EP0934284A1 - Substituted 2-amino-4-alkylamino-1,3,5-triazines as herbicides - Google Patents

Substituted 2-amino-4-alkylamino-1,3,5-triazines as herbicides

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Publication number
EP0934284A1
EP0934284A1 EP97910378A EP97910378A EP0934284A1 EP 0934284 A1 EP0934284 A1 EP 0934284A1 EP 97910378 A EP97910378 A EP 97910378A EP 97910378 A EP97910378 A EP 97910378A EP 0934284 A1 EP0934284 A1 EP 0934284A1
Authority
EP
European Patent Office
Prior art keywords
ethyl
propylamino
phenyl
group
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97910378A
Other languages
German (de)
French (fr)
Inventor
Hans-Jochem Riebel
Stefan Lehr
Uwe Stelzer
Yukiyoshi Watanabe
Markus Dollinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0934284A1 publication Critical patent/EP0934284A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new substituted 2-amino-4-alkylamino-l, 3,5-triazines, processes and new intermediates for their preparation and their use as
  • R 1 represents in each case optionally substituted alkyl having 2 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,
  • R 2 represents hydrogen or alkyl having 1 to 4 carbon atoms
  • A represents oxygen or methylene
  • Ar stands for optionally substituted phenyl, naphthyl or heterocyclyl
  • Z represents hydrogen, halogen or optionally substituted in each case
  • R 1 , R 2 , A and Ar have the meaning given above,
  • R ' represents alkyl
  • R 1 , R 2 , A, Ar and Z have the meaning given above and X 1 represents halogen or alkoxy,
  • X 2 represents halogen or alkoxy
  • R 1 , R 2 , A and Ar have the meaning given above,
  • the new substituted 2-amino-4-alkylamino-l, 3,5-triazines of the general formula (I) are notable for strong and selective herbicidal activity.
  • the compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be present in various enantiomeric (R- and S-configured forms) or diastereomeric forms.
  • the invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these isomeric compounds.
  • hydrocarbon chains such as alkyl - in each case in connection with heteroatoms, such as in alkoxy or alkylthio - are in each case straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 2 represents hydrogen, methyl or ethyl
  • A represents oxygen or methylene
  • Ar stands for optionally substituted phenyl, naphthyl or heterocyclyl
  • the possible heterocyclyl groupings are preferably selected from the following group:
  • the invention relates in particular to compounds of the formula (I) in which
  • R 1 each represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy or ethoxy or each in each case optionally by cyano, fluorine, chlorine, Methyl or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
  • R 2 represents hydrogen or methyl
  • A represents oxygen or methylene
  • Ar stands for optionally substituted phenyl, naphthyl or heterocyclyl
  • the possible heterocyclyl groupings are preferably selected from the following group:
  • Furyl benzo lactidyl, dihydrobenzo colryl, tetrahydro colryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl
  • Hydrogen methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, chlorofluoromethyl, chlorobromomethyl, chlorodifluoromethyl, fluorodichloromethyl, bromodifluoromethyl, Trichloromethyl, 1-fluoro-ethyl, 2-fluoro-ethyl, 1-chloro-ethyl, 2-chloro-ethyl, 1-chloro-1-fluoro-ethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoro-propyl, 1-fluoro-1-methyl-ethyl, 2-fluoro-1-methyl-ethyl, 1-chloro-1-methyl-ethyl, 1-fluoro-1-methyl-propyl, 1-chloro- 1-ethyl-
  • 1-methoxycarbonyl-methyl 1 -acetyl-1-ethoxycarbonyl-methyl, methoxymethyl, 1, 1-dimethoxy-methyl, 1-methoxyethyl, 2-methoxy-ethyl, 1,1-dimethoxy-ethyl, ethoxy-methyl, 1 - Ethoxyethyl, 2-ethoxy-ethyl, 2-methoxy-1-methyl-ethyl, 2-methoxy-l-ethyl-ethyl, 2-ethoxy-1-methyl-ethyl, 2-ethoxy-l-ethyl-ethyl, methylthiomethyl, Ethylthiomethyl, 1-methylthio-ethyl, 2-methylthioethyl, 1-ethylthio-ethyl, 2-ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, e
  • Group 25 has, for example, the meanings given above in Group 1.
  • Group 25 has, for example, the meanings given above in Group 1.
  • Group 40 has, for example, the meanings given above in Group 1.
  • Group 70 has, for example, the meanings given above in Group 1.
  • Group 74 has, for example, the meanings given above in Group 1.
  • Group 82 has, for example, the meanings given above in Group 1.
  • Formula (II) provides a general definition of the substituted biguanides to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I).
  • R 1 , R 2 , A and Ar have preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 , R 2 , A and Ar.
  • the following may be mentioned as examples of the substituted biguanides of the formula (II):
  • Suitable acid adducts of compounds of the formula (II) are their addition products with protonic acids, such as e.g. with hydrogen chloride (hydrogen chloride), hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • protonic acids such as e.g. with hydrogen chloride (hydrogen chloride), hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • R 1 , R 2 , A and Ar have the meaning given above,
  • reaction auxiliary e.g. Hydrogen chloride
  • diluent e.g. n-decane or
  • 1,2-dichlorobenzene at temperatures between 100 ° C and 200 ° C (see. EP 492615, manufacturing examples).
  • substituted alkylamino compounds of the general formula (VI) required for this as products are known and / or can be prepared by processes known per se (cf. J. Med. Chem. 10 (1967); 717-724; J. Am. Chem. Soc. 97 (1975), 6900-6901; Tetrahedron Lett. 35 (1994), 3745-3746; DE 3222152; DE 3221540; EP 355351; EP 601486; production examples).
  • Formula (I) further alkoxycarbonyl compounds to be used as starting materials are generally defined by the formula (III).
  • Z preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Z;
  • R ' is preferably
  • the starting materials of the formula (III) are known synthetic chemicals.
  • the substituted triazines to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I) are characterized by
  • R 1 , R 2 , A, Ar and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for R 1 , R 2 , A, Ar and Z specified were;
  • X 1 preferably represents fluorine, chlorine, bromine, methoxy or ethoxy, in particular chlorine or methoxy.
  • X 1 and Z have the meaning given above and X 3 represents halogen
  • R 1 , R 2 , A and Ar have the meaning given above,
  • an acid acceptor e.g. Ethyldiisopropylamine
  • a diluent e.g. Tetrahydrofuran or dioxane
  • Formula (V) generally defined.
  • Z preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Z;
  • X 2 preferably represents fluorine, chlorine, bromine, methoxy or ethoxy, in particular chlorine or methoxy.
  • the starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf. WO 95/11237).
  • Formula (VI) provides a general definition of the substituted alkylamines to be used further as starting materials in process (c) according to the invention.
  • R 1 , R 2 , A and Ar preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 , R 2 , A and Ar were given.
  • the starting materials of the general formula (VI) are known and / or can be prepared by processes known per se (cf. DE 3426919; DE 4000610; DE 4332738, EP 320898; EP 443606; Tetrahedron: Asymmetry 5 (1994), 817-820 ;
  • Suitable reaction auxiliaries for processes (a), (b) and (c) are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium - or
  • Calcium amide sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino
  • Inert organic solvents are particularly suitable as diluents for carrying out processes (a), (b) and (c) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform,
  • Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as methyl isopropyl ketone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol
  • reaction temperatures can be varied within a substantial range when carrying out processes (a), (b) and (c). In general, temperatures between 0 ° C and 300 ° C, preferably between 10 ° C and 250 ° C.
  • the processes (a), (b) and (c) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally agitated several hours at the required temperature. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Pisum Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances .
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as
  • Chlorobenzenes chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable Oils
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural
  • Rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example acetochlor,
  • Simazine Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben, Trallonium, Sulfuron, Trihydro -methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • the preparation and use of the active compounds according to the invention can be seen from the examples below.
  • the reaction can also be carried out at the same temperature without a solvent - i.e. in the melt - be carried out.
  • Example (II-1) Analogously to Example (II-1), it is also possible, for example, to prepare the compounds of the formula (II) listed in Table 2 below or their hydrochlorides.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Cultivated plants e.g. Corn, wheat and cotton, strong activity against weeds (see Table A).
  • WiikstoiV according to effort- maize tree- alope- digi- abu- galium matriManufacturing sample no. amount (g ai / ha) wool curus taria tilon caria
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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

Abstract

The invention relates to novel substituted 2-amino-4-alkylamino-1,3,5-triazines of formula (I), in which R1 stands for respectively optionally substituted alkyl with 2 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms, R2 stands for hydrogen or alkyl with 1 to 4 carbon atoms, A for oxygen or methylene, Ar for respectively optionally substituted phenyl, naphthyl or heterocycyl, and Z for hydrogen, for halogen or for respectively optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl or alkinyl, methods and new intermediate products for their production and their use as herbicides.

Description

SUBSTITUIERTE 2-AMINO-4-ALKYLAMINO-l ,3,5-TRIAZINE ALS HERBIZIDESUBSTITUTED 2-AMINO-4-ALKYLAMINO-l, 3,5-TRIAZINE AS HERBICIDES
Die Erfindung betrifft neue substituierte 2-Amino-4-alkylamino-l,3,5-triazine, Ver- fahren und neue Zwischenprodukte zu ihrer Herstellung sowie ihre Verwendung alsThe invention relates to new substituted 2-amino-4-alkylamino-l, 3,5-triazines, processes and new intermediates for their preparation and their use as
Herbizide.Herbicides.
Eine Reihe von substituierten 2,4-Diamino-triazinen ist bereits aus der (Patente- Literatur bekannt (vgl. US 3816419, US 3932167, EP 191496, EP 273328, EP 411153 / WO 90/09378, WO 97/00254, WO 97/08156). Diese Verbindungen haben jedoch bisher keine besondere Bedeutung erlangt.A number of substituted 2,4-diamino-triazines are already known from the (patent literature (cf. US 3816419, US 3932167, EP 191496, EP 273328, EP 411153 / WO 90/09378, WO 97/00254, WO 97 / 08156) However, these connections have so far not attained any special significance.
Es wurden nun die neuen substituierten 2-Amino-4-alkylamino-l,3,5-triazine der allgemeinen Formel (I) gefunden,The new substituted 2-amino-4-alkylamino-1,3,5-triazines of the general formula (I) have now been found
in welcherin which
R1 für jeweils gegebenenfalls substituiertes Alkyl mit 2 bis 6 Kohlenstoffatomen oder Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht,R 1 represents in each case optionally substituted alkyl having 2 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,
R2 für Wasserstoff oder für Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R 2 represents hydrogen or alkyl having 1 to 4 carbon atoms,
A für Sauerstoff oder Methylen steht,A represents oxygen or methylene,
Ar für jeweils gegebenenfalls substituiertes Phenyl, Naphthyl oder Heterocyclyl steht, undAr stands for optionally substituted phenyl, naphthyl or heterocyclyl, and
Z für Wasserstoff, für Halogen oder für jeweils gegebenenfalls substituiertesZ represents hydrogen, halogen or optionally substituted in each case
Alkyl, Alkoxy, Alkylcarbonyl, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkenyl oder Alkinyl steht. Man erhält die neuen substituierten 2-Amino-4-alkylamino-l,3,5-triazine der allgemeinen Formel (I), wenn manAlkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl or alkynyl. The new substituted 2-amino-4-alkylamino-l, 3,5-triazines of the general formula (I) are obtained if
(a) substituierte Biguanide der allgemeinen Formel (II)(a) substituted biguanides of the general formula (II)
(ll)(ll)
in welcherin which
R1, R2, A und Ar die oben angegebene Bedeutung haben,R 1 , R 2 , A and Ar have the meaning given above,
- und/oder Säureaddukte von Verbindungen der allgemeinen Formel (II) -and / or acid adducts of compounds of the general formula (II)
mit Alkoxycarbonylverbindungen der allgemeinen Formel (III)with alkoxycarbonyl compounds of the general formula (III)
Z-CO-OR' (III)Z-CO-OR '(III)
in welcherin which
Z die oben angegebene Bedeutung hat undZ has the meaning given above and
R' für Alkyl steht,R 'represents alkyl,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
oder wenn manor if you
(b) substituierte Triazine der allgemeinen Formel (IV)(b) substituted triazines of the general formula (IV)
in welcherin which
R1, R2, A, Ar und Z die oben angegebene Bedeutung haben und X1 für Halogen oder Alkoxy steht,R 1 , R 2 , A, Ar and Z have the meaning given above and X 1 represents halogen or alkoxy,
mit Ammoniak gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,with ammonia, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
oder wenn manor if you
(c) substituierte Triazine der allgemeinen Formel (V)(c) substituted triazines of the general formula (V)
in welcherin which
Z die oben angegebene Bedeutung hat undZ has the meaning given above and
X2 für Halogen oder Alkoxy steht,X 2 represents halogen or alkoxy,
mit substituierten Alkylaminen der allgemeinen Formel (VI)with substituted alkylamines of the general formula (VI)
in welcherin which
R1, R2, A und Ar die oben angegebene Bedeutung haben,R 1 , R 2 , A and Ar have the meaning given above,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegen- wart eines Verdünnungsmittels umsetzt,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
und gegebenenfalls an den gemäß den unter (a), (b) oder (c) beschriebenen Verfahren erhaltenen Verbindungen der allgemeinen Formel (I) im Rahmen der obigen Sub- stituentendefinition weitere Umwandlungen nach üblichen Methoden durchführt.and, if appropriate, on the compounds of the general formula (I) obtained according to the processes described under (a), (b) or (c), as part of the above definition of substituents, carries out further conversions by customary methods.
Die neuen substituierten 2-Amino-4-alkylamino-l,3,5-triazine der allgemeinen Formel (I) zeichnen sich durch starke und selektive herbizide Wirksamkeit aus. Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) enthalten mindestens ein asymmetrisch substituiertes Kohlenstoffatom und können deshalb in verschiedenen enantiomeren (R- und S- konfigurierten Formen) bzw. diastereomeren Formen vorliegen. Die Erfindung betrifft sowohl die verschiedenen möglichen einzelnen enantiomeren bzw. stereoisomeren Formen der Verbindungen der allgemeinen Formel (I) wie auch die Gemische dieser isomeren Verbindungen.The new substituted 2-amino-4-alkylamino-l, 3,5-triazines of the general formula (I) are notable for strong and selective herbicidal activity. The compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be present in various enantiomeric (R- and S-configured forms) or diastereomeric forms. The invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these isomeric compounds.
In den Definitionen sind die Kohlenwasserstoffketten, wie Alkyl - auch in Verbindung mit Heteroatomen, wie in Alkoxy oder Alkylthio -jeweils geradkettig oder verzweigt.In the definitions, the hydrocarbon chains, such as alkyl - in each case in connection with heteroatoms, such as in alkoxy or alkylthio - are in each case straight-chain or branched.
Halogen steht im allgemeinen für Fluor, Chlor, Brom oder Iod, vorzugsweise für Fluor, Chlor oder Brom, insbesondere für Fluor oder Chlor.Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Gegenstand der Erfindung sind vorzugsweise Verbindungen der Formel (I), in welcherThe invention preferably relates to compounds of the formula (I) in which
R1 für gegebenenfalls durch Hydroxy, Cyano, Halogen oder C1 -C4- Alkoxy substituiertes Alkyl mit 2 bis 4 Kohlenstoffatomen oder für gegebenenfalls durch Cyano, Halogen oder Cι -C4-Alkyl substituiertes Cycloalkyl mit 3 bis 6R 1 for alkyl with 2 to 4 carbon atoms optionally substituted by hydroxy, cyano, halogen or C1 -C4 alkoxy or for cycloalkyl with 3 to 6 optionally substituted by cyano, halogen or C1 -C4 alkyl
KohlenstofFatomen steht,Carbon atoms stands,
R2 für Wasserstoff, Methyl oder Ethyl steht,R 2 represents hydrogen, methyl or ethyl,
A für Sauerstoff oder Methylen steht,A represents oxygen or methylene,
Ar für jeweils gegebenenfalls substituiertes Phenyl, Naphthyl oder Heterocyclyl steht,Ar stands for optionally substituted phenyl, naphthyl or heterocyclyl,
wobei die möglichen Heterocyclylgruppierungen vorzugsweise aus der folgenden Gruppe ausgewählt sind:the possible heterocyclyl groupings are preferably selected from the following group:
Furyl, Benzofuryl, Dihydrobenzofuryl, Tetrahydrofüryl, Thienyl, Benzothienyl, Thiazolyl, Benzthiazolyl, Oxazolyl, Benzoxazolyl, Thiadiazolyl, Oxadiazolyl, PyrazolyL Pyrrolyl, Chinolinyl, Isochinolinyl, Pyridinyl und Pyrimidinyl,Furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofüryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyL pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl,
und wobei die möglichen Substituenten jeweils vorzugsweise aus folgender Gruppe ausgewählt sind:and the possible substituents are each preferably selected from the following group:
Hydroxy, Cyano, Nitro, Halogen, jeweils gegebenenfalls durch Hydroxy, Cyano oder Halogen substituiertes Alkyl oder Alkoxy mit jeweils 1 bis 6 Kohlenstoffatomen, jeweils gegebenenfalls durch Halogen substituiertes Alkylcarbonyl, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro, Halogen, C1-C4- Alkyl, Cι-C4-Halogenalkyl, C 1 -C4- Alkoxy oder C \ -C4-Halogenalkoxy substiuiertes Phenyl oder Phenoxy, sowie jeweils gegebenenfalls durch Halogen substituiertes Methylendioxy oder Ethylendioxy,Hydroxy, cyano, nitro, halogen, each optionally substituted by hydroxy, cyano or halogen-substituted alkyl or alkoxy, each with 1 to 6 Carbon atoms, each optionally substituted by halogen, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, each optionally by hydroxy, cyano, nitro, halogen, C1-C4-alkyl, C 1 -C 4 -haloalkyl, C. 1 -C4-alkoxy or C \ -C4-haloalkoxy-substituted phenyl or phenoxy, and in each case optionally substituted by halogen-substituted methylenedioxy or ethylenedioxy,
undand
Z für Wasserstoff, für Halogen, für jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro, Halogen, C \ -C4 -Alkoxy, Cι-C4-Alkyl-carbonyl, C1-C4-Z for hydrogen, for halogen, for each optionally by hydroxyl, cyano, nitro, halogen, C 4 -C 4 alkoxy, C 1 -C 4 alkyl carbonyl, C 1 -C 4
Alkoxy-carbonyl, Cι-C4-Alkylthio, C1-C4- Alkylsulfinyl oder Cj ^-Alkylsulfonyl substituiertes Alkyl, Alkoxy, Alkylcarbonyl, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Halogen sub- stituiertes Alkenyl oder Alkinyl mit jeweils 2 bis 6 Kohlenstoffatomen steht.Alkoxy-carbonyl, -C-C4-alkylthio, C1-C4-alkylsulfinyl or C j ^ -alkylsulfonyl substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, or for each optionally by Halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms.
