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WO2000047579A1 - Benzo-thiazolyl-alkylamino-1,3,5-triazines substituees utilisees comme herbicides - Google Patents

Benzo-thiazolyl-alkylamino-1,3,5-triazines substituees utilisees comme herbicides Download PDF

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Publication number
WO2000047579A1
WO2000047579A1 PCT/EP2000/000785 EP0000785W WO0047579A1 WO 2000047579 A1 WO2000047579 A1 WO 2000047579A1 EP 0000785 W EP0000785 W EP 0000785W WO 0047579 A1 WO0047579 A1 WO 0047579A1
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WO
WIPO (PCT)
Prior art keywords
fluorine
chlorine
cyano
substituted
carbon atoms
Prior art date
Application number
PCT/EP2000/000785
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German (de)
English (en)
Inventor
Hans-Jochem Riebel
Mark Wilhelm Drewes
Kristian Kather
Dieter Feucht
Rolf Kirsten
Rolf Pontzen
Stefan Lehr
Ingo Wetcholowsky
Katharina Voigt
Original Assignee
Bayer Aktiengesellschaft
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Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU25462/00A priority Critical patent/AU2546200A/en
Publication of WO2000047579A1 publication Critical patent/WO2000047579A1/fr

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Classifications

    • 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
    • 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
    • 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

