WO2001068616A1 - 1-aryl-cyclopropylmethylamino-1,3,5-triazines substituees - Google Patents

1-aryl-cyclopropylmethylamino-1,3,5-triazines substituees Download PDF

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Publication number
WO2001068616A1
WO2001068616A1 PCT/EP2001/002439 EP0102439W WO0168616A1 WO 2001068616 A1 WO2001068616 A1 WO 2001068616A1 EP 0102439 W EP0102439 W EP 0102439W WO 0168616 A1 WO0168616 A1 WO 0168616A1
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WIPO (PCT)
Prior art keywords
methyl
chlorine
fluorine
ethyl
substituted
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PCT/EP2001/002439
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German (de)
English (en)
Inventor
Stefan Herrmann
Hans-Jochem Riebel
Kristian Kather
Stefan Lehr
Mark-Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
Christoph Erdelen
Peter Lösel
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Bayer Aktiengesellschaft
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Priority to AU2001248330A priority Critical patent/AU2001248330A1/en
Publication of WO2001068616A1 publication Critical patent/WO2001068616A1/fr

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    • 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
    • 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
    • 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

Definitions

  • the invention relates to new substituted l-aryl-cyclopropylmethylamino-l, 3,5-triazines, ner processes for their preparation and their use as plant treatment agents, in particular as herbicides and as insecticides.
  • Ar represents in each case optionally substituted by hydroxyl, nitro, cyano, formyl, carboxyl, carbamoyl, thiocarbamoyl, halogen, C ⁇ -C 4 -alkyl, C haloalkyl, C ⁇ -C 4 -alkoxy, C 4 haloalkoxy, C ⁇ - C -alkylthio, C * -C 4 -haloalkyl-thio, -C-C 4 -alkylsulfmyl, C ⁇ -C 4 -haloalkylsulfmyl, C ⁇ -C -alkylsulfonyl, C ⁇ -C 4 -haloalkylsulfonyl, C ⁇ -C 4 -alkyl carbonyl, C 1 -C 4 alkoxycarbonyl, phenyl or phenoxy substituted phenyl, naphthyl, furyl.
  • R 1 for hydrogen, halogen, in each case optionally by hydroxy, cyano, halogen, C r C 4 alkoxy, C 1 -C 4 alkylthio, CC 4 alkyl sulfmyl or C 1 -C 4 - Alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each optionally substituted by halogen-substituted alkenyl or alkynyl each having up to 6 carbon atoms, or optionally cycloalkyl substituted by cyano, halogen or C] -C 4 -alkyl 3 to 6 carbon atoms,
  • R 2 represents hydrogen or alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or CC 4 alkoxy, and
  • R 3 represents hydrogen, formyl, in each case optionally by cyano, halogen or
  • 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) 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 stereoisomeric compounds.
  • radicals R 1 , R 2 and R 3 are substituents with asymmetrically substituted carbon atoms, both the diastereomer mixtures which are possible in each case and the individual possible diastereomers are the subject of the invention.
  • Ar preferably represents in each case optionally by hydroxyl, nitro, cyano, formyl, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylmethyl , Trifluoromethylthio, chlorodifluoromethylthio, methyl
  • R preferably represents hydrogen, fluorine, chlorine, bromine, in each case optionally by hydroxy, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, n- or i-pro - pylsulfinyl, 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, n
  • R preferably represents hydrogen or methyl or ethyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
  • R 3 preferably represents hydrogen, formyl, in each case optionally by
  • Ar particularly preferably represents in each case optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, trifluoromethylthio,
  • R 1 particularly preferably represents in each case optionally by hydroxy, fluorine,
  • R, 2 particularly preferably represents hydrogen, methyl or ethyl.
  • R 3 particularly preferably represents hydrogen, formyl, methyl or ethyl, or acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl optionally substituted by fluorine, chlorine, methoxy or ethoxy , Methylaminocarbonyl, ethyl aminocarbonyl, n- or i-propylaminocarbonyl.
  • Ar very particularly preferably represents in each case optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, methylsulfmyl, ethylsulfinyl, trifluoromethylsulfyl, methylsulfyl , Trifluoromethylsulfonyl, methoxycarbonyl or ethoxycarbonyl substituted phenyl or thienyl.
  • R 1 very particularly preferably represents methyl, ethyl, n-, i- or cyclo-propyl, each optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl.
  • R very particularly preferably represents hydrogen.
  • R 3 very particularly preferably represents hydrogen, formyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or phenylcarbonyl.
  • 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. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • Preferred compounds according to the invention are those of the formula (I) in which there is a combination of the meanings listed above as preferred. Particularly preferred according to the invention are those compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
  • the new substituted l-aryl-cyclopropylmethylamino-1,3,5-triazines of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal and insecticidal activity.
  • R has the meaning given above and R 'represents alkyl
  • the biguanides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (II).
  • Ar, R and R preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for Ar, R 2 and R 3 have been given.
  • Suitable acid adducts of compounds of 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.
  • 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.
  • 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.
  • the arylalkylamines of the general formula (IV) required as products are known and / or can be prepared by processes known per se (cf. DE-A-2526965, US-A-3781443, US-A-3840524, preparation examples).
  • 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 compounds of the general formula (I).
  • R 1 preferably or in particular has those meanings which have already been given above or in connection with the description of the compounds of the general formula (I) according to the invention as preferred or as particularly preferred for R 1 ;
  • 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.
  • diluents for carrying out the process according to the invention are in particular inert organic solvents. 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, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention.
  • These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, 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,
  • 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. 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:
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • 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 land as well as for selective purposes Weed control can be used 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. They can be if used as intermediate or Vo ⁇ rodukte for the synthesis of other active ingredients.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants).
  • 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 sprout, leaf, flower and root, 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
  • 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.
  • 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, e.g. 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, e.g. 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.
  • 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
  • suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates
  • 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.
  • Mineral and vegetable oils can also be used as additives.
  • 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 of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents which contain one or more known herbicides and a safener.
  • safeners substances which improve crop tolerance
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsul matterson, benazolin (beflubutamide, ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl) , Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide,
  • Flumetsulam Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flu ⁇ yr- sulfuron (-methyl, -sodium), Flurenol (-butyl), Flurypyrone (-butoxypropyl, -meptyl), fluorimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fom-safen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, P -methyl), hexazinones, imazametha- benz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, im
  • 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 calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • a mixture of 19 g (0.13 mol) of cyclopropyl-phenyl-methylamine, 250 ml of toluene, 50 ml of 1,4-dioxane and 15.5 g of 30% hydrochloric acid is heated under reflux, the water contained therein on a water separator is separated. After adding 10.8 g (0.13 mol) of cyanoguanidine, the reaction mixture is then kept at 140 ° C. for two hours, then cooled to room temperature, stirred with acetone and the crystalline product is isolated by suction.
  • a mixture of 50 g (0.34 mol) of cyclopropylphenyl ketone and 150 g of formamide is heated to 150 ° C. and at this temperature 50 ml of formic acid are added dropwise over the course of 60 minutes.
  • the mixture is heated to 160 ° C. for a further 2 hours.
  • the mixture is diluted to about three times the volume with approximately equal volumes of water and toluene, shaken well, the organic phase is separated off, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.
  • a mixture of 25 g (0.14 mol) of N- (cyclohexyl-phenyl-methyl) -formamide, 50 ml of conc. Hydrochloric acid and 50 ml of water are heated under reflux for 60 minutes. After cooling to room temperature, the mixture is filtered and the filtrate is adjusted to pH 10 by adding 20% sodium hydroxide solution. Then it is extracted with toluene, the organic phase is dried with sodium sulfate and filtered. The product is isolated from the filtrate by distillation under reduced pressure.
  • 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 active ingredient concentration in the spray liquor is selected 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 with a height of 5 to 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.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

