WO2010029066A1 - Imidazole and triazole compounds, use thereof and agents containing said compounds - Google Patents

Abstract

The invention relates to compounds of formula (I) wherein the variables have the meanings defined in the claims and the description.

Description

 Imidazole and triazole compounds, their use, and agents containing them

description

The present of the formula I

wherein the variables have the following meanings:

X is CH or N;

YO or a single bond to R ¹ ;

Z is a saturated or partially unsaturated hydrocarbon chain of three to eight carbon atoms which, when partially unsaturated, contains one to three double bonds or one or two triple bonds, where Z may contain one, two, three, four or five substituents R ^z , where R ^{z is} means:

R ^{Z is} halogen, cyano, nitro, cyanato (OCN), C -C ₈ -alkyl, C ₈ -HaIo- genalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ - C ₈ -alkenyl, C ₃ -C ₈ -

Haloalkynyl, _{Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylcarbonyl} oxy, Ci-Cs-alkylsulfonyloxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ haloalkenyloxy, C ₂ - C ₈ alkynyloxy, _C3-C8 haloalkynyloxy, C3-C ₈ -cycloalkyl, C ₃ -C ₈ -HaIo- gencycloalkyl, _C3-C8 cycloalkenyl, _C3-C8 halocycloalkenyl, C ₃ -C ₈ - cycloalkoxy , C ₃ -C 6 -cycloalkenyloxy, C ₁ -C 6 -alkylene, oxy-C ₂ -C 4 -alkylene,

Oxy-C 1 -C 3 -alkyleneoxy, phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the abovementioned groups the heteroaryl is an aromatic five-, six- or seven-membered heterocycle and the heterocyclyl is a saturated or partially unsaturated five-, is six- or seven-membered heterocycle, each one, two, three or four

Heteroatoms from the group O, N and S contain, or NA ³ A ⁴ , wherein two radicals R ^z , which are attached to the same carbon atom, together with the carbon atom to which they are attached, also form a C ₃ - Cβ-cycloalkyl ring can; wherein A ³ , A ⁴ are defined as below;

R ^{1 is} C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 3 -C 10 -cycloalkenyl, C 3 -C 10 -halocycloalkenyl, the abovementioned carbocycles being unsubstituted or one, two, three, four or five substituents independently selected from halo, hydroxy, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl and C 3 Cs-haloalkynyl or 6- to 10-membered aryl, wherein the aryl contains one, two, three, four or five independently selected substituents L, wherein L means:

L is halogen, cyano, nitro, hydroxy, cyanato (OCN), C 1 -C ₈ -alkyl, C 1 -C ₈ -haloalkyl, C 2 -C -alkenyl, C 2 -C ₈ -haloalkenyl, C 2 -C -alkynyl, Cs-C ₈ Halogenoalkynyl, C 4 -C 10 -alkadienyl, C 4 -C 10 -haloalkadienyl, C 1 -C 8 -alkoxy,

Ci-Cs-haloalkoxy, d-Cs-alkylcarbonyloxy, Ci-Cs-alkylsulfonyloxy, C2-Cs alkenyloxy, C2-C8 haloalkenyloxy, C2-C8-alkynyloxy, Cs-C ₈ - haloalkynyloxy, _C3-C8 cycloalkyl, Cs-Cs-halocycloalkyl, Cs-C ₈ - cycloalkenyl, _C3-C8 halocycloalkenyl, C3-C alkenyloxy ₈ cycloalkoxy, Cs-Cβ-cyclo, hydroxyimino-Ci-C ₈ alkyl, Ci-Cβ alkylene, oxy-C2-C4-alkylene,

Oxy-Ci-C3-alkyleneoxy, C ₈ -Alkoximino-C ₈ alkyl, C2-C ₈ -Alkenyloximino- d-Cβ-alkyl, C2-C ₈ -Alkinyloximino-C ₈ alkyl, S (= O) _n A ¹ , C (OO) A ² , C (SS) A ² , NA ³ A ⁴ , phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the abovementioned groups the heteroaryl an aromatic five-, six- or seven-membered heterocycle and the heterocyclyl is a saturated or partially unsaturated five-, six- or seven-membered heterocycle which contain in each case one, two, three or four heteroatoms from the group consisting of O, N and S, wherein two substituents L attached to the same carbon atom together with the carbon atom to which they are attached may also form a Cs-Cβ cycloalkyl ring; where n, A ¹ , A ² , A ³ , A ⁴ mean:

n is 0, 1 or 2;

A ¹ is hydrogen, hydroxy, Ci-C ₈ -alkyl, C ₈ haloalkyl, amino, Ci-C ₈ -

Alkylamino, di-C 1 -C ₈ -alkylamino, phenyl, phenylamino or phenylC 1 -C ₈ -alkylamino;

A ² A ¹ wherein one of said groups, or _C2-C8 alkenyl, C2-C ₈ - haloalkenyl, _C2-C8 alkynyl, _{C3-C8-haloalkynyl,} Ci-C ₈ alkoxy,

_{Ci-C8-haloalkoxy, C2-C8} alkenyloxy, _C2-C8 haloalkenyloxy, _C2-C8 alkynyloxy, _C3-C8 haloalkynyloxy, _C3-C8 cycloalkyl, Cs-Cs-halocycloalkyl, C3- Cs-cycloalkoxy or _C3-C8-halo cycloalkoxy;

A ³ , A ⁴ independently of one another are hydrogen, C 1 -C ₈ -alkyl, C 1 -C ₅ -haloalkyl, C 2 -C ₈ -alkenyl, C 2 -C ₅ -haloalkenyl, C 2 -C ₈ -alkynyl, C 3 -C ₈ -haloalkynyl, C 3 -C 5 -synyl -Cycloalkyl, C 3 -C 8 -halocycloalkyl, Cs-C ₈ - Cycloalkenyl or C ₃ -C ₈ -halocycloalkenyl, phenyl or 5- or ₆ -membered heteroaryl having one, two, three or four heteroatoms from the group O, N and S in the heterocycle;

the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L may themselves carry one, two, three or four identical or different groups R ^L :

R ^{L is} halogen, hydroxy, cyano, nitro, Ci-C ₈ alkyl, Ci-Cs-haloalkyl, d-Cs-alkoxy, d-Cs-haloalkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ -Halogencyclo alkyl, C ₃ -C ₈ -cycloalkenyl, C ₃ -C ₈ -cycloalkoxy, C ₃ -C ₈ -halocycloalkoxy, C ₁ -C ₆ -alkylene, oxy-C ₂ -C ₄ -alkylene, oxy-C ₁ -C ₃ - alkyleneoxy, C ₈ - alkylcarbonyl, Ci-Cs-alkylcarbonyloxy, _{Ci-C8-alkoxycarbonyl,} amino, d- Cβ-alkylamino, di-Ci-C ₈ alkylamino;

R ² is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C ₂ -Cio-alkenyl, C ₂ -C ₀ - haloalkenyl, C ₂ -C ₀ alkynyl, C3-Cio-haloalkynyl, C4-Cio-alkadienyl , C4-Ci _θ -Halogenalkadienyl, C3-Ci _θ cycloalkyl, C3-Ci _θ halocycloalkyl, C ₃ - Cio-cycloalkenyl, C3-Cio-halocycloalkenyl;

R ³ is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C ₂ -C ₀ alkenyl, C ₂ -C ₀ - haloalkenyl, C ₂ -C ₀ alkynyl, C3-Cio-haloalkynyl, d-CIO alkadienyl, C4-Ci _θ -Halogenalkadienyl, C3-Ci _θ cycloalkyl, C3-Ci _θ halocycloalkyl, C ₃ - Cio-cycloalkenyl, C3-Cio-halocycloalkenyl, carboxyl, formyl, Si (A ⁵ A ⁶ A ^7), C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR ^π , C (NR ^A ) SR ^π ,

C (S) R ^π , C (NR ^π ) N NA ³ A ⁴ , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C (O) NA ³ A ⁴ , C (S) NA ³ A ⁴ or S (= O) _n A ¹ ; in which

R ^π Ci-Cs-alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ -alkyl kinyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ - cycloalkenyl or phenyl;

R is ^A -Cs alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkenyl or phenyl;

A ⁵ , A ⁶ , A ⁷ independently of one another are C ₁ -C 10 -alkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₈ -alkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkenyl or phenyl ;

wherein R ^π , R ^A , A ⁵ , A ⁶ and A ⁷ , unless otherwise indicated, are independently unsubstituted or substituted with one, two, three, four or five L as defined above;

R ⁴ is hydrogen, Ci-C _θ alkyl, Ci-Cio-haloalkyl, C ₂ -C ₀ alkenyl, C ₂ -C ₀ - haloalkenyl, C ₂ -C ₀ alkynyl, C ₃ -C ₀ haloalkynyl, C4 -Cio-alkadienyl, C 4 -C 10 haloalkadienyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 3 -C 10 -cycloalkenyl, C 3 -C 10 -halocycloalkenyl;

R ² , R ³ , R ⁴ are, unless otherwise indicated, independently unsubstituted or substituted with one, two, three, four or five L as defined above;

R ^{5 is} hydrogen, halogen or Ci-Cio-alkyl; wherein the alkyl group in R ^{5 is} unsubstituted or substituted by one, two, three, four or five independently selected L, as defined above;

R ⁶ and R ⁷ together form a three to ten membered saturated or partially unsaturated cycle which is a carbocycle or, besides carbon atoms, one, two or three heteroatoms selected from nitrogen (N) and sulfur (S) and / or an oxygen atom (O) may contain as ring members, wherein the cycle formed is unsubstituted or may contain one, two, three, four or five substituents L as defined above;

and their agriculturally acceptable salts. Furthermore, the invention relates to the preparation of the compounds I, the intermediates for the preparation of the compounds I and their preparation and the use of the compounds according to the invention for controlling phytopathogenic fungi and agents containing them.

Triazole compounds are known from EP 0 200 149 and EP 0 199 982.

The fungicidal action of the compounds known from the prior art, however, leaves something to be desired, in particular at low application rates in some cases. It is an object of the present invention to provide novel compounds which preferably have improved properties such as a better fungicidal action and / or better toxicological properties. This object has surprisingly been achieved with the compounds of the formula I described herein.

The compounds I are able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them. This also applies to most of the precursors for compounds I described herein, of which the salts and adducts are also subject of the present invention.

Examples of inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid. Suitable organic acids are, for example, formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms ), Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl carrying one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic radicals such as phenyl and naphthyl, which is one or two

Carry phosphoric acid residues), wherein the alkyl or aryl radicals may carry further substituents, e.g. p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

The metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others into consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period. The metals can be present in the various valences that belong to them.

The compounds I according to the invention can be prepared in various ways in analogy to prior art processes known per se (see, for example, the cited prior art or EP 0 129 186, EP 0 129 152). For example, the compounds of the invention can be prepared by the syntheses shown in the following Schemes.

Thus, a compound of the formula I in which R ³ and R ^{4 are} hydrogen (compound fertilize 1-1)

wherein R ¹ , X, Y, Z, R ² , R ⁵ , R ⁶ and R ^{7 are} as defined or preferably defined for formula I, are prepared by reduction II

Boron hydrides, in particular sodium borohydride, potassium borohydride, tetra-n-butylammonium borohydride and other metal hydrides can be used as reducing agents, for example. It may be advantageous to add an additive such as a Lewis acid, generally in substoichiometric or stoichiometric proportions. Titanium halides such as titanium tetrachloride, titanium alkoxides such as titanium tetraisopropoxide or zinc or tin halides such as zinc chloride or tin chloride have proven to be particularly suitable. See, for example, Chem Ber. 121 (6), 1988, 1059 ff. Further suitable reducing agents are, for example, alkyl magnesium halides, such as, for example, isopropylmagnesium chloride or tert-butylmagnesium chloride. See eg DE3511922, DE3437919, DE3415486, DE3600812.

Another are compounds of formula II

wherein R ¹ , X, Y, Z, R ² , R ⁵ , R ⁶ and R ^{7 are} as defined or preferably defined for formula I. In one embodiment, R ^{2 is} hydrogen (compounds 11-1).

Compounds of formula II can be obtained by alkylation reactions, e.g., by reacting a compound of formula III

with a compound IV R ¹ -YZ-LG (IV) and a base in which LG is a leaving group such as halogen, in particular Cl, Br and I, or mesylate, tosylate, or for another suitable leaving group known to the skilled person, stands. R ¹ , Y and Z have the meanings or preferred meanings, as defined for formula I. Suitable bases are alkali metal or alkaline earth metal hydrides, alkali metal amides or alkoxides.

Processes for the preparation of compounds of the type IV are known to the person skilled in the art.

Alternatively, compounds 1-1 can be obtained starting from compounds V,

wherein X, Z, R ² , R ⁵ , R ⁶ and R ^{7 are} as defined or preferably defined for formula I and LG is a leaving group (Bspe. see above) or OH, which, if Z contains one or more multiple bonds , is not tied directly to a multiple bond. LG is substituted by a nucleophile such as an alkoxide to introduce a group R ¹ -Y. For this purpose, for example, a corresponding alcohol R ¹ -OH, such as in particular a possibly substituted phenol, in an inert solvent before and the reaction mixture is mixed with a base. Suitable bases are carbonates, alkali metal or alkaline earth metal hydrides, alkali metal amides and alcoholates. The reaction is usually carried out in a temperature range between 20 ⁰ C and 150 ⁰ C. For example, LG can also be generated from an OH group by methods known to the person skilled in the art. Examples which may be mentioned here are the reactions with sulfonyl chlorides or anhydrides (methane, methanesulfonyl, trifluoromethylsulfonyl or tosyl) in the presence of an amine base or with halogenating reagents, for example PBr3 or HBr.

Compounds V can be obtained by reacting the keto group in the corresponding keto compound VI

as described above is reduced to the alcohol.

Compounds VI can be prepared by reacting a compound III (see above) with a compound VII,

LG-Z-LG (VII) wherein Z is as defined or preferably defined for formula I and LG is in each case independently a leaving group (Bspe. See above) and one of the two groups LG can also be OH, where the leaving groups if Z contains one or more multiple bonds, is not tied directly to a multiple bond. Z in particular represents alkylene chain # - [CH 2] n - #, in which # indicates the sites of attachment and n and 3 to 8, in particular 3 to 5. Suitable bases are alkali metal or alkaline earth metal hydrides, alkali metal amides and alcoholates. The temperature range of these reactions is preferably between -20 ⁰ C and 160 ⁰ C, in particular, the reaction is carried out in solvents such as DMF, NMP, cyclic or acyclic ethers. Compounds II, wherein Y is a bond to R ¹ , can also be prepared starting from

Alkyl boranes of type VIII are obtained:

wherein X, Z, R ² R ⁵ , R ⁶ and R ^{7 are} as defined or preferably defined for formula I and A is independently a d-Cβ-alkyl group, Cs-Cβ-cycloalkoxy group or OH by reacting with a Compound IX

R ¹ -LG IX in which R ^{1 is} as defined or preferably defined for formula I and LG is a leaving group. Suitable leaving groups LG are halogen, preferably chlorine, bromine or iodine, alkylcarbonylate, benzoate, alkylsulfonate, haloalkylsulfonate or arylsulfonate, particularly preferably chlorine and bromine. The reaction is usually carried out in the presence of a base and a catalyst, in particular in the presence of a palladium catalyst, as described, for example, in: Synth. Commun. Vol. 1 1, p. 513 (1981); Acc. Chem. Res. Vol. 15, pp. 178-184 (1982); Chem. Rev. Vol. 95, pp. 2457-2483 (1995); Organic Letters Vol. 6 (16), p. 2808 (2004); "Metal Catalyzed Cross Coupling Reactions", 2nd Edition, Wiley, VCH 2005 (Eds. De Meijere, Diederich); "Handbook of Organopalladium Chemistry for Organic Synthesis" (Eds Negishi), Wiley, Interscience, New York, 2002; "Handbook of functionalized organometallics", (Ed. P. Knöchel), Wiley, VCH, 2005.

Suitable catalysts are tetrakis (triphenylphosphine) palladium (0); Bis (triphenylphosphine) palladium (II) chloride; Bis (acetonitrile) palladium (II) chloride; [1, 1 '- bis (diphenylphosphino) ferrocene] palladium (II) chloride / methylene chloride (1: 1) complex; Bbis [bis (1,2-diphenylphosphino) ethane] palladium (0); Bis [bis (1, 2-diphenylphosphino) butane] palladium (II) chloride; Palladium (II) acetate; Palladium (II) chloride; Palladium (II) acetate / tri-o-tolylphosphine complex or mixtures of phosphines and Pd salts or phosphines and Pd complexes, e.g. Dibenzylideneacetone palladium and tri-tert-butylphosphine (or the corresponding tetrafluoroborate), tricyclohexylphosphines or a polymer-bound Pd-triphenylphosphine catalyst system.

Suitable bases are e.g. inorganic bases such as alkali metal or alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal or alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate and calcium carbonate. Also suitable are alkali metal

Bicarbonates such as sodium bicarbonate and alkali metal or alkaline earth metal alkoxides such as sodium methoxide, sodium ethanolate, potassium ethanolate or potassium tert-butoxide. Furthermore, amine bases are suitable, in particular tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, or aromatic such as pyridines, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine. Frequently, bases such as sodium carbonate, potassium carbonate, cesium carbonate, triethylamine and sodium bicarbonate are particularly advantageous.

The base is usually used in a molar ratio of 1: 1 to 1:10, preferably in a molar ratio of 1: 1.5 to 1: 5 relative to R ¹ -LG. The boron compound is used in a molar ratio of between 1: 1 and 1: 5, preferably between 1: 1 and 1: 2.5, based on R ¹ -LG. R ¹ here preferably represents substituted phenyl.

The reaction is usually carried out in an inert organic solvent. Suitable solvents are aliphatic hydrocarbons, e.g. Pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- or p-xylene, ethers, e.g. Diisopropyl ether, methyl tert-butyl ether, dioxane, anisole, tetrahydrofuran and dimethoxyethane. In addition, ketones such as acetone, ethyl methyl ketone, diethyl ketone and methyl tert-butyl ketone are suitable. Also suitable are solvents such as dimethyl sulfoxide, dimethylformamide and dimethylacetamide. Particularly suitable are ethers such as tetrahydrofuran, dioxane and dimethoxyethane. The o.g. Solvents may preferably also be used as mixtures with one another or in admixture with water.

The coupling reaction is usually carried out at temperatures between 20 and 180 ⁰ C, preferably between 40 and 120 ⁰ C.

After completion of the reaction, the coupling products can be isolated according to standard methods. It is also possible to add a scavenger to separate minor components or residual starting material. Further details and references can be found, for example, "Synthesis and purification catalog", Argonaut, 2003.

Compounds VIII are he X

by reacting with a borane HB (A) 2. X, Z, R ² R ⁵ , R ⁶ and R ⁷ are as defined or preferably defined for formula I and A is independently a Ci-Cβ-alkyl group, Cs-Cβ-cycloalkoxy or OH, wherein Z is in particular a Alkylene chain # - [CH 2] _n - #, where # indicates the linking sites and n is in particular 1 to 3.

In this hydroboration reaction for the preparation of the compounds VIII, the borane compound used is, for example, 9-BBN, dicyclohexylborane, catecholborane, borane, dimethoxyborane borane, pinacolborane, texylborane. These reactions are known to the person skilled in the art and can be carried out, for example, analogously to literature procedures, for example as described in WO 2008055859 or Journal of the American Chemical Society (2007), 129 (47), 14632-14639. Furthermore, the addition of (transition) metal complexes as catalysts such as Ir (COD ^ Cb, Rh (Cl) (PPh3) 3 as described in Angewandte Chemie, 97 (10), 854-5, 1985, is possible.

Compounds X, wherein Z is especially an alkylene chain # - [CH 2] _n - #, where # indicates the sites of attachment and n is 1 to 4, can be prepared by reacting a ketone III (see above) via a conventional alkylation method as set forth above , is alkylated.

According to another method, compounds I (with R ³ = hydrogen) can be obtained by reacting an oxirane of the formula XI

wherein Y, Z, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ^{7 are} as defined or preferably defined for formula I, with imidazole or triazole in the presence of an epoxide-opening base to form the target products , Such processes are described, for example, in EP 0 236 884.

The oxirane XI is obtainable by reacting the corresponding olefin XII

with a peracid or an equivalent reagent (such as dimethyldioxirane or other peroxides, see also EP 0 236 884).

The olefin XII can

With

be prepared (see also EP 0 236 884).

Alternatively, olefins XII can be prepared from over the corresponding alcohol XV

which is converted into the olefin in an elimination reaction familiar to the person skilled in the art (see also EP 0 236 884). The preparation of the alcohols XV is described, for example, in DE 3400829. Optionally, an isomerization of the double bond can take place in order to make the desired configuration of the oxirane available. Processes for this are known to the person skilled in the art.

To obtain starting from compounds of formula 1-1 compounds with R ³ ≠ hydrogen

It is possible to proceed by methods known to those skilled in the art for alkylating, esterifying, etc., alcohols (see also DE 3321422, DE 3019049).

