DE19958166A1 - Pyridine carbamides - Google Patents

Abstract

The invention relates to novel pyridine carboxamides of general formula (I), to a number of methods for the production thereof and to their use for controlling harmful organisms.

Description

The invention relates to new pyridine carbamides, several processes for their manufacture and their use in combating harmful organisms.

Certain pyridine carbamides and their fungicidal activity are already known (see e.g. Tetrahedron (1998), 54 (42), 12 745-12 774, Tetrahedron Lett. (1998), 39 (24), 4363-4366, WO 99/40 081 or WO 99/11 127). The effect However, these previously known compounds are particularly inexpensive quantities and concentrations are not completely satisfied in all areas of application posed.

The new pyridinecarbamides of the general formula (I) were found

in which
A represents a single bond, substituted or unsubstituted, optionally interrupted by heteroatoms alkylene,
R ¹ represents substituted or unsubstituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl with 3 to 8 ring members and
R ^{2 represents} hydrogen, alkylcarbonyl or alkoxycarbonyl.

In the definitions are the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with heteroatoms,  as in alkoxy, alkylthio or alkylamino, in each case straight-chain or branched. Is an alkyl or alkanediyl chain is interrupted by more than one heteroatom, they can be the same or different. Is an alkyl or alkanediyl chain through interrupted more than one oxygen atom, two oxygen atoms are not directly adjacent. Unless otherwise stated, hydrocarbons are preferred chains with 1 to 6 carbon atoms.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, such as e.g. As phenyl, naphthyl, anthranyl, phenanthryl, preferably for phenyl or Naphthyl, especially for phenyl.

Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped Connections with up to eight ring links, in which at least one ring link Heteroatom, i. H. is an atom other than carbon. Contains the ring several heteroatoms, these can be the same or different. Are heteroatoms preferably oxygen, nitrogen or sulfur. If the ring contains several acids atoms of matter, these are not adjacent. If necessary, form the annular Compounds with other carbocyclic or heterocyclic, fused or bridged rings together a polycyclic ring system. Prefers are mono- or bicyclic ring systems, especially mono- or bicyclic, aromatic ring systems.

Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds that opp optionally with other carbocyclic, fused or bridged rings form a polycyclic ring system.  

Cycloalkenyl stands for carbocyclic, ring-shaped compounds that at least contain a double bond and optionally with other carbocyclic condensed or bridged rings form a polycyclic ring system.

Haloalkyl stands for partially or completely halogenated alkyl. With multiple halogenated haloalkyl, the halogen atoms may be the same or different. Preferred halogen atoms are fluorine or chlorine, especially fluorine. Wearing that Haloalkyl other substituents, the maximum possible number is reduced of the halogen atoms to the different free valences.

Furthermore, it was found that the new pyridine carbamides of the general formula (I) can be obtained if

• a) 4-methoxy-3-hydroxy-pyridine-2-carboxylic acid of the formula (II),
  with an amine of the formula (III),
  H ₂ NAR ¹ (III)
  in which
  A and R ^{1 have} the meanings given above,
  if appropriate in the presence of a diluent, if appropriate in the presence of a condensing agent and if appropriate in the presence of an acid acceptor, or if
• b) pyridine carbamides of the general formula (I) with R ² in its meaning as hydrogen with activated acid derivatives of the formula (IV),
  in which
  R ^{3 represents} alkyl or alkoxy, and
  X represents halogen or -O-CO-R ³ , where R ^{3 has} the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

Finally, it was found that the new pyridine carbamides are the general Formula (I) has a very strong action against harmful organisms. Also are the new compounds of formula (I) important intermediates, especially for Pesticides.

The compounds according to the invention are optionally in the form of mixtures various possible isomeric forms, in particular stereoisomers, such as. B. E and Z, threo and erythro and optical isomers before. Both the E as well as the Z isomers, as well as the threo- and erythro-, as well as the optical Isomers and any mixtures of these isomers claimed.