Aus den vorausgehend als bevorzugt („vorzugsweise") definierten Verbindungen der Formel (I) seien folgende Gruppen besonders herausgehoben:From the compounds of the formula (I) defined above as preferred (“preferably”), the following groups should be particularly emphasized:
(A) die Verbindungen der Formel (I), in welcher A, R1, R2 und Z die vorausgehend angegebene Bedeutung haben und Ar für jeweils gegebenenfalls substituiertes Phenyl oder Naphthyl steht, wobei die möglichen Substituenten die vorausgehend angegebene Bedeutung haben;(A) the compounds of the formula (I) in which A, R 1 , R 2 and Z have the meaning indicated above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents having the meaning indicated above;
(B) die Verbindungen der Formel (I), in welcher A, R1, R2 und Z die vorausgehend angegebene Bedeutung haben und Ar für gegebenenfalls substituiertes Heterocyclyl steht, wobei die möglichen Heterocyclylgruppierungen und die möglichen Sub- stituenten die vorausgehend angegebene Bedeutung haben.(B) the compounds of the formula (I) in which A, R 1 , R 2 and Z have the meaning indicated above and Ar represents optionally substituted heterocyclyl, the possible heterocyclyl groups and the possible substituents having the meaning indicated above .
Die Erfindung betrifft insbesondere Verbindungen der Formel (I), in welcherThe invention relates in particular to compounds of the formula (I) in which
R1 für jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl sub- stituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht,R 1 each represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy or ethoxy or each in each case optionally by cyano, fluorine, chlorine, Methyl or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R2 für Wasserstoff oder Methyl steht, A für Sauerstoff oder Methylen steht,R 2 represents hydrogen or methyl, A represents oxygen or methylene,
Ar für jeweils gegebenenfalls substituiertes Phenyl, Naphthyl oder Heterocyclyl steht,Ar stands for optionally substituted phenyl, naphthyl or heterocyclyl,
wobei die möglichen Heterocyclylgruppierungen vorzugsweise aus der folgenden Gruppe ausgewählt sind:the possible heterocyclyl groupings are preferably selected from the following group:
Furyl, Benzofüryl, Dihydrobenzofüryl, Tetrahydrofüryl, Thienyl, Benzothienyl, Thiazolyl, Benzthiazolyl, Oxazolyl, Benzoxazolyl, Thiadiazolyl, Oxadiazolyl, Pyrazolyl, Pyrrolyl, Chinolinyl, Isochinolinyl, Pyridinyl und Pyrimidinyl,Furyl, benzofüryl, dihydrobenzofüryl, tetrahydrofüryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl
und wobei die möglichen Substituenten jeweils vorzugsweise aus folgender Gruppe ausgewählt sind:and the possible substituents are each preferably selected from the following group:
Hydroxy, Cyano, Nitro, Fluor, Chlor, Brom, jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor oder Chlor substituiertes Methyl, Ethyl, n- oder i- Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methyl- sulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy,Hydroxy, cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by hydroxy, cyano, fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy , n- or i-propoxy, n-, i-, s- or t-butoxy, each optionally substituted by fluorine or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, each optionally by hydroxyl, cyano, nitro, fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
Difluormethoxy oder Trifluormethoxy substituiertes Phenyl oder Phenoxy, sowie jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Methylen- dioxy oder Ethylendioxy,Difluoromethoxy or trifluoromethoxy substituted phenyl or phenoxy, and in each case optionally methylene dioxy or ethylenedioxy substituted by fluorine or chlorine,
undand
Z für Wasserstoff, Fluor, Chlor, Brom, für jeweils gegebenenfalls durchZ for hydrogen, fluorine, chlorine, bromine, each for where appropriate
Hydroxy, Cyano, Nitro, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methyl- sulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy,Hydroxy, cyano, nitro, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl , n- or i-Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, oder für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes Ethenyl, Propenyl, Butenyl, Ethinyl, Propinyl oder Butinyl steht.Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or represents in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl.
Aus den vorausgehend als insbesondere bevorzugt definierten Verbindungen der Formel (I) seien folgende Gruppen besonders herausgehoben:From the compounds of formula (I) defined above as particularly preferred, the following groups should be particularly emphasized:
(AA) die Verbindungen der Formel (I), in welcher A, R1, R2 und Z die vorausgehend angegebene Bedeutung haben und Ar für jeweils gegebenenfalls substituiertes Phenyl oder Naphthyl steht, wobei die möglichen Substituenten die vorausgehend angegebene Bedeutung haben, mit der Maßgabe, daß die Substituenten des Kohlenstoffatoms, an das R1 gebunden ist, in R-Konfiguration angeordnet sind;(AA) the compounds of the formula (I) in which A, R 1 , R 2 and Z have the meaning indicated above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents having the meaning indicated above, with the Provided that the substituents of the carbon atom to which R 1 is attached are arranged in the R configuration;
(BB) die Verbindungen der Formel (I), in welcher A, R1, R2 und Z die vorausgehend angegebene Bedeutung haben und Ar für jeweils gegebenenfalls substituiertes Phenyl oder Naphthyl steht, wobei die möglichen Substituenten die vorausgehend angegebene Bedeutung haben, mit der Maßgabe, daß die Substituenten des Kohlenstoffatoms, an das R1 gebunden ist, in S-Konfiguration angeordnet sind;(BB) the compounds of the formula (I) in which A, R 1 , R 2 and Z have the meaning indicated above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents having the meaning indicated above, with the Provided that the substituents of the carbon atom to which R 1 is attached are arranged in the S configuration;
(CC) die Verbindungen der Formel (I), in welcher A, R1, R2 und Z die vorausgehend angegebene Bedeutung haben und Ar für jeweils gegebenenfalls substituiertes Furyl, Thienyl, Pyridinyl oder Pyrimidinyl steht, wobei die möglichen Substituenten die vorausgehend angegebene Bedeutung haben, mit der Maßgabe, daß diese Verbindungen als racemische Gemische vorliegen;(CC) the compounds of the formula (I) in which A, R 1 , R 2 and Z have the meaning given above and Ar represents in each case optionally substituted furyl, thienyl, pyridinyl or pyrimidinyl, the possible substituents having the meaning indicated above with the proviso that these compounds are present as racemic mixtures;
(DD) die Verbindungen der Formel (I), in welcher A, R1, R2 und Z die vorausgehend angegebene Bedeutung haben und Ar für jeweils gegebenenfalls substituiertes Furyl, Thienyl, Pyridinyl oder Pyrimidinyl steht, wobei die möglichen Substituenten die vorausgehend angegebene Bedeutung haben, mit der Maßgabe, daß die Substituenten des Kohlenstoffatoms, an das R1 gebunden ist, in R-Konfiguration angeordnet sind;(DD) the compounds of the formula (I) in which A, R 1 , R 2 and Z have the meaning indicated above and Ar represents in each case optionally substituted furyl, thienyl, pyridinyl or pyrimidinyl, the possible substituents having the meaning indicated above have the proviso that the substituents of the carbon atom to which R 1 is attached are arranged in the R configuration;
(EE) die Verbindungen der Formel (I), in welcher A, R1, R2 und Z die vorausgehend angegebene Bedeutung haben und Ar für jeweils gegebenenfalls substituiertes Furyl, Thienyl, Pyridinyl oder Pyrimidinyl steht, wobei die möglichen Substituenten die vorausgehend angegebene Bedeutung haben, mit der Maßgabe, daß die Substituenten des Kohlenstoffatoms, an das R1 gebunden ist, in S -Konfiguration angeordnet sind.(EE) the compounds of the formula (I) in which A, R 1 , R 2 and Z have the meaning indicated above and Ar represents in each case optionally substituted furyl, thienyl, pyridinyl or pyrimidinyl, the possible substituents having the meaning indicated above with the proviso that the substituents of the carbon atom to which R 1 is attached are arranged in the S configuration.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden.The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. This Residual definitions can be combined with one another, that is, also between the specified preferred ranges.
Beispiele für die erfindungsgemäßen Verbindungen der Formel (I) sind in den nachstehenden Gruppen aufgeführt. Die allgemeinen Formeln stehen hierbei jeweils für die R-Enantiomeren, die S-Enantiomeren und die Racemate.Examples of the compounds of formula (I) according to the invention are listed in the groups below. The general formulas stand for the R-enantiomers, the S-enantiomers and the racemates.
Gruppe 1Group 1
Z hat hierbei beispielhaft die nachfolgend angegebenen Bedeutungen:Z has, for example, the meanings given below:
Wasserstoff, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Fluormethyl, Di- fluormethyl, Trifluormethyl, Chlormethyl, Dichlormethyl, Chlorfluormethyl, Chlor- brommethyl, Chlordifluormethyl, Fluordichlormethyl, Bromdifluormethyl, Trichlor- methyl, 1-Fluor-ethyl, 2-Fluor-ethyl, 1-Chlor-ethyl, 2-Chlor-ethyl, 1 -Chlor- 1-fluor- ethyl, 1-Fluor-propyl, 2-Fluor-propyl, 3-Fluor-propyl, 1 -Fluor- 1-methyl-ethyl, 2- Fluor- 1-methyl-ethyl, 1 -Chlor- 1-methyl-ethyl, 1 -Fluor- 1-methyl-propyl, 1 -Chlor- 1- ethyl-propyl, 1 -Fluor- 1 -ethyl-propyl, 1 -Chlor- 1 -ethyl-propyl, l-Fluor-2-methyl- propyl, 1 -Chlor-2-methyl-propyl, 1-Chlor-propyl, 2-Chlor-propyl, 3-Chlor-propyl, 1- Chlor- 1-methyl-ethyl, 2-Chlor- 1-methyl-ethyl, 1,1-Difluor-ethyl, 1,2-Difluor-ethyl, 1, 1-Dichlor-ethyl, 2,2,2-Trifluor-ethyl, 1,2,2,2-Tetrafluor-ethyl, Perfluorethyl, 1,1- Difluor-propyl, 1, 1-Dichlor-propyl, Perfluorpropyl, 1-Fluor-butyl, 1-Chlor-butyl, Per- fluorpentyl, Perfluorhexyl, 1-Hydroxy-ethyl, Acetyl, 1,1-Bis-acetyl-methyl, 1-Acetyl-Hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, chlorofluoromethyl, chlorobromomethyl, chlorodifluoromethyl, fluorodichloromethyl, bromodifluoromethyl, Trichloromethyl, 1-fluoro-ethyl, 2-fluoro-ethyl, 1-chloro-ethyl, 2-chloro-ethyl, 1-chloro-1-fluoro-ethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoro-propyl, 1-fluoro-1-methyl-ethyl, 2-fluoro-1-methyl-ethyl, 1-chloro-1-methyl-ethyl, 1-fluoro-1-methyl-propyl, 1-chloro- 1-ethyl-propyl, 1-fluor-1-ethyl-propyl, 1-chloro-1-ethyl-propyl, l-fluoro-2-methyl-propyl, 1-chloro-2-methyl-propyl, 1-chloro propyl, 2-chloropropyl, 3-chloropropyl, 1-chloro-1-methyl-ethyl, 2-chloro-1-methyl-ethyl, 1,1-difluoro-ethyl, 1,2-difluoro-ethyl, 1, 1-dichloro-ethyl, 2,2,2-trifluoro-ethyl, 1,2,2,2-tetrafluoro-ethyl, perfluoroethyl, 1,1-difluoropropyl, 1, 1-dichloropropyl, perfluoropropyl, 1-fluorobutyl, 1-chlorobutyl, perfluoropentyl, perfluorohexyl, 1-hydroxyethyl, acetyl, 1.1 -Bis-acetyl-methyl, 1-acetyl-
1-methoxycarbonyl-methyl, 1 -Acetyl- 1-ethoxycarbonyl-methyl, Methoxymethyl, 1, 1- Dimethoxy-methyl, 1-Methoxyethyl, 2-Methoxy-ethyl, 1,1-Dimethoxy-ethyl, Ethoxy- methyl, 1 -Ethoxyethyl, 2-Ethoxy-ethyl, 2-Methoxy- 1-methyl-ethyl, 2-Methoxy-l- ethyl-ethyl, 2-Ethoxy- 1-methyl-ethyl, 2-Ethoxy-l-ethyl-ethyl, Methylthiomethyl, Ethylthiomethyl, 1-Methylthio-ethyl, 2-Methylthioethyl, 1-Ethylthio-ethyl, 2-Ethyl- thioethyl, Methylsulfinylmethyl, Ethylsulfinylmethyl, Methylsulfonylmethyl, Ethyl- sulfonylmethyl, Methoxy, Ethoxy, n- oder i- Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Fluor- methoxy, Difluormethoxy, Trifluormethoxy, Fluorethoxy, Difluorethoxy, Trifluor- ethoxy, Difluormethylthio, Trifluormethylthio, Vinyl, 1 -Chlor- vinyl, 2-Chlor- vinyl, 1- Fluor- vinyl, 2-Fluor- vinyl, 1 -Brom- vinyl, 2 -Brom- vinyl, 1,2-Dichlor- vinyl, 1,2- Dibrom-vinyl, 1,2-Difluor- vinyl, 2,2-Dichlor-vinyl, 2,2-Difluor-vinyl, 2,2-Dibrom- vinyl, l-Chlor-2-fluor- vinyl, 2-Brom-2-chlor- vinyl, Trichlorvinyl, Allyl, 2-Chlor-allyl, 3-Chlor-allyl, 3,3-Dichlor-allyl, 1-Propenyl, Isopropenyl, l-Chlor-2-propenyl, 1- Fluor-2-propenyl, l-Brom-2-propenyl, 1,2-Dichlor-l -propenyl, 1,2-Dibrom-l- propenyl, 1 ,2-Difluor- 1 -propenyl, 1 , 1 -Dichlor-2-propenyl, 1 , 1 -Dibrom-2-propenyl, l,l-Difluor-2-propenyl, 1, 1,3,3, 3-Pentafluor-2-propenyl, 2-Buten-l-yl, 2-Buten-2-yl, 3-Chlor-2-butenyl, 3-Brom-2-butenyl, 3,3,3-Trifluor-2-butenyl, Ethinyl, 2-Chlor- ethinyl, 2-Brom-ethinyl, 1-Propinyl, 2-Propinyl, 3,3,3-Trifluor-l-propinyl.1-methoxycarbonyl-methyl, 1 -acetyl-1-ethoxycarbonyl-methyl, methoxymethyl, 1, 1-dimethoxy-methyl, 1-methoxyethyl, 2-methoxy-ethyl, 1,1-dimethoxy-ethyl, ethoxy-methyl, 1 - Ethoxyethyl, 2-ethoxy-ethyl, 2-methoxy-1-methyl-ethyl, 2-methoxy-l-ethyl-ethyl, 2-ethoxy-1-methyl-ethyl, 2-ethoxy-l-ethyl-ethyl, methylthiomethyl, Ethylthiomethyl, 1-methylthio-ethyl, 2-methylthioethyl, 1-ethylthio-ethyl, 2-ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoro ethoxy, difluoromethylthio, trifluoromethylthio, vinyl, 1-chloro-vinyl, 2-chloro-vinyl, 1-fluoro-vinyl, 2-fluoro-vinyl, 1-bromo-vinyl, 2-bromo-vinyl, 1,2-dichloro vinyl, 1,2-dibromo-vinyl, 1,2-difluoro-vinyl, 2,2-dichloro-vinyl, 2,2-difluoro-vinyl, 2,2-dibromo-vinyl, l-chloro-2-fluoro- vinyl, 2-bromo-2-chloro-vinyl, trichlorovinyl, allyl, 2-chloro-allyl, 3-chloro-allyl, 3,3-dichloro-allyl, 1-propenyl, isopropenyl, 1-chloro-2-propenyl, 1- fluoro-2-propenyl, l-bromo-2-propenyl, 1,2-dichloro-l-propenyl, 1,2-dibromo-l-propenyl, 1, 2-difluoro-1-propenyl, 1, 1 - Dichloro-2-propenyl, 1, 1-dibromo-2-propenyl, l, l-difluoro-2-propenyl, 1, 1,3,3, 3-pentafluoro-2-propenyl, 2-buten-l-yl, 2-buten-2-yl, 3-chloro-2-butenyl, 3-bromo-2-butenyl, 3,3,3-trifluoro-2-butenyl, ethynyl, 2-chloroethynyl, 2-bromoethynyl, 1-propynyl, 2-propynyl, 3,3,3-trifluoro-l-propynyl.
Gruppe 2Group 2
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 3Group 3
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 4Group 4
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 5Z has, for example, the meanings given above in Group 1. Group 5
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 6Group 6
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 7Group 7
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 8Group 8
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 9Z has, for example, the meanings given above in Group 1. Group 9
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 10Group 10
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 1 1Group 1 1
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 12Group 12
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 13Z has, for example, the meanings given above in Group 1. Group 13
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 14Group 14
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 15Group 15
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 16Group 16
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 17Z has, for example, the meanings given above in Group 1. Group 17
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 18Group 18
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 19Group 19
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 20Group 20
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 21Z has, for example, the meanings given above in Group 1. Group 21
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 22Group 22
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 23Group 23
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 24Group 24
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 25Z has, for example, the meanings given above in Group 1. Group 25
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 26Group 26
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 27Group 27
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 28Group 28
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 29Z has, for example, the meanings given above in Group 1. Group 29
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 30Group 30
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 31Group 31
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 32Group 32
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 33Z has, for example, the meanings given above in Group 1. Group 33
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 34Group 34
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 35Group 35
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 36Group 36
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 37Group 37
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 38Group 38
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 39Group 39
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 40Z has, for example, the meanings given above in Group 1. Group 40
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 41Group 41
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 42Group 42
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 43Group 43
(1-43)(1-43)
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 44Group 44
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 45Group 45
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 46Group 46
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 47Group 47
(1-47)(1-47)
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 48Group 48
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 49Group 49
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 50Group 50
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 51Z has, for example, the meanings given above in Group 1. Group 51
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 52Group 52
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 53Group 53
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 54Group 54
(1-54)(1-54)
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 55Group 55
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 56Group 56
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 57Group 57
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 58Z has, for example, the meanings given above in Group 1. Group 58
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 59Group 59
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 60Group 60
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 61Group 61
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 62Z has, for example, the meanings given above in Group 1. Group 62
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 63Group 63
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 64Group 64
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 65Group 65
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 66Z has, for example, the meanings given above in Group 1. Group 66
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 67Group 67
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 68Group 68
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 69Group 69
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 70Z has, for example, the meanings given above in Group 1. Group 70
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 71Group 71
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 72Group 72
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 73Group 73
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 74Z has, for example, the meanings given above in Group 1. Group 74
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 75Group 75
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 76Group 76
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 77Group 77
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 78Z has, for example, the meanings given above in Group 1. Group 78
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 79Group 79
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 80Group 80
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 81Group 81
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Gruppe 82Z has, for example, the meanings given above in Group 1. Group 82
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 83Group 83
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 84Group 84
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 85Group 85
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 86Group 86
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 87Group 87
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 88Group 88
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 89Group 89
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 90Group 90
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 91Group 91
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 92Group 92
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 93Group 93
(1-93)(1-93)
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 94Group 94
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 95Group 95
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 96Group 96
NH,NH,
N X NN X N
(1-96)(1-96)
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen.Z has, for example, the meanings given above in Group 1.
