hydrocarbon radicals having 1 to 4, 6, 8 or 10 carbon atoms, (Ci-Ce alkyl) with preference from 1 to 6 carbon atoms, especially (C 1 -C 4) alkyl of 1 to 4 carbon atoms such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl , pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl , 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 , 1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; (Ci-C10 alkyl) having 1 to 10 carbon atoms: Ci-C6 alkyl as mentioned above, and also, for example, heptyl, octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, 1, 1, 3, 3-tetramethylbutyl, nonyl and decyl; Alkoxy: straight or branched chain saturated hydrocarbon radicals having 1 to 4, 6, 8 or 10 carbon atoms, preferably 1 to 6 carbon atoms, especially 1 to 4 carbon atoms, as defined herein , which is linked to the rest of the molecule through an oxygen ligation; Haloalkyl: straight or branched chain alkyl groups having 1 to 2, 4, 6, 8 or 10 carbon atoms (as mentioned above), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above: in particular C 1 -C 2 haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, ciorodifluoromethyl, 1-clproethyl, 1-bromoethyl, 1-fluoroethyl , 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2.2 , 2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl; Haloalkoxy radicals and all haloalkoxy radicals in haloalkoxyalkyl, haloalkoxy alkenyl: straight or branched chain alkyl groups having 1 to 4, 6, 8 or 10 carbon atoms, in particular (haloalkyl Ci-Ce) of 1 to 6 carbon atoms carbon, in particular (C1-C4 haloalkyl) of 1 to 4 carbon atoms, as mentioned above bound through an oxygen bond, at any bond in the alkyl group, wherein some or all of the hydrogen atoms in these groups they may be replaced by halogen atoms as mentioned above, for example, C1-C2 haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, ciorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2.2 -difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, 5-fluoropentoxy , 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy or 6-iodohexoxy and the like; Haloalkylthio: straight or branched chain alkyl group having 1 to 4 carbon atoms, as mentioned above which is linked to the rest of the molecule through a sulfur linkage, where some or all of the hydrogen atoms they may be replaced by halogen atoms as mentioned above; Haloalkylsulfinyl: straight or branched chain alkyl group having 1 to 4 carbon atoms, as mentioned above which is linked to the rest of the molecule through an SO group, wherein some or all of the hydrogen atoms may be be replaced by halogen atoms as mentioned above; Haloalkylsulfonyl: straight or branched chain alkyl group having 1 to 4 carbon atoms, as mentioned above which is linked to the remainder of the molecule through a group S02, wherein some or all of the hydrogen atoms may be be replaced by halogen atoms as mentioned above; Alkenyl: straight or branched chain unsaturated hydrocarbon radicals having 2 to 4, 6, 8 or 10 carbon atoms and one or two double bonds at any position, for example, C2-C6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2 propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, l-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4- hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl- 2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3- pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2, 3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3, 3-dimethyl-l-butenyl, 3, 3-dimethyl-2-butenyl, 1-ethyl-l-butenyl, l- ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1-trimethyl-2-propenyl, l-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl; Haloalkenyl: straight or branched chain unsaturated hydrocarbon radicals having 2 to 4 carbon atoms and one or two double bonds at any position (as mentioned above), wherein in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular with fluorine, chlorine and bromine; Alkynyl: straight or branched chain hydrocarbon groups having 2 to 4, 6, 8 or 10 carbon atoms and one or two triple bonds at any position, for example, C2-C6 alkynyl, such as ethynyl, 1-propynyl, -propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl -3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl , 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, -methyl-1-pentinyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl , 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl -3-butynyl and 1-ethyl-l-methyl-2-propynyl; Haloalkynyl: straight or branched chain unsaturated hydrocarbon radicals having 2 to 4 carbon atoms and a triple bond at any position (as mentioned above), wherein in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular with fluorine, chlorine and bromine; Cycloalkyl: saturated mono- or bicyclic hydrocarbon groups having 3 to 6 carbon ring members, for example, C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 5 to 6 carbon ring members (C5-C6 cycloalkenyl), such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen -4-ilo; Tri (C 1 -C 4 alkyl) silyl: silicon radical bearing 3 C 1 -C 4 alkyl groups, which may be the same or different, examples of which include trimethylsilyl, triethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-n-butylsilyl, dimethyl-2- butylsilyl, etc .; The terms "cyano-C 1 -C 4 alkyl", "C 1 -C 4 alkoxy-C 1 -C 4 alkyl", "C 1 -C 4 haloalkoxy-C 1 -C 4 alkyl", "di (C 1 -C 4 alkyl) amino-C 1 -C 4 alkyl" "," C3-C6 cycloalkyl-C1-C4 alkyl "," C3-C6 halocycloalkyl-C1-d alkyl "," N-heterocyclyl-saturated C1- C4 alkyl ", as used herein , refer to C 1 -C 4 alkyl, as defined herein, which is substituted with a radical selected from cyano, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, di (C 1 -C 4 alkyl) amino, C 3 -C 6 cycloalkyl , C3-C6 halocycloalkyl, saturated 5- or 6-membered N-heterocyclyl; The terms "C2-C4 cyano-alkenyl", "C2-C4 alkoxy-C2-C2 alkenyl", "C2-4 haloalkoxy-C4-alkenyl", "(C1-C4 alkyl) carbonyl-C2-alkenyl" C4"," (C 1 -C 4 alkoxy) carbonyl-C2-C4 alkenyl "," di (C1-C4 alkyl) amino-C2-C4 alkenyl "refer to C2-C4 alkenyl, as defined herein, which is substituted with a radical selected from cyano, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, (C 1 -C 4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, di (C 1 -C 4 alkyl) amino; The terms "haloalkyl Ci-C4-C2-C4 alkynyl", "C4-C4 alkyloxyC2-C4 alkynyl", "tri (C1-C4 alkyl) silyl-C2-C4 alkynyl" refer to C2-C4 alkynyl, as defined herein, which is substituted with a radical selected from C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, tri (C 1 -C 4 alkyl) silyl; A five- or six-membered heterocycle containing one, two, three or four heteroatoms of the group consisting of O, N and S is understood to mean saturated, partially unsaturated and aromatic heterocycles having 5-6 ring atoms, including: - heterocyclyl of 5 or 6 members containing one, two or three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, and which is saturated or partially unsaturated, for example, -tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl , 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-ioxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-pyrrolin-2 -yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-pi peridinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl and 2-piperazinyl; - 5-membered aromatic heterocyclyl (heteroaryl) containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl groups which, in addition to the atoms of carbon, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, for example, 2-thienyl, 3-thienyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl and 1, 3, 4-triazol-2-yl; - 6-membered heteroaryl containing one, two, three or four nitrogen atoms: 6-membered heteroaryl groups which, in addition to the carbon atoms, may contain one, two, three or four nitrogen atoms as ring members, example, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl. Likewise, a saturated heterocycle of five to eight members which is linked through a nitrogen and which may contain one, two more three heteroatoms or groups of heteroatoms of the group consisting of 0, N, S, S (0) and S ( 0) 2 as members of the ring, is a saturated heterocycle containing a nitrogen atom as ring member and which is attached to the rest of the molecule through a nitrogen atom and having 5, 6, 7 or 8 carbon atoms. ring which are carbon atoms or heteroatoms such as O, N or S or groups of heteroatoms such as S (0) or S (0> 2; examples include pyrrolidin-1-yl, piperazin-1-yl, morpholino- 4-yl, thiomorpholin-4-yl, azepane-l, etc. Fused 5 or 6-membered carbonate means a hydrocarbon ring that shares two adjacent carbon atoms with another ring, examples of which are cyclopentane, cyclopentene, cyclohexane, cyclohexene and benzene Examples of 5- or 6-membered heterocycles containing a carbocyclic ring 5 or 6 membered ico as mentioned above are indolyl, indolinyl, isoindolinyl, benzpyrazolyl, benzimidazolyl, benzotriazolyl, quinolinyl, 1, 2, 3, 4-tetrahydroquinolini, isoquinolinyl, phthalazinyl, quinazinyl, quinazolinyl, cinolinyl, benzofuranyl, benzothiophenyl, benzopyranyl, dihydrobenzopyranyl, benzothiopyranyl, 1,3-benzodioxolyl, benzoxazolyl, benzthiazolyl, benzisoxazolyl and 1,4-benzodioxanyl.

