EP3416961A1 - Quinazolinedione-6-carbonyl derivatives and their use as herbicides - Google Patents

Quinazolinedione-6-carbonyl derivatives and their use as herbicides

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Publication number
EP3416961A1
EP3416961A1 EP17703778.5A EP17703778A EP3416961A1 EP 3416961 A1 EP3416961 A1 EP 3416961A1 EP 17703778 A EP17703778 A EP 17703778A EP 3416961 A1 EP3416961 A1 EP 3416961A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
cycloalkyl
halo
halogeno
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.)
Withdrawn
Application number
EP17703778.5A
Other languages
German (de)
French (fr)
Inventor
Ralf Braun
Christian Waldraff
Anu Bheemaiah MACHETTIRA
Hansjörg Dietrich
Elmar Gatzweiler
Christopher Hugh Rosinger
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 CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3416961A1 publication Critical patent/EP3416961A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/72—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
    • A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms
    • 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
    • C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • An object of the present invention are thus quinazolinedione-6-carbonyl derivatives of the formula (I) and salts thereof
  • X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) -haloalkynyl, (C 3 -C 6) -cycloalkyl, (C 3 - C 6) halocycloalkyl, (C 3 C 6) -cycloalkyl- ( Ci-C 6) alkyl, (C3-C 6) -Halogencycloalkyl- (Ci-C 6) alkyl, COR 1, OR 1, OCOR 1, OSO2R 2, S (0) n R 2, SO2OR 1, S0 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR'C
  • Z is O or S
  • W is hydrogen, nitro, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 1 -C 4 ) -alkoxy,
  • R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, Halo (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) - Alkyl- (C3-C7) cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C 6) alkyl, (C3-C7) cycloalkyl (C3-C7) cycloalkyl, halo ( C 3 -C 7 -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -
  • R 1 is phenyl, phenylsulfonyl, W 1 -phenyl), W'-CO-phenyl), W'-CS-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 -phenyl) or W 2 - (SCH 2 -phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 3 ,
  • R 2 is hydrogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) Alkynyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -
  • Halocycloalkyl (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) - alkyl, pyridyl or (C 1 -C 6) -alkylpyridyl, where the phenyl or pyridyl rings of the four abovementioned radicals each carry s substituents R 3 , Q denotes a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
  • R cl is hydroxy or SR 4 , R c2 , R c3 , R 04 , R c5 , R c6 and R c7 are each independently hydrogen or (Ci-C 4 ) alkyl,
  • R pl is hydrogen, (C 1 -C 6) -alkylsulfonyl, (C 1 -C 4) -alkoxy- (C 1 -C 6) -alkylsulfonyl, or in each case by n identical or different radicals from the group consisting of halogen, (C 1 -C 4) - Alkyl and (C 1 -C 4) -alkoxy-substituted phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl- (C 1 -C 6) -alkyl or benzyl,
  • R p2 is (C 1 -C 4 ) -alkyl
  • R p3 is hydrogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4 ) -alkyl (C 3 -C 8 ) -cycloalkyl or (C 3 -C 6 ) -halocycloalkyl .
  • R nl represents (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (Ci-C4) alkyl- (C3-C8) cycloalkyl or (C 3 -C 6) - halocycloalkyl
  • R n2 is hydrogen, C0 2 (C 1 -C 6 ) -alkyl or S (0) n (C 1 -C 6 ) -alkyl
  • Y is O or CO
  • Y 1 represents an ethylene or vinylene group
  • Y 2 is O, CO or CH 2
  • W 1 is (C 1 -C 10) -alkylene, (C 2 -C 6 ) -alkenylene or (C 2 -C 6 ) -alkynylene
  • W 2 is (C 1 -C 10) -alkylene
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
  • R 4 is (Ci-C i) -alkyl or by p radicals from the group halogen, nitro, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy and (Ci C4) haloalkoxy-substituted phenyl, n is 0, 1 or 2, p is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is 0, 1, 2, 3 or 4, v means 2, 3, 4, 5, 6 or 7.
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl.
  • alkenyl is for example allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1 - yl, l -methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl.
  • Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can each be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic, saturated ring system having three to six carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, eg cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond may be in any position.
  • C 1 -C 10) -alkylene accordingly denotes a methylene, ethylene, in each case unbranched propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene or decylene group.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Similarly, stereoisomers occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
  • the compounds of the invention may also occur as geometric isomers (E / Z isomers) due to the oxime ether structure.
  • the invention also relates to all E / Z isomers and mixtures thereof which are encompassed by the general formula (I) but which are not specifically defined.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine and ammonium, alkali or Alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR'R "R"'] + , where R to R'"each independently of one another organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
  • the compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g.
  • a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • X is halogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - Halocycloalkyl, OR 1 , S (O) n R 2 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR'COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 or (C 1 -C 6 ) -alkyl-OR 1
  • Z is O
  • W is hydrogen, Cl, MeO, methyl or ethyl
  • R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, Halo (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl- (C 3 -C 7 ) -cycloalkyl, (C3 -C 7) cycloalkyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) - alkyl (C 3 -C 7) cycloalkyl, (Ci-C 6) alkylthio
  • R 1 is phenyl which carries s substituent R 3 ,
  • R 2 is (C 1 -C 4 ) -alkyl, means a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
  • R c2 , R c3 , R 04 , R c5 , R c6 and R c7 are each independently hydrogen or methyl, R pl is hydrogen,
  • R p2 is (C 1 -C 4 ) -alkyl
  • R p3 is hydrogen, (Ci-C i) -alkyl or cyclopropyl, R nl is cyclopropyl, R n2 is hydrogen, Y is O or CO,
  • Y 1 is an ethylene or vinylene group
  • Y 2 is CH 2
  • X is F, Cl, Br, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy, methoxymethyl,
  • W is hydrogen
  • R 1 is (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogen (C 2 -C 10) -alkenyl, halo (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl- (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl
  • R 1 is phenyl which carries s substituent R 3 ,
  • R 2 is methyl or ethyl
  • Q is a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
  • R cl is hydroxyl
  • R c2 , R c3 , R 04 , R c5 , R c6 and R c7 are each independently hydrogen or methyl
  • R pl is hydrogen
  • R p2 is (Ci-C 4 ) alkyl
  • R p3 is hydrogen, (Ci-C i) -alkyl or cyclopropyl, R nl is cyclopropyl, R n2 is hydrogen, Y is O or CO, Y 1 is an ethylene or vinylene group,
  • Y 2 is CH 2
  • R 3 represents halogen, cyano, nitro, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C2-C6) alkynyl,
  • Scheme 1 can be prepared analogously to the methods mentioned in WO 2009/018925 Al.
  • the quinazolinedione-6-carboxylic acid chlorides (II) or the quinazolinedione-6-carboxylic acids (III) on which they are based can be used, for example. be prepared according to the methods described in WO2015058519.
  • Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34.
  • Chromatographieapparaturen available, for example, the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • Solid-phase assisted synthesis methods allow a number of protocols known from the literature, which in turn can be performed manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • Both solid and liquid phases may require the performance of one or more
  • Present invention are also libraries containing at least two compounds of formula (I) and their salts.
  • the compounds according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial harmful plants, which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
  • the present invention therefore also provides a method for controlling
  • Plant cultures in which one or more compounds of the invention (s) on the plants eg harmful plants such as mono- or dicotyledonous weeds or undesirable crops
  • the seed eg grains, seeds or vegetative propagules such as tubers or sprouts with buds
  • the area on the plants grow eg the acreage
  • the compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschinen be applied.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be named, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum. depending on the structure of the respective compound of the invention and their application rate only insignificantly damaged or not at all. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in
  • Crops such as agricultural crops or ornamental plantings.
  • the compounds according to the invention depending on their respective chemical structure and the applied application rate, have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, Bacteria or viruses.
  • Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • Preferred for transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potato, cassava, tomato, pea and other vegetables.
  • the compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-242246)
  • transgenic crops with modified fatty acid composition (WO 91/13972).
  • transgenic crops which are characterized by higher yields or better quality transgenic crops characterized by a combination of z.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed.
  • reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA to provide a cosuppression effect, or expressing at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants can in principle be plants of any one
  • Plant species ie, both monocotyledonous and dicotyledonous plants.
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • the essential plant enzymes eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined.
  • Formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, Suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC oil- or water-based dispersions
  • auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen,
  • Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
  • Dispersant e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate or sodium oleoylmethyltaurine.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol ester, Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
  • Propylene oxide-ethylene oxide condensation products alkyl polyethers, sorbitan esters, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
  • Emulsions e.g. Oil-in-water emulsions (EW), for example, by means of stirrers,
  • Solvents and optionally surfactants such as e.g. listed above for the other formulation types.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or
  • Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • Methyl and W and R pl are hydrogen, and Z is oxygen.
  • Table 2 Compounds of the invention of the general formula (I) wherein Q is Q 2 , Y 1 is an ethylene bridge, Y 2 is CH 2 , R 2 is methyl, R cl is hydroxy, W, R c2 and R c4 are hydrogen , and Z means oxygen.
  • Table 3 Compounds of the general formula (I) according to the invention, in which Q is Q 1 , Y is a CO group, R cl is hydroxyl, R 2 , R c2 , R c3 , R c and R c5 are methyl, W is hydrogen stand, and Z means oxygen.
  • Table 4 Compounds of the invention of the general formula (I) wherein Q is Q, R is methyl, R nl is cyclopro l, W and R n2 are hydrogen, and Z is oxygen.
  • Table 5 Compounds of the invention of the general formula (I) in which Q is Q 5 , R 2 is methyl, R nl is cyclopropyl, W is hydrogen, and Z is oxygen.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by adding 25
  • a dispersion concentrate readily dispersible in water is obtained by adding 20 parts by weight of a compound of the formula (I) and / or its salts with 6 parts by weight
  • Alkylphenolpolyglyko lether ®Triton X 207
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granules are obtained by
  • a water-dispersible granules are also obtained by
  • Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied. After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants.
  • the compounds of the present invention Nos. 1-2, 1-3, 1-4, 1-5, 1-8, 1-19, 2-2, 2-3, 2-4, 2-7, 3-2, 3 -3, 3-4, 4-2 and 5-2 at an application rate of 0.32 kg or less per hectare have an at least 80% action against Setaria viridis and Matricaria inodora.
  • compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice in the pre-emergence process practically undamaged even at high doses of active ingredient.
  • some substances also protect dicotyledonous crops such as soya, cotton, rapeseed, sugar beet or potatoes.
  • Some of the compounds according to the invention show a high selectivity and are therefore suitable in the pre-emergence process for controlling undesired plant growth in agricultural crops.
  • Gramineous crops such as barley, wheat, rye, millet, maize or rice, post-emergence even with high doses of active ingredient virtually undamaged.
  • some substances also protect dicotyledonous crops such as soya, cotton, rapeseed, sugar beet or potatoes.
  • Some of the compounds according to the invention show a high selectivity and are therefore suitable postemergence for combating undesired plant growth in agricultural crops.

Abstract

The invention relates to quinazolinedione-6-carbonyl derivatives of general formula (I) used as herbicides. In formula (I), R1, R2, X and W stand for groups such as hydrogen, alkyl and halogen. Z is a chalcogen. Q is a five-membered heterocycle.

Description

Chinazolindion-6-carbonylderivate und ihre Verwendung als Herbizide  Quinazolinedione-6-carbonyl derivatives and their use as herbicides
Die Erfindung betrifft das technische Gebiet der Herbizide, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in Nutzpflanzenkulturen. The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
In WO 2015/058519 AI sind Chinazolindion-6-carbonylcyclohexandione als Herbizide beschrieben. Die aus diesen Schriften bekannten Verbindungen weisen jedoch nicht immer eine ausreichende herbizide Wirkung und/oder Verträglichkeit gegenüber Kulturpflanzen auf. Es wurde nun gefunden, dass Chinazolindion-6-carbonylderivate, die sich von denen aus dem Stand der Technik bekannten Verbindungen dadurch unterscheiden, daß sie andere als die in WO 2015/058519 AI beschriebenen Cyclohexandione-Reste tragen, als Herbizide besonders gut geeignet sind. In WO 2015/058519 Al Chinazolindion-6-carbonylcyclohexandione are described as herbicides. However, the compounds known from these publications do not always have a sufficient herbicidal activity and / or compatibility with crop plants. It has now been found that quinazolinedione-6-carbonyl derivatives, which differ from those known from the prior art in that they carry cyclohexanedione radicals other than those described in WO 2015/058519 A1, are particularly suitable as herbicides.