In order to prepare compounds of the formula I in which R ⁴ denotes hydrogen, (compound I-4),

it is possible to proceed analogously to the process described in DE 3126022, DE 3049542, and to convert the corresponding ketone of the formula II (see above) with a Grignard reagent (R ⁴ -Mg-Hal) into the corresponding tertiary alcohol.

Similarly, compounds I in which two or three substituents of R ² , R ³ and R ^{4 are} other than hydrogen can be prepared by combining said processes.

In the definitions of the symbols in the formulas given herein, partial collective terms are used which are generally representative of the following substituents:

Halogen: fluorine, chlorine, bromine and iodine; Alkyl and the alkyl moieties of compound groups such as alkylamino: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 carbon atoms, for example Ci-C ₆ alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl , 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1 -Dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2 , 3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl -2-methylpropyl;

Haloalkyl: alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above; in particular C 1 -C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl , 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1, 1 , 1-trifluoroprop-2-yl;

Alkenyl and the alkenyl moieties in a compound group, such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and a double bond in any position. In the present invention, it may be preferable to use small alkenyl groups such as (C 2 -C 4) alkenyl, but on the other hand, it may also be preferable to use larger alkenyl groups such as (C 5 -C 8) alkenyl. Examples of alkenyl groups are, for example, C 2 -C 6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl , 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 -Methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2- propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl 1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dime thyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3 Dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3- Dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1 - Ethyl 2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; Haloalkenyl: alkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;

Alkadienyl: unsaturated, straight-chain or branched hydrocarbon radicals having 4 to 6 or 4 to 8 carbon atoms and two double bonds in any position;

Alkynyl as well as the alkynyl moieties in compounded groups: straight or branched chain hydrocarbon groups of 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, e.g. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl 3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl 2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2- butinyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Haloalkynyl: alkynyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;

Cycloalkyl and the cycloalkyl moieties in assembled groups: mono- or bicyclic, saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, e.g. C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

Halogencycloalkyl: cycloalkyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;

Cycloalkenyl: monocyclic, monounsaturated hydrocarbon groups with preferably 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexene-3 yl, cyclohexene-4-yl and the like;

Halocycloalkenyl: cycloalkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine; Alkoxy: for an oxygen-bonded alkyl group as defined above, preferably having 1 to 8, more preferably 2 to 6 carbon atoms. Examples are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2- Ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;

Haloalkoxy: alkoxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine. Examples of these are OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ Cl, OCHCl ₂ , OCCl ₃ , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2 Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC ₂ F ₅ , 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-

Trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethoxy, 1- (CH ₂ Cl) -2-chloroethoxy, 1- (CH ₂ Br) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chloro-hexoxy, 6-bromohexoxy, 6-iodo-hexoxy or dodecafluorohexoxy.

Alkylene: divalent linear chains of CH ₂ groups. Preference is given to (C ₁ -C 6) -alkylene, more preferably (C ₂ -C 4) -alkylene, and furthermore it may be preferable to use (C ₁ -C ₃ ) -alkylene groups. Examples of preferred alkylene radicals are CH ₂ , CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ , CH ₂ (CH ₂ ) ₂ CH ₂ , CH ₂ (CH ₂ ) ₃ CH ₂ and CH ₂ (CH ₂ ) ₄ CH ₂ ;

6- to 10-membered aryl: Aromatic hydrocarbon cycle containing 6, 7, 8, 9 or 10 carbon atoms in the ring. In particular phenyl or naphthyl.

3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle containing 1, 2, 3 or 4 heteroatoms from the group O, N and S, wherein the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred for the heterocycle to be bonded via nitrogen. In particular: tri- or four-membered saturated heterocycle (hereinafter also Heterocyc IyI) containing one or two heteroatoms from the group O, N and S as ring members; A five- or six-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group O, N and S as ring members: for example monocyclic saturated or partially unsaturated heterocycles comprising, in addition to carbon ring members, one, two or three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, eg 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl. 5

Thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2,4-oxadiazolidin-3-yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4-thiadiazolidin-3-yl, 1, 2, 4-thiadiazolidin-5-yl, 1, 2,4-triazolidin-3-yl, 1, 3,4-oxadiazolidin-2-yl, 1, 3,4-thiadiazolidin-2-yl, 1, 3,4- Triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- Dihydrothien-2-yl, 2,3-dihydro-thien-3-yl,

2,4-dihydro-thien-2-yl, 2,4-dihydro-thien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrroline-3 yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2 isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3- Dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4- Dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4, 5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazole

2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazole 3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4- Dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1, 3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexa hydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydro-pyrimidinyl, 2-piperazinyl, 1, 3,5-hexahydro-triazin-2-yl and 1,2,4-hexahydro-triazin-3-yl, and the like -ylidene residues; Seven-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group O, N and S as ring members: for example mono- and bicyclic heterocycles having 7 ring members, containing in addition to carbon ring members one, two or three nitrogen atoms and / or a Oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro [1 H] azepine-1 -, -2-, -3-, -4- , -5-, -6- or -7-yl, 3,4,5,6-tetrahydro [2H] azepine-2-, -3-, -A-, -5-, -6- or - 7-yl, 2,3,4,7-tetrahydro [1 H] azepine-1, -2-, -3-, -A-, -5-, -6- or -7-yl, 2,3 , 6,7-Tetrahydro [1 H] azepine-1, -2, -3, -4, -5, 6-or 7-yl, hexahydroazepine-1, -2-, - 3- or 4-yl, tetra-. and hexahydroxene vinyls such as 2,3,4,5-tetrahydro [1 H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-Te - trahydro [1H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1H] oxepin 2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, -3- or -4-yl, tetra- and hexahydro-1,3-diazepinyl, Tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexa-hydro-1,3-dioxepinyl, tetra- and hexahydro-1, 4-oxazepinyl. and hexahydro-1,4-dioxepinyl and the corresponding ylidene residues;

5-, 6-, 7-, 8-, 9- or 10-membered aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms from the group O, N and S: in particular five- or six-membered aromatic mono- or Bicyclic heterocycle containing one, two, three or four heteroatoms from the group O, N and S: The respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred for the heterocycle to be bonded via nitrogen. The heterocycle means in particular:

5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present: 5- ring heteroaryl groups which may contain, in addition to carbon atoms, one to four nitrogen atoms or one, two or three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1, 3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, especially 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-

Isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2,4-triazol-3-yl, 1, 3,4-oxadiazol-2-yl, 1, 3,4-thiadiazol-2-yl and 1, 3, 4-triazol-2-yl;

6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, which heteroaryl can be attached via C or N, if present: 6-membered heteroaryl groups which, in addition to carbon atoms, have one to may contain four or one, two or three nitrogen atoms as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.

The novel compounds of this invention contain chiral centers and are generally obtained in the form of racemates or as diastereomeric mixtures of erythro and threo forms. The erythro and threo diastereomers can be included the compounds of the invention, for example, due to their different solubility or by column chromatography and isolate in pure form. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers. As antimicrobial agents it is possible to use both the uniform diastereomers or enantiomers and also their mixtures obtained in the synthesis. The same applies to the fungicides.

The invention therefore relates both to the pure enantiomers or diastereomers and to mixtures thereof. This applies to the compounds of the formula I according to the invention and, if appropriate, correspondingly to their precursors. In particular, the scope of the present invention includes the (R) and (S) isomers and the racemates of the compounds of the invention, in particular of formula I, which have chiral centers. Suitable compounds according to the invention, in particular of the formula I, also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.

The optionally occurring double bond (s) in the variable Z in the compounds according to the invention can be configured in each case (E) or (Z). Both the (E) and the (Z) isomers are the subject of the present invention.

The compounds according to the invention, in particular of the formula I, can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.

In the compounds I according to the invention, the following meanings of the substituents, in each case alone or in combination, are particularly preferred.

In one embodiment, X = N (triazole compounds of formula LA).

According to another embodiment, X = CH (imidazole compounds of the formula LB).

According to one embodiment of the invention, Y is O. According to another embodiment of the invention, Y represents a single bond between R ¹ and Z.

Z in the compounds of the invention is a saturated or partially unsaturated hydrocarbon chain having three, four, five, six, seven or eight carbon atoms which, when partially unsaturated, contains one, two or three double bonds or one or two triple bonds, where Z is one, two, three, four or five substituents R ^z may contain. In one embodiment, Z is a saturated hydrocarbon chain of three to eight carbon atoms wherein Z is unsubstituted or may contain one, two, three, four or five substituents R ^z .

According to one embodiment of the invention, Z stands for a group Z ¹ :

wherein # represent the attachment sites, n is 3, 4, 5, or 6, and R ^z1 and R ^{z2 are} each independently selected from hydrogen and R ^z , as defined herein.

According to one embodiment, n in the group Z ^{1 stands} for 3.

According to a further embodiment, n in the group Z ^{1 stands} for 4.

According to another embodiment, n in the group Z ^{1 stands} for 5.

In a specific embodiment of the respective embodiments mentioned, R ^z1 and R ^{z2 are} each independently selected from hydrogen and R ^z , as defined herein, wherein R ^{z is} in particular selected from Ci-C ₄ -AlkVl and Cs-Cβ-cycloalkyl, and / or R ^z1 and R ^z2 together with the carbon to which they are attached form a C3-C6 cycloalkyl ring. In another embodiment, R ^{z is} selected from F and Cl.

In another embodiment, Z is Z ¹ , where n = 4 and Y is O.

In another embodiment, Z is Z ¹ , wherein n = 3, 4 or 5 and Y is a single bond between R ¹ and Z.

In a specific embodiment of the invention, all R ^z1 and R ^z2 in Z ^{1 are} hydrogen.

According to a further embodiment, Z is a partially unsaturated hydrocarbon chain having two to eight, in particular four to six, carbon atoms which contains one to three double bonds, wherein Z may contain one, two, three, four or five substituents R ^z . In one embodiment, the hydrocarbon chain has a double bond. In another embodiment, the hydrocarbon chain has two double bonds.

According to another embodiment of the invention, Z is a group Z ²

in which # represent the attachment sites, m and p are each O, 1 or 2, where m + p> 1, in particular m + p> 2, and R ^Z1 , R ^Z2 , R ^Z3 , R ^Z4 , R ^Z5 and R ^Z6 are each independently selected from hydrogen and R ^z, wherein R ^z are each as defined herein or preferably defined.

According to one embodiment, m + p in the group Z ² gives 1, where in particular m = 0 and p = 1.

According to a further embodiment, m + p in the group Z ² gives 2, where in particular m = 1 and p = 1.

According to a further embodiment, m + p in the group Z ² gives 3, where in particular m = 0 and p = 3.

In a specific embodiment of the particular embodiments mentioned, R ^z3 and R ^{z4 are} independently selected from hydrogen and R ^z , as defined herein, wherein R ^{z is} in particular selected from Ci-C ₄ -AlkVl, in particular methyl or ethyl. R ^z1 , R ^z2 , R ^z5 and R ^z6 are each preferably independently selected from hydrogen and C 1 -C ₄ -alkyl and / or two radicals on a carbon atom together with the carbon atom to which they are attached form a C 3 -C 6 -cycloalkyl ring.

According to a further embodiment, R ^Z3 is hydrogen, R ^Z4 is selected from R ^z. According to one embodiment, R ^{Z4 is} C 1 -C ₄ -alkyl, in particular methyl. According to another embodiment, R ^{Z4 is} halogen, in particular chlorine.

According to a further embodiment, R ^Z4 is hydrogen, R ^Z3 is selected from R ^z. According to one embodiment, R ^{Z3 is} C 1 -C ₄ -alkyl, in particular methyl. According to a further embodiment, R ^{Z3 is} halogen, in particular chlorine.

According to a further embodiment, R ^Z3, and R ^Z4 are independently selected from R ^z. According to one embodiment, R ^Z4 and R ^Z5 mean Ci-C ₄ alkyl, especially methyl. According to a further embodiment, R ^{Z3 is} halogen, in particular chlorine.

According to one embodiment, all R ^Z1 , R ^Z2 , R ^Z5 and R ^{Z6 are} hydrogen. According to another embodiment, R ^Z1 , R ^Z2 , R ^Z5 and R ^{Z6 are} independent of each other. which is selected from hydrogen and halogen (especially F and Cl), wherein at least one R ^z thereof is not hydrogen.

The double bond in the group Z ² can be configured (E) or (Z). Both the (E) and the (Z) isomers are the subject of the present invention. In one embodiment, the double bond (E) is configured. According to another embodiment, the double bond (Z) is configured.

According to a further embodiment, Z is a partially unsaturated hydrocarbon chain having three to eight, in particular four to six, carbon atoms which contains one or two triple bonds, wherein Z may contain one, two, three, four or five substituents R ^z . In one embodiment, the hydrocarbon chain has a triple bond. In another embodiment, the hydrocarbon chain has two triple bonds.

According to a further embodiment of the invention, Z stands for a group Z ³

wherein # represent the attachment sites, m and p are each 0, 1 or 2, where m + p> 1, preferably m + p> 2, and R ^Z1 , R ^Z2 , R ^Z3 and R ^{Z4 are} each independently selected is hydrogen and R ^z , where R ^{z is} each as defined herein or preferably defined.

According to one embodiment, m + p in the group Z ³ gives 2, where in particular m = 1 and p = 1.

In a specific embodiment of the particular embodiments mentioned, R ^z1 , R ^z2 , R ^z3 and R ^{z4 are} independently selected from hydrogen and R ^z , as defined herein, wherein R ^{z is} in particular selected from Ci-C ₄ -AlkVl, in particular methyl or E. - Thyl.

The substituent R ^z on Z or in the group Z ¹ , Z ² and Z ³ is / are, unless stated otherwise, each independently selected from the group halogen, cyano, nitro, cyanoato (OCN), Ci -C ₈ -alkyl, C ₈ haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl,} Ci-C ₈ alkoxy, Ci-C ₈ - haloalkoxy, _{Ci-C8-alkylcarbonyloxy,} Ci-C ₈ alkylsulfonyloxy, C ₂ -C ₈ alkenyloxy, C ₂ - C ₈ haloalkenyloxy, C ₂ -C ₈ alkynyloxy, C3 -C ₈ haloalkynyloxy, _C3-C8 cycloalkyl, _{C3-C8-halocycloalkyl,} C3-C ₈ -Cycloal -alkenyl, _C3-C8 halocycloalkenyl, C 3 C ₈ - cycloalkoxy, Cs-Cβ-cycloalkenyloxy, Ci Cβ-alkylene, oxy-C ₂ -C 4 -alkylene, oxy-C ₁ -C 3 -alkyleneoxy, phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the abovementioned groups the heteroaryl is an aromatic five, six or more seven-membered heterocycle and the heterocyclyl a saturated or partially unsaturated five-, six- or seven-membered heterocycle, each containing one, two, three or four heteroatoms from the group O, N and S, or NA ³ A ⁴ , where two radicals R ^z , which are bonded to the same carbon atom, together with the carbon atom to which they are attached may also form a C3-C6 cycloalkyl ring; wherein A ³ , A ^{4 are} as defined herein.

In one embodiment, R ^z ₂ is each independently halogen, cyano, nitro, cyanato (OCN), C -C -alkyl ₈ -alkyl, Ci-C ₈ haloalkyl, C ₂ -C ₈ alkenyl, C -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy,} Ci-C ₈ - alkylcarbonyloxy, Ci-C ₈ alkylsulfonyloxy, C ₂ -C ₈ - alkenyloxy, C ₂ -C ₈ haloalkenyloxy, C ₂ -C ₈ alkynyloxy, _C3-C8 haloalkynyloxy, _C3-C8 cycloalkyl, _{C3-C8-halocycloalkyl, C3-C8} cycloalkenyl, C3-C ₈ halocycloalkenyl, Cβ-Cs-cycloalkynyl, Cβ-Cs Halogencycloalkinyl, C3-C ₈ cycloalkoxy, Cs-Cβ-cycloalkenyloxy, or NA ³ A ^fourth

According to a further embodiment, R ^z is C ₂ -C each independently Cl, F, Br, cyano, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, ₄ -alkenyl, C ₂ -C ₄ haloalkenyl, Ci- C ₄ -Alk- oxy, Ci-C ₄ -haloalkoxy, Cs-Cβ-cycloalkyl or Cs-Cβ-halocycloalkyl, in particular methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyclopropy.

According to a further embodiment, at least one R ^z denotes halogen, in particular Cl or F.

In a further embodiment, at least one R ^{z is} C 1 -C ₄ -alkyl, in particular methyl or ethyl.

In another embodiment, at least one R ^{z is} C 1 -C ₄ -haloalkyl.

In another embodiment, two R ^z radicals bound to the same carbon atom together with the carbon atom to which they are attached form a Cs-Cβ cycloalkyl ring.

R ¹ in the compounds according to the invention denotes C 3 -C ₈ -cycloalkyl, Cs-C ₈ -halo-genocycloalkyl, C 3 -C 10 -cycloalkenyl, C 3 -C 10 -halocycloalkenyl, where the abovementioned groups are unsubstituted or one, two, three, four or five substituents independently selected from halogen, hydroxy, Ci-C ₈ alkyl, Ci-C ₈ haloalkyl, C ₂ -C ₈ - alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ alkynyl, and C3 -C ₈ haloalkynyl; or 6- to 10-membered aryl wherein the aryl contains one, two, three, four or five independently selected substituents L.

According to one embodiment of the invention, R ^{1 is} substituted 6- to 10-membered aryl, in particular substituted phenyl, containing one, two, three, four or five substituents L as defined herein or preferably defined. In another embodiment, R ^{1 is} phenyl which contains exactly one substituent L ¹ . According to one embodiment, L ^{1 is} selected from F, Cl, Br, cyano, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl, C 1 -C ₄ -alkoxy, C 1 -C ₄ -haloalkoxy, C 3 -C 6 -cycloalkyl and C 5 -C 6 -cycloalkyl Halogencycloalkyl, in particular F, Cl, Br, methyl, trifluoromethyl, difluoromethyl and methoxy. According to a specific embodiment, L ^{1 is} selected from F, Cl and Br.

According to a further embodiment, R ^{1 is} phenyl which contains a substituent L ¹ and a substituent L ² , and may additionally contain one, two or three independently selected substituents L, where L, L ¹ and L ^{2 are} as L (see below) are defined. According to one embodiment, L ¹ and L ^{2 are} each independently selected from the group consisting of Cl, F, Br, cyano, nitro, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 Haloalkoxy, and the optionally contained further one, two or three substituents L are independently selected from L, as defined herein or preferably defined.

In another embodiment, R ^{1 is} phenyl which may contain a substituent L ¹ which is Cl and may additionally contain one, two, three or four independently selected substituents L, each L being independently as defined herein. In one embodiment, the phenyl group is substituted in the 2-position with Cl. In another embodiment, the phenyl group of this embodiment is substituted in the 3-position with Cl. In yet another embodiment, the phenyl group of this embodiment is substituted in the 4-position with Cl.

According to a further embodiment, the phenyl group is substituted by Cl and contains exactly one further substituent L ² . In one embodiment, the phenyl group is 2,3-disubstituted. In another embodiment, the phenyl group is 2,4-disubstituted. In yet another embodiment, the phenyl group is 2,5-disubstituted. In yet another embodiment, the phenyl group is 2,6-disubstituted.

According to a further embodiment, the phenyl group is substituted by Cl and contains exactly two further substituents, L ² and L ³ .

In another embodiment, R ^{1 is} phenyl which may have a substituent L ¹ which is F and may additionally contain one, two, three or four independently selected substituents L, each L being independently as defined herein. In one embodiment, the phenyl group is substituted in the 2-position with F. In a further embodiment, the phenyl group of this embodiment is substituted in the 3-position by F. In yet another embodiment, the phenyl group of this embodiment is substituted in the 4-position with F. According to a further embodiment, the phenyl group is substituted by F and contains exactly one further substituent L ² . In one embodiment, the phenyl group is 2,3-disubstituted. In another embodiment, the phenyl group is 2,4-disubstituted. In yet another embodiment, the phenyl group is 2,5-disubstituted. In yet another embodiment, the phenyl group is 2,6-disubstituted. Preferably, F stands in each case in the 2-position. Further preferably, the second substituent L ^{2 is} selected from F, Cl, Br, methyl and methoxy. In a specific embodiment, the phenyl group is 2,3-, 2,4-, 2,5- or 2,6-difluoro-substituted. According to another specific embodiment, the phenyl group is 2-fluoro-3-chloro, 2-fluoro-4-chloro, 2-fluoro-5-chloro or 2-fluoro-6-chloro substituted.

According to a further embodiment, the phenyl group is substituted by F and contains exactly two further substituents, L ² and L ³ .

In another embodiment, R ^{1 is} phenyl which may have a substituent L ¹ which is methyl and may additionally contain one, two, three or four independently selected substituents L, each L being independently as defined herein. In one embodiment, the phenyl group is substituted in the 2-position with methyl. In another embodiment, the phenyl group of this embodiment is substituted in the 3-position with methyl. In yet another embodiment, the phenyl group of this embodiment is substituted in the 4-position with methyl.

