DE3541722A1 - Quinoline derivatives and their use for controlling undesired vegetation - Google Patents

Quinoline derivatives and their use for controlling undesired vegetation

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Publication number
DE3541722A1
DE3541722A1 DE19853541722 DE3541722A DE3541722A1 DE 3541722 A1 DE3541722 A1 DE 3541722A1 DE 19853541722 DE19853541722 DE 19853541722 DE 3541722 A DE3541722 A DE 3541722A DE 3541722 A1 DE3541722 A1 DE 3541722A1
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Prior art keywords
substituted
alkoxycarbonyl
radical
alkyl
formula
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DE19853541722
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German (de)
Inventor
Helmut Dr Hagen
Ulrich Dr Eichenauer
Peter Dr Plath
Norbert Dr Meyer
Bruno Dr Wuerzer
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BASF SE
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BASF SE
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Priority to DE19853541722 priority Critical patent/DE3541722A1/en
Priority to JP61262063A priority patent/JPS62126175A/en
Priority to EP86116185A priority patent/EP0224823A3/en
Priority to US06/933,795 priority patent/US4797148A/en
Publication of DE3541722A1 publication Critical patent/DE3541722A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
    • A01N43/34—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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • 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
    • A01N43/80—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 1,2
    • 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
    • A01N43/82—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 three ring hetero 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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

Abstract

Quinoline derivatives of the formula <IMAGE> in which R<1>, X, Y and Z in each case have the meaning given in the description, herbicides comprising these compounds as active ingredients, and a method of controlling undesired vegetation.

Description

Die vorliegende Erfindung betrifft neue Chinolinderivate, Herbizide, die diese Verbindungen als Wirkstoffe enthalten, sowie ein Verfahren zur Bekämpfung von unerwünschtem Pflanzenwachstum mittels der neuen Verbindungen.The present invention relates to new quinoline derivatives, herbicides which contain these compounds as active ingredients, and a method for combating of undesirable plant growth using the new compounds.

Es ist bekannt, daß substituierte Chinoline herbizid wirksam sind (DE-A-31 08 873, DE-A-32 10 979, DE-A-32 29 175, DE-A-32 33 089).It is known that substituted quinolines have herbicidal activity (DE-A-31 08 873, DE-A-32 10 979, DE-A-32 29 175, DE-A-32 33 089).

Es wurde nun gefunden, daß Chinolinderivate der Formel I
in der
R1 Halogen oder C1-C4-Alkyl,
X Halogen,
Z Sauerstoff, Hydroxyimino, C1-C4-Alkoxyimino oder einen Hydrazonorest, der durch C1-C4-Alkyl, C1-C4-Alkoxycarbonyl, Arylsulfonyl, 1,3-Oxazol- 2-yl oder 1,3-Thiazol-2-yl substituiert ist, wobei die letztgenannten heterocyclischen Reste wiederum durch C1-C4-Alkyl, C2-C4- Hydroxyalkyl oder Hydroxyl substituiert sind, und
Y für den Fall, daß Z die Bedeutung von Sauerstoff besitzt, den Rest -NR2R3, in dem R2 für Wasserstoff und R3 für C1-C4-Hydroxyalkyl, C1-C4- Alkoxy, C2-C4-Alkenyl, das durch -C≡N oder C1-C4-Alkoxycarbonyl substituiert ist, Arylsulfonyl, 1,3-Oxazol-2-yl oder 1,3-Thiazol-2-yl steht, oder in dem R2 und R3 zusammen für C1-C4-Alkyliden stehen, das durch C1-C4-Dialkylamino, Hydroxyamino oder C1-C4-Alkoxyamino substituiert ist; einen Hydrazinorest, der gegebenenfalls durch C1-C4-Alkoxycarbonyl, C2-C6-Alkyliden, Thiocarbamoyl, C1-C4-Alkoxy-oxalyl, Amino-oxalyl oder Arylsulfonyl substituiert ist; C1-C4-Alkyl, das gegebenenfalls durch C1-C4-Alkoxycarbonyl substituiert ist; oder C3-C8-Cycloalkenyl, das durch C1-C4-Dialkylamino oder C4-C6-Alkylenimino substituiert ist,
für den Fall, daß Z die Bedeutung von C1-C4-Alkoxyimino oder des oben genannten substituierten Hydrazonorests besitzt, Wasserstoff oder Halogen, und
für den Fall, daß Z die Bedeutung von Hydroxyimino besitzt, Halogen, Amino, C1-C4-Alkoxy oder C1-C4-Alkylthio, das durch Carboxyl oder C1-C4-Alkoxycarbonyl substituiert ist, bedeuten,
oder in der die Gruppe für den Rest -C≡N⊕-O⊖ oder einen fünfgliedrigen Heterocyclus steht, der neben einem Stickstoffatom noch ein oder zwei weitere Heteroatome, ausgewählt aus der Gruppe, bestehend aus Stickstoff, Sauerstoff und Schwefel, sowie eine oder zwei Doppelbindungen aufweist, und der gegebenenfalls substituiert und/oder durch weitere Carbo- oder Heterocyclen anneliert und über ein Kohlenstoffatom an den Chinolinring gebunden ist, herbizid wirksam sind.It has now been found that quinoline derivatives of the formula I
in the
R 1 is halogen or C 1 -C 4 alkyl,
X halogen,
Z is oxygen, hydroxyimino, C 1 -C 4 -alkoxyimino or a hydrazone radical which is substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, arylsulfonyl, 1,3-oxazol-2-yl or 1,3- Thiazol-2-yl is substituted, the latter heterocyclic radicals in turn being substituted by C 1 -C 4 alkyl, C 2 -C 4 hydroxyalkyl or hydroxyl, and
Y if Z is oxygen, the radical -NR 2 R 3 , in which R 2 is hydrogen and R 3 is C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 2 - C 4 alkenyl which is substituted by -C≡N or C 1 -C 4 alkoxycarbonyl, arylsulfonyl, 1,3-oxazol-2-yl or 1,3-thiazol-2-yl, or in which R 2 and R 3 together represent C 1 -C 4 alkylidene which is substituted by C 1 -C 4 dialkylamino, hydroxyamino or C 1 -C 4 alkoxyamino; a hydrazine radical which is optionally substituted by C 1 -C 4 alkoxycarbonyl, C 2 -C 6 alkylidene, thiocarbamoyl, C 1 -C 4 alkoxy oxalyl, amino oxalyl or arylsulfonyl; C 1 -C 4 alkyl, which is optionally substituted by C 1 -C 4 alkoxycarbonyl; or C 3 -C 8 cycloalkenyl which is substituted by C 1 -C 4 dialkylamino or C 4 -C 6 alkyleneimino,
in the event that Z has the meaning of C 1 -C 4 -alkoxyimino or the abovementioned substituted hydrazone radical, hydrogen or halogen, and
in the event that Z has the meaning of hydroxyimino, are halogen, amino, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio which is substituted by carboxyl or C 1 -C 4 -alkoxycarbonyl,
or in the group represents the radical -C≡N⊕-O⊖ or a five-membered heterocycle which, in addition to a nitrogen atom, also has one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and one or two double bonds, and the optionally substituted and / or fused by further carbocycles or heterocycles and bound to the quinoline ring via a carbon atom, are herbicidally active.

