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WO2000043375A2 - Composes heterocycliques d'aryle substitues - Google Patents

Composes heterocycliques d'aryle substitues Download PDF

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Publication number
WO2000043375A2
WO2000043375A2 PCT/EP2000/000123 EP0000123W WO0043375A2 WO 2000043375 A2 WO2000043375 A2 WO 2000043375A2 EP 0000123 W EP0000123 W EP 0000123W WO 0043375 A2 WO0043375 A2 WO 0043375A2
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WO
WIPO (PCT)
Prior art keywords
cyano
alkyl
fluorine
chlorine
optionally
Prior art date
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PCT/EP2000/000123
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German (de)
English (en)
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WO2000043375A3 (fr
Inventor
Roland Andree
Karl-Heinz Linker
Otto Schallner
Hans-Georg Schwarz
Mark Wilhelm Drewes
Dieter Feucht
Rolf Pontzen
Ingo Wetcholowsky
Original Assignee
Bayer Aktiengesellschaft
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Priority to AU26631/00A priority Critical patent/AU2663100A/en
Publication of WO2000043375A2 publication Critical patent/WO2000043375A2/fr
Publication of WO2000043375A3 publication Critical patent/WO2000043375A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04—Aryloxy-acetic acids; Derivatives thereof
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the invention relates to new substituted aryl heterocycles, processes for their preparation and their use as herbicides.
  • n stands for the numbers 0, 1, 2, 3, 4 or 5
  • Q represents O (oxygen), S (sulfur), SO, SO 2 , NH or N (C i -C 4 alkyl),
  • R 1 represents hydrogen, cyano, thiocarbamoyl or halogen
  • R 2 represents cyano, thiocarbamoyl or in each case optionally substituted by halogen alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms,
  • X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, for each optionally by hydroxy, cyano, carboxy, carbamoyl, fluorine, chlorine, Ci-Cj-alkoxy, C1- C4- Alkylthio, Cj-C ⁇ alkylsulfinyl, C ⁇ C ⁇ alkylsulfonyl, -C-C4-alkylcarbonyl, C ⁇ -C4-alkoxy-carbonyl, C ⁇ -C4-alkylamino-carbonyl, di- (C ] -C4-alkyl) -amino -carbonyl, phenylaminocarbonyl or N- (C, -C 4 -alkyl) -phenyl-aminocarbonyl substituted alkyl, alkoxy, alkyl
  • Q 1 and Q 2 represent oxygen or sulfur
  • R 3 for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, for alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, for each optionally substituted by halogen alkenyl or alkynyl each with 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy or alkoxycarbonyl, each having 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, for optionally substituted by cyano, halogen or Cj-C4-alkoxy alkylthio having 1 to 6 carbon atoms, for each optionally substituted by halogen alkenylthio or alkyny
  • Y 1 represents O (oxygen), S (sulfur), SO, SO 2 , CH 2 , CH 2 CH 2 , NH or N (C, -C 4 alkyl), and
  • Y 2 represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , CH 2 , NH or N (C, -C 4 alkyl), found.
  • hydrocarbon chains such as alkyl or alkanediyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.
  • n preferably represents the numbers 0, 1, 2, 3 or 4.
  • Q preferably represents O (oxygen), S (sulfur), SO, SO 2 , NH or N (methyl).
  • R 1 preferably represents hydrogen, cyano, thiocarbamoyl, fluorine, chlorine or bromine.
  • R 2 is preferably cyano, thiocarbamoyl or in each case optionally
  • X preferably represents hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, each optionally by hydroxy, cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, methylthio, Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethyl, aminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl, benzylamin
  • Butinyl for methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , for propenyloxy, butenyloxy, propynyloxy or butynyloxy optionally substituted by fluorine or chlorine, for optionally substituted by cyano,
  • R 3 and R 4 - together for optionally substituted and / or optionally by oxygen, sulfur or a group from the series -SO-,
  • Y 1 preferably represents O (oxygen), S (sulfur), SO, SO 2 , CH 2 , CH 2 CH 2 , NH or N (methyl).
  • Y 2 preferably represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , CH 2 , NH or N (methyl).
  • n particularly preferably represents the numbers 1 or 2.
  • Q particularly preferably represents O (oxygen) or S (sulfur).
  • R 1 particularly preferably represents hydrogen, fluorine or chlorine.
  • R 2 particularly preferably represents cyano or thiocarbamoyl.
  • Y 1 particularly preferably represents O (oxygen), S (sulfur), CH 2 or CH 2 CH 2 .
  • Y 2 particularly preferably represents a single bond or O (oxygen), S
  • n is most preferably 1.
  • Q most preferably represents O (oxygen).
  • R 1 most preferably represents H or F.
  • R 2 most preferably represents CN.
  • Z very particularly preferably represents one of the heterocyclic groupings listed below,
  • Q 1 , Q 2 and R 3 have the meanings given above.
  • Another very particularly preferred group are those compounds of the
  • Another very particularly preferred group are those compounds of the
  • n, Q, Rl, R 2 and X have the meanings given above and
  • Another very particularly preferred group are those compounds of the formula (I) in which
