EP1706387A1 - Substituted heterocyclic amides having a fungicidal effect - Google Patents

Abstract

Disclosed are amides of formula (I), wherein the symbols have the meanings indicated in the description, a method for producing said substances, the use thereof for controlling undesired microorganisms, as well as intermediate products of formulas (IIIa) and (IIIb), wherein the symbols have the meanings indicated in the description.

Description

 SUBSTITUTED HETΞROCYC ISCHE AMIDES WITH FUNGICIDAL EFFECT

The invention relates to amides, several processes for their preparation and their use for controlling harmful organisms.

Amides with fungicidal properties are known for example from JP 2001348378. However, the fungicidal activity of these compounds leaves room for improvement in some cases.

Since the ecological and economic requirements for modern fungicides are constantly increasing, for example in terms of activity spectrum, toxicity, selectivity, application rate, residue formation and inexpensive to produce, and also e.g. Problems with resistance can arise, the constant task is to develop new fungicides that have advantages over the known ones, at least in some areas.

New compounds of the general formula (I) have been found

in which

Rl, R ² , and R ^{3 are the} same or different and are independently hydrogen, halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio. Alkylsulfonyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfmyl 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 alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;

Cycloalkyl having 3 to 6 carbon atoms, wherein

Rl, R ² , and R ^{3 are} not simultaneously hydrogen, or

R and R ² together with the carbon atoms to which they are attached form a carbocyclic ring,

Het represents an unsubstituted or substituted five-membered aromatic heterocyclic ring,

R ^ represents hydrogen, halogen, cyano, alkyl having 1 to 8 carbon atoms, alkenyl or alkynyl having 2 to 8 carbon atoms or haloalkyl having 1 to 8 carbon atoms and 1 to 9 halogen atoms,

R ⁵ and R ^ are the same or different and are independently of one another unsubstituted or halogen or cyano-substituted alkyl, alkoxyalkyl each having 1-8 carbon atoms in the respective alkyl chains or alkenyl or alkynyl each having 2-8 carbon atoms or cycloalkyl having 3-8 Carbon atoms or. Represents unsubstituted or substituted arylalkyl having 1 to 8 carbon atoms in the alkyl chain,

A represents alkanediyl or cycloalkanediyl and

Y stands for oxygen or sulfur.

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino. Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, such as. B. phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.

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

Cycloalkenyl stands for carbocyclic, ring-shaped compounds which contain at least one double bond and optionally form a polycyclic ring system with further carbocyclic, fused-on αi or bridged rings.

Furthermore, it was found that the new amides of the general formula (I) have a very good activity against harmful organisms, in particular a strong fungicidal activity.

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

The invention preferably relates to compounds of the formula (Ia)

in which

R \ R ^2, and R ³ are identical or different and independently hydrogen ^", fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, α-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy , Trifluoromethoxy, difluorochloro ethoxy, Trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoro-methylsulfinyl or trifluoromethylsulphonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, Methoximinόmethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or

Rl and R ² together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring members, where Rl, R ² and R ^{3 are} not simultaneously hydrogen,

R ^ ^{a represents} hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Is allyl, propargyl or trifluoromethyl,

R ^ and R ^ are the same or different and are independently methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl,

Allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl, or optionally by hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluor - methoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted benzyl,

A for methanediyl, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1, 1-diyl, propane-1, 2-diyl, propane-1,3-diyl, propane-2,2- diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, butane-2,2-diyl, butane-2,3-diyl, l, l-dieethyl-1,2-diyl, cyclopropane-1,1-diyl or cyclopropane-1,2-diyl,

Y stands for oxygen or sulfur and

G represents oxygen, sulfur or -R ^ ^a , where R ^{7a represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. The invention also preferably relates to compounds of the formula (Ib)

in which

A, R1, R ² , R ³ , R ^, R ^ and Y have the same meaning as preferably given for A, R% R ² , R ³ , R ⁵ , R ^ and Y in formula (Ia) is

R ^ b represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Is allyl, propargyl or trifluoromethyl,

G ^{2 represents} oxygen, sulfur or NR ^71D , where

R ^ b represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The invention further preferably relates to compounds of the formula (Ic)

in which

A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as has preferably been given for AR *, R ² , R ³ , R ⁵ , R ^ and Y in formula (la) .