In another embodiment, the phenyl group is substituted by methyl (= L ¹ ) and contains exactly one further substituent L ² . In one embodiment, the phenyl group is 2,3-disubstituted. In another embodiment, the phenyl group is 2,4-disubstituted. In yet another embodiment, the phenyl group is 2,5-disubstituted. In yet another embodiment, the phenyl group is 2,6-disubstituted.

According to a further embodiment, the phenyl group is substituted by methyl (= L ¹ ) and contains exactly two further substituents, L ² and L ³ .

In another embodiment, R ^{1 is} phenyl which may have a substituent L ¹ which is methoxy and may additionally contain one, two, three or four independently selected substituents L, each L being independently as defined herein. In one embodiment, the phenyl group is substituted in the 2-position with methoxy. In another embodiment, the phenyl group of this embodiment is substituted in the 3-position with methoxy. In yet another embodiment, the phenyl group of this embodiment is substituted in the 4-position with methoxy. According to a further embodiment, the phenyl group is substituted by methoxy (= L ¹ ) and contains exactly one further substituent L ² . In one embodiment, the phenyl group is 2,3-disubstituted. In another embodiment, the phenyl group is 2,4-disubstituted. In yet another embodiment, the phenyl group is 2,5-disubstituted. In yet another embodiment, the phenyl group is 2,6-disubstituted.

According to a further embodiment, the phenyl group is substituted by methoxy (= L ¹ ) and contains exactly two further substituents, L ² and L ³ .

In another embodiment, R ^{1 is} phenyl containing three, four or five substituents L, where L is independently defined as defined herein or preferred.

According to another embodiment of the invention, R ^{1 is} a 2,3,5-trisubstituted phenyl ring. In another embodiment, R ^{1 is} a 2,3,4-trisubstituted phenyl ring. In yet another embodiment, R ^{1 is} a 2,4,5-trisubstituted phenyl ring. In yet another embodiment, R ^{1 is} a 2,4,6-trisubstituted phenyl ring. In yet another embodiment, R ^{1 is} a 2,3,6-trisubstituted phenyl ring. According to one embodiment, at least one of the three substituents is Cl. According to one embodiment, at least one of the three substituents is F. According to a further embodiment, at least one of the three substituents is methyl. In yet another embodiment, at least one of the three substituents is methoxy.

According to a further embodiment, R ¹ is phenyl disubstituted by two L, wherein L is in each case independently selected from Cl, F, Br, cyano, nitro, hydroxy, C 1 -C ₄ -alkyl and C 1 -C ₄ -haloalkyl, C 1 -C ₄ -Aikoxy and Ci-C4-haloalkoxy. In a specific embodiment, L is in each case independently selected from Cl, F, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl. In another specific embodiment, each L is independently selected from Cl, F, Br, cyano, methyl, ethyl, iso -propyl, tert -butyl, trifluoromethyl, methoxy, ethoxy and trifluoromethoxy.

In another embodiment, R ^{1 is} C 3 -C 10 -cycloalkyl or C 3 -C 10 -halocycloalkyl. According to one embodiment, R ^{1 is} C 3 -C 7 -cycloalkyl, in particular cyclopropyl (C-C 3 H 5), cyclopentyl (C-C 5 H 9), cyclohexyl (C-C 6 Hn) or cycloheptyl (C-C 7 H 13), which may each be optionally substituted , Specific examples of R ¹ are 1-chlorocyclopropyl, 1-methylcyclopropyl, 1-chlorocyclopentyl, 1-methylcyclopentyl and 1-methylcyclohexyl.

In another embodiment, R ^{1 is} C 3 -C 10 cycloalkenyl or C 3 -C 10 halocycloalkenyl. According to the present invention, R ^{2 is} hydrogen, C ₁ -C 10 -alkyl, C ₁ -C 10 -haloalkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -haloalkenyl, C ₂ -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C ₄ -C 10 -alkyl -alkadienyl, C4-Cio-Halogenalkadienyl, C3-Cio-cycloalkyl, C ₃ -C ₀ -HaIo- gencycloalkyl, C3-Cio-cycloalkenyl or C3-Cio-halocycloalkenyl, wherein R ² is one, two, three, four or five substituents L as defined herein.

In a preferred embodiment, R ^{2 is} hydrogen.

According to a further embodiment, R ^{2 is} C ₁ -C 10 -alkyl, C ₁ -C 10 -haloalkyl, phenyl-C ₁ -C ₄ -alkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -haloalkenyl, C ₂ -C 10 -alkynyl, C -C _{3 0} - haloalkynyl, C4-Cio-alkadienyl, C4-Cio-Halogenalkadienyl, C3-Cio-cycloalkyl, C ₃ -C ₀ - halocycloalkyl, C3-Ci _θ cycloalkenyl, or C3-Ci _θ halocycloalkenyl, in particular Ci- C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₃ -C ₄ alkynyl or phenyl-Ci-C ₄ alkyl. Specific examples of R ² are methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, 2-vinyl, 3-allyl, 3-propargyl, 4-but-2-ynyl and benzyl.

According to the present invention, R C ³ is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, -C _{2 0} alkenyl, C ₂ -C ₀ haloalkenyl, C ₂ -C ₀ alkynyl, C3-Cio-haloalkynyl, C ₄ -C 10 -alkadienyl, C ₄ -C 10 -haloalkadienyl, C ₃ -C 10 -cycloalkyl, C ₃ -C 10 -Hiogeno-cycloalkyl, C ₃ -C 10 -cycloalkenyl, C ₃ -C 10 -halocycloalkenyl, carboxyl, formyl, Si (A ⁵ A ⁶ A ⁷ ), C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR ^π , C (NR ^A ) SR ^π , C (S ) R ^π , C (NR ^π ) N NA ³ A ⁴ , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C (O) NA ³ A ⁴ , C (S) NA ³ A ⁴ or S (= O) _n A ¹ ; in which

A ¹ is hydrogen, hydroxy, Ci -C ₈ -alkyl, C ₈ haloalkyl, amino, _{Ci-C8-alkylamino,} di-Ci-C ₈ alkylamino, phenyl, phenylamino or phenyl-Ci-C ₈ - alkylamino;

R ^π Ci-C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ -alkyl kinyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkenyl or phenyl ;.

R ^A Ci-Cβ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ -alkyl kinyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkenyl or phenyl;

A ^5, A ^6, A ⁷ independently of one another Ci-Cio-alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ -alkyl kinyl, C ₃ -C ₆ - cycloalkyl, C ₃ -C 6 cycloalkenyl, or phenyl .

wherein R ^π , R ^A , A ⁵ , A ⁶ and A ⁷ , unless otherwise indicated, are independently unsubstituted or substituted with one, two, three, four or five L, as defined above.

R ³ may contain one, two, three, four or five substituents L as defined herein.

According to a preferred embodiment, R ^{3 is} hydrogen. According to a further embodiment, R ^{3 is} C ₁ -C 10 -alkyl, C ₁ -C 10 -haloalkyl, phenyl-C ₁ -C 10 -alkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -haloalkenyl, C ₂ -C 10 -alkynyl, C ₃ -C ₀ - haloalkynyl, C4-Cio-alkadienyl, C4-Cio-Halogenalkadienyl, C3-Cio-cycloalkyl, C ₃ -C ₀ - halocycloalkyl, C3-Cio-cycloalkenyl, C3-Cio-halocycloalkenyl, carboxyl, formyl , Si (A ⁵ A ⁶ A ⁷ ), C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR ^π , C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) N NA ³ A ⁴ , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C (O) NA ³ A ⁴ , C (S ) NA ³ A ⁴ or S (= O) _n A ¹ , in particular C ₁ -C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkyl, halogenophenyl-C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₃ -C ₄ alkynyl, _tri-Ci-C4 alkylsilyl, C (O) R ^π or S (= O) ₂ A ^1, wherein

A ^{1 is} hydroxy, C ¹ -C ₄ -alkyl, phenyl or C ¹ -C ₄ -alkylphenyl;

R ^π Ci-C ₄ alkyl, carboxy-Ci-C ₄ alkyl or carboxyphenyl;

R ^{A is} dC ₄ alkyl, Cs-Ce-cycloalkyl or phenyl;

A ⁵ , A ⁶ , A ⁷ independently of one another are C 1 -C ₄ -alkyl or phenyl, where the phenyl ring is unsubstituted or substituted by one, two, three, four or five L, as defined herein.

Specific examples of R ³ are trimethylsilyl, Si (CH ₂ ) ₂ (CH ₂ ) SCH ₃ , Si (CH ₂ ) ₂ (C ₆ H ₅ ), methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl butyl, 2-vinyl, 3-allyl, 3-propargyl, 4-but-2-ynyl, C (= O) CH _3, C (= O) CH ₂ CH _3, C (= O) CH ₂ CH ₂ CH ₃ , C (= O) (CH ₂ ) ₂ COOH, C (= O) (CH ₂ ) ₃ COOH, C (= O) (2-COOH-C ₆ H ₄ ), SO ₂ OH, SO ₂ CH ₃ , SO ₂ C ₆ H ₅ , SO ₂ (4-methyl-C ₆ H ₄ ), benzyl and 4-chlorobenzyl.

According to a specific embodiment, R ^{3 is} trimethylsilyl.

According to the present invention, R C C C ⁴ is hydrogen, Ci-Cio-alkyl, Ci-Ci ₀ -HaIo- genalkyl, ₂ -Cio-alkenyl, ₂ -Cio-haloalkenyl, ₂ -Cio-alkynyl, Cs-Cio-haloalkynyl, C ₄ -Cio-alkadienyl, C ₄ -Cio-Halogenalkadienyl, C ₃ -Cio cycloalkyl, C ₃ -C ₀ -HaIo- gencycloalkyl, C ₃ -Cio-cycloalkenyl or Cs-Cio-halocycloalkenyl, wherein R ⁴ is one, two , three, four or five substituents L as defined herein.

In a preferred embodiment, R ^{4 is} hydrogen.

According to a further embodiment, R represents C ⁴ Ci-Cio-alkyl, Ci-Cio-haloalkyl, phenyl-Ci-C ₄ alkyl, ₂ -Cio-alkenyl, C ₂ -Cio-haloalkenyl, C ₂ -Cio-alkynyl, Cs -Cio- haloalkynyl, C ₄ -Cio-alkadienyl, C ₄ -Cio-Halogenalkadienyl, C ₃ -Cio cycloalkyl, C ₃ -C ₀ - halocycloalkyl, C ₃ -Cio-cycloalkenyl or Cs-Cio-halocycloalkenyl, in particular Ci- Ce-alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl or phenyl-C ₁ -C ₄ -alkyl. Specific examples of R ² are methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl and benzyl. In the present invention R ^{5 is} hydrogen, halogen or Ci-Cio-alkyl; wherein the alkyl group in R ^{5 is} unsubstituted or substituted by one, two, three, four or five independently selected L, as defined herein or preferably defined. R ^{5 is} preferably hydrogen, Cl or C 1 -C ₄ -alkyl. R ⁵ is in particular hydrogen, Cl, methyl, ethyl or n-propyl. In a specific embodiment, R ^{5 is} hydrogen. According to another specific embodiment, R ^{5 is} methyl. In yet another specific embodiment, R ^{5 is} Cl.

According to the present invention, R ⁶ and R ⁷ together form a saturated or partially unsaturated cycle having three to ten members, which is a carbocycle or, in addition to carbon atoms, one, two or three heteroatoms from the group consisting of nitrogen (N) and sulfur (S) and / or an oxygen atom (O) may contain as ring members, wherein the cycle formed is unsubstituted or may contain one, two, three, four or five substituents L as defined herein or preferably defined. In one embodiment, R ⁶ and R ⁷ together form a Cs-Cβ cycloalkyl group which is unsubstituted or substituted by one, two or three substituents L, wherein L is preferably independently selected from halogen and C 1 -C ₄ -alkyl. In one embodiment, the carbocycle formed is unsubstituted. Inventive examples of a saturated cabocycle formed from R ⁶ and R ⁷ are cyclopropyl, cyclopentyl and cyclohexyl. According to a preferred embodiment, R ⁵ is simultaneously hydrogen, halogen or C 1 -C ₄ -alkyl.

According to a further embodiment, R ⁶ and R ⁷ together form a Cs-Cs-cycloalkenyl group which is unsubstituted or substituted by one, two or three substituents L, wherein L is preferably independently selected from halogen and C 1 -C ₄ -alkyl. In one embodiment, the formed partially unsaturated carbocycle is unsubstituted.

According to another embodiment, R ⁶ and R ⁷ together form a saturated C ⁵ -C ⁷ heterocyclyl group containing one, two or three nitrogen atoms (N) and being unsubstituted or substituted by one, two or three substituents L. In one embodiment, the formed Heterocycle unsubstituted.

According to another embodiment, R ⁶ and R ⁷ together form a partially unsaturated Cs-Cr heterocyclyl group which contains one, two or three nitrogen atoms (N) and is unsubstituted or substituted by one, two or three substituents L. In one embodiment, the formed heterocycle unsubstituted.

According to another embodiment, R ⁶ and R ⁷ together form a saturated C ⁵ -C ⁷ heterocyclyl group which contains an oxygen atom (O) and is optionally substituted. For example, R ⁶ and R ⁷ together form an unsubstituted or substituted tetrahydropyran-3-yl or tetrahydropyran-4-yl ring. In one embodiment, the heterocycle formed is unsubstituted. L independently has the meanings or preferred meanings given above or in the claims for L. If it is not otherwise stated, L is preferably independently selected from halogen, cyano, nitro, cyanato (OCN), -C ₄ - alkyl, _{Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,} C ₃ -C ₆ cycloalkyl, C ₃ - Cβ-halocycloalkyl, SA ^1, C (= O) A ^2, C (= S) A ² NA ³ A; wherein A ^1, A ^2, A ^3, A ⁴ are: A ¹ is hydrogen, hydroxy, Ci _-C4 -alkyl, Ci-C ₄ haloalkyl;

A ² A ¹ wherein one of said groups or Ci-C ₄ alkoxy, CTC ₄ - haloalkoxy, C ₃ -C 6 cycloalkyl, Cs-Cβ-halocycloalkyl, C ₃ -Cβ-

Cycloalkoxy or C ₃ -C 6 -halocycloalkoxy;

A ³ , A ^4, independently of one another, are hydrogen, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl;

where the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L can themselves carry one, two, three or four identical or different groups R ^L :

R ^{L is} halogen, cyano, nitro, Ci-C ₄ -alkyl, _C-4 haloalkyl, Ci-C ₄ -

Alkoxy, C ₁ -C ₄ -haloalkoxy, C ₃ -C 6 -cycloalkyl, C ₁ -C 6 -halocycloalkyl, amino, C ₁ -C 8 -alkylamino, C ₁ -C -alkylamino.

Furthermore preferably, L is independently selected from halogen, amino Ci-C ₄ -alkyl, C d- ₄ alkoxy, _{Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylamino,} C1-C4- Dialkylamino, thio and Ci-C ₄ alkylthio

Furthermore preferably, L is independently selected from halogen, _Ci-C4 -alkyl, C1-C4- haloalkyl, _Ci-C4-alkoxy and _{Ci-C4-haloalkoxy.}

According to a further preferred embodiment, L is independently selected from F, Cl, Br, CH _3, C ₂ H _5, iC ₃ H _7, tC ₄ H _9, OCH _3, OC ₂ H _5, CF _3, CCl _3, CHF ₂ , CCIF ₂ , OCF ₃ , OCHF ₂ and SCF ₃ , in particular selected from F, Cl, CH ₃ , C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , CF ₃ , CHF ₂ , OCF ₃ , OCHF ₂ and SCF ₃ , According to one embodiment, L is independently excluded selected from F, Cl, CH _3, OCH _3, CF _3, OCF ₃ and OCHF. ₂ It may be preferred that L is independently F or Cl.

According to a further embodiment, L is independently selected from F, Br, CH _3, C ₂ H _5, iC ₃ H _7, tC ₄ H _9, OCH _3, OC ₂ H _5, CF _3, CCl _3, CHF ₂ CCIF ₂ , OCF ₃ , OCHF ₂ and SCF ₃ .

In yet another embodiment, L is independently selected F, Cl, Br, methyl and methoxy. The meanings of the variables R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, Y, Z and L described above for compounds I apply correspondingly to the precursors of the compounds according to the invention.

In particular, with regard to their use, the compounds LA according to the invention which are combined in the following Tables 1a to 135a are preferred, taking into account the stipulations mentioned herein. The groups mentioned in the tables for a substituent, taken individually, independently of the combination in which they are mentioned, also represent a particularly preferred embodiment of the substituent in question.

Table 1 a

Compounds LA in which Z is CH ₂ CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is each one

Row of Table A corresponds (compounds I.A.1 aA-1 to I.A.1 aA-444)

Table 2a

Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y are each corresponds to one row of Table A (compounds IA2aA-1 to IA2aA-444)

Table 3a

Compounds LA in which Z is CH ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is each one row of Table A corresponds (compounds IA3aA-1 to IA3aA-444) Table 4a

Compounds LA, wherein Z is CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y are each corresponds to one line of Table A (compounds IA4aA-1 to IA4aA-444)

Table 5a compounds LA, wherein Z is CH ₂ CH ₂ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H,

R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA5aA-1 to IA5aA-444)

Table 6a

Compounds LA, wherein Z is CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y are each corresponds to one line of Table A (compounds IA6aA-1 to IA6aA-444)

Table 7a

Compounds LA, wherein Z is CH ₂ C (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ⁵ H and R ⁶ + R ^{7 are} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA7aA-1 to IA7aA-444) Table 8a

Compounds LA in which Z is CH ₂ C (CH ₂ CH ₂ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA8aA-1 to IA8aA-444) Table 9a

Compounds LA in which Z is C (CH ₂ CH ₂ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA9aA-1 to IA9aA-444)

Table 10a

Compounds LA in which Z is CH ₂ CH (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y correspond in each case to one row of Table A (compounds IA10aA-1 to I .A.1 OaA-444)

Table 1 1a

Compounds LA, wherein Z is C (CH ₃ ) ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA1 1aA-1 to IA11 aA-444) Table 12a

Compounds LA in which Z is C (CH ₂ CH ₂ ) (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y correspond in each case to one row of Table A (compounds IA12aA-1 to IA12aA-444) Table 13a

Compounds LA, wherein Z is CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA13aA-1 to IA13aA-444) Table 14a

Compounds LA, wherein Z is CH ₂ CH ₂ CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA14aA-1 to IA14aA-444) Table 15a

Compounds LA in which Z is CH ₂ (CH ₂ ) ₃ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (Compounds IA15aA-1 to IA15aA-444) Table 16a Compounds LA, wherein Z is (E) CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ⁵

H and R ⁶ + R ^{7 are} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA16aA-1 to IA16aA-444) Table 17a

Compounds LA, wherein Z is (E) C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H,

R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA17aA-1 to IA17aA-444) Table 18a

Compounds LA in which Z is (E) C (CHs) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination each of R ¹ and Y corresponds to one row of Table A (compounds IA18aA-1 to IA18aA-

444) Table 19a

Compounds LA, wherein Z is (E) CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H,

R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA19aA-1 to IA19aA-444) Table 20a Compounds LA, wherein Z is (E) CH ₂ CH = CHCH ₂ , R ² , R ³ and R ⁴ stand for H,

R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA20aA-1 to IA20aA-444) Table 21a

Compounds LA in which Z is (E) CH ₂ C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA21 aA-1 to IA21aA-

444) Table 22a

Compounds LA in which Z is (E) CH ₂ CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA22aA-1 to IA22aA-

444) Table 23a

Compounds LA, wherein Z is (E) CH ₂ C (CHs) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA23aA-1 to IA23aA-

444) Table 24a

Compounds LA in which Z is (E) C (CH ₃ ) = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ⁷ Cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.24aA-1 to

I.A24aA-444) Table 25a

Compounds LA in which Z is (E) C (CH ₃ ) = CH (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA25aA-1 to IA25aA-

444) Table 26a

Compounds LA in which Z is (E) CH = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination from R ¹ and Y corresponds in each case to one row of Table A (compounds IA26aA-1 to IA26aA-444)

Table 27a

Compounds LA in which Z is CH ₂ OCCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is in each case one row of Table A. corresponds (compounds IA27aA-1 to IA27aA-444) Table 28a

Compounds LA in which Z is CH ₂ CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is in each case one row of Table A corresponds (compounds IA28aA-1 to IA28aA-444)

Table 29a Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ⁵

CH 3 and R ⁶ + R ⁷ denote cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA29aA-1 to IA29aA-444)

Table 30a

Compounds LA in which Z is CH ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is each corresponds to one line of Table A (compounds IA30aA-1 to IA30aA-444)

Table 31a

Compounds LA in which Z is CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA31aA-1 to IA31aA-

444)

Table 32a

Compounds LA, wherein Z is CH ₂ CH ₂ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA32aA-1 to IA32aA-

444)

