Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D231/38—Nitrogen atoms
  • C07D231/40—Acylated on said nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to the use of partially known 5-
• Amino-pyrazole derivatives to combat unwanted microorganisms.
• R 1 represents alkyl, cycloalkyl, alkoxyalkyl or haloalkyl
• R 2 represents hydrogen, halogen, cyano, nitro, haloalkylthio, alkoxycarbonyl or alkenyloxycarbonyl,
• R 3 represents optionally substituted alkyl or optionally substituted cycloalkyl
• R 4 represents hydrogen, alkyl or optionally substituted cycloalkyl
• Y represents optionally substituted alkanediyl or alkenediyl
• R 5 represents optionally substituted aryl or optionally substituted aryloxy
• Formula (I) provides a general definition of the 5-amino-pyrazole derivatives which can be used according to the invention.
• R 1 preferably represents alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkoxy part or for haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.
• R 2 preferably represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethylthio, difluoromethylthio, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part or alkenyloxycarbonyl having 2 to 4 carbon atoms in the alkenyloxy part.
• R 3 preferably represents alkyl with 1 to 4 carbon atoms which is optionally substituted by cyano or cycloalkyl with 3 to 6 carbon atoms which is optionally monosubstituted to trisubstituted, identically or differently, by halogen and / or alkyl having 1 to 4 carbon atoms.
• R 4 preferably represents hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms which is optionally monosubstituted to triple, identical or different, substituted by halogen and / or alkyl having 1 to 4 carbon atoms.
• Y preferably represents alkanediyl with 1 to 4 carbon atoms or alkenediyl with 2 to 4 carbon atoms which is optionally mono- or disubstituted by halogen and / or cycloalkyl having 3 to 6 carbon atoms.
• R 5 preferably represents phenyl or phenoxy, where each of these radicals may be monosubstituted to tetrasubstituted by identical or different halogen, nitro, cyano, C r C 12 alkyl, C 1 -C 12 alkoxy, C, -C 12 -Alkylthio, C r C 12 - haloalkyl, -C-C ⁇ 2 -haloalkoxy, C ⁇ -C ⁇ 2 -haloalkylthio, C 2 -C ⁇ - alkenyl, C r C 4 -alkoxy-C 2 -C 12 alkenyl, C r C 4th Alkylthio-C 2 -C 12 alkenyl,
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula wherein
• R 6 represents phenyl or pyridyl, where each of these radicals can be substituted once to three times, identically or differently by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and / or haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, or
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 7 for alkyl with 1 to 6 carbon atoms or alkoxyalkyl with 1 to 6 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 8 represents alkyl having 1 to 6 carbon atoms, benzyl or pyridylmethyl, where the latter two radicals can be substituted once to three times, identically or differently, by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and / or haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, or
• R 5 represents a radical of the formula
• R 1 particularly preferably represents methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl, cyclopropyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethyl, difluoromethyl, fluoromethyl, 1-chlorine - ethyl or 1-fluoro-1-ethyl.
• R 2 particularly preferably represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl or allyloxycarbonyl.
• R 3 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or 2-cyanoethyl, cyclopropyl, cyclopentyl or cyclohexyl, the three latter radicals being one to three times , may be substituted identically or differently by fluorine, chlorine, methyl and / or ethyl.
• R 4 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-, i-, s- or t-butyl or cyclopropyl, cyclopentyl or cyclohexyl, the three latter radicals being one to three times, of the same type or can be substituted differently by fluorine, chlorine, methyl and / or ethyl.
