DD296822A5 - FUNGICIDES AND PLANT GROWTH-CONTROLLING AGENTS (II) - Google Patents

Abstract

The invention relates to fungicidal and plant growth-regulating agents containing N-alkylpiperidinio-alkyl-phenyl ether salts of general formula I and can be used to combat fungal pathogens in agriculture and horticulture and to influence the development of crops. The meaning of R1, R2, R3, R4, R5 and X in the formula (I) can be taken from the description. Formula (I) {fungicidal agent; plant growth regulating agents; N-Alkylpiperidinio alkyl phenyl salts; fungal pathogens; combating; Agriculture; Horticulture; crops}

Description

Field of application of the invention

The invention relates to novel N-alkylpiperidinio-alkyl-phenylther salts and their use as fungicides in agriculture and horticulture with additional plant growth-regulating properties.

Characteristic of the known state of the art It is known that long-chain N-alkylpiperidines have a fungicidal activity (Angewandte Chemie 77 (1965),

S.327-333).

Furthermore, N-Aralkylpiperidine and their acid addition salts are suitable as fungicides (OE-PS 27 27 482, DE-PS 2830127, DE-PS 3134220, EP-PS 0005541, Angewandte Chemie 9211980], p 176-181). It is also known that quaternary ammonium compounds of N-aralkylpiperidines with alkyl, alkenyl, alkynyl, Ar alky I-

or alkoxymethyl substituents are fungicidally effective (OE-PS 3134220, DO-PS 134037, DD-PS134474, DD-PS140403).

Furthermore, it is known that N, N-dialkylpiperidinium salts are used as plant growth regulators (DE-PS 1642215, DE-PS 1642215). PS 2207575, CS-PS 190691) or fungicides (DE-PS 2810066) are suitable. It is also known that quaternary salts of piperidinoalkyl phenyl ether with lower alkyl or aralkyl groups as Plant growth regulators are described (DE-PS 2913523). Furthermore, N, N'-bis (1-formamide-2,2,2'-trichloroethylpiperazine (triforine) or 2,6-dichloro-4-nitraniline (diclorane) is already known

to be used as active substances in fungicides for combating fungal plant diseases (The Pesticide Manual,

British Crop Protection Council; London, 1984). However, the effect of the compounds mentioned is in certain areas of indication, especially at low levels Application rates and concentrations, not always fully satisfactory. In addition, they show a very high selectivity

against certain types of fungal pathogens, which severely restricts their widespread use. A further disadvantage is that the plant compatibility of these compounds is not sufficient in many cases.

Object of the invention

The aim of the invention is the development of new compounds with improved fungicidal activity and plant growth-regulating properties, a process for their preparation, and the use of such agents in agriculture and horticulture.

Explanation of the essence of the invention

The invention has for its object to provide novel N-AlkylP'peridinio-alkyl-phenyl ether salt-containing agent with good fungicidal activity and broad spectrum of activity and the highest possible plant compatibility and plant growth-regulating properties.

According to the invention fungicidal and Pflanzenwachstumsregutierende agents are proposed, which are characterized in that they contain at least one N-alkylpiperidinio-alkyl-phenyl ether salt of the general formula I,

rr ·, "ti Π

(I)

in the

R 'straight-chain or branched alkyl having 6 to 20 C atoms, R ² straight-chain or branched alkylene having 1 to 6 C atoms, R ³ , R ⁴ and R ⁵ are each independently the same or different hydrogen, straight-chain or branched alkyl with 1 to

6 C atoms, alkoxy having 1 to 4 C atoms, acyl having 1 to 4 C atoms, halogen, halogenoalkyl having 1 to 4 C atoms, cycloalkyl having 3 to 7 C atoms, aryl lower alkyl with 7 bis 12 C atoms, aryl, nitro, cyano, thiocyanato, NHCOR ', COOR' and / or CONR'R ", where R 'and R" are each independently hydrogen, straight-chain or branched alkyl having 1 to 6 C atoms, aryl or aryl-lower-alkyl having 7 to 12 carbon atoms, and

X ^- the anion of a non-phytotoxic acid,

in addition to the usual solvents, carriers and / or formulation auxiliaries.

Surprisingly, it has been found that the N-alkylpiperidinio-alkyl-phenyl-ether-Sal2e of the invention

general formula I have a strong fungicidal activity and broad spectrum of action and in particular to

Fight against phytopathogenic fungi on crops and vegetable stocks. The active ingredients show a

good plant compatibility in the amounts required to combat plant diseases. The active compounds according to the invention can positively influence crop plants in the desired manner with their growth-regulating properties.