Preferred are the new compounds of formula (I) in which
A represents a single bond or alkylene having 1 to 6 carbon atoms which is optionally interrupted by heteroatoms and is optionally substituted by phenyl,
R ¹ for each optionally one or more times, identically or differently, by halogen, cyano, carboxy, phenyl (which optionally by halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ - alkoxy or C ₁ - C ₄ haloalkoxy) C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ -alkoxycarbonyl-substituted cycloalkyl or cycloalkenyl having 3 to 12 carbon atoms;
stands for aryl with 3 to 12 ring members, which is optionally mono- or polysubstituted by identical or different substituents, or for heterocyclyl with 3 to 8 ring members, the possible substituents preferably being selected from the list below:
Halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarb amoyl;
each straight-chain or branched alkyl, alkoxy, alkylthio, alkyl sulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyl oxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched acylamino, N-acyl-N-alkylamino, alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxy carbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts;
each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
and in each case, if appropriate, once or several times, identically or differently
Halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarb amoyl;
each straight-chain or branched alkyl, alkoxy, alkylthio, alkyl sulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyl oxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched acylamino, N-acyl-N-alkylamino, alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxy carbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts;
each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
substituted aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkyl thio, aryloxyalkyl, arylthioalkyl, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkyloxy or heterocyclylalkylthio and
R ^{2 represents} hydrogen, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms.

The invention relates in particular to the new compounds of formula (I) in which
A for a single bond or for methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1- , 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3- (2-methyl propylene), 1 , 1-, 1,2-, 1,3-, 1,4-, 1,5-, 2,2-, 2,3- or 2,4-pentylene or for -CH (C ₂ H ₅ ) - CH ₂ -O-,
R ¹ for cyclopropyl, cyclobutyl, cyclobentyl, cyclobutyl, cyclopentyl, which is in each case optionally up to six times substituted by fluorine, chlorine, bromine, cyano, carboxy, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, tetralinyl, decalinyl, cyclododecatrienyl, indanyl, norbornyl or adamantyl;
or for each optionally monosubstituted to trisubstituted phenyl, 1,3-benzodioxolol, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridylidyl, quinolyl, pyridyl, quinolyl, pyridyl, quinolyl, pyridyl, quinolyl, quinolyl, quinolyl, , Pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhy dropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethyl , Difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetyl amino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethylamino, acylyloxy, methylyloxy, methylyloxy, acylyloxy, acylethyloxycarbonyl Methylsulfonyloxy, ethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
each optionally optionally up to four times, identical or different, substituted by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl,
each triple linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
and / or in each case optionally up to four times, identically or differently, by fluorine, chlorine, bromine, cyano, hydroxy, amino, carboxy, formyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, trifluoro methyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, Difluorchlor methoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, tri- fluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetyl, amino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino , Dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethyl sulfonyloxy, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
substituted phenyl, phenoxy, butyl, dichloro, trifluoropropyl, propyl, phenylalkyl, phenylthio, phenoxyalkyl, phenylthioalkyl, phenylalkyloxy or phenylalkylthio, each having 1 to 4 carbon atoms in the respective alkyl chains and
R ^{2 represents} hydrogen, acetyl, propanoyl, n- or i-butanoyl, n-, i-, s- or t-pentanoyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t -Butoxycarbonyl stands.

A particularly preferred group are the new compounds of formula (I), in which
A represents a single bond or methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene or 2,2-propylene,
R ¹ for phenoxyphenyl which is in each case monosubstituted to pentasubstituted, the possible substituents preferably being selected from the following list:
Fluorine, chlorine, bromine, cyano, hydroxy, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthioifluoromethyl, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylfluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, or Acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethyl sulfonyloxy, methoximinomethyl, ethoximinoethyl, ethoximinoethyl ,
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy and
R ^{2 represents} hydrogen, acetyl, propanoyl, n- or i-butanoyl, n-, i-, s- or t-pentanoyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t -Butoxycarbonyl stands.

A particularly preferred group are also the new compounds of formula (I), in which
A for a single bond or for methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 2,2-propylene, 1,3-butylene, -CH ₂ -CH ₂ -CH (C ₆ H ₅ ) - or -CH (C ₂ H ₅ ) -CH ₂ O-,
R ¹ for cyclopropyl, cyclobutyl, cyclopentyl, which is in each case monosubstituted to monosubstituted by fluorine, chlorine, bromine, cyano, carboxy, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, tetralinyl, decalinyl, cyclodode catrienyl, indanyl, norbornyl or adamantyl,
or for 1,3-benzodioxolol,
or represents phenyl which is optionally monosubstituted to trisubstituted, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, trifluoro methyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, chloromethoxy difluoro, trifluoroethoxy , Difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethyl amino, n- or i-propylamino, dimethylamino, acyl, methylyloxy, methylyloxy, oxyethyloxyoxy, methoxycarbonyl Methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximino methyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl and
R ^{2 represents} hydrogen or acetyl.

