WO2011069894A1 - Triazole compounds, use thereof, and agents containing same - Google Patents

Triazole compounds, use thereof, and agents containing same Download PDF

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WO2011069894A1
WO2011069894A1 PCT/EP2010/068790 EP2010068790W WO2011069894A1 WO 2011069894 A1 WO2011069894 A1 WO 2011069894A1 EP 2010068790 W EP2010068790 W EP 2010068790W WO 2011069894 A1 WO2011069894 A1 WO 2011069894A1
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compounds
c4
ci
table
individualized compound
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PCT/EP2010/068790
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French (fr)
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Jochen Dietz
Thomas Grote
Egon Haden
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Richard Riggs
Alice GLÄTTLI
Marianna Vrettou-Schultes
Wassilios Grammenos
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Basf Se
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

The invention relates to triazole methyloxiranes of formula (I), wherein the variables are defined as in the claims or the description.

Description

Triazole, USE AND AGENTS CONTAINING

description

5 The present invention relates triazolylmethyloxiranes of the formula I

Figure imgf000002_0001

wherein the variables have the following meanings:

A, B independently of one another phenyl which is unsubstituted or substituted one, two, three or four 10 independently selected substituents L, wherein L represents:

L is halogen, cyano, nitro, cyanato (OCN), Ci-C4-alkyl, Ci-C 4 -Halo- genalkyl, phenyl-Ci-C4-alkyloxy, C2-C4 alkenyl, C2-C4 haloalkenyl , C2-C4 alkynyl, C2-C4 haloalkynyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, C1-15 C 4 alkylcarbonyloxy, Ci-C4 alkylsulfonyloxy, C2-C4 alkenyloxy , C2-C 4 -

Haloalkenyloxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6 cycloalkenyl, C 3 -C 6 halocycloalkenyl, S (= 0) n A 1, C (= 0) A 2, C (= S) A 2, NA 3 A 4, phenyl or phenyloxy wherein n, A 1, A 2, A 3, A 4 are:

20 n is 0, 1 or 2;

A 1 is hydrogen, hydroxy, Ci-C4-alkyl, Ci-C 4 haloalkyl, amino, Ci-C 4 alkylamino or di-Ci-C 4 alkylamino,

25 one of said at A 1 A 2 groups or C2-C4 alkenyl, C2-C 4 -

Haloalkenyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, C3-C6 cycloalkyl or C3-C6-halocycloalkyl;

A 3, A 4 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 -Halo- 30 genalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C3-C6

Cycloalkyl or C3-C6-halocycloalkyl; wherein the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L may carry one, two, three or four 35 identical or different groups R L for their part:

R L is halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 - alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-Halogencyclo- alkyl, Ci-C4-alkylcarbonyl, Ci-C4-alkylcarbonyloxy, C1-C4 alkoxycarbonyl, amino, Ci-C4-alkylamino, di-Ci-C4-alkylamino; p is 0, 1 or 2

R 1 CH2CH2CH2CH3, CH 2 CH (CH 3) 2, CH (CH 3) C 2 H 5 or C (CH 3) 3; and their agriculturally acceptable salts. The compounds of formula I, wherein p = 0, can be in the "Thiol" form of the formula Ia or in the "thiono" form of the formula Ib:

Figure imgf000003_0001

For simplicity here usually only one of the two forms, usually the "thiol" form indicated.

Furthermore, the invention relates to the preparation of the compounds I, which are intermediates for preparing the compounds I and their preparation as well as the use of the compounds according to the invention for combating phytopathogenic fungi and to compositions containing them.

There are triazolylmethyloxiranes with substituted triazole group, for example, from WO 96/38440, WO 97/41 107, WO 97/42178, WO 97/43269, WO 97/44331, WO 97/443332, WO 99/05149 and WO 99/21853 known. WO 2009/077471 (PCT / EP2008 / 067483), WO 2009/077443 (PCT / EP2008 / 067394), WO 2009/077500 (PCT / EP2008 / 067545) and WO 2009/077497 (PCT / EP2008 / 067539) are further substituted triazolo

known compounds. In the abovementioned prior triazolo compounds are disclosed wherein the triazole ring carries a S-methyl or S-ethyl group.

The fungicidal action of the known from the prior art compounds can in particular when low amounts but in some cases to be desired. The present invention therefore had the object to provide novel compounds, which preferably have improved properties such as a better fungicidal action and / or better toxicological properties. Due to the general problems that fungicidal compounds in practice often lead tencies to reform, it is also an object to provide new alternative compounds that can be effectively used as fungicides in agriculture. This object has surprisingly been solved by the herein described compounds of formula I. The compounds I are due to the basic character of the nitrogen atoms contained in them to be able to form salts with inorganic or organic acids or with metal ions salts or adducts. This is also true for most of the precursors described herein for compounds I, from which the salts and adducts are also subjects of vorliegenedn 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 such as formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic come acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, and other aryl carboxylic acids, 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, which carry one or two sulfo groups), alkylphosphonic rylphosphonsäuren (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), O or aryldiphosphonic acids (aromatic radicals such as phenyl and naphthyl, which carry one or two phosphoric acid radicals), where the alkyl or aryl radicals to carry further substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic, 2-acetoxybenzoic acid etc.

Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, as well as the first to eighth subgroup come, 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 may be present in the various valencies.

The compounds of formula I of the invention can be prepared for example by the following syntheses.

Compounds of the invention where p = 1 or 2 may be prepared by oxi- dation of the sulfur atom to the person skilled in the known standard methods from compounds of formula I, wherein p = 0. Suitable oxidizing agents include hydrogen peroxide, optionally in the presence of roxomolybdate (organic) acids such as acetic acid or trifluoroacetic acid, hydrogen peroxide urea complex, Peroxometallate as PE, and Peroxovanadate Peroxowolframate, Oxone (Kaliumperoxomono- sulfate), MCPBA (meta-chloroperbenzoic acid), peracetic acid , sodium or bromine, N-bromosuccinimide, N-chlorosuccinimide or dibromohydantoin in aqueous solution.

The compounds of the invention wherein n = 0 may advantageously be prepared from compounds of formula II

Figure imgf000005_0001

wherein A and B are defined as described herein or as herein as is preferred, respectively, by reaction with the corresponding derivative YR 1, wherein Y is a leaving group such as halogen (eg Cl or Br) or OSO2R ', wherein R 'stands for Ci-C6-alkyl, Ci-C6-haloalkyl, aryl or substituted aryl, are prepared. In particular, is OSO2R 'something for a mesylate, triflate, phenyl or toluene sulfonate group. To a compound II with the appropriate alkyl halides halogenide (YR 1, where Y = halogen, in particular Br or Cl) is reacted (see also WO 96/38440) is advantageous. Suitable conditions for alkylation reactions are known to the expert. Compounds of formula II are known from the prior art, see for example WO 96/38440, WO 97/41 107, WO 97/42178, WO 97/43269, WO 97/44331, WO 97/443332, WO 99/05149 and WO 99/21853, WO 2009/077471 (PCT / EP2008 / 067483), WO 2009/077443 (PCT / EP2008 / 067394), WO 2009/077500 (PCT / EP2008 / 067545). The synthesis of the compounds of formula II can be carried out in accordance with the cited prior art.

For example, compounds II can be prepared from compounds of formula III

Figure imgf000005_0002

wherein A and B are defined as described herein, may be prepared by reaction with a strong base and sulfur powder. Bases which all the skilled worker for such reactions known suitable bases. Preferably, strong alkali metal bases such as n-butyllithium, lithium diisopropylamide, sodium hydride, sodium amide or potassium tert-butoxide are used. It may be preferred, the reaction in the presence of an additive such as tetramethylethylene diamine (TM EDA) to carry out.

Suitable solvents are all customary for such reactions inert organic solvent into consideration, and preferably ethers such as tetrahydrofuran, dioxane, diethyl ether and 1, 2-dimethoxyethane or liquid ammonia or strongly polar solvents such as dimethyl sulfoxide may be used. Sulfur is preferably used as a powder. For hydrolysis, water is used, optionally in the presence of an organic or inorganic acid such as acetic acid, dilute sulfuric acid or dilute hydrochloric acid. The reaction temperature is preferably between -70 ° C and + 20 ° C, in particular between -70 ° C and 0 ° C. The reaction is generally carried out under atmospheric pressure. There are in general 1 mol of the compound of formula III 1 to 3 equivalents, preferably 1 to 2.5 equivalents, of strong base used and subsequently an equivalent amount or an excess of sulfur. The reaction may for example be carried out under nitrogen or argon protective gas atmosphere. The processing takes place after the specialist well-known procedures. Typically, the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or chromatography.

It is also possible to obtain compounds II by direct reaction of compounds III with sulfur, preferably powdered sulfur, without making use of a strong base such as butyllithium.

A further possibility, starting from compounds III compounds is to prepare II, compounds III with sulfur in the presence of an aprotic polar solvent such as an amide (such as dimethylformamide (DMF)) or N-alkyl pyrrolidone (such as N-octylpyrrolidone, N-dodecylpyrrolidone or N-methylpyrrolidone (NMP)) to implement. See also WO 99/19307, WO 97/06151, WO 96/41804 and WO 97/051 19. The reaction is carried out usually at temperatures ranging from 140 ° C to 160 ° C. The reaction components are typically used in such amounts that are used to 15 moles of sulfur to 1 mol of the compound II as. 6 Sulfur is normally used in form of powder. During the reaction, air is passed over the reaction mixture.

The synthesis of the compounds of formula III can be carried out in accordance with the initially cited prior art. Compounds of formula III are written 2007/147778 sawn partially in the patent applications WO 2007/147841, WO 2007/147769 and WO.

Compounds of formula IV

Figure imgf000007_0001

wherein Z is a leaving group Y (see below) or OH and A and B are as defined herein, as well are important starting compounds.

Thus, compounds III can, for example, starting from compounds IV

Figure imgf000007_0002

be prepared in which Z is a leaving group Y, such as halogen (eg Cl or Br) or OS0 2 R ', wherein R' is Ci-C 6 alkyl, Ci-C is 6 haloalkyl, aryl or substituted aryl. In particular, is OSO2R 'for a mesylate, triflate, phenyl or toluenesulfonate group. To obtain compounds of the formula III, compounds of formula IV with 1, 2,4-triazole and a base such as sodium hydride in DMF, for example, be implemented. See also, for example EP 0421125 A2.

One way to prepare compounds IV, is the double bond in compounds of the formula V

Figure imgf000007_0003

implement to the epoxide. Z stands for a leaving group Y (see above), and A and B are as defined for formula I or preferably defined. Suitable Epoxidierungsverfah- ren are known in the art. For example, this can be used Wasserstoffpero- oxide / maleic anhydride. In formula V, the double bond may be either in (E) and in (Z) configuration. This is shown by the jagged bond between B and the double bond.

Compounds V can also ground from

Figure imgf000007_0004

by reacting compounds VI with, for example acetic acid / H2S04 in a suitable organic solvent such as an ether such as dioxane or Et.20 be reacted to form the double bond. Suitable methods are known in the art. Z is as defined for formula V and A and B are as defined for formula I.

Compounds VI are accessible, for example via a Grignard reaction according to the following scheme:

Figure imgf000008_0001

See also EP 409,049th

Compounds of formula IV, wherein Z stands for a leaving group Y may also be prepared from compounds of formula IV wherein Z is OH are obtained by insertion of the leaving group Y by means known in the art methods. See also, eg, WO 2005/056548.

Compounds of formula IV, wherein Z is OH, can be prepared from α, β- disubstituted acroleins the type of formula VII

Figure imgf000008_0002

be obtained by first epoxidized, for example with H2O2 in the presence of a base such as NaOH, or by reaction with a peracid (eg, MCPBA = m-chloroperoxybenzoic acid), or tert-butyl hydroperoxide). By reduction of the aldehyde group of the epoxides formed, for example with NaBH 4 (see also EP 0 386 557A1), the alcohols of formula IV are formed. In formula VII, the double bond may be either in (E) and in (Z) configuration. This is shown by the jagged bond between B and the double bond.

A further possibility, compounds I, wherein p = 0 means to restore, the corresponding unsubstituted sleeves III

Figure imgf000008_0003

reacting with a base and the corresponding disulfide R 1 CSS-CR 1 (VIII). A, B, R 1 are as defined as described herein. For preparing compounds I, wherein p is = 1, compounds III can be reacted with the corresponding sulfinate ester. Compounds I, wherein p is = 2 may be prepared from compounds III by reaction with the corresponding sulfonic acid ester, sulfonic acid anhydride, sulfonyl chloride or sulfonyl fluoride.

Bases which all the skilled worker for such reactions known suitable bases. Preferably, strong alkali metal bases such as n-butyllithium, lithium diisopropylamide, sodium hydride, sodium amide or potassium tert-butoxide used. It may be preferred, the reaction in the presence of an additive such as tetramethylethylenediamine (TMEDA) to perform. The disulfides are commercially available or can be synthesized by conventional manufacturing methods.

Suitable solvents are all customary for such reactions inert organic solvent into consideration, and preferably ethers such as tetrahydrofuran, dioxane, diethyl ether and 1, 2-dimethoxyethane or liquid ammonia or strongly polar solvents such as dimethyl sulfoxide may be used. The reaction temperature is preferably between -70 ° C and + 20 ° C, in particular between -70 ° C and 0 ° C. The reaction is generally carried out under atmospheric pressure.

There are in general 1 mol of the compound of formula III 1 to 3 equivalents, preferably 1 to 2.5 equivalents, of strong base used and subsequently an equivalent amount or an excess of disulfide. The reaction may for example be carried out under nitrogen or argon protective gas atmosphere. The work-up is carried out after the specialist well-known procedures. Typically, the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or chromatography. Is advantageous in the synthesis of the compounds I using disulfides (VIII), that during the reaction, besides the desired product I, the sulphide R 1 R 2 R 3 C-SH (IX) is produced and this by oxidation with a suitable Oxidatinsmittel in a organic solvent can be re-converted to the disulfide (VIII). Suitable oxidizing agents for this are eg. H2O2, air, O2, I2, NaOCl, NaOBr NaBr03, tert-butyl hydroperoxide and the like. The skilled person suitable reactions for the conversion of a sulphide to the disulfide and corresponding reaction conditions are known.

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

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl and the alkyl moieties of composite groups, such as alkylamine mino: saturated, straight-chain or branched hydrocarbon radicals having from 1 to 4, 6, 8 or 12 carbon atoms, for example Ci-C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl , 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 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 stated above, wherein all of the hydrogen atoms are replaced by halogen atoms as mentioned above partially or in these groups; in particular Ci-C2-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, Dichlorflu- ormethyl, 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 -Trifluorprop-2-yl; Alkenyl and the alkenyl moieties in composite groups, such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having from 2 to 4, 2 to 6 or 2 to 8 carbon atoms and a double bond in any position. According to the invention it may be preferred to use small alkenyl groups such as (C2-C4) -alkenyl, on the other hand, it may be preferable to employ larger alkenyl groups, such as (C5-C8) alkenyl. Beipiele alkenyl groups for example C2-C6-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1 -Methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 are - 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-3pentenyl, 2-methyl-3pentenyl, 3-methyl-3pentenyl, 4-methyl-3pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1 -butenyl, 1, 2- dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1 -butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2- dimethyl-3-butenyl, 2,3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3- butenyl, 3,3-dimethyl-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 the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine in these groups;

Alkynyl and the alkynyl moieties in composite groups: straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl such as ethynyl, 1 -propynyl, 2- propynyl, 1 -Butinyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1 -Pentinyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl- 3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butinyl, 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 -pentinyl, 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 -butinyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl 3-butynyl and 1-ethyl-1 - methyl-2-propiny l;

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

Cycloalkyl and the cycloalkyl moieties in composite groups: mono- or bicyclic, saturated hydrocarbon groups having 3 to 8, especially 3 to 6 carbon ring members, for example C3-C6-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

Halocycloalkyl: cycloalkyl, as defined above, wherein the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine in these groups; Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having preferably 3 to 8 or 4 to 6, especially 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexene-4-yl and the like;

Halocycloalkenyl: cycloalkenyl, as defined above, wherein the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine in these groups; Alkoxy: an alkyl group attached via an oxygen as defined above, preferably having from 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, for example pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1 -Dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, He xoxy, 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 and 1 -ethyl-2- methylpropoxy;

Haloalkoxy: alkoxy as defined above, wherein the hydrogen atoms are partially or completely replaced by halogen atoms as described above under genalkyl halogen, especially fluorine, chlorine or bromine in these groups. Examples are OCH 2 F, OCHF 2, OCF 3, OCH2CI, OCHC, OCCI3, chlorofluoromethoxy, Dichlorflu- ormethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2- lodethoxy, 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, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy , 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3- chloropropoxy, 2,3-dichloropropoxy, 2-bromo propoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3- trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 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; also 5-fluoropentoxy, 5-chloropentoxy, 5 Brompentoxy, 5-lodpentoxy, Undecafluorpentoxy, 6-Fluorhexoxy, 6-Chlorhexoxy, 6- Bromhexoxy, 6-lodhexoxy or Dodecafluorhexoxy.

The new compounds of the invention contain chiral centers and are generally in the form of racemates or as diastereomer mixtures of erythro and threo forms. The erythro and threo diastereomers can be separated, for example, due to their different solubility or by column chromatography, and isolated in pure form, the inventive compounds. Such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers. As antimicrobial agents, one can use both the pure diastereomers or enantiomers and their mixtures obtained in the synthesis. The same applies for the fungicidal compositions.

Accordingly, the invention provides both the pure enantiomers or diastereomers and mixtures thereof. This applies to the compounds of the formula I and, where appropriate according to their precursors. In particular, the (R) are within the scope of the present invention - and (S) -isomers and the racemates of the compounds of the invention included, having chiral centers. Suitable compounds of the invention also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.

The inventive compounds can exist in different crystal modifications whose biological activity may differ. These are included in the scope of the present invention.

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

According to the invention, A is phenyl, which is unsubstituted or contains one, two, three, or four independently selected substituents L, wherein L is as defined herein or preferably defined. According to a particular embodiment, A is unsubstituted phenyl.

