DD263689A1 - FUNGICIDAL AGENT WITH ADDITIONAL PLANT GROWTH REGULATORY EFFECT - Google Patents

Abstract

The invention relates to a mixture of N-alkyl-2,6-dimethylmorpholinio-carbonsaeureamid salts and at least 15 wt .-% proportion of N-alkyl-2,5-dimethylmorpholinio-carbonsaeureamid salts of the general formula I and its use as fungicides Means of controlling fungal pathogens in agriculture and horticulture with additional plant growth regulating properties. The meaning of R1, R2, R3, R4 and X can be taken from the description. Formula (I)

Description

Anwanclimg.ac} atueU Aqji

The invention relates to a mixture of i-i-alky 1-2,6-cis- and / or trans-dimethylmorpholinio-carboxylic acid amide salts and at least 15 percent by mass of N-alkyl ^ / ö-cis- and / or trans- <dimethyl ~ morpholinio-carboxamide salts and their use as fungicides in agriculture and horticulture with additional plant growth-regulating properties.

Ch.ar.akt.eris. t.iX .dar Ji e. k ken. .t, e.Qh.n.is.chen. .Lö, s, mig e.n

It is known to use N-alkylmorpholines and their salts and their molecular and addition compounds as fungicides (DE-PS 1 164 152, DE-PS 1 173 722, DE-PS 24 61 513). It is also known that quaternary ammonium compounds of long-chain N-alkyl-2,6-dimethylmorpholinen with lower alkyl, alkenyl, alkoxyalkyl or aralkyl substituents are fungicidally effective (DE-PS 1,167,588, Angewandte Chemie 77 (1965), S, 327-333). Furthermore, agents are known which contain substituted N-ßenzyl- or alkoxymethyl-2,6-dimethylmorpholinium salts as active ingredients for the fight against fungal pathogens (DD-PS 134 037, DD-PS 134 474, DD-PS 140 403). It is also known to use morpholine-4-carboxylic acid anilides for controlling phytopathogenic fungi (DD-PS 141 778).

Furthermore, salts of cL- aminoacetanides, which also include the morpholine ring as the amine component, with lower alkyl, cyanoalkyl, alkenyl and alkynyl substituents as agents for influencing or regulating plant week growth are mentioned (DE-PS 26 57 728 and DE-PS 26 57 728). PS 2915 250).

Furthermore, 2,3-dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiin-4,4-dioxide (oxycarboxine), N, N'-bis- (1-formamido-2,2, 2-trichloroethyl) -piperazine (triforine) or zinc ethylene-bis-di-thiocarbamate (zineb) as active ingredients in fungicidal plant disease control agents (The Pesticide Manual, British Crop Protection Council, L'ondon, 1979).

However, the action of the compounds mentioned is not always completely satisfactory in certain indication areas, in particular at low application rates and concentrations. In addition, they show a rather high selectivity against certain types of fungal pathogens, which greatly limits the broad use of these agents. A further disadvantage is that the plant compatibility of these compounds is not sufficient in many cases.

Goal of. .E.nf.irujurig

The aim of the invention is the development of new compounds having improved fungicidal activity and additional growth-regulating properties and a process for their preparation, and fungicidal compositions containing such compounds, and the use of such fungicides in agriculture and horticulture.

Har.legurig. .the. .We.sen, s. .the. .Ejr. fi

It is an object of the present invention to provide a mixture of N-alkyl-2,6-cis- and / or trans-dimethylmorpholinio-carboxylic acid amide salts and at least 15% by weight of N-alkyl-2,5-cis- and / or trans- To provide this object, fungicidal compositions are proposed, which are characterized in that they contain a mixture of N.sup. + .sup. + and .sup. + .sup. + .sup. + .sup.- phytomorpholinio-carboxylic acid amide salts Alkyl-2,6-cis- and / or trans-dimethylmorpholinio-carboxylic acid amide salts and at least 15% by weight of N-alkyl-2,5-cis- and / or trans-dimethylmorpholinio-carboxamide salts of the general formula I,

ζω cn

O JST 3 ON ₃ X

R ² -CO-N ^/ and C ₁ R 1 CO-n '' (I)

IT ^K

in the

R is straight-chain or branched alkyl having 6 to 20 C atoms,

2 R is straight-chain or branched alkylene having 1 to 6 C atoms,

4 R and W, independently of one another, denote hydrogen, gergd-chain or branched alkyl having 1 to 20 C atoms, a straight-chain or branched chain which is substituted by hydroxyl, alkoxy having 1 to 4 C atoms, cyano or dialkylamino having 2 to 16 C atoms Alkyl having 1 to 6 carbon atoms, an optionally substituted by halogen alkenyl with

3 to 6 carbon atoms,

Cycloalkyl having 3 to 7 C atoms,

Aryl, which is monosubstituted or polysubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 6 C atoms, alkoxy having 1 to 4 C atoms, aryl-boiling alkyl having 7 to 12 C atoms, cycloalkyl having 3 to 7 C atoms, acyl having 1 to 4 C atoms, alkoxyalkyl having 1 to 8 C atoms, aryl, halogen, halogenoalkyl having 1 to 4 C atoms, halogenoalkoxy having 1 to 4 C atoms, alkylthio having 1 to 4 C, -Atomen, Halogenalkylthio with 1 to

4 C atoms, nitro, cyano, thiocyanato, NHCOR ', NIICO KFR "/ COOR', CO-NR ¹ R ' ¹ , SO ₂ R ¹ and / or SO ₂ NR ¹ R ¹¹ , wherein R ¹ and R ¹¹ independently of one another can be substituted by hydrogen, straight-chain or branched alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 7 C atoms, aryl or aryl-lower alkyl having 7 to 12 C atoms,

Aryl-lower-alkyl having 7 to 12 C atoms, which is monosubstituted or polysubstituted, identically or differently, by 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 Atoms, halogen, halogenoalkyl having 1 to 4 carbon atoms, nitro and / or cyano may be substituted, 4 R and R together with the nitrogen atom is an optionally one or two times by alkyl having 1 to 4 carbon atoms and / or halogen

represents substituted five- or six-membered heterocyclic ring, aer optionally contains one or two further heteroatoms, and

X ~ da3 anion of a non-phytotoxic acid, in addition to the usual Uösungsmitteln, carriers and / or formulation excipients included.