R ^ ^{0 represents} hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Is allyl, propargyl or trifluoromethyl, G ^{3 represents} oxygen, sulfur or NR ^7c , where

R ^{7c represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The invention further preferably relates to compounds of the formula (Id)

in which

A, Rl, R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as preferably given for A, R *, R ² , R ³ , R ⁵ , R ^ and Y in formula (la) is ™ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

G ^ stands for oxygen, sulfur or N-R, where

R ^{7 (} ^ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The invention further preferably relates to compounds of the formula (Ie)

in which

A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as preferably given for AR ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y in formula (1 a) is

G ^{5 represents} oxygen, sulfur or NR ^7e , where R ^{7e represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The invention further preferably relates to compounds of the formula (If)

in which

A, R, R ² , R ³ , R ⁵ , R ^ and Y have the same meaning as has preferably been given for A, R, R ² , R ³ , R ^, R ^ and Y in formula (la) .

G ^ stands for oxygen, sulfur or -R ⁷ ^, wherein

R ⁷ ^ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The invention further preferably relates to compounds of the formula (Ig)

in which

A, R, R ² , R ³ , R ⁵ , R6 and Y have the same meaning as preferably given for A, Rl, R ² , R ³ , R ⁵ , R ° and Y in formula (Ia),

G ^{7 represents} oxygen, sulfur or NR ⁷ S, where

R ^{7§ represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In the formulas (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), A, R ¹ , R ² , R ³ , R ⁵ , RÖ and Y have the following particularly preferred meanings: Rl, R ² and R ³ are the same or different and, independently of one another, are also particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, methoximinomethyl, ethoximinomethyl, ethoximinoethyl or meth oximinoethyl, cyclopropyl, cyclobutyl, Cyclopentyl or cyclohexyl stand, or

R and R ² together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring members:

R, R ² , and R ³ do not simultaneously represent hydrogen.

A particularly preferably represents methanediyl, ethane-1,1-diyl, ethane-1, 2-diyl, propane-1, l-diyl, propane-1, 2-diyl, propane-1, 3-diyl or propane-2 , 2-diyl.

Y particularly preferably represents oxygen.

R5 and R6 are identical or different and, independently of one another, are particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl.

Stand in formula (Ia)

R ^ ^{a is} particularly preferred for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl trifluoromethyl, chlorine or cyano and

G particularly preferably represents oxygen, sulfur or NR ^7a , where R ^7a particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

Stand in formula (Ib)

R ^ b particularly preferably for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorine or cyano and G ² particularly preferably represents oxygen, sulfur or NR ^{71 :)} , where

R ^71D particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

Stand in formula (Ic)

R ^ ⁰ particularly preferably for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano and

G ³ particularly preferably for oxygen, sulfur or NR ^7c , wherein

R ^7c particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

Stand in formula (Id)

R ^ d particularly preferably for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl trifluoromethyl, chlorine or cyano and

G ^ particularly preferred for oxygen, sulfur or NR ^7c *, wherein

R ⁷ d particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In formula (Ie) stands

G ^ particularly preferably represents oxygen, sulfur or NR ^e , where

R ^7e particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

Stand in formula (If)

G ^ particularly preferably represents oxygen, sulfur or NR ⁷ ^, wherein

R ^7f particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

Stand in formula (Ig)

G ⁷ particularly preferably represents oxygen, sulfur or NR ⁷ S, where R ⁷ S particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The general definitions given above or those specified in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.

The radical definitions given for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.

Finally, it was found that the amides of the general formula (I) can be obtained if

a) carboxylic acid derivatives of the general formula (II)

in which

R, R ² , R ³ and R ^ have the meanings given above and represent hydroxyl, halogen or alkoxy,

with an amine of the general formula (DI)

in which

R- \ RÖ and A have the meanings given above,

Or with an acid addition complex thereof if appropriate in the presence of an acid acceptor, if appropriate in the presence of a condensing agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent, or if

b) reacting amides of the formula (I) with Y ^' in its meaning as oxygen with a sulfurization reagent, optionally in the presence of a diluent.

If, for example, 3- (4-chlorophenyl) -5-methylisoxazole-4-carbonyl chloride and (4-ethoxy-3-methoxybenzyl) amine are used as starting materials, the course of process (a) according to the invention can be illustrated by the following formula:

Formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out process a) according to the invention. In this formula (II), R *, R ² , R ³ and R ^ preferably, or in particular, have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R1 , R ² , R ³ and R ^ were specified; T preferably represents alkoxy having 1 to 4 carbon atoms, in particular methoxy or ethoxy, hydroxyl or chlorine.

