WO1998023598A1 - Nouveaux derives de phenyluracyle a effet herbicide - Google Patents

Nouveaux derives de phenyluracyle a effet herbicide Download PDF

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Publication number
WO1998023598A1
WO1998023598A1 PCT/EP1997/006367 EP9706367W WO9823598A1 WO 1998023598 A1 WO1998023598 A1 WO 1998023598A1 EP 9706367 W EP9706367 W EP 9706367W WO 9823598 A1 WO9823598 A1 WO 9823598A1
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WO
WIPO (PCT)
Prior art keywords
cyano
alkyl
formula
halogen
carbon atoms
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PCT/EP1997/006367
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German (de)
English (en)
Inventor
Roland Andree
Mark Wilhelm Drewes
Markus Dollinger
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
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to JP52421998A priority Critical patent/JP2001504503A/ja
Priority to CA002272657A priority patent/CA2272657A1/fr
Priority to BR9713546-1A priority patent/BR9713546A/pt
Priority to AU53222/98A priority patent/AU5322298A/en
Priority to EP97950192A priority patent/EP0944607A1/fr
Publication of WO1998023598A1 publication Critical patent/WO1998023598A1/fr

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Classifications

    • 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
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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

Definitions

  • the present invention relates to new phenyl uracil derivatives, several processes for their preparation and their use as herbicides.
  • R 1 represents hydrogen, amino or alkyl optionally substituted by cyano or halogen
  • R 2 represents formyl, hydroximinomethyl, cyano, carboxy, carbamoyl, thiocarbamoyl or alkyl optionally substituted by cyano or halogen
  • R 3 represents hydrogen, halogen or alkyl optionally substituted by cyano or halogen
  • R 4 represents cyano or thiocarbamoyl
  • R 5 for hydroxy, mercapto, amino, hydroxyamino, cyano, nitro, halogen, or for one of the radicals -R 6 , -QR 6 , -NH-R 6 , -NH-OR 6 , -NH-SO 2 -R 6 , -CQ -R 6 , -CQ 1 "Q 2 -R 6 , -CQ ⁇ NH-R 6 , -Q 2 -CQ'-R 6 , -NH-CQ J -R 6 , -Q 2 -CQ1-Q2-R6 -NH-CQ ⁇ Q Z -R 6 or -Q 2 -CQ 1 -NH-R 6 , wherein
  • Q represents O, S, SO or SO 2 ,
  • Q and Q independently of one another represent oxygen or sulfur
  • R ' represents alkyl optionally substituted by cyano, halogen, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl, represents in each case alkenyl or alkynyl optionally substituted by cyano, carboxy, halogen, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl represents cycloalkyl or cycloalkylalkyl optionally substituted by cyano, carboxy, halogen, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by hydroxy, mercapto, amino, cyano,
  • Carboxy carbamoyl, thiocarbamoyl, alkyl, haloalkyl, alkoxy,
  • Carboxy carbamoyl, thiocarbamoyl, alkyl, haloalkyl, alkoxy,
  • n the numbers 0, 1, 2 or 3
  • R 2 and R 1 have the meanings given above and
  • R represents alkyl, aryl or arylalkyl
  • R 4 , R 5 and n have the meanings given above,
  • R, R 2 and R 3 have the meanings given above,
  • R 4 , R 5 and n have the meanings given above and
  • R 7 represents alkyl, aryl or arylalkyl
  • R 2 , R, R 4 , R and n have the meanings given above,
  • R 9 represents alkyl, haloalkyl or cyanoalkyl
  • R 1 , R 2 , R 3 , R 5 and n have the meanings given above, reacted with hydrogen sulfide in the presence of a diluent.
  • the phenyluracil derivatives of the formula (I) according to the invention have a substantially better herbicidal activity than the constitutionally most similar, previously known substances of the same action.
  • the phenyl uracil derivatives according to the invention are generally defined by the formula (I).
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl - also in connection with heteroatoms, such as in alkoxy or alkylthio - are each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • R 1 represents hydrogen, amino or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, fluorine or chlorine,
  • R 2 represents formyl, hydroximinomethyl, cyano, carboxy, carbamoyl, thiocarbamoyl or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, fluorine or chlorine,
  • R 3 represents hydrogen, fluorine, chlorine, bromine or, if appropriate, by cyano
  • R 4 represents cyano or thiocarbamoyl, for hydroxy, mercapto, amino, hydroxyamino, cyano, nitro, fluorine, chlorine, bromine or for one of the radicals -R 6 , -QR 6 , -NH-R 6 , -NH-OR 6 , -NH-SO 2 -R 6 , -CQi-R 6 , -CQ ⁇ Q ⁇ R 6 , -CQ i -NH-R 6 , -Q 2 -CQ 1 -R 6 , -NH-CQ ⁇ R 6 , -Q 2 -CQ! - Q 2 -R 6 , -NH-CQ J -Q 2 ⁇ 6 or -Q 2 -CQ 1 -NH-R 6 , wherein
  • Q represents O, S, SO or SO 2 ,
  • Q 1 and Q 2 independently of one another represent oxygen or sulfur
  • R 6 for optionally by cyano, halogen, C1-C4- alkoxy, C ⁇ -C -
  • Cycloalkylalkyl each with 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, C1-C4-alkyl, C 1 -C4 -Halogen- alkyl, C1-C4-alkoxy, C 1 -C4-haloalkoxy, C 1 -C4-alkylthio, C ⁇ - C4-haloalkylthio, Cj-C4-alkylsulfinyl, Cj-C4-alkylsulfonyl, C ⁇ - C4-alkylamino and / or dimethylamino substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alky