The compounds according to the invention can be mixed in four different geometric structures as N-alkyl-2,6-cis- and / or trans-dimethylmorpholinio-carboxamide salts or N-alkyl-2,5-cis- and / or trans-dimethylmorpholinio Carboxylic acid amide salts are present.

Surprisingly, it has been found that the compounds of the general formula I according to the invention have a strong fungicidal activity and a broad activity spectrum and are particularly suitable for controlling phytopathogenic fungi and crop plants and vegetable stocks. The active compounds show good plant compatibility in the amounts required for controlling plant diseases. In addition, the compounds according to the invention, with their growth-regulating properties, can positively influence crop plants in the desired manner. It has furthermore been found that the compounds of the general formula I according to the invention are obtained by reacting a mixture of N-alkyl-2 _# 6-cis- and / or trans-dimethylmorpholine and at least 15% by weight of N-alkyl-2,5-cis ur: d / or trans-dimethylmorpholine (according to DD-PS 140 412) of the formula II,

0 'NR ¹ and 0 NR ¹ · (il)

H ₃ C CH ₃

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

R ³ X - R ¹ - CO - N - (III)

2 3 4

wherein R, R and R have the meaning given in the general formula I and X is halogen reacted

or alternatively a mixture of 2,6-cis- and / or trans-dimethylmorpholino-carboxamide and at least 15 percent by weight of 2,5-cis- and / or trans-dimethylmorpholino-carboxamide of the formula IV,

(IV)

2 3 4

in which R, R and R have the meaning given in the general formula I, with a compound of the formula V,

R ¹ - X (V)

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

H ₃ Cv  -CO-N ^X R ⁴ and U Γ * O N-R ' O N-R-CO-N H ₃ CV- ⁷ CH ₃

-6- ZiSLf 9

The conversion to the erfJndungsgemäßen compounds of formula I are optionally carried out in the presence of a Uösiings- or diluent at a temperature ranging between 10 and 180 ⁰ C, preferably between 30 and 150 ⁰ C. ₇ The starting materials of the formula II or of the formula IV are in stöchiornetrisch.en amounts with a compound of formula III or the formula V or preferably with an excess of 10 to 100% of a compound of formula III or of formula V on 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 dioxane; Alcohols, such as methanol, ethanol, propanols, butanols or hexanols; Nitriles, such as acetonitrile; Esters, such as methyl acetate; Amides, such as dimethylformamide, dimethylacetamide or N-methyl-pyrrolidone; Dimethyl sulfoxide or water or mixtures of these solvents are used.

The isolation of the compounds of the general formula I according to the invention from the reaction mixtures is not necessarily required, since they can also be used for the preparation of fungicidal preparations without further purification operation.

The erf indungsgeinäßen active compounds of the general formula I have a strong activity against microorganisms and can accordingly be used for controlling 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 general 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 treatment of inflammatory diseases caused by fungi, such as Erysiphe graminis (powdery mildew), Erysiphe cichoracearum (cucumber flour), Erysiphe polygoni (bean powdery mildew), Podosphaera leucotricha (apple powdery mildew), Sphaerotheca pannosa ( Rosenmattau), 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 ati vines; Mycosphaerella musicola on bananas; Corticum salmonicolor on Hevea; Ganoderma pseudoferreum on Hevea; Exobasidium vexane to tea; Phytophthora infestans on potatoes and tomafctii; Alternaria solani on tomatoes. Furthermore, various of these agents are also different effective against phytopathogenic fungi, such as Ustilago avenae (flare), Ophiobolus graminis (cereal foot disease), Septoria nodorum (cereal and spelled), Venturia inaequalis (apple scab) and various Specis of the genera Rhizoctonia, Tilletia , Helminthosporium, Peronospora, Pythium or Mucor.

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, oats, sugar cane, fruit, horticultural ornamentals, 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 developmental stage of the seed or plants, on the amounts of active substance applied to the plants or their surroundings and on the mode of administration.

-8th-

Furthermore, the active ingredients also have good activity against wood-discolouring and wood-destroying fungi, such as B. Pullaria pullulans, Apsergillus niger, Polystictus versicolor or Chaetomium globosum.

Furthermore, the active compounds of the general formula I according to the invention exhibit a good activity against molds, such as, for example, Penicillium, Fusarium or Aspergillus species that cause spoilage of high moisture agricultural products or processed agricultural products during storage or storage. Such products include: apples, oranges, mandarins, lemons, grapefruit, 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 activity against human pathogenic fungi, e.g. Trichophyte 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 systemic development of action ». They are taken up both via the root and the leaves and transported in the plant tissue or via the seed to the aerial parts of the plant.

The active compounds according to the invention are furthermore suitable for controlling resistant strains of fungal pathogens which are resistant to known fungicidal active compounds, such as e.g. Active substances from the group of dicarboximide fungicides, such as, for example, 5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine (Vinclozolin) or 5-methyl-S methoxyniethyl-S-CS 1 -dichlorophenyl O-1 / S-oxazole idin-2, 4-dione (myclozoline); Active ingredients from the group of ßenzimidazol- or thiophanate fungicides, such as t- (n-butylcarbamoyl) benzimidazol-2-yl-carbamic acid ethyl ester (benomyl), Benζ imidazo1-2-yl-carbamic acid methyl ester (carbendazim) or 1,2 Bis- (3-ethoxycarbonyl-2-thioureido) -benzene (thiophanate); Materials from the

- g - tin

Group of azole fungicides, such as 1- (4-chlorophenoxy-3,3-dimethyl-1- (1H-2,4-triazole-1-yl) -butan-2-one (triadimefon) or 1- / 2 '- (2 *', 4 '' -Dichlorphenyl) -2 '- (propenyloxy) -ethyl / -l, 3-imidazol (imazalil); agents from the group of aromatic hydrocarbons containing fungicides such as _2/5 Dichloro-1, 4-dimethoxybenzene (chloroneb) or 2,6-dichloro

nitroaniline (diclorane); Active substances from the group of the acylalanine fungicides, such as, for example, Dl) -N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester (.Metaiaxyl) or DL'-N- (2,6-) phenyl) -N- (2-furoyl) -alanine methyl ester (Furalaxyl) or agents from the group of pyrimidine fungicides, such as 5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine (Dimethirimol ) or 2-chlorophenyl-4-chlorophenyl-pyrimidin-5-yl-methanol (fenarimol), show signs of resistance.

