HU191848B - Fungicides containing as active substance derivatives of aminoketal and process for production of the derivatives of aminoketal - Google Patents

Abstract

The compositions of the present invention contain the aminocetal derivatives of formula (I) or their acid addition salts as active ingredients. In formula I, R1 is a dihalophenyl group, optionally substituted with one to four carbon atoms or a C5-C7 cycloalkyl radical in the phenyl moiety, either singly or with C1-4 alkyl or a nitro group and / or halogen at most doubly substituted phenoxy- (C2-C6 alkyl) or phenyl (C1-C4 alkyl), optionally substituted with 1 to 4 carbon atoms or halogen in the phenyl moiety; alkyl, while R3 and R4 are C1-6alkyl or together with the adjacent nitrogen atom, optionally substituted with C1-4 alkyl, not more than doubly substituted with C1-4alkyl or C1-4alkyl with C1-4alkoxycarbonyl. monosubstituted piperazinoc sweeper or pyrrolidino group or optionally C1-C4 alkyl group or piperidinyl substituted with ortho or phenyl. <zr2 0z "Ό 191848 -1-

Description

FIELD OF THE INVENTION The present invention relates to fungicidal compositions containing as active ingredient the aminoketals of formula (I). Some of the compounds of formula I are known.

Certain amino ketals, such as 2-methyl-2- (3,4,5-trimethoxyphenyl) -4- (1-pyrrolidinylmethyl) -1,3-dioxolane, 2-cyclohexyl-2-phenyl, are known. 4- (1-morpholinylmethyl) -1,3-dioxolane, 2-phenyl-2- (chloromethyl) -4- (1-morpholinylmethyl) -1,3-dioxolane and 2-methyl-2- [1- (4-Methyl-buten-3-yl)] -4- (1-piperidinylmethyl) -1,3-dioxolane are useful in medicine, for example as antihypertensive or diuretic agents (French Patent No. 2,163,322). Japanese Patent Application Nos. 52-33608, Belgian Patent No. 776,421, Dutch Patent 66,095,779, U.S. Patent 3,337,408, Soviet Patent 722,910; Patel, AR: J. Pharm. Sci. 52, 588-592 (1963/6); Wolinski, J. Acta Pol.

Pharm. 1980, 37 (1), 15-24. pp. 35 (6), 621-627, 1978, 35 (3), 265-272, 1977, 34 (2), 143-147. p.)

It is also known that aminoketals, such as 2,2-dimethyl-4- (1-morpholinylmethyl) -1,3-dioxolane, can be used as starting materials or intermediates in the preparation of pharmaceutically active compounds (Harris ND, J. Org. Chem. 28 , 745-748 (1963/3), Karpyszov, Bio-Org. Chim. 5, 238-241 (1979/2), and no reference has been made to the effect of known amino ketals on plant protection.

It is also known that certain aminopropiophenone derivatives, such as (4-tert-butylphenyl) (1-dimethylamino-prop-2-yl) ketone (U.S. Patent No. 3,019,497), are incorporated herein by reference. ) and organic sulfur compounds such as zinc ethylene-1,2-bis (dithiocar brownate) (R. Wegler,

Chemie dér Pflanzenschutz- und Schádlingsbekámpfungsmittel (Springer Verlag Berlin 1970, Vol. 2, pp. 65) are fungicidal. However, the effects of the compounds, in particular at low application rates and concentrations, are not always fully satisfactory.

It has now been found that the substituted aminoketals of formula (I) are represented by formula (I)

R ¹ is a dihalophenyl, phenoxy (C 2 -C 6) alkyl optionally substituted in the phenyl moiety with up to two substituents singly or singly substituted with C 1 -C 4 alkoxy or C 5 -C 7 cycloalkyl or with C 1 -C 4 alkyl or nitro and / or halogen; or phenyl (C 1 -C 4 alkyl) mono- or di-substituted in the phenyl moiety by one or two substituents optionally substituted with C 1 -C 4 alkyl or halogen;

R ² is C 1 -C 4 alkyl, mig

R ³ and R ⁴ are C 1 -C 6 alkyl or morpholino optionally substituted with up to two C 1 -C 4 alkyl optionally, or C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl mono- pyrrolidino or piperidinoc monosubstituted with phenyl, and their acid addition salts have excellent fungicidal activity.

The compounds of formula (I) may exist in the form of pure isomers or mixtures of isomers of different compositions; the invention encompasses both forms.

Surprisingly, the fungicidal activity of the substituted aminoketals of formula (I) is superior to the prior art (4-tert-butylphenyl) (1-dimethylamino-prop-2-yl) ketone and zinc-ethylene-1. , 2-bis (dithiocarbamate). Plant protection compositions containing compounds of formula I are thus advances.

The compositions of the invention may also contain the acid addition salts of the amino ketals of formula (I) as active ingredients.

The acid addition salts of the compounds of formula I are preferably formed with the following acids: haloacids such as hydrochloric acid and hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, carboxylic acids having one or two carboxyl groups and hydroxycarboxylic acids such as acetic, maleic, succinic, sulfuric acid, salicylic acid, sorbic acid, lactic acid, and sulfonic acids such as ρ-toluenesulfonic acid and 1,5-naphthalene disulfonic acid.

The acid addition salts of the compounds of formula (I) may be prepared in a simple manner by known salt-forming procedures, for example, by dissolving the compound of formula (I) in a suitable solvent and adding an acid, such as hydrochloric acid, to the solution. The salt may be isolated in a manner known per se, for example by filtration, and may be purified by washing with an inert solvent.

Some of the aminoketals of formula (I) useful as active ingredients in the compositions of the present invention are known and can be prepared by methods known in the art. Likewise, the new aminoketals of formula IA can be prepared; the substituents R ¹ , R ² , R ³ and R ^{4 in} formula IA will be discussed later.

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The compounds of formula (I) and (IA) are prepared by substitution of a substituted dioxolane of formula (II) (R ^v and R ² 'below), X is halogen, optionally substituted alkylsulfonyloxy or aryl. sulfonyloxy group) with an amine of formula III (R ³ 'and R ⁴ ' are defined below) optionally in the presence of a catalyst, optionally a base and optionally a diluent.

In the formula IA, the substituents have the following meanings:

R ¹ 'is C 6 -C 12 alkyl, haloalkyl having 1 to 5 halogens and 2 to 6 carbon atoms, benzyl monosubstituted in the phenyl moiety, optionally monosubstituted or halo in the phenyl moiety, or trifluoromethyl; phenyl (C2-C6 alkyl) monosubstituted, phenylsulfonyl (C2-C6 alkyl) monosubstituted in the phenyl moiety, phenyl (C2-C6 alkenyl) optionally substituted by halo in the phenyl moiety phenyl, thio (C2-C6 alkyl) mono- or di-substituted in the phenyl moiety with one or two halogen atoms or with C1-C4 alkyl, optionally C5-C7 cycloalkyl in the phenyl moiety, (C1-C4 alkoxy) monocarbon, C 1 -C 4 alkoxy, trifluoromethyl or phenyl, or halogen and / or C 1 -C 4 alkyl phenoxy (C 1 -C 6 -alkyl) substituted with up to two substituents at most or substituted with halogen and nitro or trifluoromethyl, or tri-substituted with C 1-4 alkyl and C 1-4 alkylthio or C 1-4 alkyl or C3-C7-cycloalkyl (C1-C4) alkyl optionally substituted in the cycloalkyl moiety with one to four carbon atoms,

R ² 'is hydrogen, C 1 -C 12 alkyl or phenyl optionally substituted by halo;

R ³ 'and R ⁴ ' are C 1 -C 6 alkyl or benzyl or phenethyl optionally substituted by halogen or C 1 -C 4 alkyl, or C 5 -C 7 cycloalkyl or C 3 -C 7 alkenyl or C 3 -C 7 alkynyl, or

R ³ 'and R ⁴ ' together with the adjacent nitrogen atom represent a pyrazolo, pyrrolidino, perhydroazepino, trimethyl perhydroazepino group or a mono- or di-substituted morpholino group, or a C 1-4 alkyl group, optionally substituted with C 1-4 alkyl; It forms a piperazino group monosubstituted with C4 alkoxycarbonyl or a piperidino group optionally substituted with benzyl, phenyl, C1-4 alkoxycarbonyl mono- or C 1-4 alkyl.

The substituted dioxolanes used as starting materials in the production process are defined by formula (II). In this formula, the preferred meaning of R ¹ 'and R ² * is the same as that of the compound of formula IA. X is preferably chlorine, methanesulfonyloxy, p-toluenesulfonyloxy or trifluoromethanesulfonyloxy.

Some of the substituted dioxolanes of formula II are known (Rec. Trav. Chim. Pays-Bas 91, 989-1001 (1972), Farm. Ed. Sci. 29, 167-174 (1974); J. med. Chem. 6, 3, 325-328 (1963), the others may be synthesized by the methods described in the literature. For the preparation of the dioxolanes of formula (TI), the aldehyde or ketone of formula (IV) - wherein R ¹ 'and R ² ' in formula (IV) are as defined above - substituted 1,2-diol of formula (V) - In Formula V, X is as defined above, in the presence of an inert organic solvent such as toluene and in the presence of a catalyst such as p-toluenesulfonic acid at a temperature between 50 ° C and 120 ° C.

The other reaction component, amines, is defined by formula (III). Preferably the substituents in formula (III) have the same meaning as those described for formula (IA). The amines of formula (III) are generally known and available chemicals.

Organic solvents are used as diluents in the process. These include aromatic hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as carbon tetrachloride or chlorobenzene, formamides such as dimethylformamide, nitriles such as acetonitrile or propionitrile, alcohols such as propanol and butanol, amines such as triethyl 3191848

amine or piperidine; and highly polar solvents such as dimethyl sulfoxide and hexamethylphosphoric triamide.

The process optionally uses an acid acceptor. Any organic or inorganic base may be used for this purpose. Alkali metal hydroxides or carbonates such as sodium hydroxide, sodium carbonate or potassium carbonate, and triethylamine or pyridine are preferably used. The excess of the base of formula (III) used as starting material may also serve as a solvent and an acid acceptor.

Optionally, the reaction is carried out in the presence of a catalyst. Preferred catalysts are alkali metal iodides such as potassium iodide.

The reaction temperature can be varied within a wide range. Generally, the components are reacted at a temperature of 50 ° C to 250 ° C, preferably 80 ° C to 200 ° C.

The reaction is carried out at atmospheric pressure or at elevated pressure. Generally, pressures of about 250-260, preferably 250-400 KPa are employed.

Preferably, from 1 to 30 moles of amine of formula (III) are used per mole of substituted dioxolane of formula (II), depending on whether the amine is also used as a solvent and / or acid scavenger. The final products are isolated in the usual manner.

The anions of the salts are preferably anions derived from the following acids: hydrogen halide acids such as hydrochloric acid and hydrobromic acid, and phosphoric acid, nitric acid and sulfuric acid.

The active compounds are formulated into conventional formulations such as solutions, emulsions, soluble powders, suspensions, powders, dusts, foams, pastes, granules, aerosol formulations, suspensions and emulsifiers. They can be impregnated with natural and synthetic materials, microcapsules can be used to form polymeric materials and seed coatings, and formulations of the active ingredients with flammable fillers, such as smoke cartridges, cans and spirals, and hot or cold formulated for use with the ULV process.

The compositions are prepared in a manner known per se, for example, by mixing the active compounds with carriers, i.e., liquid solvents, pressurized liquid gases and / or solid carriers, optionally with surfactants, i.e. emulsifiers and / or dispersants and / or foaming agents. can also be added to the mixture. When water is used as a carrier, organic solvents may also be used as co-solvents. Suitable liquid solvents are essentially aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, and alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, highly polar solvents such as dimethylformamide, dimethyl sulfoxide and water. Liquefied gas carriers are understood to include materials such as aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide. Solid carriers include natural stone flour such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and mineral fillers such as highly dispersed silica, alumina and silicates by precipitation. Solid carriers of granules include granules of crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, inorganic and organic flours, and granules of organic materials such as sawdust, coconut shells, corn cobs and tobacco stalks. Non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid ethers, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates as emulsifiers and / or foaming agents. , arylsulfonates and protein hydrolysates, and lignin, sulfite impurities and methylcellulose as dispersants.

The compositions of the present invention may contain adhesion promoters such as carboxymethylcellulose, natural and synthetic, powdered, granular or latex-like polymers such as acacia, polyvinyl alcohol, polyvinyl acetate.

The compositions of the invention also include coloring agents such as inorganic pigments, such as iron oxide, titanium oxide, ferrocyanite and organic dyes such as alizarin, azo-metal phthalocyanine dyes, and printing materials such as iron, manganese, boron, copper , cobalt, molybdenum and zinc salts.

The compositions generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of the active ingredient.

