WO2001010853A1 - 2-imino-thiazolines substituees - Google Patents

2-imino-thiazolines substituees Download PDF

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Publication number
WO2001010853A1
WO2001010853A1 PCT/EP2000/007265 EP0007265W WO0110853A1 WO 2001010853 A1 WO2001010853 A1 WO 2001010853A1 EP 0007265 W EP0007265 W EP 0007265W WO 0110853 A1 WO0110853 A1 WO 0110853A1
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WIPO (PCT)
Prior art keywords
cyano
methyl
alkyl
chlorine
ethyl
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PCT/EP2000/007265
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German (de)
English (en)
Inventor
Klaus-Helmut Müller
Mark-Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
Original Assignee
Bayer Aktiengesellschaft
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Priority to AU65674/00A priority Critical patent/AU6567400A/en
Publication of WO2001010853A1 publication Critical patent/WO2001010853A1/fr

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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • 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
    • A01N43/80—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 1,2
    • 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
    • A01N43/82—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 three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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 2-imino-thiazolines, processes for their preparation and their use as herbicides.
  • A represents a single bond or alkanediyl (alkylene) having 1 to 6 carbon atoms
  • Q oxygen or sulfur
  • R 1 for each optionally by nitro, amino, cyano, carboxy, carbamoyl,
  • R 2 stands for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having up to 6 carbon atoms,
  • R 3 represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C] -C 4 -alkoxy, each having up to 6 carbon atoms,
  • R 4 for hydrogen, cyano, halogen, for alkoxy with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 alkoxy, for each cycloalkyl optionally substituted by cyano, halogen or C 1 -C 4 alkyl, each with 3 to 6 carbon atoms, each optionally with nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, -C 4 -
  • Y represents a single bond or NH, N (CC 4 -alkyl), N (C 2 -C 4 -alkenyl) or N (C 2 -C 4 -alkynyl),
  • the general formula (I) includes the possible E and Z isomers of the compounds of the formula (I).
  • hydrocarbon chains such as alkyl
  • the hydrocarbon chains are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.
  • A preferably represents a single bond or methylene (CH 2 ), methylene (CH 2 CH 2 ) or trimethylene (CH 2 CH 2 CH 2 ).
  • Q preferably represents oxygen or sulfur. preferably represents in each case optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, fluorochloroethyl, trifluoroethyl, trichloroethyl, difluorophenyl, di-chlorofluoromethyl, fluorofluoromethyl Ethoxy, n- or i-propoxy, n-,
  • R 2 preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl.
  • R 3 preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n- or n-propyl, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy. i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
  • R 4 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Butoxy, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for each optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, flu
  • Q particularly preferably represents oxygen or sulfur.
  • R 1 particularly preferably represents in each case optionally through nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl,
  • Cyano nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy substituted phenyl, phenoxy or Phenylthio substituted, monocyclic or bicyclic heterocyclyl from the series furyl, benzo slipryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl,
  • R 2 particularly preferably represents chlorine, bromine, methyl or ethyl.
  • R 3 particularly preferably represents hydrogen, chlorine, bromine, methyl or ethyl.
  • R 4 particularly preferably represents in each case optionally through nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulfmylylethyl, ethylsulfinyl, trifluoromethylsulfonylmethyl, methyltrifluoromethylsulfonyl, methyl
  • Y particularly preferably represents a single bond or NH.
  • Q very particularly preferably stands for oxygen.
  • R 1 very particularly preferably represents in each case optionally through nitro, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n - or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfmyl, ethylsulfinyl, trifluoromethylsulfylyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsul
  • R, 2 very particularly preferably represents methyl.
  • R 3 very particularly preferably represents hydrogen.
  • R, 4 very particularly preferably represents phenyl which, in the 3 or meta position, contains a substituent from the series fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy and optionally a further substituent from the Contains fluorine, chlorine, trifluoromethyl, the group 3-trifluoromethyl-phenyl being particularly emphasized for R 4 .
  • Y very particularly preferably represents a single bond.
  • 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. According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred).
  • the new substituted 2-imino-thiazolines of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.
  • R 2 , R 3 and R 4 have the meaning given above,
  • X represents halogen, alkoxy, aryloxy, arylalkoxy or the grouping -OC (Q) -YR 1 ,