Cie ü 'the general formula I of the erf indungsgemäiJen active compounds listed anions X ~ 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, foams, pastes, soluble powders, granules, natural and synthetic substances impregnated with active substance, very fine encapsulations in polymeric substances and seed fillers, as well as UL ¹ V-KaIt and Warmseben formulations. The preparation of these formulations can be carried out in a known manner, for example by mixing or grinding the active compounds of the general formula I according to the invention with solvents and / or excipients, if appropriate using surface-active agents, such as emulsifiers and / or dispersants. such as toluene, xylene or alkylnaphthalenes; chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylenes or methylene chloride; aliphatic hydrocarbons such as cyclohexarene or paraffins, eg petroleum fractions; alcohols such as butanols or glycols and their esters and ethers; ketones such as acetone, methyl ethyl ketone .

- ίο -

Methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as water, dimethylformamide or Oimethylsulfoxid be used. Likewise, dissolved solvents which are gaseous under normal conditions, e.g. Aerosol propellants, such as halogenated hydrocarbons, propane, butane, nitrogen and carbon dioxide are used.

As solid carrier, there are e.g. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates in question. As solid carriers For granules, e.g. crushed and fractionated ground natural minerals such as calcite, marble, pumice, dolomite and synthetic granules of inorganic or organic flours and granules of organic materials such as sawdust, cellulose powder, bark and bark meal. As emulsifying agents, e.g. nonionic and anionic emulsifiers, such as. Alkali, brdalkali or ammonium salts of lignosulfonic acid, naphthalenesulfonic acids, phenolsulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, alkali and alkaline earth salts of dibutylnaphthalenesulfonic acid, uracyl 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 naphthalenesulfonic acid or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene-octylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylarylpolycthercohols, isotridecyl 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, L'ignin sulphite waste 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 in the

- Ii - ZtSC 93

Formulations of the active ingredients may be included.

The formulations generally contained between 0.1 and 95% by weight 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 are allowed to act on fungi or the objects to be protected against fungal attack in an effective amount.

The active compounds according to the invention can be mixed and applied in the formulations or in the various application forms with other known active compounds such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, growth regulators, plant nutrients and soil conditioners. In many cases, mixing with fungicides results in a widening of the fungicidal spectrum of action. In a number of mixtures of the active compounds according to the invention with known fungicides also synergistic effects occur, wherein the fungicidal activity of the combination product is greater than that of the added effectiveness of the individual components. Fungicides which can be combined with the active compounds according to the invention, without restricting the possible combinations, are, for example:

Sulfur,

Dithiocarbamates and their derivatives, such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, manganese ethylenebisdithiocarbamate, manganese-zinc ethylenediamine bis-dithiocarbamate and zinc ethylenebisdithiocarbamate,

Tetramettiyl thiuramsul f ide,

Ammonia complex of zinc-CNjNI-ethylene-bis-dithiocarbamate) and N, N "-polyethylene-bis-cthiocarbamoyo-disulfide, ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate) and N, Is propylene-bis-cthiocarbamoy-disulf id,

N-trichloromethylthiothio-tetrahydrophthalimide, N-trichloromethylthio-phthalimide,

iM- (l _/ l _/ 2,2-tetrachloroethylthiol) tetrahydrophthalimide,

4,6-dinitro-2- (l-methylheptyl) -phenylcrotonat, _{4/6-dinitro-2-sec-butylphenyl-3,3-diπlethylacrylat,} 4,6-dinitro-2-sec-butylphenyl isopropyl carbonate,

Methyl 1- (n-butylcarbamoyl) benzimidazol-2-ylcarbamate _/ benzimidazole -2 -yl-carbamic acid methyl ester, 2- ^ fur-2-yl) -benzimidazole,

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

1,2-bis- (3-methoxycarbonyl-2-thioureido) -benzene, l, 2-bis- (3-ethoxycarbonyl-2-thioureido) -benzene, ^^ - dihydro-o-methyl-S-phenylcarbamoyl-l ^ -oxathiin, 2,3-dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiin-4 _/ 4-dioxide,

Tetrachloro-isop.ithalsäuredinitril,

2,3-dichloro-l, 4-naphthoquinone,

2,3-dicyano-1 _/ 4-chlorothioanthophthalene,

l \ J-tridecyl-2,6-dimethylmorpholine or its salts, NC _{1 n} -C ₁₄ -alkyl-2,5- and / or 2,6-dimethylrnorphol in i \ -cyclododecyl-2,6-dimethylmorpholine or its Salts, N- / 3-p-tert. Butylphenyl) -2-methyl-propyl / -2 _/ 6-cis-dimethyltnorpholine or its salts

N, N'-bis (1-formamido-2,2,2-trichloroethyl) -piperazine i - (1-formamido-2,2,2-trichloroethyl) -3,4-dicloroaniline N- (1-formamido 2,2,2-trichloroethyl) -morpholine

5-butyl-2-ethyl-amino-4-hydroxy-G-me-thi-pyriinidine 5-butyl-2-dimethylamino-4-hydroxy-6-niethyl-pyridinidine

2 , 4-D-dichlorophenyl-phenyl-pyrimidin-5-yl-methanol 2-chlorophenyl-4-chlorophenyl-pyriniidin-5-yl-methanol, bis (4-chlorophenyl) -pyridin-3-yl-methanol

