EP2892344A1 - Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes - Google Patents

Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Info

Publication number
EP2892344A1
EP2892344A1 EP13756160.1A EP13756160A EP2892344A1 EP 2892344 A1 EP2892344 A1 EP 2892344A1 EP 13756160 A EP13756160 A EP 13756160A EP 2892344 A1 EP2892344 A1 EP 2892344A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
heterocyclyl
aryl
alkoxy
amino
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Withdrawn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
EP13756160.1A
Other languages
German (de)
English (en)
Inventor
Jens Frackenpohl
Ines Heinemann
Thomas Müller
Guido Bojack
Jan Dittgen
Pascal VON KOSKULL-DÖRING
Dirk Schmutzler
Martin Jeffrey Hills
Juan Pedro RUIZ-SANTAELLA MORENO
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
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP13756160.1A priority Critical patent/EP2892344A1/fr
Publication of EP2892344A1 publication Critical patent/EP2892344A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • 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
    • 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
    • A01N43/62—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms three- or four-membered rings or rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the invention relates to the use of benzodiazepinones and benzazepines or their salts as active ingredients for increasing the stress tolerance in plants to abiotic stress, in particular for strengthening plant growth and / or for increasing the plant yield.
  • substituted benzodiazepinones can be used as inhibiting agents against bacterial mono-ADP-ribosyltransferase toxins (see Antimicrobial Agents and Chemotherapy 201 1, 55, 983). It is also known that substituted tricyclic benzodiazepinones and narrow structural analogues can be used as pharmaceutical agents for the treatment of neurodegenerative diseases, neurotoxic effects in strokes, diabetes or in cancer therapy (see WO2001 16136, WO2005012305, WO2007062413). WO2003057699 and DE19946289 also describe the pharmaceutical use of tricyclic benzodiazepinones, while in WO2011008572, the use of quinuclidinyl-substituted ones
  • Dihydrobenzodiazepinoindazolonen is described as 5-HT3 receptor modulators.
  • Benzodiazepinones and Benzazepinone or their salts in each case to increase the Stress tolerance in plants to abiotic stress, to strengthen the
  • Plant growth and / or increase the plant yield Plant growth and / or increase the plant yield.
  • abiotic stress defense reactions e.g., cold, heat, drought, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others. Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106).
  • the response to salt stress involves phosphatases of the ATPK and MP2C types.
  • sucrose synthase and proline transporters are e.g. sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress control of plants against cold and
  • De-dehydrogenases which detoxify the reactive oxygen species (ROS) produced by oxidative stress (Kirch et al., 2005, Plant Mol Biol 57: 315-332). Heat Shock Factors (HSF) and Heat Shock Proteins (HSP) are activated by heat stress and act as chaperones in a similar role to dehydrins in cold and dry stress (Yu et al., 2005, Mol Cells 19: 328-333).
  • ROS reactive oxygen species
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
  • osmolytes such as glycine betaine or their biochemical precursors, eg choline derivatives
  • osmolytes such as glycine betaine or their biochemical precursors, eg choline derivatives
  • the effect of antioxidants such as naphthols and xanthines for increasing the abiotic stress tolerance in plants has also been described (Bergmann et al., DD-277832, Bergmann et al., DD-277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • plants have a number of endogenous reaction mechanisms that can effect effective defense against a variety of harmful organisms and / or natural abiotic stress.
  • the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants.
  • the present invention accordingly provides the use of substituted benzodiazepinones and benzazepines of the general formula (I) or salts thereof
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, halogen, alkyl, cycloalkyl,
  • R 4 is hydrogen, halogen, alkyl, cycloalkyl, cycloalkenyl, halocycloalkyl,
  • Alkylaminocarbonylimino bisalkylaminocarbonylimino, alkylsulfinylimino, arylsulfinylimino, cycloalkylsulfinylimino, alkylthioimino, arylthioimino,
  • Cycloalkylsulfonylimino optionally further substituted iminoalkyl, iminoaryl, iminoheteroaryl, iminoheterocyclyl,
  • W stands for oxygen, sulfur,
  • X is a group NR 10 , CR 11 R 12 , where the groups R 10 , R 11 and R 12 each have the meaning given in the definitions below,
  • R 5 , R 6 independently of one another represent hydrogen, alkyl, haloalkyl, cycloalkyl, aryl, alkenyl, alkynyl, heterocyclyl, heteroaryl, alkoxyalkyl or together form an exo-methylene group which is optionally further substituted and is part of a further ring,
  • R 7 , R 8 independently of one another represent hydrogen, alkyl, haloalkyl, cycloalkyl, aryl, alkenyl, alkynyl, heterocyclyl, heteroaryl, alkoxyalkyl,
  • R 9 is hydrogen, hydroxy, alkyl, cycloalkyl, halogen, alkenylalkyl, alkynylalkyl, haloalkyl, alkoxyalkyl, alkynyl, alkenyl, cycloalkylalkyl, cyanoalkyl, nitroalkyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, aryl, alkylamino, alkylaminoalkyl, bisalkylaminoalkyl, aminocarbonylalkyl, alkylaminocarbonylalkyl,