Ein Gegenstand der vorliegenden Erfindung sind somit Chinazolindion-6-carbonylderivate der Formel (I) und deren Salze An object of the present invention are thus quinazolinedione-6-carbonyl derivatives of the formula (I) and salts thereof
worin wherein
X bedeutet Nitro, Halogen, Cyano, Formyl, Rhodano, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)- Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C3-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Halogencycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halogencycloalkyl-(Ci-C6)-alkyl, COR1, OR1, OCOR1, OSO2R2, S(0)nR2, SO2OR1, S02N(R1)2, NR1S02R2, NR'COR1, (Ci-C6)-Alkyl- S(0)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OS02R2, (Ci-C6)-Alkyl-COOR1, (Ci-C6)-Alkyl-S02OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-S02N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1S02R2 oder NR'R2, X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) -haloalkynyl, (C 3 -C 6) -cycloalkyl, (C 3 - C 6) halocycloalkyl, (C 3 C 6) -cycloalkyl- ( Ci-C 6) alkyl, (C3-C 6) -Halogencycloalkyl- (Ci-C 6) alkyl, COR 1, OR 1, OCOR 1, OSO2R 2, S (0) n R 2, SO2OR 1, S0 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR'COR 1 , (C 1 -C 6 ) -alkyl, S (0) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , ( C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-COOR 1 , (C 1 -C 6 ) -alkyl-S0 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-S0 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , ( C 1 -C 6 ) -alkyl-NR 1 S0 2 R 2 or NR'R 2 ,
Z bedeutet O oder S, W bedeutet Wasserstoff, Nitro, Halogen, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Halogenalkyl oder (C1-C4)- Alkoxy, Z is O or S, W is hydrogen, nitro, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 1 -C 4 ) -alkoxy,
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen- (C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen-(C3-Cio)-cycloalkyl, (C1-C4)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (C3-C12)- Cycloalkenyl, Halogen-(C3-Ci2)-cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)- alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkoxy-(C3-C7)-cycloalkyl, Di-(Ci-C6)-alkoxy-(C3- C7)-cycloalkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfmyl- (Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci-C6)-alkyl, Di-(Ci-C6)- alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylamino-(Ci- Ce)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)-alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci- Ce)-Alkoxy-carbonyl, (C3-C7)-Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci- C6)-Alkylamino-carbonyl, Di-(C i-C6)-alkylamino-carbonyl, (C3-C7)-Cycloalkylamino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-(Ci- Ce)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)- cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl- carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-C7)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci- Ce)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3- Cio)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl- carbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-C6)-Alkyl-carbonyl-(Ci-C6)-alkoxy, (Ci-Ce)-R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, Halo (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) - Alkyl- (C3-C7) cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C 6) alkyl, (C3-C7) cycloalkyl (C3-C7) cycloalkyl, halo ( C 3 -C 7 -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl- (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 12) -cycloalkenyl, halo (C 3 -C 2) cycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) alkoxy (C 2 -C 6) - alkenyl, ( C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy- (C 3 -C 7 ) -cycloalkyl, di- (C 1 -C 6 ) -alkoxy- (C 3 - C 7) cycloalkyl, (C 3 -C 7) cycloalkoxy (Ci-C 6) alkyl, (C 3 -C 7) cycloalkoxy (Ci-C6) alkoxy (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (Ci -C 6) -Alkylsulfmyl- (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C 6) alkylamino (Ci-C6) alkyl , Di- (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkylamino (C 1 -C 4 ) Ce) alkyl, (Ci-C6) alkyl-carbonyl, halo (Ci-C6) alkyl-carbonyl, (C3-C7) -cycloalkyl-carbonyl, (Ci- Ce) alkoxy-carbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylamino-carbonyl, di (C 1 -C 6) -alkylamino -carbonyl, (C3-C7) cycloalkylamino-carbonyl, cyano (C-C6) alkyl, hydroxy (Ci-C 6) alkyl, (C 3 -C 7) cycloalkenyl (C 6 ) -alkyl, halo (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy -halo (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6) -alkyl, halogeno ( C3-C7) - cycloalkenyloxy (Ci-C 6) alkyl, di (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 10) -alkoxy, halogenated Cio) alkoxy, (C3-Ci2) cycloalkoxy, halo (C3-C7) cycloalkoxy, (C3-C7) -cycloalkyl- (Ci- Ce) alkoxy, (C2-Ci2) alkenyloxy, halogen - (C 2 -C 10) -alkenyloxy, (C 2 -C 10) -alkynyloxy, halo (C 3 -C 10) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkyl -carbonyloxy, halo (C 2 -C 12) -alkyl- c arbonyloxy, (C3-C7) -cycloalkyl-carbonyloxy, (Ci-C6) alkyl-carbonyl- (Ci-C6) alkoxy, (Ci-Ce) -
Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3- Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen-(Ci-C6)-alkyl-carbonylamino, (C1-C10)- Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Hydroxy, Amino, NHCHO, oder Alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 12) -cycloalkylamino, (C 1 -C 6) -alkyl- carbonylamino, halo (C 1 -C 6) alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halo (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6) -alkylamino , Hydroxy, amino, NHCHO, or
R1 bedeutet Phenyl, Phenylsulfonyl, W^Phenyl), W'-CO-Phenyl), W'-CS-Phenyl), W1-(S02-Phenyl), W2-(S02CH2-Phenyl) oder W2-(SCH2-Phenyl), wobei die Phenylringe der acht vorstehend genannten Reste jeweils s Substituenten R3 tragen, R 1 is phenyl, phenylsulfonyl, W 1 -phenyl), W'-CO-phenyl), W'-CS-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 -phenyl) or W 2 - (SCH 2 -phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 3 ,
R2 bedeutet Wasserstoff, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)- Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-R 2 is hydrogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) Alkynyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -
Halogencycloalkyl, (Ci-C6)-Alkyl-0-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl- (Ci-C6)-alkyl, Pyridyl oder (Ci-C6)-Alkylpyridyl, wobei die Phenyl- oder Pyridylringe der vier vorstehend genannten Reste jeweils s Substituenten R3 tragen, Q bedeutet einen Rest Q1, Q2, Q3, Q4 oder Q5, Halocycloalkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) - alkyl, pyridyl or (C 1 -C 6) -alkylpyridyl, where the phenyl or pyridyl rings of the four abovementioned radicals each carry s substituents R 3 , Q denotes a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
Q1 Q2 Q3 Q4 Q5 Q 1 Q 2 Q 3 Q 4 Q 5
Rcl bedeutet Hydroxy oder SR4, Rc2, Rc3, R04, Rc5, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci-C4)-Alkyl, R cl is hydroxy or SR 4 , R c2 , R c3 , R 04 , R c5 , R c6 and R c7 are each independently hydrogen or (Ci-C 4 ) alkyl,
Rpl bedeutet Wasserstoff, (Ci-C6)-Alkylsulfonyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkylsulfonyl, oder jeweils durch n gleiche oder verschiedene Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)-Alkyl und (Ci- C4)-Alkoxy substituiertes Phenylsulfonyl, Thiophenyl-2-sulfonyl, Benzoyl, Benzoyl-(Ci-C6)-alkyl oder Benzyl, R pl is hydrogen, (C 1 -C 6) -alkylsulfonyl, (C 1 -C 4) -alkoxy- (C 1 -C 6) -alkylsulfonyl, or in each case by n identical or different radicals from the group consisting of halogen, (C 1 -C 4) - Alkyl and (C 1 -C 4) -alkoxy-substituted phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl- (C 1 -C 6) -alkyl or benzyl,
Rp2 bedeutet (Ci-C4)-Alkyl, R p2 is (C 1 -C 4 ) -alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C4)-Alkyl-(C3-C8)-cycloalkyl oder (C3-C6)-Halogencycloalkyl, R p3 is hydrogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4 ) -alkyl (C 3 -C 8 ) -cycloalkyl or (C 3 -C 6 ) -halocycloalkyl .
Rnl bedeutet (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C4)-Alkyl-(C3-C8)-cycloalkyl oder (C3-C6)- Halogencycloalkyl, Rn2 bedeutet Wasserstoff, C02(Ci-C6)-Alkyl oder S(0)n(Ci-C6)-Alkyl, R nl represents (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (Ci-C4) alkyl- (C3-C8) cycloalkyl or (C 3 -C 6) - halocycloalkyl, R n2 is hydrogen, C0 2 (C 1 -C 6 ) -alkyl or S (0) n (C 1 -C 6 ) -alkyl,
Y bedeutet O oder CO, Y is O or CO,
Y1 bedeutet eine Ethylen- oder Vinylengruppe, Y 1 represents an ethylene or vinylene group,
Y2 bedeutet O, CO oder CH2 Y 2 is O, CO or CH 2
W1 bedeutet (Ci-Cio)-Alkylen, (C2-C6)-Alkenylen oder (C2-C6)-Alkinylen, W2 bedeutet (Ci-Cio)-Alkylen, R bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -C(=0)R3a, -C(=0)OR3a, W 1 is (C 1 -C 10) -alkylene, (C 2 -C 6 ) -alkenylene or (C 2 -C 6 ) -alkynylene, W 2 is (C 1 -C 10) -alkylene, R is halogen, cyano, hydroxy, amino, nitro, -C (= O) R 3a , -C (= O) OR 3a ,
-C(=0)(NR3a)2, -C(=S)NH2, -C(=0)NHCN, -C(=0)NHOH, -SH, -S02(NR3a)2, -S02NHCN, -S02NHOH, -OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Halogen-(Ci-C6)-alkyl, Halogen- (C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)- cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C8)- Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy, Halogen- (Ci-C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C6)- alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-Ce)- Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)-Cycloalkylthio, (Ci-C6)- Alkylsulfinyl, Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-C8)-alkylamino oder (C3-C8)-Cycloalkylamino, oder -C (= O) (NR 3a ) 2 , -C (= S) NH 2 , -C (= O) NHCN, -C (= O) NHOH, -SH, -SO 2 (NR 3a ) 2 , - S0 2 NHCN, -S0 2 NHOH, -OCN, -SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halogen (Ci-C 6) alkyl, halo (C 2 -C 6) alkenyl, halo (C 2 -C 6) -alkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C 6) - alkyl (C 3 -C 7) cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 8) - cycloalkenyl, halo (C 3 -C 8) - cycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 3 -C 7) cycloalkoxy (Ci-C 6) alkyl , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkyl) 8 ) -alkylsulfmyl- (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy, halogeno (C 1 -C 6 ) alkoxy, (C 3 -C 8 ) cycloalkoxy, halogeno (C 3 -C 8 ) cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (Ci-C 6) - alkoxy, (C 2 -C 6) alkenyloxy, halo (C 2 -C 6) alkenyloxy, (Ci-C6) alkoxy (Ci-C6) alkoxy, ( C 2 -Ce) - alkylcarbon yloxy, (Ci-C 6) alkylthio, halo (Ci-C 6) -alkylthio, (C 3 -C 8) -cycloalkylthio, (Ci-C6) - alkylsulphinyl, halo (Ci-C6) alkylsulfinyl , (C 1 -C 6 ) -alkylsulfonyl, halogeno (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 8 ) -cycloalkylsulfonyl, (C 1 -C 6 ) -alkylamino, di- (C 1 -C 6 ) -alkylamino, halogeno ( Ci-C6) alkylamino, halogen-di- (Ci-C 8) alkylamino or (C 3 -C 8) cycloalkylamino, or
zwei vicinale Reste R3 bilden zusammen mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen 5- bis 7-gliedrigen Ring, der v Kohlenstoffatome und p gleiche oder verschiedene Atome aus der Gruppe Sauerstoff, Schwefel oder Stickstoff enthält, und t Oxogruppen trägt, R3a bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, two vicinal radicals R 3 together with the two carbon atoms to which they are attached form a 5- to 7-membered ring containing v carbon atoms and p identical or different atoms from the group oxygen, sulfur or nitrogen, and t carries oxo groups , R 3a is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R4 bedeutet (Ci-C i)-Alkyl oder durch p Reste aus der Gruppe Halogen, Nitro, Cyano, (C1-C4)- Alkyl, (Ci-C4)-Halogenalkyl, (Ci-C4)-Alkoxy und (Ci-C4)-Halogenalkoxy substituiertes Phenyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1, 2, 3 oder 4, s bedeutet 0, 1, 2, 3, 4 oder 5, t bedeutet 0, 1, 2, 3 oder 4, v bedeutet 2, 3, 4, 5, 6 oder 7. In der Formel (I) und allen nachfolgenden Formeln können Alkylreste mit mehr als zwei Kohlenstoffatomen geradkettig oder verzweigt sein. Alkylreste bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl. Analog bedeutet Alkenyl z.B. Allyl, l -Methylprop-2-en-l -yl, 2-Methyl-prop-2-en-l -yl, But-2-en-l -yl, But-3-en-l -yl, l -Methyl-but-3-en-l -yl und l -Methyl-but-2-en-l -yl. Alkinyl bedeutet z.B. Propargyl, But-2-in-l -yl, But-3-in-l -yl, l -Methyl-but-3-in-l -yl. Die Mehrfachbindung kann sich jeweils in beliebiger Position des ungesättigten Rests befinden. Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit drei bis sechs C- Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Analog bedeutet Cycloalkenyl eine monocyclische Alkenylgruppe mit drei bis sechs Kohlenstoffringgliedern, z.B. Cyclopropenyl, Cyclobutenyl, Cyclopentenyl und Cyclohexenyl, wobei sich die Doppelbindung an beliebiger Position befinden kann. (Ci-Cio)-Alkylen bedeutet entsprechend eine Methylen-, Ethylen-, jeweils unverzweigte Propylen-, Butylen-, Pentylen-, Hexylen-, Heptylen-, Octylen-, Nonylen- oder Decylen-Gruppe. Halogen steht für Fluor, Chlor, Brom oder Iod. R 4 is (Ci-C i) -alkyl or by p radicals from the group halogen, nitro, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy and (Ci C4) haloalkoxy-substituted phenyl, n is 0, 1 or 2, p is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is 0, 1, 2, 3 or 4, v means 2, 3, 4, 5, 6 or 7. In formula (I) and all subsequent formulas, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Analogously, alkenyl is for example allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1 - yl, l -methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl. Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. The multiple bond can each be in any position of the unsaturated radical. Cycloalkyl means a carbocyclic, saturated ring system having three to six carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Analogously, cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, eg cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond may be in any position. (C 1 -C 10) -alkylene accordingly denotes a methylene, ethylene, in each case unbranched propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene or decylene group. Halogen is fluorine, chlorine, bromine or iodine.