N-alkyl-cycloammonio-alkyl-phenyl ether salts of other ring size, whose rings may also be substituted

similar fungicidal and plant growth-regulating properties as the active compounds according to the invention.

Furthermore, it has been found that the N-alkylpiperidinio-alkyl-phenyl ether salts of the general formula I are obtained,

by reacting an N-alkylpiperidine of the formula II,

NE ¹ (M)

wherein R ^{1 has} the meaning given in the general formula I, with a compound of formula III,

wherein R ² , R ³ , R ⁴ and R ^{5 have} the meaning given in the general formula III and X is halogen, or alternatively a piperidino-alkyl-phenyl ether of the formula IV,

IM - R ² - 0-Λ ¹ ^ C "<VI)

wherein R ² , R ³ , R ⁴ and R ^{s have} the meaning given in the general formula I, with a compound of the formula V,

wherein R ^{1 has} the meaning given in the general formula I and X is halogen reacted.

N-alkylpiperidine of the formula II are ζ. B. n-octyl, n-oodecyl ·. n-tridecyl iso-tridecyl, 1,5,9-trimethyldecyl, n-pent; n-didecyl-piperidine

Haloalkylphenyl ethers of the formula III are, for example, 2-bromoethylphenyl ether, 2chloroethyl-4-tert-butylphenylethet 3, 2-bromoethyl-4-nitrophenyl ether, 2-bromoethylmyanophenyl ether, 2-bromoethyl-2,6-dichlorophenyl ether, 2- Bromoethyl-3,4-dichlorophenyl ether, 2-bromoethyl-2,6-dichloro-4-cyanophenyl ether, 2-bromoethyl-3,5-dichlorophenyl ether, 2-Bro (tiethyl-4-benzylphenyl ether, 2-bromoethyl-4-aceto) amidophenyl ether, S-bromopropylphenyl ether, .alpha.-bromopropylm-tert.-butylpheny, S-bromo-propyl .delta.-dimethylphenyl ether or S-bromo-propyl .dib-dibromo-thiocyanatophenyl ether .piperidinoalkylphenyl ethers of the formula IV are, for example, 2-piperidino-ethyl-phenylether, -O-cyanophenylether, -4-terL- | ..

butylphenyl ether, 4-nitrophenyl ether, 3,4-dichlorophenyl ether, ^, (S-dichloromychenyl phenyl ether, 3-piperidino-propyl):

phenyl ether, ^ -tert-butyl-phenyl ether, -2,6-dimethylphenyl ether or - ^, e-dibromo-thiocyanato-phenyl ether. Alkyl halides of the formula V are, for example, n-decyl chloride, n-dodecyl chloride, n-tridecyl chloride, isotridecyl chloride, 1,5,9-trimethyldecyl chloride, pentadecyl bromide or ocidyl bromide.

The conversion into the compounds of the formula I according to the invention is optionally carried out in the presence of a solvent or diluent at a temperature in the range from 10 to 180 ° C., preferably between 30 and 150 ° C. The starting materials of the formula II or of the formula IV are in stoichiometric amounts with a compound of the formula III or of the formula V or preferably with an excess of 10 to 100% of a compound of the formula III or of the formula V over the stoichiometric amount, based on the starting materials of the formula II or the formula IV , implemented.

As preferred solvents or diluents, for example, aliphatic or aromatic, optionally halogenated hydrocarbons, such as n-pentane, cyclohexane, benzene, toluene, chlorobenzene, chloroform or methylene chloride; aliphatic ketones, such as acetone, methyl ethyl ketone or cyclohexanone; Ethers, such as diethyl ether, tetrahydrofuran or oioxane; Alcohols, such as methanol, ethanol, propanols, butanols or hexanote; Nitriles, such as acetonitrile; Esters, such as methyl acetate; Amides, such as dimethylformamide, oimethylacetamide or N-methyl-pyrrolidone; Dimethyl sulfoxide or water or mixtures of these solvents can be used.

The isolation of the compounds of the general formula I according to the invention from the reaction mixtures is not absolutely necessary since they can also be used without further purification to prepare fungicidal preparations. The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared by known processes.