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

Abstract

Nouvelles 1-aryl-cyclopropylamino-1,3,5-triazines substituées de formule générale (I), dans laquelle les restes R?1, R2, R3¿ et Ar possèdent la signification indiquée dans le descriptif, procédé et produits intermédiaires pour la préparation de ces nouvelles triazines et leur utilisation en tant qu'herbicides et insecticides.
PCT/EP2001/002439 2000-03-16 2001-03-05 1-aryl-cyclopropylmethylamino-1,3,5-triazines substituees WO2001068616A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001248330A AU2001248330A1 (en) 2000-03-16 2001-03-05 Substituted 1-aryl-cyclopropylmethylamino-1,3,5-triazines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10012820.3 2000-03-16
DE2000112820 DE10012820A1 (de) 2000-03-16 2000-03-16 Substituierte 1-Aryl-cyclopropylmethylamino-1,3,5-triazine

Publications (1)

Publication Number Publication Date
WO2001068616A1 true WO2001068616A1 (fr) 2001-09-20

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AU (1) AU2001248330A1 (fr)
DE (1) DE10012820A1 (fr)
WO (1) WO2001068616A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002094802A1 (fr) * 2001-05-22 2002-11-28 Grünenthal GmbH Derives substitues de c-furan-2-yl-methylamine et c-thiophen-2-yl-methylamine
WO2024022502A1 (fr) * 2022-07-29 2024-02-01 江西天宇化工有限公司 COMPOSÉ BENZYL-TRIAZINE α-SUBSTITUÉ, SON PROCÉDÉ DE PRÉPARATION, SON UTILISATION ET HERBICIDE

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3830810A (en) * 1971-12-01 1974-08-20 Ciba Geigy Corp S-triazine derivatives
DE19641692A1 (de) * 1996-10-10 1998-04-23 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
WO2001010849A2 (fr) * 1999-08-04 2001-02-15 Bayer Aktiengesellschaft Arylalkylamino-1,3,5-triazines substituees

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3830810A (en) * 1971-12-01 1974-08-20 Ciba Geigy Corp S-triazine derivatives
DE19641692A1 (de) * 1996-10-10 1998-04-23 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
WO2001010849A2 (fr) * 1999-08-04 2001-02-15 Bayer Aktiengesellschaft Arylalkylamino-1,3,5-triazines substituees

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002094802A1 (fr) * 2001-05-22 2002-11-28 Grünenthal GmbH Derives substitues de c-furan-2-yl-methylamine et c-thiophen-2-yl-methylamine
US6878740B2 (en) 2001-05-22 2005-04-12 Gruenenthal Gmbh Substituted C-furan-2-yl-methylamine and C-thiophen-2-yl-methylamine compounds
WO2024022502A1 (fr) * 2022-07-29 2024-02-01 江西天宇化工有限公司 COMPOSÉ BENZYL-TRIAZINE α-SUBSTITUÉ, SON PROCÉDÉ DE PRÉPARATION, SON UTILISATION ET HERBICIDE

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AU2001248330A1 (en) 2001-09-24
AR027974A1 (es) 2003-04-23

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