DE3917883A1 - New imidazo- and oxazolo-quinoline derivs. - useful as herbicides selective towards cultivated plants - Google Patents

Abstract

Imidazo- and oxazolo-quinoline derivs. (I) are new. R1 = H; halogen; carboxyl; or 1-6C alkyl opt. substd. by 1-4C alkoxy, 1-4C alkylthio or halogen; R2 = H; 1-6C alkyl; 3-6C cycloalkyl opt. substd. by 1-4C alkyl phenyl or naphthyl opt. substd. by nitro, amino, halogen, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, 1-4C haloalkyl, acylamino or acyloxy; or a 5- or 6-membered heterocycle contg. 1 or 2 O, S and/or N atoms and opt. substd. by nitro, 1-4C alkyl or halogen; X = O or -NR3-; R3 = H; 1-6C alkyl; 3-6C cycloalkyl; 1-4C alkylamino; or benzyl opt. substd. by halogen, 1-4C alkyl, 1-4C haloalkyl or 1-4C alkoxy. USE - Cpds. (I) are herbicides which are selective towards cultivated plants. They are formulated conventionally and can be applied in amts. of 0.001-4 kg/ha.

Description

The invention relates to 3H-imidazo [4,5-h] (oxazolo [5,4-h]) quinolines, Process for their preparation, herbicides containing these compounds as Contain active ingredients, as well as a method of combating undesirable Plant growth with these agents.

Substituted 3H-imidazo [4,5-h] (oxazolo [5,4-h]) quinolines have already been Fluorine Chem., Vol. 20, pp. 573-580 (1982); ibid., Vol. 41, Pp. 277-288 (1988)); Such compounds having herbicidal properties are not known.

It was found that 3H-imidazo [4,5-h] (oxazolo [5,4-h]) quinolines of formula

in the
R¹ is hydrogen, halogen, carboxyl or optionally C₁-C₆-alkoxy, C₁-C₄-alkylthio or halogen-substituted C₁-C₆-alkyl,
R² is hydrogen, C₁-C₆-alkyl, an optionally substituted by C₁-C₄-alkyl C₃-C₆-cycloalkyl, optionally substituted by nitro, amino, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄- Alkylthio, C₁-C₄-haloalkyl, acylamino or acyloxy-substituted phenyl or naphthyl radical or an optionally substituted by nitro, C₁-C₄-alkyl or halogen-substituted 5- or 6-membered heterocyclic radical having one or two heteroatoms selected from the group oxygen, sulfur and Nitrogen, and
X is oxygen or the radical -NR3-, where R³ is hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkylamino or optionally by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁- C₄-alkoxy substituted benzyl,
stand, have herbicidal activity and are selective to crops.

The C₁-C₆-alkyl radicals for R¹, R² and R³ in formula I can be unbranched or be branched and, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, n-pentyl or n-hexyl. The same applies to the alkoxy, alkylthio, haloalkyl and alkylamino radicals. Suitable substituents of the alkyl radicals for R¹ are halogen, such as chlorine, Bromine or fluorine, C₁-C₄-alkoxy or C₁-C₄-alkylthio, such as methoxy, ethoxy, Methylthio or ethylthio. Examples of such radicals are trichloromethyl, Trifluoromethyl, methoxymethyl, 1-methoxyethyl, methylthiomethyl, ethyl thiomethyl. Preference is given to radicals having 1 to 4 carbon atoms.

Halogen in substituents of the formula I means, for example, fluorine, chlorine or bromine.

Examples of C₃-C₆cycloalkyl radicals for R² and R³ are cyclopropyl, Cyclobutyl, cyclopentyl and cyclohexyl. The radicals for R² may additionally be substituted by C₁-C₄-alkyl, in particular methyl or ethyl.

The phenyl, 1-naphthyl and 2-naphthyl radicals for R² may be simple or be substituted several times. Examples of substituents are nitro, amino, Halogen, such as fluorine, chlorine, bromine, C₁-C₄-alkyl, preferably methyl or Ethyl, C₁-C₄-alkoxy, preferably methoxy or ethoxy, C₁-C₄-alkylthio, preferably methylthio, C₁-C₄-haloalkyl, such as trifluoromethyl, acylamino having 1 to 4 C atoms in the acyl group, for example formyl, acetyl, Propionyl, n-butyryl or i-butyryl and acyloxy with 2 to 5 carbon atoms in the acyl group, for example acetyloxy, propionyloxy, n-butyryloxy or i-butyryloxy.