Ist eine Gruppe mehrfach durch Reste substituiert, so ist darunter zu verstehen, daß diese Gruppe durch ein oder mehrere gleiche oder verschiedene der genannten Reste substituiert ist. Analoges gilt für den Aufbau von Ringsystemen durch verschiedene Atome und Elemente. Dabei sollen solche Verbindungen vom Anspruchsbegehren ausgenommen sein, von denen der Fachmann weiß, dass sie unter If a group is repeatedly substituted by radicals, it is to be understood that this group is substituted by one or more identical or different radicals. The same applies to the construction of ring systems by different atoms and elements. In this case, such compounds should be excluded from the claim, which is known to the skilled person that under
Normalbedingungen chemisch instabil sind. Normal conditions are chemically unstable.
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Ebenso treten Stereoisomere auf, wenn n für 1 steht (Sulfoxide). Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden, beispielsweise durch chromatographische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft auch alle Stereoisomeren und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Die erfindungsgemäßen Verbindungen können auf Grund der Oximether- Struktur auch als geometrische Isomere (E-/Z-Isomere) auftreten. Die Erfindung betrifft auch alle E-/Z- Isomere und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Similarly, stereoisomers occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined. The compounds of the invention may also occur as geometric isomers (E / Z isomers) due to the oxime ether structure. The invention also relates to all E / Z isomers and mixtures thereof which are encompassed by the general formula (I) but which are not specifically defined.
Die Verbindungen der Formel (I) können Salze bilden. Geeignete Basen sind beispielsweise organische Amine , wie Trialkylamine, Morpholin, Piperidin oder Pyridin sowie Ammonium-, Alkali- oder Erdalkalimetallhydroxide, -carbonate und -hydrogen-carbonate, insbesondere Natrium- und The compounds of formula (I) can form salts. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine and ammonium, alkali or Alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and
Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quaternäre) Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRR'R"R" ']+, worin R bis R' " jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR'R "R"'] + , where R to R'"each independently of one another organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and
Alkylsulfoxoniumsalze, wie (Ci-C4)-Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. Alkylsulfoxoniumsalze, such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
Die Verbindungen der Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie HCl, HBr, H2SO4, H3PO4 oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie p-Toluolsulfonsäure, an eine basische Gruppe, wie Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. The compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. For example, carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.
Bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Preference is given to compounds of the general formula (I) in which
X bedeutet Halogen, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halogencycloalkyl, OR1, S(0)nR2, S02N(R1)2, NR1S02R2, NR'COR1, (Ci-C6)-Alkyl-S(0)nR2 oder (Ci-C6)-Alkyl-OR1 X is halogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - Halocycloalkyl, OR 1 , S (O) n R 2 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR'COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 or (C 1 -C 6 ) -alkyl-OR 1
Z bedeutet O, W bedeutet Wasserstoff, Cl, MeO, Methyl oder Ethyl, Z is O, W is hydrogen, Cl, MeO, methyl or ethyl,
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen- (C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen-(C3-Cio)-cycloalkyl, (C1-C4)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)- Alkylsulfonyl-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (Ci-C6)- alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkylamino oder Di-(Ci-C6)-alkylamino , R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, Halo (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl- (C 3 -C 7 ) -cycloalkyl, (C3 -C 7) cycloalkyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) - alkyl (C 3 -C 7) cycloalkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C6) -Alkylsulfmyl- (Ci-C 6) alkyl, (Ci-C 6) - alkylsulfonyl (Ci- C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, (C 1 -C 10) -alkoxy, halogeno (C 1 -C 10) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) - alkoxy, (C 1 -C 6) -alkylamino or di- (C 1 -C 6) -alkylamino,
R1 bedeutet Phenyl, das s Substituenten R3 trägt, R 1 is phenyl which carries s substituent R 3 ,
R2 bedeutet (Ci-C4)-Alkyl, bedeutet einen Rest Q1, Q2, Q3, Q4 oder Q5, R 2 is (C 1 -C 4 ) -alkyl, means a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
Q1 Q2 Q3 Q4 Q5 Rcl bedeutet Hydroxy, Q 1 Q 2 Q 3 Q 4 Q 5 R cl is hydroxy,
Rc2, Rc3, R04, Rc5, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, Rpl bedeutet Wasserstoff, R c2 , R c3 , R 04 , R c5 , R c6 and R c7 are each independently hydrogen or methyl, R pl is hydrogen,
Rp2 bedeutet (Ci-C4)-Alkyl, R p2 is (C 1 -C 4 ) -alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C i)-Alkyl oder Cyclopropyl, Rnl bedeutet Cyclopropyl, Rn2 bedeutet Wasserstoff, Y bedeutet O oder CO, R p3 is hydrogen, (Ci-C i) -alkyl or cyclopropyl, R nl is cyclopropyl, R n2 is hydrogen, Y is O or CO,
Y1 bedeutet eine Ethylen- oder Vinylengruppe, Y2 bedeutet CH2, R3 bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -C(=0)R3a,C(=0)OR3a, Y 1 is an ethylene or vinylene group, Y 2 is CH 2 , R 3 is halogen, cyano, hydroxyl, amino, nitro, -C (= O) R 3a , C (= O) OR 3a ,
-C(=0)(NR3a)2, -C(=S)NH2, -C(=0)NHCN, -C(=0)NHOH, -SH, -S02NH2, -S02NHCN, -C (= O) (NR 3a ) 2 , -C (= S) NH 2 , -C (= O) NHCN, -C (= O) NHOH, -SH, -SO 2 NH 2 , -SO 2 NHCN .
-S02NHOH, -OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, -S0 2 NHOH, -OCN, -SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl,
Halogen-(Ci-C6)-alkyl, Halogen-(C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (C3- C8)-Cycloalkenyl, Halogen-(C3-C8)-cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkoxy- (Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C8)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C8)-Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci- Ce)-alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-Cg)-Cycloalkoxy, Halogen-(C3-Cg)- cycloalkoxy, (C3-Cg)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-C6)-Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)- alkylthio, (C3-Cg)-Cycloalkylthio, (Ci-C6)-Alkylsulfmyl, Halogen-(Ci-C6)-alkylsulfmyl, (Ci-C6)-Halo (Ci-C6) alkyl, halo (C 2 -C 6) alkenyl, halo (C 2 -C 6) -alkynyl, (C3-C8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C 6) alkyl, (C 3 - C 8) cycloalkenyl, halogen - (C 3 -C 8) cycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 3 -C 7) cycloalkoxy (Ci-C 6) alkyl, (C -C 6) alkoxy- (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 8) - Alkylsulfinyl- (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl- alkyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy, (C 3 -C 9) -cycloalkoxy, halogeno (C 3 -C 9) -cycloalkoxy, (C 3 -C 8) -cycloalkyl- (C 1 -C 6) -alkyl ) alkoxy, (C2-C6) alkenyloxy, halo (C2-C6) alkenyloxy, (Ci-C6) alkoxy (Ci-C 6) alkoxy, (C 2 -C 6) alkylcarbonyloxy, (Ci-C 6) alkylthio, halo (Ci-C 6) - alkylthio, (C3 -CG) cycloalkylthio, (Ci-C 6) -Alkylsulfmyl, halo (Ci-C 6) -alkylsulfmyl, ( Ci-C 6 ) -
Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-Cg)-Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci- C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-Cg)-alkylamino, (C3-Cg)-Cycloalkylamino oder Methylendioxo, R3a bedeutet Wasserstoff oder (Ci-C6)-Alkyl, n bedeutet 0, 1 oder 2, s bedeutet 0, 1, 2, 3, 4 oder 5. Alkylsulfonyl, halo (C 1 -C 6) -alkylsulfonyl, (C 3 -C 9) -cycloalkylsulfonyl, (C 1 -C 6) -alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halogenoalkyl di (Ci-Cg) -alkylamino, (C3-Cg) -cycloalkylamino or methylenedioxo, R 3a is hydrogen or (Ci-C 6 ) -alkyl, n means 0, 1 or 2, s means 0, 1, 2, 3, 4 or 5.
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Particular preference is given to compounds of the general formula (I) in which
X bedeutet F, Cl, Br, Methyl, Ethyl, Cyclopropyl, Trifluormethyl, Methoxy, Methoxymethyl, X is F, Cl, Br, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy, methoxymethyl,
Methoxyethoxymethyl, SMe oder S02Me, Methoxyethoxymethyl, SMe or SO 2 Me,
Z bedeutet O, Z means O,
W bedeutet Wasserstoff, R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen- (C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen-(C3-Cio)-cycloalkyl, (C1-C4)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-W is hydrogen, R 1 is (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogen (C 2 -C 10) -alkenyl, halo (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl- (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl
(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkylthio-(Ci- C6)-alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, oder (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl, (Ci-C 6 ) Alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfmyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, or
R1 bedeutet Phenyl, das s Substituenten R3 trägt, R 1 is phenyl which carries s substituent R 3 ,
R2 bedeutet Methyl oder Ethyl, R 2 is methyl or ethyl,
Q bedeutet einen Rest Q1, Q2, Q3, Q4 oder Q5, Q is a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
Q1 Q2 Q3 Q4 Q5 Q 1 Q 2 Q 3 Q 4 Q 5
Rcl bedeutet Hydroxy, Rc2, Rc3, R04, Rc5, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, Rpl bedeutet Wasserstoff, Rp2 bedeutet (Ci-C4)-Alkyl, R cl is hydroxyl, R c2 , R c3 , R 04 , R c5 , R c6 and R c7 are each independently hydrogen or methyl, R pl is hydrogen, R p2 is (Ci-C 4 ) alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C i)-Alkyl oder Cyclopropyl, Rnl bedeutet Cyclopropyl, Rn2 bedeutet Wasserstoff, Y bedeutet O oder CO, Y1 bedeutet eine Ethylen- oder Vinylengruppe, R p3 is hydrogen, (Ci-C i) -alkyl or cyclopropyl, R nl is cyclopropyl, R n2 is hydrogen, Y is O or CO, Y 1 is an ethylene or vinylene group,
Y2 bedeutet CH2, Y 2 is CH 2 ,
R3 bedeutet Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, R 3 represents halogen, cyano, nitro, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C2-C6) alkynyl,
Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy- (Ci-C6)-alkyl, (Ci-C6)-Alkylthio, (Ci-C6)-Alkylsulfmyl, (Ci-C6)-Alkylsulfonyl, Phenyl oder Halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, (Ci-C 6) alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl, phenyl or
Methylendioxo, s bedeutet 0, 1, 2, 3, 4 oder 5. In allen nachfolgend genannten Formeln haben die Substituenten und Symbole, sofern nicht anders definiert, dieselbe Bedeutung wie unter Formel (I) beschrieben. Erfindungsgemäße Verbindungen mit Q = Q1, Q2, Q3, Q4 oder Q5 können beispielsweise u.a. Methylene dioxo, s means 0, 1, 2, 3, 4 or 5. In all the formulas below, the substituents and symbols, unless otherwise defined, have the same meaning as described under formula (I). Compounds of the invention with Q = Q 1 , Q 2 , Q 3 , Q 4 or Q 5 may, for example, inter alia
Schema 1 analog den in WO 2009/018925 AI genannten Methoden hergestellt werden. Scheme 1 can be prepared analogously to the methods mentioned in WO 2009/018925 Al.
Schema 1 Scheme 1
Die Chinazolindion-6-carbonsäurechloride (II), beziehungsweise die ihnen zugrunde liegenden Chinazolindion-6-carbonsäuren (III) können z.B. nach den in WO2015058519 beschriebenen Methoden hergestellt werden. The quinazolinedione-6-carboxylic acid chlorides (II) or the quinazolinedione-6-carboxylic acids (III) on which they are based can be used, for example. be prepared according to the methods described in WO2015058519.
