EP0973765A1 - Aryluraciles substitues - Google Patents

Aryluraciles substitues

Info

Publication number
EP0973765A1
EP0973765A1 EP98919188A EP98919188A EP0973765A1 EP 0973765 A1 EP0973765 A1 EP 0973765A1 EP 98919188 A EP98919188 A EP 98919188A EP 98919188 A EP98919188 A EP 98919188A EP 0973765 A1 EP0973765 A1 EP 0973765A1
Authority
EP
European Patent Office
Prior art keywords
optionally substituted
cyano
halogen
substituted
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98919188A
Other languages
German (de)
English (en)
Inventor
Roland Andree
Markus Dollinger
Christoph Erdelen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0973765A1 publication Critical patent/EP0973765A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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 aryluracils, ner processes for their preparation and their ner use as plant treatment agents, in particular as herbicides and insecticides.
  • n the numbers 0, 1, 2 or 3
  • Q represents O, S, SO or SO 2 ,
  • R 1 represents hydrogen, amino or optionally substituted alkyl
  • R 2 stands for carboxy, cyano, carbamoyl, thiocarbamoyl or for optionally substituted alkyl or alkoxycarbonyl,
  • R 3 represents hydrogen, halogen or optionally substituted alkyl, - ⁇ -
  • Sulfo, chlorosulfonyl, aminosulfonyl, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino or alkylsulfonylamino, and
  • Z for optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, benzo exertryl, dihydrobenzofuryl, dioxolanyl, dioxanyl, benzodioxanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolol, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridyl vinyl
  • R 2 and R 3 have the meanings given above and
  • a 1 represents alkyl, aryl or arylalkyl
  • n, Q, Y and Z have the meanings given above and
  • a 2 represents alkyl, aryl or arylalkyl
  • a 3 represents optionally substituted alkyl
  • X 1 represents halogen or the grouping -O-SO2-OA 3 , - $ -
  • the new substituted aryluracils of the general formula (I) are notable for strong herbicidal and insecticidal activity.
  • the invention preferably relates to compounds of the formula (I) in which
  • n the numbers 0, 1, 2 or 3
  • Q represents O, S, SO or SO 2 ,
  • R 1 represents hydrogen, amino or optionally by cyano, halogen or Cj-
  • R 2 represents carboxy, cyano, carbamoyl, thiocarbamoyl or alkyl or alkoxycarbonyl, each of which has 1 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy,
  • R 3 represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
  • the invention relates in particular to compounds of the formula (I) in which
  • n the numbers 0, 1 or 2
  • Q represents O, S, SO or SO 2 ,
  • R 1 represents hydrogen, amino or in each case methyl or ethyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 2 represents methyl or ethyl optionally substituted by fluorine and / or chlorine
  • R 3 represents hydrogen, fluorine, chlorine, bromine or methyl
  • Y for nitro, amino, hydroxy, carboxy, cyano, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, aminosulfonyl, fluorine, chlorine, bromine, or for each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio , Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethy
  • Z for optionally substituted heterocyclyl from the series furyl, tetrahydrofyl, benzo exertryl, dihydrobenzofuryl, dioxolanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolyl, pyridinyl, quinolinyl, isoquinolazinyl, pyridinyl, isoquinolinyl, pyridinyl
  • Substituted aryluracils of the formula (Ib) are very particularly preferred - S> -
  • R 1 represents hydrogen, amino or methyl
  • Y represents hydrogen, ortho-fluorine, meta-COOC 2 H 5 or meta-NHSO 2 C 2 H 5 and
  • 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.
  • Formula (I) amino acid esters to be used as starting materials are generally defined by the formula (II).
  • R 2 and R 3 preferably or in particular have those meanings which have been given above or in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 2 and R 3 ;
  • a 1 preferably represents C ] -C4-alkyl, phenyl or benzyl, in particular methyl or ethyl.
  • the starting materials of the general formula (II) are known and / or can be prepared by known processes (cf. J. Heterocycl. Chem. 9 (1972), 513-522).
  • Formula (III) provides a general definition of the aryl urethanes (aryl carbamates) to be used further as starting materials in process (a) according to the invention.
  • n, Q, Y and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for n, Q, Y and Z were specified;
  • a 2 preferably represents C1-C4-
  • Alkyl phenyl or benzyl, especially for methyl or ethyl.
  • the starting materials of the general formula (III) are known and / or can be prepared by known processes (cf. US 4193787, US 4423237).
  • aryl urethanes (aryl carbamates) of the general formula (III) are obtained, for example, if aryl amines of the general formula (VII)
  • n, Q, Y and Z have the meanings given above,
  • a 2 has the meaning given above,
  • an acid acceptor e.g. Pyridine
  • a diluent e.g. Methylene chloride
  • Formula (IV) provides a general definition of the substituted aryluracils to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I).
  • n, Q, R 2 , R 3 and Y preferably or in particular have those meanings which are preferred or particularly preferred for, in connection with the description of the compounds of the formula (I) according to the invention n, Q, R 2 , R 3 and Y were given.
  • the starting materials of the general formula (IV) are known and / or can be prepared by known processes (cf. EP 545206, JP 04178373, US 5344812, US 5399543, WO 9517096).
  • Formula (V) provides a general definition of the halomethyl heterocycles to be used as starting materials in process (b) according to the invention.
  • Z preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Z;
  • X preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.
  • the starting materials of the general formula (V) are known organic synthetic chemicals.
  • Formula (I) used as starting materials substituted aryluracils are generally defined by the formula (Ia).
  • n, Q, R 2 , R 3 Y and Z preferably or in particular have those meanings which have already been mentioned above in the - »3- in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for n, Q, R 2 , R 3 Y and Z have been given.