The starting materials of the formula (II) are known and / or can be prepared by processes known per se (see, for example, J. Org. Chem. 27 (1962) 4305; J. Chem. Soc. (1963) 5838, 'J. Chem Soc. (1963) 5845; Chem. Ber. 106, 3275 (1973); US 3,479,365; US 3,551,440; J. Org. Chem. (1967) 32 (10) 3132; Tetrahedron 25, (1969), 389; Synthetic Com. (1987), 17 (2), 165; EP 352581; EP 352581; EP 1186598; Bioor. & Medicinal Chem. Lett, 11 (5), 641 (2001); JP 20011011060; JP 2001011059; EP 352581; Tet. Lett. 23, (2), 235 (1982); J. of Org. Chem. 55 (13), 4011 (1990); EP 352581; EP 3252581; Synthesis, (1), 64 (1996); GB 1,058,384; US 3,257,411; J. Am. Chem. Soc. (1969), 89 (21), 5462; J. Org. Chem. (1967), 27, 4305; US4,380,465; Chem. Ber. 105, (1972) 196 ; Tetrahedron Letters 17, (1971), 1281; WO95 / 04724; CH 502365; EP 785193; Heterocycles (2000), 53 (1), 159; Aust. J. Chem. (1994), 47,1375; Bulletin des Soc Chim. Beiges (1996), 105 (1), 33; Bulletin des Soc. Chim. Beiges (1996), 105 (4), 189). The further to carry out the method a) as _. The amines required for starting materials are generally defined by the formula (HI). In this formula (HI), A, R ⁵ and R ^ preferably, or in particular, have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R ^ and R ° were specified.

Some of the amines of the formula (IH) are known organic synthetic chemicals and / or can be prepared by processes known per se.

Amines of the formulas (Hl-a) are new and also an object of the invention

in which

A and R ^{5 have} the meanings given above and

R ^{8 represents} allyl, propargyl, 2-butynyl or cyanoethyl

and (iπ-b)

in which

A and RP have the meanings given above and

R9 represents allyl, propargyl, 2-butinyl or cyanomethyl.

The amines of the formulas (Hl-a) and (Hl-b) are obtained (process c) if hydroxyl compounds of the general formula (IV-a)

in which

A and R ^{5 have} the meanings given above,

or hydroxy compounds of the general formula (IV-b)

in which

A and R ° have the meanings given above,

with allyl, propargyl, 2-butynyl chloride, bromide or iodide or chloro-bromo- or iodoacetonitrile, optionally in the presence of a diluent such as acetonitrile and optionally in the presence of an acid acceptor such as potassium carbonate.

Before the alkylation, the amino group of the compounds of the formulas (IV-a) and (IV-b) is optionally provided with a protective group which is customary for amines, such as, for example, t-butoxycarbonyl, by customary methods. This gives rise to compounds of the formula (IV-a *) or (IV-b *)

(IV-a *) (IV-b *)

in which

R ⁵ and R "have the meanings given above and

PG stands for the protective group.

After the alkylation reaction, which initially leads to compounds of the formula (HJ-a *) or (HI-b *)

(lH-a *) (m-b *)

in which

R °, R ", PG, and R ^ and R ° have the meanings given above,

leads, the protective group is split off again according to usual methods (see also the preparation examples).

If, for example, 4- (aminomethyl) -2-methoxyphenol and allyl bromide are used as starting materials, the course of process (c) according to the invention can be illustrated by the following formula:

Those required as starting materials for carrying out process c) according to the invention

Hydroxy compounds are generally defined by the formula (TV-a). In this formula (IV-a) preferably, or in particular, has the meaning which has already been stated in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for R ^.

The hydroxy compounds of the formula (IV-a) are commercially available synthetic chemicals or can be obtained by known methods (compare, for example, J. Chem. Soc. 127 (1925), 560 and J. Amer. Chem. Soc. 72 (1950), 2781; JP 11130739 or DE 19958165).

Formula (IV-b) provides a general definition of the hydroxy compounds required alternatively as starting materials for carrying out process c) according to the invention. In this formula (IV-b), R ° preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for RP in connection with the description of the compounds of the formula (I) according to the invention. The hydroxy compounds of the formula (IV-b) are commercially available synthetic chemicals or can be obtained by known methods (compare, for example, Ger. Offen, 4322065; J. Org. Chem., 53 (5), 1064-71 (1988); Synth. Comm., 7 (1), 71-8 (1977)).

The compounds allyl, propargyl, 2-butynyl chloride, bromide or iodide or chlorine, bromine or iodoacetonitrile which are furthermore required as starting materials for carrying out process c) according to the invention are generally customary synthetic chemicals.

If, for example, 3- (4-chloro-henyl) -N- (4-ethoxy-3-methoxybenzyl) -5-methylisoxazole-4-carboxamide and phosphorus pentasulfide are used as starting materials, the course of process (b) according to the invention can be illustrated by the following formula are illustrated:

Amides required as starting materials for carrying out process b) according to the invention are compounds according to the invention and can be obtained by process a) according to the invention.

All reagents that are capable of exchanging carbon-bound oxygen atoms for sulfur atoms, such as e.g. Hydrogen sulfide, phosphorus pentasulfide or Lawesson's reagent.

