WO1994004529A1 - Derives 1,3-oxazolidine substitues par un pyridyle et leur utilisation comme parasiticides - Google Patents

Derives 1,3-oxazolidine substitues par un pyridyle et leur utilisation comme parasiticides Download PDF

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Publication number
WO1994004529A1
WO1994004529A1 PCT/EP1993/002076 EP9302076W WO9404529A1 WO 1994004529 A1 WO1994004529 A1 WO 1994004529A1 EP 9302076 W EP9302076 W EP 9302076W WO 9404529 A1 WO9404529 A1 WO 9404529A1
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WO
WIPO (PCT)
Prior art keywords
straight
chain
carbon atoms
branched
haloalkyl
Prior art date
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PCT/EP1993/002076
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German (de)
English (en)
Inventor
Hans-Ludwig Elbe
Ralf Tiemann
Stefan Böhm
Stefan Dutzmann
Heinz-Wilhelm Dehne
Original Assignee
Bayer Aktiengesellschaft
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Filing date
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU47070/93A priority Critical patent/AU4707093A/en
Publication of WO1994004529A1 publication Critical patent/WO1994004529A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles

Definitions

  • the invention relates to new pyridyl-substituted 1,3-oxazolidine derivatives, a process for their preparation and their use in pesticides. It is known that certain 1,3-oxazolidine derivatives, such as, for example, the compound 5-fluoromethyl-3- (4-memylthio-phenyl) -1,3-oxazolidin-2-one, have fungicidal properties (cf., for example, US Pat 4,128,654).
  • R 1 represents hydrogen, alkyl or haloalkyl
  • R 2 represents hydrogen, alkyl or haloalkyl
  • R 3 represents hydrogen, alkyl or haloalkyl
  • R 4 represents hydrogen, alkyl or haloalkyl
  • Ar represents optionally substituted aryl.
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • R 1 represents hydrogen, alkyl or haloalkyl
  • R 2 represents hydrogen, alkyl or haloalkyl
  • R 3 represents hydrogen, alkyl or haloalkyl
  • R 4 represents hydrogen, alkyl or haloalkyl
  • Ar represents optionally substituted aryl if pyridin-3-aldehyde of the formula (II) with amino alcohols of the formula (III),
  • R 1 , R 2 , R 3 , R 4 and Ar have the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
  • the pyridyl-substituted 1,3-oxazolidine derivatives of the general formula (I) according to the invention show a considerably better activity against microorganisms which damage the plants in comparison to the 1,3-oxazolidine derivatives known from the prior art, such as, for example, the compound 5-fluoromethyl -3- (4-methylthio-phenyl) -1,3-oxazolidin-2-one, which are chemically and / or functionally obvious compounds.
  • the pyridyl-substituted 1,3-oxazoHdin derivatives according to the invention are generally defined by the formula (I). Preference is given to compounds of the formula (I) in which
  • R 1 represents hydrogen, straight-chain or branched alkyl having 1 to 10 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 Carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine -,
  • R 2 represents hydrogen, straight-chain or branched alkyl having 1 to 10 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine,
  • R 3 represents hydrogen, straight-chain or branched alkyl having 1 to 10 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine,
  • R 4 represents hydrogen, straight-chain or branched alkyl having 1 to 10 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine - and
  • Ar represents aryl with 6 to 10 coblenyl atoms which is optionally mono- or polysubstituted, identically or differently, where the following are suitable as substituents:
  • R 1 represents hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine,
  • R 2 represents hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine,
  • R 3 represents hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine
  • R 4 represents hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine - and Ar is optionally Aryl with 1 to 5 substituents, identical or differently substituted, with 6 or 10 coblenyl atoms is available, the following being suitable as substituents:
  • R 1 is hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine, bromine - are very particularly preferred and / or iodine -
  • R 2 represents hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine
  • R 3 represents hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine,
  • R 4 represents hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine,
  • Ar represents phenyl which is monosubstituted to pentasubstituted by identical or different substituents, the following being suitable as substituents:
  • Formula (H) provides a general definition of the pyridine-3-aldehyde required as starting compound for carrying out the process according to the invention.
  • amino alcohols of the formula (III) are known (cf., for example, US Pat. No. 2,391,139; J. Amer. Chem. Soc. 60, 1582-1583 [1938]; J. Amer. Chem. Soc. 45, 789 [1923 ]) or obtainable in analogy to known processes, for example if oxiranes of the formula (IV) are used,
  • R 1 , R 2 , R 3 and R 4 have the meanings given above, with anilines of the formula (V),
  • Ar-NH 2 (V) in which Ar has the meaning given above optionally in the presence of a diluent such as ethanol at temperatures between 50 ° C and 150 ° C.
  • Oxiranes of the formula (IV) are generally known compounds of organic chemistry or can be obtained analogously to generally known processes (cf., for example, EP 368 656; EP 287 347; US 4,587,217; EP 91 305; J. Org. Chem. 45, 3930-3932 [1980]; EP 275221).
  • Anilines of the formula (V) are also generally known compounds of organic chemistry.
  • Inert organic solvents are suitable as diluents for carrying out the process according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride or ethers, such as diethyl ether, diisopropyl ether, dioxane or tetrahane Ethylene glycol Koldimetiyl- or -diethylether optionally in a mixture with higher alcohols, such as butanol.
  • liquid amino alcohols of the formula (III) As reaction components, it is also possible to use them in a corresponding excess at the same time as a diluent.
  • the process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary As such, all commonly used inorganic or organic acids or other conventional catalysts are suitable. Dilute aqueous or concentrated mineral acids such as hydrochloric acid, sulfuric acid or phosphoric acid or organic sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid are used with particular preference.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably at temperatures between 40 ° C and 180 ° C.
  • the process according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the end products of the formula (I) are purified using customary methods, for example by column chromatography or by recrystallization.
  • the characterization is carried out using the melting point or, in the case of non-crystallizing compounds, using the refractive index or proton nuclear magnetic resonance spectroscopy (1H-NMR).
  • the active compounds according to the invention have a strong action against pests and can be used practically to combat unwanted harmful organisms.
  • the active ingredients are suitable for use as crop protection agents, especially as fungicides.
  • Fungicidal agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Pythium species such as, for example, Pythium ultünum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Plasmopara species such as, for example, Plasmopara viticola
  • Peronospora species such as, for example, Peronospora pisi or Peronospora brassicae
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechslera, synonym: Hehninthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Altemaria species such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella he ⁇ otrichoides.
  • the active compounds according to the invention can be used with particularly good success to combat cereal diseases, such as, for example, against the pathogen causing barley mesh spot disease (Pyrenophora teres) or against the pathogen causing brown spot disease on barley or wheat (Cochliobolus sativus) or against the pathogen causing brown spawn ( Leptosphaeria nodorum) or against the pathogen of powdery mildew on wheat or barley (Erysiphe grarninis), or against the pathogen of cereal stem disease (Pseudocercosporella herpotrichoides) or for combating diseases in fruit and vegetable cultivation, such as against the pathogen of vine mildew Uncinula necator) can be used.
  • cereal diseases such as, for example, against the pathogen causing barley mesh spot disease (Pyrenophora teres) or against the pathogen causing brown spot disease on barley or wheat (Cochliobolus sativus) or against the pathogen causing brown
  • the active compounds can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV Cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimemylformamide or dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide;
  • Solid carrier materials are suitable: for example natural rock powder
  • Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; The following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine, can be used Substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredient, 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 also 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, 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 active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
  • active ingredient 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0, 0001 to 0.02 wt .-% required at the site of action.
  • Solvent 100 parts by weight of dimethylformamide emulsifier: 0.25 parts by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 25 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation.
  • the compounds according to the preparation examples: 11 and 18 at an active substance concentration of 250 ppm in the spray mixture show a clear superiority in effectiveness compared to the prior art.
  • Emulsifier 0.25 parts by weight of alkyl aryl polyglycol ether
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%.
  • Evaluation is carried out 7 days after the inoculation.
  • the compounds according to the preparation examples: 11 and 18 at an active substance concentration of 250 ppm in the spray mixture show a clear superiority in effectiveness compared to the prior art.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • a 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 ° C to 24 ° C and a relative humidity of approx. 75%.
  • Evaluation is carried out 14 days after the inoculation.
  • the compound according to preparation example 10 at an active ingredient concentration of 25 ppm shows a clear superiority in effectiveness compared to the prior art.

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

Abstract

Nouveaux dérivés 1,3-oxazolidine substitués par un pyridyle, ayant la formule (I) dans laquelle R1 à R4 ont les significations indiquées dans la description, leur procédé de fabrication et leur utilisation dans la lutte contre les parasites, par exemple des champignons, de préférence dans le règne végétal. Les nouveaux composés de formule (I) peuvent être fabriqués selon un procédé d'analogie, par exemple par réaction d'aminoalcools appropriés avec le pyridine-3-aldéhyde.
PCT/EP1993/002076 1992-08-17 1993-08-04 Derives 1,3-oxazolidine substitues par un pyridyle et leur utilisation comme parasiticides WO1994004529A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU47070/93A AU4707093A (en) 1992-08-17 1993-08-04 Pyridyl-substituted 1,3-oxazolidine derivatives and their use as pest-control agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924227073 DE4227073A1 (de) 1992-08-17 1992-08-17 Pyridylsubstituierte 1,3-Oxazolidin-Derivate
DEP4227073.1 1992-08-17

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Publication Number Publication Date
WO1994004529A1 true WO1994004529A1 (fr) 1994-03-03

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DE (1) DE4227073A1 (fr)
WO (1) WO1994004529A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005019081A1 (de) * 2005-04-23 2006-11-02 Seitz, Peter Lagerordnungskasten mit verschiebbarer Frontscheibe

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2852427A (en) * 1956-12-05 1958-09-16 Diamond Alkali Co 2-piperonyloxazolidine, process and use as control for microorganisms
US4128654A (en) * 1978-02-10 1978-12-05 E. I. Du Pont De Nemours And Company 5-Halomethyl-3-phenyl-2-oxazolidinones

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2852427A (en) * 1956-12-05 1958-09-16 Diamond Alkali Co 2-piperonyloxazolidine, process and use as control for microorganisms
US4128654A (en) * 1978-02-10 1978-12-05 E. I. Du Pont De Nemours And Company 5-Halomethyl-3-phenyl-2-oxazolidinones

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 89, no. 3, 17 July 1978, Columbus, Ohio, US; abstract no. 24451m, N.K. MAKSUDOV ET AL.: "Searching for new potential pesticides for control of cotton-plant diseases" page 663; *
UZB. KHIM. ZH., no. 2, 1978, pages 70 - 79 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005019081A1 (de) * 2005-04-23 2006-11-02 Seitz, Peter Lagerordnungskasten mit verschiebbarer Frontscheibe

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DE4227073A1 (de) 1994-02-24
AU4707093A (en) 1994-03-15

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