[go: up one dir, main page]

WO1999021841A1 - Aryloxyalkylaminotriazines substituees - Google Patents

Aryloxyalkylaminotriazines substituees Download PDF

Info

Publication number
WO1999021841A1
WO1999021841A1 PCT/EP1998/006511 EP9806511W WO9921841A1 WO 1999021841 A1 WO1999021841 A1 WO 1999021841A1 EP 9806511 W EP9806511 W EP 9806511W WO 9921841 A1 WO9921841 A1 WO 9921841A1
Authority
WO
WIPO (PCT)
Prior art keywords
cyano
fluorine
chlorine
methyl
enantiomers
Prior art date
Application number
PCT/EP1998/006511
Other languages
German (de)
English (en)
Inventor
Stefan Lehr
Hans-Jochem Riebel
Uwe Stelzer
Rolf Kirsten
Andreas Lender
Katharina Voigt
Markus Dollinger
Mark Wilhelm Drewes
Ingo Wetcholowsky
Yukiyoshi Watanabe
Randy Allen Myers
Original Assignee
Bayer Aktiengesellschaft
Nihon Bayer Agrochem K.K.
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 Aktiengesellschaft, Nihon Bayer Agrochem K.K. filed Critical Bayer Aktiengesellschaft
Priority to KR1020007003757A priority Critical patent/KR20010024451A/ko
Priority to CA002307093A priority patent/CA2307093A1/fr
Priority to EP98965133A priority patent/EP1034168A1/fr
Priority to AU20473/99A priority patent/AU2047399A/en
Priority to BR9812769-1A priority patent/BR9812769A/pt
Priority to JP2000517953A priority patent/JP2001521028A/ja
Publication of WO1999021841A1 publication Critical patent/WO1999021841A1/fr