Gruppe 97Group 97
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Gruppe 98Group 98
Z hat hierbei beispielhaft die oben in Gruppe 1 angegebenen Bedeutungen. Z has, for example, the meanings given above in Group 1.
Verwendet man beispielsweise l-(l-Ethyl-3-phenyl-propyl)-biguanid und Trifluor- essigsäuremethylester als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (a) durch das folgende Formelschema skizziert werden:If, for example, 1- (1-ethyl-3-phenyl-propyl) -biguanide and methyl trifluoroacetate are used as starting materials, the course of the reaction in process (a) according to the invention can be outlined using the following formula:
Verwendet man beispielsweise 2-Chlor-4-(l-ethyl-3-phenyl-propylamino)-6-triftuor- methyl-l,3,5-triazin und Ammoniak als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (b) durch das folgende Formelschema skizziert werden:If, for example, 2-chloro-4- (l-ethyl-3-phenyl-propylamino) -6-trifluoromethyl-l, 3,5-triazine and ammonia are used as starting materials, the course of the reaction in process (b) according to the invention can be carried out by the following formula scheme are outlined:
Verwendet man beispielsweise 2-Amino-4-methoxy-6-trifluormethyl-l,3,5-triazin und 3 -Phenyl- 1-ethyl-propylamin als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (c) durch das folgende Formelschema skizziert werden:If, for example, 2-amino-4-methoxy-6-trifluoromethyl-l, 3,5-triazine and 3-phenyl-1-ethyl-propylamine are used as starting materials, the course of the reaction in process (c) according to the invention can be outlined by the following formula become:
Die beim erfindungsgemäßen Verfahren (a) zur Herstellung von Verbindungen der Formel (I) als Ausgangsstoffe zu verwendenden substituierten Biguanide sind durch die Formel (II) allgemein definiert. In der Formel (II) haben R1, R2, A und Ar vor- zugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) vorzugsweise bzw. als insbesondere bevorzugt für R1, R2, A und Ar angegeben wurden. Als Beispiele für die substituierten Biguanide der Formel (II) seien genannt:Formula (II) provides a general definition of the substituted biguanides to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In formula (II), R 1 , R 2 , A and Ar have preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 , R 2 , A and Ar. The following may be mentioned as examples of the substituted biguanides of the formula (II):
1 -( 1 -Ethyl-3 -phenyl-propyl)-, 1 -( 1 -n-Propyl-3 -phenyl-propyl)-, 1 -( 1 -i-Propyl-3 -phe- nyl-propyl)-, 1 -( 1 -Cyclopropyl-3 -phenyl-propyl)-, 1 -( 1 -Ethyl-3 -(2-fluor-phenyl)-pro- pyl)-, 1 -( 1 -Ethyl-3 -(3 -fluor-phenyl)-propyl)-, 1 -( 1 -Ethyl-3-(4-fluor-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-chlor-phenyl)-proρyl)-, 1 -( 1 -Ethyl-3 -(3 -chlor-phenyl)-propyl)-, 1 -( 1 - Ethyl-3-(4-chlor-phenyl)-propyl)-, l-(l-Ethyl-3-(2-brom-phenyl)-propyl)-, 1-(1-Ethyl-1 - (1-ethyl-3-phenyl-propyl) -, 1 - (1-n-propyl-3-phenyl-propyl) -, 1 - (1-i-propyl-3-phenyl-propyl) - , 1 - (1-Cyclopropyl-3-phenyl-propyl) -, 1 - (1-ethyl-3 - (2-fluorophenyl) -propyl) -, 1 - (1-ethyl-3 - (3rd -fluorophenyl) propyl), 1 - (1-ethyl-3- (4-fluorophenyl) propyl), 1 - (1-ethyl-3 - (2-chlorophenyl) propyl) -, 1 - (1-Ethyl-3 - (3-chlorophenyl) propyl) -, 1 - (1 - Ethyl-3- (4-chlorophenyl) propyl) -, l- (l-ethyl -3- (2-bromo-phenyl) -propyl) -, 1- (1-ethyl-
3 -(3 -brom-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4-brom-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2- nitro-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(3 -nitro-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4-nitro- phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-methyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(3 -methyl- phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4-methyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propyl)-, l-(l-Ethyl-3-(3-trifluormethyl-phenyl)-propyl)-, 1-(1-Ethyl-3 - (3-Bromophenyl) propyl), 1 - (1-Ethyl-3 - (4-bromophenyl) propyl) -, 1 - (1-Ethyl-3 - (2-nitro-phenyl ) -propyl) -, 1 - (1-ethyl-3 - (3-nitro-phenyl) -propyl) -, 1 - (1-ethyl-3 - (4-nitro-phenyl) -propyl) -, 1 - (1-Ethyl-3 - (2-methylphenyl) propyl) -, 1 - (1-Ethyl-3 - (3-methylphenyl) propyl) -, 1 - (1-Ethyl-3 - ( 4-methyl-phenyl) -propyl) -, 1 - (1-ethyl-3 - (2-trifluoromethyl-phenyl) -propyl) -, l- (l-ethyl-3- (3-trifluoromethyl-phenyl) -propyl) -, 1- (1-ethyl-
3 -(4-trifluormethyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3-(2-methoxy-phenyl)-propyl)-, 1 -( 1 - Ethyl-3 -(3 -methoxy-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4-methoxy-phenyl)-propyl)-, 1 - ( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-difluormethoxy-phe- nyl)-propyl)-, l-(l-Ethyl-3-(2-difluormethoxy-phenyl)-propyl)-, l-(l-Ethyl-3-(2-tri- fluormethoxy-phenyl)-propyl)-, l-(l-Ethyl-3-(3-trifluormethoxy-phenyl)-propyl)-, 1-3 - (4-trifluoromethyl-phenyl) -propyl) -, 1 - (1-ethyl-3- (2-methoxy-phenyl) -propyl) -, 1 - (1 - ethyl-3 - (3-methoxy-phenyl ) -propyl) -, 1 - (1-ethyl-3 - (4-methoxy-phenyl) -propyl) -, 1 - (1-ethyl-3 - (2-difluoromethoxy-phenyl) -propyl) -, 1 - (1-Ethyl-3 - (2-difluoromethoxyphenyl) propyl), l- (l-ethyl-3- (2-difluoromethoxyphenyl) propyl), l- (l-ethyl-3 - (2-trifluoromethoxy-phenyl) -propyl) -, l- (l-ethyl-3- (3-trifluoromethoxy-phenyl) -propyl) -, 1-
( 1 -Ethyl-3 -(4-trifluormethoxy-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-methoxycarbonyl- phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-methylthio-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4-methylthio-phenyl)-pro- pyl)-, l-(l-Ethyl-3-(2-methylsulfinyl-ρhenyl)-ρropyl)-, l-(l-Ethyl-3-(4-methylsulfinyl- phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-methylsulfonyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4- methylsulfonyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(3 ,4-dichlor-phenyl)-propyl)-, 1 -( 1 - Ethyl-3-(2,4-dichlor-phenyl)-propyl)-, l-(l-Ethyl-3-(2,5-dichlor-phenyl)-propyl)-, 1- ( 1 -Ethyl-3 -(2, 6-dichlor-phenyl)-proρyl)-, 1 -( 1 -Ethyl-3 -(2, 6-difluor-phenyl)-propyl)-, l-(l-Ethyl-3-(2,5-difluor-phenyl)-propyl)-, l-(l-Ethyl-3-(2,4-difluor-phenyl)-propyl)-, l-(l-Ethyl-3-(3,4-difluor-phenyl)-propyl)-, l-(l-Ethyl-3-(3,5-difluor-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(4-fluor-2-chlor-phenyl)- propyl)-, 1 -( 1 -Ethyl-3 -(2,4-dimethyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(3 ,4-dimethyl- phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(3 , 5-dimethyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2, 5-di- methyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-chlor-6-methyl-phenyl)-propyl)-, 1 -( 1 -Ethyl- 3 -(4-fluor-2-methyl-phenyl)-propyl)-, 1 -( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-propyl) l-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propyl)-, l-(l-Ethyl-3-(5-fluor-2-methyl-phe- nyl)-propyl)-, l-(l-Ethyl-3-thien-2-yl-propyl)-, l-(l-Ethyl-3-thien-3-yl-propyl)-, 1-(1- Ethyl-3-pyridin-2-yl-propyl)-, l-(l-Ethyl-3-pyridin-3-yl-propyl)- und l-(l-Ethyl-3- pyridin-4-yl-propyl)- -biguanid.(1-Ethyl-3 - (4-trifluoromethoxyphenyl) propyl) -, 1 - (1-Ethyl-3 - (2-methoxycarbonylphenyl) propyl) -, 1 - (1-Ethyl-3 - ( 2-ethoxycarbonylphenyl) propyl), 1 - (1-ethyl-3 - (4-methoxycarbonylphenyl) propyl), 1 - (1-ethyl-3 - (4-ethoxycarbonylphenyl) propyl ) -, 1 - (1-Ethyl-3 - (2-methylthio-phenyl) propyl) -, 1 - (1-Ethyl-3 - (4-methylthio-phenyl) propyl) -, l- ( l-ethyl-3- (2-methylsulfinyl-ρhenyl) -propyl) -, l- (l-ethyl-3- (4-methylsulfinyl-phenyl) -propyl) -, 1 - (1-ethyl-3 - (2nd -methylsulfonyl-phenyl) -propyl) -, 1 - (1-ethyl-3 - (4-methylsulfonyl-phenyl) -propyl) -, 1 - (1-ethyl-3 - (3, 4-dichloro-phenyl) - propyl) -, 1 - (1 - ethyl-3- (2,4-dichlorophenyl) propyl) -, l- (l-ethyl-3- (2,5-dichlorophenyl) propyl) -, 1- (1-Ethyl-3 - (2, 6-dichlorophenyl) propyl) -, 1 - (1-Ethyl-3 - (2, 6-difluorophenyl) propyl) -, l- (l -Ethyl-3- (2,5-difluorophenyl) propyl), l- (l-ethyl-3- (2,4-difluorophenyl) propyl), l- (l-ethyl-3 - (3,4-difluorophenyl) propyl), l- (l-ethyl-3- (3,5-difluorophenyl) propyl) -, 1 - (1 -E thyl-3 - (2-fluoro-4-chlorophenyl) propyl) -, 1 - (1-ethyl-3 - (4-fluoro-2-chlorophenyl) - propyl) -, 1 - (1-ethyl-3 - (2,4-dimethyl-phenyl) -propyl) -, 1 - (1-ethyl-3 - (3, 4-dimethyl-phenyl) -propyl) -, 1 - (1-ethyl-3 - (3,5-dimethylphenyl) propyl) -, 1 - (1-ethyl-3 - (2,5-dimethylphenyl) propyl) -, 1 - (1-ethyl-3 - (2-chloro-6-methylphenyl) propyl) -, 1 - (1-ethyl-3 - (4-fluoro-2-methylphenyl) propyl) -, 1 - (1-Ethyl-3 - (2-fluoro-4-methyl-phenyl) -propyl) l- (l-ethyl-3- (2-fluoro-5-methyl-phenyl) -propyl) -, l- (l -Ethyl-3- (5-fluoro-2-methylphenyl) propyl), l- (l-ethyl-3-thien-2-yl-propyl) -, l- (l-ethyl-3 -thien-3-yl-propyl) -, 1- (1-ethyl-3-pyridin-2-yl-propyl) -, l- (l-ethyl-3-pyridin-3-yl-propyl) - and l - (l-Ethyl-3-pyridin-4-yl-propyl) - biguanide.
Geeignete Säureaddukte von Verbindungen der Formel (II) sind deren Additionsprodukte mit Protonensäuren, wie z.B. mit Chlorwasserstoff (Hydrogenchlorid), Bromwasserstoff (Hydrogenbromid), Schwefelsäure, Methansulfonsäure, Benzol- sulfonsäure und p-Toluolsulfonsäure.Suitable acid adducts of compounds of the formula (II) are their addition products with protonic acids, such as e.g. with hydrogen chloride (hydrogen chloride), hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
Die Ausgangsstoffe der allgemeinen Formel (II) sind noch nicht aus der Literatur bekannt; sie sind als neue Stoffe auch Gegenstand der vorliegenden Anmeldung.The starting materials of the general formula (II) are not yet known from the literature; as new substances they are also the subject of the present application.
Man erhält die neuen substituierten Biguanide der allgemeinen Formel (II), wenn man substituierte Alkylamine der allgemeinen Formel (VI)The new substituted biguanides of the general formula (II) are obtained if substituted alkylamines of the general formula (VI)
in welcherin which
R1, R2, A und Ar die oben angegebene Bedeutung haben,R 1 , R 2 , A and Ar have the meaning given above,
- und/oder Säureaddukte von Verbindungen der allgemeinen Formel (VI), wie z.B. die Hydrochloride - mit Cyanoguanidin („Dicyandiamid") der Formel (VII)- and / or acid adducts of compounds of the general formula (VI), such as, for example, the hydrochlorides - with cyanoguanidine ("dicyandiamide") of the formula (VII)
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels, wie z.B. Hydrogenchlorid, und gegebenenfalls in Gegenwart eines Verdünnungsmittels, wie z.B. n-Decan oderoptionally in the presence of a reaction auxiliary, e.g. Hydrogen chloride, and optionally in the presence of a diluent, e.g. n-decane or
1,2-Dichlor-benzol, bei Temperaturen zwischen 100°C und 200°C umsetzt (vgl. EP 492615, Herstellungsbeispiele).1,2-dichlorobenzene, at temperatures between 100 ° C and 200 ° C (see. EP 492615, manufacturing examples).
Die hierfür als Voφrodukte benötigten substituierten Alkylaminoverbindungen der allgemeinen Formel (VI) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. J. Med. Chem. 10 (1967); 717-724; J. Am. Chem. Soc. 97 (1975), 6900-6901; Tetrahedron Lett. 35 (1994), 3745-3746; DE 3222152; DE 3221540; EP 355351; EP 601486; Herstellungsbeispiele).The substituted alkylamino compounds of the general formula (VI) required for this as products are known and / or can be prepared by processes known per se (cf. J. Med. Chem. 10 (1967); 717-724; J. Am. Chem. Soc. 97 (1975), 6900-6901; Tetrahedron Lett. 35 (1994), 3745-3746; DE 3222152; DE 3221540; EP 355351; EP 601486; production examples).
Die beim erfindungsgemäßen Verfahren (a) zur Herstellung von Verbindungen derThe process (a) according to the invention for the preparation of compounds of
Formel (I) weiter als Ausgangsstoffe zu verwendenden Alkoxycarbonylverbindungen sind durch die Formel (III) allgemein definiert. In der Formel (III) hat Z vorzugsweise bzw. insbesondere diejenige Bedeutung, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) vorzugsweise bzw. als insbesondere bevorzugt für Z angegeben wurde; R' steht vorzugsweise fürFormula (I) further alkoxycarbonyl compounds to be used as starting materials are generally defined by the formula (III). In formula (III), Z preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Z; R 'is preferably
Alkyl mit 1 bis 4 Kohlenstoffatomen, insbesondere für Methyl oder Ethyl.Alkyl with 1 to 4 carbon atoms, especially for methyl or ethyl.
Die Ausgangsstoffe der Formel (III) sind bekannte Synthesechemikalien. Die beim erfindungsgemäßen Verfahren (b) zur Herstellung von Verbindungen der Formel (I) als Ausgangsstoffe zu verwendenden substituierten Triazine sind durch dieThe starting materials of the formula (III) are known synthetic chemicals. The substituted triazines to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I) are characterized by
Formel (IV) allgemein definiert. In der Formel (IV) haben R1, R2, A, Ar und Z vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) vorzugsweise bzw. als insbesondere bevorzugt für R1, R2, A, Ar und Z angegeben wurden; X1 steht vorzugsweise für Fluor, Chlor, Brom, Methoxy oder Ethoxy, insbesondere für Chlor oder Methoxy.Formula (IV) generally defined. In the formula (IV), R 1 , R 2 , A, Ar and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for R 1 , R 2 , A, Ar and Z specified were; X 1 preferably represents fluorine, chlorine, bromine, methoxy or ethoxy, in particular chlorine or methoxy.