  • the starting materials of the general formula (Ia) for process (c) are also the subject of the present application as new substances; they can be prepared by processes (a) or (b) according to the invention.
  • Formula (IV) provides a general definition of the alkylating agents which are further to be used as starting materials in process (c) according to the invention.
  • Formula (IV) has R 1 and R 2 preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 and R 2 .
  • a 3 preferably for alkyl with 1 to 4 carbon atoms optionally substituted by cyano, fluorine or chlorine, in particular for methyl or ethyl, and
  • X preferably for fluorine, chlorine, bromine or iodine, or for the grouping -O-SO 2 -OA 3 , in particular for chlorine or bromine.
  • the starting materials of formula (IV) are known organic synthetic chemicals.
  • Suitable reaction auxiliaries for processes (a), (b) and (c) are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, 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-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine
  • Inert organic solvents are particularly suitable as diluents for carrying out processes (a), (b) and (c) 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 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 triamide; Esters such as methyl acetate or ethyl acetate, and also sulfoxides or sulfones, such as dimethyl sulfoxide or tetramethylene sulfone (“sulfolane”).
  • Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydr
  • reaction temperatures can be varied within a substantial range when carrying out processes (a), (b) and (c). In general, temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C.
  • 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 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 in each case by 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 e.g. can be used in the following plants:
  • Galinsoga Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Dutilon, Emo Viola, galeopsis, papaver, centaurea, trifolium, ranunculus, taraxacum.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds of the formula (I) according to the invention are suitable for controlling monocotyledon and dicotyledon weeds both in the pre-emergence and in the post-emergence process.
  • the active substances are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • animal pests preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Diplopoda for example, Blaniulus guttulatus.
  • Chilopoda for example, Geophilus carpophagus and Scutigera spec.
  • Thysanura e.g. Lepisma saccharina.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • From the order of the Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Pumphi spp.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, LithocoUetis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
  • Tineola bisselliella Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura glamiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
  • Anthrenus spp. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Costimallontra pursuits.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Acarina for example Acarus siro, Argas spp, Ornithodoros spp, Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp, Rhipicephalus spp, Amblyomma spp, Hyalomma spp, Ixodes spp, Psoroptes spp,
  • Chorioptes spp Sarcoptes spp, Tarsonemus spp, Bryobia praetiosa, Panonychus spp, Tetranychus spp
  • Plant parasitic nematodes include e.g. Pratylenchus spp, Radopholus spp, Ditylenchus spp, Tylenchulus spp, Heterodera spp, Globodera spp,
  • the active ingredients can be converted into the usual formulations, such as
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents
  • organic substances can also be used.
  • Liquid solvents are essentially 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 paraflfins, e.g.
  • Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • natural rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Solid carrier materials for granules are suitable Eg 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, coconut shells, corn cobs and tobacco stalks, come as emulsifiers and / or foam-producing agents in question: eg nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, as dispersants are suitable. e.g. 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 phosphopides, such as cephalene and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%
  • active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amidochlor, amidosulfuron, asulam, atrazine, azimsulfuron, benazolin, benfuresate, bensulfuron (-methyl) , Bentazon, Benzofenap, Benzoylprop (- ethyl), Bialaphos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor,
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • the mixture is poured onto about twice the volume of water, shaken with diethyl ether / ethyl acetate (vol. 1/1), the aqueous phase is acidified with 2N hydrochloric acid and shaken with ethyl acetate.
  • the organic phase obtained last is washed with water, dried with sodium sulfate and filtered.
  • the filtrate is concentrated in a water-jet vacuum, the residue is digested with a mixture of 2 ml of ethyl acetate, 20 ml of petroleum ether and 20 ml of diethyl ether, and the crystalline product is isolated by suction.
  • the reaction mixture After the addition of 1.0 g (7.7 mmol) of 1-aminooxy-2,4-dinitro-benzene, the reaction mixture becomes two days, after the addition of a further 0.4 g of 1-aminooxy-2,4-dinitro-benzene two days and after adding a further 0.4 g of l-aminooxy-2,4-dinitro-benzene, stirred for another two days at room temperature. It is then shaken with water / diethyl ether, the organic phase is washed with 2N sodium hydroxide solution, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether and the crystalline product is isolated by suction.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray mixture is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha become
  • 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.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist
  • the death rate is determined in%. 100% means that all the beetle larvae have been killed, 0% means that no beetle larvae have been killed
  • the compound according to Preparation Example 3 shows a degree of death of 100% after 7 days at an active ingredient concentration of 0.1%

