DD265548A5 - FUNGICIDAL AGENTS - Google Patents

Abstract

1. Substituted hydroxypropylamine derivatives of the general formula (I) see diagramm : EP0256367,P35,F2 in which R**1 represents phenyl, phenoxy or phenylthio, phenylalkyl, phenoxyalkyl and phenylthioalkyl, in each case having 1 or 2 carbon atoms in the alkyl part, which are in each case optionally monosubstituted or polysubstituted in the phenyl part by halogen ; straight-chain or branched alkyl, alkoxy or alkylthio in each case having up to 5 carbon atoms ; halogenoalkyl, halogenoalkoxy or halogenoalkylthio in each case having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, the substituents being identical or different, and represents cyclohexyl, cyclohexyloxy, cyclohexylthio, cyclohexylalkyl, cyclohexyloxyalkyl and cyclohexylthioalkyl, in each case having 1 or 2 carbon atoms in the alkyl part, which are in each case optionally monosubstituted or polysubstituted in the cyclohexyl part by straight-chain or branched alkyl and alkoxy in each case having up to 5 carbon atoms, trifluoromethyl or trifluoromethoxy, the substituents being identical or different, R**2 represents hydrogen or methyl ; R**3 represents methyl or ethyl, and R**4 and R**5 , independently of one another, represent straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched alkenyl having 3 to 6 carbon atoms or R**4 and R**5 , together with the nitrogen to which they are bound, represent a 5- to 7-membered, saturated heterocyclic ring, having 1 or 2 heteroatoms, which is optionally monosubstituted or polysubstituted by methyl, ethyl or hydroxymethyl, the substituents being identical or different and their acid-addition compounds and metal salt complexes which are tolerated by plants, with the exception of the compound 1-N,N-dimethylamino-2,3-dimethyl-4-(4-chlorophenyl)-2- butanol.

Description

Field of application of the invention

The invention relates to fungicidal center !, the new substituted hydroxypropylamine derivatives as active ingredient contains η and their preparation.

Characteristic of the known state of the art

It is known that organic sulfur compounds, such as, for example, the zinc ethylone-1,2-bis-dithiocarbamate, have good fungicidal properties (compare R. Wa gler, Chemie der Pflanzenschutz- und Schädlingsbekungsmittel, Springer Verlag, 1970, Volume 2, page 65 ff).

However, the action of these compounds is, in particular at low application rates and concentrations, not always fully satisfactory in some applications.

Object of the invention

With the invention fungicidal agents are provided which contain a new active ingredient hydroxypropylamine derivatives. These new compounds have a particularly high fungicidal activity.

Explanation of the essence of the invention

The object of the invention is to provide fungicidal compositions which have a particularly high fungicidal activity.

There have been new substituted hydroxypropylamine derivatives of the general formula (I)

R ² OH CC R ³ CH

⁴

in which

R 'is each optionally substituted phenyl, phenylthio, phenylalkyl, phenoxyalkyl and phenylthioalkyl; for each

optionally substituted cyclohexyl, cyclohexyloxy, cyclohexylthio, cyclohexylalkyl, cyclohexylalkyl and

Cyclohexylthioalkyl and optionally substituted by halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or

Haiogenalkylthio substituted phenoxy; R ^{2 is} hydrogen or methyl; R ^{3 is} methyl or ethyl and

R ⁴ and R ⁵ independently of one another represent alkyl or alkenyl, or R ⁴ and R ^5, together with the nitrogen atom to which they are bonded, are substituted for a more highly substituted,

saturated heterocycle, which may optionally contain further heteroatoms, and their plant-tolerated acid addition compounds and metal salt complexes uefundone.

The compounds of the formula (I) can be obtained as geometric and / or optical isomers or mixtures of isomers of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.

Furthermore, it has been found that a) the exact substituted hydroxypropylamine derivatives of the general formula (I)

R ² OH

, 11 x ^R

R ¹ -C-C-CHO-N ^ _ (I) ₁

R ³ CH ₃

in which

R 'is each optionally substituted phenyl, phenylthio, phenylalkyl, phenoxyalkyl and phenylthioalkyl; For

optionally substituted cyclohexyl, cyclohexyloxy, cyclohexylthio, cyclohexylalkyl,

Cyclohexyloxyalkyl and cyclohexylthioalkyl and also optionally by halogens, alkyl, alkoxy, alkylthio,

Haloalkyl, haloalkoxy or haloalkylthio substituted phenoxy stsht; R 'is hydrogen of methyl; R ^{3 is} methyl or ethyl and

R ⁴ and R ⁵ independently of one another represent alkyl or alkenyl, or R ⁴ and R ⁵ together with the nitrogen atom to which they are attached represent an unsubstituted or substituted, saturated heterocycle which may optionally contain further heteroatoms,

and their plant-tolerated acid addition compounds and metal salt complexes, if epoxides of the general formula (II)

R ² OR ¹ -CC CH ₂ <»),

U ι

R ³ CH ₃

which one

R ¹ , R ² and R ^{3 have} the abovementioned meaning, with amines of the general formula (III)

HnC '"/

R ⁵

in which

R ⁴ and R ^B have the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst and, if appropriate, subsequently adding an acid or a metal salt; or b) the new substituted hydroxypropylamine derivatives of the general formula (Ia)

R ² OH

R ¹ ^ -CC-CH ₂ -N ^ (la),

IIR ⁵ i

R ³ CH ₃

in which

R '' 'is in each case optionally substituted cyclohexyl, cyclohexyloxy, cyclohexylalkyl or cyclohexyloxyalkyl R ² , R ³ , R ⁴ and R ^{6 have} the abovementioned meaning,

and their plant-tolerated acid addition compounds and metal salt complexes, if corresponding hydroxypropylamines derivatives of the general formula (Ib)

R ² OH

II / R ⁴

Rl ~ 2_ <»r» pn _Kj

in which

R ¹ ' ^{2 is} in each case optionally substituted phenyl, phenylalkyl or phenoxyalkyl and represents phenoxy optionally substituted by halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio and

