WO1999000020A1 - 3-(5-tetrazolyl carbonyl)-2-quinolones and products for protecting useful plants containing the same - Google Patents

3-(5-tetrazolyl carbonyl)-2-quinolones and products for protecting useful plants containing the same Download PDF

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Publication number
WO1999000020A1
WO1999000020A1 PCT/EP1998/002819 EP9802819W WO9900020A1 WO 1999000020 A1 WO1999000020 A1 WO 1999000020A1 EP 9802819 W EP9802819 W EP 9802819W WO 9900020 A1 WO9900020 A1 WO 9900020A1
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substituted
unsubstituted
group
optionally substituted
alkyl
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PCT/EP1998/002819
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German (de)
French (fr)
Inventor
Wolfgang Giencke
Hermann Bieringer
Christopher Rosinger
Thomas Kappe
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Hoechst Schering Agrevo Gmbh
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Priority to AU79119/98A priority Critical patent/AU7911998A/en
Publication of WO1999000020A1 publication Critical patent/WO1999000020A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/06Heterocyclic 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 linked by a carbon chain containing only aliphatic carbon atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, 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

Definitions

  • the present invention relates to crop protection agents which contain substituted 3- (5-tetrazolylcarbonyl) -2-quinolones and optionally herbicides, and to certain substituted 3- (5-tetrazolylcarbonyl) -2-quinolones.
  • EP-A 0 520 371 mentions isoxazolines and isothiazolines as suitable safeners for various types of herbicides, aryloxyphenoxycarboxylic acids, sulfonylureas and imidazolinones being mentioned as preferred herbicides.
  • WO 93/10783 describes derivatives of 2-quinolone - including 3- (5-tetrazolylcarbonyl) -2-quinolones which are unsubstituted on quinoline nitrogen - as selective, non-competitive antagonists of receptors of N-methyl-D-aspartate and 2 -Amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid. From US-A 5,378,694 the antiviral properties of derivatives of 2-quinolone are known. Substituted 2-quinolones are listed there which carry a formyl, an alkylcarbonyl or an alkenylcarbonyl, but not a 5-tetrazolylcarbonyl group in the 3-position.
  • the safener reduces the action of the herbicides against the
  • Crop plants in which the safener / herbicide is to be used are not sufficiently large; a given safener cannot be combined with a sufficiently large number of herbicides.
  • the object of the present invention is to provide crop protection agents which contain compounds with improved safener action and, if appropriate, herbicides.
  • the solution to the problem is optionally at least one herbicide-containing crop protection agent, characterized by a content of at least one substituted 3- (5-tetrazolylcarbonyl) -2-quinolone of the general formula I, optionally also in its salt form
  • Z is oxygen, sulfur or NR 4 ;
  • R ⁇ R 2 , R 3 and R 4 each independently of one another hydrogen, optionally substituted phenyl, optionally substituted phenyl-C r C 6 alkyl, optionally substituted C 2 -C 6 alkenyl, optionally substituted C 2 -C 6 alkynyl, optionally substituted C 3 -C 9 cycloalkyl, unsubstituted or substituted by one or more identical or different radicals from the group halogen, nitro, cyano, thiocyanato, C ⁇ C ⁇ alkoxy, C ⁇ C ⁇ alkylthio, C r C 4 alkylsulfinyl C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 9 cycloalkyl which may be unsubstituted or substituted, phenyl which may be unsubstituted or substituted, heterocyclyl
  • X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, carboxyl, formyl, hydroxy, halogen, nitro, cyano, thiocyanato, -BR 5 , -BR 6 , or two adjacent X together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can contain up to 3 identical or different heteroatoms from the group oxygen, sulfur and nitrogen, this ring being unsubstituted or by one or more radicals from the group halogen, C 1 -C 4 alkyl and oxo may be substituted to form;
  • R 5 each substituted or unsubstituted C 1 -C 6 -alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;
  • R 6 is a partially or unsaturated carbocyclic radical, C 3 -C 8 cycloalkyl, phenyl or heterocyclyl, each of which may be substituted or unsubstituted;
  • R 7 and R 8 are each independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, Phenyl or benzyl;
  • the compounds of the general formula I can have acidic or basic properties and form salts. If the compounds of the general formula I carry, for example, groups such as hydroxyl, carboxy or other groups which induce acidic properties or, for example, -A 3 - is a direct bond and R 3 is simultaneously hydrogen, these compounds can be reacted with bases to form salts.
  • Suitable bases are, for example, hydroxides, carbonates, hydrogen carbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (C, -C 4 ) - alkyl radicals and mono-, di - and trialkanolamines of (C r C 4 ) -alkanols.
  • the compounds of the general formula I carry or are, for example, groups such as amino, alkylamino or other groups which induce basic properties -A 2 - a bond and at the same time R 2 is hydrogen, these compounds can be reacted with acids to form salts.
  • Suitable acids are, for example, mineral acids, such as hydrochloric, sulfuric and phosphoric acids, organic acids, such as acetic acid, and acidic salts, such as NaHSO 4 and KHS0 4 .
  • the salts obtainable in this way also have crop protection properties.
  • R 1 , R 2 , R 3 and R 4 are each independently hydrogen, optionally substituted phenyl, optionally substituted phenyl-C 1 -C 6 alkyl, optionally substituted C 2 -C 6 alkenyl, optionally substituted C 2 -C 6 alkynyl, optionally substituted C 3 -C 9 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, C ⁇ C ⁇ alkoxy, C r C 4 alkylthio, C ⁇ C ⁇ - alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 9 cycloalkyl, which may be unsubstituted or substituted, phenyl, which may be unsubstituted or substituted, heterocyclyl with a total of 3 up to 6 ring atoms, of which 1 to 3 are hetero
  • X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxy, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 -Alkenyioxy, C 2 -C 6 -alkynyloxy, CC 6 -alkylthio, C, -C 4 -alkylcarbonyl, C ⁇ C ⁇ alkoxycarbonyl or C ⁇ C ⁇ alkylthiocarbonyl, the above-mentioned hydrocarbon radicals by one or more identical or different halogen atoms can be substituted;
  • -A 1 -R 1 and X 4 together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can contain up to 3 identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen, where this ring may be unsubstituted or substituted by one or more radicals from the group halogen, CC 4 -alkyl and oxo.
  • R 1 , R 2 , R 3 and R 4 each independently of one another hydrogen, optionally substituted phenyl, optionally substituted phenyl-C 1 -C 6 alkyl, optionally substituted C 2 -C 4 alkenyl, optionally substituted C 2 -C 4 - Alkynyl, optionally substituted C 3 -C 6 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, CC 4 alkoxy, C 1 -C 4 alkylthio, C r C 4 alkyl sulfonyl, C 2 - C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl which may be unsubstituted or substituted, heterocyclyl with a total of 3 to 6 ring atoms, of which 1 to 3 are hetero ring atoms and from the group nitrogen,
  • X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxy, halogen, C r C 4 alkyl, C ⁇ C ⁇ alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy , C r C 4 alkylthio, C r C 4 alkylcarbonyl or C ⁇ C alkoxycarbonyl, where the above-mentioned hydrocarbon radicals can be substituted by one or more identical or different halogen atoms;
  • a five- or six-membered partially saturated or unsaturated ring which may contain one oxygen atom or up to two nitrogen atoms and this ring is unsubstituted or by one or more radicals from the group C ⁇ C ⁇ alkyl and oxo can be substituted, forming.
  • 'halogen' includes fluorine, chlorine, bromine and iodine.
  • 'alkyl', 'alkenyl' and 'alkynyl' mean that the carbon chain can be branched or unbranched. The latter two terms are to be understood so that the multiple bond can be located at any position of the unsaturated radical in question.
  • Heterocyclyl is to be understood as meaning a radical which can be attributed to a three to six atom, mononuclear, saturated, partially saturated, unsaturated or aromatic ring, of which three to six ring atoms independently of one another come from the group nitrogen, oxygen and sulfur can, e.g. B.
  • a partially saturated or unsaturated carbocyclic radical is to be understood as a three- to eight-atom ring composed of carbon atoms, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl.
  • the term "optionally substituted” is to be understood in connection with alkenyl, alkynyl, cycloalkyl, phenyl, phenyl, C 1 -C 4 alkyl, heterocyclyl, partially saturated, unsaturated, carbocyclic radicals, that these radicals are either unsubstituted, or that one or more hydrogen atoms by the equivalent number of identical or different substituents from the group halogen, hydroxy, nitro, cyano, oxo, C 1 -C 3 alkoxy, halogen-C C 3 alkoxy, Halogen-C C 3 alkyl are replaced.
  • Halogen-C r C 3 -alkoxy, halogen-C r C 3 -alkyl mean that one or more hydrogen atoms are substituted by the corresponding number of identical or different halogen atoms.
  • the compounds of the general formula I can be present as stereoisomers.
  • stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. Stereoisomers can also be prepared selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances.
  • the invention also relates to all stereoisomers and their mixtures which are encompassed by the general formula I but are not specifically defined.
  • compositions which comprise at least one compound of the general formula I and at least one herbicide from the groups A) Phenoxyphenoxycarboxylic acids and heteroaryloxyphenoxycarboxylic acids
  • B16 is known from WO 92/13845.
  • D3 is known from US-A 4 988 812.
  • E1 and E2 are known from EP-A 0 249 707.
  • E3 is known from EP-A 0 321 846.
  • E4 is known from EP-A 0472 113.
  • G2 is known from WO 91/13548.
  • G3 is known from EP-A 0274634. All other herbicides mentioned under A) to H) are known from "The Pesticide Manual", 10th edition (1994), Brit. Crop. Prot. Council, London.
  • these agents are applied after appropriate dilution either directly to the area under cultivation or to the already germinated harmful and / or useful plants or to the already emerged harmful and / or useful plants.
  • these agents can be used in the so-called tank mix process - i.e. immediately before bringing up on the surface to be treated, the mixing takes place and
  • the weight ratio of safener to herbicide can vary within wide limits and is preferably in the range from 1:10 to 10: 1, in particular from 1:10 to 5: 1.
  • the optimal weight ratio of safener to herbicide depends on the active ingredients safener and herbicide and on the type of crop to be protected.
  • the required amount of safener can vary within wide limits, depending on the herbicide used and the type of crop to be protected, and is generally in the range from 0.001 to 5 kg, preferably 0.005 to 0.5 kg, of safener per hectare.
  • the agents according to the invention can be used to protect various crops such as cereals, cotton, rapeseed and soybeans.
  • Preferred crops are barley, oats, rye, corn, sorghum and wheat, and corn is particularly preferred.
  • the compounds of general formula I and their combinations with one or more of the herbicides mentioned can be formulated in various ways depending on the specified chemical-physical and biological parameters. Examples of suitable types of formulation are:
  • Emulsifiable concentrates which are obtained by dissolving the active ingredients in an organic solvent, e.g. Example, butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • organic solvent e.g. Example, butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • Suitable emulsifiers are, for example, alkylarylsulfonic acid calcium salts, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters; • dusts which are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, diatomaceous earth or flours;
  • Water or oil-based suspension concentrates which can be produced, for example, by wet grinding using pearl mills;
  • Granules such as water-soluble granules, water-dispersible granules and granules for spreading and soil application;
  • wettable powders which, in addition to the active ingredient, also contain diluents or inert substances and surfactants;
  • the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula I or a combination of safener and herbicide. They also contain 1 to 99.9, in particular 5 to 99.8% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25% by weight of a surfactant.
  • the active substance concentration in emulsifiable concentrates is generally 1 to 90, in particular 5 to 80,% by weight. Dusts usually contain 1 to 30, preferably 5 to 20% by weight of active ingredient.
  • the active ingredient concentration in wettable powders is generally 10 to 90% by weight.
  • the crop protection agents can, if appropriate, customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH or the like Contain viscosity-influencing agents.
  • the crop protection agents are optionally diluted in a customary manner, for example wettable powders, emulsifiable concentrates, water-soluble and water-dispersible granules are diluted with water. Other granules, dusts and sprayable solutions are usually no longer diluted before use.
  • the application rate of the crop protection agents also varies with external conditions, such as temperature and humidity.
  • the compounds of general formula I can be prepared according to the reaction scheme given below:
  • the anilines of general formula II are can be obtained commercially or according to methods known to the person skilled in the art.
  • the compounds of the general formulas III, VI and I can each be prepared from the precursors shown in the reaction scheme in accordance with reactions known to the person skilled in the art, such as alkylations or acylations of amino or hydroxy compounds.
  • alkylations or acylations are known, for example, from Houben-Weyl Vol. VI / 3, Georg-Thieme Verlag, Stuttgart, 1965, pages 24 and 49; Houben-Weyl Vol. VIII, Georg-Thieme Verlag, Stuttgart, 1952, p. 543.
  • Ph phenyl t-Bu tertiary butyl
  • Seeds or rhizome pieces of mono- and dicotyledonous harmful and useful plants are placed in pots 9 cm in diameter in sandy loam and covered with earth.
  • rice plants as well as undesirable harmful plants in this crop of crops are cultivated in a soil oversaturated with water for the rice test.