A very particularly preferred group are the new compounds of formula (I), in which
A represents a single bond or methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene or 2,2-propylene,
R ¹ for phenoxyphenyl which is in each case monosubstituted to pentasubstituted, the possible substituents preferably being selected from the following list:
Fluorine, chlorine, bromine, cyano, hydroxy, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthioifluoromethyl, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylfluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, or
R ^{2 represents} hydrogen, acetyl, propanoyl, n- or i-butanoyl, n-, i-, s- or t-pentanoyl.

A very particularly preferred group are also the new compounds of formula (I), in which
A for a single bond or for methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 2,2-propylene, 1,3-butylene, -CH ₂ -CH ₂ -CH (C ₆ H ₅ ) - or -CH (C ₂ H ₅ ) -CH ₂ O-,
R ¹ for cyclopropyl, cyclobutyl, cyclopentyl, which is in each case monosubstituted to monosubstituted by fluorine, chlorine, bromine, cyano, carboxy, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclohexyl,
or for 1,3-benzodioxolol,
or represents phenyl which is monosubstituted to trisubstituted in each case, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, trifluoro methyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, chloromethoxy difluoro, trifluoroethoxy , Difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,
R ^{2 represents} hydrogen or acetyl.

Those in the respective combinations or preferred combinations of residues radical definitions given in detail for these radicals are independent of the respectively specified combination of the residues, optionally also by residue defi nition of other preferred areas.

The radicals listed above or specified in preferred ranges definitions apply both to the end products of the formula (I) and correspondingly for the raw materials or intermediate products required for the production.  

The following compounds may be mentioned as examples of the compounds of the formula (I) described above:

The be to carry out the method a) as a starting material necessary 4-methoxy-3-hydroxy-pyridine-2-carboxylic acid of the formula (II) is known and can be produced by known methods (compare e.g. tetrahedron (1998), 54 (42), 12 745-12 774 or Tetrahedron Lett. (1998), 39 (24), 4363-4366).

Formula (III) provides a general definition of the amines required as starting materials for carrying out process a) according to the invention. In this formula (III), A and R ¹ preferably or in particular have those meanings which have already been stated as preferred or as particularly preferred for A and R ¹ in connection with the description of the compounds of the formula (I) according to the invention.

The amines of the formula (III) are known reagents in organic chemistry.

The pyridine carbamides of the general formula (I) with R ² in its meaning as hydrogen, which are required as starting materials for carrying out process b) according to the invention, are compounds according to the invention and can be prepared by process a).

Formula (IV) provides a general definition of the activated acid derivatives required to carry out process b) according to the invention as starting materials. In this formula (IV), R ³ preferably represents alkyl or alkoxy each having 1 to 6 carbon atoms. R ³ particularly preferably represents methyl, propyl, n- or i-butyl, n-, i-, s- or t-pentanyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy. R ³ particularly preferably represents methyl. X represents halogen, preferably chlorine or -O-CO-R ³ .

The activated acid derivatives of formula (IV) are known reagents in the organic chemistry.

As a diluent for carrying out processes a) and b) all inert organic solvents are suitable. These include at playful and preferably aliphatic, alicyclic or aromatic kohlwas substances such as petroleum ether, hexane, heptane, cyclohexane, methylcyclo hexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as for example chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetra chloromethane, dichloroethane or trichloroethane; Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2- Dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone, butanone, Me thylisobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, propionitrile, n- or  i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethyl acetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamid; Esters such as methyl acetate or ethyl acetate; Sulfoxides, such as Dimethyl sulfoxide; Sulfones such as sulfolane.

The process a) according to the invention is optionally in the presence of a con carried out sealing agent. As such, come by way of example and are preferred Acid halide formers such as phosgene, phosphorus tribromide, phosphorus tri chloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride Formers such as ethyl chloroformate, methyl chloroformate esters, isopropyl chloroformate, isobutyl chloroformate or Me thanesulfonyl chloride; Carbodiimides such as N, N'-dicyclohexylcarbodi imide (DCC) or other common condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycar bonyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride, questionable.

Processes a) and b) according to the invention are optionally in the presence a suitable acid acceptor. As such, all the usual ones arrive organic or organic bases in question. These include exemplary and above preferably alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcohol latex, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, Sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, Na trium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen car bonate, and tertiary amines, such as trimethylamine, triethylamine, Tribu tylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperi din, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), Diazabicyclonones (DBN) or Diazabicycloundecen (DBU).  