The active compounds are used in the form of commercially available formulations and / or forms thereof.

The active ingredient content of the formulations prepared from the formulations may be varied within wide limits.

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Concentration of spray juice is usually used when treating parts of plants

1-0,0001% by weight, preferably 0.5-0,001% by weight.

For seed dressing, 0.001 to 50 g, preferably 0.01 to 10 g of active ingredient per kg of seed are used.

For soil treatment, the active compound concentration at the site of action is 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight.

Production examples

Example 1

2- (tert-butyl) -2- (4-chloro-phenoxy) methyl-4- (l-pyrrolidinylmethyl) -l, 3-dioxolane

17.3 g (0.005 mol) of 2- (tert-butyl-2- (4-chlorophenoxy) -4-methanesulfonyloxy-1-methyl) -1,3-dioxolane and 7.1 g ²⁰ (0 (1 g mole) of pyrrolidine was heated at 120 ° C for 15 hours. After cooling, excess pyrrolidine was distilled off in vacuo and the residue dissolved in ether. ₂₅ The solution was washed twice with water, dried over sodium sulfate and concentrated in vacuo. 12.1 g (65.7% of theory) of the title compound are obtained in the form of an oil, n 0 ^ = 1.5099.

Preparation of starting material

a) 2- (tert-Butyl) -2- (4-chlorophenoxymethyl) gg -4- (methanesulfonyloxymethyl) -1,3-dioxolane

To a solution of 142 g (0.5 mol) of 2- (tert-butyl) -2- (4-chlorophenoxymethyl) -4- (hydroxymethyl) -1,3-dioxolane in 150 ml of pyridine at 0 57 g (0.5 mol) of methanesulfonic acid chloride are added dropwise. The reaction mixture was stirred at 20-25 ° C for 17 hours, then the solvent was evaporated in vacuo. The residue is dissolved in ether, the solution is washed with water, dried over sodium sulfate and concentrated in vacuo. 171 g (98% of theory) of the title compound are obtained as an oil.

1 H-NMR (CDCl 3): δ (ppm) = 7.2 (d, 2H), 6.8 (d, 2H), 4.6-3.6 (m, 7H), 3.0 50 (d, 3H), 1.05 (s, 9H).

b) 2- (tert-butyl) -2- (4-chlorophenoxymethyl) -4- (hydroxymethyl) -1,3-dioxolane

226 g (1 mole) of 1- (4-chlorophenoxy) -3,3-dimethyl-butan-2-one (prepared according to US Patent No. 2,020,063, sodium 4-chlorophenolate and < £ bromo-pinakolinból)

A solution of glycerol (120 g, 1.07 mol), p-60-toluenesulfonic acid monohydrate (19 g, 0.1 mol) and butanol (30 g) in toluene (1000 mL) was heated under reflux for 16 hours. After cooling, the toluene solution was washed with water (250 x 250 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Distillation gave 186 g (65.4% of theory) of the title compound. Mp: 161-163 ° C / 0.13 mbar.

Example 2

2- (4-chlorophenyl) -4- (N, N-di / n-butyl / methyl-amino) -2-phenyl-l, 3-dioxolane

16.1 g (0.05 mol) of 4-chloromethyl-2- (4-chlorophenylmethyl) -2-phenyl-1,3-dioxolane, 100 ml of di-n-butylamine and 13.8 g of A mixture of potassium carbonate (g) (0.1 mol) was stirred with a pinch of potassium iodide at 180 ° C and 2 bar in an autoclave for 8 hours. The excess di- (n-butyl) amine is then removed in a water-jet vacuum at a bath temperature of 40-100 ° C. The cooled residue was dissolved in toluene (50 mL), filtered, and concentrated in vacuo.

9.4 g (47% of theory) of the title compound are obtained as an oil, nn = 1.5172.

Preparation of starting material

4- (chloromethyl) -2- (4-chlorophenylmethyl) -2-phenyl-1,3-dioxolane (0.3 mol) phenyl (4-chlorophenylmethyl) ketone, A mixture of 3-chloro-1,2-propanediol (66.3 g, 0.6 mol) and p-toluenesulfonic acid (5.2 g, 0.03 mol) in toluene (600 mL) was heated under reflux for 3 days. After cooling, the reaction mixture was extracted with sodium bicarbonate solution, dried over sodium sulfate, and concentrated in vacuo. 95 g (98% of theory) of the title compound are obtained, m.p. 65 ° C.

Example 3

2- (4-Chloro-phenylmethyl) -2-phenyl-4- (1-piperidinylmethyl) -1,3-dioxolane

16.1 g (0.05 mol) of 4- (chloromethyl) -2- (4-chlorophenylmethyl) -2-phenyl-1,3-dioxolane (prepared in Example 2), 100 g A mixture of piperidine (1.18 mol), potassium carbonate (1.38 g, 0.1 mol) and a small amount of potassium iodide was heated at reflux for 16 hours. The reaction mixture was then concentrated in vacuo, diluted with 150 mL of 0.4N hydrochloric acid and washed with 3 x 50 mL of ligroin. The hydrochloric acid solution was saturated with sodium chloride and extracted with ethyl acetate (3 x 60 mL). The organic layer was washed with sodium bicarbonate solution, brine, dried over sodium sulfate, and finally stripped of solvent in vacuo at 40 ° C. 10 g (53.8% of theory) of the title compound are obtained in the form of an aqueous solid. op .:

° C.

In a similar manner, the following compounds of formula (I) are prepared.

Example number R ¹ R ^z -NR ³ R ⁴ Op. [° C] or refractive index [nol 4 C2H5 CWhen di (n-butyl) amino 1.5027 5 CzHs CH3 1-pyrrolidinyl 1.5036 6 C2H5 CHS 1-piperidinyl 1.5012 7 C2H5 CH3 4-morpholinyl 1.5047 8 C2H5 CH3 1-pyrazolyl 1.4682 9 I-C4II9 CH3 1-piperidinyl 1.5039 10 I-C4H9 CH3 4-morpholinyl 1.5041 11 I-C4H9 CH3 4-methyl-1-piperazinyl 1.5035 12 n CgHi9 CHS 1-pyrrolidinyl 1.4570 13 n-C9Hi9 CH3 1-piperidinyl 1.4535 14 n-C9Hi9 CH3 1-perhydroazepinylcarbonyl 1.4549 15 n C9Hu CHS 4 raorfolinil 1.4489 16 n-C9Hi9 CHS 4-methyl-1-piperidinyl 1.4510 17 n-C9Hi9 CH3 4-methyl-l-piperazinyl 1.4551 18 n-C9Hi9 n CaHm 1-pyrrolidinyl 1.4510 19 n CgHis n CgHis 1-piperidinyl 1.4588 20 n-C9Hi9 n-C9Hi9 1-perhydroazepinylcarbonyl 1.4578 21 n-C9Hi9 n-C9Hi9 morpholino 1.4539 22 n-C9Hi9 n-C9Hi9 4-methyl-l-piperidinyl 1.4534 23 n C9Hig n-C9Hi9 4-methylpiperazino 1.4555 24 2-chlorophenyl CH3 1-piperidinyl 1.5301 25 2-chlorophenyl CH3 morpholino 1.5326 26 2-chlorophenyl CWhen 2,6-dimethylmorpholino 1.5084 27 2,4-dichlorophenyl CH ₃ 1-piperidinyl 1.5372 28 2,4-dichlorophenyl CH ₃ 2,6-dimethylmorpholine 1.5219 29 2,5-dichlorophenyl CH3 1-piperidinyl 1.5383 30 2,5-dichlorophenyl CH3 morpholino 1.5384 31 2,5-dichlorophenyl CHS 2,6-dimethylmorpholine 1.5181 32 4-chlorobenzyl CeHs 1-pyrrolidinyl 61 33 4-chlorobenzyl CeHs 4-methylpiperazino 71 34 2- (4-chlorobenzyl) -2- propenyl CWhen 1-pyrrolidinyl 1.5261 35 2- (4-chlorobenzyl) -2-propenyl CHS 1-piperidinyl 1.5244 36 4-chloro-phenoxymethyl CH3 1-piperidinyl 1.5282 37 4-chloro-phenoxymethyl t-C4H9 di (n-propyl) amino 1.4889 38 4-chloro-phenoxymethyl t-C4H9 di (isobutyl) amino 1.5003 39 4-chloro-phenoxymethyl t-C4H9 di (cyclohexyl) amino 98 40 4-chloro-phenoxymethyl t-CíHo dibenzylamino 121 41 4-chloro-phenoxymethyl t-C4H9 n-methylamine in methyl 1.5049 42 4-chloro-phenoxymethyl t-CíHs 1-piperidinyl 1.5173 43 4-chloro-phenoxymethyl t-C4H9 2-methyl-1-piperidinyl 1.5068 44 4-chloro-phenoxymethyl t-CíHs 3-methyl-1-piperidinyl 1.5026 45 4-chloro-phenoxymethyl t-CíHu 4-methyl-l-piperidinyl 1.5032 46 4-chloro-phenoxymethyl t-C4H9 3,5-dimethyl-1-piperidinyl 1.5012 47 4-chloro-phenoxymethyl t-CíHg morpholino 40 48 4-chloro-phenoxymethyl t Cihan 2,6-dimethylmorpholino 1.5082 49 4-chloro-phenoxymethyl t-CíHg 4-methylpiperazino 1.5187 50 4-bromo-phenoxymethyl t-C4H9 1-piperidinyl 1.5271 51 4-bromo-phenoxymethyl t-CíHs 2,6-dimethylmorpholino 1.5126 52 4-fluoro-phenoxymethyl t Cihan 1-pyrrolidinyl 1.4917 53 4-fluoro-phenoxymethyl t-CíHg 1-piperidinyl 1.5026 54 4-fluoro-phenoxymethyl t-C4H9 2-methyl-1-piperidinyl 1.4992 55 4-fluoro-phenoxymethyl t-CiHs 3-methyl-1-piperidinyl 1.5023 56 4-fluoro-phenoxymethyl t-CíHo 4-methyl-l-piperidinyl 1.5045 57 4-fluoro-phenoxymethyl t-C4H9 3,5-dimethyl-1-piperidinyl 1.5008 58 4-fluoro-phenoxymethyl t-C4H9 2,6-dimethylmorpholino 1.4938

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Example number R ¹ R ² -NR ³ R ' Op. [° C] or refractive index [ηέ ° 1 59 4-fluoro-phenoxymethyl t-Ctfla dibenzylamino 134 60 2,6-dichloro-phenoxymethyl t-C4Ü9 1-piperidinyl 1.5109 61 2,6-dichloro-phenoxymethyl t-C4H9 morpholino 1.5226 62 3-phenyl-phenoxymethyl t-C4O9 1-piperidinyl 1.5577 63 3-phenyl-phenoxymethyl t-C4Hs morpholino 1.5557 64 1-phenoxy-2-methyl-2-propyl CH3 1-piperidinyl 2-methyl-1- 1.5011 65 1-Phenoxy-2-methyl-2-propyl CH3 piperidinyl 1.4998 66 1-phenoxy-2-methyl-2-propyl CH3 3-methyl-1-piperidinyl 1.4973 67 1-phenoxy-2-methyl-2- propyl CH3 4-methyl 1-1-piperidinyl 1.4939 68 1-Phenoxy-2-methyl-2-propyl CH3 3,5-dimethyl-1-piperidinyl 1.4974 69 1- (4'-chlorophenoxy) - 2- ch ₃ 1-pyrrolidinyl 1.5200 70 1- (4'-Chlorophenoxy) -2- CD3 1-piperidinyl 1.5121 71 l- (4'-chlorophenoxy) -2- CH3 1-piperidinyl X HCl 153-155 72 l- (4'-chlorophenoxy) -2- CH3 2-methyl-l-piperidinyl 1.5102 73 l- (4'-chlorophenoxy) -2- methyl-2-propyl CH3 4-phenyl-1-piperidinyl 1.5431 74 l- (4'-chlorophenoxy) -2- methyl-2-propyl CH3 morpholino 1.5191 75 1- (4'-chlorophenoxy) -2-methyl-2-propyl CH3 4- (ethoxycarbonyl) -l- piperazinom 1.4993 76 l- (4'-chlorophenoxy) -2- methyl-2-propyl CWhen di (n-butyl) amino 1.5377 77 1- (2 * -chlorophenoxy) -2-methyl-2-propyl CH3 2-methyl-l-piperidinyl 1.5047 78 l- (2'-chloro-phenoxy) -2- methyl-2-propyl CH3 3-methyl-1-piperidinyl 1.5051 79 l- (2,4-dichloro-phenoxy) - -2-methyl-2-propyl CH3 1-piperidinyl 1.5006 80 l- (2,4-dichloro-phenoxy) -2-methyl-2-propyl CH3 2-methyl-l-piperidinyl 1.4941 81 l- (2,4-dichloro-phenoxy) -2-methyl-2-propyl CH3 3-methyl-1-piperidinyl 1.5034 82 l- (2,4-dichloro-phenoxy) - -2-methyl-2-propyl CH3 4-methyl-l-piperidinyl 1.4987 83 1- (2,4-Dichlorophenoxy) -2-methyl-2-propyl CH3 3,5-dimethyl-1-piperidinyl 1.4980 84 1- (2,4-Dichlorophenoxy) -2-methyl-2-propyl CWhen 2,4-dimethyl-1-piperidinyl 1.5021 85 1- (2,4-Dichlorophenoxy) -2-methyl-2-propyl CWhen 2,6-dimethyl-1-piperidinyl 1.4980 86 l- (2,4-dichloro-phenoxy) ~ -2-methyl-2-propyl CH3 2,6-dimethylmorpholine 1.5034 87 1- (2-methylphenoxy) -2-methyl-2-propyl CH3 piperidino 1.4952 88 1- (2-methylphenoxy) -2-methyl-2-propyl CH? 2,6-dimethylmorpholino 1.4874 89 l- (3-methyl-phenoxy) -2-methyl-2-propyl CH3 4-methyl-l-piperazino 1.5023 90 1- (4-methylphenoxy) -2-methyl-2-propyl CH3 di (n-butyl) amino 1.5132 91 l- (4-methylphenoxy) ~ -2-methyl-2-propyl CH3 1-perhydroazepinylcarbonyl 1.5118 92 1- (2,4-dimethylphenoxy) -2-methyl-2-propyl CH3 1-pyrrolidinyl 1.5081 93 l- (2,4-dimethyl-phenoxy) - CWhen 1-piperidinyl 1.5064

