WO2004067518A1 - Procede et appareil de collage en surface d'une bande de papier ou de carton - Google Patents

Procede et appareil de collage en surface d'une bande de papier ou de carton Download PDF

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Publication number
WO2004067518A1
WO2004067518A1 PCT/EP2004/000345 EP2004000345W WO2004067518A1 WO 2004067518 A1 WO2004067518 A1 WO 2004067518A1 EP 2004000345 W EP2004000345 W EP 2004000345W WO 2004067518 A1 WO2004067518 A1 WO 2004067518A1
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Prior art keywords
halogen
optionally substituted
cyano
alkyl
methyl
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PCT/EP2004/000345
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German (de)
English (en)
Inventor
Ernst Rudolf Gesing
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
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Bayer Cropscience Aktiengesellschaft
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Publication of WO2004067518A1 publication Critical patent/WO2004067518A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms

Definitions

  • the invention relates to new substituted pyrimidines, processes for their preparation and their use as plant treatment agents, in particular as herbicides.
  • n stands for the numbers 0, 1 or 2
  • Q represents O (oxygen) or S (sulfur),
  • R 1 represents hydrogen, halogen or optionally substituted in each case
  • R 2 stands for hydrogen, for halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylarnino or dialkyla ino
  • R 3 represents hydrogen or represents optionally substituted alkyl or cycloalkyl
  • R 4 represents hydrogen or represents optionally substituted alkyl or phenyl
  • X stands for cyano, nitro, halogen or for each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, or two adjacent groups X also stand together for a benzo group
  • Saturated or unsaturated hydrocarbon groups such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched as far as possible, even in linkages 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 optionally contain one or more asymmetrically substituted carbon atoms and in these cases can be present in various enantiomeric (R- and S-configured forms) or diastereomeric forms.
  • the invention relates both to the use of the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (T) and to the mixtures of these isomeric compounds.
  • R 1 preferably represents hydrogen, halogen, alkyl or alkoxy each optionally substituted by halogen or d-Gi-alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or alkylthio, alkylarnino or dialkylamino, each having 1 to 6 carbon atoms in the alkyl groups.
  • R 2 preferably represents hydrogen, halogen, alkyl or alkoxy each optionally substituted by halogen or C 1 -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or alkylthio, alkylamino or dialkylamino each having 1 to 6 Carbon atoms in the
  • R 3 preferably represents hydrogen, alkyl having 1 to 6 carbon atoms optionally substituted by cyano, halogen or -Gralkoxy, or optionally substituted by cyano, halogen or - - alkyl
  • R 4 preferably represents hydrogen, alkyl having 1 to 6 carbon atoms optionally substituted by cyano, halogen or Ci-C 4 alkoxy, or optionally nitro, cyano, halogen, C 1 -C 4 alkyl, Ci-C 4 -Halogenoalkyl, C 1 -C -alkoxy or C 1 -C -haloalkoxy substituted phenyl.
  • X preferably stands for cyano, nitro, halogen or for alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl with 1 to 6 carbon atoms, which are optionally substituted by halogen, or two adjacent groups X also together for a benzo group.
  • R 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, and in each case methyl, ethyl, n- or i-propyl, methoxy optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , Ethoxy, n- or , "_ ⁇ O 004/067518
  • i-propoxy for methylthio, ethylthio, n- or i-propylthio, methylamino, emylamino, n- or i-propylarnino, dimemylamino or diethylamino.
  • R 2 particularly preferably stands for hydrogen, for fluorine, chlorine, bromine, iodine, for methyl, ethyl, n- or i-propyl, methoxy which are each optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , Ethoxy, n- or i-propoxy, for methylthio, ethylthio, n- or i-propylthio, methylamino,
  • R 3 particularly preferably represents hydrogen, in each case optionally by
  • R 4 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or optionally by nitro, cyano, fluorine, Chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or
  • X particularly preferably represents cyano, nitro, fluorine, chlorine, bromine, iodine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by fluorine and / or chlorine. Butyl, methoxy, ethoxy, n- or i-
  • R very particularly preferably represents chlorine, methyl, ethyl, methoxy or ethoxy optionally substituted by fluorine, chlorine, methoxy or ethoxy, methylthio, ethylthio, methylamine, ethylamino or dimethylamino.
  • R very particularly preferably represents chlorine, in each case methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, represents methylthio, ethylthio, methylamino, ethylamino or dimethylamino.
  • R very particularly preferably represents hydrogen, each methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine or methyl.
  • R 4 very particularly preferably represents hydrogen, in each case methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or phenyl.
  • X very particularly preferably represents cyano, nitro, fluorine, chlorine, bromine, iodine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by fluorine and / or chlorine , Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, emylsulfinyl, methylsulfonyl or ethylsulfonyl, or two adjacent groups X also together for a benzo group.
  • a very particularly preferred group are also those compounds in which Q is O (oxygen), R 1 and R 2 are methoxy and R 3 , R 4 and X have the meaning particularly preferred above.
  • R 1 and R 2 are most preferably methoxy.
  • R 3 most preferably represents hydrogen.
  • R 4 most preferably represents hydrogen, in each case methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
  • X most preferably represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, or two adjacent groups X together also for a benzo group.
  • the new substituted pyrimidines of the general formula (T) are notable for strong and selective herbicidal activity.
  • R and R have the meaning given above and.
  • Y represents halogen, alkylthio, alkylsulfonyl or alkylsulfonyl
  • Y preferably represents fluorine, chlorine, bromine, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, in particular methylsulfonyl.
  • the starting materials of the general formula (H) are known and / or can be prepared by processes known per se (cf. J. Chem. Soc. 1957, 1830; J ..
  • Formula (TU) provides a general definition of the nucleophilic compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • general formula (I) provides a general definition of the nucleophilic 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 has the meaning given above and
  • R represents alkyl, in particular methyl or ethyl
  • a diluent e.g. Water
  • a diluent e.g. Water
