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WO1999052906A1 - Herbicides a base d'axazolyle- et thiazolyle-uraciles substitues - Google Patents

Herbicides a base d'axazolyle- et thiazolyle-uraciles substitues Download PDF

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Publication number
WO1999052906A1
WO1999052906A1 PCT/EP1999/002087 EP9902087W WO9952906A1 WO 1999052906 A1 WO1999052906 A1 WO 1999052906A1 EP 9902087 W EP9902087 W EP 9902087W WO 9952906 A1 WO9952906 A1 WO 9952906A1
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WIPO (PCT)
Prior art keywords
amino
alkyl
substituted
cyano
methyl
Prior art date
Application number
PCT/EP1999/002087
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German (de)
English (en)
Inventor
Roland Andree
Markus Dollinger
Mark Wilhelm Drewes
Ingo Wetcholowsky
Christoph Erdelen
Randy Allen Myers
Original Assignee
Bayer Aktiengesellschaft
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
Priority claimed from DE19854082A external-priority patent/DE19854082A1/de
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU37026/99A priority Critical patent/AU3702699A/en
Publication of WO1999052906A1 publication Critical patent/WO1999052906A1/fr

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Classifications

    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/14—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 three or more hetero rings

Definitions

  • the present invention relates to new substituted oxazolyl- and thiazolyl-uracils, several processes for their preparation and their use as plant treatment agents, in particular as herbicides and insecticides.
  • Q oxygen or sulfur
  • R 1 represents hydrogen, amino or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, halogen or CC ⁇ alkoxy
  • R 2 represents formyl, hydroximinomethyl, cyano, carboxy, C 4 -C 4 -alkoxy-carbonyl, carbamoyl, thiocarbamoyl or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen
  • R 3 represents hydrogen, cyano, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen,
  • R 4 represents hydrogen, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen, and
  • R 5 represents in each case optionally substituted phenyl, naphthyl or pyridyl, the possible substituents being selected from the following list:
  • the hydrocarbon chains such as alkyl
  • R 1 preferably represents hydrogen, amino or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy;
  • R 2 preferably represents formyl, hydroximinomethyl, cyano, carboxy, methoxycarbonyl, ethoxycarbonyl, carbamoyl, thiocarbamoyl or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine;
  • R 3 preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine;
  • R 4 preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by fluorine and / or chlorine;
  • R 5 preferably represents in each case optionally substituted phenyl, naphthyl or pyridyl, the possible substituents preferably being selected from the following list:
  • N-ethylsulfonyl-amino Nn-butyroyl-N-methylsulfonyl-amino, Nn-butyro-yl-N-ethylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ni-buty-royl-N-ethylsulfonyl-amino, N-pivaloyl-N-methylsulfonylamino, N-pivaloyl-N-ethylsulfonylamino, cyclopropylcarbonylamino, cyclopropylsulfonylamino.
  • Q preferably represents sulfur
  • R 1 particularly preferably represents hydrogen, amino, methyl or ethyl
  • R 2 particularly preferably represents trifluoromethyl
  • R 3 particularly preferably represents hydrogen, chlorine or methyl
  • R 4 particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl
  • R 5 particularly preferably represents in each case optionally substituted phenyl or pyridyl, the possible substituents being selected in particular from the following list: Nitro, amino, hydroxyl, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine (methyl in each case optionally substituted by fluorine and / or chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl), Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl sulfinyl, ethyl sulfinyl, methyl sulfonyl, Eth
  • a very particularly preferred group are those compounds of the formula (I) in which R 1 is amino and Q, R 2 , R 3 , R 4 and R 5 have the meaning given above.
  • Another very particularly preferred group are those compounds of the formula (I) in which R 1 is methyl and Q, R 2 , R 3 , R 4 and R 5 have the meaning given above as being particularly preferred.
  • 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.
  • the new substituted oxazolyl- and thiazolyl-uracils of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal and insecticidal activity.
  • R 2 and R 3 have the meanings given above and
  • a 1 represents alkyl, aryl or arylalkyl
  • a 2 represents alkyl, aryl or arylalkyl
  • R 2 , R 3 , R 4 and R 5 have the meanings given above, with l-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (IV)
  • a 3 represents optionally substituted alkyl
  • X 1 represents halogen or the grouping -0-S0 2 -0-A 3 ,
  • reaction auxiliaries if appropriate in the presence of reaction auxiliaries and if appropriate in the presence of diluents,
  • Formula (II) provides a general definition of the aminoalkenic acid esters to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I).
  • R 2 and R 3 preferably have those meanings which have already been given as preferred, particularly preferred or very particularly preferred for R 2 and R 3 in connection with the description of the compounds of the formula (I);
  • a 1 preferably represents C 1 -C 4 -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 oxazolyl- or thiazolyl-urethanes to be used as starting materials in process (a) according to the invention.
  • Q, R 4 and R 5 preferably have those meanings which are preferred, particularly preferred or very particularly preferred for Q, R 4 and R already in connection with the description of the compounds of the formula (I) according to the invention 5 were specified;
  • a 2 preferably represents C 1 -C 4 -alkyl, phenyl or benzyl, in particular methyl or ethyl.
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. DE-A-2132431, DE-A-2453106, WO-A-8202384, WO-A-9724343, Indian J. Chem., Sect. B 28B (1989), 786-789, preparation examples).
  • Formula (Ia) generally defines the substituted oxazolyl- and thiazolyluracils to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I).
  • Q, R 2 , R 3 , R 4 and R 5 preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the invention
  • Formula (I) has been given as preferred, particularly preferred or very particularly preferred for Q, R 2 , R 3 , R 4 and R 5 .
  • the starting materials of the general formula (Ia) for process (b) are also the subject of the present application as new substances; they can be prepared by process (a) according to the invention.
  • Formula (IV) provides a general definition of the alkylating agents to be used further as starting materials in process (b) according to the invention.
  • a 3 preferably represents optionally by cyano, halogen or
  • the starting materials of formula (IV) are known organic synthetic chemicals.
  • Processes (a) and (b) are primarily inert organic solvents. These include in particular ahphatic, 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,
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries for processes (a) and (b). 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 or 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 methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; basic organic nitrogen compounds, such as 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, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N
  • DBU 1,8-diazabicyclo [5,4,0] -undec-7-en
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between -20 ° C and + 200 ° C, preferably between 0 ° C and 180 ° C.
  • Processes (a) and (b) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes 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.
  • the work-up is carried out using customary methods (cf. the manufacturing 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:
  • 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 pastures and for selective weed control in annual crops.
  • the compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active ingredients are also 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.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
  • Acarina e.g. Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Chorioptes spp ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.
  • Acarina e.g. Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus
  • the plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,. Tylenchus spp., Helicotylenchus spp., Rotylenchus spp., Tylenchulus spp.
  • the compounds of the general formula (I) according to the invention are very suitable for controlling plant-damaging insects, such as e.g. Rice leafhoppers (Nephotettix spp.).
  • the compounds of the general formula (I) according to the invention also have fungicidal activity, in particular against Phytophthora spp.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally 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 ahphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • ahphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
  • Oils such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • 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 and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite leaching 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 for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl)
  • Benzofenap Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyonaz (Chloron, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chlorambene -ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl),
  • Thidiazimin Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron.
  • Insecticides Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the 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 After cooling to room temperature, the mixture is diluted to about three times the volume with approximately equal volumes of aqueous IN sodium hydroxide solution and ethyl acetate, and after shaking, the aqueous phase is separated off and acidified with hydrochloric acid. Then it is shaken with ethyl acetate, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with ether / petroleum ether and the crystalline product is isolated by suction.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
  • 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, 8, 10 and 11 show with good tolerance to crop plants, such as e.g. Maize and rapeseed, strong against weeds.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • 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 and the given amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
  • the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.