-2-methyl-2-propyl

-715

Example number R ¹ R ² -NR ³ R ⁴ Op. F ° 0] or refractive index [nS ^ 94 l- (2,4-dimethyl-phenoxy) - -2-methyl-2-propyl CH3 4-methylpiperazino 1.5086 95 l- (2,6-dimethyl-phenoxy -2-methyl-2-propyl CH3 1-pyrrolidinyl 1.5087 96 1- (2,6-Dimethylphenoxy) -2-methyl-2-propyl CH3 1-piperidinyl 1.5074 97 l- (2,6-dimethylphenoxy) - -2-propyl-2-jnetil CWhen 4-methylpiperazino 1.5067 98 1- (2-methoxyphenoxy) -2-methyl-2-propyl CH3 di (n-butyl) amino 1.5063 99 1- (2-methoxyphenoxy) -2-methyl-2-propyl CH3 1-pyrrolidinyl 1.5057 100 l- (2-methoxy-phenoxy) -2-methyl-2-propyl CH3 1-piperidinyl 1.5070 101 1- (2-methoxyphenoxy) -2-methyl-2-propyl CHS 3,5-dimethyl-l-piperidinyl 1.4944 102 1- (2-methoxyphenoxy) -2-methyl-2-propyl CH3 morpholino 1.5067 103 1- (2-Ethoxy-phenoxy) -2-methyl-2-propyl- CH3 1-piperidinyl 1.5087 104 1- (2-Ethoxy-phenoxy) -2-methyl-2-propyl CH3 morpholino 1.5067 105 1- (2-Ethoxy-phenoxy) -2-methyl-2-propyl CWhen 4-methylpiperazine 1.5046 106 l- (4-tert-butyl-phenoxy) - -2-methyl-2-propyl CH3 1-pyrrolidinyl 1.4948 107 l- (4-tert-butyl-phenoxy) - -2-methyl-2-propyl CHS 1-piperidinyl 1.4954 108 l- (4-tert-butyl-phenoxy) -2-methyl-2-propyl CH3 morpholino 1.4962 109 l- (4-tert-Butyl-phenoxy) ~ -2-methyl-2-propyl CHS 4-methylpiperazino 1.4975 110 1- (4-Cyclohexyl-phenoxy) -2-methyl-2-propyl CH3 1-pyrrolidinyl 1.5110 111 l- (4-Cyclohexyl-phenoxy) -2-methyl-2-propyl CH3 1-piperidinyl 1.5098 112 l-phenoxy-2-methyl-2- propyl CWhen 4-methylpiperazine 1.5031 113 1-Phenoxy-2-methyl-2-propyl CH3 2,6-dimethylmorpholine 1.4925 114 l- (2-chloro-phenoxy) -2- methyl-2-propyl CWhen 4-methyl-1-piperidinyl 1.5044 115 l- (2-chloro-phenoxy) -2- methyl-2-propyl CH3 3,5-dimethyl-l-piperidinyl 1.5047 116 l- (2-chloro-phenoxy) -2- methyl-2-propyl CH3 2,4-dimethyl-l-piperidinyl 1.5040 117 1- (2-chlorophenoxy) -2-methyl-2-propyl CH3 4- (ethoxycarbonyl) -1-piperidinyl 1.5044 118 1- (4-Fluorophenoxy) -2-methyl-2-propyl CH3 1-pyrrolidinyl 1.4912 119 l- (4-fluoro-phenoxy) -2- methyl-2-propyl CWhen 1-piperidinyl 1.5044 120 1- (4-fluorophenoxy) -2-methyl-2-propyl CWhen 1-perhydroazepinil 1.4930 121 l- (4-fluoro-phenoxy) -2- methyl-2-propyl CH3 4-methyl-1-piperidinyl 1.4868 122 l- (4-fluoro-phenoxy) -2- methyl-2-propyl CH3 3-methyl-l-piperidinyl 1.4873 123 l- (4-fluoro-phenoxy) -2- CH3 2-methyl-1-piperidinyl 1.4897

methyl-2-propyl

-817

Example number R ¹ R ² -NR ³ R ⁴ Op. [° C] or refractive index [na] 124 1- (4-Fluorophenoxy) -2-methyl-2-propyl CH3 3,5-dimethyl-1-piperidinyl 1.4841 125 1- (4-Fluorophenoxy) -2-methyl-2-propyl CH3 2) 6-dimethyl-l-piperidinyl 1.4893 126 l- (4-fluoro-phenoxy) -2- methyl-2-propyl CH3 2,4-dimethyl-1-piperidinyl 1.4864 127 l- (4-fluoro-phenoxy) -2- methyl-2-propyl CH3 3,3-dimethyl-l-a Piperidine 1.4825 128 l- (4-fluoro-phenoxy) -2- methyl-2-propyl CH3 4-phenyl-1-piperidinyl 1.5118 129 l- (4-fluoro-phenoxy) -2- methyl-2-propyl CH3 2,6-ditiethylmorpholine 1.4839 130 l- (4-fluoro-phenoxy) -2-methyl-2-propyl CH3 4-methylpiperazino 1.4919 131 l- (4-chlorophenoxy) -2- methyl-2-propyl CHS 2,6-dimethylmorpholino 1.5361 132 4-chlorobenzyl 4-fluorophenyl di (n-butyl) amino 1.5214 133 4-chlorobenzyl 4-fluorophenyl di (n-propyl) -amino 1.5148 134 2- (4-chlorophenyl) vinyl C (CH3) 3 4-methyl-PI morpholino 1.5298 135 2- (4-chlorophenyl) - vinyl C (CH ₃ ) 3 1-piperidinyl 74 136 1- (4-chlorophenylthio) -2-methyl-2-propyl CWhen 1-piperidinyl 1.5491 137 1- (4-chlorophenylthio) -2-methyl-2-propyl CHS 1-pyrrolidinyl 1.5538 138 2- (2,4-dichloro- phenyl ^j) ethyl C (CH3) 3 1-piperidinyl 1.5171 139 1- (4-Fluorophenoxy) -2-methyl-2-propyl CH3 bis (1-propin-3-yl) -amino 1.4968 140 4-chlorobenzyl 4-fluorophenyl 1-piperidinyl 1.5498 141 l-phenyl-2-methyl-2-propyl CH3 1-piperidinyl 1.5091 142 2- (4-chlorophenyl) ethyl -C (CH3) 3 1-piperidinyl 1.5179 143 l- (4-chlorophenyl-sulfonic sulfonyl) -2-methyl-2-propyl CH3 1-piperidinyl 1.5231 144 l- (4-chlorophenoxy) -2- methyl-2-propyl 4-chlorophenyl 1-piperidinyl 1.5518 145 4-chlorobenzyl phenyl 1-pyrazolyl 1.5641 146 2- (3-chlorophenyl) vinyl CH3 1-piperidinyl 1.5366 147 2 F CH3-C- 2 F CH3 1-piperidinyl 1.4599 148 l- (4-chlorophenyl) -, prop-2-yl CH3 1-piperidinyl 1.5195 149 3-chlorophenyl t CíHs 1-piperidinyl 1.5179 150 CHS C6H5-S-CH2-C- CH3 CHS 1-piperidinyl 1.5445 151 CH3- (CH2) s- CH3 di (n-butyl) amino 1.4461 152 CH3- (CH2) s- CH3- (CH2) e di (n-butyl) amino oil 1.4469 153 l- (4-fluoro-phenoxy) -2-methyl-2-propyl CWhen di (n-butyl) amino 1.4702 154 l- (4-fluoro-phenoxy) - -2-methyl-2-propyl CH3 morpholino 1.4921 155 1- (2,3,5-Trimethyl-phenoxy) -2-methyl-2-propyl CH3 4-methyl-1-piperidinyl 1.5019 156 l- (2,3,5-trimethyl-phenoxy) - -2-methyl-2-propyl CH3 morpholino 1.5034 157 l- (4-chlorophenoxy) -2- methyl-2-propyl CH3 3-methyl-1-piperidinyl 1.5045 158 l- (4-chlorophenoxy) -2- CH3 4-Methyl-l-piperidinyl 1.5040

methyl-2-propyl

-919

Example number R ¹ R ² -bRhi · ¹ Op. [° G] or refractive index [ntf] 159 l- (4-chlorophenoxy) -2- methyl-2-propyl CH3 2,4-dimethyl-l-piperidinyl 1.5031 160 l- (4-chlorophenoxy) -2- methyl-2-propyl cil3 3,5-dimethyl-l-piperidinyl 1,5000 161 l- (4-chlorophenoxy) -2- methyl-2-propyl CWhen 4-methylpiperazino 1.5082 162 l- (4-chlorophenoxy) -2- methyl-2-propyl CH3 1-perhydroazepinylcarbonyl 1.5079 163 1- (2-Isopropoxy-phenoxy) -2-methyl-2-propyl CH3 1-piperidinyl 1.5087 164 1- (2-isopropoxyphenoxy) -2-methyl-2-propyl CH3 4-methyl-1-piperidinyl 1.5095 165 2- (4-methylphenoxy) - -ethyl CH3 1-piperidinyl 1.5117 166 1- (2-isopropoxyphenoxy) -2-methyl-2-propyl CH3 morpholino 1.5060 167 2- (2-chlorobenzyl) -2- propyl CH3 1-piperidinyl 1.5239 168 2-phenylethyl CH3 1-piperidinyl 1.5212 169 3-chloro-phenethyl CH3 1-piperidinyl 1.5282 170 l- (4-chlorophenyl) -2- propyl CH3 4-phenyl-1-piperidinyl 1.5506 171 2-phenyl-2-methylpropyl CH3 1-piperidinyl 1.5149 172 2- (2-fluoro-benzyl) -2- propyl CH3 1-pyrrolidinyl 1.5086 173 2- (2-fluoro-benzyl) -2- propyl CH3 1-piperidinyl 1.5077 174 2- (2-fluoro-benzyl) -2- propyl CH3 1-perhydroazepinylcarbonyl 1.5108 175 2- (2-fluoro-benzyl) -2- propyl CH3 2-methyl-1-piperidinyl 1.5070 176 2- (2-fluoro-benzyl) -2- propyl CH3 3-methyl-l-piperidinyl 1.5028 177 2- (2-fluoro-benzyl) -2- propyl CH3 4-methyl-1-piperidinyl 1.5035 178 2- (2-fluoro-benzyl) -2- propyl CH3 3,5-dimethyl-l-piperidinyl 1.4978 179 2- (4-fluoro-benzyl) -2- propyl CH3 1-pyrrolidinyl 1.5069 180 2- (4-fluoro-benzyl) -2- propyl CH3 1-piperidinyl 1.5061 181 2- (4-fluoro-benzyl) -2- propyl CWhen 1-perhydroazepinylcarbonyl 1.5086 182 2- (4-fluoro-benzyl) -2- propyl CH3 2-methyl-1-piperidinyl 1.4929 183 2- (4-fluoro-benzyl) -2- propyl CWhen 3-methyl-1-piperidinyl 1.5018 184 2- (4-fluoro-benzyl) -2- propyl CWhen 4-methyl-1-piperidinyl 1.5003 185 2- (4-Fluorobenzyl) -2-propyl CWhen 3,5-dimethyl-1-piperidinyl 1.4952 186 2- (4-fluoro-benzyl) -2- propyl CWhen 4-benzyl-1-piperidinyl 1.5356 187 2- (2-chlorobenzyl) -2- propyl CH3 1-perhydroazepinylcarbonyl 1.5272 188 2- (2-chlorobenzyl) -2- propyl CH3 2-methyl-1-piperidinyl 1.5241 189 2- (2-chlorobenzyl) -2- propyl CH3 3-methyl-1-piperidinyl 130 190 2- (2-chlorobenzyl) -2- CH3 4-methyl-1-piperidinyl 1.5193