R1 in Formel I bedeutet z. B. Fluor, Chlor oder Brom, vorzugsweise Chlor; oder Methyl, Ethyl, Propyl, Isopropyl, Butyl, Isobutyl, But-2-yl oder tert-Butyl, vorzugsweise Methyl.R 1 in formula I means z. B. fluorine, chlorine or bromine, preferably chlorine; or methyl, ethyl, propyl, isopropyl, butyl, isobutyl, but-2-yl or tert-butyl, preferably methyl.

X in Formel I bedeutet z. B. Fluor, Chlor oder Brom, vorzugsweiseChlor.X in formula I means z. Fluorine, chlorine or bromine, preferably chlorine.

Z in Formel I bedeutet z. B. Sauerstoff; Hydroxyimino; Methoxyimino, Ethoxyimino, Propoxyimino oder Butoxyimino; Methylhydrazono, Ethylhydrazono, Isopropylhydrazono, Butylhydrazono, Methoxycarbonylhydrazono, Ethoxycarbonylhydrazono, Propoxycarbonylhydrazono, tert-Butoxycarbonylhydrazono, Phenylsulfonylhydrazono, 2-Methylphenylsulfonylhydrazono, 4-Methylphenylsulfonylhydrazono, 4-Chlorphenylsulfonylhydrazono, 4-Methyl-1,3- thiazol-2-yl-hydrazono, 4-Ethyl-1,3-oxazol-2-yl-hydrazono, 4-tert-Butyl- 1,3-thiazol-2-yl-hydrazono, 4-Hydroxy-1,3-oxazol-2-yl-hydrazono, 4-Hydroxyl-1,3-thiazol-2-yl-hydrazono, 4-(2-Hydroxyethyl)-1,3-thiazol- 2-yl-hydrazono oder 3-(2-Hydroxyethyl)-4-hydroxy-1,3-thiazol-2-yl-hydrazono.Z in formula I means z. B. oxygen; Hydroxyimino; Methoxyimino, Ethoxyimino, propoxyimino or butoxyimino; Methylhydrazono, ethylhydrazono, Isopropylhydrazono, butylhydrazono, methoxycarbonylhydrazono, ethoxycarbonylhydrazono, Propoxycarbonylhydrazono, tert-butoxycarbonylhydrazono, Phenylsulfonylhydrazono, 2-methylphenylsulfonylhydrazono, 4-methylphenylsulfonylhydrazono, 4-chlorophenylsulfonylhydrazono, 4-methyl-1,3- thiazol-2-yl-hydrazono, 4-ethyl-1,3-oxazol-2-yl-hydrazono, 4-tert-butyl 1,3-thiazol-2-yl-hydrazono, 4-hydroxy-1,3-oxazol-2-yl-hydrazono, 4-hydroxyl-1,3-thiazol-2-yl-hydrazono, 4- (2-hydroxyethyl) -1,3-thiazole- 2-yl-hydrazono or 3- (2-hydroxyethyl) -4-hydroxy-1,3-thiazol-2-yl-hydrazono.

Die Bedeutung von Y in Formel I richtet sich nach der Bedeutung des Restes Z.The meaning of Y in formula I depends on the meaning of Rest Z.

Für den Fall, daß Z die Bedeutung von Sauerstoff besitzt, bedeutet Y z. B. 2-Hydroxyethylamino, (1-Methyl-2-hydroxy)ethylamino, 3-Hydroxypropylamino, (1,1-Dimethyl-2-hydroxy)ethylamino; Methoxyamino, Ethoxyamino, Propoxyamino, Isopropoxyamino, Butoxyamino, Isobutoxyamino; 2-Cyano-2- methylethenylamino, 2-(Methoxycarbonyl)ethenylamino, 2-(Ethoxycarbonyl)- 2-methylethenylamino, 3-(Ethoxycarbonyl)prop-2-en-2-ylamino; Phenylsulfonylamino; 2-Methylphenylsulfonylamino, 4-Methylphenylsulfonylamino, 4- Chlorphenylsulfonylamino, 1,3-Oxazol-2-ylamino; 1,3-Thiazol-2-ylamino; Dimethylaminomethylidenamino, 1-(Dimethylamino)ethylidenamino; Hydroxyaminomethylidenamino; 1-(Hydroxyamino)ethylidenamino; Methoxyaminomethylidenamino, 1-(Ethoxyamino)ethylidenamino; Hydrazino; Methoxycarbonylhydrazino, Ethoxycarbonylhydrazino, Isopropoxycarbonylhydrazino, tert- Butoxycarbonylhydrazino; Ethylidenhydrazino, Prop-2-ylidenhydrazino, 2- Methylbut-3-ylidenhydrazino; Thiocarbamoylhydrazino; Methoxyoxalylhydrazino, Ethoxyoxalylhydrazino; Aminooxalylhydrazino; Phenylsulfonylhydrazino, 2-Methylphenylsulfonylhydrazino, 4-Methylphenylsulfonylhydrazino, 4-Chlorphenylsulfonylhydrazino; Methyl, Ethyl, Propyl, Butyl; Ethoxycarbonylmethyl; 2-Dimethylaminocyclopent-1-en-1-yl, 2-Diethylaminocyclopent- 1-en-1-yl, 2-Pyrrolidinocyclopent-1-en-1-yl, 2-Pyrrolidinocyclohex- 1-en-1-yl oder 2-Piperidinocyclohex-1-en-1-yl.In the event that Z has the meaning of oxygen, Y means z. B. 2-hydroxyethylamino, (1-methyl-2-hydroxy) ethylamino, 3-hydroxypropylamino, (1,1-dimethyl-2-hydroxy) ethylamino; Methoxyamino, ethoxyamino, Propoxyamino, isopropoxyamino, butoxyamino, isobutoxyamino; 2-cyano-2-  methylethenylamino, 2- (methoxycarbonyl) ethenylamino, 2- (ethoxycarbonyl) - 2-methylethenylamino, 3- (ethoxycarbonyl) prop-2-en-2-ylamino; Phenylsulfonylamino; 2-methylphenylsulfonylamino, 4-methylphenylsulfonylamino, 4- Chlorophenylsulfonylamino, 1,3-oxazol-2-ylamino; 1,3-thiazol-2-ylamino; Dimethylaminomethylidenamino, 1- (dimethylamino) ethylidenamino; Hydroxyaminomethylideneamino; 1- (hydroxyamino) ethylidenamino; Methoxyaminomethylidene amino, 1- (ethoxyamino) ethylidenamino; Hydrazino; Methoxycarbonylhydrazino, Ethoxycarbonylhydrazino, isopropoxycarbonylhydrazino, tert- Butoxycarbonylhydrazino; Ethylidene hydrazino, prop-2-ylidene hydrazino, 2- Methylbut-3-ylidene hydrazino; Thiocarbamoylhydrazino; Methoxyoxalylhydrazino, Ethoxyoxalylhydrazino; Aminooxalylhydrazino; Phenylsulfonylhydrazino, 2-methylphenylsulfonylhydrazino, 4-methylphenylsulfonylhydrazino, 4-chlorophenylsulfonylhydrazino; Methyl, ethyl, propyl, butyl; Ethoxycarbonylmethyl; 2-dimethylaminocyclopent-1-en-1-yl, 2-diethylaminocyclopent- 1-en-1-yl, 2-pyrrolidinocyclopent-1-en-1-yl, 2-pyrrolidinocyclohex- 1-en-1-yl or 2-piperidinocyclohex-1-en-1-yl.