  • Another very particularly preferred group are those compounds of the
  • radicals listed above or those specified in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • the new substituted aryl heterocycles of the general formula (I) have interesting biological properties. They are particularly characterized by their strong and selective herbicidal activity.
  • R represents alkyl
  • R 1 , R 2 and Z have the meaning given above and
  • X 1 represents halogen
  • R ⁇ has the meaning given above and
  • X ⁇ represents halogen
  • R3 has the meaning given above and
  • R represents alkyl having 1 to 6 carbon atoms
  • the compounds of the general formula (I) obtained according to processes (a) to (e) are converted into other compounds of the general formula (I) by customary methods.
  • the anhydrides to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (II).
  • Q 1 and R 3 preferably have those meanings which have been given above as preferred, particularly preferred or very particularly preferred for Q 1 and R 3 in connection with the description of the compounds of the general formula (I) according to the invention have been.
  • the starting materials of the general formulas (Ila) to (IIc) are known organic synthetic chemicals.
  • Formula (III) provides a general definition of the aminoarenes to be used further as starting materials in process (a) according to the invention.
  • n, Q, R 1 , R 2 and X preferably have those meanings which are preferred, particularly preferred or very particularly preferred for, in connection with the description of the compounds of the general formula (I) according to the invention n, Q, R 1 , R 2 and X have been specified.
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. Justus Liebigs Ann. Chem. 740 (1970), 169-179; US-A-3715395; US-A-3914418 ; DE-A-2748554; DE-A-3736089, DE-A-19830693).
  • R 1 , R 2 and X 1 have the meaning given above,
  • reaction auxiliary e.g. Sodium hydride
  • a diluent e.g. N-methylpyrrolidone
  • n, Q, Q 1 , R 1 , R 2 , R 4 and X preferably have those meanings which are particularly preferred above in connection with the description of the compounds of the general formula (I) according to the invention preferably or very particularly preferably for n, Q, Q 1 , R 1 , R 2 , R 4 and X have been given; R preferably represents C 1 -C 4 -alkyl, in particular methyl or ethyl.
  • R represents alkyl (in particular methyl or ethyl)
  • a diluent e.g. Toluene
  • phosgene or a phosgene substitute or phosgene generator
  • thiophosgene in the presence of a diluent, e.g. Chlorobenzene, at temperatures between -20 ° C and + 150 ° C.
  • Formula (V) provides a general definition of the haloaryl heterocycles to be used as starting materials in process (c) according to the invention for the preparation of compounds of the general formula (I).
  • R 1 , R 2 and Z preferably have those meanings which are preferred, particularly preferred or very particularly preferred for R 1 already in connection with the description of the compounds of the general formula (I) according to the invention , R 2 and Z have been specified;
  • X 1 preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf. DE-A-4335438, DE-A-4431218, DE-A-4444741, DE-A- 19520613, DE- A-19601626, DE-A-19606594, DE-A-19815947, EP-A-403891).
  • Formula (VI) provides a general definition of the aryl compounds to be used further as starting materials in process (c) according to the invention.
  • n, Q and X preferably have those meanings which have already been mentioned above in connection with the description of the invention Compounds of the general formula (I) have been indicated as preferred, particularly preferred or very particularly preferred for n, Q and X.
  • the starting materials of the general formula (VI) are known organic synthetic chemicals.
  • Formula (VII) provides a general definition of the arylhydrazines to be used as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I).
  • n, Q, R 1 , R 2 and X preferably have those meanings which are preferred, particularly preferred or very particularly preferred for, in connection with the description of the compounds of the general formula (I) according to the invention n, Q, R 1 , R 2 and X have been specified.
  • an alkali metal nitrite such as sodium nitrite or potassium nitrite
  • an acid such as hydrochloric acid
  • a diluent such as water
  • a reducing agent such as Tin (II) chloride dihydrate
  • Formula (VIII) provides a general definition of the ß-trihalomethyl-enones to be used as starting materials in process (d) according to the invention.
  • R 3 preferably has the meaning which has 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 or very particularly preferred for R 3 ;
  • X 2 preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the starting materials of the general formula (VIII) are known and / or can be prepared by processes known per se (cf. DE-A-2706700).
  • Formula (IX) provides a general definition of the hydrazone carbonyl compounds to be used as starting materials in process (e) according to the invention for the preparation of compounds of the general formula (I).