Alkylene: divalent non-branched chains of 1 to 5 CH2 groups, for example, CH2, CH2 CH2, CH2CH2CH2, CH2CH2CH2CH2 and CH2CH2CH2CH2CH2; Alkenylene: divalent unbranched chains of 4 or 6 CH groups which are linked by conjugated double bonds C = C, for example, CH = CH or CH = CH-CH = CH. In view of the intended uses of the pyridin-4-ylmethyl amides I, particular preference is given to the following meanings of the substituents, in each case alone or in combination. The invention preferably provides compounds of the formula I in which R 1 is hydrogen, C 1 -C 4 alkyl, C 3 -C 4 alkenyl such as allyl, C 3 -C 4 alkynyl such as propargyl or benzyl, in particular hydrogen. Preference is also given to compounds of the formula I in which R2, R3, R4 and R5 are independently selected from hydrogen, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C alkynyl < i, tri-alkyl Ci-C4-silyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, S (0) pR 16 and NR 17 R 18, in particular hydrogen, C 1 -C 4 alkyl such as methyl or ethyl, halogen, such as fluorine or chlorine, haloalkyl Ci ~ C2 such as CF3, or haloalkoxy Ci-C2 such as OC F3 or OCH F2. Particular preference is given to the compounds wherein R2, R3, R4 and R5 are hydrogen. In addition, particular preference is also given to the compounds of the formula I in which at least one, in particular one or two groups selected from R2, R3, R4 and R5 are not hydrogen. Among them, preference is given to those compounds in which both R 4 and R 5 are hydrogen, while at least one of the radicals R 2, R 3 is different from hydrogen and has one of the meanings given above. In particular, R 2 and / or R 3 which is different from hydrogen is selected from C 1 -C 4 alkyl such as methyl or ethyl, halogen, such as fluorine or chlorine, C 1 -C 2 haloalkyl such as CF 3 or C 1 -C 2 haloalkoxy such as OCF 3 or OCHF2. In this embodiment, preference is also given to compounds in which one of the radicals R2 and / or R3 is selected from C2-C4 alkenyl, C2-C4 alkynyl, tri (C1-d) alkylsilyl, a radical S (0) pR16 or a radical NR R18. The remaining radical R2 or R3 is preferably hydrogen or is selected from the group consisting of C! -C4 alkyl such as methyl or ethyl, halogen, such as fluorine or chlorine, haloalkyl C1-C2 such as CF3, or haloalkoxy C1 -C2 such as OCF3 or OCHF2. Likewise, preference is also given to the compounds of the formula I, in which the radicals R 2 and R 3, together with the atoms to which they are attached, form a fused benzene ring, that is, R 2 and R 3 together form a bivalent radical -CH = CH-CH = CH-, wherein one or two of the hydrogen atoms can be replaced by the radicals R7 and / or R8. In this embodiment, R4 and R5 are preferably hydrogen. Preferably, n is 1 or 2. When n is 1 or 2, preferably at least one radical R6 is located at the meta position or for the sulfonyl group. In a first preferred embodiment, n is 1 or 2 and R6 is selected from halogen, in particular chlorine and fluorine; C1-C4 alkyl, in particular methyl and ethyl; C 1 -C 4 alkoxy, in particular methoxy and ethoxy; C1-C4 haloalkyl, in particular trifluoromethyl; C1-C4 haloalkoxy, in particular difluoromethoxy and trifluoromethoxy; (C 1 -C 4 alkoxy) carbonyl, in particular methoxycarbonyl and ethoxycarbonyl. In a second preferred embodiment, n is 1 or 2 and one of the radicals R6 is phenyl or hetaryl having 5 or 6 members, which are unsubstituted or which can preferably carry 1, 2 or 3 radicals R11 as defined above. . More preference is given to compounds in which one of the radicals R6 is phenyl, which is unsubstituted or which preferably carries 1, 2 or 3 radicals Rn as defined above. If present, the other radical R6 is preferably different from phenyl, hetaryl, hetaryloxy or phenoxy, and more preferably is selected from halogen, in particular chlorine and fluorine; C1-C4 alkyl, in particular methyl and ethyl; C1-C4 alkoxy, in particular methoxy and ethoxy; C1-C4 haloalkyl, in particular trifluoromethyl; C1-C4 haloalkoxy, in particular difluoromethoxy and trifluoromethoxy; (Ci-C) alkoxycarbonyl, in particular methoxycarbonyl and ethoxycarbonyl. In the second embodiment, n is preferably 1. In the second embodiment, the phenyl ring or the hetaryl ring is preferably located in the meta position or for the sulfonyl group. Also preferred are compounds of the formula I, wherein R6 is 5 or 6 membered hetaryl or hetaryloxy containing one or two heteroatoms as ring members, selected from the group of nitrogen, oxygen and sulfur atoms, wherein the heterocycle may be not be substituted or can carry 1, 2 or 3 radicals R11. In this embodiment, R6 is preferably 5- or 6-membered heteroaryl, in particular pyridyl, thienyl, oxazolyl, isoxyzolyl, oxadiazolyl or thiadizolyl, more preferably 2-, 3- or 4-pyridyl, oxazol-5-yl , oxazol-2-yl or 1,3,4-oxadiazol-2-yl, wherein the hetaryl may be unsubstituted or may carry 1, 2 or 3 more preferably 1 6 2 R11 radicals as defined in Preferred pentarame of carrying out the compounds I according to the invention, the index n is zero. In the compounds of the formula I, the pyridine ring in the sulfonyl group can be attached through the carbon atom in the 2, 3 or 4 position of the pyridine ring, that is, the nitrogen atom of the pyridine ring can be located in the position ortho, meta or for the sulfonyl group. Accordingly, an embodiment of the invention relates to compounds of the formula I-A, wherein R1, R2, R3, R4, R5, R6 and n are as defined herein. Among the compounds I-A, preference is given to those in which n is 1 or 2 and in which the radical R6 is located in the 6-position of the pyridine ring. These compounds are also referred to as compounds I-A. to. Preference is also given to compounds I-A, wherein n is 1 or 2, in particular 1, and wherein a radical R6 is located at the 5-position of the pyridine ring. These compounds are also referred to as compounds I-A.b. Preference is also given to the compounds I-A, wherein n is 1 or 2, in particular 1, and wherein a radical R6 is located at the 4-position of the pyridine ring. These compounds are also referred to as compounds I-A.c. In the compounds I-A. a, I-A.b and I-A.c, the radical R6, which is located at the 4, 5 or 6 position, is most preferably phenyl, which is unsubstituted or substituted as defined above. Accordingly, another embodiment of the invention relates to compounds of the formula I-B, wherein R1, R2, R3, R4, R5, R6 and n are as defined herein. Among the compounds I-B, preference is given to those in which n is 1 or 2 and a radical R6 is located in the 6-position of the pyridine ring. These compounds are also referred to as compounds I-B. to. Preference is also given to compounds I-B, wherein n is 1 or 2 and a radical R6 is located at the 5-position of the pyridine ring. These compounds are also referred to as compounds I-B.b. In compounds I-B.a, and I-B.b, the radical R6, which is located at the 5 or 6 position, is most preferably phenyl, which is unsubstituted or substituted as defined above. Accordingly, another embodiment of the invention relates to compounds of the formula I-C, wherein R1, R2, R3, R4, R5, R6 and n are as defined herein. Among the compounds I-C, preference is given to those in which n is 1 or 2 and a radical R6 is located in the 2-position of the pyridine ring. These compounds are also referred to as compounds I-C. to. In the compounds I-C. a, the radical R6, which is located at position 2, is most preferably phenyl, which is unsubstituted or substituted as defined above. R7, if present, is preferably selected from halogen, in particular chlorine and fluorine; Ci-C4 alkyl, in particular methyl, ethyl, isopropyl, tert-butyl; Ci-C4 alkoxy, in particular methoxy, ethoxy, isopropoxy, ter. -butoxy; and haloalkyl Ci-C < , In particular trifluoromethyl and pentafluoroethyl. RB, if present, is preferably selected from halogen, in particular chlorine and fluorine; C1-C alkyl in particular methyl, ethyl, isopropyl, tert-butyl; C1-C4 alkoxy, in particular methoxy, ethoxy, isopropoxy, ter. -butoxy; and C 1 -C 4 haloalkyl, in particular trifluoromethyl and pentafluoroethyl. R9, R13, R13a, if present, are preferably selected, independently from each other, from hydrogen or C1-C4 alkyl, in particular hydrogen. R10, R14, R1 < the, if present, are preferably, independently of each other, C1-C4 alkyl. R11, if present, is preferably selected from nitro, CN, OH, halogen, C1-C4 alkyl, C1-C4 haloalkyl, Ci-Cj alkoxy, C1-C4 haloalkoxy, (Ci-C4 alkoxy) carbonyl, Ci-C alkyl -carbonyl, Ci-C4 alkyl thio, Ci-C ^-thio haloalkyl, Ci-C4 alkylsulfonyl, C1-C4 haloalkyl sulfonyl, (Ci-C4 alkyl) amino, di (alkyl dC ^ lamino, tri ( C 1 -C 4 alkyl) silyl, -CH = NO (C 1 -C 4 alkyl), -C (C 1 -C 4 alkyl) = NO (C 1 -C 4 alkyl), C 2 -C 4 alkenyl, C 3 -C 4 alkynyl or CONH 2, or two R11 radicals together with two adjacent atoms of the phenyl ring can form a radical of the formulas: ((¾) 3, (2 2) 4 O-CH2-0, 0 (CH2) 3 or -CH = CH-CH = CH.-R11, if present, is more preferably selected from CN, halogen, in particular fluorine or chlorine, C1-C4 alkyl, in particular methyl, ethyl, n-propyl., isopropyl or ter. -butyl, C1-C4 haloalkyl, in particular trifluoromethyl, difluoromethyl or trifluoroethyl, C1-C4 alkoxy, in particular methoxy, haloalkoxy C1-C4, in particular trifluoromethoxy, Ci-C4 alkylcarbonyl, in particular acetyl, CONH2, -CH = NOCH 3, -C (CH 3) = NOCH 3, CH = NOCH 2 CH 3, O -C (CH 3) = NOCH 2 CH 3. R16, if present, is preferably selected from methyl, ethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl. The radical NR17R18, if present, is preferably selected from NH2, methylamino, dimethylamino, ethylamino, diethylamino, propylamino, propylmethylamino, dipro-pilamino, 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl, 4-methylpiperazin-1-yl, morpholin-4-yl, 2-methylmorpholin-4-yl or 2,6-dimethylmorpholin-4-yl. Most preferably, R6 is phenyl having one, two or three radicals R11 as defined herein, in particular as indicated in the rows of table A. In table A, the prefix indicates the position of the phenyl ring at that the radical R11 is attached. Examples of preferred compounds are given in the following tables: Table 1 Compounds of formula I-A. a, wherein R1, R2, R3, R4 and R5 are hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 to 2 radicals R11 as defined in columns of table A. Table 2 Compounds of formula IA. a, in which R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is chlorine, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as is defined in the columns of Table A. Table 3 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is chloro, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as is defined in the columns of table A. Table 4 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is chloro, R3 is chloro, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as is defined in the columns of Table A. Table 5 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as is defined in the columns of table A. Table 6 Compounds of the formula IA. a, in which R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 6 2 R radicals such as is defined in the columns of Table A. Table 7 Compounds of the formula IA. a, wherein 1, R 4 and R 5 are hydrogen, R 2 is hydrogen, R 3 is methoxy, n is 1 and R 6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R 11 such as it is defined in the columns of Table A. Table 8 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as is defined in the columns of Table A. Table 9 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 to 2 radicals R11 such as is defined in the columns of Table A. Table 10 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as it is defined in the columns of Table A.

Table 11 Compounds of the formula I-A. a, in which R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 to 2 radicals R11 such as it is defined in the columns of Table A. Table 12 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as it is defined in the columns of Table A. Table 13 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is OCHF2, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 such as is defined in the columns of table A. Table 14 Compounds of the formula IA. a, wherein R1, R4 and R5 are hydrogen, R2 is OCHF2, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 to 2 radicals R11 such as is defined in the columns of table A. Table 15 Compounds of the formula IA.b, wherein R1, R2, R3, R4 and R5 are hydrogen, n is 1 and R6 is a phenyl ring that is located at the position 5 of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A. Table 16 Compounds of the formula IA.b, in which R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is chloro, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 17 Compounds of the formula IA. b, in which R1, R4 and R5 are hydrogen, R2 is chlorine, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 6 2 radicals R11 as defined in the columns of Table A. Table 18 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R2 is chlorine, R3 is chlorine, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 19 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 Rn radicals as defined in the columns of the Table A. Table 20 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 5-position of the ring pyridine and having 1 6 2 radicals R11 as defined in the columns of Table A. Table 21 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R2 is hi is hydrogen, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 6 2 radicals R11 as defined in the columns of Table A. Table 22 Compounds of the formula IA.b, where R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and carries 1 or 2 radicals Rn as defined in the columns of table A. Table 23 Compounds of the formula IA.b, where R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methoxy, n is 1 and R6 is a ring phenyl which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 24 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R 2 is methyl, R 3 is hydrogen, n is 1 and R 6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R 11 such as or is defined in the columns of Table A. Table 25 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methyl, n is 1 and R6 is a phenyl ring it is located at position 5 of the pyridine ring and carries 1 6 2 radicals R11 as defined in the columns of table A. Table 26 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of Table A. Table 27 Compounds of the formula IA.b, where R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is OCHF2, n is 1 and R6 is a phenyl ring that is located at position 5 of the pyridine ring and carrying 1 6 2 radicals R11 as defined in the columns of table A. Table 28 Compounds of the formula IA.b, wherein R1, R4 and R5 are hydrogen, R2 is OCHF2, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 Ru radicals as defined in the columns of Table A. Table 29 Compounds of the formula IA.c, wherein R1, R2, R3, R4 and R5 are hydrogen, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 6 2 radicals R11 as defined in the columns of table A. Table 30 Compounds of the formula IA.c, wherein R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is chlorine, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 31 Compounds of the formula IA.c, wherein R1, R4 and R5 is hydrogen, R2 is chloro, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 or 2 Rn radicals as defined in the columns of Table A Table 32 Compounds of the formula IA.c, wherein R1, R4 and R5 are hydrogen, R2 is chloro, R3 is chloro, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 or 2 radicals Rn as defined in the columns of Table A.

