WO1992017066A1

WO1992017066A1 - Substituted salicylamides, agents to combat plant diseases

Info

Publication number: WO1992017066A1
Application number: PCT/EP1992/000571
Authority: WO
Inventors: Michael Haug; Klaus Jelich; Heinz-Wilhem Dehne; Stefan Dutzmann
Original assignee: Bayer Aktiengesellschaft
Priority date: 1991-03-30
Filing date: 1992-03-17
Publication date: 1992-10-15
Also published as: PL294002A1; EP0586386A1; HU9302763D0; AU1562492A; HUT65081A; BR9205820A; JPH06509320A; DE4110483A1

Abstract

The description relates to the use of partly known salicylamides of general formula (I), in which Ar, R?1, R?2, R?3 and R?4 have the meanings given in the description, for combatting parasites and novel compounds of formula (I) and their production.

Description

Substituted salicylamides, agents against plant diseases

The invention relates to the use of partially known substituted salicylamides as agents for the treatment of plant diseases, as well as new substituted salicylamides and a process for their preparation.

It is known that certain substituted salicylamides, such as, for example, the compound 2-hydroxy-5-bromo-N- (4-bromophenyl) benzamide, have fungicidal properties and can be used as agents for the treatment of plant diseases (cf. e.g. U.S. Patent 2,802,029).

However, the effectiveness of these previously known compounds is not entirely satisfactory in all fields of application, in particular at low application rates and concentrations.

It has been found that the partially known substituted salicylamides of the general formula (I)

in which

R ^{1 represents} hydrogen, cyano or trifluoromethyl and

R ^{2 represents} hydrogen or trifluoromethyl, but at least one of the radicals R ¹ and R ^{2 is} different from hydrogen,

R ^{3 represents} hydrogen, halogen or methyl,

R ^{4 represents} hydrogen, alkanoyl, or an equivalent of an inorganic or organic cation and

Ar stands for optionally substituted phenyl, possess fungicidal properties against phytopathogenic pathogens.

Surprisingly, the substituted salicylamides of the general formula (I) which can be used according to the invention have a considerably better activity against fungi which damage plants than the substituted salicylamides known from the prior art, such as, for example, the compound 2-hydroxy-5-bromo-N- (4-bromophenyl) -benzamide, which are chemically and functionally obvious compounds.

Formula (I) provides a general definition of the substituted salicylamides which can be used according to the invention. Compounds of the formula (I) in which

R ^{1 represents} hydrogen, cyano or trifluoromethyl and

R ^{2 represents} hydrogen or trifluoromethyl,

however, at least one of the radicals R ¹ and R ^{2 is} different from hydrogen, R ^{3 represents} hydrogen, halogen or methyl,

R ^{4 stands} for hydrogen, for straight-chain or branched alkanoyl with 1 to 8 carbon atoms, for one equivalent of an alkali metal or alkaline earth metal cation or for one equivalent of an optionally mono- or polysubstituted, identically or differently substituted ammonium cation, the following being possible as ammonium substituents:

straight-chain or branched alkyl with 1 to 18 Carbon atoms or benzyl and

Ar represents phenyl which may be mono- or polysubstituted by identical or different substituents, the following being suitable as substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.

Compounds of the formula (I) in which

R ¹ for hydrogen. Cyano or trifluoromethyl stands and

R ^{2 represents} hydrogen or trifluoromethyl,

however, at least one of the radicals R ¹ and R ^{2 is} different from hydrogen,

R ^{3 represents} hydrogen, chlorine, bromine or methyl, R ^{4 represents} hydrogen, acetyl, or an equivalent of a sodium, potassium, calcium or ammonium cation and

Ar represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, the following being suitable as substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, or optionally one to three times, identical or different by fluorine, chlorine, bromine, methyl and / / or ethyl substituted phenyl,

Compounds of the formula (I) in which R ^{1 is} hydrogen, cyano or trifluoromethyl are very particularly preferably used and

R ^{2 represents} hydrogen or trifluoromethyl,

R ^{3 represents} hydrogen, R ^{4 represents} hydrogen, acetyl, a sodium cation and

Ar represents phenyl which is monosubstituted or disubstituted, identically or differently, the following being suitable as substituents: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl or ethoxycarbonyl.