  • the agents according to the invention formulated as emulsifiable concentrates from safeners and herbicides and, in parallel experiments, the correspondingly formulated individual active ingredients are then applied as emulsions with a water amount of the equivalent of 800 l / ha in different dosages to the surface of the covering earth or poured into the irrigation water in the rice test . Then the Pots for further cultivation of the plants in the greenhouse kept under optimal conditions.
  • the optical evaluation of the damage to crops and harmful plants takes place after the emergence of these plants, ie about 2 to 4 weeks after the start of the test.
  • the experiments show that the agents according to the invention which contain, for example, the safener S1 in combination with one of the sulfonylureas 3- (4,6-dimethoxypyrimid-2-yl) -1- [3- (N-methylsulfonyl-N-methyiamino) pyridine -2-yl-sulfonyl] urea and 3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -1- (2-methoxycarbonyl-5-iodophenylsulfonyl) urea (sodium salt) contain in the ratio of safener to herbicide of 2: 1 or 17: 1, a good effect against a wide range of monocotyledonous and dicotyledonous plants, the damage to the useful plants such as maize or rice being significant
  • Seeds or rhizome pieces of mono- and dicotyledonous harmful and useful plants are placed in pots 9 cm in diameter in sandy loam and covered with earth.
  • rice plants as well as undesirable harmful plants in this crop of crops are cultivated in a soil oversaturated with water for the rice test.
  • the test plants are treated with the agents according to the invention from safeners and herbicides formulated as emulsifiable concentrates or dusts, and in parallel experiments with the correspondingly formulated individual active compounds.
  • the agents according to the invention and the comparative agents are sprayed with a water amount of the equivalent of 800 l / ha in different dosages onto the green parts of the plants or, in the rice test, also poured into the irrigation water.
  • the pots are kept in the greenhouse under optimal conditions for further cultivation of the plants.
  • the visual assessment of damage to crops and harmful plants takes place after a further 2 to 3 weeks.
  • the agents according to the invention which, for example, the safener S1 in combination with one of the sulfonylureas 3- (4,6-dimethoxypyrimid-2-yl) -1- [3- (N-methylsulfonyl-N-methylamino) pyridine- 2-yl-sulfonyl urea and 3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -1 - (2-methoxy-carbonyl-5-iodophenylsulfonyl) urea (sodium salt) im Ratio of safener to herbicide of 2: 1 or 17: 1 included, also have a good effect against a broad spectrum of mono- and dicotyledonous crops in post-emergence, the damage to crops such as corn or rice compared to the use of herbicides without Safener essential, ie reduced by 50 to 100%.

Abstract

The invention relates to substituted 3-(5-tetrazolyl carbonyl)-2-quinolones of general formula (I) and to products for protecting useful plants containing the same. In said general formula (I), -A1-, -A2- and -A3- can each mean a direct bond or a divalent carbonyl analogue group, and X?1, X2, X3 and X4¿ mean different organic radicals. The inventive products can be used to reduce the unwanted damage caused to useful plants by herbicides.

Description

3-(5-Tetrazolylcarbonyl)-2-chinolone und diese enthaltende nutzpflanzenschützende Mittel3- (5-tetrazolylcarbonyl) -2-quinolones and crop protection agents containing them
Die vorliegende Erfindung betrifft nutzpflanzenschützende Mittel, die substituierte 3- (5-Tetrazolylcarbonyl)-2-chinolone und gegebenenfalls Herbizide enthalten, sowie bestimmte substituierte 3-(5-Tetrazolylcarbonyl)-2-chinolone.The present invention relates to crop protection agents which contain substituted 3- (5-tetrazolylcarbonyl) -2-quinolones and optionally herbicides, and to certain substituted 3- (5-tetrazolylcarbonyl) -2-quinolones.
Bei der Bekämpfung unerwünschter Schadpflanzen in land- und forstwirtschaftlichen Nutzpflanzenkulturen mit Herbiziden werden - in an sich unerwünschter Weise - häufig auch die Nutzpflanzen durch die verwendeten Herbizide mehr oder weniger stark geschädigt. Durch den Einsatz sogenannter "Safener" oder "Antidots" können in manchen Fällen die Nutzpflanzen gegen die phytotoxischen Eigenschaften der Herbizide geschützt werden, ohne daß die herbizide Wirkung gegenüber den Schadpflanzen beeinträchtigt wird.When combating undesirable harmful plants in agricultural and forestry crops with herbicides, the crops are often - to an undesirable extent - also more or less severely damaged by the herbicides used. The use of so-called "safeners" or "antidots" can in some cases protect the useful plants against the phytotoxic properties of the herbicides without the herbicidal action against the harmful plants being impaired.
Die bislang als Safener bekannt gewordenen Verbindungen weisen unterschiedliche chemische Strukturen auf. So sind aus US-A 4,902,340 Derivate von Chinolin-8-oxy-alkancarbonsäuren als Safener für Herbizide aus der Reihe der Diphenylether und der Pyridyloxyphenoxypropionsäuren und aus US-A 4,851 ,031 analoge Chinolinstrukturen als Safener für Herbizide aus der Reihe der Imidazolinone bekannt. In WO 91/07874 werden Pyrazoline und in US-A 5,401,700 Pyrazole als Safener für Aryloxyphenoxycarbonsäuren beschrieben. EP-A 0 520 371 nennt Isoxazoline sowie Isothiazoline als geeignete Safener für verschiedene Arten von Herbiziden, wobei Aryloxyphenoxycarbonsäuren, Sulfonylhamstoffe und Imidazolinone als bevorzugte Herbizide genannt sind.The compounds that have become known as safeners have different chemical structures. For example, US Pat. No. 4,902,340 discloses derivatives of quinoline-8-oxyalkanecarboxylic acids as safeners for herbicides from the series of diphenyl ethers and pyridyloxyphenoxypropionic acids and US Pat. No. 4,851,031 analogous quinoline structures as safeners for herbicides from the series of imidazolinones. WO 91/07874 describes pyrazolines and US Pat. No. 5,401,700 pyrazoles as safeners for aryloxyphenoxycarboxylic acids. EP-A 0 520 371 mentions isoxazolines and isothiazolines as suitable safeners for various types of herbicides, aryloxyphenoxycarboxylic acids, sulfonylureas and imidazolinones being mentioned as preferred herbicides.
T. Kappe et al. beschreiben in J. Heterocyclic Chem., 21, 1881 (1984) neben der Synthese auch die entzündungshemmenden Eigenschaften einiger heterocyclischer Verbindungen, darunter auch die von 1 ,2-Dihydro-4-hydroxy-1-methyl-3-(5- tetrazolylcarbonyl)-2-chinolon. Dieselben Autoren berichten in J. Heterocyclic Chem., 26, 1555 (1989) über die Synthese und die fungiziden Eigenschaften einiger heterocyclischer Verbindungen, darunter auch 1 ,2-Dihydro-6-hydroxy-5-(5- tetrazolylcarbonyl)-4H-pyrrolo[3,2,1-/y]chinolin-4-on, das als N-überbrücktes 3-(5- Tetrazolylcarbonyl)-2-chinolon aufzufassen ist. In WO 93/10783 werden Derivate des 2-Chinolons - unter anderem am Chinolin-Stickstoff unsubstituierte 3-(5- Tetrazolylcarbonyl)-2-chinolone - als selektive nicht-kompetitive Antagonisten von Rezeptoren des N-Methyl-D-aspartats und der 2-Amino-3-hydroxy-5-methyl-4- isoxazol-propionsäure beschrieben. Aus US-A 5,378,694 sind die antiviralen Eigenschaften von ebenfalls Derivaten des 2-Chinolons bekannt. Dort werden substituierte 2-Chinolone aufgeführt, die in 3-Position eine Formyl-, eine Alkylcarbonyl- oder eine Alkenylcarbonyl-, nicht jedoch eine 5- Tetrazolylcarbonylgruppe tragen.T. Cap et al. in J. Heterocyclic Chem., 21, 1881 (1984) describe not only the synthesis but also the anti-inflammatory properties of some heterocyclic compounds, including those of 1,2-dihydro-4-hydroxy-1-methyl-3- (5- tetrazolylcarbonyl) -2-quinolone. The same authors report in J. Heterocyclic Chem., 26, 1555 (1989) about the synthesis and fungicidal properties of some heterocyclic compounds, including 1,2-dihydro-6-hydroxy-5- (5-tetrazolylcarbonyl) -4H-pyrrolo [3,2,1- / y] quinolin-4-one, which is to be understood as N-bridged 3- (5-tetrazolylcarbonyl) -2-quinolone. WO 93/10783 describes derivatives of 2-quinolone - including 3- (5-tetrazolylcarbonyl) -2-quinolones which are unsubstituted on quinoline nitrogen - as selective, non-competitive antagonists of receptors of N-methyl-D-aspartate and 2 -Amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid. From US-A 5,378,694 the antiviral properties of derivatives of 2-quinolone are known. Substituted 2-quinolones are listed there which carry a formyl, an alkylcarbonyl or an alkenylcarbonyl, but not a 5-tetrazolylcarbonyl group in the 3-position.
Die Safener-Wirkung von substituierten 3-(5-Tetrazolylcarbonyl)-2-chinolonen ist bislang nicht beschrieben.The safener effect of substituted 3- (5-tetrazolylcarbonyl) -2-quinolones has not yet been described.
Bei der Anwendung von Safenern zum Schutz der Nutzpflanzen vor den Herbizidschädigungen hat sich gezeigt, daß die bekannten Safener in vielen Fällen immer noch gewisse Nachteile aufweisen können. Dazu zählen:When using safeners to protect crops from herbicide damage, it has been found that the known safeners can still have certain disadvantages in many cases. These include:
der Safener vermindert die Wirkung der Herbizide gegen diethe safener reduces the action of the herbicides against the
Schadpflanzen, die nutzpflanzenschützenden Eigenschaften sind nicht ausreichend, in Kombination mit einem gegebenen Herbizid ist das Spektrum derHarmful plants, the crop protection properties are not sufficient, in combination with a given herbicide is the spectrum of
Nutzpflanzen, in denen der Safener/Herbizid-Einsatz erfolgen soll, nicht ausreichend groß, ein gegebener Safener ist nicht mit einer ausreichend großen Anzahl von Herbiziden kombinierbar. Aufgabe der vorliegenden Erfindung ist die Bereitstellung nutzpflanzenschützender Mittel, die Verbindungen mit verbesserter Safener-Wirkung und gegebenenfalls Herbizide enthalten.Crop plants in which the safener / herbicide is to be used are not sufficiently large; a given safener cannot be combined with a sufficiently large number of herbicides. The object of the present invention is to provide crop protection agents which contain compounds with improved safener action and, if appropriate, herbicides.
Die Lösung der Aufgabe sind gegebenenfalls mindestens ein Herbizid enthaltende nutzpflanzenschützende Mittel, gekennzeichnet durch einen Gehalt mindestens eines substituierten 3-(5-Tetrazolylcarbonyl)-2-chinolons der allgemeinen Formel I, gegebenenfalls auch in seiner SalzformThe solution to the problem is optionally at least one herbicide-containing crop protection agent, characterized by a content of at least one substituted 3- (5-tetrazolylcarbonyl) -2-quinolone of the general formula I, optionally also in its salt form
Figure imgf000005_0001
Figure imgf000005_0001
in derin the
-A1-, -A2- und -A3- jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Einheit aus der Gruppe -C(=Y)-, -C(=Y)-Z-, -S(=0)-, -SO2- und -S02NR4-; Y Sauerstoff oder Schwefel;-A 1 -, -A 2 - and -A 3 - each independently of one another a direct bond or a divalent unit from the group -C (= Y) -, -C (= Y) -Z-, -S (= 0 ) -, -SO 2 - and -S0 2 NR 4 -; Y oxygen or sulfur;
Z Sauerstoff, Schwefel oder NR4;Z is oxygen, sulfur or NR 4 ;
R\ R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenyl-CrC6-Alkyl, gegebenenfalls substituiertes C2-C6-Alkenyl, gegebenenfalls substituiertes C2-C6- Alkinyl, gegebenenfalls substituiertes C3-C9-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato, C^C^AIkoxy, C^C^Alkylthio, CrC4-Alkylsulfinyl, C^C^ Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C9-Cycloalkyl, das unsubstituiert oder substituiert sein kann, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocyclus unsubstituiert oder substituiert sein kann, substituiertes C.,-C6-Alkyl;R \ R 2 , R 3 and R 4 each independently of one another hydrogen, optionally substituted phenyl, optionally substituted phenyl-C r C 6 alkyl, optionally substituted C 2 -C 6 alkenyl, optionally substituted C 2 -C 6 alkynyl, optionally substituted C 3 -C 9 cycloalkyl, unsubstituted or substituted by one or more identical or different radicals from the group halogen, nitro, cyano, thiocyanato, C ^ C ^ alkoxy, C ^ C ^ alkylthio, C r C 4 alkylsulfinyl C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 9 cycloalkyl which may be unsubstituted or substituted, phenyl which may be unsubstituted or substituted, heterocyclyl with a total of 3 up to 6 ring atoms, of which 1 to 3 are hetero ring atoms and come from the group nitrogen, oxygen and sulfur and the heterocycle can be unsubstituted or substituted, substituted C 1 -C 6 alkyl;
X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino, Carboxyl, Formyl, Hydroxy, Halogen, Nitro, Cyano, Thiocyanato, -B-R5, -B-R6, oder zwei benachbarte X gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der bis zu 3 gleiche oder verschiedene Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, C1-C4-Alkyl und Oxo substituiert sein kann, bildend;X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, carboxyl, formyl, hydroxy, halogen, nitro, cyano, thiocyanato, -BR 5 , -BR 6 , or two adjacent X together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can contain up to 3 identical or different heteroatoms from the group oxygen, sulfur and nitrogen, this ring being unsubstituted or by one or more radicals from the group halogen, C 1 -C 4 alkyl and oxo may be substituted to form;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf-, sechs- oder siebengliedrigen teilgesättigten oder ungesättigten Ring, der bis zu 3 gleiche oder verschiedene Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, C^C^Alkyl und Oxo substituiert sein kann, bildend; -B- eine direkte Bindung oder eine divalente Einheit aus der Gruppe -NR7-, -NR7-O-, -NR7-CO-, -NR7-CO2-, -NR7-CO-NR8-, -S(=O)p-, -S(=O)p-O-, -C(=Y)-, -C(=Y)-Y-, -O-CO2- und -O-;-A 1 -R 1 and X 4 together with the ring atoms to which they are attached form a five-, six- or seven-membered partially saturated or unsaturated ring which contain up to 3 identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen may, whereby this ring may be unsubstituted or substituted by one or more radicals from the group halogen, C 1 -C 4 alkyl and oxo; -B- a direct bond or a divalent unit from the group -NR 7 -, -NR 7 -O-, -NR 7 -CO-, -NR 7 -CO 2 -, -NR 7 -CO-NR 8 -, -S (= O) p -, -S (= O) p -O-, -C (= Y) -, -C (= Y) -Y-, -O-CO 2 - and -O-;
R5 jeweils substituiertes oder unsubstituiertes C^Ce-Alkyl, C2-C6-Alkenyl oder C2-C6-Alkinyl;R 5 each substituted or unsubstituted C 1 -C 6 -alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;
R6 einen teil- oder ungesättigten carbocyclischen Rest, C3-C8-Cycloalkyl, Phenyl oder Heterocyclyl, die jeweils substituiert oder unsubstituiert sein können;R 6 is a partially or unsaturated carbocyclic radical, C 3 -C 8 cycloalkyl, phenyl or heterocyclyl, each of which may be substituted or unsubstituted;
R7 und R8 jeweils unabhängig voneinander Wasserstoff, C1-C6-Alkyl, C3-C6- Cycloalkyl,
Figure imgf000007_0001
Phenyl oder Benzyl;
R 7 and R 8 are each independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl,
Figure imgf000007_0001
Phenyl or benzyl;
p 0, 1 oder 2p 0, 1 or 2
bedeuten.mean.