Hydrogen sulfide, phosphorus pentasulfide or Lawesson's reagent are commercially available

Chemicals for synthesis.

Process a) according to the invention is optionally carried out in the presence of a diluent. As such, water and organic solvents come into consideration. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphos- phorsäuretriamid; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

Process a) according to the invention is optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as. Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecen (DBU).

Process a) according to the invention is optionally carried out in the presence of a suitable condensing agent. As such, all commonly used for such amidation condensing agent ^• come into question. Examples include acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as ethyl chloroformate, methyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; Carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ) or triphehyl- phosphine / carbon tetrachloride.

Process a) according to the invention is optionally carried out in the presence of a catalyst. Examples include 4-dimethylaminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.

The reaction temperatures can be varied within a substantial range when carrying out process a) according to the invention. In general, temperatures between - 50 ° C and + 150 ° C, preferably at temperatures between -20 ° C and 150 ° C.

To carry out process a) according to the invention, 1 to 5 mol, preferably 1.0 to 2.5 mol, of amine are generally employed per mol of carboxylic acid derivative of the formula (11). The process a) according to the invention can also be carried out as a two-stage process. The carboxylic acid derivatives of the general formula (II) are first converted into an activated form and, in a subsequent step, reacted with the amines of the general formula (TU) to give the amides of the general formula (I) according to the invention.

As the activated form of the carboxylic acid derivatives of the formula (II), all carboxy-activated derivatives can be used, e.g. Acid halides, preferably acid chlorides, acid azides, furthermore symmetrical and mixed anhydrides, such as for example the mixed o-alkyl carbonic anhydrides, further activated esters, such as e.g. p-nitrophenyl ester or N-hydroxisuccinimide ester as well as adducts with condensing agents, e.g. Dicyclohexyl carbodiimide or activated forms of the carboxylic acids generated in situ.

Suitable diluents for carrying out process b) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, ^• 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole.

The reaction temperatures can be varied within a substantial range when carrying out process b) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.

^') B for the preparation of compounds of formula (I) to carry out the process of the invention are employed per mole of the amide of formula (I) with Y in its meaning as an oxygen generally 0.1 to 15 mol, preferably 0.5 to 8 Mole of sulfurization reagent.

The reaction is carried out, worked up and isolated using known processes (see also the preparation examples).

The processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.

The reaction is carried out, worked up and isolated according to known methods. The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.

Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

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

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 hu uli 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 active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.

Plant-strengthening (resistance-inducing) substances are to be understood in the present context as substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms. Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses. The materials of the invention ^'are thus used to protect plants for a certain period of time after treatment against attack by the pathogens mentioned. The period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention can be used particularly successfully to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Alternaria, Phytophtora and Plasmopara 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.

If appropriate, the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and plant parts according to the invention with the active compounds takes place directly or by influencing their surroundings, living space or storage space according to the usual treatment methods, for example by 'dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.

In material protection, the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.

In the present context, technical materials are understood to mean non-living materials that have been prepared for use in technology. For example, technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms , In the context of the materials to be protected, parts of production plants, for example cooling water circuits, which may be impaired by the multiplication of microorganisms, may also be mentioned. In the context of the present invention, technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.

Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular molds, wood-coloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

Microorganisms of the following genera may be mentioned, for example:

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,

Aαireobasidium, 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.

Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. 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, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or Glycόl and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. Solid carrier materials come into question: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. Solid carrier materials for granules are considered: for example broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, Corn cobs and tobacco stalks. Suitable emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue 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 of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to spread the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

fungicides:

2-phenylphenol; 8-hydroxyquinoline sulfates; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benalaxyl-M; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamäcril; Benzamacril-isobutyl;

bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S; boscalid; bromuconazole; Bupirimate;

Buthiobate; butylamine; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin;

carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil;

chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine;

dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; Dimetiiomorph; Dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone;

fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil;

fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover;

flumorph; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; Flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;

Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; L azalil; Imibenconazole; hninoctadine triacetate; Iminoctadine tris (albesilate); iodocarb; ipconazole; iprobenfos; iprodione;

iprovalicarb; frumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb;

maneb; Meferi zone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; Methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil;

myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; Orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole; pencycuron; phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz; procymidone; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; Pyroquilon; Pyroxyfur; Pyirolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine;

Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen;

Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon;

triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; Tridemoφh; trifloxystrobin; Trifluamizoles; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide;

