[go: up one dir, main page]

WO2002081473A1 - Azoloazin(thi)ones substituees - Google Patents

Azoloazin(thi)ones substituees Download PDF

Info

Publication number
WO2002081473A1
WO2002081473A1 PCT/EP2002/003156 EP0203156W WO02081473A1 WO 2002081473 A1 WO2002081473 A1 WO 2002081473A1 EP 0203156 W EP0203156 W EP 0203156W WO 02081473 A1 WO02081473 A1 WO 02081473A1
Authority
WO
WIPO (PCT)
Prior art keywords
cyano
diyl
chlorine
fluorine
ethoxy
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2002/003156
Other languages
German (de)
English (en)
Inventor
Roland Andree
Rolf Kirsten
Joachim Kluth
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Bayer CropScience AG
Original Assignee
Bayer AG
Bayer CropScience AG
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
Priority to EP06026832A priority Critical patent/EP1772464B1/fr
Application filed by Bayer AG, Bayer CropScience AG filed Critical Bayer AG
Publication of WO2002081473A1 publication Critical patent/WO2002081473A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to new substituted azoloazin (thi) ones and a process for their preparation as well as the use of substituted azoloazin (thi) ones
  • Plant treatment agents in particular as herbicides.
  • Individual substituted azolotriazinones such as the compounds 3-acetyl-pyrrolo [l, 2-d] [l, 2,4] triazin-4 (3H) -one, l-oxopyrrolo [l, 2-d] [l, 2,4] triazine-2 (1H) -acetic acid, 1-oxoxyrrolo [1, 2-d] [1, 2,4] triazine-2 (1 H) -acetic acid methyl ester, 4-methyl-1 - oxo-pyrrolo [l, 2-d] [l, 2,4] triazine-2 (lH) acetic acid and 4-methyl-l-oxo-pyrrolo [l, 2-d] - [l, 2,4] triazine-2 (1H) -acetic acid methyl ester (cf.
  • imidazotriazinones optionally substituted by alkyl groups, such as, for example, the compounds imidazo [1,5-d] l, 2,4] triazin-4 (3H) -thione, 8-methylimidazo [1,5-d] [l , 2,4] triazine-4 (3H) -thione, 6-propyl-imidazo [l, 5-d] l, 2,4] triazine-4 (3H) -thione, 6,8-dimethyl-imidazo [l , 5-d] [l, 2,4] triazine-4 (3H) -thione, 6-methyl-imide-azo [l, 5-d] [l, 2,4] triazine-4 (3H) -thione , 6-propyl-imidazo [l, 5-d] [l, 2,4] triazin-4 (3H) -thione, 6,8-dimethyl-imidazo [l, 5-d] [l, 2,4] triazin-4 (3H) -one, 6-
  • a bond drawn in dashed lines represents a single bond or a double bond
  • Q 1 represents O (oxygen) or S (sulfur),
  • Q 2 represents O (oxygen) or S (sulfur),
  • the neighboring atoms Q 3 are different and Q 3 if it is for C (Carbon) is connected via a double bond to the neighboring Q 4 ,
  • R is hydrogen, hydroxyl, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, Alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, dialkylamino or aryl,
  • X is hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylamino-nylsulfonyl stands,
  • Y stands for a single bond or for optionally substituted alkanediyl, alkenediyl, alkindiyl or cycloalkanediyl, and
  • Z for hydrogen, hydroxy, mercapto, amino, hydroxyamino, hydrazino, carbamoyl, or for each optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, alkoxyamino, N-alkyl-hydroxyamino, alkylhydrazino, dialkylamino, N-alkylalkoxyamino .
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl are in each case straight-chain or branched as far as possible, even in conjunction with heteroatoms, such as in alkoxy.
  • Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitution the substituents can be the same or different.
  • the compounds of the general formula (I) according to the invention optionally contain one or more asymmetrically substituted carbon atoms and in these cases can be present in various enantiomeric (R- and S-configured forms) or diastereomeric forms.
  • the invention relates both to the use of the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the
  • Q 1 preferably represents O (oxygen).
  • Q 2 preferably represents O (oxygen).
  • Q 4 preferably represents the grouping CX.
  • R preferably represents hydrogen, hydroxy, amino, cyano, carboxy, carbamoyl, Thiocarbarnoyl, halogen, represents in each case optionally cyano-, halogen, C ⁇ -C4-alkoxy, Ci- alkylcarbonyl, C 1 -C 4 - alkoxycarbonyl, CC 4 -Alkylthio, C 1 -C 4 -Alkylsulf ⁇ nyl or C 1 -C -alkylsulfonyl substituted
  • X preferably represents hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally by cyano, halogen, CrC 4 alkoxy, C 1 -C 4 alkylcarbonyl, C ** - C 4 - Alkoxycarbonyl, -C-C 4 - alkylthio, C -C 4 alkylsulfmyl or - alkylsulfonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl in each case with the 1-bisulfonyl alkyl groups.
  • Y preferably represents a single bond or alkanediyl, alkenediyl, alkynediyl each having up to 6 carbon atoms or cycloalkanediyl having 3 to 6 carbon atoms, each of which is optionally substituted by nitro, cyano, hydroxy, mercapto, amino or the —C (Q ! ) -Z group , where appropriate the Z of the above group -C (Q 1 ) -Z may also together with the Z defined below represent O (oxygen), NH or alkanediyl having 1 to 3 carbon atoms.
  • Z preferably represents hydrogen, hydroxy, mercapto, amino, hydroxyamino, hydrazino, carbamoyl, each in each case optionally by cyano, halogen, Ci
  • Heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclicalkylamino each with up to 10 carbon atoms, up to 5 nitrogen atoms and / or up to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl part.
