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WO2002010160A2 - Heterocyclyl alkyl amino 1,3,5-triazines substituees - Google Patents

Heterocyclyl alkyl amino 1,3,5-triazines substituees Download PDF

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Publication number
WO2002010160A2
WO2002010160A2 PCT/EP2001/008386 EP0108386W WO0210160A2 WO 2002010160 A2 WO2002010160 A2 WO 2002010160A2 EP 0108386 W EP0108386 W EP 0108386W WO 0210160 A2 WO0210160 A2 WO 0210160A2
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WIPO (PCT)
Prior art keywords
cyano
substituted
methyl
carbon atoms
halogen
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PCT/EP2001/008386
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German (de)
English (en)
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WO2002010160A3 (fr
Inventor
Stefan Herrmann
Wolf-Rüdiger KOTYSCH
Kristian Kather
Stefan Lehr
Hans-Jochem Riebel
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
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Bayer Cropscience 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 Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to AU2002210423A priority Critical patent/AU2002210423A1/en
Publication of WO2002010160A2 publication Critical patent/WO2002010160A2/fr
Publication of WO2002010160A3 publication Critical patent/WO2002010160A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the invention relates to new substituted heterocyclylalkylarnino-l, 3,5-triazme, processes for their preparation, intermediates for their production, ner processes for
  • R 1 for optionally by amino, ⁇ itro, cyano, carbamoyl, thiocarbamoyl, halogen, or by alkyl, alkoxy or alkoxycarbonyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having up to 6 carbon atoms, or by in each case by optionally ⁇ itro, cyano, halogen, C 1 -C 4 alkyl, dC / t -haloalkyl, C 1 -C 4 alkoxy or
  • R 2 represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C.-C 4 alkoxy or for optionally substituted by cyano,
  • R 3 for hydrogen, for halogen, for alkyl with 1 to 6 carbon atoms substituted by cyano, halogen, hydroxy, C.-C 4 -alkoxy or C.-C 4 -alkylthio, for each optionally by cyano, halogen or C.- C 4 - Alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, or for optionally by Cyano, halogen or C.-C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
  • R 4 represents hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C.-C 4 alkoxy, and
  • R 5 represents hydrogen, formyl or alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl, each of which has 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or C.-C 4 alkoxy,
  • R 4 R 5 also represents alkylaminoalkylamino or dialkylarnmoalkylideneamino, each having up to 6 carbon atoms in the alkyl groups or alkylidene groups,
  • R 1 preferably represents optionally by amino, nitro, cyano, carbamoyl,
  • R 2 preferably represents optionally cyano-, halogen or C.-C 3 - alkoxy-substituted alkyl having 1 to 5 carbon atoms, or represents optionally cyano-, halogen or C.-C 3 alkyl substituted cycloalkyl having 3 to 6 carbon atoms.
  • R 3 preferably represents hydrogen, halogen, alkyl substituted by cyano, halogen, hydroxy, C 3 -C 3 -alkoxy or C 1 -C 3 -alkylthio, with 1 to 5 carbon atoms, each optionally substituted by cyano, halogen or C 1 -C 3 alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl each having 1 to 5 carbon atoms in the alkyl groups, each optionally substituted by halogen
  • R 4 preferably represents hydrogen or alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, halogen or C.-C 3 alkoxy.
  • R 5 preferably represents hydrogen, forrnyl or for alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl, each of which has 1 to 5 carbon atoms in the alkyl groups, which is optionally substituted by cyano, halogen or C.-C 3 alkoxy.
  • the grouping N preferably also represents alkylaminoalkylidene amino or dialkylaminoalkylidene amino each having up to 5 carbon atoms in the alkyl groups or alkylidene groups.
  • R 1 particularly preferably represents in each case optionally substituted by amino, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or by methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or by in each case optionally by nitro, cyano, fluorine, chlorine , Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy
  • R 2 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or in each case cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl.
  • R particularly preferably represents hydrogen, fluorine, chlorine, bromine, in each case optionally substituted by cyano, fluorine, chlorine, bromine, hydroxy, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio Methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, for each acetyl, propionyl, n- or optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,
  • R 4 particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
  • R 5 particularly preferably stands for hydrogen, for formyl or for any substituted by cyano, fluorine, chlorine, methoxy or ethoxy
  • the grouping N particularly preferably also represents alkylaminoalkylidene amino or dialkylaminoalkylidene amino, each having up to 3 carbon atoms in the alkyl groups or alkylidene groups.
  • R 1 very particularly preferably represents optionally substituted by nitro, cyano, fluorine, chlorine, bromine, or by methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or by in each case optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or pyridyl.
  • R very particularly preferably represents in each case optionally by fluorine or
  • R very particularly preferably represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine or chlorine, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
  • R 4 very particularly preferably represents hydrogen, methyl or ethyl.
  • R very particularly preferably represents hydrogen, formyl, methyl or
  • Ethyl or for acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.
  • the grouping N (R 4 R 5 ) very particularly preferably also represents dimethylaminomethyleneamino.
  • R most preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine or chlorine.
  • R 4 most preferably represents hydrogen.
  • R 5 most preferably stands for hydrogen, for formyl, or for methoxycarbonyl or ethoxycarbonyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.