Table 33a

Compounds LA in which Z is CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y each corresponds to one row of Table A (compounds IA33aA-1 to IA33aA-

444)

Table 34a

Compounds LA in which Z is CH ₂ C (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is corresponds in each case to one row of Table A (compounds IA34aA-1 to IA34aA-444)

Table 35a

Compounds LA in which Z is CH ₂ C (CH ₂ CH ₂ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y each because one row corresponds to Table A (compounds IA35aA-1 to IA35aA-444)

Table 36a

Compounds LA in which Z is C (CH ₂ CH ₂ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA36aA-1 to IA36aA-444)

Table 37a

Compounds LA in which Z is CH ₂ CH (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.37aA-1 to I.A.37aA-444)

Table 38a

Compounds LA, wherein Z is C (CH ₃ ) ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA38aA-1 to IA38aA-444) Table 39a

Compounds LA in which Z is C (CH ₂ CH ₂ ) (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and Combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA39aA-1 to IA39aA-444) Table 40a

Compounds LA in which Z is CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.40aA-1 to I.A.40aA-444)

Table 41a

Compounds LA in which Z is CH ₂ CH ₂ CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.41aA-1 to | .A.41aA-444)

Table 42a

Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₃ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA42aA-1 to IA42aA-444)

Table 43a

Compounds LA in which Z is (E) CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is each one Line of Table A corresponds (compounds IA43aA-1 to IA43aA-444)

Table 44a

Compounds LA, wherein Z is (E) C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA44aA-1 to IA44aA-444)

Table 45a Compounds LA in which Z is (E) C (CHs) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.45aA-1 to I.A.45aA-444)

Table 46a compounds LA, wherein Z is (E) CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H,

R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA46aA-1 to IA46aA-444)

Table 47a Compounds LA, wherein Z is (E) CH ₂ CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H,

R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA47aA-1 to IA47aA-444)

Table 48a Compounds LA, wherein Z is (E) CH ₂ C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.48aA-1 to I.A.48aA-444)

Table 49a Compounds LA, wherein Z is (E) CH ₂ CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.49aA-1 to I.A.49aA-444)

Table 50a Compounds LA, wherein Z is (E) CH ₂ C (CHs) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl mean, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.50aA-1 to I.A.50aA-444)

Table 51a compounds LA, wherein Z is (E) C (CH ₃ ) = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 is}

H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA51aA-1 to IA 51aA-444). Table 52a Compounds LA, wherein Z is (for E) C (CH ₃ ) = CH (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds IA52aA-1 to IA52aA-444) Table 53a

Compounds LA in which Z is (E) CH = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination from R ¹ and Y corresponds in each case to one row of Table A (compounds IA53aA-1 to IA53aA-444)

Table 54a

Compounds LA in which Z is CH ₂ OCCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is in each case one row of Table A. corresponds (compounds IA54aA-1 to IA54aA-444) Table 55a

Compounds LA in which Z is CH ₂ CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is in each case one row of Table A corresponds (compounds IA55aA-1 to IA55aA-444)

Table 56a Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ⁵

Cl and R ⁶ + R ^{7 are} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA56aA-1 to IA56aA-444)

Table 57a

Compounds LA in which Z is CH ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is each corresponds to one line of Table A (compounds IA57aA-1 to IA57aA-444)

Table 58a

Compounds LA in which Z is CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is each corresponds to one line of Table A (compounds IA58aA-1 to IA58aA-444)

Table 59a

Compounds LA, wherein Z is CH ₂ CH ₂ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y are each corresponds to one line of Table A (compounds IA59aA-1 to IA59aA-444) Table 60a

Compounds LA in which Z is CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is each corresponds to one line of Table A (compounds IA60aA-1 to IA60aA-444)

Table 61a Compounds LA, wherein Z is CH ₂ C (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ⁵

Cl and R ⁶ + R ^{7 are} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA61aA-1 to IA61aA-444)

Table 62a

Compounds LA, wherein Z is CH ₂ C (CH ₂ CH ₂ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA62aA-1 to IA62aA-444)

Table 63a

Compounds LA, wherein Z is C (CH ₂ CH ₂ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA63aA-1 to IA63aA-444)

Table 64a

Compounds LA in which Z is CH ₂ CH (CH 3) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA64aA-1 to IA64aA-444)

Table 65a

Compounds LA in which Z is C (CHs) ₂ (CH ₂ ) SCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA65aA-1 to IA65aA-444)

Table 66a

Compounds LA in which Z is C (CH ₂ CH ₂ ) (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA66aA-1 to IA66aA-

444)

Table 67a

Compounds LA, wherein Z is CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA67aA-1 to IA67aA-

444)

Table 68a

Compounds LA, wherein Z is CH ₂ CH ₂ CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA68aA-1 to IA68aA-

444)

Table 69a

Compounds LA in which Z is CH ₂ (CH ₂ ) ₃ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA69aA-1 to IA69aA-444)

Table 70a

Compounds LA in which Z is (E) CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is in each case one line corresponding to Table A (compounds IA70aA-1 to IA70aA-444) Table 71a

Compounds LA in which Z is (E) C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA71aA-1 to IA71 aA-444)

Table 72a relates to compounds LA in which Z is (E) C (CHa) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA72aA-1 to IA72aA-444) Table 73a

Compounds LA in which Z is (E) CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds to one row of Table A (Compounds IA73aA-1 to IA73aA-444) Table 74a

Compounds LA, wherein Z is (E) CH ₂ CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y are each corresponds to one line of Table A (compounds IA74aA-1 to IA74aA-444)

Table 75a Compounds LA, wherein Z is (E) CH ₂ C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y correspond in each case to one row of Table A (compounds IA75aA-1 to IA75aA-444)

Table 76a compounds LA, wherein Z is (E) CH ₂ CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the Combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA76aA-1 to IA76aA-444)

Table 77a Compounds LA, wherein Z is (E) CH ₂ C (CHs) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl , and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA77aA-1 to IA77aA-444)

Table 78a Compounds LA, wherein Z is (E) C (CH ₃ ) = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are}

H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA78aA-1 to I.A78aA-444)

Table 79a Compounds LA in which Z is (E) C (CH ₃ ) = CH (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA79aA-1 to IA79aA-444)

Table 80a Compounds LA, wherein Z is (E) CH = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl , and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA80aA-1 to IAδOaA-444)

Table 81a relates to compounds LA in which Z is CH ₂ C≡CCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} Cl and R ⁶ + R ^{7 is} cyclopropyl, and the combination of R ¹ and Y is in each case one Line of Table A corresponds (compounds IA81 aA-1 to IA81 aA-444) Table 82a

Compounds I.A. wherein Z is CH ₂ CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y is each one Row of Table A corresponds (Compounds IA82aA-1 to IA82aA-444) Table 83a

Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y are each corresponds to one line of Table A (compounds IA83aA-1 to IA83aA-444)

Table 84a compounds LA, wherein Z is CH ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ⁵

CH 3 and R ⁶ + R ^{7 are} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA84aA-1 to IA84aA-444)

Table 85a

Compounds LA in which Z is CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y are each corresponds to one line of Table A (compounds IA85aA-1 to IA85aA-444)

Table 86a

Compounds LA in which Z is CH ₂ CH ₂ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA86aA-1 to IA86aA-444)

Table 87a

Compounds LA in which Z is CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA87aA-1 to IA87aA-444) Table 88a

Compounds LA in which Z is CH ₂ C (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y is corresponds in each case to one row of Table A (compounds IA88aA-1 to IA88aA-444)

Table 89a compounds LA, wherein Z is CH ₂ C (CH ₂ CH ₂ ) CH ₂ , R ² , R ³ and R ^{4 are} H,

R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA89aA-1 to IA89aA-444)

Table 90a

Compounds LA in which Z is C (CH ₂ CH ₂ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA90aA-1 to IA90aA-444)

Table 91a

Compounds LA in which Z is CH ₂ CH (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination from R ¹ and Y corresponds in each case to one row of Table A (compounds IA91aA-1 to

I.A.91aA-444)

Table 92a

Compounds LA, wherein Z is C (CH ₃ ) ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA92aA-1 to IA92aA-444) Table 93a

Compounds LA in which Z is C (CH ₂ CH ₂ ) (CH ₂ ) SCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination each of R ¹ and Y corresponds to one row of Table A (compounds IA93aA-1 to IA93aA-

444) Table 94a

Compounds LA, wherein Z is CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.94aA-1 to I.A.94aA-444)

Table 95a

Compounds LA, wherein Z is CH ₂ CH ₂ CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.95aA-1 to I.A.95aA-444)

Table 96a

Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₃ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA96aA-1 to IA96aA-444) Table 97a

Compounds LA in which Z is (E) CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y is in each case one Line of Table A corresponds (compounds IA97aA-1 to IA97aA-444)

Table 98a

Compounds LA in which Z is (E) C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA98aA-1 to IA98aA-444) Table 99a

Compounds LA, wherein Z is (E) C (CHs) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the Combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.99aA-1 to I.A.99aA-444) Table 100a

Compounds LA, wherein Z is (E) CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA100aA-1 to IA100aA-444) Table 101 a compounds LA, wherein Z is (E) CH ₂ CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H stand,

R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA101 aA-1 to IA101aA-444) Table 102a

Compounds LA in which Z is (E) CH ₂ C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.102aA-1 to I.A.102aA-444)

Table 103a

Compounds LA in which Z is (E) CH ₂ CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.103aA-1 to I.A.103aA-444)

Table 104a

Compounds LA in which Z is (E) CH ₂ C (CH ₃ ) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.104aA-1 to I.A.104aA-444)

Table 105a

Compounds LA, wherein Z is (E) C (CH ₃ ) = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds I .A.105aA-1 to IA105aA-444)

Table 106a

Compounds LA in which Z is (E) C (CH ₃ ) = CH (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.106aA-1 to I.A.106aA-444)

Table 107a

Compounds LA in which Z is (E) CH =C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.107aA-1 to I.A.107aA-444)

Table 108a

Compounds LA in which Z is CH ₂ C≡CCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclohexyl, and the combination of R ¹ and Y is in each case one line corresponding to Table A (compounds IA108aA-1 to IA108aA-444) Table 109a

Compounds LA in which Z is CH ₂ CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y is in each case one line corresponds to Table A (Compounds IA109aA-1 to IA109aA-444). Table 1 10a Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ⁵

CH ₃ and R ⁶ + R ^{7 are} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds IA1 10aA-1 to IA110aA-444) Table 1 11 a

Compounds LA in which Z is CH ₂ (CH ₂ ) SCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y is each one Row of Table A corresponds (Compounds IA1 11 aA-1 to IA11 1aA-444) Table 1 12a

Compounds LA in which Z is CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y is each corresponds to one line of Table A (compounds IA1 12aA-1 to IA112aA-444) Table 1 13a

Compounds LA in which Z is CH ₂ CH ₂ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds I .A.113aA-1 to I .A.113aA-444) Table 1 14a

Compounds LA in which Z is CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA1 14aA-1 to IA114aA-444) Table 1 15a

Compounds LA in which Z is CH ₂ C (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y in each case corresponds to one row of the table A (connections IA1 15aA-1 to IA115aA-444) Table 1 16a connections LA, where Z stands for CH ₂ C (CH ₂ CH ₂ ) CH ₂ , R ² , R ³ and R ⁴ for H stand,

R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds I .A.1 16aA-1 to I .A.116aA-444) Compounds LA, wherein Z is C (CH ₂ CH ₂ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H,

R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds I .A.1 17aA-1 to I .A.117aA-444). Table 1 18a Compounds LA in which Z is CH ₂ CH (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination from R ¹ and Y corresponds in each case to one row of Table A (Compounds IA118aA-1 to IA118aA-444). Table 1 19a Compounds LA in which Z is C (CH ₃ ) ₂ (CH ₂ ) ₃ CH ₂ , R ² , R ³ and R ⁴ stand for H,

R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds I .A.1 19aA-1 to I .A.119aA-444) Table 120a

Compounds LA in which Z is C (CH ₂ CH ₂ ) (CH ₂ ) SCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA120aA-1 to IA120aA-444)

Table 121 a

Compounds LA, wherein Z is CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.121aA-1 to I.A.121aA-444)

Table 122a

Compounds LA in which Z is CH ₂ CH ₂ CH ₂ CH (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.122aA-1 to I.A.122aA-444)

Table 123a

Compounds LA, wherein Z is CH ₂ (CH ₂ ) ₃ CH (CH ₃ ), R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA123aA-1 to IA123aA-444)

Table 124a

Compounds LA in which Z is (E) CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y is in each case one Row of Table A corresponds (Compounds IA124aA-1 to IA124aA-444) Table 125a

Compounds LA in which Z is (E) C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (compounds IA125aA-1 to IA125aA-444) Table 126a

Compounds LA in which Z is (E) C (CHs) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the Combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.126aA-1 to I.A.126aA-444) Table 127a

Compounds LA, wherein Z is (E) CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one row of Table A (Compounds IA127aA-1 to IA127aA-444) Table 128a

Compounds LA in which Z is (E) CH ₂ CH = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y JE because one row corresponds to Table A (Compounds IA128aA-1 to IA128aA-444) Table 129a

Compounds LA in which Z is (E) CH ₂ C (CHs) = CHCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.129aA-1 to I.A.129aA-444)

Table 130a

Compounds LA in which Z is (E) CH ₂ CH = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH 3 and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.130aA-1 to I.A.130aA-444)

Table 131 a

Compounds LA in which Z is (E) CH ₂ C (CH ₃ ) = C (CH ₃ ) CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.131aA-1 to I.A.131aA-444)

Table 132a

Compounds LA, wherein Z is (E) C (CH ₃ ) = C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ⁷ cyclopentyl, and the combination of R ¹ and Y corresponds in each case to one line of Table A (compounds I .A.132aA-1 to IA132aA-444) Table 133a

Compounds LA in which Z is (E) C (CH ₃ ) = CH (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.133aA-1 to I.A.133aA-444)

Table 134a

Compounds LA in which Z is (E) CH =C (CH ₃ ) (CH ₂ ) ₂ CH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and

Y corresponds in each case to one row of Table A (compounds I.A.134aA-1 to I.A.134aA-444)

Table 135a

Compounds LA in which Z is CH ₂ C≡CCH ₂ , R ² , R ³ and R ^{4 are} H, R ^{5 is} CH ₃ and R ⁶ + R ^{7 is} cyclopentyl, and the combination of R ¹ and Y is in each case one line corresponding to Table A (compounds IA135aA-1 to IA135aA-444)

Table A

[ ^* ] "-" means that Y stands for a single bond

From the preceding tables, the connection names for the individual connections are derived as follows: eg. is the "compound | Λ.3aA- ^ 0" (markers added) the compound of the formula [A according to the invention in which Z is CH 2 (CH 2) ₃ CH ² , R ² , R ³ and R ^{4 are} hydrogen, R ^{5 is} H and R ⁶ + R ^{7 is} cyclopropyl (as indicated in Table 3a) and R ^{1 is} 4-cyanophenyl and Y is O (as indicated in line O of Table A).

The compounds of the formula I or the compositions according to the invention are useful as fungicides for controlling harmful fungi. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, including soil-borne pathogens, which in particular originate from the classes of the Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytriomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. In addition, they are suitable for controlling fungi that attack, among other things, the wood or the roots of plants.

Of particular importance are the compounds I and the compositions of the invention for combating a variety of pathogenic fungi on various crops such as cereals, eg. Wheat, rye, barley, triticale, oats or rice; Beets, z. Sugar or fodder beets; Kernel, stone and berry fruits, z. Apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; Legumes, z. Beans, lentils, peas, alfalfa or soybeans; Oil plants, e.g. Rapeseed, mustard, olives, sunflowers, coconut, cocoa, castor beans, oil palm, peanuts or soya; Cucurbits, z. Pumpkins, cucumbers or melons; Fiber plants, z. Cotton, flax, hemp or jute; Citrus fruit, e. Oranges, lemons, grapefruit or mandarins; Vegetables, z. Spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, squash or paprika; Laurel family, z. Avocados, cinnamon or camphor; Energy and raw material plants, eg. Corn, soy, wheat, rapeseed, sugarcane or oil palm; Corn; Tobacco; Nuts; Coffee; Tea; bananas; Wine (table and grapes); Hop; Grass, z. B. lawn; Rubber plants; Ornamental and forest plants, z. As flowers, shrubs, deciduous and coniferous trees and on the propagation material, for. B. seeds, and the crop of these plants.

Preferably, the compounds I or the compositions according to the invention for combating a variety of fungal pathogens in crops, z. Potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugarcane; Fruit, vine and ornamental plants and vegetables, eg. As cucumbers, tomatoes, beans and pumpkins and on the propagation material, for. As seeds, and the crop of these plants used.

The term plant propagating materials includes all generative parts of the plant, e.g. As seeds, and vegetative plant parts, such as cuttings and tubers (eg., Potatoes), which can be used to propagate a plant. These include seeds, roots, fruits, tubers, bulbs, rhizomes, shoots and other plant parts, including seedlings and seedlings, which are transplanted after germination or emergence. The young plants can be treated by a partial or complete treatment, eg. B. by immersion or pouring, protected from harmful fungi become.

The treatment of plant propagating materials with compounds I or the compositions according to the invention is used for combating a variety of fungal pathogens in cereal crops, e.g. Wheat, rye, barley or oats; Rice, corn, cotton and soy used.

The term "crops" also includes those plants which have been modified by breeding, mutagenesis or genetic engineering methods, including biotechnological agricultural products currently on the market or under development (see for example http://www.bio.org/speeches/pubs/ er / agri_products .asp). Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant. Such genetic engineering also includes post-translational modifications of proteins, oligo- or polypeptides, e.g. by glycolylation or binding of polymers such as e.g. prenylated, acetylated or farnelysierter residues or PEG residues.

By way of example, plants may be mentioned which, by means of breeding and genetic engineering measures, tolerate certain types of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) -I inhibitors, such as, for example, Sulfonylureas (EP-A 257 993, US Pat. No. 5,013,659) or imidazolinones (for example US Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04 / 106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors such as. Glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors such as. Glufosinate (see eg EP-A 242 236, EP-A 242 246) or oxynil herbicides (see eg US 5,559,024). By breeding and mutagenesis z. B. Clearfield ^® rapeseed (BASF SE, Germany) produced, the tolerance to imidazolinones, z. As imazamox, has. Using genetic engineering methods, crop plants such as soybean, produces cotton, corn, beets and rape, which are resistant to glyphosate or glufosinate, and sold under the trade name rou- dupReady ^® (glyphosate-resistant, Monsanto, USA) and Liberty Link ^® (Glufosinat- resistant, Bayer CropScience, Germany) are available.

Furthermore, plants are included which, with the aid of genetic engineering measures one or more toxins, eg. B. those from the bacterial strain Bacillus produce. Toxins produced by such genetically engineered plants include e.g. Insecticidal proteins of Bacillus spp., In particular B. thuringiensis such as the endotoxins CrylAb, CrylAc, CrylF, Cry1Fe2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g. Eg VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. Eg from Streptomyces; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g. Ricin, corn RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing enzymes, e.g. 3-hydroxy steroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blocker, e.g. B. inhibitors of sodium or calcium channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin receptors); Stilbene synthase, bibenzyl synthase, chitinases and glucanases. These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are described in EP-A 374 753, WO 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073 discloses. The methods for producing these genetically modified plants are known in the art and z. B. in the publications mentioned above. Many of the aforementioned toxins confer on the plants that produce them a tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera (Diptera) and butterflies (Lepidoptera) and nematodes (Nematoda). Genetically modified plants which produce one or more genes which code for insecticidal toxins are, for example, As described in the publications mentioned above and partly commercially available, such as. B. YieldGard ^® (corn cultivars producing the toxin CrylAb), YieldGard ^® Plus (corn cultivars producing the toxins CrylAb and Cry3Bb1), StarLink ^® (corn cultivars producing the toxin Cry9c), Herculex ^® RW (corn cultivars toxins which Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT] produce); NuCOTN ^® 33B (cotton varieties which toxin is

CrylAc produce), Bollgard ^® I (cotton cultivars producing the toxin CrylAc), Bollgard ^® Il (cotton cultivars producing the toxins CrylAc and Cry2Ab2); VIP COT ^® (cotton cultivars producing a VIP-toxin); NewLeaf ^® (potato cultivars producing the Cry3A toxin); Bt Xtra ^®, NatureGard® ^®, KnockOut ^®, BiteGard ^®, Protec ta ^®, bt 11 (z. B. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which the toxin CrylAb and the PAT Producing enzyme), MIR604 from Syngenta Seeds SAS, France (maize varieties producing a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe SA, Belgium (maize varieties producing the toxin Cry3Bb1), IPC 531 from Monsanto Europe SA, Belgium (cotton varieties that produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties that produce the toxin Cryl F and the PAT enzyme). Furthermore, plants are included, which produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as. For example, so-called pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties which produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lyso - zym (eg, potato varieties that are resistant to bacteria such as Erwinia amylvora due to the production of this protein).

