CS264279B2 - Fungicide with plants growth regulation activity - Google Patents

Abstract

There are described novel n-alkyl-2,6-dimethylmorpholinocarboxylic ester salts and n-alkyl-2,6-dimethylmorpholinoalkyl phenyl ether salts of the formula I <IMAGE> in which A represents the group <IMAGE> in which R<1> is alkyl having 6 to 20 carbon atoms, R<2> is alkylene having 1 to 6 carbon atoms, R<3> is alkyl, substituted alkyl, alkenyl, alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkylalkyl, aryl, substituted aryl, aryl-lower-alkyl, substituted aryl-lower-alkyl, Z is oxygen or sulphur, R<4>, R<5> and R<6> independently of one another are identical or different radicals from the series comprising hydrogen, alkyl, alkoxy, acyl, halogen, haloalkyl, cycloalkyl, aryl-lower-alkyl, aryl, nitro, cyano, thiocyanato, NHCOR', COOR' and/or CONR'R'', and X<-> is the anion of an acid, their preparation, and their use as fungicides for controlling fungal pathogens in agriculture and in horticulture. These compounds additionally also have plant-growth- regulating properties.

Description

Vyurál s® refers to a fungicidal composition with additional plant growth regulating effect.

It is known that N-alkylmorpholines and their salts, as well as their molecular and addition compounds, are used as fungicides. This is known, for example, from DE Patent Specifications 1,164,152, 1,173,722 and 2,461,515.

Further, it is known that long-chain quaternary ammonium compounds of N-alkyl-2,6-dimethyl-morpholines having alkyl, alkenyl, alkoxyalkyl or aralkyl substituents are fungicidally active. This is known, for example, from DE patent specification 1 167 588 and from Angevandte Chemie 77 (1965). 327-333. Furthermore, compositions are known which contain substituted N-benzyl-2,6-dimethylmorpholine salts or alkoxymethyl-2,6-dimethylmorpholine salts as active agents for combating fungal agents. These are described, for example, in U.S. Patent Nos. 134,037, 134,474 and 140,403. Furthermore, it is also known that salts of morpholinolecarboxylic acid esters with alkanesulfonic acids or long chain alkanecarboxylic acids exhibit fungicidal properties (see, for example, DD. 201 371).

Further, it is known that morpholinoalkyl-4-alkyl ester, morpholinoalkyl-4-alkylcyclohexyl ether and morpholinoalkyl-4-alkylaryl ether exhibit fungicidal activity, as described, for example, in DE 1,190,724 and Angewandte Chemie 77 (1965), p. 327 to 333 and Angewandte Chemie 92 (1980) pp. 176 to 181. The use of 2,3-dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiine-4,4-dioxide (Oxycarboxine) is also known. , N, N'-bis- (1-formamido-2,2,2-trichloroethyl) piperazine (Triforine) or zinc ethylene bis-dithiocarbamate (Zineb) as active ingredients in fungicidal compositions for controlling fungal plant diseases (The Pesticide Manual, British Corp Protection Council; London, 1984).

However, the effects of the compounds are not always entirely satisfactory in certain indication areas, especially at lower levels and concentrations. In addition, they exhibit high selectivity against certain types of fungal diseases, thereby greatly reducing the widespread use of these compositions. Another disadvantage is that the acceptability of these compounds for plants is in many cases insufficient.

SUMMARY OF THE INVENTION It is therefore an object of the present invention to provide novel salts of N-alkyl-dimethyl-morpholino-carboxylic acid esters and N-alkyl-2,6-dimethyl-morpholinioalkyl-phenyl ethers and to be used in fungicidal compositions with good efficacy and broad spectrum of activity. plant acceptability and a sufficient growth-regulating effect on plants.

The above object is solved by a preformed him · fungicidal composition, lambs © .Z principle consists in that _R comprises as active ingredient a salt of an N-allcyl-2,6-dimethyImorfolinio-carboxylic acid salt of N-alkyl-dimethylmorfolinlo alkyl phenyl ether of formula ^r

wherein A represents -CO-Z-R ³ or a group

whereas

R ³ denotes straight-chain or branched alkyl having 1 to 12 carbon atoms, ethyl substituted by ethoxy, nitro and / or cyano, alkenyl having 3-4 carbon atoms, propargyl, cycloalkyl having 5 to 6 carbon atoms, this may be substituted by two methyl groups, a phenyl group which may be mono- or polysubstituted, the same or differently substituted by a straight or branched alkyl group having 1 to 4 carbon atoms, a benzyl group, a halogen atom, a phenyl group, a nitro group and / or a cyano group

R ⁴ represents a hydrogen atom, a methyl group, a tert-butyl group, a methoxy group, a phenyl group, a halogen atom, a nitro group, a cyano group or an ethoxycarbonyl group,

R ⁵ represents a hydrogen atom, a chlorine atom, a methyl group, a thiocyanate group or a cyano group,

R ⁶ represents a hydrogen atom, a halogen atom or a methyl group;

Z denotes an oxygen atom,

R ^{1 is a} straight or branched alkyl group having 8 to 13 carbon atoms,

R ² a linear or branched alkylene group having 1 to 3 carbon atoms and

X - is chlorine or bromine, or

R ³ and X "are absent, whereby the composition can, besides the active ingredient contain conventional solvents, carrier substances and / or auxiliaries.

