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WO2002006277A1 - Benzo-nitro-heterocycles substitues et leur utilisation comme herbicides - Google Patents

Benzo-nitro-heterocycles substitues et leur utilisation comme herbicides Download PDF

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Publication number
WO2002006277A1
WO2002006277A1 PCT/EP2001/007668 EP0107668W WO0206277A1 WO 2002006277 A1 WO2002006277 A1 WO 2002006277A1 EP 0107668 W EP0107668 W EP 0107668W WO 0206277 A1 WO0206277 A1 WO 0206277A1
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WO
WIPO (PCT)
Prior art keywords
chlorine
methyl
fluorine
optionally substituted
cyano
Prior art date
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PCT/EP2001/007668
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German (de)
English (en)
Inventor
Otto Schallner
Hans-Georg Schwarz
Dorothee Hoischen
Karl-Heinz Linker
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
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 AU2001277526A priority Critical patent/AU2001277526A1/en
Publication of WO2002006277A1 publication Critical patent/WO2002006277A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the invention relates to new substituted benzo nitrogen heterocycles, a process for their production and their use as plant treatment agents, in particular as herbicides.
  • the action of these compounds is not satisfactory in all respects.
  • R represents hydrogen or alkyl
  • R represents hydrogen or alkyl
  • Q represents O (oxygen) or S (sulfur)
  • R 1 represents optionally substituted alkyl, alkenyl, alkmyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
  • X represents hydrogen or halogen
  • Y represents O (oxygen), S (sulfur), NH or NR 1 , and
  • Q 2 represents O (oxygen) or S (sulfur),
  • R4 for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, dialkylamino, cycloalkyl or cycloalkyl or cycloalkyl stands,
  • R5 represents hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
  • R4 and R5 - together for optionally substituted and / or optionally with O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (alkyl) - at the beginning (or at the end) or interrupted alkanediyl or alkenediyl within the hydrocarbon chain,
  • Y 1 represents O (oxygen), S (sulfur), SO, SO 2 , NH, N (alkyl) or methylene, and
  • Y 2 represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , NH or N (alkyl),
  • hydrocarbon chains such as alkyl or alkanediyl - are also straight-chain or branched, also in conjunction with heteroatoms, such as in alkoxy.
  • A preferably represents a single bond or the grouping C (R 2 , R 3 ),
  • R 2 represents hydrogen or alkyl having 1 to 6 carbon atoms
  • R 3 represents hydrogen or alkyl having 1 to 6 carbon atoms.
  • Q is preferably O (oxygen).
  • R 1 preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, formyl (CHO), halogen, CrC 4 alkoxy, C 1 -C 4 alkoximino or C 1 -C 4 alkylthio, each optionally substituted by cyano or
  • Halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or Ci- alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by ⁇ itro, amino, cyano,
  • X preferably represents hydrogen, fluorine, chlorine or bromine.
  • Y preferably represents O (oxygen), S (sulfur), NH, N-CH 3 or NC 2 H 5 .
  • Z preferably represents one of the heterocyclic groupings outlined below
  • Ql preferably represents O (oxygen).
  • Q 2 preferably represents O (oxygen).
  • R 4 preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkyl optionally substituted by cyano, halogen or CrC-alkoxy having 1 to 6 carbon atoms, alkenyl or alkynyl each optionally substituted by halogen 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or -CC alkoxy or alkoxycarbonyl, each with 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen alkenyloxy or alkynyloxy, each with 3 to 6 carbon atoms, for optionally alkylthio having 1 to 6 carbon atoms substituted by cyano, halogen or C1-C4alkoxy, for each optionally substituted by halogen substituted alkenylthio or alky
  • R5 preferably represents hydrogen, hydroxyl, amino, cyano, alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having up to 6 carbon atoms, alkenyl optionally substituted by halogen or Alkynyl each having up to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally substituted by nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, -C 4 alkoxy or C ⁇ -C 4 haloalkoxy or phenyl-C 1 -C 4 al
  • Two adjacent radicals - R 4 and R 4 , R 5 and R 5 or R 4 and R 5 - optionally together preferably represent optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (C 1 -C -alkyl) - at the beginning (or at the end) or alkanediyl or alkenediyl interrupted within the hydrocarbon chain, each having up to 5 carbon atoms.