Links

Classifications

    • 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 aryloxyalkylaminotriazines, processes for their preparation and their use as herbicides.
  • R 1 represents hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by hydroxy, cyano, halogen or Cj-Cj-alkoxy,
  • R 2 represents hydrogen, formyl or, in each case optionally by cyano
  • R 3 for alkyl optionally substituted by hydroxy, cyano, halogen or Cj-Czj-alkoxy having 2 to 6 carbon atoms or for optionally by
  • R 4 represents hydrogen or alkyl having 1 to 4 carbon atoms
  • Ar represents optionally substituted phenyl, naphthyl, tetralinyl or heterocyclyl,
  • the possible heterocyclyl groupings are preferably selected from the following group:
  • halogen for each optionally by hydroxy, cyano, halogen, C ⁇ - C4-alkoxy, -C -C4-alkylcarbonyl, -C -C4-alkoxy-carbonyl, C1-C4- alkyl thio, C 1 -C 4 alkylsulfonyl or C 4 -C 4 alkylsulfonyl substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, or for optionally by cyano, halogen or C1-C4 Alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
  • R 1 , R 2 , R 3 , R 4 and Ar have the meaning given above,
  • R 3 , R 4 , Ar and Z have the meaning given above and
  • R 1 and R 2 have the meaning given above
  • R 1 , R 2 and Z have the meaning given above and
  • Y 1 represents halogen or alkoxy
  • R 1 , R 3 , R 4 , Ar and Z have the meaning given above,
  • R 2 has the meaning given above with the exception of hydrogen
  • Y 2 represents halogen, -OR 2 or -O-CO-R 2 ,
  • the compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore exist in different enantiomeric (R and S-configured forms) or diastereomeric forms.
  • the invention relates to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) as well as the mixtures of these isomeric compounds
  • hydrocarbon chains such as alkyl
  • the hydrocarbon chains are in each case straight-chain or branched, also in conjunction with heteroatoms, such as in alkoxy or alkylthio
  • 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 1 for hydrogen or for each optionally by hydroxy, cyano, fluorine,
  • R 2 represents hydrogen, formyl, or methyl, ethyl substituted in each case by cyano, fluorine, chlorine, bromine, methoxy or ethoxy,
  • R 3 each represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy or each which is optionally substituted by cyano, fluorine, chlorine, Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl
  • R 4 represents hydrogen or methyl
  • Ar represents optionally substituted phenyl, naphthyl, tetralinyl 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 represents hydrogen or methyl or ethyl which is optionally substituted by cyano, fluorine, methoxy or ethoxy
  • R 2 represents hydrogen or methyl, ethyl, acetyl or propionyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy
  • R 3 represents ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
  • R 4 represents hydrogen
  • Ar represents in each case optionally substituted phenyl or naphthyl
  • Group 19 has, for example, the meanings given above in Group 1.
  • Group 34 has, for example, the meanings given above in Group 1.
  • Group 44 has, for example, the meanings given above in Group 1.
  • Group 49 has, for example, the meanings given above in Group 1.
  • Group 54 has, for example, the meanings given above in Group 1.
  • Group 70 has, for example, the meanings given above in Group 1.
  • Group 80 has, for example, the meanings given above in Group 1.
  • Group 85 has, for example, the meanings given above in Group 1.
  • Group 90 has, for example, the meanings given above in Group 1.
  • Formula (I) to be used as starting materials aryloxyalkyl biguanides are generally defined by formula (II).
  • R 1 , R 2 , R 3 , R 4 and Ar preferably or in particular have those meanings which have already been described above in connection with the description of the compounds of the formula (I), preferably or as in particular were preferably given for R 1 , R 2 , R 3 , R 4 and Ar.
  • Suitable acid adducts of compounds of the formula (II) are their addition products with protonic acids, such as, for example, with hydrogen chloride (hydrogen chloride), Hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • protonic acids such as, for example, with hydrogen chloride (hydrogen chloride), Hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • aryloxyalkyl biguanides of the general formula (II) are obtained if substituted aryloxyalkylamines of the general formula (VII)
  • R 3 , R 4 and Ar have the meaning given above,
  • reaction auxiliary e.g. Hydrogen chloride
  • a diluent e.g. n-Decane or 1,2-dichlorobenzene
  • Formula (VII) are known and / or can be prepared by processes known per se (cf. Acta Pol. Pharm. 53 (1996), 47-52 - cited in Chem. Abstracts 126 46897, Angew Chem 106 (1994), 1041-1043, Bull Soc Chim Belg 85 (1976), 421-425, loc cit 86 (1977), 1003-1007, 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, ZA6903772, production examples)
  • alkoxycarbonyl compounds to be used further as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) 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 being particularly preferred for Z
  • R ' preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl
  • the starting materials of the formula (III) are known synthetic chemicals
  • substituted halogentazines which are used as starting materials in the process (b) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (IV).
  • R 3 , R 4 , Ar and Z preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula according to the invention
  • (I) preferably or as particularly preferred for R 3 , R 4 , Ar and Z
  • X preferably represents fluorine or chlorine, in particular chlorine
  • X 1 represents halogen
  • R 3 , R 4 and Ar have the meaning given above,
  • an acid acceptor e.g. Ethyldiisopropylamine
  • a diluent e.g. Tetrahydrofuran or dioxane
  • Formula (VI) provides a general definition of the substituted aminotriazines to be used as starting materials in process (c) according to the invention for the preparation of compounds of the formula (I).
  • R 1 , R 2 and Z preferably or in particular have those meanings which have already been described above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 1 , R 2 and Z specified were;
  • Y 1 preferably represents fluorine, chlorine, methoxy or ethoxy, in particular chlorine or methoxy.
  • the starting materials of the general formula (VI) are known and / or can be prepared by processes known per se (cf. WO 95/11237).
  • Formula (VII) provides a general definition of the substituted aryloxyalkylamines to be used further as starting materials in process (c) according to the invention.
  • R 3 , R 4 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 3 , R 4 and Ar were specified.
  • the starting materials of the general formula (VII) are known and / or can be prepared by processes known per se (cf. DE 3426919; DE 4000610; DE
  • Formula (I) to be used as starting materials are generally defined by the formula (Ia).
  • R 1 , R 3 , R 4 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) preferably or as particularly preferred for R 1 , R 3 , R 4 Ar and Z were given.
  • LeA31995) they can be prepared by processes (a), (b) or (c) according to the invention (cf. the preparation examples).
  • Formula (VIII) provides a general definition of the alkylating or acylating agents to be used further as starting materials in process (d) according to the invention.
  • R 2 with the exception of hydrogen, 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 R 2 ;
  • Y 2 preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, acetyloxy or propionyloxy, in particular chlorine, methoxy or acetyloxy.
  • the starting materials of the general formula (VIII) are known synthetic chemicals.
  • Suitable reaction auxiliaries for processes (a), (b), (c) and (d) 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 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 - -methanolat, -ethanolat, -n- or -i-propanolat, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethyl
  • Suitable diluents for carrying out processes (a), (b), (c) and (d) in addition to water are, in particular, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline Benzene
  • ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones, such as methyl or isopropyl Methyl isobutyl ketone, nitriles, such as acetonitrile, propionitrile or butyronitrile, amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrohdon or hexamethlylphosphoric acid triamide, Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sul
  • reaction temperatures can be varied within a substantial range when carrying out processes (a), (b), (c) and (d) according to the invention. In general, temperatures between -20 ° C. and + 300 ° C., preferably between -10 ° C and + 250 ° C
  • the starting materials are generally used in approximately aquimolar 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.
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • 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 connections for weed control in permanent crops e.g. forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea -, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective weed control in annual crops
  • the compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledons
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, impregnated with active compounds
  • formulations are prepared in a known manner, e.g. B by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents
  • Aromatic solvents such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, are essentially suitable as liquid solvents or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Solid carrier materials that come into question are, for example, 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, and solid carrier materials for granules Question e.g. broken and fractionated natural rocks such as calcite, marble,
  • coconut shells, corn cobs and tobacco stalks, as emulsifying and / or foam-generating agents are suitable, for example, nonionic and anionic emulsifiers.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates, and dispersants are, for example, lignin sulfite liquor and methyl cellulose
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, 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%
  • 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.
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosul disorderson, Anilofos, Asulam, Atrazine, Azafenidin, Azimsul wholeon, Benazolin (-ethyl), Ben solutionsesate, Bensul wholeon (-methyl)
  • Benzofenap Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyidaz, Chloronben, Chloramben, Chloramben, Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cin- methylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop,
  • 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 filtrate is diluted to about three times the volume with water, shaken with ethyl acetate, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.
  • 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 on the basis of the retention times by linear interpolation between two successive alkanones)
  • a mixture of 21.6 g (0.20 mol) of m-cresol, 20.0 g (0.26 mol) of 1,2-epoxy-butane and 0.5 g (0.02 mol) of lithium hydroxide is added for 20 hours Stirred 180 ° C. Then the mixture is taken up in about twice the amount of toluene, washed with 1N sodium hydroxide solution and then with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is distilled under more reduced pressure at a bath temperature of at most about 160 ° C., the product crystallizing out in the cooler.
  • the extraction solution A is dried with sodium sulfate and filtered, the filtrate is concentrated in a water jet vacuum.
  • the (R) -N-methoxyacetyl-1-phenoxymethyl-propylamine obtained as the crude product is concentrated in 300 ml of water and 60 ml. Hydrochloric acid was taken up and heated to boiling under reflux for 20 hours. After extraction with dichloromethane, drying with sodium sulfate, filtration and concentration of the filtrate in a water jet vacuum, 30.7 g of (R) -l-phenoxymethyl-propylamine (79.5% of theory) are obtained , 93.2% ee)
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active compound preparation, so that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray mixture is chosen so that in 1 000 l of water / ha the respective desired amounts of active ingredient are applied
  • Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray broth is chosen so that in