Table 33 Compounds of the formula IA.c, in which R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methyl, n is 1 and R6 is a phenyl ring which is located in the 4-position of the pyridine ring and which it carries 1 or 2 radicals R11 as defined in the columns of table A. Table 34 Compounds of the formula IA.c, in which R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 6 2 radicals R11 as defined in the columns of Table A. Table 35 Compounds of the formula IA.c, wherein R1 , R4 and R5 are hydrogen, R2 is hydrogen, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of Table A. Table 36 Compounds of formula IA.c, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at position 4 of the pyridine ring and carrying 1 6 2 radicals R11 as defined in the columns of Table A. Table 37 Compounds of the formula IA.c, in which R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 38 Compounds of the formula IA.c, in which R1, R4 and R5 are hydrogen, R2 is methyl, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located in the 4 position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of Table A. Table 39 Compounds of the formula IA.c, in which R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at position 4 of the pyridine ring and which carries 1 or 2 Ru radicals as defined in the columns of table A. Table 40 Compounds of formula IA.c, in which R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methyl, n is 1 and R6 is a phenyl ring which is located in the 4-position of the pyridine ring and which carries 1 to 6. 2 radicals R11 as defined in the columns of table A. Table 41 Compounds of the formula IA.c, in which R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is OCHF2, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 or 2 radicals R as defined in the columns of table A. Table 42 Compounds of the formula IA.c, wherein R 1, R 4 and R5 are hydrogen, R2 is OCHF2, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 4-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A Table 43 Compounds of the formula IB.a, in which R1, R2, R3, R4 and R5 are hydrogen, n is 1 and R6 is a phenyl ring which is located in the 6-position of the pyrid ring ina and carrying 1 6 2 radicals R11 as defined in the columns of Table A. Table 44 Compounds of the formula IB.a, wherein R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is chlorine, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 6 2 radicals R11 as defined in the columns of table A. Table 45 Compounds of the formula IB.a, in those which R1, R4 and R5 are hydrogen, R2 is chlorine, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 46 Compounds of the formula IB.a, wherein R1, R4 and R5 are hydrogen, R2 is chlorine, R3 is chlorine, n is 1 and R6 is a phenyl ring which is located on the position 6 of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A. Table 47 Compounds of the formula IB.a, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals Rn as defined in the columns of table A. 48 Compounds of the formula IB.a, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals Rn as defined in the columns of Table A. Table 49 Compounds of the formula IB.a, in which R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located in position 6 of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A. Table 50 Compounds of the formula IB.a, in which R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 6 2 radicals R11 as defined in the columns of table A. Table 51 Compounds of the formula IB.a, in which R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located in the 6-position of the pyrite ring idine and carrying 1 6 2 radicals R11 as defined in the columns of Table A. Table 52 Compounds of the formula IB.a, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 53 Compounds of the formula IB.a, in those which R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of Table A. Table 54 Compounds of the formula IB.a, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methyl, n is 1 and R6 is a phenyl ring which is located on the position 6 of the pyridine ring and carrying 1 6 2 radicals R11 as defined in the columns of table A. Table 55 Compounds of the formula IB.a, in which R1, R4 and Rs are hydrogen, R2 is hydrogen, R3 is OCHF2, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A Table 56: Compounds of the formula IB.a, wherein R1, R4 and R5 are hydrogen, R2 is OCHF2, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 6-position of the pyridine ring and having 1 or 2 radicals R11 as defined in the columns of Table A. Table 57 Compounds of the formula IB.b, wherein R1, R2, R3, R4 and R5 are hydrogen, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals Ru as defined in the columns of table A. Table 58 Compounds of the formula IB.b, wherein R 1, R 4 and R5 is hydrogen, R2 is hydrogen, R3 is chloro, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of Table A. Table 59 Compounds of the formula IB.b, wherein R1, R4 and R5 are hydrogen, R2 is chloro, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 60 Compounds of the formula IB.b, in which R1, R4 and R5 are hydrogen , R2 is chlorine, R3 is chlorine, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 61 Compounds of the formula IB.b, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 6 2 Ru radicals as defined in the columns of Table A. Table 62 Compounds of the formula IB.b, wherein R 1, R 4 and R 5 are hydrogen, R 2 is methyl, R 3 is methoxy , n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 63 Compounds of the formula I-B.b, wherein R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 R radicals as defined in the columns of table A. Table 64 Compounds of the formula IB.b, where R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is hydrogen, n is 1 and R6 is a phenyl ring that is located at position 5 of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A. Table 65 Compounds of the formula IB.b, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 66 Compounds of the formula IB.b, in which R1, R4 and Rs are hydrogen, R2 is methyl, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 5-position of the ring pyridine and having 1 or 2 radicals R as defined in the columns of table A. Table 67 Compounds of the formula IB.b, wherein R 1, R 4 and R 5 are hydrogen, R 2 is hydrogen, R 3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A.

Table 68 Compounds of the formula IB.b, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 R11 radicals as defined in the columns of Table A. Table 69 Compounds of the formula IB.b, wherein R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is OCHF2, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 70 Compounds of the formula IB.b, wherein R1 , R4 and R5 are hydrogen, R2 is OCHF2, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of Table A. Table 71 Compounds of the formula IC.a, in which R1, R2, R3, R4 and R5 are hydrogen n is 1 and R6 is a phenyl ring which is located in the 2 of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A. Table 72 Compounds of the formula IC.a, in which R1, R4 and R5 are hydrogen, R2 is chlorine, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 73 Compounds of the formula IC .a, in which R1, R4 and R5 are hydrogen, R2 is chlorine, R3 is chlorine, n is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 or 2 radicals Ru such as defined in the columns of table A. Table 74 Compounds of the formula IC.a, wherein R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methyl, n is 1 and R6 is a phenyl ring it is located at position 2 of the pyridine ring and carries 1 or 2 radicals R11 as defined in the columns of table A. Table 75 Compounds of the formula IC.a, in which s that R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 76 Compounds of the formula IC.a, wherein R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located on the position 2 of the pyridine ring and carrying 1 6 2 radicals R11 as defined in the columns of table A. Table 77 Compounds of the formula IC.a, in which R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 78 Compounds of the formula IC .a, in which R1, R4 and R5 are hydrogen, R2 is methoxy, R3 is methoxy, n is 1 and R6 is a phenyl ring which is located in the 2-position of the pyridine ring and having 1 or 2 radicals R11 as defined in the columns of Table A. Table 79 Compounds of the formula IC.a, wherein R1, R4 and R5 are hydrogen, R2 is methyl, R3 is hydrogen, is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 80 Compounds of the formula IC.a, in the that R1, R4 and R5 are hydrogen, R2 is hydrogen, R3 is methyl, n is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 to 2 radicals R11 as defined in columns of table A. Table 81 Compounds of the formula IC.a, in which R1, R4 and R5 are hydrogen, R2 is methyl, R3 is methyl, n is 1 and R6 is a phenyl ring which is located in the 2 of the pyridine ring and carrying 1 or 2 R11 radicals as defined in the columns of table A. Table 82 Compounds of the formula IC.a, in which R1, R4 and R5 are n hydrogen, R2 is hydrogen, R3 is OCHF2, n is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 83 Compounds of the formula IC.a, wherein R1, R4 and R5 are hydrogen, R2 is OCHF2, R3 is hydrogen, n is 1 and R6 is a phenyl ring which is located at the 2-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 84 Compounds of the formula IC.a, in which R1, R2, R3, R4 and R5 are hydrogen, n is 1 and R6 is a phenyl ring that is located in the 2-position of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A. Table 85 Compounds of the formula IA. a, in which R1, R4 and R5 are hydrogen, R2 and R3 together form a moiety -CH = CH-CH = CH-, n is 1 and R6 is a phenyl ring that is located at the 6-position of the pyridine ring and which has 1 6 2 radicals R as defined in the columns of table A. Table 86 Compounds of the formula IA.b, in which R 1, R 4 and R 5 are hydrogen, R 2 and R 3 together form a radical -CH = CH-CH = CH-, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of table A. Table 87 Compounds of the formula IA.c, in which R1, R4 and R5 are hydrogen, R2 and R3 together form a moiety -CH = CH-CH = CH-, n is 1 and R6 is a phenyl ring which is located in the 4-position of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A. Table 88 Compounds of the formula IB.a, in which R1, R4 and R5 are hydrogen, R2 and R3 together form a rest -CH = CH-CH = CH-, n is 1 and R6 is a phenyl ring which is located in the 6-position of the pyridine ring and which carries 1 6 2 radicals R11 as defined in the columns of table A. Table 89 Compounds of the formula IB.b, in which R1, R4 and R5 are hydrogen, R2 and R3 together form a moiety -CH = CH-CH = CH-, n is 1 and R6 is a phenyl ring which is located at the 5-position of the pyridine ring and which carries 1 or 2 radicals R11 as defined in the columns of Table A.

Table 90 Compounds of the formula IC.a, in which R1, R4 and R5 are hydrogen, R2 and R3 together form a moiety -CH = CH-CH = CH-, n is 1 and R6 is a phenyl ring which is located at position 2 of the pyridine ring and carrying 1 or 2 radicals R11 as defined in the columns of table A.

