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WO1998040362A1 - Arylalkyluraciles substituees - Google Patents

Arylalkyluraciles substituees Download PDF

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Publication number
WO1998040362A1
WO1998040362A1 PCT/EP1998/001056 EP9801056W WO9840362A1 WO 1998040362 A1 WO1998040362 A1 WO 1998040362A1 EP 9801056 W EP9801056 W EP 9801056W WO 9840362 A1 WO9840362 A1 WO 9840362A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
alkyl
chlorine
general formula
optionally substituted
Prior art date
Application number
PCT/EP1998/001056
Other languages
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 AU67248/98A priority Critical patent/AU6724898A/en
Publication of WO1998040362A1 publication Critical patent/WO1998040362A1/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 invention relates to new substituted arylalkyluracils, processes for their preparation and their use as herbicides.
  • A stands for straight-chain or branched alkanediyl with two or more carbon atoms
  • Ar represents in each case optionally substituted phenyl or naphthyl
  • R 1 represents hydrogen, amino or optionally substituted alkyl
  • R 2 represents halogen substituted alkyl
  • R 3 represents hydrogen, halogen or alkyl.
  • 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
  • a 3 represents optionally substituted alkyl
  • X represents halogen or the grouping -O-SO 2 -OA 3 ,
  • the new substituted arylalkyluracils of the general formula (I) are notable for strong herbicidal activity. They also show good tolerance to important crops, such as Corn.
  • the invention preferably relates to compounds of the formula (I) in which A represents straight-chain or branched alkanediyl having two to four carbon atoms,
  • Ar for each optionally by amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, C1-C4-alkyl (which is optionally substituted by fluorine and / or chlorine) and / or C 1 -C 4 -alkoxy (which optionally substituted by fluorine and / or chlorine)
  • R 1 represents hydrogen, amino or optionally by cyano, fluorine or
  • Chlorine-substituted alkyl having 1 to 4 carbon atoms Chlorine-substituted alkyl having 1 to 4 carbon atoms
  • R 2 represents fluorine and / or chlorine-substituted alkyl having 1 to 4 carbon atoms and
  • R 3 represents hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms.
  • the invention relates in particular to compounds of the formula (I) in which
  • Ar represents phenyl optionally substituted by amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and / or trifluoromethoxy,
  • R 1 represents hydrogen, amino, methyl or ethyl
  • R 2 represents methyl or ethyl substituted by fluorine and / or chlorine and R 3 represents hydrogen, chlorine, bromine or methyl.
  • radicals listed above or those specified in preferred ranges 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.
  • 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) are: Formula (II) generally defined.
  • 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 is preferably C 4 -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 arylalkyl urethanes (arylalkyl carbamates) to be used further as starting materials in process (a) according to the invention.
  • a and Ar 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 A and Ar;
  • a 2 is preferably C j -C4 alkyl, phenyl or benzyl, especially methyl or ethyl.
  • the starting materials of the general formula (III) are known and / or can be prepared by known processes (cf. J. Org. Chem. 45 (1980), 4519-4522; loc. Cit. 48 (1983), 2520-2527; Synthesis 1980, 385-387; Tetrahedron: Asymmetry 1992, 281-286; loc. Cit. 1994, 363-370).
  • arylalkyl urethanes (arylalkyl carbamates) of the general formula (III) are obtained, for example, if arylalkyl amines of the general formula (V)
  • a 2 has the meaning given above,
  • substituted arylalkyluracils to be used as starting materials in the process (b) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (Ia)
  • A, Ar, R 2 and R 3 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 A, Ar, R 2 and R 3
  • alkylating agents to be used further as starting materials in process (b) according to the invention are generally defined by the formula (IV).
  • R 1 and R 2 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the inventive Compounds of formula (I) preferably or as particularly preferred for R 1 and R 2 have been specified
  • 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
  • the starting materials of formula (IV) are known organic synthetic chemicals.
  • 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 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, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexyl
  • Inert organic solvents are particularly suitable as diluents for carrying out processes (a) and (b) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated
  • Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrahydrofuran chlorinated carbon; 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 sulfoxides
  • 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) and (b) according to the invention are generally carried out under normal 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 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 for several hours at the required temperature.
  • 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 be used, for example, 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, for example on industrial and track systems 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, gum, oil palm, cocoa, berry fruit and hop plants are used 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 monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • 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, that is liquid solvents and / or solid
  • Carriers where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • 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
  • Silicic acid, aluminum oxide and silicates come 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 as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems, are emulsifying and / or foam-generating agents in question.
  • granules e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems, are emulsifying and / or foam-generating agents in question.
  • 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, and dispersants are, for example, lignin sulfite liquors 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, 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%
  • the active compounds according to the invention can also be used in a mixture with known herbicides for combating weeds, finished formulations or tank mixes being possible
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium),
  • Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dime roleson, Dimepiperate, Dimethachlor, Di- methametryn, dimethenamid, dinitramine, diphenamide, diquat, dithiopyr, diuron, dymron, EPTC, esprocarb, ethalfluralin, ethametsul Proceedingson (-methyl), etho colmesate, ethoxyfen, etobenzanid, fenoxaprop (-ethyl), flamprop (-isopropyliso, flamprop (-isopropyliso) - propyl-L), flamprop (-methyl), flazasulognion, fluazifop (-butyl), flumetsulam, flu
  • 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.
  • Example (III-1) for example, the compounds of the general formula (III) listed in Table 2 below can also be prepared.
  • 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 are applied in 1,000 l of water / ha Active ingredient quantities are applied
  • 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 in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compounds according to Preparation Examples 3, 12 and 13 show good compatibility with crop plants, such as e.g. Maize and strong action against weeds such as Setaria (80%), Abutilon (100%), Amaranthus (100%) and Galium (100%).

