WO1996036614A1 - Derives du type amino-uracile - Google Patents

Derives du type amino-uracile Download PDF

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Publication number
WO1996036614A1
WO1996036614A1 PCT/EP1996/001819 EP9601819W WO9636614A1 WO 1996036614 A1 WO1996036614 A1 WO 1996036614A1 EP 9601819 W EP9601819 W EP 9601819W WO 9636614 A1 WO9636614 A1 WO 9636614A1
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WO
WIPO (PCT)
Prior art keywords
chlorine
fluorine
optionally substituted
cyano
bromine
Prior art date
Application number
PCT/EP1996/001819
Other languages
German (de)
English (en)
Inventor
Roland Andree
Mark Wilhelm Drewes
Markus Dollinger
Hans-Joachim Santel
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 AU58122/96A priority Critical patent/AU5812296A/en
Publication of WO1996036614A1 publication Critical patent/WO1996036614A1/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
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Definitions

  • the invention relates to new aminouracil derivatives, a process for their preparation and their use as herbicides.
  • R 1 represents hydrogen, cyano or halogen
  • R 2 represents cyano, thiocarbamoyl, halogen or optionally substituted alkyl
  • R 3 represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl,
  • R 4 represents hydrogen, halogen or in each case optionally substituted alkyl or alkoxy and
  • R 5 represents optionally substituted alkyl.
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above,
  • the new aminouracil derivatives of the general formula (I) are notable for strong herbicidal activity.
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl, are each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents hydrogen, cyano, fluorine, chlorine, bromine or iodine
  • R 2 represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine
  • R 3 is optionally substituted by cyano, fluorine, chlorine, bromine, C r C 4 alkoxy or C] -C 4 -alkylthio-substituted alkyl having 1 to 6 carbon atoms
  • R 3 furthermore represents alkenyl or alkynyl, each with 2 to 6 carbon atoms, optionally substituted by fluorine, chlorine and / or bromine,
  • R 3 furthermore represents cycloalkyl or cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, optionally substituted by cyano, fluorine, chlorine, bromine or C 1 -C 4 alkyl,
  • R 3 furthermore for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, by C r C 4 alkyl, C r C 4 alkoxy, C r C 4 alkylthio, C r C 4 - Alkylsulf ⁇ nyl or C r C 4 -alkylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or diethylaminosulfonyl, by C - C 4 -alkoxy-carbohyl (which is optionally substituted by fluorine, chlorine, bromine,
  • Cyano, methoxy or ethoxy is substituted) by phenyl, phenyloxy or phenylthio (which are each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy) substituted phenyl, naphthyl, benzyl, phenylethyl , Thienyl, pyrazolyl, pyridinyl or quinolinyl,
  • R 4 represents hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms, and
  • R 5 represents alkyl with 1 to 4 carbon atoms optionally substituted by fluorine and / or chlorine.
  • the invention relates in particular to compounds of the formula (I) in which
  • R 1 represents hydrogen, cyano, fluorine or chlorine
  • R 2 represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl, difluoromethyl or trifluoromethyl
  • R 3 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 3 furthermore represents cyclopropyl, cyclobutyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,
  • R 3 for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy , Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio,
  • R 4 represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine, and
  • R 5 represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine.
  • the uracil derivatives to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II).
  • R 1 , R 2 , R 3 , R 4 and R 5 preferably or in particular have those meanings which have already been mentioned above for
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. EP 408382 / US 5084084 / US
  • the process according to the invention is carried out using an electrophilic aminating agent.
  • electrophilic amination agents can be used here. Examples include l-aminooxy-2,4-dinitro-benzene (2,4-dinitro-phenyl-hydroxylamine) and hydroxylamine-O-sulfonic acid.
  • the process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a suitable reaction auxiliary.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries.
  • This preferably includes 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, ethyldi
  • the process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a diluent.
  • a diluent is generally suitable as diluents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane Chloroform) or carbon tetrachloride, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, ethyl t-butyl ether, methyl t-pentyl
  • Alkanols such as, for example, methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, diethyl glycol monomethyl ether or monoethyl ether; their mixtures with water or pure water.
  • the reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -20 ° C and + 100 ° C, preferably between 0 ° C and 80 ° C, in particular between 20 ° C and 60 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are 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:
  • Matricaria Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronicaex, Abutil Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds of the formula (I) are suitable for total weed control, e.g. on industrial and track systems and on
  • 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 weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of dicotyledon weeds in monocotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
  • 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 foaming agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol 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.
  • alcohols 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 flours, such as kaolins, clays,
  • Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, 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.
  • nonionic 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; suitable dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • 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 phthalo- cyanine 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 weed control in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides for example anilides, such as e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2.4 D, 2.4 DB,
  • Aryloxy-phenoxy-alkanoic acid esters e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl
  • Azinones e.g. Chloridazon and norflurazon
  • Carbamates e.g. Chlorpropham, desmedipham, phenmedipham and propham
  • Chloroacetanilides e.g.
  • Sethoxydim and tralkoxydim Sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g. Mefenacet; Sulfonylureas, e.g.
  • Amidosulfuron bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primi sulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, e.g.
  • Atrazin cyanazin, simazin, simetryne, terbutryne and terbutylazin; Triazinones, e.g. Hexazinone, metamitron and metribuzin; Others, such as Aminotriazole, benfuresate,
  • active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also 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 the plants emerge. 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 diluted to about three times the volume with ethyl acetate.
  • the mixture is then added to approximately the same volume of a saturated aqueous sodium chloride solution, the organic phase is separated off and the aqueous phase is subsequently extracted with ethyl acetate.
  • the combined organic solutions are washed with water, dried with sodium sulfate and filtered. After concentrating the filtrate, the crude product obtained as a residue is purified by column chromatography (silica gel, cyclohexane / ethyl acetate, vol .: 1/1).
  • 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. Seeds of the test plants are sown in normal soil. After 24 hours, the soil is watered or sprayed with the active ingredient preparation. 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. After three weeks, the degree of damage to the plants is rated in%
  • the compounds according to Preparation 1, 2 and 3 show very strong activity against weeds such as abutilone (80-100%) with very good tolerance to crop plants, such as maize, (0%) and an application rate of 125 g / ha. ), Amaranthus (80-100%), Galium (90%) and Sinapis (80%).
  • weeds such as abutilone (80-100%) with very good tolerance to crop plants, such as maize, (0%) and an application rate of 125 g / ha. ), Amaranthus (80-100%), Galium (90%) and Sinapis (80%).
  • 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 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 compound according to Preparation Example 1 shows good compatibility with crop plants, such as Corn (5%) and one