  • n stands for the numbers 0, 1, 2 or 3.
  • R 1 represents hydrogen, amino, methyl or ethyl
  • R 2 stands for formyl, hydroximinomethyl, cyano, carboxy, carbamoyl, thiocarbamoyl or for methyl or ethyl which is optionally substituted by fluorine or chlorine,
  • R 3 represents hydrogen, chlorine or methyl or ethyl which is optionally substituted by fluorine or chlorine,
  • R 4 represents cyano or thiocarbamoyl
  • R 5 for hydroxy, mercapto, amino, hydroxyamino, cyano, nitro, fluorine, chlorine, bromine, or for one of the radicals R 6 , -QR 6 , -NH-R 6 , -NH-OR 6 , -NH-SO 2 -R 6 , -CO R 6 , -CQ QR 6 , -CQ NH-R 6 , -Q 2 -CQ 1 -R 6 , -NH-CQ ! -R 6 , -Q 2 -CQ
  • Q represents O, S, SO or SO 2 ,
  • Q 1 and Q 2 independently of one another represent oxygen or sulfur
  • R 6 for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, acetyl, propionyl, methoxycarbonyl,
  • n stands for the numbers 1 or 2.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • Reaction component the course of the process (c, variant ⁇ ) can be illustrated by the following formula.
  • Formula (II) provides a general definition of the aminoalkenic esters required as starting materials when carrying out process (a) and (b) according to the invention.
  • R 2 and R 3 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, preferably or as particularly preferred for R 2 and R 3 preferably represents alkyl with 1 to 4 carbon atoms, phenyl or benzyl. R particularly preferably represents methyl, ethyl or phenyl.
  • the starting materials of the formula (II) are known or can be prepared by known processes (cf. J. Heterocycl. Chem. 9 (1972), 513-522).
  • Formula (III) provides a general definition of the aryl isocyanates required as reaction components when carrying out process (a) according to the invention.
  • R 4 , R 5 and n preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R 4 , R 5 and n were specified.
  • Aryl isocyanates of the formula (III) can be prepared by using anilines of the formula
  • R 4 , R 5 and n have the meanings given above,
  • phosgene in the presence of a diluent, e.g. Chlorobenzene, at temperatures between -20 ° C and + 150 ° C.
  • a diluent e.g. Chlorobenzene
  • Formula (IV) provides a general definition of the aryl urethanes required as reaction components when carrying out process (b) according to the invention.
  • R 4 , R 5 and n preferably or particularly preferably 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 have been indicated preferably or as particularly preferred for R 4 , R 5 and n;
  • R 7 preferably represents CC 4 -alkyl, phenyl or benzyl, in particular methyl, ethyl or phenyl.
  • the aryl urethanes of the formula (IV) are known or can be prepared by known processes (cf. EPA 0 063 905).
  • Aryl urethanes of the formula (IV) are thus obtained by using anilines of the formula
  • R 4 , R 5 and n have the meaning given above,
  • R 7 has the meaning given above
  • phenyluracil derivatives of the formula (Ia) required as starting materials when carrying out process (c) according to the invention are compounds according to the invention which can be prepared by processes (a) or (b) according to the invention.
  • Formula (VI) provides a general definition of the sulfates required as reaction components when carrying out the process (c, variant ⁇ ).
  • R 8 preferably represents alkyl having 1 to 4 carbon atoms, particularly preferably methyl or ethyl.
  • halogen compounds which can also be used as reaction components when carrying out the process (c, variant ⁇ ) are as follows:
  • R 9 preferably represents alkyl, cyanoalkyl, fluoroalkyl or chloroalkyl each having 1 to 4 carbon atoms.
  • Shark is preferably bromine or iodine.
  • R 9 particularly preferably represents methyl or ethyl.
  • Shark is also particularly preferably bromine or iodine.
  • phenyluracil derivatives of the formula (Ib) required as starting materials when carrying out process (d) according to the invention are compounds according to the invention which can be prepared by processes (a), (b) or (c) according to the invention.
  • Alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates such as sodium, potassium or calcium acetate, lithium, sodium, potassium, or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium - or potassium methanolate, ethanolate, n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N, N
  • Suitable diluents for carrying out processes (a) and (b) according to the invention are all customary inert organic solvents.
  • 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 butylonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,
  • Ethylene glycol monoethyl ether diethylene glycol monomethyl ether and diethylene glycol monoethyl ether.
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C. Processes (a) to (c) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under increased pressure or, if no volatile components are used, under reduced pressure.
  • Suitable diluents for carrying out process (c) according to the invention are all inert organic solvents which are customary for such reactions.
  • aprotic polar solvents such as e.g. N, N-dimethylformamide and N-methylpyrrolidone.