  • reaction auxiliary optionally in the presence of a reaction auxiliary and optionally in the presence of a reaction auxiliary
  • reaction can run in the method according to the invention are outlined by the following formula:
  • Formula (II) provides a general definition of the 2-imino-thiazolines to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • A, R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the general formula (I) according to the invention, are preferred or particularly preferred for A. , R 2 , R 3 and R 4 have been specified.
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,459,277, EP-A-545,431).
  • Formula (III) provides a general definition of the (thio) carbonyl compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • Q and R 1 preferably or in particular have those meanings which have been given above or in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for Q and R 1 ;
  • X preferably represents fluorine, chlorine, bromine, C 1 -C 4 alkoxy, phenoxy or benzyloxy, in particular chlorine, methoxy or phenoxy.
  • the starting materials of the general formula (III) are known organic synthetic chemicals.
  • Formula (IV) provides a general definition of the iso (thio) cyanates which may be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • Q and R 1 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 Q and R 1 ,
  • the starting materials of the general formula (IV) are known organic synthetic chemicals.
  • Formula (I) is optionally carried out using a reaction auxiliary.
  • 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 acetate, 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; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N
  • Ethyl-2-methyl-pyridine 4-dimethylamino-pyridine, N-methylpiperidine, 1, 4-diaza- bicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] undec-7-ene ( DBU).
  • DABCO 4-diaza- bicyclo [2.2.2] octane
  • DBN 1,5-diazabicyclo [4.3.0] non-5-ene
  • DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
  • Phase transfer catalysts are also suitable as further reaction aids for the process according to the invention.
  • Examples of such catalysts are:
  • Tetrabutylammonium bromide Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromide,
  • diluents for carrying out the processes according to the invention are in particular inert organic solvents.
  • diluents for carrying out the processes 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 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 such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
  • reaction temperatures can be carried out when carrying out the process according to the invention.
  • Process can be varied over a wide range. 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 large excess.
  • the reaction is generally carried out in a suitable diluent 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. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsisia, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver,
  • Dactyloctenium Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagaria, Setaria, Setaria.
  • the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth.
  • the active compounds according to the invention for combating weeds in permanent crops for example forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, used on ornamental and sports turf and pasture land and for selective weed control in annual crops become.
  • 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 the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • 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 the plant cultivars 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 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.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by means of one or more layers
  • the active ingredients can be converted into the customary 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 polymers
  • 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
  • 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 as well as their ethers and esters, ketones such as
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, se
  • coconut shells, corn cobs and tobacco stems as emulsifying and / or foaming Generating agents are possible: 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 dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • 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 dispersing agents are, for example, lignin sulfite waste 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. Further,
  • 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 in a mixture with known herbicides and / or with substances which improve crop tolerance ("safenem") 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.
  • safenem crop tolerance
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin,
  • Flufenacet Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet-sulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Fluprop-acil, Flu ⁇ yrsul matterson (-methyl, -sodium), Flurenol (-uryl), , Fluroxypyr- (-meptyl), Flu ⁇ rimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop-
  • 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.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation so that the desired one
  • Amount of active ingredient is applied per unit area.
  • the active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • Solvent 5 parts by weight of acetone 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 the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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