Examples of heterocyclic radicals for R 2 are pyrrolyl, furyl, thienyl, Thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, Pyridyl, pyrimidyl, pyrazinyl, pyridazinyl. These radicals can by Nitro, C₁-C₄-alkyl, preferably methyl or ethyl, or by halogen, such as chlorine, bromine or fluorine, be substituted.

R³ in the radical -NR³ can C₁-C₆-alkyl, preferably C₁-C₄-alkyl, in particular Methyl or ethyl, or an optionally halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxy substituted benzyl radical, for example, 4-chlorobenzyl, 4-trifluoromethylbenzyl, 4-methylbenzyl, 4-methoxy-benzyl or 2,4-dichloro-benzyl.

The 3H-imidazo [4,5-h] quinolines of the formula I are obtained by reacting 7,8-diamino-quinolines of the formula

in a conventional manner with carboxylic acids of the formula R²-COOH (III) or Orthoesters of the formula R²-C (OR⁴) ₃ (IV), in which R⁴ is C₁-C₄-alkyl.

The reaction proceeds very well at a temperature in the range of 80 to 120 ° C in the presence of polyphosphoric acid or at 70 to 100 ° C below Effect of 3 to 6 equivalents IV. The amount of III is appropriate moderately 1.1 mol, based on 1 mol of II. Larger excesses of III do not disturb.

The oxazolo [5,4-h] quinolines of formula I are obtained according to the 3H-imidazo [4,5-h] quinolines by reaction of 7-hydroxy-8-amino quinolines of the formula

with carboxylic acids of the formula II or orthoesters of the formula IV the synthesis of the 3H-imidazo [4,5-h] quinolines indicated reaction conditions apply accordingly.

The diaminoquinolines II and the aminohydroxyquinolines V can, starting of 7-chloroquinolines of the formula VI, in which R¹ is the one mentioned for formula I. Meanings, are easily obtained. The synthesis proceeds in itself known manner according to the following reaction scheme:

synthesis Examples example 1 3-methyl-7-chloro-3H-imidazo [4,5-h] quinoline

24.9 g (0.12 mol) of 8-amino-3-chloro-7-methylaminochinoline are mixed with 107 g (0.72 mol) of triethyl orthoformate and heated to 100 ° C for 30 min. It is then allowed to successively cool to 0 ° C and sucks the precipitate (32 g) from. The mother liquor is concentrated in vacuo and the rear was recrystallized from an ethyl acetate / petroleum ether mixture. The combined solids thus obtained are identical.
Yield: 48.5 g (82%); Mp: 188 to 189 ° C.

example 2 2-methyl-3-ethyl-7-chloro-3H-imidazo [4,5-h] quinoline

14 g (64 mmol) of 8-amino-3-chloro-7-ethylaminoquinoline are mixed with 42 g (0.26 mol) of triethyl orthoacetate and stirred at 100 ° C for 1 hour. It is allowed to come to room temperature, excess orthoester evaporates and the residue is recrystallized from ethyl acetate.
Yield: 7.7 g (49%); Mp .: 145 to 148 ° C.

example 3 2- (4-chlorophenyl) -3-ethyl-7-chloro-3H-imidazo [4,5-h] quinoline

A mixture consisting of 4.1 g (20 mmol) of 8-amino-3-chloro-7-ethylamino quinoline, 3.1 g (20 mmol) of 4-chlorobenzoic acid and 20 ml of polyphosphoric acid is heated to 120 ° C for 1 hour. It is allowed to cool to 90 ° C and slowly gives 100 g of ice in the solution. It is then poured onto 200 g of ice and adjusted with concentrated sodium hydroxide solution to a pH of 12. The precipitate is filtered off with suction, washed thoroughly with warm water, dried at 70 ° C. in vacuo and recrystallised from ethyl acetate.
Yield: 5.5 g (80%); Mp .: 110 to 112 ° C.

example 4 2,7-Dimethyloxazolo [5,4-h] quinoline

3.48 g (20 mmol) of 8-amino-7-hydroxy-3-methylquinoline are mixed with 16.2 g (100 mmol) of triethyl orthoacetate and heated to 100 ° C. for 1 hour. It is then allowed to cool to room temperature, the reaction mixture is added with vigorous stirring with 50 ml of petroleum ether and the precipitate is filtered off with suction.
Yield: 3.05 g (77%); M.p .: = 132-134 ° C.

