Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • 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
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
  • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
  • C07C49/233—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
• • 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
  • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms

Definitions

• the present invention relates to new triazolyl-butane derivatives, a process for their preparation and their
• A represents a keto group or a CH (OH) group
• R represents alkyl, optionally substituted cycloalkylalkyl, alkenyl, alkynyl or haloalkenyl, but the meaning 3-chloro-but-2-en-1-yl is excluded, and their acid addition salts and metal salt complexes have been found «
• the compounds of formula (I) in which A represents a keto group have an asymmetrically substituted carbon atom. In both cases, the compounds of formula (I) can exist in different optical isomer forms, which can be obtained in different proportions.
• the present invention relates to both the isomer mixtures and the individual isomers.
• X represents an electron-withdrawing leaving group, in the presence of a base and in the presence of a diluent or in an aqueous-organic two-phase system in the presence of a phase transfer catalyst and, if appropriate, the resulting keto compounds of the formula
• the substances according to the invention outperform 2,2-dimethyl-1-phenyl-4- (1,2,4-triazol-1-yl) octan-3-ol and 2,2-dimethyl-1- (4th -methyl-phenyl) -4- (1,2,4-triazol-1-yl) octan-3-ol, which are structurally obvious, previously known substances with the same direction of action, with regard to their fungicidal properties.
• the new triazolylbutane derivatives of the formula (I) are interesting intermediates for the preparation of other crop protection active ingredients. For example, those compounds in which A is CO can be converted into oximes, oxime ethers, hydrazones or ketals.
• A represents a CH (OH) grouping
• Those compounds in which A represents a CH (OH) grouping can be converted into ether or converted into acyl or carbamoyl derivatives by reaction with acyl halides or carbamoyl chlorides.
• the triazolyl butane derivatives according to the invention are generally defined by the formula (I).
• A stands for a keto group or a CH (OH) group
• R preferably represents straight-chain or branched alkyl having 1 to 12 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety 1 and 1 to 4 carbon atoms in the alkyl part optionally substituted by 1 to 3 alkyl groups having 1 to 4 carbon atoms, straight-chain or branched alkenyl with 3 to 12 carbon atoms, for straight-chain or branched alkynyl with 3 to 12 carbon atoms, or for straight-chain or branched haloalkenyl with 3 to 12 carbon atoms and 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and / or bromine atoms, however, R is not 3-chloro-but-2-en-1-yl. Is particularly preferred
• R for straight-chain or branched alkyl having 1 to 10 carbon atoms, for cycloalkylalkyl optionally having 1 to 3 methyl and / or ethyl groups and having 3 to 6 carbon atoms in the cycloalkyl part and 1 or 2 carbon atoms in the
• Alkyl part for straight-chain or branched alkenyl with 3 to 10 carbon atoms, for straight-chain or branched alkynyl with 3 to 10 carbon atoms, or for straight-chain or branched haloalkenyl with 3 to 10 carbon atoms and 1 to 5 fluorine, chlorine and / or bromine atoms, where However, R does not represent 3-chloro-but-2-en-1-yl.
• Preferred substances according to the invention are also addition products of acids and triazolylbutane derivatives of the formula (I) in which A and R have the meanings given as preferred above.
• the acids which can be added preferably include hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, fumaric acid, Tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid as well as sulfonic acids such as p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid or camphorsulfonic acid, as well as saccharin and thiosaccharin.
• hydrohalic acids such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example,
• preferred compounds according to the invention are addition products from salts of metals of the II. To IV. Main and of I. and II. And IV, to VIII. Subgroup of the periodic table of the elements and triazolylbutane derivatives of the formula (I), in which A and R have the meanings given above as preferred.
• Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred.
• Anions of these salts are those which are derived from acids which lead to physiologically tolerable addition products.
• Particularly preferred such acids in this connection are the hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid and sulfuric acid.