According to another embodiment, A is phenyl, the one, two, three or four, in particular one or two, independently selected substituents L, wherein L is as defined herein or preferably defined. According to one embodiment, one of the substituents is in the 4-position of the phenyl ring. According to a further aspect, L is independently selected from F, Cl, Br, nitro, phenyl, phenoxy, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, lormethyl funnel-, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and Trifluorchlormethyl. According to another particular embodiment, L is independently selected from F, Cl and Br, especially F and Cl. According to a further embodiment, A means monosubstitiertes phenyl, which contains a substituent L wherein L is as defined herein or preferably defined. According to one aspect of this embodiment is the substituent in the para position. In a particular embodiment A is 3-fluorophenyl.

According to another embodiment, A is phenyl, containing two or three independently selected substituents L. According to a further embodiment of the present invention, A is phenyl which is substituted by an F and another substituent contains a L, wherein the phenyl may additionally contain one or two independently selected substituents L. A is according to a ine group A-1

Figure imgf000013_0001

in which # represents the point of attachment of the phenyl ring to the oxirane ring; and

L 2 is selected from F, Cl, NO2, phenyl, halophenyl, phenoxy, Halogenpheno- xy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C1-C4-halogenoalkylthio ;

L 3 is independently selected from F, Cl, Br, NO2, phenyl, halophenyl, phenoxy, halophenoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4

Haloalkoxy and Ci-C4-haloalkylthio; and

m is 0, 1 or 2.

L 2 is according to a particular embodiment selected from F, Cl, methyl, methoxy, CF3, CHF2, OCF3, OCHF2 and OCF3. According to a more particular embodiment, L 2 is F or Cl.

L 3 is according to a specific embodiment, independently selected from F, Cl, methyl, methoxy, CF 3, CHF 2, OCF 3, OCF 3 or OCHF 2. According to a more specific exemplary form, L 3 are independently F or Cl.

According to a preferred embodiment is m = 0. In another preferred embodiment, m =. 1 In formula A-1, the fluoro substituent is in accordance with a preferred embodiment, in the 4-position. According to yet another preferred embodiment, A is di-substituted phenyl, which contains exactly two independently selected substituents L, wherein L is as defined herein or preferably defined. In particular L is each independently preferably selected from F, Cl, Br, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from F, Cl, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from F, Cl, methyl, trifluoromethyl and methoxy, contains. According to a further embodiment, the second Substituenet L is selected from methyl, methoxy and chlorine. According to one embodiment thereof is one of the substituents in the 4-position of the phenyl ring. According to a particular embodiment, A is phenyl, containing an F and exactly one further substituent L, as defined herein or preferably defined.

According to a further particular embodiment of the phenyl ring A is disubstituted in the 2,4-position. According to yet another particular embodiment, the phenyl ring A disubstituted in the 2,3-position. According to approximately form a still further special execution of the phenyl ring A is disubstituted at 2,5-position. According to yet another particular embodiment, the phenyl ring A disubstituted in the 2,6-position. According to yet another particular embodiment, the phenyl ring A in 3,4-position disubstituiert.Gemäß yet another particular embodiment, the phenyl ring A disubstituted in the 3,5-position.

According to another preferred embodiment of the invention, A is phenyl which is substituted by exactly two F. According to an embodiment A is 2,3-difluoro substituted. According to a further embodiment, A is 2,4-difluorsubstituiert. According to yet a further embodiment, 2,5-difluorsubstituiert A. According to yet of a further embodiment, 2,6-difluorsubstituiert A. According to yet a further embodiment, 3,4-difluorsubstituiert A. According to still a further embodiment, A 3, 5- difluorsubstituiert.

According to yet another preferred embodiment, A is tri-substituted phenyl, which contains three independently selected substituents L, wherein L is as defined herein or preferably defined. According to a particular aspect of this embodiment, A is phenyl which is substituted with exactly three F. According to an embodiment A is 2,3,4-tri-substituted, especially 2,3, 4-trifluorsubstituiert. According to another embodiment A is 2,3,5-tri-substituted, in particular 2,3,5-trifluorsubstituiert. According to a still further embodiment A 2,3,6-trisubstituted, in particular 2,3,6-trifluorsubstituiert. According to a still further embodiment A 2,4,6-trisubstituted, in particular 2,4,6-trifluorsubstituiert. According to a still further embodiment A 3,4,5-trisubstituted, in particular 3,4,5-trifluorsubstituiert. According to a still further embodiment A 2,4,5-trifluorsubstituiert, in particular 2,4,5-trifluorsubstituiert. According to the invention, B is phenyl, which is unsubstituted or contains one, two, three or four identical or different substituents L, where L is as defined herein or preferably defined.

According to one embodiment of the invention B is unsubstituted phenyl.

According to another embodiment, B is phenyl, containing one, two, three, or four independently selected substituents L, where L is as defined herein or preferably defined. According to a further embodiment, B is phenyl which one, two or three, preferably one or two, independently selected substituents as defined herein or L bevozugt defined contains. In a particular embodiment L is each independently selected from F, Cl, Br, methyl, methoxy and trifluoromethyl. In still a specific embodiment, B is phenyl, forward by one, two or three preferably one or two halogen atoms.

According to a further embodiment, B is phenyl, containing one, two, three or four substituents L where L is independently selected from F, Cl, Br, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and Trifluorchlormethyl. According to a particular embodiment, each L is independently selected from F, Cl and Br.

In yet another embodiment, B is phenyl, which is unsubstituted or substituted with one, two or three substituents independently selected from halogen, N0 2, amino, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci- C 4 haloalkyl, Ci-C 4 - haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 dialkylamino, thio, and Ci-C 4 alkylthio.

According to a further embodiment of the phenyl ring in B is mono-substituted with exactly one substituents L, wherein L is according to a particular aspect of this embodiment in ortho-position to the point of attachment of the phenyl ring with the oxirane ring. L is as defined herin, or preferably defined. According to a further specific embodiment, B is mono-substituted by Cl phenyl, especially 2-chlorophenyl. According to another embodiment, B is phenyl, which contains two or three, especially two, independently selected substituents L, where L is as defined herein or preferably defined. According to still another embodiment of the invention, B is a phenyl ring containing a substituent L in the ortho-position, and further comprising exactly one further independently selected substituents L. According to one embodiment the phenyl ring is 2,3-disubstituted. According to another embodiment the phenyl ring is 2,4-disubstituted. According to yet a further embodiment, the phenyl ring is 2,5-disubstituted. According to a further embodiment of the phenyl ring is 2,6-disubstituted yet.

According to still another embodiment of the invention, B is a phenyl ring containing a substituent L in the ortho position and also exactly two further substituents selected irrespective L contains. According to one embodiment of the

Phenyl 2,3,5-tri-substituted. According to another embodiment the phenyl ring is 2,3,4-trisubstituted. According to a further embodiment, the phenyl is 2,4,5- or trisubstituted.

According to a further embodiment of the invention B is phenyl, which contains a substituent L in the 2-position and one, two or three independently selected substituents L. B is according to a preferred embodiment for a group B-1

Figure imgf000016_0001

in which # represents the point of attachment of the phenyl ring to the oxirane ring; and

L 1 is selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci- C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from F, Cl, methyl, ethyl, methoxy, ethoxy, CF 3, CHF 2, OCF 3, OCHF 2 and SCF 3;

L 2 is selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci- C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from F,

Cl, methyl, ethyl, methoxy, ethoxy, CF 3, CHF 2, OCF 3, OCHF 2 and SCF 3;

L 3 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4 alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from F, Cl, methyl, ethyl, methoxy , ethoxy, CF 3, CHF 2, OCF 3, OCHF 2 and SCF 3; and

m is 0, 1 or 2. In a preferred embodiment L 1 F. According means yet another preferred embodiment, L 1 is Cl. According to another preferred embodiment L 1 is methyl. According to yet another preferred embodiment, L 1 is methoxy. According to yet another preferred embodiment, L 1 is CF 3. According to yet another preferred embodiment, L 1 is ocfs or OCHF2. According to a preferred embodiment, therefore, is in the inventive compounds of formula I B represents phenyl substituted in the 2-position a substituent selected from F, Cl, CH 3, OCH 3, CF 3, CHF 2, OCF 3 and OCHF 2, and a includes two or more independently selected substituents L.

According to a preferred embodiment, L 2 F. According means yet another preferred embodiment, L 2 is Cl. According to a further preferred embodiment, L 2 is methyl. According to yet another preferred embodiment, L 2 is methoxy. According to yet another preferred embodiment, L 2 is CF 3. According to yet another preferred embodiment, L 2 is OCF 3 or OCHF. 2

According to a preferred embodiment, L 3 F. According means yet another preferred embodiment, L represents Cl 3. According to another preferred exemplary form, L 3 is methyl. According to yet a further preferred embodiment, L 3 is methoxy. According to yet a further preferred embodiment, L 3 CF3. According to yet a further preferred embodiment, L 3 OCF 3 or OCHF. 2 According to a preferred embodiment, m = 0, that is B is a disubstituted phenyl ring B-1. According to a preferred embodiment B is a 2,3-disubstituted phenyl ring. According to a further preferred embodiment the phenyl ring is B-1 2,4-disubstituted. According to a further preferred embodiment the phenyl ring is not B-1 2,5-disubstituted. According to yet another preferred embodiment the phenyl ring is 2,6-disubstituted.

According to a further preferred embodiment, m = 1, B-1 is thus a tri- substituted phenyl ring. According to a preferred embodiment the phenyl ring is B-1 2,3,5-trisubstituted. According to a preferred further embodiment, the phenyl ring is not B-1 2,3,4-trisubstituted. According to a further preferred embodiment the phenyl ring B is still 2,4,5-trisubstituted.

According to the invention L is independently halogen, cyano, nitro, cyanato (OCN), C1-C4-alkyl, Ci-C4-haloalkyl, phenyl-Ci-C4-alkyloxy, C2-C4-alkenyl, C2-C4 halo alkenyl , C2-C4 alkynyl, C2-C4-haloalkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4-alkylcarbonyloxy, Ci-C4-alkylsulfonyloxy, C2-C4-alkenyloxy, C2-C4-halogenoalkenyloxy , C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6 halocycloalkenyl, S (= 0) n A 1, C (= 0) A 2, C (= S) A 2, NA 3 A 4, phenyl or phenoxy where n, A 1, A 2, A 3, A 4: n is 0, 1 or 2;

A 1 is hydrogen, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl, amino, Ci-C4-alkylamino or di-Ci-C4-alkylamino,

A 2 is an alkyl as defined for A 1 groups or C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl or C3-C6-Halogencyclo-;

A 3, A 4 are independently hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4 alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl; wherein the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L may carry one, two, three or four identical or different groups R L for their part:

R L is halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci- C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4 - alkylcarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxycarbonyl, amino, C1-C4 alkylamino, di-Ci-C4-alkylamino;

If it is not otherwise stated, L has, independently, the following preferred meanings:

In one embodiment, L is independently selected from halogen, cyano, nitro, cyanato (OCN), Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4 alkoxy, C1-C4 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, SA 1, C (= 0) A 2, C (= S) A 2 NA 3 A 4; wherein A 1, A 2, A 3, A 4 are:

A 1 is hydrogen, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl;

A 2 A 1 wherein one of said groups or Ci-C4-alkoxy, C1-C4 haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl;

A 3, A 4 are independently hydrogen, Ci-C4-alkyl, Ci-C4-halo- genalkyl; wherein the aliphatic and / or alicyclic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups R L: R L is halogen, cyano, nitro, Ci-C4-alkyl, Ci-C 4 haloalkyl , Ci-C 4 - alkoxy, Ci-C 4 alkylamino haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, amino, Ci-C 4 alkylamino, di-Ci-C. 4

Furthermore preferably, L is independently selected from halogen, NO2, amino, Ci-C 4 - alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4 alkylamino, di- Ci-C4-alkylamino, thio, and Ci-C 4 alkylthio. Furthermore preferably, L Ci-C is independently selected from halo, 4 alkyl, Ci-C 4 - haloalkyl, Ci-C4-alkoxy, Ci-C4 haloalkoxy, and Ci-C4-haloalkylthio, in particular halogen, Ci-C 4 alkyl and Ci-C4-haloalkyl.

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,

OCHF2 and SCF 3, in particular selected from F, Cl, CH 3, C 2 H 5, OCH 3, OC2H5, CF3, CHF2, OCF3, OCHF2 and SCF3. According to one embodiment, L is independently selected from F, Cl, CH3, OCH3, CF3, OCF3 and OCHF2. It may be preferred that L is independently F or Cl.

In specific preferred embodiments according to the invention is 4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 4-methylphenyl, 3-bromo-4, in the compounds IA phenyl, 2,4-chlorophenyl fluorophenyl, 4-bromophenyl, 3,4-dichlorophenyl, 4-tert-butylphenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4-trifluoromethoxyphenyl, and B represents 2-chlorophenyl. According to a special training fürhungsform A is 4-fluorophenyl and B is 2-chlorophenyl. According to a further particular embodiment, A is 2,4-difluorophenyl and B is 2-chlorophenyl. According to another preferred embodiment, A is 4-fluorophenyl and B is 2-difluoromethoxyphenyl respectively.

According to another specific invention according to preferred embodiments, in the compounds IA is phenyl, 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4-methylphenyl, 4-fluorophenyl, 3-bromo-4-fluorophenyl, 4- bromophenyl, 3,4-dichlorophenyl, 4-tert-butylphenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4-trifluoromethoxyphenyl, and each B is 2-fluorophenyl.

According to still another specific invention according to preferred embodiments, in the compounds IA is phenyl, 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4-methylphenyl, 4-fluorophenyl, 3-bromo-4-fluorophenyl, 4 - bromophenyl, 3,4-dichlorophenyl, 4-tert-butyl-phenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4-trifluoromethoxyphenyl, and each B is 2-bromophenyl. According to a preferred embodiment of the present invention means p = 0. These compounds are also referred to as compounds 1-1.

According to a further embodiment, p =. 1 These compounds are known as compounds I-2. According to yet a further embodiment, p = 2. These compounds are also referred to as compounds I-third

According to a preferred embodiment of compounds I R 1 is

Figure imgf000020_0001

According to a further embodiment of the compounds I, R 1 is CH 2 CH (CH 3). 2

According to yet another embodiment of the compounds I, R 1 represents

CH (CH 3) C 2 H. 5

According to yet another preferred embodiment of the compounds I, R 1 is C (CH 3). 3

The compounds of the invention can be used as pure enantiomers or as

Mixture of enantiomers (racemic or in any possible

Enantiomer) are present. According to one embodiment there is a

racemic mixture, preferably the corresponding "trans" diastereoisomer (A and B show in opposite directions) Particularly preferred compounds are those listed below and the individual stereoisomers thereof.:

Stereoisomers of the compound 1.1 (p = 0), wherein A is 4-fluorophenyl, 2-chlorophenyl and B is R 1 is CH (CH 3) C 2 H 5 (2-butylamine) is:

Isomer 1.1 -a 1): 5- (2-butyl) sulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxirane-2-yl] methyl] - 1, 2,4-triazole ( "ice")

Isomer 1.1 -a2): 5- (2-butyl) sulfanyl-1 - [[(2R, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1 , 2,4-triazole ( "ice"), both "cis" -isomers also be 5- (2-butyl) sulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) - 2- (4-fluorophenyl) oxiran-2-yl] methyl] -1 named, 2,4-triazole (or 5- (2-butylsulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole)

Isomer 1.1 -a3): 5- (2-butyl) sulfanyl-1 - [[(2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1 , 2,4-triazole ( "trans") isomer I.1 -a4): 5- (2-butyl) sulfanyl-1 - [[(2R, 3S) -3- (2-chlorophenyl) -2- (4 - fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans")

Both "trans" -isomers also be 5- (2-butyl) sulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazol called (or 5- (2-butyl) sulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxirane-2-yl] methyl] - 1, 2,4-triazole)

Stereoisomers of the compound I.2 (p = 0), wherein A is 4-fluorophenyl, B is 2-chlorophenyl and R 1 is 1-n-butyl:

Isomer l.2-a1): 5- (1-n-butyl) sulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "ice") isomer l.2-a2): 5- (1-n-butyl) sulfanyl-1 - [[(2R, 3R) -3- (2-chlorophenyl ) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "ice")

Both "cis" -isomers are also 5- (1-n-butyl) sulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2- yl] methyl] -1 named, 2,4-triazole (or 5- (1 -n-butylsulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl ) oxiran-2-yl] methyl] - 1, 2,4-triazole)

Isomer l.2-a3): 5- (1-n-butyl) sulfanyl-1 - [[(2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans")

Isomer l.2-a4): 5- (1-n-butyl) sulfanyl-1 - [[(2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans")

Both "trans" -isomers are also 5- (1-n-butyl) sulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2- yl] methyl] -1 named, 2,4-triazole (or 5- (1 -n-butyl) sulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- ( 4-fluorophenyl) oxiran-2-yl] methyl] - 1, 2,4-triazole)

Stereoisomers of the compound I.3 (p = 0), wherein A is 2,4-difluorophenyl, B is 2-chlorophenyl and R 1 is 1-n-butyl:

Isomer l.3-a1): 5- (1-n-butyl) sulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2- yl] methyl] -1, 2,4-triazole ( "ice") isomer l.3-a2): 5- (1-n-butyl) sulfanyl-1 - [[(2R, 3R) -3- (2 -chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "ice"), both "cis" -isomers are also 5- (1-n-butyl ) sulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, called 2,4-triazole ( or 5- (1 -n-butylsulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] - 1, 2,4-triazole)

Isomer l.3-a3): 5- (1-n-butyl) sulfanyl-1 - [[(2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2- yl] methyl] -1, 2,4-triazole ( "trans")

Isomer l.3-a4): 5- (1-n-butyl) sulfanyl-1 - [[(2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2- yl] methyl] -1, 2,4-triazole ( "trans")

Both "trans" -isomers are also 5- (1-n-butyl) sulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane 2-yl] methyl] -1, 2,4-triazol called (or 5- (1 -n-butyl) sulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2 - (2,4-difluorophenyl) oxiran-2-yl] methyl] - 1, 2,4-triazole)

Stereoisomers of the compound I.4 (p = 0), wherein A is 4-fluorophenyl, B is 2-chlorophenyl and R 1 is CH 2 CH (CH 3) 2 (1 - (2-methylpropyl)) is: Isomer l. 4-a1): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl ] -1, 2,4-triazole ( "ice")