• Y particularly preferably represents a grouping of the formula
• R 5 particularly preferably represents phenyl or phenoxy, where each of these radicals can be substituted one to four times, in the same way or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- and i-propyl, n-, i -, s- and t-butyl, methoxy, ethoxy, n- and i-propoxy, n-, i-, s- and t-butoxy,
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 6 represents phenyl or pyridyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, haloalkyl with 1 or
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 7 represents alkyl having 1 to 4 carbon atoms or alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part,
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 8 represents alkyl having 1 to 4 carbon atoms, benzyl or pyridylmethyl, where the latter two radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, haloalkyl with 1 or 2 Carbon atoms and 1 to 3 fluorine, chlorine and / or bromine atoms and / or haloalkoxy with 1 or 2 carbon atoms and 1 to 3 fluorine, chlorine and / or bromine atoms, or
• R 5 represents a radical of the formula
• Rl very particularly preferably represents methyl, ethyl, i-propyl, tert-butyl, methoxymethyl, 1-chloro-1-ethyl, 1-fluoro-1-ethyl or cyclopropyl.
• R2 very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl or allyloxycarbonyl.
• R- very particularly preferably represents methyl, ethyl, i-propyl, tert-butyl, cyclopropyl or 2-cyanoethyl.
• R ⁇ very particularly preferably represents hydrogen, methyl, ethyl, i-propyl or
• Y very particularly preferably represents a grouping of the formula
• R 5 very particularly preferably represents phenyl or phenoxy, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, methoxy, ethoxy, n- and i-propoxy, n-, i-, s- and t-butoxy,
• Ethylcarbonyloxy or by phenyl, phenoxy, phenylthio, benzyl, benzyloxy and / or pyridyloxy, where the last six radicals in turn can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, Nitro, cyano, methyl, tert-butyl, methylthio, methoxy, ethoxy, n- and i-propoxy, n-, i-, s- and t-butoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy and / or trifluoromethylthio, or
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 6 represents phenyl or pyridyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl and / or trifluoromethoxy, or
• R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 7 represents methyl, ethyl, n-propyl or alkoxyalkyl having 1 to 4 carbon atoms or alkoxy part and 1 or 2 carbon atoms in the alkyl part, or R 5 represents phenyl or phenoxy, each of these radicals being simply substituted by a radical of the formula
• R 8 represents methyl, ethyl, n-propyl, benzyl or pyridylmethyl, where the latter two radicals can be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, trifluoromethyl and / or Trifluoromethoxy, or
• R 5 represents a radical of the formula
• the 5-amino-pyrazole derivatives of the formula (I) which can be used according to the invention are known in some cases (cf. WO-A 96-21 653).
• R 9 represents chlorine
• R 10 stands for the radicals or
• R * J represents hydrogen
• R 9 and R 1 1 are hydrogen and
• R 10 represents the rest
• R 9 represents hydrogen, chlorine, cyano or ethoxycarbonyl
• R 1 represents chlorine, bromine, methoxy or trifluoromethyl.
• the 5-amino-pyrazole derivatives of the formula (Ia) can be prepared by
• R 9 has the meanings given above,
• R 10 and R 1 * have the meanings given above and
• R 10 and R 1 J have the meanings given above,
• the remaining 5-amino-pyrazole derivatives of the formula (I) can also be prepared by the above processes.
• the 5-amino-pyrazole derivatives listed in Table 1 are also prepared by the processes given above.
• the 5-aminopyrazoles of the formula (II) and acid halides of the formula (III) required as starting materials when carrying out process (a) according to the invention are known or can be prepared by known methods (cf. WO-A 96-21 653).
• Suitable acid binders for carrying out process (a) according to the invention are all customary inorganic or organic bases.
• Alkali metal or alkaline earth metal hydroxides, carbonates or bicarbonates and also nitrogen bases can preferably be used. Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate,
• DABCO diazabicyclooctane
• DBN diazabicyclonones
• DBU diazabicycloundecene
• Suitable diluents for carrying out process (a) according to the invention are all organic solvents customary for such reactions.
• Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as e.g. Cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.
• reaction temperatures can be varied within a substantial range. In general, temperatures between -40 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
• the process (a) according to the invention is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
• 1 to 2 mol, preferably 1 to 1.5 mol, of acid halide of the formula (III) are generally employed per mol of 5-aminopyrazole of the formula (II).