5-Methyl-5-vinyl-3- (3,5 "-dichlorophenyl) -1,3-ox.-tol idin-2,4-dione S-methyl-S-methoxyniethyl-S-CS1 -dichloropheny.l) -l, 3-oxazolidine-2,4-dione

3- (3,5-dichlorophenyl) -N-isopropy 1-2, 4-dioxo-1-carbox-imidazolidiπ a πι id

iSI- (3 _/ 5-dichlorophenyl) -1 _/ 2-dimethylcyclopropane-1,2-dicarboximide

- 13 -

1- (4-chlorophenoxy) -3,3-dimethyl-1-1- (1,2,4-triazole-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 / -imidazl-1) N-Propyl-N- (2,4,6-trichlorophenoxy) -ethyl-carbamoyl / -imidazole L- / 2- (2 _/ 4-dichloropheryl) -4-ethyl-1,3-dioxolan-2-ylmethyl7 -LLL-1,2,4-triazole

1- (2- (2,4-dichlorophenyl) -4-n-phenyl-1,3-dioxolan-2-yl-methyl-7-lH-1,2,4-triazole

1- (2 _/ 4-dichlorophenyl) -2- (1,2,4-tria2-ol-1-yl) -4 _/ 4-dimethylpentan-3-one

2,5-Dicl) lor-l, 4-dimethoxy-benzene

2,6-dichloro-4-nitroaniline

diphenyl

2-methyl-benzoic acid anilide

2-üod-benzoic acid anilide

2,5-dimethyl-furan-3-carboxanilide

2 _/ 4,5-trimethyl-2-ylane-3-carboxylic acid anilide i -cyclohexyl-N-methoxy-2 _/ 5-dimethyl-furan-3-car-L) onic acid anhydride 3 - / 3 - (3 _/ 5-dimethyl-2- oxycyclohexyl) -2-hydroxyethyl / glutariinide N-dichlorofluoromethylthio-N ", N'-dimethyl-N-phenyl-sulfuric acid diamide

DL-N- (2 _/ 6-Dimethylphenyl) - \ '- (2 ^L -ethoxyacetyl) -alanine methyl ester DL ⁱ -i \ - (2,6-dimethylphenyl) -N- (2-furoyl) alanine methyl ester N - (2 _/ 6-Diynethylphenyl) -N-chloroacetyl-DL ¹ -2-aminobutyrolactone

2,4-dichloro-6- (2-chloroanilino) -s-triazine 0,0-diethyl-phthalimido-phosphonothioate

5 - / \ mino-l- (bis (dimethyl) amino) phosphine inyl) -3-phenyl-1,2,4-triazole O-diethy1-S-benzyl-thiol phosphoric acid ester 2-thio-1, 3-ditVLb- (4,5-b) quinoxaline)

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

8-llydroxyclunoline or its salts

4-Dimethylaminophenyl-diazo-suli onic acid sodium salt 5-isopropylidopropyl isopropylisophthalate

2-cyano-N- (ethyl-1-aminocarbonyl) -2- (methoxyimino) -acetamide 2-heptadecyl-2-iinidazoline acetate

Dodecyl-guanidine

200340

- 14 -

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

In the treatment of parts of plants, the drug concentrations in the use forms can be varied within a substantial range. They are generally between 0.0001 and 1 percent by mass, preferably between 0.5 and 0.001 percent by mass. The drug loadings are dependent on the specific application and are generally between 0.1 and 3 kg of active ingredient or more 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 Nacherntebehancilung 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 50 g. In the treatment of the soil are Wirkstoffkonzentrat ions of 0.0001 to 0.1 mass percent, preferably from 0.001 to 0.05 mass percent, 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.

-is-

Auaf.uKr, uqgatie.iap.ie.l.e.

The following examples illustrate the preparation of fiction, contemporary compounds and their precursors.

The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared by processes known per se, as follows from the synthesis instructions given below:

Method for the synthesis of the halocarboxamides of the formula III

Preparation of chloroacetic acid N _, N-bis (2-cyanoethyl) -amide (precursor for compound no. 32)

To a solution of 12.3 g of bis (2-cyanoethyl) amine in 100 ml of dried dioxane is added 14 ml of triethylamine. Subsequently, 12.5 g of chloroacetyl chloride (8.8 ml) in 10 ml of dried dioxane are added dropwise within 1 hour. The temperature is kept below 30 ⁰ C. After stirring for 2 hours at room temperature, the reaction mixture is poured onto 200 ml of ice-water. The product is extracted with ethyl acetate, the organic phase is washed with water, dried over sodium sulfate and concentrated in vacuo. The crude product is recrystallized from acetone / n-hexane. Yield 14 g. M.p. 68 - 68.5 ⁰ C.

Method for the synthesis of the 2,6- and 2,5-cis- and / or transdimethylmorpholinio-carboxamides of the formula IV:

Preparation of 2- (2,6- and 2,5-cis- and / or trans-dimethylmorpholino) -propionic acid 3,5-dichloroanilide

(Precursor for compound no. 80)

22.6 g of 2,6-cis-dimethylmorpholine are dissolved in 100 ml of dried dioxane. For this purpose, a solution of 29.7 g of 2-Brompropionsäurc-3,5-dichloroanilide is added dropwise in 20 ml of dried dioxane. The mixture is then heated for 3 hours to reflux. The reaction mixture is concentrated to dryness in vacuo. It is converted from methanol

crystallizes. Yield 26 g. M.p. 158 - 158.5 ⁰ C. Beisgiel_l

N- (C _{; 10} -C _{; 14} ) -alkyl-2 _/ 6-cis- and / or trans- and N-Cc ^ -C ^ -A-2,5-cis- and / or trans-dimethylinorpholio-acetic acid -N ', N'-bis (2-cyanoethyl) amide chloride