The definitions of the radicals listed here also apply in a corresponding manner to the starting and intermediate products and, if indicated, to the compounds of the formulas (Ia) and (Ib).

The combinations listed here are preferred combinations of single residue definitions. However, this definition is not limited to the combinations specified, but can be exchanged for the corresponding definitions from other preferred areas.

The substituted salicylamides of the formula (I) which can be used according to the invention are known in some cases (compare, for example, J. Amer. Chem. Soc. 76, 4476 [1954]; OS-PS

2,967,194; J. Med. Chem. 33, 136-142 [1990]; Biochem. Biophys, Res. Commun. 110, 733-739 [1983]; JP 52110835; JP 51146432; U.S. Patent 3,577,550; GB 1079177), An effectiveness as an agent against plant diseases is not described.

Not yet known and also the subject of the invention are substituted salicylamides of the formula (Ia),

R ^{1-1 stands} for cyano or trifluoromethyl,

R ^{2 represents} hydrogen or trifluoromethyl,

R ^{3 represents} hydrogen, halogen or methyl,

R ^{4 represents} hydrogen, alkanoyl or an equivalent of an inorganic or organic cation and

Ar ^{1 represents} phenyl which may be mono- or polysubstituted by identical or different substituents, the following being suitable as substituents: halogen, cyano, nitro, in each case straight-chain or branched Alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl parts and optionally phenyl which is mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms,

Also not yet known and the invention relates to substituted salicylamides of the formula (Ib)

in which

R ^{1 represents} hydrogen, cyano or trifluoromethyl,

R ^{2-1 represents} trifluoromethyl,

R ^{3 represents} hydrogen, halogen or methyl,

Ar ^{2 represents} phenyl which may be mono- or polysubstituted by identical or different substituents, the following being suitable as substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms (with the exception of the methoxy radical), each straight-chain or branched haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halo ogenatoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl parts and optionally phenyl substituted once or more, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.

The compounds of the formula (Ia) or of the formula (Ib) are obtained if salicyl acids or their esters of the formula (IIa),

or the formula (Ilb)

in we

lcher

R ^{5 represents} hydrogen or alkyl and

R ¹ , R ^1-1 or R ^2-1 , R ³ and R ^{4 have} the meaning given above, with anilines of the formula (IIIa),

Ar ¹ —NH ₂ (purple) or the formula (Illb),

Ar ² -NH ₂ (Illb)

in which

Ar ¹ or Ar ^{2 have} the meaning given above, in the presence of a condensing agent and, if appropriate, in the presence of a reaction auxiliary, and if appropriate subsequently in a subsequent reaction

Reaction the hydroxy group in the salicylic acid part of Ver Bonds acylated in a generally customary manner with a customary acylating agent or reacted with an inorganic or organic base.

If, for example, 2-hydroxy-5-trifluoromethylbenzoic acid and 4-methylaniline are used as starting materials, and acetyl chloride is used as the acylating agent, the reaction sequence of the production process can be represented by the following formula:

The formulas (IIa) and (IIb) generally define the salicyl acids and their esters required as starting materials for carrying out the production process. In these formulas (Ila) and (Ilb), R ¹ , R ² , R ³ and R ⁴ preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) which can be used according to the invention , R ^1-1 preferably represents cyano or trifluoromethyl, R ^2-1 preferably represents trifluoromethyl and R ⁵ preferably represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms. The salicylic acids and their esters of the formula (Ila) or (Ilb) are known or can be obtained in analogy to known processes

(see J. Med. Chem. 21, 1100-1104 [1978]; Chem. Pharm. Bull. 32, 4466-4477 [1984] and the

Manufacturing examples).

The one to carry out the manufacturing process

Anilines of the formula (III) required as starting materials are generally known compounds of organic chemistry.