  • Y 1 preferably represents O (oxygen), S (sulfur), SO, SO 2 , NH, N (C 1 -C 4 alkyl) or methylene.
  • Y 2 preferably represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , NH or N (C 1 -C 4 alkyl).
  • Y 1 and Y 2 are different in each individual case.
  • R 2 represents hydrogen, methyl, ethyl, n- or i-propyl
  • R 3 represents hydrogen, methyl, ethyl, n- or i-propyl.
  • R 1 particularly preferably represents in each case optionally substituted by cyano, formyl (CHO), fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoximino, ethoximino, methylthio, ethylthio, n- or i-propylthio
  • Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl each optionally by nitro, amino, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, Trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-
  • X particularly preferably represents hydrogen, fluorine or chlorine.
  • Y particularly preferably represents O (oxygen), S (sulfur) or NH.
  • Z particularly preferably stands for
  • R 4 particularly preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for methyl, ethyl, n- or i, each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy -Propyl, n-, i-, s- or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for each optionally by cyano, fluorine, chlorine, methoxy or Ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbon
  • R5 particularly preferably stands for hydrogen, hydroxyl, amino, cyano, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-substituted in each case optionally by cyano, fluorine, chlorine, bromine, methoxy or ethoxy -Butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, for ethenyl, propenyl optionally substituted by fluorine, chlorine or bromine, Butenyl, ethynyl, propynyl or butynyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropy
  • Two adjacent radicals - R 4 and R 4 , R ⁇ and ⁇ or R 4 and R ⁇ - optionally together preferably represent optionally substituted by fluorine and or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (methyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or
  • Alkenediyl each with up to 4 carbon atoms.
  • Y 1 particularly preferably represents O (oxygen), S (sulfur), SO, SO 2 , NH, N (methyl) or methylene.
  • Y 2 particularly preferably represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , NH or N (methyl).
  • Y 1 and Y 2 are different in each individual case.
  • R 2 represents hydrogen or methyl
  • R 3 represents hydrogen or methyl.
  • R 1 very particularly preferably represents in each case optionally by cyano
  • Y very particularly preferably represents O (oxygen) or S (sulfur).
  • R 4 very particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, which are each optionally substituted by fluorine and / or chlorine.
  • R5 very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and or chlorine, propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine and / or chlorine, or by each if necessary cyclopropyl or cyclopropylmethyl substituted by fluorine, chlorine or methyl.
  • Two adjacent radicals - R 4 and R 4 , R ⁇ and R ⁇ or R 4 and R ⁇ - optionally together preferably represent optionally substituted by fluorine and / or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (methyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl, each with up to 4 carbon atoms.
  • Y 1 very particularly preferably represents O (oxygen), S (sulfur), NH, N (methyl) or methylene.
  • Y 2 very particularly preferably represents a single bond or O (oxygen), S (sulfur), NH or N (methyl).
  • Y and Y are different in each individual case.
  • a very particularly preferred group are those compounds of the formula (I) in which
  • R 2 represents hydrogen or methyl
  • R 3 represents hydrogen or methyl, Q stands for O (oxygen),
  • R 1 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine and / or bromine, for each optionally substituted by fluorine, chlorine, bromine, methyl or Ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for each optionally by nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl , Trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-
  • X represents hydrogen, fluorine or chlorine
  • Q 1 represents oxygen or sulfur (especially oxygen),
  • Q 2 represents oxygen or sulfur (especially oxygen)
  • R 4 "1 stands for cyano, carbamoyl, thiocarbamoyl, or for methyl, ethyl, n- or i-propyl (in particular trifluoromethyl) which is optionally substituted by fluorine and / or chlorine,
  • R 4 "2 represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl (in particular hydrogen, chlorine or methyl) which is optionally substituted by fluorine and / or chlorine, and