  • R 11 , R 12 together form an exo-methylene group, optionally further
  • alkyl for alkyl, haloalkyl, halocycloalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthiohaloalkyl, haloalkylthiohaloalkyl, alkoxyalkoxyhaloalkyl,
  • Bisalkylaminoalkoxyhaloalkyl alkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, heteroaryl, heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryloxyheteroaryl, heteroaryloxyaryl, arylalkenyl, Heteroarylalkenyl, heterocyclylalkenyl, arylalkynyl, heteroarylalkynyl,
  • Alkyliminoalkyl aryliminoalkyl, alkoxycarbonyl, cycloalkoxycarbonyl,
  • Aminocarbonyl alkylaminocarbonyl, cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heterocyclyl-N-carbonyl, imino, alkylimino, arylimino, cycloalkylimino, cycloalkylalkylimino, hydroxyimino, alkoxyimino,
  • Cycloalkylaminoalkyl alkoxy (alkoxy) alkyl, heteroarylalkoxyalkyl,
  • Cycloalkylaminoalkylaryl alkoxy (alkoxy) alkylaryl, alkynyl, alkylalkynyl,
  • Aminocarbonylarylalkyl alkylaminocarbonylarylalkyl
  • Cycloalkylaminocarbonylarylalkyl bis-alkylaminocarbonylarylalkyl
  • Arylalkylaminoalkyl, heteroarylalkylaminoalkyl, alkylaminoalkoxyaryl, bisalkylaminoalkoxyaryl, represents hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cyanoalkyl,
  • R 14 , R 15 , R 16 independently of one another represent hydrogen, alkyl, cycloalkyl,
  • R 17 is hydrogen, alkyl, cycloalkyl, haloalkyl, arylalkyl, heteroarylalkyl,
  • Alkoxyalkyl alkylcarbonyloxyalkyl.
  • the compounds of general 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 H O 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 a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.
  • 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 H O 3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid,
  • Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
  • R 1, R 2, R 3 are independently hydrogen, halogen, (Ci-C 8) - alkyl, (Cs-Ce) - cycloalkyl, (C 4 -C 8) cycloalkenyl, (C 3 -C 8) - halocycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, aryl, aryl (Ci-C 8) alkyl, aryl (C 2 -C 8) alkenyl, heteroaryl,
  • W stands for oxygen, sulfur,
  • X is a grouping NR 10 , CR 1 R 12 , where the groups R 10 , R 11 and R 12 each have the meaning given in the definitions below,
  • R 5 , R 6 independently of one another represent hydrogen, (C 1 -C 8) -alkyl, (C 1 -C 8) -haloalkyl,
  • R 7 independently represent hydrogen, (Ci-Ce) alkyl, (Ci-C8) -haloalkyl, (C3-C8) cycloalkyl, aryl, (C2-C8) alkenyl, (Ci-Ce ) Alkynyl, heterocyclyl,
  • R 9 is hydrogen, hydroxy, (Ci-C 8) -alkyl, (C3-C8) -cycloalkyl, halogen, (C 2 -C 8) - alkenyl, (Ci-C 8) alkyl, (C2-C 8) alkynyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (Ci-C 8) - alkoxy- (d-C8) alkyl, (C 2 -C 8) alkynyl, (C 2 -C 8 ) alkenyl, (C 3 -C 8 ) cycloalkyi (C 1 -C 8 ) alkyl, cyano (C 1 -C 8 ) alkyl, nitro (C 1 -C 8 ) -acyl, aryl (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (
  • R 10 is (C 1 -C 8) -alkyl, optionally substituted (C 2 -C 8) -alkenyl, optionally substituted imino (C 1 -C 8) -alkyl, optionally further substituted imino, optionally substituted (C 1 -C 8) -alkyl (C 2 -C 4) -alkyl -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, ( C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkoxycarbonyl- (C 1 -C 8 ) -alkyl
  • R 11 , R 12 together form an exo-methylene group, optionally further
  • R 15, R 16 are independently hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) - cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C 8) alkyl, (C -C 8 ) -haloalkyl, aryl, (Ci-C 8 ) - alkoxycarbonyl, (CrCeJ-hydroxycarbonyl, aminocarbonyl, (Ci-Ce) - alkylaminocarbonyl, (C 3 -C 8) -cycloalkylaminocarbonyl, R 17 is hydrogen, (Ci -C 8) -alkyl, (C 3 -C 8) cycloalkyl, (Ci-C8) haloalkyl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (C 1 -C 8 ) -alkyl, ary
  • R 2 , R 3 independently of one another are hydrogen, halogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 3 -C 7 ) -halocycloalkyl, ( C 2 -C 7 -alkenyl, (C 2 -C 7 ) -alkynyl, aryl, aryl- (C 1 -C 7 ) -alkyl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl,
  • W stands for oxygen, sulfur,
  • X represents a group NR 10 , CR 1 1 R 12 , where the groups R 10 , R 11 and R 12 each have the meaning given in the definitions below,
  • R 5 , R 6 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, (C 1 -C 4 ) -haloalkyl,
  • R 7 , R 8 independently of one another represent hydrogen, (C 1 -C 7) -alkyl, (C 1 -C 7) -haloalkyl,
  • R 9 is hydrogen, hydroxy, (Ci-C7) alkyl, (C 3 -C 7) -cycloalkyl, halogen, (C2-C7) - alkenyl, (Ci-C7) alkyl, (C2-C7) alkynyl (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C1-C7) - alkoxy (Ci-C7) alkyl, (C2-C7) alkynyl, (C 2 -C 7 ) -alkenyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, cyano- (C 1 -C 7 ) -alkyl, nitro- (C 1 -C 7 ) -alkyl, aryl- (Ci -C 7) alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) alkyl,
  • Heteroarylsulfonyl (C 2 -C 7 ) alkynylsulfonyl, (C 1 -C 7 ) -alkylsulfinyl, arylsulfinyl, (C 3 -C 7 ) -cycloalkylsulfinyl, (C 2 -C 7 ) -alkenylsulfinyl, (C 2 -C 7 ) -alkynylsulfinyl, arylsulfinyl, heteroarylsulfinyl , Arylcarbonyl, heteroarylcarbonyl, (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl, (C 2 -C 7) -alkenyloxycarbonyl- (C 1 -C 7) -alkyl,
