Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
  • C07D285/01—Five-membered rings
  • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
  • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
  • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
• • 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
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • 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
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
  • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/30—Halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/34—One oxygen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
  • C07D239/52—Two oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
  • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
  • C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
  • C07D251/40—Nitrogen atoms
  • C07D251/48—Two nitrogen atoms
  • C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
  • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
  • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
  • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical

Definitions

• the invention relates to new fluoromethoximino compounds, processes for their preparation and their use as pesticides, as well as new intermediates and several processes for their production
• Q 1 represents oxygen or -NH-
• Q ⁇ represents oxygen or sulfur
• X represents hydrogen or halogen
• i, L ⁇ . ⁇ J > and L ⁇ are the same or different and each independently represent hydrogen, halogen, cyano, nitro, each optionally substituted by halogen substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl
• Aryl preferably represents aromatic, mono- or polycyclic hydrocarbon rings, such as in particular phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, preferably phenyl
• Halogen is preferably fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine
• X 1 , X 2 , X 3 , X 4 , X 5 and X 6 represent halogen, alkylsulfonyl or arylsulfonyl,
• Fluoromethoximino compounds of the formula (I) with Ql in their meaning as NH can also be obtained (process al) if fluoromethoximino compounds according to the invention of the formula (I) with Q in their meaning as oxygen with methylamine, optionally in the presence of a diluent, such as, for example, methanol , Ethanol or tetrahydrofuran Finally, it was found that the fluoromethoximino compounds of the formula (I) have very good microbicidal properties and can be used to protect plants against harmful organisms
• the substances according to the invention have a better activity than constitutionally similar, previously known active substances with the same direction of action
• the compounds according to the invention can optionally be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E- and Z-. Both the E- and the Z-isomers, as well as any mixtures of these isomers, are claimed
• the invention preferably relates to compounds of the formula (I) in which
• Q represents oxygen or -NH-
• Ar represents phenyl which is optionally monosubstituted to trisubstituted or naphthyl which is monosubstituted to tetrasubstituted, the possible substituents preferably being selected from the list below Halogen, cyano, nitro, amino, hydroxy, mercapto, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms. len atoms, in each case straight-chain or branched haloalkyl,
• Q 2 represents oxygen or sulfur
• X represents hydrogen, fluorine, chlorine or bromine
• L, L 2 , L 3 and L 4 are the same or different and are each independently of one another hydrogen, halogen, cyano, nitro, in each case optionally by 1 to
• halogen atoms are substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each having 1 to 6 carbon atoms
• the saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino
• Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds which optionally form a polycyclic ring system with other carbocyclic, fused or bridged rings
• the invention relates in particular to compounds of the formula (I) in which
• Q represents oxygen or -NH-
• Ar represents phenyl which is monosubstituted or disubstituted, identically or differently, the possible substituents preferably being selected from the list below:
• Q 2 represents oxygen or sulfur
• X represents hydrogen fluorine or chlorine
• L, L 2 , L 3 and L 4 are identical or different and are each independently of one another hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethylchlorofluorifluoromethyl, difluoromethylchlorofluorodifluoromethyl methylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl.
• Q represents oxygen or -NH-
• R stands for a grouping in which Ar represents phenyl which is monosubstituted or disubstituted, identically or differently, the possible substituents preferably being selected from the list below:
• Q 2 represents oxygen or sulfur
• X represents hydrogen, fluorine or chlorine
• L and L 3 are the same or different and each independently represent hydrogen or methyl and
• L 2 and L 4 represent hydrogen.
