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WO1996016043A1 - Substituted diazacyclohexane di(thi)ons having a herbicidal effect - Google Patents

Substituted diazacyclohexane di(thi)ons having a herbicidal effect Download PDF

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Publication number
WO1996016043A1
WO1996016043A1 PCT/EP1995/004353 EP9504353W WO9616043A1 WO 1996016043 A1 WO1996016043 A1 WO 1996016043A1 EP 9504353 W EP9504353 W EP 9504353W WO 9616043 A1 WO9616043 A1 WO 9616043A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
chlorine
diyl
fluorine
optionally substituted
Prior art date
Application number
PCT/EP1995/004353
Other languages
German (de)
French (fr)
Inventor
Mark Wilhelm Drewes
Roland Andree
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 AU39817/95A priority Critical patent/AU3981795A/en
Publication of WO1996016043A1 publication Critical patent/WO1996016043A1/en

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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
    • 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
    • C07D239/553—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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
    • 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
    • C07D239/56—One oxygen atom and one sulfur atom
    • 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
    • C07D239/58—Two sulfur atoms

Definitions

  • the invention relates to new diazacyclohexanedi (thi) one, a process for their preparation and their use as herbicides.
  • Q 1 represents oxygen or sulfur
  • Q 2 represents oxygen or sulfur
  • R 1 represents hydrogen, cyano, nitro, halogen, alkyl or haloalkyl
  • R 2 represents hydrogen, cyano, nitro, thiocarbamoyl, halogen or alkyl or alkoxy which is optionally substituted by halogen,
  • R 3 represents the grouping below, -A 1 -A 2 -A 3 wherein
  • a 1 stands for a single bond, for oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen (in which case R 2 does not represent halogen), hydroxy, alkyl, Alkoxy, aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl, or
  • a 1 furthermore represents optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkendiyl or arendiyl,
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy,
  • a 2 furthermore stands for optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl, and
  • R 4 represents hydrogen, halogen, alkyl or haloalkyl
  • R 5 stands for alkyl or haloalkyl
  • R 6 stands for hydrogen, amino, hydroxy or for optionally substituted alkyl or cycloalkyl.
  • Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings given above, with a hydrogenating agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent.
  • the new diazacyclohexanedi (thi) one of the general formula (I) are characterized by strong and selective herbicidal activity.
  • the invention preferably relates to compounds of the formula (I) in which
  • Q 1 represents oxygen or sulfur
  • Q 2 represents oxygen or sulfur
  • R 1 represents hydrogen, cyano, nitro, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine,
  • R 2 represents hydrogen, cyano, nitro, thiocarbamoyl, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms,
  • R 3 represents the grouping below
  • a 1 stands for a single bond, for oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 is hydrogen (in which case R 2 does not represent fluorine, chlorine or bromine), hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, phenyl, C 1 -C 4 -alkylsulfonyl or phenylsulfonyl, A 1 furthermore in each case optionally by fluorine , Chlorine or bromine substituted C 1 -C 6 alkanediyl, C 2 -C 6 alkanediyl, C 2 -C 6 azaalkenediyl, C 2 -C 6 alkynediyl, C 3 -C 6 cycloalkanediyl, C 3 -C 6 Cycloalkenediyl or phenylene,
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy,
  • a 2 furthermore for C 1 -C 6 -alkanediyl, C 2 -C 6 -alkenediyl, C 2 -C 6 -azaalkenediyl, C 2 -C 6 -alkynediyl, C 3 -C 6 each optionally substituted by fluorine, chlorine or bromine -Cycloalkanediyl, C 3 -C 6 -cycloalkenediyl or phenylene,
  • Cycloalkylalkoxy or cycloalkylideneamino each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, halogen C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkyloxy, C 1 -C 4 haloalkyloxy and / or C 1 -C 4 alkoxycarbonyl substituted phenyl, phenyloxy, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 - alkoxy, (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
  • R 4 represents hydrogen, halogen or optionally fluorine and / or
  • Chlorine-substituted alkyl having 1 to 4 carbon atoms Chlorine-substituted alkyl having 1 to 4 carbon atoms
  • R 5 represents optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms
  • R 6 represents hydrogen, amino, hydroxy, optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms.
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino - are each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably
  • the invention relates in particular to compounds of the formula (I) in which
  • Q 1 stands for oxygen
  • Q 2 stands for oxygen
  • R 1 represents hydrogen, fluorine or chlorine
  • R 2 represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl
  • R 5 represents the grouping below, -A 1 -A 2 -A 3 in which
  • a 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen (in which case R 2 does not represent chlorine or bromine), hydroxy, Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,
  • a 1 furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy,
  • a 2 furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl
  • a 3 represents hydrogen, Hydroxy, amino, cyano, nitro, carbamoyl, sulfo,
  • R 4 represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,
  • R 5 for each optionally substituted by fluorine and / or chlorine
  • R 6 for hydrogen, amino, each optionally by fluorine and / or
  • Chlorine substituted methyl or ethyl or stands for cyclopropyl Chlorine substituted methyl or ethyl or stands for cyclopropyl.
  • the general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.
  • the uracils to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I) are generally defined by the formula (II).
  • Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 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) as preferred or as particularly preferred for Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 .
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. US 5084084, US 5127935, US 5154755, US 5169430, DE 4327743, DE 4343451, DE 4414326, production examples).
  • the process according to the invention for the preparation of the compounds of the formula (I) is carried out using a hydrogenating agent.
  • a hydrogenating agent The usual agents suitable for the hydrogenation of carbon-carbon double bonds are suitable. These include, for example, hydrogen (in the presence of a catalyst), lithium alanate (LiAlH 4 ), lithium boranate (LiBH 4 ), sodium boranate (NaBH 4 ) and potassium boranate (KBH 4 ).
  • the process according to the invention is optionally carried out - in particular in the case of hydrogenation with hydrogen - in the presence of a catalyst.
  • the usual hydrogenation catalysts are preferably used here.
  • Raney nickel or Raney cobalt platinum or palladium (the latter, if appropriate, on a carrier material such as coal).
  • organic solvents are suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated
  • Hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl or diethyl ether, diethylene glycol dimethyl ether or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile, butyronitrile or benzonitrile; Amides, such as N, N-dimethyl
  • 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 at temperatures between -10 ° C and + 80 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 100 bar.
  • the starting materials required in each case are generally used in approximately equimolar amounts.
  • 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.
  • Trifolium Ranunculus, Taraxacum.
  • the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other 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 pasture land and for selective purposes
  • Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of dicotyledon weeds in monocotyledon and dicotyledon 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, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as 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, if appropriate 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 aliphatic hydrocarbons such as chlorobenzene e, chloroethyl ene or methyl enchloride
  • al ipatic 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 such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • 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 as well as synthetic granules from inorganic and organic flours as well
  • Granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; 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; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • 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
  • Possible dispersants are: e
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, 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%.
  • 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 anilides, e.g. Diflufeni can and Propanil; Aryl carboxylic acids such as e.g.
  • Methabenzthiazuron hydroxylamines, e.g. Alloxydim, clethodim, cycloxydim, 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, chlorsulfuron,
  • Hydroxylamines e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim
  • Imidazolinones e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin
  • Cinosulfuron metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuronethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl;
  • Thiol carbamates such as butylates, cycloates, dialates, EPTC, Esprocarb, Molinate, prosulfocarb, Thiobencarb and triallates;
  • Triazines such as atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin;
  • Others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate,
  • 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 used both before and after
  • Emergence of the plants can be applied. 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 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
  • 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.
  • the active ingredient preparation is used to inject test plants which are 5 -
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 2000 l of water / ha. After three weeks, 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 1, 2 and 3 show good tolerance to crop plants, such as e.g.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1
  • Seeds of the test plants are sown in normal soil. After 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. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • the compounds according to Preparation Examples 1, 2 and 3 show good tolerance to crop plants, such as e.g. Corn (0%) and an application rate of 500 g / ha strong effect against crop plants, such as e.g. Corn (0%) and an application rate of 500 g / ha strong effect against crop plants, such as e.g. Corn (0%) and an application rate of 500 g / ha strong effect against crop plants, such as e.g. Corn (0%) and an application rate of 500 g / ha strong effect against

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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

The invention concerns novel diazacyclohexane di(thi)ons of general formula (I) in which R?1, R2, R3, R4, R5, R6, Q1 and Q2¿ have the meanings given in the description. The invention further concerns a process for their preparation and their use as herbicides.