The active compounds according to the invention can be present in two different geometrical structures, such as the N-alkyl-2,6-cis-dimethylmorpholinocarboxylic acid ester salt and the N-alkyl-2,6-cis-dimethylmorpholinioalkylphenyl ether salt or the N ester salt, respectively. -alkyl-2,6-trans-dimethylmorpholinium-carboxylic acid and a salt of N-alkyl-2,6-trans-dimethylmorpholino-alkylphenyl ether, or also as a mixture of both isomers. For use as fungicides, it is possible to use both a mixture of isomers which is eliminated during manufacture and individual isomers.

Surprisingly, it has been found that the salts of the esters of N-alkyl-2,6-dimethylmorpholinio-carboxylic acids and the salts of the N-alkyl-2,6-dimethylmorpholinio-alkylphenyl ethers of the general formula I exhibit strong fungicidal activity and broad spectrum of activity and are particularly suitable for combating phytopathogenic fungi on crop plants and plant stored goods. The active substances show good tolerance to plants at the amounts required for the treatment of plants infected with diseases. In addition, the compounds according to the invention can have a positive effect on crop plants by their growth-regulating effects.

The active compounds of the formula I according to the invention show a strong activity against microorganisms and can therefore find use in combating fungal diseases in agriculture and horticulture. The active substances can kill unwanted fungi occurring on plants or plant parts. The active compounds of the formula I can furthermore serve as mordants for the treatment of sowing and plant seedlings for protection against fungal infections and can also be used against phytopathogenic fungi which occur in the soil. In addition, the active substances also have a positive effect on the growth process of crops when used.

N-alkyl-2,6-dimethylmorpholinocarboxylic acid esters salts of N-alkyl-2,6-dimethylmorpholinioalkylphenyl ether of formula (I) are prepared by reacting N-alkyl-2,6-dimethylmorpholine of formula (II)

(II) wherein R ^{1 is} as defined above, with a compound of formula III

X-R ² -A where R ² has the abovementioned meaning а X represents halogen.

The above reaction is optionally carried out in the presence of solvents or diluents at temperatures in the range of 10 to 180 ° C, preferably in the range of 30 to 150 ^: C. The starting compound of formula II is reacted in stoichiometric amounts with the compound of formula III, or an excess of 10 to 100% of the compound of formula III above the stoichiometric amount based on the starting material of formula II.

Preferred solvents or diluents are, for example, aliphatic or aromatic or halogenated hydrocarbons such as n-heptane, 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 dioxane; alcohols such as methanol, ethanol, propyl alcohols, butyl alcohols or hexanols; nitriles such as acetonitrile; esters such as acetic acid methyl ester; amides such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone; dimethylsulfoxide or water, and mixtures of these solvents.

Isolation of the compounds of formula (I) from the reaction mixture is not absolutely necessary as this reaction mixture is suitable for the production of fungicidal compositions without further purification.

Examples of N-alkyl-2,6-dimethylmorpholines of the formula II include n-decyl-2,6-dimethylmorpholine, n-dodecyl-2,6-dimethylmorpholine, n-tridecyl-2,6-dimethylmorpholine, iso-tridecyl -2,6-dimethylmorpholine, 1,5,9-trimethyldecyl-2,6-dimethylmorpholine, n-pentadecyl-2,6-dimethylmorpholine or n-didecyl-2,6-dimethylmorpholine.

As the halocarboxylic acid esters of the general formula III, for example, they can be used

C 1 -C 20 -alkyl chloroacetic acid ester, 4-chlorobutyl chloroacetic acid ester, 4-hydroxybutyl chloroacetic acid ester,

2-ethoxyethyl chloroacetate, 2-cyanoethyl chloroacetate, 2-nitroethyl chloroacetate, cyclohexyl chloroacetate, methyl 2-bromopropionate, allyl 2-bromopropionate,

2-bromopropionate 1-naphthyl ester, chloroacetic acid phenyl ester, thiol-chloroacetic acid phenyl ester, 2-bromobutyric acid methyl ester, benzyl 2-bromocaproate, 4-chlorophenyl chloroacetic acid ester, 4-tert-butylphenyl chloroacetic acid ester, (III)

Chloroacetic acid 3,4-dichlorophenyl ester,

2,6-dimethylphenyl chloroacetate,

2,6-dibromo-4-nitrophenyl chloroacetate,

2,6-dibromo-4-cyanophenyl chloroacetic acid ester,

2,6-dichlorobenzyl chloroacetate, 4-cyanobenzyl chloroacetate, 4-nitrophenyl chloroacetate or chloroacetate anion.

As haloalkylphenyl ethers of the formula III, for example, they can be used

2-bromoethylphenyl ether,

2-chloroethyl-4-tert-butylphenyl ether, 2-bromoethyl-4-nitrophenyl ether, 2-bromoethyl-4-cyanophenyl 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-bromoethyl-4-benzylphenyl ether,

2-bromoethyl-4-acetamidophenyl ether,

3-bromopropyl-phenyl ether, 3-bromopropyl-4-tert-butylphenyl ether, 3-bromopropyl-2,6-dimethylphenyl ether, or

3-Bromopropyl-2,6-dibromo-4-thiocyanato-phenyl ether.