  • R 10 is (C 1 -C 7) -alkyl, optionally substituted (C 2 -C 7) -alkenyl, optionally substituted amino (C 1 -C 7) -alkyl, optionally further substituted imino, optionally substituted (C 1 -C 7) -alkyl (C 2 -C 4) -alkyl -C7) -alkenyl, heteroaryl- (C2-C7) - alkenyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) alkyl, (C 3 -C 7) -Cycloalkoxycarbonyl- (Ci-C7) alkyl, aryl (Ci-C7) alkoxycarbony
  • Cycloalkylcarbonyl (Ci-C 7) alkoxycarbonyl, Aryloxycarbonyi, (C; rC 7) - cycloalkoxycarbonyl, (Ci-C7) alkylsulfonyl, (C3-C7) cycloalkylsulfonyl,
  • Arylsulfonyl, heteroarylsulfonyl, R 11 , R 12 together form an exo-methylene group, optionally further
  • heteroarylheteroaryl heteroarylaryl, arylaryl, aryloxyaryl, aryloxyheteroaryl, heteroaryloxyaryl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C 7 ) -alkenyl, heterocyclyl- (C 2 -C 7 ) -alkenyl, aryl- (C 2 -C 7 ) -alkenyl, C 7) alkynyl, heteroaryl (C2-C7) alkynyl, heterocyclyl- (C 2 -C 7) -alkynyl, (C3-C 7) cycloalkyl (C 2 -C 7) alkynyl, (C -C 7) alkylamino (Ci-C7) - alkyl, - bis [(Ci-C 7) alkyl] amino- (-C 7) alkyl, hydroxy (dC 7) al
  • R 13 is hydrogen, (Ci-C7) alkyl, (C 3 -C 7) -cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C7) - alkyl, (C 4 -C 7) cycloalkenyl, Cyano- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyl !
  • R 14 , R 15 , R 16 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -
  • R 17 is hydrogen, (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl, (Ci-C7) haloalkyl, aryl (Ci-C7) alkyl, heteroaryl (d-C7 ) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, aryl,
  • Very particular preference is given to the use of compounds of the general formula (I) in which
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C3 -C 6 ) -halocycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 6 ) -alkyl, aryl- (C 2 -C 6 ) -alkenyl, heteroaryl , Heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl,
  • R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl,
  • Iminoheteroaryl represents oxygen, sulfur, a moiety NR 10, CR 1 R 1 12, where the groups R 10, R 11 and R 12 each have the meaning according to the following definitions,
  • R 5 , R 6 are each independently hydrogen, (Ci-Cf,) - alkyl, (Ci-Cf,) - haloalkyl, (C3-C6) -cycloalkyl, optionally substituted phenyl, (C2-C6) alkenyl, (C2 -C 6) alkynyl, heterocyclyl, heteroaryl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl or together form an exo-methylene group which is optionally further substituted and is part of a further ring,
  • R 7 , R 8 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl,
  • R 9 is hydrogen, hydroxy, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, halogen, (C 2 -C 6) - alkenyl, (Ci-C 6) alkyl, (C2- C 6) alkynyl (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (Ci-C6) - alkoxy (CrC 6) alkyl, (C 2 -C 6) alkynyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) - alkyl, cyano- (CrC 6) alkyl, nitro, (Ci-C 6) alkyl, aryl (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (
  • Heteroarylsulfonyl (C2-C6) alkynylsulfonyl, (CRC6) alkylsulfinyl, arylsulfinyl, (C 3 -C 6) cycloalkylsulfinyl, (C2-C6) alkenylsulfinyl, (C 2 -C 6) alkynylsulfinyl, arylsulfinyl, heteroarylsulfinyl , Arylcarbonyl, heteroarylcarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyloxycarbonyl- (C 1 -C 6) -alkyl,
  • R 1 1 , R 12 together form an exo-methylene group, optionally further
  • heteroarylheteroaryl heteroarylaryl, arylaryl, aryloxyaryl, aryloxyheteroaryl, heteroaryloxyaryl, aryl- (C 2 -C 6) -alkenyl, heteroaryl- (C 2 -C 6) -alkenyl, aryl- (C 2 -C 6) alkynyl, heteroaryl- (C 2 -C 20) -alkynyl, heterocyclyl- (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl- (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -alkylamino - (C 1 -C 6 ) -alkyl, bis - [(C 1 -C 6 ) -alkyl] amino- (C 1 -C 6 ) -alkyl, bis - [(C 1 -C 6
  • R 13 is hydrogen, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, (C 4 -C 6) - cycloalkenyl, cyano- (CrC 6) alkyl, (C2-C6) alkenyl (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkynyl (Ci- C 6 ) -alkyl, aryl - (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, aryl, (C 1 -C 6 ) -alkylcarbonyl , (C 3 -C 6 ) -cycloalkylcarbonyl
  • R 14, R 15, R 16 independently represent hydrogen, (CrC 6) alkyl, (C 3 -C 6) -
  • Cycloalkyl (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, aryl, (C 1 -C 6 ) - Alkoxycarbonyl, (C 1 -C 6) -hydroxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl,
  • R 17 is hydrogen, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) -haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, aryl,
  • Residue definitions apply both to the end products of the formula (I) as well as correspondingly to the starting or in each case required for the preparation
  • haloalkyl-substituted benzodiazepinones and benzazepines of the general formula (Ia) are also not yet known in the art.
  • haloalkyl-substituted benzodiazepinones of the general formula (Ia) or salts thereof are also not yet known in the art.
  • R 1, R 2, R 3 are independently hydrogen, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) - cycloalkyl, (C 4 -C 8) cycloalkenyl, (C 3 -C 8 ) -halocycloalkyl, (C 2 -C 8 ) -alkenyl,
  • W stands for oxygen, sulfur,
  • R 5 , R 6 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl,
  • R 7 , R 8 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl,