Es kann zweckmäßig sein, Reaktionsschritte in ihrer Reihenfolge zu ändern. So sind Benzoesäuren, die ein Sulfoxid tragen, nicht ohne weiteres in ihre Säurechloride zu überführen. Hier bietet sich an, zunächst auf Thioether-Stufe das Amid zu herzustellen und danach den Thioether zum Sulfoxid zu oxidieren. It may be convenient to change reaction steps in order. Thus, benzoic acids carrying a sulfoxide are not readily converted into their acid chlorides. Here it is advisable to first produce the amide on the thioether stage and then to oxidize the thioether to the sulfoxide.
Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist. Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Calpyso-Reaktionsblöcke (Caylpso reaction blocks) der Firma Barnstead International, Dubuque, Iowa 52004-0797, USA oder Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England oder MultiPROBE Automated Workstations der Firma Perkin Elmar, Waltham, Massachusetts 02451 , USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34. For parallelized reaction performance and work-up, a number of commercially available devices may be used, for example, Calypso reaction blocks (Caylpso reaction blocks) from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill. Saffron Waiden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations of Perkin Elmar, Waltham, Massachusetts 02451, USA. For the parallelized purification of compounds of the general formula (I) and their salts or of the intermediates obtained during the preparation, inter alia
Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. Chromatographieapparaturen available, for example, the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Caliper, Hopkinton, MA 01748, USA bezogen werden. The listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed. This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer- supported reagents/Scavanger-Harze unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich). The implementation of single or several synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins. A number of experimental protocols are described in the literature, for example in ChemFiles, Vol. 1, Polymer-Supported Scavengers and Reagents for Solution Phase Synthesis (Sigma-Aldrich).
Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998 und Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or adapted for the appropriate approach synthesis are bound to a synthetic resin. Solid phase assisted synthetic methods are well described in the literature, e.g. Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998, and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999. The use of
Festphasen- unterstützten Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Die Reaktionen können beispielsweise mittels IRORI-Technologie in Mikroreaktoren (microreactors) der Firma Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA durchgeführt werden. Solid-phase assisted synthesis methods allow a number of protocols known from the literature, which in turn can be performed manually or automatically. The reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Both solid and liquid phases may require the performance of one or more
Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und a. Stadler), Verlag Wiley, 2005. Synthetic steps are supported by the use of microwave technology. In the A number of experimental protocols are described in specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (published by CO Kappe and A. Stadler), published by Wiley, 2005.
Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel (I) und deren Salze in Form von Substanzkollektionen, die Bibliotheken genannt werden. Gegenstand der The preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries. Subject of the
vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel (I) und deren Salzen enthalten. Present invention are also libraries containing at least two compounds of formula (I) and their salts.
Die erfindungsgemäßen Verbindungen weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen auf. Auch schwer bekämpfbare perennierende Schadpflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfasst. The compounds according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial harmful plants, which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von The present invention therefore also provides a method for controlling
unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in undesirable plants or for regulating the growth of plants, preferably in
Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im Einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll.  Plant cultures in which one or more compounds of the invention (s) on the plants (eg harmful plants such as mono- or dicotyledonous weeds or undesirable crops), the seed (eg grains, seeds or vegetative propagules such as tubers or sprouts with buds) or the area on the plants grow (eg the acreage), are applied. The compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufverfahren be applied. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be named, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria und Sorghum. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishamedum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola und Xanthium. Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis Galinsoga Galium Hibiscus Ipomoea Kochia Lamium Lepidium Lindernia Matricaria Mentha Mercurialis Mullugo Myosotis Papaver Pharbitis Plantago Polygonum Portulaca Ranunculus Raphanus Rorippa Rotala Rumex , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola and Xanthium. If the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks. Upon application of the active ingredients to the green parts of the plant postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that in this way harmful to the crops weed competition very early and sustainably eliminated. Although the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum. depending on the structure of the respective compound of the invention and their application rate only insignificantly damaged or not at all. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in
Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Darüber hinaus weisen die erfindungsgemäßen Verbindungen, abhängig von ihrer jeweiligen chemischen Struktur und der ausgebrachten Aufwandmenge, hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Des Weiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. Crops such as agricultural crops or ornamental plantings. In addition, the compounds according to the invention, depending on their respective chemical structure and the applied application rate, have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, Bacteria or viruses. Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
Fettsäurezusammensetzung des Ernteguts bekannt. Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Maniok, Tomate, Erbse und anderen Gemüsesorten. Fatty acid composition of the crop known. Preferred for transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potato, cassava, tomato, pea and other vegetables.
Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. The compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Conventional ways of producing new plants which have modified properties in comparison with previously occurring plants consist, for example, in classical methods
Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A- 0131624). Beschrieben wurden beispielsweise in mehreren Fällen Breeding methods and the generation of mutants. Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have been described
gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/11376, WO 92/14827, WO 91/19806),  genetically engineered crop modifications to modify the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, WO 91/19806),
transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate (WO 92/00377) oder der Sulfonylharnstoffe (EP- transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-242246)
A-0257993, US-A-5013659) resistent sind, A-0257993, US-A-5013659) are resistant,
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis- Toxine (Bt-Toxine) zu produzieren, welche die Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP-A-0193259).  Transgenic crops, such as cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259).
- transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972). transgenic crops with modified fatty acid composition (WO 91/13972).
gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte Krankheitsresistenz verursachen (EPA 309862, EPA0464461) gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398).  genetically modified crops with new content or secondary substances z. B. new phytoalexins that cause increased disease resistance (EPA 309862, EPA0464461) genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398).
- Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming") - Transgenic crops that produce pharmaceutically or diagnostically important proteins ("molecular pharming")
transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualität auszeichnen transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking"). Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt, siehe z. B. I. Potrykus und G. transgenic crops, which are characterized by higher yields or better quality transgenic crops characterized by a combination of z. B. the above-mentioned new properties ("gene stacking"). Numerous molecular biological techniques that can be used to produce novel transgenic plants with altered properties are known in principle. BI Potrykus and G.
Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, oder Christou, "Trends in Plant Science" 1 (1996) 423-431). Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA- Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. For such genetic engineering, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 The production of plant cells For example, reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA to provide a cosuppression effect, or expressing at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227, Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells. The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants can in principle be plants of any one
Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Plant species, ie, both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydroxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Preferably, the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen als Herbizide zur Bekämpfung von Schadpflanzen in transgenen Kulturpflanzen. In the application of the active compounds according to the invention in transgenic crops, in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops. The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten. The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. When
Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in- Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Mikrokapseln und Wachse. Formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, Suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemical Technology",
Band 7, C. Hanser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.  Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen,
"Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC"Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC
Publ. Corp., Ridgewood N.J., Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Publ. Corp., Ridgewood N.J., Sisley and Wood, "Encyclopaedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Geeignete Safener sind beispielsweise Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, On the basis of these formulations, combinations with other pesticidally active substances, e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix. Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,
Cloquintocet-mexyl und Dichlormid. Cloquintocet-mexyl and Dichlormid.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykol-ethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Dispersant), e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate or sodium oleoylmethyltaurine. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers). Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol ester, Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B.  Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, e.g.
Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylene. Dusts are obtained by milling the active ingredient with finely divided solids, e.g.
Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
Emulsionen, z.B. Öl-in- Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Emulsions, e.g. Oil-in-water emulsions (EW), for example, by means of stirrers,
Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Colloidal mills and / or static mixers using aqueous organic
Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Solvents and optionally surfactants, such as e.g. listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable
Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden.  Active ingredients in the usual manner for the production of fertilizer granules - if desired, mixed with fertilizers - granulated.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. Verfahren in For the preparation of plate, fluid bed, extruder and spray granules, see e.g. Procedure in
"Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. "Spray-Drying Handbook" 3rd Ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq., "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen. For more details on pesticide formulation see, for example, GC Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pp. 81-96, and JD Freyer, SA Evans, "Weed Control Handbook." 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige  In wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Powdery
Formulierungen enthalten Containing formulations
1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei  1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient. at
wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH- Wert und die Viskosität beeinflussende Mittel. In addition, the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. On the basis of these formulations, combinations with other pesticidally active substances, e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. For use, the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or
Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt.  Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Verbindungen der Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 1,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 750 g/ha. With the external conditions such as temperature, humidity, the type of herbicide used, u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
Die in nachfolgenden Tabellen aufgeführten Beispiele wurden analog oben genannten Methoden hergestellt beziehungsweise sind analog oben genannten Methoden erhältlich. Diese Verbindungen sind ganz besonders bevorzugt. Die verwendeten Abkürzungen bedeuten: Ph = Phenyl Me = Methyl The examples listed in the following tables were prepared analogously to the above-mentioned methods or are obtainable analogously to the methods mentioned above. These compounds are most preferred. The abbreviations used mean: Ph = phenyl Me = methyl
Tabelle 1 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q , R für Table 1: Compounds of the invention of the general formula (I) wherein Q is Q, R is
Methyl und W sowie Rpl für Wasserstoff stehen, und Z Sauerstoff bedeutet. Methyl and W and R pl are hydrogen, and Z is oxygen.