propyl

-1 021

Example number R ¹ R ² -NR ³ R ⁴ Op. [° C] or refractive index [nti] 191 2- (2-chlorobenzyl) -2- propyl CH3 2,6-dimethyl-l-piperidinyl 1.5375 192 2- (2-chlorobenzyl) -2- propyl CHS 3,5-dimethyl-1-piperidinyl 1.5162 193 2- (4-chlorobenzyl) -2-propyl CH3 1-perhydroazepinylcarbonyl 1.5269 194 2- (4-chlorobenzyl) -2-propyl CWhen 2-methyl-1-piperidinyl 1.5209 195 2- (4-chlorobenzyl) -2-propyl CH3 3-methyl-l-piperidinyl 1.5185 196 2- (4-chlorobenzyl) -2-propyl CHS 4-methyl-1-piperidinyl 1.5170 197 2- (4-chlorobenzyl) -2- propyl CH3 3,5-dimethyl-l-piperidinyl 1.5034 198 199 2- (4-chlorobenzyl) -2- propyl 2- (4-fluorophenoxy) -2- propyl CHS CH3 3,3-dimethyl-l-piperidinyl 1-perhydroazepinylcarbonyl 1.5154 200 2- (4-chlorobenzyl) -2- propyl CH3 1-perhydroazepinylcarbonyl 1.5341 201 2- (4-chlorobenzyl) -2- propyl CH3 3,3-dimethyl-l-piperidinyl 1.5249 202 2- (2-methylbenzyl) -2-propyl CH3 1-pyrrolidinyl 1.5189 203 2- (2-methylbenzyl) -2- propyl CHS l-piperidinyl 1.5177 204 2- (2-methylbenzyl) -2-propyl CH3 1-perhydroazepinylcarbonyl 1.5189 205 2- (2-methylbenzyl) -2-propyl CHS 2-methyl-1-piperidinyl 1.5177 206 2- (2-methylbenzyl) -2- propyl CHS 3-methyl-1-piperidinyl 1.5178 207 2- (2-methylbenzyl) -2-propyl CH3 4-methyl-l-piperidinyl 1.5126 208 2- (2-methylbenzyl) -2- propyl CHS 3,5-dimethyl-l-piperidinyl 1.5091 209 2- (4-methyl-benzyl) -2- propyl CHS 1-pyrrolidinyl 170 210 2- (4-methyl-benzyl) -2- propyl CH3 1-perhydroazepinylcarbonyl 1.5170 211 2- (4-methylbenzyl) -2-propyl CH3 2-methyl-1-piperidinyl 1.5032 212 2- (4-methyl-benzyl) -2- propyl CHS 3-methyl-l-piperidinyl 1.5111 213 2- (4-methyl-benzyl) -2- propyl CH3 4-methyl-l-piperidinyl 1.5105 214 2- (4-methyl-benzyl) -2- propyl CH3 3,5-dimethyl-l-piperidinyl 1.5072 215 2- (4-methyl-benzyl) -2- propyl CHS 3,3-dimethyl-l-piperidinyl 1.5049 216 2,4-dichloro-phenoxymethyl H l-piperidinyl 1.5433 217 2- (4-fluorophenoxy) -2-propyl CH3 3-methyl-1-piperidinyl Fp. 200 ° C / 0.39 mbar 218 2- (4-chlorophenoxy) -2-propyl CH3 3,5-dimethyl-1-piperidinyl Fp.19O ° C / 0.26 mbar 219 2- (4-chlorophenoxy) -2- propyl CH3 1-perhydroazepinylcarbonyl 1.5092 220 2- (4-chlorophenoxy) -2- propyl CH3 3,3-dimethyl-l-piperidinyl 1.5062 221 2- (4-chlorophenoxy) -2- CH3 2,6-dimethylmorpholino 1.5076

propyl

-1 123

R ¹ R ² -NR'R ⁴ Op. [° C] or refractive index [grow 2- (2-methylphenoxy) -2- CWhen 3,3-dimethyl-l-piperidinyl 1.5039 propyl 2- (4-methoxyphenoxy) -2- CH3 3,3-dimethyl-l-piperidinyl 1.5047 propyl 2- (4-methoxyphenoxy) -2- CH3 2,6-dimethylmorpholino 1.5067 propyl 4-chlorophenoxy a wash C (CHA) are the dimethylamino 1.5042 4-chloro-phenoxymethyl C (CH ₃ ) 3 diethylamino 1.4987 l- (3-chlorophenoxy) -2- CH3 1-piperidinyl 1.5073 methyl-2-propyl l- (3-chlorophenoxy) -2- CWhen 1-perhydroazepinylcarbonyl 1.4995 methyl-2-propyl l- (3-chlorophenoxy) -2- CH3 3-methyl-1-piperidinyl 1.5073 - methyl 2-propyl 1- (chlorophenoxy) -2- CWhen 3,3-dimethyl-1-piperidinyl 1.4995 methyl 2-propyl 1- (3-chlorophenoxy) -2- CWhen 2,6-dimethylmorpholino 1.4970 methyl-2-propyl 2- (4-fluorophenoxy) -2- propyl l- (4-chlorophenoxy) -2- CWhen CWhen 3.3-dimethyl-1-piperidinyl 3.3-dimethyl-1-piperidinyl 1.5105 methyl-2-propyl l- (4-chlorophenoxy) -2- CH3 1-pyrrolidinyl 1.5016 methyl-2-propyl l- (4-chlorophenoxy) -2- CWhen 1-perhydroazepinylcarbonyl 1.5076 methyl 2-propyl 1- (4-chlorophenoxy) -2- CWhen 3,3-dimethyl-l-piperidinyl 1.5044 methyl-2-propyl l- (4-chlorophenoxy) -2- CWhen morpholino 1.5064 methyl-2-propyl l- (4-chlorophenoxy) -2- CH3 4-methyl-l-piperazinyl 1.5023 methyl 2-propyl 1- (4-chlorophenoxy) -2- ch ₃ 4-phenyl-1-piperazinyl 1.5092 methyl-2-propyl l- (4-methylphenoxy) -2- CWhen 1-piperidinyl oil 1.4953 -methyl-2-propyl 1- (4-methylphenoxy) -2- CH ₃ 3-methyl-1-piperidinyl oil 1,4909 methyl-2-propyl l- (4-methylphenoxy) -2- CWhen 3,5-dimethyl-l-piperidinyl oil 1.4891 methyl-2-propyl l- (4-methylphenoxy) -2- CWhen morpholino oil 1.4987 methyl-2-propyl l- (2-ethyl-phenoxy) -2- CH3 1-pyrrolidinyl 1.5110 methyl-2-propyl l- (2-ethyl-phenoxy) -2- CWhen 3-methyl-1-piperidinyl 1.5042 methyl-2-propyl 1- (2-ethyl-1-phenoxy) -2- CWhen 4-year 1-1 -p i per id i ni I 1.5067 methyl-2-propyl 1- (2-ethyl-1-phenoxy) -2- CWhen 3,5-dimethyl-l-piperidinyl 1.5047 methyl-2-propyl l- (2-ethyl-phenoxy) -2- CWhen 3,3-dimethyl-l-piperidinyl 1.5071 -methyl-2-propyl 1- (4- (methoxycarbonyl) - CWhen 1-pyrrolidinyl 1.5085 phenoxy) -2-methyl-2-propyl l- (4- methoxy-carbonyl / / ~ CH3 1-piperidinyl 1.5043 -phenoxy) -2-methyl-2-propyl 1- (4- (methoxycarbonyl) - CH3 2-methyl-l-piperidinyl 1.5061 phenoxy) -2-methyl-2-propyl l- (4- methoxy-carbonyl / / - CH3 3-methyl-1-piperidinyl 1.5039 -phenoxy) -2-methyl-2-propyl 1- (4- (methoxycarbonyl) - CH3 4-methyl-1-piperidinyl 1.5049

phenoxy) -2-methyl-2-propyl

-1 225

R ¹ R ² -NR ³ R ⁴ Op. Tore [° C] or smutman [no] 1- (4- / methoxycarbonyl / phenoxy) -2-methyl-2-propyl CH3 3,5-dimethyl-1-piperidinyl 1.5064 1- (4- (Methoxycarbonyl-phenoxy) -2-methyl-2-propyl CHS 2,4-dimethyl-l-piperidinyl 1.5051 1- (4- (Methoxycarbonyl-phenoxy) -2-methyl-2-propyl CH3 3,3-dimethyl-l-piperidinyl 1.5047 1- (4- (methoxycarbonyl-phenoxy) -2-methyl-2-propyl CHS 2,6-dimethylmorpholine 1.5067 2- (4-chloro-2-methylphenoxy) -2-propyl- CH3 3-methyl-1-piperidinyl Fp. 210 ° C / 0.13 mbar 2- (4-chloro-2-methylphenoxy) -2-propyl CH3 3,5-dimethyl-1-Fp. piperidinyl 210 ° C / 0.26 mbar 2- (3-methyl-4- / methylthio / phenoxy) -2-propyl CH3 3-methyl-l-piperidinyl 1.5027 2- (3-methyl-4- (methylthio) phenoxy) -2-propyl CHS 3,5-dimethyl-l-piperidinyl 1.5041 l- (2-chlorophenyl) -2- methyl-2-propyl CH3 1-piperidinyl 1.5422 l- (2,4-dimethyl-phenylthio) ~ - 2-methyl-2-propyl CH3 1-piperidinyl 1.5457 2- (2-chlorobenzyl) -2- propyl CH3 1-pyrrolidinyl 1.5269 2- (2,4-dichlorobenzyl) - 2-propyl CH3 1-pyrrolidinyl 1.5346 2- (2,4-dichlorobenzyl) - 2-propyl CHS 1-piperidinyl 1.5340 2- (2,4-dichlorobenzyl) - 2-propyl CH3 2-methyl-1-piperidinyl Fp. 220 ° C / 0.26 mbar 2- (2,4-dichlorobenzyl) - 2-propyl CH3 3-methylpiperidinyl 1.5293 2- (2,4-dichlorobenzyl) - 2-propyl CH3 4-methyl-l-piperidinyl 1.5286 2- (2,4-dichlorobenzyl) - 2-propyl CH3 3,5-dimethyl-1-piperidinyl 1.5251 2- (4-methyl-benzyl) -2- propyl CH3 1-piperidinyl 1.5150 2- (4-Ethyl-phenoxy) -ethyl CH3 3-methyl-l-piperidinyl 1.5133 l- (2-chloro-phenoxy) -2-methyl-2-propyl CH3 1-pyrrolidinyl 1.5064 1- (2-chlorophenoxy) -2-methyl-2-propyl CH3 1-piperidinyl 1.5082 l- (2-chloro-phenoxy) -2- methyl-2-propyl CH3 1-perhydroazepinylcarbonyl 1.5090 l- (2-chloro-phenoxy) -2- methyl-2-propyl CH3 2,6-dimethyl-1-piperidinyl 1.5076 l- (2-chloro-phenoxy) -2-methyl-2-propyl CH3 3,3-dimethyl-l-piperidinyl 1.5045 l- (2-chloro-phenoxy) -2- methyl-2-propyl CH3 morpholino 1.5089 l- (2-chloro-phenoxy) -2- methyl-2-propyl CH3 2,6-dimethylmorpholino 1.5062 1- (2-chlorophenoxy) -2-methyl-2-propyl CHS 4-methyl-1-piperazinyl 1.5021 l- (4-chlorophenoxy) -2- methyl-2-propyl 'CH3 N-methyl-N-benzylamino 1.5171 1- (4-chlorophenoxy) -2-methyl-2-propyl 2- (4-fluorophenoxy) - CH3 CH3 dicyclohexylamine 2,6-dimethylmorpholine 1.5085