Als Beispiele für die substituierten Triazine der Formel (IV) seien genannt:The following may be mentioned as examples of the substituted triazines of the formula (IV):
2-( 1 -Ethyl-3 -phenyl-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(4-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-brom- phenyl)-propylamino)-, 2-(l-Ethyl-3-(3-brom-phenyl)-propylamino)-, 2-(l-Ethyl-3-2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3 - (2-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3-fluoro- phenyl) propylamino), 2- (1-ethyl-3 - (4-fluorophenyl) propylamino), 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (4-chlorophenyl) propylamino) -, 2- (1-Ethyl- 3 - (2-bromophenyl) propylamino), 2- (l-ethyl-3- (3-bromophenyl) propylamino), 2- (l-ethyl-3-
(4-brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-,(4-bromophenyl) propylamino) -, 2- (1-ethyl-3 - (2-nitro-phenyl) propylamino) -, 2- (1 - ethyl-3- (3-nitro-phenyl) - propylamino) -, 2- (l-ethyl-3- (4-nitro-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-methylphenyl) propylamino) -, 2- (1 -Ethyl-3 - (3-methyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (4-methyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - ( 2-trifluoromethylphenyl) propylamino) -, 2- (1-ethyl-3 - (3-trifluoromethylphenyl) propylamino) -,
2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-(l -Ethyl-3-(2-difluormethoxy-phenyl)-propylamino)-, 2-(l -Ethyl-3-(2-difluor- methoxy-phenyl)-propylamino)-, 2-(l -Ethyl-3-(2-trifluormethoxy-phenyl)-propylami- no)-, 1 -( 1 -Ethyl-3-(3 -trifluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-triflu- ormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-propyl- amino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-(l-Ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyI)-propylami- no)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(3 ,4-dichlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-dichlor-phe- nyl)-propylamino)-, 2-(l-Ethyl-3-(2,5-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-2- (1-Ethyl-3 - (4-trifluoromethyl-phenyl) propylamino) -, 2- (1-Ethyl-3 - (2-methoxy-phenyl) propylamino) -, 2- (1-Ethyl -3 - (3-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-difluoromethoxy- phenyl) propylamino), 2- (l-ethyl-3- (2-difluoromethoxy-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-difluoro-methoxy-phenyl) -propylamino ) -, 2- (l -Ethyl-3- (2-trifluoromethoxy-phenyl) -propylamino) -, 1 - (1 -Ethyl-3- (3-trifluoromethoxy-phenyl) -propylamino) -, 2- ( 1-ethyl-3 - (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl- 3 - (2-ethoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-ethoxycarbonyl-phenyl ) - propylamino) -, 2- (l-ethyl-3- (2-methylthio-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-methylthio-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (2-methylsulfinylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfinylphenyl) propy lamino) -, 2- (1-ethyl-3 - (2-methylsulfonylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfonylphenyl) propylamino) -, 2- (1-Ethyl-3 - (3, 4-dichlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2,4-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,5-dichlorophenyl) propylamino) -, 2- (l-ethyl-3-
(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-difluor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3-(3 ,4-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 , 5 -di- fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(4-fluor-2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-dimethyl-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 , 4-dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (3,5 -dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,5 -dimethyl-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(2-chlor-6-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-fluor-2- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(5-fluor-2-me- thyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -thien-2-yl-propylamino)-, 2-( 1 -Ethyl-3 - thien-3-yl-propylamino)-, 2-(l-Ethyl-3-pyridin-2-yl-propylamino)-, 2-(l-Ethyl-3- pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4,6-dichlor- 1,3,5-triazin;(2,6-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2, 5 -difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2,4-difluorophenyl) - propylamino) -, 2- (1-ethyl-3- (3,4-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3,5-di-fluorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (4-fluoro-2-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2,4-dimethylphenyl) propylamino) -, 2- (1-Ethyl-3 - (3, 4-dimethylphenyl) propylamino) -, 2- (1-Ethyl-3 - (3,5-dimethylphenyl) propylamino) -, 2- (1-Ethyl-3 - (2,5-dimethylphenyl) propylamino) -, 2- (l-ethyl-3- (2-chloro-6-methylphenyl) propylamino) -, 2- (l-ethyl-3- (4-fluoro-2-methylphenyl) propylamino) -, 2- (1-Ethyl-3 - (2-fluoro-4-methylphenyl) propylamino) -, 2- (1-ethyl-3- (2-fluoro-5-methylphenyl) propylamino) -, 2- (l-Ethyl-3- (5-fluoro-2-methylphenyl) propylamino) -, 2- (1-ethyl-3-thien-2-yl-propylamino) -, 2- (1-ethyl -3 - thien-3-yl-propylamino) -, 2- (l-ethyl-3-pyridin-2-yl-propylamino) -, 2- (l-ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) -4,6-dichloro-1,3,5-triazine;
2-( 1 -Ethyl-3 -phenyl-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-phenyl)-propylamino)-, 2- (1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(4-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-brom- phenyl)-propylamino)-, 2-(l-Ethyl-3-(3-brom-phenyl)-propylamino)-, 2-(l-Ethyl-3- (4-brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3 -(3 -nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-nitro-phenyl)-propylamino)-,2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3 - (2-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3-fluoro- phenyl) propylamino), 2- (1-ethyl-3 - (4-fluorophenyl) propylamino), 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (4-chlorophenyl) propylamino) -, 2- (1-Ethyl- 3 - (2-bromophenyl) propylamino), 2- (l-ethyl-3- (3-bromophenyl) propylamino) -, 2- (l-ethyl-3- (4-bromophenyl) ) -propylamino) -, 2- (1-ethyl-3 - (2-nitro-phenyl) -propylamino) -, 2- (1 - ethyl-3 - (3-nitro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-nitro-phenyl) propylamino) -,
2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-(l-Ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-proρylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, 1 -( 1 -Ethyl-3 -(3 -trifluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylami-no)-, 2-( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-methylsulfonyl-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(3,4-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-dichlor-phe- nyl)-propylamino)-, 2-(l-Ethyl-3-(2,5-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3- (2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,5 -difluor-ρhenyl)-ρropylamino)-, 2-( 1 -Ethyl-3 -(2, 4-difluor-phenyl)- propylamino)-, 2-(l-Ethyl-3-(3,4-difluor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,5-di- fluor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-fluor-4-chlor-phenyl)-propylamino)-, 2-2- (1-ethyl-3 - (2-methylphenyl) propylamino) -, 2- (1-ethyl-3 - (3-methylphenyl) propylamino) -, 2- (1-ethyl -3 - (4-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3 - trifluoromethylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-trifluoromethyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-methoxyphenyl) propylamino ) -, 2- (l-Ethyl-3- (3-methoxyphenyl) propylamino) -, 2- (l-Ethyl-3- (4-methoxyphenyl) propylamino) -, 2- (1 - Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino),, 2- (1-ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2 -difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, 1 - (1-ethyl-3 - (3-trifluoromethoxy-phenyl) ) -propylamino) -, 2- (1-ethyl-3 - (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (2-ethoxycarbonyl-phenyl) propylamino) -, 2- (1-Ethyl-3 - (4-methoxycarbonyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (4-ethoxycarbonylphenyl) - propylamino) -, 2- (1-ethyl-3 - (2-methylthiophenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylthiophenyl) propylamino) -, 2- (1st -Ethyl-3 - (2-methylsulfinyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (4-methylsulfinyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - ( 2-methylsulfonylphenyl) propylamino) -, 2- (l-ethyl-3- (4-methylsulfonylphenyl) propylamino) -, 2- (l-ethyl-3- (3,4- dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,5-dichloro- phenyl) propylamino), 2- (l-ethyl-3- (2,6-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) propylamino ) -, 2- (1-Ethyl-3 - (2,5 -difluoro-ρhenyl) -ropropamino) -, 2- (1 -Ethyl-3 - (2,4-difluorophenyl) propylamino) -, 2nd - (l-ethyl-3- (3,4-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (3,5-di-fluorophenyl) propylamino) -, 2- ( l-ethyl-3- (2-fluoro-4-chlorophenyl) propylamino) -, 2-
( 1 -Ethyl-3 -(4-fluor-2-chlor-phenyl)-propylamino)-, 2-(l -Ethyl-3 -(2,4-dimethyl-phe- nyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(l-Ethyl-3- (3,5-dimethyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,5-dimethyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-6-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-2- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-propylamino)-,(1-Ethyl-3 - (4-fluoro-2-chlorophenyl) propylamino) -, 2- (l-Ethyl-3 - (2,4-dimethylphenyl) propylamino) -, 2- (l-ethyl-3- (3,4-dimethylphenyl) propylamino) -, 2- (l-ethyl-3- (3,5-dimethylphenyl) propylamino) -, 2- (l-ethyl -3- (2,5-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-chloro-6-methyl-phenyl) -propylamino) -, 2- (1-ethyl -3 - (4-fluoro-2-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-fluoro-4-methyl-phenyl) -propylamino) -,
2-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(5-fluor-2-me- thyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -thien-2-yl-propylamino)-, 2-( 1 -Ethyl-3- thien-3 -yl-propylamino)-, 2-( 1 -Ethyl-3 -pyridin-2-yl-propylamino)-, 2-( 1 -Ethyl-3 -pyri- din-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4-chlor-6-me- thyl-l,3,5-triazin;2- (l-ethyl-3- (2-fluoro-5-methylphenyl) propylamino) -, 2- (l-ethyl-3- (5-fluoro-2-methylphenyl) propylamino) -, 2- (1-Ethyl-3-thien-2-yl-propylamino) -, 2- (1-ethyl-3-thien-3-y-propylamino) -, 2- (1-ethyl-3-pyridine -2-yl-propylamino) -, 2- (1-ethyl-3-pyridine-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) - -4 -chloro-6-methyl-l, 3,5-triazine;
2-( 1 -Ethyl-3 -phenyl-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3-(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-proρylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-(l-Ethyl-3-(4-chlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-brom- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-brom-phenyι)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-trifluormethyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, l-(l-Ethyl-3-(3-trifluormethoxy-phenyl)-propylamino)-,' 2-(l-Ethyl-3-(4-triflu- ormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-propyl- amino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3-(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3-(3 ,4-dichlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-dichlor- phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,5-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl- 3-(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(2,5-difluor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-difluor- phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-difluor-phenyl)-propylamino)-, 2-(l -Ethyl- 3 -(3 , 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-( 1 -Ethyl-3 -(4-fluor-2-chlor-ρhenyl)-ρropylamino)-, 2-( 1 -Ethyl-3 -(2,4-di- methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3 - (2-fluorophenyl) propylamino) -, 2- (1-ethyl-3- (3-fluoro- phenyl) propylamino) -, 2- (1-ethyl-3 - (4-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (4-chlorophenyl) propylamino) -, 2- (l-ethyl- 3- (2-bromo-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3-bromo-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-bromo-phenyl) ) -propylamino) -, 2- (1-ethyl-3 - (2-nitro-phenyl) -propylamino) -, 2- (1 - ethyl-3- (3-nitro-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-nitro-phenyl) propylamino) -, 2- (1-ethyl-3- (2-methylphenyl) propylamino) -, 2- (1-ethyl-3 - ( 3-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-trifluoromethyl) phenyl) -propylamino) -, 2- (1-ethyl-3 - (3-trifluoromethyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-trifluoromethyl-phenyl) -propylamino) -, 2 - (l-ethyl-3- (2-methoxy-phe- nyl) propylamino), 2- (1-ethyl-3 - (3-methoxyphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methoxyphenyl) propylamino) -, 2nd - (1-Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl- 3 - (2-difluoro-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, l- (l-ethyl-3- (3rd -trifluoromethoxy-phenyl) -propylamino) -, ' 2- (l-ethyl-3- (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-ethoxycarbonyl-phenyl) -propylamino) -, 2- (1 -ethyl-3- (4-methoxycarbonyl-phenyl) -propylamino) -, 2nd - (1-Ethyl-3 - (4-ethoxycarbonylphenyl) propylamino) -, 2- (1-Ethyl-3 - (2-methylthio-phenyl) propylamino) -, 2- (1-Ethyl-3 - (4-methylthiophenyl) propylamino) -, 2- (1-ethyl-3 - (2-methylsulfinyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfinyl-phenyl) ) -propylamino) -, 2- (1-ethyl-3 - (2-methylsulfonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methylsulfonylphenyl) propylamino), 2- (1-ethyl-3- (3,4-dichlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2, 4-dichlorophenyl) propylamino), 2- (l-ethyl-3- (2,5-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,6-dichloro- phenyl) propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (2,5-difluorophenyl) -propylamino) -, 2- (l-ethyl-3- (2,4-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (3,4-difluorophenyl) propylamino) - , 2- (1-Ethyl- 3 - (3,5-difluorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (4-fluoro-2-chloro-ρhenyl) -ropropamino) -, 2- (1-Ethyl-3 - (2,4-dimethyl-phenyl) -propylamino) - , 2- (l-ethyl-3- (3,4-dimethylphenyl) propylamino) -, 2-
( 1 -Ethyl-3 -(3 , 5-dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5 -dimethyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-chlor-6-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(5- fluor-2-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-thien-2-yl-propylamino)-, 2-(l-(1-Ethyl-3 - (3,5-dimethylphenyl) propylamino) -, 2- (1-ethyl-3 - (2,5-dimethylphenyl) propylamino) -, 2- (1-ethyl -3 - (2-chloro-6-methylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-fluoro-2-methylphenyl) propylamino) -, 2- (1-ethyl -3 - (2-fluoro-4-methylphenyl) propylamino) -, 2- (l-ethyl-3- (2-fluoro-5-methylphenyl) propylamino) -, 2- (l -Ethyl-3- (5-fluoro-2-methylphenyl) propylamino) -, 2- (l-ethyl-3-thien-2-yl-propylamino) -, 2- (l-
Ethyl-3 -thien-3 -yl-propylamino)-, 2-( 1 -Ethyl-3 -pyridin-2-yl-propylamino)-, 2-( 1 - Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-trifluormethyl- 1,3,5 -triazin;Ethyl-3-thien-3 -yl-propylamino) -, 2- (1-ethyl-3-pyridin-2-yl-propylamino) -, 2- (1 - ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) -4-chloro-6-trifluoromethyl-1,3,5-triazine;
2-(l-Ethyl-3-phenyl-propylamino)-, 2-(l-Ethyl-3-(2-fluor-phenyl)-propylamino)-, 2-2- (l-ethyl-3-phenyl-propylamino) -, 2- (l-ethyl-3- (2-fluorophenyl) propylamino) -, 2-
( 1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(4-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-brom- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-brom-phenyl)-propylamino)-, 2-(l -Ethyl-3-(2-nitro-phenyl)-propylamino)-, 2-(l - Ethyl-3 -(3 -nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3-(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyι)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, l-(l-Ethyl-3-(3-trifluormethoxy-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-(l-Ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-pro pylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl- sulfonyl-phenyl)-proρylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(3,4-dichlor-ρhenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-dichlor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5 -dichlor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3 -(2, 6-dichlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 6-difluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2, 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-difluor- phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-difluor-phenyl)-propylamino)-, 2-(l-Ethyl-(1-Ethyl-3 - (3-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (4-fluoro-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) -, 2- (1-ethyl-3 - (3-chlorophenyl) - propylamino) -, 2- (1-ethyl-3 - (4-chlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2-bromo-phenyl) propylamino) -, 2- (1st -Ethyl-3 - (3-bromo-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (4-bromo-phenyl) -propylamino) -, 2- (l -ethyl-3- (2- nitro-phenyl) -propylamino) -, 2- (l - ethyl-3 - (3-nitro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-nitro-phenyl) -propylamino) - , 2- (1-ethyl-3 - (2-methylphenyl) propylamino) -, 2- (1-ethyl-3 - (3-methylphenyl) propylamino) -, 2- (1 - Ethyl-3 - (4-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3rd -trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxy-phenyl) - propylamino) -, 2- (1-ethyl-3 - (3-methoxyphenyl) propylamino) -, 2- (1-ethyl-3- (4-methoxyphenyl) propylamino) -, 2- (1 -Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - ( 2-difluoro-methoxy-phenyι) -propylamino) -, 2- (1-Ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, l- (l-Ethyl-3- (3-trifluoromethoxy-phenyl) -propylamino) -, 2- (l -Ethyl-3- (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (l-ethyl-3 - (2-ethoxycarbonyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-ethoxycarbonyl-phenyl) - propylamino) -, 2- (l-ethyl-3- (2-methylthio-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-methylthio-phenyl) -propylamino) -, 2- ( 1-ethyl-3 - (2-methylsulfinyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methylsulfinyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - ( 2-methylsulfonylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfonylphenyl) propylamino) -, 2- (l-ethyl-3- (3,4- dichloro-ρhenyl) -propylamino) -, 2- (l-ethyl-3- (2,4-dichloro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2, 5-dichloro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2, 6-dichlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2, 6-difluorophenyl) propylamino ) -, 2- (1-Ethyl-3 - (2, 5-difluorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2,4-difluorophenyl) propylamino) -, 2- (l -Ethyl-3- (3,4-difluorophenyl) propylamino) -, 2- (l-ethyl-
3 -(3 , 5 -difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-(l-Ethyl-3-(4-fluor-2-chlor-ρhenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-di- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-dimethyl-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3 , 5-dimethyl-phenyl)-ρroρylamino)-, 2-( 1 -Ethyl-3 -(2, 5-dimethyl-phenyl)- propylamino)-, 2-(l-Ethyl-3-(2-chlor-6-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-3 - (3,5-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) -, 2- (l-ethyl- 3- (4-fluoro-2-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-dimethylphenyl) propylamino) -, 2- (1-ethyl- 3 - (3, 4-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3, 5-dimethyl-phenyl) -ρroρylamino) -, 2- (1-ethyl-3 - (2 , 5-dimethyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-chloro-6-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3-
(4-fluor-2-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-5-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3-(5- fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -thien-2-yl-propylamino)-, 2-( 1 - Ethyl-3 -thien-3 -yl-propylamino)-, 2-( 1 -Ethyl-3 -pyridin-2-yl-propylamino)-, 2-( 1 - Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-( 1 -fluor-ethyl)- 1 ,3 , 5-triazin;(4-fluoro-2-methylphenyl) propylamino) -, 2- (l-ethyl-3- (2-fluoro-4-methylphenyl) propylamino) -, 2- (1-ethyl- 3 - (2-fluoro-5-methylphenyl) propylamino) -, 2- (1-ethyl-3- (5- fluoro-2-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3-thien-2-yl-propylamino) -, 2- (1 - ethyl-3-thien-3-yl-propylamino) - , 2- (1-ethyl-3-pyridin-2-yl-propylamino) -, 2- (1 - ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridine- 4-yl-propylamino) - -4-chloro-6- (1-fluoro-ethyl) - 1, 3, 5-triazine;
2-( 1 -Ethyl-3 -phenyl-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-(l-Ethyl-3-(4-chlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-brom- phenyl)-propylamino)-, 2-(l-Ethyl-3-(3-brom-phenyl)-propylamino)-, 2-(l-Ethyl-3-2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3 - (2-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3-fluoro- phenyl) propylamino), 2- (1-ethyl-3 - (4-fluorophenyl) propylamino), 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (4-chlorophenyl) propylamino) -, 2- (l-ethyl- 3- (2-bromophenyl) propylamino) -, 2- (l-ethyl-3- (3-bromophenyl) propylamino) -, 2- (l-ethyl-3-