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (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)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouvelles aryloxyalkylaminotriazines substituées de formule (I), dans laquelle R1 désigne, par exemple, H ou un alkyle en C¿1?-C6, R?2¿ désigne, par exemple, H, un alkyle en C¿1?-C6 ou un alkylcarbonyle en C1-C6, R?3¿ désigne, par exemple, un alkyle en C¿2?-C6, R?4¿ désigne, par exemple, H ou un alkyle en C¿1?-C4, Ar désigne, par exemple, un phényle substitué ou non substitué, et Z désigne, par exemple, un halogène, un alkyle en C1-C6, hydroxyalkyle en C1-C6, halogénoalkyle en C1-C6 ou un cycloalkyle en C3-C6. L'invention concerne également un procédé de fabrication de ces produits ainsi que leur utilisation comme herbicides.
PCT/EP1998/006511 1997-10-24 1998-10-14 Aryloxyalkylaminotriazines substituees WO1999021841A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020007003757A KR20010024451A (ko) 1997-10-24 1998-10-14 치환된 아릴옥시 알킬 아미노 트리아진
CA002307093A CA2307093A1 (fr) 1997-10-24 1998-10-14 Aryloxyalkylaminotriazines substituees
EP98965133A EP1034168A1 (fr) 1997-10-24 1998-10-14 Aryloxyalkylaminotriazines substituees
AU20473/99A AU2047399A (en) 1997-10-24 1998-10-14 Substituted aryloxy alkyl amino triazines
BR9812769-1A BR9812769A (pt) 1997-10-24 1998-10-14 "arilóxialquilaminotriazinas substituìdas"
JP2000517953A JP2001521028A (ja) 1997-10-24 1998-10-14 置換アリールオキシアルキルアミノトリアジン

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19746994.9 1997-10-24
DE19746994A DE19746994A1 (de) 1997-10-24 1997-10-24 Substituierte Aryloxyalkylaminotriazine

Publications (1)

Publication Number Publication Date
WO1999021841A1 true WO1999021841A1 (fr) 1999-05-06