Description

SUBSTITUIERTE DIAZACYCLOHEXANDI (THI )ONE MIT HERBIZIDER WIRKUNG  SUBSTITUTED DIAZACYCLOHEXANDI (THI) ONE WITH HERBICIDAL EFFECT
Die Erfindung betrifft neue Diazacyclohexandi(thi)one, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide. The invention relates to new diazacyclohexanedi (thi) one, a process for their preparation and their use as herbicides.
Es ist bekannt, daß bestimmte Diazacyclohexandi(thi)one herbizide Eigenschaften aufweisen (vgl. US 4927451 und JP 06092943). Die aus den angegebenen Patentschriften bekannten Verbindungen haben jedoch keine nennenswerte. Bedeutung erlangt. It is known that certain diazacyclohexanedi (thi) one have herbicidal properties (cf. US 4927451 and JP 06092943). However, the compounds known from the specified patents have no significant. Gained meaning.
Es wurden nun die neuen Diazacyclohexandi(thi)one der allgemeinen Formel (I) gefunden, The new diazacyclohexanedi (thi) ones of the general formula (I) have now been found
Figure imgf000003_0001
Figure imgf000003_0001
in welcher  in which
Q1 für Sauerstoff oder Schwefel steht, Q 1 represents oxygen or sulfur,
Q2 für Sauerstoff oder Schwefel steht, R1 für Wasserstoff, Cyano, Nitro, Halogen, Alkyl oder Halogenalkyl steht, Q 2 represents oxygen or sulfur, R 1 represents hydrogen, cyano, nitro, halogen, alkyl or haloalkyl,
R2 für Wasserstoff, Cyano, Nitro, Thiocarbamoyl, Halogen oder für jeweils gegebenenfalls durch Halogen substituiertes Alkyl oder Alkoxy steht, R 2 represents hydrogen, cyano, nitro, thiocarbamoyl, halogen or alkyl or alkoxy which is optionally substituted by halogen,
R3 für die nachstehende Gruppierung steht, -A1-A2-A3 worin R 3 represents the grouping below, -A 1 -A 2 -A 3 wherein
A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff (wobei in diesem Fall R2 nicht für Halogen steht), Hydroxy, Alkyl, Alkoxy, Aryl, Alkylcarbonyl, Alkylsulfonyl oder Arylsulfonyl steht, oder A 1 stands for a single bond, for oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen (in which case R 2 does not represent halogen), hydroxy, alkyl, Alkoxy, aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl, or
A1 weiterhin für jeweils gegebenenfalls substituiertes Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cycloalkandiyl, Cycloalkendiyl oder Arendiyl steht, A 1 furthermore represents optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkendiyl or arendiyl,
A2 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy,A 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy,
Alkyl, Alkoxy, Aryl, Alkylcarbonyl, Alkylsulfonyl oder Arylsulfonyl steht, Alkyl, alkoxy, aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl,
A2 weiterhin für jeweils gegebenenfalls substituiertes Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cycloalkandiyl, Cycloalkendiyl oder Arendiyl steht, und A 2 furthermore stands for optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl, and
A3 für Wasserstoff, Hydroxy, Mercapto, Amino, Cyano, Isocyano,A 3 for hydrogen, hydroxy, mercapto, amino, cyano, isocyano,
Thiocyanato, Nitro, Carbamoyl, Thiocarbamoyl, Sulfo, Chlorsulfonyl, Halogen oder für jeweils gegebenenfalls substituiertesThiocyanato, nitro, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen or for each optionally substituted
Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, Dialkoxy(thio)phosphoryl, Alkenyl, Alkenyloxy,Alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkoxy (thio) phosphoryl, alkenyl, alkenyloxy,
Alkenylamino, Alkylidenamino, Alkinyl, Alkinyloxy, Alkinylamino, Cycloalkyl, Cycloalkyloxy, Cycloalkylalkyl, Cycloalkylalkoxy, Cycloalkylidenamino, Aryl, Aryloxy, Arylalkyl, Arylalkoxy, Heterocyclyl, Heterocyclyl alkyl oder Heterocyclylalkoxy steht, Alkenylamino, alkylidenamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, Cycloalkylidene amino, aryl, aryloxy, arylalkyl, arylalkoxy, heterocyclyl, heterocyclyl alkyl or heterocyclylalkoxy,
R4 für Wasserstoff, Halogen, Alkyl oder Halogenalkyl steht, R 4 represents hydrogen, halogen, alkyl or haloalkyl,
R5 für Alkyl oder Halogenalkyl steht, und R6 für Wasserstoff, Amino, Hydroxy oder für jeweils gegebenenfalls substituiertes Alkyl oder Cycloalkyl steht. R 5 stands for alkyl or haloalkyl, and R 6 stands for hydrogen, amino, hydroxy or for optionally substituted alkyl or cycloalkyl.
Man erhält die neuen Diazacyclohexandi(thi)one der allgemeinen Formel (I), wenn man Uracile der allgemeinen Formel (II) The new diazacyclohexanedi (thi) ones of the general formula (I) are obtained if uracils of the general formula (II)
Figure imgf000005_0001
Figure imgf000005_0001
in welcher  in which
Q1, Q2, R1, R2, R3, R4, R5 und R6 die oben angegebenen Bedeutungen haben, mit einem Hydrierungsmittel, gegebenenfalls in Gegenwart eines Katalysators und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt. Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings given above, with a hydrogenating agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent.
Die neuen Diazacyclohexandi(thi)one der allgemeinen Formel (I) zeichnen sich durch starke und selektive herbizide Wirksamkeit aus. The new diazacyclohexanedi (thi) one of the general formula (I) are characterized by strong and selective herbicidal activity.
Gegenstand der Erfindung sind vorzugsweise Verbindungen der Formel (I), in welcher The invention preferably relates to compounds of the formula (I) in which
Q1 für Sauerstoff oder Schwefel steht, Q 1 represents oxygen or sulfur,
Q2 für Sauerstoff oder Schwefel steht, R1 für Wasserstoff, Cyano, Nitro, Fluor, Chlor, Brom oder für gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht, Q 2 represents oxygen or sulfur, R 1 represents hydrogen, cyano, nitro, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine,
R2 für Wasserstoff, Cyano, Nitro, Thiocarbamoyl, Fluor, Chlor, Brom oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl oder Alkoxy mit jeweils 1 bis 4 Kohlenstoffatomen steht, R 2 represents hydrogen, cyano, nitro, thiocarbamoyl, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms,
R3 für die nachstehende Gruppierung steht, R 3 represents the grouping below,
-A1-A2-A3 in welcher A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff (wobei in diesem Fall R2 nicht für Fluor, Chlor oder Brom steht), Hydroxy, C1-C4-Alkyl, C1-C4-Alkoxy, Phenyl, C1-C4-Alkylsulfonyl oder Phenylsulfonyl steht, A1 weiterhin für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C1-C6- Alkandiyl, C2-C6-Alkendiyl, C2-C6-Azaalkendiyl, C2-C6-Alkindiyl, C3-C6-Cycloalkandiyl, C3-C6-Cycloalkendiyl oder Phenylen steht, -A 1 -A 2 -A 3 in which A 1 stands for a single bond, for oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 is hydrogen (in which case R 2 does not represent fluorine, chlorine or bromine), hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, phenyl, C 1 -C 4 -alkylsulfonyl or phenylsulfonyl, A 1 furthermore in each case optionally by fluorine , Chlorine or bromine substituted C 1 -C 6 alkanediyl, C 2 -C 6 alkanediyl, C 2 -C 6 azaalkenediyl, C 2 -C 6 alkynediyl, C 3 -C 6 cycloalkanediyl, C 3 -C 6 Cycloalkenediyl or phenylene,
A2 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy,A 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy,
C1-C4-Alkyl, C1-C4-Alkoxy, Phenyl, C1-C4-Alkylsulfonyl oder Phenylsulfonyl steht, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, phenyl, C 1 -C 4 alkylsulfonyl or phenylsulfonyl,
A2 weiterhin für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C1-C6-Alkandiyl, C2-C6-Alkendiyl, C2-C6-Azaalkendiyl, C2-C6- Alkindiyl, C3-C6-Cycloalkandiyl, C3-C6-Cycloalkendiyl oder Phenylen steht, A 2 furthermore for C 1 -C 6 -alkanediyl, C 2 -C 6 -alkenediyl, C 2 -C 6 -azaalkenediyl, C 2 -C 6 -alkynediyl, C 3 -C 6 each optionally substituted by fluorine, chlorine or bromine -Cycloalkanediyl, C 3 -C 6 -cycloalkenediyl or phenylene,
A3 für Wasserstoff, Hydroxy, Amino, Cyano, Isocyano, Thiocyanato, Nitro, Carbamoyl, Thiocarbamoyl, Sulfo, Chlorsulfonyl, Halogen, für jeweils gegebenenfalls durch Halogen oder C1-C4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, oder Dialkoxy(thio)phosphoryl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl, Alkenyloxy,A 3 for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, or dialkoxy (thio) phosphoryl each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by halogen or C 1 -C 4 alkoxy, each optionally substituted by halogen Alkenyl, alkenyloxy,