2-propyl

-1 327

Example number R ¹ R ^z -NR ³ R ⁴ Op. breaking [° C] indicator 284 l- (2-methyl-phenoxy) -2-methyl-2-propyl CH3 1-perhydroazepinylcarbonyl 1.4995 285 1- (2-methylphenoxy) -2-methyl-2-propyl CH3 3,5-dimethyl-l-piperidinyl 1.4909 286 l- (2-a wash-phenoxy) -2- methyl-2-propyl CH3 3,3-dimethyl-l-piperidinyl 1.4908 287 l- (2-methyl-phenoxy) -2-methyl-2-propyl CH3 morpholino 1.5002 288 l- (2,5-dimethyl-phenoxy) -2-methyl-2-propyl CWhen 1-piperidinyl 1.4980 289 l- (2,5-dimethyl-phenoxy) -2-methyl-2-propyl CH3 1-perhydroazepinylcarbonyl 1.4941 290 l- (2,5-dimethylphenoxy) ~ -2-methyl-2-propyl CH3 2-methyl-l-piperidinyl 1.4953 291 l- (2,5-dimethylphenoxy) ~ -2-methyl-2-propyl CH3 3-Rethyl-1-piperidinyl 1.4939 292 1- (2,5-dimethylphenoxy) -2-methyl-2-propyl CH3 3,5-dimethyl-l-piperidinyl 1.4902 293 l- (2,5-dimethyl-phenoxy) - -2-propyl-2-'metil CH3 3,3-dimethyl-l-piperidinyl 1.4900 294 l- (2,5-dimethyl-phenoxy) - -2-methyl-2-propyl CH3 morpholino 1.4979 295 l- (2,5-dimethyl-phenoxy) -2-methyl-2-propyl CH3 2,6-dimethyl-morpholine 1.4905 296 l- (2-isopropoxy-phenoxy) - -2-methyl-2-propyl CH3 3,3-dimethyl-1-piperidinyl 1.5041 297 1- (2-methyl-4-chlorophenoxy) -2-methyl-2-propyl CH3 1-piperidinyl 1.5058 298 1- (2-methyl-4-chlorophenoxy) -2-methyl-2-propyl CH3 1-perhydroazepinylcarbonyl 1.5068 299 1- (2-methyl-4-chlorophenoxy) -2-methyl-2-propyl CWhen 2-methyl-l-piperidinyl 1.5031 300 l- (2-methyl-4-chloro- phenoxy) -2-methyl-2-propyl CWhen 3-methyl-1-piperidinyl 1.5021 301 1- (2-methyl-4-chlorophenoxy) -2-methyl-2-propyl CH3 4-methyl-1-piperidinyl 1.5012 302 l- (2-methyl-4-chloro- phenoxy) -2-methyl-2-propyl CH3 3,5-dimethyl-l-piperidinyl 1.4984 303 l- (2-methyl-4-chlorophenoxy) -2-methyl-2-propyl CH3 3,3-dimethyl-l-piperidinyl 1.5069 304 l- (2-nitro-5-chloro- CH3 1-piperidinyl oil 1.5568 phenoxy) -2-methyl-2-propyl 305 1- (2-nitro-5-chlorophenoxy) -2-methyl-2-propyl CH3 2-methyl-1-piperidinyl oil 306 1- (2-nitro-5-chloro- CH3 3-methyl-1-piperidinyl oil 1.5540 phenoxy) -2-methyl-2-propyl 307 l- (2-nitro-5-chloro- phenoxy) -2-methyl-2-propyl CHS 4-methyl-l-piperidinyl oil 308 1- (2-nitro-5-chlorophenoxy) -2-methyl-2-propyl CHS 3,5-dimethyl-1-piperidinyl oil 309 l- (2-nitro-5-chlorophenoxy) -2-methyl-2-propyl CH3 3,3-dimethyl-l-piperidinyl oil 310 2- (2,3-dichlorophenoxy) - 2-propyl CH3 1-piperidinyl 332- -337 ° C 311 2- (2,3-dichlorophenoxy) - 2-propyl CWhen 1-perhydroazepinylcarbonyl 312 2- (2,3-dichlorophenoxy) - 2-propyl CH3 3-methyl-1-piperidinyl 313 2- (2,3-dichlorophenoxy) - CH3 3,5-dimethyl-1-piperidinyl

2-propyl

-1 429

R ¹

R ² -NR ³ R ⁴ op. [° c] or refractive index [no]

2- (2,3-dichlorophenoxy) - CH3 2,6-dimethylmorpholine 2-propyl 2- (2-fluorophenoxy) -2- CH3 1-piperidinyl propyl 2- (2-fluorophenoxy) -2- CH3 3-methyl-l-piperidinyl 1.5087 propyl 2- (2-fluorophenoxy) -2- CH3 3,5-dimethyl-1-piperidinyl 1.5073 - propyl 2- (2-fluorophenoxy) -2- CH3 3,3-dimethyl-1-piperidinyl 340-358 ° C propyl 2- (2-fluorophenoxy) -2- CH3 2,6-dimethylmorpholino propyl 2- (2-fluorophenoxy) -2- CH3 1-perhydroazepinylcarbonyl propyl 2- (2-chlorophenoxy) - 2- CH3 1-piperidinyl - propyl 2- (2-chlorophenoxy) -2- CH3 3-methyl-l-piperidinyl propyl 2- (2-chlorophenoxy) -2- CH3 3,5-dimethyl-1-piperidinyl propyl 2- (2-chlorophenoxy) -2- CH3 1-perhydroazepinylcarbonyl propyl 2- (2-chlorophenoxy) -2- CH3 3,3-dimethyl-1-piperidinyl propyl 2- (2-chlorophenoxy) -2- CH3 2,6-dimethylmorpholino propyl 2-phenoxy-2-propyl CH3 1-piperidinyl 2-phenoxy-2-propyl CH3 3-methyl-1-piperidinyl 2-phenoxy-2-propyl CH3 3,5-dimethyl-1-piperidinyl 2-phenoxy-2-propyl CH3 2,6-dimethylmoor folino 2-phenoxy-2-propyl CH3 1-perhydroazepinylcarbonyl 2-phenoxy-2-propyl CH3 3,3-dimethyl-l-piperidinyl 2- (2-methylphenoxy) - CH3 1-piperidinyl 2-propyl 2- (2-methylphenoxy) - CH3 3-methyl-l-piperidinyl 2-propyl 2- (2-methylphenoxy) - CH3 3,5-dimethyl-l-piperidinyl 2-propyl 2- (2-me til-f e noxi) - CH3 2,6-dimethylmorpholine 2-propyl 2- (2-methylphenoxy) - CH3 3,3-dimethyl-1-piperidinyl 2-propyl 2- (2-methylphenoxy) - CH3 1-perhydroazepinylcarbonyl 360-366 2-propyl 2- (2-ethyl-phenoxy) -2- CH3 1-piperidinyl propyl 2- (2-ethylphenoxy) -2- CH3 3-methyl-1-piperidinyl propyl 2- (2-ethyl-phenoxy) -2- CH3 3,5-dimethyl-1-piperidinyl propyl 2- (2-ethyl-phenoxy) -2- CH3 3,3-dimethyl-1-piperidinyl propyl 2- (2-ethylphenoxy) -2- CH3 2,6-dimethylmorpholino - propyl 2- (2-ethyl-phenoxy) -2- CH3 1-perhydroazepinylcarbonyl propyl 2- (4-chloro-3-methyl- CH3 1-piperidinyl 210 / 0.13 mbar phenoxy) -2-propyl 2- (4-chloro-3-methyl- CH3 1-perhydroazepinylcarbonyl 250 / 0.13 mbar

phenoxy) -2-propyl

-15or [nft)

Example number rl R ² -NR ³ R ⁴ 347 2- (4-chloro-3-methyl- CH3 3-methyl-1-piperidinyl phenoxy) -2-propyl 348 2- (4-chloro-3-methyl- CH3 3,5-dimethyl-1-piperidinyl phenoxy) -2-propyl 349 2- (4- klor- 3- me til- CH3 3,3-dimethyl-1-piperidinyl phenoxy) -2-propyl 350 2- (4-chloro-3-methyl- CH3 2,6-dimethylmorpholine phenoxy) -2-propyl CH3 351 2- (4-chlorophenoxy) -2- CHS -N methyl-2-propyl CH2-CH = C (CH3) 2 352 2- (4-chlorophenoxy) -2- CHS CHS propyl -N CH 2 -CH = C (CH 3) 3 c 353 2- (4-chlorobenzyl) -2- CH3 CH3 propyl -N CH2-CH = C (CHS) 2 354 2- (2-chlorobenzyl) -2- CH3 CH3 propyl -N CH2-CH = C (CHS) 2 355 1- (4-chlorophenylthio) -2- CHS CHS methylpropyl -N CH2-CH = C (CH3) 2 356 l- (2,4-dichloro-phenoxy) - CH3 CH3 -2-methyl-2-propyl -N CH2-CH = C (CH3) 2 357 2- (2,3-dimethylphenoxy) - CH3 1-piperidinyl 2-propyl 358 2- (2,3-dimethylphenoxy) - CH3 3-methyl-1-piperidinyl 2-propyl 359 2- (2,3-dimethylphenoxy) - CH3 3,5-Dimethyl-1-piperidinyl 2-propyl 360 2- (2,3-dimethylphenoxy) - CH3 3,3-dimethyl-1-piperidinyl 2-propyl 361 2- (2,3-dimethylphenoxy) - CH3 1-perhydroazepinylcarbonyl 2-propyl 362 2- (2,3-dimethylphenoxy) - CH3 2,6-dimethylmorpholino 2-propyl 363 2- (2,3-dimethylphenoxy) - CH3 1-piperidinyl 2-propyl 364 2- (4-chloro-3,5-dimethyl- CHS 3-methylpiperidinyl phenoxy) -2-propyl 365 2- (4-chloro-3,5-dimethyl- CH3 3,5-dimethyl-piperidinyl phenoxy) -2-propyl 366 2- (4-chloro-3,5-dimethyl- CHS 3,3-dimethyl-l-piperidinyl phenoxy) -2-propyl 367 2- (4-chloro-3,5-dimethyl- CH3 1-perhydroazepinylcarbonyl phenoxy) -2-propyl 368 2- (4-chloro-3,5-dimethyl- CHS 2,6-dimethylmorpholino phenoxy) -2-propyl 369 2- (4-chloro-2-ethyl-phenoxy) - CHS 3-methyl-1-piperidinyl 2-propyl 370 2- (4-chloro-2-ethyl- CHS 3,5-dimethyl-1-piperidinyl phenoxy) -2-propyl 371 2- (4-chloro-2-ethyl- CH3 1-perhydroazepinylcarbonyl phenoxy) -2-propyl 372 2- (4-chloro-2-ethyl- CH3 3-methyl-1-piperidinyl phenoxy) -2-propyl 373 2- (4-chloro-2-ethyl CHS 3,5-dimethyl-l-piperidinyl phenoxy) -2-propyl

Op. [° C] refractive index

230 / 0.13 mbar

250 / 0.13 mbar

374-408 ° C

1.5047

-1 633

Example number R ¹ R ² -nr ³ r ⁴ Op. [° C] or refractive index (no) 374 2- (4-Chloro-2-ethyl-phenoxy) -2-propyl CD3 1-perhydroazepinylcarbonyl 375 l- (4-chlorophenyl) -2- -n-butyl CH3 1-piperidinyl 376 l- (4-chlorophenyl) -2- -n-butyl CH3 3-methyl-l-piperidinyl 377 1- (4-chlorophenyl) -2-n-butyl CWhen 3,5-dimethyl-l-piperidinyl 378 1- (4-chlorophenyl) -2-n-butyl CH3 3,3-dimethyl-l-piperidinyl 379 l- (4-chlorophenyl) -2- -n-butyl CH3 2,6-dimethylmorpholine 380 l- (4-chlorophenyl) -2- n-butyl CD3 1-perhydroazepinylcarbonyl 381 l- (4-chlorophenyl) -l- n-buten-2-yl CH3 1-piperidinyl 382 1- (4-chlorophenyl) -1-n-buten-2-yl CH3 1-perhydroazepinylcarbonyl 383 l- (4-chlorophenyl) -l- n-buten-2-yl CD3 3-methyl-1-piperidinyl 384 l- (4-chlorophenyl) -l- n-buten-2-yl CH3 3,5-dimethyl-l-piperidinyl 385 l- (4-chlorophenyl) -l- n-buten-2-yl CD3 3,3-dimethyl-1-piperidinyl 386 l- (4-chlorophenyl) -l- n-buten-2-yl CH3 2,6-dimethylmorpholino 387 2- (cyclohexylmethyl) - -2-n-propyl CH3 1-piperidinyl 1.4853 388 2- (cyclohexylmethyl) - -2-n-propyl CH3 1-perhydroazepinylcarbonyl 1.4835 1.4835 389 2- (cyclohexylmethyl) - -2-n-propyl CD3 3-methyl-1-piperidinyl 1.4825 390 2- (cyclohexylmethyl) - -2-n-propyl CH3 3,5-dimethyl-1-piperidinyl 1.4811 391 l- (2-methoxyphenyl) -2- -n-propyl CWhen 1-perhydroazepinylcarbonyl 413-416 392 1- (2-methoxyphenyl) -2-n-propyl CWhen 3-methyl-1-piperidinyl 393 l- (2-methoxyphenyl) -2- -n-butyl CH3 3-methyl-1-piperidinyl 394 2- (4-chloro-phenylthio) - -2-n-butyl CWhen 1-piperidinyl 395 2- (4-chlorophenylthio) -2-n-propyl CH3 1-perhydroazepinylcarbonyl 1.5061 396 2- (4-chlorophenyl-thio) ~ -2-n-propyl CWhen 3-methyl-l-piperidinyl 1.5067 397 2- (4-chloro-phenylthio) - -2-n-propyl CH3 3,5-dimethyl-l-piperidinyl 1.5044 398 2- (4-chlorophenyl-thio) ~ -2-n-propyl CH3 3,3-dimethyl-1-piperidinyl 420-421 399 2- (4-chlorophenylthio) -2-n-propyl CH3 2,6-dimethylmorpholino 400 2- (4-fluorobenzyl) -2-n-propyl CH3 3,3-dimethyl-1-piperidinyl 401 2- (4-fluoro-benzyl) -2- -n-propyl CH3 3,3,5-trimethyl-l-per- hidroazepinil.