R ² , R ³ , R ⁴ and R ^{6 have} the abovementioned meaning,

optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst and optionally under Orhöhtem pressure; and optionally subsequently adding an acid or a metal salt. Furthermore, it has been found that the new substituted hydroxypropylamine derivatives of the general formula (I) have good funigzide properties. Surprisingly, the compounds of the formula (I) according to the invention show a higher fungicidal activity than the zinc ethylene-1,2-bis-dithiocarbamate known from the prior art, which is effectively an obvious compound. The compounds according to the invention thus represent an enrichment of the art. The substituted hydroxypropylamine derivatives according to the invention are generally defined by the formula (I). In this formula, R ¹ is preferably in each case optionally mono- or polysubstituted by identical or different substituents phenyl, phenoxy, phenylthio, phenylalkyl, phenoxyalkyl and phenylthioalkyl having in each case 1 or 2 carbon atoms in the alkyl moiety, suitable phenyl substituents being: halogen; straight-chain or branched alkyl, alkoxy or alkylthio each having up to 5 carbon atoms; Haloalkyl, haloalkoxy or haloalkylthio with, respectively

1 o ^r 2 carbon atoms and 1 to 5 identical or different halogen atoms, such as preferably fluorine or chlorine atoms: and in each case optionally monosubstituted or polysubstituted by identical or different substituiertos cyclohexyl, cyclohex / Ioxy, cyclohexylthio, cyclohexylalkyl, Cyclohexy loxyalky I and Cyclohexylthioalky I with in each case optionally 1 or 2 carbon atoms in the alkyl moiety, wherein as cyclohexyisubstituunten in each case come into question; straight-chain or branched alkyl and alkoxy each having up to 5 carbon atoms, trifluoromethyl or trifluoromethoxy;

R ^{2 is} hydrogen or methyl; R ^{3 is} methyl or ethyl and R ⁴ and R ^{8 are} independently of each other gcradkettiges or branched alkyl having 1 to 8 carbon atoms or for

straight-chain or branched alkenyl having 3 to 6 carbon atoms or R ⁴ and R ⁶ together with the nitrogen atom to which they are bonded, for a monosubstituted, polysubstituted, identically or differently, substituted 5 to 7-membered, saturated heterocyclic compound having 1 or

2 heteroatoms, preferably nitrogen and oxygen, are possible as substituents in question; Methyl, ethyl and hydroxymethyl.

Particularly preferred are precursors of the general formula (I) in which

R ^{1 is} in each case optionally monosubstituted to trisubstituted by identical or different substituents phenylmethyl, phenoxymethyl, phenylthiomethyl, phenoxy or phenylthio, in each case being suitable as phenyl substituents: fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl; n-, i-, s- and t-butyl, n-pentyl, 2-methyl-2-butyl, methoxy, ethoxy, n- and i-propoxy, t-butoxy, trifluoromethyl, trifluoromethoxy and trifluoromethylthio; and in each case optionally monosubstituted to trisubstituted by identical or different substituents cyclohexylmethyl, cyclohexyloxymethyl, 'tyclohexyithiomoihyl, cyclohxy or cyclohexylthio, wherein as cyclohexyl each in question. Methyl, ethyl, η- and i-propy !; n-, i-, s- and t -butyl, n -pentyl, 2-methyl-2-butyl, methoxy, ethoxy, n- and i-propoxy, t-butoxy, trifluoromethyl and trifluoromethoxy;

R 'is hydrogen or methyl; R ^{3 is} methyl or ethyl and

R ⁴ and R ^{5 are} independently methyl, ethyl, η- and i-propyl; n-, i-, s- and t-butyl, n-pentyl, allyl, 2-butenyl or 3-methyl-2-butonyl, or

R ⁴ and R ⁶ together with the nitrogen atom to which they are attached are each optionally mono- to trisubstituted by identical or different methyl, ethyl or hydroxymethyl-substituted 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl, 4-morpholinyl or 1 -Hyxyhydronzepinyl stand.

Specifically, except for the compounds mentioned in the preparation examples, the following compounds are suitable

called general formula (I):

R ² OH

JI ^

R ¹ -C-C-CH ₂ -N ^ _β (I)

Il rs

R ³ CHo

Table 1

R ¹

CH.

S-CH ₂ - CH ₃

CH-

-CHo- CHr

CH-

CHr

CH,

CH,

H; -C-CH ₂ -CH ₃ CH ₃

-N 0

CH

CH ₃

-Q

CH ₃ CH ₃

-N 0

CH ₃

CHO

-N 0

CHr

CHr

CHr

CH-

CH,

CHr

CHr

CHr

If, for example, 4- (3-chlorophenyl) -3,3-dimethyl-2-methyl-1-butene-1-oxide and piperidine are used as starting materials, the reaction procedure of the process (a) according to the invention can be represented by the following formula scheme:

CHo O

egg

CH ₃ CH ₃

Cl

CH ₃ OH

I ³ I

Ko-C C-CH ₂

CH ₃ CH ₃

-O

For example, using 3,3-dimethyl-2-methyl-4- (3-methylphenyl) -1- (morpholin-4-yl) -2-butanol as the starting material, the reaction step of the process (b) of this invention may be represented by the following Formula scheme are reproduced:

CK

CH ₃ OH

H ₉ -C-CHo-N

I i

CH ₃ CH ₃

Ru the r iun.-carbon / isopropanol

CH ₃ OH

-CH ₂ -N

CH ₃ CH ₃

The epoxides required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (II). In this formula, R ¹ , R ² and R ³ preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention for these radicals. The epoxides of the formula (II) are known (see, for example, DE-OS S) 13996) or they can be obtained in a generally known manner by reacting methyl ketones of the formula (IV)

R ¹ -C-C0-CH ₃

in which

R ', R ² and R ^{3 have} the abovementioned meaning,

either

α) with Dimnthyloxosulfonium-methylid of the formula

(CHg) ₂ SOCH ₂

in a conventional manner in the presence of a diluent, such as dimethyl sulfoxide, at temperatures between 2O ⁰ C and 80 ⁰ C (see, for this, the information in J. Am. Chem. Soc., 87.1363-1364 (19651), or 0) with trimethylsulfonylmethylsulfate of the formula

KCHjIjS ⁴ I ₃

in a conventional manner in the presence of an inert organic solvent such as acetonitrile, and in the presence of a base such. As sodium methylate, at temperatures between ^{0 0} C to 60 ° C, preferably at room temperature, converts (see also the information in Heterocycles 8.397 (1 ^ 977]).

The methyl ketones of the formula (IV) are known (cf., for example, DE-OS 3048266 and DE-OS 3210725) or they can be obtained by the processes indicated there.

The epoxides of formula (II) can also be recovered by epoxidizing corresponding olefins by processes known in principle, such as by reaction with hydrogen peroxide or peracids, optionally in the presence einbs solvent and optionally in the presence of a catalyst at temperatures between -1O ⁰ C and + 30OX.