Alkenylamino, Alkylidenamino, Alkinyl, Alkinyloxy oder Alkinyl- amino mit jeweils 2 bis 6 Kohlenstoffatomen in den Alkenyl-, Alkyliden- oder Alkinylgruppen, für jeweils gegebenenfalls durch Halogen, Cyano, Carboxy, C1-C4-Alkyl und/oder C1-C4-Alkoxycarbonyl substituiertes Cycloalkyl, Cycloalkyloxy, Cycloalkyl alkyl,Alkenylamino, alkylidene amino, alkynyl, alkynyloxy or alkynylamino each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each optionally by halogen, cyano, carboxy, C 1 -C 4 alkyl and / or C 1 - C 4 alkoxycarbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkyl alkyl,
Cycloalkylalkoxy oder Cycloalkylidenamino mit jeweils 3 bis 6 Kohlenstoffatomen in den Cycloalkylgruppen und gegebenenfalls 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Halogen C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkyloxy, C1-C4-Halogenalkyloxy und/oder C1-C4-Alkoxy-carbonyl substituiertes Phenyl, Phenyloxy, Phenyl-C1-C4-alkyl oder Phenyl-C1-C4-alkoxy, (jeweils gegebenenfalls ganz oder teilweise hydriertes) Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Iso- thiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl,Cycloalkylalkoxy or cycloalkylideneamino each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, halogen C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkyloxy, C 1 -C 4 haloalkyloxy and / or C 1 -C 4 alkoxycarbonyl substituted phenyl, phenyloxy, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 - alkoxy, (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl,
Triazinyl, Pyrazolyl-C1-C4-alkyl, FuryI-C1-C4-alkyl, Thienyl-C1-C4- alkyl, Oxazolyl-C1-C4-alkyl, Isoxazol-C1-C4-alkyl, Thiazol-C1-C4- alkyl, Pyridinyl-C1-C4-alkyl, Pyrimidinyl-C1-C4-alkyl, Pyrazolyl- methoxy, Furylmethoxy, für Perhydropyranylmethoxy oder Pyridylmethoxy steht, Triazinyl, pyrazolyl-C 1 -C 4 -alkyl, FuryI-C 1 -C 4 -alkyl, thienyl-C 1 -C 4 -alkyl, oxazolyl-C 1 -C 4 -alkyl, isoxazole-C 1 -C 4 - alkyl, thiazole-C 1 -C 4 -alkyl, pyridinyl-C 1 -C 4 -alkyl, pyrimidinyl-C 1 -C 4 -alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy,
R4 für Wasserstoff, Halogen oder für gegebenenfalls durch Fluor und/oder R 4 represents hydrogen, halogen or optionally fluorine and / or
Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht,  Chlorine-substituted alkyl having 1 to 4 carbon atoms,
R5 für gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht, und R6 für Wasserstoff, Amino, Hydroxy, für gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen oder für Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht. In den Definitionen sind die gesättigten oder ungesättigten Kohlenwasserstoffketten, wie Alkyl, Alkandiyl, Alkenyl oder Alkinyl - auch in Verbindung mit Heteroatomen, wie in Alkoxy, Alkylthio oder Alkylamino - jeweils geradkettig oder verzweigt. Halogen steht im allgemeinen für Fluor, Chlor, Brom oder lod, vorzugsweise fürR 5 represents optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms, and R 6 represents hydrogen, amino, hydroxy, optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms. In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino - are each straight-chain or branched. Halogen generally represents fluorine, chlorine, bromine or iodine, preferably
Fluor, Chlor oder Brom, insbesondere für Fluor oder Chlor. Fluorine, chlorine or bromine, especially for fluorine or chlorine.
Gegenstand der Erfindung sind insbesondere Verbindungen der Formel (I), in welcher The invention relates in particular to compounds of the formula (I) in which
Q1 für Sauerstoff steht, Q2 für Sauerstoff steht, Q 1 stands for oxygen, Q 2 stands for oxygen,
R1 für Wasserstoff, Fluor oder Chlor steht, R 1 represents hydrogen, fluorine or chlorine,
R2 für Cyano, Thiocarbamoyl, Chlor, Brom, Methyl oder Trifluormethyl steht, R 2 represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R5 für die nachstehende Gruppierung steht, -A1-A2-A3 in welcher R 5 represents the grouping below, -A 1 -A 2 -A 3 in which
A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff (wobei in diesem Fall R2 nicht für Chlor oder Brom steht), Hydroxy, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy,A 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen (in which case R 2 does not represent chlorine or bromine), hydroxy, Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,
Methylsulfonyl oder Ethylsulfonyl steht, Methylsulfonyl or ethylsulfonyl,
A1 weiterhin für Methylen, Ethan-1,1-diyl, Ethan-1,2-diyl, Propan-1,1- diyl, Propan-1,2-diyl, Propan-1,3-diyl, Ethen-1,2-diyl, Propen- 1,2- diyl, Propen-1,3-diyl, Ethin-1,2-diyl, Propin-1,2-diyl oder Propin- 1,3-diyl steht, A2 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy,A 1 furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl, A 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy,
Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i- Propoxy, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl oder Phenylsulfonyl steht, Is methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A2 weiterhin für Methylen, Ethan-1,1-diyl, Ethan-1,2-diyl, Propan-1,1- diyl, Propan-1,2-diyl, Propan-1,3-diyl, Ethen-1,2-diyl, Propen-1,2- diyl, Propen- 1,3-diyl, Ethin-1,2-diyl, Propin-1,2-diyl oder Propin- 1,3-diyl steht, A3 für Wasserstoff, Hydroxy, Amino, Cyano, Nitro, Carbamoyl, Sulfo,A 2 furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl, A 3 represents hydrogen, Hydroxy, amino, cyano, nitro, carbamoyl, sulfo,
Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- oder t-Pentyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, n-, i-, s- oder t-Pentyloxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Dimethylamino, Diethylamino, Dimethoxyphosphoryl, Diethoxyphosphoryl, Dipropoxyphosphoryl oder Diisopropoxyphosphoryl, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Propenyl, Butenyl, Propenyloxy, Butenyloxy, Propenylamino, Butenylamino, Propylidenamino, Butylidenamino, Propinyl, Butinyl, Propinyloxy, Butinyloxy, Propinylamino, Butinylamino, für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl oder Ethoxycarbonyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyl oxy, Cyclohexyloxy, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexyl- methyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino, Cyclo- hexylidenamino, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i- Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methoxycarbonyl und/oder Ethoxy carbonyl substituiertes Phenyl, Phenyloxy, Benzyl, Phenylethyl, Benzyloxy, (jeweils gegebenenfalls ganz oder teilweise hydriertes) Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Triazinyl, Pyrazolylmethyl, Furylmethyl, Thienylmethyl, Oxazolylmethyl, Isoxazolmethyl, Thiazolmethyl, Pyridinylmethyl, Pyrimidinylmethyl, Pyrazolylmethoxy, Furylmethoxy oder Pyridylmethoxy steht, Fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- substituted by fluorine, chlorine, methoxy or ethoxy or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i -Propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n -, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propenylamino, butenylamino, optionally substituted by fluorine or chlorine. Butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, each optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-Pro propyl, methoxycarbonyl or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyl oxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl methyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, Cyclopentylidenamino, cyclo hexylidenamino, or in each case optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxy carbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, (each optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, Pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy,
R4 für Wasserstoff, Fluor, Chlor, Brom oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl steht, R 4 represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,
R5 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes R 5 for each optionally substituted by fluorine and / or chlorine
Methyl oder Ethyl steht, und  Is methyl or ethyl, and
R6 für Wasserstoff, Amino, für jeweils gegebenenfalls durch Fluor und/oder R 6 for hydrogen, amino, each optionally by fluorine and / or
Chlor substituiertes Methyl oder Ethyl oder für Cyclopropyl steht. Die oben aufgeführten allgemeinen oder in Vorzugsbereichen angegebenen Restedefinitionen gelten sowohl für die Endprodukte der Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangsstoffe bzw. Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen Bereichen bevorzugter Verbindungen, beliebig kombiniert werden.  Chlorine substituted methyl or ethyl or stands for cyclopropyl. The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.