The reaction temperatures can be carried out when carrying out the process according to the invention Process a) can be varied over a wide range. Generally works one at temperatures of -20 ° C to 120 ° C, preferably at temperatures of 0 ° C to 80 ° C.

The reaction temperatures can be carried out when carrying out the process according to the invention Process b) can be varied over a wide range. Generally works one at temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C up to 80 ° C.

To carry out the method a) for the production of the verb The formula (I) is used per mole of 4-methoxy-3-hydroxy-pyridine-2-carbon Acid of formula (II) generally 1 to 10 moles, preferably 1 to 5 moles of amine of formula (III).

To carry out process b) according to the invention for the preparation of the compounds of the formula (I), per mole of pyridinecarbamides of the general formula (I) with R ² in its meaning as hydrogen is generally 1 to 10 moles, preferably 1 to 5 moles, before activated Acid derivative of the formula (IV).

The methods of the invention are generally under normal pressure carried out. However, it is also possible to increase or decrease it Pressure - generally between 0.1 bar and 10 bar - to work.

The substances according to the invention have a strong microbicidal action and can fight unwanted microorganisms, such as fungi and Bacteria can be used in crop protection and material protection.

Fungicides can be used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Use Deuteromycetes.  

Bactericides can be used in plant protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae put.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
(Conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the control of plants Concentrations necessary for diseases allow treatment above ground Parts of plants, of seedlings, and of the soil.

The active compounds according to the invention can be particularly successful Combating diseases in wine, fruit and vegetable growing, such as against Botrytis or Sphaerotheca species.

The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.

The active compounds according to the invention can optionally be used in certain concentrations trations and application rates also as herbicides, to influence the plants growth, as well as for controlling animal pests. she can optionally also be used as intermediates and precursors for the synthesis use other active ingredients.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that through conventional breeding and optimization methods or through biotech biological and genetic engineering methods or combinations of these methods can be obtained, including the transgenic plants and inclusive  plant varieties that can or cannot be protected by plant breeders' rights. Plant parts should include all above-ground and underground parts and organs of plants, such as shoot, leaf, flower and root are understood, whereby exemplary leaves, needles, stems, stems, flowers, fruiting bodies, fruits and Seeds as well as roots, tubers and rhizomes are listed. To the plants sharing also includes crops, vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.

The treatment according to the invention of the plants and parts of plants with the active ingredients substances takes place directly or by influencing their surroundings, living space or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, atomization, scattering, spreading and with propagation material, especially in the case of seeds, still by single or multi-layer coating.

In material protection, the substances according to the invention can be used to protect technical materials against infestation and destruction by undesirable microorganisms use mechanisms.

In the present context, technical materials include non-living ones Understand materials that have been prepared for use in engineering are. For example, technical materials made by the invention Active substances are to be protected against microbial change or destruction, Adhesives, glue, paper and cardboard, textiles, leather, wood, paints and Plastic items, coolants and other materials can be made by micro organisms can be attacked or decomposed. As part of the to be protected Materials are also parts of production systems, such as a cooling water circuit runs, which are impaired by the multiplication of microorganisms can. Within the scope of the present invention as technical materials preferably adhesives, glues, papers and cartons, leather, wood, paints, Cooling lubricants and heat transfer liquids called, particularly preferred Wood.  

As microorganisms that break down or change the technical Materials such as bacteria, fungi, yeasts, algae and Called slime organisms. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucous organisms and algae.

For example, microorganisms of the following genera may be mentioned:
Alternaria, such as Alternaria tenuis,
Aspergillus, such as Aspergillus niger,
Chaetomium, like Chaetomium globosum,
Coniophora, such as Coniophora puetana,
Lentinus, such as Lentinus tigrinus,
Penicillium, such as Penicillium glaucum,
Polyporus, such as Polyporus versicolor,
Aureobasidium, such as Aureobasidium pullulans,
Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, like Trichoderma viride,
Escherichia, such as Escherichia coli,
Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, such as Staphylococcus aureus.

The active ingredients can depend on their respective physical and / or chemical properties can be converted into the usual formulations, such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Fine encapsulation in polymeric substances and in coating compositions for seeds, as well ULV cold and warm fog formulations.