  • X particularly preferably represents hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl , Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl , n-, i-, s- or t-butyl, acetyl, propionyl
  • very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl tes methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,
  • X very particularly preferably represents hydrogen, nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio , Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl,
  • Y very particularly preferably represents a single bond or methylene (-CH 2 -), ethane-l, l-diyl (ethylidene, -CH (CH.) Which is optionally substituted by cyano, hydroxyl or the grouping -C (Q 1 ) -Z 3 ) -), ethane-1,2-diyl (dimethylene, -CH 2 CH 2 -), propane-l, l-diyl (propylidene, -CH (C 2 H 5 ) -),
  • Z very particularly preferably represents hydrogen, hydroxy, mercapto, amino
  • Carbamoyl for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n - or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
  • R most preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, acetyl, methoxy, ethoxy, acetyloxy, propionyloxy, methoxycarbonyl or ethoxycarbonyl.
  • X most preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, acetyl, propionyl, methoxy or ethoxy, each of which is optionally substituted by fluorine or chlorine.
  • Y most preferably represents a single bond, methylene (-CH 2 -), ethane-l, l-diyl (ethylidene, -CH (CH 3 ) -) or ethane-1,2-diyl (dimethylene,
  • Z most preferably represents hydrogen, hydroxy, amino, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-butoxy, for methylamino, ethylamino, n- or i-propylamino, for dimethylamino or diethylamino, each optionally by fluorine, chlorine, methyl, ethyl, difluoromethoxy, trifluoromethoxy substituted phenyl, phenylcarbonyl, phenyloxy, phenylamino or phenylmethyl.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • a very particularly preferred group of compounds of the general formula (I) are the compounds of the following formula (IA)
  • A represents N (nitrogen) or the grouping C-X,
  • Q 1 represents O (oxygen) or S (sulfur),
  • Q 2 represents O (oxygen) or S (sulfur), R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl,
  • X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio,
  • X I for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,
  • X 2 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine,
  • Another very particularly preferred group of compounds of the general formula (I) are the compounds of the general formula (LB)
  • Q 1 represents O (oxygen) or S (sulfur),
  • Q -.2 z represents O (oxygen) or S (sulfur),
  • R for hydrogen, cyano, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl,
  • X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl, ethy
  • X 1 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
  • X 2 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine,
  • Q 1 represents O (oxygen) or S (sulfur),
  • Q 2 represents O (oxygen) or S (sulfur),
  • R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methoxy,
  • X 1 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine,
  • Q 1 represents O (oxygen) or S (sulfur)
  • Q 2 represents O (oxygen) or S (sulfur)
  • R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino,
  • X 1 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,
  • X 2 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine,
  • Q 1 represents O (oxygen) or S (sulfur),
  • Q 2 represents O (oxygen) or S (sulfur),
  • R for hydrogen, cyano, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl,
  • X 1 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,
  • X is hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio
  • the new substituted azoloazin (thi) ones of the general formula (I) and also the compounds excluded by disclaimers are notable for strong and selective herbicidal activity.
  • X 3 represents halogen or the grouping -YC (Q 1 ) -Z, where Y, Q 1 and Z in turn have one of the meanings given above,
  • azoloazin (thi) ones to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (II), üi the general formula (II) have Q 2 , Q 3 , Q 4 and R preferably those meanings which have already been mentioned above in connection with the description of the compounds of the general Formula (I) has been given as preferred, particularly preferred, very particularly preferred or most preferred for Q 2 , Q 3 , Q 4 and R.
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. C. R. Acad. Sei., Ser. C (1972),
  • Formula (III) provides a general definition of the compounds to be used further as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • Q 1 is a general definition of the compounds to be used further as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • Q 1 is a general definition of the compounds to be used further as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • Y and Z preferably have the meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred for Q 1 , Y and Z;