Verwendet man beispielsweise 1-(2,4-Dichlor-5-methoxy-phenyl)-3,6-dihydro-2,6- dioxo-3-methyl-4-trifluormethyl-1(2H)-pyrimidin und Wasserstoff in Gegenwart von Platin als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren durch das folgende Formelschema skizziert werden: For example, 1- (2,4-dichloro-5-methoxy-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine and hydrogen are used in the presence of Platinum as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:
Figure imgf000010_0001
Die beim erfϊndungsgemäßen Verfahren zur Herstellung der Verbindungen der allgemeinen Formel (I) als Ausgangsstoffe zu verwendenden Uracile sind durch die Formel (II) allgemein definiert. In der Formel (II) haben Q1, Q2, R1, R2, R3, R4, R5 und R6 vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der Verbindungen der Formel (I) als bevorzugt bzw. als insbesondere bevorzugt für Q1, Q2, R1, R2, R3, R4, R5 und R6 angegeben wurden.
Figure imgf000010_0001
The uracils to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I) are generally defined by the formula (II). In formula (II), Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 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) as preferred or as particularly preferred for Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 .
Die Ausgangsstoffe der Formel (II) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. US 5084084, US 5127935, US 5154755, US 5169430, DE 4327743, DE 4343451, DE 4414326, Herstellungsbeispiele). The starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. US 5084084, US 5127935, US 5154755, US 5169430, DE 4327743, DE 4343451, DE 4414326, production examples).
Das erfindungsgemäße Verfahren zur Herstellung der Verbindungen der Formel (I) wird unter Verwendung eines Hydrierungsmittels durchgeführt. Es kommen die üblichen, zur Hydrierung von Kohlenstoff-Kohlenstoff-Doppelbindungen geeigneten Mittel in Betracht. Hierzu gehören beispielsweise Wasserstoff (in Gegenwart eines Katalysators), Lithiumalanat (LiAlH4), Lithiumboranat (LiBH4), Natriumboranat (NaBH4) und Kaliumboranat (KBH4). The process according to the invention for the preparation of the compounds of the formula (I) is carried out using a hydrogenating agent. The usual agents suitable for the hydrogenation of carbon-carbon double bonds are suitable. These include, for example, hydrogen (in the presence of a catalyst), lithium alanate (LiAlH 4 ), lithium boranate (LiBH 4 ), sodium boranate (NaBH 4 ) and potassium boranate (KBH 4 ).
Das erfindungsgemäße Verfahren wird gegebenenfalls - insbesondere bei Hydrierung mit Wasserstoff - in Gegenwart eines Katalysators durchgeführt. Es kommen hierbei vorzugsweise die üblichen Hydrierungskatalysatoren in Betracht.The process according to the invention is optionally carried out - in particular in the case of hydrogenation with hydrogen - in the presence of a catalyst. The usual hydrogenation catalysts are preferably used here.
Hierzu gehören beispielsweise Raney-Nickel oder Raney-Cobalt, Platin oder Palladium (letztere gegebenenfalls auf einem Trägermaterial wie Kohle). These include, for example, Raney nickel or Raney cobalt, platinum or palladium (the latter, if appropriate, on a carrier material such as coal).
Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens kommen die üblichen organischen Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicyclische oder aromatische, gegebenenfalls halogenierteThe usual organic solvents are suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated
Kohlenwasserstoffe, wie beispielsweise Pentan, Hexan, Heptan, Petrolether, Ligroin, Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Cyclohexan, Methylcyclohexan, Dichlormethan, Chloroform, Tetrachlormethan; Ether, wie Diethylether, Diisopropylether, t-Butyl-methylether, t-Pentyl-methylether, Dioxan, Tetrahydrofuran, Ethylenglykol-dimethyl- oder -diethylether, Diethylenglykoldimethylether oder -diethylether; Ketone, wie Aceton, Butanon oder Methyl-iso- butyl-keton; Nitrile, wie Acetonitril, Propionitril, Butyronitril oder Benzonitril; Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methyl-pyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäure-methylester, -ethylester, -n- oder -i-propylester, -n-, -i- oder -s-butylester, Sulfoxide, wie Dimethylsulfoxid; Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, n-, i-, s- oder t-Butanol, Ethylenglykol-monomethylether oder -monoethylether, Diethylenglykolmonomethylether, Diethylenglykolmonoethy lether; derenHydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl or diethyl ether, diethylene glycol dimethyl ether or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile, butyronitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate, ethyl ester, n- or i-propyl ester, n-, i- or s-butyl ester, sulfoxides such as dimethyl sulfoxide; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether; their
Gemische mit Wasser oder reines Wasser. Mix with water or pure water.
Die Reaktionstemperaturen können bei der Durchfuhrung des erfindungsgemäßen Verfahrens in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und +100°C, vorzugsweise bei Temperaturen zwischen -10°C und +80°C. 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 at temperatures between -10 ° C and + 80 ° C.
Das erfindungsgemäße Verfahren wird im allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, unter erhöhtem oder vermindertem Druck - im allgemeinen zwischen 0,1 bar und 100 bar - zu arbeiten. The process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 100 bar.
Zur Durchführung des erfindungsgemäßen Verfahrens werden die jeweils benötigten Ausgangsstoffe im allgemeinen in angenähert äquimolaren Mengen eingesetzt.To carry out the process according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts.
Es ist jedoch auch möglich, eine der beiden jeweils eingesetzten Komponenten in einem größeren Überschuß zu verwenden. Die Reaktionen werden im allgemeinen in einem geeigneten Verdünnungsmittel gegebenenfalls in Gegenwart eines Katalysators durchgeführt, und das Reaktionsgemisch wird mehrere Stunden bei der jeweils erforderlichen Temperatur gerührt. Die Aufarbeitung erfolgt bei dem erfindungsgemäßen Verfahren jeweils nach üblichen Methoden (vgl. die Herstellungsbeispiele). However, it is also possible to use one of the two components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent, if appropriate in the presence of a catalyst, and the reaction mixture is stirred for several hours at the temperature required in each case. Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).
Die erfindungsgemäßen Wirkstoffe können als Defoliants, Desiccants, Krautabtötungsmittel und insbesondere als Unkrautvernichtungsmittel verwendet werden. Unter Unkraut im weitesten Sinne sind alle Pflanzen zu verstehen, die an Orten aufwachsen, wo sie unerwünscht sind. Ob die erfindungsgemäßen Stoffe als totale oder selektive Herbizide wirken, hängt im wesentlichen von der angewandten Menge ab. 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.
Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen verwendet werden. Dikotyle Unkräuter der Gattungen: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea,The active compounds according to the invention can be used, for example, in the following plants. Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea,
Trifolium, Ranunculus, Taraxacum. Trifolium, Ranunculus, Taraxacum.
Dikotyle Kulturen der Gattungen: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Monokotyle Unkräuter der Gattungen: Echinochloa, Setaria, Panicum, Digitaria,Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria,
Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Monokotyle Kulturen der Gattungen: Oryza, Zea, Triticum, Hordeum, Avena,Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactylocaopium, Agrostis. Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena,
Seeale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. Seeale, sorghum, panicum, saccharum, pineapple, asparagus, allium.
Die Verwendung der erfindungsgemäßen Wirkstoffe ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen. Die Verbindungen eignen sich in Abhängigkeit von der Konzentration zur Totalunkrautbekämpfung z.B. auf Industrie- und Gleisanlagen und auf Wegen und Plätzen mit und ohne Baumbewuchs. Ebenso können die Verbindungen zur Unkrautbekämpfung in Dauerkulturen, z.B. Forst, Ziergehölz-, Obst-, Wein-, Citrus-, Nuß-, Bananen-, Kaffee-, Tee-, Gummi-, Ölpalm-, Kakao-, Beerenfrucht- und Hopfenanlagen, auf Zier- und Sportrasen und Weideflächen und zur selektiven However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants. Depending on the concentration, 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. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes
Unkrautbekämpfung in einjährigen Kulturen eingesetzt werden. Weed control can be used in annual crops.
Die erfindungsgemäßen Verbindungen der Formel (I) eignen sich insbesondere zur selektiven Bekämpfung von dikotylen Unkräutern in monokotylen und dikotylen Kulturen sowohl im Vorauflauf- als auch im Nachauflauf- Verfahren. Die Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wieThe compounds of formula (I) according to the invention are particularly suitable for the selective control of dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process. The active ingredients can be converted into the usual formulations, such as
Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoffimprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen. Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermisehen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. These 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, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzol e, Chl orethyl ene oder Methyl enchl orid, al iphati sche Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie derenIf water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzene e, chloroethyl ene or methyl enchloride, al ipatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their
Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser. 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.