(4-brom-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-nitro-phenyl)-propylamino)-, 2-(l- Ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyι)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-,(4-bromo-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-nitro-phenyl) -propylamino) -, 2- (l-ethyl-3- (3-nitro-phenyl) - propylamino) -, 2- (l-ethyl-3- (4-nitro-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-methylphenyl) propylamino) -, 2- (1 -Ethyl-3 - (3-methyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (4-methyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - ( 2-trifluoromethylphenyl) propylamino) -, 2- (1-ethyl-3 - (3-trifluoromethylphenyl) propylamino) -,
2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-trifluormethoxy-phenyl)-propylami- no)-, 1 -( 1 -Ethyl-3 -(3 -trifluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-(l-Ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methylthio-phenyl)-proρylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3-(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(3,4-dichlor-phenyl)-proρylamino)-, 2-(l -Ethyl-3-(2,4-dichlor- phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,5-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-2- (1-Ethyl-3 - (4-trifluoromethyl-phenyl) propylamino) -, 2- (1-Ethyl-3 - (2-methoxy-phenyl) propylamino) -, 2- (1-Ethyl -3 - (3-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-difluoromethoxy- phenyl) propylamino), 2- (1-ethyl-3 - (2-difluoromethoxy-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-difluoro-methoxy-phenyl) propylamino ) -, 2- (l-Ethyl-3- (2-trifluoromethoxy-phenyl) -propylamino) -, 1 - (1-Ethyl-3 - (3-trifluoromethoxy-phenyl) -propylamino) -, 2- ( 1-ethyl-3 - (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl- 3 - (2-ethoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-ethoxycarbonyl-phenyl ) - propylamino) -, 2- (l-ethyl-3- (2-methylthio-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-methylthio-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (2-methylsulfinyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfinyl-phenyl) - propylamino) -, 2- (1-ethyl-3- (2-methylsulfonylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfonylphenyl) propylamino) -, 2- (l-ethyl-3- (3,4-dichlorophenyl) propylamino) -, 2- (l -ethyl-3- (2,4-dichlorophenyl) propylamino) -, 2- (l -Ethyl-3- (2,5-dichlorophenyl) propylamino) -, 2- (l-ethyl-
3-(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2, 5 -difluor-phenyl)-proρylamino)-, 2-( 1 -Ethyl-3 -(2,4-difluor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3 -(3 , 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-(l-Ethyl-3-(4-fluor-2-chlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-di- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-dimethyl-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3,5 -dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 "-(2, 5 -dimethyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-chlor-6-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-5 -methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(5 - fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -thien-2-yl-propylamino)-, 2-( 1 - Ethyl-3-thien-3-yl-propylamino)-, 2-(l-Ethyl-3-pyridin-2-yl-propylamino)-, 2-(l-3- (2,6-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2,5-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2,4-difluoro- phenyl) propylamino), 2- (1-ethyl-3 - (3,4-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3,5-difluorophenyl) propylamino ) -, 2- (1-Ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (4-fluoro-2-chlorophenyl) -propylamino) -, 2- (1-ethyl-3- (2,4-dimethylphenyl) propylamino) -, 2- (1-ethyl-3 - (3,4-dimethylphenyl) propylamino ) -, 2- (1-ethyl-3 - (3,5-dimethylphenyl) propylamino) -, 2- (1-ethyl-3 " - (2,5-dimethylphenyl) propylamino) -, 2- (1-Ethyl-3 - (2-chloro-6-methylphenyl) propylamino) -, 2- (1-Ethyl-3 - (4-fluoro-2-methylphenyl) propylamino) -, 2- (1-Ethyl-3 - (2-fluoro-4-methylphenyl) propylamino) -, 2- (1-Ethyl-3 - (2-fluoro-5-methylphenyl) propylamino) -, 2- (1-Ethyl-3 - (5 - fluoro-2-methylphenyl) propylamino) -, 2- (1-ethyl-3-thien-2-yl-propylamino) -, 2- (1 - Ethyl-3-thien-3-yl-propylamino) -, 2- (l-ethyl-3-pyridin-2-yl-propylamino) -, 2- (l-
Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-( 1 -fluor- 1 -methyl-ethyl)- 1,3,5 -triazin;Ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) - -4-chloro-6- (1-fluoro-1-methyl-ethyl) - 1,3,5-triazine;
2-(l -Ethyl-3-phenyl-propylamino)-, 2-( 1 -Ethyl-3-(2-fluor-phenyl)-propylamino)-, 2- (1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-pro pylamino)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3-(4-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-brom- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-brom-phenyι)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-nitro-phenyl)-propylamino)-,2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3- (2-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3-fluoro- phenyl) propylamino), 2- (1-ethyl-3 - (4-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (1-Ethyl-3- (4-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2-bromo-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3-bromo-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-bromo-phenyι) -propylamino) -, 2- (1-ethyl-3 - (2-nitro-phenyl) -propylamino) -, 2- (1 - ethyl-3- (3-nitro-phenyl) -propylamino) -, 2- ( l-ethyl-3- (4-nitro-phenyl) propylamino) -,
2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-trifluormethyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-methoxy-phe- nyl)-propylamino)-, 2-(l-Ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyι)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, 1 -( 1 -Ethyl-3 -(3 -trifluormethoxy-ρhenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3-(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(3,4-dichlor-phenyl)-ρropylamino)-, 2-(l-Ethyl-3-(2,4-dichlor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5-dichlor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3-(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(2,5-difluor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-difluor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3-(3 ,4-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3 -(3 , 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-( 1 -Ethyl-3 -(4-fluor-2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-di- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-dimethyl-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3 , 5-dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5 -dimethyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-chlor-6-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propylamino)-, 2-(l -Ethyl-3-(5- fluor-2-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-thien-2-yl-propylamino)-, 2-(l- Ethyl-3 -thien-3 -yl-propylamino)-, 2-( 1 -Ethyl-3 -pyridin-2-yl-propylamino)-, 2-( 1 - Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-methoxy-l,3,5-triazin;2- (1-ethyl-3 - (2-methylphenyl) propylamino) -, 2- (1-ethyl-3 - (3-methylphenyl) propylamino) -, 2- (1-ethyl -3 - (4-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3 - trifluoromethyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-trifluoromethyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-methoxy-phenyl) -propylamino ) -, 2- (l-Ethyl-3- (3-methoxyphenyl) propylamino) -, 2- (l-Ethyl-3- (4-methoxyphenyl) propylamino) -, 2- (1 - Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino),, 2- (1-ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2 -difluoro-methoxy-phenyι) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, 1 - (1-ethyl-3 - (3-trifluoromethoxy-ρhenyl ) -propylamino) -, 2- (1-ethyl-3 - (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-ethoxycarbonyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (4-methoxycarbonyl-phenyl) propylamino) -, 2- (1-Ethyl-3 - (4-ethoxycarbonylphenyl) - propylamino) -, 2- (1-ethyl-3 - (2-methylthio-phenyl) propylamino) -, 2- (1-ethyl-3- (4-methylthio-phenyl) propylamino) -, 2- (1 -Ethyl-3 - (2-methylsulfinyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (4-methylsulfinyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - ( 2-methyl-sulfonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methyl-sulfonyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (3,4- dichlorophenyl) ρropylamino) -, 2- (l-ethyl-3- (2,4-dichlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2, 5-dichlorophenyl) -propylamino) -, 2- (1-ethyl-3- (2,6-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) propylamino ) -, 2- (l-ethyl-3- (2,5-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-difluorophenyl) propylamino) -, 2nd - (1-Ethyl-3- (3, 4-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3, 5-difluorophenyl) propylamino) -, 2- (1 - Ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (4-fluoro-2-chlorophenyl) propylamino) -, 2- ( 1-ethyl-3 - (2,4-dimethylphenyl) propylamino) -, 2- (1-ethyl-3 - (3, 4-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3, 5-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2, 5-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-chloro-6-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-fluoro- 2-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-fluoro-4-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (2- fluoro-5-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (5-fluoro-2-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3-thien-2 -yl-propylamino) -, 2- (l-ethyl-3-thien-3-yl-propylamino) -, 2- (1-ethyl-3-pyridin-2-yl-propylamino) -, 2- (1 - Ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) - -4-chloro-6-methoxy-l, 3,5-triazine;
2-( 1 -Ethyl-3 -phenyl-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-(l-Ethyl-3-(4-chlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-brom- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3-brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3 -(3 -nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-nitro-phenyl)-pro pylamino)-, 2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-pro pylamino)-, 2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3-(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, l-(l-Ethyl-3-(3-trifluormethoxy-phenyl)-propylamino)-', 2-(l-Ethyl-3-(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyι)-propylami- no)-, 2-(l-Ethyl-3-(4-methylsulfinyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-pro pylamino)-, 2-(l-Ethyl-3-(3,4-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-dichlor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5 -dichlor-phenyl)-pro pylamino)-, 2-( 1 -Ethyl- 3-(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2,5 -difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 4-difluor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3 -(3 , 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-(l-Ethyl-3-(4-fluor-2-chlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-di- methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3 - (2-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3-fluoro- phenyl) propylamino), 2- (1-ethyl-3 - (4-fluorophenyl) propylamino), 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (4-chlorophenyl) propylamino) -, 2- (l-ethyl- 3- (2-bromophenyl) propylamino) -, 2- (1-ethyl-3 - (3-bromophenyl) propylamino) -, 2- (1-ethyl-3 - (4-bromophenyl) ) -propylamino) -, 2- (1-ethyl-3 - (2-nitro-phenyl) -propylamino) -, 2- (1 - ethyl-3 - (3-nitro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-nitro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3-methylphenyl) propylamino) -, 2- (l-ethyl-3- (4-methylphenyl) propylamino) -, 2- (l-ethyl-3- (2-trifluoromethyl) -phenyl) -propylamino) -, 2- (1-ethyl-3 - (3-trifluoromethyl-phenyl) -pro pylamino) -, 2- (1-ethyl-3 - (4-trifluoromethyl-phenyl) -propylamino) - , 2- (1-Ethyl-3 - (2-methoxy-phe- nyl) propylamino) -, 2- (1-ethyl-3- (3-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxy-phenyl) -propylamino) -, 2nd - (1-Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl- 3 - (2-difluoro-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, l- (l-ethyl-3- (3rd -trifluoromethoxy-phenyl) -propylamino) - ' , 2- (l-ethyl-3- (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxycarbonyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-ethoxycarbonylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methoxycarbonylphenyl) propylamino) -, 2 - (l-ethyl-3- (4-ethoxycarbonyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-methylthio-phenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylthio-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-methylsulfinyl-phenyι) -propylamino) -, 2- (l-ethyl-3- (4-methylsulfinyl-phenyl ) -propylamino) -, 2- (l-ethyl-3- (2-methylsulfonylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-me thylsulfonylphenyl) propylamino) -, 2- (l-ethyl-3- (3,4-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-dichlorophenyl) ) -propylamino) -, 2- (1-ethyl-3 - (2, 5 -dichlorophenyl) -propylamino) -, 2- (1 -ethyl-3- (2,6-dichlorophenyl) propylamino ) -, 2- (l-Ethyl-3- (2,6-difluorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2,5-difluorophenyl) propylamino) - , 2- (1-Ethyl-3 - (2,4-difluorophenyl) propylamino) -, 2- (1-Ethyl-3 - (3,4-difluorophenyl) propylamino) -, 2- ( 1-ethyl-3 - (3,5-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) -, 2- ( l-ethyl-3- (4-fluoro-2-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-dimethylphenyl) propylamino) -, 2- ( l-ethyl-3- (3,4-dimethylphenyl) propylamino) -, 2-
( 1 -Ethyl-3 -(3 , 5-dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5-dimethyl-phenyl)- propylamino)-, 2-(l-Ethyl-3-(2-chlor-6-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3- (4-fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(5- fluor-2-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-thien-2-yl-propylamino)-, 2-(l-(1-Ethyl-3 - (3,5-dimethylphenyl) propylamino) -, 2- (1-ethyl-3 - (2,5-dimethylphenyl) propylamino) -, 2- (l-ethyl -3- (2-chloro-6-methylphenyl) propylamino) -, 2- (l-ethyl-3- (4-fluoro-2-methylphenyl) propylamino) -, 2- (1-ethyl -3 - (2-fluoro-4-methylphenyl) propylamino) -, 2- (l-ethyl-3- (2-fluoro-5-methylphenyl) propylamino) -, 2- (l -Ethyl-3- (5-fluoro-2-methylphenyl) propylamino) -, 2- (l-ethyl-3-thien-2-yl-propylamino) -, 2- (l-
Ethyl-3 -thien-3 -yl-propylamino)-, 2-( 1 -Ethyl-3 -pyridin-2-yl-propylamino)-, 2-( 1 - Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-(2,2,2-trifluor-ethoxy)-l,3,5-triazin;Ethyl-3-thien-3 -yl-propylamino) -, 2- (1-ethyl-3-pyridin-2-yl-propylamino) -, 2- (1 - ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) -4-chloro-6- (2,2,2-trifluoro-ethoxy) -l, 3,5-triazine;
2-(l-Ethyl-3-phenyl-propylamino)-, 2-(l-Ethyl-3-(2-fluor-phenyl)-propylamino)-, 2-2- (l-ethyl-3-phenyl-propylamino) -, 2- (l-ethyl-3- (2-fluorophenyl) propylamino) -, 2-
( 1 -Ethyl-3-(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-pro pylamino)-, 2-(l-Ethyl-3-(2-chlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(3-chlor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(4-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-brom- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3 -(3 -nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-nitro-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propyIamino)-, 2-( 1 -Ethyl-3 -'(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, l-(l-Ethyl-3-(3-trifluormethoxy-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(3 ,4-dichlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-dichlor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5-dichlor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3-(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propylami- no)-, 2-(l-Ethyl-3-(2,5-difluor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-difluor- phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-difluor-phenyl)-propylamino)-, 2-(l-Ethyl-(1-Ethyl-3- (3-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (4-fluorophenyl) propylamino) -, 2- (l-ethyl-3- (2-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (3-chlorophenyl) - propylamino) -, 2- (1-ethyl-3 - (4-chlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2-bromo-phenyl) propylamino) -, 2- (1st -Ethyl-3 - (3-bromo-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (4-bromo-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2- nitro-phenyl) -propylamino) -, 2- (1 - ethyl-3 - (3-nitro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-nitro-phenyl) -propylamino) - , 2- (1-Ethyl-3 - (2-methylphenyl) propylamino) -, 2- (1-Ethyl-3 - ' (3-methylphenyl) propylamino) -, 2- (1st -Ethyl-3 - (4-methyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (2-trifluoromethyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - ( 3-trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxy-phenyl)) -propylamino) -, 2- (1-ethyl-3 - (3-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxy-phenyl) -propylamino) -, 2- ( 1-ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-difluoro-methoxy-phenyl) propyl amino) -, 2- (1-Ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, l- (l-Ethyl-3- (3-trifluoromethoxy-phenyl) -propylamino) -, 2- (l-Ethyl-3- (4-trifluoromethoxyphenyl) propylamino) -, 2- (1-ethyl-3 - (2-methoxycarbonylphenyl) propylamino) -, 2- (l-ethyl -3- (2-ethoxycarbonyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-ethoxycarbonyl- phenyl) propylamino), 2- (1-ethyl-3 - (2-methylthio-phenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylthio-phenyl) propylamino) -, 2 - (1-Ethyl-3 - (2-methylsulfinyl-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (4-methylsulfinyl-phenyl) -propylamino) -, 2- (1-ethyl- 3 - (2-methylsulfonylphenyl) propylamino), 2- (1-ethyl-3 - (4-methylsulfonylphenyl) propylamino) -, 2- (1-ethyl-3 - (3rd , 4-dichlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2,4-dichlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2, 5-dichlor -phenyl) -propylamino) -, 2- (1-ethyl-3- (2,6-dichlorophenyl) -propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) - propy lamino) -, 2- (l-ethyl-3- (2,5-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (3,4-difluorophenyl) propylamino) -, 2- (l-ethyl-
3-(3,5-difluor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-(l-Ethyl-3-(4-fluor-2-chlor-ρhenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-di- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-dimethyl-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3-(3 , 5-dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5-dimethyl-phenyl)- propylamino)-, 2-(l-Ethyl-3-(2-chlor-6-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-3- (3,5-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (2-fluoro-4-chlorophenyl) propylamino) -, 2- (l-ethyl- 3- (4-fluoro-2-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-dimethylphenyl) propylamino) -, 2- (1-ethyl- 3 - (3, 4-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3- (3, 5-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2 , 5-dimethyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-chloro-6-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3-
(4-fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propylamino)-, 2-(l -Ethyl-3-(5- fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -thien-2-yl-propylamino)-, 2-( 1 - Ethyl-3 -thien-3 -yl-propylamino)-, 2-( 1 -Ethyl-3 -pyridin-2-yl-propylamino)-, 2-( 1 - Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-methylthio- 1,3,5 -triazin;(4-fluoro-2-methylphenyl) propylamino) -, 2- (1-ethyl-3 - (2-fluoro-4-methylphenyl) propylamino) -, 2- (l-ethyl- 3- (2-fluoro-5-methylphenyl) propylamino) -, 2- (l -ethyl-3- (5- fluoro-2-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3-thien-2-yl-propylamino) -, 2- (1 - ethyl-3-thien-3-yl-propylamino) - , 2- (1-ethyl-3-pyridin-2-yl-propylamino) -, 2- (1 - ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridine- 4-yl-propylamino) -4-chloro-6-methylthio-1,3,5-triazine;
2-( 1 -Ethyl-3-phenyl-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(4-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-brom- phenyl)-propylamino)-, 2-(l-Ethyl-3-(3-brom-phenyl)-propylamino)-, 2-(l-Ethyl-3-2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3 - (2-fluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3-fluoro- phenyl) propylamino), 2- (1-ethyl-3 - (4-fluorophenyl) propylamino), 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (4-chlorophenyl) propylamino) -, 2- (1-Ethyl- 3 - (2-bromophenyl) propylamino), 2- (l-ethyl-3- (3-bromophenyl) propylamino), 2- (l-ethyl-3-
(4-brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-nitro-phenyl)-pro pylamino)-, 2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-,(4-bromophenyl) propylamino) -, 2- (1-ethyl-3 - (2-nitro-phenyl) propylamino) -, 2- (1 - ethyl-3- (3-nitro-phenyl) - propylamino) -, 2- (l-ethyl-3- (4-nitro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methyl-phenyl) -propylamino) -, 2- ( 1-ethyl-3 - (3-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethylphenyl) propylamino) -, 2- (1-ethyl-3 - (3-trifluoromethylphenyl) propylamino) -,