  • R 9 is hydrogen, hydroxy, (Ci-Cs) alkyl, (C 3 -C 8) -cycloalkyl, halogen, (C 2 -C 8) - alkenyl (dC 8) alkyl, (C 2 -C 8 ) alkynyl (Ci-C 8) alkyl, (dC 8) -haloalkyl, (C, -C 8) - alkoxy (dC 8) alkyl, (C 2 -C 8) -alkynyl, (C 2 -C 8) alkenyl, (C-C8) cycloalkyl (CrC 8) - alkyl, cyano- (Ci-C 8) alkyl, nitro, (Ci-C 8) alkyl, aryl (Ci- C 8 ) -alkyl, heteroaryl
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, ( C 3 -C 6) halocycloalkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl, aryl, aryl (Ci-C 6) alkyl, aryl (C 2 -C 6 ) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkyl, (C 1 -C 6) - Alkoxy- (C 1 -C 6 ) -alkyl,
  • W stands for oxygen, sulfur,
  • R 5 , R 6 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, aryl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, heterocyclyl,
  • R 7 , R 8 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 8 -haloalkyl, (C 3 -C 6 ) -cycloalkyl, aryl, (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkynyl, heterocyclyl,
  • R 9 is hydrogen, hydroxy, (Ci-C 6) -alkyl, (C3-C6) -cycloalkyl, halogen, (C 2 -C 6) - alkenyl, (Ci-C 6) alkyl, (C 2 - C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) - Alkoxy (Ci-C 6) alkyl, (C2-C6) -alkynyl, (C 2 -C 6) alkenyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, cyano- ( C 1 -C 6 ) -alkyl, nitro (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -
  • Q is (Ci-Ci 2 ) -haloalkyl, (C 3 -C 6 ) -halocycloalkyl, (Ci-C6) -alkoxy- (Ci-C 6 ) -haloalkyl, (Ci-C 6 ) -haloalkoxy- (Ci-C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -haloalkyl,
  • R 1, R 2, R 3 are independently hydrogen, halogen, (Ci-C 8) -alkyl, (Cs-Ce) - cycloalkyl, (C 4 -C 8) cycloalkenyl, (C 3 -C 8) - halocycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, aryl, aryl (Ci-C 8) alkyl, aryl (C 2 -C 8) alkenyl, heteroaryl, heteroaryl ( -C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (dC 8) - alkoxy (dC 8) alkyl, (Ci-C8) alkylthio, (C, -C8) - haloalkylthio, (Ci-C 8) haloalkyl, (CrC 8) -alkoxy, (Ci-C8) -halo
  • W stands for oxygen, sulfur, R 5 , R 6 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 8) -haloalkyl,
  • R 7 , R 8 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 6 -haloalkyl,
  • R 9 is hydrogen, hydroxy, (Ci-Cs) alkyl, (C3-C8) -cycloalkyl, halogen, (C 2 -C 8) - alkenyl, (Ci-C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (Ci-C8) - alkoxy (Ci-C 8) alkyl, (C 2 -C 8) alkynyl , (C 2 -C 8) -alkenyl, (C 3 -C 8) cycloalkyl (Ci-C8) - alkyl, cyano- (Ci-C 8) alkyl, nitro, (Ci-C 8) - alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (
  • Q is (Ci-Ci 2 ) -haloalkyl, (C 3 -C 8 ) -halocycloalkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, (Ci-C 8 ) -haloalkoxy- (CrC 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 4) -alkyl) -C 8) alkoxy (Ci-C 8) - haloalkyl, - bis [(Ci-C 8) alkyl] amino- (Ci-C 8) alkoxy Ci-C 8) hal
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, ( C 3 -C 6 ) -halocycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 6 ) -alkyl, aryl- (C 2 -C 6 ) -alkenyl , Heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl,
  • W stands for oxygen, sulfur,
  • R 5 , R 6 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6) -haloalkyl,
  • R 7 , R 8 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl,
  • R 9 represents hydrogen, hydroxy, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, halogen, (d) -alkenyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl ( Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (dd) - alkoxy- (Ci-C 6) alkyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) - alkenyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, cyano- (Ci-C6) alkyl, nitro, (Ci-C 6) alkyl, aryl (Ci-C 6) alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (
  • R 13 is hydrogen, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) - alkyl, (C 4 -C 6) cycloalkenyl, cyano (Ci-C 6) alkyl, (C2-C6) alkenyl (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkynyl (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, aryl, (C 1 -C 4) -Alkylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbony
  • Q is (Ci-C 8 ) -haloalkyl, (C 3 -C 6 ) -halocycloalkyl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -haloalkyl, (Ci-C 6 ) -haloalkoxy- (Ci -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -haloalkyl,
  • R 2, R 3 are independently hydrogen, halogen, (DC 8) alkyl, (C 3 -C 8) - cycloalkyl, (C4-C8) cycloalkenyl, (C 3 -C 8) halocycloalkyl, (C2 -C 8) alkenyl, (C2-C8) alkynyl, aryl, aryl (Ci-C 8) alkyl, aryl (C 2 -C 8) alkenyl, heteroaryl, heteroaryl (CRC 8) - alkyl, heterocyclyl, heterocyclyl (-C 8) alkyl, (dC 8) - alkoxy (dC 8) alkyl, (Ci-C8) alkylthio, (Ci-C8) haloalkylthio, (Ci-C 8 ) haloalkyl, (CrC 8) -alkoxy, (Ci-C8) -haloalkoxy, (C 3 -
  • R 7 , R 8 independently of one another represent hydrogen, (dQ-alkyl, (dC 8 ) -haloalkyl,
  • R 9 is hydrogen, hydroxy, (DC 8) alkyl, (C 3 -C 8) -cycloalkyl, halogen, (C 2 -C 8) - alkenyl, (Ci-C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (Ci-C8) - alkoxy (dC 8) alkyl, (C 2 -C 8) -alkynyl, ( C 2 -C 8) -alkenyl, (C 3 -C 8) cycloalkyl (Ci-C8) - alkyl, cyano- (dC 8) alkyl, nitro, (Ci-C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (Ci-C 8) alkyl, aryl, (Ci
  • Q is (CrCl 2) -haloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-C 8) alkoxy (dC 8) -haloalkyl, (Ci-C8) haloalkoxy (Ci-C 8) -haloalkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -haloalkyl,