Für den Fall, daß Z die Bedeutung von C1-C4-Alkoxyimino oder des oben genannten Hydrazonorests besitzt, bedeutet Y z. B. Wasserstoff, Chlor oder Brom.In the event that Z has the meaning of C 1 -C 4 alkoxyimino or the abovementioned hydrazone radical, Y means z. B. hydrogen, chlorine or bromine.

Für den Fall schließlich, daß Z die Bedeutung von Hydroxyimino besitzt, bedeutet Y z. B. Chlor, Brom, Amino; Methoxy, Ethoxy, Propoxy, Isopropoxy, Butoxy, Isobutoxy; Carboxymethylthio oder Ethoxycarbonylmethylthio.Finally, in the event that Z has the meaning of hydroxyimino, Y means z. B. chlorine, bromine, amino; Methoxy, ethoxy, propoxy, isopropoxy, Butoxy, isobutoxy; Carboxymethylthio or ethoxycarbonylmethylthio.

Die Gruppe The group

kann auch für den Rest -C≡N⊕-O⊖ stehen oder, wie oben definiert, einen fünfgliedrigen Heterocyclus bedeuten. Dabei kann der Heterocyclus durch C1-C4-Alkyl, das gegebenenfalls durch Hydroxyl oder C1-C4-Alkoxy substituiert ist, C1-C4-Alkoxy, Hydroxyl, Amino, C1-C4-Dialkylamino, C4-C6- Alkylenimino, C1-C4-Alkoxycarbonyl, Carbamoyl oder Cyan substituiert und/oder durch Carboxyclen, wie Cyclopentan oder Cyclohexyan, oder durch Heterocyclen, wie Tetrahydrofuran oder Tetrahydropyran, anneliert sein.can also represent the radical -C≡N⊕-O⊖ or, as defined above, mean a five-membered heterocycle. The heterocycle can be C 1 -C 4 alkyl, which is optionally substituted by hydroxyl or C 1 -C 4 alkoxy, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 dialkylamino, C 4 -C 6 - Alkylenimino, C 1 -C 4 alkoxycarbonyl, carbamoyl or cyan substituted and / or fused with carboxyls, such as cyclopentane or cyclohexyan, or with heterocycles, such as tetrahydrofuran or tetrahydropyran.

Beispielhaft seien folgende heterocyclische Reste genannt: 1,3,4-Triazol- 2-yl, 5-Methyl-1,3,4-triazol-2-yl; 4,5-Dihydro-1,3-oxazol-2-yl, 4,5-Di- hydro-4-methyl-1,3-oxazol-2-yl, 1,3-Oxazol-2-yl, 4,5-Dihydro-1,2-oxazol- 3-yl, 4,5-Dihydro-5-ethoxy-1,2-oxazol-3-yl, 5-Methoxymethyl-1,2-oxazol- 3-yl, 4-Methoxycarbonyl-5-hydroxy-1,2-oxazol-3-yl, 4-Methoxycarbonyl-5- methyl-1,2-oxazol-3-yl, 4,5-Dihydro-5-hydroxymethyl-1,2-oxazol-3-yl, 4,5-Dihydro-5-methyl-5-methoxycarbonyl-1,2-oxazol-3-yl, 4,5-Dihydro-5- methoxycarbonyl-1,2-oxazol-3-yl, 4,5-Dihydro-4,5-bis(methoxycarbonyl)- 1,2-oxazol-3-yl (trans), 4,5-Dihydro-4-cyano-5-amino-1,2-oxazol-3-yl, 3a,4,5,6-Tetrahydro-6a-pyrrolidino-cyclopenta[d][1,2]oxazol-3-yl, 3a,4,5,6a-Tetrahydro-furo[3,2-d][1,2]oxazol-3-yl, 3a,4,6,6a-Tetrahydro- furo[3,4-d][1,2]oxazol-3-yl, 4H-3a,5,6,7a-Tetrahydro-pyrano[3,2- d][1,2]oxazol-3-yl, 4,5-Dihydro-1,3-thiazol-2-yl, 1,3,4-Oxdiazol-2-yl, 5-Ethyl-1,3,4-oxdiazol-2-yl, 5-Hydroxy-1,3,4-oxidiazol-2-yl, 5-Carbamoyl- 1,3,4-oxdiazol-2-yl oder 3-Methyl-1,2,4-oxdiazol-5-yl.The following heterocyclic radicals may be mentioned as examples: 1,3,4-triazole 2-yl, 5-methyl-1,3,4-triazol-2-yl; 4,5-dihydro-1,3-oxazol-2-yl, 4,5-di- hydro-4-methyl-1,3-oxazol-2-yl, 1,3-oxazol-2-yl, 4,5-dihydro-1,2-oxazol 3-yl, 4,5-dihydro-5-ethoxy-1,2-oxazol-3-yl, 5-methoxymethyl-1,2-oxazole  3-yl, 4-methoxycarbonyl-5-hydroxy-1,2-oxazol-3-yl, 4-methoxycarbonyl-5- methyl-1,2-oxazol-3-yl, 4,5-dihydro-5-hydroxymethyl-1,2-oxazol-3-yl, 4,5-dihydro-5-methyl-5-methoxycarbonyl-1,2-oxazol-3-yl, 4,5-dihydro-5- methoxycarbonyl-1,2-oxazol-3-yl, 4,5-dihydro-4,5-bis (methoxycarbonyl) - 1,2-oxazol-3-yl (trans), 4,5-dihydro-4-cyano-5-amino-1,2-oxazol-3-yl, 3a, 4,5,6-tetrahydro-6a-pyrrolidino-cyclopenta [d] [1,2] oxazol-3-yl, 3a, 4,5,6a-tetrahydro-furo [3,2-d] [1,2] oxazol-3-yl, 3a, 4,6,6a-tetrahydro- furo [3,4-d] [1,2] oxazol-3-yl, 4H-3a, 5,6,7a-tetrahydro-pyrano [3,2- d] [1,2] oxazol-3-yl, 4,5-dihydro-1,3-thiazol-2-yl, 1,3,4-oxdiazol-2-yl, 5-ethyl-1,3,4-oxdiazol-2-yl, 5-hydroxy-1,3,4-oxidiazol-2-yl, 5-carbamoyl- 1,3,4-oxdiazol-2-yl or 3-methyl-1,2,4-oxdiazol-5-yl.

Bevorzugt sind Verbindungen in denen R1 und X Halogen, insbesondere Chlor, Z Sauerstoff und Y den Rest -NHR3, wobei R3 für C1-C4-Alkoxy, insbesondere Ethoxy steht, bedeuten.Compounds in which R 1 and X are halogen, in particular chlorine, Z oxygen and Y are the radical -NHR 3 , where R 3 is C 1 -C 4 alkoxy, in particular ethoxy, are preferred.

Die erfindungsgemäßen Carbonsäureamide und Carbonsäurehydrazide (Y = O, Z = NR2R3 bzw. Hydrazinorest) werden durch Umsetzung des Säurechlorids (Y = O, Z = Cl) mit den betreffenden Aminen bzw. Hydrazinen in einem inerten Lösungsmittel unter Zusatz eines säurebindenden Mittels erhalten.The carboxylic acid amides and carboxylic acid hydrazides (Y = O, Z = NR 2 R 3 or hydrazine residue) according to the invention are obtained by reacting the acid chloride (Y = O, Z = Cl) with the amines or hydrazines in question in an inert solvent with the addition of an acid-binding agent receive.