Je nach Art der oben definierten Substituenten können die Verbindungen der allgemeinen Formel I saure oder basische Eigenschaften aufweisen und Salze bilden. Tragen die Verbindungen der allgemeinen Formel I beispielsweise Gruppen wie Hydroxy, Carboxy oder andere, saure Eigenschaften induzierende Gruppen, oder ist zum Beispiel -A3- eine direkte Bindung und gleichzeitig R3 Wasserstoff, so können diese Verbindungen mit Basen zu Salzen umgesetzt werden. Geeignete Basen sind beispielsweise Hydroxide, Carbonate, Hydrogencarbonate der Alkali- und Erdalkalimetalle, insbesondere die von Natrium, Kalium, Magnesium und Calcium, weiterhin Ammoniak, primäre, sekundäre und tertiäre Amine mit (C,-C4)- Alkylresten sowie Mono-, Di- und Trialkanolamine von (CrC4)-Alkanolen. Tragen die Verbindungen der allgemeinen Formel I beispielsweise Gruppen wie Amino, Alkylamino oder andere, basische Eigenschaften induzierende Gruppen, oder ist zum Beispiel -A2- eine Bindung und gleichzeitig R2 Wasserstoff , so können diese Verbindungen mit Säuren zu Salzen umgesetzt werden. Geeignete Säuren sind beispielsweise Mineralsäuren, wie Salz-, Schwefel- und Phosphorsäure, organische Säuren, wie Essigsäure, und saure Salze, wie NaHSO4 und KHS04. Die so erhältlichen Salze weisen ebenfalls nutzpflanzenschützende Eigenschaften auf.Depending on the nature of the substituents defined above, the compounds of the general formula I can have acidic or basic properties and form salts. If the compounds of the general formula I carry, for example, groups such as hydroxyl, carboxy or other groups which induce acidic properties or, for example, -A 3 - is a direct bond and R 3 is simultaneously hydrogen, these compounds can be reacted with bases to form salts. Suitable bases are, for example, hydroxides, carbonates, hydrogen carbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (C, -C 4 ) - alkyl radicals and mono-, di - and trialkanolamines of (C r C 4 ) -alkanols. For example, the compounds of the general formula I carry or are, for example, groups such as amino, alkylamino or other groups which induce basic properties -A 2 - a bond and at the same time R 2 is hydrogen, these compounds can be reacted with acids to form salts. Suitable acids are, for example, mineral acids, such as hydrochloric, sulfuric and phosphoric acids, organic acids, such as acetic acid, and acidic salts, such as NaHSO 4 and KHS0 4 . The salts obtainable in this way also have crop protection properties.
Substituierte 3-(5-Tetrazolylcarbonyl)-2-chinolone der allgemeinen Formel I mit den oben angegebenen Bedeutungen sind neu und ebenfalls Teil der Erfindung mit Ausnahme der Verbindungen der allgemeinen Formel I, in derSubstituted 3- (5-tetrazolylcarbonyl) -2-quinolones of the general formula I with the meanings given above are new and likewise part of the invention with the exception of the compounds of the general formula I in which
a) -A1-, -A2- und -A3- jeweils eine direkte Bindung und R1 Methyl und R2, R3, X1, X2, X3und X4 jeweils Wasserstoff, b) -A1-R1 und X4 gemeinsam -(CH2)2- und -A2- und -A3- jeweils eine direkte Bindung und R2, R3, X1, X2 und X3 jeweils Wasserstoff, c) -A1- eine direkte Bindung und R1 Wasserstoffa) -A 1 -, -A 2 - and -A 3 - each have a direct bond and R 1 is methyl and R 2 , R 3 , X 1 , X 2 , X 3 and X 4 are each hydrogen, b) -A 1 -R 1 and X 4 together - (CH 2 ) 2 - and -A 2 - and -A 3 - each have a direct bond and R 2 , R 3 , X 1 , X 2 and X 3 are each hydrogen, c) -A 1 - a direct bond and R 1 is hydrogen
bedeuten.mean.
In den nutzpflanzenschützenden Mitteln sind solche Verbindungen der allgemeinen Formel I bevorzugt, in derIn the crop protection agents, preference is given to those compounds of the general formula I in which
-A1- und -A2- jeweils eine direkte Bindung;-A 1 - and -A 2 - each have a direct bond;
-A3- eine direkte Bindung oder eine divalente Einheit aus der-A 3 - a direct bond or a divalent unit from the
Gruppe -C(=Y)- und -C(=Y)-Z-;Group -C (= Y) - and -C (= Y) -Z-;
R1, R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenyl-C1-C6-Alkyl, gegebenenfalls substituiertes C2-C6-Alkenyl, gegebenenfalls substituiertes C2-C6-Alkinyl, gegebenenfalls substituiertes C3-C9-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, C^C^-Alkoxy, CrC4-Alkylthio, C^C^- Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C9-Cycloalkyl, das unsubstituiert oder substituiert sein kann, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocyclus unsubstituiert oder substituiert sein kann, substituiertes C.,-C6-Alkyl;R 1 , R 2 , R 3 and R 4 are each independently hydrogen, optionally substituted phenyl, optionally substituted phenyl-C 1 -C 6 alkyl, optionally substituted C 2 -C 6 alkenyl, optionally substituted C 2 -C 6 alkynyl, optionally substituted C 3 -C 9 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, C ^ C ^ alkoxy, C r C 4 alkylthio, C ^ C ^ - alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 9 cycloalkyl, which may be unsubstituted or substituted, phenyl, which may be unsubstituted or substituted, heterocyclyl with a total of 3 up to 6 ring atoms, of which 1 to 3 are hetero ring atoms and come from the group nitrogen, oxygen and sulfur and the heterocycle can be unsubstituted or substituted, substituted C 1 -C 6 alkyl;
X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino, Hydroxy, Halogen, C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl,
Figure imgf000009_0001
C2-C6- Alkenyioxy, C2-C6-Alkinyloxy, C C6-Alkylthio, C,-C4-Alkylcarbonyl, C^C^ Alkoxycarbonyl oder C^C^Alkylthiocarbonyl, wobei die vorstehend genannten Kohlenwasserstoffreste durch ein oder mehrere gleiche oder verschiedene Halogenatome substituiert sein können;
X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxy, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl,
Figure imgf000009_0001
C 2 -C 6 -Alkenyioxy, C 2 -C 6 -alkynyloxy, CC 6 -alkylthio, C, -C 4 -alkylcarbonyl, C ^ C ^ alkoxycarbonyl or C ^ C ^ alkylthiocarbonyl, the above-mentioned hydrocarbon radicals by one or more identical or different halogen atoms can be substituted;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der bis zu 3 gleiche oder verschiedene Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, C C4-Alkyl und Oxo substituiert sein kann, bildend, bedeuten.-A 1 -R 1 and X 4 together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can contain up to 3 identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen, where this ring may be unsubstituted or substituted by one or more radicals from the group halogen, CC 4 -alkyl and oxo.
In den nutzpflanzenschützenden Mitteln sind solche Verbindungen der allgemeinen Formel I besonders bevorzugt, in der -A1- und -A2- jeweils eine direkte Bindung;In the crop protection agents such compounds of the general formula I are particularly preferred in which -A 1 - and -A 2 - each have a direct bond;
-A3- eine direkte Bindung oder eine divalente Einheit aus der-A 3 - a direct bond or a divalent unit from the
Gruppe -CO-, -CO2- und -CONR4-;Group -CO-, -CO 2 - and -CONR 4 -;
R1, R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenyl-C1-C6-Alkyl, gegebenenfalls substituiertes C2-C4-Alkenyl, gegebenenfalls substituiertes C2-C4-Alkinyl, gegebenenfalls substituiertes C3-C6-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, C C4-Alkoxy, C^C^Alkylthio, CrC4- Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocyclus unsubstituiert oder substituiert sein kann, substituiertes CrC6-Alkyl;R 1 , R 2 , R 3 and R 4 each independently of one another hydrogen, optionally substituted phenyl, optionally substituted phenyl-C 1 -C 6 alkyl, optionally substituted C 2 -C 4 alkenyl, optionally substituted C 2 -C 4 - Alkynyl, optionally substituted C 3 -C 6 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, CC 4 alkoxy, C 1 -C 4 alkylthio, C r C 4 alkyl sulfonyl, C 2 - C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl which may be unsubstituted or substituted, heterocyclyl with a total of 3 to 6 ring atoms, of which 1 to 3 are hetero ring atoms and from the group nitrogen, Oxygen and sulfur originate and the heterocycle can be unsubstituted or substituted, substituted C r C 6 alkyl;
X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino, Hydroxy, Halogen, CrC4-Alkyl, C^C^AIkoxy, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, Cr C4-Alkylthio, CrC4-Alkylcarbonyl oder C^C-Alkoxycarbonyl, wobei die vorstehend genannten Kohlenwasserstoffreste durch ein oder mehrere gleiche oder verschiedene Halogenatome substituiert sein können;X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxy, halogen, C r C 4 alkyl, C ^ C ^ alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy , C r C 4 alkylthio, C r C 4 alkylcarbonyl or C ^ C alkoxycarbonyl, where the above-mentioned hydrocarbon radicals can be substituted by one or more identical or different halogen atoms;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der ein Sauerstoffatom oder bis zu zwei Stickstoffatome enthalten kann und dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe C^C^Alkyl und Oxo substituiert sein kann, bildend, bedeuten.-A 1 -R 1 and X 4 together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which may contain one oxygen atom or up to two nitrogen atoms and this ring is unsubstituted or by one or more radicals from the group C ^ C ^ alkyl and oxo can be substituted, forming.
Die Bezeichnung 'Halogen' umfaßt Fluor, Chlor, Brom und Jod. Die Bezeichnungen 'Alkyl', 'Alkenyl' und 'Alkinyl' bedeuten, daß die Kohlenstoffkette verzweigt oder unverzweigt sein kann. Die beiden letztgenannten Bezeichnungen sind so zu verstehen, daß sich die Mehrfachbindung an beliebiger Position des betreffenden ungesättigten Restes befinden kann.The term 'halogen' includes fluorine, chlorine, bromine and iodine. The terms 'alkyl', 'alkenyl' and 'alkynyl' mean that the carbon chain can be branched or unbranched. The latter two terms are to be understood so that the multiple bond can be located at any position of the unsaturated radical in question.
Figure imgf000011_0001
bedeutet einen C C6-Alkylrest, der an beliebiger Position Phenyl trägt, wobei die Verknüpfung von Phenyl-C1-C6-Alkyl mit dem restlichen Teil des 3- (5-TetrazolylcarbonyI)-2-chinolons der allgemeinen Formel I über ein aliphatisches Kohlenstoffatom des
Figure imgf000011_0002
erfolgt.