Table A The compounds I according to the invention can be prepared analogously to the methods described in the art. Advantageously, they are obtained from pyridine derivatives of the formula II. An appropriate process for the preparation of the compounds I comprises the reaction of the compounds II with sulphonic acids or sulfonic acid derivatives of the formula III, under basic conditions as described in the following reaction scheme: II III In formulas II and III, n and the radicals R1, R2, R3, R4, R5 and R6 are as defined above. In formula III, L is an appropriate leaving group such as hydroxyl or halogen, preferably chlorine. This reaction is usually carried out at temperatures of (-30) ° C to 120 ° C, preferably (-10) ° C to 100 ° C, in an inert organic solvent in the presence of a base [comp. Lieb. Ann. Chem. 641 (1990)]. Suitable solvents include aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as as diethyl ether, diisopropyl ether, ether ter. -butyl methyl, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and ter. -butyl methyl ketone, and also dimethylsulfoxide, dimethylformamide and dimethylacetamide, with particular preference diisopropyl ether, diethyl ether and tetrahydrofuran. It is also possible to use mixtures of the aforementioned solvents. Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide , sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates, such as lithium carbonate , potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, more even organic bases, for example, tertiary amines, such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylamino-pyridine, and also bicyclic amines. Particular preference is given to pyridine, triethylamine and potassium carbonate.

The bases are generally used in catalytic amounts; however, they can be used preferably in equimolar amounts, in particular in excess or, if appropriate, as a solvent. The starting materials generally react with each other in equimolar amounts. In terms of performance, it may be advantageous to use an excess of II, based on III. The compounds, wherein R6 is optionally substituted phenyl or hetaryl, can also be prepared from the compounds I, wherein R6 is halogen, in particular bromine, by a coupling reaction as a Stille coupling or under coupling conditions of Suzuki, for example, by means of the reaction indicated in the following reaction scheme: In the formulas a, Ib and IV, the variables R1, R2, R3, R4, R5, and R11 are as previously defined. The variable k is 0 or 1. The variable p is 0, 1, 2 or 3. R6a has one of the meanings given for R6, except for phenyl or hetaryl of 5 or 6 members. R6b is phenyl or hetaryl of 5 or 6 members. Hal in formula is halogen, in particular bromine. X in formula IV is OH or C1-C4 alkoxy. Cat is a transition metal catalyst, in particular a Pd catalyst. The reaction conditions can be taken from the working examples or from Suzuki et al., Chem. Rev, 1995, 95, 2457-2483 and the literature cited therein. Intermediate III can be prepared from the respective pyridyl halide V by treatment with alkylmagnesium halides such as iPrMgCl, S02 and S02C12 as indicated in the following scheme. (CH3) 2CH-gCI 0 (RV © N -Hal S02, S02CI2 (R6Ht N r OhL V III The starting materials required to prepare the compounds I are commercially available or are known in the art and can be prepared by analogy to the methods described in the art. For example, the aminomethylpyridine compounds of the formula II wherein one or more of the radicals R2, R3, R4 or R5 are different from hydrogen, such as (halo) alkoxy, (halo) alkylthio, (halo) alkyl, alkenyl, trialkylsilyl or alkynyl, can be prepared from halopyridinecarbonitriles by replacing a halogen radical with a non-halogen radical, by means of a nucleophilic substitution reaction or by means of a coupling reaction, for example, by treatment with appropriate nucleophiles such as HNR11R18, (halo) alkoxide, (halo) alkylthio, an organometallic compound, optionally in the presence of a transition metal catalyst, to obtain the corresponding substituted carbonitrile [cf. Journal of Medicinal Chemistry, 22 (11), 1284-90; 1979; U. S., 4,558,134, Synthesis, (6), 763-768; 1996 and Heterocycles, 41 (4), 675-88; 1995], and subsequent hydrogenation of the radical C = N to obtain the corresponding aminomethylpyridine compound II, wherein 1 is hydrogen, [comp. Heterocycles, 41 (4), 675-88; nineteen ninety five; Recueil des Travaux Chimiques des Pais-Bas et de la Belgique, 52, 55-60; 1933; Acta Poloniae Pharmaceutica, 32 (3), 265-8; 1975; Journal of Medicinal Chemistry, 24 (1), 115-17; 1981, P 49173, Heterocycles, 41 (4), 675-88; 1995, Angewandte Chemie, International Edition, 43 (37), 4902-4906; 2004; Journal of Heterocyclic Chemistry, 19 (6), 1551-2; 1982]. The subsequent alkylation of aminomethyl nitrogen results in compounds in which R1 is different from hydrogen. The reaction mixtures are worked up in the usual manner, for example by mixing with water, separating the phases and, if appropriate, chromatographically purifying the crude products. Some of the intermediates and final products are obtained in the form of colorless or slightly brown viscous oils which can be purified or released from the volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and final products are obtained as solids, purification is also carried out by recrystallization or digestion. The N-oxides can be prepared from the compounds I according to conventional oxidation methods, for example by treating the pyridine I compounds with an organic peracid such as metachloroperbenzoic acid [Journal of Medicinal Chemistry, 38 (11), 1892 -1903 (1995); WO 03/64572] or with inorganic oxidizing agents such as hydrogen peroxide [cf. Jounal of Heterocyclic Chemistry, 18 (7), 1305-8 (1981)] or oxone [comp. Journal of the American Chemical Society, 123 (25), 5962-5973 (2001)]. Oxidation can lead to pure mono, bis- or tri-N-oxides or to a mixture of different N-oxides which can be separated by conventional methods such as chromatography. Preferably, one or two pyridine nitrogens in the compounds I are oxidized in the corresponding mono- or bis-N-oxides. If each of the compounds I can not be obtained by the routes described above, they can be prepared by derivatization of other compounds I. If the synthesis produces mixtures of isomers, the separation is not usually required, since in some cases the different isomers can interconvert during the preparation of use or during the application (for example before the action of light, acids or bases). Such conversions can also take place after use, for example in the treatment of plants of the treated plant, or in the harmful fungus or pest that is sought to be controlled. The compounds I are suitable as fungicides. They are distinguished by the remarkable effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some are effective as systemic and can be used for the protection of crops such as foliar fungicides, fungicides to cover seeds and soil fungicides. They are particularly important in the control of numerous fungi of various cultivated plants, such as wheat, rye, barley, oats, rice, corn, turf, bananas, cotton, soybeans, coffee, sugar cane, vines, fruits and ornamental plants , and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and the seeds of these plants. They are especially suitable for controlling the following phyto-diseases: • Alternate species in fruits, rapeseed, beets, rice and vegetables (for example, A. solani or A. alternata in potatoes and tomatoes), • Aphanomyces species in sugar beet and vegetables, • Ascochita species in cereals and vegetables, • Bipolaris and Drechslera species in cereals, maize, rice and turfgrass (for example D. mayáis in corn), • Blumeria graminis (powdery mildew) in cereals, • Botrytis cinerea (gray mold) in strawberries, vegetables, ornamental plants and vines, • Bremia lactucae in lettuce, • Cerospora species in corn, soybeans, rice and sugar beet, • Cocliobolus species in corn, cereals, rice ( for example Cocliobolus sativus in cereals, rice Cocliobolus miyabeanus), • Colletotrichum species on soybeans and cotton, Drechslera species •, Pyrenophora species on corn, cereals, rice and lawns (for example D. teres on barley or D . tritici-repentis wheat), • Esca on grapevines, caused by Phaeoacremonium clamydosporium, Ph. Aleophilum and Formitipora punctata (syn. Phellinus punctatus), • ampelina on vines Elsinoe, • species Exserohilum corn, • Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, • Erysiphe (without Uncinula) necator in vines, • species of Fusarium and Verticillium in various plants (for example F. graminoarum or F. culmorum in cereals or F oxisporum in various plants, for example tomatoes), • Gaeumanomyces graminis in cereals, • Gibberella species in cereals and rice (for example Gibberella fujikuroi in rice), • Glomerella cingulata in vines and other plants, • Grainstaining complex in rice, • Guignardia budwelli on vines, Helminthosporium spp • maize and rice, • Isariopsis clavispora on grapevines, Michrodochium nivale on cereals •, • Mycosphaerella species on cereals, bananas and peanuts (M. graminicola eg wheat or M. fijiesis on bananas in ) • Peronospora species in squash and onion plants (for example P. brassicae in pumpkin or P. destructor on onions), • P akopsara pachirhizi and Phakopsara meibomiae in soybeans, • Phomopsis species on soybeans and sunflower , • infestaos Phytophthora in potatoes and tomatoes, Phytophthora species • in various plants (for example P. capsici in pepper), • Plasmopara viticola in grapevines, Podosphaera leucotricha • apples, Pseudocercosporella herpotrichoides • cereals, especially wheat and barley, • Pseudoperonospora in various plants (for example P. cubensis in cucumber or P. humili in hops), • Pseudopezícula tracheifilai in vines, • Puccinia species in various plants (for example P. triticina, P. striformins, P. hordei or P. graminis on cereals or P. asparagi on asparagus), Pyrenophora • species in cereals, Pyricularia oryzae •, Corticium sasakii, Sarocladium oryzae, S.attenuatum, Entiloma oryzae on rice, Pyricularia grisea on lawns • and cereals, • Pit ium spp. in lawns, rice, corn, cotton, rapeseed, sunflower, sugar beet, vegetables and other plants (for example P. ultiumum in various plants, P. aphanidermatum in lawns), • Rhizoctonia species in cotton, rice, potatoes, lawns, corn, rapeseed, sugar beet, vegetables and in various plants (for example R. solani in turnips and various plants), • Sclerotinia species in rapeseed and sunflower, • Septoria tritici and Stagonospora nodoru in wheat, • Setospaeria species in corn and lawns, • Sphacelotheca reilinia in corn, • Thievaliopsis species in soybeans and cotton, • Tilletia species in cereals, • Uncinula necator in vines, • Ustilago species in cereals, corn and sugarcane (for example U. mayáis in corn), • Venturia species (scab) in apples and pears.

The compounds I are also suitable for controlling harmful fungi for the protection of materials (for example wood, paper, dispersions of paints, fibers or textiles) and in the protection of products. Regarding the protection of wood, the following harmful fungi should be highlighted: Ascomycetes such as Ophiostoma spp., Ceratocystis spp. , Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophillum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilo yces spp. and Zygomycetes such as Mucor spp., and addition for the protection of stored products of the following harmful yeast fungi featured: Candida spp. and Saccharomyces cerevisae. In addition, the compounds of the formula I can also be used in crops that can tolerate an attack of insects or fungi due to the crop, including genetic engineering. On the other hand, the compounds of the formula I, their N-oxides and salts, according to the invention show a high activity against harmful arthropods. They can be used as pesticides in the protection of crops and in the hygiene and protection sectors of stored products and in the veterinary sector. They can act by contact or in the stomach or have a systemic or residual action. Contact action means that the pest dies upon contact with a compound I or with the material that releases the compound I.