The amines additionally required as starting materials for process (a) according to the invention are generally defined by the formula (III). In this formula, R ⁴ and R 'preferably have those meanings which have already been mentioned in connection with the description of the substances according to the invention of the formula (I) for these radicals. The amines of the formula (III) are generally known compounds of organic chemistry.

The hydroxypropylamine derivatives required for carrying out the process (b) according to the invention as starting materials are generally defined by the formula (Ib). In this formula, R ', R ³ , R ⁴ and R ⁵ preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention for these radicals. R ^{1 "2} preferably represents in each case optionally simp r rh or polysubstituted by identical or different substituents, phenyl, phenoxy, phenylalkyl or phenoxyalkyl each having ¹ o: ler 2 carbon atoms in the alkyl moiety, where suitable phenyl substituents in each case being: straight-chain or branched alkyl, Alkoxy or alkylthio each having up to 5 carbon atoms, haloalkyl, haloalkoxy or haloalkylthio each having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, such as preferably fluorine or chlorine atoms.

The hydroxypropylamine derivatives of the formula (I b) are substances according to the invention and obtainable according to process (a). The process (a) according to the invention for the preparation of the novel substituted hydroxypropylamine derivatives of the formula (I) is preferably carried out using diluents. Suitable diluents are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated carbonaceous substances such as benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride,

Chlorobenzene and o-dichlorobenzene, ethers ₍ such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, alcohols ₍ such as methanol, ethanol, n- and i-propanol or butanol, NUrMQ ₁ WIe eg acetonitrile and

Propionitrile, amido such. B. dimethylformamide, and dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide. If liquid amines of the formula (III) are used as starting materials, these can simultaneously act as solvents, provided they are used in a sufficient excess.

If appropriate, the process (a) according to the invention can be carried out in the presence of catalysts. Preferably in question alkali metal hydroxides such. For example, sodium and potassium hydroxide, alkali metal carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium methoxide or ethylate, potassium tert-butoxide, metal salts of the amines of the formula (III) and carboxylic acids such. As acetic acid and propionic acid and sulfonic acids such. B. trifluoromethanesulfonic acid.

The reaction temperatures can be varied within a substantial range in the process (a) according to the invention. In general, one works at temperatures between -1O ⁰ C and 4 250 ° C, preferably at temperatures between + 4O ⁰ C and

The process (a) according to the invention is generally carried out under atmospheric pressure. However, it is also possible to work under increased pressure. In general, one works generally between 1.5 and 5 atm, preferably between 1.5 and

When carrying out the process (a) according to the invention, preference is given to 1 mol of epoxide of the formula (Ii) preferably from 1 to 30 mol of amine of the formula (III), after the amine has also been used as diluent and optionally from 0.1 to 10 mol , preferably 0.1 mole to 1 mole of catalyst. The isolation of the end products is carried out by conventional method.

Suitable diluent I for carrying out the process (b) according to the invention are all solvents which are inert under hydrogenation conditions. Preference is given to using hydrocarbons such as petroleum ether, pentane, hexane, heptane, cyclohexane, alcohols such as methanol, ethanol, n-propanol and i-propanol or ethers such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether. However, it is also possible to work without a diluent.

Suitable hydrogenating agents in carrying out the process (b) according to the invention are those compounds which can hydrogenate aromatics. Preferably, molecular hydrogen is used.

As the hydrogenation catalyst, in the process (b) of the present invention, any ordinary orphan can be used for such reactions

usable catalysts can be used. Preferably, Raney nickel or noble metal catalyst such as

Palladium, ruthenium, palladium oxide, platinum or platinum oxide, optionally on a suitable carrier, such as. B.

Coal.

The reaction temperatures can be varied within a substantial range in process (b) according to the invention. in the

general works at temperatures between 50 ⁰ C and 250 ° C, preferably at temperatures between 80 ° C and

The process (b) according to the invention can be carried out at normal pressure but also at elevated pressure. Prefers

is operated under elevated pressure in the presence of hydrogen. In general, one operates at pressure ratios between 6 and 300 atm, preferably between 10 and 200 atm.

In carrying out the process (b) according to the invention is used for 1 mole of hydroxypropylamine derivative of formol (I b) in

generally 3.0 to 30 moles of hydrogenating agent and 0.001 to 0.1 mole, preferably 0.01 to 0.1 mole of catalyst.

In carrying out the process (b) according to the invention, the procedure is generally such that the compounds of the

Formula (Ib) in the presence of a diluent, at the particular desired temperature with hydrogen in an autoclave

implements. The workup is done by conventional methods.

For the preparation of acid addition salts of the Vorbindungen of formula (I) are preferably the following acids in question: Hydrohalic acids, such as. Hydrochloric and hydrobromic acids, especially hydrochloric acid,

also phosphoric acid, nitric acid, mono-, bi- and trifunctional carboxylic acids and hydroxycarboxylic acids, such as. B.

Acetic, maleic, succinic, fumaric, tartaric, citric, salicylic, sorbic, lactic, and the like Sulfonic acids, e.g. p-Toluol8ulfoneäure and Ι, δ-naphthalene disulfonic acid. The acid addition salts of the compounds of the formula (I) can be prepared in a simple manner by customary salt-forming methods, such as

z. Example by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, such as. B.

Chlorwaeserstoffsfluro be obtained and in a known manner, for. B. isolated by filtration and optionally by Wash with an inert organic solvent. For the preparation of metal salt complexes of the compounds of formula (I) are preferably salts of metals of II. Bis IV. Main and I and II and IV. To VIII. Subgroup of the Periodic Table of the Elements in question, where copper, zinc, Manganese, magnesium, tin, iron and nickel are exemplified. Ale anions of salts are those which are derived preferably from the following acids: Halogenwasserstoffsäiiren such. As hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid

and sulfuric acid.

The metal salt complexes of compounds of the formula (I) can be obtained in a simple manner by customary processes,

so z. B. by dissolving de the metal salt in alcohol, eg. As ethanol, and! ·!> Add to the compound of formula (I). Metal salt complexes can be prepared in the manner known in the art, e.g. B. by filtration, it-ol on and optionally by recrystallization.

The active compounds according to the invention have a strong microbicidal action and can be used to combat

be used practically undesirable microorganisms.

