EP1761498A1 - 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide - Google Patents

1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide

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Publication number
EP1761498A1
EP1761498A1 EP05750478A EP05750478A EP1761498A1 EP 1761498 A1 EP1761498 A1 EP 1761498A1 EP 05750478 A EP05750478 A EP 05750478A EP 05750478 A EP05750478 A EP 05750478A EP 1761498 A1 EP1761498 A1 EP 1761498A1
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EP
European Patent Office
Prior art keywords
formula
compounds
methyl
meanings
anilides
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05750478A
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German (de)
French (fr)
Inventor
Markus Gewehr
Bernd Müller
Thomas Grote
Wassilios Grammenos
Anja Schwögler
Joachim Rheinheimer
Carsten Blettner
Peter Schäfer
Frank Schieweck
Oliver Wagner
Frank Werner
Jan Rether
Siegfried Strathmann
Reinhard Stierl
Maria Scherer
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BASF SE
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BASF SE
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Application filed by BASF SE filed Critical BASF SE
Publication of EP1761498A1 publication Critical patent/EP1761498A1/en
Withdrawn legal-status Critical Current

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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
    • 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

Definitions

  • the present invention relates to 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides of the formula I.
  • R 1 and R 2 are independently halogen, C ⁇ -C 6 -alkyl, C 6 halogen-alkyl, cyano, nitro, methoxy, trifluoromethoxy or difluoromethoxy.
  • the invention relates to a method for controlling harmful fungi with the compounds I and the use of the compounds I for the preparation of fungicidal compositions.
  • 1-Methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides are known from EP-A 0589301, in which also a process for their preparation and a list of possible mixing partners from the series of fungicides, bactericides , Acaricides, nematicides or insecticides.
  • WO 01/42223 likewise discloses 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides, which are monosubstituted on the phenyl ring.
  • the object of the present invention was to provide new 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid anilides which have an improved fungicidal action, in particular even at low application rates.
  • R 1 and R 2 independently of one another are fluorine, chlorine, cyano, methyl, methoxy or trifluoromethyl.
  • R 1 and R 2 are independently fluorine, chlorine, cyano or methoxy.
  • Table 17 Connection 17.1 - 17.11 Compounds of the formula Ib, in which R 1 is methoxy and R 2 is in each case one of the meaning of Table A.
  • halogen is fluorine, chlorine, bromine and iodine and in particular fluorine and chlorine.
  • alkyl includes straight-chain and branched alkyl groups. These are preferably straight-chain or branched C 1 -C 6 -alkyl groups. Examples of alkyl groups are alkyl, in particular methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl.
  • Haloalkyl is an alkyl group as defined above, which is partially or completely halogenated with one or more halogen atoms, in particular fluorine and chlorine. Preferably, 1 to 3 halogen atoms are present, with the difluoromethane / - or the trifluoromethyl group being particularly preferred.
  • the radical shark in the formula II represents a halogen atom, such as chlorine, bromine and iodine, in particular chlorine or bromine.
  • This reaction is usually carried out at temperatures from -20 ° C to 100 ° C, preferably 0 ° C to 50 ° C.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene.
  • ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and
  • Tetrahydrofuran Tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also dimethyl sulfoxide and dimethylformamide, particularly preferably toluene and tetrahydrofuran.
  • nitriles such as acetonitrile and propionitrile
  • ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone
  • alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and Calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate and alkali metal hydrogencarbonates such as sodium bicarbonate, and organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butoxide and dime
  • Triethylamine and pyridine are particularly preferably used.
  • the bases are generally used in equimolar amounts based on the compound II. But they can also be used in an excess of 5 mol% to 30 mol%, preferably 5 mol% to 10 mol%, or - in the case of using tertiary amines - optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use II in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%, based on III.
  • the compounds I according to the invention can also be present in the application form as fungicides together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • fungicides for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • When mixing the compounds I or the agents containing them in the application form as fungicides with other fungicides is obtained in many cases, an enlargement of the fungicidal spectrum of activity.
  • the following list of fungicides with which the compounds according to the invention can be used together is intended to illustrate, but not limit, the possible combinations.
  • Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc-ethylenediamine-bis-dithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zihk- (N, N-ethylene-bis-dithiocarbamate) , Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide;
  • Nitro derivatives such as dinitro (1-methylheptyl) -phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl-isopropylcarbonate, 5-nitro- isophthalate di-isopropyl;
  • Heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethyl-phthalimidophosphonothioate, 5-amino-1-bis [...
  • Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile,
  • Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) -acrylic acid morpholide, as well as various fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2- hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) -N-furoyl (2) -alaninate, DL-N- (2,6-dimethyl-phenyl) -N- (2 '-methoxyacetyl) alanine methyl ester, N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacety
  • the compounds of the formula I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes. You are currently systemically effective and can therefore also be used as foliar and soil fungicides. They can also be used for seed treatment.
  • fungi are suitable for controlling the following phytopathogenic fungi: Blumeria graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Unin cinula necator on vines, Puccinia species on cereals, Rhizoctonia species Cotton, rice and turf, Ustilago species on cereals and sugarcane, Venturia inaequalis on apples, Helminthosporium on cereals, Septoria nodorum on wheat, Botrytis cinera on gray strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudoper
  • the application rates for compound I are 0.01 to 1 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
  • application rates of mixture of 0.001 to 250 g / kg of seed preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg are generally used.
  • compound I is applied by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
  • the fungicidal compounds I according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules and by spraying, atomizing, dusting , Scattering or pouring are applied.
  • the application form depends on the intended use; It should in any case ensure the finest possible and uniform distribution of the mixture according to the invention.
  • the formulations are prepared in a manner known per se, for example by adding solvents and / or carriers, if desired using Emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • solvent mixtures may also be used, - carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals e.g., kaolins, clays, talc, chalk
  • ground synthetic minerals e.g., fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • dispersants such
  • the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or Fet- talkoholglycolethern, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tribu
  • Powder scattering and dusting agents can be prepared by mixing or co-grinding Compound I with a solid carrier.
  • Granules e.g., coated, impregnated or homogeneous granules
  • a solid carrier usually prepared by binding the active ingredient or agents to a solid carrier.
  • fillers or solid carriers are, for example, mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cornmeal, tree bark, wood and nutshell meal, cellulose powder or other solid carriers.
  • the formulations generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of the compound I.
  • the active compounds are used in a purity of 90% to 100%, preferably 95% to 100% (by NMR or HPLC spectrum).
  • formulations are: 1. Products for dilution in water
  • DC Dispersible Concentrates
  • Emulsifiable Concentrates 15 parts by weight of the active compounds are dissolved in xylene with addition of calcium
  • Emulsions (EW, EO) 40 parts by weight of the active compounds are dissolved in xylene with addition of calcium
  • Dodecylbenzenesulfonate and castor oil ethoxylate (5% each). This mixture is introduced by means of an emulsifier (Ultraturax) in water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • an emulsifier Ultraturax
  • the active ingredients 50 parts by weight of the active ingredients are finely ground with the addition of dispersants and wetting agents and prepared by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • Water-dispersible and water-soluble powders (WP, SP) 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just before use (tank mix), are added. These agents can be added to the inventive compositions in a weight ratio of 1:10 to 10: 1.
  • the application of the compound I or the corresponding formulations is carried out by treating the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free of them with a fungicidally effective amount of compound I.
  • the application can be made before or after the attack by the harmful fungi.
  • the active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in volume -Dependent solvent emulsifier from 99 to 1 ad 10 ml was made up. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below. Alternatively, the active ingredients were used as a commercial ready-made formulation and with water to the specified Wirkstoffkonz. diluted.
  • Paprika seedlings of the cultivar "Neusiedler Ideal Elite” were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below, after 2-3 leaves had developed well.
  • the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution.
  • the test plants were placed in a climatic chamber at 22 to 24 ° C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.

Abstract

The invention relates to 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides of formula (I), wherein the substituents have the following meaning: R1 and R2 independently represent halogen, C1-C6 alkyl, C1-C6 alkyl halide, cyano, nitro, methoxy, trifluoromethoxy, or difluoromethoxy.

Description

1-Methyl-3-difluormethyl-pyrazol-4-carbonsäure-(ortho-phenyl)-anilide und ihre Verwendung als Fungizid 1-Methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides and their use as fungicide
Beschreibungdescription
Die vorliegende Erfindung betrifft 1-Methyl-3-difluormethyl-pyrazol-4-carbonsäure- (ortho-phenyl)-anilide der Formel IThe present invention relates to 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides of the formula I.
in der die Substituenten die folgende Bedeutung haben: in which the substituents have the following meaning:
R1 und R 2 unabhängig voneinander Halogen, Cι-C6-Alkyl, Cι-C6 Halogen-alkyl, Cyano, Nitro, Methoxy, Trifluormethoxy oder Difluormethoxy.R 1 and R 2 are independently halogen, Cι-C 6 -alkyl, C 6 halogen-alkyl, cyano, nitro, methoxy, trifluoromethoxy or difluoromethoxy.
Außerdem betrifft die Erfindung ein Verfahren zur Bekämpfung von Schadpilzen mit der Verbindungen I und die Verwendung der Verbindungen I zur Herstellung fungizider Mittel.In addition, the invention relates to a method for controlling harmful fungi with the compounds I and the use of the compounds I for the preparation of fungicidal compositions.
1-Methyl-3-difluormethyl-pyrazol-4-carbonsäure-(ortho-phenyl)-anilide sind aus der EP- A 0589301 bekannt, in der auch ein Verfahren zu deren Herstellung sowie eine Liste möglicher Mischungspartner aus der Reihe der Fungizide, Bakterizide, Akarizide, Ne- matizide oder Insektizide angegeben ist.1-Methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides are known from EP-A 0589301, in which also a process for their preparation and a list of possible mixing partners from the series of fungicides, bactericides , Acaricides, nematicides or insecticides.
Aus der WO 01/42223 sind ebenfalls 1-Methyl-3-difluormethyl-pyrazol-4- carbonsäure(ortho-phenyl)-anilide bekannt, die am Phenylring monosubstituiert sind.WO 01/42223 likewise discloses 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides, which are monosubstituted on the phenyl ring.