The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared by methods known per se.

The active compounds according to the invention are particularly suitable for the prevention and treatment of plant diseases caused by fungi such as, for example, Erysiphe graminis, Erysiphe cichoracearum, Erysiphe polygoni, Podosphaera, Sphaerotheca pannosa, Uncinula necator; and rust diseases caused in particular by the genera Puccinia, Uromyces or Hemileia, in particular Puccinia graminis, Puccinia coronata, Puccinia sorghi, Puccinia recondita, Uromyces fabae and Hemileia vastatrix. Furthermore, these diseases are caused by the fungus Botrytis cinerea on grapevine and strawberries, Monilia fructigena on apple, Plasmopara viticola on grapevine, Mycosphaerella musicola on bananas, Corticum salmonicolor and Ganoderma pseudoferreum on hevea, exobasidium vexans on teaspoon, exobasidium vexans on potato, Alternaria solani on tomatoes. Furthermore, the various active compounds are also differently active against phytopathogenic fungi such as Ustilago avenae, Ophiobolus graminis, Septoria nonodum, Venturia inae.iualis and other agents of fungal diseases such as Rhizoctonia, Tilletia, Helminthosporium, Perenospora, Pythium, Alternaria. Mucor, Scleronia, Fusarium, Pseudocercosporella and Cladosporium.

Of particular interest are the active substances according to the invention for combating a number of fungal diseases on various crop plants or their seeds, in particular wheat, rye, barley, oats, rice, maize, cotton, soya, coffee, banana, sugarcane, fruit , ornamental plants in horticulture, vegetables such as cucumbers, beans or squashes.

In addition, the active compounds according to the invention can, by their growth-regulating properties, positively influence the development of crop plants to the desired extent. The effects of these compounds occur essentially from the time of application, are related to the stage of development of the seeds or plants and depend on the amount of active substance applied to the plants or their surroundings and the type of application.

Furthermore, the active compounds according to the invention a good activity against Talk dřevozbarvuj ^t CIM and wood-destroying fungi such as Pullaria pulluhans, Aspergillus niger, Polystictus versicolor or Chaetomium globosum.

Furthermore, the active compounds according to the invention of the general formula I have a good activity against fungi, such as Penicillium, Fusarium or Aspergillus, which cause spoilage of agricultural products with high water content or agricultural processing products during storage or intermediate storage. Talkto processes such as apples, oranges, tangerines, peanuts, cereals and grain or pulses.

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

Some of the active compounds according to the invention also show effects against human pathogenic fungi, such as Trichophyten and Candida.

Part of the active compounds of the formula I are characterized by a systemic increase in action in addition to the protective action. Thus, they are received both through the roots and leaves and are transported through the plant tissue, or are fed through the seed to the above-ground parts of the plant.

The active compounds according to the invention are furthermore suitable for combating resistant fungal disease strains which exhibit resistance to known fungicidal active substances, such as, for example, dicarboximide fungicides, such as 5-methyl-5-vinyl-3- (3,5- dichlorophenyl) -2,4-dioxo-1,3-oxazolidine (Vinclozolin) or 5-methyl-5-methoxymethyl-3- (3,5-dichlorophenyl) -1,3-oxazolidine-2,4-dione (Myclozolin) active substances from the group of benzimidazole or thiophanate fungicides, such as 1- (n-butylcarbamoyl) -benzimidaziol-2-yl-carbamic acid methyl ester (Benomyl), benzimidazol-2-ylcarbamic acid methyl ester (Carbendazim) or 1, 2-bis (3-ethoxycarbonyl-2-thioureido) -benzene (Thiophanat]; azole fungicide active compounds, such as 1- (4-chlorophenoxy-3,3-dimethyl-1- (1H-1,2); 4-triazol-1-yl) -butan-2-one (Triadimefon) or 1- (2 ', 2', 4'-dichlorophenyl) -2 '- (propenyloxy) ethyl-1,3-imida zol (Imazalil): aromatic hydrocarbon-containing fungicides such as 2,5-dichloro-1,4-dimethoxybenzene (Chloroneb) or 2,6-dichloro-4-nitroaniline (Dicloran); active substances from the group of acylalanine fungicides, such as DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) -alanine methyl ester (Metalaxyl) or DL-N- [2,6-dimethylphenyl) methyl ester - N- (2-fluoryl) -alanine (Furalaxyl) or active substances from the group of pyrimidine fungicides such as 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine (Dimethirimol) or 2-chlorophenyl-4-chlorophenyl- pyrimidin-5-yl-methanol (Fenarimol).

The anion X 'in the active compound of the formula I is not critical to the fungicidal activity of the compound.

The active compounds of the present invention can be converted into conventional formulations such as solutions, emulsions, suspensions, dust, dust, dust, foam, paste, soluble dust, granulate, active-impregnated natural and synthetic substances, fine capsules in polymeric substances and encapsulants. for seed. Said preparations are prepared by known methods, for example by mixing or grinding the active compounds according to the invention of the formula I with solvents and / or carriers, optionally using surfactants such as emulsifiers and / or dispersing agents.