The acylating agents required for the preparation of acylated end products of the formula (Ia), in particular alkanoyl halides or alkanoyl hydrides, are likewise generally known compounds of organic chemistry, as are the inorganic or organic bases required for the preparation of salts of the formula (Ia). The manufacturing process is carried out in the presence of a suitable condensing agent. As such, all condensation agents which can usually be used for such amidation reactions are suitable. Examples include acid halide formers such as phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as ethyl chloroformate or methanesulfonyl chloride; Carbodimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents such as N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride.

Inert organic solvents are suitable as diluents for carrying out the production process and, if appropriate, the subsequent acylation. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether,

Dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; or sulfoxides such as dimethyl sulfoxide. The production process, like the acylation which may subsequently be carried out, is optionally carried out in the presence of a suitable reaction auxiliary. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or also ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, alkali or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and trimethyl amine acetate or ammonium amine acetate or ammonium amine acetate or ammonium amine acetate or ammonium amine acetate or ammonium amine acetate, or ammonium amine acetate, or trimethylamine acetate or ammonium amine acetate or ammonium amine acetate or ammonium acetate, Triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be varied within a substantial range in carrying out the production process and in the acylation which may subsequently take place. In general, temperatures between -60 ° C and 220 ° C, preferably at temperatures between 0 ° C and 150 ° C,

To carry out the production process, generally 1.0 to 2.0 mol, preferably preferably, are employed per mole of salicylic acid or salicylic acid ester of the formula (II)

1.0 to 1.3 mol of aniline of the formula (III), 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol of condensing agent and optionally 1.0 to 5.0 mol, preferably 1, 0 to 2.5 mol of base used as reaction auxiliaries. The reaction is carried out, worked up and isolated by known processes (compare the preparation examples).

To carry out the optionally subsequent acylation, 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of acylating agent and optionally 1.0 to 5.0 mol are generally employed per mol of substituted salicylic acid amide of the formula (I) , preferably 1.0 to 2.5 mol of base used as reaction auxiliary. The reaction is carried out, worked up and isolated using known processes (see the preparation examples).

The active compounds according to the invention have a strong action against pests and can be used practically to combat unwanted harmful organisms. The active ingredients are suitable for use as crop protection agents, in particular as fungicides. Fungicidal agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes. Some pathogens of fungal diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation: Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as

Pseudoperonospora humuli or Pseudoperonospora

cubensis;

Plasmopara species, such as, for example, Plasmopara

viticola;

Peronospora species, such as, for example, Peronospora pisi or Peronospora brassicae;

Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or Pyrenophora graminea

(Conidial form: Drechslera, Syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces

appendiculatus;

Puccinia species, such as, for example, Puccinia recondita; Tilletia species, such as, for example, Tilletia caries;

Üstilago species, such as, for example, Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora

canescens;

Alternaria species, such as, for example, Alternaria

brassicae;

Pseudocercosporella species, such as

Pseudocercosporella herpotrichoides.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds, and the

Floor.

The active compounds according to the invention can be used with particularly good results in combating cereal diseases, such as, for example, against the pathogen causing barley spotted disease (Pyrenophora teres) or against the pathogen causing brown spot disease on barley or wheat (Cochliobolus sativus) or against the pathogen causing brown furs in wheat ( Septoria nodorum) or against the pathogen of cereal snow mold (Fusarium nivale) or for combating diseases in fruit and vegetable growing, such as against the pathogen of tomato brown rot (Phytophthora infestans) or against the pathogen of gray mold on strawberries or beans (Botrytis cinerea) or for combating rice diseases, such as, for example, against the pathogen of the rice stain disease (Pyricularia oryzae) or against the pathogen of the rice stem disease (Pellicularia sasakii). In addition, the active compounds according to the invention have a broad in vitro activity.

In addition, the active compounds according to the invention also show acaricidal and foliar-insecticidal activity in appropriate application rates. Depending on their respective physical and / or chemical properties, the active compounds can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV Cold and warm fog formulations.

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorine ethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water ; with liquefied gaseous

Extenders or carriers are those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; Solid carrier materials are suitable: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifying and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; The following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose, Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations, and further additives can be mineral and vegetable oils .

Dyes such as inorganic pigments, e.g.

Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and in mixtures with fertilizers and

Growth regulators.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc., Es it is also possible to apply the active ingredients according to the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated. When treating parts of plants, the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.

In the case of seed treatment, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required. When treating the soil, active ingredient concentrations are from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% required at the site of action.

Preparation Examples:

example 1

6.0 g (0.03 mol) of 2-hydroxy-5-trifluoromethylbenzoic acid (compare, for example, EP 31 561) and 3.9 g (0.03 mol) of 3-chloroaniline in 100 ml of toluene are added at the reflux temperature dropwise 1 ml of phosphorus trichloride and, after the addition has ended, the mixture is stirred at the reflux temperature for a further 16 hours. For working up, the cooled reaction mixture is concentrated in vacuo and the residue is recrystallized from isopropanol / water.

7.7 g (81% of theory) of 2-hydroxy-5-trifluoromethyl-N- (3-chlorophenyl) benzamide with a melting point of 170 ° C. are obtained.

Example 2:

To 3.1 g (0.015 mol) of 2-hydroxy-4-trifluoromethylbenzoic acid (compare e.g. DE-OS 26 41 556) and 1.6 g

(0.015 mol) of 4-methylaniline in 100 ml of toluene are added dropwise at the reflux temperature 0.5 ml of phosphorus trichloride and, after the addition has ended, the mixture is stirred at the reflux temperature for a further 16 hours. For working up, the cooled reaction mixture is concentrated in vacuo and the residue is acetonitrile / water recrystallized.

3.2 g (72% of theory) of 2-hydroxy-4-trifluoromethyl-N- (4-methylphenyl) benzamide with a melting point of 208 ° C. are obtained.

Example 3:

To 1.5 g (0.005 mol) of 2-hydroxy-4-trifluoromethyl-N- (2-chlorophenyl) benzamide and 0.3 g (0.005 mol) of pyridine in 100 ml of toluene is added dropwise at room temperature with stirring 0.4 g (0.005 mol) of acetyl chloride, then stirred for 16 hours at room temperature and 24 hours at 40 ° C, then concentrated in vacuo, the residue is taken up in dichloromethane, washed with dilute aqueous hydrochloric acid, the aqueous phase is separated off, the organic phase is concentrated in a vacuum and the residue is recrystallized from isopropanol / water.

0.9 g (50% of theory) of 2-acetoxy-4-trifluoromethyl-N- (2-chlorophenyl) benzamide with a melting point of 125 ° C. is obtained.

The following substituted salicylamides of the general formula (I) are obtained in a corresponding manner and in accordance with the general information on the preparation:

Examples of use:

In the following application examples, the compound listed below was used as the reference substance:

2-Hydroxy-5-bromo-N- (4-bromophenyl) benzamide (see e.g. U.S. Patent 2,802,029).

Example A

Phytophthora test (tomato) / protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the preparation of active compound to runoff. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans.

The plants are placed in an incubation cabin with 100% relative humidity and approx. 20 ° C.

Evaluation is carried out 3 days after the inoculation,

In this test, for example, the compounds according to the following preparation examples show a clear superiority in effectiveness compared to the prior art: 1, 2, 4, 5, 11, 12, 14, 17 and 18.

Example B

Venturia test (apple) / protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkyl aryl polyglycol ether

To test for protective effectiveness, young plants are sprayed with the preparation of active compound to runoff. After the spray coating has dried on, the plants are ionized with an aqueous conidia suspension

Apple scab pathogen (Venturia inaequalis) and then remain in an incubation cabin at 20 ° C and 100% relative humidity for 1 day. The plants are then placed in a greenhouse at 20 ° C. and a relative humidity of approx. 70%.

Evaluation is carried out 12 days after the inoculation.

A clear superiority in effectiveness compared to the prior art show in this test, for. B. the compounds according to the following preparation examples 1, 2, 4, 5, 8, 10, 13, 14 and 18th

Example C

Pyrenophora teres test (barley) / protective

Solvent: 100 parts by weight of dimethylformamide

Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether

To produce a suitable Wi rkst off preparation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective efficacy, young plants are sprayed with the preparation of active compound as dewy. After the spray coating has dried, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours.