• Q preferably for oxygen and especially for -NH-
• R also preferably for a grouping
• Q 2 preferably represents oxygen and in particular sulfur
• X preferably represents hydrogen or halogen and in particular fluorine and
• Ar preferably represents unsubstituted or monosubstituted to trisubstituted phenyl or unsubstituted or monosubstituted or monosubstituted naphthyl, and in particular represents monosubstituted or disubstituted phenyl
• the substituents of Ar are preferably selected from the list below: Halogen, cyano, nitro, amino, hydroxy, mercapto, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms. len atoms, in each case straight-chain or branched haloalkyl,
• the substituents of Ar are particularly preferably selected from the list below:
• L and L 3 are the same or different and independently of one another preferably each represent hydrogen, halogen, cyano, nitro, in each case alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each optionally substituted by 1 to 5 halogen atoms, each having 1 to 6 carbon atoms and in particular for
• L 2 and L 4 are identical or different and, independently of one another, are preferably each hydrogen, halogen, cyano, nitro, in each case alkyl which is optionally substituted by 1 to 5 halogen atoms, in particular methyl, alkoxy,
• Alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms and especially for hydrogen.
• radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals become independent of the combination specified in each case, and also arbitrarily by radical definitions of others
• Formula (II) provides a general definition of the hydroxyaryl compounds required as starting materials for carrying out process a) according to the invention.
• Ql, L *, L 2 , L 3 and L 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Ql, Ll, L 2 , L 3 and L 4 were given.
• hydroxyaryl compounds of the formula (II) are not yet known; as new substances, they are the subject of the present application.
• Rl represents alkyl
• R 2 represents hydrogen or alkyl
• Rl and R 2 together with the atoms to which they are attached represent a five- or six-membered heterocyclic ring and
• a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; a halogenated hydrocarbon, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; an ether, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; a nitrile, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, an ester such as methyl
• an acid preferably an inorganic or organic protonic or Lewis acid, such as, for example, hydrogen chloride, bromine Hydrogen, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, toluenesulfonic acid, boron trifluoride (also as etherate), boron tribromide, aluminum trichloride, aluminum tribromide, zinc chloride, iron or III-chloride, antimony polymeric acid such as, for example, an acidic ion exchanger, an acidic alumina or acidic silica gel,
• Hydroxyaryl compounds of the formula (II) with Ql in their meaning as NH can also be obtained (process B1) if hydroxyaryl compounds of the formula (II) with Ql in their meaning as oxygen with methylamine, optionally in the presence of a diluent, such as methanol, Ethanol or tetrahydrofuran
• the acetals required as starting materials for carrying out process b) according to the invention are generally defined by the formula (IX).
• Q1, L1, L 2 , L 3 and L 4 preferably or in particular have those meanings which already in connection with the description of the invention
• Rl represents alkyl, preferably methyl or ethyl
• R 2 represents hydrogen or alkyl, preferably methyl or ethyl
• Rl and R 2 together with the atoms to which they are attached represent a five- or six-membered, heterocyclic ring , preferably for tetrahydrofyl or tetrahydropyryl.
• Rl, R 2 , Ql, Ll, L 2 , L 3 and L 4 have the meanings given above,
• a nitrosating agent preferably with an alkali metal nitrite, such as sodium nitrite, or in particular with nitrosyl chloride or an alkyl nitrite, such as t-butyl nitrite or t-amyl nitrite, optionally in the presence of a diluent, preferably an ester, such as, for example, methyl acetate or ethyl acetate , or an alcohol, such as methanol or ethanol, and optionally in the presence of an acid acceptor, preferably an alkali metal hydroxide, carbonate or alcoholate, such as sodium methoxide or ethanolate, at temperatures from -50 ° C to 100 ° C, preferably from - 20 ° C to 50 ° C, implemented,
• a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; a halogenated hydrocarbon, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or
• Trichloroethane an ether, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, a ketone such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; a nitrile such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, an ester such as methyl acetate or ethyl acetate; one
• ether such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-die
• Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; a sulfoxide such as dimethyl sulfoxide; a sulfone such as sulfolane; an alcohol, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water,
• a base preferably an alkaline earth metal or alkali metal hydride, hydroxide, amide, alcoholate, acetate, carbonate or bicarbonate, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide , Sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, or a tertiary amine such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N -Dimethyl-benzylamine, pyridine, N-
• Methylpiperidine N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU), and optionally in the presence of a catalyst, preferably a Lewis acid, such as, for example, ferric chloride, aluminum chloride or aluminum bromide,
• Acetals of the formula (IX) with Ql in their meaning as NH can also be obtained (process cl) if acetals of the formula (IX) with Ql in their meaning as oxygen with methylamine, optionally in the presence of a diluent, for example Methanol, ethanol or tetrahydrofuran
• the aryl acetic acid derivatives required as starting materials for carrying out the process c) according to the invention for the preparation of the acetals of the formula (IX) are generally defined by the formula (X).