Acting on the stomach means that the pest dies when it ingests a quantity of pesticidal efficacy of compound I or material containing a pesticidally effective amount of compound I. Syic action means that the compound is absorbed into the plant tissues of the treated plant and the pest is controlled when it eats plant tissue or sucks the sap from the plant. The compounds I are particularly suitable for controlling insect pests, such as • insects of the order Lepidoptera, for example Agrotis ypsilon, Agrotis segetu, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Elands insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterránea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera , Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, yphantria cunea, Hyponomeuta alínellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxoe stictícalís, Lyman ispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylola, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera eridania, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis, • of the order Coleoptera (cascarudos), for example ñgrilus sinuatus, ñgriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus granáis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufi anus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorr hybrus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varívestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lyssorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cocleariae, Phyllotreta chrysocephala, Phyllophaga sp. , Phyllopertha horticultural, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophílus granaría, of the order Diptera, for example Aedes aegypti, ñedes vexans, Anastrepha ludens, Ñnopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gaophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Lírio yza sativae, Líriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Typula olerácea and Typula paludosa , • of the order Thisanoptera (trips), for example Dichromothrips spp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, • of the order Hymenoptera for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoploca pa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta, • of the order Heteroptera, for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis , Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor, • of the order Homoptera, for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gos-sypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Classroom corthum solani, Bemisa tabaci, Bemisa argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, radicola Dysaphis, Dysaulacorthum pseudosolani, Dysaphis plantaginea , Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens , Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand and Viteus vitifolii, • of the order Isoptera (termites), for example, Caloter es flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis, and • of the order Orthoptera, for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forfícula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septe fasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorusLos compounds of formula I, their N- Oxides and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians (Acariña), for example from the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatu, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Der acentor silvarum, Hyalomma truncatu, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Der anyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoní; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri and OJIigsn Efapffle -toteeniasla formula I, their N-oxides and their salts are also useful for controlling nematodes, for example, nematodes of the root of the vesicular, for example, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg, Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, nematodes of branches and leaves, for example, Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi. The compounds of formula I are particularly useful for controlling insects of the order Lepidoptera. The compounds I, their N-oxides and salts can be converted into conventional formulations (agricultural formulations), for example, solutions, emulsions, suspensions, powders, pastes and granules. Accordingly, the invention also relates to agricultural compositions comprising a solid or liquid carrier and at least one pyridin-4-ylmethyl-amide compound of the formula I or an N-oxide or an agriculturally acceptable salt thereof. The agricultural compositions of the invention generally comprise between 0.1 and 95%, preferably between 0.5 and 90% by weight of compound idiosi-formulations are prepared in a known manner, for example by spreading the compound active with solvents and / or carriers, if desired together with emulsifiers and dispersants. Suitable solvents / auxiliaries with essentially: water, aromatic solvents (for example Solvesso8, xylene products), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (methylpyrrolidone, (NMP), N-octylpyrrolidone (NOP)), acetates (glycol diacetate), glycols, fatty acid dimethylamides and fatty acid esters. In principle, mixtures of solvents - carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example high dispersion silica, silicates) can also be used; emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene acid alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite and methylcellulose waste liquors. Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, sulfates of fatty alcohols, fatty acids and ethers of glycol sulfate acid alcohol, in addition of condensates of naphthalenesulfonate and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, octylphenolpolyoxyethylene ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol condensates and acid alcohol / ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol acetal ether, sorbitol esters, lignosulfite and methyl alcohol waste liquors pulp. For the preparation of solutions, emulsions, pastes or dispersions in oil for direct spray, mineral oil fractions with a medium to high boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin are suitable. , aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone and Water. Powders, dispersion materials and products that can be transformed into powder can be prepared by mixing or concomitant grinding of the active substances with a solid carrier. Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, Fuller's earth, limestone, lime, chalk, clayey earth, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as, for example , ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and products of plant origin, such as cereal flour, tree bark flour, wood flour and nut shell flour, cellulose powders and other solid carriers . The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The following are examples of formulations: 1. Products for dilution with water A water-soluble concentrates (SL) 10 parts by weight of a compound according to the invention are dissolved in water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active compound is dissolved by dilution with water. B Dispersible concentrates (DC) 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with the addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water produces a dispersion. C Emulsifiable concentrates (EC) 15 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). Dilution with water gives an emulsion. D Emulsions (EW, EO) 40 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). This mixture is introduced into water by means of an emulsifying machine (Ultraturrax) and becomes a homogeneous emulsion. Dilution with water gives an emulsiBnSuspensiones (SC, OD) In a stirred circular mill, 20 parts by weight of a compound according to the invention are mixed with addition of dispersants and humectants and water or an organic solvent to give a fine suspension of active compound By dilution with water a stable suspension of the active compound is obtained. F Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of a compound according to the invention are ground finely with the addition of dispersants and wetting agents and prepared as hydrodispersing or water-soluble granules by a technical method (for example extrusion , spray tower, fluid bed). By dilution with water a stable dispersion or suspension of the active compound is obtained. G Powders dispersible in water and water soluble powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with the addition of dispersants, wetting agents and silica gel. By dilution with water a dispersion or solution of the active compound is obtained. 2. Products to be applied without dilution H Powders for forming powder (DP) 5 parts by weight of a compound according to the invention are ground finely and mixed well with 95% finely divided kaolin. So you get a product like dust. I Granules (GR, FG, GG, MG) 0.5 parts by weight of a compound according to the invention are ground finely and associated with 99.5% carriers. The current methods are extrusion, spray drying or fluid bed. This way granules are obtained that are applied undiluted. J Solutions ULV (UL) 10 parts by weight of a compound according to the invention are dissolved in an organic solvent, for example, xylene. This way you get a product to apply undiluted. The active ingredients can be used as such, in the form of their formulations or the forms of use prepared therefrom, for example in the form of direct spray solutions, powders, suspensions or dispersions, emulsions, dispersions in oil, pastes, products dust formers, materials for dispersion, or granules, by spraying, atomizing, dusting, dispersing or pouring. The forms of use depend entirely on the proposed purposes; the intention is to ensure in each case the distribution as fine as possible of the active compounds according to the invention. Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water. To prepare emulsions, pastes or oily dispersions, the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of a humectant, viscosante, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetting agent, viscosifier, dispersant or emulsifier and, if appropriate, solvent or oil, and said concentrates are suitable for dilution with water. The concentrations of active compound in the ready-to-use preparations can be varied within relatively broad ranges. In general, they have from 0.0001 to 10%, preferably from 0.01 to 1%. The active ingredients can also be used successfully in the ultra-low volume process (ULV), by which it is possible to apply formulations comprising more than 95% by weight of active compound, or even to apply the active compound without additives. The compositions according to the invention can also be present in the form of use of fungicides, together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. When mixing the compounds I or the compositions comprising them in the form of use as fungicides, with other fungicides an expansion of the spectrum of fungicidal activity is obtained in many cases. The following list of fungicides, together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations, without limitations: • acylalanines, such as benalaxyl, metalaxyl, ofurace or oxadixyl, • amine derivatives , such as aldimorf, dodine, dodemorf, fenpropimorf, fenpropidin, guazatin, iminoctadine, spiroxamine or tridemorph, • anilinopyrimidines, such as pyrimethanil, mepanipyrim or cyprodinil, • antibiotics, such as cycloheximide, griseofulvin, casugamycin, natamycin, polyoxin or streptomyelin-zols, such as bitertanol, bromoconazole, ciproconazole, diphenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prochlorazone, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefonone, triadimenol , triflumizole or triticonazole, • dicarboximides, such as iprodione, myclozoline, procymidone or vinclozoline, • dithiocarbamates, such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram or zineb, • heterocyclic compounds, such as anilazine, benomyl, boscalide , carbendazim, carboxy, oxycarboxine, ciazofamide, dazomet, dithianone, famoxadone, fenamidone, fenarimol, fuberidazole, flutolanil, furametpir, isoprothiolane, mepronil, nuarimol, picobenzamide, probenazole, proquinazide, pirifenox, pyroquilone, quinoxifen, silthiopham, thiabendazole, thifluzamide, thiophanate -methyl, thiadinyl, tricyclazole or triforin, • copper fungicides, such as Bordeaux mixture, copper acetate, copper oxychloride or basic copper sulfate, • nitrophenyl derivatives, such as binapacryl, dinocap, dinobutone or nitroftal-isopropyl, • phenylpyrroles, such as fenpiclonil or fludioxonil, • sulfur, • other fungicides, such as methyl-S-acibenzolar, benthiavalicarb, c arpropamide, chlorothalonil, ciflufenamide, cymoxanil, diclomezine, diclocimet, dietofencarb, edifenfos, etaboxam, fenhexamida, fentino acetate, fenoxanil, ferimzona, fluazinam, fosetil, fosetil-aluminio, phosphoric acid, iprovalicarb, hexachlorobenzene, metrafenone, pencicurona, pentropirad, propamocarb , phthalide, methyltholoclofos, quintozene or zoxamide, • strobilurins, such as azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, methylcresoxim, methominostrobin, orisastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, • sulfenic acid derivatives, such as captafol, captan, diclofluanid, folpet or tolylfluanide, • cinnamides and analogous