• the processing takes place according to usual methods.
• the 5-amino-pyrazole derivatives of the formula (Ib) required as starting materials when carrying out process (b) according to the invention are compounds which can be used according to the invention. They can be produced by process (a) according to the invention.
• Suitable chlorinating agents for carrying out process (b) according to the invention are all reagents customary for introducing chlorine. Chlorine gas, chlorine oxygen acids and their salts, such as sodium hypochlorite or potassium hypochlorite, and also chlorides, such as sulfuryl chloride, disulfur dichloride and phosphorus pentachloride, can preferably be used.
• Suitable diluents for carrying out process (b) according to the invention are all organic solvents customary for such reactions.
• Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as e.g. Cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.
• reaction temperatures can also be varied within a substantial range when carrying out process (b) according to the invention. In general I think you work at temperatures between -40 ° C and + 120 ° C, preferably between 0 ° C and 80 ° C.
• the process (b) according to the invention is generally carried out under atmospheric pressure. But it is also possible to work under increased pressure.
• the substances which can be used according to the invention have a strong microbicidal action and can be used to control undesired microorganisms, such as fungi and bacteria, in crop protection and in material protection.
• Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
• 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
• 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 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 P. graminea
• Drechslera (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
• 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 fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
• the active substances which can be used according to the invention are particularly suitable for combating Pyricularia oryzae on rice and for combating cereal diseases, such as Puccinia, Erysiphe and Fusarium species.
• the substances according to the invention can be used very well against Venturia, Podosphaera and Sphaerotheca. They also have a very good in-vitro effect
• the active substances which can be used according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
• the substances which can be used according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
• technical materials are to be understood as non-living materials that have been prepared for use in technology.
• technical materials which are to be protected from microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which attack or decompose from microorganisms can be.
• adhesives glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which attack or decompose from microorganisms can be.
• Materials are also parts of production systems, such as cooling water circuits, that can be affected by the proliferation 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 break down or change the technical materials.
• the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
• 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 like Trichoderma viride
• Escherichia such as Escherichia coli
• Pseudomonas such as Pseudomonas aeruginosa
• Staphylococcus such as Staphylococcus aureus.
• the active ingredients can be converted into the 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 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 formation of surface-active agents, ie 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, if appropriate using formation of surface-active agents, ie 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, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
• alcohols such as butanol or Glycol and its 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.
• aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
• solid carriers for example, natural rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
• Possible solid carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as 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 emulsifiers 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 ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
• Possible dispersing agents are, for example, lignin sulfate and methyl cellulose.
• adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholi- pide, such as cephalins and lecithins, and synthetic phospholipids.
• Other 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 which can be used according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to spread 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.
• Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusrimidol, Flusrimidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
• Hexachlorobenzene Hexaconazole, Hymexazol, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Iso-valedione,
• copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
• Metconazole Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin, Nickel-dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxoliniciminol, Oxyoboxicoxinolimid, Oxyobenzolimidolacid, Oxyobenzolimidolacid, Oxyobenzolimidolacid, Oxyacidoximidolacid, Oxyacidoximidolacid, Oxyacidoximidolacid, Oxyacid Oximicolin, Oxyacid Oximidolacin, Oxyacid Oximidolacid, Oxyacid Oximidolacid, Oxyacidoximidolacid, Oxyacid Oximidolacid, Oxyacid Oximidolacid, Oxyacidoximidolacid
• Thicyofen Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,
• Tricyclazole tridemoph, triflumizole, triforin, triticonazole, uniconazole,
• N- (2,3-dichloro-4-hydroxyphenyl) -l-methyl-cyclohexane carboxamide N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2 -oxo-3-thienyl) -acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) - 1, 4,5,6-tetrahydro- 2-pyrimidinamine, N- (4-hexylpheny 1) - 1, 4, 5, 6-tetrahydro-2-pyrimidinamine,
• Bacillus thuringiensis 4-bromo-2- (4-chloro-phenyl) -l - (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox , Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloetho- carb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-chloro-3-pyridinyl) methyl] -N'-cyano-N-methyl
• Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Prome- carb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetroos, Pyri- phllos daphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,
• Tebufenozide Tebufenpyrad
• Tebupirimiphos Teflubenzuron
• Tefluthrin Temephos
• Terbam Terbufos
• Tetrachlorvinphos Thiafenox, Thiamethoxam, Thiodicarb, Thiofanox, Thiomethon, Thionazine, Thomethenen, Trine
• Triazophos triazuron, trichlorfon, triflumuron, trimethacarb, Vamidothione, XMC, xylylcarb, zetamethrin.