As liquid solvents, aromatics such as toluene, xylene or alkyl naphthalenes can be used; chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzene, chlorethylene or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions; alkanols such as alcohols or glycols, as well as esters and ethers thereof; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents such as water, dimethylformamide or dimethylsulfoxide. Liquefying solvents which are normally gaseous, such as aerosol carrier gases, for example halogenated hydrocarbons, propane, butane, nitrogen and carbon dioxide, may also be used.

Suitable solid carriers are, for example, natural ground minerals, such as kaolins, clays, talc, chalk, (quartz, montmorillonite or diatomite, and synthetic flours such as highly disperse silica, alumina and silicates).

For example, crushed and fractionated ground rocks such as limestone, marble, pumice or dolomite, as well as synthetic granules of inorganic or organic flours, as well as granules of organic materials such as wood flour, cellulose powder, flour of tree bark or nut shells.

Non-ionic and anionic emulsifiers such as alkali, alkaline-earth and ammonium salts of ligninsulfonic acids, naphthenesulfonic acids (acids, phenolsulfonic acids, arylsulfonates, alkylsulfates, alkylsulfonates, alkaline and alkaline earth salts, dibutyl laphthalenesethers) fatty alcohol sulphates, alkali and alkaline earth salts of fatty acids, salts of sulfated hexadecanols, heptadecanols or octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalenes and derivatives of naphthalenes with formaldehyde, condensation products of naphthalenes, formal and naphthalenesulfone -octylphenol ether, alkylarylpolyetheralkanols, iso-tridecyl alcohol, condensates of ethylene oxide and fatty alcohols, ethoxylated castor oil, polyoxyethylene alkyl] ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal and sorbitester.

Suitable dispersing agents may be, for example, lignin sulphite spirits and methylcellulose.

Sizing agents such as carboxymethylcellulose, natural and synthetic latex polymers such as acacia, polyvinyl alcohol and polyvinyl acetate may be used in the formulations.

As further additives, the preparations may contain colored substances and fertilizers in trace amounts. The formulations generally contain 0.1 to 95% by weight of active ingredient, preferably 0.5 to 90% by weight.

According to the present invention, the method for combating fungal diseases is characterized in that the fungicidal composition with the active compound according to the invention of the formula I is treated in an effective amount on fungi or objects protected against fungal attack.

The active compounds according to the invention can be mixed in the preparations with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, growth regulators, fertilizers and soil improvers and co-applied. In many cases, when mixed with fungicides, the fungicidal spectrum of action is broadened. When the active compounds according to the invention are mixed with known fungicides, a synergistic effect is often obtained, the func424279 gicidal activity of the combination being higher than the sum of the effects of the individual components.

The fungicides which can be combined with the active compounds according to the invention are, without limiting the possibilities of combinations, as follows:

sulfur, dithiocarbamates and derivatives thereof such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, manganethylenebis-dithiocarbamate, manganese-zinc-ethylenediamine-bis-dithiocarbamate and zinc-ethylene-bis-dithiocarbamate, tetramethylenediamine, -dithiocarbamate and N, N'-polyethylene-bls- (thiocarbamoyl) -disulfide, an ammoniacal complex of zinc- (N, N'-propylene-bis-dithiocarbamate and N, N ^: -propylene-bis- (thiocarbamoyl) -disulfide,

N-trichloromethylthio-tetrahydrophthalmide, N-trichloromethylthio-phthalimide,

N- [1,1,2,2-tetrachloroethylthio] -tetrahydrophthalimide,

4,6-dinitro-2- (1-methylheptyl) -phenyl crotonate,

4,6-dinitro-2-sec-butylphenyl-3,3-dimethylacrylate,

4,6-dinitro-2-sec-butylphenyl isopropyl carbonate, 1- (n-butylcarbanioyl) -benzimidazol-2-yl-carbamic acid methyl ester, benzimidazol-2-yl-carbamic acid methyl ester,

2- (2-furyl) -benzimidazole,

2- (thiazol-4-yl) -benzimidazole,

1,2-bis- (3-methoxycarbonyl-2-thioureido) -benzene,

1,2-bls- (3-ethoxycarbonyl-2-thioureido) -benzene,

2,3-dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiin,

2,3-dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiine-4,4-dioxide, tetrachloroisophthalic acid dinitrile,

2,3-dichloro-1,4-naphthoquinone,

2,3-Dilkyano-1,4-dithioanthraquinone, N-tridecyl-2,6-dimethyl-morpholine or its salts,

N — C10 to Cid-alkyl-2,5- and / or -2,6-dimethylmorpholine,

N-cyclododecyl-2,6-dimethylmorpholine or its salts,

N - [(3-p-tert-butylphenyl) -2-methylpropyl] -2,6-cis-dimethylmethylmorpholine or its salts,