2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, 1 -( 1 -Ethyl-3 -(3 -trifluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-(l-Ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4- methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3-(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methyl- sulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-propylami- no)-, 2-( 1 -EthyI-3 -(3 ,4-dichlor-phenyl)-proρylamino)-, 2-( 1 -Ethyl-3 -(2,4-dichlor- phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,5-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-2- (1-Ethyl-3 - (4-trifluoromethyl-phenyl) propylamino) -, 2- (1-Ethyl-3 - (2-methoxy-phenyl) propylamino) -, 2- (1-Ethyl -3 - (3-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-difluoromethoxy- phenyl) propylamino), 2- (1-ethyl-3 - (2-difluoromethoxy-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-difluoro-methoxy-phenyl) propylamino ) -, 2- (1-Ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, 1 - (1-Ethyl-3 - (3-trifluoromethoxy-phenyl) -propylamino) -, 2- ( 1-ethyl-3 - (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl- 3 - (2-ethoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-ethoxycarbonyl-phenyl ) - propylamino) -, 2- (l-ethyl-3- (2-methylthio-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-methylthio-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (2-methylsulfinyl-phenyl) propylamino) -, 2- (1-ethyl-3- (4-methylsulfinyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-methylsulfonylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfonylphenyl) propylamino) - , 2- (1-Ethyl-3 - (3, 4-dichlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (2,4-dichlorophenyl) propylamino) -, 2- ( l-ethyl-3- (2,5-dichlorophenyl) propylamino) -, 2- (l-ethyl-
3-(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-proρylami- no)-, 2-(l-Ethyl-3-(2,5-difluor-phenyl)-ρropylamino)-, 2-(l-Ethyl-3-(2,4-difluor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3 -(3 , 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-( 1 -Ethyl-3 -(4-fluor-2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-di- methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3,5 -dimethyl-phenyl)-pro pylamino)-, 2-( 1 -Ethyl-3"-(2, 5 -dimethyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-chlor-6-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(2-fluor-5-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(5- fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -thien-2-yl-propylamino)-, 2-( 1 - Ethyl-3-thien-3-yl-propylamino)-, 2-(l-Ethyl-3-pyridin-2-yl-propylamino)-, 2-(l-3- (2,6-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) propylamino) -, 2- (l-ethyl-3- (2,5-difluorophenyl) ρropylamino) -, 2- (l-ethyl-3- (2,4-difluoro- phenyl) propylamino), 2- (1-ethyl-3 - (3,4-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (3,5-difluorophenyl) propylamino ) -, 2- (1-Ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) -, 2- (1-Ethyl-3 - (4-fluoro-2-chlorophenyl) -propylamino) -, 2- (1-ethyl-3 - (2,4-dimethyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (3,4-dimethyl-phenyl) -propylamino ) -, 2- (1-Ethyl-3 - (3,5-dimethylphenyl) propylamino) -, 2- (1-Ethyl-3 " - (2,5-dimethylphenyl) propylamino) - , 2- (1-ethyl-3 - (2-chloro-6-methylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-fluoro-2-methylphenyl) propylamino) - , 2- (1-Ethyl-3 - (2-fluoro-4-methylphenyl) propylamino) -, 2- (l-Ethyl-3- (2-fluoro-5-methylphenyl) propylamino ) -, 2- (l-Ethyl-3- (5-fluoro-2-methylphenyl) propylamino) -, 2- (1-Ethyl-3-thien-2-yl-propylamino) -, 2- ( 1 - ethyl-3-thien-3-yl-propylamino) -, 2- (l-ethyl-3-pyridin-2-yl-propylamino) -, 2- (l-
Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-methylsulfinyl- 1 , 3 , 5-triazin;Ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) - -4-chloro-6-methylsulfinyl-1, 3, 5-triazine;
2-( 1 -Ethyl-3 -phenyl-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-phenyl)-propylamino)-, 2- (1 -Ethyl-3 -(3 -fluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-fluor-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -chlor-phenyl)- propylamino)-, 2-( 1 -Ethyl-3-(4-chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-brom- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-brom-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-nitro-phenyl)-propylamino)-, 2-( 1 - Ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(l-Ethyl-3-(4-nitro-phenyl)-pro pylamino)-,2- (1-ethyl-3-phenyl-propylamino) -, 2- (1-ethyl-3 - (2-fluoro-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3-fluoro- phenyl) propylamino), 2- (1-ethyl-3 - (4-fluorophenyl) propylamino), 2- (1-ethyl-3 - (2-chlorophenyl) propylamino) - , 2- (1-Ethyl-3 - (3-chlorophenyl) propylamino) -, 2- (1-Ethyl-3- (4-chlorophenyl) propylamino) -, 2- (1-Ethyl- 3 - (2-bromo-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3-bromo-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-bromo-phenyl ) -propylamino) -, 2- (1-ethyl-3 - (2-nitro-phenyl) -propylamino) -, 2- (1 - ethyl-3- (3-nitro-phenyl) -propylamino) -, 2- (l-ethyl-3- (4-nitro-phenyl) propylamino) -,
2-( 1 -Ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluor- methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-trifluormethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-methoxy-phe- nyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 -methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylami- no)-, 2-( 1 -Ethyl-3 -(2-difluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-difluor- methoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-trifluormethoxy-phenyl)-propylami- no)-, 1 -( 1 -Ethyl-3 -(3 -trifluormethoxy-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-tri- fluormethoxy-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-methoxycarbonyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-ethoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methoxycarbonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-ethoxycarbonyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-methylthio-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4- methylthio-phenyl)-proρylamino)-, 2-( 1 -Ethyl-3 -(2-methylsulfinyl-phenyl)-propyl- amino)-, 2-( 1 -Ethyl-3 -(4-methylsulfinyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2- methylsulfonyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(4-methylsulfonyl-phenyl)-pro- pylamino)-, 2-(l-Ethyl-3-(3,4-dichlor-phenyl)-propylamino)-,' 2-(l-Ethyl-3-(2,4-di- chlor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5-dichlor-phenyl)-propylamino)-, 2-( 1 - Ethyl-3-(2,6-dichlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,6-difluor-phenyl)-propyl- amino)-, 2-( 1 -Ethyl-3 -(2, 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2,4-difluor- phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(3 ,4-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl- 3 -(3 , 5-difluor-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-4-chlor-phenyl)-propyl- amino)-, 2-(l-Ethyl-3-(4-fluor-2-chlor-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2,4-di- methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2- ( 1 -Ethyl-3 -(3 , 5-dimethyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(2, 5-dimethyl-phenyl)- propylamino)-, 2-( 1 -Ethyl-3 -(2-chlor-6-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 - (4-fluor-2-methyl-phenyl)-propylamino)-, 2-(l-Ethyl-3-(2-fluor-4-methyl-phenyl)-pro- pylamino)-, 2-( 1 -Ethyl-3 -(2-fluor-5 -methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -(5 - fluor-2-methyl-phenyl)-propylamino)-, 2-( 1 -Ethyl-3 -thien-2-yl-propylamino)-, 2-( 1 - Ethyl-3 -thien-3 -yl-propylamino)-, 2-( 1 -Ethyl-3 -pyridin-2-yl-propylamino)-, 2-( 1 - Ethyl-3-pyridin-3-yl-propylamino)- und 2-(l-Ethyl-3-pyridin-4-yl-propylamino)- -4- chlor-6-methylsulfonyl- 1 ,3,5-triazin.2- (1-ethyl-3 - (2-methylphenyl) propylamino) -, 2- (1-ethyl-3 - (3-methylphenyl) propylamino) -, 2- (1-ethyl -3 - (4-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3 - trifluoromethylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-trifluoromethyl-phenyl) propylamino) -, 2- (1-ethyl-3 - (2-methoxyphenyl) propylamino ) -, 2- (1-Ethyl-3 - (3-methoxy-phenyl) propylamino) -, 2- (1-Ethyl-3 - (4-methoxy-phenyl) propylamino) -, 2- (1 - Ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino),, 2- (1-ethyl-3 - (2-difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2 -difluoromethoxy-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-trifluoromethoxy-phenyl) -propylamino) -, 1 - (1-ethyl-3 - (3-trifluoromethoxy-phenyl) ) -propylamino) -, 2- (1-ethyl-3 - (4-trifluoromethoxy-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-methoxycarbonyl-phenyl) -propylamino) -, 2- (1-Ethyl-3 - (2-ethoxycarbonylphenyl) propylamino) -, 2- (1-Ethyl-3 - (4-methoxycarbonylphenyl) propylami no) -, 2- (1-Ethyl-3 - (4-ethoxycarbonyl-phenyl) - propylamino) -, 2- (1-ethyl-3 - (2-methylthio-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4-methylthio-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (2-methylsulfinyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - (4-methylsulfinyl-phenyl) -propylamino) -, 2- (1 -Ethyl-3 - ( 2-methylsulfonylphenyl) propylamino) -, 2- (1-ethyl-3 - (4-methylsulfonylphenyl) propylamino) -, 2- (l-ethyl-3- (3,4-dichloro- phenyl) propylamino) -, ' 2- (l-ethyl-3- (2,4-di-chlorophenyl) propylamino) -, 2- (1-ethyl-3 - (2,5-dichlorophenyl ) -propylamino) -, 2- (1 - ethyl-3- (2,6-dichlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,6-difluorophenyl) propyl- amino) -, 2- (1-ethyl-3 - (2, 5-difluorophenyl) propylamino) -, 2- (1-ethyl-3 - (2,4-difluorophenyl) propylamino) -, 2- (1-Ethyl-3 - (3, 4-difluorophenyl) propylamino) -, 2- (1-Ethyl-3 - (3, 5-difluorophenyl) propylamino) -, 2- (1st -Ethyl-3 - (2-fluoro-4-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (4-fluoro-2-chlorophenyl) propylamino) -, 2- (l-ethyl-3- (2,4-dimethylphenyl) propylamino) -, 2- (l-ethyl l-3- (3,4-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (3, 5-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2,5-dimethyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-chloro-6-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (4th -fluoro-2-methyl-phenyl) -propylamino) -, 2- (l-ethyl-3- (2-fluoro-4-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (2-fluoro-5-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - (5-fluoro-2-methyl-phenyl) -propylamino) -, 2- (1-ethyl-3 - thien-2-yl-propylamino) -, 2- (1 - ethyl-3-thien-3-yl-propylamino) -, 2- (1-ethyl-3-pyridin-2-yl-propylamino) -, 2- (1 - ethyl-3-pyridin-3-yl-propylamino) - and 2- (l-ethyl-3-pyridin-4-yl-propylamino) - -4- chloro-6-methylsulfonyl- 1, 3,5- triazine.
Die Ausgangsstoffe der allgemeinen Formel (IV) sind noch nicht aus der Literatur bekannt; sie sind als neue Stoffe auch Gegenstand der vorliegenden Anmeldung.The starting materials of the general formula (IV) are not yet known from the literature; as new substances they are also the subject of the present application.
Man erhält die neuen substituierten Triazine der allgemeinen Formel (IV), wenn manThe new substituted triazines of the general formula (IV) are obtained if
Triazine der allgemeinen Formel (VIII)Triazines of the general formula (VIII)
X1 X 1
N ^ N (VIII)N ^ N (VIII)
N X° in welcherNX ° in which
X1 und Z die oben angegebene Bedeutung haben und X3 für Halogen steht,X 1 and Z have the meaning given above and X 3 represents halogen,
mit substituierten Alkylaminen der allgemeinen Formel (VI)with substituted alkylamines of the general formula (VI)
in welcherin which
R1, R2, A und Ar die oben angegebene Bedeutung haben,R 1 , R 2 , A and Ar have the meaning given above,
gegebenenfalls in Gegenwart eines Säureakzeptors, wie z.B. Ethyldiisopropylamin, und gegebenenfalls in Gegenwart eines Verdünnungsmittels, wie z.B. Tetrahydrofuran oder Dioxan, bei Temperaturen zwischen -50°C und +50°C umsetzt (vgl. die Herstellungsbeispiele).optionally in the presence of an acid acceptor, e.g. Ethyldiisopropylamine, and optionally in the presence of a diluent, e.g. Tetrahydrofuran or dioxane, at temperatures between -50 ° C and + 50 ° C (see. The manufacturing examples).
Die beim erfindungsgemäßen Verfahren (c) zur Herstellung von Verbindungen der Formel (I) als Ausgangsstoffe zu verwendenden substituierten Triazine sind durch dieThe substituted triazines to be used as starting materials in process (c) according to the invention for the preparation of compounds of the formula (I) are characterized by
Formel (V) allgemein definiert. In der Formel (V) hat Z vorzugsweise bzw. insbesondere diejenige Bedeutung, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) vorzugsweise bzw. als insbesondere bevorzugt für Z angegeben wurde; X2 steht vorzugsweise für Fluor, Chlor, Brom, Methoxy oder Ethoxy, insbesondere für Chlor doer Methoxy.Formula (V) generally defined. In formula (V), Z preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Z; X 2 preferably represents fluorine, chlorine, bromine, methoxy or ethoxy, in particular chlorine or methoxy.
Die Ausgangsstoffe der allgemeinen Formel (V) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. WO 95/11237). Die beim erfindungsgemäßen Verfahren (c) weiter als Ausgangsstoffe zu verwendenden substituierten Alkylamine sind durch die Formel (VI) allgemein definiert. In der Formel (VI) haben R1, R2, A und Ar vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) vorzugsweise bzw. als insbesondere bevorzugt für R1, R2, A und Ar angegeben wurden.The starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf. WO 95/11237). Formula (VI) provides a general definition of the substituted alkylamines to be used further as starting materials in process (c) according to the invention. In the formula (VI), R 1 , R 2 , A and Ar preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 , R 2 , A and Ar were given.
Die Ausgangsstoffe der allgemeinen Formel (VI) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. DE 3426919; DE 4000610; DE 4332738, EP 320898; EP 443606; Tetrahedron: Asymmetry 5 (1994), 817-820;The starting materials of the general formula (VI) are known and / or can be prepared by processes known per se (cf. DE 3426919; DE 4000610; DE 4332738, EP 320898; EP 443606; Tetrahedron: Asymmetry 5 (1994), 817-820 ;
Tetrahedron Lett. 29 (1988), 223-224; loc. cit. 36 (1995), 3917-3920; Herstellungsbeispiele).Tetrahedron Lett. 29: 223-224 (1988); loc. cit. 36: 3917-3920 (1995); Manufacturing examples).
Die erfindungsgemäßen Verfahren zur Herstellung der Verbindungen der Formel (I) werden gegebenenfalls unter Verwendung eines Reaktionshilfsmittels durchgeführt.The processes according to the invention for the preparation of the compounds of the formula (I) are optionally carried out using a reaction auxiliary.
Als Reaktionshilfsmittel für die Verfahren (a), (b) und (c) kommen im allgemeinen die üblichen anorganischen oder organischen Basen oder Säureakzeptoren in Betracht. Hierzu gehören vorzugsweise Alkalimetall- oder Erdalkalimetall- -acetate, -amide, -carbonate, -hydrogencarbonate, -hydride, -hydroxide oder -alkanolate, wie beispiels- weise Natrium-, Kalium- oder Calcium-acetat, Lithium-, Natrium-, Kalium- oderSuitable reaction auxiliaries for processes (a), (b) and (c) are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium - or
Calcium-amid, Natrium-, Kalium- oder Calcium-carbonat, Natrium-, Kalium- oder Calcium-hydrogencarbonat, Lithium-, Natrium-, Kalium- oder Calcium-hydrid, Lithium-, Natrium-, Kalium- oder Calcium-hydroxid, Natrium- oder Kalium- -methanolat, -ethanolat, -n- oder -i-propanolat, -n-, -i-, -s- oder -t-butanolat; weiterhin auch basische organische Stickstoffverbindungen, wie beispielsweise Tri- methylamin, Triethylamin, Tripropylamin, Tributylamin, Ethyl-diisopropylamin, N,N- Dimethyl-cyclohexylamin, Dicyclohexylamin, Ethyl-dicyclohexylamin, N,N-Dimethyl- anilin, N,N-Dimethyl-benzylamin, Pyridin, 2-Methyl-, 3-Methyl-, 4-Methyl-, 2,4-Di- methyl-, 2,6-Dimethyl-, 3,4-Dimethyl- und 3,5-Dimethyl-pyridin, 5-Ethyl-2-methyl- pyridin, 4-Dimethylamino-pyridin, N-Methyl-piperidin, l,4-Diazabicyclo[2,2,2]-octanCalcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane
(DABCO), l,5-Diazabicyclo[4,3,0]-non-5-en (DBN), oder 1,8-Diazabicyclo[5,4,0]- undec-7-en (DBU). Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren (a), (b) und (c) kommen vor allem inerte organische Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicyclische oder aromatische, gegebenenfalls halo- genierte Kohlenwasserstoffe, wie beispielsweise Benzin, Benzol, Toluol, Xylol, Chlor- benzol, Dichlorbenzol, Petrolether, Hexan, Cyclohexan, DichTormethan, Chloroform,(DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU). Inert organic solvents are particularly suitable as diluents for carrying out processes (a), (b) and (c) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform,
Tetrachlorkohlenstoff; Ether, wie Diethylether, Diisopropylether, Dioxan, Tetrahydrofuran oder Ethylenglykoldimethyl- oder -diethylether; Ketone, wie Methyl-isopropyl- keton oder Methyl-isobutyl-keton; Nitrile, wie Acetonitril, Propionitril oder Butyro- nitril; Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methyl-form- anilid, N-Methyl-pyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester, Sulfoxide, wie Dimethylsulfoxid, Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, Ethylenglykolmonomethylether, Ethylenglykolmonoethylether, Diethylenglykolmonomethylether, Diethylenglykol- monoethylether, deren Gemische mit Wasser oder reines Wasser.Carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as methyl isopropyl ketone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
Die Reaktionstemperaturen können bei der Durchführung der erfindungsgemäßen Verfahren (a), (b) und (c) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 300 °C, vorzugsweise zwischen 10°C und 250°C.The reaction temperatures can be varied within a substantial range when carrying out processes (a), (b) and (c). In general, temperatures between 0 ° C and 300 ° C, preferably between 10 ° C and 250 ° C.
Die erfindungsgemäßen Verfahren (a), (b) und (c) werden im allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, die erfindungsgemäßen Verfahren unter erhöhtem oder vermindertem Druck - im allgemeinen zwischen 0, 1 bar und 10 bar - durchzuführen.The processes (a), (b) and (c) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
Zur Durchführung der erfindungsgemäßen Verfahren werden die Ausgangsstoffe im allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, eine der Komponenten in einem größeren Überschuß zu verwenden. Die Umsetzung wird im allgemeinen in einem geeigneten Verdünnungsmittel in Gegen- wart eines Reaktionshilfsmittels durchgeführt und das Reaktionsgemisch wird im all- gemeinen mehrere Stunden bei der erforderlichen Temperatur gerührt. Die Aufarbeitung wird nach üblichen Methoden durchgeführt (vgl. die Herstellungsbeispiele).To carry out the processes according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally agitated several hours at the required temperature. Working up is carried out according to customary methods (cf. the production examples).
Die erfindungsgemäßen Wirkstoffe können als Defoliants, Desiccants, Krautab- tötungsmittel und insbesondere als Unkrautvernichtungsmitfel verwendet werden.The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
Unter Unkraut im weitesten Sinne sind alle Pflanzen zu verstehen, die an Orten aufwachsen, wo sie unerwünscht sind. Ob die erfindungsgemäßen Stoffe als totale oder selektive Herbizide wirken, hängt im wesentlichen von der angewendeten Menge ab.Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen verwendet werden:The active compounds according to the invention can e.g. can be used in the following plants:
Dikotyle Unkräuter der Gattungen: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium,Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium,
Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dikotyle Kulturen der Gattungen: Gossypium, Glycine, Beta, Daucus, Phaseolus,Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus,
Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monokotyle Unkräuter der Gattungen: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,
Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris.Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris.
Monokotyle Kulturen der Gattungen: Oryza, Zea, Triticum, Hordeum, Avena, Seeale,Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale,
Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. Die Verwendung der erfindungsgemäßen Wirkstoffe ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium. However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
Die Verbindungen eignen sich in Abhängigkeit von der Konzentration zur Total- unkrautbekämpfüng z.B. auf Industrie- und Gleisanlagen und auf Wegen und Plätzen mit und ohne Baumbewuchs. Ebenso können die Verbindungen zur Unkrautbekämpfung in Dauerkulturen, z.B. Forst, Ziergehölz-, Obst-, Wein-, Citrus-, Nuß-, Bananen-, Kaffee-, Tee-, Gummi-, Ölpalm-, Kakao-, Beerenfrucht- und Hopfen- anlagen, auf Zier- und Sportrasen und Weideflächen und zur selektiven Unkrautbekämpfung in einjährigen Kulturen eingesetzt werden.Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops.