  • the general or preferred residues 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. These residual definitions can be combined with one another, that is, also between the specified preferred ranges.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • alkyl or alkenyl are in each case straight-chain or branched as far as possible, even in conjunction with heteroatoms, such as in alkoxy.
  • Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitution the substituents can be the same or different.
  • 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 diasteromeric forms.
  • the invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general
  • the new substituted heterocyclylal] cylamino-1,3,5-triazines of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.
  • R 3 has the meaning given above and
  • R ' represents alkyl, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent
  • R5 preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for Rl, R ⁇ , R4 and R5.
  • 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.
  • reaction auxiliary such as hydrogen chloride
  • diluent such as toluene, n-decane or 1,2-dichlorobenzene
  • the biguanides of the general formula (II) can also be used directly for the preparation of the compounds of the general formula (I) by the process according to the invention, without intermediate isolation.
  • Formula (III) provides a general definition of the alkoxycarbonyl compounds to be used as starting materials in the process according to the invention for the preparation of Neritatien of the general formula (I).
  • R preferably or in particular has the meaning which has already been mentioned above in connection with the description of the inventive compounds of the general formula (I), preferably or as particularly preferred, for R 3 ;
  • R ' preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
  • the starting materials of the general formula (III) are known synthetic chemicals.
  • the process according to the invention for producing the compounds of the general formula (I) is preferably carried out using a reaction auxiliary.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as 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 trimethylamine, trifethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-dimethylcyclohexyl
  • aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tefrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone 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.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process 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 stirred at the required temperature for several hours.
  • the up work is carried out according to customary methods (cf. the manufacturing 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:
  • Scirpus, Setaria, Sorghum Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on
  • the active compounds according to the invention 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 pasture areas and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for selective use
  • the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • Plants are understood to mean all plants and plant populations, such as wanted and unwanted wild plants or crops (including naturally occurring crops).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those by
  • Plant variety rights of protectable or non-protectable plant varieties Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
  • the active ingredients can be converted into the usual formulations, such as
  • Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary 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.
  • 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,
  • emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol
  • Ethers e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching 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, for example 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 of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be mixed with known herbicides and / or with substances which
  • safeners Improving crop compatibility
  • ready-to-use formulations or tank mixes being possible.
  • Mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Arnidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenimole, cafenimole Carbetamides, Carfentrazone (-ethyl), Chlomefhoxyfen, Chlor
  • Diflufenican Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimetha- metryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, EthobenzanidPhenox, Fenox Flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,
  • Flumetsulam Flumetsulam, flumiclorac (-pentyl), flnmioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridyl-fluridyl-fluridyl-fluridyl-fluridyl-fluridyl ), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-isopropylammonium),
  • Halosafen Haloxyfop (-ethoxyethyl, -P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, hnazosulfuron, Iodosulfuron (-methyl, -sodium), Ialinolophenil Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotrione, Metamitron, Metazachlor, Metha benzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolacholamiboramamibor metsulfuron (-methyl), molinate, monolinuron, Napro- anilides, napropamide,
  • Piperophos Pretilachlor, Primisulfuron (-methyl), Profluazol, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosul possiblyon, Pyraflufen (-ethyl), Pyrazogyl, Pyrazolonate, Pyrazolonate Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyridatol, Pyriftalid, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl, -P-tefuryl), Rimsulfuron, Simine , Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulf
  • 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 calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the
  • a solution of 20 g of sodium hydroxide in 80 ml of water is added to a mixture of 44 g of l- (2-methyl-thiazol-5-yl) ethanone, 20 g of hydroxylamine hydrochloride and 150 ml of methanol at 20 ° C. to 40 ° C. given dropwise.
  • the reaction mixture is then stirred for 15 hours at room temperature (approx. 20 ° C.) and then concentrated under reduced pressure. The residue is dissolved in acetone and filtered.
  • the solvent is carefully distilled off from the filtrate under reduced pressure.
  • Literature known; as a new substance, it is also the subject of the present application.
  • 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 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the concentration of active ingredient in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants which have 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