The active ingredients are suitable for use as pesticides, especially as fungicides. Fungicides in crop protection are used to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetoe, Deuteromycetes. Exemplary but not limiting are some pathogens of fungal diseases, which are listed below Generic terms fall, called: Pythlum species such as PyUiium ultimum; Phytophthora species, such as Phytophthora infestans; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara species, such as Plasmopara viticola; Peronospora species such as Peronospora pisi or P. brasslcae; Erysiphe species, such as Erysipho graminis; Sphaerotheca species, such as Sphaerotheca fuliginea; Podosphaera species, such as Podosphaera leucotricha; Venturia species, such as Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea

(Conidia form: Drechslera, Syn: Helminthcsporium);

Cochliobolus species, such as Cochliobolus sativus

(Conidia form: Orechslera, Syn: Helminthosporium);

Uromyces species, such as, for example, Uromyccs appendiculatus; Puccinia species, such as Puccinia recondite; Tilletia species, such as Tilletia caries; Ustllago species such as Ustllago nuda or Ustilago avenae; Pellicularla species, such as, for example, Pellicularia sasakii; Pyricularla species, such as Pyricularia oryzae; Fuearium species such as Fusarium culmorum; Botrytls species, such as Botrytis cinerea; Septoria species, such as the example nodorum; Leptosphaeria species, such as Leptosphaeria nodorum; Cercospora species, such as Cercospora canescens; Alternarla species, such as Alternaria brassicae; Pseudocercosporella species, such as Pseudocercosporeila herpotrichoides. The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant pests / ankheiten

allows treatment of above-ground parts of plants, of planting and seed, and the soil. The new active ingredients can be used to combat cereal diseases, such as the causative agent of the disease, with particular success

Barley powdery mildew (Erysiphe graminis) are used. In addition, the compounds of formula (I) show a very broad

fungicidal action z. B. against the causative agent of blotch disease on rice (Pyricularia oryzae).

The active compounds can be converted into conventional, depending on their respective physical and / or chemical properties Formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Active substance-impregnated natural and synthetic substances, ultra-fine encapsulations in polymeric substances and in encapsulants for Seeds, as well as ULV-KaIt- and warm-mist Forrnulierungen. These formulations are prepared in known catfish, e.g. by mixing the active ingredients with extenders, ie

liquid solvents, liquefied gases under pressure and / or '*> most carriers, optionally under

Use of surface-active agents, ie emulsifiers and / or dispersants and / or foaming agents Means. In the case of using water as an extender z. As well as organic solvents as Hllfslösungsmittel

be used. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or

Alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic.) Hydrocarbons, such as chlorobenzenes, chloroethylenes or Methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. As petroleum fractions, alcohols, such as butanol

or Glyco! and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water; By liquefied gaseous diluents or carriers is meant liquids which are gaseous at normal temperature and under normal pressure,

z. B. aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers come into question: z. As natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or

Diatomaceous earth and ground synthetic minerals, such as fumed silica, alumina and silicates; as solid Carriers for granules come into question: z. Broken and fractionated natural rocks such as calcite, marble, pumice, Sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic Material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents

are suitable: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene

Fatty alcohol ethers, e.g. B. Alkylarylpoiyglykol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; when Dispersants are suitable: e.g. Lignin-sulphite liquors and methylcellulose. It may contain in the formulations adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or

latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural

Phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and

be vegetable oils.

It can dyes such as inorganic pigments, eg. For example, iron oxide, titanium oxide, Ferrocyanblau and organic dyes, such as Alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc are used. The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.6 and 90%. The active compounds according to the invention can be present in the formulations in a mixture with other known active compounds

such as fungicides, insecticides, acaricides and herbicides as well as in mixtures with fertilizers and growth regulators.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom

ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules are used. The application happens in common catfish, z. B. by casting, spraying, spraying, scattering, dusting,

Foaming, brushing, etc. It is also possible to deploy the active ingredients according to the ultra-low-volume method or

Inject the active ingredient preparation or the active ingredient itself into the soil. It can also be treated the seed of the plants.

In the treatment of parts of plants, the drug concentrations in the use forms in a larger Range can be varied. They are generally between 1 and 0.0001 wt .-%, preferably between 0.6 and 0.001%. In the seed treatment, in general, amounts of active ingredient of 0.001 to 60 g per kilogram of seed, preferably

0.01 to 10g needed.

When treating the soil, active ingredient concentrations of 0.00001 to 0.1 wt .-%, preferably from 0.0001 to 0.02% on Site of action required.

-9- 265 548 SAMPLE INFORMATION Example 1

CK, OH

CH ₀ - CC - CH ₀ - N .0

² · .2 \ J

Oh, J

'3

(Method·)

To 6.1 g (0.07 mol) of morpholine in 40 ml of n-butanol and 0.2 ml of glacial acetic acid, 14 g (0.069 mol) of 3,3-dimethyl-2-methyl-4- (3

methyl-phenyl) butene-1-oxide in 20 ml of n-butanol was added dropwise and heated under reflux for 17 hours. Subsequently, the

Distilled off solvent in Waxserstrahlvakuum. The residue is passed through a silica gel column in succession with the Elutlon methylene chloride and methylene chloride / methanol (9: 1) chromatographies. This gives 11.4 g (67% of theory) of 3,3-dimethyl-2-methyl-4- (3-methyl-phenyl) -1 - (morpholin-4-yl) -2-butanol as oils of Refractive index nj °: 1.5215. The structure is confirmed by NMR spectra and the purity by gas chromatography. Example 2

OH

CH ₃

H y is -CH ₂ - CC - CH ₂ - NO

CH ₃ CH ₃

(Vei drive b)

6 g (0.02 mol) of 3,3-dimethyl-2-methyl-4- (3-methyl-pfienyl) -1- (morpholin-4-yl) -2-butanol (Example 1) are dissolved in 100 ml of isopropanol and washed with ² g of 6% ruthenium carbon at 130 ⁰ C and 200atm Hydrogenated within 1 hour. The catalyst is filtered off and the solvent distilled off in a water-jet vacuum.

This gives 4.8 g (77% of theory) of 3,3-dimethyl-2-methyl-4- (3-methyl-cyclohexyl) -1- (morpholin-4-yl-2-butanol of Refractive index n & °: 1.4852. The structure is confirmed by NMR spectra and purity by gas chromatography. Analogously to Examples 1 and 2 or according to process variants (a) and (b), the following compounds of the formula

R ² OH

R ¹ -C-C-CH ₂ -Nv ,,. (I)

R ³ CH ₃

R ⁵

are obtained: Table 2

^ R ⁴ physics.

Ex., No. R ¹ R ^z R ³ -N _n . Konet.

R ⁵

CH ₃ CH ₃ -N y ng ⁰ ! 1.5302

Cl

^ y -CH ₂ - CH ₃ CH ₃ -NO ng ⁰ ! 1.5221 Cl (CiS) CH ₃

Table 2 (continued)

Bsp.Nr.

