EP0000333B1 - Derivate cyclischer Amine und diese enthaltende Fungizide - Google Patents

Derivate cyclischer Amine und diese enthaltende Fungizide Download PDF

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EP0000333B1
EP0000333B1 EP78100174A EP78100174A EP0000333B1 EP 0000333 B1 EP0000333 B1 EP 0000333B1 EP 78100174 A EP78100174 A EP 78100174A EP 78100174 A EP78100174 A EP 78100174A EP 0000333 B1 EP0000333 B1 EP 0000333B1
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weight
parts
bis
acid
active ingredient
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EP78100174A
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French (fr)
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EP0000333A3 (en
EP0000333A2 (de
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Walter Dr. Himmele
Ernst-Heinrich Dr. Pommer
Norbert Dr. Goetz
Bernd Dr. Zeeh
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom

Definitions

  • the present invention relates to new valuable derivatives of cyclic amines and their salts and molecular and addition compounds with good fungicidal activity, fungicides containing these compounds and methods for combating fungi with these compounds.
  • N-tridecyl-2,6-dimethylmorpholine and its salts and its molecular and addition compounds as fungicides (DT-PS 11 64 152, DT-PS 11 73 722, DT-OS 24 61 513).
  • Salts are, for example, the salts with inorganic or organic acids, for example chlorides, fluorides, bromides, iodides, sulfates, nitrates, phosphates, acetates, propionates, molecular compounds or addition compounds are formed, for example, with acids of surfactants, for example dodecylbenzenesulfonic acid,
  • the new compounds are prepared, for example, by reacting 3-hydroxymethylpiperidine with 3-p-tertiary-butylphenyl-2-methylpropanol in the presence of a reducing agent, e.g. Formic acid at temperatures from 50 to 110 ° C.
  • a reducing agent e.g. Formic acid at temperatures from 50 to 110 ° C.
  • the active compounds according to the invention and the corresponding fungicides are particularly suitable for controlling plant diseases, e.g. Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichloriacearum (powdery mildew) on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Erysiphe polygoni on beans. Sphaerotheca pannosa on roses, Microsphaera querci on oaks, Botrytis cinerea on strawberries, vines, Mycosphaerella musicola on bananas, Puccinia species (rust fungi) on cereals, Uromyces appendiculatus and U. phaseoli on beans, Hemileia vastatrix on coffee and Rhizoctonia solani. They are systematically effective; they are absorbed both through the roots and the leaves and transported in the plant tissue.
  • plant diseases e.g. Erysip
  • the application rates are between 0.025 and 5 kg active ingredient / ha area.
  • the active ingredients can also be used in conjunction with plastic dispersions at 0.25 percent, based on the weight of the dispersion.
  • the fungicides generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the application is e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering, pickling or pouring.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, are used to produce directly sprayable solutions, emulsions, pastes and oil dispersions.
  • Xylene paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., strongly polar solvents, for example Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. into consideration.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders), oil dispersions by adding water.
  • emulsions, pastes or old dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • Powders, materials for spreading and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, talc, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as e.g. Ammonium sulfates, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, talc, bolus, loe
  • Oils of various types, herbicides, fungicides, nemtatocides, insecticides, bactericides, trace elements, fertilizers, anti-foaming agents (e.g. silicones), growth regulators, antidote agents or other active compounds can be added to the mixtures or individual active compounds.
  • Leaves of potted wheat seedlings of the "Jubilar” variety are sprayed with aqueous emulsions of 80% (weight percent) active ingredient and 20% emulsifier and, after the spray coating has dried on, are dusted with oidia (spores) of the powdery mildew (Erysiphe graminis var. Tritici).
  • the test plants are then placed in the greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 10 days, the extent of the development of mildew is determined.
  • Leaves of wheat plants grown in pots are artificially infected with spores of the white rust (Puccinia recondita) and placed in a water-saturated chamber for 48 hours at 20 to 25 ° C.
  • the plants are then sprayed with aqueous spray liquors which contain a mixture of 80% of the active ingredient to be tested and 20% sodium lignosulfonate in the water or emulsified and in a greenhouse at temperatures between 20 and 22 ° C. and at 75 to 80% relative atmospheric humidity set up. After 10 days, the extent of the rust fungus development is assessed.
  • leaves of barley plants with spores of the dwarf rust (Puccinia hordei) and leaves of oat plants with spores of the crown rust (Puccinia coronata) are artificially infected and treated with the active substances to be tested.
  • active ingredient 3 20 parts by weight of active ingredient 3 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • a spray mixture is obtained which contains 0.1 percent by weight of the active ingredient.
  • compound 2 30 parts by weight of compound 2 are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. In this way a preparation of the active ingredient with good adhesiveness is obtained.
  • active ingredient 3 40 parts by weight of active ingredient 3 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid urea formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
  • active ingredient 5 20 parts of active ingredient 5 are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

  • Die vorliegende Erfindung betrifft neue wertvolle Derivate cyclischer Amine und ihre Salze und Molekül- und Additionsverbindungen mit guter fungizider Wirkung, Fungizide, die diese Verbindungen enthalten, und Verfahren zur Bekämpfung von Pilzen mit diesen Verbindungen.
  • Es ist bekannt, N-Tridecyl-2,6-dimethylmorpholin und seine Salze und seine Molekül- und Additionsverbindungen als Fungizide zu verwenden (DT-PS 11 64 152, DT-PS 11 73 722, DT-OS 24 61 513).
  • Es wurde gefunden, daß Derivate cyclischer Amine der Formel
    Figure imgb0001
    in der
    • R die Hydroxylgruppe, die Hydroxymethylgruppe, die Phenylgruppe oder die Reste ‾O‾CO‾CH3 oder O‾CO‾C2H5 bedeutet und ihre Salze, Molekül- und Additionsverbindungen eine gute fungizide Wirkung haben, die der Wirkung der bekannten Morpholinderivate überlegen ist.
  • Salze sind beispielsweise die Salze mit anorganischen oder organischen Säuren, z.B. Chloride, Fluoride, Bromide, Jodide, Sulfate, Nitrate, Phosphate, Acetate, Propionate, Molekül- oder Additionsverbindungen entstehen beispielsweise mit Säuren von Tensiden, z.B. Dodecylbenzolsulfonsäure,
    Figure imgb0002
  • Die Herstellung der neuen Verbindungen erfolgt beispielsweise durch Umsetzung von 3-Hydroxymethylpiperidin mit 3-p-Tertiär-butyl-phenyl-2-methyl-propanol in Gegenwart eines Redutionsmittels, z.B. Ameisensäure bei Temperaturen von 50 bis 110°C.
  • Von den erfindungsgemäßen Verbindungen werden beispielsweise die folgenden genannt:
    Figure imgb0003
    Figure imgb0004
  • Die erfindungsgemäßen Wirkstoffe und die entsprechenden Fungizide sind insbesondere geeignet zur Bekämpfung von Pflanzenkrankheiten, z.B. Erysiphe graminis (echter Mehltau) an Getriede, Erysiphe cichloriacearum (echter Mehltau) an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Erysiphe polygoni an Bohnen. Sphaerotheca pannosa an Rosen, Microsphaera querci an Eichen, Botrytis cinerea an Erdbeeren, Reben, Mycosphaerella musicola an Bananen, Puccinia-Arten (Rostpilze) an Getreide, Uromyces appendiculatus und U. phaseoli an Bohnen, Hemileia vastatrix an Kaffee und Rhizoctonia solani. Sie sind systematisch wirksam; sie werden sowohl über die Wurzeln als auch über die Blätter aufgenommen und im Pflanzengewebe transportiert.
  • Bei der Anwendung der neuen Wirkstoffe zur Behandlung von Pflanzen gegen Pilzinfektionen liegen die Aufwandmengen zwischen 0,025 und 5 kg Wirkstoff/ha Fläche. Zum Oberflächenschutz von Bäumen oder Früchten können die Wirkstoffe auch in Verbindung mit Kunststoffdispersionen 0,25 prozentig, bezogen auf das Gewicht der Dispersion, verwendet werden. Die Fungizide enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90%.
  • Die Wirkstoffe können mit anderen bekannten Fungiziden gemischt werden. In vielen Fällen erhält man dabei eine Vergrößerung des fungiziden Wirkungssepektrums; bei einer Anzahl von Fungizidmischungen in den Gewichtsverhältnissen 1 : 10 bis 10 : 1 treten auch synergistische Effekte auf, d.h., die fungizide Wirksamkeit des Kombinationsproduktes ist größer als die der addierten Wirksamkeiten der Einzelkomponenten. Fungizide, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, sind beispielsweise:
    • Dithiocarbamate und deren Derivate, wie Zinkdimethyldithiocarbamat,
    • Manganäthylenbisdithiocarbamat,
    • Mangan-Zink-äthylendiamin-bis-dithiocarbamat,
    • Zinkäthylenbisdithiocarbamat,
    • Tetramethylthiuramdisulfid,
    • Ammoniak-Komplez von Zink-(N,N-äthylen-bis-dithiocarbamat) und
    • N,N'-Polyäthylen-bis-(thlocarbamoyl)-difulsid,
    • Zink-(n,N'-propylen-bis-dithiocarbamat),
    • Ammoniak-Komplex von Zink-(N,N'-propylen-bis-dithiocarbamat) und
    • N,N'-Polypropylen-bis-(thiocarbamoyl)-disulfid;
    • heterocyclische Verbindungen, wie N-Trichlormethylthio-tetrahydrophthalimid,
    • N-Trichlormethylthio-phthalimid,
    • N-( 1,1,2,2-Tetrachloräthylthio)-tetrahydrophthali mid,
    • 1-(Butylcarbamoyl)-2-benzimidazol-carbaminsäuremethylester,
    • 2-Methyloxycarbonylamino-benzimidazol,
    • 2,3-Dihydro-5-carboxaniiido-6-methy)-1,4-oxathiin-4,4-dioxid,
    • 2,3-Dihydro-5-carboxani!ido-6-methy)-1,4-oxathiin,
    • 5-Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidin,
    • 1,2-Bis-(3-äthoxycarbonyl-2-thioureido)-benzol,
    • 1,2-Bis-(3-methoxycarbonyl-2-thioureido)-benzol
    • und verschiedene andere Fungizide, wie Dodecylguanidinacetat,
    • N-Dichlorfluormethylthio-N',N'-dimethyl-N-phenyl-schwefelsäurediamid,
    • 2,5-Dimethyl-furan-3-carbonsäureanilid,
    • 2,5-Dimethyl-furan-3-carbonsäure-cyclohexylamid,
    • 2-Jodbenzoesäureanilid,
    • 2-Brombenzoesäureanilid,
    • 3-Nitro-isophthalsäure-diisopropylester,
    • 1-( 1,2,4-Triazolyl-1')-1-(4'-chlorphenoxy)-3,3-dimethylbutan-2-on,
    • 1-(1-lmidazolyl)-2-allyloxy-2-(2,4-dichlorphenyl)-äthan,
    • Piperazin-1,4-diyi-bis-1-(2,2,2-Trichloräthyl)-formamid,
    • 2,4,5,6-Tetrachloro-isophthalonitril,
    • 1,2-Dimethyl-3,5-diphenyl-pyrazoliniummethylsulfat.
  • Die Anwendung erfolgt z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen, Beizen oder Gießen. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffen gewährleisten.
  • Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten und Öldispersionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle usw., sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, zum Beispiel Benzol, Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate zum Beispiel Methanol, Äthanol, Propanol, Butanol, Chloroform, Tetrachlorkohlenstoff, Cyclohexanol, Cyclohexanon, Chlorbenzol, Isophoron usw., stark polare Lösungsmittel, z.B. Dimethylformamid, Dimethylsulfoxid, N-Methylpyrrolidon, Wasser usw. in Betracht.
  • Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvem), Öldispersionen durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Oldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.
  • An oberflächenaktiven Stoffen sind zu nennen:
    • Alkali-, Erdalkali-, Ammoniumsalze von Ligninsulfonsäure, Naphthalinsulfonsäuren, Phenolsulfonsäuren, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Alkali- und Erdalkalisalze der Dibutylnaphthalinsulfonsäure, Lauryläthersulfat, Fettalkoholsulfate, fettsaure Alkali- und Erdalkalisalze, Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole, Salze von sulfatiertem Fettalkoholglykoläther, Kondensationsprodukte von sulfoniertem Naphthalin und Naphthalinderivaten mit Formealdehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyäthylen-octylphenoläther, äthoxyliertes Isooctylphenol-, Octylphenol-, Nonylphenol, Alkylphenolpolyglykoläther, Tributylphenylpolyglykoläther, Alkylarylpolyätheralkohole, Isotridecylalkohol, Fettalkoholäthylenoxid-Kondensate, äthoxyliertes Rizinusöl, Polyoxyäthylenalkyläther, äthoxyliertes Polyoxypropylen, Laurylalkoholpolyglykolätheracetal, Sorbitester, Lignin, Sulfitblaugen und Methylcellulose.
  • Pulver, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermahlen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.
  • Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z.B. Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Talkum, Bolus, Löß, Ton, Dolomit, Diatemeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z.B. Ammoniumsulfate, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehle, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe.
  • Zu den Mischungen oder Einzelwirkstoffen können Öle verschiedenen Typs, Herbizide, Fungizide, Nemtatozide, Insektizide, Bakterizide, Spurenelemente, Düngemittel, Antischaummittel (z.B. Silikone), Wachstumsregulatoren, Antidotmittel oder andere wirksame Verbindungen, zugesetzt werden.
  • Für die folgenden Versuche wurden folgende bekannte Vergleichssubstanzen verwendet.
    Figure imgb0005
    Figure imgb0006
    Figure imgb0007
    • Beispiel 1
  • Blätter von in Töpfen gewachsenen Weizenkeimlingen der Sorte "Jubilar" werden mit wäßrigen Emulsionen aus 80% (Gewichtsprozent) Wirkstoff und 20% Emulgiermittel besprüht und nach dem Antrocknen des Spritzbelages mit Oidien (Sporen) des Weizenmehltaus (Erysiphe graminis var. tritici) bestäubt. Die Versuchspflanzen werden anschließend im Gewäschshaus bei Temperaturen zwischen 20 und 22°C und 75 bis 80% relativer Luftfeuchtigkeit aufgestellt. Nach 10 Tagen wird das Ausmaß der Mehltaupilzentwicklung ermittelt.
    Figure imgb0008
    • Beispiel 2
  • In einem weiteren Versuch werden, wie in Beispiel 3 beschrieben, Blätter von in Töpfen gewachsenen Gerstenkeimlingen der Sorte "Firlbecks Union" behandelt und mit Sporen (Konidien) des Gerstenmehltaus (Erysiphe graminis var. hordei) bestäubt.
    Figure imgb0009
    • Beispiel 3
  • Blätter von in Töpfen gewachsenen Weizenpflanzen werden mit Sporen des Weisenbraunrostes (Puccinia recondita) künstlich infiziert und 48 Stunden lang bei 20 bis 25°C in einer wasserdampfgesättigten Kammer aufgestellt. Danach werden die Pflanzen mit wäßrigen Spritzbrühen, die in dem Wasser gelöst oder emulgiert eine Mischung aus 80% des zu prüfenden Wirkstoffes und 20% Natriumligninsulfonat enthalten, besprüht und im Gewächshaus bei Temperaturen zwischen 20 und 22°C und bei 75 bis 80% relativer Luftfeuchtigkeit aufgestellt. Nach 10 Tagen wird das Ausmaß der Rostpilzentwicklung beurteilt.
  • In gleicher Weise werden Blätter von Gerstenpflanzen mit Sporen des Zwergrostes (Puccinia hordei) und Blätter von Haferpflanzen mit Sporen des Kronenrostes (Puccinia coronata) künstlich infiziert und mit den zu prüfenden Wirkstoffen behandelt.
    Figure imgb0010
    Figure imgb0011
    • Beispiel 4
  • Man vermischt 90 Gewichtsteile der Verbindung 3 mit 10 Gewichtsteilen N-Methyl-a-pyrrolidon und erhält eine Lösung, die zur Anwendung in Form kleinster Tropen geeignet ist.
    • Beispiel 5
  • 20 Gewichtsteile der Verbindung 2 werden in einer Mischung gelöst, die aus 80 Gewichtsteilen Xylol, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Äthylenoxid an 1 Mol Ölsäure-N-mono-äthanolamid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.
    • Beispiel 6
  • 20 Gewichtsteile der Verbindung 3 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen lsobutanol, 20 Gewichtsteilen des Anlagerungsproduktes von 7 Mol Äthylenoxid an 1 Mol Isooctylphenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.
    • Beispiel 7
  • 20 Gewichtsteile der Verbindung 2 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanol, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man ein wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.
    • Beispiel 8
  • 20 Gewichtsteile des Wirkstoffs 3 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphthalin-a-sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulferförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermahlen. Durch feines Verteilen der Mischung in 20000 Gewichtsteilen Wasser erhält man eine Spritzbrühe die 0,1 Gewichtsprozent des Wirkstoffs enthält.
    • Beispiel 9
  • 3 Gewichtsteile der Verbindung 3 werden mit 57 Gewichtsteilen feinteiligem Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gewichtsprozent des Wirkstoffs enthält.
    • Beispiel 10
  • 30 Gewichtsteile der Verbindung 2 werden mit einer Mischung aus 92 Gewichtsteilen pulverförmigem Kieselsäuregel und 8 Gewichtsteilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit.
    • Beispiel 11
  • 40 Gewichtsteile des Wirkstoffs 3 werden mit 10 Teilen Natriumsalz eines Phenolsulfonsäureharnstoff-formaldehyd-kondensats, 2 Teilen Kieselgel und 48 Teilen Wasser innig vermischt. Man erhält eine stabile wäßrige Dispersion. Durch Verdünnen mit 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,04 Gewichtsprozent Wirkstoff enthält.
    • Beispiel 12
  • 20 Teile des Wirkstoffs 5 werden mit 2 Teilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Teilen Fettalkohol-polyglykoläther, 2 Teilen Natriumsalz eines Phenolsulfonsäure-harnstoff-formaldehydkondensats und 68 Teile eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.

Claims (2)

1. Derivate cyclischer Amine der Formel
Figure imgb0012
in der R die Hydroxylgruppe, die Hydroxymethylgruppe, die Phenylgruppe oder die Reste ‾O‾CO‾CH3 oder O‾CO‾C2H5 bedeutet und ihre Salze, Molekül- und Additionsverbindungen.
2. Fungizid, enthaltend ein Derivat eines cyclischen Amins gemäß Anspruch 1.
EP78100174A 1977-06-18 1978-06-16 Derivate cyclischer Amine und diese enthaltende Fungizide Expired EP0000333B1 (de)

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DE2727482 1977-06-18

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EP0000333A3 EP0000333A3 (en) 1979-07-25
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DE2822326A1 (de) * 1978-05-22 1979-11-29 Basf Ag Antimykotische mittel
DE2830127A1 (de) * 1978-07-08 1980-01-17 Basf Ag N-arylpropyl-substituierte cyclische amine
DE2965247D1 (en) * 1978-08-08 1983-05-26 Hoffmann La Roche Synthesis of phenyl-propyl morpholine and piperidine derivatives
US4283534A (en) * 1979-04-11 1981-08-11 Basf Aktiengesellschaft Reductive alkylation of nitrogen heterocycles
DE3101233A1 (de) * 1981-01-16 1982-08-26 Basf Ag, 6700 Ludwigshafen N-3'-(p-tertiaer-butylphenyl)-2'-methyl-propyl-1'-piperidin-derivate, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit diesen verbindungen
US4599335A (en) * 1983-05-06 1986-07-08 Basf Aktiengesellschaft Diamine derivatives, compositions and use
DE3433036A1 (de) * 1984-09-08 1986-03-20 Basf Ag, 6700 Ludwigshafen Piperidinderivate und diese enthaltende fungizide sowie verfahren zur bekaempfung von pilzen
DE3614906A1 (de) * 1986-05-02 1987-11-05 Basf Ag Phenyl- und cyclohexyl-isobutylpyrrolidinderivate
DE3614907A1 (de) * 1986-05-02 1987-11-05 Basf Ag N-substituierte pyrrolidon- und piperidinderivate und deren salze
DE3627071A1 (de) * 1986-08-09 1988-02-11 Bayer Ag Substituierte hydroxypropylamin-derivate
DE3732930A1 (de) * 1987-09-30 1989-04-20 Basf Ag Fungizide n-substituierte 3-aryl-pyrrolidin-derivate
DE3732910A1 (de) * 1987-09-30 1989-04-20 Basf Ag Fungizide n-substituierte 3-alkyl-4-aryl-pyrrolidin-derivate
DE3803860A1 (de) * 1988-02-09 1989-08-17 Basf Ag N,n'-disubstituierte piperazine
DE3901246A1 (de) * 1989-01-18 1990-07-19 Basf Ag Verwendung von 2,2,6,6-tetramethyl-4-aminopiperidinamiden als fungizide
GB9100505D0 (en) * 1991-01-10 1991-02-20 Shell Int Research Piperidine derivatives

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GB809760A (en) * 1956-04-20 1959-03-04 Lab Pharmaceutica Dr C Janssen Improvements in or relating to pharmacologically active piperazine derivatives and processes for preparing them
GB1409438A (en) * 1972-12-21 1975-10-08 Wyeth John & Brother Ltd Piperidine derivatives
US4008276A (en) * 1975-01-20 1977-02-15 Sterling Drug Inc. Phenyl-lower-alkylamines
AT354187B (de) * 1976-11-22 1979-12-27 Hoffmann La Roche Fungizides mittel
DE2656747C2 (de) * 1976-12-15 1984-07-05 Basf Ag, 6700 Ludwigshafen Morpholinderivate

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DE2727482A1 (de) 1979-01-11

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