• Q1, L1, L 2 , L 3 and L 4 preferably have or in particular those meanings which have already been given in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for Q1, L1, L 2 , L 3 and L 4 .
• Rl and R 2 preferably have those meanings which have already been given as preferred in connection with the description of the compounds of the formula (IX).
• arylacetic acid derivatives of the formula (X) are known and / or can be prepared by known processes (see, for example, J. Org Chem 1994, 203-13, and DE-9 611 653).
• heterocyclyl derivatives also required as starting materials for carrying out process a) according to the invention are generally defined by the formulas (III), (IV), (V), (VI), (VII) and (VIII)
• formulas (III), ( IV), (V), (VI), (VII) and (VIII) have Ar, Q 2 and X preferably or in particular those meanings which have already been preferred in connection with the description of the compounds of the formula (I) according to the invention or as particularly preferred for Ar, Q 2 and X were given.
• ⁇ l, X 2 , X 3 , X 4 , X 5 and X ⁇ are independently halogen, preferably fluorine or chlorine, or alkylsulfonyl or arylsulfonyl, preferably methylsulfonyl, benzylsulfonyl or tolylsulfonyl.
• heterocyclyl derivatives of the formulas (III), (IV), (V), (VI), (VII) and (VIII) are known synthetic chemicals and / or can be prepared by known processes (see, for example, J. Heterocyclic Chem. 30, 357 (1993), J. Chem. Soc, 1955; 3478, 3480, Chem. Ber., 97, 225-237, (1964), DE-9 611 653)
• Suitable diluents for carrying out processes a) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, halogenated hydrocarbons , such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone
• Process a) according to the invention is optionally carried out in the presence of a suitable acid acceptor.
• a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or
• Alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as sodium hydride, sodium amide, sodium methylate, Sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecen (DBU)
• reaction temperatures can be varied within a substantial range when carrying out process a) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
• 0.2 to 5 mol, preferably 0.5 to 2 mol, of a heterocyclyl derivative of the formulas are generally employed per mol of the hydroxyaryl compounds of the general formula (II) (III), (IV), (V), (VI), (VII) or (VIII).
• All of the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
• the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
• Fungicides can be used to control Plasmodiophoromycetes
• Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae
• Xanthomonas species such as, for example, Xanthomonas campestris pv oryzae
• Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
• Erwinia species such as, for example, Erwinia amylovora;
• Pythium species such as, for example, Pythium ultimum
• Phytophthora species such as, for example, Phytophthora infestans
• Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
• Plasmopara species such as, for example, Plasmopara viticola
• Bremia species such as, for example, Bremia lactucae
• Peronospora species such as, for example, Peronospora pisi or P. brassicae,
• Erysiphe species such as, for example, Erysiphe graminis
• Sphaerotheca species such as, for example, Sphaerotheca Sleepiginea
• 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 P graminea
• Cochliobolus species such as, for example, Cochliobolus sativus
• Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
• Uromyces species such as, for example, Uromyces appendiculatus
• Puccinia species such as, for example, Puccinia recondita
• Sclerotinia species such as, for example, Sclerotinia sclerotiorum
• Tilletia species such as, for example, Tilletia caries
• Ustilago 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, for example, Pseudocercosporella herpotrichoides
• the active compounds according to the invention can be used with particularly good success in combating cereal diseases, for example against Puccinia species, and for diseases in wine, fruit and vegetable cultivation, for example against Venutia and Plasmopara species Active ingredients are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance
• the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
• technical materials that are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastics, cooling lubricants and other materials that are attacked or decomposed by microorganisms can.
• parts of production systems, such as cooling water circuit runs which can be impaired by the multiplication of microorganisms.
• technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
• Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
• the active compounds according to the invention preferably act against fungi, in particular mold, wood-staining and wood-destroying fungi
• microorganisms of the following genera may be mentioned
• Alternaria such as Alternaria tenuis
• Aspergillus such as Aspergillus niger
• Chaetomium like Chaetomium globosum
• Coniophora such as Coniophora puetana
• Lentinus such as Lentinus tigrinus
• Penicillium such as Penicillium glaucum
• Polyporus such as Polyporus versicolor
• Aureobasidium such as Aureobasidium pullulans
• Sclerophoma such as Sclerophoma pityophila
• Trichoderma such as Trichoderma viride
• Escherichia such as Escherichia coli
• Pseudomonas such as Pseudomonas aeruginosa
• Staphylococcus such as Staphylococcus aureus.
• the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Fine encapsulation in polymeric materials and in coating compositions for seeds, as well as ULV cold and warm mist formulations.
• customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Fine encapsulation in polymeric materials and in coating compositions for seeds, as well as ULV cold and warm mist 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, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate 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.
• water e.g. organic solvents can also be used as auxiliary solvents.
• aromatics such as xylene, toluene or alkylnaphthalenes
• chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes 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.
• Liquefied gaseous extenders or carriers mean 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.
• Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates.
• the following are suitable as solid carriers for granules: e.g. broken and fractionated natural stones such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic
• Flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
• Possible emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
• Possible dispersing agents are, 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.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, for example 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 also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
• synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components
• Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole- M, dinocap, diphenylamine, dipyrithione, ditalimfos, dorphianolodin, dithianonodon, dithianonodonone
• Famoxadone, fenapanil, fenarimol, fenbuconazole, fen assumes that it is not necessary to produce a conjugate or a conjugate.
• fenazolutol flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusila
• Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovededione,
• Kasugamycin, Kresoxim-methyl, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Borodux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Meth tartroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
• Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
• Paclobutrazole peognize, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb,
• Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thycyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazcutichlamidol, triazbutil, triazoxide
• Tridemorph triflumizole, triforin, triticonazole
• Methane tetrathiol sodium salt methyl l- (2,3-dihydro-2,2-dimethyl-lH-inden-l-yl) -lH-imidazole-5-carboxylate,
• Bacillus thuringiensis 4-bromo-2- (4-chlorophenyl) -1 - (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, bendiocarb, benufracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, Brofenprox , Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,
• Chlorpyrifos M Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,
• Mecarbam Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
• Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Prome- carb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrophosin, Pyridlhentrozin, Pyridl Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
• Tebufenozide Tebufenpyrad
• Tebupirimiphos Teflubenzuron
• Tefluthrin Temephos
• Terbam Terbufos
• Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thiomethonon, Thionazin, Thuringiensin, Tralomenhriazonium, Tronomenhriazurononium, Tronomenhriazonium Vamidothione, XMC, xylylcarb, zetamethrin
• the active substances 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 ,
• the application rates can be varied within a substantial range, depending on the type of application.
• the application rates of active compound are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha ha
• the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
• the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
• the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%
• the application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on dei
• composition of the material to be protected The optimal amount can be determined by test series. In general, the application trations in the range of 0.001 to 5 wt .-%, preferably 0.05 to 1.0 wt .-%, based on the material to be protected.
• the effectiveness and the spectrum of activity of the active substances to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active substances are used to enlarge the spectrum of activity or Achieving special effects such as additional protection against insects can be added. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
• logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0, 1% aqueous phosphoric acid).
• Emulsifier 3 parts by weight of alkylaryl 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 spray coating is inoculated with an aqueous spore suspension of Plasmopara viticola and then remains for 1 day in an incubation cabin at approx. 20 ° C and 100% relative humidity.
• the plants are then placed in a greenhouse at about 21 ° C. and about 90% relative atmospheric humidity for 5 days.
• the plants are then moistened and placed in an incubation cabin for 1 day.
• Emulsifier 3 parts by weight of alkylaryl 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 then placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.
• Evaluation is carried out 12 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• Emulsifier "0.6 parts by weight of alkylaryl 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 then placed in a greenhouse at a temperature of approximately 20.degree. C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.
• Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• Emulsifier 0.6 parts by weight of alkylaryl 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 a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of rust pustules.
• Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

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• Organic Chemistry (AREA)
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• 1997
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