Als inerte Lösungsmittel kommen chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder Chlorbenzol; Ether, wie Tetrahydrofuran, Dioxan, 1,2-Di- methoxyethan oder Diethylenglykoldimethylether; aromatische Kohlenwasserstoffe, wie Toluol oder Xylol in Frage. Bevorzugt sind 1,2-Dimethoxyethan und Methylenchlorid.Chlorinated hydrocarbons such as methylene chloride come as inert solvents or chlorobenzene; Ethers, such as tetrahydrofuran, dioxane, 1,2-di methoxyethane or diethylene glycol dimethyl ether; aromatic hydrocarbons, like toluene or xylene in question. 1,2-Dimethoxyethane are preferred and methylene chloride.

Als säurebindendes Mittel kommen tertiäre Amine, wie Triethylamin, Pyridin oder N,N-Dimethylaminopyridin in Betracht. Zweckmäßig verwendet man 1 bis 2 Mol säurebindendes Mittel pro Mol Säurechlorid.Tertiary amines such as triethylamine and pyridine come as acid-binding agents or N, N-dimethylaminopyridine. It is advisable to use 1 up to 2 moles of acid-binding agent per mole of acid chloride.

In manchen Fällen kann auch ein entsprechender Überschuß der Amin- bzw. Hydrazinkomponente vorteilhaft als Säurebinder eingesetzt werden. Bevorzugt verwendet man Triethylamin.In some cases, a corresponding excess of the amine or Hydrazine component can be used advantageously as an acid binder. Prefers one uses triethylamine.

Die Reaktionstemperatur kann innerhalb eines größeren Bereichs variiert werden. Im allgemeinen arbeitet man bei einer Temperatur von -30 bis +80°C, vorzugsweise -10 bis +25°C.The reaction temperature can vary within a wide range will. Generally one works at a temperature of -30 to + 80 ° C, preferably -10 to + 25 ° C.

Eine Möglichkeit zur Herstellung von Säureamiden, die das Strukturelement aufweisen (R2, R3 = Alkyliden) besteht darin, das entsprechende freie Amid mit Amidacetalen (z. B. N,N-Dimethylformaid-dimethylacetal oder N,N-Dimethylacetamid-dimethylacetal) oder Orthocarbonsäureestern (z. B. Orthoameisensäuretrimethylester oder Orthoessigsäuretriethylester) umzusetzen.One way to make acid amides, which is the structural element (R 2 , R 3 = alkylidene) consists of the corresponding free amide with amido acetals (e.g. N, N-dimethylformaid dimethylacetal or N, N-dimethylacetamide dimethylacetal) or orthocarboxylic acid esters (e.g. trimethyl orthoformate or triethyl orthoacetate) ) to implement.

Als Lösungsmittel kommen N,N-Dimethylformamid, N,N-Dimethylacetamid sowie inerte hochsiedende Lösungsmittel (z. B. Toluol, Xylol oder Chlorbenzol) in Frage. In manchen Fällen ist es auch zweckmäßig, die Umsetzung in überschüssigem Amidacetal oder Orthocarbonsäureester durchzuführen. Der bei der Reaktion entstehende Alkohol kann im Reaktionsgemisch belassen werden oder wird vorzugsweise mittels Destillation entfernt.N, N-dimethylformamide, N, N-dimethylacetamide and inert high-boiling solvents (e.g. toluene, xylene or chlorobenzene) in question. In some cases it is also advisable to implement the excess amid acetal or orthocarboxylic acid ester. The Alcohol formed during the reaction can remain in the reaction mixture are or are preferably removed by distillation.

Als Reaktionsgemisch wählt man zweckmäßig die Rückflußtemperatur des Reaktionsgemisches, die im allgemeinen bei 100 bis 150°C liegt.The reflux temperature of the is advantageously chosen as the reaction mixture Reaction mixture, which is generally 100 to 150 ° C.

Die erfindungsgemäßen Keto-Verbindungen können in an sich bekannter Weise aus dem Carbonsäureester mittels einer Grignard-Reaktion erhalten werden, wobei es überraschend ist, daß in diesem Fall die Grignard-Reaktion auf der Keto-Stufe stehen bleibt und kein tertiärer Alkohol gebildet wird.The keto compounds according to the invention can be used in a manner known per se are obtained from the carboxylic acid ester by means of a Grignard reaction, it is surprising that in this case the Grignard reaction to the keto stage remains and no tertiary alcohol is formed.

Diejenigen erfindungsgemäßen Verbindungen, die heterocyclische Substituenten tragen, können nach an sich bekannten Methoden der Heterocyclensynthese, wie sie z. B. in R. A. Katritzky, C. W. Rees "Comprehensive Heterocyclic Chemistry", Band 4 und 5, Pergamon Press 1984 und A. Weissberger "Chemistry of Heterocyclic Compounds", Interscience Publishers beschrieben sind, erhalten werden.Those compounds according to the invention, the heterocyclic substituents can carry out, according to known methods of heterocycle synthesis, as they e.g. B. R. A. Katritzky, C. W. Rees "Comprehensive Heterocyclic Chemistry ", Vol. 4 and 5, Pergamon Press 1984 and A. Weissberger "Chemistry of Heterocyclic Compounds", Interscience Publishers are described.

Für den Fall, daß die Gruppe für den Rest -C≡N⊕-O⊖ steht, stellt man das Nitriloxid ausgehend vom Oxim über das Hydroxamsäurechlorid als Zwischenstufe und sich anschließender Chlorwasserstoffabspaltung her.In the event that the group stands for the rest -C≡N⊕-O⊖, the nitrile oxide is prepared starting from the oxime via the hydroxamic acid chloride as an intermediate and then splitting off hydrogen chloride.

Die weiteren erfindungsgemäßen Verbindungen (z. B. Oxime, Hydrazone oder Oximester) können ebenfalls nach an sich bekannten Methoden, wie sie beispielsweise in Houben-Weyl, "Methoden der organischen Chemie", Band 10/2 und 10/4 beschrieben sind, erhalten werden.The further compounds according to the invention (e.g. oximes, hydrazones or Oxime esters) can also be used according to methods known per se, such as, for example in Houben-Weyl, "Methods of Organic Chemistry", Volume 10/2 and 10/4 can be obtained.

Die nachfolgenden Beispiele sollen die Erfindung näher erläutern. The following examples are intended to explain the invention in more detail.  

Beispiel 1example 1

25 g (0,5 mol) Hydrazinhydrat und 50 g (0,5 mol) Triethylamin wurden in 500 ml Dimethoxyethan gelöst. In die Lösung wurden unter Eiskühlung 130 g (0,5 mol) 3,7-Dichlorchinolin-8-carbonsäurechlorid langsam eingetragen, so daß die Temperatur 20°C nicht überstieg. Nach 3-stündigem Rühren bei Raumtemperatur wurde das Lösungsmittel am Rotationsverdampfer entfernt, der Rückstand in Wasser aufgenommen und abgesaugt. Man erhielt 101,5 g (79%) 3,7-Dichlorchinolin-8-carbonsäurehydrazid vom Schmp. 136°C (Verb. 1).25 g (0.5 mol) hydrazine hydrate and 50 g (0.5 mol) triethylamine were in 500 ml of dimethoxyethane dissolved. 130 g were added to the solution while cooling with ice (0.5 mol) 3,7-dichloroquinoline-8-carboxylic acid chloride slowly added, so that the temperature did not exceed 20 ° C. After stirring for 3 hours The solvent was removed at room temperature on a rotary evaporator, the residue is taken up in water and suction filtered. 101.5 g were obtained (79%) 3,7-dichloroquinoline-8-carboxylic acid hydrazide, mp. 136 ° C (Verb. 1).