  • X 3 preferably represents chlorine, bromine, iodine or the grouping -YC (Q 1 ) -Z, where Q 1 , Y and Z have the meanings given above as preferred, particularly preferred, very particularly preferred or most preferred.
  • the starting materials of the general formula (HI) are organic synthetic chemicals known to the person skilled in the art.
  • reaction auxiliaries The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanols, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium , Potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or
  • Phase transfer catalysts are also suitable as further reaction aids for the process according to the invention.
  • Examples of such catalysts are:
  • Formula (I) is preferably carried out using one or more diluents. carried out medium.
  • diluents for carrying out the process according to the invention are in particular inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as
  • reaction temperatures can be varied over a wide range in the implementation of the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally mine stirred for several hours at the required temperature. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Scirpus, Setaria, Sorghum Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on
  • the active compounds according to the invention 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 as well as for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crops).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying,
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • Alcohols such as butanol or glycol, and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite,
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are also possible possible with weed control agents which contain one or more known herbicides and a safener.
  • safeners substances which improve crop tolerance
  • Diflufenican Diflufenzopyr, Dimefiiron, Dimepiperate, Dimethachlor, Dimetha- metryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, EtobenzanidPenamide, Fenoxap, Flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,
  • Flumetsulam Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurpyr-sul matterson (-methyl, -sodium), Flurenol (-butyl), Fluroxyryl (-butoxy-propyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fom-safen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl, - P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaqui
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Organisms and their parts treated.
  • the term “parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive superadditive effects.
  • Active substances - better plant growth of the crop plants, increased tolerance of the crop plants to high or low temperatures, increased tolerance of the crop plants to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of crop products, higher
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, received genetic material which contained them Gives plants special beneficial valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicides
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryLA (b), CryLA (c), CryLIA, CrylllA, CryIILB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of "Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YLELD GARD® (e.g.
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rapeseed), LMI® (tolerance against Imidazolinone) and STS®
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market with these or future-developed genetic properties ("traits").
  • the plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I or the active compound mixtures according to the invention, the above-mentioned synergistic effects also occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • Table 1 Examples of the compounds of the formula (I) or of the formulas (LA), (ffi), (IC), (LD) or (IE)
  • the lambda max values were determined using the UN spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • Example B the compounds according to Preparation Examples 4, 5 and 14, with good tolerance to crop plants, such as, for example, maize, show a strong action against weeds.
  • Example B the compounds according to Preparation Examples 4, 5 and 14, with good tolerance to crop plants, such as, for example, maize, show a strong action against weeds.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants with a height of 5 - 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the compounds according to Preparation Examples 1, 4, 5 and 14 show that they are well tolerated by crop plants, such as e.g. Corn and sugar beet, strong weed control.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne de nouvelles azoloazin(thi)ones substituées de formule générale (I), dans laquelle Q<1>, Q<2>, Q<3>, Q<4>, R, Y et Z ont la signification indiquée dans la description. L'invention concerne également des procédés pour leur production ainsi que leur utilisation comme agent de traitement de plantes.
PCT/EP2002/003156 2001-02-09 2002-03-21 Azoloazin(thi)ones substituees Ceased WO2002081473A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06026832A EP1772464B1 (fr) 2001-02-09 2002-02-01 Procédés d'identification d'agonistes indirects de IGF-1