N, N'-bis- (1-formamido-2,2,2-trichloroethyl) -piperazine,

N- (1-formamido-2,2,2-trichloroethyl) -3,4-dichloroaniline,

N- (1-formamido-2,2,2-trichloroethyl) morpholine,

5-Butyl-2-ethylamino-4-hydroxy-6-methyl-pyrlinidine,

5-Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine

2,4-dichlorophenyl-phenyl-pyrimidin-5-yl-methanol,

2-chlorophenyl-4-chlorophenyl-pyrimidin-5-yl-methanol, bis- (4-chlorophenyl) -pyridin-3-yl-methanol, 5-methyl-5-vinyl-3- (3,5-dichlorophenyl) - 1,3-oxazolidine-2,4-dione,

5-methyl-5-methoxymethyl-3- (3,5-dichlorophenyl) -1,3-oxazolidine-2,4-dione,

3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxo-imidazolidine-1-carboxamide,

N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide,

1- (4-chlorophenoxy) -3,3-dimethyl-1,1- (1,2,4-triazol-1-yl) butan-2-one,

1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) butan-2-ol,

1- [2- (2,4-Dichlorophenyl) -2- (propenyloxy) ethyl] imidazole

1- | N-propyl-N- (2,4,6-trichlorophenoxy) ethylcarbamoyl-imidazole, 1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolane-2- yl-methyl] -1H-1,2,4-triazole, 1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-ylmethyl] -1H, 1,2,4-triazole,

1- (2,4-Dichlorophenyl) -2- (1,2,4-triazol-1-yl) -4,4-dimethylpentan-3-one;

2,5-dichloro-1,4-dimethoxybenzene,

2,6-dichloro-4-nitroaniline, diphenyl, 2-methylbenzoic acid anilide, 2-iodobenzoic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid anilide, 2,4,5-trimethyl-furan-3- anilide carboxylic acid N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxylic acid amide,

3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] -glutarimide, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenyl-sulfuric acid diamide, DL -N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) -alanine, DL-N- (2,6-dimethylphenyl) -N- (2-furoyl) -alanine methyl ester,

N- (2,6-dimethylphenyl) -N-chloroacetyl-DL-6-aminobutyrolactone,

2,4-dichloro-6- (2-chloroanilino) -s-triazine, 0, 0-diethylphthalimido-phosphonothioate, 5-amino-1 - [(bis (dimethylamino) -phosphinyl] -3 -phenyl-1,2,4-triazole, O, O-diethyl-S-benzyl-thiophosphoric acid ester,

2-thio-1,3-di-thio- (4,5-b-quinoxaline),

4- (2-chlorophenylhydrazone) -3-methyl-5-isoxazolone, pyridine-2-thiol-1-oxide,

8-hydroxyquinoline or salts thereof, 4-dimethylaminophenyl diazosulfonic acid sodium salt, 5-nitroisophthalic acid diisopropyl ester,

2-cyano-N- (ethylaminocarbonyl) -2- (methoxyimino) acetamide,

2-heptadecyl-2-imidazoline acetate, dodecyl guanidine acetate.

The active ingredients can be used as such, in the form of preparations or by further diluting the formulations prepared therefrom in a conventional manner, for example by pouring, dipping, spraying, spraying, misting, injecting, dry pickling, wetting pickling, dry, wet pickling, wet pickling, sludge pickling or incrustation.

When processing plant parts, the concentration of active ingredient in the formulation used may vary within wide limits. It is generally in the range from 0.000 to 1% by weight, preferably from 0.001 to 0.5% by weight. The amount of active compound to be used depends on the specific purpose of use and is generally in the range of 0.1 to 3 kg of active compound per hectare.

In the treatment of seed, generally 0.001 to 50 g or more of active ingredient per kilogram of seed, preferably 0.01 to 10 g, is required.

For the preservation or post-treatment of agricultural or agricultural products, the amount of active ingredient required is 0.01 to 100 g per kilogram of raw material to be processed, preferably 0.1 to 50 g.

In soil treatment, active compound concentrations of from 0.000 to 0.1% by weight, preferably from 0.001 to 0.05% by weight, are required per site of action.

The following Examples illustrate and demonstrate the effect of the compounds of Formula I.

The following examples illustrate the preparation of the compounds of the invention in more detail

Example 1

N-iso-tridecyl-2,6-dimethylmorpholinol acetic acid methyl ester g of N-iso-tridecyl-2,6-dimethylmorpholine and 10.9 g of chloroacetic acid methyl ester are heated to reflux with the addition of a catalytic amount of sodium iodide. in 20 ml of acetonitrile. The reaction mixture was cooled and the solvent was evaporated in vacuo. The product was digested with n-hexane. Concentration in vacuo afforded 38 g of a tan oil (Compound No. 3).

IR spectrum (film):

C = O - absorption 1,740 cm ^-1 .

Example 2

3,4-Dichlorophenyl acid chloride chloride

N-iso-tridecyl-2,6-dimethylmorpholinoacetate g of N-iso-tridecyl-2,6-dimethylmorpholine and 24 g of 3,4-dichlorophenyl chloroacetic acid ester are refluxed for 16 hours with the addition of a catalytic amount of sodium iodide. in 100 ml of n-butyl alcohol. The reaction mixture was then cooled and the solvent was evaporated in vacuo. The residual product is dissolved in a small amount of diethyl ether and treated with n-hexane until completely separated as an oily phase. Concentration in vacuo gave 48 g of a dark brown resin (Compound No. 29).