Isomer l.4-a2): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2R, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2- yl] methyl] -1, 2,4-triazole ( "ice")

Both "cis" -isomers are also 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxirane 2-yl] methyl] -1, 2,4-triazol called (or 5- (1 - (2-methylpropyl) sulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2 - (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole)

Isomer l.4-a3): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2- yl] methyl] -1, 2,4-triazole ( "trans")

Isomer l.4-a4): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2- yl] methyl] -1, 2,4-triazole ( "trans")

Both "trans" -isomers are also 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxirane 2-yl] methyl] -1 2,4-triazole called (or 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole) stereoisomers of the compound 1.5 (p = 0), wherein A is 2,4-difluorophenyl, 2-chlorophenyl and B R 1 is CH (CH 3) C 2 H 5 represents:

Isomer l.5-a1): 5- (2-butyl) sulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "ice")

Isomer l.5-a2): 5- (2-butyl) sulfanyl-1 - [[(2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "ice"), both "cis" -isomers also be 5- (2-butyl) sulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl ) - 2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazol called (or 5- (2-butyl) sulfanyl 1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole)

Isomer l.5-a3) 5- (2-butyl) sulfanyl-1 - [[(2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans")

Isomer l.5-a4): 5- (2-butyl) sulfanyl-1 - [[(2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans") Both "trans" -isomers also be 5- (2-butyl) sulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl ) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1 named, 2,4-triazole (or 5- (2-

Butyl) sulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -

1, 2,4-triazole) stereoisomers of the compound I.6 (p = 0), wherein A is 2,4-difluorophenyl, B 2-chlorophenyl and R 1 is (CH 2 CH CH 3) 2 (1 - ( 2-methylpropyl)) is:

Isomer L.6-a1): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane 2-yl] methyl] -1, 2,4-triazole ( "ice")

Isomer L.6-a2): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane 2-yl] methyl] -1, 2,4-triazole ( "ice")

Both "cis" -isomers are also 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2-yl] methyl] -1, 2,4-triazol called (or 5- (1 - (2-methylpropyl) sulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole)

Isomer L.6-a3): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane 2-yl] methyl] -1, 2,4-triazole ( "trans") isomers L.6-a4): 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[(2R, 3S) - 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans")

Both "trans" -isomers are also 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2-yl] methyl] -1, 2,4-triazol called (or 5- (1 - (2-methylpropyl)) sulfanyl-1 - [[- rel- (2R, 3S) -3- (2- chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole)

Stereoisomers of the compound I.7 (p = 0), wherein A is 4-fluorophenyl, B is 2-chlorophenyl and R 1 represents tert-butyl:

Isomer l .7-a1): 5- (tert-butyl) sulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "ice") isomer l .7-a2): 5- (tert-butyl) sulfanyl-1 - [[(2R, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "ice")

Both "cis" -isomers are also 5- (tert-butyl) sulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1 named, 2,4-triazole (or 5- (tert-butyl) sulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxirane -2-yl] methyl] - 1, 2,4-triazole)

Isomer l .7-a3): 5- (tert-butyl) sulfanyl-1 - [[(2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans")

Isomer l .7-a4): 5- (tert-butyl) sulfanyl-1 - [[(2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazole ( "trans")

Both "trans" -isomers are also 5- (tert-butyl) sulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] -1, 2,4-triazol called (or 5- (tert-butyl) sulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxirane-2-yl] methyl] - 1, 2,4-triazole).

The meanings of the variables A, B and L connects foregoing fertilize I apply if it is not otherwise specified, correspondingly to the precursors of the compounds of the invention.

Figure imgf000024_0001
In particular, the results summarized in the following tables 1 a to 137a compounds 1-1 according to the invention are preferred in view of their use. The groups mentioned in the tables for a substituent are furthermore per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question. From the above-mentioned in the following tables compounds in each case all stereoisomers are object of the present Invention.

Table 1a

Compounds 1-1 where A is 2,3-difluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.1 aA-1 to I-1 .1 aA-1 18)

table 2a

Compounds 1-1 where A is 2,4-difluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.2aA-1 to I-1 .2aA-1 18)

table 3a

Compounds 1-1 where A is 2,5-difluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.3aA-1 to I-1 .3aA-1 18)

table 4a

Compounds 1-1, wherein A is 2,6-difluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.4aA-1 to I-1 .4aA-1 18)

table 5a

Compounds 1-1, wherein A is 3,4-difluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.5aA-1 to I-1 .5aA-1 18)

table 6a

Compounds 1-1 where A is 3,5-difluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.6aA-1 to I-1 .6aA-1 18)

table 7a

Compounds 1-1, wherein A is 2-fluoro-3-chlorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .7aA-1 to I-

1 .7aA-1 18)

table 8a

Compounds 1-1, wherein A is 2-fluoro-4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .8aA-1 to I-1 .8aA-1 18)

table 9a

Compounds 1-1, wherein A is 2-fluoro-5-chlorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .9aA-1 to I-1 .9aA-1 18)

table 10a

Compounds 1-1, wherein A is 2-fluoro-6-chlorophenyl I and the combination of B and R 1 corresponds to one row of Table A (compounds 1 to 1-1.1 OAA OAA 1-1.1-1 18)

Table 1 1 a

Compounds 1-1 in which A is 3-fluoro-4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .1 1 aA-1 to 1-1 .1 1 aA -1 18)

table 12a

Compounds 1-1, wherein A is 3-fluoro-5-chlorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .12aA-1 to L-1 .12aA-1 18)

table 13a

Compounds 1-1, wherein A is 2-chloro-3-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .13aA-1 to L-1 .13aA-1 18)

table 14a

Compounds 1-1, wherein A is 2-chloro-4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .14aA-1 to L-1 .14aA-1 18)

table 15a

Compounds 1-1, wherein A is 2-chloro-5-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .15aA-1 to L-1 .15aA-1 18)

table 16a

Compounds 1-1, wherein A is 3-chloro-4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .16aA-1 to L-1 .16aA-1 18)

table 17a

Compounds 1-1, wherein A is 2-methyl-3-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .17aA-1 to L-1 .17aA-1 18)

table 18a

Compounds 1-1, wherein A is 2-methyl-4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .18aA-1 to L-1 .18aA-1 18)

table 19a

Compounds 1-1, wherein A is 2-methyl-5-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .19aA-1 to L-1 .19aA-1 18) table 20a

Compounds 1-1, wherein A is 2-methyl-6-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .20aA-1 to L-1 .20aA-1 18)

Table 21a

Compounds 1-1 in which A is 3-methyl-4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .21 aA-1 to L-1 .21 aA-1 18)

table 22a

Compounds 1-1, wherein A is 3-methyl-5-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1 .22aA-1 to L-1 .22aA-1 18)

table 23a

Compounds 1-1, wherein A is 2-fluoro-3-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.23aA-1 to L-1.23aA-1 18)

table 24a

Compounds 1-1, wherein A is 2-fluoro-4-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.24aA-1 to 1-1.24aA-1 18)

table 25a

Compounds 1-1, wherein A is 2-fluoro-5-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.25aA-1 to L-1.25aA-1 18)

table 26a

Compounds 1-1, wherein A is 3-fluoro-4-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.26aA-1 to L-1.26aA-1 18)

table 27a

Compounds 1-1, wherein A is 2-methoxy-3-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.27aA-1 to L-1 .27aA-1 18)

table 28a

Compounds 1-1, wherein A is 2-methoxy-4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.28aA-1 to L-1 .28aA-1 18)

table 29a

Compounds 1-1, wherein A is 2-methoxy-5-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.29aA-1 to 1-1 .29aA-1 18)

table 30a

Compounds 1-1, wherein A is 2-methoxy-6-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.30aA-1 to L-1 .30aA-1 18)

Table 31a

Compounds 1-1 in which A is 3-methoxy-4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.31 aA-1 to 1-1 .31 aA-1 18)

table 32a

Compounds 1-1, wherein A is 3-methoxy-5-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.32aA-1 to 1-1 .32aA-1 18)

table 33a

Compounds 1-1, wherein A is 2-fluoro-3-methoxyphenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.33aA-1 to L-1 .33aA-1 18)

table 34a

Compounds 1-1, wherein A is 2-fluoro-4-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.34aA-1 to L-1 .34aA-1 18)

table 35a

Compounds 1-1, wherein A is 2-fluoro-5-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.35aA-1 to L-1 .35aA-1 18)

table 36a

Compounds 1-1, wherein A is 3-fluoro-4-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.36aA-1 to L-1 .36aA-1 18)

table 37a

Compounds 1-1, wherein A is 3-fluoro-5-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.37aA-1 to 1-1 .37aA-1 18)

table 38a

Compounds 1-1, wherein A is 2- (difluoromethoxy) -3-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .38aA-1 to L-1 1.38aA 18 )

table 39a

Compounds 1-1, wherein A is 2- (difluoromethoxy) -4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .39aA-1 to L-1 1.39aA 18 )

table 40a

Compounds 1-1, wherein A is 2- (difluoromethoxy) -5-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .40aA-1 to L-1 1.40aA 18 ) Table 41a

Compounds 1-1, wherein A is 2- (difluoromethoxy) -6-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .41 aA-1 to 1-1.41 aA-1 18)

table 42a

Compounds 1-1, wherein A is 3- (difluoromethoxy) -4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .42aA-1 to L-1 1.42aA 18 )

table 43a

Compounds 1-1, wherein A is 3- (difluoromethoxy) -5-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .43aA-1 to L-1 1.43aA 18 )

table 44a

Compounds 1-1, wherein A is 2-fluoro-3- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .44aA-1 to L-1.44aA -1 18)

table 45a

Compounds 1-1, wherein A is 2-fluoro-4- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .45aA-1 to L-1 1.45aA 18)

table 46a

Compounds 1-1, wherein A is 2-fluoro-5- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .46aA-1 to L-1 1.46aA 18)

table 47a

Compounds 1-1 in which A is 3-fluoro-4- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds I- 1 .47aA-1 to L-1 1.47aA 18)

table 48a

Compounds 1-1, wherein A is 2,3,4-trifluorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.48aA-1 to I-1 .48aA-1 18)

table 49a

Compounds 1-1, wherein A is 2,3,5-trifluorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.49aA-1 to I-1 .49aA-1 18)

table 50a

Compounds 1-1, wherein A is 2,3,6-trifluorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.50aA-1 to I-1 .50aA-1 18)

Table 51a

Compounds 1-1, wherein A is 2,4,5-trifluorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.51 aA-1 to I-1 .51 aA-1 18)

table 52a

Compounds 1-1, wherein A is 2,4,6-trifluorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.52aA-1 to I-1 .52aA-1 18)

table 53a

Compounds 1-1, wherein A is 3,4,5-trifluorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds 1-1.53aA-1 to I-1 .53aA-1 18)

table 54a

Compounds I, wherein A is phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.54aA-1 to l.54aA-1 18) Table 55a

Compounds I, wherein A is 2-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.55aA-1 to l.55aA-1 18) Table 56a

Compounds I in which A is 3-chlorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.56aA-1 to l.56aA-1 18) Table 57a

Compounds I, wherein A is 4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.57aA-1 to l.57aA-1 18) Table 58a

Compounds I, wherein A is 2-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.58aA-1 to l.58aA-1 18) Table 59a

Compounds I, wherein A is 3-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.59aA-1 to l.59aA-1 18) Table 60a

Compounds I, wherein A is 4-fluorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.60aA-1 to l.60aA-1 18) Table 61 a

Compounds I, wherein A is 2-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.61 to 1.61 aA aA-1 1 18)

Table 62a v

Compounds I, wherein A is 3-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.62aA-1 to l.62aA- 1 18)

table 63a

Compounds I, wherein A is 4-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.63aA-1 to l.63aA- 1 18)

table 64a

Compounds I, wherein A is 2-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.64aA-1 to l.64aA-

1 18)

table 65a

Compounds I in which A is 3-methoxyphenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.65aA-1 to l.65aA- 1 18)

table 66a

Compounds I, wherein A is 4-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.66aA-1 to l.66aA- 1 18)

table 67a

Compounds I, wherein A is 2-trifluoromethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.67aA-1 to l.67aA-1 18)

table 68a

Compounds I, wherein A is 3-trifluoromethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.68aA-1 to l.68aA-1 18)

table 69a

Compounds I, wherein A is 4-trifluoromethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.69aA-1 to l.69aA-1 18)

table 70a

Compounds I, wherein A is 2-difluoromethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.70aA-1 to l.70aA-1 18)

Table 71a

Compounds I in which A is 3-difluoromethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.71 aA-1 to l.71 aA-1 18)

table 72a

Compounds I, wherein A is 4-difluoromethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.72aA-1 to l.72aA-1 18)

table 73a

Compounds I, wherein A is 2,3-dichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.73aA-1 to 1 l.73aA- 18) Table 74a

Compounds I, wherein A is 2,4-dichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.74aA-1 to l.74aA- 1 18)

table 75a

Compounds I, wherein A is 2,5-dichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.75aA-1 to l.75aA- 1 18)

table 76a

Compounds I, wherein A represents 2,6-dichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.76aA-1 to l.76aA- 1 18)

table 77a

Compounds I, wherein A represents 3,4-dichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.77aA-1 to l.77aA-

1 18)

table 78a

Compounds I, wherein A is 3,5-dichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.78aA-1 to l.78aA- 1 18)

table 79a

Compounds I, wherein A is 2,3-dimethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.79aA-1 to l.79aA-1 18)

table 80a

Compounds I, wherein A is 2,4-dimethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.80aA-1 to l.80aA-1 18)

Table 81a

Compounds I, wherein A is 2,5-dimethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.81 aA-1 to l.81 aA-1 18)

table 82a

Compounds I, wherein A is 2,6-dimethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.82aA-1 to l.82aA-1 18)

table 83a

Compounds I, wherein A is 3,4-dimethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.83aA-1 to l.83aA-1 18)

table 84a

Compounds I, wherein A is 3,5-dimethylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.84aA-1 to l.84aA-1 18)

table 85a

Compounds I, wherein A is 2,3-dimethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.85aA-1 to l.85aA-1 18)

table 86a

Compounds I, wherein A is 2,4-dimethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.86aA-1 to l.86aA-1 18)

table 87a

Compounds I, wherein A is 2,5-dimethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.87aA-1 to l.87aA-1 18)

table 88a

Compounds I, wherein A is 2,6-dimethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.88aA-1 to l.88aA-1 18)

table 89a

Compounds I, wherein A is 3,4-dimethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.89aA-1 to l.894aA-1 18)

table 90a

Compounds I, wherein A is 3,5-dimethoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.90aA-1 to l.90aA-1 18)

Table 91a

Compounds I, wherein A is 2-methyl-3-chlorophenyl and the combination of

B and R 1 corresponds to one row of Table A (compounds L.91 aA-1 to L.91 aA-1 18)

table 92a

Compounds I, wherein A is 2-methyl-4-chlorophenyl and the combination of

B and R 1 corresponds to one row of Table A (compounds l.92aA-1 to l.92aA-1 18)

table 93a

Compounds I, wherein A is 2-methyl-5-chlorophenyl and the combination of

B and R 1 corresponds to one row of Table A (compounds l.93aA-1 to l.93aA-1 18)

table 94a

Compounds I, wherein A is 2-methyl-6-chlorophenyl and the combination of

B and R 1 corresponds to one row of Table A (compounds l.94aA-1 to l.94aA-1 18) Table 95a

Compounds I, wherein A is 3-methyl-4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.95aA-1 to l.95aA-1 18)

table 96a

Compounds I, wherein A is 3-methyl-5-chlorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.96aA-1 to l.96aA-1 18)

table 97a

Compounds I, wherein A is 2-chloro-3-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.97aA-1 to l.97aA-1 18)

table 98a

Compounds I, wherein A is 2-chloro-4-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.98aA-1 to l.98aA-1 18)

table 99a

Compounds I, wherein A is 2-chloro-5-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.99aA-1 to l.99aA-1 18)

table 100a

Compounds I, wherein A is 3-chloro-4-methylphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.100aA-1 to l.100aA-1 18)

Table 101 a

Compounds I, wherein A is 2-methoxy-3-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.101 aA-1 to l.101 aA-1 18)

table 102

Compounds I, wherein A represents 2-methoxy-4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.102aA-1 to l.102aA-1 18)

table 103

Compounds I, wherein A represents 2-methoxy-5-chlorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.103aA-1 to l.103aA-1 18)

table 104

Compounds I, wherein A represents 2-methoxy-6-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.104aA-1 to l.104aA-1 18)

table 105

Compounds I, wherein A is 3-methoxy-4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.105aA-1 to l.105aA-1 18)

table 106

Compounds I, wherein A is 3-methoxy-5-chlorophenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.106aA-1 to l.106aA-1 18)

table 107

Compounds I, wherein A is 2-chloro-3-methoxyphenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.107aA-1 to l.107aA-1 18)

table 108

Compounds I, wherein A is 2-chloro-4-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.108aA-1 to l.108aA-1 18)

table 109

Compounds I, wherein A is 2-chloro-5-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.109aA-1 to l.109aA-1 18)

Table 1 10a

Compounds I, in which A is 3-chloro-4-methoxyphenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.1 10aA-1 to l.1 10aA-1 18)

Table 1 1 1 a

Compounds I, wherein A is 2- (trifluoromethyl) -3-chlorophenyl is stopped and the combination of B and R 1 corresponds to one row of Table A (compounds l.1 10aA-1 to l.1 10aA-1 18)

Table 1 12a

Compounds I, wherein A is 2- (trifluoromethyl) -4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.1 12aA-1 to 1.1 12aA-1 18)

Table 1 13a

Compounds I, wherein A is 2- (trifluoromethyl) -5-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.1 13Aa-1 to 13Aa l.1-1 18)

Table 1 14a

Compounds I, wherein A is 2- (trifluoromethyl) -6-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.1 14aA-1 to l.1 14aA-1 18)

Table 1 15a

Compounds I, wherein A is 3- (trifluoromethyl) -4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds 1.1 15Aa-1 to 15Aa-1 l.1 18) Table 1 16a

Compounds I, wherein A is 3- (trifluoromethyl) -5-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.1 16Aa-1 to 16Aa l.1-1 18)