  • aprotic, polar solvents such as e.g. Acetone, acetonitrile, N, N-dimethylformamide and dimethyl sulfoxide.
  • reaction temperatures can also be varied within a certain range.
  • the variant ( ⁇ ) is generally carried out at temperatures between 0 ° C. and 100 ° C., preferably between 10 ° C. and 50 ° C.
  • the variant ( ⁇ ) is generally carried out at temperatures between 0 ° C. and 200 ° C., preferably between 10 ° C. and 120 ° C.
  • Suitable diluents for carrying out process (d) according to the invention are all inert organic solvents which are customary for such reactions.
  • Hydrocarbons such as e.g. Toluene, or also organic bases, such as e.g. Pyridine, triethylamine and tributylamine.
  • reaction temperatures can also be varied within a certain range. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 100 ° C.
  • process is optionally carried out under elevated pressure, preferably under a pressure between 1 and 5 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 an acid binder, 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 phenyluracil derivatives of the formula (I) according to the invention are notable for strong herbicidal activity. They also show good tolerance to important crops, such as Wheat.
  • 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 as total or selective
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Taraxacum Dicotyledon cultures of the genera Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita
  • the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops 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 fields and for selective weed control in annual crops
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops both in the pre-emergence and in the post-emergence process
  • the active ingredients can be converted into the usual formulations, such as
  • Solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances These 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, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • Liquid solvents are essentially suitable.
  • Aromatics such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as
  • Chlorobenzenes chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example 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
  • Solid carrier materials are possible: 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 silicic acid, aluminum oxide and silicates are used as solid carriers for granules
  • 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
  • dispersants include, for example, lignin sulfite waste liquors and methyl cellulose
  • adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amidochlor, amidosulfuron, asulam, atrazine, azimsulfuron, benzazoline, benfuresate, bensulfuron (-methyl) , Bentazon, Benzofenap, Benzoylprop (- ethyl), Bialaphos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor,
  • Fluazifop (-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, Flurenol, Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (- ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethazyr, Imazamoxaza, Imazamoxaza, Imazamoxaza Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxafluto
  • MCPP Mefenacet, Meta itron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (- methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Norbenzonon, Nicbenulonazon, Nicalinulazuron, Nicalinulazuron, Nicalinulazuron, Nicalinulazuron Oxyfluorfen, paraquat, penimethalin, phenmedipham, piperophos, pretilachlor, primisulfuron (-methyl),
  • Prometryn Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Prosulfonon, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-ethyl) - tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, tebutam, tebuthiuron, terbuthylazine,
  • 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.
  • a mixture of 8.1 g (27 mmol) of 3-amino-4,4,4-trifluoro-crotonic acid ethyl ester, 7.5 g of potassium carbonate and 100 ml of N-methyl-pyrrolidone is heated for one hour on a water separator. Then 7.0 g (27 mmol) of N- (5-cyano-2,4-dichlorophenyl) -O-ethyl-urethane are added, and the reaction mixture is stirred at 130 ° C. for a further 4 hours. After cooling to room temperature, the mixture is diluted to about four times the volume with approximately equal volumes of water and ethyl acetate and acidified to approximately pH 3 with concentrated hydrochloric acid.
  • 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.
  • Example B the substances according to the invention listed in Examples 2, 3 and 6, at application rates of 60 to 250 g / ha and with good tolerance to wheat, show an efficiency of 80% or more against various weeds.
  • Example B the substances according to the invention listed in Examples 2, 3 and 6, at application rates of 60 to 250 g / ha and with good tolerance to wheat, show an efficiency of 80% or more against various weeds.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • Test plants which have 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.
  • the substances according to the invention listed in Examples 2, 3 and 6 show an efficiency of 80% or more compared to various weeds at application rates between 60 and 2000 g / ha.