Nr. RP2 RP3 X R1 Physikalische Daten No. RP 2 RP 3 XR 1 Physical data
OH-NMR, DMSO-de or CDC13 ,400 MHz)OH-NMR, DMSO-de or CDC1 3 , 400 MHz)
1-1 Me H Me Ph 1-1 Me H Me Ph
1-2 Me H Me 2-Me-Ph (DMSO-d6): 7.69 (d,lH), 7.46 (d,lH),  1-2 Me H Me 2-Me-Ph (DMSO-d6): 7.69 (d, 1H), 7.46 (d, 1H),
7.37-7.27 (m,4H), 7.22 (d,lH), 3.57 (s,3H), 3.55 (s,3H), 2.61 (s,3H), 2.06 (s,3H)  7.37-7.27 (m, 4H), 7.22 (d, 1H), 3.57 (s, 3H), 3.55 (s, 3H), 2.61 (s, 3H), 2.06 (s, 3H)
1-3 Me Me Me 2-Me-Ph (DMSO-d6): 7.58 (d,lH), 7.42 (d,lH),  1-3 Me Me Me 2-Me-Ph (DMSO-d6): 7.58 (d, 1H), 7.42 (d, 1H),
7.37-7.30 (m,3H), 7.22 (d,lH), 3.57 (s,3H), 3.41 (s,3H), 2.57 (s,3H), 2.54 (s,3H), 2.05 (s,3H)  7.37-7.30 (m, 3H), 7.22 (d, 1H), 3.57 (s, 3H), 3.41 (s, 3H), 2.57 (s, 3H), 2.54 (s, 3H), 2.05 (s, 3H)
1-4 Me H Me 2-Me,4-F-Ph (DMSO-d6): 7.70 (d,lH), 7.46 (d,lH),  1-4 MeH Me 2-Me, 4-F-Ph (DMSO-d6): 7.70 (d, 1H), 7.46 (d, 1H),
7.30-7.22 (m,2H), 7.27 (s,lH), 7.13 (m,lH), 3.57 (s,3H), 3.55 (s,3H), 2.61 (s,3H), 2.06 (s,3H)  7.30-7.22 (m, 2H), 7.27 (s, 1H), 7.13 (m, 1H), 3.57 (s, 3H), 3.55 (s, 3H), 2.61 (s, 3H), 2.06 (s, 3H)
1-5 Me H Me 2-Et-Ph (DMSO-d6): 7.69 (d,lH), 7.46 (d,lH),  1-5 MeH Me 2-Et-Ph (DMSO-d6): 7.69 (d, 1H), 7.46 (d, 1H),
7.37-7.26 (m,4H), 7.21 (d,lH), 3.57 (s,3H), 3.55 (s,3H), 2.60 (s,3H), 2.38 (q,2H), 1.07 (t,3H)  7.37-7.26 (m, 4H), 7.21 (d, 1H), 3.57 (s, 3H), 3.55 (s, 3H), 2.60 (s, 3H), 2.38 (q, 2H), 1.07 (t, 3H)
1-6 Me H Me 2-CF3-Ph 1-6 MeH Me 2-CF 3 -Ph
1-7 Me H Me 2-CN-Ph  1-7 Me H Me 2-CN-Ph
1-8 Me H Me 2-MeO-Ph (DMSO-d6): 7.68 (d,lH), 7.44 (d,lH),  1-8 MeH Me 2-MeO-Ph (DMSO-d6): 7.68 (d, 1H), 7.44 (d, 1H),
7.41 (d,lH), 7.28 (s,lH), 7.24 (dd,lH), 7.17 (d,lH), 7.04 (dd,lH), 3.73 (s,3H), 3.56 (s,3H), 3.55 (s,3H), 2.59 (s,3H) 7.41 (d, 1H), 7.28 (s, 1H), 7.24 (dd, 1H), 7.17 (d, 1H), 7.04 (dd, 1H), 3.73 (s, 3H), 3.56 (s, 3H), 3.55 (s, 3H), 2.59 (s, 3H)
1-9 Me H Me 3-MeO-Ph 1-9 MeH Me 3-MeO-Ph
1-10 Me H Me 4-MeO-Ph  1-10 Me H Me 4 MeO Ph
1-11 Me H Me 2-F-Ph  1-11 Me H Me 2-F-Ph
1-12 Me H Me 3-F-Ph  1-12 MeH Me 3-F-Ph
1-13 Me H Me 4-F-Ph  1-13 Me H Me 4-F-Ph
1-14 Me H Me 2-Cl-Ph  1-14 Me H Me 2 Cl-Ph
1-15 Me H Me 3-Cl-Ph  1-15 Me H Me 3-Cl-Ph
1-16 Me H Me 4-Cl-Ph Nr. RP2 RP3 X R1 Physikalische Daten 1-16 Me H Me 4-Cl-Ph No. RP 2 RP 3 XR 1 Physical data
OH-NMP, DMSO-de or CDC13 ,400 MHz)-17 Me H Me 2,6-Me2-PhOH-NMP, DMSO-de or CDC1 3 , 400 MHz) -17 Me H Me 2,6-Me 2 -Ph
-18 Et H Me Ph-18 Et H Me Ph
-19 Et H Me 2-Me-Ph (DMSO-d6): 77.1 (d,lH), 7.45 (d,lH), EtH Me 2-Me-Ph (DMSO-d6): 77.1 (d, 1H), 7.45 (d, 1H),
7.37-7.29 (m,4H), 7.22 (d,lH), 3.93 (q,2H), 3.58 (s,3H), 2.55 (s,3H), 2.06 (s,3H) 7.37-7.29 (m, 4H), 7.22 (d, 1H), 3.93 (q, 2H), 3.58 (s, 3H), 2.55 (s, 3H), 2.06 (s, 3H)
-20 Et H Me 2-CF3-Ph-20 EtH Me 2-CF 3 -Ph
-21 Et H Me 2-CN-Ph-21 Et H Me 2-CN-Ph
-22 Et H Me 2-MeO-Ph-22 EtH Me 2-MeO-Ph
-23 Et H Me 3-MeO-Ph-23 Et H Me 3-MeO-Ph
-24 Et H Me 4-MeO-Ph-24 Et H Me 4-MeO-Ph
-25 Et H Me 2-F-Ph-25 Et H Me 2-F-Ph
-26 Et H Me 3-F-Ph-26 Et H Me 3-F-Ph
-27 Et H Me 4-F-Ph-27 Et H Me 4-F-Ph
-28 Et H Me 2-Cl-Ph-28 Et H Me 2-Cl-Ph
-29 Et H Me 3-Cl-Ph-29 Et H Me 3-Cl-Ph
-30 Et H Me 4-Cl-Ph-30 Et H Me 4-Cl-Ph
-31 Et H Me 2,6-Me2-Ph-31 Et H Me 2,6-Me 2 -Ph
-32 Me H Cl Ph-32 Me H Cl Ph
-33 Me H Cl 2-Me-Ph (DMSO-d6): 7.75 (d,lH), 7.58 (d,lH), -33 Me H Cl 2-Me-Ph (DMSO-d6): 7.75 (d, 1H), 7.58 (d, 1H),
7.38-7.28 (m,4H), 7.23 (d,lH), 3.58 (s,3H), 3.54 (s,3H), 2.07 (s,3H) 7.38-7.28 (m, 4H), 7.23 (d, 1H), 3.58 (s, 3H), 3.54 (s, 3H), 2.07 (s, 3H)
-34 Me H Cl 2-CF3-Ph-34 Me H Cl 2-CF 3 Ph
-35 Me H Cl 2-CN-Ph-35 Me H Cl 2-CN-Ph
-36 Me H Cl 2-MeO-Ph-36 Me H Cl 2-MeO-Ph
-37 Me H Cl 3-MeO-Ph-37 Me H Cl 3-MeO-Ph
-38 Me H Cl 4-MeO-Ph-38 Me H Cl 4-MeO-Ph
-39 Me H Cl 2-F-Ph-39 Me H Cl 2-F-Ph
-40 Me H Cl 3-F-Ph-40 Me H Cl 3-F-Ph
-41 Me H Cl 4-F-Ph-41 Me H Cl 4-F-Ph
-42 Me H Cl 2-Cl-Ph-42 Me H Cl 2 Cl-Ph
-43 Me H Cl 3-Cl-Ph-43 Me H Cl 3-Cl-Ph
-44 Me H Cl 4-Cl-Ph-44 Me H Cl 4-Cl-Ph
-45 Me H Cl 2,6-Me2-Ph-45 Me H Cl 2.6 Me 2 Ph
-46 Et H Cl Ph-46 Et H Cl Ph
-47 Et H Cl 2-Me-Ph-47 Et H Cl 2-Me-Ph
-48 Et H Cl 2-CF3-Ph-48 Et H Cl 2-CF 3 Ph
-49 Et H Cl 2-CN-Ph-49 Et H Cl 2-CN-Ph
-50 Et H Cl 2-MeO-Ph-50 Et H Cl 2-MeO-Ph
-51 Et H Cl 3-MeO-Ph-51 Et H Cl 3-MeO-Ph
-52 Et H Cl 4-MeO-Ph Nr. RP2 RP3 X R1 Physikalische Daten -52 Et H Cl 4-MeO-Ph No. RP 2 RP 3 XR 1 Physical data
OH-NMR, DMSO-de or CDC13 ,400 MHz)OH-NMR, DMSO-de or CDC1 3 , 400 MHz)
1-53 Et H Cl 2-F-Ph 1-53 Et H Cl 2-F-Ph
1-54 Et H Cl 3-F-Ph  1-54 Et H Cl 3-F-Ph
1-55 Et H Cl 4-F-Ph  1-55 Et H Cl 4-F-Ph
1-56 Et H Cl 2-Cl-Ph  1-56 Et H Cl 2-Cl-Ph
1-57 Et H Cl 3-Cl-Ph  1-57 Et H Cl 3-Cl-Ph
1-58 Et H Cl 4-Cl-Ph  1-58 Et H Cl 4-Cl-Ph
1-59 Et H Cl 2,6-Me2-Ph 1-59 Et H Cl 2,6-Me 2 -Ph
Tabelle 2: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Y1 für eine Ethylenbrücke, Y2 für CH2, R2 für Methyl, Rcl für Hydroxy, W, Rc2 und Rc4 für Wasserstoff stehen, und Z Sauerstoff bedeutet. Table 2: Compounds of the invention of the general formula (I) wherein Q is Q 2 , Y 1 is an ethylene bridge, Y 2 is CH 2 , R 2 is methyl, R cl is hydroxy, W, R c2 and R c4 are hydrogen , and Z means oxygen.
Tabelle 3: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1, Y für eine CO-Gruppe, Rcl für Hydroxy, R2, Rc2, Rc3, R^ und Rc5 für Methyl, W für Wasserstoff stehen, und Z Sauerstoff bedeutet. Table 3: Compounds of the general formula (I) according to the invention, in which Q is Q 1 , Y is a CO group, R cl is hydroxyl, R 2 , R c2 , R c3 , R c and R c5 are methyl, W is hydrogen stand, and Z means oxygen.
Nr. X R1 Physikalische Daten No. XR 1 Physical Data
OH-NMR, DMSO-de or CDC13 ,400 MHz)OH-NMR, DMSO-de or CDC1 3 , 400 MHz)
3-1 Me Ph 3-1 Me Ph
3-2 Me 2-Me-Ph (DMSO-d6): 7.60 (d,lH), 7.42 (d,lH), 7.37- 7.28 (m,3H), 7.24 (d,lH), 3.56 (s,3H), 2.60 (s,3H), 2.07 (s,3H), 1.35 (s,12H)  3-2 Me 2-Me-Ph (DMSO-d6): 7.60 (d, 1H), 7.42 (d, 1H), 7.37- 7.28 (m, 3H), 7.24 (d, 1H), 3.56 (s, 3H ), 2.60 (s, 3H), 2.07 (s, 3H), 1.35 (s, 12H)
3-3 Me 2-Me,4-F-Ph (DMSO-d6): 7.60 (d,lH), 7.43 (d,lH), 7.34- 7.24 (m,2H), 7.14 (m,lH), 3.56 (s,3H), 2.60 (s,3H), 2.07 (s,3H), 1.35 (s,12H)  3-3 Me 2-Me, 4-F-Ph (DMSO-d 6): 7.60 (d, 1H), 7.43 (d, 1H), 7.34- 7.24 (m, 2H), 7.14 (m, 1H), 3.56 (s, 3H), 2.60 (s, 3H), 2.07 (s, 3H), 1.35 (s, 12H)
3-4 Me 2-Et-Ph (DMSO-d6): 7.60 (d,lH), 7.43 (d,lH), 7.40- 7.28 (m,3H), 7.23 (d,lH), 3.56 (s,3H), 2.59 (s,3H), 2.39 (q,2H), 1.35 (s,12H), 1.08 (t,3H) 3-4 Me 2-Et-Ph (DMSO-d6): 7.60 (d, 1H), 7.43 (d, 1H), 7.40- 7.28 (m, 3H), 7.23 (d, 1H), 3.56 (s, 3H ), 2.59 (s, 3H), 2.39 (q, 2H), 1.35 (s, 12H), 1.08 (t, 3H)
3-5 Me 2-CF3-Ph 3-5 Me 2-CF 3 -Ph
3-6 Me 2-CN-Ph  3-6 Me 2-CN-Ph
3-7 Me 2-MeO-Ph  3-7 Me 2 MeO Ph
3-8 Me 3-MeO-Ph  3-8 Me 3-MeO-Ph
3-9 Me 4-MeO-Ph  3-9 Me 4 MeO Ph
3-10 Me 2-F-Ph  3-10 Me 2-F-Ph
3-11 Me 3-F-Ph  3-11 Me 3-F-Ph
3-12 Me 4-F-Ph  3-12 Me 4-F-Ph
3-13 Me 2-Cl-Ph  3-13 Me 2 Cl-Ph
3-14 Me 3-Cl-Ph  3-14 Me 3-Cl-Ph
3-15 Me 4-Cl-Ph  3-15 Me 4-Cl-Ph
3-16 Me 2,6-Me2-Ph 3-16 Me 2,6 Me 2 Ph
3-17 Cl Me  3-17 Cl Me
3-18 Cl C2H4OMe 3-18 Cl C 2 H 4 OMe
3-19 Cl CH2-Ph 3-19 Cl CH 2 -Ph
3-20 Cl Ph  3-20 Cl Ph
3-21 Cl 2-Me-Ph  3-21 Cl 2-Me-Ph
3-22 Cl 2-CF3-Ph 3-22 Cl 2-CF 3 -Ph
3-23 Cl 2-CN-Ph  3-23 Cl 2-CN-Ph
3-24 Cl 2-MeO-Ph  3-24 Cl 2-MeO-Ph
3-25 Cl 3-MeO-Ph  3-25 Cl 3-MeO-Ph
3-26 Cl 4-MeO-Ph Nr. X R1 Physikalische Daten 3-26 Cl 4-MeO-Ph No. XR 1 Physical Data
OH-NMR, DMSO-de or CDC13 ,400 MHz)OH-NMR, DMSO-de or CDC1 3 , 400 MHz)
3-27 Cl 2-F-Ph 3-27 Cl 2-F-Ph
3-28 Cl 3-F-Ph  3-28 Cl 3-F-Ph
3-29 Cl 4-F-Ph  3-29 Cl 4-F-Ph
3-30 Cl 2-Cl-Ph  3-30 Cl 2 Cl-Ph
3-31 Cl 3-Cl-Ph  3-31 Cl 3-Cl-Ph
3-32 Cl 4-Cl-Ph  3-32 Cl 4-Cl-Ph
3-33 Cl 2,6-Me2-Ph 3-33 Cl 2,6-Me 2 -Ph
Tabelle 4: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q , R für Methyl, Rnl für Cyclopro l, W und Rn2 für Wasserstoff stehen, und Z Sauerstoff bedeutet. Table 4: Compounds of the invention of the general formula (I) wherein Q is Q, R is methyl, R nl is cyclopro l, W and R n2 are hydrogen, and Z is oxygen.