The active compounds of the general formula I according to the invention have a strong activity against microorganisms and can accordingly be used for combating fungal pathogens in agriculture and horticulture. With the active substances occurring on plants or parts of plants undesirable fungi can be combated. The active compounds of the formula I are also suitable as mordants for the treatment of seed and plant cuttings for protection against fungal infections and can be used against occurring in the soil phytopathogenic fungi. In addition, the active ingredients in their application influence the growth processes of crops in a positive way. The active compounds according to the invention are particularly suitable for the prevention and cure of plant diseases caused by fungi, such as. B. Erysiphegraminis (powdery mildew), Erysiphe cichoracearum (cucumber powdery mildew), Erysiphe polygoni (bean powdery mildew), Podosphaera leucotricha (apple powdery mildew), Sphaerotheca pannosa (rose mildew), Uncinula necator (vineyard powdery mildew); Rust diseases, such as those of the genera Puccinia, Uromyces or Hemileia, in particular Puccinia graminis (cereal rust rust), Puccinia coronata (oat crown rust), Puccinia sorghi (corn rust), Puccinia recondita (cereal rust), Uromyces fabae (bush bean rust), Hemileia vastatrix (coffee rust); Botrytis cinerea on vines and strawberries; Monilia fructigena on apples; Plasmopara viticola on vines; Mycosphaerella musicola on bananas; Corticum salmoncolor on Hevea; Ganoderma pseudoferreum on Hevea; Exobasidium vexans to tea; Phytophthora infestans on potatoes and tomatoes; Alternaria solani on tomatoes. Furthermore, various of these agents are also different effective against phytopathogenic fungi, such. B. Ustilago avenae (avian blight), Ophiobolus graminis (cereal foot diseases), Septoria nodorum (cereal leaf and teal), Venturia inaequalis (apple scab) and other fungal pathogens, such as Rhizoctonia, Tilletia, Helminthosporium, Peronospora, Pythium, Altemaria, Mucor, Sclerotinia, Fusarium, Pseudocercosporella and Cladosporium. Particularly interesting are the active compounds according to the invention for combating a variety of fungal diseases on various crops or their seeds, especially wheat, rye, barley, oats, rice, corn, cotton, soybeans, coffee, bananas, sugarcane, fruit, ornamentals in horticulture, vegetables like cucumbers, beans or cucurbits. In addition, the active compounds according to the invention, with their plant growth-regulating properties, can positively influence the development of crop plants in the desired manner. The effects of the compounds are essentially dependent on the time of application, based on the stage of development of the seed or the plants, the amount of active ingredients applied to the plants or their environment and the mode of administration. Furthermore, the active ingredients also provide good activity against wood-discoloring and wood-destroying fungi, such. Pullaria pullulans, Aspergillus niger, Polystictus versicolor or Chaetomium globosum.

Furthermore, the active compounds of the general formula I according to the invention show a good activity against molds, such. Penicillium, Fusarium or Aspergillus species causing spoilage of high moisture agricultural products or processed agricultural products during storage or intermediate storage. Such products to be treated include e.g. Apples, oranges, mandarins, lemons, grapefruits, peanuts, cereals and cereal products or pulses and meal.

The active compounds according to the invention, in addition to their broad spectrum of fungicidal activity, are also effective against phytopathogenic bacteria, such as, for example, Xanthomonas or Erwinia species.

Some of the active ingredients also show an action against human pathogenic fungi, such. B. Trtchophyten and Candida species. A part of the active compounds of the general formula I is distinguished not only by the protective action but also by a systematic development of activity. Thus, they are absorbed both via the root and the leaves and transported in the plant tissue or fed via the seed to the aerial parts of the plant.

The active compounds according to the invention are furthermore suitable for combating resistant strains of fungal pathogens which are resistant to known fungicidal active compounds, such as, for example, Active substances from the group of dicarboximide fungicides, such as, for example, 5-methyl-S