30 g _/ (C ₁₀ -C ₁₄ ) -alkyl-2 _/ 6-cis- and / or trans- and at least 15% by weight of N- (C ₃₀ -C ₁ ) -alkyl-2 _/ 5-cis fraction - and / or transdimethylmorpholine and 20 g of chloroacetic acid-N, N-di- (2-cyanoethyl) -amide are heated to reflux with addition of a catalytic amount of sodium iodide in 10ü ml of acetonitrile for 24 hours. It is cooled and the solvent is distilled off in vacuo. The product is dissolved in a little diethyl ether and mixed with n-llexan until complete precipitation. Concentration in vacuo gives 45 g of a yellow-brown viscous oil (Compound No. 32). IR spectrum (film): C = O absorption 1660 cm

Beisp_iel_2

2- / N- (C ₁₀ -C ₁₄ ) -alkyl-2,6-c'is- and / or trans- and N- (C ₁₀ -C ₁₄ ) -alkyl-2,5-cis- and / or trans -dimethylmorpholinioZ-propionic acid 3,5-chloroanilide bromide

30 g of N- (C ₁₀ -C ₁₄ ) -alkyl-2 _/ 6-cis- and / or trans- and at least 15 percent by weight of N- (C ₁₀ -C ₁₄ ) -alkyl-2,5-cis- and / or or transdimethylmorpholine and 29.8 g of 2-bromopropionic acid 3,5-dichloroanilide are refluxed in 100 ml of n-butanol with the addition of a catalytic amount of sodium iodide for 24 hours. It is cooled and the solvent is distilled off in vacuo. The remaining product is dissolved in a little diethyl ether and mixed with n-mexan until complete precipitation. The oily phase is separated off and freed from solvent residues in vacuo. This gives 54 g of a yellow-brown, high-viscosity oil (compound no. 80). IR spectrum (film): C = O absorption 1690 cm

Beisgiel_3

N- (C ₁₀ -C ₁₄ ) alkyl-2,6-cis- and / or trans- and N- (C ₁₀ -C ₄ ) -alkyl-2,5-cis- and / or tris-dimethylmorpholinio-acetic acid -3 _/ 4-you!! Oranilide chloride

31.7 g of 2,6-cis- and / or trans-dimethylmorpholinio-acetic acid-3,4-dichloroanilide and at least 15 percent by weight of 2,5-cis- and / or trans-dimethylmorpholino-acetic acid S, -dichloroanilide and , 9 g of iso-tridecyl chloride (mixture of various C ₁₀ -C, / - alkyl chlorides containing 60 to 70% n-tridecyl chloride) in 100 ml of dimethylformamide are heated to reflux for 12 hours. After cooling, the solvent is distilled off in vacuo. The crude product is dissolved in a little diethyl ether and mixed with η-hexane until completely precipitated. The oily phase is separated and freed from L'ooungsmittelresten in vacuo. This gives 48 g of a light brown resin (Compound No. 75) IR spectrum (film): C = O absorption 1690 cm " ¹

In a similar manner, the following compounds of general formula I are prepared, which are usually yellow to brown viscous oils or resins, in polar solvents, e.g. Alcohols, acetone, dimethylformamide and dimethyl sulfoxide, are well soluble and in the IR spectra the characteristic.

have the carbonyl group.

- 18 -

O N

- σο - ν;

and

-co-n;

Θ ^x (D.

1 n ~ hexyl CH ₂ " H H Cl 2 η-octyl I CH ₂ H H Cl 3 n-decyl CH ₂ H H ' Cl 4 n-dodecyl CH ₂ hl H Cl 5 n-tridecyl CH ₂ , H "St! Cl 6 1,5,9-trimethyl- CH " H H Cl thyldecyl 7 iso-tridecyl Chg H H Cl 8th isn-tridecyl CH ₂ W methyl Cl 9 iso-tridecyl Chg H ethyl Cl 10 iso-tridecyl Chg H sec-butyl Cl 11 iso-tridecyl CII ₂ H 2-ethylhexyl Cl 12 iso-tridecyl Chg H n-dodecyl Cl 13 iso-tridecyl Chg Il n-octadecyl Cl 14 iso-tridecyl Chg H 3-hydroxypropyl Cl 15 iso-tridecyl CH ₂ H 3-ethoxypropyl Cl 16 iso-tridecyl Chg Il 2-cyanoethyl Cl 17 iso-tridecyl Chg H 2-diethylaminoethyl CJ. 18 iso-tridecyl CH (CH ₃ ) H H br 19 iso-tridecyl CH (CH ₃ ) Il n-dodecyl br 20 iso-tridecyl CH (CgH ₅ ) Il n-butyl br 21 iso-tridecyl C (CHg) ₂ H n-butyl br

- 19 -

No.

22 iso-tridecyl CH (C ₅ M ₁₁ ) H n-butyl br 23 iso-tridecyl (CH ₂ ) ₃ H n-butyl Cl 24 iso-tridecyl (CH ₂ ) ₆ H n-butyl br 25 HC ₁₅ H ₃₁ CH ₂ H n-butyl Cl 26 ⁿ " ^C 20 ^H 41 CH ₂ H n-butyl Cl 27 iso-tridecyl CH ₂ ethyl ethyl Cl 28 iso-tridecyl CH ₂ n-octyl n-octyl Cl 29 iso-tridecyl CH (CH ₃ ) n-butyl n-butyl Br ' 30 iso-tridecyl CH ₉ 2-hydroxy 2-hydroxyethyl Cl ethyl 31 n-octyl CH ₂ 2-cyanoethyl 2-cyanoethyl Cl 32 iso-tridecyl CH ₂ 2-cyanoethyl 2-cyanoethyl Cl 33 iso-tridecyl CH ₂ / methyl 3-cyanopropyl Cl 34 iso-tridecyl CH ₂ H allyl Cl 35 iso-tridecyl CH (ClO allyl allyl br 36 iso-tridecyl CH ₂ methyl crotyl Cl 37 iso-tridecyl CH ₂ methyl 4-chlorobut-2-en-l-yl Cl 38 iso-tridecyl CH ₂ methyl propargyl Cl 39 iso-tridecyl CH ₂ H cyclopropyl Cl 40 iso-tridecyl CH (CH ₃ ) H cyclopentyl br 41 iso-tridecyl CH (CH ₃ ) Hi cyclohexyl br 42 iso-tridecyl CH ₂ Il cycloheptyl Cl 43 iso-tridecyl CH ₂ ethyl cyclohexyl Cl 44 iso-tridecyl CH ₂ H phenyl Cl 45 iso-tridecyl CH ₂ methyl phenyl Cl 46 iso-tridecyl CH ₂ n-propyl phenyl Cl 47 iso-tridecyl cu ₂ allyl phenyl Cl 48 iso-tridecyl CH ₂ propargyl phenyl Cl 49 iso-tridecyl CH ₂ benzyl phenyl Cl 50 iso-tridecyl CH (CII ₃ ) allyl phenyl br 51 iso-tridecyl CII ₂ H naphth-1-yl Cl 52 iso-tridecyl CII ₂ H biphen-2-yl Cl 53 iso-tridecyl CH ₂ H 2-chlorophenyl Cl 54 iso-tridecyl CH " , H 3-fluorophenyl Cl