Table 1 17a

Compounds I, wherein A is 2-chloro-3- (trifluoromethyl) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.1 17Aa-1 to 17Aa l.1-1 18)

Table 1 18a

Compounds I, wherein A is 2-chloro-4- (trifluoromethyl) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.1 18Aa-1 to 18Aa l.1-1 18)

Table 1 19a

Compounds I, wherein A is 2-chloro-5- (trifluoromethyl) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.1-19aa 19aa-l.1 1 to 1 18 )

table 120

Compounds I, in which A is 3-chloro-4- (trifluoromethyl) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.120aA-1 to l.120aA-1 18)

Table 121a

Compounds I, wherein A is 2- (trifluoromethoxy) -3-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.121 aA-1 to l.121 aA-1 18)

table 122

Compounds I, wherein A is 2- (difluoromethoxy) -3-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.122aA-1 to l.122aA-1 18)

table 123

Compounds I, wherein A is 2- (difluoromethoxy) -4-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.123aA-1 to l.123aA-1 18)

table 124

Compounds I, wherein A is 2- (difluoromethoxy) -5-chlorophenyl is stopped and the combination of B and R 1 corresponds to one row of Table A (compounds l.124aA-1 to l.124aA-1 18)

table 125

Compounds I, wherein A is 2- (difluoromethoxy) -6-chlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.125aA-1 to l.125aA-1 18)

table 126

Compounds I, wherein A is 3- (difluoromethoxy) -4-chlorophenyl is stopped and the combination of B and R 1 corresponds to one row of Table A (compounds l.126aA-1 to l.126aA-1 18)

table 127

Compounds I, wherein A is 3- (difluoromethoxy) -5-chlorophenyl is stopped and the combination of B and R 1 corresponds to one row of Table A (compounds l.127aA-1 to l.127aA-1 18)

table 128a

Compounds I, wherein A is 2-chloro-3- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.128aA-1 to l.128aA-1 18)

table 129

Compounds I, wherein A is 2-chloro-4- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.129aA-1 to l.129aA-1 18)

table 130

Compounds I, wherein A is 2-chloro-5- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.130aA-1 to l.130aA-1 18)

Table 131 a

Compounds I, in which A is 3-chloro-4- (difluoromethoxy) phenyl, and the combination of B and R 1 corresponds to one row of Table A (compounds l.131 aA-1 to l.131 aA-1 18)

table 132

Compounds I, wherein A is 2,3,4-trichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.132aA-1 to l.132aA-1 18)

table 133a

Compounds I, wherein A is 2,3,5-trichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.133aA-1 to l.133aA-1 18)

table 134

Compounds I, wherein A is 2,3,6-trichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.134aA-1 to l.134aA-1 18)

table 135

Compounds I, wherein A is 2,4,5-trichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.135aA-1 to l.135aA-1 18)

table 136

Compounds I, wherein A is 2,4,6-trichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.136aA-1 to l.136aA-1 18) table 137a

Compounds I, wherein A is 3,4,5-trichlorophenyl and the combination of B and R 1 corresponds to one row of Table A (compounds l.137aA-1 to l.137aA-1 18)

table A

Line BR 1

A-1 phenyl C (CH 3) 3

A-2 2-chlorophenyl C (CH3) 3

A-3 3-chlorophenyl C (CH3) 3

A-4 4-chlorophenyl C (CH3) 3

A-5 2-Fluorophenyl C (CH 3) 3

A-6 3-Fluorophenyl C (CH 3) 3

A-7 4-Fluorophenyl C (CH 3) 3

A-8 2-methylphenyl C (CH 3) 3

A-9 3-methylphenyl C (CH 3) 3

A-10 4-methylphenyl C (CH 3) 3

A-1 1 2-Methoxyphenyl C (CH 3) 3

A-12 3-Methoxyphenyl C (CH 3) 3

A-13 4-Methoxyphenyl C (CH 3) 3

A-14 2-trifluoromethylphenyl C (CH 3) 3

A-15 3-trifluoromethylphenyl C (CH 3) 3

A-16 4-trifluoromethylphenyl C (CH 3) 3

A-17 2-difluoromethoxyphenyl C (CH 3) 3

A-18 3-difluoromethoxyphenyl C (CH 3) 3

A-19 4-difluoromethoxyphenyl C (CH 3) 3

A-20 2,3-dichlorophenyl C (CH 3) 3

A-21 2,4-dichlorophenyl C (CH 3) 3

A-22 2,5-dichlorophenyl C (CH 3) 3

A-23 2,6-dichlorophenyl C (CH 3) 3

A-24 3,4-dichlorophenyl C (CH 3) 3

A-25 3,5-dichlorophenyl C (CH 3) 3

A-26 2,3-difluorophenyl C (CH 3) 3

A-27 2,4-difluorophenyl C (CH 3) 3

A-28 2,5-difluorophenyl C (CH 3) 3

A-29 2,6-difluorophenyl C (CH 3) 3

A-30 3,4-difluorophenyl C (CH 3) 3

A-31 3,5-difluorophenyl C (CH 3) 3

A-32 2,3-dimethylphenyl C (CH 3) 3

A-33 2,4-dimethylphenyl C (CH 3) 3

A-34 2,5-dimethylphenyl C (CH 3) 3

A-35 2,6-dimethylphenyl C (CH 3) 3 line BR 1

A-36 3,4-dimethylphenyl C (CH 3) 3

A-37 3,5-dimethylphenyl C (CH 3) 3

A-38 2-fluoro-3-chlorophenyl C (CH3) 3

A-39 2-fluoro-4-chlorophenyl C (CH3) 3

A-40 2-fluoro-5-chlorophenyl C (CH3) 3

A-41 2-fluoro-6-chlorophenyl C (CH3) 3

A-42 3-fluoro-4-chlorophenyl C (CH3) 3

A-43 3-fluoro-5-chlorophenyl C (CH3) 3

A-44 2-chloro-3-fluorophenyl C (CH 3) 3

A-45 2-chloro-4-fluoro-phenyl C (CH 3) 3

A-46 2-chloro-5-fluoro-phenyl C (CH 3) 3

A-47 3-chloro-4-fluoro-phenyl C (CH 3) 3

A-48 2,3,4-trichlorophenyl C (CH 3) 3

A-49 2,3,5-trichlorophenyl C (CH 3) 3

A-50 2,3,6-trichlorophenyl C (CH 3) 3

A-51 2,4,5-trichlorophenyl C (CH 3) 3

A-52 2,4,6-trichlorophenyl C (CH 3) 3

A-53 3,4,5-trichlorophenyl C (CH 3) 3

A-54 2,3,4-trifluorophenyl C (CH 3) 3

A-55 2,3,5-trifluorophenyl C (CH 3) 3

A-56 2,3,6-trifluorophenyl C (CH 3) 3

A-57 2,4,5-trifluorophenyl C (CH 3) 3

A-58 2,4,6-trifluorophenyl C (CH 3) 3

A-59 3,4,5-trifluorophenyl C (CH 3) 3

A-60 phenyl CH2CH2CH2CH 3

A-61 2-chlorophenyl CH2CH2CH2CH 3

A-62 3-chlorophenyl CH2CH2CH2CH 3

A-63 4-chlorophenyl 3 CH2CH2CH2CH

A-64 2-fluorophenyl CH2CH2CH2CH3

A-65 3-fluorophenyl CH2CH2CH2CH3

A-66 4-fluorophenyl CH2CH2CH2CH3

A-67 2-methylphenyl CH2CH2CH2CH3

A-68 3-methylphenyl CH2CH2CH2CH3

A-69 4-methylphenyl CH2CH2CH2CH3

A-70 2-methoxyphenyl CH2CH2CH2CH3

A-71 3-methoxyphenyl CH2CH2CH2CH3

A-72 4-methoxyphenyl CH2CH2CH2CH3

A-73 2-trifluoromethylphenyl CH2CH2CH2CH3

A-74 3-trifluoromethylphenyl CH2CH2CH2CH3

A-75 4-trifluoromethylphenyl CH2CH2CH2CH3 line BR 1

A-76 2-difluoromethoxyphenyl CH2CH2CH2CH3

A-77 3-difluoromethoxyphenyl CH2CH2CH2CH3

A-78 4-difluoromethoxyphenyl CH2CH2CH2CH3

A-79 2,3-dichlorophenyl CH2CH2CH2CH3

A-80 2,4-dichlorophenyl CH2CH2CH2CH3

A-81 2,5-dichlorophenyl CH2CH2CH2CH3

A-82 2,6-dichlorophenyl CH2CH2CH2CH3

A-83 3,4-dichlorophenyl CH2CH2CH2CH3

A-84 3,5-dichlorophenyl CH2CH2CH2CH3

A-85 2,3-difluorophenyl CH2CH2CH2CH3

A-86 2,4-difluorophenyl CH2CH2CH2CH3

A-87 2,5-difluorophenyl CH2CH2CH2CH3

A-88 2,6-difluorophenyl CH2CH2CH2CH3

A-89 3,4-difluorophenyl CH2CH2CH2CH3

A-90 3,5-difluorophenyl CH2CH2CH2CH3

A-91 2,3-dimethylphenyl CH2CH2CH2CH3

A-92 2,4-dimethylphenyl CH2CH2CH2CH3

A-93 2,5-dimethylphenyl CH2CH2CH2CH3

A-94 2,6-dimethylphenyl CH2CH2CH2CH3

A-95 3,4-dimethylphenyl CH2CH2CH2CH3

A-96 3,5-dimethylphenyl CH2CH2CH2CH3

A-97 2-fluoro-3-chlorophenyl CH2CH2CH2CH3

A-98 2-fluoro-4-chlorophenyl CH2CH2CH2CH3

A-99 2-fluoro-5-chlorophenyl CH2CH2CH2CH3

A-100 2-fluoro-6-chlorophenyl CH2CH2CH2CH3

A-101 3-fluoro-4-chlorophenyl CH2CH2CH2CH3

A-102 3-fluoro-5-chlorophenyl CH2CH2CH2CH3

A-103 2-chloro-3-fluorophenyl CH2CH2CH2CH3

A-104 2-chloro-4-fluorophenyl CH2CH2CH2CH3

A-105 2-chloro-5-fluorophenyl CH2CH2CH2CH3

A-106 3-chloro-4-fluorophenyl CH2CH2CH2CH3

A-107 2,3,4-trichlorophenyl CH2CH2CH2CH3

A-108 2,3,5-trichlorophenyl CH2CH2CH2CH3

A-109 2,3,6-trichlorophenyl CH2CH2CH2CH3

A-1 10 2,4,5-trichlorophenyl CH2CH2CH2CH3

A-1 1 1 2,4,6-trichlorophenyl CH2CH2CH2CH3

A-1 12 3,4,5-trichlorophenyl CH2CH2CH2CH3

A-1 13 2,3,4-trifluorophenyl CH2CH2CH2CH3

A-1 14 2,3,5-trifluorophenyl CH2CH2CH2CH3

A-1 15 2,3,6-trifluorophenyl CH2CH2CH2CH3 line BR 1

A-1 16 2,4,5-trifluorophenyl CH2CH2CH2CH3

A-1 17 2,4,6-trifluorophenyl CH2CH2CH2CH3

A-1 18 3,4,5-trifluorophenyl CH2CH2CH2CH3

From the above tables, the compound names for the individual compounds are derived as follows: For example. is the "Connection / -l3aA-10" (marks added) the compound of formula in which A is 2,5-difluorophenyl (as indicated in Table 3a) and B is 4-methylphenyl and R 1 is C (CH 3) (as indicated in line 10 of Table A). 3

The compounds of the formula I or compositions of the invention are suitable as fungicides for controlling harmful fungi. They are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi including soilborne pathogens which particular from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes diomyceten, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. imperfect fungi) originate. Some are systemically effective and they can be used in crop protection as foliar, dressing and soil fungicides. In addition, they are suitable for controlling fungi which attack, among others, the wood or the roots of plants.

Of particular importance are the compounds I and compositions of the invention for controlling a large number of pathogenic fungi on various crop plants such as cereals, for example. As wheat, rye, barley, triticale, oats or rice; Beets, eg. B. Zucker or fodder beet; Nuclear, stone fruit and soft fruit, such. As apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; Legumes such. As beans, lentils, peas, alfalfa or soy; Oil plants, such. As rape, mustard, olive, sunflower, coconut, cocoa, castor beans, oil palm, peanut or soya; Cucurbits such. As pumpkins, cucumbers or melons; Fiber plants, such. As cotton, flax, hemp or jute; Citrus fruits such. As oranges, lemons, grapefruit or tangerines; Vegetables such. As spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, squash or peppers; Laurel family such. As avocados, cinnamon or camphor; Energy and raw material plants, for example. As corn, soybeans, wheat, canola, sugarcane and oil palm; Corn; Tobacco; Nuts; Coffee; Tea; bananas; Wine (Table and grapes); Hop; Grass, z. B. turf; Süßkraut (Stevia rebaudania); Rubber plants; Ornamental and forest plants, for. B. Blumen, shrubs, deciduous and coniferous trees, and on the propagation material, for. Example seeds, and the crop material of these plants.

Preferably, the compounds I, or compositions of the invention for controlling a variety of fungal pathogens in agricultural cultures, z. As potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; Fruit, grapes, ornamentals and vegetables such. As cucumbers, tomatoes, beans and pumpkins also on the propagation material, for. Example seeds, and the crop material of these plants.

The term plant propagation materials comprises all generative parts of the plant, for. B. Seed, and vegetative parts of plants, such as cuttings and tubers (for. Example potatoes), which can be used to propagate a plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots and other plant parts including seedlings and young plants which are transplanted after germination or emergence. The young plants can by a partial or complete treatment, for. B. be protected by dipping or casting, from fungi.

The treatment of plant propagation materials with compounds I and the compositions according to the invention is used for controlling a variety of fungal pathogens in crops of cereals, z. As wheat, rye, barley or oats; Rice, corn, cotton and soybeans used.

The term crop plants also includes those plants, which have been modified by breeding, mutagenesis or genetic engineering methods including on the market or in development biotechnological agricultural products (see eg http://www.bio.org/speeches/pubs/er/agri_products .asp). Genetically modified plants are plants, which genetic material has been altered in a way that does not occur (ie, recombination of the genetic information) in natural conditions by crossing, mutations or natural recombination. Here are a generally or more genes integrated into the genome of the plant in order to improve the properties of the plant. Such genetic modifications include post-translational modifications of proteins, oligo- or polypeptides, for example by glycosylation or attachment of polymers such as prenylated, acetylated or farnesylated moieties or PEG moieties.

Examples are plants (ALS) inhibitors through breeding and genetic engineering tolerance to certain classes of herbicides, such as hydroxyphenylpyruvate ruvat dioxygenase (HPPD) inhibitors, acetolactate synthase such. B. sulfonylureas (EP-A 257 993 US 5,013,659) or imidazolinones (z. B.

US 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. B. Glyphosate (see, e.g., WO 92/00377.), Glutamine synthetase (GS) - inhibitors such. have as glufosinate (see, for. example, EP-A 242 236, EP-A 242 246) or Oxynil- herbicides (see, for. example, US 5,559,024) were acquired. z was by breeding and mutagenesis. B. Clearfield ® canola (BASF SE, Germany) is generated, which is tolerant to imidazolinones, z. B. 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 ® (glufosinate-resistant, Bayer CropScience, Germany) are available.

Furthermore, also included are plants, which with aid of genetic engineering one or more toxins, such. B. those of the bacterial strain Bacillus produce. Toxins produced by such genetically modified plants, such environmentally grasp. . B. insecticidal proteins from Bacillus spp, especially B. thuringiensis endotoxins such as CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, or Cry34Ab1 Cry35Ab1; or vegetative insecticidal proteins (VIP), for example. As VIP1, VIP2, VIP3, or VIP3A; Insecticidal proteins of bacteria colonizing nematodes, for example. Example Photorhabdus spp. or Xenorhabdus spp .; Toxins of animal organisms men such. Example wasp - spider or scorpion toxins; fungal toxins such. B. from Streptomyces tomyceten; plant lectins such. As pea or barley; agglutinins; Proteinase inhibitors, such. As trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome-inactivating proteins (RIPs), z. As ricin, maize-RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing enzymes such. B. 3-hydroxy steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors or HMG-CoA reductase; ion channel blockers such. B. inhibitors of sodium or calcium channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin); Stilbene, bibenzyl synthase, chitinases and glucanases. These toxins can be used in the plants as pretoxins, hybrid proteins, truncated or otherwise modified proteins are produced. Hybrid proteins are characterized by a new combination of different protein domains (see, eg., 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 such. As set out in the above mentioned publications. Many of the toxins mentioned above bestow the plants that produce them, thinking let a tolerance to pests from all taxonomic classes of arthropods, especially to beetles (Coeleropta) (Diptera) and

Butterflies (Lepidoptera) and to nematodes (Nematoda). Genetically engineered plants which have one or more genes that encode toxins of insecticides produce z. As described in the above mentioned publications and some are commercially available, such. 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 Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyl transferase [PAT]); NuCOTN ® 33B (cotton cultivars producing the toxin CrylAc), Bollgard ® I (cotton cultivars producing the toxin CrylAc), Bollgard ® II (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 ®, Bt1 1 (z. B. Agrisure ® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties that the toxin and the CrylAb PAT enzyme production), MIR604 from Syngen- ta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe SA, Belgium (corn varieties which the toxin Cry3Bb1 produce), IPC 531 from Monsanto Europe SA, Belgium (cotton varieties which produce a modified version of the toxin CrylAc) and 1507 (Pioneer Overseas Corporation, Belgium corn varieties which produce the toxin Cryl F and the PAT enzyme).

Furthermore, also included are plants, which genetic engineering to produce with the aid of one or more proteins which cause increased resistance or Widerstandfähig- ness against bacterial, viral or fungal pathogens, such. As so-called pathogenesis-related proteins (PR proteins, see EP-A 0,392,225), resistance proteins (eg., Potato varieties which produce two genes for resistance to Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4-lyso-zym (z. B. potato varieties which are resistant criteria by producing this protein to Bak as Erwinia is amylvora).

Furthermore, also included are plants whose productivity has been improved with the aid of recombinant methods by z. For example, the potential yield (for. Example biomass, grain yield, starch, oil or protein content), tolerance to drought, salinity or other limiting environmental factors or the resistance to pests and fungal, bacterial and viral pathogens.