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, ( C 3 -C 6) halocycloalkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl, optionally substituted phenyl, aryl (Ci-C 6) alkyl, aryl (C 2 - C6) -alkenyl, heteroaryl, heteroaryl- (Ci-Ce) -alkyl, heterocyclyl,
  • W stands for oxygen, sulfur,
  • R 5 , R 6 independently of one another represent hydrogen, (C 1 -C 6 -alkyl, (C 1 -C 6) -haloalkyl,
  • R 7 , R 6 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl,
  • R 9 is hydrogen, hydroxy, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, halogen, (C 2 -C 6) - alkenyl, (Ci-C 6) alkyl, (C2- C 6) alkynyl (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, (C 2 -C 6) - alkynyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) - alkyl, cyano- (Ci-C6) alkyl, nitro, (Ci-C 6) alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, hetero
  • arylsulfonyi is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyi, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
  • Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl, Ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl.
  • heteroarylsulfonyl represents optionally substituted
  • substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
  • Alkylcarbonylamino, dialkylamino or alkoxy groups Alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio.
  • Alkenylthio means an Aikenyirest bound via a sulfur atom
  • Alkinylthio means an alkynyl radical bonded via a sulfur atom
  • Cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • Cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom.
  • Alkoxy denotes an alkyl radical bonded via an oxygen atom
  • alkenyloxy denotes an alkynyl radical bonded via an oxygen atom
  • aikynyloxy denotes an alkynyl radical bound via an oxygen atom
  • cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
  • Aryl is also generally known from the term “optionally substituted phenyl ".
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
  • Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
  • heteroatom from the group N, O and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2, 3-dihydro-1 H-pyrrole 1- or 2- or
  • Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of
  • Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 or 3 or 4 or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1 - or 5-
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-Dioxazepan-2 or 3 or 5 or
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, Alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also known as SO) and S (O) 2 (also abbreviated to SO 2) occur and form in the heterocyclic ring.
  • N (O), S (O) (also known as SO) and S (O) 2 also abbreviated to SO 2
  • heteroaryl is heteroaromatic
  • Compounds ie fully unsaturated aromatic heterocyclic Compounds, preferably for 5- to 7-membered rings having 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N.
  • Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are annelated heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl denotes a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted, preferably unsubstituted
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, Particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • Haloalkyl means the same or different
  • Polyhaloalkyl such as CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
  • Hydrocarbon chain can be located, such as. B. CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CF 3 CHFCF 2
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
  • Carbon atoms corresponding to the range for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, 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, heptyls such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained.
  • alkenyl also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulative double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, eg P.sub.p-1 -ene-1.
  • alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl.
  • C 2 -C 6) -alkynyl is, for example, ethynyl, propargyl, 1-methylprop-2-yn-1-yl, 2-butynyl,
  • 2-pentynyl or 2-hexynyl preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methylbut-3-yn-1-yl.
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl
  • substituents also have one
  • an alkylidene group such as methylidene, are included.
  • optionally substituted cycloalkyl also become
  • polycyclic aliphatic systems such as, for example, bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1 .0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), bicyclo [2.2.2] octan-2-yl, adamantane 1 -yl and adamantan-2-yl.
  • (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl having from three to seven carbon atoms corresponding to the range of C atoms.
  • substituted cycloalkyl are also spirocyclic aliphatic
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl radical, for example a
  • Alkylidene group such as methylidene, are included. In case of if necessary
  • Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
  • stannyl stands for a further substituted radical containing a tin atom
  • “Germanyl” is analogous to a further substituted radical which is a
  • Zeroconyl represents a further substituted radical containing a zirconium atom.
  • Hafnyl represents a further substituted radical containing a
  • Boryl borolanyl