Die erfindungsgemäßen Verbindungen der Formel (I) eignen sich insbesondere zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern in monokotylen und dikotylen Kulturen sowohl im Vorauflauf- als auch im Nachauflauf- Verfahren.The compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
Die Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkap seiungen in polymeren Stoffen.The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances .
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkyl- naphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wieIf water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as
Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage: z.B. Ammoniumsalze und natürlichePossible solid carriers are: e.g. Ammonium salts and natural
Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Mont- morillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkyl- arylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweiß- hydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.Rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospho- lipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarb- stoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 GewichtsprozentThe formulations generally contain between 0.1 and 95 percent by weight
Wirkstoff, vorzugsweise zwischen 0,5 und 90 %. Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formulierungen auch in Mischung mit bekannten Herbiziden zur Unkrautbekämpfung Verwendung finden, wobei Fertigformulierungen oder Tankmischungen möglich sind.Active ingredient, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
Für die Mischungen kommen bekannte Herbizide infrage, beispielsweise Acetochlor,Known herbicides are suitable for the mixtures, for example acetochlor,
Acifluorfen(-sodium), Aclonifen, Alachlor, Alloxydim(-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Ben- furesate, Bensulfuron(-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Biala- phos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlor- imuron(-ethyl), Chlor nitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cino- sulfuron, Clethodim, Clodinafop(-propargyl), Clomazone, Clopyralid, Clopyra- sulfuron, Cloransulam(-methyl), Cumyluron, Cyanazine, Cycloate, Cyclo- sulfamuron, Cycloxydim, Cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedi- pham, Diallate, Dicamba, Diclofop(-methyl), Difenzoquat, Diflufenican, Di- mefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Di- nitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron(-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop(-isopropyl), Flamprop(-isopropyl-L), Flamprop(- methyl), Flazasulfuron, Fluazifop(-butyl), Flumetsulam, Flumiclorac(-pentyl),Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl) Bialaphos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chloro-imuron (-ethyl), Chlor nitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cimosulfonon, Clon- sulfurod (-propargyl), Clomazone, Clopyralid, Clopyra-sulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2 , 4-DP, desmedipham, dialate, dicamba, diclofop (-methyl), difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, di-nitramine, diphenamide, diquat, dithiopyr, diuron, dymron , Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl ), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (- methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl),
Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen(- ethyl), Flupoxam, Flupropacil, Flurenol, Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate(-ammonium), Glyphosate(-isopropyl- ammonium), Halosafen, Haloxyfop(-ethoxyethyl), Hexazinone, Imazamethabenz(- methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazo- sulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron(-methyl), Molinate, Monolinuron, Napro- anilide, Napropamide, Neburon, Nicosulfuron, Norflurazon Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron(-methyl), Prometryn, Propachlor, Propanil, Propaquiza- fop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron(-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac(-sodium), Quinchlorac, Quin- merac, Quizalofop(-ethyl), Quizalofop(-p-tefuryl), Rimsulfuron, Sethoxydim,Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (- ethyl), Flupoxam, Flupropacil, Flurenol, Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropyl- ammonium ), Hexazinone, Imazamethabenz (- methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfonone, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Mef, MCP, MCP, MCP, MCP, MCP, MCP Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Napro-anilide, Napropamide, Neburon, Nicosulfuron, Norfluryzalin Orbencarb, Orbencarb, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquiza- fop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfidon, Pyrazosulfidon (Pyrazosulfuron) Pyrithiobac (-sodium), quinchlorac, quinmerac, quizalofop (-ethyl), quizalofop (-p-tefuryl), rimsulfuron, sethoxydim,
Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron(-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron(-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron(-methyl), Triclopyr, Tridiphane, Trifluralin und Triflusulfuron.Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben, Trallonium, Sulfuron, Trihydro -methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Pflanzennährstoffen und Bodenstruktur-verbesserungsmitteln ist möglich.A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Streuen.The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
Die erfindungsgemäßen Wirkstoffe können sowohl vor als auch nach dem Auflaufen der Pflanzen appliziert werden. Sie können auch vor der Saat in den Boden eingearbeitet werden.The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
Die angewandte Wirkstoffmenge kann in einem größeren Bereich schwanken. Sie hängt im wesentlichen von der Art des gewünschten Effektes ab. Im allgemeinen liegen die Aufwandmengen zwischen 1 g und 10 kg Wirkstoff pro Hektar Bodenfläche, vorzugsweise zwischen 5 g und 5 kg pro ha. Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe geht aus den nachfolgenden Beispielen hervor. The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha. The preparation and use of the active compounds according to the invention can be seen from the examples below.
Herstellungsbeispiele:Preparation Examples:
Beispiel 1example 1
Eine Mischung aus 2,0 g (7 mMol) (R/S)-l-(l-Ethyl-3-phenyl-propyl)-biguanid- Hydrochlorid (racemisch), 1,89 g (14 mMol) 2-Fluor-isobuttersäure-ethylester, 0,76 g (14 mMol) Natriummethylat und 12 ml Methanol wird ca. 15 Stunden bei ca. 22°C gerührt. Dann wird mit Wasser auf etwa das dreifache Volumen verdünnt, mit Essig- säureethylester geschüttelt, die organische Phase abgetrennt mit Wasser gewaschen, mit Natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel im Wasserstrahlvakuum sorgfältig abdestilliert. Der Rückstand wird durch Säulen- Chromatographie (Kieselgel, Essigsäureethylester) gereinigt.A mixture of 2.0 g (7 mmol) (R / S) -l- (l-ethyl-3-phenyl-propyl) -biguanide hydrochloride (racemic), 1.89 g (14 mmol) 2-fluoro- Ethyl isobutyrate, 0.76 g (14 mmol) of sodium methylate and 12 ml of methanol are stirred at about 22 ° C. for about 15 hours. The mixture is then diluted to about three times the volume with water, shaken with ethyl acetate, the organic phase is separated off with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum. The residue is purified by column chromatography (silica gel, ethyl acetate).
Man erhält 1,44 g (64% der Theorie) (R/S)-2-Amino-4-(l-fluor-l-methyl-ethyl)-6-(l- ethyl-3 -phenyl-propylamino)- 1,3,5 -triazin (Racemat) .1.44 g (64% of theory) of (R / S) -2-amino-4- (l-fluoro-l-methyl-ethyl) -6- (l-ethyl-3-phenyl-propylamino) - 1,3,5-triazine (racemate).
Analog Beispiel 1 sowie entsprechend der allgemeinen Beschreibung der erfindungsgemäßen Herstellungsverfahren können beispielsweise auch die in der nachstehenden Tabelle 1 aufgeführten Verbindungen der Formel (I) hergestellt werden.Analogously to Example 1 and in accordance with the general description of the production processes according to the invention, for example the compounds of the formula (I) listed in Table 1 below can also be prepared.
Tabelle 1: Beispiele für die Verbindungen der Formel (I) Table 1: Examples of the compounds of the formula (I)
Tabelle 1 (Fortsetzung) Table 1 (continued)
Tabelle 1 (Fortsetzung) Table 1 (continued)
Tabelle 1 (Fortsetzung) Table 1 (continued)
Tabelle 1 (Fortsetzung) Table 1 (continued)
Tabelle 1 (Fortsetzung) Table 1 (continued)
Tabelle 1 (Fortsetzung) Table 1 (continued)
Ausgangsstoffe der Formel (II):Starting materials of formula (II):
Beispiel (11-1Example (11-1
Eine Mischung aus 2,9 g (14,5 mMol) l-Ethyl-3-phenyl-propylamin-Hydrochlorid (racemisch), 1,22 g (14,5 mMol) Cyanoguanidin (Dicyandiamid) und 30 ml 1,2- Dichlor-benzol wird 8 Stunden auf 140°C bis 150°C erhitzt. Das nach Abkühlen kristallin angefallene Produkt wird durch Absaugen isoliert.A mixture of 2.9 g (14.5 mmol) of 1-ethyl-3-phenyl-propylamine hydrochloride (racemic), 1.22 g (14.5 mmol) of cyanoguanidine (dicyandiamide) and 30 ml of 1,2-dichloro -benzene is heated to 140 ° C to 150 ° C for 8 hours. The product obtained in crystalline form after cooling is isolated by suction.
Man erhält 3,6 g (87% der Theorie) l-(l-Ethyl-3-phenyl-propyl)-biguanid-Hydro- chlorid (Racemat).3.6 g (87% of theory) of l- (l-ethyl-3-phenyl-propyl) -biguanide hydrochloride (racemate) are obtained.
Die Umsetzung kann bei gleicher Temperatur auch ohne Lösungsmittel - d.h. in der Schmelze - durchgeführt werden.The reaction can also be carried out at the same temperature without a solvent - i.e. in the melt - be carried out.
Analog Beispiel (II- 1) können beispielsweise auch die in der nachstehenden Tabelle 2 aufgeführten Verbindungen der Formel (II) bzw. deren Hydrochloride hergestellt werden.Analogously to Example (II-1), it is also possible, for example, to prepare the compounds of the formula (II) listed in Table 2 below or their hydrochlorides.
Tabelle 2: Beispiele für die Verbindungen der Formel (II) - (Hydrochloride) Table 2: Examples of the compounds of the formula (II) - (hydrochloride)
Tabelle 2 (Fortsetzung) Table 2 (continued)
Ausgangsstoffe der Formel (V):Starting materials of formula (V):
Beispiel (V-lExample (V-l
Stufe 1step 1
Eine Mischung aus 19,3 g (0,134 Mol) Propionylessigsäure-ethylester, 7,5 g (0, 11 Mol) Natriumethylat, 60 ml Ethanol und 50 ml 10%iger wässriger Natronlauge wird bei Raumtemperatur (ca. 20°C) vorgelegt und nach Zutropfen von 12,6 g (0,10 Mol) Benzylchlorid wird die Reaktionsmischung ca. 5 Stunden bei ca. 60°C gerührt. Anschließend wird im Wasserstrahlvakuum eingeengt und der Rückstand mit 50 ml 10%iger Natronlauge 3 Stunden bei ca. 60°C gerührt. Dann wird mit 10%iger wässriger Salzsäure auf pH 4 gestellt und mit Diethylether geschüttelt. Die organischeA mixture of 19.3 g (0.134 mol) of ethyl propionyl acetate, 7.5 g (0.11 mol) of sodium ethylate, 60 ml of ethanol and 50 ml of 10% strength aqueous sodium hydroxide solution is initially introduced at room temperature (approx. 20 ° C.) and after 12.6 g (0.10 mol) of benzyl chloride are added dropwise, the reaction mixture is stirred at about 60 ° C. for about 5 hours. The mixture is then concentrated in a water jet vacuum and the residue is stirred at 50 ° C. for 3 hours with 50 ml of 10% sodium hydroxide solution. Then it is adjusted to pH 4 with 10% aqueous hydrochloric acid and shaken with diethyl ether. The organic
Phase wird mit Natriumsulfat getrocknet und filtriert. Das Filtrat wird im Wasserstrahlvakuum eingeengt und der Rückstand durch Säulenchromatographie (Kieselgel/Essigsäureethylester) gereinigt.Phase is dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is purified by column chromatography (silica gel / ethyl acetate).
Man erhält 13,9 g (85% der Theorie) l-Phenyl-pentan-3-on.13.9 g (85% of theory) of l-phenylpentan-3-one are obtained.
Stufe 2Level 2
Eine Mischung aus 13,9 g (86 mMol) l-Phenyl-pentan-3-on, 8,9 g (128 mMol) Hydroxylamin-Hydrochlorid und 10,1 g (128 mMol) Pyridin wird 2 Stunden bei ca. 75 °C gerührt. Nach Abkühlen wird mit Wasser/Essigsäureethylester geschüttelt, die organische Phase abgetrennt, mit Natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel im Wasserstrahlvakuum sorgfältig abdestilliert. Der Rückstand, der im wesentlichen die Verbindung l-Phenyl-pentan-3-on-oxim der obigen Formel enthält, wird ohne weitere Reinigung für die nächst Stufe eingesetzt. A mixture of 13.9 g (86 mmol) l-phenylpentan-3-one, 8.9 g (128 mmol) hydroxylamine hydrochloride and 10.1 g (128 mmol) pyridine is 2 hours at about 75 ° C stirred. After cooling, the mixture is shaken with water / ethyl acetate, the organic phase is separated off, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum. The residue, which essentially contains the compound l-phenylpentan-3-one oxime of the above formula, is used for the next step without further purification.
Stufe 3level 3
6,5 g (0, 17 Mol) Lithiumaluminiumhydrid in 130 ml Tetrahydrofuran werden unter Rühren zu einer Mischung aus dem gemäß Beschreibung von Stufe 2 erhaltenen Produkt und 130 ml Tetrahydrofuran gegeben und die Reaktionsmischung wird 30 Minuten bei ca. 60°C gerührt. Nach Abkühlen wird mit einer Lösung von 1 g Natriumhydroxid in 30 ml Wasser versetzt und die Mischung wird 30 Minuten bei ca. 60°C gerührt. Nach Abkühlen wird filtriert und das Filtrat im Wasserstrahlvakuum eingeengt. Der Rückstand wird durch Säulenchromatographie (Kieselgel, Essigsäure- ethylester) gereinigt.6.5 g (0.17 mol) of lithium aluminum hydride in 130 ml of tetrahydrofuran are added with stirring to a mixture of the product obtained as described in step 2 and 130 ml of tetrahydrofuran, and the reaction mixture is stirred at approx. 60 ° C. for 30 minutes. After cooling, a solution of 1 g of sodium hydroxide in 30 ml of water is added and the mixture is stirred at approx. 60 ° C. for 30 minutes. After cooling, the mixture is filtered and the filtrate is concentrated in a water jet vacuum. The residue is purified by column chromatography (silica gel, ethyl acetate).
Man erhält 6,3 g (45% der Theorie) (R/S)-l-Ethyl-3-phenyl-propylamin (Racemat). 6.3 g (45% of theory) of (R / S) -1-ethyl-3-phenyl-propylamine (racemate) are obtained.
Anwendungsbeispiele:Examples of use:
Beispiel A Pre-emergence-TestExample A Pre-emergence test
Lösungsmittel: 5 Gewichtsteile AcetonSolvent: 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Samen der Testpflanzen werden in normalen Boden ausgesät. Nach ca. 24 Stunden wird der Boden mit der Wirkstoffzubereitung begossen. Dabei hält man die Wassermenge pro Flächeneinheit zweckmäßigerweise konstant. Die Wirkstoffkonzentration in der Zubereitung spielt keine Rolle, entscheidend ist nur die Aufwandmenge des Wirkstoffs pro Flächeneinheit.Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle.After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
Es bedeuten:It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 100 % = totale Vernichtung0% = no effect (like untreated control) 100% = total destruction
In diesem Test zeigen beispielsweise die Verbindungen gemäß Herstellungsbeispiel 1, 2, 12, 19, 21, 22, 29, 33, 41 und 45 bei teilweise guter Verträglichkeit gegenüberIn this test, for example, the compounds according to Preparation Example 1, 2, 12, 19, 21, 22, 29, 33, 41 and 45 show with good compatibility in some cases
Kultuφflanzen, wie z.B. Mais, Weizen und Baumwolle, starke Wirkung gegen Unkräuter (vgl. Tabelle A).Cultivated plants, e.g. Corn, wheat and cotton, strong activity against weeds (see Table A).