Furthermore, plants are included whose productivity with the help of genetic engineering

Methods has been improved by z. For example, yield (eg biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens may be increased. Furthermore, plants are included whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z. As oil plants producing health long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Nexera ^® - rape, DOW Agro Sciences, Canada.) Produce.

Furthermore, plants are included, which have been modified for the improved production of raw materials by means of genetic engineering methods by z. B. the amylopectin content of potatoes (Amflora ^® potato, BASF SE, Germany) was increased.

In particular, the compounds I or the compositions according to the invention are suitable for controlling the following plant diseases:

Albugo spp. (White rust) on ornamental plants, vegetable crops (eg A. Candida) and sunflowers (eg BA tragopogonis); Alternaria spp. (Blackness, black spotiness) on vegetables, oilseed rape (for example BA brassicola or A. brassicae), sugar beet (for example BA tenuis), fruit, rice, soybeans and on potatoes (eg A. solani or A. alternata) and tomatoes (eg BA solani or A. alternata) and Alternaria spp. (Earwires) on wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, eg. BA tritici (leaf drought) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (Teleomorph: Cochliobolus spp.) Z. B. leaf spot diseases (D. maydis and B. zeicola) on maize, e.g. B. brown spot (B. sorokiniana) on cereals and B. B. oryzae on rice and on lawn; Blumeria (formerly: Erysiphe) graminis (powdery mildew) on cereals (eg wheat or barley); Botryosphaeria spp. ('Black Dead Arm Disease') on vines (eg BB obtusa); Botrytis cinerea (Teleomorph: Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz) on deciduous and coniferous trees, z. BC ulmi (elm dying, Dutch elm disease) on elms; Cercospora spp. (Cercospo- ra leaf spots) on corn (e.g., BC zeae-maydis), rice, sugar beets (e.g., BC beticola), sugar cane, vegetables, coffee, soybeans (e.g., BC sojina, or C. kikuchii) and rice; Cladosporium spp. on tomato (eg BC fulvum: velvet spot disease) and cereals, eg. BC herbarum (earwax) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorph: Helminthosporium or Bipolaris) spp. (Leaf spot) on maize (for example BC carbonum), cereals (for example B. sativus, anamorph: B. sorokinia-na: brown spot) and rice (for example BC miyabeanus, anamorph: H. oryzae); Colletotricum (teleomorph: Glomerella) spp. (Burning stains, anthracnose) on cotton (eg BC gossypii), corn (eg BC graminicola: stalk rot and stinging spots), soft fruit, potatoes (eg BC coccodes: wilting), beans (eg BC lindemuthianum) and soybeans (eg. BC truncatum); Corticium spp., Z. BC sasakii (leaf sheath burn) on rice; Corynespora cassiicola (leaf spot) on soybeans and ornamental plants; Cycloconium spp., Z. BC oleaginum on olive; Cylindrocarpon spp. (eg, fruit tree crayfish or vine dying, Teleomorph: Nectria or Neonectria spp.) on fruit trees, grapevines (eg, C. liriodendri, Teleomorph: Neonectria liriodendri, 'Black Foot Disease') and many ornamental shrubs; Dematophora (Teleomorph: Rosellinia) necatrix (root / stalk rot) on soybeans; Diaporthe spp. z. BD phaseolorum (stalk disease) on soybeans; Drechslera (Syn. Helminthosporium, Teleomorph: Pyrenophora) spp. on corn, cereals such as barley (eg BD teres, nettles) and wheat (eg BD tritici- repentis: DTR leaf drought), rice and turf; Esca disease (grapevine dying, apoplexy) on grapevine caused by Formitiporia (Syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe spp. on nuclear (E. pyri) and soft fruit (E. veneta: burning spots) and grapevine (E. ampelina: burning spots); Entyloma oryzae (leaf sting) on rice; Epicoccum spp. (Earwires) on wheat; Erysiphe spp. (Powdery mildew) on sugar beet (E. betae), vegetables (eg BE pisi), such as cucumber (for example BE cichoracearum) and cabbage plants, such as rapeseed (for example, B. cruciferarum); Eutypa lata (Eutypa crab or extinction, anamorphic: Cyto- sporina lata, Syn. Libertella blepharis) on fruit trees, vines and many ornamental trees; Exserohilum (Syn. Helminthosporium) spp. on maize (eg BE turcicum); Fusarium (Teleomorph: Gibberella) spp. (Wilt, root and stalk rot) on various plants, such. BF graminearum or F. culmorum (root rot and Tauboder whiteness) on cereals (eg wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on maize; Gaeumannomyces graminis (blackleg) on cereals (eg wheat or barley) and maize; Gibberella spp. cereals (eg BG zeae) and rice (eg BG fujikuroi: Bakanae disease); Glomerella cingulata on grapevine, pome fruit and other plants and G. gossypii on cotton; Grainstaining complex of rice; Guignardia bidwellii (black rot) on grapevine; Gymnosporangium spp. on rosaceae and juniper, eg. BG sabinae (pear lattice rust) on pears; Helminthosporium spp. (Syn. Drechslera, Teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., E.g. BH vastatrix (coffee leaf rust) of coffee; Isariopsis clavispora (Syn. Cladosporium vitis) on grapevine; Macrophomina phasolina (Syn. Phaseoli) (root / stem rot) on soybeans and cotton; Micro- dochium (Syn. Fusarium) nivale (snow mold) on cereals (eg wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., Z. BM laxa, M. fructicola and M. fructigena (flower and lace drought) on stone fruits and other rosaceae; Mycosphaerella spp. cereals, bananas, berries and peanuts, such as BM graminicola (Anamorph: Septoria tritici, Septoria leaf drought) on wheat or M. fijiensis (Black Sigatoka disease) on bananas; Peronospora spp. (Downy mildew) on cabbage (for example BP brassicae), oilseed rape (for example P. parasitica), onion plants (for example B. destructor), tobacco (P. tabacina) and soybeans (for example P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phallophora spp. z. On grapevines (eg BP tracheiphila and P. tetraspora) and soybeans (eg BP gregata: stalk disease); Phoma Hungary (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spots) on sugar beet; Phomopsis spp. on sunflowers, grapevine (eg BP viticola: black spot disease) and soybeans (eg stalk rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora spp. (Wilt, root, leaf, stem and fruit rot) on various plants, such as on paprika and cucurbits (eg BP capsici), soybeans (eg BP megasperma, Syn. P. sojae), potatoes and tomatoes (eg. BP infestans: herbaceous and brown rot) and deciduous trees (eg BP ramorum: sudden oak mortality); Plasmodiophora brassicae (cabbage hernia) on cabbage, oilseed rape, radish and other plants; Plasmopara spp., E.g. BP viticola (vine peronospora, downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (Powdery mildew) of rosaceae, hops, kernels and berries, eg. BP leucotricha to apple; Polymyxa spp., Z. To cereals such as barley and wheat (P. graminis) and sugar beet (P. betae) and the viral diseases conferred thereby; Pseudocercosporella herpotrichoides (straw break, teleomorph: Tapesia yallundae) on cereals, e.g. Wheat or barley; Pseudoperonospora (downy mildew) on various plants, e.g. BP cubensis on cucurbits or P. humili on hops; Pseudo-pezicula tracheiphila (red burner, anamorph: Phialophora) on grapevine; Puccinia spp. (Rust disease) on various plants, eg. BP triticina (wheat brown rust), P. striiformis (yellow rust), P. hordei (dwarf rust), P. graminis (black rust) or P. recondita (rye brown rust) on cereals, such as. Wheat, barley or rye, and asparagus (eg BP asparagi); Pyrenophora (anamorph: Drechslera) tritici-repentis (leaf drought) on wheat or P. teres (net stains) on barley; Pyricularia spp., E.g. BP oryzae (teleomorph: Magnaporthe grisea, rice leaf-brandy) on rice and P. grisea on seeds and cereals; Pythium spp. (Turnip disease) on turf, rice, corn, wheat,

Cotton, rapeseed, sunflower, sugar beet, vegetables and other plants (eg BP ultimum or P. aphanidermatum); Ramularia spp., Z. BR collo-cygni (speckled disease / sunburn complex / Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and various other plants, eg. BR solani (root / stem rot) on soybeans, R. solani (leaf-sheathing) on rice or R. cerealis (pointed eye-spot) on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevine and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (Stem or white rot) in vegetables and crops such as oilseed rape, sunflowers (eg Sclerotinia sclerotium rum) and soybeans (eg BS rolfsii); Septoria spp. on different plants, eg. BS glycines (leaf spot) on soybeans, S. tritici (Septoria leaf drought) on wheat and S. (Syn. Stagonospora) nodorum (leaf and spelled tan) on cereals; Uncinula (Syn. Erysiphe) necator (powdery mildew, anamorphic: Oidium tuckeri) on grapevine; Sexspaeria spp. (Leaf spot) on corn (for example, S. turcicum, Syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (Dust fires) on maize, (for example BS reiliana: flask brandy), millet and sugarcane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powder scab) on potatoes and the viral diseases transmitted thereby; Stagonospora spp. on cereals, z. BS nodorum (leaf and tan, Teleomorph: Leptosphaeria [Syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato cancer); Taphrina spp., Z. BT deformans (curling disease) on peach and T. pruni (pocket disease) on plums; Thielaviopsis spp. (Black root rot) on tobacco, pome fruit, vegetable crops, soybeans and cotton, eg. BT basicola (Syn: Chalara elegans); Tilletia spp. (Stone or Stinkbrand) of cereals, such. BT tritici (Syn. T. caries, Weizensteinbrand) and T. controversa (Zwergsteinbrand) on wheat; Typhula incarnata (snow rot) on barley or wheat; Urocystis spp., E.g. BU occulta (stalk brandy) on rye; Uromyces spp. (Rust) on vegetables, such as beans (for example, appendiculatus appendix, Syn. U. phaseoli) and sugar beet (for example, Betae); Ustilago spp. (Firefighting) on cereals (for example BU nuda and U. avaenae), maize (for example, maydis: corn buckthorn brandy) and sugarcane; Venturia spp. (Scab) on apples (eg BV inaequalis) and pears; and Verticillium spp. (Deciduous and cloudy wilt) on various plants, such as fruit and ornamental trees, vines, soft fruit, vegetables and crops, such. BV dahliae on strawberries, rapeseed, potatoes and tomatoes.

The compounds I and the compositions according to the invention are also suitable for controlling harmful fungi in the storage protection (also of crops) and in the protection of materials and buildings. The term "material and building protection" covers the protection of technical and non-living materials such. As adhesives, glues, wood, paper and cardboard, textiles, leather, color dispersions, plastics, coolants, fibers and tissues, against the infestation and destruction by unwanted microorganisms such as fungi and bacteria. In wood and material protection, particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae. The compounds of the formula I can be present in various crystal modifications whose biological activity can be different. These are included in the scope of the present invention.

The compounds I and the compositions according to the invention are suitable for increasing plant health. Moreover, the invention relates to a method for enhancing plant health by treating the plants, the plant propagating material and / or the place where the plants are to grow or grow with an effective amount of the compounds I or the compositions according to the invention.

The term "plant health" includes those conditions of a plant and / or its crop which are determined by various indicators individually or in combination with one another, such as yield (eg increased biomass and / or increased content of utilizable ingredients), Plant vitality (eg, increased plant growth and / or greener leaves), quality (eg, increased content or composition of certain ingredients), and tolerance to biotic and / or abiotic stress. These plant health status indicators listed here may occur independently of each other or may be mutually exclusive.

The compounds I are used as such or in the form of a composition by the harmful fungi, their habitat or the plants to be protected against fungal attack, plant propagating materials, eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the compounds I. The application may be both before and after the infection of the plants, plant propagation materials, eg. As seeds, the soil, the surfaces, materials or spaces made by the fungi.

Plant propagating materials may be treated preventively together with or even before sowing or together with or even before transplanting with compounds I as such or with a composition containing at least one compound I.

In addition, the invention relates to agrochemical compositions containing a solvent or solid carrier and at least one compound I and their use for controlling harmful fungi.

An agrochemical composition contains a fungicidally effective amount of a compound I. The term "effective amount" means an amount of the agrochemical composition or compound I which is sufficient for controlling harmful fungi on crop plants or in the protection of materials and buildings and not too causes considerable damage to the treated crops. Such an amount may vary within a wide range and is dependent on numerous factors, such as: As the harmful fungus to be controlled, the respective treated crop or materials, the climatic conditions and compounds influenced.

The compounds I, their N-oxides and their salts can be converted into the types customary for agrochemical compositions, e.g. As solutions, emulsions, suspensions, dusts, powders, pastes and granules. The type of composition depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.

Examples of composition types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which may either be soluble (soluble) or dispersible (wettable) in water, as well as gels for the treatment of plant propagating materials such as seeds (GF).

In general, the composition types (eg EC, SC, OD, FS, WG, SG, WP, SP, SS, WS, GF) are used diluted. Composition types such as DP, DS, GR, FG, GG and MG are generally used undiluted.

The agrochemical compositions are prepared in a known manner (see, for example, US 3,060,084, EP-A 707,445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th ed., McGraw-Hill, New York, 1963, 8-57 and et seq., WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030, GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science (John Wiley & Sons, New York, 1961), Hance et al .: Weed Control Handbook (8th Ed., Blackwell Scientific Publications, Oxford, 1989) and Mollet, H. and Grubemann, A. : Formulation technology (Wiley VCH Verlag, Weinheim, 2001).

The agrochemical compositions can furthermore also contain auxiliaries customary for crop protection agents, the choice of auxiliaries being based on the specific application form or the active substance.

Examples of suitable auxiliaries are solvents, solid carriers, surface-active substances (such as further solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if appropriate dyes and adhesives (for example for seed treatment).

The solvents used include water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons. aliphatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones such as cyclohexanone, gamma-butyrolactone, dimethyl fatty acid amides, fatty acids and fatty acid esters and strongly polar solvents, for example amines such as N-methylpyrrolidone, into consideration. In principle, solvent mixtures and mixtures of the abovementioned solvents and water can also be used.

Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

As surface-active substances (adjuvants, wetting agents, adhesives, dispersants or emulsifiers), the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. B. of lignin (Borresperse ^® grades, Borregaard, Norway), phenol, naphtha lin (Morwet ^® types, Akzo Nobel, USA) and dibutyl (nekal ^® - types, BASF, Germany), and of fatty acids , Alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with Phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecylalcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulphite liquors and Proteins, denatured proteins, polysaccharides (eg methylc ellulose), hydro- phobic modified starches, polyvinyl alcohol (Mowiol ^® types, Clariant, Switzerland), poly-carboxylate (Sokalan ^® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lu pamin ^® types, BASF, Germany) , polyethyleneimine (Lupasol ^® types, BASF, Germany), polyvinylpyrrolidone and copolymers thereof.

Examples of thickeners (ie, compounds that give the composition a modified flow properties, ie high viscosity at rest and low viscosity in motion) are polysaccharides and organic and inorganic sheet minerals, such as xanthan gum (Kelzan ^®, CP Kelco, U.S.A.), Rhodopol ^® 23 (Rhodia, France) or Veegum ^® (RT Vanderbilt, USA) or attaclay ^® (Engelhard Corp., NJ, USA).

Bactericides may be added to stabilize the composition. Examples of bactericides are those based on diclorophene and benzyl alcohol hemiformal (Proxel ^® from. ICI or Acticide ^® RS from. Thor Chemie and Kathon ^® MK from. Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide ^® MBS from Thor Chemie)..

Examples of suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

Examples of defoamers are silicone emulsions (such as, for example, silicone ^® SRE, Wacker, Germany or Rhodorsil ^®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

Examples of colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned are those under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1, Pigment Blue 15: 4, Pigment Blue 15: 3, Pigment Blue 15: 2, Pigment Blue 15: 1, Pigment Blue 80, Pigment yel- low 1, Pigment yellow 13, Pigment red 48: 2, Pigment red 48: 1, Pigment red 57: 1, Pigment red 53: 1, Pigment orange 43, Pigment orange 34, Pigment orange 5, Pigment green 36, Pigment green 7, Pigment white 6, Pigment brown 25, Basic violet 10, Basic violet 49, Acid red 51, Acid red 52, Acid red 14, Acid blue 9, Acid yellow 23, Basic red 10, Basic red 108 well-known dyes and pigments ,

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and cellulose ethers (Tylose ^®, Shin-Etsu, Japan).

For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.

Powders, litter and dusts can be prepared by mixing or joint grinding of the compounds I and, if present, other active ingredients with at least one solid carrier.

Granules, for. As coated, impregnated and homogeneous granules can be prepared by binding the active ingredients to at least one solid carrier. Solid carriers are z. As mineral earths, such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate , Ureas and vegetable products such as cereal flour, bark, wood and nutshell flour, cellulose powders and other solid carriers.

Examples of composition types are: 1. Compositions for dilution in water i) Water-soluble concentrates (SL, LS)

10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a composition with 10 wt .-% active ingredient content. ii) Dispersible Concentrates (DC)

20 parts by weight of the active ingredients are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant z. B. dissolved polyvinylpyrrolidone. Dilution in water results in a dispersion. The active ingredient content is 20% by weight iii) Emulsifiable Concentrates (EC)

15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion. The composition has 15% by weight active ingredient content. iv) Emulsions (EW, EO, ES)

25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added by means of an emulsifying machine (eg Ultra-Turrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion. The composition has an active ingredient content of 25 wt .-%. v) suspensions (SC, OD, FS)

20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the composition is 20% by weight. vi) Water-dispersible and Water-soluble Granules (WG, SG) 50 parts by weight of the active ingredients are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and water-dispersible by means of technical equipment (eg extrusion, spray tower, fluidized bed) or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient. The composition has an active substance content of 50% by weight. vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the active ingredients are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the composition is 75% by weight. viii) gels (GF)

In a ball mill, 20 parts by weight of the active ingredients, 10 parts by weight of dispersant, 1 part by weight of swelling agent ("gelling agent") and 70 parts by weight of water or an organic solvent are ground to a fine suspension thinners With water gives a stable suspension with 20 wt .-% active ingredient content. 2. Composition types for direct application ix) dusts (DP, DS)

5 parts by weight of the active ingredients are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content. x) Granules (GR, FG, GG, MG)

0.5 part by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes include extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content. xi) ULV solutions (UL)

10 parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent z. B. XyIoI solved. This gives a composition for direct application with 10% by weight of active ingredient content.

The compositions of the compounds according to the invention generally contain 0.01 to 95 wt .-%, preferably 0.1 to 90 wt .-% of the compounds I. The compounds are preferably in a purity of 90% to 100%, preferably 95% to 100% used.

For the treatment of plant propagation materials, in particular seed, usually water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gels ( GF). These compositions can be applied to the propagating materials, in particular seeds, undiluted or, preferably, diluted. In this case, the corresponding composition can be diluted 2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight, of active substance is present in the compositions to be used for the stain. The application can be done before or during sowing.

The treatment of plant propagation material, in particular the treatment of seed, are known to the person skilled in the art and are carried out by dusting, coating, pelleting, dipping or impregnating the plant propagation material, wherein the treatment preferably takes place by pelleting, coating and dusting or by furrow treatment, so that z. B. premature germination of the seed is prevented.

For seed treatment, suspensions are preferably used. Typically, such compositions contain 1 to 800 g / l active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water ,

The compounds may be used as such or in the form of their compositions, e.g. B. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules be applied by spraying, misting, dusting, scattering, brushing, dipping or pouring. The composition types depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention. Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water. For the preparation of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.

The active ingredients can also be successfully used in the ultra-low-volume (ULV) process, whereby it is possible to apply compositions containing more than 95% by weight of active ingredient or even the active ingredient without additives.

The application rates in the application in crop protection, depending on the nature of the desired effect between 0.001 and 2.0 kg of active ingredient per ha, preferably between 0.005 and 2 kg per ha, more preferably between 0.05 and 0.9 kg per ha, in particular between 0.1 and 0.75 kg per ha.

In the treatment of plant propagation materials, eg. B. State, are generally active amounts of from 0.1 to 1000 g / 100 kg of propagating material or seed, preferably 1 to 1000 g / 100 kg, more preferably 1 to 100 g / 100 kg, in particular 5 to 100 g / 100 kg used.

When used in material or storage protection, the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.

Oils of various types, wetting agents, adjuvants, herbicides, bactericides, other fungicides and / or pesticides may also be added to the active substances or the compositions containing them, if appropriate also immediately before use (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.

As adjuvants in this sense are in particular: organically modified polysiloxanes, eg. B. Break Thru S ^240® ; Alcohol alkoxylates, eg. B. Atplus 245 ^®, Atplus MBA ^® 1303 Plurafac ^® LF 300 ^® and Lutensol ON 30; EO-PO block polymers, eg. B. Pluronic RPE 2035 ^® and Genapol B ^®; Alcohol ethoxylates, eg. B. Lutensol ^® XP 80; and sodium dioctylsulfosuccinate, e.g. B. Leophen ^® RA.