ty

oxazolidine-2,4-dione (myclozoline); Active substances from the group of the eenzimida2ol or thiophanate fungicides, such as, for example, i-fn-butyl-carbarrioyl-benzimidazol-a-yl-carbamic acid methyl ester f -benomyl), benzimidazole-1-methylcarboxylic acid (carbendazim) or 1,2-bis (3-ethoxy) carbonyl-2-thioureido) -benzene (thiophanate); Agents from the group of azole fungicides, such as 1- (4-chlorophenoxy-3,3-dimethyl-1- (1 H-1,2,4-triazol-1-yl) -butan-2-one (Triadimefon ) or 1/2 '- (2 ", 4 ~ -dichtophenyl) -2' - (propenyloxy) -ethyl / -1,3-imidazole (imazalil); active compounds from the group of aromatic hydrocarbons containing fungicides, such as 2 , 5-dichloro, 4-dimethoxybenzene (chloroneb) or 2,6-dichloro-4-nitroaniline (dichloran); acylalanine fungicidal actives such as OL-N- (2,6-dimethylphenyl ) -N- (2'-methoxyacetyl] alanine methyl ester (Metala) <yl) or DL-N- (2,6-dimethylphenyl) - N- (2-furoyl) alanine methyl ester (Furalaxyl) or active substances from the group of pyrimidine Fungicides, such as S-butyl-a-dimethylamino-A-hydroxy-6-methyl-pyrimidine (Oimethirimol) or 2-chlorophenyl-4-chlorophenyl-pyrimidin-5-yl-methanol (fenarimol), show signs of resistance.

The anions X ~ listed in the general formula I of the active compounds according to the invention are not decisive for the fungicidal action.

The active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, very fine encapsulations in polymeric substances and in seed coating compositions and ULV-KaIt and warm mist formulations.

The preparation of these formulations can be carried out in a known manner, e.g. by mixing or grinding the active compounds of the general formula I according to the invention with solvents and / or carriers, if appropriate using surface-active agents, such as emulsifiers and / or dispersants.

As liquid solvents, aromatics such as toluene, xylene or alkylnaphthalenes; chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions; Alcohols, such as butanols or glycols, and their esters and ethers; Ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strong polar solvents such as water, dimethylformamide or dimethyl sulfoxide can be used. Likewise, liquefied solvents which are gaseous under normal conditions, such as. As aerosol propellants, such as halogenated hydrocarbons, propane, butane, nitrogen and carbon dioxide are used.

As solid carriers come z. As natural minerals, such as kaolins, clays, talc, chalk, quartz, montmorillonite or Diatonmeenerde and synthetic minerals, such as finely divided silica, alumina and silicates in question. As solid carriers for granules z. For example, crushed and fractionated natural minerals such as calcite, marble, pumice, dolomite and synthetic granules of inorganic or organic meals, and granules of organic materials such as sawdust, cellulose powder, tree bark and nutshell meal can be used. As emulsifying agents, e.g. nonionic and anionic emulsifiers, such as alkali metal, alkaline earth or ammonium salts of liginesulfonic acid, naphtholsulfonic acids, phenolsulfonic acids, alkylarylsulfonates, alkylsulfates, alkylsulfonates, alkali and alkaline earth salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols or octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalenes or naphtholsulfonic acids with phenol and formaldehyde, polyethylene octylphenol ethers, alkylphenol polyglycol ethers.Tributylphenylpolyglycol ethers.Alkylarylpolyether alcohols.iso-tridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated Castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal and sorbitol esters.

Suitable dispersants are, for example, lignin-sulphite liquors and methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic latex polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the formulations.

As further additives dyes and trace nutrients may be included in the formulations of the active ingredients. The formulations generally contain between 0.1 and 95% by mass of active ingredient, preferably between 0.5 and 90% by mass. The method according to the invention for controlling fungi is characterized in that fungicidal agents with the active compounds of the general formula I according to the invention can be acted upon by fungi or the objects to be protected against fungal attack in an effective amount.

The active compounds may be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution in a customary manner, e.g. By casting, dipping, spraying, spraying, atomizing, injecting, silting, spreading, dusting, spreading, dry pickling, wet pickling, wet pickling, slurry pickling or encrusting.

In the treatment of plant matter, the Wirkstoffkonzemrationen can be varied in the use forms in a wider range. They are generally between 0.0001 and 1 mass%, preferably between 0.5 and 0.001 mass%. The drug application rates depend on the specific application and are generally between 0.1 and 3 kg of active ingredient per hectare.

In the seed treatment, in general, amounts of active ingredient of 0.001 to 50 g or more per kilogram of seed, preferably 0.01 to 10 g, needed.

For preservation or post-harvest treatment of agricultural products or processing products of agricultural products, the required amounts of active ingredient 0.01 to 100 g per kilogram of material to be treated, preferably 0.1 to 50g.

In the treatment of the soil, drug concentrations of 0.0001 to 0.1 mass%, preferably 0.001 to 0.05 mass%, are required at the site of action.

