WO2017140612A1 - Dérivés de quinazolindion-6-carbonyle et leur utilisation comme herbicides - Google Patents

Dérivés de quinazolindion-6-carbonyle et leur utilisation comme herbicides Download PDF

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Publication number
WO2017140612A1
WO2017140612A1 PCT/EP2017/053121 EP2017053121W WO2017140612A1 WO 2017140612 A1 WO2017140612 A1 WO 2017140612A1 EP 2017053121 W EP2017053121 W EP 2017053121W WO 2017140612 A1 WO2017140612 A1 WO 2017140612A1
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Prior art keywords
alkyl
alkoxy
cycloalkyl
halo
halogeno
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German (de)
English (en)
Inventor
Ralf Braun
Christian Waldraff
Anu Bheemaiah MACHETTIRA
Hansjörg Dietrich
Elmar Gatzweiler
Christopher Hugh Rosinger
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Bayer CropScience AG
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Bayer CropScience AG
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Priority to EP17703778.5A priority Critical patent/EP3416961A1/fr
Priority to MX2018010025A priority patent/MX2018010025A/es
Priority to CA3014687A priority patent/CA3014687A1/fr
Priority to CN201780011406.1A priority patent/CN108699042A/zh
Priority to BR112018016864A priority patent/BR112018016864A2/pt
Priority to JP2018543343A priority patent/JP2019507145A/ja
Priority to AU2017219708A priority patent/AU2017219708A1/en
Publication of WO2017140612A1 publication Critical patent/WO2017140612A1/fr
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    • 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.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des dérivés de quinazolindion-6-carbonyle de la formule générale (I) et leur utilisation comme herbicides. (I), dans la formule (I), R1, R2, X et W représentent des groupes tels que hydrogène, alkyle et halogène. Z représentant un chalcogène. Q représentant un hétérocycle à cinq chaînons.
PCT/EP2017/053121 2016-02-18 2017-02-13 Dérivés de quinazolindion-6-carbonyle et leur utilisation comme herbicides Ceased WO2017140612A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP17703778.5A EP3416961A1 (fr) 2016-02-18 2017-02-13 Dérivés de quinazolindion-6-carbonyle et leur utilisation comme herbicides
MX2018010025A MX2018010025A (es) 2016-02-18 2017-02-13 Derivados de quinazolindion-6-carbonilo y su utilizacion como herbicidas.
CA3014687A CA3014687A1 (fr) 2016-02-18 2017-02-13 Derives de quinazolindion-6-carbonyle et leur utilisation comme herbicides
CN201780011406.1A CN108699042A (zh) 2016-02-18 2017-02-13 喹唑啉二酮-6-羰基衍生物及其作为除草剂的用途
BR112018016864A BR112018016864A2 (pt) 2016-02-18 2017-02-13 derivados de quinazolinodiona-6-carbonil e seu uso como herbicidas
JP2018543343A JP2019507145A (ja) 2016-02-18 2017-02-13 キナゾリンジオン−６−カルボニル誘導体及び除草剤としてのそれらの使用
AU2017219708A AU2017219708A1 (en) 2016-02-18 2017-02-13 Quinazolinedione-6-carbonyl derivatives and their use as herbicides

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EP16156346.5 2016-02-18

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WO2018202544A1 (fr) 2017-05-04 2018-11-08 Bayer Cropscience Aktiengesellschaft Compositions de phytoprotection contenant des dérivés de quinazolindion-6-carbonyle
WO2019196908A1 (fr) * 2018-04-11 2019-10-17 山东先达农化股份有限公司 Composé de pyrazole quinazolinedione, ses applications et pesticide/herbicide associé
CN110669016A (zh) * 2018-09-29 2020-01-10 山东先达农化股份有限公司 三酮类化合物及其制备方法和应用以及一种除草剂
CN110963973A (zh) * 2018-09-29 2020-04-07 山东先达农化股份有限公司 含喹唑啉二酮片段的三酮类化合物及其制备方法和应用以及一种除草剂
CN112574128A (zh) * 2019-09-29 2021-03-30 山东先达农化股份有限公司 喹唑啉二酮类化合物及其制备方法和应用以及一种除草剂

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JP2021517592A (ja) * 2018-04-11 2021-07-26 山▲東▼先▲達▼▲農▼▲化▼股▲ふん▼有限公司Ｓｈａｎｄｏｎｇ Ｃｙｎｄａ Ｃｈｅｍｉｃａｌ Ｃｏ．，Ｌｔｄ． キナゾリンジオン系化合物、その使用および農薬除草剤
WO2019196908A1 (fr) * 2018-04-11 2019-10-17 山东先达农化股份有限公司 Composé de pyrazole quinazolinedione, ses applications et pesticide/herbicide associé
WO2019196904A1 (fr) * 2018-04-11 2019-10-17 山东先达农化股份有限公司 Composé de quinazolinedione, ses applications et pesticide/herbicide associé
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CN112574128A (zh) * 2019-09-29 2021-03-30 山东先达农化股份有限公司 喹唑啉二酮类化合物及其制备方法和应用以及一种除草剂
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MX2018010025A (es) 2018-12-17
AU2017219708A1 (en) 2018-08-23
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BR112018016864A2 (pt) 2019-02-05
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