Figure imgf000011_0001
means a CC 6 -alkyl radical which carries phenyl at any position, the linkage of phenyl-C 1 -C 6 -alkyl to the remaining part of the 3- (5-tetrazolylcarbonyI) -2-quinolone of the general formula I via an aliphatic Carbon atom of
Figure imgf000011_0002
he follows.
Unter Heterocyclyl ist ein Rest zu verstehen, der auf einen drei- bis sechsatomigen, einkernigen, gesättigten, teilgesättigten, ungesättigten oder aromatischen Ring zurückzuführen ist, von dessen drei bis sechs Ringatomen ein bis drei Atome unabhängig voneinander aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen können, z. B. Aziridin, Azirin, Oxiran, Thietan, Dioxolan, Furan, Thiophen, Pyrrol, Pyrrolidin, Imidazol, Imidazolidin, Pyran, Tetrahydropyran, Thiapyran, Pyridin, Piperidin, Dioxan, Pyrimidin, Morpholin, wobei die Verknüpfung zum Tetrazolylcarbonyl-2-chinolon an beliebiger Position des heterocyclischen Ringes erfolgen kann, sofern es die Bindigkeit des Verknüpfungsatoms erlaubt. Unter einem teilgesättigten oder ungesättigten carbocyclischen Rest ist ein drei- bis achtatomiger aus Kohlenstoffatomen aufgebauter Ring zu verstehen, wie Cyclopropenyl, Cyclobutenyl, Cyclopentenyl, Cyclopentadienyl, Cyclohexenyl.Heterocyclyl is to be understood as meaning a radical which can be attributed to a three to six atom, mononuclear, saturated, partially saturated, unsaturated or aromatic ring, of which three to six ring atoms independently of one another come from the group nitrogen, oxygen and sulfur can, e.g. B. aziridine, azirine, oxirane, thietane, dioxolane, furan, thiophene, pyrrole, pyrrolidine, imidazole, imidazolidine, pyran, tetrahydropyran, thiapyran, pyridine, piperidine, dioxane, pyrimidine, morpholine, the linkage to tetrazololcarbonon-2 Any position of the heterocyclic ring can take place, provided that the binding atom allows. A partially saturated or unsaturated carbocyclic radical is to be understood as a three- to eight-atom ring composed of carbon atoms, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl.
Falls nicht ausdrücklich anders definiert, ist unter dem Begriff 'gegebenenfalls substituiert' im Zusammenhang mit Alkenyl-, Alkinyl-, Cycloalkyl-, Phenyl-, Phenyl- C^Ce-Alkyl-, Heterocyclyl-, teilgesättigten, ungesättigten, carbocyclischen Resten zu verstehen, daß diese Reste entweder unsubstituiert sind, oder daß ein oder mehrere Wasserstoffatome durch die äquivalente Anzahl gleicher oder verschiedener Substituenten aus der Gruppe Halogen, Hydroxy, Nitro, Cyano, Oxo, C1-C3-Alkoxy, Halogen-C C3-alkoxy, Halogen-C C3-alkyl ersetzt sind. Halogen-Cr C3-alkoxy, Halogen-CrC3-alkyl bedeuten, daß ein oder mehrere Wasserstoffatome durch die entsprechende Anzahl gleicher oder verschiedener Halogenatome substituiert sind.Unless expressly defined otherwise, the term "optionally substituted" is to be understood in connection with alkenyl, alkynyl, cycloalkyl, phenyl, phenyl, C 1 -C 4 alkyl, heterocyclyl, partially saturated, unsaturated, carbocyclic radicals, that these radicals are either unsubstituted, or that one or more hydrogen atoms by the equivalent number of identical or different substituents from the group halogen, hydroxy, nitro, cyano, oxo, C 1 -C 3 alkoxy, halogen-C C 3 alkoxy, Halogen-C C 3 alkyl are replaced. Halogen-C r C 3 -alkoxy, halogen-C r C 3 -alkyl mean that one or more hydrogen atoms are substituted by the corresponding number of identical or different halogen atoms.
Für den Fall daß -A1-, -A2- und/oder -A3- eine divalente Einheit bedeuten, die unsymmetrisch ist, d.h. daß sie zwei Möglichkeiten der Verknüpfung erlaubt, sind jeweils beide Möglichkeiten der Verknüpfung von -A1-, -A2- und/oder -A3- mit R\ R2 und/oder R3 einerseits und dem 3-(5-Tetrazolylcarbonyl)-2-chinolon andererseits durch die allgemeine Formel I umfaßt. Das gleiche gilt sinngemäß für -B- und R5 beziehungsweise R6.In the event that -A 1 -, -A 2 - and / or -A 3 - mean a divalent unit which is asymmetrical, ie that it allows two possibilities of linking, both options of linking -A 1 - are -A 2 - and / or -A 3 - with R \ R 2 and / or R 3 on the one hand and the 3- (5-tetrazolylcarbonyl) -2-quinolone on the other hand encompassed by the general formula I. The same applies analogously to -B- and R 5 or R 6 .
Die Verbindungen der allgemeinen Formel I können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden, beispielsweise durch chromatographische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft auch alle Stereoisomeren und deren Gemische, die von der allgemeinen Formel I umfaßt, jedoch nicht spezifisch definiert sind.Depending on the nature and linkage of the substituents, the compounds of the general formula I can be present as stereoisomers. For example, if one or more alkenyl groups are present, diastereomers can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. Stereoisomers can also be prepared selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances. The invention also relates to all stereoisomers and their mixtures which are encompassed by the general formula I but are not specifically defined.
Die Kombinationsmöglichkeiten der verschiedenen Substituenten der allgemeinen Formel I sind so zu verstehen, daß die allgemeinen Grundsätze des Aufbaus chemischer Verbindungen zu beachten sind, d.h. daß nicht Verbindungen gebildet werden, von denen der Fachmann weiß, daß sie chemisch instabil oder nicht möglich sind.The possible combinations of the various substituents of the general formula I are to be understood in such a way that the general principles of the structure of chemical compounds must be observed, i.e. that no compounds are formed which the person skilled in the art knows that they are chemically unstable or not possible.
Bevorzugt sind auch solche Mittel, die mindestens eine Verbindung der allgemeinen Formel I und mindestens ein Herbizid aus den Gruppen A) Phenoxyphenoxycarbonsäuren und HeteroaryloxyphenoxycarbonsäurenPreference is also given to those compositions which comprise at least one compound of the general formula I and at least one herbicide from the groups A) Phenoxyphenoxycarboxylic acids and heteroaryloxyphenoxycarboxylic acids
B) SulfonylharnstoffeB) sulfonylureas
C) ImidazolinoneC) Imidazolinones
D) TriazolopyrimidinsulfonamideD) Triazolopyrimidine sulfonamides
E) Pyrimidinyloxy-pyridincarbonsäurederivate, Pyrimidinyloxy-benzoesäure derivateE) Pyrimidinyloxy-pyridinecarboxylic acid derivatives, pyrimidinyloxy-benzoic acid derivatives
F) CyclohexandionoximeF) Cyclohexanedione oximes
G) Benzoylcyclohexandione oderG) benzoylcyclohexanedione or
H) S-(N-Alkyl-carbaniloylmethyl)-dithiophosphorsäurederivateH) S- (N-alkyl-carbaniloylmethyl) dithiophosphoric acid derivatives
enthalten.contain.
Beispiele solcher für eine Kombination mit Verbindungen der allgemeinen Formel I geeigneter Herbizide sindExamples of such herbicides which are suitable for a combination with compounds of the general formula I are
A) Phenoxyphenoxycarbonsäure- und Heteroaryloxyphenoxycarbonsäure-^- C4)-alkyl-, -(C2-C4)-alkenyl-, -(C2-C4)-alkinylester;A) phenoxyphenoxycarboxylic acid and heteroaryloxyphenoxycarboxylic acid - ^ - C 4 ) alkyl, - - (C 2 -C 4 ) alkenyl, - (C 2 -C 4 ) alkynyl ester;
B) Pyrimidinaminocarbonyl- und Triazinylaminocarbonyl-[benzol-, pyridin-, pyrazol-, thiophen- und (alkylsulfonyl)alkylamino-]sulfamide;B) pyrimidinaminocarbonyl and triazinylaminocarbonyl [benzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) alkylamino] sulfamides;
C) Alkyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)pyridincarbonsäuren, Alkyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzolcarbonsäuren, 2- (4-lsopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)chinolincarbonsäuren;C) alkyl-2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) pyridinecarboxylic acids, alkyl-2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin- 2-yl) benzenecarboxylic acids, 2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) quinoline carboxylic acids;
D) N-Phenyl-1 ,2,4-triazolo[1 ,5-c]pyrimidin-2-sulfonamide;D) N-phenyl-1, 2,4-triazolo [1,5-c] pyrimidine-2-sulfonamides;
E) 3-Pyrimidin-2-yl-oxy-pyridin-2-carbonsäureester, 2,6-Bis(pyrimidin-2-yl- oxy)benzoesäureesterE) 3-pyrimidin-2-yl-oxy-pyridine-2-carboxylic acid ester, 2,6-bis (pyrimidin-2-yl-oxy) benzoic acid ester
F) 5-substituierte 2-(1 -Alkoxyiminoalkyl)-3-hydroxy-cyclohex-2-en-1 -one;F) 5-substituted 2- (1-alkoxyiminoalkyl) -3-hydroxy-cyclohex-2-en-1-one;
G) 2-Benzoylcyclohexan-1 ,3-dione;G) 2-benzoylcyclohexane-1,3-dione;
H) S-(N-Alkyl-carbaniloylmethyl)-dithiophosphorsäure-O,O-dialkylester. Beispiele besonders geeigneter Herbizide sind solche, die aus den GruppenH) S- (N-Alkyl-carbaniloylmethyl) -dithiophosphoric acid-O, O-dialkyl ester. Examples of particularly suitable herbicides are those from the groups
A) 2-(4-(2,4-Dichlorphenoxy)phenoxy)propionsäuremethylester (A1 ), 2-(4-(5-Trifluormethyl-2-pyridyloxy)phenoxy)propionsäurebutylester (A2), 2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäuremethylester (A3), 2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäureethylester (A4), 2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäure (A5), 2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäure-2-isopropyliden- aminooxyethylester (A6),A) 2- (4- (2,4-dichlorophenoxy) phenoxy) propionic acid methyl ester (A1), 2- (4- (5-trifluoromethyl-2-pyridyloxy) phenoxy) propionic acid butyl ester (A2), 2- (4- (6- Chloro-2-quinoxalyloxy) phenoxy) propionic acid methyl ester (A3), 2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionic acid ethyl ester (A4), 2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionic acid (A5), 2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionic acid 2-isopropylidene aminooxyethyl ester (A6),
2-(4-(6-Chlorbenzoxazol-2-yloxy)phenoxy)propionsäureethylester (A7), 2-(4-(6-Chlorbenzoxazol-2-yloxy)phenoxy)propionsäureethylester D(+)lsomer (A8), 2-(4-(6-Chlorbenzthiazol-2-yloxy)phenoxy)propionsäureethylester (A9);Ethyl 2- (4- (6-chlorobenzoxazol-2-yloxy) phenoxy) propionate (A7), ethyl 2- (4- (6-chlorobenzoxazol-2-yloxy) phenoxy) propionate (D (+) isomer (A8), 2- ( 4- (6-Chlorobenzthiazol-2-yloxy) phenoxy) propionic acid ethyl ester (A9);