  • R 5 represents hydrogen, amino, methyl, ethyl, n- or i-propyl, propenyl, propynyl, cyclopropyl or cyclopropylmethyl (in particular amino or methyl).
  • Another very particularly preferred group are those compounds of the formula (I) in which A, Q, R 1 , X and Y have one of the meanings mentioned above, and
  • Z represents the heterocyclic grouping outlined below
  • Q 1 represents oxygen or sulfur (especially oxygen),
  • Q 2 represents oxygen or sulfur (especially oxygen), and
  • R 5 for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine and / or chlorine, or for each optionally optionally substituted by fluorine , Chlorine or methyl substituted Cyclopropyl or cyclopropylmethyl (especially for methyl or difluoromethyl) is.
  • Another very particularly preferred group are those compounds of the formula (T) in which A, Q, R 1 , X and Y have one of the meanings given above, and
  • Z represents the heterocyclic grouping outlined below
  • R 4 "1 represents hydrogen, cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl (in particular hydrogen, chlorine or bromine) substituted by fluorine and / or chlorine, and
  • R 4 "2 stands for cyano or for methyl, ethyl, n- or i-propyl (in particular for trifluoromethyl) which is optionally substituted by fluorine and / or chlorine, and
  • R 5 stands for methyl, ethyl, n- or i-propyl (especially for methyl).
  • Preferred compounds according to the invention are those of the formula (I) in which there is a combination of the meanings listed above as preferred.
  • 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.
  • the new substituted benzo nitrogen heterocycles have interesting biological properties. They are particularly characterized by their strong herbicidal activity.
  • X 1 represents halogen
  • Formula (II) provides a general definition of the benzo nitrogen heterocycles to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • Q, X, Y and Z 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 preferred or very particularly preferred for Q, X, Y and Z have been specified.
  • the starting materials of the general formula (II) are known and or can be prepared by processes known per se (cf. EP-A-170191, EP-A-311135, EP-A-328 001, EP-A-360 072, EP -A-379 894, EP-A-408 382, EP-A-415 642, EP-A-454444, EP-A-488 220, EP-A-568 041, US-A-4755 217, US-A -4 761 174, US-A-5 084 084, US-A-5 281 571, WO-A-90/10626, WO-A-92/06962, WO-A-97/26248, WO-A-97 / 28127, WO-A-98/07720, WO-A-99/59983).
  • Formula (HI) provides a general definition of the sulfenoic acid halides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • R 1 preferably has the meaning which has already been given as preferred, particularly preferred or very particularly preferred for R 1 in connection with the description of the compounds of the general formula) according to the invention.
  • X 1 preferably represents fluorine, chlorine or bromine, especially chlorine.
  • the starting materials of the general formula (III) are known organic synthetic chemicals.
  • reaction auxiliaries preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine
  • a diluent inert organic solvents are particularly suitable as diluents. 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 N
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -60 ° C and + 60 ° C, preferably between -40 ° C and
  • 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 large excess.
  • the reaction is generally carried out in a suitable diluent in the presence a reaction auxiliary and the reaction mixture is generally 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. 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 e.g. can be used in the following plants:
  • Apera Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus,
  • Dactyloctenium Digitaria, Echinochloa, Eleochans, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
  • 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 trees, 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 weed control 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 be used in certain concentrations or
  • 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).
  • 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 the plants, such as sprout, leaf, flower and root, examples being leaves,
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • all plants and their parts can be treated according to the invention.
  • wild plants weeds, harmful plants
  • conventional organic breeding methods such as e.g. Crossing or protoplast fusion, preserved plant species and plant varieties (crop plants) and their parts treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms) and their parts are treated.
  • the term "parts” or "parts of plants” or "plant parts” was explained above.