example 5 2- (4-chlorophenyl) -7-chloro-oxazolo [5,4-h] quinoline

A mixture consisting of 3.89 g (20 mmol) of 8-amino-3-chloro-7-hydroxy quinoline, 3.44 g (22 mmol) of 4-chlorobenzoic acid and 20 ml of polyphosphoric acid is heated to 120 ° C for 2 hours. It is allowed to cool to 90 ° C, added Carefully 100 g of ice and 500 ml of water. The suspension thus obtained is with concentrated sodium hydroxide solution to pH 12, which is precipitate filtered off, washed thoroughly with salt-free water and in vacuo at 60 ° C. dried. After recrystallization from ethyl acetate remain 3.2 g (51%); M.p. <250 ° C.

The rules given in the Synthesis Examples are suitable with appropriate modification of the starting compounds for recovery further compounds of the formula I. Examples of such compounds are listed in the following tables. They leave because of their nearness structural relationships to those mentioned in the synthesis examples Compounds expect a similar effect.  

Table 1

Table 2

The 3H-imidazo [4,5-h] (oxazolo [5,4-h]) quinolines I or the containing them herbicidal agents can, for example, in the form of directly sprayable Solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, Pastes, dusts, litter or granules by spraying, Nebulizing, dusting, scattering or pouring are applied. The Application forms depend on the intended use; they should be in in each case as possible the finest distribution of the invention Ensure active ingredients.

The compounds I are generally suitable for the preparation of direct sprayable solutions, emulsions, pastes or oil dispersions Mineral oil fractions of medium to high boiling point, such as kerosene or Diesel oil, coal tar oils and vegetable or animal oils Origin, aliphatic, cyclic and aromatic hydrocarbons, z. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, Cyclohexanone, chlorobenzene, isophorone or strongly polar solvents, such as N, N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone or water.

Aqueous application forms can be prepared from emulsion concentrations, dispersions, Pastes, wettable powders or water-dispersible granules Addition of water to be prepared. For the preparation of emulsions, pastes or oil dispersions may be the substrates as such or in an oil or Solvent dissolved by means of wetting, adhesive, dispersing or emulsifying be homogenized in water. It can also be more effective Substance, wetting, adhesion, dispersing or emulsifying agents and possibly Solvent or oil existing concentrates are produced, the Dilution with water are suitable.

As surface-active substances are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. As lignin, phenol, naphthalene and Dibutylnaphthalenesulfonic acid, as well as fatty acids, alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts sulfated hexa-, hepta- and octadecanols, as well as fatty alcohol Glycol ethers, condensation products of sulfonated naphthalene and its Derivatives with formaldehyde, condensation products of naphthalene or the Naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octyl phenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkyl phenol, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, Isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated Castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulphite liquors or methyl cellulose into consideration.  

Powders, litter and dusts can be mixed or mixed Milling the active substances with a solid carrier getting produced.

Granules, for. B. coated, impregnated and homogeneous granules be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths such as silica gel, silicic acid, pebbles gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, Dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, urea and vegetable products, such as cereal flour, Bark, wood and nutshell flour, cellulose powder or other solid Carriers.

The formulations contain between 0.1 and 95% by weight, preferably between 0.5 and 90 wt .-%, active ingredient.

Examples of formulations are:

• I. Mix 90 parts by weight of compound no. 82 with 10 parts by weight of N-methyl- α- pyrrolidone and obtain a solution which is suitable for use in the form of very small drops.
• II. 20 parts by weight of Compound No. 35 are in a mixture dissolved, consisting of 80 parts by weight of xylene, 10 parts by weight of Addition product of 8 to 10 moles of ethylene oxide to 1 mole of oil acid N-monoethanolamide, 5 parts by weight calcium salt of the Dode Cyclbenzenesulfonic acid and 5 parts by weight of the addition product Tes of 40 moles of ethylene oxide to 1 mole of castor oil. By Pour and finely distribute the solution in 100,000 weight water, an aqueous dispersion containing 0.02% by weight is obtained. of the active ingredient.
• III. 20 parts by weight of compound no. 36 are in a mixture dissolved, consisting of 40 parts by weight of cyclohexanone, 30 parts by weight Isobutanol, 20 parts by weight of the adduct of 7 moles Ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight of Addition product of 40 moles of ethylene oxide to 1 mole of castor oil consists. By pouring and finely distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion, containing 0.02% by weight of the active substance.  
• IV. 20 parts by weight of drug no. 49 are in a mixture dissolved, which consists of 25 parts by weight of cyclohexanone, 65 parts by weight a mineral oil fraction of boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and fine distribution The solution in 100 000 parts by weight gives you one aqueous dispersions containing 0.02 wt .-% of the active ingredient.
• V. 20 parts by weight of the active ingredient No. 35 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene- α- sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water to obtain a spray mixture containing 0.1 wt .-% of the active ingredient.
• VI. 3 parts by weight of drug no. 37 are 97 weight divided finely divided kaolin mixed. You get that way a dust containing 3% by weight of the active ingredient.
• VII. 30 parts by weight of Active Ingredient No. 58 are mixed from 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil, which is on the surface of this Silica gel was sprayed, intimately mixed. You get up this way, a treatment of the active substance with good adhesion ness.
• VIII. 20 parts by weight of Active Ingredient No. 52 are used at 2 weight share calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight Fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a Phenol-urea-formaldehyde condensate and 68 parts by weight a paraffinic mineral oil intimately mixed. You get one stable oily dispersion.