R ² R ³

Physics. Const.

C p-CH ₂ -

CH ₃ CH ₃

-N) ng ⁰ ! 1.5261

Cl

Cl

7 tC ₄ H ₉ 8 tC ₄ H ₉ CH,

^H 2 ~

^CH 3 ^CH 3N>

(ice)

ng ⁰ ! 1.5205

CH ₃

-NO Fp! 68 ⁰ C

(Cis) CH ₃

CH ₃ CH ₃ -N \ mp 55-57 ° C

9 tC ₄ H ₉

10 tC ₄ H ₉

^H 2 ~ ^CH 3

CHo -N ) mp 65 ° C

(Cis) CH ₃

^H 2 ~ ^CH 3 ^CH 3

ng ⁰ ! 1.5079

CHr

U tC ₄ H ₉

H ₂ - CH ₃ CH ₃ -NO mp 89 ⁰ C!

12 tC ₄ H ₉ CH,

H ₂ "H CH ₃ -N ρ ng ⁰ ! 1.5082

(Cis) CH ₃

-11- 265 848

Table 2 (continued)

Bsp.Nr.Physik. Const.

13 tC ₄ H ₉

14 tC ₄ H ₉

15 cl

H ₂ - H

H ₂ - H

Cl

Cl

Cl

Cl

Cl

Ho- H

CH ₃

CH ₃ -N> ng ⁰ : 1.5059

(Cis) CH ₃

CH ₃ -N 0 ng ⁰ : 1.5176

CH ₃ -N> ng ⁰ $ 1,5240 (ice) CHo

H ₂ - HC ₂ H ₅ -N 0 ng ⁰ $ 1.5263

CHr

H ₉ - H CoHc -N O ng⁰ $ 1.5111

(ice) CH ₃

H, - H C

jH ₅ - \ _) ng ⁰ : 1,

5231

^C 2 ^H 5N y ng ⁰

1.5175

C ₂ H ₅

CICH,

CHr

CHr

ng ⁰ 51.5124

Table 2 (continued)

Bsp.Nr. R ¹ R 1 R '

-CH ₂ -

ClPhysik. Const.

CH,

-N ) ng ⁰ ί 1, 5135 (ice) CH ₃

22 cl

/ V

HC ₂ H ₅ -N y ng ⁰ : 1.5213

23 Cl-C /> ~~ CH ₂ - HC ₂ H ₅ ~ N> ng ⁰ Jl, 5167

CHr

24 cl

HC ₂ H ₅ -NO ng ⁰ : 1.5264

25 Cl- <Λ-CHo-H CoHc ~ N) ng ⁰ : 1.5126

26 cl

27 cl

H ₂ "CH-

CH

H, - H

-N> ng ⁰ : 1.5134 (cie) CHo

H ^C 2 ^H 5 / ^CH 2 ng ⁰ : 1.5250

Table · 2 (continued)

Bsp.Nr.

R ² R ³ -N _n .

Physics. Const.

28 cl

CHr

HC ₂ H ₅ -N. , 0 ng ⁰ : 1.5137

H CH-.

(ice) CH ₃ • V y ng ⁰ ί 1,

5123

H CH ₃ -NO ng ⁰ : 1,

31 HoC32 H ₃

33 H ₃ C

34 H ₃ C

Cl

H ₂ -

H ₂ "

H CH ₃

CH,

H CH ₃ -N> ng ⁰ : 1.5049

CH,

-N ^ ng ⁰ ί 1.5088 CH ₃ CHo

-NO ng ⁰ : 1.5055

(cie) CH ₃

H ₂ -H CH ₃ -N ^ CH ₂ ng ⁰ : 1.5162

H CH ₃

5256

Table 2 (continued)

Bsp.Nr.

Cl

Cl

ClR ² R ³ -N>

Physics. Can.

CH ₃ "N 0 ng ⁰ Ί , 5300

H ₉ - H

CH _{3 χ} y ng ⁰ ί 1,

5148

CH

/ V

_χ y η? ⁰ ! 1.5187

CH ₃

Cl

Cl

Cl

Cl

Ho- H

-CH ₉ - H

-N 0 ng ⁰ : 1.5166

(ice) CH ₃ CH ₃

-N y ng ⁰ ί 1.5149 (ice) CH ₃

H-CH ₃ N CH ₂ ng ⁰ : 1, E, 272

H ₉ - H CH ₃ -N>, ng ⁰ : 1.5044

CH ₉

H ₃ C-CH-CH ₃

Table 2 (continued) Example no. R ¹

R ² R ³ -N>

Physics. Konet.

43 cl

CH.

CH-;

45 cl

CH,

46 cl

CHr

47 cl

CH-

"CH ₂ " CH ₃ CH-:

-N y ng ⁰ : 1.5256

44 Cl-ζ> -O-CH ₂ -CH ₃ CH ₃ -NO ng ⁰ : 1.5239

CH ₂ - CH ₃

CHo -N> ηβ °? 1.5213

CHr

CHr

CH ₂ - CH ₃

CH

ng ⁰ : 1.5169

CH-

CHr

"urio" ^ "3

CH

~ Ν 0 ng ⁰ : l, 5138

(ice) CH ₃

48 Cl-C ρ-O -CH ₂ -CH ₃ CH ₃ -N CH ₂ ng ⁰ : 1.5278

50 H ₃ CC H

^ 2 "^ H ₃ CH ₃

^ y mp: 54-56 ° C

CH ₃ ~ N

( ) ng ⁰ : 1,

4806

Table 2 (continued)

Bsp.Nr.

Physics, Konst,

51 H ₃ C- <H

H ₂ - H CH ₃ NO ~ ng ^0; 1.4825

H / ~ CHr> - H CHr

H / -CHo- H CHr

CH.

55 H ₃ C- <H

Ho-

CH ₃ CH ₃

Η, - Η CH.

-V y ng ⁰ :

1.4774

CHO

CH,

-N> ng ⁰ : 1,4760

CH ₃ -N y ng ⁰ ί 1.5185

CH ₃

-N 0 ng ⁰ si, 4746

(ice) CH ₃

56 H ₃ C-> H / -CH ₂ - H -CH ₃ N ^ CH ₂ ng ⁰ ! 1.4841

V / "^ H ₂ -

CHr

CH ₃ CH ₃ -N

> ng ⁰ : l,

5134

CHr

-CH ₂ - CH ₃ ^ n ₃

CHr / CH ₂ ^ CH-, -N CH ₂ ng ⁰ ί 1.5219

Table 2 (continued)

Bsp.Nr. R ¹ R ²

Physics. Const.