IR spectrum (film):

C = O — absorption of 1 740 cm ^-1 ,

С = C - absorption (flavor 1 590 cm ¹ .

Example 3

2- (Noso-tridecyl-2,6-dimethylmorpholinio) -propionic acid methyl ester chloride 2- (2,6-dimethylmorpholinio) -propionic acid methyl ester and 22 g of iso-tridecyl chloride (a mixture of various C 6 -C 14 alkyl chlorides containing 60 to 70 n-tridecyl chloride) was heated to reflux in 100 ml of dimethylformamide for 10 hours. After cooling the reaction mixture, the solvent was distilled off in vacuo. The product was dissolved in a small amount of acetone and treated with n-hexane until the oily phase completely formed. Concentration in vacuo afforded 19 g of a light brown resin (Compound No. 5).

IR spectrum (film):

C = O - absorption of 1 735 cm ^-1 .

Example 4

3- (N-iso-tridecyl-2,6-dimethylmorpholinio) -propyl-2,6-dimethylphenyl ether bromide g of N-iso-tridecyl-2,6-dimethylmorpholine and 12.2 g of 3-bromopropyl-2,6- dimethylphenyl ether was refluxed in 50 ml of acetonitrile for 23 hours with the addition of a catalytic amount of sodium iodide. The reaction mixture was then cooled and the solvent was distilled off in vacuo. The residue is taken up in a small amount of acetone and the solution is mixed with n-hexane until complete precipitation. The oily phase was separated and the solvent was removed in vacuo. 21 g of a tan, viscous oil is obtained (compound 54).

Example 5

2- (N-iso-tridecyl-2,6-dimethylmorpholinio) -ethyl-3,4-dichlorophenyl ether chloride g of 2- (2,6-dimethylmorpholinol) ethyl-3,4-dichlorophenyl ether and 11 g of iso -tridecyl chloride (a mixture of various C 1 to C 14 -alkyl halides containing 60 to 70% by weight of n-tridecyl chloride) was heated under reflux in 5.0 ml of dimethylformamide for 10 hours. The reaction mixture was then cooled and the solvent was distilled off in vacuo. The evaporation residue is dissolved in a small amount of acetone and mixed with n-hexane until completely separated as an oily phase. The product was separated and the solvent was removed in vacuo. 19 g of brown resin product (Compound No. 53) are obtained.

The following compounds of formula (I) are prepared in a corresponding manner, mostly in yellow form _; to brown oily liquid or resin. Said compounds are well soluble in polar solvents such as alcohols, acetone, dimethylformamide and dimethylsulfoxide. They are characterized by the IC spectrum.

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

Example I

Solution concentrate:

80 parts by weight of compound 5 with 20 parts by weight of N-methyl-2-pyrrolidone are obtained. Z ^r twisted in a solution which is suitable к application in the form of very small drops.

Example II

Emulsifiable Concentrate n:

25 parts by weight of compound 55 are mixed with 2.5 parts by weight of epoxidized vegetable oil, 10 parts by weight of a mixture of alkylarylsulfonate and fatty alcohol polyglycol ether, 5 parts by weight of methylformamide and 57.5 parts by weight of xylene. An emulsion of any concentration can be obtained from this concentrate by dilution with water.

Example III

Spray powder:

parts by weight of compound 65 are mixed well with 5 parts by weight of sodium lignin sulphonic acid from the sulphite liquor, one part by weight of di-isobutylnaphthalenesulphonic acid sodium salt and 54 parts by weight of silica gel and the mixture is ground well in a corresponding mill. A spray powder is obtained which can be diluted with water to a suspension of any desired concentration.

Example IV

Spread:

parts by weight of compound 55 are mixed well with 95 parts by weight of finely divided kaolin and the mixture is ground. The spreading can be applied directly.

Example V

Granulate:

parts by weight of compound 57 are mixed with 0.25 parts by weight of epichlorohydrin and this mixture is dissolved in 6 parts by weight of acetone. Then 3.5 parts by weight of polyethylene glycol and 0.25 parts by weight of cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and then the acetone is evaporated in vacuo. A microgranulate is obtained which can be used in this form.

The following examples illustrate and demonstrate the effect of the compounds of formula J.

P г í к 1 a d А

Mycelium growth test

At the same time, the fungicidal effect of the fungal agents is found to suppress the radial growth of mycelium on malt agar broth (2% malt) in 9 cm diameter petri dishes at an incubation temperature of 25 ° C. To this end, the active ingredient is dissolved in dimethylformamide, diluted with water and admixed with liquid agar to obtain the desired active ingredient concentration in the nutrient medium. The dimethylformamide content does not exceed 0.5% by volume. After cooling, the plates were inoculated. The evaluation is always carried out on the basis of the growth rate of the fungus when 70 to 90% of the diameter of the dish is grown on the control dish without the addition of the active ingredient. The percentage inhibition of growth by the active substance is then calculated. Values for some compounds are shown in Table A.