Definitions

  • the invention relates to new substituted benzthiazolylalkylamino-l, 3,5-triazines, processes for their preparation, intermediates for their preparation, processes for the preparation of these intermediates and the use of the benzothiazolylalkylamino-l, 3,5-triazines as herbicides.
  • n stands for the numbers 0, 1, 2, 3 or 4,
  • R stands for nitro, cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy each having 1 to 6 carbon atoms each optionally substituted by cyano, halogen or -CC alkoxy,
  • R is optionally substituted by cyano, halogen or C j -C 4 alkoxy
  • R for hydrogen, for halogen, for alkyl with 1 to 6 carbon atoms substituted by cyano, halogen, hydroxy, C.-C.- alkoxy or C j -C 4 -alkylthio, for each optionally by cyano, halogen or C j -C 4 - Alkoxy substituted alkylcarbonyl, alkoxycarbonyl, alkoxy, alkylthio, alkylsulfyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl or alkynyl optionally substituted by halogen each having 2 to 6 carbon atoms, or for optionally by cyano, halogen or C j -C ⁇ alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
  • alkoxy-substituted alkyl having 1 to 6 carbon atoms and - R represents hydrogen or represents optionally cyano-, halogen or C j -C 4
  • R 5 represents hydrogen, represents formyl or represents in each case optionally cyano-, halogen or C j -C 4 - in the alkyl groups substituted alkoxy alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case 1 to 6 carbon atoms,
  • R 4 R 5 also represents alkylaminoalkylidene amino or dialkylaminoalkylidene amino each having up to 6 carbon atoms in the alkyl groups or alkylidene groups,
  • n preferably represents the numbers 0, 1, 2 or 3.
  • R preferably stands for nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or for alkyl or alkoxy, each substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, each having 1 up to 5 carbon atoms.
  • R preferably represents alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy or cycloalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl up to 6 carbon atoms.
  • R preferably represents hydrogen, fluorine, chlorine, bromine, cyano, fluorine, chlorine, bromine, hydroxy, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio substituted alkyl with 1 to 5 carbon atoms, each optionally with cyano, fluorine, chlorine, methoxy,
  • alkylcarbonyl alkoxycarbonyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 5 carbon atoms in the alkyl groups, for alkenyl or alkynyl each optionally substituted by fluorine, chlorine or bromine, each having 3 to 5 carbon atoms, or for optionally by cyano, fluorine, chlorine,
  • R preferably represents hydrogen or alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy.
  • R preferably represents hydrogen, formyl or alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, each having 1 to 5
  • the grouping N preferably also represents alkylaminoalkylidene amino or dialkylaminoalkylidene amino each having up to 4 carbon atoms in the alkyl groups or alkylidene groups.
  • n particularly preferably represents the numbers 0, 1 or 2.
  • R 1 particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R particularly preferably represents in each case optionally by cyano, fluorine,
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, each substituted by cyano, fluorine, chlorine, bromine, hydroxyl, methoxy, ethoxy, methylthio or ethylthio, i- or s-butyl, for in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl thio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, for propenyl, butenyl, propynyl or but
  • R particularly preferably represents hydrogen, formyl or methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, which are each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, Ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl.
  • n very particularly preferably stands for the numbers 0 or 1.
  • R, ⁇ very particularly preferably represents fluorine, chlorine, bromine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine or chlorine.
  • R " very particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine or chlorine.
  • R very particularly preferably represents methyl, ethyl, n- or i-propyl each substituted by fluorine or chlorine.
  • R, 4 very particularly preferably represents hydrogen, methyl or ethyl.
  • R 5 very particularly preferably represents hydrogen, formyl, methyl or
  • Ethyl or for each optionally by fluorine, chlorine, methoxy or Ethoxy substituted acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl.
  • R 1 most preferably represents fluorine, chlorine or methyl or methoxy which is optionally substituted by fluorine.
  • R 2 most preferably represents methyl or ethyl.
  • R most preferably represents 1-fluoroeth-1-yl or 2-fluoro-prop-2-yl.
  • R most preferably represents hydrogen.
  • R> 5 most preferably represents hydrogen or formyl.
  • Residual definitions can be combined with one another, that is, also between the specified preferred ranges.
  • Preferred compounds according to the invention are those of the formula (I) in which a combination of those listed above as preferred (“preferably”)
  • 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 formula (I) and to the mixtures of these isomeric compounds.
  • the new substituted benzothiazolylalkylamino-1,3,5-triazines of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.
  • R R ⁇ , R4 and R ⁇ have the meaning given above,
  • R ' represents alkyl
  • n, R 1 , R 2 , R 4 and R 5 preferably have those meanings which are preferred for n, R 1 , R above in connection with the description of the compounds of the general formula (I) according to the invention 2 , R 4 and R 5 have been specified.
  • 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.
  • n, R and R ⁇ have the meaning given above, - and / or acid adducts of compounds of the general formula (IV), such as, for example, the hydrochlorides -
  • reaction auxiliary e.g. Hydrogen chloride
  • diluent e.g. 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.
  • benzothiazolylalkylamines of the general formula (IV) required as precursors are known and / or can be prepared by processes known per se (cf. WO-A-96/04252).
  • 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 3 preferably has the meaning already given above in connection with the description of the compounds of the general invention
  • Formula (I) has been indicated as preferred or 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.
  • a diluent for carrying out the process according to the invention is preferably carried out using a diluent.
  • suitable diluents for carrying out the process according to the invention are, above all, 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 butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene
  • 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, 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 - - methanolate, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds, such as trimethylamine, Triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclo
  • DBU 1,8 diazabicyclo [5,4,0] undec-7-ene
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention for the preparation of the triazines.
  • temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • 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 processing is carried out according to customary methods (cf. the
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow in places grow where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can e.g. can be used with the following plants:
  • Brassica, lactuca, cucumis, cucurbita Brassica, lactuca, cucumis, cucurbita.
  • Scirpus Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopeeurus, Apera, Aegilops, Phalaris.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants that are grown by conventional breeding and optimization methods or by Biotechnological and genetic engineering methods of combinations of these methods can be obtained, including the transgenic plants and including the plant varieties which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves 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 propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and plant parts and plant parts with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
  • 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,
  • 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 aerial parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active ingredients can be overfilled in 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 and 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.
  • 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
  • eg broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks
  • Possible 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, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • MCPP Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Nicroanulfononon, Napropur Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonic acid, Pendimethalin,
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. 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 effort is between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • a mixture of 6.3 g (29 mmol) of l- (benzothiazol-2-yl) ethylamine and 2.4 g (29 mmol) of cyanoguanidine is heated to a (bath) temperature of 160 ° C. A melt forms after approx. 30 minutes. After a further 30 minutes, the heating bath is removed and, after cooling to room temperature, the crude product is digested with diethyl ether and the crystalline product is isolated by suction.
  • Example II-1 Analogously to Example II-1, for example, the compounds of the general formula (I) listed in Table 2 below can also be prepared.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the 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 the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • 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
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants with a height of 5 - 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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