-1 735

Example number R ¹ R ² = CH 3 unless otherwise indicated in the table -NR ³ R ⁴ Op · [° C] or refractive index [ηΐή f.p. 402 CH ₃ - (CH 2) 8- 3-methyl-1-piperidinyl 1.4501 403 C3- (CH2) s- 3,3-methyl-l-piperidinyl 1.4488 404 CH 3 - (CH 2) ₈ - 3,5-methyl-l-piperidinyl 1.4482 405 CH 3 (CH) "- 2,4-dimethyl-1-piperidinyl 1.4515 406 C3- (CH2) e- 2,6-dimethylmorpholine 1.4466 407 4- (tert-butyl) phenyl 3-methyl-1-piperidinyl 1.4960 408 4- (tert-butyl) phenyl 3,3-dimethyl-l-piperidinyl 1.4929 409 4- (tert-butyl) phenyl 3,5-dimethyl-l-piperidinyl 1.4922 410 2-phenylethyl 3-methyl-1-piperidinyl 1.5168 411 2-phenylethyl 4-methyl-1-piperidinyl 1.5166 412 2-phenylethyl 3,5-dimethyl-1-piperidinyl 1.5151 413 2-phenylethyl 2,6-dimethylmorpholino 1.5203 414 2-cyclohexyl-l-methylethyl l-piperidinyl 1.4810 415 2-cyclohexyl-1-methyl-ethyl 3-methyl-1-piperidinyl 1.4811 416 2-cyclohexyl-l-methylethyl 4-methyl-l-piperidinyl 1.4789 417 2-cyclohexyl-l-methylethyl 3,3-dimethyl-l-piperidinyl 1.4763 Example R ¹ R ² = CH 3 if different -NR ³ R ⁴ Op. [° C] or number not shown the refractive index in the table [Nm); bp 418 2-cyclohexyl-l-methylethyl 3,5-dimethyl-1-piperidinyl 1.5017 419 2-cyclohexyl-l-methylethyl 1-perhydroazepinylcarbonyl 1.4820 420 2-cyclohexyl-l-methylethyl morpholino 1.4825 421 2-cyclohexyl-l-methylethyl 2,6-dime tilmorpholine 1.4763 422 2- (3-methylcyclohexyl) -1-methylethyl 3-methyl-1-piperidinyl 1.4786 423 2- (3-methylcyclohexyl) -l-methylethyl 3,5-dimethyl-1-piperidinyl 1.4771 424 2- (3-methylcyclohexyl) -1-methylethyl morpholino 1.4805 425 2- (3-methylcyclohexyl) -1-methylethyl 2,6-dimethylmorpholino 1.4758 426 2- (4-fluorophenyl) -1-methylethyl 4-methyl-1-piperidinyl 1.4977 427 2- (4-Fluorophenyl) -1-methyl-ethyl 3,5-dimethyl-1-piperidinyl 1.4942 428 2- (4-Fluorophenyl) -1-methylethyl 2,6-dimethylmorpholino 1.4939 429 2- (4-fluorophenyl) -1-methylethyl 3-methyl-1-piperidinyl 1.4977 430 2- (2-chlorophenyl) -1-methylethyl 3-methyl-1-piperidinyl 1.5229 431 2- (2-chlorophenyl) -1-methylethyl 3,5-dimethyl-1-piperidinyl 1.5161 432 2- (2-chlorophenyl) -1-methylethyl 2,6-dimethylmorpholino 1.5158 433 2- (4-chlorophenyl) -1-methyl-phenyl 3-methyl-1-piperidinyl 1.5137 434 2- (4-chlorophenyl) -1-methyl-phenyl 2,6-dimethylmorpholino 1.5123 435 2- (3-methylphenyl) -l-methylethyl 3-methyl-1-piperidinyl 1.5049 436 2- (3-methylphenyl) -l-methylethyl 3,5-dimethyl-1-piperidinyl 1.5017 437 2- (3-methylphenyl) -1-methylethyl morpholino 1.5112 438 2- (3-methylphenyl) -1-methylethyl 2,6-dimethylmorpholino 1.5017 439 2- (4-methylphenyl) -l-methylethyl 3-methyl-1-piperidinyl 1.5064 440 2- (4-methylphenyl) -l-methyl-ethyl 3,5-dimethyl-l-piperidinyl 1.4999 441 2- (4-methylphenyl) -l-methylethyl perhidroazepino 1.5099 442 2- (4-methylphenyl) -1-methylethyl 2,6-dimethylmorpholino 1.5007 443 2- (2-ethoxyphenyl) -l-methylethyl 2,6-dimethylmorpholino 1.5045 444 2- (2-ethoxyphenyl) -1-methylethyl 3-methylpiperidino 1.5045 445 2- (3- / ~ trifluoro methyl / phenyl) -l- methylethyl 3,5-dimethyl-l-piperidinyl 1.4750 446 2- (3- / trifluoromethyl / phenyl) -l- methylethyl 2,6-dimethylmorpholino 1.4783 447 l- (3,4-dichlorobenzyl) -l-propyl 3,5-dimethyl-1-piperidinyl 1.5170 448 l- (3,4-dichlorobenzyl) -l-propyl 3-methyl-1-piperidinyl 1.5346 449 l- (3,4-dichlorobenzyl) -l-propyl 2,6-dimethylmorpholino 1.5195 450 l-cyclohexyl-2-methyl-2-propyl 4-methyl-1-piperidinyl 1.4853 451 l-cyclohexyl-2-methyl-2-propyl 3,3-dimethyl-l-piperidinyl 1.4791 452 l-cyclohexyl-2-methyl-2-propyl 3,3,4-trimethyl-perhydroazepino 1,4828 453 l-cyclohexyl-2-methyl-2-propyl morpholino 1.4855 454 1-cyclohexyl-2-methyl-2-propyl 2,6-dimethylmorpholine 1.4825 455 2 into nyl-2-propyl 3,5-dimethylpiperidine 1.5030 456 2- (2-fluoro-benzyl) -2-propyl 2,6-dimethylmorpholino 1.4996 457 2- (3-fluoro-benzyl) -2-propyl 3-methyl-1-piperidinyl 1.5019 458 2- (3-fluoro-benzyl) -2-propyl 3,5-dimethyl-l-piperidinyl 1.4987

-1 837

Example R ^{1 is a} serial number

R ² = CH ³ , unless otherwise stated -NR ³ R ⁴ not listed in the table

Op. [° C] or refractive index [nP]; bp

459 2- (3-fluorobenzyl) -2-propyl 2,6-dimethylmorpholino 1.4962 460 2- (4-fluorobenzyl) -2-propyl 3-methylpiperidino 143 ° C (HCl) 461 2- (4-fluorobenzyl) -2-propyl 3- (methoxycarbonyl) -1- 1.5070 462 2- (4-fluorobenzyl) -2-propyl piperidinyl 3,5-diethyl-1-piperidinyl 1.5577 463 2- {4-fluoro-benzyl) -2-propyl 2,6-dimethylmorpholino 1.4959 464 2- (2-chlorobenzyl) -2-propyl 2,6-dimethylmorpholino 1.5208 465 2- (3-chlorobenzyl) -2-propyl N-ethyl-N- (isopropyl) -amino 1.5076 466 2- (3-chlorobenzyl) -2-propyl piperidino 207 ° C (HCl) 467 2- (3-chlorobenzyl) -2-propyl 3-methyl-1-piperidinyl 1.5183 468 2- (3-chlorobenzyl) -2-propyl 3,5-dimethyl-1-200 ° C / 0.13 mbar 469 2- (3-chlorobenzyl) -2-propyl piperidinyl 3,5-diethyl-l-210 ° C / 0.13 mbar 470 2- (3-chlorobenzyl) -2-propyl piperidinyl perhidroazepino 1.5253 471 2- (3-chlorobenzyl) -2-propyl morpholino 1.5211 472 2- (3-chlorobenzyl) -2-propyl 2,6-dimethylmorpholine 1.5156 473 2- (4-chlorobenzyl) -2-propyl N-eyl-N- (i-propyl) -amino 1.5082 474 475 476 477 2- (4-chlorobenzyl) -2-propyl 2- (4-chlorobenzyl) -2-propyl 2- (4-chlorobenzyl) -2-propyl 2- (4-chlorobenzyl) -2-propyl N-methyl-N- (2-chlorobenzyl) amino N-methyl-N- (4-chlorobenzyl) amino N-methyl-N- (3-methylbenzyl) amino N-methyl-N- (4-methyl- 1.5434 1.5841 1.5437 1.5423 478 2- (4-chlorobenzyl) -2-propyl benzyl) amino 3,5-diethyl-piperidino 1.4982 479 2- (4-chlorobenzyl) -2-propyl morpholino 1.5246 480 2- (4-chlorobenzyl) -2-propyl 2,6-dimethylmorpholine 1.5146 481 2- (4-methylbenzyl) -2-propyl 2,6-dimethylmorpholino 1.5069 482 2- (2,4-dichlorobenzyl) -2-propyl 2,6-dimethylmorpholino 1.5234 483 2- (3,4-dichlorobenzyl) -2-propyl piperidino 73 ° C 484 2- (3,4-dichlorobenzyl) -2-propyl 2-methylpiperidino 1.5297 485 2- (3,4-dichlorobenzyl) -2-propyl 3-methylpiperidino 1.5293 486 2- (3,4-dichlorobenzyl) -2-propyl 3,5-dimethylpiperidino 1.5247 487 2- (3,4-dichlorobenzyl) -2-propyl 3,5-diethylpiperidine perhydroazepine 1.5170 488 2- (3,4-dichlorobenzyl) -2-propyl 1.5355 489 2- (3,4-dichlorobenzyl) -2-propyl 3,3,5-trimethyl resin 490 2- (3,4-dichlorobenzyl) -2-propyl -perhydroazepine morpholino 1.5318 491 2- (3,4-dichlorobenzyl) -2-propyl 2,6-dimethyl- 163 ° C (HCl) 492 2- (3,4-dichlorobenzyl) -2-propyl morpholino 2,6-dimethylmorpholino 1.5246 493 2,4-dichloro-phenoxymethyl 3,5-diethyl-piperidino 1.5230 494 2,4-dichloro-phenoxymethyl r ² = h 2,6-dimethylmorpholino 1.5249 495 1- (3,4-dichlorophenoxy) -1-propyl r ² = h 3-methylpiperidino 1.5110 496 l- (3,4-dichloro-phenoxy) -l-propyl 3,5-dimethylpiperidino 1.5071 497 l- (3,4-dichloro-phenoxy) -l-propyl morpholino 1.5189 498 1- (3,4-dichlorophenoxy) -1-propyl 2,6-dimethylmorpholino 1.5087 499 2- (3- / trifluoromethyl / -phenoxy) - N-methyl-N- (2-methyl- 1.4928 500 - 2-propyl 2- (3- (trifluoromethyl) phenoxy) - -but-2-en-l-yl) amino piperidino 1.4711 501 502 2-propyl 2- (3- (trifluoromethyl) -phenoxy) -2-propyl 2- (3- / trifluoromethyl / -phenoxy) - piperidino 1 3-methyl-piperidin.o (x HCl) 114 ° C 1.4676 503 2-propyl 2- (3- (trifluoromethyl) phenoxy) - 3,3-dimethylpiperidino 1.4650 504 2-propyl 2- (3- (trifluoromethyl) phenoxy) - 3,5-dimethylpiperidine 1.4653