TABLE А

Suppression of fungal growth in a mycelial growth assay

Compound growth suppression in% C. Botrytis cinerea Phytophtora cactorum concentration of account 1. 10 jug / liter 50 .mu.g / l Охусаrboxin (known) 20 May 50 3 88 85 5 91 48 6 92 51 8 89 100 ALIGN! 9 79 100 ALIGN! 13 91 20 May 78 67 22nd 86 100 ALIGN! 25 84 60 29 97 100 ALIGN! 31 94 100 ALIGN! N-iso-tridecyl-2,6-dimethylmorpholinic acetic acid 2,6-dibromo-4-nitrophenyl ester chloride 92 100 ALIGN! 34 95. 100 ALIGN! 36 78 37 22nd 39 90 40 87 43 85 48 86 100 ALIGN! 52 88 81 53 88 54 80 60 92 100 ALIGN!

Example В

Test for barley powdery mildew (Erysiphe graminis)

In the sand rhizome, the barley plants of the "Astacus" species are moistened in a single leaf stage with an active ingredient preparation consisting of one part by weight of active substance, 100 parts by weight of diinomethylformamide and 0.25 parts by weight of alkylaryl polyglycol ether and diluted with water to the desired concentration . After spraying, the plants are dusted with conidia of mildew of barley (Erysiphe graminis var. Hordei). Thereafter, the test plants are placed in an incubation cabinet at 90-100% relative humidity for 2 to 3 hours and then in a greenhouse at a temperature of 20-22 ^° C and a relative air humidity of 75-80%. After seven days, the infestation of barley plants by powdery mildew is detected. The values obtained by Stephana [Arch. Phytopath. Pfl.-schutz 14 (1978), 163-175] were converted to Krüger's degree of attack (Nachr.-Bl. Pflanzenschutz DDR 1981, 145-147). This implies a degree of effect according to Abbot, corresponding to the degree of effect (%) = degree of attack (control) - degree of attack (variant) degree of attack (control x 100

The results obtained are shown in Table B below:

TABLE В

Example D

Effect against Erysiphe graminis on barley

Active substance concentration: 10 mg / l compound no.

degree of effect (%)

N-methyl-N-tridecyl-2,6-dimethylmorpholine methosulfate

) according to DE-PS 11 67 588) 82 forine (known) 86 3 88 5 82 6 87 8 93 13 97 20: 94 29 88 34 90 39 96 52 92 53 93 54 95 60 97

Example С

Cereal rust test (Puccinia recondila)

The wheat plants planted in mugs are cut to a height of 12 cm at the two leaf stage. The secondary leaves of the plants are removed. Then the wheat plants are sprayed with an active ingredient preparation consisting of 10 parts by weight of polyoxyethylene sorbitan monostearate (Tween 60), 5 parts by weight of cyclohexanone and 40 parts by weight of toluene and diluted with water to the desired concentration. The plants are inoculated with spores of wheat rust (Puccinia recondita), which are applied as a suspension in water with the addition of Tween-60. The test plants are then placed in a steam-saturated incubation cabinet for 24 hours and then placed in a greenhouse at 20 to 22 ° C and relative humidity 70 to 80 ° / o.

After 10 days the plants were examined for rust. The degree of action of the composition was calculated by the method described in Example B. The results are shown in Table D below.

Wheat powdery mildew test (Erysiphe graminis)

In single-leaf stage wheat-planted "Alcedo" plants, they are sprayed moist with the active ingredient preparation consisting of one part by weight of active ingredient, 100 parts by weight of dimethylformamide and 0.25 parts by weight of alkyl aryl polyglycol ether and diluted with water to the desired concentration active substance. After spray drying, the plants are dusted with conidia (spores) of wheat mildew [Erysiphe graminis var. tritici). Thereafter, the test plants are placed in an incubation cabinet for 2 to 3 hours at a relative humidity of 90 to 100% and then placed in a greenhouse at 20 to 22 ° C and a relative humidity of 75 to 80%. After five days, the infestation of the wheat plants by the powdery mildew. The degree of action of the composition was calculated as described in Example B. The results are shown in Table C below.

TABLE D

Activity against Puccinia recondita on wheat Concentration of active substance: 500 mg / l compound

C.

Triforine (known)

Example E

TABLE С

Effect against Erysiphe graminis on wheat

Active substance concentration 100 mg / l Compound no.

degree of effect (%) degree of effect (%)

N-methyl-N-tridecyl-2,6-dimethylmorpholinium methosulfate (according to DE-PS 11 67 588)

Cucumber mold test (mixed culture of Erysiphe cichorarearum and Sphaerotheca fuliginea)

The 'Eva' cucumber plants planted in pots, at the four-star stage, are inoculated with a suspension of conidia of a mixed culture of Erysiphe cichoracearum and Sphaerotheca fuliginea. After four days, the plants are sprayed wet with the active ingredient preparation, which consists of one part by weight of the active substance, 100 parts by weight of dimethylformamide and 0.25 parts by weight of alkylaryl polyglycol ether and which is diluted with water to the desired concentration of active substance. After the spraying has dried, the plants are placed in a greenhouse at a temperature of 20 ° C and a relative humidity of 70 to 80%.

After 6 or 9 days, cucumber fungal infections are observed on cucumber plants.

Values determined by Bolle [Nach07 richtbl. Dt. Pflanzenschutzdienst 16 (1964), The results given in the following ta92-94] are converted to the degree of attack of E.

Krůger, of which the degree of effect according to Abbot.