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2001116399 DE10116399A1 (de) 2001-04-03 2001-04-03 Substituierte Azolazin(thi)one
DE10116399.1 2001-04-03

Publications (1)

Publication Number Publication Date
WO2002081473A1 true WO2002081473A1 (fr) 2002-10-17

Family

ID=7680107

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/003156 Ceased WO2002081473A1 (fr) 2001-02-09 2002-03-21 Azoloazin(thi)ones substituees

Country Status (2)

Country Link
DE (1) DE10116399A1 (fr)
WO (1) WO2002081473A1 (fr)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8097712B2 (en) 2007-11-07 2012-01-17 Beelogics Inc. Compositions for conferring tolerance to viral disease in social insects, and the use thereof
US8962584B2 (en) 2009-10-14 2015-02-24 Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. Compositions for controlling Varroa mites in bees
ES2641642T3 (es) 2010-03-08 2017-11-10 Monsanto Technology Llc Moléculas de polinucleótido para regulación génica en plantas
UY34328A (es) 2011-09-13 2013-04-30 Monsanto Technology Llc ?composiciones y métodos para controlar malezas comprendiendo un polinucleótido y agente de transferencia, y que modulan protoporfirinógeno ix oxidasa?.
CN107739737A (zh) 2011-09-13 2018-02-27 孟山都技术公司 用于杂草控制的方法和组合物
US10829828B2 (en) 2011-09-13 2020-11-10 Monsanto Technology Llc Methods and compositions for weed control
BR112014005958A2 (pt) 2011-09-13 2020-10-13 Monsanto Technology Llc métodos e composições químicas agrícolas para controle de planta, método de redução de expressão de um gene accase em uma planta, cassete de expressão microbiana, método para fazer um polinucleotídeo, método de identificação de polinucleotídeos úteis na modulação de expressão do gene accase e composição herbicida
AR087862A1 (es) 2011-09-13 2014-04-23 Monsanto Technology Llc Metodos y composiciones para el control de malezas
US10760086B2 (en) 2011-09-13 2020-09-01 Monsanto Technology Llc Methods and compositions for weed control
WO2013040057A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
US10806146B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
IN2014MN02404A (fr) 2012-05-24 2015-08-21 Seeds Ltd Ab
US10683505B2 (en) 2013-01-01 2020-06-16 Monsanto Technology Llc Methods of introducing dsRNA to plant seeds for modulating gene expression
EA032406B1 (ru) 2013-01-01 2019-05-31 Эй.Би. СИДЗ ЛТД. СПОСОБЫ ВВЕДЕНИЯ дсРНК В СЕМЕНА РАСТЕНИЙ ДЛЯ МОДУЛЯЦИИ ЭКСПРЕССИИ ГЕНОВ
WO2014164761A1 (fr) 2013-03-13 2014-10-09 Monsanto Technology Llc Procédés et compositions utilisables pour lutter contre les mauvaises herbes
CA2905104A1 (fr) 2013-03-13 2014-10-09 Monsanto Technology Llc Controle des ivraies par application topique d'une composition herbicidecomprenant de l'arn a double brin
US10568328B2 (en) 2013-03-15 2020-02-25 Monsanto Technology Llc Methods and compositions for weed control
US9850496B2 (en) 2013-07-19 2017-12-26 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
PL3030663T3 (pl) 2013-07-19 2020-04-30 Monsanto Technology Llc Kompozycje i sposoby kontroli leptinotarsa
UY35817A (es) 2013-11-04 2015-05-29 Us Agriculture ?composiciones y métodos para controlar infestaciones de plagas y parásitos de los artrópodos?.
UA119253C2 (uk) 2013-12-10 2019-05-27 Біолоджикс, Інк. Спосіб боротьби із вірусом у кліща varroa та у бджіл
AR099092A1 (es) 2014-01-15 2016-06-29 Monsanto Technology Llc Métodos y composiciones para el control de malezas utilizando polinucleótidos epsps
EP3420809A1 (fr) 2014-04-01 2019-01-02 Monsanto Technology LLC Compositions et procédés pour lutter contre les insectes nuisibles
US10988764B2 (en) 2014-06-23 2021-04-27 Monsanto Technology Llc Compositions and methods for regulating gene expression via RNA interference
US11807857B2 (en) 2014-06-25 2023-11-07 Monsanto Technology Llc Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression
CN114009454A (zh) 2014-07-29 2022-02-08 孟山都技术公司 用于控制昆虫害虫的组合物和方法
CN108064288B (zh) 2015-01-22 2021-11-26 孟山都技术公司 用于控制叶甲属的组合物和方法
AU2016270870A1 (en) 2015-06-02 2018-01-04 Monsanto Technology Llc Compositions and methods for delivery of a polynucleotide into a plant
WO2016196782A1 (fr) 2015-06-03 2016-12-08 Monsanto Technology Llc Procédés et compositions pour l'introduction d'acides nucléiques dans des plantes