2-propyl

-1 939

Example R ¹ R ² = CH 3 if different -NR ³ R ⁴ Op · [° C] or number not listed in the table refractive index [ri]; bp 505 2- (3- (trifluoromethyl) phenoxy) -2-propyl morpholino 1.4684 506 2- {3- / trifluoromethyl / -phenoxy) -2- propyl 2,6-dimethylmorpholino 1.4649 507 2- (3- (trifluoromethyl) -phenoxy) -2-propyl 2,6-Dimethyl-morpholino (X CH3-C6H4-SO3H) amorphous 508 2- (2,4-dichlorophenoxy) - 2-propyl piperidino 220 ° C / 0.13 mbar 509 2- (2,4-dichlorophenoxy) - 2-propyl 3-methylpiperidino 230 ° C / 0.13 mbar 510 2- (2,4-dichlorophenoxy) - 2-propyl 3,3-dimethyl-pipe- -ridino 240 ° C / 0.13 mbar 511 2- (2,4-dichlorophenoxy) -2-propyl 3,5-diethyl-pipe- piperidinopropyi 250 ° C / 0.13 mbar 512 2- (2,4-dichlorophenoxy) -2-propyl 3,5-diethyl-piperidino 250 ° C / 0.13 mbar 513 2- (2,4-dichloro-phenoxy) ~ 2-propyl perhidro- Hazepino 250 ° C / 0.13 mbar 514 2- (3,4-dichlorophenoxy) -2-propyl piperidino 240 ° C / 0.13 mbar 515 2- (3,4-dichlorophenoxy) -2-propyl 3-methyl-pipe- piperidinopropyi 240 ° C / 0.13 mbar 516 2- (3,4-dichlorophenoxy) -2-propyl 3,3-dimethyl-PI piperidinopropiophenone 250 ° C / 0.13 mbar 517 2- (3,4-dichlorophenoxy) -2-propyl 3,3-dimethylpiperidino (X CH3-C6H4-SO3H) 131 ° C 518 2- (3,4-dichlorophenoxy) -2-propyl 3,5-diraetil- piperidino 250 ° C / 0.13 mbar 519 2- (3,4-dichlorophenoxy) -2-propyl 3,5-Dimethyl-piperidino (X CH3C6H4-SO3H) 148 ° C 520 2- (3,4-dichloro-phenoxy) -2-propyl perhidroazepino 250 ° C / 0.13 mbar 521 2- (3,4-dichlorophenoxy) -2-propyl 2,6-dimethylmorpholino 250 ° C / 0.1 lbar 522 2- (2-methyl-3-chlorophenoxy) -2- propyl 3-methylpiperidino 1.5012 523 2- (2-methyl-3-chlorophenoxy) -2-propyl 3,5-dimethylpiperidino 1.5034 524 2- (2-methyl-3-chlorophenoxy) -2- propyl perhidroazepino 1.5021 525 2- (3-methyl-4-chlorophenoxy) -2- propyl 3,5-diethyl-piperidino 230 ° C / 0.13 mbar 526 2- (3-ethyl-4-chlorophenoxy) -2-propyl 1-piperidinyl 1.5082 527 2- (3-ethyl-4-chlorophenoxy) -2-propyl 3-methyl-l-piperidinyl 1.5043 528 2- (3-ethyl-4-chlorophenoxy) -2-propyl 3,5-dimethyl-1-piperidinyl 1.5012 529 2- (3-ethyl-4-chlorophenoxy) -2-propyl 2,6-d is tilmor f olino 1.5010 530 2- (3- (trifluoromethyl) -4-chlorophenoxy) -2-propyl 3-methyl-l-piperidinyl 1.4795 531 2- (3- / trifluoromethyl / -4-chloro-phenoxy) - 2-propyl 3,3-dimethyl-1-piperidinyl 1.4770 532 2- (3- / trifluoromethyl / -4-chloro-phenoxy) - 2-propyl 3,5-dimethyl-1-piperidinyl 1.4761 533 2- (3- (trifluoromethyl) -4-chlorophenoxy) -2-propyl morpholino 1.4849 534 2- (3- (trifluoromethyl) -4-chlorophenoxy) -2-propyl 2,6-dimethylmorpholino 1.4827 535 2- (3,4-dichlorophenyl) thio-2-propyl 3-methylpiperidino 1.5360 536 2- (3,4-dichlorophenyl) thio-2-propyl 3,5-dimethylpiperidino 1.5342 537 2- (2,5-dimethyl-4-chlorophenyl) -2- propyl 2,6-dimethylmorpholino 1.5164 538 l- (4-fluoro-phenoxy) -2-methyl-2- propyl 3,3-dimethyl-1-piperidinyl (X CH 3 C 6 H 4 SO 3 H) amorphous (X CH3C6H4SO3H)

-2 041

Example R ¹ R ² = CH 3 if different -NR ³ R ⁴ Op. [° C] or number not listed in the table the refractive index [woman]; bp 539 l- (3-chloro-phenoxy) -2-methyl-2-propyl 3,5-dimethyl-1-piperidinyl 200 ° C / 0.13 mbar 540 l- (3-chloro-phenoxy) -2-methyl-2-propyl morpholino 1.5114 541 l- (3-chloro-phenoxy) -2-methyl-2-propyl 2,6-dimethylmorpholino 141 ° C (X HCl) 542 1- (3-chlorophenoxy) -2-methyl-2-propyl 2,6-dimethylmorpholino 135 ° C

(X CHa-CefD-SOaH) (X CH3-C6H4-SO3H)

543 l- (3-chloro-phenoxy) -2-methyl-2-propyl 2,6-dimethylmorpholino (X naphtha 176 ° C talin disulfonate) 544 l- (4-chlorophenoxy) -2-methyl-propyl N-methyl-N- (2-ethylbutyl) - amino 1.4910 545 l- (4-chlorophenoxy) -2-methyl-propyl 3,5-die til-pipe ridino 1.5062 546 l- (2-methyl-phenoxy) -2-methyl-propyl 1-piperidinyl amorphous (x CH3SO3H) 547 l- (2-methylphenoxy) -2-methylpropyl 1-piperidinyl 110 ° C (x CH3C6H4SO3H) 548 1- (2-methylphenoxy) -2-methylpropyl 1-piperidinyl 118 ° C (x naphthalenesulfonic acid) 549 1- (2-me til-f e noxi) - 2-me til-p r opil 1-piperidinyl 46-48 ° C (x citric acid) 550 l- (2-methylphenoxy) -2-methylpropyl 3-methyl-1-piperidinyl 1.4922 551 l- (3-methylphenoxy) -2-methylpropyl 3-methyl-1-piperidinyl 1.4890 552 l- (3-methylphenoxy) -2-methylpropyl 3,3-dimethyl-1-piperidinyl 1.5112 553 1- (3-methylphenoxy) -2-methylpropyl 3,5-dimethyl-1-piperidinyl 200 ° C / 0.13 mbar 554 l- (3-methylphenoxy) -2-methylpropyl 3,5-dimethyl-l- piperidinyl 139 ° C (x HCl) 555 l- (3-methylphenoxy) -2-methylpropyl perhidro- Hazepino 200 ° C / 0.13 mbar 556 l- (3-methylphenoxy) -2-methylpropyl 2,6-dimethyl- morpholino 200 ° C / 0.1 lbar 557 l- (2-ethyl-phenoxy) -2-methyl-propyl N-methyl-N- (2-chlorobenzylamino) 1.5112 558 l- (2-ethyl-phenoxy) -2-methyl-propyl N-methyl-N- (2-methylbenzyl) amino 1.5104 559 l- (2-ethyl-phenoxy) -2-methyl-propyl 3,3,5-trimethyl -perhydroazepine 1.5094 560 l- (2-ethyl-phenoxy) -2-methyl-2-propyl 3,3,5-trimethyl -perhydroazepine 1.5110 561 l- (2-ethyl-phenoxy) -2-methyl-2-propyl 2,6-dimethylmorpholine 1.5031 562 l- (3- / trifluoromethyl / -phenoxy) -2-methyl- 2-propyl 1-piperidinyl 1.4709 563 l- (3- / trifluoromethyl / -phenoxy) -2-methyl- 2-propyl 3-methyl-l-piperidinyl 1.4708 564 l- (3- / trifluoromethyl / -phenoxy) -2-methyl-2-propyl 4-methyl-1-piperidinyl 1.4684 565 1- (3- (trifluoromethyl) -phenoxy) -2-methyl-1-2-propyl 3,5-dimethyl-1-piperidinyl 1.4675 566 l- (3- / trifluoromethyl / -phenoxy) -2-methyl- 2-propyl morpholino 1.4729 567 l- (3- / trifluoromethyl / -phenoxy) -2-methyl- 2-propyl 2,6-dimethylmorpholino 1.4662 568 l- (3,4-dichloro-phenoxy) -2-methyl-2- propyl 3-methyl-1-piperidinyl 1.5094 569 1- (3,4-dichlorophenoxy) -2-methyl-2-propyl 3,3-dimethyl-1-piperidinyl 1.5108 570 1- (3,4-dichlorophenoxy) -2-methyl-2-propyl 3,3-dimethyl-1-piperidinyl 168 ° C (x HCl)

-2 143

Example R ^{1 is a} serial number

R ² = CH ³ , unless otherwise stated -NR ³ R ⁴ not listed in the table

Op. [° C] or refractive index [no]; bp

571 l- (3,4-dichloro-phenoxy) -2-methyl-2- propyl 3,5-dimethyl-1-piperidinyl 1.5087 572 1- (3,4-dichlorophenoxy) -2-roethyl-2-propyl 3,5-dimethyl-l- piperidinyl 208 (x HCl) 573 l- (3,4-dichloro-phenoxy) -2-methyl-2- propyl 3,5-dimethyl-l-piperidinyl amorphous (X CH3C6H4SO3H) 574 l- (3,4-dichloro-phenoxy) -2-methyl-2- propyl perhidroazepino 1.5128 575 l- (3,4-dichloro-phenoxy) -2-methyl-2- propyl 2,6-dimethylmorpholine 1.5122 576 1- (3,4-dichlorophenoxy) -2-methylpropyl 2,6-dimethylmorpholine 197 ° C (x HCl) 577 l- (2,3-dimethyl-phenoxy) -2-methyl- propyl 3-methyl-1-piperidinyl 1.5066 578 l '- {2,4-dimethyl-phenoxy) -2-methyl- propyl 2,6-dimethylmorpholine 1.4921 579 l- (2-methyl-3-chlorophenoxy) -2-methyl) - propyl 3-methyl-l-piperidinyl 1.5052 580 l- (2-methyl-3-chlorophenoxy) -2-methyl- 2-propyl 3,3-dimethyl-1-piperidinyl 1.5042 581 l- (2-methyl-3-chlorophenoxy) -2-methyl- 2-propyl 3,5-dimethyl-1-piperidinyl 1.5039 582 1- (2-methyl-3-chlorophenoxy) -2-methyl-2-propyl perhidroazepino 1.5044 583 l- (2-methyl-3-chlorophenoxy) -2-methyl-2-propyl 2,6-dimethylmorpholine 1.5067 584 l- (3-methyl-4-chlorophenoxy) -2-methyl-2-propyl 1-piperidinyl 1.5074 585 l- (3-methyl-4-chlorophenoxy) -2-methyl 2-propyl 3-methyl-l-piperidinyl 1.5052 586 l- (3-methyl-4-chlorophenoxy) -2-methyl 2-propyl 3,5-dimethyl-1-piperidinyl 1.5035 587 l- (3-methyl-4-chlorophenoxy) -2-methyl- 2-propyl 2,6-dimethylmorpholino 1.5019 588 1- (2-chloro-5-methylphenoxy) -2-methyl-2-propyl N-methyl-N- (2-chlorobenzylamino) 1.5080 589 1- (2-chloro-5-methylphenoxy) -2-methyl-2-propyl 3-methyl-l-piperidinyl 1.5004 590 1- (2-chloro-5-methylphenoxy) -2-methyl-2-propyl 3,3-dimethyl-1-piperidinyl 1.5027 591 1- (2-chloro-5-methylphenoxy) -2-methyl-2-propyl 3,5-dimethyl-1-piperidinyl 1.5017 592 l- (2-chloro-5-methylphenoxy) -2- -raetil-2-propyl perhidroazepino 1.5031 593 1- (2-chloro-5-methylphenoxy) -2-methyl-2-propyl 2,6-dimethylmorpholine 1.5062 594 l- (2-bromo-4-methylphenoxy) -2- methylpropyl 1-piperidinyl 1.5208 595 l- (3-bromo-4-methyl-phenoxy) -2-methyl-2-propyl 3-methyl-l-piperidinyl 1.5150 596 1- (3- (trifluoromethyl) -4-chlorophenoxy) -2-methyl-2-propyl 1-piperidinyl 1.4870 597 1- (3- (trifluoromethyl) -4-chlorophenoxy) -2-methyl-2-propyl 3-methyl-l-piperidinyl 1.4809 598 1- (3-methyl-4- (methylthio) phenoxy) -2-methyl-2-propyl 1-piperidinyl 1.5230 599 l- (3-methyl-4- / methylthio / -phenoxy) - -2-methyl-2-propyl 4-methyl-l-piperidinyl 1.5202 600 l- (3-methyl-4- / methylthio / phenoxy) ~ -2-methyl-2-propyl 3,5-dimethyl-l-piperidinyl 1.5189

-22Example R ^{1 is a} serial number

R ² = CH ³ , unless otherwise stated -NR ³ R ⁴ not listed in the table

[° C] or refractive index [nnl; bp

601 1- (4- (methylthio) phenoxy) -2-methyl-2,6-dimethylmorpholine 2-propyl 1.5182 602 1- (4-chlorophenylthio) -2-methyl-2- 4-methyl-1-piperidinyl propyl 1.5260 603 1- (4-chlorophenylthio) -2-methyl-2- 3,5-dimethyl-1-piperidinyl propyl 1.5201 604 1- (4-chlorophenylthio) -2-methyl-2- 2,6-dimethylmorpholino propyl 1.5241 605 2- (4-chlorophenyl) vinyl-1-pyrrolidinyl (R ² = tert-butyl) 86-97 606 phenoxymethyl (R ² = H) 1-piperidinyl 1.5222

In the following pharmacological examples, the known compounds of formula (A) and (20) (B) were used as comparators.