Furthermore Also included are plants whose ingredients particular to improve human or animal nutrition using genetic engineering methods have been changed by such. 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 Also included are plants that have been modified for improved production of raw materials using genetic engineering methods by such. As the amylopectin content of potatoes (Amflora ® potato, BASF SE, Germany) has been increased.

Specifically, the compounds I and cooperation settlement of the invention for controlling the following plant diseases are:

Albugo spp. (White rust) on ornamentals, vegetables crops (for example: A. Candida) and sunflowers (for tragopogonis.); Alternaria spp. (Ink, black spot) on vegetables, oilseed rape (eg. BA brassicola or A brassicae), sugar beet (eg. Tenuis), fruit, rice, soybeans and also on potatoes (eg. Solani or A. alternata) and To- maten ( z. A. solani or A. alternata) and Alternaria spp. (Black head) on wheat; Aphanomyces spp. on sugar beet and vegetables; Ascochyta spp. in cereals and vegetables, for example. BA tritici (leaf blotch) 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 corn, for example. B. glume blotch (ß. Sorokiniana) on cereals and, for example, ß. oryzae on rice and turf; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (for example wheat or barley.); Botryosphaeria spp. ( 'Black Dead Arm Disease') on grapevines (. Eg ß obtusa.); Botrytis cinerea (Teleomorph: Botryotinia fuckeliana: gray mold, rot) on soft fruit and pome fruit (including strawberries), vegetables (such as lettuce, carrots, celery and cabbage), rapeseed, flowers, grapevines, forest crops and wheat (ear mold); Bremia lactucae (downy mildew) on lettuce; Cera tocystis (syn. Ophiostoma) spp. (Blue stain) to deciduous and coniferous trees, for example. C. ulmi (Dutch elm disease, Dutch elm disease) on elms; Cercospora spp. (Cercospo- ra-leaf spots) on corn (. Eg C. zeae-maydis), rice, sugar beet (. Eg C. beticola), sugar cane, vegetables, coffee, soybeans (. Z BC sojina or C. kikuchii) and rice; Cladosporium spp. of tomato (example C. fulvum:. Samtflecken disease), and cereals, for example. BC herbarum (black head) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorphic: Helminthosporium or Bipolaris) spp. (Leaf spot) on corn (. Z BC carbonum), cereals (. Eg C. sativus, anamorph: B. na sorokinia-: blotch) and rice: (z BC miyabeanus, Anamorphic H. oryzae.) Colletotrichum (Teleomorph: Glomerella) spp. (Focal spots, anthracnose) on cotton, corn (for example C. gossypii.) (For example C. graminicola. Stem rot and burn), soft fruit, potatoes (for BC coccodes. Wilt), beans (for example C. lindemuthianum.) And soybeans (for example. BC truncatum); Corticium spp., Z. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., Z. BC oleaginum of olive; Cylindrocarpon spp. (.., For example, fruit tree canker or vines, teleomorph: Nectria or Neonectria spp) on fruit trees, Weinre- ben: and many ornamental trees (z BC liriodendri, teleomorph Neonectria liriodendri, black foot disease). Dematophora (teleomorph: Rosellinia) necatrix (root / stem rot rot) on soybeans; Diaporthe spp. z. D. phaseolorum (stem disease) on soybeans; Drechslera (Helminthosporium Syn, Teleomorph. Pyrenophorä) spp. on corn, cereals, such as barley (for example D. teres, net blotch.) and wheat (for example D. tritici repentis: DTR leaf spot.), rice and lawns; Esca disease (dieback, apoplexy) on grapevines, caused by Formitiporia (Syn Phellinus.) Punctata, F. mediter- Ranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe spp. in core (. £ pyri) and soft fruit (£ Veneta: focal spots.) and grape vine (£ ampelina: focal spots.); Entyloma oryzae (leaf blight) on rice; Epicoccum spp. (Black head) on wheat; Erysiphe spp. (Powdery mildew) on sugar beet (£. Betae), vegetables (eg. E. pisi), such as cucumber (eg. E. cichoracearum) and cabbage plants, such as oilseed rape (e.g., BE cruciferarum) .; woody plants on fruit trees, vines and many ornamental; Eutypa lata (Cy tosporina lata, syn Libertella blepharis Eutypa cancer or -Absterben, Anamorphic.) Exserohilum (syn. Helminthosporium) spp. on corn (. as E. turcicum); Fusarium (Teleomorph: Gibberella) spp. (Wilt, root and stem rot) on various plants, such. F. graminearum or F. culmorum (root rot and deaf or ear blight) on cereals (for example wheat or barley.), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on corn; Gaeumannomyces graminis () on cereals (for example wheat or barley.) And corn; Gibberella spp. on cereals (for BG zeae.) and rice (e.g. BG fujikuror Bakanae disease..); Glomerella cingulata on grapevines, pome fruit and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on grapevines; Gymnosporangium spp. on Rosaceae and juniper, for example. G. sabinae (pear rust) on pears; Helminthosporium spp. (Syn Drechslera, Teleomorph: Cochliobolus.) On corn, cereals and rice; Hemileia spp., Z. BH vastatrix (coffee leaf rust) on KAF fee; Isariopsis clavispora (syn Cladosporium vitis.) On grapevines; Macrophomina phase-seolina (syn. Phaseoli) (root / stem rot) on soybeans and cotton; Micro dochium (Syn Fusarium.) Nivale (snow mold) on cereals (for example wheat or barley.); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., Z. M. laxa, M. fructicola and M. fructigena (bloom and twig blight) on stone fruits and on the other ren Rosaceae; Mycosphaerella spp. on cereals, bananas, soft fruit and peanuts such. M. graminicola (anamorph: Septoria tritici, Septoria leaf blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (Downy mildew) on cabbage (. E.g. P. brassicae), rape, bulbous plants, tobacco (P tabacina) and soybeans (e.g. BP manshuri- approx.) (E.g. BP parasitica.) (E.g. BP destructor.); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phia- lophora spp. z. B. on grapevines (for example P. tracheiphila and P. tetraspora.) And soybeans (for example P. gregata: stem disease). Phoma lingam (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spot) on sugar beet; Phomopsis spp. on sunflowers, vines (. for example P. viticola: black spot disease), and soybean (e.g., stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum.); Physoderma May- dis (glume blotch) on corn; Phytophthora spp. (Wilt, root, leaf, stem and fruit rot) on various plants, such as bell peppers and cucurbits (eg. BP capsici), soybeans (for example, BP megasperma, syn. P. sojae), potatoes and tomatoes (for example. P. infestans: late blight) and deciduous trees (for example P. ramorum pending sudden oak death);.. Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., Z. P. viticola (grapevine downy mildew, downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (Powdery mildew) on rosaceous plants, hop, pome and soft fruits, for example. P. leucotricha on apple; Polymyxa spp., Z. As in cereals, such as barley and wheat (P. graminis) and sugar beet (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, Teleomorph: Tapesia yallundae) on cereals, for. For example, wheat or barley; Pseudoperonospora (downy mildew) on various plants, for example. P. cubensis on cucurbits or P. humili on hops; Pseudo Pezicula tracheiphila (red fire, anamorph: Phialophora) on grapevines; Puccinia spp. (Rusts) on various plants, for example. P. triticina (brown rust of wheat), P. striiformis (yellow rust), P. hordei (dwarf rust), P. graminis (stem rust) or P. recondi- ta (rye Brown rust) on cereals, such as. For example, wheat, barley or rye, and asparagus (for example P. asparagi.); Pyrenophora (anamorph: Drechslera) tritici repentis (leaf blotch) on wheat or P. teres (net blotch) on barley; Pyricularia spp., Z. BP ory- zae (Teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on lawns and cereals; Pythium spp. (Damping-off) on lawn, rice, corn, wheat, cotton, rapeseed, sunflower, sugar beet, vegetables and other plants (for example P. ultimum or P. aphanidermatum.); Ramularia spp., Z. R. collo-cygni (Sprenkel- disease / sunburn complex / Physiological leaf spots) on barley and R. beticola on sugar beet; Rhizoctonia spp. on cotton, rice, potatoes, lawns, corn, rapeseed, potatoes, sugar beet, vegetables and on various other plants such. R. solani (root / stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (sharp eye spot) on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (leaf spots) on barley, rye and triticale; Sarocladium oryzae and S. at- tenuatum (Blattscheidenfäule) on rice; Sclerotinia spp. (Stem or white rot) on vegetables and field crops, such as rapeseed, sunflower (. For example, Sclerotinia sclerotiorum) and soybeans (for example S. rolfsii.); Septoria spp. on various plants, such. BS glycines (leaf spot) on soybeans, S. tritici (Septoria leaf blotch) on wheat and S. (syn Stagonosporä.) Nodorum (Leaf and glume blotch) on cereals; Uncinula (syn Erysiphe.) Necator (powdery mildew, anamorph: Oidium tuckeri) on grapevines; Se tospaeria spp. (Leaf spots) on corn (. Z BS turcicum, Helminthosporium turcicum Syn.) And turf; Sphacelotheca spp. (Smut) on corn, (for BS reiliana: Piston fire.), Millet and sugarcane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonosporä spp. on cereals, for. S. nodorum (Leaf and glume blotch, teleomorph: Leptosphaeria [syn Phaeosphaeria.] Nodorum) on wheat; SYNCHYTRIUM ENDOBIOTICUM on potatoes (potato wart disease); Taphrina spp., Z. T. deformans (leaf curl) pruni on peach and T. (pocket disease) on plums; Thielaviopsis spp. (Black root rot) on tobacco, pome fruit, vegetable crops, soybeans and cotton, for example. BT basicola (Syn Chalara elegans.); Tilletia spp. (Bunt or stinking smut) on cereals, such. T. tritici (syn T. caries, wheat bunt.) And T. controversa (dwarf bunt) on wheat; Typhula incarnata (snow mold) on barley or wheat; Urocystis spp., Z. BU occulta (stem blight) on rye; Uromyces spp. (Rust) on vegetables, such as beans (e.g. BU appendiculatus, syn U. phaseoli..) And sugar beet (for BU betae.); Ustilago spp. (Smut) on cereals overall (e.g. U. nuda and U. avaenae.), Corn (e.g. U. maydis: corn smut.) And sugar cane; Venturia spp. (Scab) on apples (for example V. inaequalis.) And pears; and Verticillium spp. (Leaf and shoot wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, such. V. dahliae on strawberries, rape, potatoes and tomatoes.

The compounds I and compositions of the invention are also suitable for controlling harmful fungi in the protection of stored products (also from crops) and in the materials and buildings. The term "materials and buildings" includes the protection of industrial and non-living materials such. As adhesives, glues, wood, paper and cardboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fibers and fabrics, against the infestation and destruction by undesirable microorganisms such as fungi and bacteria. In wood and material protection, in particular the following harmful fungi are respected:...... Ascomycetes, such as Ophiostoma spp, Cerato- Cystis spp, Aureobasidium pullulans, Sclerophoma spp, Chaetomium spp, Humicola spp, Petri spp, Trichurus spp .; Basidiomycetes such 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., Altemaria spp., Paecilomyces spp. and Zygomycetes such as / Wu cor spp, beyond the protection of materials the following yeasts:. Candida spp. and Sac charomyces cerevisiae.

The compounds of formula I can be present in different crystal modifications whose biological activity may differ. These are included in the scope of the present invention.

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

The term "plant health" includes those states of a plant and / or its crop, designated individually by different indicators or determined in combination with one another, such as. Yield (z. B. increased biomass and / or elevated ter content utilizable ingredients), plant vigor (for. example, increased plant growth and / or greener leaves ( "greening effect")), quality (for. example increased content or composition of certain ingredients) and tolerance to biotic and / or abiotic stress. The indicators mentioned here for a state of plant health may occur independently or are mutually dependent.

The compounds I are employed as such or in form of a composition by treating the harmful fungi, their habitat or against fungal attack plants to be protected, plant propagation materials, such. Example seed, the soil, areas, materials or spaces with a fungicidally effective amount of the compounds I treated comparison. Application can be both before and after infection of the plants, plant propagation materials,. Example seed, the soil, the effected areas, materials or rooms by the fungi.

Plant propagation materials may be treated as such or with a composition containing at least one compound I prophylactically or already before sowing or during or even before transplanting with supply connections I.

Moreover, the invention agrochemical compositions comprising a solvent or solid carrier and at least one compound I and to their use for controlling harmful fungi is concerned.

An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" means an amount of the agrochemical composition or of the compound I, the zen for controlling Schadpil- on crop plants or in the materials and buildings is sufficient and not too to a substantial damage to the treated crops. such an amount can vary within a wide range and is used by many factors, such as, for example, plant the the harmful fungus that each treated culture or material, the climatic conditions and compounds impressive - enced.

The compounds I, their N-oxides and their salts can be converted into the customary for agrochemical compositions types such. As solutions, emulsions, suspensions, dusts, powders, pastes and granules. The type of composition depends on the particular intended use; it should ensure a fine and uniform distribution of the compound of the invention in any case.

Examples for composition types are here Suspensions (SC, OD, FS), e- mulgierbare 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 are either soluble in water (soluble) or dispersible (wettable) may be as well as gels for treatment of plant propagation materials such as seeds (GF).

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

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 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 Grubenmann, A .: Formulation technology (Wiley VCH Verlag, Weinheim, 2001).

The agrochemical compositions may further contain auxiliaries customary for crop protection agents, wherein the selection of the aid according to the specific application form or the active compound.

Examples of suitable auxiliaries are solvents, solid carriers, surface-active agents (such as further solubilizers, protective colloids, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, optionally colorants and adhesives (for. Example, for seed treatment) ,

As the solvent, water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore oils coal tar and line oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg 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 acids and fatty acid esters and strongly polar solvents, for example amines such as N-methylpyrrolidone. In principle, solvent mixtures can be used as well as mixtures of the aforementioned solvents and water.

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

Suitable surfactants (adjuvants, wetting agents, adhesives, dispersants or emulsifiers) are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic ren, z. 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- alkyl- and alkylarylsulfonates, Al, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers of condensation products of sulfonated naphthalene and its derivatives ned with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, Polyoxye- octylphenol, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl, tributylphenyl, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol holethylenoxid condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene pylenalkylether, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and proteins, denatured proteins, polysaccharides (eg Methylc ellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol ® types, Clariant, Switzerland), poly carboxylate (Sokalan ® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lu pamin ® types, BASF, Germany), polyethylenimine (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 can be added to stabilize the composition. Examples of bactericides are those based on dichlorophen and benzyl alcohol hemiformal (Proxel ®.. Of Messrs. ICI or Acetide ® RS from Thor Chemie and Kathon ® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acetide ® MBS Fa. 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 sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned under the names Rhodamine B, CI Pigment Red 1 12 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 yellow 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 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 are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, XY lol, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.

Powders, dusts and broadcasting agents may be prepared with at least one solid carrier by mixing or jointly grinding the compounds I and, if present, other active ingredients.

Granules, for. Example coated, impregnated and homogeneous granules, can advertising at least produced a solid carrier by binding the active compounds to. Solid carriers are eg. For example, mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, Calzi- implement and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate ureas, and vegetable products such as grain flour, tree bark, wood and nutshell meal, cellulose powders and other solid carriers.

Examples of composition types are:

1 . Composition types for dilution with water

i) Water-soluble concentrates (SL, LS)

10 parts by weight of the active compounds are dissolved in 90 parts by weight of water or a water- soluble solvent. Alternative, wetters or other auxiliaries are added. On dilution in water, the active compound dissolves. Obtained in this way, a composition with 10 wt .-% active ingredient.

ii) Dispersible concentrates (DC)

20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersing agent such. As polyvinylpyrrolidone dissolved. When diluted with water gives a dispersion. The active compound content is 20 wt .-% iii) Emulsifiable concentrates (EC) 15 parts by weight of the active compounds are dissolved with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) in 75 parts by weight of xylene. Dilution with water gives an emulsion. The composition has 15% by weight active substance content.

iv) Emulsions (EW, EO, ES)

25 parts by weight of the active compounds are dissolved with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) in 35 parts by weight of xylene. This mixture is added by means of an emulsifying machine (z. B. Ultra-Turrax) in 30 parts by weight of water and made into a homogeneous emulsion. Dilution with water gives an emulsion. The composition has an active ingredient content of 25 wt .-%.

v) Suspensions (SC, OD, FS)

20 parts by weight of the active compounds are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent in a stirred ball mill to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active substance content in the composition is 20 wt .-%.

vi) Water-dispersible and water-soluble granules (WG, SG)

50 parts by weight of the active compounds are ground finely with addition of dispersants and wetters of 50 parts by weight and by means of technical appliances (for. Example extrusion, spray tower, fluidized bed) prepared as water-dispersible or water-soluble granules. Dilution with water gives a stable dispersion or solution of the active compound. The composition has an active ingredient content of 50 wt .-%. vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the active compounds are ground mill with addition of 25 parts by weight of dispersants, wetters and silica gel in a rotor-stator. Dilution with water gives a stable dispersion or solution of the active compound. The active ingredient content of the composition is 75 wt .-%.

viii) gels (GF)

In a ball mill 20 parts by weight of the active ingredients, 10 parts by weight of dispersants, 1 part by weight are ground source means ( "gelling agent") and 70 parts by weight of water or an organic solvent to give a fine suspension. The dilution with water gives a stable suspension with active compound content of 20 wt .-%. 2. composition types to be applied undiluted

ix) Dustable powders (DP, DS)

5 parts by weight of the active compounds are ground finely and mixed intimately with 95 parts by weight of kaolin feinteili- gem. This gives a dustable product having 5 wt .-% active ingredient.

x) Granules (GR, FG, GG, MG)

0.5 parts by weight of the active compounds is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active substance content of 0.5 wt .-%.

xi) ULV solutions (UL)

10 parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent eg. B. xylene dissolved. This provides a composition for the di- rektapplikation with 10 wt .-% active ingredient.