The application can take place preemergence or postemergence. If the active ingredients are less compatible for certain crops, so Application techniques may be used in which the herbicidal Means be sprayed using the sprayers so that the leaves of sensitive crops are not taken if possible while the active ingredients on the leaves underneath are growing more unwanted Plants or the uncovered ground surface arrive (post-directed, lay-by).  

The application rates of active ingredient are depending on the control target, year time, target plants and growth stages 0.001 to 4, preferably 0.01 to 2 kg / ha.

To broaden the spectrum of action and to achieve synergistic Effects can be the compounds I with numerous representatives of others mixed herbicidal or growth-regulating active ingredient groups and be deployed together. For example, come as a mixing partner Diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitro anilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines, Amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, Cyclohexane-1,3-dione derivatives, quinolinecarboxylic acid derivatives, phenoxy or Heteroaryloxy-phenoxypropionic acids and their salts, esters and amides and others into consideration.

In addition, it may be useful to use the compounds alone or in a Combination with other herbicides also with other plants mixed with protection agents, for example, with funds for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which be used to address nutritional and trace element deficiencies. It It is also possible to add non-phytotoxic oils and oil concentrates.

In view of the versatility of the application methods, the Compounds according to the invention or agents containing them in one large number of crops to eliminate unwanted plants be used. For example, the following cultures may be considered:

Botanical name German name Allium cepa onion Pineapple comosus pineapple Arachis hypogaea Peanut Asparagus officinalis asparagus Avena sativa oats Beta vulgaris spp. altissima sugar beet Beta vulgaris spp. rapa mangel Beta vulgaris spp. esculenta Red beet Brassica napus var. Napus rape Brassica napus var. Napobrassica Turnip Brassica napus var. Rapa White turnip Brassica rapa var. Silvestris beets Camellia sinensis Teestrauch Carthamus tinctorius Safflower - safflower Carya illinoinensis Pekanußbaum Citrus limon lemon Citrus maxima grapefruit Citrus reticulata tangerine Citrus sinensis Orange, orange Coffea arabica (Coffea canephora, Coffea liberica) coffee Cucumis melo melon Cucumis sativus cucumber Cynodon dactylon Bermuda grass Daucus carota carrot Elaeis guineensis oil palm Fragaria vesca strawberry Glycine max Soybean Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) cotton Helianthus annuus sunflower Helianthus tuberosus Jerusalem artichokes Hevea brasiliensis Para rubber tree Hordeum vulgare barley Humulus lupulus hop Ipomoea batatas sweet potatoes Juglans regia walnut tree Lactuca sativa lettuce Lens culinaris lens Linum usitatissimum flax Lycopersicon lycopersicum tomato Malus spp. Apple Manihot esculenta manioc Medicago sativa alfalfa Mentha piperita peppermint Musa spp. Fruit and flour banana Nicotiana tabacum (N. rustica) tobacco Olea europaea olive tree Oryza sativa rice Panicum miliaceum Rispenhirse Phaseolus lunatus butterbean Phaseolus mungo Erdbohne Phaseolus vulgaris bush beans Pennisetum glaucum Perl or cattail millet Petroselinum crispum spp. tuberosum root parsley Picea abies Rotfichte Abies alba white fir Pinus spp. pine Pisum sativum garden pea Prunus avium sweet cherry