Die beschriebenen 1-Methyl-3-difluormethyl-pyrazol-4-carbonsäure-anilide können jedoch, insbesondere bei niedrigen Aufwandmengen, nicht in vollem Umfang zufrieden stellen.However, the described 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid anilides can not be fully satisfied, in particular at low application rates.
Aufgabe der vorliegenden Erfindungen war es, neue 1-Methyl-3-difluormethyl-pyrazol- 4-carbonsäure-anilide zur Verfügung zu stellen, die eine verbesserte fungizide Wirkung aufweisen, insbesondere auch bei niedrigen Aufwandmengen.The object of the present invention was to provide new 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid anilides which have an improved fungicidal action, in particular even at low application rates.
Demgemäss wurde die eingangs definierten Verbindungen der Formel I gefunden. Bevorzugt sind 1 -Methyl-3-difluormethyl-pyrazol-4-carbonsäure-(ortho-phenyl)-anilide der Formel IAccordingly, the compounds of formula I defined above were found. Preference is given to 1-methyl-3-difluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl) -anilides of the formula I.
in der die Substituenten die folgende Bedeutung haben: in which the substituents have the following meaning:
R1 und R 2 unabhängig voneinander Fluor, Chlor, Cyano, Methyl, Methoxy oder Triflu- ormethyl.R 1 and R 2 independently of one another are fluorine, chlorine, cyano, methyl, methoxy or trifluoromethyl.
Weiterhin sind Verbindungen der Formel I bevorzugt, bei denen R1 und R2 unabhängig voneinander Fluor, Chlor, Cyano oder Methoxy bedeuten.Furthermore, compounds of the formula I are preferred in which R 1 and R 2 are independently fluorine, chlorine, cyano or methoxy.
Besonders bevorzugt sind Verbindungen der Formel I , bei denen R1 und R2 unabhängig voneinander Fluor oder Chlor bedeuten.Particular preference is given to compounds of the formula I in which R 1 and R 2 independently of one another are fluorine or chlorine.
Ganz besonders bevorzugt sind Verbindungen der Formel I bei denen R1 und R2 in der 3- und 4-Position des Phenylrings stehen.Very particular preference is given to compounds of the formula I in which R 1 and R 2 are in the 3- and 4-position of the phenyl ring.
Von den erfindungsgemäßen Verbindungen I sind Verbindungen der Formeln la bis If bevorzugt, die in den folgenden Tabellen aufgeführt sind.Of the compounds I according to the invention compounds of the formulas Ia to If are preferred, which are listed in the following tables.
Tabelle A Table A
Tabelle 1 : Table 1 :
Verbindung 1.1 - 1.11Connection 1.1 - 1.11
Verbindungen der Formel la, in denen R1 Fluor bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht.Compounds of the formula Ia in which R 1 is fluorine and R 2 is in each case one of the meanings of Table A.
Tabelle 2:Table 2:
Verbindung 2.1 - 2.11Connection 2.1 - 2.11
Verbindungen der Formel la, in denen R1 Chlor bedeutet und R2 für jeweils eine Be- deutung der Tabelle A steht.Compounds of the formula Ia in which R 1 is chlorine and R 2 is in each case one of the meanings of Table A.
Tabelle 3:Table 3:
Verbindung 3.1 - 3.11Connection 3.1 - 3.11
Verbindungen der Formel la, in denen R1 Brom bedeutet und R2 für jeweils eine Be- deutung der Tabelle A steht.Compounds of the formula Ia in which R 1 is bromine and R 2 is in each case one of the meanings of Table A.
Tabelle 4:Table 4:
Verbindung 4.1 - 4.11Connection 4.1 - 4.11
Verbindungen der Formel la, in denen R1 Jod bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht.Compounds of the formula Ia in which R 1 is iodine and R 2 is in each case one of the meanings of Table A.
Tabelle 5:Table 5:
Verbindung 5.1 - 5.11Connection 5.1 - 5.11
Verbindungen der Formel la, in denen R1 Methyl bedeutet und R2 für jeweils eine Be- deutung der Tabelle A steht.Compounds of the formula Ia in which R 1 is methyl and R 2 is each one of the meanings of Table A.
Tabelle 6:Table 6:
Verbindung 6.1 - 6.11Connection 6.1 - 6.11
Verbindungen der Formel la, in denen R1 Methoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ia in which R 1 is methoxy and R 2 is each one of the meanings of Table A.
Tabelle 7:Table 7:
Verbindung 7.1 - 7.11Connection 7.1 - 7.11
Verbindungen der Formel la, in denen R1 Trifluormethyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ia in which R 1 is trifluoromethyl and R 2 is in each case one of the meanings of Table A.
Tabelle 8:Table 8:
Verbindung 8.1 - 8.11Connection 8.1 - 8.11
Verbindungen der Formel la, in denen R1 Trifluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht. Tabelle 9:Compounds of the formula Ia in which R 1 is trifluoromethoxy and R 2 is each one of the meanings of Table A. Table 9:
Verbindung 9.1 - 9.11Connection 9.1 - 9.11
Verbindungen der Formel la, in denen R1 Cyano bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ia in which R 1 is cyano and R 2 is each one of the meanings of Table A.
Tabelle 10:Table 10:
Verbindung 10.1 - 10.11Connection 10.1 - 10.11
Verbindungen der Formel la, in denen R1 Nitro bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ia in which R 1 is nitro and R 2 is each one of the meanings of Table A.
Tabelle n:Table n:
Verbindung 11.1 - 11.11Connection 11.1 - 11.11
Verbindungen der Formel Ib, in denen R1 Difluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is difluoromethoxy and R 2 is in each case one of the meanings of Table A.
Tabelle 12:Table 12:
Verbindung 12.1 - 12.11Connection 12.1 - 12.11
Verbindungen der Formel Ib, in denen R1 Fluor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is fluorine and R 2 is each one of the meanings of Table A.
Tabelle 13:Table 13:
Verbindung 13.1 - 13.11Connection 13.1 - 13.11
Verbindungen der Formel Ib, in denen R1 Chlor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is chlorine and R 2 is each one of the meanings of Table A.
Tabelle 14:Table 14:
Verbindung 14.1 - 14.11Connection 14.1 - 14.11
Verbindungen der Formel Ib, in denen R1 Brom bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is bromine and R 2 is each one of the meanings of Table A.
Tabelle 15:Table 15:
Verbindung 15.1 - 15.11Connection 15.1 - 15.11
Verbindungen der Formel Ib, in denen R1 Jod bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is iodine and R 2 is each one of the meanings of Table A.
Tabelle 16:Table 16:
Verbindung 16.1 - 16.11Connection 16.1 - 16.11
Verbindungen der Formel Ib, in denen R1 Methyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is methyl and R 2 is each one of the meanings of Table A.
Tabelle 17: Verbindung 17.1 - 17.11 Verbindungen der Formel Ib, in denen R1 Methoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Table 17: Connection 17.1 - 17.11 Compounds of the formula Ib, in which R 1 is methoxy and R 2 is in each case one of the meaning of Table A.
Tabelle 18: Verbindung 18.1 - 18.11Table 18: Compound 18.1 - 18.11
Verbindungen der Formel Ib, in denen R1 Trifluormethyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is trifluoromethyl and R 2 is each one of the meanings of Table A.
Tabelle 19: Verbindung 19.1 - 19.11Table 19: Compound 19.1 - 19.11
Verbindungen der Formel Ib, in denen R1 Trifluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is trifluoromethoxy and R 2 is each one of the meanings of Table A.
Tabelle 20: Verbindung 20.1 - 20.11Table 20: Compound 20.1 - 20.11
Verbindungen der Formel Ib, in denen R1 Cyano bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is cyano and R 2 is each one of the meanings of Table A.
Tabelle 21: Verbindung 21.1 - 21.11Table 21: Connection 21.1 - 21.11
Verbindungen der Formel Ib, in denen R1 Nitro bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is nitro and R 2 is each one of the meanings of Table A.
Tabelle 22: Verbindung 22.1 - 22.11Table 22: Connection 22.1 - 22.11
Verbindungen der Formel Ib, in denen R1 Difluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ib in which R 1 is difluoromethoxy and R 2 is in each case one of the meanings of Table A.
Tabelle 23: Verbindung 23.1 - 23.11Table 23: Connection 23.1 - 23.11
Verbindungen der Formel Ic, in denen R1 Fluor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ic in which R 1 is fluorine and R 2 is each one of the meanings of Table A.
Tabelle 24: Verbindung 24.1 - 24.11Table 24: Connection 24.1 - 24.11
Verbindungen der Formel Ic, in denen R1 Chluor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ic in which R 1 is chloro and R 2 is in each case one of the meanings of Table A.
Tabelle 25: Verbindung 25.1 - 25.11Table 25: Compound 25.1 - 25.11
Verbindungen der Formel Ic, in denen R1 Brom bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht. Tabelle 26:Compounds of the formula Ic in which R 1 is bromine and R 2 is each one of the meanings of Table A. Table 26:
Verbindung 26.1 - 26.11Connection 26.1 - 26.11
Verbindungen der Formel Ic, in denen R1 Jod bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht.Compounds of the formula Ic in which R 1 is iodine and R 2 is in each case one of the meanings of Table A.
Tabelle 27:Table 27:
Verbindung 27.1 - 27.11Connection 27.1 - 27.11
Verbindungen der Formel Ic, in denen R1 Methyl bedeutet und R2 für jeweils eine Be- deutung der Tabelle A steht.Compounds of the formula Ic in which R 1 is methyl and R 2 is each one of the meanings of Table A.
Tabelle 28:Table 28:
Verbindung 28.1 - 28.11Connection 28.1 - 28.11
Verbindungen der Formel Ic, in denen R1 Methoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ic in which R 1 is methoxy and R 2 is each a meaning of Table A.
Tabelle 29:Table 29:
Verbindung 29.1 - 29.11Compound 29.1 - 29.11
Verbindungen der Formel Ic, in denen R1 Trifluormethyl bedeutet und Rz für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ic in which R 1 is trifluoromethyl and R z is each a meaning of Table A.