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

For the treatment of plant propagation materials, particularly seeds, are 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 propagation materials, particularly seeds, undiluted or, preferably, diluted. Here, the corresponding composition may be 2 to 10-fold diluted, so that 60% wt .-%, preferably 0.1 to 40% wt .-% of active ingredient present in the compositions used for the stain to 0.01 tons. The application can take place before or during sowing. The treatment of plant propagation material, in particular the treatment of seeds, are known in the art, or by dusting, coating, pelleting, dipping or soaking the plant propagation material, wherein the treatment is preferably carried out 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 preferred. Typically, such compositions contain 1 to 800 g / l active substance, 1 to 200 g / l tensides, 0 to 200 g / l antifreeze agents, 0 to 400 g / l binders, 0 to 200 g / l colorants and solvents, preferably water ,

The compounds can be used as such or in the form of their compositions, eg. B. be applied in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, spreading, swabbing, dipping or pouring. The composition types depend entirely on the intended purposes; they should ensure the finest possible distribution of the active compounds in each case.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agent, tackifier, dispersant or emulsifier. but it can also consist of active substance, wetter, tackifier, dispersant or emulsifier and solvent or oil, and such concentrates are prepared contingent tulle, which are suitable for dilution with water.

The active ingredient concentrations in the finished formulations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.

The active compounds can also be used with success in ultra-low-volume process (ULV), it being possible to apply compositions comprising over 95 wt .-% active compound or even the active ingredient without additives.

The application rates for the use in crop protection depending on the type of effect desired, from 0.001 to 2.0 kg of active compound per ha, preferably from 0.005 to 2 kg per ha, particularly preferably between 0.05 and 0.9 kg of per ha, in particular from 0.1 and 0.75 kg per ha.

In the treatment of plant propagation materials such. Example seed, are generally amounts of active compound of 0.1 to 1000 g / 100 kg of propagation material or seeds, preferably 1 to 1000 g / 100 kg, particularly preferably 1 to 100 g / 100 kg, in particular 5 to 100 g / 100 kg used.

When used in the protection of materials or stored products, the amount of active ingredient depends on the type of application area and on the desired effect. Customary application rates in the protection of materials, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.

To the active substances or the compositions comprising them can be added Various types of oils, wetters, adjuvants, herbicides, bactericides, other fungicides and / or pesticides, if appropriate also only immediately prior to use (tank mix). These means can be the erfindungsge- MAESSEN compositions in a weight ratio of 1: 100 to 100: 1, preferably 1: 1 mixed: 10 to 10 degrees.

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

The compositions of the invention may also be present in the application form as fungicides together with other active ingredients, for. Example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre mix or, if appropriate, not until immediately prior to use (tank mix).

Mixing the compounds I or the compositions comprising them with one or more further active compounds, in particular fungicides, the spectrum of action can for example be broadened or resistance to prevent the development in many cases. In many cases obtained here synergistic effects see.

The list of active substances with which the compounds of the invention can be used is intended to illustrate the possible combinations but does not limit:

A) strobilurins:

Azoxystrobin, dimoxystrobin, Coumoxystrobin, Coumethoxystrobin, enestroburin, Fenaminstrobin, Fenoxystrobin / Flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, Pyrametostrobin, Py- raoxystrobin, pyribencarb, Triclopyricarb / Chlorodincarb, trifloxystrobin, 2- [2- ( 2,5-dimethylphenoxymethyl) phenyl) -3-methoxy-acrylic acid methyl ester, 2- (2- (3- (2,6-di- chlorophenyl) -1-methyl-allylideneaminooxymethyl) phenyl) -2-methoxyimino-N-methyl - acetamide;

B) carboxamides:

- carboxanilides: benalaxyl, benalaxyl-M, Benodanil, bixafen, boscalid, carbonyl xin, fenfuram, fenhexamid, 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-1 H-pyrazol-4-car- boxamid), penthiopyrad, sedaxane, tecloftalam, Thifluzamide, tiadinil, 2-amino-4-methyl-thiazol-5-carboxanilide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1 - methyl-1 H-pyrazol-4- carboxamide, N- (4'-Trifluormethylthiobiphenyl-2-yl) -3-difluoro-methyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2- (1, 3,3-trimethyl-butyl) phenyl) -1, 3- dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;

- Carbonsäuremorpholide: dimethomorph, flumorph, Pyrimorph;

- benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide;

- other carboxamides: carpropamid, diclocymet, mandipropamid, oxytetracycline, silthiofam, N- (6-methoxy-pyridin-3-yl) cyclopropanecarboxamide;

C) azoles:

- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, Oxpo- conazole, paclobutrazol, penconazole, propiconazole , prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole; - imidazoles: cyazofamid, Imazalil, Imazalilsulfat, pefurazoate, prochloraz, triflumizole;

- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

- others: ethaboxam, etridiazole, hymexazole, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxy-phenyl) -isoxazole-5-yl] -2-prop-2-ynyloxy-acetamide ;

D) nitrogen-containing heterocyclyl

- pyridines: fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] - pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethyl-isoxazolidin-3-yl] -pyridine (Pyrisoxazol);

- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, Ferimzone, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;

- piperazines: triforine;

- pyrroles: fludioxonil, fenpiclonil;

- morpholines: aldimorph, dodemorph, Dodemorphacetat, fenpropimorph, tridemorph;

- piperidines: fenpropidin; - dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin;

- non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazol-1 - thiocarbonsäureS allyl ester (fenpyrazamine) ;

- Other: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, cap tan, chinomethionat, dazomet, debacarb, Diclomezine, difenzoquat, Difenzoquat- methyl sulfate, fenoxanil, folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, Qui - noxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro- 1 - (4,6-dimethoxy-pyrimidin-2-yl) -2-methyl-1 H-benzoimidazole, 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluoro-phenyl) - [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) carb aminsäure- (4-fluorophenyl) ester;

F) Other fungicides

- guanidines: dodine, dodine free base, guazatine, Guazatinacetat, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilate);

- Antibiotics: ycin kasugamycin Kasugamycinhydrochlorid hydrate, polyoxins, Streptom-, validamycin A;

- nitrophenyl derivatives: binapacryl, dicloran, dinobuton, dinocap, nitro Thal-isopropyl, tecnazene;

- organometallic compounds: fentin salts, such as fentin-acetate, fentin chloride, fentin hydroxide;

- sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane;

- organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;

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

- inorganic active substances: phosphorous acid and its salts, Bordeaux mixture, copper fersalze such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

- Biological fungicide, plant strengtheners: Bacillus subtilis strain NRRL no. B-21661 (for example, the products Rhapsody ®, SERENADE ® MAX and SERENADE ® ASO of Fa. AgraQuest, Inc., USA.), Bacillus pum / '/ us strain NRRL no. B- 30087 (eg SONATA ® and BALLAD ® Plus from. AgraQuest, Inc., USA), Ulocladi- to oudemansii (eg BOTRY ZEN Fa. BotriZen Ltd., New Zealand), chitosan (eg ARMOR ZEN Fa. BotriZen Ltd., New Zealand). - others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (cyclo- propylmethoxyimino- (6-difluoromethoxy-2,3-difluoro-phenyl) - methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylforma- midin, N' - (4- (4-fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-meth- ylformamidin, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl- propoxy) phenyl) - N-ethyl-N-methyl formamidine, N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl- propoxy) -phenyl) -N-ethyl-N-methyl formamidine, 2- { 1 - [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -thiazole-4-carboxylic acid-methyl- (1, 2,3,4-tetra- hydronaphthalen-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-tetrahydronaphthalen-1 -yl amide, acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl-es ter, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester, A / -methyl-2- {1 - [2- (5-meth - yl-3-trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -A / - [(1 R) -1, 2,3,4-tetrahydro-naphthalen-1 - yl] -4-thiazolecarboxamide, 1 - [4- [4- [5- (2,6-difluorophenyl) -4,5-dihydro-3- isoxazolyl] -2-thiazolyl] -1-piperidinyl] -2- [ 5-methyl-3- (trifluoromethyl) -1 H-pyrazol-1 - yl] ethanone;

G) Growth regulators

Abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-Dimethylpuridin, ethephon, flumetralin, flurprimidol, fluthiacet, research chlorfenuron, gibberellic acid, inabenfide , indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), metconazole, naphthaleneacetic acid, N-6-benzoyl zyladenin, paclobutrazol, prohexadione (prohexadione-calcium), Prohydrojasmon, Azuron Thidi-, triapenthenol, tributylphosphorotrithioate, 2,3 , 5-tri-iodobenzoic acid, Trinexa- pac-ethyl and uniconazole;

H) herbicides

- acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, Flufena- cet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;

- amino acid analogs: bilanafos, glyphosate, glufosinate, sulfosate;

- aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, Ha- loxyfop, Metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;

- bipyridyls: diquat, paraquat;

- carbamates and thiocarbamates: mepiperat asulam, butylate, carbetamide, desmedipham, di-, Eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, focarb Prosul-, pyributicarb, thiobencarb, triallate;

- Cyclohexanedione: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;

- dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, Prodi amines Triflura- lin;

- diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, Lac tofen, oxyfluorfen;

- hydroxybenzonitriles: bromoxynil, dichlobenil, ioxynil;

- imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, Imaze- thapyr;

- phenoxy acetic 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, pilot cloram, picolinafen, thiazopyr;

- sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl,

Chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, Fluce- tosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, Prosul- furon, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-propyl-imidazo [1, 2-b] pyridazin-3-yl) sulfonyl) -3- (4,6-dimethoxy-pyrimidin- 2-yl) urea;

- triazines: mitron ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, meta-, metribuzin, Prometryne, simazine, terbuthylazine, terbutryn, triaziflam;

- ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metal thabenzthiazuron, tebuthiuron;

- other acetolactate synthase inhibitors: bispyribac-sodium, Cloransulam- methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho sulfamuron, penoxsulam, propoxycarbazone, Pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, Pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;

- Other: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, Bencarba- zon, Benfluresat, benzofenap, bentazone, benzobicyclon, bromacil, bromobutide, Bu tafenacil, butamifos, Cafenstrole, carfentrazone, cinidon-Ethlyl, Chlorthal, Cinme- thylin, clomazone , cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslers monoceras, endothal, ethofumesate, etobenzanid, Fentrazamide, Flumi- clorac-pentyl, flumioxazin, flupoxam, Fluorochloridon, flurtamone, indanofan, Isoxa- ben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsenic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, Pyraclonil, pyraflufen-ethyl, Pyrasulfotol, pyrazoxyfen, pyrazolynate, noclamin Qui, saflufenacil, sulcotrione, sulfentrazone, terbacil, Tefuryltrion, tembotrione, Thiencarbazon, 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-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl) -phenoxy] -pyridine-2 yloxy) -acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidin-4-carboxylsäuremethylester, 6-chloro-3- (2-cyclopropyl-6-methyl-phenoxy) - pyridazin-4-ol, 4- amino-3-chloro-6- (4-chloro-phenyl) -5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxy-phenyl ) -pyridin-2-carboxylsäuremethylester and 4-amino-3-chloro-6- (4-chloro-3-dimethylamino-2-fluoro-phenyl) -pyridin-2- carboxylsäuremethylester;

I) Insecticides

- organo (thio) phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, at Dimetho-, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, Methamido- phos, methidathion , methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, Phenthoate, Phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, Sulprophos, tetra- chlorvinphos, terbufos, triazophos, trichlorfon;

- carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, Triazamate;

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

- inhibitors of insect growth: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, Cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, He xaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; Buprofezin, Diofe- nolan, hexythiazox, etoxazole, Clofentazin; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen rotetramat, spiromesifen, SPI;

- Nicotine Receptor agonists / antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 - (2-chloro-thiazol-5-yl methyl) -2-nitrimino-3,5-dimethyl- [1, 3,5] triazinane;

- GABA antagonists: endosulfan, ethiprole, fipronil, Vaniliprol, Pyrafluprol, pyriprole, 5-amino-1 - (2,6-dichloro-4-methyl-phenyl) -4-sulfinamoyl-1 H-pyrazol-3-thiocarboxylic acid amide;

- Macrocyclic lactones: abamectin, emamectin, milbemectin, lepimectin, Spino- sad, spinetoram;

- Mitochondrial electron transport chain inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;

- METI II and III compounds: acequinocyl, Fluacyprim, hydramethylnon;

- uncoupling: chlorfenapyr;

- inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, Fenbutatin- oxide, propargite;

- molting inhibitors insects: cryomazine;

- inhibitors, mixed function oxidases': piperonyl butoxide;

- Sodium channel blockers: indoxacarb, metaflumizone; - Other: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamide, chlorantraniliprole, Cyazypyr (HGW86); nopyrafen Cye-, Flupyrazofos, Cyflumetofen, amidoflumet, Imicyafos, bistrifluoron and Py rifluquinazon.

The present invention also relates to fungicidal compositions comprising at least one compound of general formula I and at least one further crop protection agent, in particular at least one fungicidally active compound, z. B. one or example, contain 1 or 2 active substances of the abovementioned groups A) to F), and optionally one or more agriculturally suitable carrier more. With a view to reducing the application rates, these mixtures are of interest because many at a reduced total amount of active compounds show an improved activity against harmful fungi, in particular for certain indications. By simultaneous joint or separate application of compound (s) I with at least one active substance from groups A) to I), the fungicidal efficacy can be enhanced in a superadditive manner.

Co-administration in the context of this application means that at least one compound I and at least one further active ingredient (simultaneously at the site of action ie to be controlled plant-damaging fungi and their habitat, such as infected plants, plant propagation materials, in particular seed, soils, materials or spaces as well as the front fungal infestation to be protected plants, plant propagation materials, particularly seeds, soils, materials or spaces) are present in an amount sufficient for effective control of fungal growth amount. This can be achieved, that the compounds I and at least one further active compound jointly in a common active compound preparation or in at least two separate active-substance preparations or by applying the active compounds in succession at the site of action, wherein the interval between the individual active ingredient applications chosen so is that the first is, active at the time of application of the / of the other active substance s / substances present in sufficient quantity at the site of action. The order in which the active compounds is of minor importance.

In binary mixtures, that is, 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 other active ingredient depends on the weight ratio of compound I to the first further active ingredient of the properties of the respective active compounds, usually it is in the range from 1: 100 to 100: 1, often in the range of 1: 50 to 50: 1, preferably in the range of 1: 20 to 20: 1, more preferably in the range from 1: 10 to 10: 1, in particular in the range from 1: 3 to 3: 1.

In ternary mixtures, ie compositions of the invention containing an active compound I and a first further active substance and a second further active substance, such. B. contain two different active compounds from groups A) to I), the weight ratio of compound I will depend on 1 further active ingredient of the properties of the respective active compounds, preferably it is in the range of from 1: 50 to 50: 1 and in particular in the range from 1: 10 to 10: 1. The weight ratio of compound I to the 2nd further active compound 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 the first further active compound to 2nd further active compound 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 packaged and used individually or already mixed or as parts of a modular design (kit of parts).

In one embodiment of the invention, the kits (kits), one or more, also contain all components that can be used for the preparation of an agrochemical composition according to the invention. Example, these kits may include one or more fungicide component (s) and / or an adjuvant component and / or a insecticide component and / or a growth regulator component and / or a herbicide. One or more components may be combined together or pre-formulated. In the embodiments in which more than two components are provided in a kit, the components may be combined and packaged in a single container such as a vessel, bottle, can, pouch, bag or canister. In other embodiments, two or more components of a kit may be packaged separately, ie not preformulated or mixed. Kits may contain one or more separate containers such as containers, bottles, cans, pouches, bags or canisters, each container containing a separate component of the agrochemical composition. The components of the composition of the invention can be used individually or already mixed, or as parts of a modular design (, kit of parts') packaged and used further. In both forms, a component can be separately or together with the further components or as part of the invention, be kit of parts' used for preparing the mixture according to the invention.

The user uses the composition of the invention usually for use in a predosage device, a knapsack sprayer, a spray tank or a spray plane. The agrochemical composition with water and / or buffer is brought to the desired application concentration, optionally with other excipients may be added and so, the ready-use spray liquor or the agrochemical composition according to the invention is obtained. Usually, 50 to 500 liters of the ready spray mixture per hectare of agricultural land applied, preferably 100 to 400 liters.

In one embodiment, the user individual components such can. As parts of a kit or a two- or three-component mixture of the feed composition according to the invention himself in a spray tank and, if appropriate, other auxiliaries admit (tank mix).

In a further embodiment, the user can both individual components of the inventive composition as well as partially premixed components, such as components comprising compounds I and / or active compounds from groups A) to I), in a spray tank and, if appropriate, further auxiliaries to admit (tank mix) ,

In a further embodiment, the user can both individual components of the inventive composition as well as partially premixed components, such as components comprising compounds I and / or use active compounds from groups A) to I), together (for. Example as tank mix) or sequentially.