Abstract

L'invention concerne des nouvelles benzo-thiazolyl-alkylamino-1,3,5-triazines substituées de formule générale (I), dans laquelle n, R?1, R2, R3, R4 et R5¿ ont la signification indiquée dans la description; un procédé permettant de les produire; les produits intermédiaires nécessaires à leur production, y compris le procédé permettant de produire lesdits intermédiaires; et l'utilisation desdites benzo-thiazolyl-alkylamino-1,3,5-triazines comme herbicides.
PCT/EP2000/000785 1999-02-11 2000-02-01 Benzo-thiazolyl-alkylamino-1,3,5-triazines substituees utilisees comme herbicides WO2000047579A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU25462/00A AU2546200A (en) 1999-02-11 2000-02-01 Substituted benzthiazolylalkylamino-1,3,5-triazines as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19905609.9 1999-02-11
DE1999105609 DE19905609A1 (de) 1999-02-11 1999-02-11 Substituierte Benzthiazolylalkylamino-1,3,5-triazine

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Publication Number Publication Date
WO2000047579A1 true WO2000047579A1 (fr) 2000-08-17

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012012528A1 (fr) * 2010-07-20 2012-01-26 Vestaron Corporation Triazines et pyrimidines insecticides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0283522A1 (fr) * 1986-09-30 1988-09-28 Idemitsu Kosan Company Limited Derive de triazine, production de ce derive, et herbicide le contenant en tant que principe actif
EP0411153A1 (fr) * 1989-02-20 1991-02-06 Idemitsu Kosan Company Limited Derive de triazine et herbicide le contenant a titre d'ingredient actif
WO1997029095A1 (fr) * 1996-02-06 1997-08-14 Hoechst Schering Agrevo Gmbh 2,4-diamino-1,3,5-triazines, procedes permettant de les preparer et de les utiliser comme herbicides et regulateurs de croissance vegetale
WO1999018100A1 (fr) * 1997-10-07 1999-04-15 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees et leur utilisation comme herbicides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0283522A1 (fr) * 1986-09-30 1988-09-28 Idemitsu Kosan Company Limited Derive de triazine, production de ce derive, et herbicide le contenant en tant que principe actif
EP0411153A1 (fr) * 1989-02-20 1991-02-06 Idemitsu Kosan Company Limited Derive de triazine et herbicide le contenant a titre d'ingredient actif
EP0620220A2 (fr) * 1989-02-20 1994-10-19 Idemitsu Kosan Company Limited Dérivés de triazines comme herbicides
WO1997029095A1 (fr) * 1996-02-06 1997-08-14 Hoechst Schering Agrevo Gmbh 2,4-diamino-1,3,5-triazines, procedes permettant de les preparer et de les utiliser comme herbicides et regulateurs de croissance vegetale
WO1999018100A1 (fr) * 1997-10-07 1999-04-15 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees et leur utilisation comme herbicides

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012012528A1 (fr) * 2010-07-20 2012-01-26 Vestaron Corporation Triazines et pyrimidines insecticides
US8389718B2 (en) 2010-07-20 2013-03-05 Vestaron Corporation Insecticidal triazines and pyrimidines
CN103052628A (zh) * 2010-07-20 2013-04-17 韦斯塔隆公司 三嗪类和嘧啶类杀虫剂
JP2013532659A (ja) * 2010-07-20 2013-08-19 ベスタロン コーポレイション トリアジン系およびピリミジン系殺虫剤
US8785630B2 (en) 2010-07-20 2014-07-22 Vestaron Corporation Insecticidal triazines and pyrimidines
CN103052628B (zh) * 2010-07-20 2016-05-18 韦斯塔隆公司 三嗪类和嘧啶类杀虫剂
CN106035343A (zh) * 2010-07-20 2016-10-26 韦斯塔隆公司 三嗪类和嘧啶类杀虫剂
CN106035343B (zh) * 2010-07-20 2019-07-02 韦斯塔隆公司 三嗪类和嘧啶类杀虫剂

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