Tabelle 30:Table 30:
Verbindung 30.1 - 30.11Connection 30.1 - 30.11
Verbindungen der Formel Ic, in denen R1 Trifluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ic in which R 1 is trifluoromethoxy and R 2 is each a meaning of Table A.
Tabelle 31:Table 31:
Verbindung 31.1 - 31.11Connection 31.1 - 31.11
Verbindungen der Formel Ic, in denen R1 Cyano bedeutet und R2 für jeweils eine Be- deutung der Tabelle A steht.Compounds of the formula Ic in which R 1 is cyano and R 2 is in each case one of the meanings of Table A.
Tabelle 32:Table 32:
Verbindung 32.1 - 32.11Connection 32.1 - 32.11
Verbindungen der Formel Ic, in denen R1 Nitro bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht.Compounds of the formula Ic in which R 1 is nitro and R 2 is each one of the meanings of Table A.
Tabelle 33:Table 33:
Verbindung 33.1 - 33.11Compound 33.1 - 33.11
Verbindungen der Formel Ic, in denen R1 Difluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht. Tabelle 34:Compounds of the formula Ic in which R 1 is difluoromethoxy and R 2 is each one of the meanings of Table A. Table 34:
Verbindung 34.1 - 34.11Connection 34.1 - 34.11
Verbindungen der Formel Id, in denen R1 Fluor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id, in which R 1 is fluorine and R 2 is each one of the meanings of Table A.
Tabelle 35:Table 35:
Verbindung 35.1 -35.11Compound 35.1 -35.11
Verbindungen der Formel Id, in denen R1 Chlor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id, in which R 1 is chlorine and R 2 is in each case one of the meaning of Table A.
Tabelle 36:Table 36:
Verbindung 36.1 - 36.11Compound 36.1 - 36.11
Verbindungen der Formel Id, in denen R1 Brom bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id, in which R 1 is bromine and R 2 is in each case one of the meaning of Table A.
Tabelle 37:Table 37:
Verbindung 37.1 - 37.11Compound 37.1 - 37.11
Verbindungen der Formel Id, in denen R1 Jod bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id in which R 1 is iodine and R 2 is each one of the meanings of Table A.
Tabelle 38:Table 38:
Verbindung 38.1 - 38.11Compound 38.1 - 38.11
Verbindungen der Formel Id, in denen R1 Methyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id in which R 1 is methyl and R 2 is each one of the meanings of Table A.
Tabelle 39:Table 39:
Verbindung 39.1 - 39.11Compound 39.1 - 39.11
Verbindungen der Formel Id, in denen R1 Methoxy bedeutet und R2 für jeweils eineCompounds of the formula Id, in which R 1 is methoxy and R 2 is in each case one
Bedeutung der Tabelle A steht.Meaning of Table A stands.
Tabelle 40:Table 40:
Verbindung 40.1 - 40.11Connection 40.1 - 40.11
Verbindungen der Formel Id, in denen R1 Trifluormethyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id, in which R 1 is trifluoromethyl and R 2 is each one of the meanings of Table A.
Tabelle 41:Table 41:
Verbindung 41.1 - 41.11Connection 41.1 - 41.11
Verbindungen der Formel Id, in denen R1 Trifluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id, in which R 1 is trifluoromethoxy and R 2 is in each case one of the meaning of Table A.
Tabelle 42Table 42
Verbindung 42.1 - 42.11 Verbindungen der Formel Id, in denen R1 Cyano bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compound 42.1 - 42.11 Compounds of formula Id in which R 1 is cyano and R 2 is in each case one of the meaning of Table A.
Tabelle 43: Verbindung 43.1 - 43.11Table 43: Compound 43.1 - 43.11
Verbindungen der Formel Id, in denen R1 Nitro bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id, in which R 1 is nitro and R 2 is each one of the meanings of Table A.
Tabelle 44: Verbindung 44.1 - 44.11Table 44: Compound 44.1 - 44.11
Verbindungen der Formel Id, in denen R1 Difluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Id, in which R 1 is difluoromethoxy and R 2 is in each case one of the meaning of Table A.
Tabelle 45: Verbindung 45.1 - 45.11Table 45: Compound 45.1 - 45.11
Verbindungen der Formel le, in denen R1 Fluor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is fluorine and R 2 is in each case one of the meanings of Table A.
Tabelle 46: Verbindung 46.1 - 46.11Table 46: Compound 46.1 - 46.11
Verbindungen der Formel le, in denen R1 Chlor bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is chlorine and R 2 is in each case one of the meanings of Table A.
Tabelle 47: Verbindung 47.1 -47.11Table 47: Compound 47.1 -47.11
Verbindungen der Formel le, in denen R1 Brom bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is bromine and R 2 is in each case one of the meanings of Table A.
Tabelle 48: Verbindung 48.1 - 48.11Table 48: Compound 48.1 - 48.11
Verbindungen der Formel le, in denen R1 Jod bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is iodine and R 2 is in each case one of the meanings of Table A.
Tabelle 49: Verbindung 49.1 - 49.11Table 49: Compound 49.1 - 49.11
Verbindungen der Formel le, in denen R1 Methyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is methyl and R 2 is in each case one of the meanings of Table A.
Tabelle 50: Verbindung 50.1 - 50.11Table 50: Compound 50.1 - 50.11
Verbindungen der Formel le, in denen R1 Methoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht. Tabelle 51:Compounds of the formula Ie in which R 1 is methoxy and R 2 is in each case one of the meanings of Table A. Table 51:
Verbindung 51.1 - 51.11Connection 51.1 - 51.11
Verbindungen der Formel le, in denen R1 Trifluormethyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is trifluoromethyl and R 2 is in each case one of the meanings of Table A.
Tabelle 52:Table 52:
Verbindung 52.1 - 52.11Connection 52.1 - 52.11
Verbindungen der Formel le, in denen R1 Trifluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is trifluoromethoxy and R 2 is in each case one of the meanings of Table A.
Tabelle 53:Table 53:
Verbindung 53.1 - 53.11Compound 53.1 - 53.11
Verbindungen der Formel le, in denen R1 Cyano bedeutet und R2 für jeweils eine Be- deutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is cyano and R 2 is in each case one of the meanings of Table A.
Tabelle 54:Table 54:
Verbindung 54.1 - 54.11Connection 54.1 - 54.11
Verbindungen der Formel le, in denen R1 Nitro bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht.Compounds of the formula Ie in which R 1 is nitro and R 2 is in each case one of the meanings of Table A.
Tabelle 55:Table 55:
Verbindung 55.1 - 55.11Connection 55.1 - 55.11
Verbindungen der Formel le, in denen R1 Difluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula Ie in which R 1 is difluoromethoxy and R 2 is in each case one of the meanings of Table A.
Tabelle 56:Table 56:
Verbindung 56.1 - 56.11Compound 56.1 - 56.11
Verbindungen der Formel If, in denen R1 Fluor bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht.Compounds of the formula If in which R 1 is fluorine and R 2 is in each case one of the meanings of Table A.
Tabelle 57:Table 57:
Verbindung 57.1 - 57.11Connection 57.1 - 57.11
Verbindungen der Formel If, in denen R1 Chlor bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht.Compounds of the formula If in which R 1 is chlorine and R 2 is in each case one of the meanings of Table A.
Tabelle 58:Table 58:
Verbindung 58.1 - 58.11Compound 58.1 - 58.11
Verbindungen der Formel If, in denen R1 Brom bedeutet und R2 für jeweils eine Bedeu- tung der Tabelle A steht. Tabelle 59:Compounds of the formula If in which R 1 is bromine and R 2 is in each case one of the meanings of Table A. Table 59:
Verbindung 59.1 - 59.11Compound 59.1 - 59.11
Verbindungen der Formel If, in denen R1 Jod bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula If, in which R 1 is iodine and R 2 is each a meaning of Table A.
Tabelle 60:Table 60:
Verbindung 60.1 - 60.11Connection 60.1 - 60.11
Verbindungen der Formel If, in denen R1 Methyl bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula If in which R 1 is methyl and R 2 is in each case one of the meaning of Table A.
Tabelle 61:Table 61:
Verbindung 61.1 - 61.11Connection 61.1 - 61.11
Verbindungen der Formel If, in denen R1 Methoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula If, in which R 1 is methoxy and R 2 is each a meaning of Table A.
Tabelle 62:Table 62:
Verbindung 62.1 - 62.11Compound 62.1 - 62.11
Verbindungen der Formel If, in denen R1 Trifluormethyl bedeutet und R2 für jeweils eineCompounds of the formula If in which R 1 is trifluoromethyl and R 2 is in each case one
Bedeutung der Tabelle A steht.Meaning of Table A stands.
Tabelle 63:Table 63:
Verbindung 63.1 - 63.11Compound 63.1 - 63.11
Verbindungen der Formel If, in denen R1 Trifluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula If, in which R 1 is trifluoromethoxy and R 2 is in each case one of the meanings of Table A.
Tabelle 64:Table 64:
Verbindung 64.1 - 64.11Connection 64.1 - 64.11
Verbindungen der Formel If, in denen R1 Cyano bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula If in which R 1 is cyano and R 2 is in each case one of the meanings of Table A.
Tabelle 65:Table 65:
Verbindung 65.1 - 65.11Compound 65.1 - 65.11
Verbindungen der Formel If, in denen R1 Nitro bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht.Compounds of the formula If in which R 1 is nitro and R 2 is in each case one of the meanings of Table A.
Tabelle 66:Table 66:
Verbindung 66.1 - 66.11Connection 66.1 - 66.11
Verbindungen der Formel If, in denen R1 Difluormethoxy bedeutet und R2 für jeweils eine Bedeutung der Tabelle A steht. Im Rahmen der vorliegenden Erfindung steht Halogen für Fluor, Chlor, Brom und Jod und insbesondere für Fluor und Chlor.Compounds of the formula If in which R 1 is difluoromethoxy and R 2 is in each case one of the meanings of Table A. In the context of the present invention, halogen is fluorine, chlorine, bromine and iodine and in particular fluorine and chlorine.