(2S) -N- [2- [4 - [[3- (4-chloro-phenyl) -2-propyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] -butanarrιid; l- (l-naphthalenyl) -lH-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methyl sulfonyl) pyridine; 2-Ammo-4-memyl-N-phenyl-5-thiazolcarboxarnid; 2-chloro-N- (2,3-dihydro-l, 1,3-trimethyl-lH-inden-4-yl) -3-pyridiricarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol; Methyl l- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) - 1H-imidazole-5-carboxylate; Monokaliumcarbonat; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide;

N-butyl-8- (l, l-dinαethyle yl) -l-oxaspiro [4.5] decan-3-arrώι; Natriumtetracarbonat; as well as copper salts and preparations, such as Bordeaux mixture; Copper hydroxide, rupfer naphthenate; copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Kupferoxin.

bactericides:

, Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid. Oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides:

1. Acetylcholinesterase (AC E) inhibitors

1.1 Carbamates (e.g. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Chloethocarb, Coumaphos, Cyanophosphos, Cyanophosphos, Cyanophosphos, Cyanophosphos Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methio-carb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb)

1.2 Organophosphates (e.g. acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorophyros (-methyl / -ethyl) Coumaphos, Cyanofenphos, 'Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Ethulophone, EthN. EPN , Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobefos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathec, Methathionos, Methathionos, Malathion Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methylΛethyl), Profenofos, Propaphos, Pro petamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon), vamidothion

2. Sodium channel modulators / voltage-dependent sodium channel blockers

2.1 Pyrethroids (e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-chlorothrinet -Resmethrin, Cis-Perrnethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Delta-methrin, Empenthrin (lR-isomer), Esfenxerate, Fenofen, Etofen , Fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, hniprothrin, kadethrin, lambda-cyhalothrin, perofluthrin (perofluthrin) (perofluthrin) (perofluthrin) (perofluthrin) (perofluthrin) trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetra-methrin (lR-isomer), Tralomethrin, Transfluthrin, Pyrirhrin, ZXIir9090 2.2 oxadiazines (e.g. indoxacarb)

3. Acetylcholine receptor agonist antagonists

3.1 Chloronicotinyls / neonicotinoids (e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam)

3.2 Nicotine, Bensultap, Cartap

4. Acetylcholine receptor modulators

4.1 Spinosyne (e.g. Spinosad)

5. GABA-gated chloride channel antagonists

5.1 Cyclodienes Organochlorins (e.g. Camphechlor, Chlordane, Endosulfan, ^' Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor

5.2 Fiprole (e.g. Acetoprole, Ethiprole, Fipronil, Vaniliprole)

6. Chloride channel activators

6.1 Mectins (e.g. abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, mitemectin, milbemycin)

7. Juvenile hormone mimetics

(e.g. Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene)

8. Ecdysonagonists / disruptors

8.1 Diacylhydrazine (e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide)

9. Inhibitors of chitin biosynthesis

9.1 Benzoyl ureas (e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron)

9.2 Buprofezin

9.3 Cyromazines 10. Inhibitors of oxidative phosphorylation, ATP disruptors

10.1 Diafenthiuron

10.2 organotins (e.g. azocyclotin, cyhexatin, fenbutatin-oxide)

11. Decoupler of oxidative phosphorylation by interrupting the H proton gradient

11.1 pyrroles (e.g. chlorfenapyr)

11.2 Dinitrophenols (e.g. Binapacyrl, Dinobuton, Dinocap, DNOC)

12. Site I electron transport inhibitors

12.1 METI's (e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)

12.2 Hydramethylnone

12.3 Dicofol

13. Site II electron transport inhibitors

13.1 Rotenone

14. Site III electron transport inhibitors

14.1 acequinocyl, fluacrypyrim

15. Microbial disruptors of the insect intestinal membrane

Bacillus thuringiensis strains

16. Inhibitors of fat synthesis

16.1 tetronic acids (e.g. spirodiclofen, spiromesifen)

16.2 tetramic acids [e.g. 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3- (2, 5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] - dec-3-en-4-yl ethyl ester, CAS Reg.No .: 382608-10-8) and carbonic acid, cis-3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg.-No .: 203313- 25-1)] 17. Carboxamides

(e.g. flonicamide)

18. Octopaminergic agonists

(e.g. Amitraz)

19. Inhibitors of magnesium-stimulated ATPase

(e.g. propargite)

20. Phthalamides

(e.g. N ² - [l, l-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N ¹ - [2-methyl-4- [l, 2,2,2-tetrafluoro-l- (tτi- fluoromethyl) ethyl] phenyl] -l, 2-benzenedicarboxamide (CAS Reg.-No .: 272451-65-7), flubendiamides)

21. Nereistoxin analogs

(e.g. Thiocyclam hydrogen oxalate, Thiosultap-sodium)

22. Biologicals, hormones or pheromones

(e.g. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhician spec, Paecüomyces spec, Thuringiensin, Verticillium spec.)