- 20 ZCHiS

55 iso-triclecyl CH ₀ H 56 iso-lridecyl CH (CH,) methyl 57 iso-tridecyl CH ₂ • H 58 iso-tricJecyl CH (CHg) methyl 59th iso-tridecyl CH (CHg) methyl 60 iso-tridecyl CH (CH ₃ ) methyl 61 iso-tridecyl CH ₂ H Ö2 iso-tridecyl CH ₂ Il 63 iso-tridecyl CH ₂ Il iso-tridecyl CII ₂ H 65 iso-lr idecyl CH ₂ H 66 iso-tridecyl CH ₂ Il 67 iso-tridecyl CII ₂ H 68 iso-tridecyl CH ₂ H 69 iso-tridecyl CII ₂ Il 70 iso-tridecyl CH ₂ Il 71 iso-tridecyl CH ₂ H 72 iso-tridecyl CH ₂ H 73 iso-tridecyl CH ₂ Il 74 iso-tridecyl CII ₂ Il 75 iso-tridecyl CH ₂ H 76 n-octyl CH ₂ H 77 n-octyl CH ₂ methyl 78 n-octyl CH (CH ₃ ) H 79 iso-tridecyl CH ₂ Il »0 iso-tridecyl CH (CHg) Il 81 iso-tridecyl CH (Ciig) methyl 82 iso-tridecyl CH (CHg) allyl 83 iso-tridecyl CH, Il 84 iso-tridecyl Cll (-: ilg) Hi 85 iso-tridecyl CH (CHg) methyl 86 iso-tridecyl CII ₀ H

4-chlorophenyl ul

3-bromophenyl Br

4-ethylphenyl Cl

4-n-butoxyphenyl Br

4-formylphenyl Br

4-acetophenyl 3r

3-nitrophenyl Cl

4-cyanophenyl Cl 3-trifluoromethylphenyl Cl 4-thiocyanatophenyl 'Cl

4-acetaminophenyl Cl

4-methoxycarbonyl-C1-phenyl

4-N, N-dimethylamido-C1 carbonylphenyl

4-N _, -diynediylureido-C1-phenyl

4-N, N-dimethyl-indido-C1-sulfenylphenyl

4-phenylsulfonylphenyl Cl

2,3-dichlorophenyl Cl

2,4-dichlorophenyl Cl

2,5-dichlorophenyl Cl

2,6-dibromophenyl Cl

3,4-dichlorophenyl Cl

3,5-dichlorophenyl Cl

3,5-dichlorophenyl Cl

3,5-dichlorophenyl Br

3,5-dichlorophenyl Cl

3,5-dichlorophenyl Br

3,5-dichlorophenyl Br

3,5-dichlorophenyl Br

3,5-dibromophenyl Cl 3,5-dibromophenyl * Br

3,5-dibromophenyl Br

2,6-diethylphenyl Cl

- 21 -

No.

87 iso-tridecyl CH ₂ H 3,4-dimethyl phenyl Cl 88 Isotridecyl CH ₂ H 3,5-d! Methyl phenyl Cl 89 iso-tridecyl CH ₂ H 2-nitro-4-trifluoromethylphenyl U 90 iso-tridecyl CH ₂ H 2-methyl-4-chlorophenyl Cl 91 iso-tridecyl CH (ClO H 2-methyl-4-chlorophenyl Br ' 92 iso-tridecyl Chg H 2-cyano-4-nitrophenyl Cl 93 iso-tridecyl Chg H 3,5-dinitrophenyl Cl 94 iso-tridecyl CH ₂ H 2,6-dibromo-4-nitro-phenyl Cl 95 iso-tridecyl Chg methyl 2,6-dibromo-4-nitro-phenyl Cl 96 iso-tridecyl CH (CH ₁ J H 2,6-dibromo-4-nitro-phenyl br 97 iso-tridecyl CH (CH ₃ ) methyl 2,6-dibromo-4-nitro-phenyl br 98 iso-tridecyl CII ₂ H 2,6-dichloro-4-cyanophenyl Cl y9 iso-tridecyl CH ₂ methyl 2,6-dichloro-4-cyanophenyl Cl 100 iso-tridecyl CH (CH,) H 2,6-dichloro-4-cyanophenyl br 101 iso-tridecyl CH (ChU) methyl 2 _/ 6-dichloro-4-cyano-phenyl · br 102 iso-tridecyl CII ₂ H 3,4,5-trichlorophenyl Cl 103 iso-tridecyl Chg methyl 3,4,5-trichlorophenyl ci 104 iso-tridecyl CH (CH ₃ ) H 3,4,5-trichlorophenyl br 105 iso-tridecyl CH (CH ₃ ) methyl 3,4,5-trichlorophenyl br 106 iso-tridecyl Chg H 2,6-dibromo-4-thio-cyanato-phenyl Cl 107 iso-tridecyl CH _? methyl 2,6-dibromo-4-thio-cyanato-phenyl.l Cl 108 iso-tridecyl CH (CH ₃ ) Il 2 _/ 6-dibromo-4-thiocyanato-phenyl br 1:09 iso-tridecyl CH (CH ₃ ) methyl 2,6-dibromo-4-thiocyanato-phenyl br 110 iso-tridecyl Ciig H 3,5-dichloro-4-methoxyphenyl Cl