compounds, such as dimetomorph, flumetover or flumorf. The insecticidal compositions of the present invention may also contain other active ingredients, for example other pesticides such as insecticides and herbicides, fertilizers such as ammonium nitrate, urea, potassium hydroxide, and superphosphate, phytotoxics and plant growth regulators, insurers and nematicides. These additional ingredients can be used in sequence or in combination with the above-described compositions, so that aggregates are also only immediately before use (tank mixing). For example, the plants may be sprayed with a composition of the present invention before or after being treated with other active ingredients. In general, these agents are mixed with the agents according to the invention in a weight ratio of 1: 100 to 100: 1. The following list of pesticides, together with the compounds according to the invention that can be used, is intended to illustrate the possible combinations, without limitations: A.l. Organo (thio) phosphates: for example acephate, azamethiphos, methylazinphos, chlorpyrifos, methylchlorpyrifos, chlorfenvinphos, diazinone, dichlorvos, dicrotophos, dimethoate, disulfotone, ethion, fenitrothione, fenthion, isoxationa, malathion, methamidophos, methidathione, methyl parathion, mevinfos, monocrotophos, methyloxydometone, paraoxone, parathion, phenoate, fosalone, phosmet, phosphamidone, phorate, foxima, methylpyrimiphos, profenofos, protiofos, sulprofos, tetrachlorvinfos, terbufos, triazophos, trichlorphona; A.2. Carbamates: for example alanicarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate; A.3. Pyrethroids: for example allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvaleriato, etofenprox, fenpropathrin, fenvaleriato, imiprotrina, lambda-cyhalothrin, permethrin, praletrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralometrine, transfluthrin, profluthrin, dimefluthrin; A.4. Growth regulators: a) inhibitors of chitin synthesis: for example benzoylureas: chlorfluazurone, diflubenzurone, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolane, hexythiazox, ethoxazole, clofentazine b) ecdysone antagonists: for example halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: for example pyriproxyfen, methoprene, phenoxycarb; d) inhibitors of lipid synthesis: for example spirodiclofen, spiromesifen or spirotetramate; TO 5. Nicotinic receptor agonist / antagonist compounds (nicotinoid or neonicotinoid insecticides): for example clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamipride, thiaclopride or the thiazole compound of the formula A.6. GABA antagonist compounds: for example acetoprol, endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprol, pyriprole, 5-amino-3- (aminothiocarbonyl) -1- (2,6-dichloro-4-trifluoromethylphenyl) -4- (trifluoromethylsulfinyl) -pirazol; A.7. Macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, lepimectin, spinosad, A.8. Electron transport inhibitors of the mitochondrial complex I (METI I compounds): for example phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerimA; 9. Inhibitors of electron transport of the mitochondrial complex II and / or complex III (compounds METI II and III): for example acequinocyl, fluaciprim, hydramethylnon; A.10. Non-coupling compounds: for example chlorfenapyr; A.11. Oxidative phosphorylation inhibiting compounds: cyhexatin, diafentiurone, fenbutatin oxide, propargite; A.12. Mutative alteration compounds: for example, cyromazine; A.13. Mixed function oxidase inhibitor compounds: for example piperonyl butoxide; A.14. Sodium channel blocking compounds: for example, indoxacarb, metaflumi zone, A.15. Miscellaneous: benclotiaz, bifenazato, cartap, flonicamida, piridalilo, pimetrozina, sulfur, thiociclam, flubendiamida, cienopi rafeno, flupirazofos, ciflumetofeno, amidoflumet, compounds of the formula P2: wherein X and Y are each independently halogen, in particular chlorine; is halogen or haloalkyl Cj-C2, in particular trifluoromethyl; R1 is Ci-C6 alkyl, C2-C6 alkenyl, C2-Ce alkynyl, Ci-C4 alkoxy-C1-C4 alkyl or C3-C6 cycloalkyl each of which may be substituted with 1, 2, 3, 4 or 5 atoms halogen; in particular R1 is methyl or ethyl; R 2 and R 3 are C 1 -C 6 alkyl, in particular methyl, or they can form together with the adjacent carbon atom a C 3 -C 6 cycloalkyl residue, in particular a cyclopropyl residue, which can carry 1, 2 or 3 halogen atoms, where the examples include 2,2-dichlorocyclopropyl and 2,2-dibromocyclopropyl; and R 4 is hydrogen or C 1 -C 6 alkyl, in particular hydrogen, methyl or ethyl; anthranilamide compounds of the formula P3 wherein A1 is CH3, Cl, Br, I, X is CH, C-Cl, CF or N, Y 'is Cl, or Br, Y' 'is F, Cl, CF3, B1 is hydrogen, Cl, Br, I, CN, B2 is Cl, Br, CF3, OCH2CF3, OCF2H, and B is hydrogen, CH3 or CH (CH3) 2; and malononitrile compounds as described in JP 2002 284608, WO 02/89579, O 02/90320, WO 02/90321, WO 04/06677, WO 04/20399 or JP 2004 99597. Suitable pesticide compounds also include microorganisms such as Bacillus turingiensis, Bacillus tenebrionis and Bacillus subtilis. The aforementioned compositions are of particular utility to protect the plants against infestation by said pests and also to protect the plants against infections by phytopathogenic fungi or to combat these pests / fungi in infested / infected plants. However, the compounds of the formula I are also suitable for the treatment of seeds. The application to the seeds is done before sowing, either directly on the seeds or after germination. Compositions which are useful for the treatment of seeds are for example: A Soluble concentrates (SL, LS) D Emulsions (EW, EO, ES) E Suspensions (SC, OD, FS) F Water dispersible granules and water soluble granules (WG, SG) G Water-dispersible powders and water-soluble powders (P, SP, WS) H Dust-forming powders (DP, DS) The formulations FS preferably of the compounds of the formula I for the treatment of seeds usually comprise from 0.5 to 80% of the active ingredient, from 0.05 to 5% of a humectant, from 0.5 to 15% of a dispersing agent, from 0.1 to 5% of a thickener, from 5 to 20% of an antifreeze agent, from 0.1 to 2% of an antifoaming agent, from 1 to 20% of a pigment and / or a colorant, from 0 to 15% of a fixing / adhesion agent, from 0 to 75% of a a filler / vehicle, and from 0.01 to 1% of a preservative. The pigments or dyes suitable for the formulations for the treatment of the seeds are blue pigment 15: 4, blue pigment 15: 3, blue pigment 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48: 2, pigment red 48: 1, pigment red 57 : 1, red pigment 53: 1, orange pigment 43, orange pigment 34, orange pigment 5, green pigment 36, green pigment 7, white pigment 6, brown pigment 25, basic violet 10, basic violet 49, red acid 51, acid red 52, red acid 14, blue acid 9, yellow acid 23, red basic 10, red basic 108. The fixation / adhesion agents are added to improve the adhesion of the active materials on the seeds after treatment. Suitable adhesives are block copolymers of EO / PO surfactants but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polimin®), polyethers and copolymers derived from these polymers. . For use against ants, termites, wasps, flies, mosquitoes, crickets, or cockroaches, the compounds of formula I are preferably used in a bait composition. The bait can be a liquid, solid or semi-solid preparation (for example a gel). The solid baits can be molded in various forms suitable for the respective application, for example, granules, blocks, adhesives, disks. The liquid baits can be filled in various devices to ensure proper application, for example open containers, spray devices, droplet sources, or evaporation sources. The gels can be based on aqueous or oily matrices and can be formulated according to particular needs in terms of adhesiveness, moisture retention or aging characteristics. The bait used in the composition is a sufficiently attractive product to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets, etc., or cockroaches, to eat it. The attraction can be manipulated through the use of food stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, animal and / or vegetable proteins (meat, fish or blood meal, insect parts, egg yolk), fats and oils of animal origin and / or vegetable, or mono, oligo or polyorganososaccharides, especially sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. The fresh or degraded parts of fruits, crops, plants, animals, insects or their specific parts can also serve as food stimulants. It is known that sex pheromones are more specific to insects. Specific pheromones are described in the literature and are known to those skilled in the art. The formulations of the compounds of the formula I as aerosols (for example in spray cans), oil spraying or pump spray are very suitable for the non-professional user, in order to control pests such as flies, fleas, mites, mosquitoes or cockroaches. Preferably, the aerosol recipes are composed of the active compound, solvents such as lower alcohols (for example methanol, ethanol, propanol, butanol), ketones (for example acetone, methyl ethyl ketone), paraffinic hydrocarbons (for example kerosene) with boiling points ranging from about 50 to 250 ° C, dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, aromatic hydrocarbons such as toluene, xylene, water, other auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate with 3-7 moles of ethylene, acid alcohol ethoxylate, perfumed oils such as ether oils, medium fatty acid esters with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and if required, propellants such as propane, butane, nitrogen, comsed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases. Oily spray formulations differ from aerosol recipes for not using propellants. The compounds of the formula I and their respective compositions can also be used in spirals for mosquitoes and fumigation, smoke reels, vaporizing plates or long-lasting vaporizers and also in papers against moths, moth-proof plates or other heat-independent vaporizing systems. The compounds of formula I and their compositions can be used to protect inanimate material, in particular cellulose-based materials such as wood materials, for example, trees, fences, chairs, etc. and constructions such as houses, warehouses, factories, but also construction materials, furniture, leather, fibers, vinyl items, electric cables and wires, etc. against ants and / or termites, and to control ants and termites so that they do not damage crops or human beings (for example when the plague invades homes or public buildings). The compounds of the formula I are applied not only to the surface of the surrounding soil or to the floor under the floor, in order to protect the wood materials, they can also be applied to woodworking articles such as the concrete surfaces under the floor. , poles of rooms, beams, plywood, furniture, etc., wood articles such as chipboard, countertops, etc. and vinyl items such as coated electrical cables, vinyl sheets, thermal insulating material such as styrene foams, etc. In the case of application against ants that damage crops or humans, the ant controller of the ent invention is applied to the crops or the surrounding soil, or is applied directly on the anthills or the like. In the methods according to the invention the pests are controlled by contacting the parasite / white pest, its food source, habitat, feed site or locus with an effective pesticidal amount of at least one compound I, or its N -oxide or salt, or with a composition containing an effective amount as a pesticide of at least one compound I, or its N-oxide or salt. "Locus" means a habitat, feeding site, plant, seed, soil, area, material or environment in which a pest or parasite develops or may develop. In general, "pesticidally effective amount" means the amount of active ingredient necessary to achieve an observable effect on development, including the effects of necrosis, death, retardation, ention, and elimination, destruction, or otherwise reduction of the ence and activity of the target organism. The pesticidally effective amount may vary for the various compounds / compositions used in the invention. An effective pesticidal amount of the compositions will vary according to the ailing conditions such as pesticide effect of interest and duration, weather, target species, locus, mode of application, and the like. The compounds of the invention can also be applied entatively at the sites at which the pests are expected to appear. The compounds of the formula I can also be used to protect the developing plants against attack or infestation by pests upon contacting the plant with pesticide-effective amount of the compounds of the formula I. Thus, "contacting" includes direct contact (by application of the compounds / compositions directly on the pest and / or the plant, in general the foliage, stems or roots of the plant) and indirect contact (by application of the compounds / compositions to the locus of the plague and / or plant). The compounds I are used to treat the fungi, pests or plants, seeds, materials or soil to be protected against attack by fungi or pests by an effective pesticidal or fungicidal amount of at least one active compound I, its N-oxide or salt. The application can be made before and after the infection / infestation of the materials, plants or seeds by the fungus or pest.