  • n, Q, R 1 , R 2 , R 3 and X preferably have those meanings which are already preferred above in connection with the description of the compounds of the general formula (I) according to the invention, particularly preferably or very particularly preferably for n, Q, R 1 , R 2 , R 3 and X have been specified.
  • R 3 has the meaning given above and
  • X 3 represents halogen (especially chlorine or bromine),
  • a diluent e.g. Water
  • a reaction auxiliary e.g. Sodium acetate
  • diluents for carrying out processes (a), (b), (c), (d) and (e) in addition to water are, in particular, inert organic solvents.
  • inert organic solvents include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,
  • Suitable reaction auxiliaries for processes (a), (b), (c), (d) and (e) according to the invention are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate,
  • Phase transfer catalysts are also suitable as further reaction auxiliaries for processes (a), (b), (c), (d) and (e) according to the invention.
  • Examples of such catalysts are: Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromide, benzylchloride, benzylchloride, benzyl methylammonium hydroxide, benzyl triethylammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tribut
  • reaction temperatures can be varied within a substantial range when carrying out processes (a), (b), (c), (d) and (e). In general, temperatures between -20 ° C and + 200 ° C, preferably between 0 ° C and 150 ° C.
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Crop 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.
  • Parts and organs of the plants such as sprout, leaf, flower and root, are to be understood, 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
  • 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 diving,
  • 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,
  • Brassica, lactuca, cucumis, cucurbita Brassica, lactuca, cucumis, cucurbita.
  • Scirpus Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • 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,
  • 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 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, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is liquid solvents and / or solid carriers
  • 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
  • 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.
  • 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.
  • 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 Question: eg broken and fractionated natural rocks such as calcite,
  • emulsifying and / or foaming agents are possible: e.g. non-ionic 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.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, 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%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • known herbicides are suitable for the mixtures, for example
  • Diflufenican Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethofumesmethyl-, Ethofumesmethyl- Ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl),
  • MCPP Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzaline, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, picolinafen, piperophos, pretilochlor, primisulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, py
  • 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.
  • a mixture of 1.0 g (3.88 mmol) of 4-amino-5-fluoro-2- (4-methoxy-phenoxy) benzonitrile, 0.57 g (3.88 mmol) of phthalic anhydride and 50 ml of acetic acid turns 60 Minutes at room temperature (about 20 ° C) and then heated to reflux for 30 hours. It is then concentrated in a water jet vacuum, the residue is shaken with water / ethyl acetate, the organic phase is separated off, washed twice with saturated aqueous sodium hydrogen carbonate solution and then with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether and the crystalline product is isolated by suction.
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Example (V-1) Analogously to Example (V-1), for example, the compounds of the general formula (V) listed in Table 2 below can also be prepared.
  • the mixture is then heated to 140 ° C to 150 ° C and stirred at this temperature for two hours, the gas evolution gradually subsiding.
  • the mixture is then concentrated at 50 ° C. under reduced pressure.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 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 concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Example B the compound according to Preparation Example 10, with good tolerance to crop plants, such as, for example, maize, shows a strong action against weeds.
  • Example B the compound according to Preparation Example 10, with good tolerance to crop plants, such as, for example, maize, shows 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 degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouveaux composés hétérocycliques d'aryle substitués, de formule générale (I), dans laquelle n, Q, R1, R2 et X ont la signification indiquée dans la description, ainsi que des procédés pour la production desdits composés, et leur utilisation comme herbicides.
PCT/EP2000/000123 1999-01-19 2000-01-11 Composes heterocycliques d'aryle substitues WO2000043375A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU26631/00A AU2663100A (en) 1999-01-19 2000-01-11 Substituted aryl heterocyclic compounds