Der Ausdruck "Alkyl" umfasst geradkettige und verzweigte Alkylgruppen. Vorzugsweise handelt es sich dabei um geradkettige oder verzweigte CrC6-Alkylgruppen. Beispiele für Alkylgruppen sind Alkyl wie insbesondere Methyl, Ethyl, Propyl, 1-MethyIethyl, Bu- tyl, 1-Methylpropyl, 2-Methylpropyl 1,1-Dimethylethyl.The term "alkyl" includes straight-chain and branched alkyl groups. These are preferably straight-chain or branched C 1 -C 6 -alkyl groups. Examples of alkyl groups are alkyl, in particular methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl.
Halogenalkyl steht für eine wie oben definierte Alkylgruppe, die mit einem oder mehre- ren Halogenatomen, insbesondere Fluor und Chlor, teilweise oder vollständig haloge- niert ist. Vorzugsweise sind 1 bis 3 Halogenatome vorhanden, wobei die Difluor- methan/- oder die Trifluormethylgruppe besonders bevorzugt ist.Haloalkyl is an alkyl group as defined above, which is partially or completely halogenated with one or more halogen atoms, in particular fluorine and chlorine. Preferably, 1 to 3 halogen atoms are present, with the difluoromethane / - or the trifluoromethyl group being particularly preferred.
Verfahren zur Herstellung der Verbindungen der allgemeinen Formel F sind aus der EP-A 0 589 301 bekannt.Process for the preparation of the compounds of general formula F are known from EP-A 0 589 301.
Beispielsweise setzt man das 1-Methyl-3-difluormethyl-pyrazolcarbonsäure-halogenid der Formel II mit einem Anilin der Formel III zu den Verbindungen der Formel I um:For example, the 1-methyl-3-difluoromethyl-pyrazolecarboxylic acid halide of the formula II is reacted with an aniline of the formula III to give the compounds of the formula I:
Der Rest Hai in der Formel II steht für ein Halogenatom wie Chlor, Brom und Jod, insbesondere Chlor oder Brom.The radical shark in the formula II represents a halogen atom, such as chlorine, bromine and iodine, in particular chlorine or bromine.
Diese Umsetzung erfolgt üblicherweise bei Temperaturen von -20 °C bis 100 °C, vor- zugsweise 0 °C bis 50 °C.This reaction is usually carried out at temperatures from -20 ° C to 100 ° C, preferably 0 ° C to 50 ° C.
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Petrolether, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p- Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorben- zol, Etherwie Diethylether, Diisopropylether, tert.-Butylmethylether, Dioxan, Anisol undSuitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene. ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and
Tetrahydrofuran, Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethyl- keton, Diethylketon und tert.-Butylmethylketon, Alkohole wie Methanol, Ethanol, n- Propanol, Isopropanol, n-ButanoI und tert.-Butanol sowie Dimethylsulfoxid und Di- methylformamid, besonders bevorzugt Toluol und Tetrahydrofuran.Tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also dimethyl sulfoxide and dimethylformamide, particularly preferably toluene and tetrahydrofuran.
Es können auch Gemische der genannten Lösungsmittel verwendet werden.It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdal- kalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calzi- umhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calzi- umoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calziumhydrid, Alkalimetallamide wie Lithiuma- mid, Natriumamid und Kaliumamid, Alkalimetall- und Erdalkalimetallcarbonate wie Li- thiumcarbonat und Calziumcarbonat sowie Alkalimetallhydrogencarbonate wie Natri- umhydrogencarbonat, und metallorganische Verbindungen, insbesondere Alkalimetal- lalkyle wie Methyllithium, Butyllithium und Phenyllithium, Alkylmagnesiumhalogenide wie Methylmagnesiumchlorid sowie Alkalimetall- und Erdalkalimetallalkoholate wie Natriummethanolat, Natriumethanolat, Kaliumethanolat, Kalium-tert.-Butanolat und Dimethoxymagnesium außerdem organische Basen, z.B. tertiäre Amine wie Trimethy- lamin, Triethylamin, Tri-isopropylethylamin und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyclische Amine in Betracht.Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and Calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate and alkali metal hydrogencarbonates such as sodium bicarbonate, and organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butoxide and dimethoxy magnesium also organic bases, eg tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration.
Besonders bevorzugt werden Triethylamin und Pyridin verwendet.Triethylamine and pyridine are particularly preferably used.
Die Basen werden im allgemeinen in äquimolarem Mengen bezogen auf die Verbindung II eingesetzt. Sie können aber auch in einem Überschuß von 5 mol-% bis 30 mol- %, vorzugsweise 5 mol-% bis 10 mol-%, oder - im Falle der Verwendung von tertiären Aminen - gegebenenfalls als Lösungsmittel verwendet werden.The bases are generally used in equimolar amounts based on the compound II. But they can also be used in an excess of 5 mol% to 30 mol%, preferably 5 mol% to 10 mol%, or - in the case of using tertiary amines - optionally as a solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann für die Ausbeute vorteilhaft sein, II in einem Überschuß von 1 mol-% bis 20 mol- %, vorzugsweise 1 mol-% bis 10 mol-%, bezogen auf III einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use II in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%, based on III.
Die erfindungsgemäßen Verbindungen I können in der Anwendungsform als Fungizide auch zusammen mit anderen Wirkstoffen vorliegen, z.B. mit Herbiziden, Insektiziden, Wachstumsregulatoren, Fungiziden oder auch mit Düngemitteln. Beim Vermischen der Verbindungen I bzw. der sie enthaltenden Mittel in der Anwendungsform als Fungizide mit anderen Fungiziden erhält man in vielen Fällen eine Vergrößerung des fungiziden Wirkungsspektrums. Die folgende Liste von Fungiziden, mit denen die erfindungsgemäßen Verbindungen gemeinsam angewendet werden können, soll die Kombinationsmöglichkeiten erläutern, nicht aber einschränken:The compounds I according to the invention can also be present in the application form as fungicides together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. When mixing the compounds I or the agents containing them in the application form as fungicides with other fungicides is obtained in many cases, an enlargement of the fungicidal spectrum of activity. The following list of fungicides with which the compounds according to the invention can be used together is intended to illustrate, but not limit, the possible combinations.
• Schwefel, Dithiocarbamate und deren Derivate, wie Ferridimethyldithiocarbamat, Zinkdimethyldithiocarbamat, Zinkethylenbisdithiocarbamat, Manganethylenbis- dithiocarbamat, Mangan-Zink-ethylendiamin-bis-dithiocarbamat, Tetramethylthiu- ramdisulfide, Ammoniak-Komplex von Zihk-(N,N-ethylen-bis-dithiocarbamat), Ammoniak-Komplex von Zink-(N,N'-propylen-bis-dithiocarbamat), Zink-(N,N'- propylenbis-dithiocarbamat), N,N'-Polypropylen-bis-(thiocarbamoyl)disulfid;Sulfur, dithiocarbamates and their derivatives, such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc-ethylenediamine-bis-dithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zihk- (N, N-ethylene-bis-dithiocarbamate) , Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide;
• Nitroderivate, wie Dinitro-(1-methylheptyl)-phenylcrotonat, 2-sec-Butyl-4,6- dinitrophenyl-3,3-dimethylacrylat, 2-sec-Butyl-4,6-dinitrophenyl- isopropylcarbonat, 5-Nitro-isophthalsäure-di-isopropylester;Nitro derivatives, such as dinitro (1-methylheptyl) -phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl-isopropylcarbonate, 5-nitro- isophthalate di-isopropyl;
• heterocyclische Substanzen, wie 2-Heptadecyl-2-imidazolin-acetat, 2,4-Dichlor-6- (o-chloranilino)-s-triazin, O,O-Diethyl-phthalimidophosphonothioat, 5-Amino-1- [bis-(dimethylamino)-phosphinyl]-3-phenyl-1 ,2,4- triazol, 2,3-Dicyano-1 ,4- dithioanthrachinon, 2-Thio-1 ,3-dithiolo[4,5-b]chinoxalin, 1-(Butylcarbamoyl)-2- benzimidazol-carbaminsäuremethylester, 2-Methoxycarbonylamino- benzimidazol, 2-(Furyl-(2))-benzimidazol, 2-(Thiazolyl-(4))-benzimidazol, N- (1,1 ,2,2-Tetrachlorethylthio)-tetrahydrophthalimid, N-Trichlormethylthio- tetrahydrophthalimid, N-Trichlormethylthio-phthalimid,Heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethyl-phthalimidophosphonothioate, 5-amino-1-bis [... (dimethylamino) -phosphinyl] -3-phenyl-1, 2,4-triazole, 2,3-dicyano-1, 4-dithioanthraquinone, 2-thio-1,3-dithiolo [4,5-b] quinoxaline, 1 (Butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylaminobenzimidazole, 2- (furyl- (2)) benzimidazole, 2- (thiazolyl- (4)) benzimidazole, N- (1,1, 2, 2-tetrachloroethylthio) -tetrahydrophthalimide, N-trichloromethylthiothetrahydrophthalimide, N-trichloromethylthio-phthalimide,