L'invention concerne de nouvelles 2-imino-thiazolines substituées de la formule générale (I) dans laquelle R<1>, R<2>, R<3>, R<4>, A, Q et Y ont la signification mentionnée dans la description. L'invention concerne en outre un procédé permettant de les préparer et leur utilisation comme herbicides.
PCT/EP2000/007265 1999-08-10 2000-07-28 2-imino-thiazolines substituees WO2001010853A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU65674/00A AU6567400A (en) 1999-08-10 2000-07-28 Substituted 2-imino-thiazolines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999137771 DE19937771A1 (de) 1999-08-10 1999-08-10 Substituierte 2-Imino-thiazoline
DE19937771.5 1999-08-10

Publications (1)

Publication Number Publication Date
WO2001010853A1 true WO2001010853A1 (fr) 2001-02-15

Family

ID=7917877

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/007265 WO2001010853A1 (fr) 1999-08-10 2000-07-28 2-imino-thiazolines substituees

Country Status (4)

Country Link
AR (1) AR025092A1 (fr)
AU (1) AU6567400A (fr)
DE (1) DE19937771A1 (fr)
WO (1) WO2001010853A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009086163A3 (fr) * 2007-12-21 2009-09-03 Abbott Laboratories Dérivés de thiazolylidine urée et d'amides et leurs méthodes d'utilisation
US7683084B2 (en) 2006-06-27 2010-03-23 Abbott Laboratories Thiazoline and oxazoline derivatives and their methods of use
JP2016539116A (ja) * 2013-11-22 2016-12-15 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Ｎ−アシルイミノ複素環式化合物
CN106810545A (zh) * 2015-12-01 2017-06-09 浙江省化工研究院有限公司 一种杂环酰基亚胺噻唑类化合物、其制备方法及应用

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0446802A1 (fr) * 1990-03-12 1991-09-18 Sumitomo Chemical Company, Limited Iminothiazolines, leur production, leur utilisation comme herbicide et les intermédiaires nécessaires à leur production
EP0529482A1 (fr) * 1991-08-23 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides et intermédiaires necessaires à leur production
EP0529481A1 (fr) * 1991-08-28 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides
EP0531970A1 (fr) * 1991-09-11 1993-03-17 Sumitomo Chemical Company, Limited Composition herbicide
EP0545431A1 (fr) * 1991-12-05 1993-06-09 Sumitomo Chemical Company Limited Procédé de préparation d'iminothiazolins
JPH07291954A (ja) * 1994-04-27 1995-11-07 Sumitomo Chem Co Ltd ２−アシルイミノチアゾリン誘導体の製造法
JPH07291953A (ja) * 1994-04-27 1995-11-07 Sumitomo Chem Co Ltd ２−アシルイミノチアゾリン誘導体の製造法
WO1998042703A1 (fr) * 1997-03-24 1998-10-01 Basf Aktiengesellschaft Derives de thiazolimine

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0446802A1 (fr) * 1990-03-12 1991-09-18 Sumitomo Chemical Company, Limited Iminothiazolines, leur production, leur utilisation comme herbicide et les intermédiaires nécessaires à leur production
EP0529482A1 (fr) * 1991-08-23 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides et intermédiaires necessaires à leur production
US5459277A (en) * 1991-08-23 1995-10-17 Sumitomo Chemical Company, Limited Iminothiazolines, their production and use as herbicides, and intermediates for their production
EP0529481A1 (fr) * 1991-08-28 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides
EP0531970A1 (fr) * 1991-09-11 1993-03-17 Sumitomo Chemical Company, Limited Composition herbicide
EP0545431A1 (fr) * 1991-12-05 1993-06-09 Sumitomo Chemical Company Limited Procédé de préparation d'iminothiazolins
JPH07291954A (ja) * 1994-04-27 1995-11-07 Sumitomo Chem Co Ltd ２−アシルイミノチアゾリン誘導体の製造法
JPH07291953A (ja) * 1994-04-27 1995-11-07 Sumitomo Chem Co Ltd ２−アシルイミノチアゾリン誘導体の製造法
WO1998042703A1 (fr) * 1997-03-24 1998-10-01 Basf Aktiengesellschaft Derives de thiazolimine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 03 29 March 1996 (1996-03-29) *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7683084B2 (en) 2006-06-27 2010-03-23 Abbott Laboratories Thiazoline and oxazoline derivatives and their methods of use
US8470813B2 (en) 2006-06-27 2013-06-25 Abbvie Inc. Thiazoline and oxazoline derivatives and their methods of use
WO2009086163A3 (fr) * 2007-12-21 2009-09-03 Abbott Laboratories Dérivés de thiazolylidine urée et d'amides et leurs méthodes d'utilisation
JP2011508734A (ja) * 2007-12-21 2011-03-17 アボット・ラボラトリーズ チアゾリリジン尿素およびアミド誘導体ならびにこの使用方法
US8383657B2 (en) 2007-12-21 2013-02-26 Abbott Laboratories Thiazolylidine urea and amide derivatives and methods of use thereof
JP2016539116A (ja) * 2013-11-22 2016-12-15 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Ｎ−アシルイミノ複素環式化合物
CN106810545A (zh) * 2015-12-01 2017-06-09 浙江省化工研究院有限公司 一种杂环酰基亚胺噻唑类化合物、其制备方法及应用

Also Published As

Publication number Publication date
AR025092A1 (es) 2002-11-06
AU6567400A (en) 2001-03-05
DE19937771A1 (de) 2001-02-15

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