The following examples are intended to further illustrate the invention without, however, limiting it and demonstrating the effect of the compounds of general formula I according to the invention.

embodiments The following examples illustrate the preparation of the compounds of the invention. The starting compounds for preparing the compounds of the invention are known per se or may according to

known methods are produced. !

example 1

3- (N-iso-tridecyl piperidinio) propyl-2,6-dichl <xphenylether bromide

13.4 g of N-isotridecyl-piperidine and 14.2 g of 3-bromopropyl-2,6-dichlorophenyl ether in 50 ml of n-butanol are refluxed for 24 hours with the addition of a catalytic amount of sodium iodide. After cooling, the solvent is distilled off in vacuo. It is taken up in a little acetone and the solution is added to complete deposition with η-hexane. The oily

Phase is separated and freed of solvent residues in vacuo. This gives 20.5 g of a yellow-brown resin

(Compound no.24).

Example 2

2- (N-iso-tridecyl-piperidinio) -ethyl-4-chlorophenyl ether chloride

12.7 g of 2-piperidino-ethyl-4-chlorophenyl ether and 11 g of isotridecyl chloride (mixture of various C ₁ , C, _4- alkyl! Halides containing 60 to 70% n-tridecyl chloride) in 50 ml of n-butanol become 24 hours heated to reflux. It is allowed to cool and the solvent is distilled off in vacuo. The remaining residue is dissolved in a little acetone and treated with η-hexane until complete precipitation as an oily phase. The product is separated and freed from solvent residues in vacuo. This gives 18 g of a brown resinous product (Compound No. 6).

In a corresponding manner, the following compounds of general formula I are prepared, which in the Usually yellow to brown viscous oils or resins, in polar solvents, such. For example, alcohols, acetone, Dimethylformamide and dimethyl sulfoxide, are readily soluble and characterized by IR spectra.

No.

R ¹

R ²

R ³

1 n-octyl (CH ₂ ) ₂ 2-CI 6-Cl H br 2 n-dodecyl (CH ₂ ), 4-CI H H br 3 n-tridecyl (CH ₂ ), 4-CI H H br 4 1,5,9-trimethyldecyl (CH ₂ ), 4-CI H H br 5 iso-tridecyl (CH ₂ ) j H H H br 6 iso-tridecyl (CH ₂ J ₂ 4-CI H H Cl 7 iso-tridecyl (CH ₂ ) ₂ 3-F H H br 8th iso-tridecyl (CH ₂ ), 4-tert-butyl H H Cl 9 iso-tridecyl (CHj) ₃ 4-tert-butyl H H br 10 iso-tridecyl (CHj) ₂ 4-OCH ₃ H H br 11 iso-tridecyl (CH ₂ ), 4-CH ₃ H H br 12 iso-tridecyl (CH ₂ ), 4-CO-CH ₃ H H br 13 iso-tridecyl (CH ₂ J ₂ 3-NH-CO-CH ₃ H H br 14 iso-tridecyl (CH ₂ ) ₂ 3-CCMDC ₂ Hs H H br 15 iso-tridecyl (CH ₂ ), 3-CO-N (C ₂ Hs) ₂ H H br 16 iso-tridecyl (CH ₂ J ₂ 4-NO ₂ H H br 17 iso-tridecyl (CHj) ₂ 4-CN H H br 18 iso-tridecyl (CH ₂ ), 4-phenyl H H Cl 19 iso-tridecyl (CH ₂ ), 4-benzyl H H Cl 20 iso-tridecyl (CH ₂ ), 2-Br 4-Br H br 21 iso-tridecyl (CH,) ₂ 2-CI 3-CI H br 22 iso-tridecyl (CH ₂ ), 2-CI 4-CI H br 23 iso-tridecyl (CH,), 2-CI 5-CI H br 24 iso-tridecyl (CHj) ₃ 2-CI 6-Cl H br 25 iso-tridecyl (CH ₂ ), 3-CI 4-CI H br 26 iso-tridecyl (CH ₂ ), 2-CH ₃ 6-CHj H br 27 iso-tridecyl (CHj) ₃ 3-CH ₃ 4-CH ₃ H br 28 iso-tridecyl (CH ₂ ), 3-CI 5-CI H br 29 iso-tridecyl (CH ₂ I ₂ 2-CI 4-NO ₂ H br 30 iso-tridecyl (CH ₂ ), 2-CI 4-CI 6-Cl br 31 iso-tridecyl (CHj) ₂ 2-CH ₃ 4-CH ₃ 6-CH ₃ br 32 iso-tridecyl (CH ₂ J ₂ 2-CH ₃ 4-CI 6-CH ₃ br 33 iso-tridecyl (CH ₂ ) ₄ 2-CH ₃ 4-CI 6-CH ₃ br 34 iso-tridecyl (CH ₂ J ₂ 2-CI 4-CN 6-Cl br 35 iso-tridecyl (CH ₂ J, 2-CI 4-NO ₂ 6-Cl br 36 iso-tridecyl (CH ₂ J ₃ 2-Br 4-SCN 6br br 37 HC ₁₅ H ₃ I (CHj) ₃ 4-CI H H br 38 nC _{? 0} H «i (CHj) ₂ 4-CI H H br