When used in the protection of a plant, the quantities applied, according to the type of effect desired, are in the range of 0.1 g to 4000 g per hectare, preferably from 25 g to 600 g per hectare, and with greater preference for 50 g to 500 g per hectare. In the treatment of the seed, the application rates of the active compounds are generally from 0.001 g to 100 g per kg of seed, preferably from 0.01 g to 50 g per kg of seed, in particular 0.01 g. 2 g per kg of seed. In the case of soil treatment or application to the nests of the pests, the amount of the active ingredient varies from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2. The application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m2 of treated material, preferably from 0.1 g to 50 g per m2. Insecticidal compositions for use in the impregnation of materials generally contain from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight, and more preferably from 1 to 25% by weight of at least one repellent insecticide For use in compositions as baits, the typical content of active ingredient is from 0.001% by weight to 15% by weight, preferably from 0.001% by weight to 5%% by weight of active compound.

For use in spray compositions, the content of active ingredient is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight and more preferably from 0.01 to 15% by weight. When used in the protection of stored materials or products, the amount of active compound applied depends on the kind of application area and the desired effect. The amounts that are usually applied in the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active compound per cubic meter of treated material. Under outdoor conditions, the rate of application of the active compound to control the pests is from 0.1 to 2.0, preferably from 0.2 to 1.0, kg / ha. Different types of oils, humectants, adjuvants, herbicides, fungicides, other pesticides, or bactericides can be added to the active compounds, if applicable, not until immediately before use (tank mixing). These agents can be mixed with the agents according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1. The adjuvants that can be used are in particular modified organic polysiloxanes such as Break Tru S 240®; alcohol alkoxylates such as Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol in 30®; EO / PO block polymers, for example, Pluronic RPE 2035® and Genapol Bs; alcohol ethoxylates such as Lutensol XP 80®; and sodium dioctyl sulfosuccinate such as Leofen RA®.

Synthesis Examples The procedures described in the following synthesis examples were used to prepare other compounds I by suitable modification of the starting compounds. The compounds thus obtained are listed in the following tables, together with the physical data. Example 1: Preparation of picolylamide of 5-bromo-pi Ridine-2-su1 phonic acid At 0 ° C, a solution of isopropylmagnesium chloride (2 M in tetrahydrofuran, 1.1 equivalents (eq.)) Was added slowly to 80 mmol of 3-bromo-6-iodo-pyridine in 80 ml of tetrahydrofuran, maintaining the temperature between 0 and 10 ° C. After stirring for 1 h at about 20 ° C, the solution was cooled to (-40) ° C. Then 2.5 eq. of SO2 under intense cooling to maintain a temperature of (-40) ° C. After 30 minutes at this temperature, 1.1 eq. of SO2CI2. The reaction mixture was then heated to 0 ° C. After stirring for 30 minutes, 10% aqueous hydrochloric acid was carefully added. Then, the crude reaction mixture was extracted with 100 ml of diethyl ether three times. The combined organic phases were washed with saturated aqueous sodium chloride and then dried over sodium sulfate. The solvent was removed and the crude sulfochloride was dissolved in 40 ml of acetonitrile. In the meantime, 1.1 equivalents of picolylamine and 1.1 equivalents of triethylamine were dissolved in 50 ml of methyl cyanide and cooled to 0 ° C. The crude sulfochloride in methyl cyanide was added through a dropping funnel keeping the temperature below 10 ° C. The solution was heated to about 20 ° C and stirred overnight. The precipitated solid was then filtered and washed with 30 ml of water. The product obtained was an off-white solid. Yield: 20.0 g (82%); p. f .: 156 ° C. Example 2: Preparation of 5- (4-methoxyphenyl) -pyridine-2-sulfonic acid picolylamide A solution of 0.4 g (1.2 mmol) of bromine from Example 1, 0.22 g (1.5 mmol) of 4-methoxybenzanboronic acid, 0.03 g of PdCl2 [P (C6H5) 3] 2, 0.020 g of P [C (CH3) 3] 3 * HBF4 and triethylamine was dissolved in 5 ml of methyl cyanide and 2 ml of Water. The reaction mixture was heated to reflux for 2 hours. After purification by chromatography, 0.28 g of the title compound was obtained as an off-white solid. P. f. : 172 ° C. The compounds of Examples 3 to 132 were prepared in an analogous manner and are listed in Table B, Table C and Table D.

Table B: P. f .: melting point Table C: P. f .: melting point P. f. melting point Examples of the action against harmful fungi The fungicidal action of the compounds of the formula I was demonstrated by means of the following experiments: The active compounds were prepared together or separately as a stock solution with 0.25% by weight of active compound in acetone or dimethyl sulfoxide. 1% by weight of the emulsifier Uniperol® EL (wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.

Example of use 1 - Activity against tomato alternariosis caused by Alternaria solani Young tomato seedlings were planted in pots. These plants were sprayed until soaked with an aqueous suspension containing the concentration of active compound set forth below. The next day, the treated plants were inoculated with an aqueous spore suspension of Alternaria solani with 0.17 x 106 spores per ml. Then the test plants were transferred immediately to a humid chamber. After 5 days at 20 and 22 ° C and a relative humidity of close to 100%, the extent of the fungal attack on the leaves was evaluated visually as% leaf area. In this test, the plants that were treated with 250 ppm of active compound of the examples 8, 66, 69, 70, 72, 75, 78, 90 and 113 showed, respectively, an infection not higher than 5% and the plants that had been treated with 250 ppm of active compound of examples 2, 9, 13, 61, 67, 74, 84, 91, 111 and 112 showed, respectively, an infection not higher than 20%, where the untreated plants were infected by 90%.

Example of use 2: Activity against the disease caused by Phytophthora infestans, protective treatment Young seedlings of tomato were planted in pots. The plants were sprayed until soaked with an aqueous suspension containing the concentration of active compounds set forth below. The next day, the treated plants were infected with an aqueous suspension of sporangias of Phytophthora infestans. After inoculation, the test plants were immediately transferred to a humid chamber. After six days of 18 to 20 ° C and a relative humidity close to 100%, the extent of the fungal attack on the leaves as% of diseased surface was visually evaluated. In this test, the plants that were treated with 250 ppm of the active compound of Examples 5, 7, 10, 19, 21, 66, 67, 68, 69, 70, 75, 78 and 112 respectively showed an infection not greater than 5% and plants that had been treated with 250 ppm of active compound of examples 6, 8, 13, 17, 18, 25, 28, 72, 74, 86, 92, 119 and 122 showed, respectively, a infection not higher than 20%, where the untreated plants were infected by 90%.

Example of use 3 - Healing activity against brown rot of wheat caused by recondite Puccinia Leaves of wheat seedlings in pots of the variety "Kanzler" were sprayed with spores of Puccinia recondite. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber without light and high humidity and 20 to 22 ° C for 24 hours. The next day, the plants were sprayed until soaked with an aqueous suspension containing the concentration of active compound as described below. The plants were allowed to dry outdoors. The test plants were then grown for 8 days in a greenhouse at approximately 22 ° C and a relative humidity of between 65 and 70%. The extent of the fungal attack was evaluated visually as% of diseased leaf surface. In this test, plants that were treated with 250 ppm of the active compound of example 34 showed an infection of no more than 5% and plants that had been treated with 250 ppm of the active compound of examples 32, 62, 95 and 97 showed , respectively, an infection not exceeding 20%, where the untreated plants were infected by 90%.

Example of use 4 - Protective activity against brown rot of wheat caused by recondite Puccinia Wheat leaves in the "Kanzler" cultivar were sprayed until soaked with an aqueous suspension containing the concentration of active principle described below. On the following day, the plants were inoculated with spores of recondite Puccinia. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber without light and high humidity of 20 to 22 ° C for 24 h. Then, the test plants were grown for 6 days in a greenhouse at approximately 22 ° C and a relative humidity of between 65 and 70%. The extent of the fungal attack on the leaves was evaluated visually as% of diseased area. In this test, the plants that were treated with 250 ppm of active compound of Examples 77 and 82 showed, respectively, an infection not higher than 20%, where the untreated plants were 90% infected.

Example of use 5 - Healing activity against soya rot caused by Phakopsora pachirhizi Soybean seedlings planted in pots of the "Oxford" variety were inoculated with spores of Phakopsora pachirhizi. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of approximately 95% and 23 to 27 ° C for 24 h. The next day, the plants were sprayed until soaked with an aqueous suspension containing the concentration of active ingredient described below. The plants were allowed to dry outdoors. Then, the test plants were grown for 14 days in a greenhouse at 23 to 27 CC and a relative humidity of between 60 and 80%. The extent of the fungal attack on the leaves was evaluated visually as an area of diseased leaf surface. In this test, the plants that were treated with 250 ppm of active compound of the examples 28, 29, 58, 59, 88, 89 and 125 showed, respectively, an infection not superior to 5% and the plants that had been treated with 250 ppm of active compound of examples 54, 55, 83 and 126 showed, respectively, an infection not higher than 20%, where the untreated plants were infected by 90%. The action of the compounds of the formula I against harmful pests was demonstrated by means of the following experiments: 1. Activity against Boil weevil (Antonomus grandis) The active compounds were formulated in 1: 3 dimethyl sulfoxide: water. 10 to 15 eggs were placed in microtiter plates filled with 2% agar-agar in water and 300 ppm formalin. The eggs were sprayed with 20 μ? of the test solution, the plates were sealed with perforated sheets and kept at 24-26 ° C and 75-85% humidity with a day / night cycle for 3 to 5 days. Mortality was evaluated on the basis of non-embryonated eggs or larvae on the surface of the agar and / or the amount and depth of the channels excavated by the incubated larvae. The tests were replicated22 Ttetes / idad against the Mediterranean fruit fly (Ceratitis capitata) The active compounds were formulated in 1: 3 DMSO: water. 50 to 80 eggs were placed in microtitre plates filled with 0.5% agar-agar and 14% diet in water. The eggs were sprayed with 5 μ? of the test solution, the plates were sealed with perforated sheets and kept at 27-29 ° C and 75-85% humidity under fluorescent light for 6 days. Mortality was evaluated based on the agility of the incubated larvae. The tests were replicated 2 times. 3. Activity against Tobacco Heliotis virescens The active compounds were formulated in 1: 3 dimethylsulfoxide: water. 15 to 25 eggs were placed in microtitre plates filled with diet. The eggs were sprayed with 10 μ? of the test solution, the plates were sealed with perforated sheets and kept at 27-29 ° C and 75-85% humidity under fluorescent light for 6 days. Mortality was evaluated based on the agility and comparative feeding of the incubated larvae. The tests were replicated 2 times. 4. Activity against Megoura viciae The active compounds were formulated in 1: 3 DMSO: water. Discs of bean leaves were placed in microtitre plates filled with 0, 8% agar-agar and 2.5 ppm OPUS ™. The leaf discs were sprayed with 2.5 μ? of the test solution and 5 to 8 adult aphids were placed in the microtiter plates which were then closed and kept at 22-24 ° C and 35-45% under fluorescent light for 6 days. Mortality was evaluated on the basis of vital reproduced aphids. The tests were replicated 2 times. 5. Activity against wheat Rhopalosifum padi The active compounds were formulated in 1: 3 dimethyl sulfoxide: water. Discs of barley leaves were placed in microtiter plates filled with 0.8% agar-agar and 2.5 ppm OPUS. The leaf discs were sprayed with 2.5 μ? of the test solution and 3 to 8 adult aphids were placed in the microtiter plates which were then closed and kept at 22-24 ° C and 35-45% humidity under the fluorescent light for 5 days. Mortality was evaluated on the basis of vital aphids. The tests were replicated 2 times.