23. Active substances with unknown or non-specific mechanisms of action

23.1 fumigants (e.g. aluminum phosphide, methyl bromide, sulfuryl fluoride)

23.2 Selective feeding inhibitors (e.g. cryolite, flonicamide, pymetrozine)

23.3 mite growth inhibitors (e.g. clofentezine, etoxazole, hexythiazox)

23.4 amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, Chinome- thionate, chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, flufenerim, Flutenzin, Gossyplure, methyl hydrazine none, Japonilure, Metoxadiazone , Petroleum, piperonyl butoxide, potassium oleate, pyrafluprole, pyridalyl, pyriprole, sulfluramide, tetradifon, tetrasul, triarathene, verbutin, furthermore the compound 3-methyl-phenyl-propylcarbamate (Tsu acid Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoro1hyl) -8-azabicyclo [3.2.l] octane-3-carbonitrile (CAS Reg.No. 185982-80-3) and the corresponding 3-endo isomer (CAS Reg.No. 185984-60-5) (see WO 96/37494, WO 98/25923), and preparations which contain insecticidal plant extracts, nematodes, fungi or viruses.

A mixture with other known active compounds, such as herbicides or with fertilizers and growth regulators, safeners or semiochemicals, is also possible.

In addition, the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, molds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, microsporon species such as microsporon canis and audouinii. The list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.

When the active compounds according to the invention are used as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

As already mentioned above, according to the invention, all plants and their parts can be treated. In a preferred embodiment, plant plants which occur wildly or are obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are species and plant cultivars and their parts are treated; in a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The term “parts” or “parts of plants” or “parts of plants” was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention can also result in superadditive (“synergistic”) effects Strengthening the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.

The preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant wax. growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and or workability Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or vir and an increased tolerance of the plants to certain herbicidal active ingredients. The important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned as examples of transgenic plants, corn, soybeans, potatoes, cotton, tobacco and rapeseed are particularly emphasized. The traits are particularly emphasized as the increased defense of the plants against insects, arachnids, namatodes and snails by toxins that arise in the plants, especially those that are caused by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryIA (b), CryΙA (c), CryllA, CrylEA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter referred to as "Bt plants"). Properties ("traits") are also used Particularly emphasized is the increased, defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins. The properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazoline, ■ sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene). The desired properties (“traits”) ) conferring genes can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready © (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), LMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or to be marketed in the future with these or future-developed genetic properties ("traits").

The plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

The preparation and use of the active compounds according to the invention can be seen from the following examples. Preparation Examples

example 1

Procedure a)

To a solution of 1.201 g (5.518 mmol) of 4-ethoxy-3-methoxy-benzylamine hydrochloride in 20 ml of dichloroethane and 1.117 g (11.035 mmol) of triethylamine are added 1.285 g (5.061 mmol) of 3- (4-chloro-phenyl) at room temperature. -5-methyl-4-isoxazole-carbonyl chloride and stirred under reflux for 1 hour. The mixture is cooled to room temperature, mixed with 10O ml of ice water, with conc. Acidified hydrochloric acid, mixed with dichloroethane, the organic phase separated, washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from isopropanol. 1.1 g (55% of theory) of N4- (4-ethoxy-3-methoxy-benzyl) -3- (4-chloro-phenyl) -5-methylisoxazole-4-carboxamide with a melting point of 158 ° C. are obtained.

HPLC: LogP = 2.93

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

Table 1

The logP values were determined in accordance with EEC Directive 79/831 Annex V. A ^0, by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)

Preparation of the precursors of formula (III)

Procedure c)

To a solution of 4.1 g (21.620 mmol) of 4-hydroxy-3-methoxybenzylamine hydrochloride in 50 ml of ethyl acetate and 5 ml of triethylamine are added 4.954 g (22.7 mmol) of pyrocarbonic acid diet. -butyl ester and stirred for 18 hours at room temperature. Then 100 ml of ethyl acetate are added, the mixture is washed with 50 ml of water, then with 50 ml of dilute citric acid and 50 ml of sodium hydrogen carbonate solution and finally with 50 ml of saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated under reduced pressure.

3.7 g (67% of theory) of 4-hydroxy-3-methoxybenzylcarbamic acid tert are obtained. -butyl ester (VI-a * -l)

HPLC: logP = 1.91

5.43 g (36.519 mmol) propargyl bromide, 5 g anhydrous, are added to a solution of 3.7 g (14.607 mmol) tert-butyl 4-hydroxy-3-methoxybenzylcarbamic acid (VI-a * -l) in 50 ml acetone Potassium carbonate and 0.15 g of potassium iodide added and heated under reflux for 18 hours. The reaction mixture is added to 100 ml of water and extracted with 200 ml of ether. The organic phase is washed twice with 10% sodium hydroxide solution, dried over sodium sulfate and concentrated. 3.2 g (73% of theory) of 4- (propargyloxy) -3-methoxybenzylcarbamic acid butyl ester (IH-a * -l) are obtained.