  • borinanyl represent further substituted and optionally cyclic groups, each containing a boron atom.
  • Plumbanyl represents a further substituted radical containing a lead atom.
  • Haldra rgyl stands for a further substituted radical containing a mercury atom.
  • Al stands for a further substituted radical containing an aluminum atom.
  • Magnetic represents a further substituted radical containing a magnesium atom.
  • Zincyl represents a further substituted radical containing a zinc atom.
  • the compounds of the general formula (I) can, depending on the nature and linkage of Substituents exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof
  • Substituted benzodiazepinones and benzazepinones can be prepared according to known
  • the relevant optionally further substituted 2-halo-3-nitrobenzoic acid can be converted into the corresponding benzoic acid ester with the aid of a suitable acid chloride (eg thionyl chloride or oxalyl chloride) and a suitable alcohol (eg methanol or ethanol).
  • a suitable acid chloride eg thionyl chloride or oxalyl chloride
  • a suitable alcohol eg methanol or ethanol
  • the optionally further substituted 2-halo-3-nitrobenzoic acid ester thus obtained is then reacted by reaction with an optionally further substituted diaminoethane using a suitable base (eg sodium carbonate or potassium carbonate) in a polar solvent.
  • a suitable base eg sodium carbonate or potassium carbonate
  • aprotic solvents eg, isopropanol, n-propanol, 1-butanol, 2-butanol
  • 9-nitro-5H-1,4-benzodiazepin-5-one reacted with either hydrogen in the presence of palladium on carbon in a suitable solvent or with tin (II) chloride is reduced to an optionally further substituted 9-amino-5H-1,4-benzodiazepin-5-one (Scheme 1).
  • the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and Q mentioned in the following scheme 1 have the meanings defined above.
  • terephthalaldehyde monodiethyl acetal can be converted to the desired target compound by condensation with an optionally substituted 9-amino-5H-1,4-benzodiazepin-5-one and the acetal group subsequently purified using a suitable acid (eg sulfuric acid in a suitable protic solvent) are cleaved to an aldehyde group.
  • a suitable acid eg sulfuric acid in a suitable protic solvent
  • the aldehyde group in question can be converted by sodium cyanoborohydride-mediated reductive amination into corresponding amines or by hydride-mediated reduction in the corresponding alcohol.
  • the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and Q mentioned in the following scheme 2 have the meanings defined above.
  • methyl and ethyl are exemplified as substituents as a proxy for the groups of this invention.
  • the functionalization of the benzodiazepinone NH group succeeds by deprotonation with a suitable base, e.g. Sodium hydride in an aprotic solvent, and subsequent reaction with a suitable electrophile, e.g. one
  • Substituted 3,4-dihydro [1, 4] diazepino [6,7,1 -hi] indole-1 (2H) -ones according to the invention can be prepared in a multistage synthesis starting from 2-iodoaniline.
  • further substituted 2-iodoaniline is optionally N-alkylated with the aid of propiolactone and then reacted via a Friedel-Crafts acylation to form an intermediate substituted 2,3-dihydroquinoline-4 (1H) -one.
  • Transition metal catalyzed reaction using a suitable palladium catalyst eg palladium (II) chloride
  • a suitable polar aprotic solvent eg palladium (II) chloride
  • Dissolved solvent eg acetonitrile
  • 3,4-dihydro [1, 4] diazepino [6,7,1-hi] indole-1 (2H) -one (Scheme 3).
  • the radicals R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and Q mentioned in the following scheme 3 have the meanings defined above.
  • Inventive optionally further substituted 4,5-dihydro-6H-pyrrolo [1, 2 a] [1, 4] benzodiazepine-6-ones can be prepared via a multi-step synthesis route starting from optionally further substituted Aminomethylfuranen.
  • a suitable amine base eg triethylamine or diisopropylethylamine
  • a suitable polar aprotic solvent eg tetrahydrofuran
  • Reaction solution was heated to 70 ° C and stirred at this temperature for 2 hours. After cooling to room temperature, the solvent was concentrated under reduced pressure. The remaining residue was dissolved in methanol (10 mL).
  • A1 1 Compounds A1 1 -1 to A1 1 -300 of the general formula (I) in which R 2 is methyl, R 1 , R 3 and R 9 are hydrogen and X, W, R 4 , R 5 , R 6 , R 7 , R 8 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 300, corresponding to compounds A1 1 -1 to A1 1 -300).
  • both groups R 5 and R 7 in this case together form a saturated or partially saturated ring.
  • R 3 and R 9 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective
  • Trifluoromethyl, R 2 , R 3 and R 9 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective individual compound are the radical definitions given in Table 2 (Nos 1 to 949, corresponding to compounds B5-1 to B5-949).
  • Trifluoromethylthio, R 2 , R 3 and R 9 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective individual compound, the remaining definitions given in Table 2 (Nos 1 to 949, corresponding to compounds B6-1 to B6-949).
  • Trifluoromethoxy, R 2 , R 3 and R 9 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective individual compound to the definitions given in Table 2 (Nos 1 to 949, corresponding to compounds B7-1 to B7-949).