By way of example, the following compounds according to the invention are characterized by their IR spectra: Verb.-Nr. IR spectra (Rim) / Cm ^- V

5 3 400.2 950.1 610.1 510.1470, 13.0, 1245.950

6 2 950.2 640.1 600.1 585.1 500.1460.1 245.1 100.830

9 3 370.2 935.2 910.2 850.1590.1490.1440.1 230.1165.810

22 3 360.2 930.2 850.1 470.1450.1365.1 270.1 250.1 090.1 045.850

28 3 400.2 955.1 920.2 870.1595.1 580.1450.1 265.1 060

24 3 350.2 950.2 870.2 630.2 540.1 565.1 450.1 380.1 070.1 040

30 3 350.2 950.2 870.2 640.2 530.1 555.1450.1 385.1 260.1 050.860

The compounds of the general formula 1 according to the invention can be used, for example, in the form of the following preparations:

I.Beispiel

Solution concentrates: 80 parts by weight of compound 22 are mixed with 20 parts by weight of N-methyl-2-pyrrolidone. It will

to obtain a solution which is suitable for use in the form of very small drops.

II. Example

Emulsifiable concentrates: 25 parts by weight of compound 9 are mixed with 2.5 parts by weight of epoxidized vegetable oil, 10 parts by weight of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture, 5 parts by weight of dimethylformamide and 57.5 parts by weight of xylene. From this concentrate emulsions of any desired concentration can be prepared by dilution with water.

III. example

Injection powder: 40 parts by weight of compound 28 are mixed well with 5 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite liquor, 1 part by weight of sodium salt of di-iso-butylnaphthalene-sulfonic acid and 54 parts by weight of silica gel and ground in a corresponding mill. A spray powder is obtained which can be diluted with water to give suspensions of any desired concentration.

IV. Example

Dusts: 5 parts by weight of compound 9 are intimately mixed and ground with 95 parts by weight of fine kaolin. The dusts can be dusted in this form for use.

V.Beispiel

Granules: 5 parts by weight of Compound 30 are mixed with 0.25 parts by weight of epichlorohydrin and 6 parts by weight Acetone dissolved. Thereafter, 3.5 parts by weight of polyethylene glycol and 0.25 parts by weight of cetyl polyglycol ether are added. The

thus obtained solution is sprayed on kaolin. Subsequently, the acetone is evaporated in vacuo. It will be a

Micro granules obtained, which can be used in this form. The following examples are intended to further illustrate the invention without, however, limiting it, and the biological effect

the compounds of general formula I prove.

Example A Wheaty mildew test (Erysiphe graminis / wheat) Potted "Alcedo" wheat plants are doused in the single-leaf stage with active compound preparations

sprayed, which are prepared from 1 part by weight of active compound, 100 parts by weight of acetone and 0.25 parts by weight of alkylaryl polyglycol ether and diluted with water to the desired active ingredient concentration. After the drying of the

Spritzbelages the plants are dusted with conidia (spores) of wheat powdery mildew (Erysiphe graminis var. Tritici). Subsequently, the test plants for a period of 2 to 3 hours at 90 to 100% relative humidity in

an incubation cabin and then at temperatures between 20 and 22 ° C and 75 to 80% relative humidity in the

Greenhouse set up. After 5 days, the powdery mildew of the wheat plants is determined. The efficiency of the funds is from ABBOTT

calculated.

The results of the experiments showed that, for example, Compound No. 30 using an active ingredient concentration

of 100 mg χ Γ ^{1 achieved} a better effect (100% efficiency) than the known fungicide sparol (N, N'-bis- (1-formamido-2,2,2-trichloroethylpiperazine) (activity level 85%).