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

Abstract

L'invention concerne de nouveaux aryluraciles substitués de la formule générale (I) dans laquelle n représente les nombres 0, 1, 2 ou 3, Q désigne O, S, SO ou bien SO2, R<1> représente hydrogène, amino ou alkyle éventuellement substitué, R<2> représente carboxy, cyano, carbamoyle, thiocarbamoyle, ou bien alkyle ou alcoxycarbonyle respectivement éventuellement substitués, R<3> désigne hydrogène, halogène ou alkyle éventuellement substitué, Y représente nitro, amino, hydroxy, carboxy, cyano, carbamoyle, thiocarbamoyle, sulfo, chlorsulfonyle, aminosulfonyle, halogène, ou bien alkyle, alcoxy, alkylthio, alkylsulfynyle, alkylsulfonyle, alkylamino, alkylcarbonyle, alcoxycarbonyle, alkylaminocarbonyle, alkylcarbonylamino, alcoxycarbonylamino ou alkylsulfonylamino respectivement éventuellement substitués, et Z désigne hétérocyclyle éventuellement substitué et appartenant à la série furyle, tétrahydrofuryle, benzofuryle, dihydrobenzofuryle, dioxolanyle, dioxanyle, benzodioxanyle, pyrrolyle, pyrazolyle, imidazolyle, triazolyle, oxazolyle, isoxazolyle, benzoxazolyle, pyridinyle, quinoléinyle, isoquinoléinyle, pyrimidinyle, pyrazinyle, pyridazinyle, quinazolinyle, quinoxalinyle, ou bien thiazolyle, isothiazolyle, benzothiazolyle ou benzimidazolyle respectivement substitués, leurs procédés de préparation et leur utilisation comme produits phytosanitaires.
EP98919188A 1997-04-11 1998-03-30 Aryluraciles substitues Withdrawn EP0973765A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19715017 1997-04-11
DE19715017A DE19715017A1 (de) 1997-04-11 1997-04-11 Substituierte Aryluracile
PCT/EP1998/001847 WO1998046592A1 (fr) 1997-04-11 1998-03-30 Aryluraciles substitues

Publications (1)

Publication Number Publication Date
EP0973765A1 true EP0973765A1 (fr) 2000-01-26

Family

ID=7826133

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98919188A Withdrawn EP0973765A1 (fr) 1997-04-11 1998-03-30 Aryluraciles substitues

Country Status (9)

Country Link
US (1) US6448203B1 (fr)
EP (1) EP0973765A1 (fr)
JP (1) JP2001519819A (fr)
CN (1) CN1259943A (fr)
AU (1) AU733843B2 (fr)
BR (1) BR9809085A (fr)
CA (1) CA2286053A1 (fr)
DE (1) DE19715017A1 (fr)
WO (1) WO1998046592A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19752748A1 (de) * 1997-11-28 1999-06-02 Bayer Ag Substituierte Phenyluracile
DE19846008A1 (de) * 1998-10-06 2000-04-13 Bayer Ag Phenylessigsäure-heterocyclylamide

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US4193787A (en) * 1978-08-31 1980-03-18 Stauffer Chemical Company Benzodioxane herbicides
US4423237A (en) 1980-01-24 1983-12-27 Stauffer Chemical Company Benzodioxane herbicides
US5134145A (en) * 1989-11-17 1992-07-28 Uniroyal Chemical Company, Inc. Pesticidal pyrimidinyl benzoic acids and esters
US5134144A (en) * 1989-11-20 1992-07-28 Uniroyal Chemical Company, Inc. Pesticidal 3-arylpyrimidinyl ethers and thioethers
JPH04178373A (ja) 1990-11-13 1992-06-25 Nissan Chem Ind Ltd ６―ハロアルキル―３―フェニルウラシル誘導体及び製法
JPH0539272A (ja) * 1991-01-09 1993-02-19 Nissan Chem Ind Ltd ピリミジンジオン誘導体および除草剤
JPH0525144A (ja) * 1991-04-15 1993-02-02 Nissan Chem Ind Ltd ウラシル誘導体及び有害生物防除剤
DE4139952A1 (de) 1991-12-04 1993-06-09 Bayer Ag, 5090 Leverkusen, De N-aryl-stickstoffheterocyclen
JPH05202031A (ja) * 1992-01-28 1993-08-10 Nissan Chem Ind Ltd Ｎ−アミノピリミジンジオン誘導体および除草剤
US5262390A (en) 1992-08-26 1993-11-16 Fmc Corporation Herbicical 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates
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See references of WO9846592A1 *

Also Published As

Publication number Publication date
CA2286053A1 (fr) 1998-10-22
WO1998046592A1 (fr) 1998-10-22
BR9809085A (pt) 2000-08-01
DE19715017A1 (de) 1998-10-15
US6448203B1 (en) 2002-09-10
AU7212698A (en) 1998-11-11
JP2001519819A (ja) 2001-10-23
AU733843B2 (en) 2001-05-31
CN1259943A (zh) 2000-07-12

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