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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)

Abstract

L'invention concerne de nouveaux oxazolyle- et thiazolyle-uraciles substitués de la formule générale (I) dans laquelle Q désigne oxygène ou soufre, R1 désigne hydrogène, amino ou alkyle éventuellement substitué par halogène ou alcoxy C¿1?-C4 et ayant entre 1 et 4 atomes de carbone, R?2¿ désigne formyle, hydroximinométhyle, cyano, carboxy, alcoxy C¿1?-C4-carbonyle, carbamoyle, thiocarbamoyle ou alkyle éventuellement substitué par halogène et ayant entre 1 et 4 atomes de carbone, R?3¿ désigne hydrogène, cyano, halogène ou alkyle éventuellement substitué par halogène et ayant entre 1 et 4 atomes de carbone, R4 désigne hydrogène, halogène ou alkyle éventuellement substitué par halogène et ayant entre 1 et 4 atomes de carbone, et R5 désigne phényle, naphtyle ou pyridyle, dans chaque cas éventuellement substitué, les substituants possibles étant sélectionnés dans l'énumération suivante : nitro, amino, hydroxy, mercapto, carboxy, cyano, carbamoyle, thiocarbamoyle, halogène et un des radicaux suivants (éventuellement substitué dans chaque cas par cyano, halogène, alcoxy C¿1?-C4, alcoxy C1-C4-carbonyle, alkylamino C1-C4-carbonyle, di-(alkyle C1-C4)-amino-carbonyle, phénylamino-carbonyle ou N-(alkyle C1-C4)-phénylamino-carbonyle): alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, alkylamino, dialkylamino, alkylcarbonyle, alcoxycarbonyle, alkylaminocarbonyle, dialkylaminocarbonyle, alkylcarbonylamino, alkylsulfonylamino, N,N-bis-alkylcarbonyle-amino, N,N-bis-alkylsulfonyle-amino et N-alkylcarbonyle-N-alkylsulfonyl-amino ayant chacun jusqu'à 6 atomes de carbone dans les groupes alkyle, ainsi que cycloalkylcarbonylamino et cycloalkylsulfonylamino ayant chacun entre 3 et 6 atomes de carbone dans les groupes cycloalkyle. L'invention concerne en outre plusieurs procédés permettant de les préparer et leur utilisation comme agents phytosanitaires, notamment comme herbicides et insecticides.
PCT/EP1999/002087 1998-04-08 1999-03-26 Herbicides a base d'axazolyle- et thiazolyle-uraciles substitues WO1999052906A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU37026/99A AU3702699A (en) 1998-04-08 1999-03-26 Substituted oxazolyle and thiazolyl uracil herbicides

