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WO1996016043A1 - Di(thi)ones de diazacyclohexane substitues et leur action herbicide - Google Patents

Di(thi)ones de diazacyclohexane substitues et leur action herbicide 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
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
chlorine
diyl
fluorine
optionally substituted
Prior art date
Application number
PCT/EP1995/004353
Other languages
German (de)
English (en)
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/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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

L'invention concerne de nouveaux di(thi)ones de diazacyclohexane de la formule générale (I) dans laquelle R?1, R2, R3, R4, R5, R6, Q1 et Q2¿ ont la notation mentionnée dans la description. L'invention concerne par ailleurs leur procédé de préparation et leur utilisation comme herbicides.
PCT/EP1995/004353 1994-11-17 1995-11-06 Di(thi)ones de diazacyclohexane substitues et leur action herbicide WO1996016043A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU39817/95A AU3981795A (en) 1994-11-17 1995-11-06 Substituted diazacyclohexane di(thi)ons having a herbicidal effect

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944440914 DE4440914A1 (de) 1994-11-17 1994-11-17 Substituierte Diazacyclohexandi(thi)one
DEP4440914.1 1994-11-17

Publications (1)

Publication Number Publication Date
WO1996016043A1 true WO1996016043A1 (fr) 1996-05-30

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PCT/EP1995/004353 WO1996016043A1 (fr) 1994-11-17 1995-11-06 Di(thi)ones de diazacyclohexane substitues et leur action herbicide

Country Status (3)

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AU (1) AU3981795A (fr)
DE (1) DE4440914A1 (fr)
WO (1) WO1996016043A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998039304A1 (fr) * 1997-03-05 1998-09-11 Bayer Aktiengesellschaft Composes amines aromatiques substitues a action herbicide
JP2001316375A (ja) * 1999-11-01 2001-11-13 Sumitomo Chem Co Ltd ６−ヒドロキシ−５，６−ジヒドロウラシル化合物
US6537948B1 (en) 2000-02-04 2003-03-25 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
CN109232442A (zh) * 2018-09-13 2019-01-18 深圳大学 芳基尿嘧啶类化合物或其农药学上可接受的盐、其制备方法、除草剂组合物
WO2020237823A1 (fr) * 2019-05-31 2020-12-03 深圳大学 Composé d'aryluracile, son procédé de préparation et composition pesticide
WO2021063821A1 (fr) 2019-10-01 2021-04-08 Bayer Aktiengesellschaft Dérivés de pyrimidinedione

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19651036A1 (de) * 1996-12-09 1998-06-10 Bayer Ag 3-Amino-l-cyanophenyl-uracile

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JPS55108858A (en) * 1979-02-14 1980-08-21 Kyowa Hakko Kogyo Co Ltd Novel dihydrouracil derivative and herbicide
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Cited By (7)

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WO1998039304A1 (fr) * 1997-03-05 1998-09-11 Bayer Aktiengesellschaft Composes amines aromatiques substitues a action herbicide
JP2001316375A (ja) * 1999-11-01 2001-11-13 Sumitomo Chem Co Ltd ６−ヒドロキシ−５，６−ジヒドロウラシル化合物
US6537948B1 (en) 2000-02-04 2003-03-25 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
CN109232442A (zh) * 2018-09-13 2019-01-18 深圳大学 芳基尿嘧啶类化合物或其农药学上可接受的盐、其制备方法、除草剂组合物
CN109232442B (zh) * 2018-09-13 2021-11-02 深圳大学 芳基尿嘧啶类化合物或其农药学上可接受的盐、其制备方法、除草剂组合物
WO2020237823A1 (fr) * 2019-05-31 2020-12-03 深圳大学 Composé d'aryluracile, son procédé de préparation et composition pesticide
WO2021063821A1 (fr) 2019-10-01 2021-04-08 Bayer Aktiengesellschaft Dérivés de pyrimidinedione

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