- 22 -

^RJ

111 iso-tridecyl

112 iso-tridecyl

113 iso-tridecyl

114 115 116 117 118 119 120 121 122 123 124 125

127 128 129 130 131 132 133 134 135

1S07

isoi isoisoisoisoisoisoisoisoisoisoisoisoisoisoisoisoisoisoisisisoi

tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl tridecyl

136 iso-tridecyl

137 iso-tridecyl

138 iso-tridecyl

139 iso-tridecyi

CH,

CH (CH ₃ )

CH (CH 2) methyl

CII ₂

CH (CII ₃ )

CH (CH ₃ )

CH ₂

CH ₂

CH ₂

CH ₂

CH ₂

CH (CH ₃ )

CH ₂

CH ₂

CH ₂

CH ₂

CH ₂

CH ₂

CH ₂

CH ₂

CH ₂

CH ₂

CII ₂

CH (CH ₃ )

CH (CH ₃ )

CH (CH.,) CII (CH ₃ )

CII,

methyl 3,5-dichloro-4-methoxy-C1-phenyl

H 3 _/ 5-dichloro-4-methoxy-Br phenyl

3 _/ 5-dichloro-4-methoxy-Br phenyl

H benzyl Cl

H phenethyl Br

methyl 4-chlorobenzyl Br

II 4-methylbenzyl Cl

H 4-tert-butylbenzyl Cl

H 4-methoxybenzyl Cl

H 3-trifluoromethylbenzyl Cl

methyl 4-cyanobenzyl Cl

H 4-nitrobenzyl Br

H 3 _; 4-dichlorobenzyl Cl

H, 2,3,4-trichlorobenzyl Cl

aziridin-3-yl Cl

pyrrol-1-yl Cl

pyrrolidin-1-yl Cl

pyrazol-1-yl Cl

1H-imidazol-1-yl, Cl

1H-l, 2,4-triazol-1-yl Cl

piperidin-1-yl Cl

3,5-dimethylpiperidin-1-yl Cl

4-methylpiperazin-1-yl Cl

tetrahydro-1 _/ 4-oxazin-4-yl Br

2,6-cis / trans-dimethyl-tetra-Br-hydro-1,4-oxazin-4-yl

tetrahydro-1,4-thiazin-4-yl Br

2,6-cis / trans-dimethyl-tetra-Br-hydro-1,4-triazin-4-yl

oxazolidin-3-yl Cl thiazolidin-3-yl .... Cl

"23 - ^

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

Solution concentrates: 80 parts by weight of compound 7 are mixed with 20 parts by weight of N-methyl-2-pyrrolidine. A solution is obtained which is suitable for use in the form of very small drops. "

IX ... as Un te i

Emulsifiable concentrates 25 parts by weight of Verbindung55 are mixed with 2.5 parts by weight epoxydiertöre vegetable oil $ g _(lu 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 can be prepared by dilution with water, emulsions of any desired concentration. getting produced.

Spray powder: 40 parts by weight of compound 86 are mixed well with 5 parts by weight of the sodium salt of a Üigninsulfonsäure from a sulfite liquor, 1 part by weight of sodium salt of di-iso-butylnaphthalen-sulfonic acid and 54 parts by weight of silica gel and ground in an appropriate mill. A spray powder is obtained which can be diluted with water to give suspensions of any desired concentration.

Dusts: 5 parts by weight of compound 80 are intimately mixed and ground with 95 parts by weight of finely divided kaolin. The dusts can be dusted in this form for use.

Granules: 5 parts by weight of compound 86 are mixed with 0.25 parts by weight of epichlorohydrin and dissolved with 6 parts by weight of acetone. Thereafter, 3.5 parts by weight of polyethylene glycol and 0.25 parts by weight of cetyl polyglycol ether are added. The resulting solution is sprayed on kaolin. Subsequently, the acetone is evaporated in vacuo. F.s will receive a microgranulate, which i.i this form can be used.

-24-

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

Bei.sgj.el _A

Mycelial growth test

The fungicidal activity of the agent against the test fungi is in a conventional manner as inhibition of radial mycelial growth on malt agar medium (2% malt) determined in Petri dishes of 9 oin diameter at a Inkubationstemperjtur of 25 ⁰ C. The active compounds are dissolved in dimethylformamide, diluted with water and then added to the liquid Agnr in such a way that the desired concentration of active ingredient in the nutrient medium is achieved. The DMF content does not exceed 0.5% by volume. After cooling, the plates are brained. The evaluation is carried out according to the growth sensitivity of the fungi when the controls without the addition of active substance have grown through to 70 to 90 % of the shell diameter. The percentage growth inhibition of the active substances is calculated (Table A).

Table A: Growth inhibition of Dotrytis cinereti in the mycelium growth test. Active substance concentration: 10 pg / ml

Compound No. Growth inhibition in percent

Oxycarboxine (known) 20

7 45

16 28

27 75

31 39

32 65 41 77 44 86 55 61 75 58 79 55

-25-

Continuation Table A:

Compound No. Growth inhibition in percent

80 91

86 90

94 78

114 45

129 '77

130 92

Beisgiel_B

Grain moth test (Erysiphe graminis / barley leaf pieces) of barley plants of the variety "Astacus" are prepared together with a conidia suspension of Erysiphe graminis var. Hordei and active ingredient preparations consisting of 1 part by weight of active ingredient and 100 parts by weight of dimethylformamide Water to the desired drug concentration to be diluted, shaken at 20 C for 2 hours. Subsequently, the leaf pieces are kept for 7 days in an incubation in trays at temperatures of 20 to 22 ⁰ C and 90 to 100 % relative humidity. Efficacy is determined by calculating the percentage inhibition of infection from the reduction in the number of pustules over the controls without added drug. The results are listed in Table B.