Compositions of a compound I (component 1) with at least one active compound of group A) (component 2) and particularly of the strobilurins selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin are preferred.

also preferred are compositions of a compound I (component 1) with at least one active compound selected from the group B) (component 2) of the carboxamides and particularly selected from bixafen, boscalid, isopyrazam, fluopyram, Penflufen, penthiopyrad, sedaxane, fenhexamid, metalaxyl , mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (Picobenzamid), zoxamide, carpropamid, Man- dipropamid and N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide.

also preferred are compositions of a compound I (component 1) with at least one active compound selected from the group C) (component 2) of the azoles, and particularly selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole , propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam.

also relates to compositions of a compound I are preferred (component 1) with at least one active compound selected from the group D) (component 2) of the nitrogen-containing heterocyclyl and particularly selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforine, fludioxonil, Fodemorph, fenpropimorph, noxyfen tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, Fenami- don, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil, Qui and 5-ethyl-6-octyl- [1, 2,4] triazolo [1, 5-a] pyrimidin-7-ylamine.

also preferred are compositions of a compound I (component 1) with at least one active compound selected from the group E) (component 2) of the carbamates, and particularly selected from mancozeb, metiram, propineb, thiram, licarb Iprova-, benthiavalicarb and propamocarb.

also relates to compositions of a compound I (component 1) with at least one active substance selected from fungicides of the group F) (component 2) and particularly selected from dithianon, fentin salts, such as fentin acetate are preferred,

Fosetyl, fosetyl-aluminum, H3PO3 and salts thereof, chlorothalonil, dichlofluanid, thionyl ophanat-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfuric fei, cymoxanil, metrafenone, spiroxamine and A / -methyl-2- {1 - [ (5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -A / - [(1 R) -1, 2,3,4-tetrahydronaphthalen-1 - yl] -4-thionyl azolcarboxamid.

also preferred are compositions of a compound I (component 1) with at least one active substance selected from the fungicides of Biological antifungal agent (component 2) and particularly selected from Bacillus subti- // s strain NRRL no. B-21661, Bacillus pum / '/ us strain NRRL no. B-30087 and U oudemansii locladium. In particular, such biological antifungal agents, plant strengthening agents are:

- Ampelomyces quisqualis (eg the product AQ 10 ® from Intrachem Bio GmbH & Co. KG, Germany.), Aspergillus flavus (eg the product AFLAGUARD ® from Syngenta, Switzerland.), Aureobasidium pullulans (eg the product BOTECTOR ® from . bio-ferm GmbH, Germany), Bacillus pumilus (eg strain NRRL no. B-30087 ® in SONATA ®, and BALLAD Plus. Fa. AgraQuest Inc., USA), Bacillus subtilis (eg strain NRRL No. B-21661 in RHAPSODY ®, SERENADE ® MAX and SERENADE ®

. ASO of Fa. AgraQuest Inc., USA), Bacillus subtilis var amyloliquefaciens FZB24 (eg the product TAEGRO ® from. Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (for example, the product ASPIRE ® from. Ecogen Inc., USA), Candida saitoana (eg the products BIOCURE ® (mixed with lysozyme) and BIOCOAT ® of Micro Flo Company USA (BASF SE) and Arysta), chitosan (eg ARMOR ZEN Fa companies. Botri- Zen Ltd., New Zealand), Clonostachys rosea catenulata, also called Gliocladium catenulatum (eg strain J1446. presTop ® from Verdera, Finland), Coniothyrium minitans (eg the product Contans ® from Prophyta, Germany), Cryphonectna parasitica (eg. product Endothia parasitica the company CNICM, France), Cryptoworks tococcus albidus (eg the product YIELD PLUS ® from. Anchor Bio-Technologies, South Africa), Fusarium oxysporum (eg the products biofox ® from. Siapa, Italy, and FUSACLEAN ® from. Natural Plant Protection, France), Metschniko- wia fructicola (eg Prod ukt Shemer ® from. AgroGreen, Israel), Microdochium dimerum (eg the product AntiBot ® from. Agrauxine, France), Phlebiopsis gi- gantea (eg the product ROTSOP ® from. Verdera, Finland), Pseudozyma flocculo- sa ( eg the product SPORODEX ® from. Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (eg paraty the product POLYVERSUM ® from. Remeslo SSRO, Biopre-, Czech Republic), Reynoutria sachlinensis (eg the product REGALIA ® of company Marrone Biolnnovations, USA), Talaromyces flavus V1 17b (eg the product protus ® from. Prophyta, Germany), Trichoderma asperellum SKT-1 (eg, the product ECO-HOPE ® from. Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (eg the product SENTINEL ® from. Agrimm Technologies Ltd, New Zealand), T. harzianum T-22 (eg the product PLANT SHIELD ® from BioWorks Inc., USA), T. harzianum JH 35 ( eg the product ROOT PRO ® from MyControl Ltd., Israel), T. harzianum T-39 (for example, the products TRICHODEX ® and TRICHODERMA 2000 ® from. MyControl Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (eg the product TRICHOPEL the company Agrimm Technologies Ltd, New Zealand), T. harzianum and T. viride ICC012 ICC080 (eg the product remédier ® WP Fa. Isagro Ricerca, Italy), T. polysporum and T. harzianum (eg the product Binab ® from. Binab Bio-innovation AB, Sweden), T. stromaticum (eg the product TRICOVAB ® from Ceplac, Brazil), T. virens GL-21 (eg the product SOILGARD ® from Certis LLC, USA), T. viride (eg the products TRIECO ® from Ecosense Labs. (India) Pvt. Ltd., India and BIO-CURE ® F from. T. Stanes & Co. Ltd., India), T. viride TV1 (eg the product T. viride TV1 company Agribiotec srl, Italy), Ulocladium oudeman- S / / HRU3 (eg the product BOTRY ZEN ® of Botry-Zen Ltd Company, New Zealand). Accordingly, the present invention further relates to compositions of a compound I (component 1) with a further active substance (component 2), the latter selected from the lines B-1 to B-344 in the column of "Component 2" of Table B.

A further embodiment of the invention relates to the compositions listed in Table B B-1 to B-344, wherein in each case one line of Table B corresponds to an agrochemical composition comprising an individualized in the present description, compounds of the formula I (component 1) and the respectively indicated in that row further active substance from groups A) to I) (component 2). According to one embodiment the component 1 corresponds to a I. in Tables 1 a to 257a individualized compound The active ingredients in the compositions described, are each preferably present in synergistically effective amounts.

Table B: active composition comprising an individualized compound I and one further active substance from groups A) to I)

Line Component 1 Component 2

B-1 individualized compound I azoxystrobin

B-2 individualized compound I dimoxystrobin

B-3 individualized compound I enestroburin

B-4 individualized compound I fluoxastrobin

B-5 an individualized compound I kresoxim-methyl

B-6 an individualized compound I metominostrobin

B-7 an individualized compound I orysastrobin

B-8 an individualized compound I picoxystrobin

B-9 an individualized compound I pyraclostrobin

B-10 an individualized compound I Pyrametostrobin

B-1 1 individualized compound I Pyraoxystrobin

B-12 an individualized compound I pyribencarb

B-13 an individualized compound I trifloxystrobin

2- (o - ((2,5-dimethylphenyl-oxymethylene) -

B-14 an individualized compound I

phenyl) -3-methoxy-acrylic acid methyl ester

2- (2- (3- (2,6-dichlorophenyl) -1-methyl-allyl

B-15 an individualized compound I idenaminooxymethyl) phenyl) -2-methoxy- imino-N-methyl-acetamide line Component 1 Component 2

B-16 an individualized compound I benalaxyl

B-17 an individualized compound I benalaxyl-M

B-18 an individualized compound I Benodanil

B-19 an individualized compound I bixafen

B-20 an individualized compound I boscalid

B-21 an individualized compound I carboxin

B-22 an individualized compound I fenfuram

B-23 an individualized compound I fenhexamid

B-24 an individualized compound I flutolanil

B-25 an individualized compound I furametpyr

B-26 an individualized compound I Isopyrazam

B-27 an individualized compound I Isotianil

B-28 an individualized compound I Kiralaxyl

B-29 an individualized compound I mepronil

B-30 an individualized compound I metalaxyl

B-31 an individualized compound I metalaxyl-M

B-32 an individualized compound I Ofurace

B-33 an individualized compound I oxadixyl

B-34 an individualized compound I oxycarboxin

B-35 an individualized compound I Penflufen

B-36 an individualized compound I penthiopyrad

B-37 an individualized compound I Sedaxane

B-38 an individualized compound I tecloftalam

B-39 an individualized compound I Thifluzamide

B-40 an individualized compound I tiadinil

B-41 an individualized compound I 2-amino-4-methyl-thiazol-5-carboxanilide

N- (3 \ 4 \ 5'-trifluorobiphenyl-2-yl) -3-difluoro-

B-42 an individualized compound I methyl-1-methyl-1H-pyrazol-4-carbox- amide

N- (4'-Trifluormethylthiobiphenyl-2-yl) -

B-43 individualized Compound I 3- difluoromethyl-1 -methyl-1 H-pyrazol

4-carboxamide

N- (2- (1, 3,3-trimethyl-butyl) -phenyl) -1, 3-di-

B-44 an individualized compound I

methyl-5-fluoro-1 H-pyrazole-4-carboxamide

B-45 an individualized compound I dimethomorph

B-46 an individualized compound I flumorph

B-47 an individualized compound I Pyrimorph

B-48 an individualized compound I flumetover

B-49 an individualized compound I fluopicolide

B-50 an individualized compound I Fluopyram line Component 1 Component 2

B-51 an individualized compound I zoxamide

B-52 an individualized compound I carpropamid

B-53 an individualized compound I diclocymet

B-54 an individualized compound I mandipropamid

B-55 an individualized compound I oxytetracycline

B-56 an individualized compound I silthiofam

N- (6-methoxy-pyridin-3-yl) cyclopropane

B-57 an individualized compound I

carboxamide

B-58 an individualized compound I azaconazole

B-59 an individualized compound I bitertanol

B-60 an individualized compound I bromuconazole

B-61 an individualized compound I cyproconazole

B-62 an individualized compound I difenoconazole

B-63 an individualized compound I diniconazole

B-64 an individualized compound I diniconazole-M

B-65 an individualized compound I epoxiconazole

B-66 an individualized compound I fenbuconazole

B-67 an individualized compound I fluquinconazole

B-68 an individualized compound I flusilazole

B-69 an individualized compound I flutriafol

B-70 an individualized compound I hexaconazole

B-71 an individualized compound I imibenconazole

B-72 an individualized compound I ipconazole

B-73 an individualized compound I metconazole

B-74 an individualized compound I myclobutanil

B-75 an individualized compound I oxpoconazole

B-76 an individualized compound I paclobutrazol

B-77 an individualized compound I penconazole

B-78 an individualized compound I propiconazole

B-79 an individualized compound I prothioconazole

B-80 an individualized compound I simeconazole

B-81 an individualized compound I tebuconazole

B-82 an individualized compound I tetraconazole

B-83 an individualized compound I triadimefon

B-84 an individualized compound I triadimenol

B-85 an individualized compound I triticonazole

B-86 an individualized compound I uniconazole

B-87 an individualized compound I cyazofamid

B-88 an individualized compound I imazalil

B-89 an individualized compound I imazalil sulfate row Component 1 Component 2

B-90 an individualized compound I pefurazoate

B-91 an individualized compound I Prochloraz

B-92 an individualized compound I triflumizole

B-93 an individualized compound I Benomyl

B-94 an individualized compound I carbendazim

B-95 an individualized compound I fuberidazole

B-96 an individualized compound I thiabendazole

B-97 an individualized compound I ethaboxam

B-98 an individualized compound I etridiazole

B-99 an individualized compound I hymexazol

2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxy-

B-100, a compound I individualized phenyl) -isoxazole-5-yl] -2-prop-2-acetamide inyloxy-

B-101, a compound I individualized fluazinam

B-102, a compound I individualized pyrifenox

3- [5- (4-chloro-phenyl) -2,3-dimethyl-

B-103 individualized compound I

isoxazolidine-3-yl] -pyridine

3- [5- (4-methyl-phenyl) -2,3-dimethyl-

B-104 individualized Compound I

isoxazolidine-3-yl] -pyridine (Pyrisoxazol)

B-105, a compound I individualized 3,4,5-trichloro-pyridine-2,6-dicarbonitrile

B-106, a compound I individualized bupirimate

B-107, a compound I individualized Cyprodinil

B-108 individualized compound I diflumetorim

B-109, a compound I individualized fenarimol

B-1 10 an individualized compound I Ferimzone

B-1 1 1 individualized compound I mepanipyrim

B-1 12 an individualized compound I nitrapyrin

B-1 13 an individualized compound I nuarimol

B-1 14 an individualized compound I pyrimethanil

B-1 15 an individualized compound I triforine

B-1 16 an individualized compound I Fenpiclonil

B-1 17 an individualized compound I fludioxonil

B-1 18 an individualized compound I aldimorph

B-1 19 an individualized compound I dodemorph

B-120, a compound I individualized Dodemorphacetat

B-121 individualized compound I fenpropimorph

B-122 individualized compound I tridemorph

B-123 individualized compound I fenpropidin

B-124, a compound I individualized fluoroimide

B-125, a compound I individualized iprodione line Component 1 Component 2

B-126, a compound I individualized procymidone

B-127 individualized compound I vinclozolin

B-128 individualized compound I famoxadone

B-129 individualized compound I fenamidone

B-130, a compound I individualized flutianil

B-131 individualized compound I octhilinone

B-132 individualized compound I probenazole

5-amino-2-iso-propyl-4-ortho-tolyl-pyr

B-133 individualized compound I

azol-3-one-1-carbothioic acid S-allyl ester

B-134, a compound I individualized acibenzolar-S-methyl

B-135 individualized compound I amisulbrom

B-136 individualized compound I anilazine

B-137 individualized compound I blasticidin S

B-138 individualized compound I captafol

B-139 individualized compound I captan

B-140 I individualized connection chinomethionat

B-141, a compound I individualized dazomet

B-142, a compound I individualized debacarb

B-143 individualized compound I Diclomezine

B-144, a compound I individualized difenzoquat

B-145 individualized compound I difenzoquat methylsulfate

B-146 individualized compound I fenoxanil

B-147 individualized compound I folpet

B-148 individualized compound I oxolinic

B-149 individualized compound I piperalin

B-150 individualized compound I proquinazid

B-151 individualized compound I pyroquilon

B-152, a compound I individualized Quinoxyfen

B-153 individualized compound I triazoxide

B-154 individualized compound I tricyclazole

B-155 I 2-butoxy-6-iodo-3-propyl-chromen-4-on an individualized compound

5-chloro-1 - (4,6-dimethoxy-pyrimidin-2-yl) -

B-156 individualized compound I

2-methyl-1 H-benzoimidazole

5-chloro-7- (4-methyl-piperidin-1-yl) -

B-157 individualized Compound I 6- (2,4,6-trifluoro-phenyl) - [1, 2,4] tri- azolo [1, 5-a] pyrimidine

5-ethyl-6-octyl- [1, 2,4] triazolo [1, 5-a] pyridine

B-158 individualized Compound I

midin-7-ylamine

B-159 individualized compound I ferbam

B-160, a compound I individualized mancozeb line Component 1 Component 2

B-161 individualized compound I maneb

B-162 individualized compound I metam

B-163 individualized compound I Methasulphocarb

B-164 individualized compound I metiram

B-165 individualized compound I propineb

B-166 individualized compound I thiram

B-167 individualized compound I Zineb

B-168 individualized compound I ziram

B-169 individualized compound I diethofencarb

B-170 individualized compound I benthiavalicarb

B-171 individualized compound I iprovalicarb

B-172 individualized compound I propamocarb

B-173 individualized compound I propamocarb hydrochloride

B-174 individualized compound I valiphenal

N- (1 - (1 - (4-cyanophenyl) ethanesulfonyl) -

B-175 individualized compound I

but-2-yl) carbamate (4-fluorophenyl) ester

B-176 individualized compound I Dodin

B-177 individualized compound I Dodin free base

B-178 individualized compound I guazatine

B-179 individualized compound I guazatine acetate

B-180 individualized compound I iminoctadine

B-181 individualized compound I iminoctadine triacetate

B-182 individualized compound I iminoctadine-tris (albesilate)

B-183 individualized compound I kasugamycin

B-184 individualized compound I kasugamycin hydrochloride hydrate

B-185 individualized compound I polyoxin

B-186 individualized compound I streptomycin

B-187 individualized compound I Validamycin A

B-188 individualized compound I binapacryl

B-189 individualized compound I dicloran

B-190 individualized compound I dinobuton

B-191 individualized compound I dinocap

B-192 individualized compound I nitrothal-isopropyl

B-193 individualized compound I tecnazene

B-194, a compound I individualized fentin salts

B-195 individualized compound I dithianon

B-196 individualized compound I isoprothiolane

B-197 individualized compound I edifenphos

B-198 individualized compound I fosetyl, fosetyl-aluminum

B-199 individualized compound I iprobenfos line Component 1 Component 2

B-200, a compound I individualized phosphorous acid and derivatives

B-201, a compound I individualized pyrazophos

B-202, a compound I individualized tolclofos-methyl

B-203, a compound I individualized chlorothalonil

B-204, a compound I individualized dichlofluanid

B-205 individualized compound I dichlorphen

B-206, a compound I individualized flusulfamide

B-207 individualized compound I hexachlorobenzene

B-208, a compound I individualized pencycuron

B-209 individualized compound I pentachlorophenol and salts

B-210, a compound I individualized phthalide

B-21 1 individualized compound I Quintozene

B-212, a compound I individualized thiophanate-methyl

B-213, a compound I individualized tolylfluanid

N- (4-chloro-2-nitrophenyl) -N-ethyl

B-214 individualized compound I

4-methylbenzenesulfonamide

B-215, a compound I individualized Bordeaux mixture

B-216 individualized compound I copper

B-217 individualized compound I copper hydroxide

B-218, a compound I individualized copper oxychloride

B-219 individualized compound I basic copper sulfate

B-220, a compound I individualized sulfur

B-221, a compound I individualized biphenyl

B-222, a compound I individualized Bronopol

B-223, a compound I individualized cyflufenamid

B-224, a compound I individualized cymoxanil

B-225 individualized compound I diphenylamine

B-226 individualized compound I metrafenone

B-227 individualized compound I mildiomycin

B-228, a compound I individualized oxine-copper

B-229 individualized compound I prohexadione-calcium

B-230 individualized compound I spiroxamine

B-231 individualized compound I tolylfluanid

N- (Cyclopropylmethoxyimino- (6-difluoro-

B-232 individualized compound I methoxy-2,3-difluorophenyl) -methyl) -

2-phenylacetamide

N '- (4- (4-chloro-3-trifluoromethylphenoxy) -

B-233 individualized compound I 2,5-dimethyl-phenyl) -N-ethyl-N-methyl-formamidine

B-234 individualized compound I N '- (4- (4-fluoro-3-trifluoromethyl-phenoxy) - Line Component 1 Component 2