B) 1 -(2-Chlorphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)hamstoff (B1 ), 1 -(2-Ethoxycarbonylphenylsulfonyl)-3-(4-chlor-6-methoxy-pyrimidin-2- yl)harnstoff (B2), 1 -(2-Methoxyphenyisulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5- triazin-2-yl)-hamstoff (B3), 1 -(2-Chlorethoxyphenylsulfonyl)-3-(4-methoxy-6- methyl-1 ,3,5-triazin-2-yl)harnstoff (B4), 1 -(2-Methoxycarbonyl- phenylsulfonyl)-3-(4,6-dimethylpyhmidin-2-yl)hamstoff (B5), 1 -(2- Methoxycarbonyl-phenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2- yl)harnstoff (B6), 1-(2-Methoxycarbonylbenzylsulfonyl)-3-(4,6- dimethoxypyrimidin-2-yl)hamstoff (B7), 1 -(2-Methoxycarbonyl- phenylsulfonyl)-3-(4,6-difluormethoxypyrimidin-2-yl)harnstoff (B8), 1 -(2- Methoxycarbonylthiophen-3-yl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2- yl)harnstoff (B9), 1 -(4-Ethoxycarbonyl-1 -methylpyrazol-5-yl-sulfonyl)-3-(4,6- dimethoxypyrimidin-2-yl)harnstoff (B10), 5-(4,6-Dimethylpyrimidin-2-yl- carbamoylsulfamoyl)-1-(2-pyridyl)pyrazol-4-carbonsäuremethylester (B11 ), 3- (4,6-Dimethoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonylaminosul- fonyl)hamstoff (B12), 1-(3-N,N-Dimethylaminocarbonylpyridin-2-ylsulfonyl)-3- (4,6-dimethoxy-pyrimidin-2-yl)hamstoff (B13), 1 -(3-Ethylsulfonylpyridin-2- ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)hamstoff (B14), 2-[3-(4,6-Dimethoxypyrimidin-2-yl)ureidosulfonyI]-6-trifluormethyl-3-pyhdin- carbonsäuremethylester (B15), 3-(4-Methoxy-6-methyl-1 ,3,5-tήazin-2-yl)-1 -(2- methoxycarbonyl-5-iodphenylsulfonyl)-3-(4,6-dimethylpyhmidin-2-yl)hamstoff (B16), lod- oder aminosubstituierte Pyndylsulfonylharnstoffe, wie sie in DE-A 40 00 503 und DE-A 40 30 577 beschrieben sind, Alkoxyphenoxy-sulfo- nylharnstoffe wie sie in EP-A 0 342 569 beschrieben sind;B) 1 - (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea (B1), 1 - (2-ethoxycarbonylphenylsulfonyl) -3- (4th -chloro-6-methoxy-pyrimidin-2-yl) urea (B2), 1 - (2-methoxyphenyisulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) - urea (B3), 1 - (2-chloroethoxyphenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea (B4), 1 - (2-methoxycarbonylphenylsulfonyl) -3- (4,6-dimethylpyhmidin-2-yl) urea (B5), 1 - (2- methoxycarbonyl-phenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2- yl) urea (B6), 1- (2-methoxycarbonylbenzylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (B7), 1 - (2-methoxycarbonylphenylsulfonyl) -3- (4,6- difluoromethoxypyrimidin-2-yl) urea (B8), 1 - (2-methoxycarbonylthiophen-3-yl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea (B9) , 1 - (4-Ethoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (B10), 5- (4,6-dimethylpyrimidin-2-yl- carbamoylsulfamoyl) -1- (2-pyridyl) pyrazole-4-carboxylic acid meth yl ester (B11), 3- (4,6-dimethoxypyrimidin-2-yl) -1- (N-methyl-N-methylsulfonylaminosulphonyl) urea (B12), 1- (3-N, N-dimethylaminocarbonylpyridine-2- ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (B13), 1 - (3-ethylsulfonylpyridin-2-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea ( B14), 2- [3- (4,6-Dimethoxypyrimidin-2-yl) ureidosulfonyI] -6-trifluoromethyl-3-pyhdin-carboxylic acid methyl ester (B15), 3- (4-methoxy-6-methyl-1, 3,5-tήazin -2-yl) -1 - (2-methoxycarbonyl-5-iodophenylsulfonyl) -3- (4,6-dimethylpyhmidin-2-yl) urea (B16), iodine- or amino-substituted pyndylsulfonylureas, as described in DE-A 40 00 503 and DE-A 40 30 577 are described, alkoxyphenoxy-sulfonylureas as described in EP-A 0 342 569;
C) 2-(4-lsopropyl-4-methyl-5-oxo-2-imidazolidin-2-yl)-4-methylbenzoesäure (C1 ), 5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolidin-2-yl)pyridin-3- carbonsäure (C2), 2-(4-lsopropyl-4-methyl-5-oxo-2-imidazolidin-2-yl)chinolin- 3-carbonsäure (C3), 2-(4-lsopropyl-4-methyl-5-oxo-2-imidazolidin-2- yl)pyridin-3-carbonsäure (C4), 5-Methyl-2-(4-isopropyl-4-methyl-5-oxo-2- imidazolidin-2-yl)pyridin-3-carbonsäure (C5);C) 2- (4-isopropyl-4-methyl-5-oxo-2-imidazolidin-2-yl) -4-methylbenzoic acid (C1), 5-ethyl-2- (4-isopropyl-4-methyl-5- oxo-2-imidazolidin-2-yl) pyridine-3-carboxylic acid (C2), 2- (4-isopropyl-4-methyl-5-oxo-2-imidazolidin-2-yl) quinoline-3-carboxylic acid (C3) , 2- (4-isopropyl-4-methyl-5-oxo-2-imidazolidin-2-yl) pyridine-3-carboxylic acid (C4), 5-methyl-2- (4-isopropyl-4-methyl-5- oxo-2-imidazolidin-2-yl) pyridine-3-carboxylic acid (C5);
D) N-(2,6-Difluorphenyl)-7-methyl-1 ,2,4-triazolo[1 ,5-c]pyrimidin-2-sulfon-amid (D1 ), N-(2,6-Dichlor-3-methylphenyl)-5,7-dimethoxy-1 ,2,4-triazolo[1 ,5- c]pyrimidin-2-sulfonamid (D2), N-(2-Chlor-6-methoxycarbonylphenyl)-5,7- dimethyl-1 ,2,4-thazolo[1 ,5-c]pyrimidin-2-sulfonamid (D3);D) N- (2,6-difluorophenyl) -7-methyl-1, 2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide (D1), N- (2,6-dichloro- 3-methylphenyl) -5,7-dimethoxy-1, 2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide (D2), N- (2-chloro-6-methoxycarbonylphenyl) -5,7- dimethyl-1, 2,4-thazolo [1,5-c] pyrimidine-2-sulfonamide (D3);
E) 3-(4,6-Dimethoxypyrimidin-2-yl)oxy-pyridin-2-carbonsäurebenzylester (E1 ), 3- (4,6-Dimethoxypyrimidin-2-yl)oxy-pyridin-2-carbonsäuremethylester (E2), 2,6- Bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoesäureester (E3), 2,6-Bis[(4,6- dimethoxypyrimidin-2-yl)oxy]benzoesäure-(1-ethoxycarbonyloxyethyl)ester (E4);E) 3- (4,6-dimethoxypyrimidin-2-yl) oxy-pyridine-2-carboxylic acid benzyl ester (E1), 3- (4,6-dimethoxypyrimidin-2-yl) oxy-pyridine-2-carboxylic acid methyl ester (E2), 2,6-bis [(4,6-dimethoxypyrimidin-2-yl) oxy] benzoic acid ester (E3), 2,6-bis [(4,6-dimethoxypyrimidin-2-yl) oxy] benzoic acid (1-ethoxycarbonyloxyethyl) ester (E4);
F) 3-(1-Allyloxyiminobutyl)-4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-en- carbonsäuremethylester (F1 ), 2-(1-Ethoxyiminobutyl)-5-(2-ethylthiopropyl)-3- hydroxy-2-cyclohex-2-en-1 -on (F2), 2-(1 -Ethoxyiminobutyl)-5-(2-phenylthio- propyl)-3-hydroxy-2-cyclohex-2-en-1 -on (F3), 2-(1 -(3-Chlorallyloxy)imino- propyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohex-2-en-1-on (F4),F) Methyl 3- (1-allyloxyiminobutyl) -4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-ene carboxylate (F1), 2- (1-ethoxyiminobutyl) -5- (2-ethylthiopropyl) -3 - hydroxy-2-cyclohex-2-en-1 -one (F2), 2- (1-ethoxyiminobutyl) -5- (2-phenylthio-propyl) -3-hydroxy-2-cyclohex-2-en-1 - on (F3), 2- (1 - (3-chloroallyloxy) iminopropyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohex-2-en-1-one (F4),
2-(1 -Ethoxyiminobutyl)-3-hydroxy-5-(thian-3-yl)-2-cyclohex-2-en-1 -on (F5), 2- (1-Ethoxyiminopropy)-5-(2,4,6-trimethylphenyl)-3-hydroxy-2-cyclohex-2-en-1- on (F6); G) 2-(2-Chlor-4-methylsulfonylbenzoyl)cyclohexan-1 ,3-dion (G1 ), 2-(2-2- (1-ethoxyiminobutyl) -3-hydroxy-5- (thian-3-yl) -2-cyclohex-2-en-1-one (F5), 2- (1-ethoxyiminopropy) -5- (2, 4,6-trimethylphenyl) -3-hydroxy-2-cyclohex-2-en-1-one (F6); G) 2- (2-chloro-4-methylsulfonylbenzoyl) cyclohexane-1,3-dione (G1), 2- (2-
Nitro-3-methylsulfonylbenzoyl)-4,4-dimethylcyclohexan-1 ,3-dion (G2), 2-(2- Nitrobenzoyl)-4,4-dimethylcyclohexan-1 ,3-dion (G3);Nitro-3-methylsulfonylbenzoyl) -4,4-dimethylcyclohexane-1,3-dione (G2), 2- (2-nitrobenzoyl) -4,4-dimethylcyclohexane-1,3-dione (G3);
H) S-(4-Chlor-N-isopropyl-carbaniloylmethyl)-dithiophosphorsäure-O,O- dimethylester stammen.H) S- (4-Chloro-N-isopropyl-carbaniloylmethyl) -dithiophosphoric acid-O, O-dimethyl ester.
Die folgenden Zitate stehen beispielhaft:The following quotes are examples:
B16 ist bekannt aus WO 92/13845. D3 ist bekannt aus US-A 4 988 812. E1 und E2 sind bekannt aus EP-A 0 249 707. E3 ist bekannt aus EP-A 0 321 846. E4 ist bekannt aus EP-A 0472 113. G2 ist bekannt aus WO 91/13548. G3 ist bekannt aus EP-A 0274634. Alle anderen unter A) bis H) genannten Herbizide sind bekannt aus "The Pesticide Manual", 10. Aufl. (1994), Brit. Crop. Prot. Council, London.B16 is known from WO 92/13845. D3 is known from US-A 4 988 812. E1 and E2 are known from EP-A 0 249 707. E3 is known from EP-A 0 321 846. E4 is known from EP-A 0472 113. G2 is known from WO 91/13548. G3 is known from EP-A 0274634. All other herbicides mentioned under A) to H) are known from "The Pesticide Manual", 10th edition (1994), Brit. Crop. Prot. Council, London.
Für den Fall, daß die erfindungsgemäßen Mittel Herbizide enthalten, werden diese Mittel nach entsprechender Verdünnung entweder direkt auf die Anbaufläche oder auf die bereits gekeimten Schad- und/oder Nutzpflanzen oder auf die bereits aufgelaufenen Schad- und/oder Nutzpflanzen appliziert. Für den Fall, daß die erfindungsgemäßen Mittel kein Herbizid enthalten, können diese Mittel im sogenannten Tankmix-Verfahren - d.h. unmittelbar vor dem Auf bringen auf die zu behandelnde Fläche erfolgt anwenderseits die Vermischung undIn the event that the agents according to the invention contain herbicides, these agents are applied after appropriate dilution either directly to the area under cultivation or to the already germinated harmful and / or useful plants or to the already emerged harmful and / or useful plants. In the event that the agents according to the invention do not contain any herbicide, these agents can be used in the so-called tank mix process - i.e. immediately before bringing up on the surface to be treated, the mixing takes place and
Verdünnung der separat käuflichen Produkte nutzpflanzenschützendes Mittel und Herbizid -, oder zeitlich vor der Anwendung eines Herbizids, oder zeitlich nach der Anwendung eines Herbizids, oder zur Saatgut-Vorbehandlung, d.h. zur Beizung des Nutzpflanzensaatguts verwendet werden.Dilution of the separately available products crop protection agent and herbicide - or before the application of a herbicide, or after the application of a herbicide, or for seed pretreatment, i.e. be used for dressing the crop seeds.
Bevorzugt ist die gemeinsame Anwendung von Safener und Herbizid als Fertigformulierung oder die Anwendung im Tankmix-Verfahren. Das Gewichtsverhältnis Safener zu Herbizid kann innerhalb weiter Grenzen variieren und liegt vorzugsweise im Bereich von 1 :10 bis 10:1 , insbesondere von 1 :10 bis 5:1. Das optimale Gewichtsverhältnis Safener zu Herbizid hängt von den eingesetzten Wirkstoffen Safener und Herbizid und von der Art der zu schützenden Nutzpflanzen ab. Die erforderliche Aufwandmenge an Safener kann je nach verwendetem Herbizid und Art der zu schützenden Nutzpflanze innerhalb weiter Grenzen variieren und liegt in der Regel im Bereich von 0,001 bis 5 kg, vorzugsweise 0,005 bis 0,5 kg Safener je Hektar.Preferred is the joint use of safener and herbicide as a finished formulation or use in the tank mix process. The weight ratio of safener to herbicide can vary within wide limits and is preferably in the range from 1:10 to 10: 1, in particular from 1:10 to 5: 1. The optimal weight ratio of safener to herbicide depends on the active ingredients safener and herbicide and on the type of crop to be protected. The required amount of safener can vary within wide limits, depending on the herbicide used and the type of crop to be protected, and is generally in the range from 0.001 to 5 kg, preferably 0.005 to 0.5 kg, of safener per hectare.
In der Regel können die erfindungsgemäßen Mittel zum Schutz verschiedener Nutzpflanzenkulturen wie Getreide, Baumwolle, Raps und Sojabohne eingesetzt werden. Bevorzugte Nutzpflanzenkulturen sind Gerste, Hafer, Roggen, Mais, Sorghum und Weizen, besonders bevorzugt ist Mais.As a rule, the agents according to the invention can be used to protect various crops such as cereals, cotton, rapeseed and soybeans. Preferred crops are barley, oats, rye, corn, sorghum and wheat, and corn is particularly preferred.