Als feste Trägerstoffe kommen in Frage: The following are suitable as solid carriers:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, e.g. Ammonium salts and natural rock flours, such as kaolins, clays,
Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowieTalc, 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 as well as synthetic granules from inorganic and organic flours as well
Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen- Fettsäure-Ester, Polyoxyethylen-Fettalkohol -Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose. Granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; 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; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein. Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. 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.
Die Formulierungen enthalten im allgemeinen zwischen 0, 1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %. Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formul i erungen auch i n Mi schung mi t bekannten Herbi ziden zur Unkrautbekämpfung Verwendung finden, wobei Fertigformulierύngen oder Tankmischungen möglich sind. 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, as such or in their formulations, can also be used in a mixture with known herbicides for combating weeds, finished formulations or tank mixes being possible.
Für die Mischungen kommen bekannte Herbizide infrage, beispielsweise Anilide, wie z.B . Diflufeni can und Propanil ; Arylcarbonsäuren, wi e z.B .Known herbicides are suitable for the mixtures, for example anilides, e.g. Diflufeni can and Propanil; Aryl carboxylic acids such as e.g.
Dichlorpicolinsäure, Dicamba und Picloram; Aryl oxy alkansäuren, wie z.B. 2,4 D, 2,4 DB, 2,4 DP, Fluroxypyr, MCPA, MCPP und Triclopyr; Aryloxy-phenoxyalkansäureester, wie z.B. Diclofop-methyl, Fenoxaprop-ethyl, Fluazifop-butyl, Haloxyfop-methyl und Quizalofop-ethyl; Azinone, wie z.B. Chloridazon und Norflurazon; Carbamate, wie z.B. Chlorpropham, Desmedipham, Phenmedipham und Propham; Chloracetanilide, wie z.B. Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor und Propachlor; Dinitroaniline, wie z.B. Oryzalin, Pendimethalin und Trifluralin; Diphenylether, wie z.B. Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen und Oxyfluorfen; Harnstoffe, wie z.B. Chlortoluron, Diuron, Fluometuron, Isoproturon, Linuron undDichloropicolinic acid, dicamba and picloram; Aryl oxy alkanoic acids, e.g. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxyalkanoic 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. Alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines, e.g. Oryzalin, pendimethalin and trifluralin; Diphenyl ethers, e.g. Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; Ureas, e.g. Chlorotoluron, Diuron, Fluometuron, Isoproturon, Linuron and
Methabenzthiazuron; Hydroxylamine, wie z.B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim und Tralkoxydim; Imidazolinone, wie z.B. Imazethapyr, Imazamethabenz, Imazapyr und Imazaquin; Nitrile, wie z.B. Bromoxynil, Dichlobenil und Ioxynil; Oxyacetamide, wie z.B. Mefenacet; Sulfonylharnstoffe, wie z.B. Amidosulfuron, Bensulfuron-methyl, Chlorimuron-ethyl, Chlorsulfuron,Methabenzthiazuron; Hydroxylamines, e.g. Alloxydim, clethodim, cycloxydim, 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, chlorsulfuron,
Cinosulfuron, Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuronethyl, Thifensulfuron-methyl, Triasulfuron und Tribenuron-methyl; Thiol carbamate, wie z.B. Butylate, Cycloate, Diallate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb und Triallate; Triazine, wie z.B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne und Terbutylazin; Triazinone, wie z.B. Hexazinon, Metamitron und Metribuzin; Sonstige, wie z.B. Aminotriazol, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate,Cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuronethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, such as butylates, cycloates, dialates, EPTC, Esprocarb, Molinate, prosulfocarb, Thiobencarb and triallates; Triazines such as atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin; Others, such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate,
Quinchlorac, Quinmerac, Sulphosate und Tridiphane. Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Streuen. Die erfindungsgemäßen Wirkstoffe können sowohl vor als auch nach demA 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 used both before and after
Auflaufen der Pflanzen appliziert werden. Sie können auch vor der Saat in den Boden eingearbeitet werden. Emergence of the plants can be applied. They can also be worked into the soil before sowing.
Die angewandte Wirkstoffmenge kann in einem größeren Bereich schwanken. Sie hängt im wesentlichen von der Art des gewünschten Effektes ab. Im allgemeinen liegen die Aufwandmengen zwischen 10 g und 10 kg Wirkstoff pro Hektar Bodenfläche, vorzugsweise zwischen 50 g und 5 kg pro ha. 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 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe geht aus den nachfolgenden Beispielen hervor. Herstellungsbeispiele: The preparation and use of the active compounds according to the invention can be seen from the examples below. Manufacturing examples:
Beispiel 1 example 1
Figure imgf000017_0002
Figure imgf000017_0002
2,03 g (5 mMol) 1-(4-Cyano-2-fluor-5-methylsulfonyl-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluormethyl-1(2H)-pyrimidin und 300 mg Palladium auf Kohle (10%ig) werden in 30 ml Tetrahydrofuran vorgelegt. Bei 20°C wird Wasserstoff aufgedrückt und die Reaktionsmischung wird dann unter der Wasserstoffatmosphäre 24 Stunden gerührt. Anschließend wird filtriert, das Filtrat im Wasserstrahlvakuum eingeengt und der Rückstand säulenchromatographisch (Kieselgel, Chloroform/Essigsäureethylester, Vol.: 1 :1) aufgearbeitet.  2.03 g (5 mmol) of 1- (4-cyano-2-fluoro-5-methylsulfonylphenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine and 300 mg palladium on carbon (10%) are placed in 30 ml tetrahydrofuran. Hydrogen is injected at 20 ° C. and the reaction mixture is then stirred under the hydrogen atmosphere for 24 hours. The mixture is then filtered, the filtrate is concentrated in a water jet vacuum and the residue is worked up by column chromatography (silica gel, chloroform / ethyl acetate, vol .: 1: 1).
Man erhält 0,5 g (25% der Theorie) 1-(4-Cyano-2-fluor-5-methylsulfonyl-phenyl)- hexahydro-2,6-dioxo-3-methyl-4-trifluormethyl-pyrimidin. 0.5 g (25% of theory) of 1- (4-cyano-2-fluoro-5-methylsulfonyl-phenyl) hexahydro-2,6-dioxo-3-methyl-4-trifluoromethyl-pyrimidine are obtained.
Schmelzpunkt >250°C.  Melting point> 250 ° C.
Beispiel 2 Example 2
Figure imgf000017_0001
Figure imgf000017_0001
2,03 g (5 mMol) 1-(4-Cyano-2-fluor-5-methylsulfonyl-phenyl)-3,6-dihydro-2,6- dioxo-3-methyl-4-trifluormethyl-1(2H)-pyrimidin werden in 20 ml Tetrahydrofuran vorgelegt und auf 0°C abgekühlt. Bei dieser Temperatur werden 210 mg (5,5 mMol) Natriumboranat (NaBH4) dazu gegeben und die Reaktionsmischung wird dann 3 Stunden bei 0°C gerührt. Anschließend werden 30 ml 5%ige Salzsäure dazu gegeben und die Mischung wird mit 50 ml Essigsäureethylester durchgeschüttelt. Die organische Phase wird abgetrennt, mit Natriumsulfat getrocknet und filtriert. Das Filtrat wird im Wasserstrahlvakuum eingeengt und der Rückstand säulenchromatographisch (Kieselgel, Chloroform/Essigsäureethylester, Vol.: 1:1) aufgearbeitet. 2.03 g (5 mmol) of 1- (4-cyano-2-fluoro-5-methylsulfonylphenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine are placed in 20 ml of tetrahydrofuran and cooled to 0 ° C. At this temperature 210 mg (5.5 mmol) of sodium boranate (NaBH 4 ) are added and the reaction mixture is then stirred for 3 hours at 0 ° C. Then 30 ml of 5% hydrochloric acid are added and the mixture is shaken with 50 ml of ethyl acetate. The organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is worked up by column chromatography (silica gel, chloroform / ethyl acetate, vol .: 1: 1).
Man erhält 0,5 g (25% der Theorie) 1-(4-Cyano-2-fluor-5-methylsulfonyl-phenyl)-hexahydro-2,6-dioxo-3-methyl-4-trifluormethyl-pyrimidin. 0.5 g (25% of theory) of 1- (4-cyano-2-fluoro-5-methylsulfonylphenyl) hexahydro-2,6-dioxo-3-methyl-4-trifluoromethyl-pyrimidine are obtained.