These formulations are prepared in a known manner, e.g. B. by mixing of the active substances with extenders, i.e. liquid solvents, under pressure liquefied gases and / or solid carriers, optionally using  of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In the case of using water as a stretch means can e.g. B. also used organic solvents as auxiliary solvents become. The following are essentially suitable as liquid solvents: aromatics, such as Xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, alipha table hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, Alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solution medium, such as dimethylformamide and dimethyl sulfoxide, and water. With liquefied gaseous extenders or carriers are meant such liquids which are gaseous at normal temperature and pressure, e.g. B. Aerosol Propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and Carbon dioxide. The following are suitable as solid carriers: B. natural stone powder, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diato sea earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, Dolomite and synthetic granules from inorganic and organic flours as well as granules of organic material such as sawdust, coconut shells, corn piston and tobacco stem. Coming as emulsifying and / or foaming agents in question: e.g. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fat acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. As a dispersant are possible: B. lignin sulfite and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholi pide, such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.  

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides can be used, e.g. B. to broaden the spectrum of activity or to prevent the development of resistance. In many cases you get syner gistic effects, d. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

Fungicides

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazon, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodinconol, cypodinconol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, Ihiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK-8705,
OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-1 - [[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole, 1- [1- [2 - [(2,4-dichlorophenyl) methoxy] - phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) pentandinitrile,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1 1I-inden-4-yl) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N - (isothiocyanatomethyl) acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,
3- (1,1-dimethylpropyl) -1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decane-2-methanamine,
8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis- (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethyl] morpholine hydrochloride,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
Potassium hydrogen carbonate,
Methane tetrathiol sodium salt,
Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide.
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N- (4-cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidiriamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide,
N - ((6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide,
N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxymanimidamide,
N-formyl-N-hydroxy-DL-alanine sodium salt,
O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran-3'-one.

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, Copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60 541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Biethanomofufoxin, Bethanomethofinoxin, Bethenomethrin Butyl pyridaben
Cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, Chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, Chlovaporthrin, cis-resmethrin, Cispermethrin, Clocythrin, cloethocarb, clofentezine, cyanophos, Cycloprene, cycloprothrin, cyfluthrin , Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxinon, Flutoxinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, , Furathiocarb,
Granulosis viruses
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,
Nuclear polyhedron viruses
Lambda cyhalothrin, lufenuron
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron
Omethoate, Oxamyl, Oxydemethon M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,
Quinalphos,
Ribavirin
Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,
Tau-fluvalinate, oxalate hydrogen tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, theta cypermethrin, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate, triazophos , Triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302 Zeta-cypermethrin, Zolaprofos
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate
(3-phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) - imine
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole
2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione
2-Chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] benzamide
2-Chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] benzamide
3-methylphenyl propyl carbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone
4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) pyridazinone
Bacillus thuringiensis strain EG-2348
Benzoic acid [2-benzoyl-1- (1,1-dimethylethyl) hydrazide
Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester
[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] cyanamide
Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) carboxaldehyde
Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate
N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine
N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazinedicarbothioamide
N-methyl-N'-2-propenyl-1,2-hydrazinedicarbothioamide
O, O-Diethyl- [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

In addition, the compounds of the formula (I) according to the invention also very good antifungal effects. They have a very broad antimyko spectrum of activity, in particular against dermatophytes and fungi, Mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) such as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species like Tri chophyton mentagrophytes, Microsporon species like Microsporon canis and audouinii. The list of these mushrooms is in no way a limitation of the detectable mycotic spectrum, but is only explanatory.

The active substances can be used as such, in the form of their formulations or in the form thereof rode application forms, such as ready-made solutions, suspensions, spray  powders, pastes, soluble powders, dusts and granules can be used. The Application happens in the usual way, e.g. B. by pouring, spraying, spraying, Scattering, dusting, foaming, brushing, etc. It is also possible to use the Apply active ingredients according to the ultra-low-volume process or the active ingredient preparation or inject the active substance yourself into the soil. It can also do that Seeds of the plants are treated.

When using the active compounds according to the invention as fungicides, the effort can be reduced quantities can be varied within a wide range depending on the type of application. When treating parts of plants, the active compound application rates are in the Generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are in general between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. When treating the floor, there are problems wall amounts of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

The following examples serve to explain the invention. The invention is but not limited to the examples.