Nr. X R1 Physikalische Daten No. XR 1 Physical Data
('H-NMR, DMSO-de or CDC13 ,400 MHz)('H-NMR, DMSO-de or CDC1 3 , 400 MHz)
4-19 Cl 2-Me-Ph 4-19 Cl 2-Me-Ph
4-20 Cl 2-CF3-Ph 4-20 Cl 2-CF 3 -Ph
4-21 Cl 2-CN-Ph  4-21 Cl 2-CN-Ph
4-22 Cl 2-MeO-Ph  4-22 Cl 2-MeO-Ph
4-23 Cl 3-MeO-Ph  4-23 Cl 3-MeO-Ph
4-24 Cl 4-MeO-Ph  4-24 Cl 4-MeO-Ph
4-25 Cl 2-F-Ph  4-25 Cl 2-F-Ph
4-26 Cl 3-F-Ph  4-26 Cl 3-F-Ph
4-27 Cl 4-F-Ph  4-27 Cl 4-F-Ph
4-28 Cl 2-Cl-Ph  4-28 Cl 2 Cl-Ph
4-29 Cl 3-Cl-Ph  4-29 Cl 3-Cl-Ph
4-30 Cl 4-Cl-Ph  4-30 Cl 4-Cl-Ph
4-31 Cl 2,6-Me2-Ph 4-31 Cl 2,6-Me 2 -Ph
Tabelle 5: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q5, R2 für Methyl, Rnl für Cyclopropyl, W für Wasserstoff stehen, und Z Sauerstoff bedeutet. Table 5: Compounds of the invention of the general formula (I) in which Q is Q 5 , R 2 is methyl, R nl is cyclopropyl, W is hydrogen, and Z is oxygen.
Nr. X R1 Physikalische Daten No. XR 1 Physical Data
OH-NMP, DMSO-de or CDC13 ,400 MHz)OH-NMP, DMSO-de or CDC1 3 , 400 MHz)
5-13 Me 4-Cl-Ph 5-13 Me 4-Cl-Ph
5-14 Me 2,6-Me2-Ph 5-14 Me 2,6-Me 2 -Ph
5-15 Cl Me  5-15 Cl Me
5-16 Cl C2H4OMe 5-16 Cl C 2 H 4 OMe
5-17 Cl CH2-Ph 5-17 Cl CH 2 -Ph
5-18 Cl Ph  5-18 Cl Ph
5-19 Cl 2-Me-Ph  5-19 Cl 2-Me-Ph
5-20 Cl 2-CF3-Ph 5-20 Cl 2-CF 3 Ph
5-21 Cl 2-CN-Ph  5-21 Cl 2-CN-Ph
5-22 Cl 2-MeO-Ph  5-22 Cl 2-MeO-Ph
5-23 Cl 3-MeO-Ph  5-23 Cl 3-MeO-Ph
5-24 Cl 4-MeO-Ph  5-24 Cl 4-MeO-Ph
5-25 Cl 2-F-Ph  5-25 Cl 2-F-Ph
5-26 Cl 3-F-Ph  5-26 Cl 3-F-Ph
5-27 Cl 4-F-Ph  5-27 Cl 4-F-Ph
5-28 Cl 2-Cl-Ph  5-28 Cl 2 Cl-Ph
5-29 Cl 3-Cl-Ph  5-29 Cl 3-Cl-Ph
5-30 Cl 4-Cl-Ph  5-30 Cl 4-Cl-Ph
5-31 Cl 2,6-Me2-Ph 5-31 Cl 2,6-Me 2 -Ph
Formulierungsbeispiele formulation Examples
Ein Stäubemittel wird erhalten, indem man 10 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew. -Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.  A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 A wettable powder readily dispersible in water is obtained by adding 25
Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 Gew. -Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gew. -Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.  Parts by weight of a compound of formula (I) and / or salts thereof, 64 parts by weight kaolinhaltigen quartz as inert material, 10 parts by weight lignosulfonate potassium and 1 part by weight oleoylmethyltaurinsaures sodium as wetting and dispersing and grinding in a pin mill.
Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew. -Teilen A dispersion concentrate readily dispersible in water is obtained by adding 20 parts by weight of a compound of the formula (I) and / or its salts with 6 parts by weight
Alkylphenolpolyglyko lether (®Triton X 207), 3 Gew. -Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew. -Teilen paraffinischem Mineralöl (Siedebereich z.B. ca. 255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew. -Teilen einer Verbindung der Formel (I) und/oder deren Salze, 75 Gew. -Teilen Cyclohexanon als Lösungsmittel und 10 Gew. -Teilen oxethyliertes Nonylphenol als Emulgator. e) Ein in Wasser dispergierbares Granulat wird erhalten indem man Alkylphenolpolyglyko lether (®Triton X 207), 3 parts by weight Isotridecanolpolyglykolether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) mixed and in a ball mill to a fineness of less than 5 microns married. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier. e) A water-dispersible granules are obtained by
75 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze,  75 parts by weight of a compound of the formula (I) and / or salts thereof,
10 Gew. -Teile ligninsulfonsaures Calcium,  10 parts by weight of lignosulfonic acid calcium,
5 Gew. -Teile Natriumlaurylsulfat,  5 parts by weight of sodium lauryl sulfate,
3 Gew. -Teile Polyvinylalkohol und  3 parts by weight of polyvinyl alcohol and
7 Gew. -Teile Kaolin  7 parts by weight kaolin
mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert. f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man  milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit. f) A water-dispersible granules are also obtained by
25 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze,  25 parts by weight of a compound of the formula (I) and / or salts thereof,
5 Gew. -Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium  5 parts by wt. 2,2'-dinaphthylmethane-6,6'-disulfonate sodium
2 Gew. -Teile oleoylmethyltaurinsaures Natrium,  2 parts by weight oleoylmethyltaurine acid sodium,
1 Gew. -Teil Polyvinylalkohol,  1 part by weight of polyvinyl alcohol,
17 Gew. -Teile Calciumcarbonat und  17 parts by weight calcium carbonate and
50 Gew. -Teile Wasser  50 parts by weight of water
auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet.  Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.
C. Biologische Beispiele C. Biological examples
1. Herbizide Wirkung gegen Schadpflanzen im Vorauflauf  1. Herbicidal action against harmful plants in the pre-emergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in Holzfasertöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 1/ha unter Zusatz von 0,2% Netzmittel auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Die visuelle Bonitur der Schäden an den Versuchspflanzen erfolgt nach einer Versuchszeit von 3 Wochen im Vergleich zu unbehandelten Kontrollen (herbizide Wirkung in Prozent (%): 100%) Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Dabei zeigten beispielsweise die erfindungsgemäßenVerbindungen Nr. 1-2, 1-3, 1-4, 1-5, 1-8, 1-19, 2-2, 2-3, 2-4, 2-7, 3-2, 3-3, 3-4, 4-2 sowie 5-2 bei einer Aufwandmenge von 0,32 kg oder weniger pro Hektar eine mindestens 80%-ige Wirkung gegen Setaria viridis und Matricaria inodora. Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil. The compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied. After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100%) effect = plants have died, 0% effect = like control plants). Showed for example, the compounds of the present invention Nos. 1-2, 1-3, 1-4, 1-5, 1-8, 1-19, 2-2, 2-3, 2-4, 2-7, 3-2, 3 -3, 3-4, 4-2 and 5-2 at an application rate of 0.32 kg or less per hectare have an at least 80% action against Setaria viridis and Matricaria inodora.
Gleichzeitig lassen erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais oder Reis im Vorauflaufverfahren selbst bei hohen Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblättrige Kulturen wie Soja, Baumwolle, Raps, Zuckerrüben oder Kartoffeln. Die erfindungsgemäßen Verbindungen zeigen teilweise eine hohe Selektivität und eignen sich deshalb im Vorauflaufverfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen.  At the same time, compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice in the pre-emergence process practically undamaged even at high doses of active ingredient. In addition, some substances also protect dicotyledonous crops such as soya, cotton, rapeseed, sugar beet or potatoes. Some of the compounds according to the invention show a high selectivity and are therefore suitable in the pre-emergence process for controlling undesired plant growth in agricultural crops.
2. Herbizide Wirkung gegen Schadpflanzen im Nachauflauf 2. Herbicidal action against harmful plants in postemergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 1/ha unter Zusatz von 0,2% Netzmittel auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert (herbizide Wirkung in Prozent (%>): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Dabei zeigten beispielsweise die  Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. The compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green parts of plants as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with addition of 0.2% wetting agent , After about 3 weeks life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is scored visually in comparison to untreated controls (herbicidal action in percent (%)): 100% action = plants are dead, 0% effect = like control plants) , Here, for example, showed the
erfindungsgemäßenVerbindungen Nr. 1-2, 1-3, 1-4, 1-5, 1-8, 1-19, 2-2, 2-3, 2-4, 2-7, 3-2, 3-3, 3-4, 4-2 sowie 5-2 bei einer Aufwandmenge von 0,08 kg oder weniger pro Hektar eine mindestens 80%>-ige Wirkung gegen Abuthilon theophrasti und Amaranthus retroflexus. Gleichzeitig lassen Compounds of the invention Nos. 1-2, 1-3, 1-4, 1-5, 1-8, 1-19, 2-2, 2-3, 2-4, 2-7, 3-2, 3-3 , 3-4, 4-2 and 5-2 at an application rate of 0.08 kg or less per hectare at least 80% against Abuthilon theophrasti and Amaranthus retroflexus. At the same time let
erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais oder Reis im Nachauflaufverfahren selbst bei hohen Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblättrige Kulturen wie Soja, Baumwolle, Raps, Zuckerrüben oder Kartoffeln. Die erfindungsgemäßen Verbindungen zeigen teilweise eine hohe Selektivität und eignen sich deshalb im Nachauflaufverfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen. Compounds According to the Invention Gramineous crops such as barley, wheat, rye, millet, maize or rice, post-emergence even with high doses of active ingredient virtually undamaged. In addition, some substances also protect dicotyledonous crops such as soya, cotton, rapeseed, sugar beet or potatoes. Some of the compounds according to the invention show a high selectivity and are therefore suitable postemergence for combating undesired plant growth in agricultural crops.