  • Plant varieties are cultivated 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 transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or water salt or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • transgenic plants are the important crop plants such as cereals (including rice), maize, soybeans, potatoes, cotton, beets, rapeseed, cultivated grasses such as golf and ornamental turf, fruit plants (with the fruits apples, pears, citrus fruits and grapes) and Plantation crops such as oil and rubber trees are mentioned, with cereals (including rice), corn, soybeans, potatoes, cotton, beets and rapeseed being particularly emphasized.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringjensis (for example by the genes Cry ⁇ A (a), CryIA (b), CryIA (c), CryllA, CrylHA, Cryi ⁇ B2, Cry9c, Cry2Ab, Cry3Bb and CryLF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the traits that are particularly emphasized are the elevated ones
  • SAR systemic acquired resistance
  • systemin phytoalexins
  • elicitors as well as resistance genes and correspondingly expressed proteins and toxins.
  • the traits are also particularly emphasized as the increased tolerance of the plants to certain herbicidal active substances and classes of active substances such as glyphosate or glufosinate / phosphinothricin (eg "PAT" gene), ALS materials such as imida- zolinones, sulfonylureas and others, PPO inhibitors (eg plants with acuron genes), 4-HPD inhibitors such as isoxazoles (eg isoxaflutole), ACCase inhibitors such as sethoxydim, and bromoxynil.
  • PPO inhibitors eg plants with acuron genes
  • 4-HPD inhibitors such as isoxazoles (eg isoxaflutole)
  • ACCase inhibitors such as sethoxydim, and bromoxynil.
  • genes imparting the desired properties can also occur in combinations with one another in the transgenic plants.
  • “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties, soy varieties, cereals including rice varieties, beet varieties and rapeseed varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosates e.g. corn, cotton, soybean, beet, rapeseed), Liberty Link® (tolerance against glufosinates, eg rapeseed, maize, beets), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas eg maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g. maize, rice).
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemicals
  • Active ingredients - better plant growth of crops, increased tolerance of Crop plants against high or low temperatures, increased tolerance of the crop plants to dryness or to water salt or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of harvested products possible that go beyond the expected effects.
  • 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, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
  • 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 Agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents 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, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse 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 as granules from organic material such as sawdust,
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • 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, marble, pumice, se
  • coconut shells, corn cobs and tobacco stems as 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. Ligmn sulfite liquor and
  • 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 phospho- lipids 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%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop plant tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible Mixtures with weed control agents are also possible which contain one or more known herbicides and a safener.
  • safeners crop plant tolerance
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime,
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil stain remedies, is also possible.
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. 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.
  • the lambda maximums were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • 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 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 active ingredient in the spray liquor is selected so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • the compounds according to preparation example 1, 2, 3, 4, 5, 6, 7, 8, 13, 14, 15, 16, 17, 18 and 28 show, in some cases, good tolerance to crop plants, such as, for example, maize, Wheat and soy, very effective against weeds.
  • crop plants such as, for example, maize, Wheat and soy, very effective against weeds.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray liquor is chosen so that in