Example B Botrytis test (Botrytis cinerea / field bean (Vicia (aba) leaffed) Clipped leaf spring of potted bean plants (Vicia faba) of the variety 'Fribo' in the four-leaf stage

are briefly dipped in active ingredient preparations prepared from 1 part by weight of active compound, 100 parts by weight of acetone and 0.25 parts by weight of alkylaryl polyglycol ether and diluted with water to the desired active ingredient concentration

become. After the spray coating has dried on, the leaves are inoculated with a conidia suspension of Botrytis cinerea, which is obtained by washing away 12 to 16-day-old fungal cultures on malt agar medium (2% malt). The

Field bean leaflets are more in an incubation cabin in trays at a temperature of 22 ° C and 90 to 100% relative Humidity kept. After 2 days, the Botrytis infestation of field bean leaflet is determined. The infections were counted

and multiplied by a factor for the strength of infection (rating scale from 1 = no infestation to 5 = very severe infestation). The

Resulting value was given in% infection and calculated therefrom in relation to the untreated control of the efficiency.

The results of the experiments showed that, for example, the compound no. 9 when used in an active compound concentration of 500mg χ Γ ¹ a better effect (efficiency of more than 90%) than the known active ingredient diclorane (2,6-dichloro-nitraniline) (efficiency 65%).

Example C Test against Phvtophthora infestans on tomato leaf disks The active ingredients are dissolved in a little DMF and distilled with dist. Water adjusted to the desired concentration. To perform the test, leaf disks are punched out of adult leaves of tomato plants. The zoospore suspension needed for the infection becomes more susceptible to swelling fungal turf halves Produced potato varieties. . The treatment with the active substances and the infection take place at the same time by adding certain concentrations of active ingredient to j Zoosporensuspension of Phytophthora infestans are added and these mixtures after shaking on the in Petri dishes

designed leaf discs are poured. After 2 hours, the supernatant liquid is poured off. The dishes are stored at 15 to 20 ° C under exposure. After 3 to 4 days, the evaluation is carried out by determining the proportion of necrotic leaf area per leaf disc. From the testing of a concentration series, the infection inhibition is determined.

The results of the experiments showed that, for example, the compounds Nos. S, 22,28,24 and 30 in a Drug concentration of 5 mg χ I ' ^{1 achieved} a 100% effect. Example D Plant growth regulatory test Cucumber plants of the variety 'Eva' are in pots in humus soil, which is sufficiently supplied with nutrients, up to a Growth height of 9cm used in the greenhouse. 10 plants are used per experimental variant. The cucumber plants

are sprayed with active compound preparations which are prepared from 1 part by weight of active compound, 100 parts by weight of acetone and 0.25 parts by weight of alkylaryl polyglycol ether and diluted with water to the desired active substance concentration.

After a growth time of 14 days after the application of the medium, the treated plants and the

untreated control plants length measurements made.

The results of the experiments showed that, for example, the compound No. 28 in a drug concentration of

1250mg X Γ ¹ inhibited the growth of cucumber plants by 12%.

Claims (3)

2S claims: 1. Fungicides and plant growth-regulating agents, characterized in that they contain at least one N-alkylpiperidinio-alkyl-phenyl ether salt of the general formula I, (I) in the R ¹ straight-chain or branched alkyl having 6 to 20 C atoms, R ² straight-chain or branched alkylene having 1 to 6 C atoms, R ³ , R ⁴ and R ^5, independently of one another, are identical or different, are hydrogen, straight-chain or branched alkyl having 1 to 6 C atoms, alkoxy having 1 to 4 C atoms, acyl having 1 to 4 C atoms, halogen, haloalkyl having 1 to 4 C atoms, cycloalkyl having 3 to 7 C atoms, aryl-lower-alkyl having 7 to 12 C atoms, aryl, nitro, cyano, thiocyano, NHCOR ', COOR' and / or CONR'R ", where R ' and R "are independently hydrogen, straight or branched alkyl of 1 to 6 carbon atoms, aryl or aryl lower alkyl of 7 to 12 carbon atoms, and X "mean the anion of a non-phytotoxic acid, in addition to the usual solvents, carriers and / or formulation excipients included. 2. A method for controlling fungi, characterized in that means according to item 1 is allowed to act on fungi or the objects to be protected against fungal attack. 3. Use of agents according to item 1, characterized in that they are used to combat fungi