• the 1- (4-trifluoromethylphenyl) -2,2-dimethyl-4- (1,2,4-triazol-1-yl) butan-3-one of the formula (II) required as starting material for carrying out the process according to the invention is not yet known. It can be prepared by using halogen ketones of the formula
• Hai represents chlorine or bromine, with 1, 2,4-triazole of the formula
• Diluents used in the preparation of 1- (4-trifluoromethyl-phenyl) -2,2-dimethyl-4- (1,2,4-triazol-1-yl) butan-3-one of the formula (II) are inert organic solvents in question. Are preferably usable
• Ketones such as acetone, diethyl ketone and methyl ethyl ketone; Nitriles such as propionitrile and ⁇ cetonitrile; Alcohols such as ethanol or isopropanol ether, such as tetrahydrofuran or dioxane; aromatic hydrocarbons such as toluene, benzene or chlorobenzene; Formamides such as dimethylformamide; and halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride.
• Alkaline metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, or lower tertiary alkylamines, cycloalkylamines or aralkylamines, for example triethylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, N, N-dimethylbenzylamine, are preferably usable. further pyridine and diazabicyclooctane, or an excess of 1, 2,4-triazole.
• reaction temperatures can be in the above process for the preparation of 1- (4-trifluoromethyl-phenyl) -2,2-dimethyl-4- (1,2,4-triazol-1-yl) butan-3-one of the formula (II) can be varied over a wide range. In general, temperatures between 20 ° C and 150 ° C, preferably between 40 ° C and 120 ° C.
• the 1- (4-trifluoromethyl-phenyl) -2,2-dimethyl-butan-3-one of the formula (VI) is also not yet known. It can be prepared by using methyl isopropyl ketone of the formula
• Hai is chlorine or bromine, in the presence of a base, such as an alkali or alkaline earth metal hydroxide, such as powdered potassium and sodium hydroxide, and in the presence of a diluent, such as a (cyclo) aliphatic or optionally chlorinated aromatic
• Hydrocarbon such as benzene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, petroleum ether, pentane, hexane or toluene, and in the presence of a phase transfer catalyst, such as a derivative of an ammo nium salt, triethylbenzylammonium chloride, tetrabutylammonium iodide, bromide or chloride being specifically mentioned, at temperatures between 0 ° C. and 150 ° C.,
• Methyl isopropyl ketone of the formula (VII) and the halides of the formula (VIII) are known compounds of organic chemistry.
• Formula (III) provides a general definition of the compounds required as reaction components when carrying out the process according to the invention.
• R preferably represents those radicals which have already been mentioned as preferred for this substituent in connection with the description of the triazolylbutane derivatives of the formula (I) according to the invention.
• X preferably represents chlorine, bromine, iodine, 4-methylphenylsulfonyloxy, the grouping -O-SO 2 -OR 1 or NR 1 3 , where R 1 represents methyl, ethyl, n-propyl or isopropyl.
• the compounds of the formula (III) are generally known substances in organic chemistry,
• Inert organic solvents are suitable as diluents when carrying out the first stage of the process according to the invention.
• Aromatic hydrocarbons such as benzene, toluene or xylene, can also be used, furthermore halogenated hydrocarbons, such as methylene chloride, carbon tetrachloride, chloroform or Chlorobenzene, also esters, such as ethyl acetate, further amides, such as dimethyl formamide, and also strongly polar solvents, such as dimethyl sulfoxide.
• Suitable bases for carrying out the first stage of the process according to the invention are all customary organic and inorganic acid binders,
• Alkali metal hydroxides or alkali metal carbonates are preferably usable.
• the reaction temperatures can be varied within a substantial range when carrying out the first stage of the process according to the invention. In general, temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 100 ° C.
• the first stage of the method according to the invention can also be carried out in a two-phase system, for example a system aqueous sodium or potassium hydroxide solution / toluene or methylene chloride, optionally with the addition of 0.1 to 1 mol of a phase transfer catalyst, for example an ammonium or phosphonium compound, such as benzyldodecyldimethylammonium chloride or triethylbenzylamraonium chloride.