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%.

Evaluation is carried out 7 days after the inoculation. A clear superiority in effectiveness compared to the prior art show in this test z. B. the compounds according to the following preparation examples: 4, 6, 8, 10, 12, 14.

Claims

1. A method for controlling pests, characterized in that salicylamides of the general formula (I),

in which

R ^{1 represents} hydrogen, cyano or trifluoromethyl and

R ^{3 represents} hydrogen, halogen or methyl,

R ⁴ for hydrogen. Alkanoyl, or for a

Equivalent to an inorganic or organic cation

Ar stands for optionally substituted phenyl on pests and / or their habitat.

2. The method according to claim 1, wherein

R ^{1 is} hydrogen, cyano or trifluoromethyl

stands and

R ^{2 represents} hydrogen or trifluoromethyl, but at least one of the radicals R ¹ and

R ^{2 is} different from hydrogen, R ^{3 is} hydrogen, halogen or methyl, R ^{4 is} hydrogen, straight-chain or

is a branched alkanoyl with 1 to 8 carbon atoms, for one equivalent of an alkali metal or alkaline earth metal cation or for an equivalent of a possibly single or multiple, identically or differently substituted ammonium cation, the ammonium substituents being suitable: straight-chain or branched alkyl having 1 to 18 carbon atoms or benzyl and

Ar for single or multiple, if necessary,

is the same or different substituted phenyl, the following being suitable as substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 4 carbon atoms in each

Alkyl parts and optionally single or multiple, identical or different phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms. A method according to claim 1, in which

R ^{1 is} hydrogen, cyano or trifluoromethyl

stands

and

R ^{2 represents} hydrogen or trifluoromethyl,

however, at least one of the radicals R ¹ and R ^{2 is} different from hydrogen, R ^{3 is} hydrogen, chlorine, bromine or methyl

stands.

R ⁴ for hydrogen, acetyl, or for a

Equivalent to a sodium, potassium, calcium or ammonium cation and

Fluorine, chlorine, bromine, cyano, nitro, methyl,

Ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-but-oxy, methylthio, ethylthio,

Trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl, or optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl, phenyl.

Salicylamides of the formula (Ic)

lcher

R ^{1-1 stands} for cyano or trifluoromethyl

R ^{2 represents} hydrogen or trifluoromethyl,

R ^{3 represents} hydrogen, halogen or methyl, represents hydrogen, alkanoyl or a

Equivalent to an inorganic or organic cation Ar ^{1 represents} phenyl which is optionally mono- or polysubstituted by identical or different substituents, the substituents being: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio, each with 1 to

4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio, each with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each with 1 to 4 carbon atoms in the individual alkyl parts, and optionally one or more times, the same or different phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.

lcher

R ¹ for hydrogen, cyano or

Trifluoromethyl stands,

R ^{2-1 represents} trifluoromethyl,

R ^{3 represents} hydrogen, halogen or methyl, R ^{4 represents} hydrogen, alkanoyl or an equivalent of an inorganic or organic cation and

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms (with the exception of the methoxy radical), each straight-chain or branched halogenoalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different Halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms substituted phenyl.

6. pesticides containing at least one salicylamide of the formula (I) according to claim 1. 7. Process for the preparation of compounds of

Formula (Ia) or (Ib) according to Claims 4 or 5, characterized in that salicylic acids or their esters of the formula (Ila),

in which represents hydrogen or alkylene and

R ¹ , R ^1-1 or R ^2-1 , R ³ and R ^{4 have} the meaning given in claims 5 and 6, respectively, with anilines of the formula (IIIa),

Ar ¹ --NH ₂ (lIIa) or the formula (Illb),

Ar ² -NH ₂ (Illb) in which

A ¹ or Ar ^{2 have} the meaning given above, in the presence of a condensing agent and, if appropriate, in the presence of a reaction auxiliary and, if appropriate, then subsequently, in a subsequent reaction, the hydroxyl group in the salicylic acid part of Ver Bonds acylated in a generally customary manner with a customary acylating agent or reacted with an inorganic or organic base.