• N-Dichlorfluormethylthio-N',N'-dimethyl-N-phenyl-schwefelsäure- diamid, 5- Ethoxy-3-trichIormethyl-1 ,2,3-thiadiazol, 2-Rhodanmethylthiobenzthiazol, 1 ,4- Dichlor-2,5-dimethoxybenzol, 4-(2-Chlorphenylhydrazono)-3-methyl-5-isoxazolon, Pyridin-2-thio-1-oxid, 8-Hydroxychinolin bzw. dessen Kupfersalz, 2,3-Dihydro-5- carboxanilido-6-methyl-1 ,4-oxathiin, 2,3-Dihydro-5-carboxanilido-6-methyl-1 ,4- oxathiin-4,4-dioxid, 2-Methyl-5,6-dihydro-4H-pyran-3-carbonsäure-anilid, 2- Methyl-furan-3-carbonsäureanilid, 2,5-Dimethyl-furan-3-carbonsäureanilid, 2,4,5- Trimethyl-furan-3-carbonsäureanilid, 2,5-Dimethyl-furan-3- carbonsäurecyclohexylamid, N-Cyclohexyl-N-methoxy-2,5-dimethyl-furan-3- carbonsäureamid, 2-Methyl-benzoesäure-anilid, 2-lod-benzoesäure-anilid, N- Formyl-N-morpholin-2,2,2-trichlorethylacetal, Piperazin-1,4-diylbis-1- (2,2,2-trichlorethyl)-formamid, 1-(3,4-Dichloranilino)-1-formylamino-2,2,2- trichlorethan, 2,6-Dimethyl-N-tridecyl-morpholin bzw. dessen Salze, 2,6-Dimethyl- N-cyclododecyl-morpholin bzw. dessen Salze, N-[3-(p-tert.-ButylphenyI)-2- methylpropyl]-cis-2,6-dimethyl-morpholin, N-[3-(p-tert.-Butylphenyl)- 2-methylpropyl]-piperidin, 1-[2-(2,4-Dichlorphenyl)-4-ethyl- 1 ,3-dioxolan-2-yl-ethyl]-1 H-1 ,2,4-triazol, 1-[2-(2,4-Dichlorphenyl)-4-n-propyl-1 ,3- dioxolan-2-yl-ethyl]-1 H-1 ,2,4-triazol, N-(n-Propyl)-N-(2,4,6-trichlorphenoxyethyI)- N'-imidazol-yl-harnstoff, 1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1 H-1 ,2,4-triazol-1- yl)-2-butanon, 1 -(4-Chlorphenoxy)-3,3-dimethyl-1 -(1 H- 1,2,4-triazol-1-yl)-2-butanol, (2RS,3RS)-1-[3-(2-Chlorphenyl)-2-(4-fluorphenyl)- oxiran-2-ylmethyl]-1 H-1 ,2,4-triazol, a-(2-Chlorphenyl)-a-(4-chlorphenyl)-5- pyrimidin-methanol, 5-Butyl-2-dimethylamino-4-hydroxy-6-methyI-pyrimidin, Bis- (p-chlorphenyl)-3-pyridinmethanol, 1 ,2-Bis-(3-ethoxycarbonyl-2- thioureido)-benzol, 1,2-Bis-(3-methoxycarbonyl-2-thioureido)-benzol, • Strobilurine wie Methyl-E-methoxyimino-[a-(o-tolyloxy)-o-tolyl]acetat, Methyl-E-2- {2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylat, Methyl-E- methoxyimino-[a-(2- phenoxyphenyl)]-acetamid, Methyl-E-methoxyimino-[a-(2,5-dimethylphenoxy)-o- tolylj-acetamid, • Anilinopyrimidine wie N-(4,6-Dimethylpyrimidin-2-yl)-anilin, N-[4-Methyl-6-(1- propinyl)-pyrimidin-2-yl]-anilin, N-[4-Methyl-6-cyclopropyl-pyrimidin-2-yl]-anilin,N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenyl-sulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-rhodanemethylthiobenzothiazole, 1, 4-dichloro-2,5 -dimethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl -1, 4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid -anilide, 2-methyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid anilide, 2,4,5-trimethyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide , N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxylic acid amide, 2-methylbenzoic acid anilide, 2-iodo-benzoic acid anilide, N-formyl-N-morpholine-2,2,2 trichloroethyl acetal, piperazine-1,4-diylbis-1- (2,2,2-trichloroethyl) -formamide, 1- (3,4-dichloroanilino) -1-formylamino-2,2,2-trichloroethane, 2.6 -Dimethyl-N-tridecyl-morpholine or its salts, 2,6-dimethyl- N-cyclododecyl-morpholine or its salts, N- [3- (p-tert.-butylphenyI) -2-methylpropyl] -cis-2,6-dimethyl-morpholine, N- [3- (p-tert. Butylphenyl) - 2-methylpropyl] -piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole , 1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, N- (n-propyl ) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl urea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1, 2,4-triazole -1-yl) -2-butanone, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, (2RS, 3RS) -1- [3- (2-chlorophenyl) -2- (4-fluorophenyl) - oxiran-2-ylmethyl] -1H-1, 2,4-triazole, a- (2-chlorophenyl) -a- (4-chlorophenyl) -5-pyrimidine-methanol, 5-butyl-2-dimethylamino-4 hydroxy-6-methyl-pyrimidine, bis (p-chlorophenyl) -3-pyridinemethanol, 1, 2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-methoxycarbonyl-2 thioureido) benzene, strobilurins such as methyl-E-methoxyimino [a- (o-tolyloxy) -o-tolyl] acetate, methyl E-2- {2- [6- (2-cyanophenoxy) -pyrimidine 4-yloxy] -phenyl} -3-methoxyacrylate, methyl-E-methoxyimino [a- (2-phenoxyphenyl)] - acetamide, methyl-E-methoxyimino [a- (2,5-dimethylphenoxy) -o-tolylj acetamide, • anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) -aniline, N- [4-methyl-6- (1-propynyl) -pyrimidin-2-yl] -aniline, N- [4 methyl-6-cyclopropyl-pyrimidin-2-yl] aniline,
• Phenylpyrrole wie 4-(2,2-Difluor-1 ,3-benzodioxol-4-yl)-pyrrol-3-carbonitril,Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile,
• Zimtsäureamide wie 3-(4-Chlorphenyl)-3-(3,4-dimethoxyphenyl)- acrylsäuremorpholid, • sowie verschiedene Fungizide, wie Dodecylguanidinacetat, 3-[3- (3,5-Dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimid, Hexachlorbenzol, DL- Methyl-N-(2,6-dimethyl-phenyl)-N-furoyl(2)-alaninat, DL-N-(2,6-Dimethyl-phenyl)- N-(2'-methoxyacetyl)-alanin-methyl- ester, N-(2,6-Dimethylphenyl)-N-chloracetyl- D,L-2-aminobutyrolacton, DL-N-(2,6-Dimethylphenyl)-N-(phenylacetyl)- alaninmethylester, 5-Methyl-5-vinyl-3-(3,5-dichlorphenyl)-2,4-dioxo-1 ,3- oxazolidin, 3-[3,5-Dichlorphenyl(-5-methyl-5-methoxymethyl]-1 ,3-oxazoIidin- 2,4- dion, 3-(3,5-Dichlorphenyl)-1-isopropylcarbamoylhydantoin, N-(3,5- Dichlorphenyl)-1 ,2-dimethylcyclopropan-1 ,2-dicarbonsäureimid, 2-Cyano-[N- (ethyiaminocarbonyl)-2-methoximino]-acetamid, 1 -[2-(2,4- Dichlorphenyl)-pentyl]-1 H-1 ,2,4-triazol, 2,4-Difluor-a-(1 H- 1 ,2,4-triazolyl-1-methyl)-benzhydrylalkohol, N-(3-Chlor-2,6- dinitro-4-trifluormethyl-phenyl)-5-trifluormethyl-3-chlor-2- aminopyridin, 1-((bis-(4-Fluorphenyl)-methylsilyl)-methyl)-1 H-1 ,2,4-triazol.Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) -acrylic acid morpholide, as well as various fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2- hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) -N-furoyl (2) -alaninate, DL-N- (2,6-dimethyl-phenyl) -N- (2 '-methoxyacetyl) alanine methyl ester, N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl (-5-methyl-5-methoxymethyl ] -1,3-oxazolidine-2,4-dione, 3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboxylic acid imide, 2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] -acetamide, 1 - [2- (2,4-dichlorophenyl) -pentyl] -1H-1, 2,4-triazole, 2,4-difluoro -a- (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol, N- (3-chloro-2,6-dinitro-4-trifluoromethylphenyl) -5-trifluoromethyl- 3-chloro-2-aminopyridine, 1 - ((bis (4-fluorophenyl) methylsilyl) methyl) -1H-1, 2,4-triazole.
Die Verbindungen der Formel I zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Basidiomyceten, Phycomyceten und Deuteromyceten aus. Sie sind z.T. systemisch wirksam und können daher auch als Blatt- und Bodenfungizide eingesetzt werden. Sie können auch zur Saatgutbehandlung verwendet werden.The compounds of the formula I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes. You are currently systemically effective and can therefore also be used as foliar and soil fungicides. They can also be used for seed treatment.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemüsepflanzen (z.B. Gurken, Bohnen, Tomaten, Kartoffeln und Kürbisgewächse), Gerste, Gras, Hafer, Bananen, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, Weizen, Zierpflanzen, Zuckerrohr so- wie an einer Vielzahl von Samen. Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Blumeria graminis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Un- cinula necator an Reben, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwol- le, Reis und Rasen, Ustilago-Arten an Getreide und Zuckerrohr, Venturia inaequalis (Schorf) an Äpfeln, Helminthosporium-Arten an Getreide, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudocercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Arten in Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, Mycosphaerella-Arten in Bananen sowie Fusarium- und Verticillium-Arten, Phakopsora pachyrhizi sowie P. meibomiae an Soja.Of particular importance for the control of a variety of fungi on various crops such as cotton, vegetables (eg cucumbers, beans, tomatoes, potatoes and cucurbits), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye, soybean , Wine, wheat, ornamentals, sugar cane and a variety of seeds. In particular, they are suitable for controlling the following phytopathogenic fungi: Blumeria graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Unin cinula necator on vines, Puccinia species on cereals, Rhizoctonia species Cotton, rice and turf, Ustilago species on cereals and sugarcane, Venturia inaequalis on apples, Helminthosporium on cereals, Septoria nodorum on wheat, Botrytis cinera on gray strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudoperonospora species in hops and cucumbers, Alternaria species on vegetables and fruits, Mycosphaerella species in bananas, and Fusarium and Verticillium species, Phakopsora pachyrhizi and P. meibomiae on soya.
Die Aufwandmengen der erfindungsgemäßen Verbindungen der Formel I liegen, vor allem bei landwirtschaftlichen Kulturflächen, je nach Art des gewünschten Effekts bei 0,01 bis 8 kg/ha, vorzugsweise 0,1 bis 5 kg/ha, insbesondere 0,1 bis 3,0 kg/ha.The application rates of the compounds of formula I according to the invention, especially in agricultural crops, depending on the nature of the desired effect at 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.1 to 3.0 kg / ha.