  • arylalkylamines of the formula (TV) required as precursors are known and / or can be prepared by processes known per se (cf. J. Am. Chem. Soc. 76/1954, 5589-5597; Synthetic Commun. 7 (1977), 71-78; manufacturing examples).
  • N-cyano-imidates of the formula (V) required as precursors are known organic synthetic chemicals.
  • reaction auxiliaries 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, cesium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, -n- or -i-propanolate, -n -
  • DABCO 1,4-diazabicyclo [2,2,2] octane
  • DBN 1,5-diazabicyclo [ 4,3,0] -non-5-ene
  • DBU 1,8-diazabicyclo [5,4,0] -undec-7-ene
  • Formula (I) is preferably carried out using one or more diluents.
  • Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention. 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 emylene 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-
  • the reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up 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 e.g. can be used in the following plants:
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on
  • the active compounds according to the invention for combating herbaceous weed in Da ⁇ erkulturen for example forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants , on ornamental and sports turf and pasture land as well as for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for 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 compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants 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 crop plants (including naturally occurring crop plants).
  • Crop 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 shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • 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, for example by dipping, spraying, Evaporation, nebulization, scattering, spreading and, in the case of propagation material, in particular seeds, also by means of single- or multi-layer coating.
  • 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 substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or the 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 as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite,
  • 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; The following may be used as dispersants: for example lignin sulfite waste 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, 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
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
  • safeners substances which improve crop tolerance
  • herbicides are suitable for the mixtures, for example Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamide, Benazolin (-ethyl), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime,
  • Metolachlor Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, naproanilide, napropa ide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxamidafen, pentoxamidafen, pentoxamidon, pentoxamidon, pentoxamidon, poxy , Pretilachlor, Primisulfuron (-methyl), Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Pro
  • Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, dichlormid, Dymron, Fenclorim, Fenchlorazole (-ethyl) , Flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-
  • 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,
  • 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.
  • plants and their parts can be treated.
  • plant species and plant cultivars which occur wildly or are obtained by conventional organic breeding methods, such as crossing or protoplast fusion, and parts thereof are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, optionally in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term "parts” or "parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained by conventional breeding, by mutagenesis, or else by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of activity and / or an increase in the effect of the reversible substances and agents - also in combination with other agrochemical active ingredients, better growth of crop plants, increased tolerance of crop plants to high or low temperatures, increased tolerance of crop plants to dryness or to water or soil salt content, increased flowering performance, easier harvesting, acceleration the ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or processability of the harvested products, which go beyond the effects that are actually to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, have received genetic material which gives these plants particularly advantageous properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to
  • Pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants include the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryUA, CrylUA, CryIlTß2, Cry9c Cry2Ab,
  • Cry3Bb and CrylF and their combinations are generated in the plants (in following "Bt plants”).
  • the increased defense of plants against are also particularly emphasized as traits. Fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the increased tolerance of the plants to certain herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example “PAT” gene), is also particularly emphasized as characteristic traits.
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YLELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, e.g.
  • rapeseed rapeseed
  • EVA® tolerance against imidazolinones
  • STS® tolerance to sulfonylureas such as corn.
  • herbicide-resistant plants are the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention, the synergistic effects mentioned above occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants.
  • the preferred ranges given above for the active ingredients or mixtures also apply to the treatment of these plants.
  • Especially plant treatment with the compounds or mixtures specifically listed in the present text should be emphasized.
  • the calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the
  • the lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants with a height of 5 - 15 cm are sprayed with the active ingredient preparation in such a way that the desired quantities of active substances 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.
  • the compounds according to Preparation Examples 2, 5, 10 and 12 show some of which are well tolerated by crop plants, such as e.g. Corn and sugar beet, strong weed control.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouvelles pyrimidines substituées de formule (I) dans laquelle R<1>, R<2>, R<3>, R<4>, Q, X et n ont la signification mentionnée dans la description, ainsi que des procédés et des produits intermédiaires permettant de les produire. L'invention concerne également leur utilisation comme agents phytosanitaires, notamment comme herbicides.
PCT/EP2004/000345 2003-01-31 2004-01-19 Procede et appareil de collage en surface d'une bande de papier ou de carton WO2004067518A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2003103883 DE10303883A1 (de) 2003-01-31 2003-01-31 Substituierte Pyrimidine
DE10303883.3 2003-01-31

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CN100333641C (zh) * 2003-07-04 2007-08-29 浙江化工科技集团有限公司 含丙酯草醚或异丙酯草醚和草除灵的油菜田除草剂组合物
CN100361978C (zh) * 2005-09-02 2008-01-16 中国科学院上海有机化学研究所 2-嘧啶氧基-n-芳基-7-腈基或磷酸酯基苄胺类化合物、制备方法及其用途
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