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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)

Abstract

L'invention concerne de nouvelles arylalkyluraciles substituées de la formule générale (I) dans laquelle A désigne un alcanediyle ayant deux atomes de carbone ou davantage, Ar désigne dans chaque cas phényle éventuellement substitué ou naphtyle, R1 désigne hydrogène, amino ou alkyle éventuellement substitué, R2 désigne alkyle substitué par halogène et R3 désigne hydrogène, halogène ou alkyle. L'invention concerne également des procédés permettant de les préparer et leur utilisation comme herbicides.
PCT/EP1998/001056 1997-03-10 1998-02-25 Arylalkyluraciles substituees WO1998040362A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU67248/98A AU6724898A (en) 1997-03-10 1998-02-25 Substituted arylalkyluracils

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997109703 DE19709703A1 (de) 1997-03-10 1997-03-10 Substituierte Arylalkyluracile
DE19709703.0 1997-03-10

Publications (1)

Publication Number Publication Date
WO1998040362A1 true WO1998040362A1 (fr) 1998-09-17

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ID=7822781

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/001056 WO1998040362A1 (fr) 1997-03-10 1998-02-25 Arylalkyluraciles substituees

Country Status (3)

Country Link
AU (1) AU6724898A (fr)
DE (1) DE19709703A1 (fr)
WO (1) WO1998040362A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2019727A1 (de) * 1969-04-19 1971-02-04 Dr Prof Shigeo Senda 1,3,6-substituierte Halogenuracile und ihre Herstellung
JPH0543555A (ja) * 1991-08-13 1993-02-23 Nissan Chem Ind Ltd ウラシル誘導体及び有害生物防除剤
WO1995004461A1 (fr) * 1993-08-11 1995-02-16 Fmc Corporation 3-(substitue-benzyle-)-1-methyle-6-trifluoromethyluraciles herbicides
WO1997001543A1 (fr) * 1995-06-29 1997-01-16 Basf Aktiengesellschaft 1-amino-3-benzyluraciles

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2019727A1 (de) * 1969-04-19 1971-02-04 Dr Prof Shigeo Senda 1,3,6-substituierte Halogenuracile und ihre Herstellung
JPH0543555A (ja) * 1991-08-13 1993-02-23 Nissan Chem Ind Ltd ウラシル誘導体及び有害生物防除剤
WO1995004461A1 (fr) * 1993-08-11 1995-02-16 Fmc Corporation 3-(substitue-benzyle-)-1-methyle-6-trifluoromethyluraciles herbicides
US5391541A (en) * 1993-08-11 1995-02-21 Fmc Corporation Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils
WO1997001543A1 (fr) * 1995-06-29 1997-01-16 Basf Aktiengesellschaft 1-amino-3-benzyluraciles

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
M. YOSHIMOTO ET AL., JOURNAL OF MEDICINAL CHEMISTRY, vol. 19, no. 1, 1976, pages 71 - 98, XP000609047 *
PATENT ABSTRACTS OF JAPAN vol. 17, no. 345 (C - 1077) 30 June 1993 (1993-06-30) *
S. SENDA ET AL., JOURNAL OF MEDICINAL CHEMISTRY, vol. 15, no. 5, 1972, pages 471 - 6, XP002072039 *
Y. KITA ET AL., JOURNAL OF ORGANIC CHEMISTRY, vol. 45, 1980, pages 4519 - 22, XP002072041 *

Also Published As

Publication number Publication date
AU6724898A (en) 1998-09-29
DE19709703A1 (de) 1998-09-17

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