Die nachfolgenden Beispiele in Tabelle 1 wurden in analoger Weise erhalten. The following examples in Table 1 were obtained in an analogous manner.

Beispiel 21Example 21 3,7-Dichlorchinolin-8-hydroxamsäure-O-ethylester3,7-dichloroquinoline-8-hydroxamic acid-O-ethyl ester

13,0 g (50 mmol) 3,7-Dichlorchinolin-8-carbonsäurechlorid wurden in 50 ml Dimethoxyethan suspendiert und 5,8 g (60 mmol) O-Ethylhydroxylamin-hydrochlorid sowie 15 g (150 mmol) Triethylamin zugegeben. Nach 5-stündigem Rühren bei Raumtemperatur wurde das Lösungsmittel am Rotationsverdampfer entfernt, der Rückstand mit Wasser verrieben und abgesaugt. Man erhielt 11,0 g (77%), Schmp.: 140°C (Verb. 21).13.0 g (50 mmol) of 3,7-dichloroquinoline-8-carboxylic acid chloride were dissolved in 50 ml Suspended dimethoxyethane and 5.8 g (60 mmol) of O-ethylhydroxylamine hydrochloride and 15 g (150 mmol) of triethylamine were added. After 5 hours The solvent was stirred on a rotary evaporator at room temperature removed, the residue triturated with water and suction filtered. You got 11.0 g (77%), mp: 140 ° C (Verb. 21).

Beispiel 22Example 22 N,N-Dimethyl-N′-(7-Chlor-3methyl-8-chinolinoyl)-formamidinN, N-Dimethyl-N '- (7-chloro-3methyl-8-quinolinoyl) formamidine

Man löste 55,1 g (0,25 mol) 7-Chlor-3-methylchinolin-8-carboxamid in 50 ml N,N-Dimethylformamid, gab 39,3 g (0,32 mol) N,N-Dimethylformamid- dimethylacetal zu und erhitzte 4 Stunden unter Rückfluß. Nach Fällen auf Ether isolierte man 44,0 g (64%) farblose Kristalle, Schmp. 183 bis 185°C (Zers.) (Verbindung Nr. 22)55.1 g (0.25 mol) of 7-chloro-3-methylquinoline-8-carboxamide were dissolved in 50 ml of N, N-dimethylformamide gave 39.3 g (0.32 mol) of N, N-dimethylformamide dimethyl acetal and heated under reflux for 4 hours. After cases on Ether was isolated 44.0 g (64%) colorless crystals, mp. 183 bis 185 ° C (dec.) (Compound no. 22)

Die nachfolgenden Beispiele in Tabelle 2 wurden in analoger Weise erhalten.The following examples in Table 2 were obtained in an analogous manner.

Tabelle 2 Table 2

Beispiel 26Example 26 N-(7-Chlor-3-methyl-8-chinolinoyl)-formamidoximN- (7-chloro-3-methyl-8-quinolinoyl) formamide oxime

13,8 g (50 mmol) Amidin aus Beispiel 21 suspendierte man in 50 ml Eisessig, gab 4,2 g (60 mmol) Hydroxylammoniumhydrochlorid und 5,0 g (60 mmol) Natriumacetat zu, erhitzte 5 Stunden unter Rückfluß, fällte auf Wasser und saugte ab. 6,0 g (45%), Schmp. 235-238°C (Verbindung Nr. 26). Die entsprechende 3-Chlorchinolinverbindung wurde analog erhalten, Schmp. 220 bis 230°C (Verbindung Nr. 27).13.8 g (50 mmol) of amidine from Example 21 were suspended in 50 ml of glacial acetic acid, gave 4.2 g (60 mmol) of hydroxylammonium hydrochloride and 5.0 g (60 mmol) sodium acetate, heated under reflux for 5 hours, attracted attention Water and sucked off. 6.0 g (45%), m.p. 235-238 ° C (Compound No. 26).  The corresponding 3-chloroquinoline compound was obtained analogously, mp. 220 to 230 ° C (compound no.27).

Beispiel 28Example 28 2-(7-Chlor-3-methylchinolin-8-yl)-1,3,4-oxdiazol2- (7-chloro-3-methylquinolin-8-yl) -1,3,4-oxdiazole

12,0 g (50 mmol) 7-Chlor-3-methylchinolin-8-carbonsäurehydrazid (Verbindung Nr. 8) wurden in Triethylorthoformiat 3 Stunden auf 120°C erhitzt und der entstehende Alkohol abdestilliert. Abziehen des überschüssigen Orthoesters und Anreiben mit Ether lieferte 9,4 g (77%), Schmp. 165°C (Verbindung Nr. 28).12.0 g (50 mmol) 7-chloro-3-methylquinoline-8-carboxylic acid hydrazide (compound No. 8) were heated in triethyl orthoformate at 120 ° C. for 3 hours and the resulting alcohol is distilled off. Deduct the excess Orthoesters and trituration with ether gave 9.4 g (77%), mp. 165 ° C. (Compound No. 28).

Die Verbindungen der Tabelle 3 wurden analog erhalten.The compounds of Table 3 were obtained analogously.

Tabelle 3 Table 3

Beispiel 32Example 32 5-(3,7-Dichlorchinolin-8-yl)-1,3,4-oxdiazol-2-carboxamid5- (3,7-dichloroquinolin-8-yl) -1,3,4-oxdiazol-2-carboxamide

26,0 g (80 mmol) von Verbindung Nr. 4 rührte man 6 Stunden bei 130°C in 100 g Polyphosphorsäure. Danach rührte man in Wasser ein und ließ über Nacht auskristallisieren. 16,3 g (66%), Schmp. 220°C (Zers.) (Verbindung Nr. 31). 26.0 g (80 mmol) of compound no. 4 was stirred in at 130 ° C. for 6 hours 100 g polyphosphoric acid. Thereafter, the mixture was stirred into water and left over Crystallize night. 16.3 g (66%), mp. 220 ° C (dec.) (Compound No. 31).  

Beispiel 33Example 33 5-(3,7-Dichlorchinolin-8-yl)-1,3,4-oxdiazol-2-on5- (3,7-dichloroquinolin-8-yl) -1,3,4-oxdiazol-2-one

12,8 g (50 mmol) 3,7-Dichlorchinolin-8-carbonsäurehydrazid (Verbindung Nr. 1) wurden in 100 ml Dimethoxyethan suspendiert, 7,9 g (100 mmol) Pyridin zugegeben und danach Phosgen über einen Zeitraum von 4 Stunden bei 25°C eingeleitet. Nach Entfernen von überschüssigem Phosgen und Lösungsmittel rührte man in Wasser ein, und saugte ab: 8,7 g (62%), Schmp.: 87°C (Verbindung Nr. 33).12.8 g (50 mmol) of 3,7-dichloroquinoline-8-carboxylic acid hydrazide (compound No. 1) were suspended in 100 ml of dimethoxyethane, 7.9 g (100 mmol) Pyridine added and then phosgene over a period of 4 hours initiated at 25 ° C. After removing excess phosgene and Solvent was stirred into water and suction filtered: 8.7 g (62%), Mp: 87 ° C (compound no.33).

Analog gewann man das 3-Methylderivat. Schmp.: 232°C (Verbindung Nr. 34).The 3-methyl derivative was obtained analogously. Mp: 232 ° C (compound no.34).