Family

ID=7846487

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/006511 WO1999021841A1 (fr) 1997-10-24 1998-10-14 Aryloxyalkylaminotriazines substituees

Country Status (9)

Country Link
EP (1) EP1034168A1 (fr)
JP (1) JP2001521028A (fr)
KR (1) KR20010024451A (fr)
CN (1) CN1277606A (fr)
AU (1) AU2047399A (fr)
BR (1) BR9812769A (fr)
CA (1) CA2307093A1 (fr)
DE (1) DE19746994A1 (fr)
WO (1) WO1999021841A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005025900A1 (de) * 2005-06-06 2006-12-07 Basf Ag Verfahren zur Entfernung von Salzen aus einem Alkoxycarbonylaminotriazin enthaltenden Reaktionsgemisch

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273328A2 (fr) * 1986-12-27 1988-07-06 Idemitsu Kosan Company Limited Dérivés de la triazine et herbicides les contenant
EP0411153A1 (fr) * 1989-02-20 1991-02-06 Idemitsu Kosan Company Limited Derive de triazine et herbicide le contenant a titre d'ingredient actif
DE19531084A1 (de) * 1995-08-24 1997-02-27 Hoechst Schering Agrevo Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO1998015538A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273328A2 (fr) * 1986-12-27 1988-07-06 Idemitsu Kosan Company Limited Dérivés de la triazine et herbicides les contenant
EP0411153A1 (fr) * 1989-02-20 1991-02-06 Idemitsu Kosan Company Limited Derive de triazine et herbicide le contenant a titre d'ingredient actif
DE19531084A1 (de) * 1995-08-24 1997-02-27 Hoechst Schering Agrevo Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO1998015538A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides

Also Published As

Publication number Publication date
CA2307093A1 (fr) 1999-05-06
DE19746994A1 (de) 1999-04-29
KR20010024451A (ko) 2001-03-26
CN1277606A (zh) 2000-12-20
AU2047399A (en) 1999-05-17
BR9812769A (pt) 2000-10-10
JP2001521028A (ja) 2001-11-06
EP1034168A1 (fr) 2000-09-13

Similar Documents

Publication Publication Date Title
WO1998015536A1 (fr) 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides
EP0934285A1 (fr) 2-amino-4-alkylamino-1,3,5-triazines substituees utilisees comme herbicides
WO1998015537A1 (fr) 2-amino-4-alkylamino-1,3,5-triazines substituees utilisees comme herbicides
DE19744711A1 (de) Substituierte 2,4-Diamino-1,3,5-triazine
WO1998015538A1 (fr) 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides
WO1999018100A1 (fr) 2,4-diamino-1,3,5-triazines substituees et leur utilisation comme herbicides
WO1999037627A1 (fr) Aminoalkylidenaminotriazines substituees utilisees comme herbicides
DE19711825A1 (de) Substituierte 2,4-Diamino-1,3,5-triazine
WO1999046249A1 (fr) Derives de 2,4-diamino-1,3,5-triazine substitues en position 6, comportant au moins deux atomes de carbone a substitution asymetrique, leur production et leur utilisation comme herbicides
WO2000069854A1 (fr) Thienocycloalk(en)ylamino-1,3,5-triazines substituees
EP1037882B1 (fr) 2,4-diamino-1,3,5-triazines substituees
DE19936633A1 (de) Substituierte Arylalkylamino-1,3,5-triazine
DE19812879A1 (de) Substituierte 2,4-Diamino-1,3,5-triazine
WO2000021938A1 (fr) Herbicides a base de formylaminotriazines substituees
WO1999021841A1 (fr) Aryloxyalkylaminotriazines substituees
DE19924370A1 (de) Substituierte Cyclohexylalkylamino-1,3,5-triazine
WO2001005786A2 (fr) Thienylalkylamino-1,3,5-triazines a activite optique
DE19905609A1 (de) Substituierte Benzthiazolylalkylamino-1,3,5-triazine
DE19809360A1 (de) Optisch aktive substituierte 2,4-Diamino-1,3,5-triazine
DE19816055A1 (de) Thienylalkylamino-1,3,5-triazine

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 98810521.7

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GD GE GH GM HR HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1998965133

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 1020007003757

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: 20473/99

Country of ref document: AU

ENP Entry into the national phase

Ref document number: 2307093

Country of ref document: CA

Ref document number: 2307093

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PA/a/2000/003951

Country of ref document: MX

WWP Wipo information: published in national office

Ref document number: 1998965133

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1020007003757

Country of ref document: KR

WWW Wipo information: withdrawn in national office

Ref document number: 1998965133

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1020007003757

Country of ref document: KR