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

Abstract

L'invention concerne de nouveaux dérivés de phényluracyle, de la formule (I), dans laquelle R?1, R2, R3, R4, R5¿ et n ont la signification donnée dans la description, plusieurs procédés permettant de produire ces dérivés, et leur utilisation comme herbicides.
PCT/EP1997/006367 1996-11-27 1997-11-14 Nouveaux derives de phenyluracyle a effet herbicide WO1998023598A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP52421998A JP2001504503A (ja) 1996-11-27 1997-11-14 除草剤効果を有するフェニル―ウラシル誘導体
CA002272657A CA2272657A1 (fr) 1996-11-27 1997-11-14 Nouveaux derives de phenyluracyle a effet herbicide
BR9713546-1A BR9713546A (pt) 1996-11-27 1997-11-14 Derivados de fenil-uracila com efeito herbicida
AU53222/98A AU5322298A (en) 1996-11-27 1997-11-14 Phenyl-uracil derivatives with herbicide effect
EP97950192A EP0944607A1 (fr) 1996-11-27 1997-11-14 Nouveaux derives de phenyluracyle a effet herbicide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19649094A DE19649094A1 (de) 1996-11-27 1996-11-27 Phenyl-uracil-Derivate
DE19649094.4 1996-11-27

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WO1998023598A1 true WO1998023598A1 (fr) 1998-06-04

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JP (1) JP2001504503A (fr)
KR (1) KR20000053150A (fr)
CN (1) CN1253550A (fr)
AU (1) AU5322298A (fr)
BR (1) BR9713546A (fr)
CA (1) CA2272657A1 (fr)
DE (1) DE19649094A1 (fr)
WO (1) WO1998023598A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001316375A (ja) * 1999-11-01 2001-11-13 Sumitomo Chem Co Ltd ６−ヒドロキシ−５，６−ジヒドロウラシル化合物

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0255047A1 (fr) * 1986-07-31 1988-02-03 Ciba-Geigy Ag Aryl-3 uraciles et leur application comme herbicides
WO1988010254A1 (fr) * 1987-06-19 1988-12-29 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1989002891A1 (fr) * 1987-09-23 1989-04-06 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1989003825A1 (fr) * 1987-10-22 1989-05-05 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1991000278A1 (fr) * 1989-06-29 1991-01-10 Ciba-Geigy Ag Composes heterocycliques
EP0408382A2 (fr) * 1989-07-14 1991-01-16 Nissan Chemical Industries, Limited Dérivés d'uraciles et herbicides les contenant comme ingrédient actif
EP0438209A1 (fr) * 1990-01-18 1991-07-24 Nissan Chemical Industries, Limited Dérivés de l'uracil et pesticides contenant ces dérivés comme agent actif
JPH0525142A (ja) * 1991-07-12 1993-02-02 Nissan Chem Ind Ltd ウラシル誘導体及び有害生物防除剤
WO1993006090A1 (fr) * 1991-09-20 1993-04-01 Basf Aktiengesellschaft 3-phenyluraciles substitues utilises comme herbicides
EP0542685A1 (fr) * 1991-11-13 1993-05-19 Ciba-Geigy Ag Dérivés du 3-Aryluracile et leur utilisation dans la lutte contre les mauvaises herbes

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WO1989003825A1 (fr) * 1987-10-22 1989-05-05 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1991000278A1 (fr) * 1989-06-29 1991-01-10 Ciba-Geigy Ag Composes heterocycliques
EP0408382A2 (fr) * 1989-07-14 1991-01-16 Nissan Chemical Industries, Limited Dérivés d'uraciles et herbicides les contenant comme ingrédient actif
EP0438209A1 (fr) * 1990-01-18 1991-07-24 Nissan Chemical Industries, Limited Dérivés de l'uracil et pesticides contenant ces dérivés comme agent actif
JPH0525142A (ja) * 1991-07-12 1993-02-02 Nissan Chem Ind Ltd ウラシル誘導体及び有害生物防除剤
WO1993006090A1 (fr) * 1991-09-20 1993-04-01 Basf Aktiengesellschaft 3-phenyluraciles substitues utilises comme herbicides
EP0542685A1 (fr) * 1991-11-13 1993-05-19 Ciba-Geigy Ag Dérivés du 3-Aryluracile et leur utilisation dans la lutte contre les mauvaises herbes

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* Cited by examiner, † Cited by third party
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JP2001316375A (ja) * 1999-11-01 2001-11-13 Sumitomo Chem Co Ltd ６−ヒドロキシ−５，６−ジヒドロウラシル化合物
JP4639459B2 (ja) * 1999-11-01 2011-02-23 住友化学株式会社 ６−ヒドロキシ−５，６−ジヒドロウラシル化合物

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KR20000053150A (ko) 2000-08-25
CN1253550A (zh) 2000-05-17
DE19649094A1 (de) 1998-05-28
CA2272657A1 (fr) 1998-06-04
BR9713546A (pt) 2000-01-25
EP0944607A1 (fr) 1999-09-29
AU5322298A (en) 1998-06-22

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