Applications Claiming Priority (2)

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DE19901846.4 1999-01-19
DE1999101846 DE19901846A1 (de) 1999-01-19 1999-01-19 Substituierte Arylheterocyclen

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WO2000043375A2 true WO2000043375A2 (fr) 2000-07-27
WO2000043375A3 WO2000043375A3 (fr) 2002-09-26

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WO2002038562A1 (fr) * 2000-11-08 2002-05-16 Sumitomo Chemical Takeda Agro Company, Limited Derives de triazolone bicycliques et herbicides contenant ces derniers
WO2003051119A1 (fr) * 2001-12-15 2003-06-26 Bayer Cropscience Limited Nouveaux composes herbicides et procede
CN111356693A (zh) * 2017-11-23 2020-06-30 巴斯夫欧洲公司 除草的苯基醚类
US20210216011A1 (en) * 2019-12-26 2021-07-15 Tcl China Star Optoelectronics Technology Co., Ltd. Photoresist material, method of fabcricating same, and color filter substrate

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HUP0203448A3 (en) * 1999-10-13 2005-07-28 Pfizer Prod Inc Biaryl ether derivatives useful as monoamine reuptake inhibitors and pharmaceutical compositions containing them
US6410736B1 (en) 1999-11-29 2002-06-25 Pfizer Inc. Biaryl ether derivatives useful as monoamine reuptake inhibitors
EP3532474B1 (fr) 2016-10-27 2024-03-27 Bayer AG 1,2,4-triazolones 4,5-annelées

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002038562A1 (fr) * 2000-11-08 2002-05-16 Sumitomo Chemical Takeda Agro Company, Limited Derives de triazolone bicycliques et herbicides contenant ces derniers
WO2003051119A1 (fr) * 2001-12-15 2003-06-26 Bayer Cropscience Limited Nouveaux composes herbicides et procede
CN111356693A (zh) * 2017-11-23 2020-06-30 巴斯夫欧洲公司 除草的苯基醚类
US20210216011A1 (en) * 2019-12-26 2021-07-15 Tcl China Star Optoelectronics Technology Co., Ltd. Photoresist material, method of fabcricating same, and color filter substrate
US11506975B2 (en) * 2019-12-26 2022-11-22 Tcl China Star Optoelectronics Technology Co., Ltd. Photoresist material, method of fabcricating same, and color filter substrate

Also Published As

Publication number Publication date
AU2663100A (en) 2000-08-07
DE19901846A1 (de) 2000-07-20
WO2000043375A3 (fr) 2002-09-26

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