Table B: Action against Erysiphe grominis on barley flakes. Active substance concentration: 0.05 pg / inl

Compound No. Inhibition of infection in percent

Triforine (known) 35

7 44

27 100

31 47

32 76 41 55

-26-Continued Table B: Compound No. Inhibition of infection in percent

44 HO

75 52

76 41

79 83

80 92 86 77 94 92

114 100

130 34

Bei8giel_C

Phytophthora test (Phytophthora infestans / tomato leaf discs)

To perform the test, leaf disks are punched out of adult leaves of tomato plants of the "Tamina" variety. The zoospore suspension of Phytophthora infestans needed for inoculation is obtained by flushing fungal turf from tuber halves of susceptible potato varieties.

The active compound preparations are prepared from 1 part by weight of active compound and 100 parts by weight of dimethylformamide, which are diluted with water to the desired active substance concentration. The treatment of the tomato leaf pieces with the active ingredients and the inoculation are carried out simultaneously by adding the active compound preparation of the desired concentration to the zoospore suspension of Phytophthora infestans and, after shaking, pouring these mixtures onto the leaf disks laid out in petri dishes. After 2 hours, the supernatant liquid is poured off. The dishes are kept in an incubation chamber at temperatures between 18 and 20 ^° C. and 95 to 100% relative humidity under artificial lighting

 After 3 to 4 days, the effectiveness of the funds is determined. To

- 27 -

the percentage inhibition of infection is calculated from the proportion of necrotic leaf area per leaf disc compared to controls without added funds

 The results are listed in Table C.

Table C: Action against Phytophthora infestans on tomato leaf discs. Active substance concentration: 5 pg / ml

Compound No. Inhibition of infection in percent

Zineb (known) 5

7 62

44 77

55 26

75 45

79 19

114 26

BeisDiel_O

Plant growth regulation test

Cucumber plants of the variety "Eva" are used in pots in humus soil, which is sufficiently supplied with nutrients, up to a stature height of 9 cm in the greenhouse. For each experimental variant IC plants are used. The cucumber plants are sprayed with active ingredient preparations prepared from 1 part by weight of active ingredient, 100 parts by weight of dimethylformamide and 0.25 parts by weight of alkylaryl polyglycol ether and diluted with water to the desired active ingredient concentration.

After a growth time of 14 days after the medium application, initial measurements are made on the treated plants and the untreated control plants. The results are shown in Table D.

- 28 -

Table D: Effect on length growth of cucumber plants in foliar treatment. Active ingredient concentration: 1000 mg / l

Compound No. Plant height

in cm relative

Untreated Control 26.5 100

79 21.5 81.6

Claims (4)

1. A fungicidal composition having an additional plant growth -regulating action, characterized in that a mixture of N-alkyl-2,6-cis- and / or trans-dimethylmorpholinio-carboxylic acid amide salts and at least 15% by weight of N-alkyl-2,5 cis- and / or trans-dimethylmorpholinio-carboxamide salts of the general formula I, / \ ^ y λ ο / \ ^ y ' X ο ON R- * ONR ³ ) / ^X R ² -CO-N ^ \ / ^X R ² - CO - N ' HC R ⁴ OH ^ r4 * and ^3K in the R is straight-chain or branched alkyl having 6 to 20 C atoms, 2
R is straight-chain or branched alkylene having 1 to 6 C atoms, 4
R 'and R independently of one another are identical or different hydrogen, straight-chain or branched ALkyi having 1 to 20 C atoms, a straight-chain or branched chain which is substituted by hydroxyl, alkoxy having 3 to 4 C atoms, cyano or dialkylamirio having 2 to 16 C atoms Alkyl having 1 to 6 C atoms, an optionally halogen-substituted alkenyl having 3 to 6 C atoms,
Cycloalkyl having 3 to 7 C atoms, Aryl, which is monosubstituted or polysubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 6 C atoms, alkoxy having 1 to 4 C atoms, aryl-lower-alkyl having 7 to 12 C atoms, cycloalkyl having 3 to 7 C atoms, acyl having 1 to 4 C atoms, alkoxyalkyl having 1 to 8 C atoms, aryl, halogen, halogenoalkyl having 1 to 4 C atoms, haloalkoxy having 1 to 4 C atoms, alkylthio having 1 to 4 C, -Atomen, halogenoalkylthio having 1 to 4 carbon atoms, nitro, cyano, thiocyanato, NHCOR ¹ , NHCONH ¹ R ", COOR ', CO-NR ¹ R' ¹ , SO ₂ R ¹ and / or SO ₂ NR ¹ R ¹¹ where R ¹ and R ' ¹ independently of one another are hydrogen, straight-chain or branched alkyl having ί to 6 C atoms, cycloalkyl having 3 to 7 C atoms, aryl or aryl-lower-alkyl having 7 to 12 C atoms, -30- / 636/3 may be substituted Aryl-lower-alkyl having 7 to 12 C atoms, which is monosubstituted or polysubstituted, identically or differently, by 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 Atoms, halogen, haloalkyl having 1 to 4 carbon atoms, nitro and / or cyano may be substituted, 4
R and R together with the nitrogen atom optionally mono- or disubstituted by alkyl having 1 to 4 carbon atoms and / or halogen-substituted five- or six-membered heterocyclic ring, which optionally contains one or two further heteroatoms, and X denote the anion of a non-phytotoxic acid, in addition to the usual solvents , Carriers and / or Formierungshiflsstoffen included. 2. A method for controlling fungi, characterized in that means according to item 1 on mushrooms or the objects to be protected against fungal attack läP ^ t. 3. Use of agents according to item 1, characterized dadu rch that they are used to combat fungi. 4. Use of funds according to point .1, characterized by the fact that they are used to regulate Pf.lanzenvvachstums.