CH,

^H 2 ' ^CH 3

-N> ng ⁰ : 1,

5083

CH.

LI f * \ J

M ₂ CM ₃

CHr

C / ~ ° ^Η 2 "

CH ₃ -NO ng ⁰ : 1.5097

(ice) CH ₃ ^ CH ₃

ng ⁰ ί 1,5001

^CH

CHr

^C 2 ^H 5H ₃ C-CH-CH ₃ _ ^ CH ₃ CHo

ng ⁰ : 1.5032

Cl

CHr

CHrH ₃ C-CH-CH ₃

CH

: 1,4886

64 (Η V-CHO CHO CH

CHr

/ V

-ti> ng ⁰ .'1,4844

^ CH ₃

^ ₃ 65 Cl C> -CH ₂ - HC ₂ H ₅ -N _v ng ^0: l, 5034

CH,

H ₃ C-CH-CH ₃

Table 2 (continued)

XLl ₁ O

Bsp.Nr. R ¹

R ² R ³ -N>

Physics. Const.

66 <H y- CH ₂ -CH ₃

CHO

CH ₃ -N CH ₂ ng ⁰ : 1.4818

67 cl

-CH ₂ - CH ₃

CHr

CH,

68 H ₃ C

H CHr

-N _x ng ⁰ 5 1.5067

CH ₂ IH ₃ C-CH-CH ₃

ng ⁰ : 1.4967

CH

H ₃ C-CH-CH ₃ CHo

CHo CHr

CH.

Hj-CH ₂ - ^l 3

CHo CHr

-N 0 ng ⁰ : 1.4777

(ice) CH ₃ CH ₃ -Ν _χ y ng ⁰ : 1.4788

CH

CH ₃ CH ₃

CH

ng ⁰ : 1.4678

H ₃ C-CH-CH ₃

Cl

^ ₃ CH ₃ -N _x ng ⁰ ί1,5069

H ₃ C-CH-CH ₃

Table 2 (continued) Ref. R ¹

R ² R ³ -N>

Physics. Const.

O-CH

O -CH-;

O-CH

O-CH

O-CH

79 (H

0-CH ₃

73 HoC-C H / -CHO-H CH-

ng ⁰ : 1.4646

Ho-H CH.

Ho- H CH-

Ho- H

H ₃ C-CH-CH ₃ CH ₃

-NC ng ⁰ ! 1.5143

(ice) CH ₃ Cn ₃

-N y ng ⁰ : 1.5120 CH ₃

-N y ng ⁰ : l, 5159

CHQ

Ho- H CHo -N

Q »I ·.»

, 4756

Ho-H CH

CH ₃ CH ₃

-N ) ng ⁰ ! 1.4759 CH ₃

Ho- H CH,

-MO ng ⁰ ! 1.4776

CHO

Table 2 (continued)

Bsp.Nr. R ¹ R ² R ³

Physics. Const.

H ₂ - CH ₃

-ν 'ρ ng ⁰ i 1.5222

^H 2-

CHo CH

-N y ng ⁰ ! 1.5122 CH ^

^H 2T

CKq CH '

CH,

CH,

ng ⁰ : 1,5093

CHo CH,

CH-

-NO ng ⁰ : 1.5103

CH ₃

H ₂ - CH ₃ CH ₃ -N _xy CH ₂ ng ⁰ : 1.5216

^H 2-

ng ⁰ ί 1.4990

CH

H ₃ C-CH CH ₃

CHo CH-

^C 2 ^H 5

ng ⁰ : 1.4998

H> -CH ₂ -CH ₃ CH ₃ -N _v ^ CH ₂ ng ⁰ ! 1,4912 Table 2 (continued)

Bsp.Nr. R ¹ R ² R ³

Physics. Const.

H ₂ - H CH ₃ -N

H ₂ "CH ₃ CH ₃ -N

H ₂ - H

H ₂ - CH

H ₂ - CH

( ) ng ⁰ : 1,

5037

₍ ^CH 3 O ng ⁰ ! 1.4796

CH ₃

H ₂ - H CH ₃ -NO ng ⁰ ! 1.5082

91 FC // - CH ₉ - H CH-

- / S ng ⁰ :

1.4985

CH,

CH-

CH ₃ -N> ng ⁰ '. 1 CH ₃ , 4958 CH ₃ -Nv. ng ⁰ ! 1 CHo I , 4694 H ₃ C-CH-CH ₃ CH ₃ -Nv. ng ⁰ ! 1 C ₄ H ₉ , 4714

Ho- H CHo -NO ng ⁰ ! 1.4976

(ice) CH,

Table 2 ^ Continued)

Example, no. R

R ² R ³ -N-

Physics. const ·

H> -CH ₂ -CH ₃ CH ₃ -N 0 ng ⁰ : 1,4891

97 <H> -CH, -

CH ₃ -N y ng ⁰ ! 1.4870

CH ₃ -N CH ₂ ng ⁰ S1,5071

H ₂ - H

ng ⁰ ; 1.4839

H ₃ C-CH-CH ₃

H ₂ "H

ng ⁰ S 1.4847

C ₄ H ₉

101 cl

Cl

-CH ₂ - CH ₃ CH _:

ng ⁰ : 1.5329

102 cl

Cl

-CH ₂ -

CH

-N> ng ⁰ : 1.5281

CHO

103 cl

Cl

-CH ₂ -

CHCH ₃ -N y ng ⁰ ί 1.5230

CHO

Table 2 (continued)

Bsp.Nr.

Phyeik. Const.

Cl 104 Cl- ^ ^ -Q-

CH ₃ CH CH

ng ⁰ : l, 5138

Cl 105 Cl- ^ ^ -O-CH ₂ -CH ₃

CH

H ₃ C-CH-CH ₃ -NO ng ⁰ : 1, 5235 (ice) CH ₃

106 <H> -CH ₂ -

CHo CH-

ng ⁰ : l, 4835

107 (H> -CH ₂ -

CH

Q--

CH ₃ CH ₃

Cl -N> ng ⁰ : 1.4805 CH ₃

-N> ng ⁰ s 1.5213 CH ₃

Ho- CHo CHo -N

Cl

O ng ⁰ ! 1, 5197

CHO

CH. CH ₃ -NJ ng ⁰ Sl,

5297

Cl

Table 2 (continued)

Bsp.Nr.

R ² R ³

Physics. Const.