La présente invention concerne des hétérocyclyl alkyl amino-1,3,5-triazines substituées de formule générale (I) dans laquelle R?1, R2, R3, R4, et R5¿ correspondent aux éléments indiqués dans la description, leur utilisation en tant qu'herbicides sélectifs, ainsi qu'un procédé et des produits intermédiaires permettant leur préparation.
PCT/EP2001/008386 2000-08-02 2001-07-20 Heterocyclyl alkyl amino 1,3,5-triazines substituees WO2002010160A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002210423A AU2002210423A1 (en) 2000-08-02 2001-07-20 Substituted heterocyclyl alkylamino-1,3,5-triazines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10037618.5 2000-08-02
DE2000137618 DE10037618A1 (de) 2000-08-02 2000-08-02 Substituierte Heterocyclylakylamino-1,3,5-triazine

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WO2002010160A2 true WO2002010160A2 (fr) 2002-02-07
WO2002010160A3 WO2002010160A3 (fr) 2002-08-01

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PCT/EP2001/008386 WO2002010160A2 (fr) 2000-08-02 2001-07-20 Heterocyclyl alkyl amino 1,3,5-triazines substituees

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DE (1) DE10037618A1 (fr)
WO (1) WO2002010160A2 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103254144A (zh) * 2013-04-12 2013-08-21 武汉工程大学 一种三聚氯氰衍生物及其制备方法和应用
WO2015150541A1 (fr) 2014-04-03 2015-10-08 Basf Se Composé diaminotriazine utile en tant qu'herbicide
US10029992B2 (en) 2014-04-23 2018-07-24 Basf Se Diaminotriazine compounds and their use as herbicides
US10479777B2 (en) 2013-07-16 2019-11-19 Basf Se Herbicidal azines
US10941122B2 (en) 2014-04-11 2021-03-09 Basf Se Diaminotriazine derivatives as herbicides

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DE19604191A1 (de) * 1996-02-06 1997-08-07 Hoechst Schering Agrevo Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE19755016A1 (de) * 1997-12-11 1999-06-17 Bayer Ag Substituierte 2,4-Diamino-1,3,5-triazine
DE19925329A1 (de) * 1998-06-16 1999-12-23 Hoechst Schering Agrevo Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
DE19604191A1 (de) * 1996-02-06 1997-08-07 Hoechst Schering Agrevo Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE19755016A1 (de) * 1997-12-11 1999-06-17 Bayer Ag Substituierte 2,4-Diamino-1,3,5-triazine
DE19925329A1 (de) * 1998-06-16 1999-12-23 Hoechst Schering Agrevo Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103254144A (zh) * 2013-04-12 2013-08-21 武汉工程大学 一种三聚氯氰衍生物及其制备方法和应用
CN103254144B (zh) * 2013-04-12 2015-10-28 武汉工程大学 一种三聚氯氰衍生物及其制备方法和应用
US10479777B2 (en) 2013-07-16 2019-11-19 Basf Se Herbicidal azines
WO2015150541A1 (fr) 2014-04-03 2015-10-08 Basf Se Composé diaminotriazine utile en tant qu'herbicide
CN106132948A (zh) * 2014-04-03 2016-11-16 巴斯夫欧洲公司 可用作除草剂的二氨基三嗪化合物
US10941122B2 (en) 2014-04-11 2021-03-09 Basf Se Diaminotriazine derivatives as herbicides
US10029992B2 (en) 2014-04-23 2018-07-24 Basf Se Diaminotriazine compounds and their use as herbicides

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AU2002210423A1 (en) 2002-02-13
WO2002010160A3 (fr) 2002-08-01

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