Die Verbindungen der allgemeinen Formel I und deren Kombinationen mit einem oder mehreren der genannten Herbizide können in Abhängigkeit von den vorgegebenen chemisch-physikalischen und biologischen Parametern auf verschiedene Arten formuliert werden. Als Formulierungsarten sind beispielsweise geeignet:The compounds of general formula I and their combinations with one or more of the herbicides mentioned can be formulated in various ways depending on the specified chemical-physical and biological parameters. Examples of suitable types of formulation are:
• Emulgierbare Konzentrate, die durch Auflösen der Wirkstoffe in einem organischen Lösungsmittel, z. B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höher siedenden Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt werden. Geeignete Emulgatoren sind beispielsweise alkylarylsulfonsaure Calcium- Salze, Fettsäurepolyglykolester, Alkyarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester und Polyoxyethylensorbitanfettsäureester; • Stäubemittel, die durch Vermählen der Wirkstoffe mit fein verteilten festen anorganischen oder organischen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, Diatomeenerde oder Mehlen erhalten werden;• Emulsifiable concentrates, which are obtained by dissolving the active ingredients in an organic solvent, e.g. Example, butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Suitable emulsifiers are, for example, alkylarylsulfonic acid calcium salts, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters; • dusts which are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, diatomaceous earth or flours;
• Auf Wasser oder öl basierende Suspensionskonzentrate, die beispiels weise durch Naß-Vermahlung mittels Perlmühlen hergestellt werden können;• Water or oil-based suspension concentrates, which can be produced, for example, by wet grinding using pearl mills;
• Wasserlösliche Pulver;• water soluble powders;
• Wasserlösliche Konzentrate;• water-soluble concentrates;
• Granulate, wie wasserlösliche Granulate, wasserdispergierbare Granulate sowie Granulate für die Streu- und Bodenapplikation;• Granules, such as water-soluble granules, water-dispersible granules and granules for spreading and soil application;
• Spritzpulver, die neben Wirkstoff noch Verdünnungs- oder Inertstoffe und Tenside enthalten;• wettable powders which, in addition to the active ingredient, also contain diluents or inert substances and surfactants;
• Kapselsuspensionen und Mikrokapseln;• capsule suspensions and microcapsules;
• Ultra-Low-Volume-Formulierungen.• Ultra low volume formulations.
Die oben genannten Formulierungsarten sind dem Fachmann bekannt und werden beispielsweise beschrieben in: K. Martens, "Spray Drying Handbook", 3rd Ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y. 1973; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Auflage 1986; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, N.Y. 1973, Seiten 8-57.The above-mentioned types of formulation are known to the person skilled in the art and are described, for example, in: K. Martens, "Spray Drying Handbook", 3rd Ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y. 1973; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th edition 1986; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, N.Y. 1973, pages 8-57.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y.; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Auflage 1986.The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; C. Marsden, Solvents Guide, 2nd Ed., Interscience, NY 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th edition 1986.
Je nach Art der Formulierung enthalten die nutzpflanzenschützenden Mittel in der Regel 0,1 bis 99 Gew.-%, insbesondere 0,2 bis 95 Gew.-%, eines oder mehrerer Safener der allgemeinen Formel I oder einer Kombination von Safener und Herbizid. Weiterhin enthalten sie 1 bis 99,9, insbesondere 5 bis 99,8 Gew.-%, eines oder mehrerer fester oder flüssiger Zusatzstoffe und 0 bis 25, insbesondere 0,1 bis 25 Gew.-% eines Tensids. In emulgierbaren Konzentraten beträgt die Wirkstoffkonzentration in der Regel 1 bis 90, insbesondere 5 bis 80 Gew.-%. Stäubemittel enthalten üblicherweise 1 bis 30, vorzugsweise 5 bis 20 Gew.-% Wirkstoff. In Spritzpulvern beträgt die Wirkstoffkonzentration in der Regel 10 bis 90 Gew. -%.Depending on the type of formulation, the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula I or a combination of safener and herbicide. They also contain 1 to 99.9, in particular 5 to 99.8% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25% by weight of a surfactant. The active substance concentration in emulsifiable concentrates is generally 1 to 90, in particular 5 to 80,% by weight. Dusts usually contain 1 to 30, preferably 5 to 20% by weight of active ingredient. The active ingredient concentration in wettable powders is generally 10 to 90% by weight.
Außer den vorstehend genannten Formulierungshilfsmitteln können die nutzpflanzenschützenden Mittel gegebenenfalls übliche Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz-, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer sowie den pH-Wert oder die Viskosität beeinflussende Mittel enthalten.In addition to the formulation auxiliaries mentioned above, the crop protection agents can, if appropriate, customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH or the like Contain viscosity-influencing agents.
Vor der Anwendung werden die nutzpflanzenschützenden Mittel gegebenenfalls in üblicher Weise verdünnt, beispielsweise werden Spritzpulver, emulgierbare Konzentrate, wasserlösliche und wasserdispergierbare Granulate mit Wasser verdünnt. Andere Granulate, Stäubemittel sowie sprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr verdünnt. Die erforderliche Aufwandmenge der nutzpflanzenschützenden Mittel variiert auch mit äußeren Bedingungen, wie Temperatur und Feuchtigkeit.Before use, the crop protection agents are optionally diluted in a customary manner, for example wettable powders, emulsifiable concentrates, water-soluble and water-dispersible granules are diluted with water. Other granules, dusts and sprayable solutions are usually no longer diluted before use. The application rate of the crop protection agents also varies with external conditions, such as temperature and humidity.
Die Verbindungen der allgemeinen Formel I können nach dem unten angegebenen Reaktionsschema hergestellt werden: Die Aniline der allgemeinen Formel II sind käuflich oder gemäß dem Fachmann bekannten Methoden herstellbar. Die Verbindungen der allgemeinen Formeln III, VI und I können jeweils aus den im Reaktionsschema gezeigten Vorstufen gemäß dem Fachmann bekannten Reaktionen, wie Alkylierungen oder Acylierungen von Amino- oder Hydroxyverbindungen, hergestellt werden. Solche Alkylierungen oder Acylierungen sind beispielsweise bekannt aus Houben-Weyl Bd. VI/3, Georg-Thieme Verlag, Stuttgart, 1965, Seiten 24 und 49; Houben-Weyl Bd. VIII, Georg-Thieme Verlag, Stuttgart, 1952, S. 543. Die Reaktionen, die zu den Verbindungen der allgemeinen Formeln IV, V und VII führen, sind beispielsweise aus J. Heterocyclic Chem., 21, 1881 (1984), Aus. J. Chem., 16, 480 (1963) und J. Chem. Soc, 1959, 444 bekannt. The compounds of general formula I can be prepared according to the reaction scheme given below: The anilines of general formula II are can be obtained commercially or according to methods known to the person skilled in the art. The compounds of the general formulas III, VI and I can each be prepared from the precursors shown in the reaction scheme in accordance with reactions known to the person skilled in the art, such as alkylations or acylations of amino or hydroxy compounds. Such alkylations or acylations are known, for example, from Houben-Weyl Vol. VI / 3, Georg-Thieme Verlag, Stuttgart, 1965, pages 24 and 49; Houben-Weyl Vol. VIII, Georg-Thieme Verlag, Stuttgart, 1952, p. 543. The reactions which lead to the compounds of the general formulas IV, V and VII are, for example, from J. Heterocyclic Chem., 21, 1881 ( 1984), Aus. J. Chem., 16, 480 (1963) and J. Chem. Soc, 1959, 444.
Figure imgf000021_0001
Figure imgf000021_0001
Figure imgf000021_0002
Figure imgf000021_0002
(V) (VI)(V) (VI)
Figure imgf000021_0003
Figure imgf000021_0003
(VII) (I) Beispiele(VII) (I) Examples
1. FORMULIERUNGSBEISPIELE 1.1 STÄUBEMITTEL1. FORMULATION EXAMPLES 1.1 DUST
10 Gew.-% einer Verbindung der allgemeinen Formel I oder einer Mischung eines Herbizids mit einer Verbindung der allgemeinen Formel I und 90 Gew.-% Talkum werden gemischt und in einer Schlagmühle feinst gemahlen.10% by weight of a compound of general formula I or a mixture of a herbicide with a compound of general formula I and 90% by weight of talc are mixed and finely ground in a hammer mill.
1.2. WASSERDISPERGIERBARES GRANULAT1.2. WATER-DISPERSIBLE GRANULES
75 Gew.-% einer Verbindung der allgemeinen Formel I oder einer Mischung eines Herbizids mit einer Verbindung der allgemeinen Formel I, 10 Gew.-% ligninsulfonsaures Calcium, 5 Gew.-% Natriumlaurylsulfat, 3 Gew.-% Polyvi- nylalkohol und 7 Gew.-% Kaolin werden gemischt, in einer Stiftmühle gemahlen und das so erhaltene Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert.75% by weight of a compound of the general formula I or a mixture of a herbicide with a compound of the general formula I, 10% by weight of calcium lignosulfonate, 5% by weight sodium lauryl sulfate, 3% by weight polyvinyl alcohol and 7% by weight .-% kaolin are mixed, ground in a pin mill and the powder thus obtained is granulated in a fluidized bed by spraying water as the granulating liquid.
2. HERSTELLBEISPIELE2. MANUFACTURING EXAMPLES
2.1. 1 ,2-DLHYDRO-4-HYDROXY-1 -ETHYL-3-(5-TETRAZOLYLCARBONYL)-2-CHINOLON2.1. 1, 2-DLHYDRO-4-HYDROXY-1 -ETHYL-3- (5-TETRAZOLYLCARBONYL) -2-QUINOLONE
2,6 g (40 mmol) Natriumazid werden zu einer Lösung von 3,0 g (10 mol) 3- Dichloracetyl-1-ethyl-1 ,2-dihydro-4-hydroxy-2-chinolon in 50 ml Dimethylformamid gegeben und 36 Stunden bei Raumtemperatur gerührt. Nach Verdünnen mit 500 ml Eiswasser wird abfiltriert und das Filtrat mit verdünnter Salzsäure auf einen pH-Wert von 4 eingestellt. Der ausgefallene Feststoff wird abgesaugt, mit Wasser gewaschen und getrocknet. Man erhält 2,0 g (70% der Theorie) 1 ,2-Dihydro-4- hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon mit einem Schmelzpunkt von 229° C. Die in nachfolgenden Tabellen aufgeführten Verbindungen der allgemeinen Formel I können in analoger Weise hergestellt werden. Die hier verwendeten Abkürzungen bedeuten:2.6 g (40 mmol) of sodium azide are added to a solution of 3.0 g (10 mol) of 3-dichloroacetyl-1-ethyl-1, 2-dihydro-4-hydroxy-2-quinolone in 50 ml of dimethylformamide and 36 Stirred for hours at room temperature. After dilution with 500 ml of ice water, the mixture is filtered off and the filtrate is adjusted to a pH of 4 with dilute hydrochloric acid. The precipitated solid is filtered off, washed with water and dried. 2.0 g (70% of theory) of 1,2-dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone with a melting point of 229 ° C. are obtained. The compounds of the general formula I listed in the tables below can be prepared in an analogous manner. The abbreviations used here mean:
Bn Benzyl c-Pr : cyclo-Propyl i-Pr iso-Propyl Pr PropylBn Benzyl c-Pr: cyclo-propyl i-Pr iso-propyl Pr propyl
Ph Phenyl t-Bu : tertiär-ButylPh phenyl t-Bu: tertiary butyl
F.P. FestpunktF.P. Benchmark
Figure imgf000023_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
3. BIOLOGISCHE BEISPIELE
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
3. BIOLOGICAL EXAMPLES
Figure imgf000032_0001
Figure imgf000032_0001
S1S1
Die Schadwirkung an den Pflanzen wird auf einer Skala von 0 bis 100% optisch im Vergleich zu unbehandelten Kontrollpflanzen bewertet. Dabei bedeuten:The harmful effects on the plants are assessed optically on a scale from 0 to 100% in comparison to untreated control plants. Here mean:
0% keine erkennbare Schädigung im Vergleich zu unbehandelten0% no noticeable damage compared to untreated
KontrollpflanzenControl plants
100% : totale Schädigung, d.h. Pflanze stirbt ab.100%: total damage, i.e. Plant dies.