Beispiel 35Example 35 4,5-Dihydro-2-(3,7-dichlorchinolin-8-yl)-oxazol4,5-dihydro-2- (3,7-dichloroquinolin-8-yl) oxazole

20,9 g (80 mmol) Verbindung Nr. 14 wurden in 50 ml Thionylchlorid 4 Stunden unter Rückfluß erhitzt. Man fällte auf Eis und gewann 18,3 g (86%), Schmp.: 145°C (Verbindung Nr. 35).20.9 g (80 mmol) of compound No. 14 were in 50 ml of thionyl chloride for 4 hours heated under reflux. It fell on ice and won 18.3 g (86%), Mp: 145 ° C (compound no.35).

Analog wurden die in Tabelle 4 aufgeführten Verbindungen hergestellt.The compounds listed in Table 4 were prepared analogously.

Tabelle 4 Table 4

Beispiel 39Example 39 3-(7-Chlor-3-methylchinolin-8-yl)-1,2,4-triazol3- (7-chloro-3-methylquinolin-8-yl) -1,2,4-triazole

13,8 g (50 mmol) Verbindung Nr. 21 wurden mit 3,0 (60 mmol) Hydrazinhydrat in 50 ml Eisessig 4 Stunden bei 70°C gerührt. Nach Fällen auf Wasser und Absaugen isolierte man 9,5 g (78%), Schmp. 274-276°C (Verbindung Nr. 39).13.8 g (50 mmol) of compound No. 21 were mixed with 3.0 (60 mmol) of hydrazine hydrate stirred in 50 ml of glacial acetic acid at 70 ° C for 4 hours. After cases on Water and suction were isolated 9.5 g (78%), mp. 274-276 ° C (compound No. 39).

In analoger Weise stellte man die Verbindung der Tabelle 5 dar.The compound of Table 5 was represented in an analogous manner.

Tabelle 5 Table 5

Beispiel 45Example 45 3,7-Dichlorchinolin-8-hydroxamsäurechlorid-hydrochlorid3,7-dichloroquinoline-8-hydroxamic acid chloride hydrochloride

In eine Suspension von 48,2 g (0,2 mol) 3,7-Dichlorchinolin-8-aldoxim in Chloroform leitete man 3 Stunden bei 40°C Chlor ein, saugte ab, wusch mit Ether und trocknete: 59,3 g (95%), Schmp.: ≦λτ300°C (Verb. Nr. 45). In a suspension of 48.2 g (0.2 mol) of 3,7-dichloroquinoline-8-aldoxime in Chloroform was introduced for 3 hours at 40 ° C chlorine, suction filtered, washed with Ether and dried: 59.3 g (95%), mp: ≦ λτ300 ° C (Verb.No. 45).  

Analog wurde erhalten:The following was obtained analogously:

3,7-Dichlorchinolin-8-hydroxamsäure-bromid-hydrobromid (Verb. Nr. 45).3,7-dichloroquinoline-8-hydroxamic acid bromide hydrobromide (Verb.No. 45).

Beispiel 47Example 47 3,7-Dichlorchinolin-8-nitriloxid3,7-dichloroquinoline-8-nitrile oxide

15,6 g (50 mmol) der Verbindung Nr. 45 wurden in 100 ml 10%ige Natriumcarbonat- Lösung eingerührt, 2 Stunden bei Raumtemperatur gerührt und abgesaugt: 108 g (90%), Schmp.: 185°C (Verb. Nr. 47).15.6 g (50 mmol) of compound no. 45 were dissolved in 100 ml of 10% sodium carbonate Solution stirred in, stirred at room temperature for 2 hours and suction filtered: 108 g (90%), mp: 185 ° C (Verb.No. 47).

Das Nitriloxid ist in analoger Weise auch aus Verbindung Nr. 46 zugänglich.The nitrile oxide can also be obtained from compound no. 46 in an analogous manner.

Beispiel 48Example 48 3-(3′,7′-Dichlorchinolin-8′-yl)-1,2-oxazol-4,5-dicarbonsäure- dimethylester3- (3 ′, 7′-dichloroquinolin-8′-yl) -1,2-oxazol-4,5-dicarboxylic acid dimethyl ester

12,0 g (50 mmol) 3,7-Dichlorchinolin-8-nitriloxid (Verb. Nr. 47) wurden in 100 ml Dimethoxyethan suspendiert, 8,50 g (60 ml) Acetylendicarbonsäuredimethylester zugegeben und 4 Stunden unter Rückfluß erhitzt. Nach Fällen auf Wasser, Absaugen und Trocknen erhielt man 17,8 g (93%), Schmp.: 135°C (Verb. Nr. 48).12.0 g (50 mmol) of 3,7-dichloroquinoline-8-nitrile oxide (compound no. 47) were added to 100 ml of dimethoxyethane suspended, 8.50 g (60 ml) of dimethyl acetylenedicarboxylate added and heated under reflux for 4 hours. After cases 17.8 g (93%) were obtained on water, suction and drying, Mp: 135 ° C (Verb.No. 48).

In analoger Weise erhielt man die in der Tabelle 6 aufgeführten Verbindungen.The compounds listed in Table 6 were obtained in an analogous manner.

Tabelle 6 Table 6

Beispiel 59Example 59 3,7-Dichlorchinolin-8-hydroxamsäure-(carboxymethylthio)ester3,7-dichloroquinoline-8-hydroxamic acid (carboxymethylthio) ester

12,0 g (50 mmol) 3,7-Dichlorchinolin-8-nitriloxid (Verb. Nr. 47) wurden in 100 ml Dimethoxyethan suspendiert und 5,6 g (60 mmol) Mercaptoessigsäure zugefügt. Nach 6stündigem Rühren bei Raumtemperatur wurde vom Lösungsmittel befreit, mit Wasser versetzt und abgesaugt. 13,5 g (81%), Schmp.: 174°C (Verb. Nr. 59).12.0 g (50 mmol) of 3,7-dichloroquinoline-8-nitrile oxide (compound no. 47) were added to 100 ml of dimethoxyethane suspended and 5.6 g (60 mmol) of mercaptoacetic acid added. After stirring for 6 hours at room temperature, the solvent freed, mixed with water and suctioned off. 13.5 g (81%), mp: 174 ° C (Verb.No. 59).

Analog wurden die in der Tabelle 7 aufgeführten Verbindungen erhalten.The compounds listed in Table 7 were obtained analogously.

Tabelle 7 Table 7

Beispiel 62Example 62 3,7-Dichlor-8-propionylchinolin3,7-dichloro-8-propionylquinoline

Die Lösung eines Grignard-Reagenzes, hergestellt aus 7,2 g (60 mmol) Ethylbromid und 1,6 g (60 mmol) Magnesium-Spänen in 30 ml abs. Tetrahydrofuran, wurde bei -70°C zu einer Suspension von 6,4 g (25 mmol) 3,7- Dichlorchinolin-8-carbonsäuremethylester in 25 ml abs. Tetrahydrofuran getropft, und das Gemisch langsam auf Raumtemperatur gebracht. Danach goß man auf Eis, säuerte mit 10% Salzsäure an, saugte ab und trocknete: 4,5 g (71%), Schmp.: 108-110°C (Verb. Nr. 62).The solution of a Grignard reagent, made from 7.2 g (60 mmol) Ethyl bromide and 1.6 g (60 mmol) magnesium shavings in 30 ml abs. Tetrahydrofuran, was at -70 ° C to a suspension of 6.4 g (25 mmol) 3.7- Dichloroquinoline-8-carboxylic acid methyl ester in 25 ml abs. Tetrahydrofuran added dropwise, and the mixture was slowly brought to room temperature. Then poured one on ice, acidified with 10% hydrochloric acid, sucked off and dried: 4.5 g (71%), mp: 108-110 ° C (Verb.No. 62).