  • Methylthio, R 2 , R 3 and R 9 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound are the radical definitions given in Table 2 (Nos 1 to 949, corresponding to compounds B9-1 to B9-949).
  • B1 Compounds B1 1 -1 to B1 1 -949 of the general formula (Ia) in which R 2 is chlorine, R 3 R 3 and R 9 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 is the respective ones
  • R 1 , R 3 and R 9 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective
  • R 1, R 2 and R 3 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound are the radical definitions given in Table 2 (Nos 1 to 949 corresponding to compounds B36-1 to B36-949).
  • Trifluoromethyl, R 2 , R 3 , R 9 and R 13 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective individual compound to the definitions given in Table 2 (Nos 1 to 949, corresponding compounds C5-1 to C5-949).
  • C16 Compounds C16-1 to C 16-949 of the general formula (Ib) in which R 2 is trifluoromethylthio, R 1 , R 3 , R 9 and R 13 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound correspond to the radical definitions given in Table 2 (Nos 1 to 949, corresponding to compounds C16-1 to C16-949).
  • C17 Compounds C17-1 to C 17-949 of the general formula (Ib) in which R 2 is ethyl, R 3 , R 9 and R 13 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound the radical definitions given in Table 2 (Nos 1 to 949;
  • C36 Compounds C36-1 to C36-949 of the general formula (Ib) in which R 9 and R 13 are n-propyl, R 1, R 2 and R 3 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound correspond to the radical definitions given in Table 2 (Nos 1 to 949, corresponding to compounds C36-1 to C36-949).
  • C37 Compounds C37-1 to C37-949 of the general formula (Ib) in which R 9 is allyl, R 1 , R 3 and R 13 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound, the radical definitions given in Table 2 (Nos 1 to 949;
  • Trifluoromethyl, R 2 , R 3 , R 9 and R 17 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound are the radical definitions given in Table 2 (Nos 1 to 949; D5-1 to D5-949).
  • D16 Compounds D16-1 to D 16-949 of the general formula (Id) in which R 2 is trifluoromethylthio, R ⁇ R 3 , R 9 and R 17 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective one-member compound correspond to the radical definitions given in Table 2 (Nos 1 to 949, corresponding to compounds D16-1 to D 16-949).
  • D17 Compounds D17-1 to D 17-949 of the general formula (Id) in which R 2 is ethyl, R 3 , R 9 and R 17 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the particular individual compound the radical definitions given in Table 2 (Nos 1 to 949;
  • R 1 , R 2 , R 3 and R 17 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for each individual compound to the definitions given in Table 2 (Nos 1 to 949, corresponding compounds D30-1 to D30-949).
  • Pr, R 1 , R 2 , R 3 and R 17 are hydrogen and Q, W, R 5 , R 6 , R 7 , R 8 for the respective individual compound, the radical definitions given in Table 2 (Nos 1 to 949;
  • D40-1 compounds to D40-949 of the general formula (Id) wherein R 17 is CH ( NOH) R ⁇ R 2, R 3 and R 9 are hydrogen, and Q, W, R 5, R 6, R 7 , R 8 for the particular individual compound correspond to the radical definitions given in Table 2 (Nos 1 to 949, corresponding to compounds D40-1 to D40-949).
  • R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for the particular individual compound are the radical definitions given in Table 3 (Nos 1 to 250, corresponding to compounds E2-1 to E2-250).
  • R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for the respective individual compound are the radical definitions given in Table 3 (Nos 1 to 250, corresponding to compounds E4-1 to E4-250).
  • R 3 and R 4 are hydrogen and W
  • R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for each individual compound are the radical definitions given in Table 3 (Nos 1 to 250, corresponding to compounds E5-1 to E 5-250).
  • E6. Compounds E6-1 to E6-250 of the general formula (Ic) in which R 1 is methyl, R 2 , R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for the particular individual compound correspond to the radical definitions given in Table 3 (Nos 1 to 250, corresponding to compounds E6-1 to E 6-250).
  • Trifluoromethyl, R 2 , R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for the respective individual compound to the definitions given in Table 3 (Nos 1 to 250; Connections E8-1 to E8-250).
  • Phenyl, R 1 , R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for the particular individual compound are the radical definitions given in Table 3 (Nos 1 to 250; Connections E17-1 to E17-250).
  • E18. Compounds E18-1 to E 18-250 of the general formula (Ic) in which R 2 is ethyl, R 1 , R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 4 , R 15 and R 16 for the particular individual compound correspond to the radical definitions given in Table 3 (Nos 1 to 250, corresponding to compounds E18-1 to E 18-250).
  • Methylthio, R 1 , R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for the respective single-compound, the rest definitions given in Table 3 (Nos 1 to 250; Connections E30-1 to E30-250).
  • E31. Compounds E31-1 to E31-250 of the general formula (Ic) in which R 2 is trifluoromethylthio, R 1 , R 3 and R 4 are hydrogen and W, R 7 , R 8 , R 9 , R 14 , R 15 and R 16 for each individual compound referred to in Table 3