Insbesondere liegen die Aufwandmengen dabei für die Verbindung I bei 0,01 bis 1 kg/ha, vorzugsweise 0,05 bis 0,5 kg/ha, insbesondere 0,05 bis 0,3 kg/ha.In particular, the application rates for compound I are 0.01 to 1 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 0,001 bis 250 g/kg Saatgut, vorzugsweise 0,01 bis 100 g/kg, insbesondere 0,01 bis 50 g/kg verwendet.In the seed treatment, application rates of mixture of 0.001 to 250 g / kg of seed, preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg are generally used.
Sofern für Pflanzen pathogene Schadpilze zu bekämpfen sind, erfolgt die Applikation der Verbindung I durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen.If pathogenic harmful fungi are to be controlled for plants, compound I is applied by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
Die erfindungsgemäßen fungiziden Verbindungen I können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen, Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten aufbereitet und durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsform ist abhängig vom Verwendungszweck; sie soll in jedem Fall eine möglichst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten.The fungicidal compounds I according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules and by spraying, atomizing, dusting , Scattering or pouring are applied. The application form depends on the intended use; It should in any case ensure the finest possible and uniform distribution of the mixture according to the invention.
Die Formulierungen werden in an sich bekannter Weise hergestellt, z.B. durch Zugabe von Lösungsmitteln und/oder Trägerstoffen gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln. Als Lösungsmittel / Hilfsstoffe kommen dafür im wesentlichen in Betracht:The formulations are prepared in a manner known per se, for example by adding solvents and / or carriers, if desired using Emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially:
Wasser, aromatische Lösungsmittel (z.B. Solvesso Produkte, Xylol), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol, Pentanol, Benzylalko- hol), Ketone (z.B. Cyclohexanon, gamma-Butryolacton), Pyrrolidone (NMP, NOP), Acetate (Glykoldiacetat), Glykole, Dimethylfettsäureamide, Fettsäuren und Fettsäureester. Grundsätzlich können auch Lösungsmittelgemische verwendet werden, - Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate); Emulgiermittel wie nichtionogene und anionische Emulgatoren (z.B. Polyoxy- ethylen-Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin-Sulfitablaugen und Methylcellulose.Water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (Glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used, - carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsul- fonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fet- talkoholglycolethern, Kondensationsprodukte von sulfoniertem Naphthalin und seinen Derivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naph- thalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, e- thoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol- oder Tributylphenylpo- lyglycolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid- Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Polyoxypropylen, Laurylalkoholpolyglycoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.As surfactants, the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or Fet- talkoholglycolethern, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecylalcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, Polyoxyethylene alkyl or polyoxypropylene, Laurylalkoholpolyglycoletheracetat, sorbitol esters, lignin-Sulphatablaugen or methylcellulose into consideration.
Pulver Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der Verbindung I mit einem festen Trägerstoff hergestellt werden.Powder scattering and dusting agents can be prepared by mixing or co-grinding Compound I with a solid carrier.
Granulate (z.B. Umhüllungs-, Imprägnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Trägerstoff hergestellt.Granules (e.g., coated, impregnated or homogeneous granules) are usually prepared by binding the active ingredient or agents to a solid carrier.
Als Füllstoffe bzw. feste Trägerstoffe dienen beispielsweise Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe. Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.-% der Verbindung I.As fillers or solid carriers are, for example, mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cornmeal, tree bark, wood and nutshell meal, cellulose powder or other solid carriers. The formulations generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of the compound I.
Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR- oder HPLC-Spektrum) eingesetzt.The active compounds are used in a purity of 90% to 100%, preferably 95% to 100% (by NMR or HPLC spectrum).
Beispiele für Formulierungen sind: 1. Produkte zur Verdünnung in WasserExamples of formulations are: 1. Products for dilution in water
A) Wasserlösliche Konzentrate (SL) 10 Gew.-Teile der Wirkstoffe werden in Wasser oder einem wasserlöslichen Lösungsmittel gelöst. Alternativ werden Netzmittel oder andere Hilfsmittel zugefügt. Bei der Verdünnung in Wasser löst sich der Wirkstoff.A) Water-soluble concentrates (SL) 10 parts by weight of the active compounds are dissolved in water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves.
B) Dispergierbare Konzentrate (DC) 20 Gew.-Teile der Wirkstoffe werden in Cyclohexanon unter Zusatz eines Dispergiermittels z.B. Polyvinylpyrrolidon gelöst. Bei Verdünnung in Wasser ergibt sich eine Dispersion.B) Dispersible Concentrates (DC) 20 parts by weight of the active compounds are dissolved in cyclohexanone with the addition of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
C) Emulgierbare Konzentrate (EC) 15 Gew.-Teile der Wirkstoffe werden in Xylol unter Zusatz von Ca-C) Emulsifiable Concentrates (EC) 15 parts by weight of the active compounds are dissolved in xylene with addition of calcium
Dodecylbenzoisulfonat und Ricinusölethoxylat (jeweils 5 %) gelöst. Bei der Verdünnung in Wasser ergibt sich eine Emulsion.Dodecylbenzoisulfonate and castor oil ethoxylate (each 5%) dissolved. Dilution in water results in an emulsion.
D) Emulsionen (EW, EO) 40 Gew.-Teile der Wirkstoffe werden in Xylol unter Zusatz von Ca-D) Emulsions (EW, EO) 40 parts by weight of the active compounds are dissolved in xylene with addition of calcium
Dodecylbenzolsulfonat und Ricinusölethoxylat (jeweils 5 %) gelöst. Diese Mischung wird mittels einer Emulgiermaschine (Ultraturax) in Wasser eingebracht und zu einer homogenen Emulsion gebracht. Bei der Verdünnung in Wasser ergibt sich eine Emulsion.Dodecylbenzenesulfonate and castor oil ethoxylate (5% each). This mixture is introduced by means of an emulsifier (Ultraturax) in water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
E) Suspensionen (SC, OD)E) suspensions (SC, OD)
20 Gew.-Teile der Wirkstoffe werden unter Zusatz von Dispergier- und Netzmitteln und Wasser oder einem organischen Lösungsmittel in einer Rührwerkskugelmühle zu einer feinen Wirkstoffsuspension zerkleinert. Bei der Verdünnung in Wasser ergibt sich eine stabile Suspension des Wirkstoffs.20 parts by weight of the active ingredients are comminuted with the addition of dispersing and wetting agents and water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
F) Wasserdispergierbare und wasserlösliche Granulate (WG, SG)F) Water-dispersible and water-soluble granules (WG, SG)
50 Gew.-Teile der Wirkstoffe werden unter Zusatz von Dispergier- und Netzmitteln fein gemahlen und mittels technischer Geräte (z.B. Extrusion, Sprühturm, Wirbelschicht) als wasserdispergierbare oder wasserlösliche Granulate hergestellt. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs. G) Wasserdispergierbare und wasserlösliche Pulver (WP, SP) 75 Gew.-Teile der Wirkstoffe werden unter Zusatz von Dispergier- und Netzmitteln sowie Kieselsäuregel in einer Rotor-Strator Mühle vermählen. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs.50 parts by weight of the active ingredients are finely ground with the addition of dispersants and wetting agents and prepared by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient. G) Water-dispersible and water-soluble powders (WP, SP) 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
2. Produkte für die Direktapplikation2. Products for direct application
H) Stäube (DP)H) dusts (DP)
5 Gew.Teile der Wirkstoffe werden fein gemahlen und mit 95 % feinteiligem Kaolin in- nig vermischt. Man erhält dadurch ein Stäubmittel.5 parts by weight of the active ingredients are finely ground and mixed intimately with 95% finely divided kaolin. This gives you a dust.
I) Granulate (GR, FG, GG, MG)I) Granules (GR, FG, GG, MG)
0.5 Gew-Teile der Wirkstoffe werden fein gemahlen und mit 95.5 % Trägerstoffe verbunden. Gängige Verfahren sind dabei die Extrusion, die Sprühtrocknung oder die Wirbelschicht. Man erhält dadurch ein Granulat für die Direktapplikation.0.5 parts by weight of the active ingredients are finely ground and combined with 95.5% excipients. Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application.
J) ULV- Lösungen (UL)J) ULV solutions (UL)
10 Gew.-Teile der Wirkstoffe werden in einem organischen Lösungsmittel z.B. Xylol gelöst. Dadurch erhält man ein Produkt für die Direktapplikation.10 parts by weight of the active compounds are dissolved in an organic solvent, e.g. Xylene dissolved. This gives you a product for direct application.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubmitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring. The forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netz- baren Pulvern (Spritzpulver, Öldispersionen) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermitttel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Netz-, Haft-, Dispergier- oder Emulgiermittel und even- tuell Lösungsmittel oder öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water. For the preparation of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare from effective substance wetting, adhesion, dispersing or emulsifying agents and any solvents or oil concentrates which are suitable for dilution with water.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. Im allgemeinen liegen sie zwischen 0,0001 und 10%, vorzugsweise zwischen 0,01 und 1%. Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.-% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen.The active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. The active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
Zu den Wirkstoffen können Öle verschiedenen Typs, Netzmittel, Adjuvants, Herbizide, Fungizide, andere Schädlingsbekämpfungsmittel, Bakterizide, gegebenenfalls auch erst unmittelbar vor der Anwendung (Tankmix), zugesetzt werden. Diese Mittel können zu den erfindungsgemäßen Mitteln im Gewichtsverhältnis 1:10 bis 10:1 zugemischt werden.To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just before use (tank mix), are added. These agents can be added to the inventive compositions in a weight ratio of 1:10 to 10: 1.
Die Anwendung der Verbindung I oder der entsprechenden Formulierungen erfolgt so, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einer fungizid wirksamen Menge der Verbindung I behandelt.The application of the compound I or the corresponding formulations is carried out by treating the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free of them with a fungicidally effective amount of compound I.
Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen.The application can be made before or after the attack by the harmful fungi.