Claims

Patentansprüche claims
1. Chinazolindion-6-carbonylderivate der Formel (I) und deren Salze 1. quinazolinedione-6-carbonyl derivatives of the formula (I) and salts thereof
worin wherein
X bedeutet Nitro, Halogen, Cyano, Formyl, Rhodano, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-Ce)- Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C3-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Halogencycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halogencycloalkyl-(Ci-C6)-alkyl, COR1, OR1, OCOR1, OSO2R2, S(0)nR2, SO2OR1, S02N(R1)2, NR1S02R2, NR'COR1, (Ci-C6)-Alkyl- S(0)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OS02R2, (Ci-C6)-Alkyl-COOR1, (Ci-C6)-Alkyl-S02OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-S02N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1S02R2 oder NR'R2, X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C6) alkyl, (Ci-C6) -haloalkyl, (C2 -Ce) - alkenyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) -haloalkynyl, (C 3 -C 6) -cycloalkyl, (C 3 - C 6) halocycloalkyl, (C 3 C 6) -cycloalkyl- (Ci-C 6) alkyl, (C3-C 6) -Halogencycloalkyl- (Ci-C 6) alkyl, COR 1, OR 1, OCOR 1, OSO2R 2, S (0) n R 2, SO2OR 1, S0 2 N ( R 1 ) 2 , NR 1 S0 2 R 2 , NR'COR 1 , (C 1 -C 6 ) -alkyl, S (0) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 4 ) 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-COOR 1 , (C 1 -C 6 ) -alkyl-S0 2 OR 1 , (Ci -C 6) alkyl-CON (R 1) 2, (Ci-C 6) alkyl-S0 2 N (R 1) 2, (Ci-C 6) alkyl-NR 1 COR 1, (Ci-C 6 ) -alkyl-NR 1 S0 2 R 2 or NR'R 2 ,
Z bedeutet O oder S, bedeutet Wasserstoff, Nitro, Halogen, Cyano, (Ci-C i)-Alkyl, (Ci-C4)-Halogenalkyl oder (C1-C4)-Z is O or S, is hydrogen, nitro, halogen, cyano, (C 1 -C 12) -alkyl, (C 1 -C 4) -haloalkyl or (C 1 -C 4) -
Alkoxy, alkoxy,
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen- (C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen-(C3-Cio)-cycloalkyl, (C1-C4)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (C3-C12)- Cycloalkenyl, Halogen-(C3-Ci2)-cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)- alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkoxy-(C3-C7)-cycloalkyl, Di-(Ci-C6)-alkoxy-(C3- C7)-cycloalkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfmyl- (Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci-C6)-alkyl, Di-(Ci-C6)- alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylamino-(Ci- Ce)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)-alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci- Ce)-Alkoxy-carbonyl, (C3-C7)-Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci- C6)-Alkylamino-carbonyl, Di-(C i-C6)-alkylamino-carbonyl, (C3-C7)-Cycloalkylamino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-(Ci- Ce)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-Cv)-Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-Cv)- cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl- carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-Cv)-cycloalkoxy, (C3-Cv)-Cycloalkyl-(Ci- Ce)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3- Cio)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl- carbonyloxy, (C3-Cv)-Cycloalkyl-carbonyloxy, (Ci-C6)-Alkyl-carbonyl-(Ci-C6)-alkoxy, (Ci-Ce)- Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3- Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen-(Ci-C6)-alkyl-carbonylamino, (C1-C10)- Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Hydroxy, Amino, NHCHO, oder R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, Halogeno (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl- (C 3 -C 7 ) -cycloalkyl, ( C3-C7) -cycloalkyl- (Ci-C 6) alkyl, (C3-C7) cycloalkyl (C3-C7) cycloalkyl, halo (C3-C7) cycloalkyl- (Ci-C6 ) alkyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl- (Ci-C6) alkyl, (C3-C 12) - cycloalkenyl, halo (C 3 -C 2) -cycloalkenyl , (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) alkoxy (C 2 -C 6) - alkenyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) alkoxy (C 3 -C 7) cycloalkyl, di- (Ci-C 6) alkoxy (C 3 - C 7) cycloalkyl, (C 3 -C 7) cycloalkoxy (Ci-C 6) alkyl, (C 3 -C 7) cycloalkoxy (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) - Alkoxy- (Ci-C6) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkylthio (Ci-C 6 ) -alkyl, (Ci-C 6 ) -alkylsulfmyl- (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C6) alkylamino (Ci-C 6) alkyl, di (Ci-C 6) - alkyl amino- (C 1 -C 6) -alkyl, halogeno (C 1 -C 6 ) -alkylamino (C 1 -C 6) -alkyl, (C 3 -C 7 ) -cycloalkylamino (C 1 -C 4) -alkyl, (C 1 -C 6) Alkyl-carbonyl, halo (C 1 -C 6 ) -alkyl-carbonyl, (C 3 -C 7 ) -cycloalkyl-carbonyl, (ci-Ce) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, ( C 3 -C 7 -cycloalkyl- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylamino-carbonyl, di- (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkylamino carbonyl, cyano (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy- (Ci - Ce) -alkyl, (Ci-C6) -alkoxy-halogen- (Ci-C6) -alkyl, halogen- (Ci-C6) -alkoxy-halo- (Ci-C6) -alkyl, halogen- (C3-C7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 4) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 4) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, di- ( C 1 -C 6 -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkoxycarbonyl- C 6) -alkyl, halogeno (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 10) -alkoxy, halogeno (C 1 -C 10) -alkoxy, (C 3 -C 12) -cycloalkoxy, halogeno (C 3 -C 4) -cycloalkoxy, (C 3 -C 4) -cycloalkyl- (ci-Ce) -alkoxy, (C 2 -C 12) -alkenyloxy, halogeno (C 2 -C 10) -alkenyloxy, (C 2 -C 10) -alkynyloxy, halogeno (C 3 -C 10) -alkyloxy, Cio) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkylcarbonyloxy, halogeno (C 2 -C 12) -alkylcarbonyloxy, (C 3 -C 4) -cycloalkyl -carbonyloxy, (C 1 -C 6) -alkylcarbonyl- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halogen -di- (C 1 -C 6) -alkylamino, (C 3 -C 12) -C ycloalkylamino, (C 1 -C 6) -alkylcarbonylamino, halogeno (C 1 -C 6) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkyl-amino, hydroxy, amino, NHCHO, or
R1 bedeutet Phenyl, Phenylsulfonyl, W^Phenyl), W^O-Phenyl), W^S-Phenyl), W1-(S02-Phenyl), W2-(S02CH2-Phenyl) oder W2-(SCH2-Phenyl), wobei die Phenylringe der acht vorstehend genannten Reste jeweils s Substituenten R3 tragen, R 1 is phenyl, phenylsulfonyl, W ^ phenyl), W ^ O-phenyl), W ^ S-phenyl), W 1 - (S0 2 -phenyl), W 2 - (SO 2 CH 2 -phenyl) or W 2 - (SCH 2 Phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 3 ,
R2 bedeutet Wasserstoff, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)- Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Halogencycloalkyl, (Ci-C6)-Alkyl-0-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl- (Ci-C6)-alkyl, Pyridyl oder (Ci-C6)-Alkylpyridyl, wobei die Phenyl- oder Pyridylringe der vier vorstehend genannten Reste jeweils s Substituenten R3 tragen, R 2 is hydrogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - halocycloalkyl, (Ci-C6) alkyl-0- (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, phenyl, phenyl (Ci-C6) alkyl, pyridyl, or (Ci-C6) alkylpyridyl, wherein the phenyl or pyridyl rings of four radicals mentioned above each bear s substituents R 3 ,
Q bedeutet einen Rest Q1, Q2, Q3, Q4 oder Q5, Q is a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
Q1 Q2 Q3 Q4 Q5 Q 1 Q 2 Q 3 Q 4 Q 5
Rcl bedeutet Hydroxy oder SR4, Rc2, Rc3, R^, Rc5, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci-C4)-Alkyl, Rpl bedeutet Wasserstoff, (Ci-C6)-Alkylsulfonyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkylsulfonyl, oder jeweils durch n gleiche oder verschiedene Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)-Alkyl und (Ci- C4)-Alkoxy substituiertes Phenylsulfonyl, Thiophenyl-2-sulfonyl, Benzoyl, Benzoyl-(Ci-C6)-alkyl oder Benzyl, R cl is hydroxy or SR 4 , R c2 , R c3 , R ^, R c5 , R c6 and R c7 are each independently hydrogen or (Ci-C 4 ) alkyl, R pl is hydrogen, (C 1 -C 6) -alkylsulfonyl, (C 1 -C 4) -alkoxy- (C 1 -C 6) -alkylsulfonyl, or in each case by n identical or different radicals from the group consisting of halogen, (C 1 -C 4) - Alkyl and (C 1 -C 4) -alkoxy-substituted phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl- (C 1 -C 6) -alkyl or benzyl,
Rp2 bedeutet (Ci-C4)-Alkyl, R p2 is (C 1 -C 4 ) -alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C4)-Alkyl-(C3-C8)-cycloalkyl oder (C3-C6)-Halogencycloalkyl, R p3 is hydrogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4 ) -alkyl (C 3 -C 8 ) -cycloalkyl or (C 3 -C 6 ) -halocycloalkyl .
Rnl bedeutet (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C4)-Alkyl-(C3-C8)-cycloalkyl oder (C3-C6)- Halogencycloalkyl, R nl represents (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (Ci-C4) alkyl- (C3-C8) cycloalkyl or (C 3 -C 6) - halocycloalkyl,
Rn2 bedeutet Wasserstoff, C02(Ci-C6)-Alkyl oder S(0)n(Ci-C6)-Alkyl, R n2 is hydrogen, C0 2 (C 1 -C 6 ) -alkyl or S (0) n (C 1 -C 6 ) -alkyl,
Y bedeutet O oder CO, Y1 bedeutet eine Ethylen- oder Vinylengruppe, Y2 bedeutet O, CO oder CH2 Y is O or CO, Y 1 is an ethylene or vinylene group, Y 2 is O, CO or CH 2
W1 bedeutet (Ci-Cio)-Alkylen, (C2-C6)-Alkenylen oder (C2-C6)-Alkinylen, W2 bedeutet (Ci-Cio)-Alkylen, W 1 is (C 1 -C 10) -alkylene, (C 2 -C 6 ) -alkenylene or (C 2 -C 6 ) -alkynylene, W 2 is (C 1 -C 10) -alkylene,
R3 bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -C(=0)R3a, -C(=0)OR3a, R 3 is halogen, cyano, hydroxy, amino, nitro, -C (= O) R 3a , -C (= O) OR 3a ,
-C(=0)(NR3a)2, -C(=S)NH2, -C(=0)NHCN, -C(=0)NHOH, -SH, -S02(NR3a)2, -S02NHCN, -S02NHOH,-C (= O) (NR 3a ) 2 , -C (= S) NH 2 , -C (= O) NHCN, -C (= O) NHOH, -SH, -SO 2 (NR 3a ) 2 , - S0 2 NHCN, -S0 2 NHOH,
-OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Halogen-(Ci-C6)-alkyl, Halogen- (C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)- cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C8)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C8)- Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy, Halogen- (Ci-C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C6)- alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-Ce)- Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)-Cycloalkylthio, (Ci-C6)- Alkylsulfinyl, Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-C8)-alkylamino oder (C3-C8)-Cycloalkylamino, oder -OCN, -SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (Ci-C 6) alkyl, Halogeno (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkynyl, (C 3 -C 8 ) cycloalkyl, halo (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) - alkyl- (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkenyl, halogen- (C 3 -) C 8) - cycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 3 -C 7) cycloalkoxy (Ci-C 6) alkyl, (Ci-C 6) - Alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkylsulfmyl- (C 1 -C 4) -alkyl; C 6 ) -alkyl, (C 1 -C 8 ) -alkoxy-halo (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) Alkoxy, halo (C 1 -C 6 ) alkoxy, (C 3 -C 8 ) cycloalkoxy, halo (C 3 -C 8 ) cycloalkoxy, (C 3 -C 8 ) cycloalkyl (Ci-C 6) - alkoxy, (C 2 -C 6) alkenyloxy, halo (C 2 -C 6) alkenyloxy, (Ci-C6) alkoxy (Ci-C6) alkoxy, (C2 -Ce) - alkylcarbonyloxy, (Ci-C 6) alkylthio, halo (Ci-C 6) -alkylthio, (C 3 -C 8) -cycloalkylthio, (Ci-C 6) - Alkylsulfinyl, halo (C 1 -C 6) -alkylsulfinyl, (C 1 -C 6) -alkylsulfonyl, halo (C 1 -C 6) -alkylsulfonyl, (C 3 -C 8) -cycloalkylsulfonyl, (C 1 -C 6) -alkylamino, di (Ci -C 6) -alkylamino, halogeno (Ci-C6) -alkylamino, halo-di- (Ci-C8) -alkylamino or (C3-C8) -cycloalkylamino, or
zwei vicinale Reste R3 bilden zusammen mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen 5- bis 7-gliedrigen Ring, der v Kohlenstoffatome und p gleiche oder verschiedene Atome aus der Gruppe Sauerstoff, Schwefel oder Stickstoff enthält, und t Oxogruppen trägt, two vicinal radicals R 3 together with the two carbon atoms to which they are attached form a 5- to 7-membered ring containing v carbon atoms and p identical or different atoms from the group oxygen, sulfur or nitrogen, and t carries oxo groups .
R3a bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3a is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R4 bedeutet (Ci-C i)-Alkyl oder durch p Reste aus der Gruppe Halogen, Nitro, Cyano, (C1-C4)- Alkyl, (Ci-C4)-Halogenalkyl, (Ci-C4)-Alkoxy und (Ci-C4)-Halogenalkoxy substituiertes Phenyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1, 2, 3 oder 4, s bedeutet 0, 1, 2, 3, 4 oder 5, t bedeutet 0, 1, 2, 3 oder 4, v bedeutet 2, 3, 4, 5, 6 oder 7. R 4 is (Ci-C i) -alkyl or by p radicals from the group halogen, nitro, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy and (Ci C4) haloalkoxy-substituted phenyl, n is 0, 1 or 2, p is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is 0, 1, 2, 3 or 4, v means 2, 3, 4, 5, 6 or 7.