The compositions of the invention may also be present in the application form as fungicides together with other active ingredients, for. With herbicides, Insecticides, growth regulators, fungicides or even with fertilizers, as a pre-mix or, if appropriate, only immediately before use (tank mix).

When mixing the compounds I or the compositions containing them with one or more further active compounds, in particular fungicides, for example, in many cases, the activity spectrum can be broadened or resistance developments can be prevented. In many cases, synergistic effects are obtained.

The following list of active ingredients with which the compounds according to the invention can be used together is intended to illustrate, but not limit, the possible combinations: A) strobilurins:

Azoxystrobin, Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metomino Strobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxy-imino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -

Methyl 3-methoxy-acrylate, methyl 3-methoxy-2- (2- (N- (4-methoxyphenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) acrylate, 2- (2- (3- (2,6-dichlorophenyl ) -1-methyl-allylideneaminooxymethyl) -phenyl) -2-methoxy-imino-N-methyl-acetamide; B) Carboxylic acid amides:

- carboxylic acid anilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carbo-xin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, Penflufen (N- (2- (1,3-dimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide), penthiopyrad, sedaxanes, tecloftalam, thifluzamide, Tiadinil, 2-amino

4-methyl-thiazole-5-carboxanilide, 2-chloro-N- (1,1,3-trimethyl-indan-4-yl) nicotinamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl ) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'-trifluoromethylthiobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide , N- (2- (1,3,3-trimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide;

- Carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph;

Benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;

Other carboxamides: carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;

C) Azoles:

- Triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole , Prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro-phenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol;

- imidazoles: cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole; Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

- Other: ethaboxam, etridiazole, hymexazole, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxyphenyl) -isoxazol-5-yl] -2-prop-2-ynyloxy-acetamide ;

D) Nitrogen-containing heterocyclyl compounds - pyridines: fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine, 3- [5- (4-methylphenyl ) -2,3-dimethylisoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N - (1- (5-bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloro-nicotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4-dichlornicotinamid; Pyrimidines: Bupirimat, Cyprodinil, Diflumetorim, Fenarimol, Ferimzone, Mepanipyrim, Nitrapyrin, Nuarimol, Pyrimethanil;

- piperazines: triforins;

- Pyrroles: fludioxonil, fenpiclonil;

- morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; - piperidines: fenpropidine;

Dicarboximides: fluorimide, iprodione, procymidone, vinclozolin;

non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester; - Other: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoquatmethylsulfate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazid, pyroquilon, qui - Noxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1 - (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1 H-benzoimidazole, 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a ] pyrimidine, 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine;

E) carbamates and dithiocarbamates

Thio and dithiocarbamates: Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram; Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb, Propamocarb hydrochloride, Valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid- (4-fluorophenyl) ester;

F) Other fungicides

Guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadin tris (albesilat);

- antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;

Nitrophenyl derivatives: binapacryl, diclorane, dinobutone, dinocap, nitrothal-isopropyl, tecnazene; Organometallics: fentin salts such as fentin acetate, fentin chloride, fentin hydroxide;

Sulfur-containing heterocyclyl compounds: dithianone, isoprothiolanes;

Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, Phosphoric acid and its salts, pyrazophos, tolclofos-methyl;

Organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophene, flusulphamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4- methyl-benzenesulfonamide;

Inorganic active ingredients: phosphorous acid and its salts, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

- Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (cyclopropylmethoxyimino- (6-difluoromethoxy-2,3-difluorophenyl) - methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamide, N' - (4- (4-Fluoro-3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl) propoxy) -phenyl) -N-ethyl-N-methylformamidine, N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine, 2- { 1- [2- (5-Methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -thiazole-4-carboxylic acid-methyl- (1,2,3,4-tetra- hydronaphthalene-1-yl) -amide, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -thiazole-4-carboxylic acid-methyl - (R) -1, 2,3,4-tetrahydronaphthalene-1-yl-amide, acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl-ester, M ethoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl-ester, N-methyl-2- {1- [2- (5-methyl) 3-trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -N - [(1R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -4 -thiazolcarboxamid; G) growth regulators abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butraline, chlormequat (chlormoquat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipine, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, Gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), metconazole, naphthalene acetic acid, N-6-benzyladenine, paclobutrazole, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazoron, tri-penthenol, tributylphosphorotrithioate, 2,3,5-tri-iodobenzoic acid, trinexapac-ethyl and uniconazole; H) herbicides

Acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamide,

Pretilachlor, propachlor, thenylchloride;

Amino acid analogues: bilanafos, glyphosate, glufosinate, sulfosate;

Aryloxyphenoxypropionates: Clodinafop, Cyhalofop-butyl, Fenoxaprop, Fluazifop, Haloxyfop, Metamifop, Propaquizafop, Quizalofop, Quizalofop-P-tefuryl; Bipyridyls: diquat, paraquat;

Carbamates and thiocarbamates: asulam, butylates, carbamides, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinates, orbencarb, phenmedipham, prosulphocarb, pyributicarb, thiobencarb, triallates; - cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;

- Dinitroanilines: Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Prodiamine, Trifluralin; Diphenyl ether: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;

Hydroxybenzonitriles: bromoxynil, dichlobenil, loxynil;

Imidazolinone: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr; Phenoxyacetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop;

- Pyrazines: Chloridazon, Flufenpyr-ethyl, Fluthiacet, Norflurazon, Pyridate;

- pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, pilinoram, picolinafen, thiazopyr; Sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl,

Chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, Triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-propylimidazo [1,2-b] pyridazin-3-yl) sulfonyl) -3- (4,6-dimethoxypyrimidine) 2-yl) urea;

Triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozine, hexazinone, metachronon, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam; Ureas: chlorotoluron, da- muron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;

- other inhibitors of acetolactate synthase: bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxime, pyriftalid, pyriminobac-methyl, pyrimisulphane, pyrithiobac, pyroxasulphone, pyroxsulam;

- Other: Amicarbazone, Aminotriazole, Anilofos, Beflubutamide, Benazoline, Bencarbazone, Benfluresat, Benzofenap, Bentazone, Benzobicyclone, Bromacil, Bromobutide, Bu- tattacil, Butamifos, Cafenstrole, Carfentrazone, Cinidone-Ethlyl, Chlorthal, Cinnamethyl-, Clomazone , Cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanide, fentrazamide, flumigorac-pentyl, flumioxazine, flupoxam, fluorochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, Quinclorac, quinmerac, mesotrione, methylarsenoic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefon, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamin, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, Topramezone, 4-hydroxy-3- [2- (2-methoxy-ethoxymethyl) -6-trifluoromethyl-pyridine-3-carbonyl] -bicyclo [3.2.1] oct-3-en-2-one, (3- [ 2-chloro-4-fluoro-5- (3-methyl-2,6-di oxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidine 1-yl) -phenoxy] -pyridin-2-yloxy) -acetic acid ethyl ester, θ-amino-δ-chloro-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3- (2-cyclopropyl-6-methyl-phenoxy ) - pyridazin-4-ol, 4-amino-3-chloro-6- (4-chlorophenyl) -5-fluoropyridine-2-carboxylic acid, 4-amino-3-chloro-6- (4-chloro 2-fluoro-3-methoxy-phenyl) -pyridine-2-carboxylic acid methyl ester and 4-amino-3-chloro-6- (4-chloro-3-dimethylamino-2-fluoro-phenyl) -pyridine-2 carboxylsäuremethylester; I) insecticides

Organo (thio) phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulphoton, ethion, fenitrothion, fenthione, isoxathione, malathion, methamidophosphate, methidathion , Methyl parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidone, phorates, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorinophos, terbufos, triazophos, trichlorfon; Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamates;

- pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalo- thrin, permethrin, prallethrin , Pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin,

Insect growth inhibitors: a) chitin synthesis inhibitors: benzoylureas: chlorofluorazuron, cyramazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; Buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) Juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spinotetramat; Nicotine receptor agonists / antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1- (2-chlorothiazol-5-ylmethyl) -2-nitrimino-3,5-dimethyl- [1, 3,5] triazinane;

GABA antagonists: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1- (2,6-dichloro-4-methylphenyl) -4-sulfinamoyl-1H-pyrazole-3-thiocarbon acid amide;

Macrocyclic lactones: Abamectin, Emamectin, Milbemectin, Lepimectin, Spinosid, Spinetoram;

- mitochondrial electron transport chain inhibitor (METI) I acaricides: Fenazaquin, Pyridaben, Tebufenpyrad, Tolfenpyrad, Flufenerim; - METI II and III substances: Acequinocyl, Fluacyprim, Hydramethylnon;

- decoupler: chlorfenapyr;

Inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite; Inhibitors of the sloughing of insects: Cryomazine;

Inhibitors of mixed function oxidases: piperonyl butoxide;

Sodium channel blocker: indoxacarb, metaflumizone;

- Other: Benclothiaz, Bifenazate, Cartap, Flonicamid, Pyridalyl, Pymetrozine, Sulfur, Thiocyclam, Flubendiamid, Chlorantraniliprole, Cyazypyr (HGW86); Cynopyphron, Flupyrazofos, Cyflumetofen, Amidoflumet, Imicyafos, Bistrifluron and Pyrifluquinazone.

The present invention also relates, in particular, to fungicidal compositions which comprise at least one compound of the general formula I and at least one further crop protection active ingredient, in particular at least one fungicidal active ingredient, eg. One or more, e.g. 1 or 2 active compounds of the abovementioned groups A) to F) and optionally one or more agriculturally suitable carriers. With regard to a reduction of the application rates, these mixtures are of interest, since many show an improved action against harmful fungi, especially for certain indications, with a reduced total quantity of applied active substances. By simultaneous joint or separate application of compound (s) I with at least one active compound of groups A) to I), the fungicidal activity can be increased to a superadditive extent.

Common application within the meaning of this application means that the at least one compound I and the at least one other active ingredient at the same time at the site of action (ie the attacking plant-damaging fungi and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or rooms and the before Fungal attack on plants to be protected, plant propagation materials, in particular seeds, soil, materials or spaces) in an amount sufficient for effective control of fungal growth. This can be achieved by simultaneously applying the compounds I and at least one further active ingredient together in a common active ingredient preparation or in at least two separate active ingredient preparations or by applying the active ingredients one after the other at the site of action, whereby the time interval of the individual active substance applications is selected is that the first applied active ingredient at the time of application of / the other drug / substances in sufficient amount is present at the site of action. The time sequence of the application of the active ingredients is of minor importance.

In binary mixtures, ie compositions according to the invention which contain a compound I and a further active ingredient, for example an active compound from groups A) to I), the weight ratio of compound I to the further active ingredient depends on the weight ratio of compound I to the first further active ingredient usually from 1: 100 to 100: 1, often in the range from 1:50 to 50: 1, preferably in the range from 1:20 to 20: 1, more preferably in the range from 1:10 to 10: 1, especially in the range of 1: 3 to 3: 1.

In ternary mixtures, d. H. compositions according to the invention comprising an active substance I and a further active ingredient and a further active ingredient, eg. B. contain two different agents from groups A) to I), the weight ratio of compound I to 1 further active ingredient depends on the properties of the respective active ingredients, preferably in the range of 1:50 to 50: 1 and in particular in Range from 1:10 to 10: 1. The weight ratio of compound I to the second further active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 1. The weight ratio of 1. further active ingredient to the second further active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 1.

The components of the composition according to the invention can be mixed individually or already mixed or packaged as parts according to the kit of parts and reused.

In one embodiment of the invention, the kits (kits) may contain one or more, even all, components which can be used to prepare an agrochemical composition according to the invention. For example, these kits may contain one or more fungicidal component (s) and / or an adjuvant component and / or an insecticidal component and / or a growth regulator component and / or a herbicide. One or more components may be combined or pre-formulated. In embodiments where more than two components are provided in a kit, the components may be combined together and packaged in a single container such as a vessel, bottle, can, bag, sack or canister. In other embodiments, two or more components of a kit may be packaged separately, i. H. not pre-formulated or mixed. Kits may contain one or more separate containers such as containers, bottles, cans, bags, sacks or canisters, each container containing a separate component of the agrochemical composition. The components of the composition according to the invention can be mixed individually or already mixed or packaged as parts according to the "kit of parts" and reused. In both forms, one component can be used separately or together with the other components or as part of a kit of parts according to the invention for the preparation of the mixture according to the invention.

The user usually uses the composition according to the invention for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane. In this case, the agrochemical composition is brought to the desired application concentration with water and / or buffer, optionally further adjuvants are added, and thus obtain the ready-spray mixture or the agrochemical composition of the invention becomes. Usually, 50 to 500 liters of ready-spray mixture per hectare of agricultural land, preferably 100 to 400 liters.

In one embodiment, the user may include individual components such as B. parts of a kit or a two or three-mixture of the composition of the invention itself in the spray tank and optionally add further auxiliaries (tank mix).

In a further embodiment, the user can mix both individual components of the composition according to the invention and partially premixed components, for example components containing compounds I and / or active compounds from groups A) to I), in the spray tank and optionally add further auxiliaries (tank mix). ,

In a further embodiment, the user can use both individual components of the composition according to the invention and partially premixed components, for example components containing compounds I and / or active compounds from groups A) to I), together (for example as tank mix) or in succession. Preference is given to compositions of a compound I (component 1) with at least one active ingredient from group A) (component 2) of strobilurins and especially selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.

Preference is also given to compositions of a compound I (component 1) having at least one active compound selected from the group B) (component 2) of the carboxamides and especially selected from bixafen, boscalid, isopyrazam, fluopyram, penflufen, penthiopyrad, sedaxanes, fenhexamide, metalaxyl , Mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamide), zoxamide, carpropamide, man- dipropamide and N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide.

Preference is also given to compositions of a compound I (component 1) having at least one active compound selected from group C) (component 2) of the azoles and especially selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole , Propiconazole, Prothioconazole, Triadimefon, Triadimenol, Tebuconazole, Tetraconazole, Triticonazole, Prochloraz, Cyazofamide, Benomyl, Carbendazim and Ethaboxam.

Also preferred are compositions of a compound I (component 1) with at least one active ingredient selected from group D) (component 2) of the nitrogen-containing heterocyclyl compounds and especially selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, fodemorph, fenpropimorph, Tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenami don, probenazole, proquinazide, acibenzolar-S-methyl, captafol, folpet, fenoxanil, quinoxyfen and 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine ,

Preference is also given to compositions of a compound I (component 1) having at least one active compound selected from the group E) (component 2) of the carambamates and especially selected from mancozeb, metiram, propineb, thiram, iprovalacarb, benthiavalicarb and propamocarb.

Also preferred are compositions of a compound I (component 1) with at least one active ingredient selected from the fungicides of group F) (component 2) and especially selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl-aluminum, H3PO3 and their salts , Chlorothalonil, dichlofluanid, thiophosphate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone, spiroxamine and N-methyl-2- {1 - [(5-methyl-3-trifluoromethyl-1H-pyrazole -1-yl) -acetyl] -piperidin-4-yl} -N - [(1R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -4-thiazolecarboxamide.

Accordingly, the present invention further relates to compositions of a compound I (component 1) with a further active ingredient (component 2), the latter being selected from the lines B-1 to B-347 in the column "component 2" of table B.

A further embodiment of the invention relates to the compositions B-1 to B-347 listed in Table B, wherein in each case one row of Table B corresponds to an agrochemical composition comprising an individualized in the present specification compounds of formula I (component 1) and the in each case indicated in the relevant line further active compound from groups A) to I) (component 2). According to one embodiment, component 1 corresponds to a compound I which is individualized in Tables 1a to 135a. The active compounds in the described compositions are each preferably present in synergistically effective amounts.

Table B: Active ingredient composition comprising an individualized compound I and a further active compound from groups A) to I)

The active ingredients mentioned above as component 2, their preparation and their action against harmful fungi are known (cf .: http://www.alanwood.net/pesticides/); they are commercially available. The compounds named after IUPAC, their preparation and their fungicidal action are also known (see Can. J. Plant Sci 48 (6), 587-94, 1968; EP-A 141 317; EP-A 152 031; A 226 917, EP-A 243 970, EP-A 256 503, EP-A 428 941, EP-A 532 022, EP-A 1 028 125, EP-A 1 035 122, EP-A 1 201 648, EP DE 1 922 244, JP 2002316902, DE 19650197, DE 10021412, DE 102005009458, US 3,296,272, US 3,325,503, WO 98/46608, WO 99/14187, WO 99/24413, WO 99/27783, WO 00/29404, WO WO 00/65913, WO 01/54501, WO 01/56358, WO 02/22583, WO 02/40431, WO 03/10149, WO 03/11853, WO 03/14103, WO 03/16286, WO WO 03/63688, WO 03/61388, WO 03/66609, WO 03/74491, WO 04/49804, WO 05/120234, WO 05/123689, WO 05/123690, WO 05/63721, WO 05/87772, WO WO 06/15866, WO 06/87325, WO 06/87343, WO 07/82098, WO 07/90624).

The preparation of the compositions for mixtures of active ingredients in a known manner in the form of compositions containing in addition to the active ingredients, a solvent or solid carrier, for. B. in the manner as indicated for compositions of the compounds I. With regard to the usual ingredients of such compositions, reference is made to the comments on the compositions containing the compounds I.

The compositions for mixtures of active substances are suitable as fungicides for controlling harmful fungi. They are characterized by excellent efficacy against a wide range of phytopathogenic fungi including soil-borne pathogens derived in particular from the classes of the Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti). Furthermore, reference is made to the comments on the effectiveness of the compounds I and the compositions containing the compounds I.

Another object of the present invention is the use of compounds I and their pharmaceutically acceptable salts for the treatment of diseases, in particular the use of the compounds I as an antimycotic. Thus, one embodiment of the invention relates to a pharmaceutical composition comprising at least one compound of the formula I and / or a pharmaceutically acceptable salt thereof. Another embodiment relates to the use of a compound I and / or a pharmaceutically active salt thereof for the manufacture of an antimycotic.

Yet another object of the present invention is the use of compounds I and their pharmaceutically acceptable salts for the treatment of tumors in mammals, such as humans. Thus, one embodiment of the invention relates to the use of a compound I and / or a pharmaceutically acceptable salt thereof for the manufacture of an agent which inhibits the growth of tumors and cancer in mammals. By "cancer" is meant in particular a malignant or malignant tumor, e.g. Breast cancer, prostate cancer, lung cancer, CNS cancer, melanocarcinoma, ovarian cancer or kidney cancer, especially in humans.

Yet another object of the present invention is the use of compounds I and their pharmaceutically acceptable salts for the treatment of viral infections, in particular viral infections, which lead to diseases in warm-blooded animals. Thus, one embodiment of the invention relates to the use of a compound I and / or a pharmaceutically active salt thereof for the manufacture of an agent for the treatment of viral infections. The viral diseases to be treated include retrovirus diseases such as: HIV and HTLV, influenza virus, rhino-virus diseases, herpes and the like.

synthesis Examples

The instructions given in the following synthesis examples were used, with a corresponding modification of the starting compounds, to obtain further compounds of the formula I or the precursors thereof, for example for the preparation of the compounds according to the invention indicated in Table E.

Example 1 1.1 Preparation of 3-acetyl-3-chlorodihydrofuran-2 (3H) -one

Sulfuryl chloride (8 mL, 100 mmol) was slowly added dropwise at room temperature to α-acetobutyrolactone (10.8 mL, 100 mmol) (note: the reaction is spontaneously exothermic, with large amounts of gaseous hydrogen chloride and sulfur dioxide being added). the released). The reaction mixture was stirred for a further 2 h at room temperature. Then the mixture was diluted with ether (200 ml), then washed with water (2 × 200 ml), saturated NaCl solution (200 ml). The organic phase was separated, dried over sodium sulfate and concentrated in vacuo to give pure chloro lactone (13 g, 80%): ¹ H NMR (300 MHz, CDCl ₃ ) δ 2.45-2.54 (m, 1H), 2.59 (s, 3H), 3.18-3.27 (m, 1H), 4.35 ^ .45 (m, 2H).

1.2 Preparation of 3,5-dichloropentan-2-one

Glacial acetic acid (6 ml) and hydrochloric acid (37%, 15 ml) were added to 3-acetyl-3-chlorodihydrofuran-2 (3H) -one (13.0 g, 80 mmol) with stirring. The reaction was heated at 100 ^° C. for 20 minutes and then refluxed at 120 ^° C. for 2 hours. Thereafter, the reaction was cooled to room temperature, diluted with water (200 ml) and extracted with ether (2 x 100 ml). The organic phase was washed with NaHCO ₃ (2x50 ml, aq. Sat.), Saturated NaCl solution (200 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by vacuum distillation to give 3,5-dichloropentan-2-one (7.3 g, 59%): ¹ H NMR (300 MHz, CDCl ₃ ) δ 2.21-2.25 (m, 1H), 2.37- 2.40 (m, 4H), 3.70-3.75 (m, 4H), 4.49-4.54 (m, 2H).