• a phase transfer catalyst for example an ammonium or phosphonium compound, such as benzyldodecyldimethylammonium chloride or triethylbenzylamraonium chloride.
• Both the first stage and the second stage of the process according to the invention and also the reactions described above for the production of intermediate products are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• keto compounds of the formula (Ia) formed when the first step of the process according to the invention is carried out can be reduced either with the aid of complex hydrides or aluminum isopropylate.
• Sodium borohydride and lithium aluminum hydride are preferably suitable as complex hydrides when carrying out the second stage of the process according to the invention (variant ⁇ ).
• Suitable diluents for carrying out the second stage of the process according to variant ⁇ are polar organic solvents.
• Alcohols such as methanol, ethanol, isopropanol or butanol
• ethers such as diethyl ether or tetrahydrofuran, or else water in a mixture with an alcohol, are preferably usable.
• the reaction temperatures can be varied within a certain range when carrying out the second stage of the process according to variant oc. In general, temperatures between 0 ° C and 30 ° C, preferably between 0 ° C and 20 ° C.
• keto compound of the formula (Ia) When carrying out the second stage of the process according to variant oc according to the invention, an equivalent amount or an excess of complex hydride is employed per mole of keto compound of the formula (Ia).
• the processing takes place according to usual methods. In general, the procedure is such that water is added to the reaction mixture, extracted with a water-immiscible organic solvent, the combined organic phases are dried and concentrated. However, it is also possible to first add dilute aqueous acid, for example hydrochloric acid, to the reaction mixture, then to make it alkaline and then to work in the manner described above.
• dilute aqueous acid for example hydrochloric acid
• the diluents used are preferably alcohols, such as isopropanol, or hydrocarbons, such as benzene.
• the reaction temperatures can be varied within a substantial range. In general, temperatures between 20 ° C and 120 ° C, preferably between 50 ° C and 100 ° C.
• 1 to 2 mol of aluminum isopropylate are generally employed per mol of keto compound of the formula (Ia). The processing takes place according to usual methods.
• reaction mixture is concentrated, the remaining residue is treated with dilute aqueous acid or base, then extracted with an organic solvent which is not very miscible with water, and the combined organic phases are dried and concentrated.
• the triazolylbutane derivatives of the formula (I) according to the invention can be converted into acid addition salts or metal salt complexes.
• acid addition salts of the compounds of formula (I) preference is given to those acids which have already been mentioned as preferred acids in connection with the description of the acid addition salts according to the invention.
• the acid addition salts of the compounds of the formula (I) can be obtained in a simple manner by customary salt formation methods, for example by dissolving a compound of the formula (I) in a suitable inert solvent and adding the acid, for example hydrochloric acid, and in a known manner, for example by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
• metal salt complexes of the compounds of formula (I) preference is given to those salts of metals which have already been mentioned as preferred metal salts in connection with the description of the metal salt complexes according to the invention.
• the metal salt complexes of the compounds of the formula (I) can be obtained in a simple manner by customary processes, for example by dissolving the metal salt in alcohol, for example ethanol and adding it to compounds of the formula (I).
• Metal salt complexes can be isolated in a known manner, for example by filtering off and, if appropriate, purified by recrystallization.
• the active compounds according to the invention have a strong microbicidal action and can be used as fungicides.
• Fungicides are used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes,
• Xanthomonas species such as Xanthomonas oryzae
• Pseudomonas species such as Pseudomonas lachrymans
• Erwinia species such as Erwinia amylovora
• Pythium species such as Pythium ultimum
• Phytophthora species such as Phytophthora infestans
• Pseudoperonospora species such as Pseudoperonospora humuli or Pseudoperonospora cubensis;
• Plasmopara species such as Plasmopara viticola
• Peronospora species such as Peronospora pisi or P,
• Erysiphe species such as Erysiphe graminis
• Sphaerotheca species such as Sphaerotheca fuliginea
• P ⁇ dosphaera species such as Podosphaera leucotricha
• Venturia species such as Venturia inaequalis
• Pyrenophora species such as Pyrenophora teres or P, graminea
• Drechslera (Conidial form: Drechslera, Syn: Helminthosporium).