2. Chinazolindion-6-carbonylderivate nach Anspruch 1, worin 2. quinazolinedione-6-carbonyl derivatives according to claim 1, wherein
X bedeutet Halogen, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halogencycloalkyl, OR1, S(0)nR2, S02N(R1)2, NR^C R2, NR'COR1, (Ci-C6)-Alkyl-S(0)nR2 oder (Ci-C6)-Alkyl-OR1 X is halogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - Halocycloalkyl, OR 1 , S (O) n R 2 , SO 2 N (R 1 ) 2 , NR 1 , CR 2 , NR'COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 or ( C 1 -C 6 ) -alkyl-OR 1
Z bedeutet O, Z means O,
W bedeutet Wasserstoff, Cl, MeO, Methyl oder Ethyl, R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen- (C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen-(C3-Cio)-cycloalkyl, (C1-C4)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)- Alkylsulfonyl-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (Ci-C6)- alkoxy-(Ci-Ce)-alkoxy, (Ci-C6)-Alkylamino oder Di-(Ci-C6)-alkylamino , R1 bedeutet Phenyl, das s Substituenten R1 trägt, W is hydrogen, Cl, MeO, methyl or ethyl, R 1 is (Ci-Cio) alkyl, (C 2 -Cio) alkenyl, (C 2 -Cio) alkynyl, halogeno (Ci-Cio) alkyl , Halo (C 2 -C 10) alkenyl, halo (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4) -alkyl - (C 3 -C 7) cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C -C 6 ) - Alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C6) -Alkylsulfmyl- (Ci-C 6) alkyl, (Ci- C 6) - alkylsulfonyl (Ci-C 6) alkyl, cyano (Ci-C 6) alkyl, (Ci-Cio) alkoxy, halo (Ci-Cio) alkoxy, (Ci-C 6) alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkylamino or di- (C 1 -C 6) -alkylamino, R 1 denotes phenyl which carries s substituent R 1 ,
R2 bedeutet (Ci-C4)-Alkyl, R 2 is (C 1 -C 4 ) -alkyl,
Q bedeutet einen Rest Q1, Q2, Q3, Q4 oder Q5, Q is a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
Q1 Q2 Q3 Q4 Q5 Q 1 Q 2 Q 3 Q 4 Q 5
Rcl bedeutet Hydroxy, Rc2, Rc3, R^, Rc5, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, R cl is hydroxy, R c2 , R c3 , R ^, R c5 , R c6 and R c7 are each independently hydrogen or methyl,
Rpl bedeutet Wasserstoff, R pl is hydrogen,
Rp2 bedeutet (Ci-C4)-Alkyl, R p2 is (C 1 -C 4 ) -alkyl,
Rp3 bedeutet Wasserstoff, (G-C4)-Alkyl oder Cyclopropyl, R p3 is hydrogen, (GC 4 ) -alkyl or cyclopropyl,
Rnl bedeutet Cyclopropyl, Rn2 bedeutet Wasserstoff, R nl is cyclopropyl, R n2 is hydrogen,
Y bedeutet O oder CO, Y is O or CO,
Y1 bedeutet eine Ethylen- oder Vinylengruppe, Y 1 represents an ethylene or vinylene group,
Y2 bedeutet CH2, R bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -C(=0)R3a,C(=0)OR3a, Y 2 is CH 2 , R is halogen, cyano, hydroxy, amino, nitro, -C (= O) R 3a , C (= O) OR 3a ,
-C(=0)(NR3a)2, -C(=S)NH2, -C(=0)NHCN, -C(=0)NHOH, -SH, -S02NH2, -S02NHCN, -C (= O) (NR 3a ) 2 , -C (= S) NH 2 , -C (= O) NHCN, -C (= O) NHOH, -SH, -SO 2 NH 2 , -SO 2 NHCN .
-S02NHOH, -OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, -S0 2 NHOH, -OCN, -SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl,
Halogen-(Ci-C6)-alkyl, Halogen-(C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-Cg)-Cycloalkyl,Halogeno (C 1 -C 6) -alkyl, halogeno (C 2 -C 6) -alkenyl, halogeno (C 2 -C 6) -alkynyl, (C 3 -C 9) -cycloalkyl,
Halogen-(C3-C8)-cycloalkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (C3- Cg)-Cycloalkenyl, Halogen-(C3-Cg)-cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkoxy- (Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C8)- Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C8)-Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci- C6)-alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)- cycloalkoxy, (C3-Cg)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-C6)-Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)- alkylthio, (C3-C8)-Cycloalkylthio, (Ci-C6)-Alkylsulfmyl, Halogen-(Ci-C6)-alkylsulfmyl, (Ci-C6)- Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci- C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-C8)-alkylamino, (C3-C8)-Cycloalkylamino oder Methylendioxo, Halo (C 3 -C 8) cycloalkyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C 6) alkyl, (C 3 - Cg) cycloalkenyl, halo (C3-Cg) cycloalkenyl, (Ci-C6) alkoxy (Ci-C6) alkyl, (C3-C7) cycloalkoxy (Ci-C 6) alkyl , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 8) ) - alkylsulfmyl (Ci-C 6 ) -alkyl, (Ci-C8) -alkoxy-halo (Ci-C 6 ) -alkyl, cyano (Ci-C 6 ) -alkyl, hydroxy (Ci- C 6 ) alkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, (C 3 -C 8) cycloalkoxy, halo (C 3 -C 8) - cycloalkoxy, (C3-Cg ) -Cycloalkyl- (C 1 -C 6) -alkoxy, (C 2 -C 6) -alkenyloxy, halogeno (C 2 -C 6) -alkenyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 2 -C 6) alkylcarbonyloxy, (Ci-C 6) alkylthio, halo (Ci-C 6) - alkylthio, (C 3 -C 8) -cycloalkylthio, (Ci-C 6) -Alkylsulfmyl, halogen (C 1 -C 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl, halogeno (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 8) -cycloalkylsulfonyl, (C 1 -C 6 ) -alkylamino, di- (C 1 -C 4) -alkylsulfonyl, C6) -alkylamino, halo (Ci-C6) -alkylamino, halo gen-di- (C 1 -C 8) -alkylamino, (C 3 -C 8) -cycloalkylamino or methylenedioxo,
R3a bedeutet Wasserstoff oder (Ci-C6)-Alkyl, n bedeutet 0, 1 oder 2, s bedeutet 0, 1, 2, 3, 4 oder 5. R 3a is hydrogen or (C 1 -C 6 ) -alkyl, n is 0, 1 or 2, s is 0, 1, 2, 3, 4 or 5.
3. Chinazolindion-6-carbonylderivate nach Anspruch 1 oder 2, worin 3. Quinazolinedione-6-carbonyl derivatives according to claim 1 or 2, wherein
X bedeutet F, Cl, Br, Methyl, Ethyl, Cyclopropyl, Trifluormethyl, Methoxy, Methoxymethyl, Methoxyethoxymethyl, SMe oder S02Me, X is F, Cl, Br, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy, methoxymethyl, methoxyethoxymethyl, SMe or SO 2 Me,
Z bedeutet O, Z means O,
W bedeutet Wasserstoff, W means hydrogen,
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen- (C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen-(C3-Cio)-cycloalkyl, (C1-C4)- Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, Halogeno (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl- (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) cycloalkyl
(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkylthio-(Ci- C6)-alkyl, (Ci-C6)-Alkylsulfmyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, oder R1 bedeutet Phenyl, das s Substituenten R3 trägt, (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl, (Ci-C 6 ) Alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfmyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, or R 1 is phenyl which carries s substituent R 3 ,
R2 bedeutet Methyl oder Ethyl, R 2 is methyl or ethyl,
Q bedeutet einen Rest Q1, Q2, Q3, Q4 oder Q5, Q is a radical Q 1 , Q 2 , Q 3 , Q 4 or Q 5 ,
Q1 Q2 Q3 Q4 Q5 Q1 Q 2 Q 3 Q 4 Q 5
Rcl bedeutet Hydroxy, R cl is hydroxy,
Rc2, Rc3, R04, Rc5, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl,R c2, R c3, R 04, R c5, R c6 and c7 R are each independently hydrogen or methyl,
Rpl bedeutet Wasserstoff, R pl is hydrogen,
Rp2 bedeutet (Ci-C4)-Alkyl, R p2 is (C 1 -C 4 ) -alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C4)-Alkyl oder Cyclopropyl, R p3 is hydrogen, (C 1 -C 4 ) -alkyl or cyclopropyl,
Rnl bedeutet Cyclopropyl, R nl is cyclopropyl,
Rn2 bedeutet Wasserstoff, R n2 is hydrogen,
Y bedeutet O oder CO,  Y is O or CO,
Y1 bedeutet eine Ethylen- oder Vinylengruppe, Y 1 represents an ethylene or vinylene group,
Y2 bedeutet CH2, Y 2 is CH 2 ,
R3 bedeutet Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy- (Ci-C6)-alkyl, (Ci-C6)-Alkylthio, (Ci-C6)-Alkylsulfmyl, (Ci-C6)-Alkylsulfonyl, Phenyl oder R 3 represents halogen, cyano, nitro, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C2-C6) alkynyl, Halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, (Ci-C 6) alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl, phenyl or
Methylendioxo, s bedeutet 0, 1 , 2, 3, 4 oder 5. Methylene dioxo, s means 0, 1, 2, 3, 4 or 5.
4. Herbizide Mittel gemäß einem der Ansprüche 1 bis 3 in Mischung mit Formulierungshilfsmitteln. 4. A herbicidal composition according to any one of claims 1 to 3 in admixture with formulation auxiliaries.
5. Herbizide Mittel nach Anspruch 4 enthaltend mindestens einen weiteren pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren. 5. A herbicidal composition according to claim 4 containing at least one further pesticidal active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
6. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach Anspruch 4 oder 5 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 6. A method for controlling undesirable plants, characterized in that an effective amount of at least one compound of formula (I) according to any one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 on the plants or on the site of undesired plant growth applied.
7. Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach Anspruch 4 oder 5 zur Bekämpfung unerwünschter Pflanzen. 7. Use of compounds of the formula (I) according to any one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 for controlling unwanted plants.
8. Verwendung nach Anspruch 7, dadurch gekennzeichnet, daß die Verbindungen der Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden. 8. Use according to claim 7, characterized in that the compounds of formula (I) are used for controlling undesirable plants in crops of crops.
9. Verwendung nach Anspruch 8, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind. 9. Use according to claim 8, characterized in that the crops are transgenic crops.
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Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018202544A1 (en) 2017-05-04 2018-11-08 Bayer Cropscience Aktiengesellschaft Herbicide safener compositions containing quinazolinedione-6-carbonyl derivatives
CN110357860B (en) * 2018-04-11 2020-12-15 山东先达农化股份有限公司 Quinazoline diketone compound and application thereof as well as pesticide herbicide
CN110669016B (en) * 2018-09-29 2021-05-25 山东先达农化股份有限公司 Triketone compound, preparation method and application thereof, and herbicide
CN110963973B (en) * 2018-09-29 2023-04-25 山东先达农化股份有限公司 Triketone compound containing quinazoline diketone fragment, preparation method and application thereof, and herbicide
CN111820231A (en) * 2019-04-16 2020-10-27 山东先达农化股份有限公司 Weeding composition, application thereof and herbicide
CN112574128B (en) * 2019-09-29 2022-08-09 山东先达农化股份有限公司 Quinazoline diketone compound, preparation method and application thereof, and herbicide
CN112608282B (en) * 2019-12-20 2022-07-26 山东先达农化股份有限公司 Compound containing quinazolinedione and N-O structure and preparation method and application thereof
CN113149913B (en) * 2020-01-07 2022-09-02 山东先达农化股份有限公司 alpha-C position modified benzyl substituted quinazoline diketone compound, preparation method and application thereof, and HPPD herbicide
CN113439750A (en) * 2020-03-27 2021-09-28 辽宁先达农业科学有限公司 Herbicide composition, application thereof and herbicide
CN114573516B (en) * 2020-11-30 2023-10-24 山东先达农化股份有限公司 Trione-quinazolinone compound, preparation method and application thereof, and herbicide
WO2024008191A1 (en) * 2022-07-08 2024-01-11 山东先达农化股份有限公司 Quinazolinedione-containing compound, method for preparing same, and use thereof

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0131624B1 (en) 1983-01-17 1992-09-16 Monsanto Company Plasmids for transforming plant cells
BR8404834A (en) 1983-09-26 1985-08-13 Agrigenetics Res Ass METHOD TO GENETICALLY MODIFY A PLANT CELL
BR8600161A (en) 1985-01-18 1986-09-23 Plant Genetic Systems Nv CHEMICAL GENE, HYBRID, INTERMEDIATE PLASMIDIO VECTORS, PROCESS TO CONTROL INSECTS IN AGRICULTURE OR HORTICULTURE, INSECTICIDE COMPOSITION, PROCESS TO TRANSFORM PLANT CELLS TO EXPRESS A PLANTINIDE TOXIN, PRODUCED BY CULTURES, UNITED BY BACILLA
ATE80182T1 (en) 1985-10-25 1992-09-15 Monsanto Co PLANT VECTORS.
EP0242236B2 (en) 1986-03-11 1996-08-21 Plant Genetic Systems N.V. Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
IL83348A (en) 1986-08-26 1995-12-08 Du Pont Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
ATE241007T1 (en) 1990-03-16 2003-06-15 Calgene Llc DNAS CODING FOR PLANT DESATURASES AND THEIR APPLICATIONS
EP0536293B1 (en) 1990-06-18 2002-01-30 Monsanto Technology LLC Increased starch content in plants
DK0536330T3 (en) 1990-06-25 2002-04-22 Monsanto Technology Llc Glyphosate tolerant plants
SE467358B (en) 1990-12-21 1992-07-06 Amylogene Hb GENETIC CHANGE OF POTATISE BEFORE EDUCATION OF AMYLOPECT TYPE STARCH
DE4104782B4 (en) 1991-02-13 2006-05-11 Bayer Cropscience Gmbh Novel plasmids containing DNA sequences that cause changes in carbohydrate concentration and carbohydrate composition in plants, as well as plants and plant cells containing these plasmids
EP0973764A1 (en) * 1997-02-14 2000-01-26 E.I. Du Pont De Nemours And Company Bicyclic hydrazone herbicides
KR20010085893A (en) * 1998-10-06 2001-09-07 도미나가 가즈토 Triketone derivative and herbicide
JP5300225B2 (en) 2007-08-03 2013-09-25 バイエル・クロップサイエンス・アーゲー Herbicide triazolyl pyridine ketones
CN104557739B (en) 2013-10-25 2016-11-09 山东先达农化股份有限公司 Triketone compound and preparation method and application thereof

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