2,5-dimethylphenyl) -N-ethyl-N-methyl-formamidine

N '- (2-methyl-5-trifluoromethyl-4- (3-tri-

B-235 individualized compound I methylsilanylpropoxy) phenyl) -N-ethyl

N-methyl formamidine

N '- (5-difluoromethyl-2-methyl-4- (3-tri-

B-236 individualized compound I methylsilanylpropoxy) phenyl) -N-ethyl

N-methyl formamidine

2- {1 - [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -thiazol-4-car-

B-237 individualized compound I

boxylsäure-methyl- (1, 2,3,4-tetrahydro-naphthalen-1-yl) -amide

2- {1 - [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -thiazol-4-car-

B-238 individualized compound I

boxylsäure-methyl- (R) -1, 2,3,4-tetrahydro-naphthalen-1-yl-amide

Acetic acid 6-tert-butyl-8-fluoro-2,3-di-

B-239 individualized compound I

methyl-quinolin-4-yl ester

Methoxy-acetic acid 6-tert-butyl-8-fluoro-

B-240 individualized Compound I

2,3-dimethyl-quinolin-4-yl ester

A / -methyl-2- {1 - [(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -

B-241 individualized Compound I

Λ / - [(1 R) -1, 2,3,4-tetrahydronaphthalen- 1 -yl] -4-thiazolecarboxamide

Bacillus subtilis strain NRRL no. B-

B-242 individualized Compound I

21661

Bacillus pumilus strain NRRL no. B-

B-243 individualized compound I

30087

B-244 individualized compound I Ulocladium oudemansii

B-245 individualized compound I carbaryl

B-246 individualized compound I carbofuran

B-247 individualized compound I carbosulfan

B-248 individualized compound I Methomylthiodicarb

B-249 individualized compound I bifenthrin

B-250, a compound I individualized cyfluthrin

B-251 individualized compound I cypermethrin

B-252, a compound I individualized alpha-cypermethrin

B-253 individualized compound I zeta-cypermethrin

B-254 individualized compound I deltamethrin

B-255 individualized compound I esfenvalerate line Component 1 Component 2

B-256 individualized compound I Lambda-cyhalothrin

B-257 individualized compound I Permethrin

B-258 individualized compound I tefluthrin

B-259 individualized compound I Diflubenzuron

B-260 individualized compound I Flufenoxuron

B-261 individualized compound I lufenuron

B-262 individualized compound I Teflubenzuron

B-263 individualized compound I spirotetramat

B-264 individualized compound I clothianidin

B-265 individualized compound I dinotefuran

B-266 individualized compound I imidacloprid

B-267 individualized compound I thiamethoxam

B-268 individualized compound I Acetamiprid

B-269 individualized compound I thiacloprid

B-270 individualized compound I endosulfan

B-271 individualized compound I Fipronil

B-272 individualized compound I Abamectin

B-273 individualized compound I emamectin

B-274 individualized compound I Spinosad

B-275 individualized compound I spinetoram

B-276 individualized compound I hydramethylnon

B-277 individualized compound I chlorfenapyr

B-278 individualized compound I fenbutatin oxide

B-279 individualized compound I indoxacarb

B-280, a compound I individualized metaflumizone

B-281 individualized compound I flonicamid

B-282 individualized compound I Lubendiamid

B-283 individualized compound I chlorantraniliprole

B-284 individualized compound I Cyazypyr (HGW86)

B-285 individualized compound I Cyflumetofen

B-286 individualized compound I acetochlor

B-287 individualized compound I dimethenamid

B-288 individualized compound I metolachlor

B-289 individualized compound I metazachlor

B-290 individualized compound I glyphosate

B-291 individualized compound I glufosinate

B-292 individualized compound I sulfosate

B-293 individualized compound I clodinafop

B-294 individualized compound I fenoxaprop

B-295 individualized compound I fluazifop line Component 1 Component 2

B-296 individualized compound I haloxyfop

B-297 individualized compound I paraquat

B-298 individualized compound I phenmedipham

B-299 individualized compound I clethodim

B-300 individualized compound I cycloxydim

B-301, a compound I individualized profoxydim

B-302, a compound I individualized sethoxydim

B-303, a compound I individualized tepraloxydim

B-304, a compound I individualized pendimethalin

B-305 individualized compound I Prodi amines

B-306 individualized compound I trifluralin

B-307 individualized compound I acifluorfen

B-308 individualized compound I bromoxynil

B-309 individualized compound I imazamethabenz

B-310, a compound I individualized imazamox

B-31 1 individualized compound I imazapic

B-312 individualized compound I imazapyr

B-313 individualized compound I imazaquin

B-314 individualized compound I imazethapyr

B-315, a compound I individualized 2,4-dichlorophenoxyacetic acid (2,4-D)

B-316 individualized compound I chloridazon

B-317 individualized compound I clopyralid

B-318 individualized compound I fluroxypyr

B-319 individualized compound I picloram

B-320 individualized compound I picolinafen

B-321 individualized compound I bensulfuron

B-322, a compound I individualized chlorimuron-ethyl

B-323 individualized compound I cyclosulfamuron

B-324 iodosulfuron an individualized compound I

B-325 individualized compound I mesosulfuron

B-326 individualized compound I metsulfuron-methyl

B-327 individualized compound I nicosulfuron

B-328 individualized compound I rimsulfuron

B-329 individualized compound I triflusulfuron

B-330, a compound I individualized atrazine

B-331 individualized compound I hexazinone

B-332 individualized compound I diuron

B-333 individualized compound I florasulam

B-334 individualized compound I pyroxasulfone

B-335 individualized compound I bentazone line Component 1 Component 2

B-336 individualized compound I cinidon-ethlyl

B-337 individualized compound I Cinmethylin

B-338 individualized compound I dicamba

B-339 individualized compound I diflufenzopyr

B-340 individualized compound I quinclorac

B-341 individualized compound I quinmerac

B-342 individualized compound I mesotrione

B-343 individualized compound I saflufenacil

B-344 individualized compound I Topramezone

The active substances 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 according to IUPAC, their preparation and their fungicidal action are likewise known (cf. Can J. Plant Sci 48 (6), 587- 94, 1968;... EP-A 141 317; EP-A 152 031; EP- A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1028125, EP-A 1035122, EP-A 1201648, EP -A 1,122,244, 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 00/46148; WO 00/65913; WO 01/54501;

WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO 03/1 1853;

WO 03/14103; WO 03/16286; WO 03/53145; 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 05/87773; 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 compounds, a solvent or solid carrier, for example. As indicated in the manner as described for compositions of the compounds I.

Concerning usual ingredients of such compositions containing made to the details of the compositions, the compounds I.

The compositions for mixtures of active ingredients are suitable as fungicides for controlling harmful fungi. They are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi including soilborne pathogens which mycetes in particular from the classes of Plasmodiophoro-, Peronosporomycetes (syn. Oomycetes), chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti ) come. Furthermore is made to the statements containing the effectiveness of the compounds I and the compositions, the compounds I.

Another object of the present invention is the use of compounds I and their pharmaceutically acceptable salts for the treatment of disease units, in particular the use of the compounds I as an antifungal agent. 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. A further embodiment relates to the use of a compound I and / or a pharmaceutically effective salt thereof for preparing an antimycotic. The invention accordingly also provides a process for producing an antifungal agent, comprising the use of at least one compound of the formula I and / or a pharmaceutically acceptable salt thereof. 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 effective salt thereof for the preparation of an agent that inhibits the growth of tumors and cancers in mammals. "Cancer" means a malignant or malignant tumor is particularly meant as breast cancer, prostate cancer, lung cancer, CNS cancer, melanocarcinomas, ovarian carcinoma, 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, particularly viral infections, which cause diseases in warm-blooded animals. Thus, one embodiment of the invention relates to the use of a compound I and / or a pharmaceutically effective salt thereof for the preparation of an agent for the treatment of viral infections. The behandlenden to viral diseases include retrovirus diseases such as HIV and HTLV, influenza virus, noviruserkrankungen RHI, herpes and the like.

Synthesis Examples:

The procedures given in the synthesis examples were used with appropriate modification of the starting compounds to obtain further compounds of formula I or precursors thereof.

Melting points were obtained on a Mel-Temp II apparatus and are uncorrected. HPLC / MS: retention time in min. (HPLC-MS) / m / z (High Performance Liquid chroma tography mass spectrometry), HPLC column: RP-18 column (Chromolith Speed ​​ROD from Merck KgaA, Germany), mobile phase: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0.1% TFA in a gradient of 5:95 to 95: 5 in 5 minutes; at 40 ° C. MS: quadrupole electrospray, 80 V (positive mode) Example 1: Preparation of 1 - [[rel (2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2-yl ] methyl] -5-n-butylsulfanyl-1, 2,4-triazole (I.3) to a solution of 2.50 g of 2 - [[rel (2S, 3R) -3- (2-chlorophenyl) -2 - (2,4-difluorophenyl) oxiran-2-yl] methyl] -4H-1, 2,4-triazole-3-thione in 25 mL DMF at room temperature was 1, 37 g potassium carbonate added. After 5 minutes, dropwise 1 was added 82 g of n-butyl iodide and the reaction mixture stirred until complete conversion at room temperature. It was then poured onto ice water and extracted with MTBE. The organic phase was then washed 3 x with water and the combined aqueous phases were extracted once with MTBE exhaustive. The combined organic phases were dried over sodium sulfate, concentrated and purified by column chromatography. (74%), thereby obtaining 2.22 g of the desired product.

Table E: Additional compounds of formula I in which p is = 0:

Figure imgf000076_0001

VerA BR physically bond chemical data

1.1 4- 2- CH (CH 3) CH 2 CH 3 HPLC-MS:

Fluorophenyl chlorophenyl 4.23min, Mass

418

"Trans" -

diastereomer

I.2 4- 2- CH2CH2CH2CH3 Mp:

Fluorophenyl chlorophenyl 59 ° C

"Trans" - diastereomer

I.3 2.4 2 CH2CH2CH2CH3 HPLC-MS:

Difluoro-chlorophenyl 4.31 min, mass phenyl 435

"Trans" -

diastereomer

I.4 4- 2- CH 2 CH (CH 3) 2 HPLC-MS:

Fluorophenyl chlorophenyl 4.26min, Mass

418

"Trans" -

diastereomer

I.5 2,4- 2- CH (CH 3) CH 2 CH 3 HPLC-MS:

Difluoro-chlorophenyl 4.26min, Mass phenyl 435

"Trans" - VerA BR physically bond chemical data

diastereomer

1.6 2,4-2-CH 2 CH (CH 3) 2 HPLC-MS:

Difluoro-chlorophenyl 4.28min, Mass phenyl 435

"Trans" -

diastereomer

1.7 4- 2- C (CH 3) 3 HPLC-MS:

Fluorophenyl chlorophenyl 4.18min, Mass

418

"Trans" -

diastereomer

Biological Examples:

Glasshouse

drug treatment

The active compounds were prepared separately or together as a stock solution containing 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Wettol EM 31 (wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio of solvent emulsifier was made up of 99 to 1. 10 ml. Then to 100 ml was filled with water. DIE se stock solution was given with the solvent-emulsifier-water mixture to the bottom diluted drug concentration. Alternatively, the active ingredients were used as commercial finished formulations and diluted with water to the stated active compound concentration.

Example G1 - Protective Activity Against Puccinia recondita on Wheat

(Wheat brown rust) (Puccrt P1)

Leaves of potted wheat seedlings were sprayed with an aqueous suspension having the concentration of active compound stated below until dripping wet. The next day, the treated plants were a

Spore suspension of brown rust of wheat (Puccinia recondita) was inoculated. The plants for 24 hours in a chamber with high atmospheric humidity (90 to 95%) were found at 20 to 24 ° C. During this time, the spores germinated and the

Germ tubes penetrated into the leaf tissue. The following day, the

Test plants returned to the greenhouse and cultivated at temperatures between 20 and 24 ° C and 65 to 70% relative atmospheric humidity for a further 7 days. The extent of the rust fungus development on the leaves was determined visually. The compounds I.6 and 1.1 resulted in 300 ppm to an infestation of 20%, whereas the untreated control to 90% infestation showed.

Example G2 - Curative activity against soybean rust caused by Phakopsora pachyrhizi (Phakpa K3) Leaves of pot-grown soybean seedlings (Phakopsora pachyrhizi) were inoculated with a spore suspension of soybean rust. Thereafter, the pots for 24 hours in a chamber with high atmospheric humidity (90 to 95%) and 20 to 24 ° C were observed. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The infected plants were then in the greenhouse

Temperatures 23 to 27 ° C and 60 to 80% relative humidity cultured further. After two days, the plants were treated with the above

Active ingredient solution is sprayed into the compound concentration stated below until dripping wet. After the spray coating has dried, the test plants were cultivated in a greenhouse at 23 to 27 ° C and 60 to 80% relative atmospheric humidity for a further 10 days. Thereafter, the amount was the

Rust fungus development on the leaves visually in% infection determined. The compounds I.7 and 1.1 resulted in 300 ppm to an infestation of more than 3%, whereas the untreated control to 90% infestation showed.

Example C3 - Activity Against Early Blight of Tomato Caused by Alternaria solani (Alteso P1)

Leaves of potted tomato plants were sprayed with an aqueous suspension having the concentration of active compound stated below until dripping wet. The following day, the leaves were inoculated with an aqueous spore suspension of Alternaria solani in 2% biomalt. The plants were in a

water-vapor-saturated chamber at temperatures between 18 and 20 ° C

established. After 5 days, the disease had such a great extent on the untreated, but infected control plants that the infection could be determined visually in%.

Comparative test

Figure imgf000078_0001
Compound infestation in% at 300ppm in Alteso

P1

untreated control 90

microtest

The active compounds, separately as a stock solution having a concentration of 10000 ppm in DMSO.

Example M1 - Activity against Septoria Leaf Septoria tritici in the Microtiter Test (Septtr)

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated active compound concentration. Then adding an aqueous spore suspension of Septoria tritici was on malt. The plates were placed in a water vapor-saturated chamber at temperatures of 18 ° C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were charged (100%) and the fungus and active compound-with the growth of drug-free control variant to determine the relative growth in% of the pathogens in the individual active ingredients. , The compound I.3 resulted in 31 ppm concentration of active compound to a growth rate of 0%.

Example M2 - activity against the Rice Blast Pathogen Pyricularia oryzae in the microtiter test (Pyrior)

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated active compound concentration. Then adding an aqueous spore suspension of Pyricularia oryzae was performed on malt. The plates were placed in a water vapor-saturated chamber at temperatures of 18 ° C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The parameters measured were (= 100%) and the fungus and active compound-off against the growth of drug-free control variant to determine the relative growth in% of the pathogens in the individual active ingredients. The compounds I.5, 1.7 and 1.1 resulted in 31 ppm concentration of active compound to a growth rate of at most 7%.

Example M3 - Activity Against the blotch, Leptosphaeria nodorum in the Microtiter Test (Leptno)

The stock solution is pipetted into a microtiter plate (MTP) and diluted with water to the stated active compound concentration. Then adding an aqueous spore suspension of malt of Leptosphaeria nodorum done. The plates were placed in a water vapor-saturated chamber at temperatures of 18 ° C. Using an absorption photometer, the MTPs were on the 7th day after the Inokula- tion measured at 405nm. The measured parameters were calculated with the growth of the active compound-free control variant and the fungus and active compound-to determine the relative growth in% of the pathogens in the individual active ingredients. The compound 1.2 resulted in 31 ppm concentration of active ingredient in a growth of 10%.

Claims

claims
Triazolylmethyloxiranes of the formula I
Figure imgf000081_0001
wherein the variables have the following meanings:
A, B independently of one another phenyl which is unsubstituted or substituted one, two, three, or four independently selected substituents L, wherein L represents:
L is halogen, cyano, nitro, cyanato (OCN), Ci-C4-alkyl, Ci-C 4 -Halo- genalkyl, phenyl-Ci-C4-alkyloxy, C2-C4 alkenyl, C2-C4 haloalkenyl , C2-C4 alkynyl, C2-C4 haloalkynyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, C1-C4-alkylcarbonyloxy, Ci-C4 alkylsulfonyloxy, C2-C 4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6 cycloalkenyl, C 3 -C 6 halocycloalkenyl, S (= 0) n A 1, C (= 0) A 2, C (= S) A 2 NA 3 A 4, phenyl or phenoxy where n, A 1, A 2, A 3, A 4: n is 0, 1 or 2;
Hydrogen, hydroxy, Ci-C4-alkyl, Ci-C 4 haloalkyl, amino, Ci-C 4 alkylamino or di-Ci-C4-alkylamino, one of said at A 1 groups or C2-C 4 alkenyl , C2-C4-haloalkenyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, C3-C6 cycloalkyl or C3-C6-halocycloalkyl;
A 3, A 4 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 -Halo- genalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C3-C6 cycloalkyl or C3-C6-halocycloalkyl ; wherein the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L may carry one, two, three or four identical or different groups R L for their part:
R L is halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4 alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-Halogencyclo- alkyl, C -C4-alkylcarbonyl, Ci-C4-alkylcarbonyloxy, C1-C4 alkoxycarbonyl, amino, Ci-C4-alkylamino, di-Ci-C4-alkylamino; p is 0, 1 or 2
R 1 CH2CH2CH2CH3, CH 2 CH (CH 3) 2, CH (CH 3) C 2 H 5 or C (CH 3) 3; and their agriculturally acceptable salts. Compounds according to claim 1, wherein p is the 0th
Compounds according to claim 1 or 2, wherein A is phenyl, containing one, two or three L, where L is independently selected from halogen, C1-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci C4-haloalkoxy and C1-C4 haloalkylthio.
Compounds according to claim 1 or 2, wherein A is unsubstituted phenyl.
Compounds according to one of claims 1 to 4, wherein B is phenyl, containing one, two or three L, where L is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy , Ci-C4-haloalkoxy and Ci-C4-halogenoalkylthio.
Compounds according to one of claims 1 to 4, wherein B is unsubstituted phenyl.
Compounds according to one of claims 1 to 6, wherein R 1 is CH2CH2CH2CH. 3
Compounds according to one of claims 1 to 6, wherein R 1 is C (CH 3) 3 is.
Use of compounds of the formula I as claimed in one of claims 1 to 8, and their agriculturally acceptable salts for controlling phytopatho- genes fungi.
A composition comprising a compound of formula I according to one of claims 1 to 8 and / or a salt thereof.
The composition of claim 10 further comprising at least one solid or liquid carrier.
12. The composition according to claim 10 or 1 1, further comprising at least one further fungicidal, insecticidal and / or herbicidal active ingredient.
13. Seed, comprising at least one compound of formula I according to one of claims 1 to 8 and / or an agriculturally acceptable salt thereof.
14. A method for controlling phytopathogenic fungi, characterized in that the fungi or against fungal attack on protective materials, plants, the soil or seeds with an effective amount of a connects one dung of the formula I as claimed in any one of claims 1 to 8 or a treated agriculturally acceptable salt thereof.
15. A pharmaceutical composition comprising at least one compound of formula I according to one of claims 1 to 8 and / or a pharmaceutically acceptable salt thereof.
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