• Cochliobolus species such as Cochliobolus sativus
• Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
• Uromyces species such as Uromyces appendiculatus
• Puccinia species such as Puccinia recondita
• Tilletia species such as Tilletia caries
• Ust ilago species such as Ustilago nuda or Ustilago avenae;
• Pellicularia species such as Pellicularia sasakii
• Pyricularia species such as Pyricularia oryzae
• Fusarium species such as Fusarium culmorum
• Botrytis species such as Botrytis cinerea
• Septoria species such as Septoria nodorum
• Leptosphaeria species such as Leptosphaeria nodorum
• Cercospora species such as Cercospora canescens
• Alternaria species such as Alternaria brassicae
• Pseudocercosporella species such as Pseudocercosporel la herpotrichoides.
• the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds and of the soil.
• the active compounds according to the invention are particularly suitable for combating Pyricularia oryzae and Pellicularia sasakii on rice and for combating cereal diseases, such as Leptosphaeria nodorum, Cochliobolus sativus, Pyrenophora teres, Pseudocercosporella herpotrichoides, Puccinia recondita, Erysiphe and Fusarium species.
• the substances according to the invention have a very good action against Uncinula. They also have a broad in-vitro action.
• the substances according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
• These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• aromatics such as xylene, toluene, or Alkyl
• Chlorethylene or methylene chloride aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water ;
• Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide;
• Solid carrier materials are suitable: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmoril lonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; Possible solid carriers for granules are:
• Adhesives such as carbokymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g.
• Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal lphthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and in mixtures with fertilizers and growth regulators.
• the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
• the application rate can be varied over a wide range depending on the type of application.
• the active substance concentrations in the treatment of parts of plants in the use forms are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
• amounts of active compound of 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g are generally required.
• active substance concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% are required at the place of action.
• a solution of 4.15 g (0.074 mol) of potassium hydroxide in 25 ml of water is stirred at room temperature, starting with 10 minutes, into a solution of 15 g (0.048 mol) of 1- (4-trifluoromethylphenyl) -2,2-dimethyl- 4- (1,2,4-triazol-1-yl) butan-2-one and 10.5 g (0.074 mol) of methyl iodide were added dropwise in 130 ml of dimethyl sulfoxide.
• the reaction mixture is kept at 40 ° C. by cooling. After the addition has ended, the mixture is stirred at 40 ° C. for 5 hours. For working up, the reaction mixture is poured into water.
• Emulsifier 0.25 parts by weight of alkylaryl polyglycol ether
• the plants are placed in a greenhouse at a temperature of approx. 10 ° C. and a relative humidity of approx. 80 5.
• Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.
• the substances according to the invention of the formulas (1-5), (1-11), (1-12) and (1-14) at a concentration of 0.025% by weight in the spray mixture show a substantially better activity than the reference substance (A).
• Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
• the plants are then placed in a greenhouse at 23 to 24 ° C and at a relative humidity of approx. 75%.
• Evaluation is carried out 14 days after the inoculation.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)

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• 1992
  • 1992-07-09 DE DE4222541A patent/DE4222541A1/de not_active Withdrawn
• 1993
  • 1993-06-28 WO PCT/EP1993/001654 patent/WO1994001418A1/de not_active Application Discontinuation
  • 1993-06-28 JP JP6502891A patent/JPH07508737A/ja active Pending
  • 1993-06-28 KR KR1019950700055A patent/KR950702542A/ko not_active Application Discontinuation
  • 1993-06-28 AU AU45603/93A patent/AU4560393A/en not_active Abandoned
  • 1993-06-28 EP EP93915724A patent/EP0649416A1/de not_active Withdrawn
  • 1993-06-28 BR BR9306706A patent/BR9306706A/pt not_active Application Discontinuation

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