• the active compounds 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 usual way, e.g. by watering, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume process 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 application rates can be varied within a relatively wide range, depending on the type of application.
• the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / 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 ingredient 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% by weight, preferably 10 to 75% by weight.
• the application concentrations of the active compounds which can be used according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
• the optimal one The amount used can be determined by test series.
• the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, 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 increase the activity. Spectrum or achieving special effects such as the additional protection from
• Insects can be added. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
• 0.47 g (0.006 mol) of pyridine are added at room temperature to a solution of 0.99 g (0.005 mol) of 5-amino-4-ethoxycarbonyl-3-ethyl-1-methylpyrazole in 80 ml of dichloromethane.
• a solution of 1.11 g (0.006 mol) of 4-methoxyphenylacetyl chloride in 20 ml of dichloromethane is then added dropwise at the same temperature. It is stirred overnight at room temperature and then under reflux for 24 hours. After cooling, the reaction mixture is washed with dilute HCl and with dilute aqueous NaHCO 3 solution. The organic phase is dried over MgSO4, filtered and evaporated to dryness.
• Dichloromethane are added at room temperature to 0.95 g (0.012 mol) of pyridine.
• a solution of 3.37 g (0.012 mol) of 4- (4-chloro-phenoxy) phenylacetyl chloride in 30 ml of dichloromethane is then added dropwise at the same temperature. After stirring overnight at room temperature, the mixture is washed successively with dilute HCl and dilute aqueous NaHCO 3 solution, dried over MgSO 4, filtered and evaporated to dryness.
• a mixture of 1.0 g (4.70 mmol) of 5-amino-3-ethyl-4-ethoxycarbonyl-1-methylpyrazole, 0.75 g (9.40 mmol) of pyridine and 10 ml of methylene chloride is mixed with 1. 07 g (5.60 mmol) of (3-chlorophenyl) acetic acid chloride were added and the mixture was stirred at 20 ° C. for 18 hours.
• the reaction mixture is then mixed with methylene chloride and water.
• the organic phase is separated off, washed successively with 10% aqueous hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, then dried over magnesium sulfate, filtered and concentrated under reduced pressure.
• Solvent 25 parts by weight of N, N-dimethylacetamide emulsifier: 0.6 part 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 mildew pustules.
• Evaluation is carried out 7 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 part 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%.
• Evaluation is carried out 7 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 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.
• 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.
• 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 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.

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• 1998
  • 1998-08-26 DE DE19838708A patent/DE19838708A1/de not_active Withdrawn
• 1999
  • 1999-08-18 EP EP99942879A patent/EP1107956A2/de not_active Withdrawn
  • 1999-08-18 US US09/763,428 patent/US6444612B1/en not_active Expired - Fee Related
  • 1999-08-18 AU AU56225/99A patent/AU5622599A/en not_active Abandoned
  • 1999-08-18 JP JP2000571015A patent/JP2002525272A/ja active Pending
  • 1999-08-18 WO PCT/EP1999/006043 patent/WO2000011951A2/de not_active Application Discontinuation
  • 1999-08-18 CN CN99810381A patent/CN1315943A/zh active Pending

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