TABLE E

Action against Erysiphe cicinoracearum and Sphaerotliece fuliginea (mixed culture) on cucumbers

Active substance concentration: 500 mg / 1 compound degree of action (%)

No after 6 days after 9 days

Tridemorph (known) 100 88

100 100

Example F

Botritis test (Botrytis cinerea / Broad beans - Vicia ta baťť)

The four leaf leaves of the 'Fribo' bean leaves of Vicia faba are sprayed with the active substance preparation, which consists of one part by weight of the active substance, 100 parts by weight of dimethylformamide and 0.25 parts by weight of alkylaryl polyglycol ether and which is diluted with water to the desired concentration of active ingredient. After spraying, the leaves are inoculated with Iconidium Botrytis cinerea suspension, which is obtained by rinsing a 12 to 16 day fungus culture on wort agar (2% malt). The bean leaves are then placed in an incubation chamber in the dishes, the temperature here being 22 ^° C and the relative humidity of the air in the range of 90-100%.

After four days, the infection of the bean root with botritis is examined. The percentage attack on the total leaf area is calculated according to Abbott to the degree of effect of the composition. The results are shown in Table F below.

TABLE F

Action against Botrytis cinerea on common bean (Vicia faba)

Active substance concentration: 100 mg / l compound grade

No. of effect (%) Compound No.

degree of effect (%)

Example G

Phytophtor test [Phy tophtor and infestans / tomatoes)

In pots planted "Tamina" tomato plants, they are sprayed at three leaf stages with an active ingredient preparation consisting of one part by weight of active substance, 100 parts by weight of dimethylformamide and 0.25 parts by weight of alkylaryl glycol ether diluted with water to the desired concentration active substance. After spray drying, the plants are inoculated with an aqueous zoospore suspension of Phythosphory infestans. The fracture is dropped into the incubation chamber at a temperature in the range of 18-20 ° C and a relative air humidity of 95-100%.

After five days, Phytophtora infestation of tomato plants is examined. The values obtained are converted to the degree of attack and the degree of action of the composition as described in Example B. The results are shown in Table G below.

Tridemorph (known)

TABLE G

Effect against Phytophtora infestans on tomatoes

compound no. conc. active substances (mg / l) degree, effect (° / o) Zineb (known) 100 ALIGN! 57 200 61 52 100 ALIGN! 66 200 79

Example Η

TABLE rostlin plant height in cm relative

Plant growth control test

Cucumber plants of the "Ev.a" class are grown in pots with humus soil, which is sufficiently supplied with nutrients, in a greenhouse up to 9 cm in size. 10 plants were used for the experimental variant. Cucumber plants are sprayed with the active ingredient preparation, which consists of one part by weight of active substance, 100 parts by weight of dimethylformamide and 0.25 parts by weight of alicylaryl polyglycol ether and which is diluted with water to the desired concentration of active substance.

After a growth period of 14 days after application of the composition, length measurements are taken for the treated plants and the untreated control plants. The results are shown in Table H.

TABLE H

Effect on longitudinal growth of cucumber plants in leaf processing

Active substance concentration: 1000 mg / l compound no.

unprocessed check 25 100 ALIGN! 3 15.6 68 52 15 Dec 65

For clarity, the following compounds are used in the following bioassays for reference purposes, with reference to the respective Examples A to H.

hLC (I)

ТА ВU L К A

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(0

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Claims (2)

SUBJECT OF THE INVENTION A fungicidal composition having an additional growth-regulating effect on a plant, characterized in that it contains, as active ingredient, a salt of N-alkyl-2,6-dimethylmorpholinocarboxylic acid and a salt of N-alkyl-2,6-dimethylmorpholinioalkylphenyl ether of the general formula I wherein A represents -CO-Z-R ⁵ or a group -O where R ³ denotes a straight-chained alkyl group having 1 to 12 carbon atoms, an ethyl group substituted with ethoxy, nitro and / or cyano, an alkenyl group having 3 to 4 carbon atoms, a propargyl group, a cycloalkyl group having 5 to 6 carbon atoms, be substituted by two methyl groups, a phenyl group which may be mono- or polysubstituted, the same or differently substituted by a straight or branched alkyl group having 1 to 4 carbon atoms, a benzyl group, a halogen atom, a phenyl group, a nitro group and / or a cyano group; R ⁴ represents a hydrogen atom, a methyl group, a tert-butyl group, a methoxy group, a phenyl group, a halogen atom, a nitro group, a cyano group or an ethoxycarbonyl group, R ⁵ represents a hydrogen atom, a chlorine atom, a methyl group, a thiocyanate group or a cyano group, R ⁶ represents a hydrogen atom, a halogen atom or a methyl group; Z denotes an oxygen atom, R @ ^{1 is a} straight or branched alkyl group having from 8 to 13 carbon atoms, R ² a linear or branched alkylene group having 1 to 3 carbon atoms and X - is chlorine or bromine, or R ³ and X - are not present. 2. A process according to claim 1, which comprises reacting an N-alkyl-2,6-dimethylmorpholine of the formula (II) in which: R ¹ as defined above, with a compound of formula III X - R ² - and (III) in which it has R ^{2 and} A as defined above and X represent a halogen atom.