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4126444A (en) * 1977-11-22 1978-11-21 American Cynamid Company Substituted imidazo (1,5-D)-as-triazin-4-ols, and herbicidal use thereof
EP0297490A1 (fr) * 1987-07-01 1989-01-04 Schering Aktiengesellschaft 6,7-Dihydro-pyrazolo[1,5-a][1,3,5]triazine-2-sulfonamides, procédé pour leur préparation et leur utilisation comme compositions herbicides et régulatrices de croissance de plantes
EP0713876A1 (fr) * 1994-11-24 1996-05-29 Wakamoto Pharmaceutical Co., Ltd. Dérivés de triazine, inhibiteurs de chymase et de la production d'oxyde nitrique
JP2001058958A (ja) * 1999-08-20 2001-03-06 Senju Pharmaceut Co Ltd 涙液分泌促進剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4126444A (en) * 1977-11-22 1978-11-21 American Cynamid Company Substituted imidazo (1,5-D)-as-triazin-4-ols, and herbicidal use thereof
EP0297490A1 (fr) * 1987-07-01 1989-01-04 Schering Aktiengesellschaft 6,7-Dihydro-pyrazolo[1,5-a][1,3,5]triazine-2-sulfonamides, procédé pour leur préparation et leur utilisation comme compositions herbicides et régulatrices de croissance de plantes
EP0713876A1 (fr) * 1994-11-24 1996-05-29 Wakamoto Pharmaceutical Co., Ltd. Dérivés de triazine, inhibiteurs de chymase et de la production d'oxyde nitrique
JP2001058958A (ja) * 1999-08-20 2001-03-06 Senju Pharmaceut Co Ltd 涙液分泌促進剤

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; AJELLO, ENRICO ET AL: "Polycondensed nitrogen heterocycles. IV. Pyrazolo[1,5-d]-s- triazolo[3,4-f]-as-triazine", XP002205288, retrieved from STN Database accession no. 78:136235 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PAUL, ROLF ET AL: "Imidazo[1,5-d][1,2,4]triazines as potential antiasthma agents", XP002205287, retrieved from STN Database accession no. 104:5848 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TSUZUKI, HIROKATSU ET AL: "Tear secretion promoters containing chymase inhibitors", XP002205286, retrieved from STN Database accession no. 134:202714 *
J. HETEROCYCL. CHEM. (1973), 10(1), 103-5 *
J. MED. CHEM. (1985), 28(11), 1704-16 *

Also Published As

Publication number Publication date
DE10116399A1 (de) 2002-10-10

Similar Documents

Publication Publication Date Title
WO2002081473A1 (fr) Azoloazin(thi)ones substituees
EP1444208A1 (fr) Pyrimidines substituees
WO2004067518A1 (fr) Procede et appareil de collage en surface d&#39;une bande de papier ou de carton
WO2003093269A2 (fr) Pyrazolopyrimidine-4-one substituee
WO2002006244A1 (fr) Anilide de l&#39;acide sulfonique herbicide heterocycliquement substitue
EP1373228A1 (fr) Fluoroalcoxyphenylsulfonylurees substituees
WO2001090102A2 (fr) 6-heteroclyclyl-3-oxo-3,4-dihydro-quinoxalines
EP1208098A2 (fr) Heterocyclyl-2h-chromenes substitues
EP1330443A1 (fr) Phenyluraciles substitues
EP1395565A1 (fr) Benzoylpyrazoles substitues a action herbicide
WO2002096884A2 (fr) Benzoyl-cetones substituees
WO2002010160A2 (fr) Heterocyclyl alkyl amino 1,3,5-triazines substituees
EP1511383A1 (fr) Phenyluraciles substitues
DE10255416A1 (de) Substituierte 2-Aryl-1,2,4-triazin-3,5-di(thi)one
EP1204651B1 (fr) 5-chlorodifluoromethyl-1,3-4-thiadiazol-2yl-oxyacetanilides herbicides
WO2002020487A1 (fr) 1-aryl-pyridin-2-(thi)ones substituees
EP1409484A1 (fr) Heterocycles benzo-azotes substitues
DE10117673A1 (de) Substituierte Fluoralkoxyphenylsulfonylamino(thio)carbonyl-triazolin(thi)one
DE10206792A1 (de) Substituierte Arylketone
WO2003056922A1 (fr) Thiazolylsulfonylurees substituees
EP1776012A1 (fr) Thienosulfonylamino (thio) carbonyltriazoline (thi) ones, procedes pour leur production et leur utilisation
WO2006012981A1 (fr) Thienylsulfonylurees substituees par aminocarbonyle
EP1773825A1 (fr) Composes thienylsulfonylaminocarbonyles substitues par dioxazinyle
WO2001068616A1 (fr) 1-aryl-cyclopropylmethylamino-1,3,5-triazines substituees
EP1501360A1 (fr) Derives de pyridin-3-carbonyle 2,6 substitues utilises comme produits phytosanitaires a action herbicide

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP