DE69006290T2 - N-Substituierte Benzyloxyiminderivate, Verfahren zu deren Herstellung und deren Verwendung. - Google Patents

N-Substituierte Benzyloxyiminderivate, Verfahren zu deren Herstellung und deren Verwendung.

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Publication number
DE69006290T2
DE69006290T2 DE90115822T DE69006290T DE69006290T2 DE 69006290 T2 DE69006290 T2 DE 69006290T2 DE 90115822 T DE90115822 T DE 90115822T DE 69006290 T DE69006290 T DE 69006290T DE 69006290 T2 DE69006290 T2 DE 69006290T2
Authority
DE
Germany
Prior art keywords
substituted
group
benzyloxyimine
alkyl group
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
DE90115822T
Other languages
English (en)
Other versions
DE69006290D1 (de
Inventor
Katsutoshi Endo
Hideo Kanno
Nobuyuki Niino
Kenji Tsubata
Yoshinobu Yamamoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nihon Nohyaku Co Ltd
Original Assignee
Nihon Nohyaku Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd
Publication of DE69006290D1 publication Critical patent/DE69006290D1/de
Application granted granted Critical
Publication of DE69006290T2 publication Critical patent/DE69006290T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Description

  • Diese Erfindung betrifft N-substituierte Benzyloxyiminderivate, Landwirtschafts- und Gartenbaufungizide, die sie als aktiven Bestandteil enthalten, ein Verfahren für deren Herstellung und ein Verfahren zum Kontrollieren von Pflanzenkrankheit
  • JP-A-61-106538 und JP-A-61-28045 offenbaren Verbindungen, die den erfindungsgemäßen Vebindungen strukturell ähnlich sind, und sie beschreiben, daß solche Vebindungen nützlich sind als ein landwirtschaftliches Fungizid oder Insektizid. Ihre Aktivitäten sind jedoch nicht unbedingt zufriedenstellend.
  • EP-A-370 629, die gemäß Atrikel 54(3) EPÜ zum Stand der Technik gehört, offenbart Verbindungen der allgemeinen Formel
  • und Stereoisomere davon, worin A Wasserstoff, Halogen, Hydroxyl, C&sub1;&submin;&sub4;-Alkyl, C&sub1;&submin;&sub4;-Alkoxy, C&sub1;&submin;&sub4;&submin;Halogenalkyl, C&sub1;&submin;&sub4;-Halogenalkoxy, C&sub1;&submin;&sub4;-Alkylcarbonyl, C&sub1;&submin;&sub4;-Alkoxycarbonyl, Phenoxy, Nitro oder Cyano ist; R¹ und R², die gleich oder verschieden sein können, Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substituiertes Heterocycloalkyl, gegebenenfalls substituiertes Cycloalkylalkyl, gegebenenfalls Aralkyl, gegebenenfalls substituiertes Heteroarylalkyl, gegebenenfallls substituiertes Aryloxyalkyl, gegebenenfalls substituiertes Heteroaryloxyalkyl, gegebenenfalls substituiertes Alkenyl gegebenenfalls substituiertes Alkynyl, gegebenenfalls substituiertes Alkoxy, gegebenenfalls substituiertes Aryl, gegebenenfalls substituiertes Heteroaryl, gegebenenfalls substituiertes Aryloxy, gegebenenfalls substituiertes Heteroaryloxy, Nitro, Halogen, Cyano, -NR³R&sup4;, -CO&sub2;R³, - CONR³R&sup4;, -COR³, -S(O)nR³, worin n 0, 1 oder 2 ist, (CH&sub2;)mPO(OR³)&sub2;, worin m 0 oder 1 ist, sind oder R¹ und R² zusammen ein carbocylisches oder heterocyclisches Ringsystem bilden; und R³ und R&sup4;, die gleich oder verschieden sein können, Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Aralkyl, gegebenenfalls substituiertes Alkenyl, gegebenenfalls substituiertes Aryl oder gegebenenfalls substituiertes Heteroaryl sind. Von diesen Verbindungen wird berichtet, daß sie fungizide, insektizide und mitizide Eigenschaften besitzen.
  • Weitere Verbindungen fungizider Wirksamkeit sind in WO-A- 90/07493 beschrieben, die auch gemäß Artikel 54(3) zum Stand der Technik gehören. Diese Verbindungen gehören der allgemeinen Formel
  • an, worin X eine Aldimingruppe oder Ketimingruppe darstellt, und x insbesondere eine Gruppe der Formel
  • TEXT FEHLT
  • darstellt, worin R¹ und R² unabhängig voneinander Wasserstoff, C&sub1;&submin;&sub1;&sub2;-Alkyl, C&sub1;&submin;&sub4;-Halogenalkyl, C&sub1;&submin;&sub4;-Alkoxy-C&sub1;&submin;&sub4;-alkyl, C&sub1;&submin;&sub4;-Alkylthio-C&sub1;&submin;&sub4;-alkyl, Aryl-C&sub1;&submin;&sub4;-alkyl, Aryloxy- C&sub1;&submin;&sub4;-alkyl, Arylthio-C&sub1;&submin;&sub4;-alkyl, Heteroaryl-C&sub1;&submin;&sub4;&submin;alkyl, C&sub2;&submin;&sub1;&sub2;-Alkenyl, Aryl-C&sub2;&submin;&sub4;-alkenyl, Heteroaryl-C&sub2;&submin;&sub4;-alkenyl, C&sub2;&submin;&sub1;&sub2;-Alkynyl, C&sub3;&submin;&sub6;-Cycloalkyl, Aryl, Heteroaryl, Cyano, COOR³, CONR&sup4;R&sup5;, COR&sup6; oder CR&sup7;=NOR&sup8; sind, worin R³ bis R&sup8; jeweils Wasserstoff, C&sub1;&submin;&sub4;-Alkyl, Aryl oder Heteroaryl darstellen, oder R¹ und R² zusammen mit dem C-Atom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der gegebenenfalls ein O- oder 5-Atom enthält.
  • Es ist die der vorliegenden Erfindung zugrundeliegende Aufgabe, neue Verbindungen mit beachtlicher fungizider Wirksamkeit und ein Verfahren für ihre Herstellung, sowie ein Fungizid enthaltend diese Verbindungen und ein Verfahren zum Kontrollieren von Pflanzenkrankheit, umfassend die Verwendung der Verbindungen, bereitzustellen.
  • Gemäß der vorliegenden Erfindung wird diese Aufgabe mit N- substituierten Benzyloxyiminderivaten der allgemeinen Formel (I):
  • gelöst, worin R¹ und R² jeweils unabhängig voneinander eine C&sub1;-C&sub6;-Alkylgruppe darstellen;
  • eines von R³ und R&sup4; eine C&sub1;-C&sub6;-Alkylgruppe, eine C&sub1;-C&sub6;-Halogenalkylgruppe oder eine niedrige Alkoxyalkylgruppe darstellt, und
  • das andere ein stickstoffatomhaltiger Heteroring ist, ausgewählt aus der Gruppe, bestehend aus substituiertem und unsubstituiertem Pyrrolidin, Piperidin, Morpholin, Thiomorpholin, Piperazin, Hexamethylenimin, Tetrahydrochinolin und Tetrahydroisochinolin, und das Stickstoffatom in dem Heteroring immer die Bindung als ein Substituent von entweder R³ oder R&sup4; bildet.
  • Gemäß der vorliegenden Erfindung wird auch ein Verfahren zum Herstellen von N-substituierten Benzyloxyiminderivaten der allgemeinen Formel (I):
  • bereitgestellt, worin R¹ und R² jeweils unabhängig voneinander eine C&sub1;-C&sub6;-Alkylgruppe darstellen;
  • eines von R³ und R&sup4; eine C&sub1;-C&sub6;-Alkylgruppe, eine C&sub1;-C&sub6;-Halogenalkylgruppe oder eine niedrige Alkoxyalkylgruppe darstellt, und
  • das andere ein stickstoffatomhaltiger Heteroring ist, ausgewählt aus der Gruppe, bestehend aus substituiertem oder unsubstituiertem Pyrrolidin, Piperidin, Morpholin, Thiomorpholin, Piperazin, Hexamethylenimin, Tetrahydrochinolin und Tetrahydroisochinolin, und das Stickstoffatom in dem Heteroring immer die Bindung als ein Substituent von entweder R³ oder R&sup4; bildet;
  • welches das Reagierenlassen einer Verbindung der allgemeinen Formel (II):
  • worin R¹ und R² wie in der vorstehenden Formel (I) definiert sind, und X ein Halogenatom darstellt, mit einer Verbindung der allgemeinen Formel (III):
  • worin R³ und R&sup4; wie in der vorstehenden Formel (I) definiert sind, umfaßt.
  • Die vorliegende Erfindung stellt weiterhin ein Landwirtschafts- oder Gartenbaufungizid zur Verfügung, welches ein N-substituiertes Benzyloxyiminderivat der vorliegenden Erfindung in solch einer Menge, die eine landwirtschaftliche oder gartenbauliche fungizide Wirksamkeit zeigt, und einen Träger, der als landwirtschaftlicher oder gartenbaulicher inerter Träger annehmbar ist, umfaßt; und ein Verfahren zum Kontrollieren von Pflanzenkrankheit, welches das Aufbringen des Landwirtschafts- oder Gartenbaufungizids in einer Menge, als aktives Bestandteil, von 0,1 bis 1.000 g pro 10 Ar umfaßt.
  • Das N-substituierte Benzyloxyiminderivat dieser Erfindung liegt als ein Isomer mit einer E-Form oder Z-Form, bezogen auf die Kohlenstoff-Stickstoff-Doppelbindungen und Kohlenstoff-Kohlenstoff-Doppelbindungen, vor, und diese Isomere und das Gemisch aus ihnen sind vom Umfang dieser Erfindung umfaßt.
  • Das erfindungsgemäße N-substituierte Benzyloxyiminderivat kann als ein quartäres Salz, z. B. als Salz von Tosylat, isoliert werden.
  • Vorzugsweise ist der Heteroring in dem vorliegenden N- substituierten Benzyloxyiminderivat mit mindestens einer Gruppe substituiert, ausgewählt aus der Gruppe, bestehend aus einem Halogenatom, einer C&sub1;-C&sub6;-Alkylgruppe, einer Phenylgruppe, die 1 bis 5 Substituenten aufweisen kann, unabhänging ausgewählt aus Halogenatomen, Benzylgruppen, Pyridylgruppen, Pyrimidylgruppen und Dioxolangruppen, insbesondere 1 bis 3 Alkylgruppen. Es ist weiterhin bevorzugt, daß eines von R³ und R&sup4; eine Morpholinogruppe ist, die mit einer C&sub1;-C&sub6;-Alkylgruppe substituiert sein kann, und das andere eine C&sub1;-C&sub6;-Alkylgruppe, eine C&sub1;-C&sub6;-Halogenalkylgruppe oder eine niedrige Alkoxyalkylgruppe ist, insbesondere wenn das andere eine C&sub1;-C2-Alkylgruppe oder eine C&sub1;-C&sub6;-Halogenalkylgruppe ist.
  • Das N-substituierte Benzyloxyiminderivat der allgemeinen Formel (I) kann durch Reagierenlassen einer Verbindung der allgemeinen Formel (II) mit einer Verbindung der allgemeinen Formel (III) in Anwesenheit einer Base oder einer Silberverbindung und in der Anwesenheit eines inerten Lösungsmittels hergestellt werden.
  • Jedes inerte Lösungsmittel, das die vorliegende Reaktion nicht verhindert, kann in dieser Erfindung verwendet werden. Beispiele solch eines Lösungsmittels sind Alkohole, wie Isopropanol, Butanol und Diethylenglykol; Ketone, wie Aceton, Methylethylketon und Cyclohexanon, Ether, wie Diethylether, Diisopropylether, Tetrahydrofuran, Dioxan, Monoglykolether, Diglykolether; halogenierte Kohlenwasserstoffe, wie Dichlorethan, Chloroform, Tetrachlorkohlenstoff und Tetrachlorethan; aromatische Kohlenwasserstoffe, wie Benzol, Chlorbenzol, Nitrobenzol und Toluol; Nitrile, wie Acetonitril; Dimethylformamid; Dimethylsulfoxid; Wasser und ein gemischtes Lösungsmittel aus diesen.
  • Wenn eine Zwei-Phasen-Reaktion in dem gemischten Lösungsmittel durchgeführt wird, kann ein Phasen-Transfer-Katalysator, wie z. B. Triethylbenzylammoniumchlorid oder Trioctylmethylammoniumchlorid, verwendet werden.
  • Anorganische Basen und organische Basen sind als Basen verwendbar. Beispiele der anorganischen Basen sind Carbonate von Alkalimetallen oder Erdalkalimetallen, wie Natriumcarbonat, Kaliumcarbonat, Calciumcarbonat und Natriumhydrogencarbonat; Hydroxide von Alkalimetallen oder Erdalkalimetallen, wie Natriumhydroxid, Kaliumhydroxid und Calciumhydroxid; Hydride von Alkalimetallen, wie Lithiumhydrid und Natriumhydrid. Beispiele der organischen Basen sind Alkoxide von Alkalimetallatomen, wie Natriummethoxid und Kalium-tertbutoxid, Diethylamin, Triethylamin, Pyridin und Benzyltrimethylammoniumhydroxid.
  • Eine Silberverbindung, beispielsweise Silberoxid, kann verwendet werden.
  • Die Reaktionstemperatur liegt geeignet zwischen -70ºC und dem Siedepunkt des Lösungsmittels, und sie liegt vorzugsweise zwischen -40ºC und 30ºC. Die Reaktionszeit variiert in Abhängigkeit von der Reaktionstemperatur und dem Reaktionsmaßstab. Sie beträgt im allgemeinen 30 min bis 12 h.
  • Die vorliegende Reaktion ist eine äquimolare Reaktion, und eine Verbindung der allgemeinen Formel (II) und eine Verbindung der allgemeinen Formel (III) können daher in äquimolaren Mengen verwendet werden. Eine dieser Verbindungen kann jedoch in einer überschüssigen Menge verwendet werden.
  • Die Base kann in einer äquimolaren Menge, bezogen auf eine Verbindung der allgemeinen Formel (III), verwendet werden.
  • Sie kann jedoch in einer überschüssigen Menge verwendet werden.
  • Nach Beendigung der Reaktion wird das beabsichtigte Produkt durch eine gewöhnliche Methode isoliert und gegebenenfalls gereinigt, z. B. durch Säulenchromatographie oder eine Rekristallisationsmethode.
  • Die Verbindung der allgemeinen Formel (II) kann gemäß dem in JP-A-61-280452 offenbarten Verfahren hergestellt werden. Die Verbindung der allgemeinen Formel (III), deren Umfang einige neue Verbindungen umfaßt, kann gemäß einem Verfahren für die Herstellung bekannter Verbindungen [z. B. Org. Syn. Coll. Band 2, 313 (1943), dito, 363 (1943) und J. Org. Chem., 1980, 45, 4198] hergestellt werden.
  • Tabelle 1 zeigt typische Beispiele des N-substituierten Benzyloxyiminderivates der allgemeinen Formel (I). Tabelle 1 Verbindung Nr. Physikalische Eigenschaften (Schmelzpunkt oder Brechungsindex) *H-NMR Chemische Verschiebung Paste Tabelle 1 (Fortsetzung) Tabelle 1 (Fortsetzung) Tabelle 1 (Fortsetzung) Tabelle 1 (Fortsetzung) Tabelle 1 (Fortsetzung) Tabelle 1 (Fortsetzung) blaßgelbe Paste blaßbraune Paste Tabelle 1 (Fortsetzung) Tabelle 1 (Fortsetzung) Tabelle 1 (Fortsetzung)
  • *¹H-NMR chemische Verschiebung der olefinischen Protonen des Methoxyacrylatteils, registriert in Deuterochloroform mit Tetramethylsilan als interner Standard [&delta;-Wert (ppm)].
  • Die folgenden Beispiele illustrieren typische Ausführungsformen des N-substituierten Benzyloxyiminderivats der allgemeinen Formel (I).
    • Beispiel 1 Methyl-2-[2-{1-(cis-2,6-dimethylmorpholino)-ethylidenaminooxymethylphenyl]-3-methoxyacrylat (Verbindung Nr. 15)
  • 1,72 g 1-(cis-2,6-Dimethylmorpholino)-acetoaldoxim wurden in 30 ml Dimethylformamid aufgelöst, und 0,66 g Kaliumhydroxidpulver wurden zugefügt, und das Gemisch wurde 10 min bei 0ºc gerührt. 2,85 g Methyl-2-(2-Brommethylphenyl)-3-methoxyacrylat wurden zugefügt, und das erhaltene Gemisch wurde weiterhin 1 h bei Raumtemperatur gerührt, um die Reaktion durchzuführen. Nach Beendigung der Reaktion wurde das Reaktionsgemisch in Eiswasser gegossen und mit Ethylacetat extrahiert. Die Extrakte wurden mit Wasser gewaschen und über Magnesiumsulfat getrocknet. Die Extrakte wurden filtriert und unter vermindertem Druck konzentriert, und der erhaltene Rest wurde durch Kieselgel-Trockensäulenchromatographie gereinigt, um 0,4 g des beabsichtigten Produktes zu ergeben.
  • Ausbeute: 10,6%, Eigenschaften: 107-109ºC
  • Die N-substituierten Benzyloxyiminoderivate der allgemeinen Formel (1) sind nützlich als Landwirtschafts- und Gartenbaufungizide, und sie sind sehr wirksam bei der Kontrolle verschiedener Pflanzenkrankheiten, Reisbrand (Pyricularia oryzae), Reishüllenbrand (Rhizoctonia solani), braune Reisflecken (Cochliobolus miyabeanus), pulveriger Mehltau von Gerste (Frysiphe graminis f.sp. hordei) und anderer Pflanzen, Rost verschiedener Pflanzen und der Krankheiten, verursacht durch Oomycetes-Pilze, wie später Tomatenbrand (Phytophthora infestans) und flaumiger Gurkenmehltau (Pseudoperonaspora cubensis).
  • Die erfindungsgemäßen Verbindungen besitzen ausgezeichnete Wirksamkeit bei der Kontrolle von Krankheiten von Reisfeldfrüchten, Hochlandfeldfrüchten, Obstbäumen, Gemüsen, anderen Feldfrüchten und blühenden Pflanzen durch die Anwendung auf Pflanzenlaub, Berieselungswasser oder Erde vor oder nach dem Auftreten der Krankheit.
  • Wenn das N-substituierte Benzyloxyiminderivat der allgemeinen Formel (I) als Landwirtschafts- und Gartenbaufungizid verwendet wird, wird es im allgemeinen in geeignete verwendbare Formen gemäß herkömmlicher Art zur Herstellung von Agrochemikalien zubereitet.
  • Das heißt, das N-substituierte Benzyloxyiminderivat der allgemeinen Formel (I) und gegebenenfalls ein Zusatzstoff werden mit einem geeigneten inerten Träger vermischt und in eine geeignete Präparatform, wie eine Suspension, ein emulgierbares Konzentrat, ein lösliches Konzentrat, ein benetzbares Pulver, Granulate, ein Stäubemittel oder eine Tablette, durch Auflösen, Dispersion, Suspension, Mischen, Imprägnation, Adsorption oder Anhaften gebracht.
  • Der inerte Träger in dieser Erfindung kann fest oder flüssig sein. Beispiele des festen Trägers sind Sojabohnenmehl, Getreidemehl, Holzmehl, Rindenmehl, Sägestaub, pulverisierte Tabakstiele, pulverisierte Walnußschalen, Kleie, pulverisierte Cellulose, Extraktionsreste von Gemüsen, pulverisierte synthetische Polymere oder Harze, Tonerden (z. B. Kaolin, Betonit und Tonsäure), Talke (z. B. Talk und pyrophyllit), Kieselpulver oder -flocken (z. B. Diatomit, Quarzsand, Glimmer und Quarzpulver, d. h. synthetische Hochdispersionskieselsäure, genannt feinzerteiltes, hydriertes Siliciumoxid oder hydrierte Kieselsäure), aktivierter Kohlenstoff, pulverisierter Schwefel, pulverisierter Bimsstein, calcinierter Diatomit, gemahlener Ziegel, Flugasche, Sand, Calciumcarbonatpulver, Calciumphosphatpulver und andere anorganischen oder Mineralpulver, chemische Dünger (z. B. Ammoniumsulfat, Ammoniumnitrat, Harnstoff und Ammoniumchlorid) und Kompost. Diese Träger können allein oder in Kombination verwendet werden.
  • Der flüssige Träger weist entweder selbst Löslichkeit auf oder besitzt keine solche Löslichkeit, er ist aber fähig, einen aktiven Bestandteil mit Hilfe eines Zusatzstoffes zu dispergieren. Die folgenden sind typische Beispiele von flüssigen Trägerstoffen, die allein oder in Kombination verwendet werden können. Wasser; Alkohole, wie Methanol, Ethanol, Isopropanol, Butanol und Ethylenglykol; Ketone, wie Aceton, Methylethylketon, Methylisobutylketon, Diisobutylketon und Cyclohexanon; Ether, wie Ethylether, Dioxan, Cellosolve, Dipropylether und Tetrahydrofuran; aliphatische Kohlenwasserstoffe, wie Benzin und Mineralöle; aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Solventnaphtha und Alkylnaphthalen; halogenierte Kohlenwasserstoffe, wie Dichlorethan, Chloroform, Tetrachlorkohlenstoff und Chlorbenzol; Ester, wie Ethylacetat, Diisopropylphthalat, Dibutylphthalat und Dioctylphthalat; Amide, wie Dimethylformamid und Dimethylacetamid; Nitrile, wie Acetonitril; und Dimethylsulfoxid.
  • Die folgenden Beispiele sind typische Beispiele von Zusatzstoffen, die in Abhängigkeit von dem Zweck und alleine oder in einigen Fällen in Kombination verwendet werden, oder überhaupt nicht verwendet werden können.
  • Um einen aktiven Bestandteil zu emulgieren, dispergieren, aufzulösen und/oder zu benetzen, wird ein oberflächenaktiver Stoff verwendet. Beispiele des oberflächenaktiven Stoffes sind Polyoxyethylenalkylether, Polyoxyethylenalkylarylether, Polyoxyethylen höherer Fettsäureester, Polyoxyethylenresinate, Polyoxyethylensorbitanmonolaurat, Polyoxyethylensorbitanmonooleat, Alkylarylsulfonate, Naphthalen-Sulfonsäure-Kondensationsprodukte, Ligninsulfonate und höhere Alkoholsulfatester.
  • Weiterhin kann ein Zusatzstoff verwendet werden, um die Dispersion eines aktiven Bestandteils zu stabilisieren, sie klebrig zu machen und/oder zu binden. Beispiele solch eines Zusatzstoffes sind Casein, Gelatine, Stärke, Methylcellulose, Carboxymethylcellulose, Gummiarabikum, Polyvinylalkohol, Terpentin, Kleieöl, Bentonit und Ligninsulfonate.
  • Um die Fließbarkeit eines festen Produktes zu verbessern, können Zusatzstoffe verwendet werden. Beispiele solcher Zusatzstoffe sind Wachse, Stearate und Alkylphosphate.
  • Zusatzstoffe, wie Naphthalen-Sulfonsäure-Kondensationsprodukte und Polykondensate von Phosphaten, können als Peptisierungsmittel für dispergierbare Produkte verwendet werden.
  • Zusatzstoffe, z. B. Siliconöle, können auch als Entschäumungsmittel verwendet werden.
  • Der Gehalt des aktiven Bestandteils kann wie erforderlich variiert werden. In Bestäubungsmitteln oder Granulaten ist der geeignete Gehalt davon 0,1 bis 50 Gew.-%. In emulgierbaren Konzentraten, fließbaren, benetzbaren Pulvern ist er von 0,1 bis 90 Gew.-%.
  • Ein Landwirtschafts- oder Gartenbaufungizid, enthaltend das N-substituierte Benzyloxyiminderivat der allgemeinen Formel (I) als aktiven Bestandteil, wird verwendet, um eine Vielzahl von Pflanzenkrankheiten auf folgende Weise zu kontrollieren. Das heißt, es wird auf eine Pflanze, von der man annimmt, daß Krankheiten auftreten, oder auf eine Stelle, wo das Auftreten von Krankheiten unerwünscht ist, direkt oder durch geeignetes Verdünnen mit Wasser oder Suspendieren in Wasser in solch einer Menge aufgetragen, die wirksam ist, um die Krankheiten zu kontrollieren.
  • Die Menge des Landwirtschafts- oder Gartenbaufungizids, enthaltend das N-substituierte Benzyloxyiminderivat der allgemeinen Formel (I) als aktiven Bestandteil, variiert in Abhängigkeit von verschiedenen Faktoren, wie dem Zweck, den zu kontrollierenden Krankheiten, dem Wachstumsstadium einer Pflanze, der Tendenz der Krankheitenerscheinung, dem Wetter, den Umgebungsbedingungen, der Zubereitungsform, der Anwendungsmethode, der Anwendungsstelle und dem Anwendungszeitpunkt. Sie wird jedoch in einer Menge von 0,1 g bis 1.000 g pro 10 Ar als aktiven Bestandteil, abhängig von dem Zweck, verwendet.
  • Das Landwirtschafts- oder Gartenbaufungizid, enthaltend das N-substituierte Benzyloxyiminderivat der allgemeinen Formel (I) als aktiven Bestandteil, kann als Gemisch davon mit einer Agrochemikalie, Dünger und/oder Pflanzennährstoff, die zu seiner Anwendungszeit verwendbar sind, oder nur in Kombination mit diesen verwendet werden.
  • Wenn das Landwirtschafts- oder Gartenbaufungizid, enthaltend die erfindungsgemäße Verbindung als aktiven Bestandteil, verwendet wird, um Pflanzenkrankheiten zu kontrollieren, kann es mit einem anderen Kontrolleur(en) gemischt werden, um eine andere Pflanzenschädigung, die gleichzeitig mit Pflanzenkrankheiten auftritt, die durch das erfindungsgemäße Fungizid zu kontrollieren sind, zu kontrollieren, und das Gemisch kann als Mehrzweck-Kontrolleur verwendet werden. Beispiele solcher anderer Kontrolleure sind folgende.
  • O,O-Dimethyl-O-(3-methyl-4-nitrophenyl)-phosphorothioat (Fenitrothion)
  • O,O-Dimethyl-O-(3-methyl-4-methylthiophenyl)-phosphorothioat (Fenthion)
  • S-&alpha;-Ethoxycarbonylbenzyl-O,O-diemethyl-phosphorodithioat (Phenthioat)
  • O,O-Diethyl-O-(2-isopropyl-6-methyl-4- pyriinidinyl)phosphorothioat (Diazinon)
  • Dimethyl-2,2,2-trichlor-1-hydroxyethylphosphonat (Trichlorphon)
  • O-4-Cyanophenyl-O-ethylphenylphosphonothioat (Cyanophenphos)
  • O-Ethyl-O-4-nitrophenyl-phenylphosphonothioat (EPN)
  • 4-(Methylthio)phenyl-dipropylphosphat (Propaphos)
  • O,O-Dimethyl-S-phthalimidomethyl-phosphorodithioat (Phosmet)
  • 2,2-Dichlorvinyl-dimethylphosphat (DDVP)
  • O,O-Dimethyl-S-methylcarbamoylmethyl-phosphorodithioat (Dimethoat)
  • 5-1,2-Bis (ethoxycarbonyl)ethyl-O,O-dimethyl-phosphorodithiat (Malathion)
  • 1-Naphthylmethylcarbamat (Carbaryl)
  • m-Tolylmethylcarbamat (Metocarb)
  • 2-Isopropoxyphenyl-methylcarbamat (Propoxur)
  • S-(N-Ethoxycarbonyl-N-methylcarbamoylmethyl)-O,O-diethylphosphorodithioat (Mecarbam)
  • 3,4-Xylylmethylcarbamat (Xylylcarb)
  • 2-sec-Butylphenylmethylcarbamat (BPMC)
  • 2-Isopropylphenylmethylcarbamat (Isoprocarb)
  • 2-Chlorphenylmethylcarbamat (CPMC)
  • 3,5-Xylylmethylcarbamat (XMC)
  • 2-(1,3-Dioxolan-2-yl)phenylmethylcarbamat (Dioxacarb)
  • 3-tert-Butylphenylmethylcarbamat (Terbam)
  • 4-Diallylamino-3,5-xylylmethylcarbamat (Allyxycarb)
  • S-Methyl-N-(methylcarbamoyloxy)thioacetimidat (Methomyl)
  • N-(4-Chlor-o-tolyl)-N,N-dimethlyformamidinhydrogenchlorid (Chlordimeform)
  • 1,3-Bis-(carbamoylthio)-2-dimethylaminopropan-hydrogenchlorid (Cartap)
  • Diisopropyl-1,3-dithiolan-2-ylidenmalonat (Isoprothiolan)
  • S-Benzyl-O,O-diisopropylphosphorothjoat (IBP)
    • TESTBEISPIELE Testbeispiel 1. Kontrolleffekt auf pulverigen Mehltau von Gerste (Erysiphe graminis f.s. hordei)
  • Gerstenkeimlinge im Zwei-Blatt-Stadium wurden mit der Testverbindung (200 ppm) einen Tag nach der Inokulation mit Conidia von Erysiphe graminis f.sp. hordei besprüht. Die Keimlinge wurden bei konstanter Raumtemperatur bei 25ºC eine Woche lang gehalten, und der Prozentanteil der befallenen Fläche pro Blatt wurde untersucht. Die Krankheitskontrollwirksamkeit wurde im Vergleich mit dem unbehandelten Stück wie folgt bewertet.
  • A: Kontrollrate 100-95%
  • B: Kontrollrate 94-80%
  • C: Kontrollrate 79-60%
  • D: Kontrollrate 59- 0%
  • Tabelle 2 zeigt die Ergebnisse Tabelle 2 Verbindung Nr. Fungizider Effekt Bezugsverbindung Bemerkung: Bezugsverbindung A: Verbindung von JP-A-61-28 0452 Bezugsverbindung B: Verbindung von JP-A-61-106538 Bezugsverbindung D: Verbindung von JP-A-61-106538
    • Testbeispiel 2. Kontrolleffekt auf flaumigen Mehltau von Gurke (Pseudoperonospora cubensis)
  • Gurkenpflanzen im Zwei-Blatt-Stadium wurden mit der Testverbindung (200 ppm) einen Tag vor der Inokulation mit Zoosporen von Pseudoperonospora cubensis besprüht. Nachdem die Pflanzen in einem feuchten Raum einen Tag bei 25ºC und dann 6 Tage in einen Gewächshaus gehalten worden war, wurde der Grad des Befalls pro Blatt untersucht. Die Krankheitskontrollwirksamkeit wurde auf dieselbe Weise wie in dem Testbeispiel 1 ermittelt. Die Ergebnisse sind in Tabelle 3 gezeigt. Tabelle 3 Verbindung Nr. Fungizider Effekt
    • Testbeispiel 3. Kontrolleffekt auf Reisbrand (Pyricularia oryzae)
  • Reiskeimlinge in Fünf-Blatt-Stadium wurden mit der Testverbindung (200 ppm) einen Tag vor der Inokulation mit Conidia von Pyricularia oryzae besprüht. Nachdem die Keimlinge in einem feuchten Raum bei 25ºC einen Tag und dann 6 Tage in einem Gewächshaus gehalten worden waren, wurde die Zahl der auftretenden Veränderungen pro Blatt untersucht. Die Krankheitskontrollwirksamkeit wurde auf dieselbe Weise wie in dem Testbeispiel 1 ermittelt. Die Ergebnisse sind in der Tabelle 4 gezeigt. Tabelle 4 Verbindung Nr. Fungizider Effekt Bezugsverbindung

Claims (8)

1. N-substituierte Benzyloxyiminderivate der allgemeinen Formel (I):
worin R¹ und R² jeweils unabhängig voneinander eine C&sub1;- C&sub6;-Alkylgruppe darstellen;
eines von R³ und R&sup4; eine C&sub1;-C&sub6;-Alkylgruppe, eine C&sub1;-C&sub6;- Halogenalkylgruppe oder eine niedrige Alkoxyalkylgruppe darstellt, und
das andere ein stickstoffatomhaltiger Heteroring ist, ausgewählt aus der Gruppe, bestehend aus substuiertem und unsubstituiertem Pyrrolidin, Piperidin, Morpholin, Thiomorpholin, Piperazin, Mexamethylenimin, Tetrahydrochinolin und Tetrahydroisochinolin, und das Stickstoffatom in dem Heteroring immer die Bindung als ein Substituent von entweder R³ oder R&sup4; bildet.