1.3 Preparation of 1- (1-chlorocyclopropyl) ethanone

Potassium fluoride (5.46 g, 94 mmol) and diethylene glycol (20 ml) were placed in a two-neck round bottom flask equipped with magnetic stirrer, pressure equalization tube and short path nozzle with vacuum connection. To this mixture, the dichloroketone (7.3 g, 47 mmol) from the previous step was added dropwise with stirring and constant Vacuum (60 torr) at 1 10 ⁰ C was added. Upon completion of the addition, the pressure was gradually reduced to 10 torr to complete the distillation of the product, resulting in a yield of 1- (1-chlorocyclopropyl) ethanone of 2.5 g, 45%: ¹ H NMR (300 MHz, CDCl 2 ₃ ) δ 1.44-1.49 (m, 2H), 1.73-1.78 (m, 2H), 4.94 (s, 2H).

1.4 General Preparation of Bromoketones

To a cooled solution (0 ⁰ C) of the corresponding ketone (35 mmol) in MeOH (100 ml) was added dropwise with stirring Br 2 (35 mmol). The reaction mixture was allowed to come to room temperature and stirred for 2 h before being poured onto ice / water (30 g) and extracted with ether (50 ml). The organic phase was separated, washed with saturated NaCl solution (2 x 50 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, eluent: hexanes: dichloromethane, 4: 1) to give the corresponding bromoketones.

1.4a 2-bromo-1- (1-methylcyclohexyl) ethanone yellow oil (6.6 g, 43%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 4.18 (s, 2H), 1.97-1.94 (m, 2H),

1.65-1.35 (m, 8H), 1.17 (s, 3H).

1.4b 2-bromo-1 - (1-chlorocyclopropyl) ethanone yellow oil (2.8 g, 69%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 4.49 (s, 2H), 1.75 (m, 2H), 1.46 (m, 2H).

2-bromo-1- (1-methylcyclopropyl) ethanone was commercially obtained and used further.

1.5 General preparation of 1- [1- (substituted) cycloalkyl] -2- (1H-1, 2,4-triazol-1-yl) ethanones

A solution of the corresponding bromoketone in acetone (30 mmol) was added dropwise with stirring to a mixture of 1, 2,4-triazole (48 mmol) and potassium carbonate (39 mmol) in acetone (50 ml). After stirring at room temperature for 18 hours, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was taken up in ethyl acetate (50 ml) and washed with saturated NaCl solution (2 × 50 ml). The organic phase was dried over sodium sulfate and concentrated in vacuo to give the substituted triazolyl derivatives.

1.5a 1 - (1-Methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) ethanone colorless oil (6.2 g, quantitative yield); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.15 (s, 1H), 7.96 (s, 1H), 5.15 (s, 2H), 2.05-1.94 (m, 2H), 1.65-1.35 (m, 8H ), 1.24 (s, 3H).

1.5b 1 - (1-chlorocyclopropyl) -2- (1 H-1, 2,4-triazol-1-yl) ethanone orange solid (2.1 g, 80%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.12 (s, 1H), 7.98

(s, 1H), 5.61 (s, 2H), 1.79 (m, 2H), 1.52 (m, 2H).

1.5c 1 - (1-methylcyclopropyl) -2- (1H-1, 2,4-triazol-1-yl) ethanone orange oil (3.5 g, 75%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.16 (s, 1 H), 7.96 (s,

1 H), 5.17 (s, 2H), 3.48 (s, 3H), 1.40 (m, 2H), 0.91 (m, 2H).

1.6 Preparation of (E / Z) -3- (2,4-dichlorophenyl) -2-methyl-propenal Propionaldehyde (17.5 mL, 239 mmol) was added dropwise at room temperature to a stirred solution of 2,4-dichlorobenzaldehyde (40.00 g, 228 mmol) and NaOH (0.91 g, 22 mmol) in MeOH (400 mL). After stirring for 1 h, the pH of the mixture was adjusted to pH 6 with acetic acid (1.4 ml) and stirred for a further 16 h. The mixture was diluted with EtOAc (100 mL) and washed with saturated NaCl solution (2x50 mL). The organic phase was separated, dried with sodium sulfate and concentrated to give (E / Z) -3- (2,4-dichlorophenyl) -2-methyl-propenal as a gray-white solid. Yield: 42.1 g (86%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 9.66 (s, 1H), 7.51 (s, 1H), 7.50 (s, 1H), 7.39 (s, 1H), 7.28-7.27 (m, 1 H), 1.96 (d, J = 1.5 Hz, 3H).

1.7 Preparation of 3- (2,4-dichlorophenyl) -2-methyl-propanol

A solution of (E / Z) -3- (2,4-dichlorophenyl) -2-methyl-propenal (3.0 g, 14 mmol) in THF (20 ml) at 0 ⁰ C to a stirred suspension of LiAlH ₄ (850 mg, 22 mmol) in THF (60 ml). The reaction mixture became at this temperature stirred for 30 min and then for 3 h at room temperature before adding water (0.85 ml) and ice-cold HCl (2M aq., 50 ml). The mixture was extracted with MTBE (2x50 ml), the combined organic extracts were separated, anhydrous sodium sulfate and concentrated in vacuo to give 3- (2,4-dichlorophenyl) -2-methyl-propanol as a colorless oil. Yield: 2.7 g (88%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 7.36 (s, 1H), 7.16-7.12 (m, 2H), 3.53-3.51 (m, 2H), 2.91-2.84 (m, 1H), 2.53-2.46 (m, 1H), 2.04-1.91 (m, 1H), 0.93 (d, J = 6.6Hz, 3H).

1.8 Preparation of 3- (2,4-dichlorophenyl) -2-methyl-bromopropane A mixture of 3- (2,4-dichlorophenyl) -2-methyl-propanol (13.6 g, 62 mmol) and HBr (48%). aq., 120 ml) was refluxed for 16 h, then cooled to room temperature and extracted with CH 2 Cl 2 (2x50 ml). The combined organic extracts were separated, dried with anhydrous sodium sulfate and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, eluent: hexane) to give 3- (2,4-dichlorophenyl) -2-methyl-bromopropane as a light yellow oil. Yield: 15.5 g (87%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 7.37 (s, 1 H,), 7.19- 7.18 (m, 2H), 3.36 (ABqd, J = 4.5, 15 Hz, 2H), 2.75 (ABqd, J = 7.2 , 21 Hz, 2H), 2.25- 2.12 (m, 1H), 1.04 (d, J = 6.6 Hz, 3H).

1.9 General procedure for the preparation of 4- (2,4-dichlorophenyl) -3-methyl-1 - (1H-

1, 2,4-triazol-1-yl) butyl (substituted) ketones

A mixture of 3- (2,4-dichlorophenyl) -2-methyl-bromopropane (2.5 g, 8.86 mmol), Cs 2 CO ₃ (3.9 g, 12 mmol), and the corresponding triazolyl ketone (8.05 mmol) in DMF (30 ml) was stirred at 70 ⁰ C for 16 h. The mixture was cooled to room temperature, treated with NH ₄ Cl (aq sat, 50 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were washed with saturated NaCl solution (2x30 ml), separated, dried with anhydrous sodium sulfate, and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, eluent: hexane: EtOAc, 7: 3) to give the corresponding ketones.

1.9a 5- (2,4-dichlorophenyl) -4-methyl-1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) -pentan-1-one yellow oil, Yield: 1.2 g (37%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.27 (s, 0.5H), 8.06 (s, 0.5H), 7.92 (s, 0.5H), 7.87 (s, 0.5H), 7.35-7.34 (m, 1 H), 7.19-7.1 1 (m, 1H), 7.08-6.95 (m, 1H,), 5.49-5.35 (m, 1H,), 2.95-2.82 (m, 0.5H), 2.73-2.39 ( m, 1.5H), 2.15-1.71 (m, 2H), 1.70-1.50 (m, 1H), 1.41-1.37 (m, 3H), 1.01-0.97 (m, 2H), 0.95-0.89 (m, 3H ), 0.88-0.87 (m, 2H).

1.9b 5- (2,4-dichlorophenyl) -4-methyl-1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) -pentan-1-one yellow oil, Yield: 1.7 g (39%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.20-8.07 (m, 1 H),

7.98-7.83 (m, 1H), 7.41-7.33 (m, 1H), 7.21-7.12 (m, 1H), 7.08-6.95 (m, 1H), 5.89-5.61 (m, 1H), 3.61-3.43 (m, 1H), 2.94-2.83 (m, 1H), 2.55-2.21 (m, 2H), 1.90-1.70 (m, 5H), 1.60-1.25 (m, 6H), 1.20-1.09 (m, 3H), 1.06-0.95 (m, 3H). 1.9c 1 - (1-Chlorocyclopropyl) -5- (2,4-dichlorophenyl) -4-methyl-2- (1H-1,2,4-triazol-1-yl) -pentan-1-one yellow oil, Yield: 1.1 g (18%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.28 (s, 0.5H), 8.07 (s, 0.5H), 7.98 (s, 0.5H), 7.92 (s, 0.5H), 7.40-7.31 (m, 1 H), 7.15-6.95 (m, 2H), 6.18-6.05 (m, 1H), 2.72-2.52 (m, 1H), 2.50-2.30 (m, 1H), 2.22-1.90 (m, 2H) , 1.90-1.62 (m, 2H), 1.50-1.38 (m, 2H), 1.12-1.01 (m, 1H), 0.92-0.75 (m, 3H).

1.10 General procedure for the preparation of 1- (substituted) -5- (2,4-dichlorophenyl) -4-methyl-2- (1H-1, 2,4-triazol-1-yl) pentane-1-oils a stirred and cooled (0 ⁰ C) solution of the corresponding ketone (3.3 mmol) in EtOH (10 ml) was added sodium borohydride (136 mg, 3.6 mmol). The mixture was then stirred for 2 h at room temperature, treated with NH ₄ Cl (aq sat., 20 mL) and extracted with EtOAc (2x20 mL). The combined organic extracts were separated, dried with anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, eluent: hexanes: EtOAc, 3: 2) to give the title compounds.

1.10a 1- (1-Methylcyclopropyl) -5- (2,4-dichlorophenyl) -4-methyl-2- (1H-1, 2,4-triazole)

1-yl) pentan-1-ol colorless resin, yield: 0.49 g (41%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.03 (s, 0.5H), 8.01 (s, 0.5H), 7.95 (s, 0.5H), 7.90 (s, 0.5H), 7.35-7.34 (m, 1 H), 7.17-7.10 (m, 1H), 7.05-6.95 (m, 1H), 4.55-4.35 (m, 1H,), 3.25-3.22 (m, 1H), 2.92-2.88 (m, 0.5H), 2.60-2.40 (m, 1.5H), 2.25-2.24 (m, 1H), 2.21-1.85 (m, 2H), 1.40-1.21 (m, 1H), 1.07-1.02 (m, 3H ), 0.93-0.91 (m, 1.7H), 0.77-0.74 (m, 1.3H), 0.37-0.35 (m, 1H), 0.22-0.21 (m, 1H), 0.00-0.02 (m, 2H) ; APCI, m / z 368 [M + H] ⁺ .

1.10b 1- (1-methylcyclohexyl) -5- (2,4-dichlorophenyl) -4-methyl-2- (1H-1,2,4-triazol-1-yl) pentan-1-ol colorless resin, Yield: 1.1 g (63%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.07-8.06 (m, 1H), 7.93-7.89 (m, 1H), 7.45-7.37 (m, 1H), 7.17-7.06 (m, 1H) , 6.96-6.94 (m, 1H), 4.67-4.53 (m, 1H), 3.41-3.36 (m, 2H), 2.84-2.77 (m, 0.5H), 2.67-2.60 (m, 0.5H), 2.50-2.47 (m, 1H), 2.35-2.28 (m, 0.5H), 2.13-2.04 (m, 0.5H), 1.95-1.93 (m, 0.4H), 1.69-1.66 (m, 0.1H), 1.61-1.13 (m, 10.5H), 1.00-0.93 (m, 1H), 0.94-0.79 (m, 3H), 0.43-0.39 (m, 3H); APCI, m / z 410 [M + H] ⁺ 1.10c 1- (1-Chlorocyclopropyl) -5- (2,4-dichlorophenyl) -4-methyl-2- (1H-1, 2,4-triazole) 1-yl) pentan-1-ol colorless resin, yield: 0.37 g (34%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.16 (s, 0.5H), 8.12 (s, 0.5H), 7.98 (s, 0.5H), 7.93 (s, 0.5H), 7.35-7.30 (m, 1 H), 7.18-6.96 (m, 2H), 4.85-4.52 (m, 1H,), 3.42-3.32 (m, 1H), 3.12-2.38 (m, 3H), 2.28-1.92 (m, 2H) , 1.65-1.31 (m, 1H), 1.07-0.64 (m, 6H), 0.35-0.21 (m, 1H); ESI, m / z 388 [M + H] ⁺ .

Example 2

2.1 General preparation of 1- (4-bromobutoxy) - (substituted) benzenes A mixture of the appropriate substituted phenol (44 mmol) and potassium carbonate (66 mmol) in DMF (50 ml) was stirred for 1 h at room temperature. Then 1, 4-dibromobutane (89 mmol) was added dropwise to the mixture, followed by the addition of Kl (cat.). After stirring at room temperature for 18 hours, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was taken up with EtOAc (50 ml), washed with saturated NaCl solution (3x50 ml), dried over sodium sulfate and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, eluent: hexane) to obtain the corresponding substituted bromobutoxybenzene.

2.1a 1- (4-bromobutoxy) -2-fluorobenzene white solid (4.1 g, 38%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 7.07-6.95 (m, 4H), 4.07 (t,

J = 5.8 Hz, 2H), 3.50 (t, 2H), 2.09-2.00 (m, 4H)

2.1b 1- (4-bromobutoxy) -2,4-difluorobenzene colorless oil (3.5 g, 35%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 6.89-6.74 (m, 3H), 4.05-4.01 (m, 2H), 3.51-3.47 (m, 2H), 2.11-1.92 (m, 4H). 2.1 C 1- (4-bromobutoxy) -2,3-difluorobenzene colorless oil (5.3 g, 53%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 6.89-6.74 (m, 3H), 4.05-4.01 (m, 2H), 3.51-3.47 (m, 2H), 2.11-1.92 (m, 4H). 2.1d 1- (4-bromobutoxy) -3-chlorobenzene colorless oil (3.8 g, 37%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 6.91-6.93 (m, 1H), 6.93-6.75 (m, 3H), 3.98 (t, J = 6.2 Hz, 2H), 3.48 (t, J = 5.5 Hz , 2H), 2.08-1.91 (m, 4H).

2.2 General preparation of 6 - [(substituted) phenoxy] -1- [1- (substituted) cycloalkyl)] - 2- (1H-1, 2,4-triazol-1-yl) hexan-1-one

To a mixture of the appropriate 1- [1- (substituted) cycloalkyl] -2- (1H-1, 2,4-triazol-1-yl) ethanone (4 mmol) in CH ₃ CN (15 ml) was added potassium hydroxide ( 9 mmol), the corresponding substituted bromobutoxybenzene (3 mmol), and PEG-400 (cat.) Were added. The mixture was heated at 60 ^° C. with stirring for 6 h. The mixture was then cooled down, diluted the reaction mixture with ethyl acetate and washed with saturated NaCl solution (2 ^χ 50ml). The organic phase was separated, dried over sodium sulfate and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, eluent: 9: 1 to 1: 1 hexane: EtOAc) to give the corresponding substituted hexanone.

2.2a 6- (2-fluorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) hexan-1-one yellow oil (138 mg, 8%) ; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.31 (s, 1H), 7.88 (s, 1H), 7.07-6.95 (m, 4H), 5.59-5.54 (m, 1H), 3.99-3.95 ( m, 2H), 2.09-1.77 (m, 5H), 1.65-1.35 (m, 11H), 1.17 (s, 3H).

2.2b 6- (2,4-Difluorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) -hexan-1-one yellow oil (158 mg, 9%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.31 (s, 1H), 7.88 (s, 1H), 6.87-6.83 (m, 3H), 5.59-5.49 (m, 1H), 3.93 (t, J = 7.0 Hz, 2H), 2.17-1.14 (m, 19H). 2.2c 6- (2,3-Difluorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) -hexan-1-one yellow oil (230 mg, 13 %); ¹ H NMR (300 MHz, CDCI ₃₎ δ ^1H NMR (300 MHz, CDCI ₃₎ δ 8.31 (s, 1 H), 7.88 (s, 1 H), 6.99-6.59 (m, 3H), 5:56 to 5:49 (m, 1H), 3.93 (t, J = 7.0Hz, 2H), 2.17-1.14 (m, 19H). 2.2d 6- (3-chlorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) hexane

1-on yellow oil (440 mg, 30%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.31 (s, 1H), 7.98 (s, 1H), 7.19 (t, J = 8.4 Hz, 2H), 6.92-6.62 (m, 3H), 5.59- 5.54 (m, 1H), 3.90-3.86 (m, 2H), 2.09-1.77 (m, 5H), 1.65-1.35 (m, 11H), 1.17 (s, 3H). 2.2e 1 - (1-Chlorocyclopropyl) -6- (3-fluorophenoxy) -2- (1H-1, 2,4-triazol-1-yl) hexan-1-one colorless oil (350 mg, 40%) ; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.30 (s, 1H), 7.95 (s, 1H), 6.06-7.00 (m, 2H), 6.93-6.87 (m, 2H), 6.04-5.95 (m , 1H), 4.06-3.96 (m, 2H), 2.49-2.30 (m, 1H), 2.10-1.35 (m, 9H). 2.2f 1 - (1-Chlorocyclopropyl) -6- (2-3-difluorophenoxy) -2- (1H-1,2,4-triazol-1-yl) -hexan-1-one yellow oil (220 mg, 31% ); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.30 (s, 1H), 7.95 (s, 1H), 7.01-6.90 (m, 1H), 6.83-6.60 (m, 2H), 6.04-5.95 ( m, 1H), 4.06-3.96 (m, 2H), 2.49-2.30 (m, 1H), 2.10-1.35 (m, 9H). 2.2 g of 1- (1-chlorocyclopropyl) -6- (3-chlorophenoxy) -2- (1H-1,2,4-triazol-1-yl) hexan-1-one yellow oil (153 mg, 20%). ; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.28 (s, 1H), 7.95 (s, 1H), 7.15 (t, J = 8.2 Hz, 1H), 6.93-6.60 (m, 3H), 6.01 -5.99 (m, 1H), 3.90-3.86 (m, 2H), 2.49-2.30 (m, 1H), 2.10-1.35 (m, 9H). 2.2h 6- (2,4-Difluorophenoxy) -1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) hexan-1-one colorless oil (200 mg, 25 %); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.30 (s, 1 H), 7.90 (s, 1 H),

7.12-6.84 (m, 4H), 5.38-5.26 (m, 1H), 3.97-3.93 (m, 2H), 2.27-2.12 (m, 1H), 1.89-1.38

(m, 10H), 0.94-0.87 (m, 2H).

2.2i 6- (2,4-Difluorophenoxy) -1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) hexan-1-one colorless oil (320mg, 25 %); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.30 (s, 1 H), 7.90 (s, 1 H),

6.87-6.84 (m, 3H), 5.38-5.26 (m, 1H), 3.97-3.93 (m, 2H), 2.27-2.12 (m, 1H), 1.89-1.38

(m, 10H), 0.94-0.87 (m, 2H).

2.2j 6- (2,3-Difluorophenoxy) -1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) -hexan-1-one colorless oil (370 mg, 18 %); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.30 (s, 1H), 7.90 (s, 1H), 6.97-6.94 (m, 1H), 6.74-6.68 (m, 2H), 5.33-5.28 ( m, 1H), 3.97-3.93 (m, 2H), 2.27-2.12 (m, 1H), 1.89-1.38 (m, 10H), 0.94-0.87 (m, 2H). 2.2k 6- (3-chlorophenoxy) -1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) hexane

1-on pale yellow oil (750 mg, 52%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.29 (s, 1H), 7.90 (s, 1H), 7.16 (t, J = 8.2 Hz, 1H), 6.90 (m, 1H), 6.85 ( s, 1H), 6.72 (m, 1H), 5.29 (m, 1H), 3.90 (m, 2H), 1.75-2.17 (m, 4H), 1.42-1.47 (m, 7H), 0.88 (m , 2H).

2.3 General Preparation of 6 - [(substituted) phenoxy] -1- [1

(substituted) cycloalkyl] -2- (1H-1,2,4-triazol-1-yl) hexan-1-ols (tetra-n-butylammonium borohydride / titanium tetrachloride reduction (RS / SR diastereomers)

A solution of the corresponding substituted hexanone (0.4 mmol) in anhydrous CH2Cl2 (10ml) was cooled with stirring to -78 ⁰ C, followed by dropwise addition of TiCl (0.7 mmol). The reaction mixture was stirred for 0.5 h. Thereafter, tetra-n-butylammonium borohydride was added and stirring was continued for 3 hours. The mixture was added with NH ₄ Cl (aq sat, 10 ml) and extracted with CH 2 Cl 2 (25 ml). The organic phase was separated, washed with saturated NaCl solution (2 × 20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, eluent: 10: 1 to 2: 1 hexane: EtOAc) to give the corresponding target compound.