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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)
  • Plural Heterocyclic Compounds (AREA)
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Abstract

L'invention concerne de nouveaux benzo-nitro-hétérocycles substitués de formule (I), dans laquelle A représente une liaison simple ou le groupement C(R?2,R3), R2¿ représentant hydrogène ou alkyle et R3 représentant hydrogène ou alkyle, Q représente O (oxygène) ou S (soufre), R1 représente alkyle, alcényle, alcynyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle, chacun éventuellement substitué, X représente hydrogène ou halogène, Y représente O (oxygène), S (soufre), NH ou N-R1, et Z représente un groupement hétérocyclique. L'invention concerne également un procédé pour leur production et leur utilisation comme herbicides.
PCT/EP2001/007668 2000-07-18 2001-07-05 Benzo-nitro-heterocycles substitues et leur utilisation comme herbicides WO2002006277A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001277526A AU2001277526A1 (en) 2000-07-18 2001-07-05 Substituted benzo-nitro-heterocycles and use thereof as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10034800.9 2000-07-18
DE2000134800 DE10034800A1 (de) 2000-07-18 2000-07-18 Substituierte Benzostickstoffheterocyclen

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AU (1) AU2001277526A1 (fr)
DE (1) DE10034800A1 (fr)
WO (1) WO2002006277A1 (fr)

Cited By (25)

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JP2007501416A (ja) * 2003-05-27 2007-01-25 アレクサンダー・メンゼル 光ルミネセンスを用いて痕跡量の爆発物を検出するための方法
US8114868B2 (en) 2008-07-25 2012-02-14 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8138178B2 (en) 2008-05-01 2012-03-20 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8202857B2 (en) 2008-02-11 2012-06-19 Vitae Pharmaceuticals, Inc. 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8242111B2 (en) 2008-05-01 2012-08-14 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8329897B2 (en) 2007-07-26 2012-12-11 Vitae Pharmaceuticals, Inc. Synthesis of inhibitors of 11β-hydroxysteroid dehydrogenase type 1
US8440658B2 (en) 2007-12-11 2013-05-14 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8569292B2 (en) 2008-05-01 2013-10-29 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8592409B2 (en) 2008-01-24 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic carbazate and semicarbazide inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8592410B2 (en) 2008-05-01 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
US8598160B2 (en) 2008-02-15 2013-12-03 Vitae Pharmaceuticals, Inc. Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
US8637505B2 (en) 2009-02-04 2014-01-28 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8680093B2 (en) 2009-04-30 2014-03-25 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8765744B2 (en) 2010-06-25 2014-07-01 Boehringer Ingelheim International Gmbh Azaspirohexanones
US8835449B2 (en) 2011-11-11 2014-09-16 Pfizer Inc. 2-thiopyrimidinones
US8835426B2 (en) 2007-02-26 2014-09-16 Vitae Pharmaceuticals, Inc. Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8846668B2 (en) 2008-07-25 2014-09-30 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8846613B2 (en) 2010-11-02 2014-09-30 Boehringer Ingelheim International Gmbh Pharmaceutical combinations for the treatment of metabolic disorders
US8883778B2 (en) 2009-07-01 2014-11-11 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1
US8927539B2 (en) 2009-06-11 2015-01-06 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
US8933072B2 (en) 2010-06-16 2015-01-13 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
CN105272973A (zh) * 2014-06-10 2016-01-27 华中师范大学 一种含有苯并噁嗪环的嘧啶二酮类化合物及其应用
US9771332B2 (en) 2015-05-05 2017-09-26 Pfizer Inc. 2-thiopyrimidinones
US11352332B2 (en) 2018-02-26 2022-06-07 AlzeCure Pharma AB Triazine derivatives for treating diseases relating to neurotrophins
US11840524B2 (en) 2018-06-28 2023-12-12 AlzeCure Pharma AB 4-substituted phenyl-1,3,5-triazine derivatives as modulators of TrK receptors

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EP0334055A2 (fr) * 1988-03-10 1989-09-27 Bayer Ag Benzoxazinones substituées, plusieurs procédés et intermédiaires pour leur préparation ainsi que leur application comme herbicides
DE3922107A1 (de) * 1989-07-05 1991-01-17 Bayer Ag N-aryl-stickstoffheterocyclen

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US4804394A (en) * 1986-09-09 1989-02-14 Nihon Tokushu Noyaku Seizo K.K. Benzoxazines and use as herbicides
US4755217A (en) * 1987-01-15 1988-07-05 Fmc Corporation Triazinedione herbicides
EP0334055A2 (fr) * 1988-03-10 1989-09-27 Bayer Ag Benzoxazinones substituées, plusieurs procédés et intermédiaires pour leur préparation ainsi que leur application comme herbicides
DE3922107A1 (de) * 1989-07-05 1991-01-17 Bayer Ag N-aryl-stickstoffheterocyclen