3.1. WIRKUNG IM VORAUFLAUF3.1. EARLY EFFECT
Samen beziehungsweise Rhizomstücke mono- und dikotyler Schad- und Nutzpflanzen werden in Töpfchen von 9 cm Durchmesser in sandiger Lehmerde ausgelegt und mit Erde bedeckt. Hierzu alternativ werden für den Reis-Test Reispflanzen sowie in dieser Nutzpflanzenkultur unerwünschte Schadpflanzen in einem mit Wasser übersättigten Boden kultiviert. Die als emulgierbare Konzentrate formulierten erfindungsgemäßen Mittel aus Safener und Herbiziden sowie in parallelen Versuchen die entsprechend formulierten Einzelwirkstoffe werden dann als Emulsionen mit einer Wassermenge von umgerechnet 800 l/ha in unterschiedlichen Dosierungen auf die Oberfläche der Abdeckerde appliziert oder beim Reis-Test in das Bewässerungswasser gegossen. Anschließend werden die Töpfe zur weiteren Kultivierung der Pflanzen im Gewächshaus unter optimalen Bedingungen gehalten. Die optische Bewertung der Schäden an Nutz- und Schadpflanzen erfolgt nach dem Auflaufen dieser Pflanzen, d.h. etwa 2 bis 4 Wochen nach Versuchsbeginn. Die Versuche zeigen, daß die erfindungsgemäßen Mittel, welche beispielsweise den Safener S1 in Kombination mit jeweils einem der Sulfonylhamstoffe 3-(4,6-Dimethoxypyrimid-2-yl)-1-[3-(N-methylsulfonyl-N- methyiamino)pyridin-2-yl-sulfonyl]harnstoff und 3-(4-Methoxy-6-methyl-1 ,3,5-triazin- 2-yl)-1-(2-methoxycarbonyl-5-iod-phenylsulfonyl)hamstoff (Natriumsalz) im Verhältnis von Safener zu Herbizid von 2:1 oder 17:1 enthalten, eine gute Wirkung gegen ein breites Spektrum von mono- und dikotylen Schadpflanzen auf, wobei die Schäden an den Nutzpflanzen wie Mais oder Reis im Vergleich zur Anwendung der Herbizide ohne Safener wesentlich, d.h. um 50 bis 100 % reduziert sind.Seeds or rhizome pieces of mono- and dicotyledonous harmful and useful plants are placed in pots 9 cm in diameter in sandy loam and covered with earth. Alternatively, rice plants as well as undesirable harmful plants in this crop of crops are cultivated in a soil oversaturated with water for the rice test. The agents according to the invention formulated as emulsifiable concentrates from safeners and herbicides and, in parallel experiments, the correspondingly formulated individual active ingredients are then applied as emulsions with a water amount of the equivalent of 800 l / ha in different dosages to the surface of the covering earth or poured into the irrigation water in the rice test . Then the Pots for further cultivation of the plants in the greenhouse kept under optimal conditions. The optical evaluation of the damage to crops and harmful plants takes place after the emergence of these plants, ie about 2 to 4 weeks after the start of the test. The experiments show that the agents according to the invention which contain, for example, the safener S1 in combination with one of the sulfonylureas 3- (4,6-dimethoxypyrimid-2-yl) -1- [3- (N-methylsulfonyl-N-methyiamino) pyridine -2-yl-sulfonyl] urea and 3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -1- (2-methoxycarbonyl-5-iodophenylsulfonyl) urea (sodium salt) contain in the ratio of safener to herbicide of 2: 1 or 17: 1, a good effect against a wide range of monocotyledonous and dicotyledonous plants, the damage to the useful plants such as maize or rice being significant compared to the use of the herbicides without safener , ie reduced by 50 to 100%.
3.2. WIRKUNG IM NACHAUFLAUF3.2. EFFECT AFTER THE CLEARANCE
Samen beziehungsweise Rhizomstücke mono- und dikotyler Schad- und Nutzpflanzen werden in Töpfchen von 9 cm Durchmesser in sandiger Lehmerde ausgelegt und mit Erde bedeckt. Hierzu alternativ werden für den Reis-Test Reispflanzen sowie in dieser Nutzpflanzenkultur unerwünschte Schadpflanzen in einem mit Wasser übersättigten Boden kultiviert. Im Dreiblattstadium, d.h. etwa drei Wochen nach Beginn der Aufzucht werden die Versuchspflanzen mit den als emulgierbare Konzentrate oder Stäubemittel formulierten erfindungsgemäßen Mitteln aus Safener und Herbiziden sowie in parallelen Versuchen mit den entsprechend formulierten Einzelwirkstoffe behandelt. Dazu werden die erfindungsgemäßen Mittel und die Vergleichsmittel mit einer Wassermenge von umgerechnet 800 l/ha in unterschiedlichen Dosierungen auf die grünen Pflanzenteile gesprüht oder beim Reis-Test auch in das Bewässerungswasser gegossen. Die Töpfe werden zur weiteren Kultivierung der Pflanzen im Gewächshaus unter optimalen Bedingungen gehalten. Die optische Bewertung der Schäden an Nutz- und Schadpflanzen erfolgt nach weiteren 2 bis 3 Wochen. Die Versuche zeigen, daß die erfindungsgemäßen Mittel, welche beispielsweise den Safener S1 in Kombination mit jeweils einem der Sulfonylharnstoffe 3-(4,6- Dimethoxypyrimid-2-yl)-1-[3-(N-methylsulfonyl-N-methylamino)pyridin-2-yl- sulfonyljharnstoff und 3-(4-Methoxy-6-methyl-1 ,3,5-triazin-2-yl)-1 -(2-methox- ycarbonyl-5-iod-phenylsulfonyl)hamstoff (Natriumsalz) im Verhältnis von Safener zu Herbizid von 2:1 oder 17:1 enthalten, im Nachauflauf ebenfalls eine gute Wirkung gegen ein breites Spektrum von mono- und dikotylen Schadpflanzen aufweisen, wobei die Schäden an den Nutzpflanzen wie Mais oder Reis im Vergleich zur Anwendung der Herbizide ohne Safener wesentlich, d.h. um 50 bis 100% reduziert sind. Seeds or rhizome pieces of mono- and dicotyledonous harmful and useful plants are placed in pots 9 cm in diameter in sandy loam and covered with earth. Alternatively, rice plants as well as undesirable harmful plants in this crop of crops are cultivated in a soil oversaturated with water for the rice test. In the three-leaf stage, ie about three weeks after the start of rearing, the test plants are treated with the agents according to the invention from safeners and herbicides formulated as emulsifiable concentrates or dusts, and in parallel experiments with the correspondingly formulated individual active compounds. For this purpose, the agents according to the invention and the comparative agents are sprayed with a water amount of the equivalent of 800 l / ha in different dosages onto the green parts of the plants or, in the rice test, also poured into the irrigation water. The pots are kept in the greenhouse under optimal conditions for further cultivation of the plants. The visual assessment of damage to crops and harmful plants takes place after a further 2 to 3 weeks. The Experiments show that the agents according to the invention, which, for example, the safener S1 in combination with one of the sulfonylureas 3- (4,6-dimethoxypyrimid-2-yl) -1- [3- (N-methylsulfonyl-N-methylamino) pyridine- 2-yl-sulfonyl urea and 3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -1 - (2-methoxy-carbonyl-5-iodophenylsulfonyl) urea (sodium salt) im Ratio of safener to herbicide of 2: 1 or 17: 1 included, also have a good effect against a broad spectrum of mono- and dicotyledonous crops in post-emergence, the damage to crops such as corn or rice compared to the use of herbicides without Safener essential, ie reduced by 50 to 100%.

Claims

Patentansprüche claims
1. Gegebenenfalls mindestens ein Herbizid enthaltende nutzpflanzenschützende Mittel, gekennzeichnet durch einen Gehalt mindestens eines substituierten 3-(5- Tetrazolylcarbonyl)-2-chinolons der allgemeinen Formel I, gegebenenfalls auch in seiner Salzform1. If appropriate, at least one herbicide-containing crop protection agent, characterized by a content of at least one substituted 3- (5-tetrazolylcarbonyl) -2-quinolone of the general formula I, optionally also in its salt form
Figure imgf000035_0001
Figure imgf000035_0001
in derin the
-A1-, -A2- und -A3- jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Einheit aus der Gruppe -C(=Y)-, -C(=Y)-Z-, -S(=O)-, -SO2- und -S02NR4-;-A 1 -, -A 2 - and -A 3 - each independently of one another a direct bond or a divalent unit from the group -C (= Y) -, -C (= Y) -Z-, -S (= O ) -, -SO 2 - and -S0 2 NR 4 -;
Y Sauerstoff oder Schwefel; Z Sauerstoff, Schwefel oder NR4;Y oxygen or sulfur; Z is oxygen, sulfur or NR 4 ;
R1, R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenyl-CrC6-Alkyl, gegebenenfalls substituiertes C2-C6-Alkenyl, gegebenenfalls substituiertes C2-C6-Alkinyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato, CrC4-Alkoxy, CrC4-Alkylthio, CrC4-Alkylsulfinyl, CrC4- Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C9-Cycloalkyl, das unsubstituiert oder substituiert sein kann, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocy- clus unsubstituiert oder substituiert sein kann, substituiertes C.,-C6-Alkyl;R 1 , R 2 , R 3 and R 4 each independently of one another hydrogen, optionally substituted phenyl, optionally substituted phenyl-C r C 6 alkyl, optionally substituted C 2 -C 6 alkenyl, optionally substituted C 2 -C 6 alkynyl , optionally substituted C 3 -C 8 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, nitro, cyano, thiocyanato, C r C 4 alkoxy, C r C 4 alkylthio, C r C 4 -Alkylsulfinyl, C r C 4 - Alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 9 cycloalkyl which may be unsubstituted or substituted, phenyl which may be unsubstituted or substituted, heterocyclyl with a total of 3 to 6 ring atoms, of which 1 to 3 are hetero ring atoms and come from the group nitrogen, oxygen and sulfur and the heterocycle can be unsubstituted or substituted, substituted C 1 -C 6 alkyl;
X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino,X 1 , X 2 , X 3 and X 4 each independently of one another are hydrogen, amino,
Carboxyl, Formyl, Hydroxy, Halogen, Nitro, Cyano, Thiocyanato, -B-R5, -B-R6, oder zwei benachbarte X gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der bis zu 3 gleiche oder verschiedene Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, C^C^-Alkyl und Oxo substituiert sein kann, bildend;Carboxyl, formyl, hydroxy, halogen, nitro, cyano, thiocyanato, -BR 5 , -BR 6 , or two adjacent X together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can be up to 3 may contain identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen, this ring being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C 1 -C 4 -alkyl and oxo;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf-, sechs- oder siebengliedrigen teilgesättigten oder ungesättigten Ring, der bis zu 3 gleiche oder verschiedene Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, C1-C4-Alkyl und Oxo substituiert sein kann, bildend;-A 1 -R 1 and X 4 together with the ring atoms to which they are attached form a five-, six- or seven-membered partially saturated or unsaturated ring which contain up to 3 identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen may, whereby this ring may be unsubstituted or substituted by one or more radicals from the group halogen, C 1 -C 4 alkyl and oxo;
-B- eine direkte Bindung oder eine divalente Einheit aus der-B- a direct bond or a divalent unit from the
Gruppe -S(=O)p-, -S(=O)p-O-, -C(=Y)-, -C(=Y)-Y-, -O-CO2-, -NR7-, -NR7-O-, -NR7-(C=O)-, -NR7-CO2-, -NR7-CO-NR8- und -O-;Group -S (= O) p -, -S (= O) p -O-, -C (= Y) -, -C (= Y) -Y-, -O-CO 2 -, -NR 7 - , -NR 7 -O-, -NR 7 - (C = O) -, -NR 7 -CO 2 -, -NR 7 -CO-NR 8 - and -O-;
R5 jeweils substituiertes oder unsubstituiertes
Figure imgf000036_0001
R 5 each substituted or unsubstituted
Figure imgf000036_0001
C2-C6-Alkenyl oder C2-C6-Alkinyl; R6 einen teil- oder ungesättigten carbocyclischen Rest, C3-C8-C 2 -C 6 alkenyl or C 2 -C 6 alkynyl; R 6 is a partially or unsaturated carbocyclic radical, C 3 -C 8 -
Cycloalkyl, Phenyl oder Heterocyclyl, die jeweils substituiert oder unsubstituiert sein können;Cycloalkyl, phenyl or heterocyclyl, each of which may be substituted or unsubstituted;
R7 und R8 jeweils unabhängig voneinander Wasserstoff, CVCVAlkyl, C3-R 7 and R 8 each independently of one another are hydrogen, CVCV alkyl, C 3 -
C6-Cycloalkyl, C^Cs-Alkylcarbonyl, Phenyl oder Benzyl;C 6 cycloalkyl, C 1 -C 4 alkylcarbonyl, phenyl or benzyl;
p 0, 1 oder 2p 0, 1 or 2
bedeuten.mean.
2. Nutzpflanzenschützende Mittel nach Anspruch 1 , worin2. A crop protection agent according to claim 1, wherein
-A1- und -A2- eine direkte Bindung;-A 1 - and -A 2 - a direct bond;
-A3- eine direkte Bindung oder eine divalente Einheit aus der-A 3 - a direct bond or a divalent unit from the
Gruppe -C(=Y)- und -C(=Y)-Z-;Group -C (= Y) - and -C (= Y) -Z-;
R1, R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes
Figure imgf000037_0001
gegebenenfalls substituiertes C2-C6-Alkenyl, gegebenenfalls substituiertes C2-C6-Alkinyl, gegebenenfalls substituiertes C3-C9-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, CrC4-Alkoxy, CrC4-Alkylthio, CrC4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C9-Cycloalkyl, das unsubstituiert oder substituiert sein kann, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocyclus unsubstituiert oder substituiert sein kann, substituiertes CVCe-Alkyl;
R 1 , R 2 , R 3 and R 4 are each independently hydrogen, optionally substituted phenyl, optionally substituted
Figure imgf000037_0001
optionally substituted C 2 -C 6 alkenyl, optionally substituted C 2 -C 6 alkynyl, optionally substituted C 3 -C 9 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, C r C 4 -alkoxy, C r C 4 -alkylthio, C r C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 - C 9 -cycloalkyl, which may be unsubstituted or substituted, phenyl , which may be unsubstituted or substituted, heterocyclyl with a total of 3 to 6 ring atoms, of which 1 to 3 are hetero ring atoms and come from the group nitrogen, oxygen and sulfur and the heterocycle can be unsubstituted or substituted, substituted CVCe-alkyl;
X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino, Hydroxy, Halogen, CrC6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C C6-Alkylthio, C^C^Alkylcarbonyl, C C4-AIkoxycarbonyl oder C1-C4-Alkylthiocarbonyl, wobei die vorstehend genannten Kohlenwasserstoffreste durch ein oder mehrere gleiche oder verschiedene Halogenatome substituiert sein können;X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxy, halogen, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, CC 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, CC 6 -alkylthio, C 1 -C 4 -alkylcarbonyl, CC 4 -alkoxycarbonyl or C 1 -C 4 -alkylthiocarbonyl, it being possible for the above-mentioned hydrocarbon radicals to be substituted by one or more identical or different halogen atoms;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der bis zu 3 gleiche oder verschiedene Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, C1-C4-Alkyl und Oxo substituiert sein kann, bildend;-A 1 -R 1 and X 4 together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can contain up to 3 identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen, where this ring can be unsubstituted or substituted by one or more radicals from the group consisting of halogen, C 1 -C 4 alkyl and oxo;
bedeuten.mean.
