Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
  • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
  • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
  • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
  • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
  • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
  • C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton

Definitions

• 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.
• R 1 represents hydrogen, cyano or trifluoromethyl
• 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
• Ar stands for optionally substituted phenyl, possess fungicidal properties against phytopathogenic pathogens.
• 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.
• R 1 represents hydrogen, cyano or trifluoromethyl
• R 2 represents hydrogen or trifluoromethyl
• radicals R 1 and R 2 are 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:
• Ar represents phenyl which may be mono- or polysubstituted by identical or different substituents, the following being suitable as substituents:
• R 2 represents hydrogen or trifluoromethyl
• 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:
• R 2 represents hydrogen or trifluoromethyl
• At least one of the radicals R 1 and R 2 is different from hydrogen
• R 3 represents hydrogen
• R 4 represents hydrogen, acetyl, a sodium cation
• 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.
• 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
• 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
• 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,
• R 1 represents hydrogen, cyano or trifluoromethyl
• 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
• Ar 2 represents phenyl which may be mono- or polysubstituted by identical or different substituents, the following being suitable as substituents:
• R 5 represents hydrogen or alkyl
• 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 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 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.
• 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
• 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
• Anilines of the formula (III) required as starting materials are generally known compounds of organic chemistry.
• 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.
• acid halide formers such as phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride
• Anhydride formers such as ethyl chloroformate or methan
• 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,
• 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.
• 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 amine acetate or ammonium acetate, Triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine
• 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,
• 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
• Plasmopara species such as, for example, Plasmopara
• 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
• Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
• Cochliobolus species such as, for example, Cochliobolus sativus
• Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
• Uromyces species such as, for example, Uromyces
• 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
• Alternaria species such as, for example, Alternaria
• Pseudocercosporella species such as
• 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).
• the active compounds according to the invention have a broad in vitro activity.
• the active compounds according to the invention also show acaricidal and foliar-insecticidal activity in appropriate application rates.
• 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.
• 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.
• 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.
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary 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
• 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
• 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
• 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.
• 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%.
• active ingredient 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.
• Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
• 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.
• the plants are placed in an incubation cabin with 100% relative humidity and approx. 20 ° C.
• Emulsifier 0.3 parts by weight of alkyl aryl polyglycol ether
• 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.
• 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.
• Emulsifier 0.25 parts by weight of alkylaryl polyglycol ether
• 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.
• the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1991
  • 1991-03-30 DE DE19914110483 patent/DE4110483A1/de not_active Withdrawn
• 1992
  • 1992-03-17 BR BR9205820A patent/BR9205820A/pt not_active Application Discontinuation
  • 1992-03-17 HU HU9302763A patent/HUT65081A/hu unknown
  • 1992-03-17 EP EP19920906625 patent/EP0586386A1/de not_active Withdrawn
  • 1992-03-17 WO PCT/EP1992/000571 patent/WO1992017066A1/de not_active Application Discontinuation
  • 1992-03-17 AU AU15624/92A patent/AU1562492A/en not_active Abandoned
  • 1992-03-17 JP JP4506350A patent/JPH06509320A/ja active Pending
  • 1992-03-27 PL PL29400292A patent/PL294002A1/xx unknown

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