Example A)

Protective effect against Phytophthora in tomatoes

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether 30

To prepare a suitable formulation of the active ingredient, 1 part by weight of the active ingredient is mixed with the indicated amount of solvent and emulsifier and diluted with water to a concentration of 0.005% by weight of the active ingredient. Young tomato plants are sprayed with dewatering with the above composition. After the spray juice had dried, the plants were infected with an aqueous spore suspension of Phytophora infestans and kept in a cabinet at 20 ° C and 100% relative humidity for 3 days. The plants are then evaluated for infectivity. The results are given in the table below.

The table

Protective effect against Phytophthora in tomatoes

agent Percentage of infection At a concentration of 0.005% w / v Known active ingredient of formula (A) 60 Example 71 16 the hydrochloride

Continuation of Table A) Example number % contamination at a concentration of 0.005% w / v 157 30 158 27 159 27 160 27 73 30 212 27 206 27 167 23 214 10 197 17 291 27 286 23 285 20 306 27

-2 347

Example number percent contamination at 0.005% active ingredient concentration

307 37 274 18 238 17 277 17 270 23 267 23

Example B)

Treatment of barley seeds against Drechslera graminea (= Helminthosporium gramineum).

The active ingredients are used in dry dressings. The seed dressing is prepared by mixing the active ingredient with finely ground stone powder; according to formulation example 1. This formulation ensures uniform distribution of the active ingredients.

During dressing, the infected seeds are shaken in a glass container sealed with the dressing agent for 3 minutes. The seeds were then placed in a screened petri dish containing sieved, wet garden soil for 10 days in a refrigerator at 4 ° C. At this temperature, the germination of the barley grains (and, where appropriate, the fungal spores) begins. The pre-germinated vasculature grains (2x50) are seeded in cultures at a depth of 3 cm and grown in a greenhouse at about 18 ° C and exposed to light for 15 hours daily. About 3 weeks after sowing, the plants are examined for signs of leaf stripping. The results are given in Table B).

Table B)

Treatment of barley seeds against Drechslera gramineae

agent quantity used in mg / kg of seed diseased plants as a percentage of total plants untreated 24.0 Known formula (B) 600 19.0 agent Example 74 500 1.1 Example 71 500 1.2 the hydrochloride Example 96 500 2.5 Example 102 500 3.6 Example C) dew spray it and then -

after drying - Erysiphe graminis f. sp.

Powdery mildew barley Solvent: 100 parts by weight of dimethylformamide Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether part by weight with the indicated amount of solvent and emulsifier, and the resulting concentrate is diluted with water to a concentration of 0.025% by weight.

Young barley plants are sprinkled with the spore of the composition which is used to carry powdery mildew pests. The plants are kept in a greenhouse under favorable conditions for the development of powdery mildew, i.e. at about 20 ° C and 80% relative humidity. 7 days after infection, the degree of infectivity is evaluated and expressed as a percentage of untreated control. The results are shown in Table C).

-2 449

Active ingredient Degree of infection in untreated control

C) Table

Protection against powdery mildew in barley

Is a known active ingredient of formula (B) 100 the active ingredient of Example 74 3.8 hydrochloride of the compound of Example 71 3.8 the compound of Example 76 12.5 the compound of Example 73 12.5 the compound of Example 29 25.0 the active ingredient of Example 72 12.5 the compound of Example 88 12.5 the compound of Example 87 0.0 the compound of Example 111 25.0 the compound of Example 90 12.5 the active ingredient of Example 103 8.8 the active ingredient of Example 104 12.5 the compound of Example 105 16.3 the compound of Example 93 10.0 the compound of Example 96 3.8 the compound of Example 95 12.5 the compound of Example 92 12.5 the compound of Example 98 33.8 the compound of Example 102 21.3 the compound of Example 100 12.5 the compound of Example 75 33.8

Example D 35

Protective effect against rabies

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl-poly-glycol ether are dissolved in the specified amount of solvent, the indicated amount of emulsifier is added and the resulting concentrate is diluted with water to a concentration of 250 ppm.

Young apple vines are infected with an aqueous conidium suspension of the apple rabies agent (Venturia inaequalis). The plants were kept in an incubation booth at 20 ° C and 100% relative humidity for 1 day and then transferred to the greenhouse. 42 hours after infection, the plants were sprayed with dripping water into dripping water and kept in a greenhouse at 20 ° C and 70% relative humidity for 12 days, after which the experiment was evaluated. The results are given in the table below.

Presentation examples

1. Dusting agent

The active ingredient prepared according to Example 206 is 65

0.5 parts by weight of the mixture is mixed with 99.5 parts by weight of natural stone powder, and the mixture is finely ground, and the composition is powdered to the plants to be treated and their surroundings.

2. Dispersible powder

(a) liquid active ingredient formulation

The bulk of the active ingredient prepared in Example 238 is mixed with 1 part by weight of dibutyl naphthalene sulfonate. 4 parts by weight of lignin sulfonate, 8 parts by weight of highly dispersed silica and 62 parts by weight of limestone powder and the mixture is ground to a fine powder. Before use, sufficient water is added to achieve the desired drug concentration.

(b) the formulation of the active substance in solid form

50 parts by weight of the compound of Example 71 are mixed with 1 part by weight of dibutylnaphthalene sulfonate. 6 parts by weight of lignin sulfonate, 6 parts by weight of highly dispersed silica and 37 parts by weight of natural stone powder. The mixture was ground to a fine powder. Prior to use, sufficient water is added to the dispersible powder to achieve the desired drug concentration.

-2 551

3. Emulsifiable concentrate

25 parts by weight of the compound of Example 67 are dissolved in a mixture of 55 parts by weight of xylene and 10 parts by weight of cyclohexanone. As emulsifier, 10 parts by weight of a mixture of dodecylbenzenesulfonic acid Ca and nonylphenol polyglycolol ether are added. Prior to use, the emulsifiable concentrate is diluted with water to achieve the desired drug concentration.

4. Granules

(a) liquid active ingredient formulation

One part by weight of the active ingredient prepared according to Example 235 is sprayed onto 9 parts by weight of granulated absorbent clay. The resulting granulate is sprayed onto the plants and their surroundings.

b) Formulation of solid active ingredient 0.5 parts by weight to 1.0 mm Particle size sand is added with 2 parts by weight of spindle oil followed by 7 parts by weight of premix. The drug premix consists of 75 parts by weight of the active ingredient of Example 39 and 25 parts by weight of natural stone powder. The mixture is treated in a suitable blender until a homogeneous bulk powder-free granulate is obtained. The granulate is sprayed onto the plants to be treated and their surroundings.

5. ULV preparation

To 90 parts by weight of the compound of Example 47 was added 3 parts by weight of polyethylene oxide as an emulsifier and the resulting mixture was dissolved in 7 parts by weight of an aromatic mineral oil fraction. The resulting composition is applied to the area to be treated by the ULV procedure.

Claims (6)

Fungicidal compositions, characterized in that they contain from 0.1 to 95% by weight of an aminoketal derivative of the formula I or an acid addition salt thereof, preferably with hydrochloric acid - in which R ¹ is a dihalophenyl group. , phenoxy (C2-C6-alkyl) optionally substituted in the phenyl moiety with up to two groups optionally substituted by C1-C4 alkoxy or C5-C7 cycloalkyl, or mono- or C1-C4 alkyl or nitro and / or optionally substituted in the phenyl moiety; Phenyl (C 1 -C 4) alkyl, mono- or di-substituted with C 4 alkyl or halo, R ² is C 1-4 alkyl, while R ³ and R ⁴ are C 1 -C 6 alkyl or, with a adjacent nitrogen atom, a morpholino group * or a C 1 -C 4 alkyl or P 1 -C 4 alkoxylcarbonyl group or a piperazino group monosubstituted with up to two substituents; or piperidino optionally monosubstituted with C1-C4 alkyl or phenyl, with solid carriers, preferably mineral flour such as limestone powder or inorganic fillers formed by precipitation, and liquid carriers, preferably aromatic hydrocarbons or mineral oil fractions and surfactants, aryl polyglycol ethers with dodecyl benzenesulfonic acid salts. Spreadsheet agent % Of infection (250 ppm) Formula C (known) 62 Formula D (known) 75 66 0 68 16 86 3 81 6 270 1 269 10 267 11 244 14 246 3 -26Hatóanyag % Of infection (250 ppm) 245 247 248,268 299 301 87 286 285 212 206 233 291 297 300 302 157 158 159 160 70 170 189 3 8 1 1 0 0 0 9 4 14 2. A process for the preparation of the amnoketal derivatives of the formula IA and their acid addition salts, preferably with hydrochloric acid, wherein R ^{16 is C} 6 -C 12 alkyl, haloalkyl having 1 to 5 halogens and 2 to 6 carbon atoms, gg being benzyl monosubstituted in the phenyl moiety, optionally monosubstituted or halo in the phenyl moiety, or C 1 -C 4 alkyl or trifluoromethyl. phenyl (C2-C6) alkyl monosubstituted, phenylsulfonyl (C2-C6 alkyl) monosubstituted in the phenyl moiety, phenyl optionally substituted by halo optionally in the phenyl moiety; C 6 -C 50 alkenyl), phenyl-thio (C 2 -C 6 -C 5 alkyl) optionally substituted on the phenyl moiety with one or two halo or C 1 -C 4 alkyl, optionally C 5 -C 7 cycloalkyl in the phenyl moiety -, C 1 -C 4 alkoxy-carbonyl, C 1 -C 4 alkoxy, trifluoromethyl 60 or phenyl, singly or with a halogen atom and / or for 1 to 4 s up to twice with C 1 -C 4 alkyl, or with halogen and twice with nitro or trifluoromethyl, or twice with C 1 -C 4 -alkyl and C 1 -C 4 -alkyl, or with C 1 -C 4 -alkyl, or with C 1 -C 4 -alkyl a tri-substituted phenoxy (C 1 -C 6) alkyl or a (C 1 -C 4) alkyl optionally substituted in the cycloalkyl moiety ( C3-C7 cycloalkyl) - (1- C4 alkyl), R ² 'is hydrogen, C 1 -C 12 alkyl or phenyl optionally substituted by halo; R ³ 'and R ⁴ ' are C 1 -C 6 alkyl or benzyl or phenethyl optionally substituted by halogen or C 1 -C 4 alkyl, or C 5 -C 7 cycloalkyl or C 3 -C 7 alkenyl or C 3 -C 7 alkynyl, or R ³ 'and R ⁴ ' together with the adjacent nitrogen atom represent a pyrazolo, pyrrolidino, perhydroazepino, trimethyl perhydroazepino group or a morpholine or a (1-4C) alkyl or (1-4C) alkyl or a (1-4C) alkyl group; C 4 alk Piperazino monosubstituted with -255 oxy) carbonyl or piperidino monosubstituted or mono- or di-substituted with C 1-4 alkyl optionally with benzyl, phenyl, C 1-4 alkoxy) carbonyl; characterized in that a substituted dioxolane of formula II - in formula XI - wherein R ¹ 'and R ² ' are as defined above and X is halogen is optionally substituted alkylsulfonyloxy or arylsulfonyloxy; group - one (III) general 5 is reacted with an amine of formula 5, wherein R ³ 'and R ⁴ ' are as defined above, optionally in the presence of a catalyst, optionally a base and optionally a solvent, and the resulting compound is optionally Converted into 10 acid addition salts.