(HPLC: logP = 2.57).

To a solution of 3.2 g (10.984 mmol) of 4- (propargyloxy) -3-methoxybenzylcarbamic acid tert-butyl ester in 50 ml of ethyl acetate are added 3 ml of a conc. Hydrogen chloride solution, stirred for 18 hours at room temperature and filtered off the precipitate formed. This is washed twice with ethyl acetate and dried in vacuo. 2.0 g (79% of theory) of 4- (propargyloxy) -3-methoxybenzylamine hydrochloride (HI-a-1) are obtained

(HPLC: logP = 0.20). Analogously, and in accordance with the general description of the production process c) according to the invention, the compounds of the formula (III) listed in Table 2 below can also be prepared:

Table 2

The logP values were determined in accordance with EEC Directive 79/831 Annex V. A ⁸ by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)

Examples of use:

Example A

Phytophthora test (tomato) / protective

Solvent: 24.5 parts by weight of acetone, 24.5 parts by weight of dimethylacetamide

Emulsifier:. • 1 part by weight of alkyl aryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at approx. 20 ° C and 100% relative humidity.

Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, the substances according to the invention listed in Examples 1, 24, 38, 39, 40, 41, 42, 46, 47, 48, 50, 51, 54, 58, 61, 6 and 68 show at an application rate of 100 g / ha an efficiency of 94% or more.

Example B

Plasmopara test (vine) / protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in an incubation cabin at about 20 ° C. and 100% relative atmospheric humidity for 1 day. The plants are then placed in a greenhouse for 4 days at approx. 21 ° C and approx. 90% humidity. The plants are then moistened and placed in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, those in Examples 1, 24, 35, 36, 38, 39, 40, 41, 42, 43, 44, 46, 47, 48, 49, 50, 51, 54, 56, 58, 61, 62 and 68 listed substances according to the invention with an application rate of 100 g / ha an efficiency of 90% or more.

Claims

claims

Amides of formula (I)

in which

R, R- ² , and R- are the same or different and are independently hydrogen, halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched alkenyl, alkynyl, alkenyloxy or alkynyloxy 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 alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;

Cycloalkyl having 3 to 6 carbon atoms, wherein

R, R ² , and R ^{3 are} not simultaneously hydrogen, or R and R ² together with the carbon atoms to which they are attached form a carbocyclic ring,

Het represents an unsubstituted or substituted five-membered aromatic heterocyclic ring, R ^ represents hydrogen, halogen, cyano, alkyl having 1 to 8 carbon atoms, alkenyl or alkynyl having 2 to 8 carbon atoms or haloalkyl having 1 to 8 carbon atoms and 1 to 9 halogen atoms stands,

R5 and R6 are the same or different and are independently of one another unsubstituted or halogen or cyano-substituted alkyl, alkoxyalkyl each having 1-8 carbon atoms in the respective alkyl chains or alkenyl or alkynyl each having 2-8 carbon atoms or cycloalkyl having 3-8 Represents carbon atoms or represents unsubstituted or substituted ^' arylalkyl having 1 to 8 carbon atoms in the alkyl chain,

A represents alkanediyl or cycloalkanediyl and Y represents oxygen or sulfur.

2. Compounds of formula (I) according to claim 1, from the group of compounds of formula (Ia), a)

in which

R, R ² , and R ^{3 are the} same or different and are independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, Methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or

R and R ² together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring members, where R *, R ² and R ³ do not simultaneously represent hydrogen,

R ^ ^{a represents} hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Is allyl, propargyl or trifluoromethyl,

R ⁵ and R6 are the same or different and are independently methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl,

Allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl, or optionally by hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy , Trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, methylimoxomoxomethyloxoxomethylethyloximethylethyloximethylethyloximethylethyloximinoethyloximethylmethylimoxomoxyloximethylethyloximethylethyloximethylethyloximethylmethylimoxomoxyloxymoxyloxymoxyloxymoxyloxymethyloxy

A for methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2- diyl, butane-1,1-diyl, butane-1, 2-diyl, butane-1,3-diyl, butane-l, 4-diyl, butane-2,2-diyl, butane-2,3-diyl, l, l-diethyletane-l, 2-diyl, cyclopropane-1, 1-diyl or cyclopropane-1, 2-diyl,