Claims

Claims Pyridin-4-ylmethyl-amide compounds of the general formula I characterized because: R1 is hydrogen, Ci-C6 alkoxy Ci-C6 alkyl, cyano-C1-C4, haloalkyl Ci-C4alkyl, C1-C4 alkyl C1-C4, haloalkoxy C1-C4 C C4 alkyl, di (Ci-C4) amino-C1-C4 alkyl, C3-C6-alkyl d-C4 halocycloalkyl C3-C6-C1-C4 alkyl, (alkyl Ci-C4) alkoxycarbonyl, (alkoxy Ci-C4) alkoxycarbonyl, C2-C6 alkenyl, C3 -C6, C3-C6 halocycloalkyl, C5-C6 cycloalkenyl, N-heterocyclyl-saturated C6-C4 alkyl, C2-C4 cyano-alkenyl, C2-C4 haloalkenyl, C2-C4 alkoxyC4-alkenyl, haloalkoxy- C4-C1 C2-C4 alkenyl, (Ci-C4 alkyl) carbonyl C2-C4 alkenyl, (C1-C4 alkoxy) carbonyl C2-C4 alkenyl, d¡ (Ci-C4 alkyl) amino-C2-C4, C2-C6 alkynyl, C2-C4 haloalkynyl, CrC4 haloalkyl-C2-C4 alkynyl, C1-C4 alkoxy-C2-C4 alkynyl, tri (Cry4 alkyl) silyl-C2-C4 alkynyl, di (CrC4 alkyl) amino, naphthylmethyl or benzyl, wherein the last two mentioned radicals can carry in the ring phenyl or naphthyl 1, 2, or 3 radicals, selected from cyano, halogen, C 1 -C 4 alkyl, Ci-C 4 haloalkyl) C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, (C 1 -C 4 alkyl) carbonyl, (C 4 C) alkoxycarbonyl and di (C 1 -C 4 alkyl) amino; R2, R3, R4, R5 are selected independently of each other, hydrogen, halogen, C1-C4 alkyl, C2-C4, C2-C4 alkynyl, tri- alkylsilyl C1-C4 alkyl, C1-C4 haloalkyl, C1 -C4, C1-C4 haloalkoxy, S (0) pR16 and NR17R18; or R2 and R3 together with the carbon atoms to which they are attached can form a 5 or 6-membered fused carbocycle containing one, two or three heteroatoms as ring members, being selected from the group consisting of nitrogen atoms, oxygen and sulfur, it being possible for the fused ring to carry one or two radicals R7 and / or Re; R6 is halogen, cyano, nitro, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy, C1-C10 haloalkyl, C1-C10 haloalkoxy, (CrC4 alkyl) carbonyl, (Ci-C4 alkoxy) carbonyl, -C (R9) = NOR10, (Ci-C4 alkyl) aminocarbonyl, di (C1-C4) aminocarbonyl, hetaryl or 5 or 6 membered hetaryloxy containing one or two heteroatoms as ring members being selected from the group of nitrogen, oxygen and sulfur atoms, phenyl or phenoxy, wherein the phenyl or hetaryl ring in the last four radicals mentioned may carry one, two or three radicals R11; two R6 radicals together with two adjacent carbon atoms of the pyridyl ring to which they are attached may also form a 5 or 6 membered fused carbocycle which may be substituted with 1, 2 or 3 radicals R12; R8 are, independently of each other, halogen, C1-C4 alkyl, haloalkyl C1-C4, C1-C4 alkoxy or haloCalkoxy CrC4; is 0, 1 or 2; is hydrogen, C1-C4 alkyl, C1-C4 alkoxy Ci-C4-alkyl C1-C4, haloalkoxy CRC4-C1-C4 alkyl, phenyl which may carry a cyano radical, halogen, C1-C4 alkoxy or C1-C4 haloalkoxy , or benzyl which may be unsubstituted or substituted by 1, 2 or 3 radicals, selected from cyano, halogen and C 1 -C 4 alkyl; is C 1 -C 6 alkyl, benzyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 1 -C 4 alkynyl or C 2 -C 4 haloalkynyl; is nitro, cyano, OH, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C4 alkoxy, C1-C4 haloalpoxy, (CrC4 alkoxy) carbonyl, Ci-C4 alkyl carbonyl, CHO, CO-NH2, CrC4-aminocarbonyl alkyl , di (alkyi) Ci-C4) aminocarbonyl, C4-4 alkylthio, haloalkyl C4, thio, C1-C4alkylsulfinyl, haloalkyl C1-C4 sulfinyl, alkyl CrC4Sulphonyl, haloalkyl Ci-C4 sulfonyl, (Ci-C4alkylamino) , d (C 1 -C 4) amino, tri (C 1 -C 4 alkyl) silyl, -C (R 13) = NOR 14, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl; two radicals R1 1 together with two adjacent atoms of the phenyl ring to which they are attached can form a 5 or 6 membered fused carbocycle or a 5 or 6 membered fused heterocycle containing one, two or three heteroatoms as ring members, being selected from the group consisting of nitrogen, oxygen and sulfur atoms, it being possible for the fused ring to carry 1, 2 or 3 radicals R 2a; R12, R12a are independently selected from halogen, cyano, nitro, Ci-Cs alkyl, haloalkyl d-Ce, Ci-Ce alkoxy, Ci-C8 haloalkoxy, (Ci-C4 alkyl) carbonyl, (CrC4 alkoxy) carbonyl, -C (R13a) = NOR 4a, (C4 alkyl) aminocarbonyl, di (Ci-C4 alkyl) aminocarbonyl, phenyl and phenoxy, wherein the ring in the last two mentioned radicals can carry one, two or three groups R15; R 3, R 13a are independently selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkyl, phenyl which may be unsubstituted or which may be substituted with 1, 2 or 3 radicals, selected from cyano, halogen, dC-alkoxy and C 1 -C 4 haloalkoxy, or benzyl which may be unsubstituted or substituted by 1, 2 or 3 radicals, selected from cyano, halogen and C 1 -C 4 alkyl; R14, R14a are independently selected from Ci-C6 alkyl, benzyl, C2-C4 alkenyl, Ci-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 alkynyl and C2-C4 haloalkynyl; R15 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1 haloalkyl or haloalkoxy d; R16 is C2-C4 alkyl or C2-C4 haloalkyl and p is 0, 1 or 2; Y R17, R8 are independently selected from hydrogen, C1-C6 alkyl or R17 and R8 together with the nitrogen atom to which they are attached, form a saturated heterocycle of five to eight members which is attached through of a nitrogen and which may contain one, two or three more heteroatoms or groups of heteroatoms of the group consisting of O, N, S, S (O) and S (0) 2 as ring members, it being possible for the heterocycle to carry 1, 2, 3 or 4 substituents selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or halogen; and the N-oxides and the agriculturally acceptable salts of the compounds I. The compounds of the general formula I according to claim 1, characterized in that R2, R3, R4 and R5 are hydrogen. The compounds of the general formula I according to claim 1, characterized in that R 2 and R 3 are independently selected from hydrogen, halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, tri -C1-C4 alkyl silyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, S (0) pR16 and NR 7R18, R4 and R5 are hydrogen, wherein at least one of the radicals R2 and R3 is different from hydrogen. The compounds of the general formula I according to any of claims 1 to 3, characterized in that n is 1 and R6 is 5- or 6-membered heterate or heteryloxy containing one or two heteroatoms as ring members, selected from the group of atoms of nitrogen, oxygen and sulfur, wherein the heterocycle may be unsubstituted or may carry 1, 2 or 3 R11 radicals. A process for the preparation of pyridin-4-ylmethylamide compounds of the formula I according to claim 1, which comprises reacting a 4-aminomethylpyridine compound of the formula II characterized in that R1 to R5 are as defined in claim 1, under basic conditions with a pyridine sulfonic acid compound of the formula III wherein R6 and n are as defined in claim 1 and L is hydroxy or halogen. An agricultural composition, characterized in that it comprises a solid or liquid carrier and at least one pyridin-4-ylmethyl-amide compound of the formula I and / or an N-oxide or one of its acceptable salts in agriculture, according to the claim 1. The use of pyridin-4-ylmethyl-amides of the formula I and its N-oxides or their acceptable agricultural salts, according to claim 1, characterized in that it serves to combat phytopathogenic fungi. The use of pyridin-4-ylmethyl-amides of the formula I and its N-oxides or their acceptable agricultural salts, according to claim 1, characterized in that it serves to combat an arthropod pest. The use of pyridin-4-ylmethyl-amides of the formula I and its N-oxides or their acceptable salts in agriculture, according to claim 1, characterized in that it serves to protect seeds, the roots of the seedlings and the shoots of a infestation by arthropod pests and / or phytopathogenic fungi. A method for combating phytopathogenic fungi, characterized in that it comprises the treatment of the fungi or the materials, the plants, the soil or the seeds to be protected from a fungal attack, with at least one pyridin-4-ylmethyl-amide compound of the formula I and / or an N-oxide or one of its acceptable salts in agriculture, according to claim 1. A method for combating arthropod pests, characterized in that it comprises contacting said plants, their habitat, nutrient soil, food supply, plant, seed, soil, area, material or environment where the arthropod pests grow or can grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from an attack or infestation by said pests, with at least one pyridin-4-ylmethyl-amide compound of the formula I and / or an N-oxide or one of their acceptable agricultural salts, according to claim 1, or with a composition comprising at least one pyridin-4-ylmethyl-amide compound of the formula I and / or an N-oxide or one of its acceptable salts in agriculture . A method for protecting crops from attack or infestation by arthropod pests, characterized in that it comprises contacting a culture with at least one pyridin-4-ylmethyl-amide compound of the formula I, and / or an N-oxide or one of its acceptable salts in agriculture, according to claim 1. A method to protect seeds from an infestation by arthropod pests and from the roots of plants and outbreaks of an infestation by arthropod pests, characterized in that it comprises contacting the seed or the roots of the seedlings and the shoots with at least a pyridin-4-ylmethylamide compound of the formula I, and / or an N-oxide or an agriculturally acceptable salt thereof, according to claim 1. A method for protecting non-living materials from attack or infestation by arthropod pests, characterized in that it comprises contacting the non-living material with at least one pyridin-4-ylmethyl-amide compound of the formula I, and / or an N -oxide or one of its acceptable salts in agriculture, according to claim 1. Seed, characterized in that it comprises at least one pyridin-4-ylmethylamide compound of the formula I, and / or an N-oxide or one of its agriculturally acceptable salts, according to claim 1, in an amount of 0 , 1 g to 10 kg per 100 kg of seed.