Manufacturing examples example 1 N- [4- (2,4-dichlorophenoxy) phenyl] -3-hydroxy-4-methoxy-2-pyridinecarboxamide Procedure a)

422 mg (2.5 mmol) of 2-hydroxy-3-methoxy-pyridine-2-carboxylic acid are dissolved in 15 ml of dimethylformamide at room temperature. 405 mg (3 mmol) of 1-hydroxy-1H-benzotriazole, 603 mg (3 mmol) of 4- (2,4-dichlorophenoxy) aniline, 573 mg (3 mmol) (N '- (3- Add dimethylaminopropyl) -N ethyl carbodiimide hydrochloride) and 1.26 g (12.5 mmol) of N-methylmorpholine. After stirring at room temperature for 18 hours, the dimethylformamide is removed in vacuo and the residue is taken up in 100 ml of 1N hydrochloric acid and 200 ml of ethyl acetate. After the phases have been separated, the aqueous phase is extracted twice more with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo and the residue is chromatographed on silica gel using cyclohexane / ethyl acetate (3: 1). 540 mg (53% theoretical yield) of N- [4- (2,4-dichlorophenoxy) phenyl] -3-hydroxy-4-methoxy-2-pyridine carboxamide are obtained.
MS (MS-ESI): 405.1 (M + H +)
NMR (500 MHz, CDCl ₃ ): δ = 4.01 (s, 3H), 6.94 (d, J = 5.2 Hz, 1H), 8.07 (d, J = 5.2 Hz, 1H), 10.10 (s, 1H), 12.21 (s, 1H) ppm.

Example 2 2- {4- (2,4-dichlorophenoxy) anilino] carbonyl} -4-methoxy-3-pyridinyl acetate Procedure b)

121 mg (0.3 mmol) of N- [4- (2,4-dichlorophenoxy) phenyl] -3-hydroxy-4-methoxy-2-pyridinecarboxamide are dissolved in 10 ml of methylene chloride and at 0 ° C. with 90 mg (0.9 mmol) Triethylamine and 60 mg (0.72 mmol) acetyl chloride. After stirring at room temperature for 18 hours, the mixture is diluted to 100 ml with methylene chloride and washed with 1N hydrochloric acid and saturated sodium chloride solution. It is dried over sodium sulfate and the solvent is removed in vacuo. The crude product thus obtained is chromatographed on silica gel using cyclohexane / ethyl acetate (3: 1). 100 mg (75% theoretical yield) of 2 - {[4- (2,4-dichlorophenoxy) anilino] carbonyl} -4-methoxy-3-pyridinyl acetate are obtained.
MS (MS-ESI): 447 (M + H +)
NMR (500 MHz, CDCl ₃ ): δ = 2.48 (s, 3H), 3.98 (s, 3H), 10.18 (s; 1H) ppm.

Analogously to Examples 1 and 2, and in accordance with the general description of the production processes a) and b) according to the invention, the compounds of the formula (I) listed in Table 1 below can also be prepared:

Example 14

δ = 2.80 (t, 2H, J = 7.3 Hz), 3.53 (q, 2H, J = 6.9 Hz), 3.71 (s, 6H), 3.91 (s, 3 H), 6.74 (dd, 1H, J = 7.5 and J = 1.5 Hz), 6.83 (d, 1H, J = 2.0 Hz), 6. 86 (d, 1H, J = 8.1 Hz), 7.23 (d, 1H, J = 5.1 Hz), 8.05 (d, 1H, J = 5.5 Hz), 9.14 (t, 1H, J = 5.9 Hz) ppm.

Example 15

δ = 3.91 (s, 3H), 4.49 (d, 2H, J = 6.5 Hz), 7.24 (d, 1H, J = 5.5 Hz), 7.34 (dd, 1H, J = 8.0 and 2.0 Hz), 7.60 (m, 2H), 8.07 (d, 1H, J = 5.5 Hz), 9. 83 (t, 1H, J = 5.9 Hz) ppm.

Example 16

δ = 2.33 (m, 2H), 3.24 (m, 2H), 3.90 (s, 3H), 4.01 (t, 1H, J = 7.8 Hz), 7.16 (dd, 2H, J = 7.0 and 1.4 Hz), 7.21 (d, 1H, J = 5.5 Hz), 7.24-7.35 (m, 8H), 8.03 (d, 1H, J = 5.0 Hz), 9.23 (t, 1H, J = 5.9 Hz) ppm.

Example 17

δ = 3.88 (s, 3H), 4.38 (d, 2H, J = 6.6 Hz), 5.98 (s, 2H), 6.79-6.87 (m, 2H), 6.93 (d, 1H, J = 1.5 Hz), 7.19 (d, 1H, J = 5.5 Hz), 8.02 (d, 1H, J = 5.0 Hz), 9.68 (m, 1H) ppm.  