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouveaux dérivés du type amino-uracile, de la formule générale (I) dans laquelle R?1, R2, R3, R4 et R5¿ ont la signification données dans la description. L'invention concerne également un procédé permettant de les préparer et leur utilisation comme herbicides.
PCT/EP1996/001819 1995-05-15 1996-05-02 Derives du type amino-uracile WO1996036614A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU58122/96A AU5812296A (en) 1995-05-15 1996-05-02 Aminouracil derivates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19517732.0 1995-05-15
DE1995117732 DE19517732A1 (de) 1995-05-15 1995-05-15 Aminouracilderivate

Publications (1)

Publication Number Publication Date
WO1996036614A1 true WO1996036614A1 (fr) 1996-11-21

Family

ID=7761914

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/001819 WO1996036614A1 (fr) 1995-05-15 1996-05-02 Derives du type amino-uracile

Country Status (3)

Country Link
AU (1) AU5812296A (fr)
DE (1) DE19517732A1 (fr)
WO (1) WO1996036614A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0408382A2 (fr) * 1989-07-14 1991-01-16 Nissan Chemical Industries, Limited Dérivés d'uraciles et herbicides les contenant comme ingrédient actif
WO1994004511A1 (fr) * 1992-08-21 1994-03-03 Nissan Chemical Industries, Ltd. Derive de pyrimidine et herbicide
EP0648749A2 (fr) * 1993-08-18 1995-04-19 Bayer Ag N-cyanoaryle hétérocycles azotés

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0408382A2 (fr) * 1989-07-14 1991-01-16 Nissan Chemical Industries, Limited Dérivés d'uraciles et herbicides les contenant comme ingrédient actif
WO1994004511A1 (fr) * 1992-08-21 1994-03-03 Nissan Chemical Industries, Ltd. Derive de pyrimidine et herbicide
EP0648749A2 (fr) * 1993-08-18 1995-04-19 Bayer Ag N-cyanoaryle hétérocycles azotés

Also Published As

Publication number Publication date
AU5812296A (en) 1996-11-29
DE19517732A1 (de) 1996-11-21

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