Analog wurde 7-Chlor-3-methyl-8-propionylchinolin (Verb. Nr. 63) erhalten. 7-Chloro-3-methyl-8-propionylquinoline (compound no. 63) was obtained analogously.  

Beispiel 64Example 64 3-(7′-Chlor-3′-methylchinolin-8′-yl)propan-3-oncarbonsäureethylester3- (7'-Chloro-3'-methylquinolin-8'-yl) propan-3-oncarboxylic acid ethyl ester

70,8 g (0,3 mol) 7-Chlor-3-methylchinolin-8-carbonsäuremethylester wurden in 150 ml Essigester suspendiert, 16 g 80% Natriumhydrid zugegeben und das Gemisch 5 Stunden unter Rückfluß erhitzt. Nach Fällen auf Eis und Ansäuern mit verd. Salzsäure wurde abgesaugt und getrocknet, 51 g (58%), Schmp.: 143-145°C (Verb. Nr. 64).70.8 g (0.3 mol) of 7-chloro-3-methylquinoline-8-carboxylic acid methyl ester suspended in 150 ml of ethyl acetate, 16 g of 80% sodium hydride added and the mixture was heated under reflux for 5 hours. After falls on ice and Acidification with dil. Hydrochloric acid was filtered off and dried, 51 g (58%), Mp: 143-145 ° C (Verb.No. 64).

Die Chinolinderivate der Formel I können beispielsweise in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungformen richten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The quinoline derivatives of the formula I can, for example, in the form of directly sprayable solutions, powders, suspensions, also high-proof aqueous, oily or other suspensions or dispersions, emulsions, Oil dispersions, pastes, dusts, spreading agents or granules by spraying, atomizing, dusting, scattering or pouring be applied. The application forms depend entirely on the purposes; in any case, they should have the finest possible distribution ensure the active ingredients according to the invention.

Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldispersionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z. B. Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Cyclohexanon, Chlorbenzol, Isophoron oder stark polare Lösungsmittel, wie N,N-Dimethylformamid, Dimethylsulfoxid, N-Methylpyrrolidon oder Wasser in Betracht.For the production of directly sprayable solutions, emulsions, pastes or oil dispersions come mineral oil fractions from medium to high Boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic Hydrocarbons, e.g. B. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, Ethanol, propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or strongly polar solvents, such as N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water.

Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Dispersionen, Pasten, netzbaren Pulvern oder wasserdispergierbaren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substrate 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.Aqueous use forms can be made from emulsion concentrates, dispersions, Pastes, wettable powders or water-dispersible granules by adding be prepared by water. For the production of emulsions, pastes or oil dispersions, the substrates as such or in an oil or Solvent dissolved, using wetting agents, adhesives, dispersants or emulsifiers be homogenized in water. But it can also be more effective Substance wetting, adhesive, dispersing or emulsifying agent and possibly solvent or oil existing concentrates are produced which are used for Dilution with water are suitable.

Als oberflächenaktive Stoffe kommen Alkali-, Erdalkali-, Ammoniumsalze von Ligninsulfonsäure, Naphthalinsulfonsäure, Phenolsulfonsäure, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Alkali- und Erdalkalisalze der Dibutylnaphthalinsulfonsäure, Laurylethersulfat, Fettalkoholsulfate, Heptadecanole, Octadecanole, Salze von sulfatiertem Fettalkoholglykolfettsaure Alkali- und Erdalkalisalze, Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole, Salze von sulfatiertem Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol oder Nonylphenol, Alkylphenolpolyglykolether, Tributylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin, Sulfitablaugen oder Methylcellulose in Betracht.Alkali, alkaline earth, ammonium salts come as surface-active substances of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, alkylarylsulfonates, Alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, Heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol fatty acid  Alkali and alkaline earth salts, salts of sulfated hexadecanols, Heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, Alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, Isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, Lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin, sulfite waste liquor or methyl cellulose.

Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermahlen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for spreading and dusts can be mixed or combined Grinding the active substances with a solid carrier will.

Granulate, z. B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silica gel, silicas, silica gels, Silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, Dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground Plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, Tree bark, wood and nutshell flour, cellulose powder or other solid Carriers.

Die Formulierungen enthalten zwischen 0,1 und 95 Gew.%, vorzugsweise zwischen 0,5 und 90 Gew.%, Wirkstoff.The formulations contain between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight, active ingredient.

Die Applikation kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die Wirkstoffe bei Nachauflaufanwendung für gewisse Kulturpflanzen weniger verträglich, so können auch Aufbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by).The application can take place pre- or post-emergence. Are the active ingredients in post-emergence use for certain crops less compatible, so application techniques can be applied in which the herbicidal agents with the help of sprayers be sprayed so that the leaves of sensitive crops if possible not to be taken while the active ingredients on the leaves including unwanted plants or the uncovered ones Floor space (post-directed, lay-by).

Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die Diphenyletherderivate der Formel I und ihre Salze mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner Diazine, 4H-3,1-Benzoxazinderivate, Benzothiadiazinone, 2,6-Dinitroaniline, N-Phenylcarbamate, Thiolcarbamate, Halogencarbonsäuren, Triazine, Amide, Harnstoffe, Triazinone, Uracile, Benzofuranderivate, Cyclohexan-1,3-dionderivate oder Diphenyletherderivate sowie andere herbizide Wirkstoffe in Betracht.To broaden the spectrum of activity and to achieve synergistic The diphenyl ether derivatives of the formula I and their salts can have effects numerous representatives of other herbicides or growth regulators Active ingredient groups are mixed and applied together. For example come as mixing partners diazines, 4H-3,1-benzoxazine derivatives,  Benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, Halogen carboxylic acids, triazines, amides, ureas, triazinones, uraciles, Benzofuran derivatives, cyclohexane-1,3-dione derivatives or diphenyl ether derivatives as well as other herbicidal active ingredients.

Außerdem kann es von Nutzen sein, die Verbindungen der Formel I allein oder in Kombination mit anderen Herbiziden, auch noch mit weiteren Pflanzenschutzmitteln gemischt gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Bekämpfung von Ernährungs- und Spurenelementmängeln eingesetzt werden.It may also be useful to use the compounds of formula I alone or in combination with other herbicides, also with other crop protection agents to apply mixed together, for example with Agents for controlling pests or phytopathogenic fungi or Bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to combat nutritional and trace element deficiencies be used.