3. Nutzpflanzenschützende Mittel nach Anspruch 1 oder 2, worin3. A crop protection agent according to claim 1 or 2, wherein
-A1- und -A2- jeweils eine direkte Bindung;-A 1 - and -A 2 - each have a direct bond;
-A3- eine direkte Bindung oder eine divalente Einheit aus der-A 3 - a direct bond or a divalent unit from the
Gruppe -CO-, -CO2- und -CONR4-;Group -CO-, -CO 2 - and -CONR 4 -;
R\ R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes
Figure imgf000038_0001
gegebenenfalls substituiertes C2-C4-Alkenyl, gegebenenfalls substituiertes C2-C4-Alkinyl, gegebenenfalls substituiertes C3-C6-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, CrC4-Alkoxy, CrC4-Alkylthio, CΛ-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocyclus unsubstituiert oder substituiert sein kann, substituiertes C1-C6-Alkyl; X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino, Hydroxy, Halogen, CrC4-Alkyl, CrC4-Alkoxy, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, CrC4- Alkylthio, C^C-Alkylcarbonyl oder C C4-Alkoxycarbonyl, wobei die vorstehend genannten Kohlenwasserstoffreste durch ein oder mehrere gleiche oder verschiedene Halogenatome substituiert sein können;
R \ R 2 , R 3 and R 4 each independently of one another hydrogen, optionally substituted phenyl, optionally substituted
Figure imgf000038_0001
optionally substituted C 2 -C 4 alkenyl, optionally substituted C 2 -C 4 alkynyl, optionally substituted C 3 -C 6 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, C r C 4 -alkoxy, C r C 4 -alkylthio, CΛ-alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 - C 6 -cycloalkyl, phenyl, which may be unsubstituted or substituted, with heterocyclyl a total of 3 to 6 ring atoms, of which 1 to 3 are hetero ring atoms and come from the group nitrogen, oxygen and sulfur and the heterocycle can be unsubstituted or substituted, substituted C 1 -C 6 alkyl; X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxy, halogen, C r C 4 alkyl, C r C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 - alkynyloxy, C r C 4 - alkylthio, C ^ C alkyl-carbonyl or C 4 alkoxycarbonyl, wherein the hydrocarbon radicals mentioned above may be substituted by one or more identical or different halogen atoms;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der ein Sauerstoffatom oder bis zu zwei Stickstoffatome enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe C^OrAlkyl und Oxo substituiert sein kann, bildend;-A 1 -R 1 and X 4 together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which may contain one oxygen atom or up to two nitrogen atoms, this ring being unsubstituted or by one or more Radicals from the group C ^ OrAlkyl and oxo can be substituted, forming;
bedeuten.mean.
4. Nutzpflanzenschützende Mittel nach einem der Ansprüche 1 bis 3 enthaltend mindestens ein Herbizid.4. crop protection agents according to one of claims 1 to 3 containing at least one herbicide.
5. Nutzpflanzenschützende Mittel nach einem der Ansprüche 1 bis 4, enthaltend mindestens ein Herbizid aus den Gruppen5. crop protection agents according to one of claims 1 to 4, containing at least one herbicide from the groups
A) Phenoxyphenoxycarbonsäuren und HeteroaryloxyphenoxycarbonsäurenA) Phenoxyphenoxycarboxylic acids and heteroaryloxyphenoxycarboxylic acids
B) SulfonylhamstoffeB) sulfonylureas
C) ImidazolinoneC) Imidazolinones
D) TriazolopyrimidinsulfonamideD) Triazolopyrimidine sulfonamides
E) Pyrimidinyloxy-pyrimidincarbonsäurederivateE) Pyrimidinyloxy-pyrimidinecarboxylic acid derivatives
F) Pyrimidinyloxy-benzoesäurederivateF) Pyrimidinyloxy-benzoic acid derivatives
G) Cyclohexandionoxime H) Benzoylcyclohexandione oderG) cyclohexanedione oximes H) benzoylcyclohexanediones or
I) S-(N-Aryl-N-alkyl-carbamoylmethyl)-dithiophosphonsäureester. I) S- (N-aryl-N-alkyl-carbamoylmethyl) dithiophosphonic acid ester.
6. Verfahren zum Schutz von Nutzpflanzen vor den phytotoxischen Eigenschaften von Herbiziden, dadurch gekennzeichnet, daß Mittel gemäß einem der Ansprüche 1 bis 5 in einer Nutzpflanzenkultur verwendet werden.6. A method for protecting crops from the phytotoxic properties of herbicides, characterized in that agents according to one of claims 1 to 5 are used in a crop of crops.
7. Substituierte 3-(5-Tetrazolylcarbonyl)-2-chinolone der allgemeinen Formel I nach Anspruch I, mit der Maßgabe, daß7. Substituted 3- (5-tetrazolylcarbonyl) -2-quinolones of the general formula I according to claim I, with the proviso that
a) R1 nicht Methyl ist, wenn -A1-, -A2- und -A3- jeweils eine direkte Bindung und R2, R3, X1, X2, X3 und X4 jeweils Wasserstoff sind; b) -A1- R1 und X4 nicht gemeinsam -(CH2)2- bilden, wenn -A2- und -A3 jeweils eine direkte Bindung und R2, R3, X1, X2 und X3 jeweils Wasserstoff sind; c) -A1- nicht eine direkte Bindung bedeutet, wenn R1 Wasserstoff ist.a) R 1 is not methyl if -A 1 -, -A 2 - and -A 3 - are each a direct bond and R 2 , R 3 , X 1 , X 2 , X 3 and X 4 are each hydrogen; b) -A 1 - R 1 and X 4 do not form together - (CH 2 ) 2 - if -A 2 - and -A 3 each form a direct bond and R 2 , R 3 , X 1 , X 2 and X 3 are each hydrogen; c) -A 1 - does not mean a direct bond when R 1 is hydrogen.
8. Substituierte 3-(5-Tetrazolylcarbonyl)-2-chinolone nach Anspruch 7, in denen8. Substituted 3- (5-tetrazolylcarbonyl) -2-quinolones according to claim 7, in which
-A1- und -A2- jeweils eine direkte Bindung-A 1 - and -A 2 - each have a direct bond
-A3- eine direkte Bindung oder eine divalente Einheit aus der Gruppe-A 3 - a direct bond or a divalent unit from the group
-C(=Y)- und -C(=Y)-Z-;-C (= Y) - and -C (= Y) -Z-;
R\ R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenyl-C^Ce-Alkyl, gegebenenfalls substituiertes C2-C6-Alkenyl, gegebenenfalls substituiertes C2-C6-Alkinyl, gegebenenfalls substituiertes C3-C9-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, CrC4-Alkoxy, CrC4-Alkylthio, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C9-Cycloalkyl, das unsubstituiert oder substituiert sein kann, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocyclus unsubstituiert oder substituiert sein kann, substituiertes C.,-C6-Alkyl; X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino, Hydroxy, Halogen, CrC6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C Cβ-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, CrC6-Alkylthio, C^C^Alkylcarbonyl, C^C^AIkoxycarbonyl, CrC4- Alkylthiocarbonyl, wobei die vorstehend genannten Kohlenwasserstoffreste durch ein oder mehrere gleiche oder verschiedene Halogenatome substituiert sein können;R \ R 2, R 3 and R 4 are each independently hydrogen, optionally substituted phenyl, optionally substituted phenyl-C ^ Ce-alkyl, optionally substituted C 2 -C 6 -alkenyl, optionally substituted C 2 -C 6 alkynyl optionally substituted C 3 -C 9 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, C r C 4 alkoxy, C r C 4 alkylthio, CC 4 alkylsulfonyl, C 2 -C 4 Alkenyl, C 2 -C 4 alkynyl, C 3 - C 9 cycloalkyl which may be unsubstituted or substituted, phenyl which may be unsubstituted or substituted, heterocyclyl with a total of 3 to 6 ring atoms, of which 1 to 3 are hetero ring atoms and come from the group nitrogen, oxygen and sulfur and the heterocycle can be unsubstituted or substituted, substituted C 1 -C 6 alkyl; X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxyl, halogen, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C Cβ alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C r C 6 alkylthio, C ^ C ^ alkylcarbonyl, C ^ C ^ alkoxycarbonyl, C r C 4 - alkylthiocarbonyl, the above-mentioned hydrocarbon radicals by one or several identical or different halogen atoms can be substituted;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der bis zu 3 gleiche oder verschiedene Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, wobei dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, C^C^-Alkyl und Oxo substituiert sein kann, bildend;-A 1 -R 1 and X 4 together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can contain up to 3 identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen, where this ring may be unsubstituted or substituted by one or more radicals from the group consisting of halogen, C 1 -C 4 -alkyl and oxo;
bedeuten.mean.
9. Substituierte 3-(5-Tetrazolylcarbonyl)-2-chinolone nach Anspruch 7 oder 8, in denen9. Substituted 3- (5-tetrazolylcarbonyl) -2-quinolones according to claim 7 or 8, in which
-A1- und -A2- jeweils eine direkte Bindung,-A 1 - and -A 2 - each have a direct bond,
-A3- eine direkte Bindung oder eine divalente Einheit aus der-A 3 - a direct bond or a divalent unit from the
Gruppe -C(=O)-, -C(=0)-O- und -C(=O)-NR4-;Group -C (= O) -, -C (= 0) -O- and -C (= O) -NR 4 -;
R\ R2, R3 und R4 jeweils unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenyl-C C6-Alkyl, gegebenenfalls substituiertes C2-C4-Alkenyl, gegebenenfalls substituiertes C2-C4-Alkinyl, gegebenenfalls substituiertes C3-C6-Cycloalkyl, unsubstituiertes oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, CrC^AIkoxy, C^C^Alkylthio, C^C^Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3- C6-Cycloalkyl, Phenyl, das unsubstituiert oder substituiert sein kann, Heterocyclyl mit insgesamt 3 bis 6 Ringatomen, wovon 1 bis 3 Heteroringatome sind und aus der Gruppe Stickstoff, Sauerstoff und Schwefel stammen und der Heterocyclus unsubstituiert oder substituiert sein kann, substituiertes CrC6-Alkyl;R \ R 2 , R 3 and R 4 each independently of one another hydrogen, optionally substituted phenyl, optionally substituted phenyl-C 6 alkyl, optionally substituted C 2 -C 4 alkenyl, optionally substituted C 2 -C 4 alkynyl, optionally substituted C 3 -C 6 cycloalkyl, unsubstituted or by one or more identical or different radicals from the group halogen, cyano, CrC ^ alkoxy, C ^ C ^ alkylthio, C ^ C ^ alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 - C 6 cycloalkyl, phenyl, which can be unsubstituted or substituted, heterocyclyl with a total of 3 to 6 ring atoms, of which 1 to 3 are hetero ring atoms and from which Group nitrogen, oxygen and sulfur originate and the heterocycle can be unsubstituted or substituted, substituted C r C 6 alkyl;
X1, X2, X3 und X4 jeweils unabhängig voneinander Wasserstoff, Amino, Hydroxy, Halogen, C^C^Alkyl, CrC4-Alkoxy, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, C^C Alkylthio, C^C-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, wobei die vorstehend genannten Kohlenwasserstoffreste durch ein oder mehrere gleiche oder verschiedene Halogenatome substituiert sein können;X 1 , X 2 , X 3 and X 4 each independently of one another hydrogen, amino, hydroxy, halogen, C ^ C ^ alkyl, C r C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy C 1 -C 4 -alkylthio, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, it being possible for the abovementioned hydrocarbon radicals to be substituted by one or more identical or different halogen atoms;
-A1-R1 und X4 gemeinsam mit den Ringatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen teilgesättigten oder ungesättigten Ring, der bis zu zwei Stickstoffatome enthalten kann und dieser Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe C C4-Alkyl und Oxo substituiert sein kann, bildend;-A 1 -R 1 and X 4 together with the ring atoms to which they are attached, a five- or six-membered partially saturated or unsaturated ring which can contain up to two nitrogen atoms and this ring is unsubstituted or by one or more radicals from the group CC 4 alkyl and oxo may be substituted forming;
bedeuten. mean.
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