Schmelzpunkt >250°C. Analog zu den Beispielen 1 und 2 sowie entsprechend der allgemeinen Melting point> 250 ° C. Analogous to Examples 1 and 2 and in accordance with the general
Beschreibung des erfindungsgemäßen Herstellungsverfahrens können beispielsweise auch die in der nachstehenden Tabelle 1 aufgeführten Verbindungen der Formel (I) hergestellt werden. A description of the production process according to the invention can also be used, for example, to prepare the compounds of the formula (I) listed in Table 1 below.
Figure imgf000018_0001
Figure imgf000018_0001
Figure imgf000019_0001
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000023_0001
Ausgangsstoffe der Formel (II): Beispiel (II-1) Starting materials of formula (II): Example (II-1)
Figure imgf000024_0001
Figure imgf000024_0001
1,8 g (10 mMol) 3-Amino-4,4,4-trifluor-crotonsäureethylester werden in 30 ml Di-methylformamid und 2 ml Toluol vorgelegt und bei 0°C bis 5°C mit 0,3 g (10 mMol) Natriumhydrid (80%ig) versetzt. Das Gemisch wird 30 Minuten bei 0°C bis 5°C gerührt. Nach Abkühlen der Mischung auf -70°C werden 0,9 g (5 mMol) 4-Cyano-2,5-difluor-phenylisocyanat - gelöst in 10 ml Toluol - dazu gegeben und das Gemisch wird 150 Minuten bei -60°C bis -70°C gerührt. Nach Entfernen des Kühlbades werden 2 ml Essigsäure dazu gegeben. Dann wird mit Wasser auf etwa das doppelte Volumen verdünnt und mit Essigsäureethylester extrahiert. Die organische Phase wird eingeengt und der Rückstand mit Diisopropylether zur Kristallisation gebracht.  1.8 g (10 mmol) of 3-amino-4,4,4-trifluoro-crotonic acid ethyl ester are placed in 30 ml of dimethylformamide and 2 ml of toluene and at 0 ° C to 5 ° C with 0.3 g (10 mmol ) Sodium hydride (80%) added. The mixture is stirred at 0 ° C to 5 ° C for 30 minutes. After cooling the mixture to -70 ° C, 0.9 g (5 mmol) of 4-cyano-2,5-difluoro-phenyl isocyanate - dissolved in 10 ml of toluene - are added and the mixture is at -60 ° C for 150 minutes -70 ° C stirred. After removing the cooling bath, 2 ml of acetic acid are added. The mixture is then diluted to about twice the volume with water and extracted with ethyl acetate. The organic phase is concentrated and the residue is crystallized with diisopropyl ether.
Man erhält 1,1 g (69% der Theorie) 1-(4-Cyano-2,5-difluor-phenyl)-3,6-dihydro- 2,6-dioxo-4-trifluormethyl-1(2H)-pyrimidin vom Schmelzpunkt 194°C. 1.1 g (69% of theory) of 1- (4-cyano-2,5-difluorophenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) pyrimidine are obtained melting point 194 ° C.
Beispiel (II-2) Example (II-2)
Figure imgf000025_0001
Figure imgf000025_0001
Eine Mischung aus 0,83 g (3 mMol) 1-(4-Cyano-2,5-difluor-phenyl)-3,6-dihydro-2,6-dioxo-3,4-dimethyl-1(2H)-pyrimidin, 0,32 g (3 mMol) Methansulfonamid, 0,6 g Kaliumcarbonat und 10 ml Dimethylsulfoxid wird 10 Stunden auf 120°C erhitzt. A mixture of 0.83 g (3 mmol) of 1- (4-cyano-2,5-difluorophenyl) -3,6-dihydro-2,6-dioxo-3,4-dimethyl-1 (2H) - pyrimidine, 0.32 g (3 mmol) of methanesulfonamide, 0.6 g of potassium carbonate and 10 ml of dimethyl sulfoxide is heated at 120 ° C. for 10 hours.
Nach Abkühlen wird die Mischung auf Eiswasser gegossen und mit 2N-Salzsäure angesäuert. Dann wird mit Essigsäureethylester extrahiert, die organische Phase mit Wasser gewaschen, mit Natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel im Wasserstrahlvakuum sorgfältig abdestilliert. Man erhält 0,8 g (76% der Theorie) 1-(4-Cyano-2-fluor-5-methylsulfonylamino)- 3,6-dihydro-2,6-dioxo-3,4-dimethyl-1(2H)-pyrimidin als kristallinen Rückstand (Schmelzpunkt >250°C). After cooling, the mixture is poured onto ice water and acidified with 2N hydrochloric acid. Then it is extracted with ethyl acetate, the organic phase is washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum. 0.8 g (76% of theory) of 1- (4-cyano-2-fluoro-5-methylsulfonylamino) -3,6-dihydro-2,6-dioxo-3,4-dimethyl-1 (2H) are obtained. -pyrimidine as a crystalline residue (melting point> 250 ° C).
Anwendungsbeispiele: Examples of use:
Beispiel A Example A
Post-emergence-Test Post emergence test
Lösungsmittel. 5 Gewichtsteile Aceton Solvent. 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil Alkylarylpolyglykolether Emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Mit der Wirkstoffzubereitung spritzt man Testpflanzen, welche eine Höhe von 5 -To produce a suitable preparation of 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. The active ingredient preparation is used to inject test plants which are 5 -
15 cm haben so, daß die jeweils gewünschten Wirkstoffmengen pro Flächeneinheit ausgebracht werden. Die Konzentration der Spritzbrühe wird so gewählt, daß in 2000 1 Wasser/ha die jeweils gewünschten Wirkstoffmengen ausgebracht werden. Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle. 15 cm so that the desired amounts of active ingredient are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 2000 l of water / ha. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
Es bedeuten: It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 0% = no effect (like untreated control)
100 % = totale Vernichtung  100% = total annihilation
In diesem Test zeigen beispielsweise die Verbindungen gemäß den Herstellungsbeispielen 1, 2 und 3 bei guter Verträglichkeit gegenüber Kulturpflanzen, wie z.B.In this test, for example, the compounds according to Preparation Examples 1, 2 and 3 show good tolerance to crop plants, such as e.g.
Weizen (19 %) und einer Aufwandmenge von 500 g/ha starke Wirkung gegen Unkräuter wie Amaranthus (95-100 %), Ambrosia (90-100 %), Polygonum (100 %), Viola (90-95 %) und Xanthium (95-100 %). Beispiel B Wheat (19%) and an application rate of 500 g / ha strong action against weeds such as amaranthus (95-100%), ambrosia (90-100%), polygonum (100%), viola (90-95%) and xanthium ( 95-100%). Example B
Pre-emergence-Test Pre-emergence test
Lösungsmittel: 5 Gewichtsteile Aceton Solvent: 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1
Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Part by weight of active ingredient with the stated amount of solvent, adds the stated amount of emulsifier and dilutes the concentrate with water to the desired concentration.
Samen der Testpflanzen werden in normalen Boden ausgesät. Nach 24 Stunden wird der Boden mit der Wirkstoffzubereitung begossen. Dabei hält man die Wassermenge pro Flächeneinheit zweckmäßigerweise konstant. Die Wirkstoffkonzentration in der Zubereitung spielt keine Rolle, entscheidend ist nur die Aufwandmenge des Wirkstoffs pro Flächeneinheit. Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle. Es bedeuten: Seeds of the test plants are sown in normal soil. After 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. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 0% = no effect (like untreated control)
100 % = totale Vernichtung  100% = total annihilation
In diesem Test zeigen beispielsweise die Verbindungen gemäß den Herstellungsbeispielen 1, 2 und 3 bei guter Verträglichkeit gegenüber Kulturpflanzen, wie z.B. Mais (0 %) und einer Aufwandmenge von 500 g/ha starke Wirkung gegenIn this test, for example, the compounds according to Preparation Examples 1, 2 and 3 show good tolerance to crop plants, such as e.g. Corn (0%) and an application rate of 500 g / ha strong effect against
Unkräuter wie Amaranthus (95-100 %), Ambrosia (100 %), Galinsoga (100 %), Polygonum (90-100 %) und Solanum (95-100 %). Weeds such as Amaranthus (95-100%), Ambrosia (100%), Galinsoga (100%), Polygonum (90-100%) and Solanum (95-100%).