2.3a 6- (2-fluorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) hexan-1-ol White solid (130 mg, 24%) , mp 70-72 ⁰ C; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.10 (s, 1H,), 7.95 (s, 1H), 7.05-7.02 (m, 2H), 6.89-6.87 (m, 2H), 4.48-4.44 ( m, 1H), 3.99-3.93 (m, 2H), 3.60-3.58 (m, 1H), 2.92-2.91 (m, 1H), 2.25-0.99 (m, 19H); MS (ESI) m / z 376 [M + H] ⁺ . 2.3b 6- (2,4-Difluorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) hexan-1-ol colorless oil (80 mg, 51 %); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.31 (s, 1H), 7.88 (s, 1H), 6.87-6.83 (m, 3H), 4.49-4.39 (m, 1H), 3.92-3.89 ( m, 2H), 3.60-3.58 (m, 1H), 2.94 (br s, 1H), 2.24-0.99 (m, 15H), 0.45-0.0 (m, 4H); MS (ESI) m / z 394 [M + H] ⁺ . 2.3c 6- (2,3-Difluorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) -hexan-1-ol White solid (130mg, 57 %), mp 93-95 ⁰ C; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.1 1 (s, 1H,), 7.94 (s, 1H), 6.92-6.95 (m, 1H), 6.76-6.60 (m, 2H), 4.48- 4.44 (m, 1H), 3.98-3.91 (m, 2H), 3.60-3.58 (m, 1H), 3.10-3.09 (m, 1H), 2.34-0.99 (m, 19H); MS (ESI) m / z 394 [M + H] ⁺ .

2.3d 6- (3-chlorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) hexane

1-ol a yellow solid (213 mg, 39%), mp 97-99 ⁰ C; ¹ H NMR (300 MHz, CDCI ₃₎ δ 8.10 (s, 1 H), 7.95 (s, 1 H), 7:19 to 7:13 (m, 1 H), 6.92-6.82 (m, 2H), 6.74-6.70 (m, 1H), 4.49-4.42 (m, 1H), 3.90-3.82 (m, 2H), 3.60-3.58 (m, 1H), 2.97 (br s, 1H), 2.34-0.99 (m , 19H); MS (ESI) m / z 392 [M + H] ⁺ 2.3e 1 - (1-Chlorocyclopropyl) -6- (2-fluorophenoxy) -2- (1 H-1, 2,4-triazol-1-yl) hexan-1-ol White solid (74 mg, 23%) , mp 1 16-120 ⁰ C; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.21 (s, 1H,), 7.98 (s, 1H), 6.06-7.00 (m, 2H), 6.93-6.87 (m, 2H), 4.61-4.49 ( m, 1H), 4.00-3.94 (m, 2H), 3.47-3.42 (m, 1H), 2.66 (d, J = 5.8Hz, 1H), 2.39-2.09 (m, 2H), 1.91-1.70 (m, 2H), 1.40-0.66 (m, 5H), 0.45-0.38 (m, 1H); MS (ESI) m / z 354 [M + H] ⁺ 2.3f 1 - (1-chlorocyclopropyl) -6- (2,3-difluorophenoxy) -2- (1H-1, 2,4-triazole-1 - yl) hexan-1-ol white solid (70 mg, 30%), mp 134-136 ⁰ C; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.21 (s, 1H,), 7.98 (s, 1H), 6.92-6.95 (m, 1H), 6.76-6.66 (m, 2H), 4.61-4.49 (m, 1H), 3.99-3.94 (m, 2H), 3.47-3.42 (m, 1H), 2.54 (d, J = 6.0Hz, 1H), 2.43-2.09 (m, 2H), 1.91- 1.70 (m, 2H), 1.45-0.59 (m, 5H), 0.45-0.38 (m, 1H); MS (ESI) m / z 372 [M + H] ⁺ 2.3g 1 - (1-chlorocyclopropyl) -6- (3-chlorophenoxy) -2- (1H-1, 2,4-triazol-1-yl) hexan-1 - ol a white solid (71 mg, 45%), mp 145-148 ⁰ C; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.21 (s, 1H), 7.95 (s, 1H), 7.15 (t, J = 8.2 Hz, 1H), 6.92-6.97 (m, 1H), 6.83 (br s, 1H), 6.75-6.70 (m, 1H), 4.58-4.51 (m, 1H), 3.93-3.81 (m, 2H), 3.49-3.40 (m, 1H), 2.47 ( d, J = 6.2 Hz, 1H), 2.31-2.19 (m, 1H), 1.91-1.70 (m, 1H), 1.45-0.59 (m, 7H), 0.45-0.38 (m, 1H); MS (ESI) m / z 370 [M + H] ⁺ 2.3h 6- (2-fluorophenoxy) -1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) hexane-

1-ol White solid (85 mg, 42%), mp: 85-90 ⁰ C; ¹ H NMR (300 MHz, CDCI ₃₎ δ 8.10 (s, 1 H), 7.95 (s, 1 H), 7.04-6.79 (m, 4H), 4:44 ^ .30 (m, 1 H), 4.05-3.93 (m, 2H), 3.31-3.27 (m, 1H), 2.23-1.71 (m, 4H), 1.42-1.06 (m, 6H), 0.39-0.0 (m, 4H); MS (ESI) m / z 334 [M + H] ⁺

2,3i 6- (2,4-Difluorophenoxy) -1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) hexan-1-ol White solid (125mg, 40 %), mp 85-90 ⁰ C; ¹ H NMR (300 MHz, CDCI ₃₎ δ 8.10 (s, 1 H), 7.95 (s, 1 H), 6.87-6.75 (m, 3H), 4:44 ^ .30 (m, 1 H), 3:31 to 3:27 (m, 1H), 2.23-1.71 (m, 6H), 1.42-1.06 (m, 6H), 0.45-0.0 (m, 4H); MS (ESI) m / z 352 [M + H] ⁺ .

2.3j 6- (2,3-Difluorophenoxy) -1- (1-methylcyclopropyl) -2- (1H-1,2,4-triazoM-yl) hexan-1-ol Gray-white solid (62mg, 17 %), mp 1 10-1 15 ⁰ C; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.15 (s, 1H,), 7.94 (s, 1H), 6.92-6.95 (m, 1H), 6.76-6.66 (m, 2H), 4.44 ^. 30 (m, 1H), 3.31-3.27 (m, 1H), 2.23-1.71 (m, 6H), 1.42-1.06 (m, 6H), 0.45-0.0 (m, 4H); MS (ESI) m / z 352 [M + H] ⁺ 2.3k 6- (3-chlorophenoxy) -1 - (1-methylcyclopropyl) -2- (1H-1,2,4-triazol-1-yl) hexane-

1-ol white solid (250 mg, 33%), mp 108-1 10 ⁰ C; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.09 (s, 1H), 7.96 (s, 1H), 7.13-7.19 (t, J = 8.5 Hz, 1H), 6.91-6.92 (m, 1H ), 6.83-6.89 (m, 1H), 6.70-6.74 (m, 1H), 4.36 (m, 1H), 3.84-3.90 (m, 2H), 3.27-3.30 (d, 1H), 2.10 -2.30 (m, 3H), 1.70-1.85 (m, 3H), 1.25-1.28 (m, 4H), 1.06 (s, 1H), 0.88 (m, 1H), 0.21-0.38 (m, 2H) , MS (APCI) m / z 350 [M + H] ⁺ . 1.14 General Preparation of 6 - [(substituted) phenoxy] -1- [1-

(substituted) cycloalkyl] -2- (1H-1, 2,4-triazol-1-yl) hexane-1-oils (sodium borohydride reduction (RR / SS diastereomers) A solution of the corresponding substituted hexanone (0.3 mmol) in MeOH (4 ml) was cooled to 0 ⁰ C. sodium borohydride was added portionwise (2x0,35 mmol). After complete addition the reaction was warmed to room temperature and stirred for 2 h. then the reaction mixture (with NH ₄ CI aq sat, 10 ml) The mixture was extracted with EtOAc (25 ml), the organic phase was separated, washed with saturated NaCl solution (2 × 20 ml), dried over sodium sulfate and concentrated in vacuo to give the crude product purified by column chromatography (silica gel, eluent: 10: 1 to 2: 1 hexane / EtOAc) to give the corresponding target compound.

1.14a 6- (2-Fluorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) hexan-1-ol colorless oil (120 mg, 87%) ; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.15 (s, 1H), 7.94 (s, 1H), 7.07-6.95 (m, 4H), 4.61-4.50 (m, 1H), 3.99-3.95 ( m, 2H), 3.59-3.46 (m, 2H), 2.34-2.19 (m, 1H), 1.95-0.95 (m, 15H), 0.47 (s, 3H); MS (ESI) m / z 376 [M + H] ⁺ .

1.14b 6- (3-Chlorophenoxy) -1- (1-methylcyclohexyl) -2- (1H-1,2,4-triazol-1-yl) hexane

1-ol colorless oil (250 mg, 57%); ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.13 (s, 1H,), 7.95 (s, 1H), 7.19-7.13 (m, 1H), 6.92-6.62 (m, 3H), 4.56 ^. 42 (m, 1H), 3.90-3.82 (m, 2H), 3.56-3.48 (m, 2H), 2.34-0.99 (m, 16H), 0.45 (s, 3H); MS (ESI) m / z 392 [M + H] +.

Biological experiments

microtest

The active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO.

Example M1 Activity against the causative agent of the gray mold Botrytis cinerea im

Microtiter test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. Subsequently, a malt-based aqueous spore suspension of Botrytis cinerea was added. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation. The measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs. The active compounds I.A1a, I.A2, I .A4, I.A10, I.A1b and I.A6b led at 31 ppm active ingredient concentration to a maximum growth of 7%. Example M2 Activity against the causative agent of the Septoria leaf drought Septoria tritici in a microtiter test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. This was followed by the addition of an aqueous spore suspension based on malt of Septoria tritici .. The plates were placed in a water vapor-saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation. The measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs. The active compounds I.A1a, I.A2, 1.A3, 1.A4, 1.A5, 1.A10, 1.A1b, I.A6b, I.A13 and I.A14 led to a concentration of 31 ppm of active compound Growth of at most 13%.

Table E:

CD CD

OO

O

O CO

S

O oil

O

O

[ ^* ] Melting point ⁰ C

O OO

Claims

claims

1. Compounds of the formula I

wherein the variables have the following meanings:

X is CH or N;

YO or a single bond to R ¹ ;

Z is a saturated or partially unsaturated hydrocarbon chain of three to eight carbon atoms which, when partially unsaturated, contains one to three double bonds or one or two triple bonds, where Z may contain one, two, three, four or five substituents R ^z , where R ^{z is} means:

R ^{Z is} halogen, cyano, nitro, cyanato (OCN), C ₈ alkyl, Ci-C ₈ -HaIo- genalkyl, C ₂ -C ₈ -alkenyl -alkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -Al kinyl, C ₃ -C ₈ - haloalkynyl, _{Ci-C8-alkoxy, Ci-C8-haloalkoxy,} Ci-C ₈ alkylcarbonyl oxy, Ci-Cs-alkylsulfonyloxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ haloalkenyloxy,

C ₂ -C ₈ alkynyloxy, _C3-C8 haloalkynyloxy, _C3-C8 cycloalkyl, Cs-C ₈ -HaIo- gencycloalkyl, _C3-C8 cycloalkenyl, _C3-C8 halocycloalkenyl, C 3 C ₈ - Cycloalkoxy, Cs-Cβ-cycloalkenyloxy, C ₁ -C 6 -alkylene, oxy-C ₂ -C 4 -alkylene, oxy-C ₁ -C 3 -alkyleneoxy, phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the abovementioned groups the heteroa - ryl is an aromatic five-, six- or seven-membered heterocycle and the heterocyclyl is a saturated or partially unsaturated five-, six- or seven-membered heterocycle, each containing one, two, three or four heteroatoms from the group O, N and S, or NA ³ A ⁴ , wherein two R ^z radicals attached to the same carbon atom together with the carbon atom to which they are attached may also form a C 3 -C 6 cycloalkyl ring; wherein A ³ , A ⁴ are defined as below;

R ^{1 is} C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 3 -C 10 -cycloalkenyl, C 3 -C 10 -halocycloalkenyl, where the abovementioned carbocycles are unsubstituted or independently represent one, two, three, four or five substituents selected from halogen, hydroxy, Ci-C ₈ alkyl, Ci-C ₈ haloalkyl, C ₂ -C ₈ - alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, and C3-C contain ₈ haloalkynyl, or 6 - to 10-membered aryl, wherein the aryl contains one, two, three, four or five independently selected substituents L, wherein L means:

L is halogen, cyano, nitro, hydroxy, cyanato (OCN), C -C ₈ -alkyl, Cs-haloalkyl, C ₂ -C ₈ -alkenyl -alkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -Al kinyl, Cs-Cs haloalkynyl, C4-Cio-alkadienyl, C4-Cio-Halogenalkadienyl, _{Ci-C8-alkoxy,} d-Cs-haloalkoxy, d-Cs-alkylcarbonyloxy, Ci-Cs-alkylsulfonyloxy, C ₂ -

Cs-alkenyloxy, C ₂ -C ₈ haloalkenyloxy, C ₂ -C ₈ alkynyloxy, Cs-C ₈ - haloalkynyloxy, C3-Cs-cycloalkyl, _{C3-C8-halocycloalkyl,} C3-C ₈ - cycloalkenyl, C3-C ₈ halocycloalkenyl, C 3 -C ₈ cycloalkoxy, Cs-Cβ-cyclo- alkenyloxy, hydroxyimino-Ci-C ₈ alkyl, Ci-Cβ alkylene, oxy-C ₂ -C 4 -alkylene, oxy-Ci-C3-alkyleneoxy , C ₈ -Alkoximino-C ₈ alkyl, C ₂ -C ₈ -Alkenyloximino- d-Cβ-alkyl, C ₂ -C ₈ -Alkinyloximino-Ci-C ₈ alkyl, S (= O) _n A ¹ , C (OO) A ² , C (SS) A ² , NA ³ A ⁴ , phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the abovementioned groups the heteroaryl is an aromatic five-, is a six- or seven-membered heterocycle and the heterocyclyl is a saturated or partially unsaturated five-, six- or seven-membered heterocycle, each containing one, two, three or four heteroatoms from the group O, N and S, wherein two substituents L, the the same carbon atom are attached together with the carbon atom they are attached, can also form a Cs-Cβ-cycloalkyl ring; where n, A ¹ , A ² , A ³ , A ⁴ mean:

n is 0, 1 or 2;

A ¹ is hydrogen, hydroxy, Ci-C ₈ -alkyl, C ₈ haloalkyl, amino, Ci-C ₈ - alkylamino, di-Ci-C ₈ alkylamino, phenyl, phenylamino or phenyl

_{Ci-C8-alkylamino;}

A ^{2 is} one of the groups mentioned at A ¹ or C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -

Haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl, Ci-C8-alkoxy,} Ci-C ₈ haloalkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ haloalkenyloxy,

C ₂ -C ₈ alkynyloxy, _C3-C8 haloalkynyloxy, _C3-C8 cycloalkyl, Cs-C ₈ - halocycloalkyl, _C3-C8 cycloalkoxy or _C3-C8-halo cycloalkoxy;

A ^3, A ⁴ are independently hydrogen, Ci-C ₈ alkyl, Ci-C ₈ -HaIo- genalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl , Cs-Cs haloalkynyl, C3-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C ₈ - Cycloalkenyl or C ₃ -C ₈ -halocycloalkenyl, phenyl or 5- or ₆ -membered heteroaryl having one, two, three or four heteroatoms from the group O, N and S in the heterocycle;

the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L may themselves carry one, two, three or four identical or different groups R ^L :

R ^{L is} halogen, hydroxy, cyano, nitro, Ci-C ₈ alkyl, Ci-Cs-haloalkyl, d-Cs-alkoxy, d-Cs-haloalkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ -Halogencyclo alkyl, C ₃ -C ₈ -cycloalkenyl, C ₃ -C ₈ -cycloalkoxy, C ₃ -C ₈ -halocycloalkoxy, C ₁ -C ₆ -alkylene, oxy-C ₂ -C ₄ -alkylene, oxy-C ₁ -C ₃ - alkyleneoxy, C ₈ - alkylcarbonyl, Ci-Cs-alkylcarbonyloxy, _{Ci-C8-alkoxycarbonyl,} amino, d- Cβ-alkylamino, di-Ci-C ₈ alkylamino;

R ² is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C ₂ -Cio-alkenyl, C ₂ -C ₀ - haloalkenyl, C ₂ -C ₀ alkynyl, C3-Cio-haloalkynyl, d-do-alkadienyl , C4-Ci _θ -Halogenalkadienyl, C3-Ci _θ cycloalkyl, C3-Ci _θ halocycloalkyl, C ₃ - do-cycloalkenyl, C3-Cio-halocycloalkenyl;

R ³ is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C ₂ -C ₀ alkenyl, C ₂ -C ₀ - haloalkenyl, C ₂ -C ₀ alkynyl, C3-Cio-haloalkynyl, C4-CIO alkadienyl, C4-Ci _θ -Halogenalkadienyl, C3-Ci _θ cycloalkyl, C3-Ci _θ halocycloalkyl, C ₃ - Cio-cycloalkenyl, C3-Cio-halocycloalkenyl, carboxyl, formyl, Si (A ⁵ A ⁶ A ^7), C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR ^π ,

C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) N NA ³ A ⁴ , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C (O) NA ³ A ⁴ , C (S) NA ³ A ⁴ or S (= O) n A ¹ ; in which

R ^π Ci-Cs-alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ -alkyl kinyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ - cycloalkenyl or phenyl;

R is ^A -Cs alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkenyl or phenyl;

A ⁵ , A ⁶ , A ⁷ independently of one another are C ₁ -C 10 -alkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₈ -alkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkenyl or phenyl ;

wherein R ^π , R ^A , A ⁵ , A ⁶ and A ⁷ , unless otherwise indicated, are independently unsubstituted or substituted with one, two, three, four or five L as defined above; R ^{4 is} hydrogen, C ₁ -C 10 -alkyl, C ₁ -C 10 -haloalkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -haloalkenyl, C ₂ -C 10 -alkynyl, C ₃ -C 10 -haloalkynyl, C ₄ -C 10 -alkadienyl, C ₄ -C 10 -alkyl -Haloalkadienyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 3 -C 10 -cycloalkenyl, C 3 -C 10 -halocycloalkenyl;

R ² , R ³ , R ⁴ are, unless otherwise indicated, independently unsubstituted or substituted with one, two, three, four or five L as defined above;

R ^{5 is} hydrogen, halogen or Ci-Cio-alkyl; wherein the alkyl group in R ^{5 is} unsubstituted or substituted by one, two, three, four or five independently selected L as defined above;

R ⁶ and R ⁷ together form a three to ten membered saturated or partially unsaturated cycle which is a carbocycle or, besides carbon atoms, one, two or three heteroatoms selected from nitrogen (N) and sulfur (S) and / or an oxygen atom (O) may contain as ring members, wherein the cycle formed is unsubstituted or may contain one, two, three, four or five substituents L as defined above;

and their agriculturally acceptable salts.

2. Compounds according to claim 1, wherein Z is a group Z ¹ :

wherein # represents the attachment sites, n represents 3, 4, 5 or 6, and R ^z1 and R ^{z2 are} each independently selected from hydrogen and R ^z as defined in claim 1.

3. Compounds according to claim 1, wherein Z is a group Z ²

wherein # represent the attachment sites, m and p are each 0, 1 or 2, wherein m + p> 1, and R ^Z1 , R ^Z2 , R ^Z3 , R ^Z4 , R ^Z5 and R ^{Z6 are} each independently selected from hydrogen and R ^z , as defined in claim 1.

4. Compounds according to any one of claims 1 to 3, wherein X is N.

5. Compounds according to any one of claims 1 to 4, wherein Y is O.

6. Compounds according to any one of claims 1 to 4, wherein Y is a bond.

7. active ingredient composition comprising at least one compound of the formula I according to any one of claims 1 to 6 and / or a salt thereof and at least one further fungicidal, insecticidal and / or herbicidal active ingredient.

The active ingredient composition of claim 7, further comprising at least one solid or liquid carrier.

9. Seed comprising at least one compound of formula I according to any one of claims 1 to 6 and / or an agriculturally acceptable salt thereof.

10. Method for controlling phytopathogenic fungi, characterized in that the fungi or the materials, plants, the soil or seeds to be protected from fungal attack are treated with an effective amount of a compound of the formula I according to one of claims 1 to 6 or a farmer Socially acceptable salt treated.

1 1. A pharmaceutical composition comprising at least one compound of the formula I according to any one of claims 1 to 6 and / or a pharmaceutically acceptable salt thereof.

12. A process for the preparation of an antimycotic comprising the use of at least one compound of the formula I according to any one of claims 1 to 6 and / or a pharmaceutically acceptable salt thereof.