Examples of use Example A Botrytis test (bean) / protective

Solvent: 24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
Emulsifier: 1.0 part by weight of alkyl aryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are treated with the active ingredient sprayed substance preparation in the specified application rate. After the Spray pads are covered with 2 small botrytis cinerea on each leaf Pieces of agar placed on top. The inoculated plants are darkened in a Chamber set up at about 20 ° C and 100% relative humidity.

2 days after the inoculation, the size of the infection spots on the leaves evaluated. 0% means an efficiency level that that of the control corresponds, while an efficiency of 100% means that no infestation is observed.

In this test, the substance according to the invention listed in example (1) is shown an application rate of 500 g / ha an efficiency of 91% or more.  

Example B Sphaerotheca test (cucumber) / protective

Solvent: 49 parts by weight of N, N-dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young cucumber plants are sprayed with the Active ingredient preparation in the specified application rate. 1 day after treatment the plants are inoculated with a spore suspension of Sphaerotheca fuliginea. Then the plants in a greenhouse at 70% relative Humidity and a temperature of 23 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means 0 Efficiency that corresponds to that of the control, while an efficiency 100% means that no infection is observed.

In this test, the substance according to the invention listed in examples (1) is shown an application rate of 750 g / ha an efficiency of 90% or more.

Claims (12)