Claims

Patentansprüche  Claims
1. Diazacyclohexandi(thi)one der allgemeinen Formel (I) 1. Diazacyclohexanedi (thi) one of the general formula (I)
Figure imgf000028_0001
Figure imgf000028_0001
in welcher  in which
Q1 für Sauerstoff oder Schwefel steht, Q 1 represents oxygen or sulfur,
Q2 für Sauerstoff oder Schwefel steht, Q 2 represents oxygen or sulfur,
R1 für Wasserstoff, Cyano, Nitro, Halogen, Alkyl oder Halogenalkyl steht, R 1 represents hydrogen, cyano, nitro, halogen, alkyl or haloalkyl,
R2 für Wasserstoff, Cyano, Nitro, Thiocarbamoyl, Halogen oder für jeweils gegebenenfalls durch Halogen substituiertes Alkyl oder Alkoxy steht, R 2 represents hydrogen, cyano, nitro, thiocarbamoyl, halogen or alkyl or alkoxy which is optionally substituted by halogen,
R3 für die nachstehende Gruppierung steht, R 3 represents the grouping below,
-A'-A2-A3 worin für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff (wobei in diesem Fall R2 nicht für Halogen steht), Hydroxy, Alkyl, Alkoxy, Aryl, Alkylcarbonyl, Alkylsulfonyl oder Arylsulfonyl steht, oder A1 weiterhin für jeweils gegebenenfalls substituiertes Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cycloalkandiyl, Cycloalkendiyl oder Arendiyl steht, -A'-A 2 -A 3 wherein stands for a single bond, for oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 is hydrogen (in which case R 2 is not for Halogen is), hydroxy, alkyl, alkoxy, aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl, or A 1 furthermore represents optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkendiyl or arendiyl,
A2 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy, Alkyl, Alkoxy, Aryl, Alkylcarbonyl, Alkylsulfonyl oder Arylsulfonyl steht, A 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl,
A2 weiterhin für jeweils gegebenenfalls substituiertes Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cycloalkandiyl, Cycloalkendiyl oder Arendiyl steht, und A 2 furthermore stands for optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl, and
A3 für Wasserstoff, Hydroxy, Mercapto, Amino, Cyano, Isocyano, Thiocyanato, Nitro, Carbamoyl, Thiocarbamoyl, Sulfo, Chlorsulfonyl, Halogen oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, Dialkoxy(thio)phosphoryl, Alkenyl,A 3 for hydrogen, hydroxy, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkoxy (thio ) phosphoryl, alkenyl,
Alkenyloxy, Alkenylamino, Alkylidenamino, Alkinyl, Alkinyloxy, Alkinylamino, Cycloalkyl, Cycloalkyloxy, Cycloalkylalkyl, Cycloalkylalkoxy, Cycloalkylidenamino, Aryl, Aryloxy, Arylalkyl, Arylalkoxy, Heterocyclyl, Heterocyclylalkyl oder Heterocyclylalkoxy steht, Alkenyloxy, alkenylamino, alkylidenamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, aryl, aryloxy, arylalkyl, arylalkoxy, heterocyclyl, heterocyclylalkyl or heterocyclylalkoxy,
R4 für Wasserstoff, Halogen, Alkyl oder Halogenalkyl steht, R 4 represents hydrogen, halogen, alkyl or haloalkyl,
R5 für Alkyl oder Halogenalkyl steht, und R 5 represents alkyl or haloalkyl, and
R6 für Wasserstoff, Amino, Hydroxy oder für jeweils gegebenenfalls substituiertes Alkyl oder Cycloalkyl steht. Diazacyclohexandi(thi)one der allgemeinen Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß R 6 stands for hydrogen, amino, hydroxy or for optionally substituted alkyl or cycloalkyl. Diazacyclohexanedi (thi) one of the general formula (I) according to claim 1, characterized in that
Q1 für Sauerstoff oder Schwefel steht, Q 1 represents oxygen or sulfur,
Q2 für Sauerstoff oder Schwefel steht, R1 für Wasserstoff, Cyano, Nitro, Fluor, Chlor, Brom oder für gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht, Q 2 represents oxygen or sulfur, R 1 represents hydrogen, cyano, nitro, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine,
R2 für Wasserstoff, Cyano, Nitro, Thiocarbamoyl, Fluor, Chlor, Brom oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl oder Alkoxy mit jeweils 1 bis 4 Kohlenstoffatomen steht, R 2 represents hydrogen, cyano, nitro, thiocarbamoyl, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms,
R3 für die nachstehende Gruppierung steht, R 3 represents the grouping below,
-A1-A2-A3 in welcher A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff (wobei in diesem Fall R2 nicht für Fluor, Chlor oder Brom steht), Hydroxy, C1-C4-Alkyl, C1-C4-Alkoxy, Phenyl, C1-C4- Alkylsulfonyl oder Phenylsulfonyl steht, A1 weiterhin für jeweils gegebenenfalls durch Fluor, Chlor oder-A 1 -A 2 -A 3 in which A 1 stands for a single bond, for oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 is hydrogen (in which case R 2 does not represent fluorine, chlorine or bromine), hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, phenyl, C 1 -C 4 -alkylsulfonyl or phenylsulfonyl, A 1 also represents in each case optionally by fluorine , Chlorine or
Brom substituiertes C1-C6-Alkandiyl, C2-C6- Alkendiyl, C2-C6- Azaalkendiyl, C2-C6-Alkindiyl, C3-C6-Cycloalkandiyl, C3-C6- Cycloalkendiyl oder Phenylen steht, Bromine substituted C 1 -C 6 alkanediyl, C 2 -C 6 alkenediyl, C 2 -C 6 azaalkenediyl, C 2 -C 6 alkynediyl, C 3 -C 6 cycloalkanediyl, C 3 -C 6 cycloalkenediyl or Phenylene stands,
A2 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff,A 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen,
Hydroxy, C1-C4-Alkyl, C1-C4-Alkoxy, Phenyl, C1-C4-Alkylsulfonyl oder Phenylsulfonyl steht, Is hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, phenyl, C 1 -C 4 alkylsulfonyl or phenylsulfonyl,
A2 weiterhin für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C1-C8-Alkandiyl, C2-C6- Alkendiyl, C2-C6-Azaalkendiyl, C2-C6. Alkindiyl,A 2 furthermore for C 1 -C 8 -alkanediyl, C 2 -C 6 -alkenediyl, C 2 -C 6 -azaalkenediyl, C 2 -C 6 -alkynediyl, each optionally substituted by fluorine, chlorine or bromine,
C3-C6-Cycloalkandiyl, C3-C6-Cycloalkendiyl oder Phenylen steht, A3 für Wasserstoff, Hydroxy, Amino, Cyano, Isocyano, Thio- cyanato, Nitro, Carbamoyl, Thiocarbamoyl, Sulfo, Chlor- sulfonyl, Halogen, für jeweils gegebenenfalls durch Halogen oder C1-C4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, oderC 3 -C 6 cycloalkanediyl, C 3 -C 6 cycloalkanediyl or phenylene, A 3 for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio which are each optionally substituted by halogen or C 1 -C 4 alkoxy , Alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, or
Dialkoxy(thio)phosphoryl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl, Alkenyloxy, Alkenylamino, Alkylidenamino, Alkinyl, Alkinyloxy oder Alkinylamino mit jeweils 2 bis 6 Kohlenstoffatomen in den Alkenyl-, Alkyliden- oder Alkinylgruppen, für jeweils gegebenenfalls durch Halogen, Cyano, Carboxy, C1-C4-Alkyl und/oder C1-C4- Alkoxy-carbonyl substituiertes Cycloalkyl, Cycloalkyloxy, Cycloalkyl alkyl, Cycloalkylalkoxy oder Cycloalkylidenamino mit jeweils 3 bis 6 Kohlenstoffatomen in den Cycloalkylgruppen und gegebenenfalls 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Halogen C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-AIkyloxy, C1-C4-Halogenalkyloxy und/oder C1-C4- Alkoxy-carbonyl substituiertes Phenyl, Phenyloxy, Phenyl-C1- C4-alkyl oder Phenyl-C1-C4-alkoxy, (jeweils gegebenenfalls ganz oder teilweise hydriertes) Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Iso- thiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Triazinyl, Pyrazolyl-CrC4-alkyl, Furyl-C1-C4-alkyl, Thienyl-Dialkoxy (thio) phosphoryl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkynyl, alkynyloxy or alkynylamino each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each optionally substituted by halogen, for in each case optionally substituted by halogen, cyano, carboxy, C 1 -C 4 alkyl and / or C 1 -C 4 alkoxycarbonyl cycloalkyl, cycloalkyloxy, cycloalkyl alkyl, cycloalkylalkoxy or cycloalkylideneamino, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, halogen C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkyloxy, C 1 -C 4 -Halogenalkyloxy and / or C 1 -C 4 - alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C 1 - C 4 -alkyl or phenyl-C 1 -C 4 -alkoxy, (each optionally fully or partially hydrogenated) pyrr olyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C r C 4 -alkyl, furyl-C 1 -C 4 -alkyl , Thienyl
C1-C4-alkyl, Oxazolyl-C 1-C4-alkyl, Isoxazol-C1-C4 -alkyl, Thiazol-C1-C4-alkyl, Pyridinyl-C1-C4-alkyl, Pyrimidinyl-C1-C4- alkyl, Pyrazolylmethoxy, Furylmethoxy, für Perhydropyranylmethoxy oder Pyridylmethoxy steht, R4 für Wasserstoff, Halogen oder für gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht, C 1 -C 4 alkyl, oxazolyl-C 1 -C 4 alkyl, isoxazole-C 1 -C 4 alkyl, thiazole-C 1 -C 4 alkyl, pyridinyl-C 1 -C 4 alkyl, pyrimidinyl- C 1 -C 4 -alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, R 4 represents hydrogen, halogen or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine,
R5 für gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht, und R6 für Wasserstoff, Amino, Hydroxy, für gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen oder für Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht. R 5 represents optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms, and R 6 represents hydrogen, amino, hydroxy, alkyl optionally substituted by fluorine and / or chlorine with 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms.