Abstract

Utilisation de benzodiazépinones et de benzazépinone substituées de formule générale (I) ou de leurs sels, les groupes de la formule générale (I) ayant les définitions figurant dans la description, pour augmenter la tolérance des plantes au stress abiotique, renforcer la croissance des plantes et/ou augmenter le rendement des plantes, et procédés spéciaux pour produire les composés susmentionnés.
EP13756160.1A 2012-09-05 2013-09-02 Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes Withdrawn EP2892344A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP13756160.1A EP2892344A1 (fr) 2012-09-05 2013-09-02 Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12183164 2012-09-05
EP13756160.1A EP2892344A1 (fr) 2012-09-05 2013-09-02 Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes
PCT/EP2013/068112 WO2014037313A1 (fr) 2012-09-05 2013-09-02 Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Publications (1)

Publication Number Publication Date
EP2892344A1 true EP2892344A1 (fr) 2015-07-15

Family

ID=46832241

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13756160.1A Withdrawn EP2892344A1 (fr) 2012-09-05 2013-09-02 Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Country Status (6)

Country Link
US (1) US20150218110A1 (fr)
EP (1) EP2892344A1 (fr)
JP (1) JP2015533783A (fr)
CN (1) CN104754942A (fr)
BR (1) BR112015004311A2 (fr)
WO (1) WO2014037313A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9403803B2 (en) 2014-10-08 2016-08-02 Allergan, Inc. Indole-3-carboxamides as kinase inhibitors
CN104604879A (zh) * 2014-12-31 2015-05-13 江阴苏利化学股份有限公司 一种含有氮杂卓的防治甘蓝蚜虫的农药组合物的新应用
CN105367507B (zh) * 2015-07-21 2018-06-01 华中师范大学 化合物及其制备方法和用途
CN107286166B (zh) * 2016-04-11 2020-03-31 上海勋和医药科技有限公司 取代1，3，4，5-四氢-6h-吡咯并[4，3，2-ef][2]苯并氮杂-6-酮衍生物
CN106070243A (zh) * 2016-07-13 2016-11-09 陈志勤 一种苯并二氮杂卓类化合物作为农用杀虫剂的新用途
CN106070242A (zh) * 2016-07-13 2016-11-09 陈志勤 一种苯并二氮杂卓类化合物作为杀菌剂的用途
WO2018115984A1 (fr) 2016-12-19 2018-06-28 Cellix Bio Private Limited Compositions et méthodes pour le traitement d'une inflammation
JP2020128340A (ja) * 2017-04-27 2020-08-27 日本農薬株式会社 ５員環の含窒素複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
CN109651377B (zh) * 2017-10-12 2020-10-20 成都海创药业有限公司 一种治疗癌症的化合物及其用途
CN108047229A (zh) * 2017-12-15 2018-05-18 宜昌人福药业有限责任公司 苯并二氮杂*类化合物
CN111662299B (zh) * 2020-07-10 2022-07-26 中山大学 一种取代吲哚并氮杂酮类化合物及其制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ECSP003637A (es) * 1999-08-31 2002-03-25 Agouron Pharma Inhibidores triciclicos de poli (adp-ribosa) polimerasas
DE19946289A1 (de) * 1999-09-28 2001-03-29 Basf Ag Benzodiazepin-Derivate, deren Herstellung und Anwendung
JP4323802B2 (ja) * 2000-12-01 2009-09-02 エムジーアイ・ジーピー・インコーポレーテッド 化合物およびその使用
NZ544989A (en) * 2003-07-25 2009-10-30 Cancer Rec Tech Ltd Tricyclic PARP inhibitors
ES2523503T3 (es) * 2010-03-04 2014-11-26 Bayer Intellectual Property Gmbh 2-Amidobencimidazoles sustituidos con fluoroalquilo y su uso para el aumento de la tolerancia al estrés en plantas

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2014037313A1 *

Also Published As

Publication number Publication date
WO2014037313A1 (fr) 2014-03-13
BR112015004311A2 (pt) 2017-07-04
JP2015533783A (ja) 2015-11-26
CN104754942A (zh) 2015-07-01
US20150218110A1 (en) 2015-08-06

Similar Documents

Publication Publication Date Title
EP2892345A1 (fr) Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes
EP2611300B1 (fr) Dérivés de dihydropyrimdinone annelés et substitués
EP2658376A1 (fr) Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.
AU2012242124B2 (en) Substituted 5-(cyclohex-2-en-1-yl)-penta-2,4-dienes and 5-(cyclohex-2-en-1-yl)-pent-2-en-4-ynes as active agents against abiotic stress in plants
EP2729007A1 (fr) Utilisation d'isoquinoléinones, d'isoquinoléinediones, d'isoquinoléinetriones et de dihydroisoquinoléinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes
WO2014037313A1 (fr) Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes
EP2697214A1 (fr) Vinyl- et alcinyl-cyclohexénols substitués en tant que principes actifs contre le stress abiotique des végétaux
EP2547204A2 (fr) Aryl- et hétarylsulfonamides en tant que substances actives contre le stress abiotique des végétaux
WO2013041602A1 (fr) Utilisation de dérivés d'acide 1-phényl-pyrazol-3-carboxylique à substitution en position 4 en tant qu'agents actifs contre le stress abiotique chez les végétaux
EP2928297A1 (fr) Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes
WO2014086751A1 (fr) Utilisation de 1-(aryléthinyl)-cyclohexanols, 1-(hétéroaryléthinyl)-cyclohexanols, 1-(hétérocyclyléthinyl)-cyclohexanols et 1-(cyloalcényléthinyl)-cyclohexanols substitués comme principes actifs contre le stress abiotique des plantes
EP2555619A2 (fr) Utilisation de l'acide 4-phényl butyrique et/ou de ses sels pour augmenter la tolérance au stress chez des végétaux
EP2542533A1 (fr) 2-amidobenzimidazoles substitués par fluoroalkyle et leur utilisation pour augmenter la tolérance au stress chez les végétaux
EP2510786A1 (fr) Dérivés de prop-2-yn-1-ol et prop-2-en-1-ol substitués
JP2014515746A (ja) 非生物的植物ストレスに対する活性化合物としての置換５−（ビシクロ［４．１．０］ヘプト−３−エン−２−イル）ペンタ−２，４−ジエン類および５−（ビシクロ［４．１．０］ヘプト−３−エン−２−イル）ペント−２−エン−４−イン類
WO2014037349A1 (fr) Utilisation d'acide 2,3-dihydro-1-benzofurane-4-carboxylique substitué ou de ses sels comme principes actifs contre le stress abiotique des plantes
EP2740356A1 (fr) Dérivés d'acides (2Z)-5(1-hydroxycyclohexyl)pent-2-en-4-ines substitués
EP2740720A1 (fr) Dérivés d'acides pent-2-en-4-ines bicycliques et tricycliques substitués et leur utilisation pour augmenter la tolérance au stress chez les plantes
WO2011124553A2 (fr) Utilisation de dérivés de l'acide (1-cyanocyclopropyl)phényl phosphinique, de leurs esters et/ou de leurs sels pour augmenter la tolérance de végétaux au stress abiotique

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20150407

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20151028