Claims (4)

1. Chinolinderivate der Formel I in der
R1 Halogen oder C1-C4-Alkyl,
X Halogen,
Z Sauerstoff, Hydroxyimino, C1-C4-Alkoxyimino oder einen Hydrazonorest, der durch C1-C4-Alkyl, C1-C4-Alkoxycarbonyl, Arylsulfonyl, 1,3-Oxazol-2-yl oder 1,3-Thiazol-2-yl substituiert ist, wobei die letztgenannten heterocyclischen Reste wiederum durch C1-C4-Alkyl, C2-C4-Hydroxyalkyl oder Hydroxyl substituiert sind, und
Y für den Fall, daß Z die Bedeutung von Sauerstoff besitzt, den Rest -NR2R3, in dem R2 für Wasserstoff und R3 für C1-C4-Hydroxyalkyl, C1-C4-Alkoxy, C2-C4-Alkenyl, das durch -C≡N oder C1-C4- Alkoxycarbonyl substituiert ist, Arylsulfonyl, 1,3-Oxazol-2-yl oder 1,3-Thiazol-2-yl steht, oder in dem R2 und R3 zusammen für C1-C4-Alkyliden stehen, das durch C1-C4-Dialkylamino, Hydroxyamino oder C1-C4-Alkoxyamino substituiert ist; einen Hydrazinorest, der gegebenenfalls durch C1-C4-Alkoxycarbonyl, C2-C6-Alkyliden, Thiocarbamoyl, C1-C4-Alkoxy-oxalyl, Amino-oxalyl oder Arylsulfonyl substituiert ist; C1-C4-Alkyl, das gegebenenfalls durch C1-C4-Alkoxycarbonyl substituiert ist; oder C3-C8-Cycloalkenyl, das durch C1-C4-Dialkylamino oder C4-C6-Alkylenimino substituiert ist,
für den Fall, daß Z die Bedeutung von C1-C4-Alkoxyimino oder des oben genannten substituierten Hydrazonorests besitzt, Wasserstoff oder Halogen, und
für den Fall, daß Z die Bedeutung von Hydroxyimino besitzt, Halogen, Amino, C1-C4-Alkoxy oder C1-C4-Alkylthio, das durch Carboxyl oder C1-C4-Alkoxycarbonyl substituiert ist, bedeuten, oder in der die Gruppe
für den Rest -C≡N⊕-O⊖ oder einen fünfgliedrigen Heterocyclus steht, der neben einem Stickstoffatom noch ein oder zwei weitere Heteroatome, ausgewählt aus der Gruppe, bestehend aus Stickstoff, Sauerstoff und Schwefel, sowie eine oder zwei Doppelbindungen aufweist, und der gegebenenfalls substituiert und/oder durch weitere Carbo- oder Heterocyclen anneliert und über ein Kohlenstoffatom an den Chinolinring gebunden ist.1. Quinoline derivatives of the formula I. in the
R 1 is halogen or C 1 -C 4 alkyl,
X halogen,
Z is oxygen, hydroxyimino, C 1 -C 4 alkoxyimino or a hydrazone radical which is substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl, arylsulfonyl, 1,3-oxazol-2-yl or 1,3- Thiazol-2-yl is substituted, the latter heterocyclic radicals in turn being substituted by C 1 -C 4 alkyl, C 2 -C 4 hydroxyalkyl or hydroxyl, and
Y if Z is oxygen, the radical -NR 2 R 3 , in which R 2 is hydrogen and R 3 is C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 2 - C 4 alkenyl which is substituted by -C≡N or C 1 -C 4 alkoxycarbonyl, arylsulfonyl, 1,3-oxazol-2-yl or 1,3-thiazol-2-yl, or in which R 2 and R 3 together represent C 1 -C 4 alkylidene which is substituted by C 1 -C 4 dialkylamino, hydroxyamino or C 1 -C 4 alkoxyamino; a hydrazine radical which is optionally substituted by C 1 -C 4 alkoxycarbonyl, C 2 -C 6 alkylidene, thiocarbamoyl, C 1 -C 4 alkoxy oxalyl, amino oxalyl or arylsulfonyl; C 1 -C 4 alkyl, which is optionally substituted by C 1 -C 4 alkoxycarbonyl; or C 3 -C 8 cycloalkenyl which is substituted by C 1 -C 4 dialkylamino or C 4 -C 6 alkyleneimino,
in the event that Z has the meaning of C 1 -C 4 alkoxyimino or the abovementioned substituted hydrazone radical, hydrogen or halogen, and
in the event that Z has the meaning of hydroxyimino, are halogen, amino, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio which is substituted by carboxyl or C 1 -C 4 alkoxycarbonyl, or in of the group
represents the radical -C≡N⊕-O⊖ or a five-membered heterocycle which, in addition to a nitrogen atom, also has one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and one or two double bonds, and the optionally substituted and / or fused by further carbocycles or heterocycles and bound to the quinoline ring via a carbon atom. 2. Herbizid, enthaltend ein Chinolinderivat der Formel I gemäß Anspruch 1.2. Herbicide containing a quinoline derivative of the formula I according to Claim 1. 3. Herbizid, enthaltend inerte Zusatzstoffe und ein Chinolinderivat der Formel I gemäß Anspruch 1.3. Herbicide containing inert additives and a quinoline derivative Formula I according to claim 1. 4. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwachstum, dadurch gekennzeichnet, daß man die unerwünschten Pflanzen und/oder die von unerwünschtem Pflanzenwachstum freizuhaltende Fläche mit einer herbizid wirksamen Menge eines Chinolinderivats der Formel I gemäß Anspruch 1 behandelt.4. Process for combating undesirable plant growth, thereby characterized in that the undesirable plants and / or those of undesirable plant growth area to be kept free with a herbicide effective amount of a quinoline derivative of the formula I according to claim 1 treated.
DE19853541722 1985-11-26 1985-11-26 Quinoline derivatives and their use for controlling undesired vegetation Withdrawn DE3541722A1 (en)

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DE19853541722 DE3541722A1 (en) 1985-11-26 1985-11-26 Quinoline derivatives and their use for controlling undesired vegetation
JP61262063A JPS62126175A (en) 1985-11-26 1986-11-05 Quinoline derivative and herbicide
EP86116185A EP0224823A3 (en) 1985-11-26 1986-11-22 Quinoline derivatives and their use in combating unwanted plant growth
US06/933,795 US4797148A (en) 1985-11-26 1986-11-24 Quinoline derivatives and their use for controlling undesirable plant growth

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994004530A1 (en) * 1992-08-14 1994-03-03 Korea Research Institute Of Chemical Technology Herbicidal quinolinyloxadiazoles
WO2018135649A1 (en) 2017-01-20 2018-07-26 北興化学工業株式会社 Isoxazolin-5-one derivative and herbicide containing same as active ingredient
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US5500098A (en) * 1993-08-05 1996-03-19 Eco-Tec Limited Process for regeneration of volatile acids
US8389506B2 (en) * 2007-12-07 2013-03-05 Prana Biotechnology Ltd. Compounds for therapy and diagnosis
WO2014048827A1 (en) * 2012-09-25 2014-04-03 Bayer Cropscience Ag 3-phenylisoxazolin derivatives with herbicidal action
KR102492715B1 (en) * 2016-07-14 2023-01-26 브리스톨-마이어스 스큅 컴퍼니 Monocyclic Heteroaryl Substituted Compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994004530A1 (en) * 1992-08-14 1994-03-03 Korea Research Institute Of Chemical Technology Herbicidal quinolinyloxadiazoles
WO2018135649A1 (en) 2017-01-20 2018-07-26 北興化学工業株式会社 Isoxazolin-5-one derivative and herbicide containing same as active ingredient
US11109593B2 (en) 2017-01-20 2021-09-07 Hokko Chemical Industry Co., Ltd. Isoxazolin-5-one derivative and herbicide containing same as active ingredient
WO2020022350A1 (en) 2018-07-24 2020-01-30 北興化学工業株式会社 Isoxazolin-5-one derivative, and herbicide containing same as active ingredient

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