3. Diazacyclohexandi/thi)one der allgemeinen Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß 3. Diazacyclohexandi / thi) one of the general formula (I) according to claim 1, characterized in that
Q1 für Sauerstoff steht, Q 1 represents oxygen,
Q2 für Sauerstoff steht, Q 2 represents oxygen,
R1 für Wasserstoff, Fluor oder Chlor steht, R 1 represents hydrogen, fluorine or chlorine,
R2 für Cyano, Thiocarbamoyl, Chlor, Brom, Methyl oder Trifluormethyl steht, R2 represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R3 für die nachstehende Gruppierung steht, R 3 represents the grouping below,
-A1-A2-A3 in welcher -A 1 -A 2 -A 3 in which
A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für WasserstoffA 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen
(wobei in diesem Fall R2 nicht für Chlor oder Brom steht), Hydroxy, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylsulfonyl oder Ethylsulfonyl steht, (in which case R 2 does not represent chlorine or bromine), hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A1 weiterhin für Methylen, Ethan-1,1-diyl, Ethan-1,2-diyl, Propan- 1 ,1-diyl, Propan-1,2-diyl, Propan-1,3-diyl, Ethen-1,2-diyl,A 1 furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl,
Propen- 1,2-diyl, Propen- 1,3-diyl, Ethin-1,2-diyl, Propin-1,2- diyl oder Propin-1,3-diyl steht, Propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
A2 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylsulfonyl, Ethylsulfonyl, n- oder i- Propylsulfonyl oder Phenylsulfonyl steht, A 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 - or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy , n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A2 weiterhin für Methylen, Ethan-1,1-diyl, Ethan-1,2-diyl, Propan- 1,1-diyl, Propan-1,2-diyl, Propan-1,3-diyl, Ethen-1,2-diyl, Propen-1,2-diyl, Propen-1,3-diyl, Ethin-1,2-diyl, Propin-1,2- diyl oder Propin- 1,3-diyl steht, A 2 furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
A3 für Wasserstoff, Hydroxy, Amino, Cyano, Nitro, Carbamoyl,A 3 for hydrogen, hydroxy, amino, cyano, nitro, carbamoyl,
Sulfo, Fluor, Chlor, Brom, für jeweils gegebenenfalls durchSulfo, fluorine, chlorine, bromine, for each optionally by
Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- oder t- Pentyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t- Butoxy, n-, i-, s- oder t-Pentyloxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethyl- sulfonyl, n- oder i-Propylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Dimethylamino, Diethylamino, Dimethoxyphosphoryl, Diethoxyphosphoryl, Dipropoxyphosphoryl oder Diisopropoxyphosphoryl, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Propenyl, Butenyl, Propenyloxy, Butenyloxy,Fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n - or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s - or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy which are optionally substituted by fluorine or chlorine,
Propenylamino, Butenylamino, Propylidenamino, Butylidenamino, Propinyl, Butinyl, Propinyloxy, Butinyloxy, Propinylamino, Butinylamino, für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl oder Ethoxycarbonyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino,Propenylamino, butenylamino, propylidenamino, butylidenamino, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, each for cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino,
Cyclohexylidenamino, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Trifluorm ethyl, Methoxy, Ethoxy, n- oder i- Propoxy, Difluormethoxy, Trifluormethoxy, Methoxycarbonyl und/oder Ethoxycarbonyl substituiertes Phenyl, Phenyloxy, Benzyl, Phenylethyl, Benzyloxy, (jeweils gegebenenfalls ganz oder teilweise hydriertes) Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Triazinyl, Pyrazolylmethyl, Furylmethyl, Thienylmethyl, Oxazolylmethyl, Isoxazolmethyl, Thiazolmethyl, Pyridinylmethyl, Pyrimidinylmethyl, Pyrazolylmethoxy, Furylmethoxy oder Pyridylmethoxy steht, Cyclohexylidenamino, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, Benzyl, phenylethyl, benzyloxy, (each optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazethyl, furylmylylyl, pyrazylyl, pyrazolyl Oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy,
R4 für Wasserstoff, Fluor, Chlor, Brom oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl steht, R 4 represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,
R5 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl steht, und R 5 represents in each case optionally substituted by fluorine and / or chlorine methyl or ethyl, and
R6 für Wasserstoff, Amino, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl oder für Cyclopropyl steht. R 6 represents hydrogen, amino, methyl or ethyl optionally substituted by fluorine and / or chlorine or cyclopropyl.
4. Verfahren zur Herstellung der Diazacyclohexandi(thi)one der allgemeinen Formel (I) 4. Process for the preparation of the diazacyclohexanedi (thi) ones of the general formula (I)
Figure imgf000034_0001
Figure imgf000034_0001
in welcher  in which
R1, R2, R3, R4, R5, R6, Q1 und Q2 die in Anspruch 1 genannten Bedeutungen haben, dadurch gekennzeichnet, daß man Uracile der allgemeinen Formel (II)
Figure imgf000035_0001
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q 1 and Q 2 have the meanings given in Claim 1, characterized in that uracils of the general formula (II)
Figure imgf000035_0001
in welcher Q1, Q2, R1, R2, R3, R4, R5 und R6 die oben angegebenen Bedeutungen haben, mit einem Hydrierungsmittel, gegebenenfalls in Gegenwart eines Katalysators und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt. 5. Herbizide Mittel, gekennzeichnet durch einen Gehalt an mindestens einem substituierten Diazacyclohexandi(thi)on der allgemeinen Formel (I) gemäß den Ansprüchen 1 bis 4. in which Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings given above, with a hydrogenating agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent. 5. Herbicidal agents, characterized by a content of at least one substituted diazacyclohexanedi (thi) on of the general formula (I) according to claims 1 to 4.
6. Verfahren zur Bekämpfung von unerwünschten Pflanzen, dadurch gekennzeichnet, daß man substituierte Diazacyclohexandi(thi)one der allgemeinen Formel (I) gemäß den Ansprüchen 1 bis 4 auf unerwünschte Pflanzen und/oder ihren Lebensraum einwirken läßt. 7. Verwendung von substituierten Diazacyclohexandi(thi)one der allgemeinen6. A method for controlling unwanted plants, characterized in that substituted diazacyclohexanedi (thi) ones of the general formula (I) according to Claims 1 to 4 are allowed to act on undesired plants and / or their habitat. 7. Use of substituted diazacyclohexanedi (thi) one of the general
Formel (I) gemäß der Ansprüche 1 bis 4 zur Bekämpfung von unerwünschten Pflanzen. 8. Verfahren zur Herstellung von herbiziden Mitteln, dadurch gekennzeichnet, daß man subsituierte Diazacyclohexandi(thi)one der allgemeinen Formel (I) gemäß der Ansprüche 1 bis 4 mit Streckmitteln und/oder oberflächenaktiven Substanzen vermischt. Formula (I) according to claims 1 to 4 for controlling unwanted plants. 8. A process for the preparation of herbicidal compositions, characterized in that substituted diazacyclohexanedi (thi) ones of the general formula (I) according to Claims 1 to 4 are mixed with extenders and / or surface-active substances.
PCT/EP1995/004353 1994-11-17 1995-11-06 Substituted diazacyclohexane di(thi)ons having a herbicidal effect WO1996016043A1 (en)

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WO2020237823A1 (en) * 2019-05-31 2020-12-03 深圳大学 Aryluracil compound and preparation method therefor, and pesticide composition
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