Ul Cl

CH ₃ CH ₃

I 1, 5218

CH-;

112 cl

CHr

CH ₃ CH ₃ -NO ng ⁰ S1.5171

113 Cl

CH ₃ CH ₃ -NJ ng ⁰ ίΐ, 5331

• Q

ng ⁰ ί1,5096

OC ₂ H ₅

(h "/ - ch ₂ - η

ng ⁰ 8 1.4760

CHr

CH-

CH ₃ CH ₃

pH ₃ CH ₃

Ü.5215

-NO ng ⁰ Sl, 5253

CHrj

CHr

H ₂ - CH ₃ CH ₃

-N) η

g °: l, 5166

CH.

Table 2 (continued)

Bsp.Nr.

126 BPhysics. Const.

CH

ig CH ₃

CH

CHQ CHQ -N CH ₃

n8 ° »1.5121 CH ₃ CH ₃

Ο n8 ° »1.5134 CH ₃

CHo CHr-Qn

CHr

S ⁰ Sl, 5247 ng ⁰ J 1,5035

"2-

/ CH ₃ CH ₃ CH ₃ -N-CH ₂ -CH (CHy) ₂

CH.

H is T-CH ₂ - CH ₃ CH ₃

-CH ₂ - CH ₃ CH ₃

-O

V /

n8 °! 1,4872

n8 ° »1.4996 CH ₃

CH

-CH ₂ "CH ₃ • Ν Ο ng ⁰ » 1,4972

η6 ° »1.5338 CH ₃

Table 2 (continued)

Bep.Nr. R ¹ R ² R ³

Physics. Konet.

R ^:

127 Br-C TO-CH ₂ -CH ₃ CH ₃

CHr

CHo CH »

CHr

H ₂ "CH ₃ CH ₃

CHr

-N 0 ηδ ° ί 1.5262

CHr

ng ⁰ si, 4842 CH ₃

-NO ng ⁰ : 1,4886

CHr

CHr

H / - CHr> ~

CH

H> ~CH ₂ - CH ₃

CH

CHr

: l, 4817

~ CHO ~ CH ₃ CH ₃ CH ₃

-NO ng ⁰ Sl, 4819

CH ₃

NJ ng ⁰ si, 4917

ng ⁰ 11,5205

CHr

Table 2 (continued)

Bsp.Nr.

F ² R ³

Physics »Const.

ng ⁰ 5 1.4701 CH ₃ CH ₃ -N-CH ₂ -CH (CHg) ₂

CHO

Cl

Cl

Cl

-CH ₂ - CH ₃

-CH ₂ - CH ₃

H ₂ - CH ₃ CH ₃

-CH ₂ - CH ₃ CH ₃ -NO ng ⁰ : 1.5153

CH,

-CH ₂ - CH ₃ CH ₃ -N) ng ⁰ S1.5239

CHO

CHr

-CH ₂ - CH ₃ CH ₃ -N 0 ng ⁰ i1.5178

CHr

ng ⁰ Jl .5093

CH-

CH-

CH ₃ -N 0 ng ⁰ : 1, 5056

CHr

ng ⁰ : 1.5034

CHr

Table 2 (continued)

Bsp.Nr.

F ² R ³

Phyeik. Konst,

-CH ₂ "CH ₃

Cl

Q-CH ₂ -

H> -O-CH ₂ - CH ₃

H> -O-CH ₂ - CH ₃

V ^ n8 "J

: L, 5164

CHr

CH ₃ CH ₃ -N 0 mp: 65-68 ° C

CHr

CH ₃

-NO ng ⁰ ί 1.4742

CH ₃

/ v

N> ng ⁰ : 1.4756

CHO

C = / ⁰ " ² "

CHo CHr

CF

Ho "CHo. CHr

CF

-N ^^ y ng ⁰ : 1.4918

: 1, 4847

CHr

CHr

CH ₃ CH ₃ -NO ng ⁰ 5 1.4861

CHr

Table 2 (continued)

Example, no.

R ² R ³

Physics. Const.

148 F ₃

149

150 F ₃

151

152

Ho-

Ho-

CF

H) -CH-

153 FoC-C H y- CHO-

154 FoC-C H y- CHO-

155 FoC-K H> -CHO-CH ₃ CH ₃

CH ₃ CH ₃

V y ng ⁰ S 1,

4853

ng ⁰ 5 1,4827

UM ₃ CH ₃

CH ₃ CH ₃

-NO n8 ° 5l, 4 ^p, O9

CH

CH ₃ CH ₃

 Q

ng ⁰ ti, 4631

CH ₃

CHO

( ³ CH ₃ CH ₃ -N 0 ng ⁰ 5 1, 4611

CH ₃

CH ₃ CH ₃

CH ₃ CH ₃

-N _v y n8 °: 1.4605

Tough oil

CH

CH ₃ CH ₃

CH

-NO ng ⁰ 5 1.4589 CH ₃

Table 2 (continued)

Bsp.Nr. R ¹

R ² R

Physics. Const.

CJ

j- CH ₃ CH ₃ -Ν- ng ⁰ S 1.5277

-CH ₂ - CH ₃ CH ₃ -N> ng ⁰ : 1.5182

Cl

-CH ₂ - CH ₃ CH ₃

CH-

ng ⁰ ti, 5091 ₃ -K-CH ₂ -CH (CH ₃ ) ₂

Cl CH.

-CH ₂ - CH ₃ ng ⁰ ί 1, 5116

CH ₃ -N- (CH ₂ J ₃ -CH ₃

Cl

* CH ₃ -N

CH ₃

0 ng ⁰ Sl, 4999

_/ C

ng ⁰ : 1.5043

OC ₂ H

2 "5CH-

CHr

H CH ₃ -NO ng ⁰ : 1.5064

CHr

Table 2 (continued)

Bsp.Nr,

⁴

Physics. Const.

163

CH ₃

N y ng ⁰ : 1

, 4753

164

OC ₉ H

2 "5" 2-

Preparation of the starting materials of the formula (II)

CH ₃ -NO ng ⁰ ! 1, 4746

CH * (ice) *

ς>

CH ₂ -C-

CH ₃ O-

96 g (0.6 mol) of 2,2-dimethyl-1 - (3-i. ^% Ethyl-phenyl) -butan-3-one are dissolved in 630 ml of tetrahydrofuran. This solution is added to a suspension of 132,8g (0.6 mol) Thinethylsulfoxoniumiodld and 68g (0.6 mole) of potassium tert-butylate in 160 ml of dimethylsulfoxide, which was 6 Stu ends stirred at 60 ⁰ C before dropwise. The internal temperature rises to 27 ° C and stirred for 16 hours at 45 ⁰ C after. The mixture is then poured into 21 ice-water, extracted 4 times with 500 ml of methylene chloride and 2 times with 500 ml of water. The organic phase is dried and the solvent distilled off in the vacuum. This gives 97.3 g of crude 3,3-dimethyl-2-methyl-4- (3-methyl-phenyl) -butene-1-t xid.