Botanical name German name Prunus domestica plum Prunus dulcis almond Prunus persica peach Pyrus communis pear Ribes sylvestre Red currant Ribes uva-crispa gooseberry Ricinus communis castor-oil plant Saccharum officinarum sugarcane Secale cereal rye Sesamum indicum sesame Solanum tuberosum potato Sorghum bicolor (see vulgare) sorghum Sorghum dochna sweet sorghum Spinacia oleracea spinach Theobroma cacao cacao Trifolium pratense Red clover Triticum aestivum wheat Triticum durum durum wheat Vaccinium corymbosum Cultivated blueberry Vaccinium vitis-idaea Preißelbeere Vicia faba horse beans Vigna sinensis (V. unguiculata) cowpea Vitis vinifera grapevine Zea mays Corn

applications

The herbicidal action of 3H-imidazo [4,5-h] (oxazolo [5,4-h]) quinolines Formula I on the growth of the test plants is by the following Greenhouse experiments shown.

As culture vessels serve plastic flower pots with 300 cm³ content and loamy Sand with about 3.0% humus as substrate. The seeds of the test plants are Seeded separately by species.

For postemergence treatment, either sown directly or in selected or grown on the same vessels grown plants first dressed as seedlings separately and a few days before Transplanted treatment in the test vessels.  

Depending on the growth form, the test plants are at a stature height of 3 to 15 cm then with the suspended in water as a distribution agent or emulsified active ingredients that are sprayed through finely distributing nozzles are going to be treated. The application rate for the post-treatment is 1.0 kg of active ingredient / ha.

The test tubes are placed in the greenhouse, where for heat loving species warmer areas (20 to 35 ° C) and more temperate for those Climates 10 to 20 ° C are preferred. The trial period extends over 2 to 4 weeks. During this time, the plants are maintained and their response to each treatment is evaluated.

The rating is based on a scale from 0 to 100. 100 means no Rising of the plants or complete destruction of at least the above ground Parts and 0 no damage or normal growth.

The plants used in the greenhouse experiments are precipitated following types together:

Latin name German name Cassia tora - Ipomoea spp. Wind pomp species Lamium amplexicaule Stems surrounding deadnettle

At an application rate of 1.0 kg of active ingredient / ha can be in Nachauf Run procedure with the drug no. 35 broad-leaved undesirable Fight plants very well, with the active ingredient at the same time compatible is for the crop corn.

Claims (6)

1. 3H-imidazo [4,5-h] (oxazolo [5,4-h]) quinolines of the formula in the
R¹ is hydrogen, halogen, carboxyl or optionally C₁-C₆-alkoxy, C₁-C₄-alkylthio or halogen-substituted C₁-C₆-alkyl,
R² is hydrogen, C₁-C₆-alkyl, an optionally substituted by C₁-C₄-alkyl C₃-C₆-cycloalkyl, optionally substituted by nitro, amino, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄- Alkyl thio, C₁-C₄-haloalkyl, acylamino or acyloxy-substituted phenyl or naphthyl or an optionally substituted by nitro, C₁-C₄-alkyl or halogen-substituted 5- or 6-membered heterocyclic radical having one or two heteroatoms selected from the group oxygen, sulfur and nitrogen, and
X is oxygen or the radical -NR³-, wherein R³ is hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkylamino or optionally by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁- C₄-alkoxy substituted benzyl,
stand. 2. A process for the preparation of 3H-imidazo [4,5-h] quinolines of the formula I according to claim 1, characterized in that 7,8-diamino-quinolines of the formula in a conventional manner with carboxylic acids of the formula R²-COOH (III) or ortho esters of the formula R²C (OR⁴) ₃ (IV) in which R⁴ is C₁-C₄-alkyl, is reacted. 3. A process for the preparation of oxazolo [5,4-h] quinolines of the formula I according to claim 1, characterized in that 7-hydroxy-8-amino quinolines of the formula in a conventional manner with carboxylic acids of the formula R²-COOH (III) or ortho esters of the formula R²-C (OR⁴) ₃ (IV), in which R⁴ is C₁-C₄-alkyl, is reacted. 4. A herbicide containing a 3H-imidazo [4,5-h] (oxazolo [5,4-h]) quinoline Formula I according to claim 1. 5. Herbicide containing inert additives and a 3H-imidazo [4,5-h] (Oxazolo [5,4-h]) quinoline of the formula I according to claim 1. 6. A method for controlling undesired plant growth, characterized characterized in that the plants and / or their location with a herbicidally effective amount of a 3H-imidazo [4,5-h] (oxazolo [5,4-h]) Quinolines of the formula I according to claim 1 treated.