1. Compounds of the general formula (I)
in which
A represents a single bond, substituted or unsubstituted alkylene, optionally interrupted by heteroatoms,
R ^{1 stands} for substituted or unsubstituted cycloalkyl, cyclo alkenyl, aryl or heterocyclyl with 3 to 8 ring members and
R ^{2 represents} hydrogen, alkylcarbonyl or alkoxycarbonyl. 2. Compounds of formula (I), according to claim 1, characterized in that
A represents a single bond or alkylene having 1 to 6 carbon atoms which is optionally interrupted by heteroatoms and is optionally substituted by phenyl,
R ¹ for each optionally one or more times, the same or different, by halogen, cyano, carboxy, phenyl (which may be by halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy is substituted), C ₁ - C ₄ -alkyl, C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -alkoxycarbonyl-substituted cycloalkyl or cycloalkenyl having 3 to 12 carbon atoms;
represents in each case mono- or polysubstituted, identically or differently substituted aryl with 3 to 12 ring members or for heterocyclyl with 3 to 8 ring members, the possible substituents preferably being selected from the list below:
Halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched acylamino, N-acyl-N-alkylamino, alkylamino, dialkylamino, alkylcarbonyl, alkyl carbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
as well as, if necessary, single or multiple, the same or different
Halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched acylamino, N-acyl-N-alkylamino, alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
substituted aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio, aryloxyalkyl, arylthioalkyl, heterocyclyl, heterocyclicoxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkyloxy or heterocyclylalkylthio and
R ^{2 represents} hydrogen, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms. 3. Compounds of formula (I), according to claim 1, characterized in that
A for a single bond or for methylene, 1,1-ethylene, 1,2-ethylene, 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3- (2-methylpropylene) is 1.1 -, 1,2-, 1,3-, 1,4-, 1,5-, 2,2-, 2,3- or 2,4-pentylene or for -CH (C ₂ H ₅ ) -CH ₂ -O- stands,
R ¹ for cyclopropyl, cyclobutyl, cyclobentyl, cyclobutyl, cyclopentyl, which is in each case optionally up to six times substituted by fluorine, chlorine, bromine, cyano, carboxy, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, tetralinyl, decalinyl, cyclododecatrienyl, indanyl, norbornyl or adamantyl;
or for each optionally monosubstituted to trisubstituted phenyl, 1,3-benzodioxolol, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridylidyl, quinolyl, pyridyl, quinolyl, pyridyl, quinolyl, pyridyl, quinolyl, quinolyl, quinolyl, , Pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhy dropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, Difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethylamino, acyletyloxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxyl sulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximino ethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylene dioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
and / or in each case optionally up to four times, identically or differently by fluorine, chlorine, bromine, cyano, hydroxy, amino, carboxy, formyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy , Trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethyl, trifluoromethylamino, dimethylamino, methylamino, formylamino, formylamino, formylamino , Diethyl amino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxy carbonyl, methylsulfonyloxy, ethylsulfonyloxy, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylene dioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
substituted phenyl, phenoxy, butyl, dichloro, trifluoropropyl, propyl, phenylalkyl, phenylthio, phenoxyalkyl, phenylthioalkyl, phenyl alkyloxy or phenylalkylthio, each having 1 to 4 carbon atoms in the respective alkyl chains and
R ² for hydrogen, acetyl, propanoyl, n- or i-butanoyl, n-, i-, s- or t-pentanoyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarb onyl, n-, i-, s- or t-Butoxycarbonyl stands. 4. Compounds of formula (I) according to claim 1, characterized in that
A represents a single bond or methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene or 2,2-propylene,
R ¹ for phen to oxyphenyl which is in each case monosubstituted to pentasubstituted, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, hydroxy, amino, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy; Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthlifluoromethylfluoromethylfluoromethylfluoromethyl, difluoromethyl Formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoxim
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylene dioxy and
R ² for hydrogen, acetyl, propanoyl, n- or i-butanoyl, n-, i-, s- or t-pentanoyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, n-, i-, s- or t-Butoxycarbonyl stands. 5. Compounds of formula (I), according to claim 1, characterized in that
A for a single bond or for methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 2,2-propylene, 1,3-butylene, -CH ₂ -CH ₂ -CH (C ₆ H ₅ ) - or -CH (C ₂ H ₅ ) -CH ₂ O-,
R ¹ for cyclopropyl, cyclobutyl, cyclobentyl, cyclobutyl, cyclopentyl, which is in each case optionally up to six times substituted by fluorine, chlorine, bromine, cyano, carboxy, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, tetralinyl, decalinyl, cyclododecatrienyl, indanyl, norbornyl or adamantyl;
or for 1,3-benzodioxolol;
or represents in each case optionally mono- to trisubstituted phenyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, Difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethylamino, acyletyloxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxy, methoxyl sulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximino ethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylene dioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl and
R ^{2 represents} hydrogen or acetyl. 6. Compounds of formula (I) according to claim 1, characterized in that
A represents a single bond or methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene or 2,2-propylene,
R ¹ for phen to oxyphenyl which is in each case monosubstituted to pentasubstituted, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, hydroxy, amino, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethyl, difluoromethylfluifluoromethyl, difluoromethylfluifluoromethyl, difluoromethylfluifluoromethyl
R ^{2 represents} hydrogen, acetyl, propanoyl, n- or i-butanoyl, n-, i-, s- or t-pentanoyl. 7. Compounds of formula (I) according to claim 1, characterized in that
A for a single bond or for methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 2,2-propylene, 1,3-butylene, -CH ₂ -CH ₂ -CH (C ₆ H ₅ ) - or -CH (C ₂ H ₅ ) -CH ₂ O-,
R ¹ for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, which is optionally monosubstituted to 6-fold substituted by fluorine, chlorine, bromine, cyano, carboxy, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl;
or for 1,3-benzodioxolol;
or represents in each case optionally mono- to trisubstituted phenyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl, ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, trifluoromethyl, trifluorethyl, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxyl, Difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and
R ^{2 represents} hydrogen or acetyl. 8. A process for the preparation of compounds of formula (I) as defined in claim 1, characterized in that

• a) 4-methoxy-3-hydroxy-pyridine-2-carboxylic acid of the formula (II),
  with an amine of the formula (III),
  H ₂ NAR ¹ (III)
  in which
  A and R ^{1 have} the meanings given above,
  if appropriate in the presence of a diluent, if appropriate in the presence of a condensing agent and if appropriate in the presence of an acid acceptor, or if
• b) pyridinecarbamides of the general formula (I) with R ² in its meaning as hydrogen with activated acid derivatives of the formula (IV)
  in which
  R ^{3 represents} alkyl or alkoxy, and
  X represents halogen or -O-CO-R ³ , where R ^{3 has} the meaning given above,
  optionally in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.

9. agents containing extenders and / or carriers and optionally surface-active substances, characterized by a content of at least one of the substances as defined in claims 1 to 7. 10. A method for controlling harmful organisms, thereby records that compounds as in claims 1 to 7 or means as defined in claim 9 on harmful organisms and / or their Living space. 11. Use of compounds as defined in claims 1 to 7 for Pest control. 12. A method for producing agents as defined in claim 9, characterized characterized in that compounds as in claims 1 to 7 defined with extenders and / or carriers and / or surfaces active funds mixed.