Preparation of the starting materials of the formula (IV) CH ₃ P

il

H ₂ -C-CH ₃

CHr

161, g (3 mol) of Kalluinhydroxld are charged with 24.4g (0.076 mol) TMrebutylemmonlumbromid in 1.261 cyclohexane and treated under reflux with a solution of 258g (3 mol) of methyl isopropyl acetate and 210g (1.611 mol) of 3-methylbenzyl chloride. The mixture is then heated at reflux for 30 hours on a water, filtered off with suction through kieselguhr and distilled in vacuo

 This gives 100 g (35% of theory) of 2,2-dimethyl-1- (3-methyl-'/ heriyl) -butan-3or> of boiling point Kp: 52 ° C / 0.16 Torr.

Example A

Eryslphe test (barley) / protective / solution: 100 parts by weight of dimethylformamide emulsifier: 0.25 part by weight of alkyleryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound with the stated amounts of solvent and Hmulgetor and dilute the concentrate ml '; Water to the desired concentration.

To test for protektlve effectiveness sprayed young plants dewy with the preparation of active compound. After the SpriUbelages had dried, the plants were dusted with spores of Erysiphe graminls f.sp.hordei.

The plants are placed in a greenhouse at a temperature of about 2O ⁰ C and a relative humidity of about 80% to dl? To promote the development of mildew pustules.

7 days after the inoculation the evaluation takes place.

The compounds according to the invention show in this test a clear supersaturation in the activity over the

State of the art.

Claims (6)

1. Fungicidal agents, characterized in that they are substituted as active ingredients hydroxypropylamine derivatives of the general formula (I) R ² OH. r4 R ¹ - C 0 CH ₂ - <^, (I) ₇ in which Each R ¹ is optionally substituted phenyl, phenylthio, phenylalkyl, phenoxyalkyl and phenylthioalkyl; in each case optionally substituted cyclohexyl, cyclohexyloxy, cyclohexylthio, cyclohexylalkyl, cyclohexyloxyalkyl and cyclohexylthioalkyl and also optionally by halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or Haloalkylthio substituted phenoxy;
R ^{2 is} hydrogen or methyl;
R ^{3 is} methyl or ethyl and R ⁴ and R ^s independently of one another represent alkyl or alkenyl, or R ⁴ and R ⁵ together with the nitrogen atom to which they are attached represent an optionally substituted, saturated heterocycle which may optionally contain further heteroatoms τ, and their plant-tolerable acid addition compounds and metal salt complexes in addition to extenders and / or surface-active agents. 2. Composition according to claim 1, characterized in that the active ingredient according to claim 1, wherein in formula (I)
R ^{1 is} in each case optionally mono- or polysubstituted, identical or different, in the phenyl moiety by halogen; straight-chain or branched alkyl, alkoxy or alkylthio, each with up to 5 carbon atoms; Halogenoalkyl, haloalkoxy or haloalkylthio with in each case 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms substituted phenyl, phenoxy or phenylthio, phenylalkyl, phenoxyalkyl and phenylthioalkyl having in each case 1 or 2 carbon atoms in the alkyl moiety, and in each case optionally mono- or polysubstituted, the same or various in the cyclohexyl moiety by straight-chain or branched alkyl and alkoxy each having up to 5 carbon atoms, Trif luormethyl or trifluoromethoxy substituted cyclohexyl, cyclohexyloxy, cyclohexylthio, cyclohexylalkyl, cyclohexyloxyalkyl and cyclohexylthioalkyl each having 1 or 2 carbon atoms in the alkyl moiety. R ^{2 is} hydrogen or methyl;
R ^{3 is} methyl or ethyl and R ⁴ and R ⁵ independently of one another represent straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched alkenyl having 3 to 6 carbon atoms or R ⁴ and R ^6, together with the nitrogen to which they are bonded, represent a 5- to 7-membered, saturated heterocycle having 1 or 2 heteroatoms which is optionally monosubstituted or polysubstituted, identically or differently by methyl, ethyl or hydroxymethyl, is included. -2 2G5 3. Composition according to claim 1, characterized in that the active ingredient according to claim 1, wöbe · in formula (I) R ^{1 is} in each case optionally monosubstituted to trisubstituted by identical or different substituents in the phenyl moiety by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl; n-, i-, s- and t-butyl, n-pentyl, 2-methyl-2-butyl, methoxy, ethoxy, n- and i-propoxy, t-butoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio-substituted phenylmethyl, phenoxymethyl, Phenylthiomethyl, phenoxy or phenylthio, and in each case optionally monosubstituted to trisubstituted or different in the cyclohexyl moiety by methyl, ethyl, η- and i-propyl; n-, i-, s- and t-butyl, n-pentyl, 2-methyl-2-butyl, methoxy, ethoxy, n- and i-propoxy, t-butoxy, trifluoromethyl or trifluoromethoxy substituted cyclohexylmethyl.cyclohexylmethyl, cyclohexylthiomethyl, cyclohexyloxy or cyclohexylthio stands; R ^{2 is} hydrogen or methyl; R ^{3 is} methyl or ethyl and R ⁴ and R ^{6 are} independently methyl, ethyl, η- and i-propyl; n-, i-, s- and t-butyl, n-pentyl, allyl, 2-butenyl or 3-methyl-2-buienyl, or R ⁴ and R ⁶ together with the nitrogen atom to which they are bonded, in each case optionally mono- to trisubstituted by identical or different methyl, ethyl or hydroxymethyl-substituted 1-pyrrolidinyl, 1-piperidirinyl, 1-piperazinyl, 4-morpholinyl or 1- Hexahydroazepinyl stand, is included. 4. Use of substituted hydroxypropylamine-dodecides of the general formula (I) according to claim 1, characterized in that it is used for controlling fungal pests. 5. A method for controlling fungal pests, characterized in that one allows substituted hydroxypropylamine derivatives of the general formula (I) according to claim 1 to act on fungal pests and / or their habitat. 6. A process for the preparation of fungicidal agents, characterized in that one mixes substituted hydroxypropylamine derivatives according to claim 1 with extenders and / or surface-active agents.