In den nachfolgenden Tabellen bedeutet „ai." („active ingredient") = Wirkstoff.. Tabelle A Pre-emergence-Test/GewachshausIn the tables below, “ai.” Means “active ingredient”. Table A Pre-emergence test / greenhouse
WiikstoiV gemäß Aufwand- Mais Baum- Alope- Digi- Abu- Galium MatriHerstellungsbeispiel-Nr. menge (g ai /ha) wolle curus taria tilon cariaWiikstoiV according to effort- maize tree- alope- digi- abu- galium matriManufacturing sample no. amount (g ai / ha) wool curus taria tilon caria
500 100 100 100 100 100 m Ω m r- r σ> 500 100 100 100 100 100 m Ω m r- r σ>
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Weizen Baum- Cheno- Solanum Veronica Viola Herstellungsbeispiel-Nr. menge (g ai./ha) wolle podiumActive ingredient according to expenditure- Wheat tree- Cheno- Solanum Veronica Viola Production example no. amount (g ai./ha) wool podium
30 m (22) 500 100 100 100 100 Q m r r σ> 30 m (22) 500 100 100 100 100 Q mrr σ>
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Wei- Digi- Echi- Abu- Amaran- Da- Poly- Vero- Herstellungsbeispiel-Nr. menge (g ai./ha) zen taria nochloa tilon thus tura gonu nicaActive ingredient according to effort- Wei- Digi- Echi- Abu- Amaran- Da- Poly- Vero Production example no. quantity (g ai./ha) zen taria nochloa tilon thus tura gonu nica
.σ».σ »
(12) 500 80 100 100 100 100 100 100 (12) 500 80 100 100 100 100 100 100
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Wei- Digi- Echi- Abu- Amaran- Da- Poly- Vero- Herstellungsbeispiel-Nr. menge (g ai./ha) zen taria nochloa tilon thus tura gonu nicaActive ingredient according to effort- Wei- Digi- Echi- Abu- Amaran- Da- Poly- Vero Production example no. quantity (g ai./ha) zen taria nochloa tilon thus tura gonu nica
33 m Ω m (19) 500 100 100 100 100 100 100 100 r 33 m Ω m (19) 500 100 100 100 100 100 100 100 r
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Mais Abuti- Amaran- Sinapis Herstellungsbeispiel-Nr. menge (g ai./ha) Ion thusActive ingredient according to expenditure - corn Abuti- Amaran- Sinapis Preparation example no. amount (g ai./ha) Ion thus
(2) 1000 20 80 100 100 (2) 1000 20 80 100 100
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Alope- Setaria Abuti- Ama- Galium Herstellungsbeispiel-Nr. menge (g ai./ha) curus Ion ranthusActive ingredient according to effort - Alope- Setaria Abuti- Ama- Galium Preparation example no. quantity (g ai./ha) curus ion ranthus
(22) 1000 90 70 100 95 100 (22) 1000 90 70 100 95 100
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Alope- Setaria Abuti- Ama- Galium Herstellungsbeispiel-Nr. menge (g ai./ha) curus Ion ranthus Active ingredient according to effort - Alope- Setaria Abuti- Ama- Galium Preparation example no. quantity (g ai./ha) curus ion ranthus
(41) 1000 90 100 100 100 95(41) 1000 90 100 100 100 95
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Alope- Setaria Abuti- A a- Galium Herstellungsbeispiel-Nr. menge (g ai./ha) curus Ion ranthusActive ingredient according to effort - Alope- Setaria Abuti- A a- Galium Preparation example no. quantity (g ai./ha) curus ion ranthus
Tabelle A (Fortsetzung)Table A (continued)
Wirkstoff gemäß Aufwand- Alo- Setaria Abu- Ama- Sinapis Xan- Herstellungsbeispiel-Nr. menge (g ai./ha) pecurus tilon ranthus thiumActive ingredient according to effort - Alo- Setaria Abu- Ama- Sinapis Xan- Manufacturing example no. quantity (g ai./ha) pecurus tilon ranthus thium
33 0 m Ω (33) 1000 100 100 90 100 100 90 m33 0 m Ω (33) 1000 100 100 90 100 100 90 m
1414
.cn .cn
Beispiel BExample B
Post-emergence-TestPost emergence test
Lösungsmittel: 5 Gewichtsteile AcetonSolvent: 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die ange- gebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Mit der Wirkstoffzubereitung spritzt man Testpflanzen, welche eine Höhe von 5 - 15 cm haben so, daß die jeweils gewünschten Wirkstoffmengen pro Flächeneinheit ausgebracht werden. Die Konzentration der Spritzbrühe wird so gewählt, daß inTest plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in
1000 1 Wasser/ha die jeweils gewünschten Wirkstoffmengen ausgebracht werden.1000 1 water / ha the desired amounts of active ingredient are applied.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle.After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
Es bedeuten:It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 100 % = totale Vernichtung0% = no effect (like untreated control) 100% = total destruction
In diesem Test zeigen beispielsweise die Verbindungen gemäß Herstellungsbeispiel 1, 2, 4, 11, 12, 19, 22, 23, 24, 33, 41, 43, 44, 45 und 46 bei teilweise guter Verträglichkeit gegenüber Kultuφflanzen, wie z.B. Mais und Weizen, starke Wirkung gegen Unkräuter (vgl. Tabelle B). Tabelle B: Post-emergence-Test/GewächshausIn this test, for example, the compounds according to Preparation Example 1, 2, 4, 11, 12, 19, 22, 23, 24, 33, 41, 43, 44, 45 and 46 show with good tolerance to cultivated plants, such as corn and wheat , strong action against weeds (see Table B). Table B: Post emergence test / greenhouse
Wirkstoff gemäß Aufwand- Weizen Echino- Abutilon Datura Ipomoea VeronicaActive ingredient according to expenditure- Wheat Echino- Abutilon Datura Ipomoea Veronica
I lerstellungsbeispiel-Nr. menge (g ai./ha) chloaProduction example no. amount (g ai./ha) chloa
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Mais Setaria Ama- Xanthium Herstellungsbeispiel-Nr. menge (g ai./ha) ranthusActive ingredient according to expenditure - maize Setaria ama- xanthium preparation example no. quantity (g ai./ha) ranthus
(46) 1000 100 100 70 (46) 1000 100 100 70
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Weizen Echino- Setaria Ama- Ipo- Poly- Sola-Active ingredient according to expenditure- Wheat Echino- Setaria Ama- Ipo- Poly- Sola-
1 lerstellungsbeispiel-Nr. menge (g ai./ha) chloa ranthus moea gonum nu1 Production example no. amount (g ai./ha) chloa ranthus moea gonum nu
N3 CDN3 CD
(12) 500 10 90 95 100 100 100 100(12) 500 10 90 95 100 100 100 100
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Weizen Echino- Setaria Ama- Ipo- Poly- Sola- Herslellungsbeispiel-Nr. menge (g ai./ha) chloa ranthus oea gonu numActive ingredient according to expenditure- Wheat Echino- Setaria Ama- Ipo- Poly- Sol- Manufacture example no. quantity (g ai./ha) chloa ranthus oea gonu num
(1 1) 500 10 80 95 100 100 100 100 (1 1) 500 10 80 95 100 100 100 100
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Weizen Echino- Setaria Ama- Ipo- Poly- Sola- Herstellungsbeispiel-Nr. menge (g ai./ha) chloa ranthus moea gonum numActive ingredient according to expenditure- Wheat Echino- Setaria Ama- Ipo- Poly- Sola- Production example no. quantity (g ai./ha) chloa ranthus moea gonum num
(43) 500 10 90 100 100 100 100 (43) 500 10 90 100 100 100 100
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Alope- Seta- Abu- Ama- Galium Xan- Herstellungsbeispiel-Nr. menge (g ai./ha) curus ria tilon ranthus thiuActive ingredient according to effort- Alope- Seta- Abu- Ama- Galium Xan- Preparation example no. quantity (g ai./ha) curus ria tilon ranthus thiu
3J m Ω m3J m Ω m
(22) 1000 80 70 95 80 70 t(22) 1000 80 70 95 80 70 t
CDCD
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Alope- Seta- Abu- Ama- Galium Xan- Herstellungsbeispiel-Nr. menge (g ai./ha) curus ria tilon ranthus thiumActive ingredient according to effort- Alope- Seta- Abu- Ama- Galium Xan- Preparation example no. quantity (g ai./ha) curus ria tilon ranthus thium
(41) 1000 80 100 100 100 100 100 (41) 1000 80 100 100 100 100 100
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Alope- Seta- Abu- Ama- Galium Xan- Herstellungsbeispiel-Nr. menge (g ai./ha) curus ria tilon ranthus thiuActive ingredient according to effort- Alope- Seta- Abu- Ama- Galium Xan- Preparation example no. quantity (g ai./ha) curus ria tilon ranthus thiu
(2) 1000 70 100 100 100 100 100(2) 1000 70 100 100 100 100 100
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Alope- Seta- Abu- Ama- Galium Xan- Herstellungsbeispiel-Nr. menge (g ai./ha) curus ria tilon ranthus thiumActive ingredient according to effort- Alope- Seta- Abu- Ama- Galium Xan- Preparation example no. quantity (g ai./ha) curus ria tilon ranthus thium
(43)(43)
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Alope- Seta- Abu- Ama- Galiu Xan- Herstellungsbeispiel-Nr. menge (g ai./ha) curus ria tilon ranthus thiumActive ingredient according to effort- Alope- Seta- Abu- Ama- Galiu Xan- Preparation example no. quantity (g ai./ha) curus ria tilon ranthus thium
(44) (44)
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Alope- Seta- Abu- Ama- Galiuni Xan- Herstellungsbeispiel-Nr. enge (g ai./ha) curus ria tilon ranthus thiumActive ingredient according to effort- Alope- Seta- Abu- Ama- Galiuni Xan- Preparation example no. tight (g ai./ha) curus ria tilon ranthus thium
(45) (45)
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff gemäß Aufwand- Alope- Seta- Abu- Ama- Galium Xan- Herstellungsbeispiel-Nr. menge (g ai./ha) curus ria tilon ranthus ihiumActive ingredient according to effort- Alope- Seta- Abu- Ama- Galium Xan- Production example no. quantity (g ai./ha) curus ria tilon ranthus ihium
to to
(4) (4)
Tabelle B (Fortsetzung)Table B (continued)
Wirkstoff" gemäß Aufwand- Alope- Avena Cy- Se- Abu- Ama- Sina- Xan- Herstellungsbeispiel-Nr. enge (g ai./ha) curus fatua perus taria tilon ranthus pis thiumActive ingredient " according to effort- Alope- Avena Cy- Se- Abu- Ama- Sina- Xan- Production Example No. close (g ai./ha) curus fatua perus taria tilon ranthus pis thium
(33) 1000 80 100 90 100 100 100 100 (33) 1000 80 100 90 100 100 100 100

Claims

Patentansprücheclaims
1. Substituierte 2-Amino-4-alkylamino-l,3,5-triazine der allgemeinen Formel (I)1. Substituted 2-amino-4-alkylamino-l, 3,5-triazines of the general formula (I)
in welcherin which
R1 für jeweils gegebenenfalls substituiertes Alkyl mit 2 bis 6 Kohlenstoffatomen oder Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht,R 1 represents in each case optionally substituted alkyl having 2 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,
R2 für Wasserstoff oder für Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R 2 represents hydrogen or alkyl having 1 to 4 carbon atoms,
A für Sauerstoff oder Methylen steht,A represents oxygen or methylene,
Ar für jeweils gegebenenfalls substituiertes Phenyl, Naphthyl oder Heterocyclyl steht, undAr stands for optionally substituted phenyl, naphthyl or heterocyclyl, and
Z für Wasserstoff, für Halogen oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylcarbonyl, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkenyl oder Alkinyl steht.Z represents hydrogen, halogen or optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl or alkynyl.
2. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß darin2. Compounds of formula (I) according to claim 1, characterized in that therein
R1 für gegebenenfalls durch Hydroxy, Cyano, Halogen oder C1-C4- Alkoxy substituiertes Alkyl mit 2 bis 4 Kohlenstoffatomen oder für ge- gebenenfalls durch Cyano, Halogen oder C1-C4- Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht,R 1 for alkyl with 2 to 4 carbon atoms optionally substituted by hydroxy, cyano, halogen or C1-C4-alkoxy or for optionally cycloalkyl with 3 to 6 carbon atoms substituted by cyano, halogen or C1-C4-alkyl,
R2 für Wasserstoff, Methyl oder Ethyl steht,R 2 represents hydrogen, methyl or ethyl,
A für Sauerstoff oder Methylen steht,A represents oxygen or methylene,
Ar für jeweils gegebenenfalls substituiertes Phenyl, Naphthyl oder Heterocyclyl steht, wobei die möglichen Heterocyclylgruppierungen aus der folgendenAr stands for optionally substituted phenyl, naphthyl or heterocyclyl, the possible heterocyclyl groupings from the following
Gruppe ausgewählt sind:Group are selected:
Furyl, Benzofuryl, Dihydrobenzofuryl, Tetrahydrofuryl, Thienyl, Benzothienyl, Thiazolyl, Benzthiazolyl, Oxazolyl, Benzoxazolyl, Thia- diazolyl, Oxadiazolyl, Pyrazolyl, Pyrrolyl, Chinolinyl, Isochinolinyl, Pyridinyl und Pyrimidinyl, und wobei die möglichen Substituenten jeweils aus folgender Gruppe ausgewählt sind:Furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxazolyl, thidiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl, each of which are selected from the group consisting of substituid and pyrimidinyl
Hydroxy, Cyano, Nitro, Halogen, jeweils gegebenenfalls durch Hydroxy, Cyano oder Halogen substituiertes Alkyl oder Alkoxy mit jeweils 1 bis 6 Kohlenstoffatomen, jeweils gegebenenfalls durchHydroxy, cyano, nitro, halogen, each optionally substituted by hydroxy, cyano or halogen-substituted alkyl or alkoxy each having 1 to 6 carbon atoms, each optionally by
Halogen substituiertes Alkylcarbonyl, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro, Halogen, C1 -C4- Alkyl, Cι-C4~Halogenalkyl, Cι -C4-Alkoxy oder Cι-C4-Halogenalkoxy substiuiertes Phenyl oder Phenoxy, sowie jeweils gegebenenfalls durch Halogen substituiertes Methylendioxy oder Ethylendioxy,Halogen substituted alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, each optionally by hydroxy, cyano, nitro, halogen, C1-C4-alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy substituted phenyl or phenoxy, and in each case optionally substituted by halogen methylenedioxy or ethylenedioxy,
undand
für Wasserstoff, für Halogen, für jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro, Halogen, Cι-C4-Alko y, Cι-C4-Alkyl- carbonyl, Cι-C4-Alkoxy-carbonyl, C1 -C4- Alkylthio, C1-C4- Alkyl- sulfinyl oder Cι-C4-Alkylsulfonyl substituiertes Alkyl, Alkoxy, Alkylcarbonyl, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl oder Alkinyl mit jeweils 2 bis 6 Kohlenstoffatomen steht.for hydrogen, for halogen, each optionally by hydroxy, cyano, nitro, halogen, -C-C4-Alko y, -C-C4-alkylcarbonyl, Cι-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4 - alkyl sulfinyl or -CC-C4-alkylsulfonyl substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, or for each optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms.
3. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß darin3. Compounds of formula (I) according to claim 1, characterized in that therein
R1 für jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor, Chlor,R 1 for each optionally by hydroxy, cyano, fluorine, chlorine,
Methoxy oder Ethoxy substituiertes Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht,Methoxy or ethoxy substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl or represents in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R2 für Wasserstoff oder Methyl steht,R 2 represents hydrogen or methyl,
A für Sauerstoff oder Methylen steht,A represents oxygen or methylene,
Ar für jeweils gegebenenfalls substituiertes Phenyl, Naphthyl oder Heterocyclyl steht, wobei die möglichen Heterocyclylgruppierungen aus der folgenden Gruppe ausgewählt sind: Furyl, Benzofüryl, Dihydrobenzofuryl, Tetrahydrofüryl, Thienyl, Benzothienyl, Thiazolyl, Benzthiazolyl, Oxazolyl, Benzoxazolyl, Thia- diazolyl, Oxadiazolyl, Pyrazolyl, Pyrrolyl, Chinolinyl, Isochinolinyl, Pyridinyl und Pyrimidinyl, und wobei die möglichen Substituenten jeweils aus folgender Gruppe ausgewählt sind: Hydroxy, Cyano, Nitro, Fluor, Chlor, Brom, jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i- Propoxy, n-, i-, s- oder t-Butoxy, jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Acetyl, PropionyL n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro,Ar stands for optionally substituted phenyl, naphthyl or heterocyclyl, the possible heterocyclyl groupings being selected from the following group: furyl, benzofüryl, dihydrobenzofuryl, tetrahydrofüryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxadoliazolyl, oxoxazolylol, benzoxazolylol , Pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl, and where the possible substituents are each selected from the following group: hydroxyl, cyano, nitro, fluorine, chlorine, bromine, each methyl, ethyl optionally substituted by hydroxy, cyano, fluorine or chlorine, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, each optionally by fluorine or chlorine-substituted acetyl, propionyl n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, each optionally by hydroxy, cyano, nitro,
Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl oder Phenoxy, sowie jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Methylendioxy oder Ethylendioxy,Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s - or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenoxy, and also methylene dioxy or ethylenedioxy optionally substituted by fluorine or chlorine,
undand
Z für Wasserstoff, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Z for hydrogen, fluorine, chlorine, bromine, for each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methoxy, ethoxy, n- or i-
Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i- Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i- Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, oder für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes Ethenyl, Propenyl, Butenyl, Ethinyl, Propinyl oder Butinyl steht.Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or for ethenyl, propenyl, butenyl, butenyl, ethynyl, propynyl or optionally substituted by fluorine, chlorine or bromine Butinyl stands.
4. Verfahren zur Herstellung von Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß man4. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that
(a) substituierte Biguanide der allgemeinen Formel (II) (a) substituted biguanides of the general formula (II)
in welcherin which
R1, R2, A und Ar die in Anspruch 1 angegebene Bedeutung haben,R 1 , R 2 , A and Ar have the meaning given in claim 1,
- und/oder Säureaddukte von Verbindungen der allgemeinen Formel (II) -and / or acid adducts of compounds of the general formula (II)
mit Alkoxycarbonylverbindungen der allgemeinen Formel (III)with alkoxycarbonyl compounds of the general formula (III)
in welcherin which
Z die in Anspruch 1 angegebene Bedeutung hat undZ has the meaning given in claim 1 and
R' für Alkyl steht,R 'represents alkyl,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
oder daß manor that one
(b) substituierte Triazine der allgemeinen Formel (IV)(b) substituted triazines of the general formula (IV)
X1 N ^ N R1 (IV)X 1 N ^ NR 1 (IV)
H R2 in welcherHR 2 in which
R1, R2, A, Ar und Z die oben angegebene Bedeutung haben undR 1 , R 2 , A, Ar and Z have the meaning given above and
X1 für Halogen oder Alkoxy steht,X 1 represents halogen or alkoxy,
mit Ammoniak gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,with ammonia, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
oder daß manor that one
(c) substituierte Triazine der allgemeinen Formel (V)(c) substituted triazines of the general formula (V)
in welcherin which
Z die oben angegebene Bedeutung hat undZ has the meaning given above and
X2 für Halogen oder Alkoxy steht,X 2 represents halogen or alkoxy,
mit substituierten Alkylaminen der allgemeinen Formel (VI)with substituted alkylamines of the general formula (VI)
in welcher R1, R2, A und Ar die oben angegebene Bedeutung haben,in which R 1 , R 2 , A and Ar have the meaning given above,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
und gegebenenfalls an den gemäß den unter (a), (b) oder (c) beschriebenen Verfahren erhaltenen Verbindungen der allgemeinen Formel (I) im Rahmen der obigen Substituentendefinition weitere Umwandlungen nach üblichen Methoden durchführt.and optionally on the compounds of the general formula (I) obtained according to the processes described under (a), (b) or (c), as part of the above definition of substituents, by further conversions by customary methods.
Herbizide Mittel, gekennzeichnet durch einen Gehalt an mindestens einer Verbindung der Formel (I) gemäß Anspruch 1.Herbicidal agents, characterized in that they contain at least one compound of the formula (I) according to Claim 1.
6. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 zur Bekämpfung von unerwünschtem Pflanzenwachstum.6. Use of compounds of formula (I) according to claim 1 for combating undesirable plant growth.
7. Verfahren zur Bekämpfung von Unkräutern, dadurch gekennzeichnet, daß man Verbindungen der Formel (I) gemäß Anspruch 1 auf die Unkräuter oder ihren Lebensraum einwirken läßt.7. A method of combating weeds, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on the weeds or their habitat.
8. Verfahren zur Herstellung von herbiziden Mitteln, dadurch gekennzeichznet, daß man Verbindungen der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Mitteln vermischt.8. A process for the preparation of herbicidal compositions, characterized in that compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents.
9. Substituierte Triazine der allgemeinen Formel (IV),9. Substituted triazines of the general formula (IV),
in welcher R1, R2, A, Ar und Z die in Anspruch 1 angegebene Bedeutung haben undin which R 1 , R 2 , A, Ar and Z have the meaning given in claim 1 and
X1 für Halogen oder Alkoxy steht.X 1 represents halogen or alkoxy.
10. Substituierte Biguanide der allgemeinen Formel (II),10. Substituted biguanides of the general formula (II),
in welcherin which
R1, R2, A und Ar die in Anspruch 1 angegebene Bedeutung haben,R 1 , R 2 , A and Ar have the meaning given in claim 1,
und/oder Säureaddukte von Verbindungen der allgemeinen Formel (II). and / or acid adducts of compounds of the general formula (II).
EP97910378A 1996-10-10 1997-09-29 Substituted 2-amino-4-alkylamino-1,3,5-triazines as herbicides Withdrawn EP0934284A1 (en)

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