Y stands for oxygen or sulfur and G represents oxygen, sulfur or NR ^7a , where

R ^ ^{a represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

b) compounds of the formula (Ib),

in which

A, R, R ² , R ³ , R ⁵ , R ^ and Y have the same meaning as in formula (Ia),

P 4 "b ^ _r hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n- Heptyl, allyl, propargyl or trifluoromethyl,

G ^{2 represents} oxygen, sulfur or NR ^7b , where

R ^{7b represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

c) compounds of the formula (Ic),

in which

A., R, R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as in formula (Ia), R ^4c for hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl , Propargyl or trifluoromethyl,

G ^{3 represents} oxygen, sulfur or NR ^7c , where

R ^{7c represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

d) compounds of the formula (Id),

in which

A, R, R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as in formula (Ia),

R ^ d represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, G ^{4 represents} oxygen, sulfur or NR ^{7 (} where

R ^{7d represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; e) compounds of the formula (Ie),

in which A, R, R ² , R ³ , R ⁵ , R ^ and Y have the same meaning as in formula (Ia),

G ^{5 represents} oxygen, sulfur or NR ^7e , where

R ^{7e represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

f) compounds of the formula (If),

in which

A, R, R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as in formula (Ia),

G ^ stands for oxygen, sulfur or NR ⁷ ^, wherein

R ^{7f represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl and

g) compounds of the formula (Ig),

in which

A, R, R ² , R ³ , R ⁵ , R6 and Y have the same meaning as in formula (Ia), G ^{7 represents} oxygen, sulfur or NR ⁷ S, where R ⁷ § represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

3. ■ Compounds of the formulas (Ia) to (Ig) according to claim 2, where the symbols have the following meanings:

R, R ² and R ³ are identical or different and, independently of one another, are also particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfonyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethoxy trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoro-methylsulfinyl or trifluoromethylsulphonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or and R ² together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring equ ieder,, R ² , and R ³ do not simultaneously represent hydrogen,

A particularly preferably represents methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl or propane-2 , 2-diyl,

Y particularly preferably represents oxygen,

Rp ^~ and RP are the same or different and, independently of one another, are particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl , Allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl, a) are in formula (Ia)

R4a fij _R is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano and

G for oxygen, sulfur or NR ^7a , where R ^{7a represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

b) are in formula (Ib)

R ⁴ ^ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorine or cyano and

G ² for oxygen, sulfur or NR ^7b , where

R ^{7b represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

c) are in formula (Ic)

R ^{c is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano and

G ³ for oxygen, sulfur or NR ^7c , where

R ^{7c represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

d) are in formula (Id)

R ⁴ ^ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl trifluoromethyl, chlorine or cyano and

G ⁴ for oxygen, sulfur or N-R ^7d , where

R ^{7d represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

e) in formula (Ie)

G ^{5 represents} oxygen, sulfur or NR ^7e , where

R ^{7e represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

f) are in formula (If)

G for oxygen, sulfur or N-R ⁷ f, where R ^{7f represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

g) are in formula (Ig)

G ⁷ for oxygen, sulfur or NR ^7§ , whereby

R ⁷ S represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

Process for the preparation of amides of formula (I), wherein

a) carboxylic acid derivatives of the general formula (II)

in which

Rl, R ^, R ³ and R ^{4 have} the meanings given in the formula (I) in claim 1 and

T represents hydroxy, halogen or alkoxy,

with an amine of the general formula (IH)

in which

R5, R6 and A have the meanings given in formula (I) in claim 1, or with an acid addition complex thereof - if appropriate in the presence of an acid acceptor, if appropriate in the presence of a condensing agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent, and b) if appropriate (if Y in the formula (I) is S) with a sulfurization reagent, if appropriate in the presence of a diluent implements.

5. Agent for combating undesirable microorganisms, characterized by a content of at least one amide of the film (I) according to one or more of claims 1 to 3 in addition to extenders and / or surface-active substances.

6. Use of amides of Foπnel (I) according to one or more of claims 1 to 3 for controlling unwanted microorganisms.

7. A method for controlling undesirable microorganisms, characterized in that amides of the formula (I) according to one or more of claims 1 to 3 are applied to the undesired microorganisms and / or their habitat.

8. A process for the preparation of agents for controlling unwanted microorganisms, characterized in that amides of the formula (I) according to one or more of claims 1 to 3 are mixed with extenders and / or surface-active substances.

9. Amines of the formulas

in which

A and R5 have the meanings given in formula (I) in Claim 1 and R ^{s represents} allyl, propargyl, 2-butinyl or cyanomethyl and (fll-b)

in which

A and RP have the meanings given in formula (I) in claim 1 and

R9 represents allyl, propargyl, 2-butinyl or cyanomethyl.