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US7910376B2 (en) 2003-05-27 2011-03-22 Alexander Menzel Method for detecting trace explosives using photoluminescence
JP4673312B2 (ja) * 2003-05-27 2011-04-20 アレクサンダー・メンゼル 光ルミネセンスを用いて痕跡量の爆発物を検出するための方法
JP2007501416A (ja) * 2003-05-27 2007-01-25 アレクサンダー・メンゼル 光ルミネセンスを用いて痕跡量の爆発物を検出するための方法
US8835426B2 (en) 2007-02-26 2014-09-16 Vitae Pharmaceuticals, Inc. Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8575156B2 (en) 2007-07-26 2013-11-05 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8329897B2 (en) 2007-07-26 2012-12-11 Vitae Pharmaceuticals, Inc. Synthesis of inhibitors of 11β-hydroxysteroid dehydrogenase type 1
US8748444B2 (en) 2007-12-11 2014-06-10 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8440658B2 (en) 2007-12-11 2013-05-14 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8592409B2 (en) 2008-01-24 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic carbazate and semicarbazide inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8202857B2 (en) 2008-02-11 2012-06-19 Vitae Pharmaceuticals, Inc. 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8598160B2 (en) 2008-02-15 2013-12-03 Vitae Pharmaceuticals, Inc. Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
US8569292B2 (en) 2008-05-01 2013-10-29 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8242111B2 (en) 2008-05-01 2012-08-14 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8592410B2 (en) 2008-05-01 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
US8138178B2 (en) 2008-05-01 2012-03-20 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8846668B2 (en) 2008-07-25 2014-09-30 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8754076B2 (en) 2008-07-25 2014-06-17 Vitae Pharmaceuticals, Inc./Boehringer-Ingelheim Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8114868B2 (en) 2008-07-25 2012-02-14 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8637505B2 (en) 2009-02-04 2014-01-28 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8680093B2 (en) 2009-04-30 2014-03-25 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8927539B2 (en) 2009-06-11 2015-01-06 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
US8883778B2 (en) 2009-07-01 2014-11-11 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1
US9090605B2 (en) 2010-06-16 2015-07-28 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
US8933072B2 (en) 2010-06-16 2015-01-13 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
US8765744B2 (en) 2010-06-25 2014-07-01 Boehringer Ingelheim International Gmbh Azaspirohexanones
US8846613B2 (en) 2010-11-02 2014-09-30 Boehringer Ingelheim International Gmbh Pharmaceutical combinations for the treatment of metabolic disorders
US9399626B2 (en) 2011-11-11 2016-07-26 Pfizer Inc. 2-thiopyrimidinones
US8835449B2 (en) 2011-11-11 2014-09-16 Pfizer Inc. 2-thiopyrimidinones
US8841314B2 (en) 2011-11-11 2014-09-23 Pfizer Inc. 2-Thiopyrimidinones
US9873673B2 (en) 2011-11-11 2018-01-23 Pfizer Inc. 2-thiopyrimidinones
CN105272973A (zh) * 2014-06-10 2016-01-27 华中师范大学 一种含有苯并噁嗪环的嘧啶二酮类化合物及其应用
CN105272973B (zh) * 2014-06-10 2019-02-01 华中师范大学 一种含有苯并噁嗪环的嘧啶二酮类化合物及其应用
US9771332B2 (en) 2015-05-05 2017-09-26 Pfizer Inc. 2-thiopyrimidinones
US11352332B2 (en) 2018-02-26 2022-06-07 AlzeCure Pharma AB Triazine derivatives for treating diseases relating to neurotrophins
US12209071B2 (en) 2018-02-26 2025-01-28 AlzeCure Pharma AB Triazine derivatives for treating diseases relating to neurotrophins
US11840524B2 (en) 2018-06-28 2023-12-12 AlzeCure Pharma AB 4-substituted phenyl-1,3,5-triazine derivatives as modulators of TrK receptors

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AU2001277526A1 (en) 2002-01-30
DE10034800A1 (de) 2002-01-31

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