2. N-substituierte Benzyloxyiminderivate nach Anspruch 1, worin der Heteroring mit mindestens einem Mitglied, ausgewählt aus der Gruppe, bestehend aus einem Halogenatom, einer C&sub1;-C&sub6;-Alkylgruppe, einer Phenylgruppe, die 1 bis 5 Substituenten aufweisen kann, unabhängig voneinander ausgewählt aus Halogenatomen, Benzylgruppen, Pyridylgruppen, Pyrimidylgruppen und Dioxolangruppen, substituiert ist.
3. N-substituierte Benzyloxyiminderivate nach Anspruch 2, worin der Heteroring mit 1 bis 3 Alkylgruppen substituiert ist.
4. N-substituiertes Benzyloxyiminderivat nach Anspruch 1, worin eines von R³ und R&sup4; eine Morpholinogruppe ist, die mit einer C&sub1;-C&sub6;-Alkylgruppe substituiert sein kann, und das andere eine C&sub1;-C&sub6;-Alkylgruppe, eine C&sub1;-C&sub6;-Halogenalkylgruppe oder eine niedrige Alkoxyalkylgruppe ist.
5. N-substituiertes Benzyloxyiminderivat nach Anspruch 4, worin das andere eine C&sub1;-C&sub6;-Alkylgruppe oder eine C&sub1;- C&sub6;-Halogenalkylgruppe ist.
6. Verfahren zum Herstellen von N-substituierten Benzyloxyiminderivaten der allgemeinen Formel (I):
worin R¹ und R² jeweils unabhängig voneinander eine C&sub1;- C&sub6;-Alkylgruppe darstellen;
eines von R³ und R&sup4; eine C&sub1;-C&sub6;-Alkylgruppe, eine C&sub1;-C&sub6;- Halogenalkylgruppe oder eine niedrige Alkoxyalkylgruppe darstellt, und
das andere ein stickstoffatomhaltiger Heteroring ist, ausgewählt aus der Gruppe, bestehend aus substuiertem und unsubstituiertem Pyrrolidin, Piperidin, Morpholin, Thiomorpholin, Piperazin, Hexamethylenimin, Tetrahydrochinolin und Tetrahydroisochinolin, und das Stickstoffatom in dem Heteroring immer die Bindung als ein Substituent von entweder R³ oder R&sup4; bildet;
welches das Reagierenlassen einer Verbindung der allgemeinen Formel (II):
worin R¹ und R² wie in der vorstehenden Formel (I) definiert sind, und X ein Halogenatom darstellt, mit einer Verbindung der allgemeinen Formel (III):
worin R³ und R&sup4; wie in der vorstehenden Formel (I) definiert sind, umfaßt.
7. Landwirtschafts- und Gartenbaufungizid, welches ein N- substituiertes Benzyloxyiminderivat nach einem der Ansprüche 1 bis 5 in solch einer Menge, die eine landwirtschaftliche und gartenbauliche Fungizidwirkung zeigt, und einen Träger, der als landwirtschaftlicher und gartenbaulicher inerter Träger annehmbar ist, umfaßt.
8. Verfahren zum Kontrollieren von Pflanzenkrankheit, welches das Aufbringen eines Landwirtschafts- oder Gartenbaufungizids nach Anspruch 7 in einer Menge, als aktiver Bestandteil, von 0,1 bis 1.000 g pro 10 Ar umfaßt.
DE90115822T 1989-08-22 1990-08-17 N-Substituierte Benzyloxyiminderivate, Verfahren zu deren Herstellung und deren Verwendung. Expired - Fee Related DE69006290T2 (de)

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CN1088384A (zh) 1994-06-29
KR950002839B1 (ko) 1995-03-27
KR910004546A (ko) 1991-03-28
DE69006290D1 (de) 1994-03-10
AU628625B2 (en) 1992-09-17
EP0414153A1 (de) 1991-02-27
CA2023515C (en) 1997-02-11
CA2023515A1 (en) 1991-02-23
US5104872A (en) 1992-04-14
EP0414153B1 (de) 1994-01-26
AU6112790A (en) 1991-02-28
JPH03169842A (ja) 1991-07-23
CN1049654A (zh) 1991-03-06
CN1024662C (zh) 1994-05-25

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