HerstellungsbeispielePreparation Examples
Beispiel 1example 1
1.) Synthese von 4,4-Difluoro-3-oxo-buttersäureethylester 1 1.) Synthesis of 4,4-difluoro-3-oxo-butyric acid ethyl ester 1
In 300 ml absolutem Tetrahydrofuran wurden 13,9 g Natriumhydrid gegeben. Bei 35- 40°C gab man eine Lösung von 62 g Difluoressigsäureethylester in 44 g Essigsäure- ethylester zu. Nachdem 7 h bei 40°C gerührt wurde, rührte man das Reaktionsgemisch in 1 I Eiswasser ein, stellte mit 10%iger Schwefelsäure auf pH=3 und extrahierte zweimal mit je 300 ml Methyl-tert-butylether. Die vereinigte organische Phase wurde zweimal mit NaCI-Lösung gewaschen, über Natriumsulfat getrocknet und im Vakuum eingeengt. Der Rückstand wurde destilliert. Man erhielt 59,1 g des Produktes als farbloses ÖI Kp(100mb) = 90-94°C.In 300 ml of absolute tetrahydrofuran was added 13.9 g of sodium hydride. At 35 ° -40 ° C., a solution of 62 g of ethyl difluoroacetate in 44 g of ethyl acetate was added. After 7 h at 40 ° C was stirred, the reaction mixture was stirred into 1 l of ice water, adjusted with 10% sulfuric acid to pH = 3 and extracted twice with 300 ml of methyl tert-butyl ether. The combined organic phase was washed twice with NaCl solution, dried over sodium sulfate and concentrated in vacuo. The residue was distilled. This gave 59.1 g of the product as a colorless oil Kp (100mb) = 90-94 ° C.
2.) Synthese von 2-Ethoxymethylen-4,4-difluoro-3-oxo-buttersäureethylester 22.) Synthesis of 2-ethoxymethylene-4,4-difluoro-3-oxo-butyric acid ethyl ester 2
Eine Mischung von 30 g 4,4-Difluoro-3-oxo-buttersäureethyIester 1 , 44 g ortho- Ameisensäuretriethylether und 55 g Acetanhydrid wurde 4 h unter Ruckfluß gerührt. Anschließend wurde destilliert. Man erhielt 35 g des Produktes als farbloses Öl. Kp = 85-87°C.A mixture of 30 g of 4,4-difluoro-3-oxo-ButtersäureethyIester 1, 44 g of ortho-formic triethyl ether and 55 g of acetic anhydride was stirred under reflux for 4 h. It was then distilled. 35 g of the product were obtained as a colorless oil. Bp = 85-87 ° C.
3.) Synthese von 3-Difluormethyl-1-methyl-pyrazol-4-carbonsäureethylester 33.) Synthesis of 3-Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid ethyl ester 3
In 250 ml absol. Ethanol wurden bei -40°C 33,5 g 2-Ethoxymethylen-4,4-difluoro-3-oxo- buttersäureethylester 2 gelöst. Es wurden 7 g Methylhydrazin zugegeben, 1 h bei - 40°C und 15 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde im Vakuum eingeengt. Der Rückstand wurde aus Pentan umkristallisiert. Man erhielt 29,6 g des Produktes. Fp = 50-51 °C.In 250 ml absol. Ethanol were dissolved at -40 ° C 33.5 g of 2-ethoxymethylene-4,4-difluoro-3-oxobutyrate 2. 7 g of methylhydrazine were added, stirred at -40 ° C. for 1 h and at room temperature for 15 h. The reaction mixture was concentrated in vacuo. The residue was recrystallized from pentane. This gave 29.6 g of the product. Mp = 50-51 ° C.
4.) Synthese von 3-Difluormethyl-1-methyl-pyrazol-4-carbonsäure 44.) Synthesis of 3-Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid 4
In einer Mischung von 80 ml Ethanol und 40 ml Wasser wurden 19,3 g 3-Difluormethyl- 1-methyl-pyrazol-4-carbonsäureethylester 3 und 5,7 g Natriumhydroxid gelöst. Man rührte 2 h bei 60°C. Anschließend wurde im Vakuum eingeengt und der Rückstand in 500 ml Eiswasser aufgenommen und mit 10%iger Salzsäure auf pH=3 gestellt. Es wurde zweimal mit einer Mischung von 300 ml THF und Methyl-tert-butylether (2:3) extrahiert. Die vereinigte organische Phase wurden dreimal mit verdünnter Natrium- Chloridlösung gewaschen, über Natriumsulfat getrocknet und im Vakuum eingeengt. Man erhielt 14,5 g des Produktes als hellgelbes Pulver. Fp = 192-193°C.In a mixture of 80 ml of ethanol and 40 ml of water were dissolved 19.3 g of ethyl 3-difluoromethyl-1-methyl-pyrazole-4-carboxylate 3 and 5.7 g of sodium hydroxide. The mixture was stirred at 60 ° C. for 2 h. The mixture was then concentrated in vacuo and the residue taken up in 500 ml of ice water and adjusted to pH = 3 with 10% hydrochloric acid. It was extracted twice with a mixture of 300 ml of THF and methyl tert-butyl ether (2: 3). The combined organic phase was washed three times with dilute sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. 14.5 g of the product were obtained as a light yellow powder. Mp = 192-193 ° C.
5.) Synthese von ortho-(3,4-Dichlophenyl)-anilin 55.) Synthesis of ortho- (3,4-dichlorophenyl) -aniline 5
Zu einer Lösung von 20,47 g 2-Brom-anilin, 24,98 g 3,4-Dichlorphenylboronsäure und 25,23 g Natriumcarbonat in einer Mischung von 150 ml Wasser und 450 ml Ethylengly- coldimehtylether wurden 0,14 g Tetrakistriphenylphosphin-Palladium(O) gegeben. Man rührte 48 Std. unter Rückfluß. Der Ansatz wurde im Vakuum eingeengt. Der Rückstand wurde mit Methyl-tert-butylether aufgenommen, einmal mit Natriumhydrogen- carbonatlösung und viermal mit Wasser gewaschen, über Natriumsulfat getrocknet und im Vakuum eingeengt. Nach chromatographischer Reinigung mit einer Mischung von Toluol und Cyclohexan (1:2) erhielt man 15,5 g des Produktes als hellgelbes Pulver.To a solution of 20.47 g of 2-bromoaniline, 24.98 g of 3,4-dichlorophenylboronic acid and 25.23 g of sodium carbonate in a mixture of 150 ml of water and 450 ml of ethylene glycol dimethyl ether were added 0.14 g of tetrakistriphenylphosphine palladium (O) given. you stirred for 48 hrs. under reflux. The reaction was concentrated in vacuo. The residue was taken up in methyl tert-butyl ether, washed once with sodium bicarbonate solution and four times with water, dried over sodium sulfate and concentrated in vacuo. After chromatographic purification with a mixture of toluene and cyclohexane (1: 2) gave 15.5 g of the product as a light yellow powder.
6.) Synthese von 3-Difluormethyl-1-methyl-N-(ortho-(3,4-dichlorphenyI)phenyl)-pyrazol- 4-carbonsäureamid 66.) Synthesis of 3-difluoromethyl-1-methyl-N- (ortho- (3,4-dichlorophenyl) phenyl) -pyrazole-4-carboxamide 6
In 20 ml Toluol wurden 0,35 g 3-Difluormethyl-1-methyl-pyrazol-4-carbonsäure 4, 0,47 g ortho-(3,4-Dichlorphenyl)anilin 5, 0,3 g Triethylamin und 0,55 g Bis-(2-oxo-3- oxazolidinyl)phosphorylchlorid gelöst. Nachdem 15 h bei Raumtemperatur gerührt wurde, wurden 20 ml Methyl-tert-butylether zugegeben, zweimal mit 5%iger Natronlauge, zweimal mit 5%iger Salzsäure und einmal mit Natriumchloridlösugung gewaschen. Die organische Phase wurde über Natriumsulfat getrocknet und im Vakuum getrocknet. Nach chromatographischer Reinigung mit einer Mischung von Toluol und Methyl-tert- butylether (5:1) erhielt man 0,47 g des Produktes als farbloses Pulver. Fp = 129-130°C.In 20 ml of toluene were added 0.35 g of 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid 4, 0.47 g of ortho- (3,4-dichlorophenyl) aniline 5, 0.3 g of triethylamine and 0.55 g Bis (2-oxo-3-oxazolidinyl) phosphoryl chloride dissolved. After stirring at room temperature for 15 h, 20 ml of methyl tert-butyl ether were added, washed twice with 5% sodium hydroxide solution, twice with 5% hydrochloric acid and once with sodium chloride solution. The organic phase was dried over sodium sulfate and dried in vacuo. After chromatographic purification with a mixture of toluene and methyl tert-butyl ether (5: 1), 0.47 g of the product was obtained as a colorless powder. Mp = 129-130 ° C.
Tabelle 67Table 67
Anwendungsbeispiel example
Wirkstoffaufbereitungdrug treatment
Die Wirkstoffe wurden getrennt oder gemeinsam als eine Stammlösung aufbereitet mit 25 mg Wirkstoff, welcher mit einem Gemisch aus Aceton und/oder DMSO und dem Emulga- tor Uniperol® EL (Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylier- ter Alkylphenole) im Volumen-Verhältnis Lösungsmittel-Emulgator von 99 zu 1 ad 10 ml aufgefüllt wurde. Anschließend wurde ad 100 ml mit Wasser aufgefüllt. Diese Stammlösung wurde mit dem beschriebenen Lösungsmittel-Emulgator-Wasser Gemisch zu der unten angegeben Wirkstoffkonzentration verdünnt. Alternativ dazu wurden die Wirkstoffe als handelsübliche Fertigformulierung verwendet und mit Wasser auf die angegebene Wirkstoffkonz. verdünnt.The active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in volume -Dependent solvent emulsifier from 99 to 1 ad 10 ml was made up. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below. Alternatively, the active ingredients were used as a commercial ready-made formulation and with water to the specified Wirkstoffkonz. diluted.