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19815716 1998-04-08
DE19815716.9 1998-04-08
DE19854082A DE19854082A1 (de) 1998-04-08 1998-11-24 Substituierte Oxazolyl- und Thiazolyl-uracile
DE19854082.5 1998-11-24

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8362017B2 (en) * 2003-08-29 2013-01-29 Exelixis, Inc. C-kit modulators and methods of use
US9663529B2 (en) 2013-07-02 2017-05-30 Bristol-Myers Squibb Company Tricyclic pyrido-carboxamide derivatives as rock inhibitors
US9914740B2 (en) 2013-07-02 2018-03-13 Bristol-Myers Squibb Company Tricyclic pyrido-carboxamide derivatives as rock inhibitors

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2207549A1 (de) * 1972-02-18 1973-08-23 Bayer Ag 1-aminouracile und deren salze, verfahren zu ihrer herstellung und ihre verwendung als herbizide
JPH03287585A (ja) * 1990-04-03 1991-12-18 Nissan Chem Ind Ltd ウラシル誘導体および有害生物防除剤
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
WO1997008170A1 (fr) * 1995-08-31 1997-03-06 Fmc Corporation 3-(benzoxazol-7-yl substitue) et 3-(benzothiazol-7-yl substitue)-1-substitue-6-trifluoromethyl-2,4-(1h, 3h)pyrimidinediones herbicides
WO1998006706A1 (fr) * 1996-08-08 1998-02-19 Bayer Aktiengesellschaft P-trifluormethylphenyluraciles substitues
WO1998027083A1 (fr) * 1996-12-17 1998-06-25 Bayer Aktiengesellschaft Heterocyclyluraciles

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2207549A1 (de) * 1972-02-18 1973-08-23 Bayer Ag 1-aminouracile und deren salze, verfahren zu ihrer herstellung und ihre verwendung als herbizide
JPH03287585A (ja) * 1990-04-03 1991-12-18 Nissan Chem Ind Ltd ウラシル誘導体および有害生物防除剤
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
WO1997008170A1 (fr) * 1995-08-31 1997-03-06 Fmc Corporation 3-(benzoxazol-7-yl substitue) et 3-(benzothiazol-7-yl substitue)-1-substitue-6-trifluoromethyl-2,4-(1h, 3h)pyrimidinediones herbicides
US5753595A (en) * 1995-08-31 1998-05-19 Fmc Corporation Herbicidal 3-(substituted benzoxazol-7-yl) and 3-(Substituted benzothiazol-7-yl)-1-substituted-6-trifluoromethyl-2 4-(1h 3h)pyrimidinediones
WO1998006706A1 (fr) * 1996-08-08 1998-02-19 Bayer Aktiengesellschaft P-trifluormethylphenyluraciles substitues
WO1998027083A1 (fr) * 1996-12-17 1998-06-25 Bayer Aktiengesellschaft Heterocyclyluraciles

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 016, no. 114 (C - 0921) 23 March 1992 (1992-03-23) *
PATENT ABSTRACTS OF JAPAN vol. 017, no. 644 (C - 1134) 30 November 1993 (1993-11-30) *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8362017B2 (en) * 2003-08-29 2013-01-29 Exelixis, Inc. C-kit modulators and methods of use
US9663529B2 (en) 2013-07-02 2017-05-30 Bristol-Myers Squibb Company Tricyclic pyrido-carboxamide derivatives as rock inhibitors
US9914740B2 (en) 2013-07-02 2018-03-13 Bristol-Myers Squibb Company Tricyclic pyrido-carboxamide derivatives as rock inhibitors

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