Anwendungsbeispiel 1 - Kurative Wirksamkeit gegen Weizenbraunrost verursacht durch Puccinia reconditaUse Example 1 - Curative activity against wheat brown rust caused by Puccinia recondita
Blätter von in Töpfen gewachsenen Weizensämlingen der Sorte "Kanzler" wurden mit einer Sporensuspension des Braunrostes (Puccinia recondita) inokuliert. Danach wurden die Töpfe für 24 Stunden in eine Kammer mit hoher Luftfeuchtigkeit (90 bis 95 %) und 20 bis 22° C gestellt. Während dieser Zeit keimten die Sporen aus und die Keimschläuche drangen in das Blattgewebe ein. Die infizierten Pflanzen wurden am nächsten Tag mit einer wässriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropf-nässe besprüht. Die Suspension oder Emulsion wurde wie oben beschrieben hergestellt. Nach dem Antrocknen des Spritzbelages wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 22° C und 65 bis 70 % relativer Luftfeuchte für 7 Tage kultiviert. Dann wurde das Ausmaß der Rostpilzentwicklung auf den Blättern ermittelt.Leaves of potted wheat seedlings of the variety "Chancellor" were inoculated with a spore suspension of the brown rust (Puccinia recondita). Thereafter, the pots were placed in a high humidity chamber (90-95%) and 20-22 ° C for 24 hours. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The infected plants were sprayed the next day with an aqueous suspension in the active ingredient concentration below to dripping wetness. The suspension or emulsion was prepared as described above. After the spray coating had dried on, the test plants were cultivated in the greenhouse at temperatures between 20 and 22 ° C. and 65 to 70% relative atmospheric humidity for 7 days. Then the extent of rust fungus development on the leaves was determined.
Anwendungsbeispiel 2a) - Wirksamkeit gegen den Grauschimmel an Paprikablättern verursacht durch Botrytis cinerea bei protektiver AnwendungApplication Example 2a) - Activity against the gray mold on pepper leaves caused by Botrytis cinerea in protective application
Paprikasämlinge der Sorte "Neusiedler Ideal Elite" wurden, nachdem sich 2 - 3 Blätter gut entwickelt hatten, mit einer wässrigen Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. Am nächsten Tag wurden die behandelten Pflanzen mit einer Sporensuspension von Botrytis cinerea, die 1.7 x 106 Sporen/ml in einer 2 %igen wässrigen Biomalzlösung enthielt, inokuliert. Anschließend wurden die Versuchspflanzen in eine Klimakammer mit 22 bis 24°C, Dunkelheit und hoher Luftfeuchtigkeit gestellt. Nach 5 Tagen konnte das Ausmaß des Pilzbefalls auf den Blättern visuell in % ermittelt werden.Paprika seedlings of the cultivar "Neusiedler Ideal Elite" were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below, after 2-3 leaves had developed well. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution. Subsequently, the test plants were placed in a climatic chamber at 22 to 24 ° C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
Anwendungsbeispiel 2b) - Wirksamkeit gegen die Netzfleckenkrankheit der Gerste verursacht durch Pyrenophora teres bei 1 Tag protektiver AnwendungApplication Example 2b) - Efficacy against the net blotch of barley caused by Pyrenophora teres at 1 day of protective application
Blätter von in Töpfen gewachsenen Gerstenkeimlingen wurden mit wässriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. 24 Stunden nach dem Antrocknen des Spritzbelages wurden die Versuchspflanzen mit einer wässrigen Sporensuspension von Pyrenophora [syn. Drechslera] teres, dem Erreger der Netzfleckenkrankheit inokuliert. Anschließend wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 24° C und 95 bis 100 % relativer Luftfeuchtigkeit aufgestellt. Nach 6 Tagen wurde das Ausmaß der Krankheitsentwicklung visuell in % Befall der gesamten Blattfläche ermittelt.Leaves of potted barley seedlings were sprayed to drip point with aqueous suspension in the concentration of active compound given below. 24 hours after the spray coating had dried on, the test plants were incubated with an aqueous spore suspension of Pyrenophora [syn. Drechslera] teres, the causative agent of net blotch inoculation. Subsequently, the test plants were placed in the greenhouse at temperatures between 20 and 24 ° C and 95 to 100% relative humidity. After 6 days, the extent of disease development was determined visually as% of total leaf area.
Vergleichsversuch 1Comparative experiment 1
Kurative Wirksamkeit gegen Weizenbraunrost verursacht durch Puccinia reconditaCurative efficacy against wheat brown rust caused by Puccinia recondita
Verglichen wurde die Verb. 35 der EP-A 0589301 mit den erfindungsgemäßen Verbindungen 67.1 - 67.14 der Tabelle 67. Blätter von in Töpfen gewachsenen Weizensämlingen der Sorte "Kanzler" wurden mit einer Sporensuspension des Braunrostes (Puccinia recondita) inokuliert. Danach wurden die Töpfe für 24 Stunden in eine Kammer mit hoher Luftfeuchtigkeit (90 bis 95 %) und 20 bis 22° C gestellt. Während dieser Zeit keimten die Sporen aus und die Keimschläuche drangen in das Blattgewebe ein. Die infizierten Pflanzen wurden am nächsten Tag mit einer wässriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. Die Suspension oder Emulsion wurde wie oben beschrieben hergestellt. Nach dem Antrocknen des Spritzbelages wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 22° C und 65 bis 70 % relativer Luftfeuchte für 7 Tage kultiviert. Dann wurde das Ausmaß der Rostpilzentwicklung auf den Blättern ermittelt.Compound 35 of EP-A 0589301 was compared with the compounds 67.1-67.14 according to the invention of Table 67. Leaves of potted wheat seedlings of the "Chancellor" variety were inoculated with a spore suspension of the brown rust (Puccinia recondita). Thereafter, the pots were placed in a high humidity chamber (90-95%) and 20-22 ° C for 24 hours. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The infected plants were sprayed the next day with an aqueous suspension in the drug concentration given below to dripping wet. The suspension or emulsion was prepared as described above. After the spray coating had dried on, the test plants were cultivated in the greenhouse at temperatures between 20 and 22 ° C. and 65 to 70% relative atmospheric humidity for 7 days. Then the extent of rust fungus development on the leaves was determined.
Vergleichsversuch 2Comparative experiment 2
Wirksamkeit gegen die Blattfleckenkrankheit an Weizen verursacht durch Lep- tosphaeria nodorumEfficacy against leaf spot disease on wheat caused by Leposphaeria nodorum
Verglichen wurde die Verb. 35 der EP-A 0589301 mit den erfindungsgemäßen Verbindungen 67.1 - 67.14 der Tabelle 67. Töpfe mit Weizenpflanzen der Sorte „Kanzler" wurden mit einer wässrigen Suspension in der unten angegebenen Wirkstoffkonzentra- tion bis zur Tropf-nässe besprüht. Am folgenden Tag wurden die Töpfe mit einer wässrigen Sporensuspension von Leptosphaeria nodorum (syn.Stagonospora nodorum, Septoria nodorum) inokuliert. Anschließend wurden die Pflanzen in einer Kammer bei 20°C und maximaler Luftfeuchte aufgestellt. Nach 8 Tagen hatte sich die Blattfieckenkrankheit auf den unbehandelten, jedoch infizierten Kontrollpflanzen so stark entwi- ekelt, dass der Befall visuell in % ermittelt werden konnte. Comp. 35 of EP-A 0589301 was compared with the compounds 67.1-67.14 according to the invention of Table 67. Pots of wheat plants of the "Chancellor" variety were sprayed to drip point with an aqueous suspension in the concentration of active substance specified below the next day, the pots were inoculated with an aqueous spore suspension of Leptosphaeria nodorum (syn. Stagonospora nodorum, Septoria nodorum) and then placed in a chamber at 20 ° C and maximum humidity. However, infected control plants developed so much that the infestation could be determined visually in%.

Claims

Patentansprüche claims
1. 1 -Methyl-3-difluormethyl-pyra∑ol-4-carbonsäure-(ortho-phenyl)-anilide der Formel I1. 1-Methyl-3-difluoromethyl-pyraΣol-4-carboxylic acid (ortho-phenyl) -anilide of the formula I.
in der die Substituenten die folgende Bedeutung haben: in which the substituents have the following meaning:
R1 und R 2 unabhängig voneinander Halogen, Cι-C6-Alkyl, CrC6 Halogen-alkyl, Cyano, Nitro, Methoxy, Trifluormethoxy oder Difluormethoxy.R 1 and R 2 are independently halogen, Cι-C6 alkyl, -C 6 halogen-alkyl, cyano, nitro, methoxy, trifluoromethoxy or difluoromethoxy.
2. Anilide der Formel I nach Anspruch 1 , in der R1 und R2 unabhängig voneinander für Fluor, Chlor, Cyano, Methyl, Methoxy oder Trifluormethyl stehen.2. anilides of the formula I according to claim 1, in which R 1 and R 2 are independently fluorine, chlorine, cyano, methyl, methoxy or trifluoromethyl.
3. Anilide der Formel I nach Anspruch 1 oder 2, in der R1 und R2 unabhängig voneinander für Fluor, Chlor, Cyano oder Methoxy stehen.3. Anilides of the formula I according to claim 1 or 2, in which R 1 and R 2 independently of one another represent fluorine, chlorine, cyano or methoxy.
4. Anilide der Formel I nach Anspruch 1 , in der R1 und R2 unabhängig voneinander für Fluor oder Chlor stehen.4. anilides of the formula I according to claim 1, in which R 1 and R 2 are independently fluorine or chlorine.
5. Anilide der Formel I nach einem der Ansprüche 1 bis 4, enthaltend eine Verbindung der Formel I, in der die Substituenten R1 und R2 in der 3- und 4-Position des Phenylringes stehen.5. Anilides of the formula I according to any one of claims 1 to 4, containing a compound of formula I, in which the substituents R 1 and R 2 are in the 3- and 4-position of the phenyl ring.
6. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, dass man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einem Anilid der Formel I gemäß einem der Ansprüche 1 bis 5 behandelt.6. A method for controlling harmful fungi, which comprises treating the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free of them with an anilide of the formula I according to one of claims 1 to 5.
7. Fungizide Mittel, enthaltend ein Anilid der Formel I gemäß Anspruch 1 sowie einen festen oder flüssigen Träger. 7. A fungicidal composition containing an anilide of the formula I according to claim 1 and a solid or liquid carrier.
EP05750478A 2004-06-18 2005-06-16 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide Withdrawn EP1761498A1 (en)

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